KR101731102B1 - Novel Quinolinone Derivatives and Uses Thereof - Google Patents

Novel Quinolinone Derivatives and Uses Thereof Download PDF

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KR101731102B1
KR101731102B1 KR1020167008791A KR20167008791A KR101731102B1 KR 101731102 B1 KR101731102 B1 KR 101731102B1 KR 1020167008791 A KR1020167008791 A KR 1020167008791A KR 20167008791 A KR20167008791 A KR 20167008791A KR 101731102 B1 KR101731102 B1 KR 101731102B1
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dihydroquinoline
carboxamide
mmol
ethyl
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김용철
고효진
곽승화
김민정
이소덕
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광주과학기술원
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract

본 발명은 다양한 신규 퀴놀리논(quinolinone) 유도체 화합물 및 이들을 유효성분으로 포함하는 IL-2 활성 억제용 조성물에 관한 것이다. 본 발명은 과도한 IL-2 발현/활성과 관련된 다양한 질환, 즉 만성 염증성 질환 또는 자가면역 질환의 예방 또는 치료에 유용하게 이용될 수 있다.The present invention relates to various novel quinolinone derivative compounds and a composition for inhibiting IL-2 activity comprising these as an active ingredient. The present invention can be usefully used for the prevention or treatment of various diseases associated with excessive IL-2 expression / activity, i.e. chronic inflammatory diseases or autoimmune diseases.

Description

신규한 퀴놀리논 유도체 및 이의 용도{Novel Quinolinone Derivatives and Uses Thereof}Novel Quinolinone Derivatives and Uses Thereof < RTI ID = 0.0 >

본 발명은 신규한 퀴놀리논 유도체 및 이의 과도한 IL-2 활성과 관련된 질환의 예방 및 치료용도에 관한 것이다.The present invention relates to novel quinolinone derivatives and their use for the prevention and treatment of diseases associated with excessive IL-2 activity.

T-세포 성장인자(T-cell growth factor)라고도 불리우는 인터루킨-2(Interleukin-2, IL-2)는 T-세포 의존성 면역반응에서 중요한 역할을 한다. IL-2는 4개의 번들로 15kDa 크기의 이로어진 α-나선 단백질로, T 세포에서 생성 및 분비되며, T 세포의 증식 및 활성화와 분화에 관여할 뿐만 아니라, B 세포나 대식세포 등과 같은 다른 면역세포들의 활성화에도 영향을 미치는 중요한 사이토카인(cytokine)이다. IL-2는 타겟 세포막의 IL-2Rα(CD25), IL-2Rβ (CD122) 및 IL-2Rγ(CD132) 서브유닛으로 이루어진 고-친화도 수용체와 결합하며, 이중 IL-2Rβ 및 IL-2Rγ는 세포 내 신호전달에 중요한 역할을 하고, IL-2Rα는 세포질내 도메인이 짧아 신호전달에 관여하지는 않지만 수용체의 친화도를 10-100배 증가시킨다.Interleukin-2 (IL-2), also called T-cell growth factor, plays an important role in T-cell dependent immune responses. IL-2 is a 15-kDa α-helical protein with four bundles. It is produced and secreted by T cells, and is involved in the proliferation, activation and differentiation of T cells, as well as other immunity such as B cells or macrophages It is an important cytokine that also affects the activation of cells. IL-2 binds to high-affinity receptors composed of IL-2R? (CD25), IL-2R? (CD122) and IL-2R? (CD132) subunits of the target cell membrane, It plays an important role in my signal transduction, and IL-2Rα is not involved in signal transduction due to its short intracellular domain but it increases receptor affinity 10-100 times.

IL-2를 코딩하는 유전자 발현은 NF-AT, AP-1, NF-κB, Oct 등의 전자조절인자들에 의하여 조절되며, 평상시에는 거의 발현되지 않다가, 면역체계가 활성화될 경우에 급격히 그러나 한시적으로 발현이 유도되어 단백질이 합성 및 분비된다.Expression of IL-2-encoding genes is regulated by electron-regulating factors such as NF-AT, AP-1, NF-κB and Oct and is rarely expressed in normal cases. Expression is induced for a limited time, and protein is synthesized and secreted.

한편, IL-2가 과도하게 발현될 경우, 염증이나 자가면역 질환을 비롯한 다양한 면역계 질환을 야기한다. 이에, IL-2의 생물학적 활성을 간섭하거나, IL-2와 IL-2 수용체의 각 서브유닛 간의 상호작용을 억제하는 것이 과도한 IL-2의 발현 및 활성에 기인한 질환의 치료에 대한 효과적인 접근이 될 것이다. 지금까지 IL-2 저해제로서 제시된 사이클로스포린 A(사이클로sporin A), FK506 등의 화합물은 부작용이 심해 많은 만성 질환들을 포함하는 염증 및 조절되지 않은 면역 반응관련 질환에 있어 장기 투여가 불가능했으며, 이에 보다 효율적이며 안전하고 단순한 기전을 가지는 IL-2 저해제의 개발이 절실한 상황이다.On the other hand, when IL-2 is overexpressed, it causes various immune system diseases including inflammation and autoimmune diseases. Thus, it is believed that interfering with the biological activity of IL-2 or inhibiting the interaction between each subunit of IL-2 and IL-2 receptors is an effective approach to the treatment of diseases caused by excessive IL-2 expression and activity Will be. Compounds such as cyclosporin A (cyclosporin A) and FK506, which have been proposed as IL-2 inhibitors so far, have been unable to be administered for a long time in inflammatory and unregulated immune response-related diseases including many chronic diseases, And the development of an IL-2 inhibitor having a safe and simple mechanism is urgently needed.

본 명세서 전체에 걸쳐 다수의 논문 및 특허문헌이 참조되고 그 인용이 표시되어 있다. 인용된 논문 및 특허문헌의 개시 내용은 그 전체로서 본 명세서에 참조로 삽입되어 본 발명이 속하는 기술 분야의 수준 및 본 발명의 내용이 보다 명확하게 설명된다.Numerous papers and patent documents are referenced and cited throughout this specification. The disclosures of the cited papers and patent documents are incorporated herein by reference in their entirety to better understand the state of the art to which the present invention pertains and the content of the present invention.

본 발명자들은 면역조절 관련 질환의 발병에 중요한 역할을 하는 염증성 사이토카인인 IL-2의 효과적인 길항제를 발굴함으로써 다양한 염증성 질환 및 자가면역 질환의 예방 또는 치료용 조성물을 개발하기 위하여 예의 연구 노력하였다. 그 결과 본 발명의 신규 퀴놀리논 유도체가 IL-2의 활성을 매우 효과적으로 억제함을 발견함으로써, 본 발명을 완성하게 되었다.The present inventors have sought to develop a composition for the prevention or treatment of various inflammatory diseases and autoimmune diseases by identifying effective antagonists of IL-2, an inflammatory cytokine that plays an important role in the development of diseases related to immunomodulation. As a result, it was found that the novel quinolinone derivatives of the present invention inhibit the activity of IL-2 very effectively, thereby completing the present invention.

따라서 본 발명의 목적은 신규한 퀴놀리논 유도체를 제공하는 데 있다.Accordingly, an object of the present invention is to provide a novel quinolinone derivative.

본 발명의 다른 목적은 IL-2(Interleukin-2)의 활성 억제용 조성물을 제공하는 데 있다.It is another object of the present invention to provide a composition for inhibiting the activity of IL-2 (Interleukin-2).

본 발명의 또 다른 목적은 염증성 질환 또는 자가면역 질환의 예방 또는 치료용 조성물을 제공하는 데 있다.It is still another object of the present invention to provide a composition for the prophylaxis or treatment of inflammatory diseases or autoimmune diseases.

본 발명의 다른 목적 및 이점은 하기의 발명의 상세한 설명, 청구범위 및 도면에 의해 보다 명확하게 된다.Other objects and advantages of the present invention will become more apparent from the following detailed description of the invention, claims and drawings.

본 발명의 일 양태에 따르면, 본 발명은 다음의 화학식 1로 표시되는 퀴놀리논(quinolinone) 유도체 또는 이의 약제학적으로 허용되는 염을 제공한다:According to one aspect of the present invention, there is provided a quinolinone derivative represented by the following formula (I) or a pharmaceutically acceptable salt thereof:

화학식 1Formula 1

Figure 112016031927621-pct00001
Figure 112016031927621-pct00001

상기 화학식에서, R1, R2 및 R3는 각각 독립적으로 수소, 니트로, 할로겐, -NH2, 하이드라지노 또는

Figure 112016031927621-pct00002
(A1은 비치환되거나 C1-C5 알킬, 할로겐, C2-C5 알케닐, 니트로, 하이드록시, 하이드록시 C1-C5 알킬, C1-C3 알콕시 또는 페닐로 치환된 C6-C10 아릴; 비치환되거나 할로겐, 니트로, C2-C5 알케닐로 치환된 C1-C5 알킬; C5-C6 사이클로알킬; 비치환되거나 할로겐 또는 C1-C3 알킬로 치환된 아다만테인; C1-C3 알콕시; C1-C5 알킬티오, 또는 벤조디옥솔이고; n은 0-2의 정수이다)이고; R4는 수소, C1-C5 알킬,
Figure 112016031927621-pct00003
(A2는 비치환되거나 할로겐, C1-C5 알킬, C1-C3 알콕시, 니트로, -NH2, C1-C5 알킬티오, 페닐, 페닐 C1-C5 알킬, 페녹시, 시아노, 하이드록시, 하이드록시 C1-C5 알킬, 포르밀, 페닐티오 또는 피라졸로 치환된 C6-C10 아릴; 사이클로펜타디엔; 피롤; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 C1-C5 알킬, C1-C3 알콕시, 할로겐, 니트로, 시아노, 하이드록시, 포르밀, C1-C5 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; m은 0-2의 정수이다) 또는
Figure 112016031927621-pct00004
(A3는 C1-C5 알킬; C1-C3 알콕시; 비치환되거나 C1-C3 알콕시, C1-C5 알킬, 하이드록시, 할로겐, 니트로, -NH2, 포르밀, 시아노, C1-C5 알킬티오, 페녹시, 페닐티오, 페닐 C1-C3 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피롤; C5-C6 사이클로알킬; 비치환되거나 C1-C5 알킬, C1-C3 알콕시, 할로겐, 니트로, 하이드록시, C1-C5 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p 및 q는 각각 독립적으로 0-2의 정수이다)이고; R5는 수소, C1-C5 알콕시 C1-C3 알킬, -NA4A5(A4 및 A5는 각각 독립적으로 수소; 비치환되거나 페닐, 디하이드로인덴, 나프탈릴, C1-C3 알콕시 또는 C1-C3 알킬티오로 치환된 C1-C5 알킬; 비치환되거나 C1-C5 알킬, 할로겐, 하이드록시 C1-C5 알킬, C2-C5 알케닐, 설폰아마이드, C1-C3 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다) 또는
Figure 112016031927621-pct00005
[A6는 C1-C3 알콕시, 할로겐, 하이드록시, C1-C3 알킬티오 또는 -NA7A8(A7 및 A8은 각각 독립적으로 수소; 비치환되거나 페닐, 니트로, 하이드록시, 할로겐, 디하이드로인덴, 나프탈릴, C1-C3 알콕시, C1-C3 알킬아민 또는 C1-C3 알킬티오로 치환된 C1-C5 알킬; C2-C5 알케닐; 비치환되거나 C1-C5 알킬, 할로겐, 하이드록시 C1-C5 알킬, C2-C5 알케닐, 설폰아마이드, C1-C3 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다)]이다.In the above formulas, R 1 , R 2 and R 3 are each independently hydrogen, nitro, halogen, -NH 2 , hydrazino or
Figure 112016031927621-pct00002
Wherein A 1 is C 1 -C 5 alkyl which is unsubstituted or substituted by C 1 -C 5 alkyl, halogen, C 2 -C 5 alkenyl, nitro, hydroxy, hydroxy C 1 -C 5 alkyl, C 1 -C 3 alkoxy or phenyl C 6 -C 10 aryl, C 1 -C 5 alkyl unsubstituted or substituted by halogen, nitro, C 2 -C 5 alkenyl, C 5 -C 6 cycloalkyl, unsubstituted or substituted by halogen or C 1 -C 3 alkyl substituted adamantane; C 1 -C 3 alkoxy; C 1 -C 5 alkylthio, or benzodioxole and; n is an integer from 0 to 2), and; R 4 is hydrogen, C 1 -C 5 alkyl,
Figure 112016031927621-pct00003
(A 2 is unsubstituted or substituted by halogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy, nitro, -NH 2, C 1 -C 5 alkylthio, phenyl, phenyl-C 1 -C 5 alkyl, phenoxy, C 6 -C 10 aryl substituted by cyano, hydroxy, hydroxy C 1 -C 5 alkyl, formyl, phenylthio or pyrazole, cyclopentadiene, pyrrole, furan, thiophene, C 5 -C 6 cycloalkyl A dihydroindene unsubstituted or substituted with C 1 -C 5 alkyl, C 1 -C 3 alkoxy, halogen, nitro, cyano, hydroxy, formyl, C 1 -C 5 alkylthio or -NH 2 ; Or diphenylmethyl; m is an integer of 0-2) or
Figure 112016031927621-pct00004
(A 3 is a C 1 -C 5 alkyl; C 1 -C 3 alkoxy, unsubstituted or C 1 -C 3 alkoxy, C 1 -C 5 alkyl, hydroxy, halogen, nitro, -NH 2, formyl, cyano no, C 1 -C 5 alkylthio, phenoxy, phenylthio, phenyl-C 1 -C 3 alkyl or pyrazolo-substituted phenyl, furan; thiophene; pyrrole; C 5 -C 6 cycloalkyl, unsubstituted or C 1 -C 5 alkyl, C 1 -C 3 alkoxy, halogen, nitro, hydroxy, C 1 -C indene substituted with a 5-dihydro-alkylthio or -NH 2; or diphenyl methyl; p and q are each independently Lt; / RTI > is an integer of 0-2; R 5 is hydrogen, C 1 -C 5 alkoxy C 1 -C 3 alkyl, -NA 4 A 5 (wherein A 4 and A 5 are each independently hydrogen, unsubstituted or substituted with phenyl, dihydroindene, naphthalyl, C 1 C 1 -C 5 alkyl substituted with C 1 -C 3 alkoxy or C 1 -C 3 alkylthio, unsubstituted or substituted with C 1 -C 5 alkyl, halogen, hydroxy C 1 -C 5 alkyl, C 2 -C 5 alkenyl , Sulfonamide, C 1 -C 3 alkoxy, hydroxy or nitro, or
Figure 112016031927621-pct00005
[A 6 is selected from the group consisting of C 1 -C 3 alkoxy, halogen, hydroxy, C 1 -C 3 alkylthio or -NA 7 A 8 , wherein A 7 and A 8 are each independently hydrogen, , C 1 -C 5 alkyl substituted with halogen, dihydroidene, naphtalyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamine or C 1 -C 3 alkylthio, C 2 -C 5 alkenyl Phenyl which is unsubstituted or substituted by C 1 -C 5 alkyl, halogen, hydroxy C 1 -C 5 alkyl, C 2 -C 5 alkenyl, sulfonamido, C 1 -C 3 alkoxy, hydroxy or nitro) ]to be.

본 발명자들은 면역조절 관련 질환의 발병에 중요한 역할을 하는 염증성 사이토카인인 IL-2의 효과적인 길항제를 발굴함으로써 다양한 염증성 질환 및 자가면역 질환의 예방 또는 치료용 조성물을 개발하기 위하여 예의 연구 노력하였다. 그 결과 상기 화학식 1로 표시되는 신규 퀴놀리논 유도체가 IL-2의 활성을 매우 효과적으로 억제함을 발견함으로써, 본 발명을 완성하게 되었다.The present inventors have sought to develop a composition for the prevention or treatment of various inflammatory diseases and autoimmune diseases by identifying effective antagonists of IL-2, an inflammatory cytokine that plays an important role in the development of diseases related to immunomodulation. As a result, it was found that the novel quinolinone derivative represented by the above formula (1) extremely effectively inhibited the activity of IL-2, thereby completing the present invention.

본 명세서에서 용어 "알킬" 은 직쇄 또는 분쇄의 포화 탄화수소기를 의미하며, 예를 들어, 메틸, 에틸, 프로필, 이소부틸 또는 펜틸 등을 포함한다. C1-C5 알킬은 탄소수 1 내지 5의 알킬 유니트를 가지는 알킬기를 의미하며, C1-C5 알킬이 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다. 화학식 1에서, C1-C5 알킬은 구체적으로는 C1-C3 알킬이다.As used herein, the term "alkyl" means a straight or branched saturated hydrocarbon group, including, for example, methyl, ethyl, propyl, isobutyl or pentyl. C 1 -C 5 alkyl means an alkyl group having an alkyl unit of 1 to 5 carbon atoms, and when C 1 -C 5 alkyl is substituted, the number of carbon atoms of the substituent is not included. In formula (1), C 1 -C 5 alkyl is specifically C 1 -C 3 alkyl.

본 명세서에서 용어 "할로겐" 은 할로겐족 원소를 나타내며, 예컨대, 플루오로, 클로로, 브로모 및 요오도를 포함한다.As used herein, the term "halogen " refers to a halogen group element and includes, for example, fluoro, chloro, bromo and iodo.

본 명세서에서 용어 "알케닐" 은 이중결합이 포함된 불포화 탄화수소기를 의미하며, C2-C5 알케닐이 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다..The term "alkenyl" as used herein refers to an unsaturated hydrocarbon group containing a double bond, and when the C 2 -C 5 alkenyl is substituted, the number of carbon atoms of the substituent is not included.

본 명세서에서 용어 "알콕시" 는 알코올에서 수소가 제거되어 형성된 라디칼을 의미하며, C1-C3 알콕시가 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다.As used herein, the term "alkoxy" means a radical formed by removing hydrogen from an alcohol, and when C 1 -C 3 alkoxy is substituted, the number of carbon atoms of the substituent is not included.

본 명세서에서 용어 "아릴" 은 전체적으로 또는 부분적으로 불포화되고 방향성(aromaticity)를 가지는 치환 또는 비치환된 모노사이클릭 또는 폴리사이클릭 탄소 고리를 의미한다.As used herein, the term "aryl " means a substituted or unsubstituted monocyclic or polycyclic carbon ring that is totally or partially unsaturated and has aromaticity.

본 명세서에서 용어 "알킬티오" 은 티올(티오l)에서 수소가 제거되어 형성된 라디칼을 의미하며, C1-C5 알킬티오가 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다.As used herein, the term "alkylthio" means a radical formed by removal of hydrogen from thiol (thio) and does not include the carbon number of the substituent when C 1 -C 5 alkylthio is substituted.

본 명세서에서 용어 "아릴알킬" 은 아릴기로 치환된 알킬을 의미한다. 아릴 C1-C4 알킬은 아릴기로 치환된 탄소수 1 내지 4의 알킬 유니트를 의미한다.As used herein, the term "arylalkyl" means an alkyl substituted with an aryl group. Aryl C 1 -C 4 alkyl means an alkyl unit having from 1 to 4 carbon atoms substituted with an aryl group.

본 명세서에서 용어 "페닐티오" 는 티오페놀(티오페놀)에서 수소가 제거되어 형성된 라디칼을 의미한다.As used herein, the term "phenylthio" means a radical formed by removing hydrogen from thiophenol (thiophenol).

본 발명의 퀴놀리논 유도체는 약학적으로 허용 가능한 염의 형태로 사용될 수 있으며, 염으로는 약학적으로 허용 가능한 유리산(free acid)에 의해 형성된 산 부가염을 사용될 수 있다. 산 부가염은 염산, 질산, 인산, 황산, 브롬화수소산, 요드화수소산, 아질산 또는 아인산과 같은 무기산류와 지방족 모노 및 디카르복실레이트, 페닐-치환된 알카노에이트, 하이드록시 알카노에이트 및 알칸디오에이트, 방향족 산류, 지방족 및 방향족 설폰산류와 같은 무독성 유기산, 아세트산, 안식향산, 구연산, 젖산, 말레인산, 글루콘산, 메탄설폰산, 4-톨루엔설폰산, 주석산, 푸마르산과 같은 유기산으로부터 얻는다. 이러한 약학적으로 무독한 염류로는 설페이트, 피로설페이트, 바이설페이트, 설파이트, 바이설파이트, 니트레이트, 포스페이트, 모노하이드로겐 포스페이트, 디하이드로겐 포스페이트, 메타포스페이트, 피로포스페이트 클로라이드, 브로마이드, 아이오다이드, 플루오라이드, 아세테이트, 프로피오네이트, 데카노에이트, 카프릴레이트, 아크릴레이트, 포메이트, 이소부티레이트, 카프레이트, 헵타노에이트, 프로피올레이트, 옥살레이트, 말로네이트, 석시네이트, 수베레이트, 세바케이트, 푸마레이트, 말리에이트, 부틴-1,4-디오에이트, 헥산-1,6-디오에이트, 벤조에이트, 클로로벤조에이트, 메틸벤조에이트, 디니트로벤조에이트, 하이드록시벤조에이트, 메톡시벤조에이트, 프탈레이트, 테레프탈레이트, 벤젠설포네이트, 톨루엔설포네이트, 클로로벤젠설포네이트, 크실렌설포네이트, 페닐아세테이트, 페닐프로피오네이트, 페닐부티레이트, 시트레이트, 락테이트, β-하이드록시부티레이트, 글리콜레이트, 말레이트, 타트레이트, 메탄설포네이트, 프로판설포네이트, 나프탈렌-1-설포네이트, 나프탈렌-2-설포네이트 또는 만델레이트를 포함하나, 이에 제한되는 것은 아니다.The quinolinone derivative of the present invention may be used in the form of a pharmaceutically acceptable salt. As the salt, an acid addition salt formed by a pharmaceutically acceptable free acid may be used. Acid addition salts include those derived from inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid, and aliphatic mono- and dicarboxylates, phenyl-substituted alkanoates, hydroxyalkanoates, Derived from organic acids such as acetic acid, benzoic acid, citric acid, lactic acid, maleic acid, gluconic acid, methanesulfonic acid, 4-toluenesulfonic acid, tartaric acid, fumaric acid, and the like. Such pharmaceutically innocuous salts include, but are not limited to, sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihydrogenphosphate, metaphosphate, pyrophosphate chloride, bromide, Butyrate, caprate, heptanoate, propiolate, oxalate, malonate, succinate, succinate, maleic anhydride, maleic anhydride, , Sebacate, fumarate, maleate, butyne-1,4-dioate, hexane-1,6-dioate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, Methoxybenzoate, phthalate, terephthalate, benzenesulfonate, toluene sulfonate, chlorobenzene sulfoxide Propyl sulphonate, naphthalene-1-yne, xylenesulfonate, phenylsulfate, phenylbutyrate, citrate, lactate,? -Hydroxybutyrate, glycolate, maleate, Sulfonate, naphthalene-2-sulfonate or mandelate.

본 발명에 따른 산 부가염은 통상의 방법, 예를 들면, 화학식 1의 유도체를 유기용매, 예를 들면 메탄올, 에탄올, 아세톤, 메틸렌클로라이드, 아세토니트릴 등에 녹이고 유기산 또는 무기산을 가하여 생성된 침전물을 여과, 건조하여 제조되거나, 용매와 과량의 산을 감압 증류한 후 건조하거나 유기용매 하에서 결정화시켜셔 제조할 수 있다.The acid addition salt according to the present invention can be obtained by a conventional method, for example, by dissolving a derivative of Chemical Formula 1 in an organic solvent such as methanol, ethanol, acetone, methylene chloride, acetonitrile, , Or may be prepared by drying, or after the solvent and excess acid are distilled off under reduced pressure, followed by drying or crystallization in an organic solvent.

또한, 염기를 사용하여 약학적으로 허용 가능한 금속염을 만들 수 있다. 알칼리 금속 또는 알칼리 토금속 염은 예를 들면 화합물을 과량의 알칼리 금속 수산화물 또는 알칼리 토금속 수산화물 용액 중에 용해하고, 비용해 화합물 염을 여과하고, 여액을 증발, 건조시켜 얻는다. 이때, 금속 염으로는 나트륨, 칼륨 또는 칼슘염을 제조하는 것이 제약상 적합하다. 또한, 이에 대응하는 은염은 알칼리 금속 또는 알칼리 토금속 염을 적당한 음염(예, 질산은)과 반응시켜 얻는다. 또한, 본 발명은 상기 화학식 1로 표시되는 퀴놀리논 유도체 및 이의 약학적으로 허용되는 염뿐만 아니라, 이로부터 제조될 수 있는 가능한 용매화물, 수화물, 입체이성질체 등을 모두 포함한다.In addition, bases can be used to make pharmaceutically acceptable metal salts. The alkali metal or alkaline earth metal salt is obtained, for example, by dissolving the compound in an excess amount of an alkali metal hydroxide or an alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is preferable for the metal salt to produce sodium, potassium or calcium salt. In addition, the corresponding silver salt is obtained by reacting an alkali metal or alkaline earth metal salt with a suitable salt (such as silver nitrate). The present invention also encompasses quinolinone derivatives represented by the above formula (1) and pharmaceutically acceptable salts thereof, as well as possible solvates, hydrates, stereoisomers and the like which can be prepared therefrom.

본 발명의 구체적인 구현예에 따르면, 본 발명의 화학식 1의 R1, R2 및 R3는 각각 독립적으로 수소, 니트로, 할로겐, -NH2, 하이드라지노 또는

Figure 112016031927621-pct00006
(A1은 비치환되거나 C1-C3 알킬, 할로겐, C2-C3 알케닐, 니트로, 하이드록시, 하이드록시 C1-C3 알킬, C1-C3 알콕시 또는 페닐로 치환된 페닐; 나프탈릴; 비치환되거나 할로겐, 니트로, C2-C3 알케닐로 치환된 C1-C3 알킬; C5-C6 사이클로알킬; 비치환되거나 할로겐 또는 메틸로 치환된 아다만테인; C1-C3 알콕시; C1-C3 알킬티오; 또는 벤조디옥솔이고; n은 0-2의 정수이다)이다.According to a specific embodiment of the present invention, R 1 , R 2 and R 3 in formula (1) of the present invention are each independently hydrogen, nitro, halogen, -NH 2 , hydrazino or
Figure 112016031927621-pct00006
Wherein A 1 is phenyl which is unsubstituted or substituted by C 1 -C 3 alkyl, halogen, C 2 -C 3 alkenyl, nitro, hydroxy, hydroxy C 1 -C 3 alkyl, C 1 -C 3 alkoxy or phenyl Naphthalenyl, C 1 -C 3 alkyl unsubstituted or substituted by halogen, nitro, C 2 -C 3 alkenyl, C 5 -C 6 cycloalkyl, adamantane unsubstituted or substituted by halogen or methyl, C 1 -C 3 alkoxy; C 1 -C 3 alkylthio; or benzodioxole and; n is an integer from 0 to 2).

본 발명의 구체적인 구현예에 따르면, 본 발명의 화학식 1의 R4는 수소, C1-C3 알킬,

Figure 112016031927621-pct00007
(A2는 비치환되거나 할로겐, C1-C3 알킬, C1-C3 알콕시, 니트로, -NH2, C1-C3 알킬티오, 페닐, 페닐 C1-C3 알킬, 페녹시, 시아노, 하이드록시, 하이드록시 C1-C3 알킬, 포르밀, 페닐티오 또는 피라졸로 치환된 페닐; 나프탈릴; 사이클로펜타디엔; 피롤; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 C1-C3 알킬, C1-C3 알콕시, 할로겐, 니트로, 시아노, 하이드록시, 포르밀, C1-C3 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; m은 0-2의 정수이다) 또는
Figure 112016031927621-pct00008
(A3는 C1-C3 알킬; C1-C3 알콕시; 비치환되거나 C1-C3 알콕시, C1-C3 알킬, 하이드록시, 할로겐, 니트로, -NH2, 포르밀, 시아노, C1-C3 알킬티오, 페녹시, 페닐티오, 페닐 C1-C3 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피롤; C5-C6 사이클로알킬; 비치환되거나 C1-C3 알킬, C1-C3 알콕시, 할로겐, 니트로, 하이드록시, C1-C3 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p는 0이며 q는 0-2의 정수이다)이다.According to a specific embodiment of the invention, R 4 of formula (I) of the present invention are hydrogen, C 1 -C 3 alkyl,
Figure 112016031927621-pct00007
(A 2 is phenyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, nitro, -NH 2 , C 1 -C 3 alkylthio, phenyl C 1 -C 3 alkyl, phenoxy, cyano, hydroxy, hydroxy C 1 -C 3 alkyl, formyl, phenylthio or pyrazolo-substituted phenyl, naphthyl talril; dicyclopentadiene; pyrrole; furan; thiophene; C 5 -C 6 cycloalkyl; Beach Or a dihydroindene substituted with C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halogen, nitro, cyano, hydroxy, formyl, C 1 -C 3 alkylthio or -NH 2 ; Phenylmethyl, and m is an integer of 0-2) or
Figure 112016031927621-pct00008
(A 3 is a C 1 -C 3 alkyl; C 1 -C 3 alkoxy, unsubstituted or C 1 -C 3 alkoxy, C 1 -C 3 alkyl, hydroxy, halogen, nitro, -NH 2, formyl, cyano no, C 1 -C 3 alkylthio, phenoxy, phenylthio, phenyl-C 1 -C 3 alkyl or pyrazolo-substituted phenyl, furan; thiophene; pyrrole; C 5 -C 6 cycloalkyl, unsubstituted or C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halogen, nitro, hydroxy, a cost-dihydro-substituted by C 1 -C 3 alkylthio or -NH 2 Den; or diphenyl methyl; p is 0, q is 0 < / RTI >

본 발명의 구체적인 구현예에 따르면, 본 발명의 화학식 1의 R5는 수소, C1-C3 알콕시 C1-C2 알킬, -NA4A5(A4 및 A5는 각각 독립적으로 수소; 비치환되거나 페닐, 디하이드로인덴, 나프탈릴, C1-C3 알콕시 또는 C1-C3 알킬티오로 치환된 C1-C3 알킬; 비치환되거나 C1-C3 알킬, 할로겐, 하이드록시 C1-C3 알킬, C2-C3 알케닐, 설폰아마이드, C1-C3 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다) 또는

Figure 112016031927621-pct00009
[A6는 C1-C3 알콕시, 할로겐 하이드록시, C1-C2 알킬티오 또는 -NA7A8(A7 및 A8은 각각 독립적으로 수소; 비치환되거나 페닐, 니트로, 하이드록시, 할로겐, 디하이드로인덴, 나프탈릴, C1-C3 알콕시, C1-C3 알킬아민 또는 C1-C2 알킬티오로 치환된 C1-C3 알킬; C2-C3 알케닐; 비치환되거나 C1-C3 알킬, 할로겐, 하이드록시 C1-C3 알킬, C2-C3 알케닐, 설폰아마이드, C1-C3 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다)]이다.According to a specific embodiment of the invention, R 5 of the general formula (I) of the present invention are hydrogen, C 1 -C 3 alkoxy C 1 -C 2 alkyl, -NA 4 A 5 (A 4 and A 5 are each independently hydrogen, unsubstituted or substituted phenyl, dihydro-indene, naphthyl talril, C 1 -C 3 alkoxy or C 1 -C 3 alkyl substituted with a C 1 -C 3 alkylthio; unsubstituted or C 1 -C 3 alkyl, halogen, hydroxy C 1 -C 3 alkyl, C 2 -C 3 alkenyl, sulfonamide, C 1 -C 3 alkoxy, hydroxy, or nitro; or
Figure 112016031927621-pct00009
[A 6 is C 1 -C 3 alkoxy, halogenhydroxy, C 1 -C 2 alkylthio or -NA 7 A 8 , wherein A 7 and A 8 are each independently hydrogen or unsubstituted or substituted with phenyl, nitro, halogen, dihydro-indene, naphthyl talril, C 1 -C 3 alkoxy, C 1 -C 3 alkylamine or C 1 -C 2 alkyl substituted with a C 1 -C 3 alkylthio; C 2 -C 3 alkenyl; Is phenyl which is unsubstituted or substituted by C 1 -C 3 alkyl, halogen, hydroxy C 1 -C 3 alkyl, C 2 -C 3 alkenyl, sulfonamido, C 1 -C 3 alkoxy, hydroxy or nitro] to be.

본 발명의 보다 구체적인 구현예에 따르면, 본 발명의 퀴놀리논 유도체는According to a more specific embodiment of the present invention, the quinolinone derivative of the present invention is

(1) 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(1) 1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(2) 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(2) 1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(3) 1-(4-플루오로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(3) 1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(4) 1-(4-플루오로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(4) 1- (4-Fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(5) 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(5) 1- (4-Chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(6) 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(6) 5-Nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(7) 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(7) 1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(8) 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(8) 1- (4-Cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(9) 1-(나프탈렌-2-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(9) 1- (Naphthalen-2-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(10) 1-([1,1'-비페닐]-4-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(10) 1 - ([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(11) 1-(4-벤질벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(11) 1- (4-Benzylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(12) 5-니트로-2-옥소-N-펜에틸-1-(4-페녹시벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;(12) 5-Nitro-2-oxo-N-phenethyl-1- (4-phenoxybenzyl) -1,2-dihydroquinoline-3-carboxamide;

(13) 1-(4-클로로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(13) 1- (4-Chlorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(14) 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(14) 1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(15) 1-(4-시아노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(15) 1- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(16) 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(16) 5-Nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(17) 메틸 7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(17) methyl 7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(18) 메틸 1-(2-(사이클로펜타-1,3-디엔-1-일)에틸)-7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(18) Methyl 1- (2- (cyclopenta-1,3-dien-1-yl) ethyl) -7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(19) 메틸 5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(19) methyl 5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(20) 메틸 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(20) Methyl 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(21) 메틸 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(21) methyl 1-methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(22) 메틸 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(22) methyl 1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate;

(23) 메틸 2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트;(23) methyl 2-oxo-1,2-dihydroquinoline-3-carboxylate;

(24) 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 클로라이드;(24) 2-oxo-1,2-dihydroquinoline-3-carbonyl chloride;

(25) 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 브로마이드;(25) 2-oxo-1,2-dihydroquinoline-3-carbonylbromide;

(26) 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 플루오라이드;(26) 2-oxo-1,2-dihydroquinoline-3-carbonyl fluoride;

(27) 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 아이오다이드;(27) 2-oxo-1,2-dihydroquinoline-3-carbonyl iodide;

(28) 2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(28) 2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(29) 1-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(29) 1-Methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(30) 1-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(30) 1-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(31) 1-아세틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(31) 1-acetyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(32) 5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(32) 5-benzamido-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(33) 1-((2H-피롤-2-일)메틸)-5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(33) 1 - ((2H-pyrrol-2-yl) methyl) -5-benzamido-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(34) 5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(34) 5- (4-Methylbenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(35) 1-(2-(2H-피롤-2-일)에틸)-5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(35) 1- (2- (2H-Pyrrol-2-yl) ethyl) -5- (4-methylbenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline- Copymade;

(36) 5-(4-브로모벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(36) 5- (4-Bromobenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(37) 2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(37) 2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(38) 1-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(38) 1-Methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(39) 1-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(39) 1-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(40) 5-(4-클로로벤즈아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(40) 5- (4-Chlorobenzamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(41) N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(41) N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(42) 5-(4-플루오로벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(42) 5- (4-Fluorobenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(43) 5-(4-에틸벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(43) 5- (4-Ethylbenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(44) N-(4-브로모페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(44) N- (4-bromophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(45) N-(4-브로모페닐)-2-옥소-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(45) N- (4-bromophenyl) -2-oxo-5- (4-vinylbenzamido) -1,2-dihydroquinoline-3-carboxamide;

(46) N-(4-브로모페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(46) Synthesis of N- (4-bromophenyl) -2-oxo-1- (2- (thiophen- Quinolin-3-carboxamide;

(47) N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(47) N- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(48) N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(48) N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(49) N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(49) N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(50) N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(50) N- (4-chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(51) N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(51) N- (4-Chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(52) N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(52) N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(53) 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(53) 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(54) 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(54) 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(55) 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(55) 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(56) N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(56) N- (4-Chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(57) N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(57) N- (4-Chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(58) N-(4-클로로페닐)-1-에틸-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(58) N- (4-Chlorophenyl) -1-ethyl-5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(59) N-(4-클로로페닐)-1-(퓨란-2-일메틸)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(59) A mixture of N- (4-chlorophenyl) -1- (furan-2-ylmethyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline- 3-carboxamide;

(60) N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(60) N- (4-chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(61) N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(61) N- (4-chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(62) N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(62) N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(63) N-(4-클로로페닐)-1-(2-(퓨란-2-일)에틸)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(63) A mixture of N- (4-chlorophenyl) -1- (2- (furan-2-yl) ethyl) 3-carboxamide;

(64) N-(4-클로로페닐)-2-옥소-5-(2-페닐아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(64) N- (4-chlorophenyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline-3-carboxamide;

(65) 5-벤즈아미도-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(65) 5-benzamido-N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(66) 5-벤즈아미도-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(66) 5-benzamido-N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(67) N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(67) N- (4-Chlorophenyl) -5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(68) N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(68) N- (4-Chlorophenyl) -5- (4-ethylbenzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(69) N-(4-클로로페닐)-1-에틸-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(69) N- (4-chlorophenyl) -1-ethyl-5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(70) N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(70) N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(71) N-(4-플루오로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(71) N- (4-fluorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(72) 1-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(72) 1-Ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(73) 1-((2H-피롤-3-일)메틸)-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(73) 1 - ((2H-pyrrol-3-yl) methyl) -N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(74) N-(4-플루오로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(74) N- (4-fluorophenyl) -2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-3-carboxamide;

(75) N-(4-플루오로페닐)-1-메틸-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(75) N- (4-fluorophenyl) -1-methyl-2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-3-carboxamide;

(76) 1-에틸-N-(4-플루오로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(76) 1-Ethyl-N- (4-fluorophenyl) -2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-3-carboxamide;

(77) N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(77) N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(78) N-(4-에틸페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(78) N- (4-ethylphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(79) 1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(79) 1-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(80) 1-(2-(2H-피롤-3-일)에틸)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린 -3-카복사마이드;(80) 1- (2- (2H-pyrrol-3-yl) ethyl) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(81) 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(81) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(82) 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1-(티오펜-2-일메틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(82) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo- Hydroquinoline-3-carboxamide;

(83) 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(83) Synthesis of 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -1- methyl-2-oxo-1,2-dihydroquinoline- ;

(84) 5-(2-(4-브로모페닐)아세트아미도)-1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(84) Synthesis of 5- (2- (4-bromophenyl) acetamido) -1-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- ;

(85) N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(85) N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(86) N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(86) N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(87) 1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(87) 1-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(88) N-(4-하이드록시페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(88) N- (4-hydroxyphenyl) -2-oxo-1- (2- (thiophen-2-yl) ethyl) -1,2-dihydroquinoline-3-carboxamide;

(89) 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(89) 5- (2- (4-chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(90) 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(90) 5- (2- (4-Chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- ;

(91) 5-(2-(4-클로로페닐)아세트아미도)-1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(91) 5- (2- (4-chlorophenyl) acetamido) -1-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline- ;

(92) N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(92) N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(93) 5-(2-(4-플루오로페닐)아세트아미도)-N-(4-리트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(93) 5- (2- (4-Fluorophenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(94) 5-(2-(4-에틸페닐)아세트아미도)-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(94) 5- (2- (4-Ethylphenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(95) N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(95) N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(96) N-(4-(N,N-디메틸설파모일)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(96) N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(97) N-(4-(N,N-디메틸설파모일)페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(97) N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(98) 1-(사이클로헥실메틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(98) 1- (Cyclohexylmethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(99) 1-(2-사이클로헥실에틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(99) 1- (2-Cyclohexylethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(100) N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(100) N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(101) N-(4-(하이드록시메틸)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(101) N- (4- (hydroxymethyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(102) 1-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(102) 1-ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(103) 1-(사이클로펜틸메틸)-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(103) 1- (Cyclopentylmethyl) -N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(104) 2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(104) 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(105) 1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(105) 1-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(106) 1-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(106) 1-ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(107) 1-(2-사이클로펜틸에틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(107) 1- (2-Cyclopentylethyl) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(108) 5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(108) 5- (2- (4-Hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(109) 5-(2-(4-하이드록시페닐)아세트아미도)-1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(109) Synthesis of 5- (2- (4-hydroxyphenyl) acetamido) -1-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- ;

(110) 1-에틸-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(110) Synthesis of 1-ethyl-5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- ;

(111) 1-((2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(4-hydroxyphenyl) acetamido) -2-oxo-N- (4-methoxyphenyl) -Vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(112) 5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(112) 5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(113) 1-메틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(113) 1-Methyl-5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(114) 1-에틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(114) 1-ethyl-5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(115) 1-((4-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(115) Synthesis of 1 - ((4-methoxy-2,3-dihydro-1H-inden-2-yl) methyl) N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(116) 1-((5-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(116) Synthesis of 1 - ((5-methoxy-2,3-dihydro-1H-inden-2-yl) methyl) N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(117) N-벤질-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(117) N-benzyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(118) N-벤질-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(118) N-benzyl-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(119) N-벤질-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(119) N-benzyl-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(120) 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(120) 5- (2- (4-Methoxyphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(121) 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(121) Synthesis of 1 - ((5-ethyl-2,3-dihydro-1H-inden- N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(122) 1-((5-플루오로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(122) Synthesis of 1 - ((5-fluoro-2,3-dihydro-1H-inden-2-yl) -N-phenyl-l, 2-dihydroquinoline-3-carboxamide;

(123)1-((5-클로로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(123) Synthesis of 1 - ((5-chloro-2,3-dihydro-1H-inden- N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(124) 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(124) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(125) 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-아이오도-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(125) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1 - ((5-iodo-2,3-dihydro- 2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide;

(126) 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-니트로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(126) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1- (5-nitro-2,3-dihydro- -Oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide;

(127) 2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(127) 2-oxo-N-phenyl-5- (3-phenylpropanamido) -1,2-dihydroquinoline-3-carboxamide;

(128) 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카복사마이드;(128) Synthesis of 1 - ((5-ethyl-2,3-dihydro-1H-inden-2-yl) 2-dihydroquinoline-3-carboxamide;

(129) 5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(129) 5- (2- (4-ethylphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(130) 1-(2-(2,3-디하이드로-1H-인덴-2-일)에틸)-5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(130) Synthesis of 1- (2- (2,3-dihydro-1H-inden-2-yl) ethyl) -1,2-dihydroquinoline-3-carboxamide;

(131) 2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(131) 2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(132) 1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(132) 1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(133) 2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;(133) 2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;

(134) 1-(2-(4-메톡시-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(134) 1- (2- (4-Methoxy-2,3-dihydro-1H-inden-2-yl) ethyl) -2-oxo-N-phenethyl-1,2-dihydroquinolin- - carboxamide;

(135) 2-옥소-N-펜에틸-1-(2-(4-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(135) Synthesis of 2-oxo-N-phenethyl-1- (2- (4- (trifluoromethoxy) -2,3-dihydro- Hydroquinoline-3-carboxamide;

(136) 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(136) 5- (2- (4-Methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(137) 1-(4-메톡시벤질)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(137) 1- (4-methoxybenzyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline- Copymade;

(138) 1-((4-하이드록시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(138) Synthesis of 1- ((4-hydroxy-2,3-dihydro-1H-inden-2-yl) N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(139) 1-((4-포르밀-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(139) Synthesis of 1 - ((4-formyl-2,3-dihydro-1H-inden-2-yl) N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(140) 1-((4-시아노-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(140) Synthesis of 1 - ((4-cyano-2,3-dihydro-1H-inden-2-yl) N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(141)5-(2-(4-브로모페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(141) 5- (2- (4-Bromophenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(142) 5-(2-(4-브로모페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(142) 5- (2- (4-Bromophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline- Copymade;

(143) 2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카복사마이드;(143) 2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide;

(144) 1-(4-메톡시벤질)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카복사마이드;(144) 1- (4-methoxybenzyl) -2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide;

(145) 1-(2-(5-포르밀-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카복사마이드;(145) Synthesis of 1- (2- (5-formyl-2,3-dihydro-1H-inden-2-yl) Hydroquinoline-3-carboxamide;

(146) 1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카복사마이드;(146) 1- (2- (5- (Methylthio) -2,3-dihydro-1H-inden-2-yl) Dihydroquinoline-3-carboxamide;

(147) N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(147) N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(148) 1-(4-메톡시벤질)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(148) 1- (4-methoxybenzyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(149) N-(4-메틸벤질)-2-옥소-1-(3-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(149) N- (4-methylbenzyl) -2-oxo-1- (3- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3-carboxamide;

(150) 1-(3-시아노펜에틸)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(150) 1- (3-cyanophenethyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(151) N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(151) N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(152) 1-(4-(하이드록시메틸)벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(152) 1- (4- (hydroxymethyl) benzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(153) 1-(4-에틸벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(153) 1- (4-Ethylbenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(154) 1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(154) 1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(155) 5-(2-(4-클로로페닐)아세트아미도)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(155) 5- (2- (4-Chlorophenyl) acetamido) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(156) 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(156) 5- (2- (4-chlorophenyl) acetamido) -1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide;

(157) N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(157) N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(158) 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(158) 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) Hydroquinoline-3-carboxamide;

(159) 1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(159) 1- (2- (5-Ethyl-2,3-dihydro-1H-inden-2-yl) ethyl) -N- (4-methoxybenzyl) Hydroquinoline-3-carboxamide;

(160) N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(160) N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(161) 1-(4-메톡시벤질)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(161) 1- (4-methoxybenzyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(162) 1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(162) 1- (2- (5-Hydroxy-2,3-dihydro-1H-inden-2-yl) ethyl) -N- (4-methoxyphenethyl) Dihydroquinoline-3-carboxamide;

(163) 1-((2,3-디하이드로-1H-인덴-5-일)메틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;Yl) methyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinolin-3- Carboxamide;

(164) 1-(2-(2,3-디하이드로-1H-인덴-5-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;Yl) ethyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide;

(165) 5-(2-(4-플루오로페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(165) 5- (2- (4-Fluorophenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(166) 5-(2-(4-에틸페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(166) 5- (2- (4-ethylphenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(167) N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(167) N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(168) 1-벤조일-N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(168) 1-Benzoyl-N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(169) N-(4-브로모벤질)-1-(4-메톡시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(169) N- (4-bromobenzyl) -1- (4-methoxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(170) N-(4-브로모펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(170) N- (4-bromophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(171) N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(171) N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(172) N-(4-브로모펜에틸)-2-옥소-1-(4-(트리플루오로메톡시)벤조일)-1,2-디하이드로퀴놀린-3-카복사마이드;(172) N- (4-Bromophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzoyl) -1,2-dihydroquinoline-3-carboxamide;

(173) N-(4-브로모펜에틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(173) N- (4-bromophenethyl) -5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(174) N-(4-클로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(174) N- (4-chlorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(175) N-(4-클로로벤질)-1-(4-에틸벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(175) N- (4-chlorobenzyl) -1- (4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(176) N-(4-클로로벤질)-1-(4-하이드록시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(176) N- (4-chlorobenzyl) -1- (4-hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(177) N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(177) N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(178) N-(4-클로로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(178) N- (4-chlorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(179) 1-(4-클로로벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(179) 1- (4-Chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(180) N-(4-클로로펜에틸)-1-(4-아이오도벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(180) N- (4-chlorophenethyl) -1- (4-iodobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(181) N-(4-클로로펜에틸)-1-(4-니트로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(181) N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(182) 1-(4-아미노벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(182) 1- (4-aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(183) N-(4-클로로펜에틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(183) N- (4-chlorophenethyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(184) N-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(184) N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(185) N-(4-플루오로벤질)-1-(4-포르밀벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(185) N- (4-fluorobenzyl) -1- (4-formylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(186) 1-(4-시아노벤조일)-N-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(186) 1- (4-cyanobenzoyl) -N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(187) N-(4-플루오로벤질)-1-(4-(메틸티오)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(187) N- (4-fluorobenzyl) -1- (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(188) N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(188) N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(189) N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(189) N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(190) 1-(4-(디플루오로메틸)벤조일)-N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로 퀴놀린-3-카복사마이드;(190) 1- (4- (difluoromethyl) benzoyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(191) N-(4-플루오로펜에틸)-1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(191) N- (4-fluorophenethyl) -1- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(192) N-(4-플루오로펜에틸)-2-옥소-1-(2-(4-(트리플루오로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(192) Synthesis of N- (4-fluorophenethyl) -2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline- ;

(193) N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(193) N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(194) N-(4-에틸벤질)-1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(194) N- (4-ethylbenzyl) -1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(195) N-(4-에틸벤질)-1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(195) N- (4-ethylbenzyl) -1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(196) N-(4-에틸벤질)-1-(2-(4-플루오로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(196) N- (4-ethylbenzyl) -1- (2- (4-fluorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(197) 1-(2-(4-클로로페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(197) 1- (2- (4-Chlorophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(198) N-(4-에틸벤질)-1-(2-(4-아이오도페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(198) N- (4-ethylbenzyl) -1- (2- (4-iodophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(199) N-(4-에틸벤질)-1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(199) N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(200) 1-(2-(4-아미노페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(200) 1- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(201) N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(201) N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(202) N-(4-에틸펜에틸)-1-(2-(4-포르밀페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(202) N- (4-ethylphenethyl) -1- (2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(203) 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(203) 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(204) N-(4-에틸펜에틸)-1-(2-(4-(메틸티오)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(204) N- (4-ethylphenethyl) -1- (2- (4- (methylthio) phenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(205) 1-(2-(4-(디플루오로메틸)페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(205) 1- (2- (4- (difluoromethyl) phenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(206) N-(4-하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(206) N- (4-hydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(207) N-(4-하이드록시벤질)-1-(4-(메틸티오)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(207) N- (4-hydroxybenzyl) -1- (4- (methylthio) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(208) N-(4-하이드록시벤질)-1-(4-(메틸티오)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(208) N- (4-hydroxybenzyl) -1- (4- (methylthio) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(209) N-(4-하이드록시벤질)-2-옥소-1-(4-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(209) N- (4-hydroxybenzyl) -2-oxo-1- (4- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3-carboxamide;

(210) N-(4-하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(210) N- (4-hydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(211) N-(4-하이드록시펜에틸)-1-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(211) N- (4-hydroxyphenethyl) -1- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(212) N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(212) N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(213) 1-(4-아이오도벤질)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(213) 1- (4-Iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(214) 1-(4-아이오도펜에틸)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린 -3-카복사마이드;(214) 1- (4-Iodophenethyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(215) N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(215) N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(216) 1-(4-포르밀벤질)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(216) 1- (4-formylbenzyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(217) 1-(4-포르밀펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(217) 1- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(218) 1-(4-(디플루오로메틸)펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(218) 1- (4- (difluoromethyl) phenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(219) N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(219) N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(220) 1-(4-(디플루오로메틸)벤질)-N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(220) 1- (4- (difluoromethyl) benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline- Mide;

(221) N-(4-(N,N-디메틸설파모일)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(221) N- (4- (N, N-dimethylsulfamoyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(222) N-(4-(하이드록시메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(222) N- (4- (hydroxymethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(223) N-(4-(하이드록시메틸)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(223) N- (4- (hydroxymethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(224) 2-옥소-N-(4-비닐벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;(224) 2-oxo-N- (4-vinylbenzyl) -1,2-dihydroquinoline-3-carboxamide;

(225) 2-옥소-N-(4-비닐펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(225) 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(226) N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(226) N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(227) 1-(2,3-디하이드로-1H-인덴-2-카르보닐)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(227) 1- (2,3-Dihydro-1H-indene-2-carbonyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(228) 1-(2-(2,3-디하이드로-1H-인덴-2-일)아세틸)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;Yl) acetyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carbaldehyde (228) Copymade;

(229) 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(229) 1- (3- (2,3-dihydro-1H-inden-2-yl) propanoyl) -N-methyl- - carboxamide;

(230) N-에틸-1-(2-(5-메톡시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(230) Synthesis of N-ethyl-1- (2- (5-methoxy-2,3-dihydro-1H- Quinolin-3-carboxamide;

(231) N-에틸-1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(231) Synthesis of N-ethyl-1- (2- (5- (methylthio) -2,3-dihydro- Dihydroquinoline-3-carboxamide;

(232) N-에틸-2-옥소-N-페닐-1-(2-(5-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(232) N-ethyl-2-oxo-N-phenyl-1- (2- (5- (trifluoromethoxy) -2,3- dihydro- 2-dihydroquinoline-3-carboxamide;

(233) N-에틸-1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(233) Synthesis of N-ethyl-1- (2- (5-hydroxy-2,3-dihydro-1H- Quinolin-3-carboxamide;

(234) N-에틸-1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline (234) -3-carboxamide;

(235) N-에틸-1-(2-(5-플루오로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(235) Synthesis of N-ethyl-1- (2- (5-fluoro-2,3-dihydro-1H- Quinolin-3-carboxamide;

(236) 1-(2-(5-클로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(236) 1- (2- (5-Chloro-2,3-dihydro-1H-inden-2-yl) acetyl) -N- -3-carboxamide;

(237) N-에틸-1-(2-(5-아이오도-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(237) Synthesis of N-ethyl-1- (2- (5-iodo-2,3-dihydro-1H- Quinolin-3-carboxamide;

(238) N-에틸-1-(2-(5-니트로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(238) Synthesis of N-ethyl-1- (2- (5-nitro-2,3-dihydro-1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline -3-carboxamide;

(239) 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(239) 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) acetyl) -N- -3-carboxamide;

(240) N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(240) N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(241) 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(241) Synthesis of 1- (3- (2,3-dihydro-1H-inden-2-yl) propanoyl) -N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinolin- - carboxamide;

(242) N-에틸-2-옥소-N-페닐-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카복사마이드;(242) N-ethyl-2-oxo-N-phenyl-5-propionamido-1,2-dihydroquinoline-3-carboxamide;

(243) 5-부티라미도-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;(243) 5-Butyramido-N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;

(244) N-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(244) N-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(245) N-에틸-2-옥소-5-펜탄아미도-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(245) N-ethyl-2-oxo-5-pentanamido-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(246) N-에틸-5-(2-메톡시아세트아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(246) N-ethyl-5- (2-methoxyacetamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(247) N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(247) N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(248) N-에틸-2-옥소-1-(4-(페닐티오)벤질)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(248) N-ethyl-2-oxo-1- (4- (phenylthio) benzyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(249) N-에틸-2-옥소-1-(4-페녹시벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(249) N-ethyl-2-oxo-1- (4-phenoxybenzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(250) N-에틸-2-옥소-1-(4-(페닐티오)벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(250) N-ethyl-2-oxo-1- (4- (phenylthio) benzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(251) N-에틸-2-옥소-1-(2-(4-(페닐티오)페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(251) N-ethyl-2-oxo-1- (2- (4- (phenylthio) phenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(252) N-에틸-2-옥소-1-(2-(4-페녹시페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(252) N-ethyl-2-oxo-1- (2- (4-phenoxyphenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(253) 1-(2-(4-벤질페닐)아세틸)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(253) 1- (2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(254) 1-(4-벤질벤조일)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;(254) 1- (4-benzylbenzoyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;

(255) N-(4-메톡시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(255) N- (4-methoxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(256) N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(256) N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(257) 5-(2-브로모아세트아미도)-N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(257) 5- (2-Bromoacetamido) -N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(258) N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(258) N- (4-bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(259) N-(4-브로모페닐)-1-(사이클로펜타-1,3-디엔카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(259) N- (4-bromophenyl) -1- (cyclopenta-1,3-dienecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(260) N-(4-브로모페닐)-N-메틸-2-옥소-1-(2H-피롤-3-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(260) N- (4-bromophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-3-carbonyl) -1,2-dihydroquinoline-3-carboxamide;

(261) N-(4-브로모페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(261) N- (4-bromophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;

(262)N-(4-브로모페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(262) N- (4-bromophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(263) N-(4-브로모페닐)-N-메틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(263) Synthesis of N- (4-bromophenyl) -N-methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline- ;

(264) N-(4-브로모페닐)-1-(2-(퓨란-2-일)아세틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(264) N- (4-bromophenyl) -1- (2- (furan-2-yl) acetyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(265) 1-(2-(2H-피롤-2-일)아세틸)-N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(265) 1- (2- (2H-pyrrol-2-yl) acetyl) -N- (4-bromophenyl) Mide;

(266) N-(4-브로모페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(266) N- (4-bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(267) N-(4-브로모페닐)-1-(사이클로헥산카르보닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(267) N- (4-bromophenyl) -1- (cyclohexanecarbonyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(268) N-(4-브로모페닐)-1-(3-사이클로헥실프로파노일)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(268) N- (4-bromophenyl) -1- (3-cyclohexylpropanoyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(269) N-(4-브로모페닐)-5-(2-클로로아세트아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(269) N- (4-bromophenyl) -5- (2-chloroacetamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(270) N-(4-클로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(270) N- (4-chlorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(271) N-(4-클로로페닐)-1-(사이클로펜탄카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(271) N- (4-Chlorophenyl) -1- (cyclopentanecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(272) N-(4-클로로페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(272) N- (4-Chlorophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(273) N-(4-클로로페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(273) N- (4-chlorophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;

(274) N-(4-클로로페닐)-N-메틸-2-옥소-1-(2H-피롤-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(274) N- (4-chlorophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;

(275) N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(275) N- (4-chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(276) N-(4-클로로페닐)-1-(2-사이클로펜틸아세틸)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(276) N- (4-chlorophenyl) -1- (2-cyclopentyl acetyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(277) N-(4-클로로페닐)-N-에틸-1-(2-(퓨란-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(277) N- (4-Chlorophenyl) -N-ethyl-1- (2- (furan-2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(278) N-(4-클로로페닐)-N-에틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(278) N- (4-chlorophenyl) -N-ethyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxamide;

(279) 1-(2-(2H-피롤-2-일)아세틸)-N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(279) 1- (2- (2H-pyrrol-2-yl) acetyl) -N- (4- chlorophenyl) -N- ;

(280) N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(280) N- (4-fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(281) N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-페닐에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(281) N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2-oxo-2-phenylethyl) -1,2-dihydroquinoline-3-carboxamide;

(282) N-(4-플루오로페닐)-1-(2-(4-메톡시페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(282) N- (4-fluorophenyl) -1- (2- (4-methoxyphenyl) -2-oxo-ethyl) - carboxamide;

(283) N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-(4-(트리플루오로메톡시)페닐)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(283) N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2- Quinolin-3-carboxamide;

(284) N-(4-플루오로페닐)-N-메틸-1-(2-(4-니트로페닐)-2-옥소-에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(284) N- (4-fluorophenyl) -N-methyl-1- (2- (4- nitrophenyl) Carboxamide;

(285) N-(4-플루오로페닐)-1-(2-(4-하이드록시페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(285) N- (4-fluorophenyl) -1- (2- (4-hydroxyphenyl) -2-oxo-ethyl) - carboxamide;

(286) N-(4-플루오로페닐)-1-(2-(4-플루오로페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(286) N- (4-fluorophenyl) -1- (2- (4-fluorophenyl) -2-oxo-ethyl) - carboxamide;

(287) 1-(2-(4-에틸페닐)-2-옥소-에틸)-N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(287) 1- (2- (4-Ethylphenyl) -2-oxo-ethyl) -N- (4-fluorophenyl) Carboxamide;

(288) 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(288) 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(289) N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(289) N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(290) 1-(2-(4-아미노페닐)-2-옥소-에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(290) 1- (2- (4-aminophenyl) -2-oxo-ethyl) Carboxamide;

(291) 1-(2-(4-시아노페닐)-2-옥소-에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(291) 1- (2- (4-cyanophenyl) -2-oxo-ethyl) -N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinolin- - carboxamide;

(292) N-에틸-N-(4-플루오로페닐)-1-(2-(4-(메틸티오)페닐)-2-옥소-에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(292) N-Ethyl-N- (4-fluorophenyl) -1- (2- (4- (methylthio) phenyl) -2-oxo-ethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide;

(293) N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(293) N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(294) 1-(2,4-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(294) 1- (2,4-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(295) 1-(2,4-디메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(295) 1- (2,4-Dimethylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(296) N-(4-에틸페닐)-1-(4-하이드록시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(296) N- (4-ethylphenyl) -1- (4-hydroxy-2-methylbenzyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(297) N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(297) N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(298) 1-(4-에틸-2-메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(298) 1- (4-ethyl-2-methylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(299) N-(4-에틸페닐)-1-(4-하이드록시-2-메틸펜에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(299) N- (4-ethylphenyl) -1- (4-hydroxy-2-methylphenethyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(300) N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(300) N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(301) 1-(4-에틸-2-메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(301) 1- (4-Ethyl-2-methylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(302) 1-(2,3-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(302) 1- (2,3-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(303) N-(4-에틸페닐)-5-(2-플루오로아세트아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(303) N- (4-ethylphenyl) -5- (2-fluoroacetamido) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(304) N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(304) N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(305) 1-(2,5-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(305) 1- (2,5-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(306) 1-(3,4-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(306) 1- (3,4-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(307) 1-(2,6-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(307) 1- (2,6-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(308) N-에틸-N-(4-에틸페닐)-2-옥소-1-(2,4,6-트리메틸벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;(308) N-ethyl-N- (4-ethylphenyl) -2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydroquinoline-3-carboxamide;

(309) 1-(4-(디플루오로메틸)-2-메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(309) Synthesis of 1- (4- (difluoromethyl) -2-methylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- Mide;

(310) (E)-1-(2-(4-(디플루오로메틸)-2-메틸사이클로헥사-2,4-디엔-1-일리딘)에틸)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(310) (E) -1- (2- (4- (difluoromethyl) -2-methylcyclohexa-2,4-dien- 1 -ylidine) ethyl) -Ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(311) N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(311) N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(312) N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(312) N- (4-hydroxyphenyl) -1- (4-methoxy-2-methylbenzyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(313) N-(4-하이드록시페닐)-N-메틸-2-옥소-1-(2,3,4,5,6-펜타메틸벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;(313) N- (4-hydroxyphenyl) -N-methyl-2-oxo-1- (2,3,4,5,6-pentamethylbenzyl) -1,2-dihydroquinoline- Copymade;

(314) (E)-5-(부트-2-엔아미도)-N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(314) (E) -5- (But-2-enamido) -N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- ;

(315) N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(315) N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(316) N-에틸-N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(316) N-ethyl-N- (4-hydroxyphenyl) -1- (4-methoxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(317) 1-(2,3-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(317) 1- (2,3-Dimethylphenyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(318) 1-(2,5-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(318) 1- (2,5-dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(319) 1-(2,6-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(319) 1- (2,6-Dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(320) N-에틸-N-(4-하이드록시페닐)-2-옥소-1-(2,4,6-트리메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(320) N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1- (2,4,6-trimethylphenethyl) -1,2-dihydroquinoline-3-carboxamide;

(321) N-메틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(321) N-methyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(322) N-메틸-N-(4-니트로페닐)-2-옥소-1-(2,3,4,5,6-펜타메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;(322) Synthesis of N-methyl-N- (4-nitrophenyl) -2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) -1,2-dihydroquinoline- Copymade;

(323) N-에틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(323) N-ethyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(324) N-(4-(N,N-디메틸설파모일)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(324) N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(325) N-(4-(N,N-디메틸설파모일)페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(325) N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(326) N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(326) N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(327) 1-(4-(1H-피라졸-1-일)벤질)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(327) 1- (4- (1H-pyrazol-1-yl) benzyl) -N- (4- (hydroxymethyl) 3-carboxamide;

(328) 1-(4-(1H-피라졸-1-일)벤조일)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(328) 1- (4- (1H-pyrazol-1-yl) benzoyl) -N- (4- (hydroxymethyl) phenyl) -N- 3-carboxamide;

(329) 1-(2,2-디페닐아세틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(329) 1- (2,2-Diphenylacetyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(330) 1-(2,2-디페닐에틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(330) 1- (2,2-diphenylethyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(331) N-(4-(하이드록시메틸)페닐)-5-(3-하이드록시프로판아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(331) N- (4- (hydroxymethyl) phenyl) -5- (3-hydroxypropanamido) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(332) N-(4-(하이드록시메틸)페닐)-N-메틸-5-(2-니트로아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(332) N- (4- (hydroxymethyl) phenyl) -N-methyl-5- (2-nitroacetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(333) N-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(333) N-ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(334) N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(334) N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(335) (E)-5-(부트-2-엔아미도)-N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(335) (E) -5- (But-2-enamido) -N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(336) N-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드;(336) N-ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;

(337) N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(337) N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(338) 5-벤즈아미도-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(338) 5-benzamido-N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(339) 5-(3,4-디하이드록시벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린 -3-카복사마이드;(339) 5- (3,4-Dihydroxybenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(340) 5-(3,4-디메틸벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(340) 5- (3,4-dimethylbenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(341) N-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(341) N- (methoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(342) N-(브로모메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(342) N- (bromomethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(343) N-(클로로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(343) N- (chloromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(344) N-(플루오로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(344) N- (fluoromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(345) N-(하이드록시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(345) N- (hydroxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(346) N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(346) N- (Nitromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(347) 5-(2-(벤조[d][1,3]디옥솔-5-일)아세트아미도)-N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(347) 5- (2- (Benzo [d] [1,3] dioxol-5-yl) acetamido) -N- (nitromethyl) -2-oxo-1,2-dihydroquinolin- - carboxamide;

(348) N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(348) N- (2-hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(349) 2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카복사마이드;(349) 2-oxo-N-propyl-l, 2-dihydroquinoline-3-carboxamide;

(350) 5-(3-(벤조[d][1,3]디옥솔-5-일)프로판아미도)-2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카복사마이드;(350) 5- (3- (Benzo [d] [1,3] dioxol-5-yl) propanamido) -2-oxo-N-propyl-l, 2-dihydroquinoline- Mide;

(351) (E)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드;(351) (E) -2-oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline-3-carboxamide;

(352) (E)-5-(3-(나프탈렌-2-일)프로판아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드;(352) (E) -5- (3- (Naphthalen-2-yl) propanamido) -2-oxo-N- (prop- 1-en-1-yl) -1,2-dihydroquinoline -3-carboxamide;

(353) (E)-5-(2-(나프탈렌-2-일)아세트아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드;(353) Synthesis of (E) -5- (2- (naphthalen-2-yl) acetamido) -2-oxo-N- (prop- 1-en-1-yl) -1,2-dihydroquinoline -3-carboxamide;

(354) N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(354) N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(355) N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(355) N- (2-bromoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(356) 5-(2-([1,1'-비페닐]-4-일)아세트아미도)-N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(356) 5- (2 - ([1,1'-biphenyl] -4- yl) acetamido) -N- (2-bromoethyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide;

(357) N-(2-클로로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(357) N- (2-chloroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(358) N-(2-플루오로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(358) N- (2-fluoroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(359) N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(359) N- (2-hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(360) N-(2-니트로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(360) N- (2-nitroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(361) N-(3-하이드록시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(361) N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(362) (E)-2-옥소-N-(펜트-3-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드;(362) (E) -2-oxo-N- (pent-3-en-1-yl) -1,2-dihydroquinoline-3-carboxamide;

(363) N-부틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(363) N-butyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(364) N-(3-메톡시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(364) N- (3-methoxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(365) N-(3-브로모프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(365) N- (3-bromopropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(366) N-(3-클로로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(366) N- (3-chloropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(367) N-(3-플루오로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(367) N- (3-fluoropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(368) (E)-N-(헥스-4-엔-1-일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(368) (E) -N- (hex-4-en-1-yl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(369) N-(3-하이드록시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(369) N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(370) N-(3-니트로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(370) N- (3-Nitropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(371) N-(4-하이드록시부틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(371) N- (4-hydroxybutyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(372) N-(3,4-디하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(372) N- (3,4-dihydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(373) N-(3,4-디에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(373) N- (3,4-diethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(374) N-(3,4-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(374) N- (3,4-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(375) N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(375) N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(376) 5-(2-(4-벤질페닐)아세트아미도)-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(376) Synthesis of 5- (2- (4-benzylphenyl) acetamido) -N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline- ;

(377) N-(3,4-디하이드록시펜에틸)-2-옥소-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카복사마이드;(377) N- (3,4-dihydroxyphenethyl) -2-oxo-5-propionamido-1,2-dihydroquinoline-3-carboxamide;

(378) 5-부티라미도-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(378) 5-Butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(379) N-(3,4-디하이드록시펜에틸)-2-옥소-5-펜탄아미도-1,2-디하이드로퀴놀린-3-카복사마이드;(379) N- (3,4-dihydroxyphenethyl) -2-oxo-5-pentanamido-1,2-dihydroquinoline-3-carboxamide;

(380) N-(3,4-디에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(380) N- (3,4-diethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(381) N-(3,4-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(381) N- (3,4-dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(382) N-(벤조[d][1,3]디옥솔-5-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(382) N- (benzo [d] [1,3] dioxol-5-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(383) N-(2-(벤조[d][1,3]디옥솔-5-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(383) N- (2- (benzo [d] [1,3] dioxol-5-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(384) N-(나프탈렌-2-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(384) N- (Naphthalen-2-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(385) N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(385) N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(386) 5-(2-(에틸티오)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(386) 5- (2- (Ethylthio) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(387) 5-(2-(에틸아미노)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(387) 5- (2- (ethylamino) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(388) 5-(2-에톡시아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(388) 5- (2-Ethoxyacetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(389) N-([1,1'-비페닐]-4-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(389) N - ([1,1'-biphenyl] -4-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(390) N-(2-([1,1'-비페닐]-4-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(390) N- (2 - ([1,1'-biphenyl] -4-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(391) N-(4-벤질벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(391) N- (4-benzylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(392) N-(4-벤질펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(392) N- (4-benzylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(393) N-(에톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(393) N- (ethoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(394) N-((에틸티오)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(394) N - ((ethylthio) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(395) N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(395) N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(396) N-((에틸아미노)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(396) N - ((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(397) N-(2-(메틸티오)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(397) N- (2- (methylthio) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(398) N-(2-(메틸아미노)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;(398) N- (2- (methylamino) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(399) 3-(페닐아미노)퀴놀린-2(1H)-온;(399) 3- (Phenylamino) quinolin-2 (1H) -one;

(400) 3-(p-톨일아미노)퀴놀린-2(1H)-온;(400) 3- (p-Tolylamino) quinolin-2 (1H) -one;

(401) 3-((4-메톡시페닐)아미노)퀴놀린-2(1H)-온;(401) 3 - ((4-methoxyphenyl) amino) quinolin-2 (1H) -one;

(402) 3-((4-브로모페닐)아미노)퀴놀린-2(1H)-온;(402) 3 - ((4-bromophenyl) amino) quinolin-2 (1H) -one;

(403) 3-((4-클로로페닐)아미노)퀴놀린-2(1H)-온;(403) 3 - ((4-chlorophenyl) amino) quinolin-2 (1H) -one;

(404) 3-((4-플루오로페닐)아미노)퀴놀린-2(1H)-온;(404) 3 - ((4-fluorophenyl) amino) quinolin-2 (1H) -one;

(405) 3-((4-에틸페닐)아미노)퀴놀린-2(1H)-온;(405) 3 - ((4-ethylphenyl) amino) quinolin-2 (1H) -one;

(406) 3-((4-하이드록시페닐)아미노)퀴놀린-2(1H)-온;(406) 3 - ((4-hydroxyphenyl) amino) quinolin-2 (1H) -one;

(407) 3-((4-니트로페닐)아미노)퀴놀린-2(1H)-온;(407) 3 - ((4-nitrophenyl) amino) quinolin-2 (1H) -one;

(408) 3-((4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온;(408) 3 - ((4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H) -one;

(409) 3-((4-비닐페닐)아미노)퀴놀린-2(1H)-온;(409) 3 - ((4-vinylphenyl) amino) quinolin-2 (1H) -one;

(410) N,N-디메틸-4-((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)벤젠설폰아미드;(410) N, N-dimethyl-4 - ((2-oxo-1,2-dihydroquinolin-3-yl) amino) benzenesulfonamide;

(411) 3-(벤질아미노)퀴놀린-2(1H)-온;(411) 3- (benzylamino) quinolin-2 (1H) -one;

(412) 3-((4-메틸벤질)아미노)퀴놀린-2(1H)-온;(412) 3 - ((4-methylbenzyl) amino) quinolin-2 (1H) -one;

(413) 3-((4-메톡시벤질)아미노)퀴놀린-2(1H)-온;(413) 3 - ((4-methoxybenzyl) amino) quinolin-2 (1H) -one;

(414) 3-((4-브로모벤질)아미노)퀴놀린-2(1H)-온;(414) 3 - ((4-bromobenzyl) amino) quinolin-2 (1H) -one;

(415) 3-((4-클로로벤질)아미노)퀴놀린-2(1H)-온;(415) 3 - ((4-chlorobenzyl) amino) quinolin-2 (1H) -one;

(416) 3-((4-클로로벤질)아미노)퀴놀린-2(1H)-온;(416) 3 - ((4-chlorobenzyl) amino) quinolin-2 (1H) -one;

(417) 3-((4-에틸벤질)아미노)퀴놀린-2(1H)-온;(417) 3 - ((4-ethylbenzyl) amino) quinolin-2 (1H) -one;

(418) 3-((4-하이드록시벤질)아미노)퀴놀린-2(1H)-온;(418) 3 - ((4-hydroxybenzyl) amino) quinolin-2 (1H) -one;

(419) 3-((4-니트로벤질)아미노)퀴놀린-2(1H)-온;(419) 3 - ((4-nitrobenzyl) amino) quinolin-2 (1H) -one;

(420) N,N-디메틸-4-(((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)메틸)벤젠설폰아미드;(420) N, N-Dimethyl-4 - (((2-oxo-1,2-dihydroquinolin-3-yl) amino) methyl) benzenesulfonamide;

(421) 3-((4-(하이드록시메틸)벤질)아미노)퀴놀린-2(1H)-온;(421) 3 - ((4- (hydroxymethyl) benzyl) amino) quinolin-2 (1H) -one;

(422) 3-((4-비닐벤질)아미노)퀴놀린-2(1H)-온;(422) 3 - ((4-vinylbenzyl) amino) quinolin-2 (1H) -one;

(423) 3-(메틸(페닐)아미노)퀴놀린-2(1H)-온;(423) 3- (Methyl (phenyl) amino) quinolin-2 (1H) -one;

(424) 3-(에틸(페닐)아미노)퀴놀린-2(1H)-온;(424) 3- (ethyl (phenyl) amino) quinolin-2 (1H) -one;

(425) 3-(에틸(p-톨일)아미노)퀴놀린-2(1H)-온;(425) 3- (ethyl (p-tolyl) amino) quinolin-2 (1H) -one;

(426) 3-(메틸(p-톨일)아미노)퀴놀린-2(1H)-온;(426) 3- (methyl (p-tolyl) amino) quinolin-2 (1H) -one;

(427) 3-((4-메톡시페닐)(메틸)아미노)퀴놀린-2(1H)-온;(427) 3 - ((4-methoxyphenyl) (methyl) amino) quinolin-2 (1H) -one;

(428) 3-(에틸(4-메톡시페닐)아미노)퀴놀린-2(1H)-온;(428) 3- (ethyl (4-methoxyphenyl) amino) quinolin-2 (1H) -one;

(429) 3-((4-브로모페닐)(에틸)아미노)퀴놀린-2(1H)-온;(429) 3 - ((4-bromophenyl) (ethyl) amino) quinolin-2 (1H) -one;

(430) 3-((4-브로모페닐)(메틸)아미노)퀴놀린-2(1H)-온;(430) 3 - ((4-Bromophenyl) (methyl) amino) quinolin-2 (1H) -one;

(431) 3-((4-클로로페닐)(에틸)아미노)퀴놀린-2(1H)-온;(431) 3 - ((4-chlorophenyl) (ethyl) amino) quinolin-2 (1H) -one;

(432) 3-((4-클로로페닐)(에틸)아미노)퀴놀린-2(1H)-온;(432) 3 - ((4-chlorophenyl) (ethyl) amino) quinolin-2 (1H) -one;

(433) 3-((4-플루오로페닐)(메틸)아미노)퀴놀린-2(1H)-온;(433) 3 - ((4-fluorophenyl) (methyl) amino) quinolin-2 (1H) -one;

(434) 3-(에틸(4-플루오로페닐)아미로)퀴놀린-2(1H)-온;(434) 3- (ethyl (4-fluorophenyl) amyl) quinolin-2 (1H) -one;

(435) 3-(에틸(4-에틸페닐)아미노)퀴놀린-2(1H)-온;(435) 3- (ethyl (4-ethylphenyl) amino) quinolin-2 (1H) -one;

(436) 3-((4-에틸페닐)(메틸)아미노)퀴놀린-2(1H)-온;(436) 3 - ((4-ethylphenyl) (methyl) amino) quinolin-2 (1H) -one;

(437) 3-(에틸(4-하이드록시페닐)아미노)퀴놀린-2(1H)-온;(437) 3- (ethyl (4-hydroxyphenyl) amino) quinolin-2 (1H) -one;

(438) 3-(에틸(4-하이드록시페닐)아미노)퀴놀린-2(1H)-온;(438) 3- (ethyl (4-hydroxyphenyl) amino) quinolin-2 (1H) -one;

(439) 3-(메틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온;(439) 3- (Methyl (4-nitrophenyl) amino) quinolin-2 (1H) -one;

(440) 3-(에틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온;(440) 3- (ethyl (4-nitrophenyl) amino) quinolin-2 (1H) -one;

(441) 3-(에틸(4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온;(441) 3- (ethyl (4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H) -one;

(442) 3-((4-(하이드록시메틸)페닐)(메틸)아미노)퀴놀린-2(1H)-온;(442) 3 - ((4- (hydroxymethyl) phenyl) (methyl) amino) quinolin-2 (1H) -one;

(443) 3-(메틸(4-비닐페닐)아미노)퀴놀린-2(1H)-온;(443) 3- (methyl (4-vinylphenyl) amino) quinolin-2 (1H) -one;

(444) 3-(에틸(4-비닐페닐)아미노)퀴놀린-2(1H)-온;(444) 3- (ethyl (4-vinylphenyl) amino) quinolin-2 (1H) -one;

(445) 3-((3,4-디메틸페닐)아미노)퀴놀린-2(1H)-온;(445) 3 - ((3,4-dimethylphenyl) amino) quinolin-2 (1H) -one;

(446) 3-((3,4-디메틸벤질)아미노)퀴놀린-2(1H)-온;(446) 3 - ((3,4-dimethylbenzyl) amino) quinolin-2 (1H) -one;

(447) 3-((3,4-디하이드록시페닐)아미노)퀴놀린-2(1H)-온;(447) 3 - ((3,4-dihydroxyphenyl) amino) quinolin-2 (1H) -one;

(448) 3-((3,4-디하이드록시벤질)아미노)퀴놀린-2(1H)-온;(448) 3 - ((3,4-dihydroxybenzyl) amino) quinolin-2 (1H) -one;

(449) 3-((벤조[d][1,3]디옥솔-5-일메틸)아미노)퀴놀린-2(1H)-온;(449) 3 - ((benzo [d] [1,3] dioxol-5-ylmethyl) amino) quinolin-2 (1H) -one;

(450) 3-((2-(벤조[d][1,3]디옥솔-5-일)에틸)아미노)퀴놀린-2(1H)-온;(450) 3 - ((2- (Benzo [d] [1,3] dioxol-5-yl) ethyl) amino) quinolin-2 (1H) -one;

(451) 3-((나프탈렌-2-일메틸)아미노)퀴놀린-2(1H)-온;(451) 3 - ((Naphthalen-2-ylmethyl) amino) quinolin-2 (1H) -one;

(452) 3-((2-(나프탈렌-2-일)에틸)아미노)퀴놀린-2(1H)-온(452) 3 - ((2- (naphthalen-2-yl) ethyl) amino) quinolin-

(453) 3-(([1,1'-비페닐]-4-일메틸)아미노)퀴놀린-2(1H)-온;(453) 3 - (([1,1'-biphenyl] -4-ylmethyl) amino) quinolin-2 (1H) -one;

(454) 3-((2-([1,1'-비페닐]-4-일)에틸)아미노)퀴놀린-2(1H)-온;(454) 3 - ((2 - ([1,1'-biphenyl] -4-yl) ethyl) amino) quinolin-2 (1H) -one;

(455) 3-((4-벤질펜에틸)아미노)퀴놀린-2(1H)-온;(455) 3 - ((4-benzylphenethyl) amino) quinolin-2 (1H) -one;

(456) 3-((4-벤질벤질)아미노)퀴놀린-2(1H)-온;(456) 3 - ((4-benzylbenzyl) amino) quinolin-2 (1H) -one;

(457) 3-(에틸아미노)퀴놀린-2(1H)-온;(457) 3- (ethylamino) quinolin-2 (1H) -one;

(458) 3-(프로필아미노)퀴놀린-2(1H)-온;(458) 3- (propylamino) quinolin-2 (1H) -one;

(459) 3-(부틸아미노)퀴놀린-2(1H)-온;(459) 3- (butylamino) quinolin-2 (1H) -one;

(460) 3-((에톡시메틸)아미노)퀴놀린-2(1H)-온;(460) 3 - ((Ethoxymethyl) amino) quinolin-2 (1H) -one;

(461) 3-(((에틸티오)메틸)아미노)퀴놀린-2(1H)-온; 및(461) 3 - (((ethylthio) methyl) amino) quinolin-2 (1H) -one; And

(462) 메틸 5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트(462) Methyl 5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

(463) 5-클로로-2-옥소-N-페네틸-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드;(463) 5-chloro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;

(464) 5-클로로-1-(4-에틸벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카프복스아미드;(464) 5-Chloro-1- (4-ethylbenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(465) 5-클로로-1-(4-아이소프로필벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;(465) 5-Chloro-l- (4-isopropylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline-3-carboxamide;

(466) 5-클로로-1-(4-나이트로벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;(466) 5-Chloro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(467) 5-클로로-1-(4-메톡시벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;(467) 5-Chloro-1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(468) 5-클로로-1-(4-에틸벤질)-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카프복스아미드;(468) 5-Chloro-1- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(469) 5-클로로-N-(4-플루오로페네틸)-1-(4-아이소프로필벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;(469) 5-Chloro-N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(470) 5-클로로-N-(4-플루오로페네틸)-1-(4-나이트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;(470) 5-Chloro-N- (4-fluorophenethyl) -1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(471) 5-클로로-N-(4-플루오로페네틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;(471) 5-Chloro-N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(472) 5-클로로-N-(4-플루오로페네틸)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드;(472) 5-chloro-N- (4-fluorophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;

(473) 1-(4-에틸벤질)-N-(4-플루오로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드;(473) 1- (4-Ethylbenzyl) -N- (4-fluorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(474) N-(4-플루오로펜에틸)-1-(4-이소프로필벤질)-5-니트로닉-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드);(474) N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitronic-oxo-1,2-dihydroquinoline-3-carboxamide);

(475) N-(4-플루오로펜에틸)-5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드;(475) N- (4-fluorophenethyl) -5-nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(476) 5-아미노-N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드);(476) 5-Amino-N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;

(477) 1-(4-메톡시벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드;(477) 1- (4-methoxybenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(478) N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드;(478) N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(479) 5-니트로-2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드;(479) 5-Nitro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;

(480) N-(4-플루오로펜에틸)-5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드;(480) N- (4-Fluorophenethyl) -5-nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;

(481) 1-(4-이소프로필벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드;(481) 1- (4-Isopropylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(482) 메틸 1-(4-메톡시벤질)-2-옥소-5-(3-페닐프로파나미노)-1,2-디하이드로퀴놀린-3-카복실레이트;(482) Methyl 1- (4-methoxybenzyl) -2-oxo-5- (3-phenylpropanamino) -1,2-dihydroquinoline-3-carboxylate;

(483) 메틸 5-(3-사이클로펜틸프로파나미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(483) Methyl 5- (3-cyclopentylpropanamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(484) 메틸 1-(4-메톡시벤질)-2-옥소-5-(2-페닐아세타미도)-1,2-디하이드로퀴놀린-3-카복실레이트;(484) Methyl 1- (4-methoxybenzyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline-3-carboxylate;

(485) 메틸 5-벤즈아미도-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(485) Methyl 5-benzamido-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(486) 메틸 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(486) Methyl 5- (2- (4-chlorophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(487) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(487) Methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(488) 메틸 5-(3,5-디메틸아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(488) Methyl 5- (3,5-dimethyladamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(489) 메틸 5-(3-브로모아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(489) Methyl 5- (3-bromoadamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(490) 메틸 1-(4-메톡시벤질)-5-(3-메틸아다만테인-1-카복시아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(490) Methyl 1- (4-methoxybenzyl) -5- (3-methyladamantane-1-carboxyamido) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(491) 메틸 5-(2-(아다만테인-1-일)아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;(491) Methyl 5- (2- (adamantan-1-yl) amido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;

(492) 메틸 5-(2-(3,5-디메틸아다만테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이하이드록시퀴놀린-3-카복실레이트;(492) Methyl 5- (2- (3,5-dimethyladamantan-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroxyquinoline -3-carboxylate;

(493) 메틸 5-(2-(3-브로모메테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(493) Methyl 5- (2- (3-bromometh-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline- Rate;

(494) 메틸 1-(4-메톡시벤질)-5-(2-(3-메틸아다만테인-1-일)아세트아미도)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(494) Methyl 1- (4-methoxybenzyl) -5- (2- (3-methyladamantan-1- yl) acetamido) -2-oxo-1,2-dichloroquinoline- Rate;

(495) 메틸 5-(2-사이크로헥실아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(495) Methyl 5- (2-cyclohexylacetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(496) 메틸 5-(사이클로헥센카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(496) Methyl 5- (cyclohexecarboxamidoido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(497) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-에틸벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(497) Methyl 5- (adamantane-1-carboxyamido) -1- (4-ethylbenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(498) 메틸 5-(아다만테인-1-카복시아미도)-1-(3-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(498) Methyl 5- (adamantane-1-carboxyamido) -1- (3-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(499) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-나이트로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(499) Methyl 5- (adamantane-1-carboxyamido) -1- (4-nitrobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(500) 메틸 5-(아다만테인-1-카복시아미도)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디클로로퀴놀린-3-카복실레이트;(500) Methyl 5- (adamantane-1-carboxyamido) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dichloroquinoline-3-carboxylate;

(501) 메틸 5-(아다만테인-1-카복소아미도)-1-(4-사이아노벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(501) Methyl 5- (adamantane-1-carboxamido) -1- (4-cyanobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(502) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-플루오로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(502) Methyl 5- (adamantane-1-carboxyamido) -1- (4-fluorobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(503) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드;(503) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid;

(504) 에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(504) Ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(505) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N-메틸-2-옥소-1,2-디클로로퀴놀린-3-카복시아미도;(505) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N-methyl-2-oxo-1,2-dichloroquinoline-3-carboxamido;

(506) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N,N-디메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복시아마이드;(506) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N, N-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;

(507) 프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(507) propyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(508) 아이소프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;(508) isopropyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;

(509) N-(1-(4-메톡시벤질)-3-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린 -5-일)아다만테인-1-카복시아마이드;(509) N- (1- (4-methoxybenzyl) -3- (methoxymethyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxyamide;

(510) N-(3-(에톡시메틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린 -5-일)아다만테인-1-카복시아마이드;(510) N- (3- (ethoxymethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxyamide;

(511) S-메틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트;(511) S-Methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate;

(512) S-에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트;(512) S-ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate;

(513) 1-(4-메톡시벤질)-5-나이트로퀴놀린-2(1H)-온;(513) 1- (4-methoxybenzyl) -5-nitroquinolin-2 (1H) -one;

(514) 5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온;(514) 5-Amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one;

(515) 5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온;(515) 5-hydrazinyl-l- (4-methoxybenzyl) quinolin-2 (lH) -one;

(516) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테 인-1-카복사마이드;(516) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;

(517) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카복사마이드;(517) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carboxamide;

(518) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-디메틸아다만테인-1-카복사마이드;(518) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyladamantane-1-carboxamide;

(519) 3-브로모-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드;(519) 3-Bromo-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;

(520) 3-클로로-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드;(520) 3-Chloro-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;

(521) 2-(아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로 퀴놀린-5-일)아세트아마이드;(521) 2- (Adamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;

(522) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세트아마이드;(522) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -2- (3-methyladamantan-1-yl) acetamide;

(523) 2-(3,5-디메틸아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;(523) 2- (3,5-Dimethyladamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Amide;

(524) 2-(3-브로모아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;(524) 2- (3-Bromo-adamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;

(525) 2-(3-클로로아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;(525) 2- (3-Chloroadamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;

(526) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;(526) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;

(527) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카르보하이드라자이드;(527) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carbohydrazide;

(528) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-디메틸아다만테인-1-카르보하이드라자이드;(528) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyladamantane-1-carbohydrazide ;

(529) 3-브로모-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;(529) 3-Bromo-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;

(530) 3-클로로-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;(530) 3-Chloro-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;

(531) 2-(아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드;(531) 2- (Adamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetohydrazide;

(532) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세토하이드라자이드;(532) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Draazide;

(533) 2-(3,5-디메틸아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드;(533) 2- (3,5-Dimethyladamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Acetohydrazide;

(534) 2-(3-브로모아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드; 및(534) 2- (3-Bromo-adamantan-1-yl) -N '- (1- (4- methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Draazide; And

(535) 2-(3-클로로아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드(535) 2- (3-Chloroadamantan-1-yl) -N '- (1- (4- methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Draazide

로 구성된 군으로부터 선택된다.≪ / RTI >

본 발명의 보다 더 구체적인 구현예에 따르면, 본 발명의 퀴놀리논 유도체는According to a more specific embodiment of the present invention, the quinolinone derivative of the present invention is

(1) 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(1) 1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(2) 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(2) 1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(3) 1-(4-플루오로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(3) 1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(4) 1-(4-플루오로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(4) 1- (4-Fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(5) 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(5) 1- (4-Chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(6) 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(6) 5-Nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(7) 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(7) 1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(8) 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;(8) 1- (4-Cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;

(14) 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드; 및(14) 1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide; And

(16) 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드(16) Synthesis of 5-nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

로 구성된 군으로부터 선택된다.≪ / RTI >

본 발명에 따르면, 상기 나열한 10가지 화합물은 동일한 농도(10μM)를 투여하였을 때 IL-2에 대해 매우 높은 억제율(% Inhibition)을 가짐이 확인되었다. 따라서 이들은 과도한 IL-2 활성과 관련된 다양한 질환의 효과적인 치료 조성물로 이용될 수 있다.According to the present invention, it was confirmed that the 10 compounds listed above had a very high% inhibition of IL-2 when administered at the same concentration (10 μM). They can therefore be used as effective therapeutic compositions for a variety of diseases associated with excessive IL-2 activity.

본 발명의 다른 양태에 따르면, 본 발명은 본 발명에서 개시하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 IL-2 (Interleukin-2)의 활성 억제용 조성물을 제공한다.According to another aspect of the present invention, there is provided a composition for inhibiting the activity of IL-2 (Interleukin-2), which comprises the quinolinone derivative of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient .

본 발명의 또 다른 양태에 따르면, 본 발명은 본 발명에서 개시하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 IL-2 과발현 또는 IL-2 과다활성과 관련된 질환의 예방 또는 치료용 조성물을 제공한다.According to another aspect of the present invention, there is provided a method for preventing IL-2 overexpression or IL-2 hyperactivity related disease comprising the quinolinone derivative or pharmaceutically acceptable salt thereof disclosed in the present invention as an active ingredient Or a therapeutic composition.

본 발명의 조성물이 약제학적 조성물로 제조되는 경우, 본 발명의 약제학적 조성물은 약제학적으로 허용되는 담체를 포함한다. 본 발명의 약제학적 조성물에 포함되는 약제학적으로 허용되는 담체는 제제시에 통상적으로 이용되는 것으로서, 락토스, 덱스트로스, 수크로스, 솔비톨, 만니톨, 전분, 아카시아 고무, 인산 칼슘, 알기네이트, 젤라틴, 규산 칼슘, 미세결정성 셀룰로스, 폴리비닐피롤리돈, 셀룰로스, 물, 시럽, 메틸 셀룰로스, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 활석, 스테아르산 마그네슘 및 미네랄 오일 등을 포함하나, 이에 한정되는 것은 아니다. 본 발명의 약제학적 조성물은 상기 성분들 이외에 윤활제, 습윤제, 감미제, 향미제, 유화제, 현탁제, 보존제 등을 추가로 포함할 수 있다. 적합한 약제학적으로 허용되는 담체 및 제제는 Remington's Pharmaceutical Sciences (19th ed., 1995)에 상세히 기재되어 있다.When the composition of the present invention is manufactured from a pharmaceutical composition, the pharmaceutical composition of the present invention includes a pharmaceutically acceptable carrier. The pharmaceutically acceptable carriers to be contained in the pharmaceutical composition of the present invention are those conventionally used in the present invention and include lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia rubber, calcium phosphate, alginate, gelatin, But are not limited to, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrups, methylcellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. It is not. The pharmaceutical composition of the present invention may further contain a lubricant, a wetting agent, a sweetening agent, a flavoring agent, an emulsifying agent, a suspending agent, a preservative, etc. in addition to the above components. Suitable pharmaceutically acceptable carriers and formulations are described in detail in Remington ' s Pharmaceutical Sciences (19th ed., 1995).

본 발명의 약제학적 조성물은 경구 또는 비경구 투여할 수 있으며, 비경구 투여인 경우에는 정맥내 주입, 피하 주입, 근육 주입, 복강 주입, 경피 투여 등으로 투여할 수 있다.The pharmaceutical composition of the present invention can be administered orally or parenterally, and in the case of parenteral administration, it can be administered by intravenous injection, subcutaneous injection, muscle injection, intraperitoneal injection, transdermal administration or the like.

본 발명의 약제학적 조성물의 적합한 투여량은 제제화 방법, 투여 방식, 환자의 연령, 체중, 성, 병적 상태, 음식, 투여 시간, 투여 경로, 배설 속도 및 반응 감응성과 같은 요인들에 의해 다양하게 처방될 수 있다. 본 발명의 약제학적 조성물의 1일 투여량은 예컨대 0.001-100 mg/kg이다.The appropriate dosage of the pharmaceutical composition of the present invention may vary depending on factors such as the formulation method, administration method, age, body weight, sex, pathological condition, food, administration time, administration route, excretion rate, . The daily dosage of the pharmaceutical composition of the present invention is, for example, 0.001-100 mg / kg.

본 발명의 약제학적 조성물은 당해 발명이 속하는 기술분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있는 방법에 따라, 약제학적으로 허용되는 담체 및/또는 부형제를 이용하여 제제화함으로써 단위 용량 형태로 제조되거나 또는 다용량 용기 내에 내입시켜 제조될 수 있다. 이때 제형은 오일 또는 수성 매질중의 용액, 현탁액, 시럽제 또는 유화액 형태이거나 엑스제, 산제, 분말제, 과립제, 정제 또는 캅셀제 형태일 수도 있으며, 분산제 또는 안정화제를 추가적으로 포함할 수 있다.The pharmaceutical composition of the present invention may be formulated into a unit dose form by formulating it using a pharmaceutically acceptable carrier and / or excipient according to a method which can be easily carried out by a person having ordinary skill in the art to which the present invention belongs. Or by intrusion into a multi-dose container. The formulations may be in the form of solutions, suspensions, syrups or emulsions in oils or aqueous media, or in the form of excipients, powders, powders, granules, tablets or capsules, and may additionally contain dispersing or stabilizing agents.

본 발명의 구체적인 구현예에 따르면, 본 발명의 조성물로 치료되는 IL-2 과발현 또는 IL-2 과다활성과 관련된 질환은 염증성 질환 또는 자가면역 질환이다.According to a specific embodiment of the present invention, diseases associated with IL-2 overexpression or IL-2 hyperactivity which are treated with the composition of the invention are inflammatory diseases or autoimmune diseases.

보다 구체적으로, 상기 염증성 질환은 만성폐쇄성 폐질환(chronic obstructive pulmonary disease), 기도 과민성 질환(airways hyper-responsiveness), 폐혈성 쇼크(septic shock), 사구체 신염, 염증성 장질환, 크론병(Crohn's disease), 궤양잘록창자염(ulcerative colitis), 아테롬성 동맥경화증, 골수아구 세포성 백혈병(myoblastic leukaemia), 당뇨, 화상, 허혈성 심장질환, 뇌졸중, 수막염 및 정맥류로 구성된 군으로부터 선택된다.More specifically, the inflammatory disease is selected from the group consisting of chronic obstructive pulmonary disease, airways hyper-responsiveness, septic shock, glomerulonephritis, inflammatory bowel disease, Crohn's disease, , Ulcerative colitis, atherosclerosis, myoblastic leukemia, diabetes, burns, ischemic heart disease, stroke, meningitis and varicose veins.

보다 구체적으로, 상기 자가면역 질환은 류마티스 관절염, 건선, 알러지성 피부염, 다발성 경화증, 루프스 및 천식으로 구성된 군으로부터 선택되는 질환이다.More specifically, the autoimmune disease is a disease selected from the group consisting of rheumatoid arthritis, psoriasis, allergic dermatitis, multiple sclerosis, lupus and asthma.

본 발명의 또 다른 양태에 따르면, 본 발명은 본 발명의 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 조성물을 대상체에 투여하는 단계를 포함하는 염증성 질환 또는 자가면역 질환의 예방 또는 치료방법을 제공한다. 본 발명에서 사용되는 퀴놀리논 유도체 화합물 및 본 발명의 조성물로 예방 또는 치료될 수 있는 염증성 질환 또는 자가면역 질환에 대해서는 이미 상술하였으므로, 과도한 중복을 피하기 위하여 그 기재를 생략한다.According to still another aspect of the present invention, there is provided a method of treating inflammatory diseases or autoimmune diseases, comprising administering to a subject a composition comprising the quinolinone derivative of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient Prevention or treatment. Since the inflammatory diseases or autoimmune diseases that can be prevented or treated by the quinolinone derivative compounds and the composition of the present invention used in the present invention have already been described above, the description thereof will be omitted in order to avoid excessive redundancy.

본 발명의 특징 및 이점을 요약하면 다음과 같다:The features and advantages of the present invention are summarized as follows:

(a) 본 발명은 다양한 신규 퀴놀리논 유도체 화합물 및 이들을 유효성분으로 포함하는 IL-2 활성 억제용 조성물을 제공한다.(a) The present invention provides various novel quinolinone derivative compounds and a composition for inhibiting IL-2 activity comprising the same as an active ingredient.

(b) 본 발명은 IL-2의 과도한 발현 또는 활성과 관련된 다양한 질환, 즉 만성 염증성 질환, 염증성 통증 또는 자가면역 질환의 예방 또는 치료에 유용하게 이용될 수 있다.(b) The present invention can be usefully used for the prevention or treatment of various diseases associated with excessive expression or activity of IL-2, i.e. chronic inflammatory diseases, inflammatory pain or autoimmune diseases.

이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지 않는다는 것은 당업계에서 통상의 지식을 가진 자에 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention .

실시예Example

후보 화합물의 스크리닝Screening of candidate compounds

퀴놀리논 물질은 식물에서 추출한 천연물의 일종으로 다양한 생물학적 활성을 가지고 있다고 알려져 있다. 뿐만 아니라 퀴놀리논은 화학적인 구조가 밝혀져 있고 그 안에 포함되어 있는 락탐 부분이 수소 결합을 할 수 있는 가능성을 보이고 있다. 이 같은 사실을 바탕으로 퀴놀리논에 대한 생물학적 활성을 알아보기 위해 퀴놀리논 화합물을 효율적으로 다량 합성하였다. 합성한 퀴놀리논 물질들을 기반으로 IL-2 ELISA 분석을 통해 Jurkat T 세포에서 면역 억제제로서의 가능성을 탐색한 결과 특정 물질들이 면역 억제제로서의 높은 잠재력을 가짐을 확인하였다. IL-2는 주로 T 세포에서 생성되지만 살생(NK) 세포에서도 생성된다. 이는 세포주기를 진행시키는 진행인자로서 작용해 호중구에 의한 종양괴사인자의 생산, 대식세포로부터의 형질전환 증식인자의 생산, IL-8의 생산, TNF의 생산, T 세포로부터의 IL-5의 생산 등이 알려져 있지만 T 세포, NK세포에서 인터페론γ생산의 유도는 시토카인 네트워크 형성에도 중요한 위치를 차지한다. T 세포나 인터페론γ생산의 유도는 시토카인 네트워크 형성에도 중요한 위치를 차지한다. IL-2유전자의 녹아웃 마우스로는 염증성 장질환, 용혈성 빈혈의 발생이 알려져 있다. IgG1, IgE의 생산을 증가시키는 것도 알려져 있으며, IL-2는 TH1/TH2의 균형 유지에 중요한 기능을 담당하고 있다.Quinolinone is a natural product extracted from plants and is known to have various biological activities. In addition, quinolinone has a chemical structure, and the lactam moiety contained in it has the possibility of hydrogen bonding. Based on these facts, quinolinone compounds were efficiently synthesized in large amounts in order to investigate the biological activity of quinolinone. Based on the synthesized quinolinone substances, IL-2 ELISA analysis revealed that certain substances have high potential as immunosuppressants in Jurkat T cells. Although IL-2 is mainly produced in T cells, it is also produced in killing (NK) cells. It acts as a progressive factor in the progression of the cell cycle, leading to the production of tumor necrosis factor by neutrophils, production of transforming growth factors from macrophages, production of IL-8, production of TNF, production of IL-5 from T cells . However, induction of interferon gamma production in T cells and NK cells is also important for cytokine network formation. Induction of T cell or interferon gamma production is also important for cytokine network formation. IL-2 gene knockout mice are known to have inflammatory bowel disease and hemolytic anemia. It is also known to increase the production of IgG1 and IgE, and IL-2 plays an important role in maintaining the balance of T H 1 / T H 2.

합성 모식도Synthetic pattern diagram

Figure 112016031927621-pct00010
Figure 112016031927621-pct00010

이하 실시예에서 기재하는 화합물 번호, 반응과정 및 치환기는 상기 합성 모식도 상의 화합물 번호, 반응과정 및 치환기를 의미한다.The compound number, the reaction process and the substituent described in the following examples mean the compound number on the synthetic scheme, the reaction process and the substituent.

일반적 합성과정General synthesis process

단계(a)의 일반적 과정The general process of step (a)

출발물질(10.0 g, 60.2 mmol)을 무수 MeOH(100 mL)에 용해시켰다. 디메틸 말로네이트(20.7 mL, 180.6 mmol) 및 CH3ONa(13.0g, 240.8mmol)를 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다.The starting material (10.0 g, 60.2 mmol) was dissolved in anhydrous MeOH (100 mL). Dimethyl malonate (20.7 mL, 180.6 mmol) and CH 3 ONa (13.0 g, 240.8 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours, and after filtration, the filtrate was washed with MeOH to obtain the desired compound.

합성예 65 : 메틸 7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 65: Synthesis of methyl 7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate

2-아미노-4-니트로벤즈알데하이드(1 mmol)를 무수 MeOH(2 mL)에 용해시켰다. 디메틸말로네이트(3 mmol) 및 CH3ONa(4mmol)를 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다(수율=85%).2-Amino-4-nitrobenzaldehyde (1 mmol) was dissolved in anhydrous MeOH (2 mL). Dimethyl malonate (3 mmol) and CH 3 ONa (4 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours, and after filtration, the filtrate was washed with MeOH to give the target compound (yield = 85%).

1H NMR(400MHz, CDCl3)δ 8.69 (s, 1H), 8.24 (s, 1H), 8.0 (s, 1H, -NH), 7.95 (d, 1H), 7.62 (s, 1H), 3.77 (s, 3H). MASS = 248.04 1 H NMR (400MHz, CDCl 3 )? 8.69 (s, IH), 8.24 (s, IH), 8.0 s, 3H). MASS = 248.04

합성예 67 : 메틸 5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 67: Synthesis of methyl 5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate

2-아미노-6-니트로벤즈알데하이드 (1 mmol)를 무수 MeOH(2 mL)로 용해시켰다. 디메틸말로네이트 (3 mmol) 및 CH3ONa(4mmol)를 용액에 첨가하였다.혼합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다(수율=78%)2-Amino-6-nitrobenzaldehyde (1 mmol) was dissolved in anhydrous MeOH (2 mL). Dimethyl malonate (3 mmol) and CH 3 ONa (4 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours, and after filtration, the filtrate was washed with MeOH to give the title compound (Yield = 78%

1H NMR(400MHz, CDCl3) δ8.76(s, 1H), 7.92 (dd, 1.2, 1H), 7.77(t, 1H), 7.64 (d, 1H), 3.80(s, 3H) MASS=248.04 1 H NMR (400MHz, CDCl 3 ) δ8.76 (s, 1H), 7.92 (dd, 1.2, 1H), 7.77 (t, 1H), 7.64 (d, 1H), 3.80 (s, 3H) MASS = 248.04

합성예 71 : 메틸 2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 71: Synthesis of methyl 2-oxo-1,2-dihydroquinoline-3-carboxylate

2-아미노벤즈알데하이드 (1 mmol)를 무수 MeOH (2 mL)에 용해시켰다. 디메틸 말로네이트(3 mmol) 및 CH3ONa(4mmol)를 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다(수율=82%).2-Aminobenzaldehyde (1 mmol) was dissolved in anhydrous MeOH (2 mL). Dimethyl malonate (3 mmol) and CH 3 ONa (4 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours, and after filtration, the filtrate was washed with MeOH to give the target compound (yield = 82%).

1HNMR(400MHz, CDCl3)δ 8.37(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.77(s, 3H). MASS = 203.06 1 H NMR (400 MHz, CDCl 3 )? 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , ≪ / RTI > 1H), 3.77 (s, 3H). MASS = 203.06

합성예 510 : 메틸 5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 510: Methyl 5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

2,6-디아미노벤즈알데하이드(1 mmol)를 무수 MeOH(2 mL)에 용해시켰다. 디메틸 말로네이트(3 mmol) 및 CH3ONa(4mmol)를 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다(수율=77%).2,6-diaminobenzaldehyde (1 mmol) was dissolved in anhydrous MeOH (2 mL). Dimethyl malonate (3 mmol) and CH 3 ONa (4 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours, and after filtration, the filtrate was washed with MeOH to obtain the target compound (yield = 77%).

1H NMR (400MHz, CDCl3) δ11.62(s, 1H), 8.21(s, 1H, -NH), 7.17(t, 1H), 6.33 (dd, 1H), 6.22(s, 1H), 3.77(s, 1H). MASS=218.07 1 H NMR (400MHz, CDCl 3 ) δ11.62 (s, 1H), 8.21 (s, 1H, -NH), 7.17 (t, 1H), 6.33 (dd, 1H), 6.22 (s, 1H), 3.77 (s, 1 H). MASS = 218.07

단계(b-2)의 일반적 과정General procedure of step (b-2)

1번 화합물(7.0g,32.0mmol)을 DMF(230mL)에 용해시켰다. Cs2CO3(12.5g, 38.4mmol) 및 R2-Cl 또는 R2-Br(5.2mL, 38.4mmol)를 반응 혼합물에 첨가하고 22시간 동안 교반한 뒤, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 브린(brine)으로세척하고 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 2번 화합물을 수득하였다.Compound No. 1 (7.0 g, 32.0 mmol) was dissolved in DMF (230 mL). Cs 2 CO 3 (12.5 g, 38.4 mmol) and R 2 -Cl or R 2 -Br (5.2 mL, 38.4 mmol) were added to the reaction mixture and stirred for 22 h before extraction with ethyl acetate and H 2 O . The combined organic layers were washed with Dublin (brine) and dried over anhydrous Na 2 SO 4, and concentrated in vacuo. Purification by column chromatography gave compound No. 2.

합성예 66 : 메틸 1-(2-(사이클로펜타-1,3-디엔-1-일)에틸)-7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 66: Synthesis of methyl 1- (2- (cyclopenta-1,3-dien-1-yl) ethyl) -7-nitro-2-oxo-1,2-dihydroquinoline-

합성예 65의 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. Cs2CO3(1.2mmol) 및 5-(2-클로로에틸)사이클로펜타-1,3-디엔(1.2mmol)를 반응 혼합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다.합쳐진 유기층을 브린(brine)으로세척하고 무수 Na2SO4로 건조시키고, 진공에서 농축하였다.컬럼 크로마토그래피로 정제하여 합성예 66의 화합물을 수득하였다(수율=67%).The compound of Synthesis Example 65 (1 mmol) was dissolved in DMF (2 mL). Cs 2 CO 3 (1.2mmol) and 5- (2-chloroethyl) stirred cyclopenta-1,3-diene-22 hours after the addition of (1.2mmol) the reaction mixture and extracted with ethyl acetate and H 2 O The combined organic layers were washed with brine, dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography gave the compound of Synthesis Example 66 (Yield = 67%).

1H NMR (400MHz,CDCl3)δ 8.69 (s, 1H), 8.24 (s, 1H), 7.95 (d, 1H), 7.62 (d, 1H), 6.5 (d, 1H), 6.4 (d, 1H), 6.28 (s, 1H), 3.77 (s, 3H), 3.00 (s, 2H), 2.9 (s, 1H), 2.22 (s, 2H). MASS = 340.11 1 H NMR (400MHz, CDCl 3 ) δ 8.69 (s, 1H), 8.24 (s, 1H), 7.95 (d, 1H), 7.62 (d, 1H), 6.5 (d, 1H), 6.4 (d, 1H ), 6.28 (s, 1H), 3.77 (s, 3H), 3.00 (s, 2H), 2.9 (s, MASS = 340.11

합성예 68 : 메틸 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 68: Methyl 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate

합성예 67 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. Cs2CO3(1.2mmol) 및 클로로에탄(1.2mmol)를 반응 혼합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 브린(brine)으로 세척하고 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 68 화합물을 수득하였다(수율=67%).SYNTHESIS EXAMPLE 67 The compound (1 mmol) was dissolved in DMF (2 mL). Cs 2 CO 3 while stirring (1.2mmol) and dichloroethane 22 hours after the addition of (1.2mmol) the reaction mixture, which was extracted with ethyl acetate and H 2 O. The combined organic layers were washed with Dublin (brine) and dried over anhydrous Na 2 SO 4, and concentrated in vacuo. Purification by column chromatography gave the compound of Synthesis Example 68 (Yield = 67%).

1H NMR (400MHz, CDCl3)δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 3.77 (s, 3H), 1.31 (s, 3H). MASS= 276.07 1 H NMR (400 MHz, CDCl 3 )? 8.66 (s, IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 ), 1.31 (s, 3H). MASS = 276.07

합성예 69 : 메틸 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 69: Methyl 1-methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate

합성예 67 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. Cs2CO3(1.2mmol) 및 클로로메탄(1.2mmol)을 반응 혼합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 브린(brine)으로 세척하고 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 69 화합물을 수득하였다(수율=65%).SYNTHESIS EXAMPLE 67 The compound (1 mmol) was dissolved in DMF (2 mL). Cs 2 CO 3 while stirring (1.2mmol) and dichloromethane after 22 hours by the addition of (1.2mmol) the reaction mixture, which was extracted with ethyl acetate and H 2 O. The combined organic layers were washed with Dublin (brine) and dried over anhydrous Na 2 SO 4, and concentrated in vacuo. Purification by column chromatography afforded the compound of Synthesis Example 69 (yield = 65%).

1H NMR (400MHz, CDCl3)δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H). MASS= 262.06 1 H NMR (400MHz, CDCl 3 ) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H ). MASS = 262.06

합성예 70 : 메틸 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Synthesis Example 70: Synthesis of methyl 1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-

합성예 67 (1 mmol)를 DMF(2 mL)에 용해시켰다. Cs2CO3 (1.2 mmol) 및 아세틸클로라이드(1.2mmol)를 반응 혼합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 브린(brine)으로 세척하고 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 70의 화합물을 수득하였다(수율=63%).Synthesis Example 67 (1 mmol) was dissolved in DMF (2 mL). After the addition of Cs 2 CO 3 (1.2 mmol) and acetyl chloride (1.2mmol) the reaction mixture was stirred for 22 hours and extracted with ethyl acetate and H 2 O. The combined organic layers were washed with Dublin (brine) and dried over anhydrous Na 2 SO 4, and concentrated in vacuo. The residue was purified by column chromatography to give the compound of Synthesis Example 70 (yield = 63%).

1H NMR (400MHz, CDCl3)δ 8.66(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 3.77(s, 3H), 1.31(s, 3H). MASS= 290.05 1 H NMR (400MHz, CDCl 3 ) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H ). MASS = 290.05

단계(c-3)의 일반적 과정General procedure of step (c-3)

2번 화합물(2.4g, 7.0mmol) 을 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 3번 화합물을 수득하였다.Compound No. 2 (2.4 g, 7.0 mmol) was stirred with 10% KOH in MeOH (200 mL) for 12 h at 80 <0> C, the mixture was filtered and the filtrate was washed with H 2 O to give compound 3 .

합성예 25 : 2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 25: 2-oxo-1,2-dihydroquinoline-3-carboxylic acid

합성예 71 화합물을 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 25 화합물을 수득하였다(수율=88%).After the mixture was stirred at 80 ℃, and for 12 hours in Synthesis Example 71 compound in 10% KOH was dissolved in MeOH (200mL) filtered, the filtrate to give the washing Synthesis Example 25 compound with H 2 O (Yield = 88% ).

1H NMR (400MHz, CDCl3)δ 11.0(s, 1H, -OH), 8.14(d, 1H), 8.34(s, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H). MASS= 189.04 1 H NMR (400 MHz, CDCl 3 )? 11.0 (s, IH, -OH), 8.14 (d, IH), 8.34 (s, IH), 7.36 t, 1 H). MASS = 189.04

합성예 26 : 1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 26: Synthesis of 1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 26 화합물을 수득하였다(수율=90%).The methyl 1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) And the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 26 (yield = 90%).

1H NMR(400MHz, CDCl3)δ 8.34(s, 1H), 7.65(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 3.83(s, 2H). MASS= 309.10 1 H NMR (400MHz, CDCl 3 )? 8.34 (s, IH), 7.65 (d, IH), 7.36 ), 6.87 (dd, 2H), 3.83 (s, 2H). MASS = 309.10

합성예 27 : 2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 27: Synthesis of 2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxylic acid

메틸 2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 27 화합물을 수득하였다(수율=87%).A solution of methyl 2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxylate in 10% KOH in MeOH (200 mL) After stirring, the mixture was filtered and the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 27 (yield = 87%).

1H NMR (400MHz,CDCl3)δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H). MASS= 363.07 1 H NMR (400MHz, CDCl 3 )? 8.34 (s, IH), 7.65 (d, IH), 7.36 ), 6.87 (dd, 2H). MASS = 363.07

합성예 28 : 1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 28: 1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 28 화합물을 수득하였다(수율=67%).Methyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) and the mixture was filtered, H 2 O to give the compound of Synthesis Example 28 (Yield = 67%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.65(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.44(s, 3H). MASS= 203.06 1 H NMR (400 MHz, CDCl 3 )? 8.34 (s, IH), 7.65 (d, IH), 7.36 (d, IH), 7.31 ). MASS = 203.06

합성예 29 : 1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 29: 1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 29 화합물을 수득하였다(수율=88%).Methyl 1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL), the mixture was filtered, H 2 O to give the compound of Synthesis Example 29 (yield = 88%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.65(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 4.28(s, 2H), 1.31(s, 3H) MASS= 217.07 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.28 (s, 2H ), 1.31 (s, 3H) MASS = 217.07

합성예 30 : 2-옥소-1-프로필-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 30: Synthesis of 2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid

메틸 2-옥소-1-프로필-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 30 화합물을 수득하였다(수율=90%).Methyl 2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL), the mixture was filtered, H 2 O to give the compound of Synthesis Example 30 (yield = 90%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.65(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 4.28(s, 2H), 3.6(s, 2H), 1.31(s, 3H) MASS= 231.09 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.28 (s, 2H ), 3.6 (s, 2H), 1.31 (s, 3H) MASS = 231.09

합성예 31 : 1-아세틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 31: 1-Acetyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-아세틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 31 화합물을 수득하였다(수율=98%).Methyl 1-acetyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL), the mixture was filtered, H 2 O to give the compound of Synthesis Example 31 (yield = 98%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 8.25(d, 1H), 7.59(t, 1H), 7.36(s, 1H), 7.14(t, 1H), 2.66(s, 3H). MASS= 231.05 1 H NMR (400 MHz, CDCl 3 )? 8.34 (s, IH), 8.25 (d, IH), 7.59 (t, IH), 7.36 ). MASS = 231.05

합성예 32 : 5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 32: 5-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

합성예 510의 화합물을 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 32 화합물을 수득하였다(수율=88%).The mixture was stirred at 80 ℃, and for 12 hours, the compound of Synthetic Example 510 in 10% KOH was dissolved in MeOH (200mL) and then filtered, the filtrate to give the washing Synthesis Example 32 compound with H 2 O (yield = 88 %).

1H NMR(400MHz,CDCl3)δ 11.0(s, 1H, -OH), 8.34(s, 1H), 8.0(s, 1H, -NH), 7.5(d, 1H), 7.06(t, 1H), 6.32(d, 1H), 6.27(s, 2H, -NH2). MASS=204.05 1 H NMR (400MHz, CDCl 3 ) δ 11.0 (s, 1H, -OH), 8.34 (s, 1H), 8.0 (s, 1H, -NH), 7.5 (d, 1H), 7.06 (t, 1H) , 6.32 (d, 1 H), 6.27 (s, 2H, -NH 2 ). MASS = 204.05

합성예 33 : 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 33: Synthesis of 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 33 화합물을 수득하였다(수율=87%).A solution of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate in 10% KOH in MeOH (200 mL) Stirred, and the mixture was filtered and the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 33 (yield = 87%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.25(dd, 2H), 7.06(t, 1H), 7.01(d, 1H), 6.87(dd, 2H), 6.32(d, 1H), 6.27(s, 2H, -NH2),3.83(s,3H). MASS=324.11 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.25 (dd, 2H), 7.06 (t, 1H), 7.01 (d, 1H), 6.87 (dd, 2H), 6.32 (d, 1H ), 6.27 (s, 2H, -NH 2), 3.83 (s, 3H). MASS = 324.11

합성예 34 : 5-아미노-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 34: 5-Amino-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 5-아미노-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 34 화합물을 수득하였다(수율=90%).Methyl 5-amino-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred in 10% KOH in MeOH (200 mL) for 12 hours at 80 ° C, The post-filtrate was washed with H 2 O to give the compound of Synthesis Example 34 (yield = 90%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.44(s, 3H).MASS=218.07 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3H). MASS = 218.07

합성예 35 : 5-아미노-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 35: Synthesis of 5-amino-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 5-아미노-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH (200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 35 화합물을 수득하였다(수율=78%).Methyl-5-amino-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) The post-filtrate was washed with H 2 O to give the compound of Synthesis Example 35 (yield = 78%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.32(d, 1H), 6.27(s, 2H, -NH2), 4.28(s, 2H), 3.44(s, 3H).MASS=232.08 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 4.28 (s, 2 H), 3.44 (s, 3 H). MASS = 232.08

합성예 36 : 1-아세틸-5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 36: 1-Acetyl-5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

에틸 1-아세틸-5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 36 화합물을 수득하였다(수율=88%).Ethyl 1-acetyl-5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) The post-filtrate was washed with H 2 O to give the compound of Synthesis Example 36 (yield = 88%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.44(s, 3H) MASS=246.06 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3H) MASS = 246.06

합성예 37 : 5-아미노-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 37: Synthesis of 5-amino-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylic acid

메틸 5-아미노-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 37 화합물을 수득하였다(수율=66%).Methyl 5-amino-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) After filtration, the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 37 (yield = 66%).

1H NMR(400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.32(d, 1H), 6.27 (s, 2H, -NH2), 4.28(s,2H),3.44(s,3H).MASS=260.08 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 4.28 (s, 2 H), 3.44 (s, 3 H). MASS = 260.08

합성예 38 : 5-아미노-1-(메톡시카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 38: Synthesis of 5-amino-1- (methoxycarbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid

디메틸 5-아미노-2-옥소퀴놀린-1,3(2H)-디카르복실레이트를 MeOH(200 mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 38 화합물을 수득하였다(수율=90%).The dimethyl 5-amino-2-oxoquinoline-1,3 (2H) -dicarboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) and the mixture was filtered, H 2 O to give the compound of Synthesis Example 38 (yield = 90%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.44(s, 3H). MASS=262.06 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3 H). MASS = 262.06

합성예 39 : 5-아미노-1-(사이클로펜타-1,3-디엔-1-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 39: Synthesis of 5-amino-1- (cyclopenta-1,3-dien-1-ylmethyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(사이클로펜타-1,3-디엔-1-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 39 화합물을 수득하였다(수율=89%).Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) and 10% after the mixture was stirred at 80 ℃, and for 12 hours with KOH was filtered to give the filtrate washed synthesis example 39 compound with H 2 O (yield = 89%).

1H NMR (400MHz, CDCl3)δ 8.34(s, 1H), 7.06(t, 1H), 7.01(d, 1H), 6.50(d, 1H), 6.40(m, 2H), 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.63(s, 2H), 2.9(s, 1H). MASS=282.10 1 H NMR (400MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.50 (d, 1H), 6.40 (m, 2H), 6.32 (d, 1H ), 6.27 (s, 2H, -NH 2), 3.63 (s, 2H), 2.9 (s, 1H). MASS = 282.10

합성예 40 : 5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 40: Synthesis of 5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

합성예 67 화합물을 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 40 화합물을 수득하였다(수율=78%)1 After the mixture was stirred at 80 ℃, and for 12 hours in Synthesis Example 67 compound in 10% KOH was dissolved in MeOH (200mL) filtered, the filtrate to give the washing Synthesis Example 40 compound with H 2 O (Yield = 78% ) 1

1H NMR (400MHz, CDCl3)δ 11.0(s, 1H, -OH), 8.63(s, 1H), 8.53(d, 1H), 7.95(d, 1H), 7.57(t, 1H). MASS= 234.03 1 H NMR (400 MHz, CDCl 3 )? 11.0 (s, IH, -OH), 8.63 (s, IH), 8.53 (d, IH), 7.95 MASS = 234.03

합성예 41 : 1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 41: 1- (4-Methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 41 화합물을 수득하였다(수율=78%)Methyl-1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate in 10% KOH in MeOH After stirring, the mixture was filtered and the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 41 (yield = 78%).

1H NMR (400MHz, CDCl3)δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.25(dd, 2H), 6.87(dd, 2H), 4.94(s, 2H), 3.83(s, 3H). MASS= 354.09 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.25 (dd, 2H), 6.87 (dd, 2H ), 4.94 (s, 2H), 3.83 (s, 3H). MASS = 354.09

합성예 42 : 1-(4-메톡시펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 42: 1- (4-methoxyphenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-(4-메톡시펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 42 화합물을 수득하였다(수율=80%).Methyl-1- (4-methoxyphenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate in 10% KOH in MeOH (200 mL) And the mixture was filtered, and the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 42 (yield = 80%).

1H NMR (400MHz,CDCl3)δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.18(dd, 2H), 6.94(dd, 2H), 4.62(s, 2H), 3.83(s, 3H), 3.09(s, 2H). MASS= 368.10 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.18 (dd, 2H), 6.94 (dd, 2H ), 4.62 (s, 2H), 3.83 (s, 3H), 3.09 (s, 2H). MASS = 368.10

합성예 43 : 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 43: 1-Methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 43 화합물을 수득하였다(수율=78%).Methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) The after filtrate was washed with H 2 O to obtain the compound of Synthesis Example 43 (yield = 78%).

1H NMR (400MHz, CDCl3)δ 8.63(s, 1H), 8.04(s, 1H), 7.95(d, 1H), 7.57(t, 1H), 3.44(s, 3H). MASS=248.04 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (s, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.44 (s, 3H). MASS = 248.04

합성예 44 : 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 44: 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

에틸 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 44 화합물을 수득하였다(수율=68%).Ethyl 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) The post-filtrate was washed with H 2 O to give the compound of Synthesis Example 44 (yield = 68%).

1H NMR (400MHz, CDCl3)δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 4.28(s, 2H), 1.31(s, 3H). MASS= 262.06 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H ). MASS = 262.06

합성예 45 : 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 45: 1-Acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

메틸 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 45 화합물을 수득하였다(수율=70%).Methyl 1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) The post-filtrate was washed with H 2 O to obtain the compound of Synthesis Example 45 (yield = 70%).

1H NMR(400MHz, CDCl3)δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 4.28(s, 2H), 1.31(s, 3H). MASS= 276.04 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H ). MASS = 276.04

합성예 46 : 5-니트로-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 46: Synthesis of 5-nitro-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylic acid

메틸 5-니트로-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 46 화합물을 수득하였다(수율=67%).Methyl 5-nitro-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL) After filtration, the filtrate was washed with H 2 O to obtain the compound of Synthesis Example 46 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.63(s, 1H), 8.64(d, 1H), 7.95(s, 1H), 7.57(t, 1H), 2.32(s, 2H), 1.02(s, 3H). MASS= 290.05 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.64 (d, 1H), 7.95 (s, 1H), 7.57 (t, 1H), 2.32 (s, 2H), 1.02 (s, 3H ). MASS = 290.05

합성예 47 : 1-(메톡시카르보닐)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 47: Synthesis of 1- (methoxycarbonyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

디메틸 5-니트로-2-옥소퀴놀린-1,3(2H)-디카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 47 화합물을 수득하였다(수율=70%).The dimethyl 5-nitro-2-oxoquinoline-1,3 (2H) -dicarboxylate was stirred for 12 hours at 80 ° C with 10% KOH in MeOH (200 mL), the mixture was filtered and the filtrate was washed with H 2 O to give the compound of Synthesis Example 47 (yield = 70%).

1H NMR(400MHz, CDCl3)δ 8.63(s, 1H), 8.64(d, 1H), 7.95(s, 1H), 7.57(t, 1H), 1.02(s, 3H). MASS= 292.03 1 H NMR (400 MHz, CDCl 3 )? 8.63 (s, IH), 8.64 (d, IH), 7.95 (s, IH), 7.57 (t, MASS = 292.03

합성예 48 : 1-(사이클로펜타-1,3-디엔-1-일메틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드Synthesis Example 48: Synthesis of 1- (cyclopenta-1,3-dien-1-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-

메틸 1-(사이클로펜타-1,3-디엔-1-일메틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과후 여과물을 H2O로 세척하여 합성예 47 화합물을 수득하였다(수율=78%).1-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) after the mixture was stirred at 80 ℃, and for 12 hours with KOH was filtered to give the filtrate washed synthesis example 47 compound with H 2 O (yield = 78%).

1H NMR(400MHz, CDCl3)δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 6.5(d, 1H), 6.4(m, 2H), 3.63(s, 2H), 2.9(s, 1H). MASS= 312.07 1 H NMR (400MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 6.5 (d, 1H), 6.4 (m, 2H ), 3.63 (s, 2H), 2.9 (s, IH). MASS = 312.07

단계(d-4)의 일반적 과정General procedure of step (d-4)

3번 화합물(450mg, 0.9mmol)을 DMF(5mL)에 용해시켰다. DIPEA(0.5mL, 2.7mmol), R3-NH2(0.2mL,1.3mmol) 및 PyBop(0.9mg,1.8mmol)을 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 4번 화합물을 수득하였다.Compound No. 3 (450 mg, 0.9 mmol) was dissolved in DMF (5 mL). DIPEA (0.5 mL, 2.7 mmol), R 3 -NH 2 (0.2 mL, 1.3 mmol) and PyBop (0.9 mg, 1.8 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain Compound No. 4.

합성예 49 : 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 49: 1- (4-Ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-에틸벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 49 화합물을 수득하였다(수율=56%).1- (4-Ethylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 49 (yield = 56%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(t, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.29(dd, 2H), 7.18(dd, 2H), 6.98(dd, 2H), 7.27(m, 1H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.60(m, 2H), 1.25(s, 3H). MASS=455.18 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (t, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H) 2H), 2.60 (d, 2H), 2.38 (d, 2H), 3.40 (s, 1.25 (s, 3 H). MASS = 455.18

합성예 50 : 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 50: Synthesis of 1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-에틸펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 50 화합물을 수득하였다(수율=56%).1 - (4-ethylphenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 50 (yield = 56%).

1HNMR(400MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.05(m, 4H), 4.62(s, 2H), 3.55 (s, 2H), 3.09(s, 2H), 2.83(s, 2H), 2.60(s, 2H), 1.25(s, 3H) MASS=469.20 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H) , 7.27 (m, IH), 7.05 (m, 4H), 4.62 (s, 2H), 3.55 (s, 2H), 3.09 1.25 (s, 3 H) MASS = 469.20

합성예 51 : 1-(4-플루오로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 51: 1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-플루오로벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 51 화합물을 수득하였다(수율=60%)1- (4-Fluorobenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Then, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 51 (yield = 60%).

1H NMR(400MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS= 445.14 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H ), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 MASS = 445.14

합성예 52 : 1-(4-플루오로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 52: 1- (4-Fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-플루오로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 52 화합물을 수득하였다(수율=60%).1- (4-Fluorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 52 (yield = 60%).

1H NMR (400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95 (d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.29(dd, 2H), 7.27(dd, 2H), 7.19(dd, 2H), 4.62(s, 2H), 3.55(m, 2H), 3.09(s, 2H), 2.83(s, 2H). MASS=459.16 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 ( (dd, 2H), 7.29 (dd, 2H), 7.27 (dd, 2H), 7.19 (dd, 2H), 4.62 , 2H). MASS = 459.16

합성예 53 : 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 53: 1- (4-Chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-클로로벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 53 화합물을 수득하였다(수율=58%).1- (4-Chlorobenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 53 (yield = 58%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=461.11 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 461.11

합성예 54 : 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 54: 5-nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 54 화합물을 수득하였다(수율=64%).5-Nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 54 (yield = 64%).

1H NMR(400MHz,CDCl3)δ 8.57 (s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=472.14 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H ), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 MASS = 472.14

합성예 55 : 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 55: Synthesis of 1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-아미노벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(3 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 55 화합물을 수득하였다(수율=57%)1- (4-Aminobenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (3 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 55 (yield = 57%).

1H NMR (400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.12(dd, 2H), 6.27(s, 2H, -NH2), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=442.16 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, , 2H). MASS = 442.16

합성예 56 : 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 56: Synthesis of 1- (4-cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-시아노벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 56 화합물을 수득하였다(수율=48%).1 - (4-cyanobenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 56 (yield = 48%).

1H NMR (400MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.27(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=452.15 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H ), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 MASS = 452.15

합성예 57 : 1-(나프탈렌-2-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 57: 1- (Naphthalen-2-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(나프탈렌-2-일메틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 57 화합물을 수득하였다(수율=50%).1-Naphthalen-2-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 57 (yield = 50%).

1H NMR (400MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95 (d, 1H), 7.57(t, 1H), 7.51(m, 4H), 7.42(m, 3H), 7.32(dd, 2H), 7.29(m, 5H), 4.99(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=477.17 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 ( (m, 2H), 7.32 (d, 2H), 7.29 (m, 2H). MASS = 477.17

합성예 58 : 1-([1,1'-비페닐]-4-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 58: Synthesis of 1 - ([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-([1,1'-비페닐]-4-일메틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 58 화합물을 수득하였다(수율= 60%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL) &Lt; / RTI &gt; DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 58 (yield = 60%).

1HNMR(400MHz,CDCl3)δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95(d, 1H), 7.57(t, 1H), 7.52(m, 4H), 7.42(m, 3H), 7.33(dd, 2H), 7.29(m, 5H), 4.99(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS= 503.18 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (m (M, 2H), 7.42 (m, 3H), 7.33 (dd, 2H), 7.29 (m, 2H). MASS = 503.18

합성예 59 : 1-(4-벤질벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 59: 1- (4-benzylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-벤질벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 59 화합물을 수득하였다(수율=46%).1- (4-Benzylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 59 (yield = 46%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95(d, 1H), 7.57(t, 1H), 7.51(m, 4H), 7.42 (m, 3H), 7.32 (dd, 2H), 7.29(m, 5H), 4.99(s, 2H), 4.76 3.55(m, 2H), 2.83(m, 2H). MASS= 517.20 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 (m 2H), 4.83 (s, 2H), 4.76 (m, 2H), 2.83 (m, 2H). MASS = 517.20

합성예 60 : 5-니트로-2-옥소-N-펜에틸-1-(4-페녹시벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 60: 5-nitro-2-oxo-N-phenethyl-1- (4-phenoxybenzyl) -1,2-dihydroquinoline-

5-니트로-2-옥소-1-(4-페녹시벤질)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 60 화합물을 수득하였다(수율=48%).5-Nitro-2-oxo-1- (4-phenoxybenzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain a compound of Synthesis Example 60 (yield = 48%).

1HNMR(400MHz,CDCl3)δ 8.57 (s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95(d, 1H), 7.57(t, 1H), 7.52(m, 4H), 7.42(m, 3H), 7.33(dd, 2H), 7.29(m, 5H), 4.99(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS= 519.18 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (m (M, 2H), 7.42 (m, 3H), 7.33 (dd, 2H), 7.29 (m, 2H). MASS = 519.18

합성예 61 : 1-(4-클로로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 61: 1- (4-Chlorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-클로로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다 이후 실리카 겔 크로마토그래프로 정제하여 합성예 61 화합물을 수득하였다(수율=59%).1- (4-Chlorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water, and then purified by silica gel chromatography to obtain a compound of Synthesis Example 61 (yield = 59%).

1H NMR (400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95(d, 1H), 7.57(t, 1H), 7.44(dd, 2H), 7.40(dd, 2H), 7.29(dd, 2H), 7.23(dd, 2H), 4.62(s, 2H), 3.09(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=475.13 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 ( (d, 2H), 7.40 (d, 2H), 7.29 (dd, 2H), 7.23 , 2H). MASS = 475.13

합성예 62 : 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 62: 1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-아미노펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 62 화합물을 수득하였다(수율=47%).1- (4-Aminophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 62 (yield = 47%).

1H NMR (400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95 (d, 1H), 7.57(t, 1H), 7.44(dd, 2H), 7.40(dd, 2H), 7.29(dd, 2H), 7.23(dd, 2H), 6.27(s, 2H, -NH2), 4.62(s, 2H), 3.09(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS= 456.18 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 ( dd, 2H), 7.40 (dd , 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 6.27 (s, 2H, -NH 2), 4.62 (s, 2H), 3.09 (s, 2H) , 3.55 (m, 2H), 2.83 (m, 2H). MASS = 456.18

합성예 63 : 1-(4-시아노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 63: Synthesis of 1- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-시아노펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 63 화합물을 수득하였다(수율=52%).1- (4-cyanophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 63 (yield = 52%).

1H NMR (400MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95 (d, 1H), 7.57(t, 1H), 7.44(dd, 2H), 7.40(dd, 2H), 7.29(dd, 2H), 7.23(dd, 2H), 4.62(s, 2H), 3.09(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=466.16 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 ( (d, 2H), 7.40 (d, 2H), 7.29 (dd, 2H), 7.23 , 2H). MASS = 466.16

합성예 64 : 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 64: Synthesis of 5-nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

5-니트로-1-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 64 화합물을 수득하였다(수율= 43%).5-Nitro-1- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 64 (yield = 43%).

1H NMR (400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -NH), 7.95 (d, 1H), 7.57(t, 1H), 7.44(dd, 2H), 7.40(dd, 2H), 7.29(dd, 2H), 7.23(dd, 2H), 4.62(s, 2H), 3.09(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=486.15 1 H NMR (400MHz, CDCl 3 ) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 ( (d, 2H), 7.40 (d, 2H), 7.29 (dd, 2H), 7.23 , 2H). MASS = 486.15

합성예 76 : 2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 76: 2-Oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 76 화합물을 수득하였다(수율=42%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenylmetamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 76 (yield = 42%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.61 (dd, 2H), 7.43(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.19(t, 1H), 7.14(t, 1H). MASS=264.09 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 ( d, 1 H), 7.31 (t, IH), 7.19 (t, IH), 7.14 (t, IH). MASS = 264.09

합성예 77 : 1-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 77: 1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide)

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mL)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 77 화합물을 수득하였다(수율=44%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mL) was dissolved in DMF (2 mL). DIPEA (3 mmol), aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 77 (yield = 44%).

1H NMR (400MHz,CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, 1H), 7.19 (m, 1H), 7.14 (t, 1H), 3.44 (s, 3H). MASS= 278.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 ( (s, 1H), 7.31 (t, IH), 7.19 (m, IH), 7.14 (t, IH), 3.44 (s, 3H). MASS = 278.11

합성예 78 : 1-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 78: 1-Ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 78 화합물을 수득하였다(수율=45%)1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 78 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.65(d, 1H), 7.61 (dd, 2H), 7.43(dd, 2H), 7.36(s, 1H), 7.31(t, 1H), 7.19(m, 1H), 7.14(t, 1H), 4.28(s, 2H), 3.44(s, 3H). MASS=292.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 ( (s, 1H), 7.31 (t, IH), 7.19 (m, IH), 7.14 (t, IH), 4.28 (s, 2H), 3.44 MASS = 292.12

합성예 79: 1-아세틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 79: 1-Acetyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

1-아세틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 79 화합물을 수득하였다(수율=50%).1-Acetyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 79 (yield = 50%).

1H NMR (400MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, 1H), 7.19 (m, 1H), 7.14 (t, 1H), 3.44 (s, 3H), MASS= 306.10 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 ( 1H), 7.31 (t, IH), 7.19 (m, IH), 7.14

합성예 85 (2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 85 (2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide)

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨루이딘(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 85 화합물을 수득하였다(수율= 48%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-toluidine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain a compound of Synthesis Example 85 (yield = 48%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.36 (d, 1H), 7.31(t, 1H), 7.21(dd, 2H), 7.17(dd, 2H), 7.14(t, 1H), 2.34(s, 3H). MASS=278.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 ( dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 2.34 (s, 3H). MASS = 278.11

합성예 86 : 1-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 86: Synthesis of 1-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨루이딘(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예86 화합물을 수득하였다(수율=52%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-toluidine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 86 (yield = 52%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.65(d, 1H), 7.36 (d, 1H), 7.31(t, 1H), 7.21(dd, 2H), 7.17(dd, 2H), 7.14(t, 1H), 3.44(s, 3H), 2.34(s, 3H). MASS= 292.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 ( dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 3.44 (s, 3H), 2.34 (s, 3H). MASS = 292.12

합성예 87 : 1-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 87: 1-Ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨루이딘(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 87 화합물을 수득하였다(수율=46%).1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-toluidine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 87 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 4.23 (s, 2H), 3.44 (s, 3H), 2.34 (s, 3H). MASS= 306.14 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 ( (d, 2H), 7.17 (dd, 2H), 7.14 (s, 3H). MASS = 306.14

합성예 89 : N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation Example 89: Preparation of N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF (2 mL)에 용해시켰다. DIPEA(3 mmol), 4-메톡시아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 89 화합물을 수득하였다(수율=43%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-methoxyaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 89 (yield = 43%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.65(d, 1H), 7.36 (d, 1H), 7.31(t, 1H), 7.21(dd, 2H), 7.17(dd, 2H), 7.14(t, 1H), 4.23(s, 2H), 3.44(s, 3H), 2.34(s, 3H). MASS= 306.14 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 ( (d, 2H), 7.17 (dd, 2H), 7.14 (s, 3H). MASS = 306.14

합성예 92: N-(4-브로모페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 92: N- (4-bromophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 92 화합물을 수득하였다(수율=48%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromoaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 92 (yield = 48%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H). MASS= 342.00 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H). MASS = 342.00

합성예 95 : N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 95: N- (4-Chlorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 95 화합물을 수득하였다(수율=42%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 95 (yield = 42%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H). MASS= 298.05 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H). MASS = 298.05

합성예 96 : N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 96: N- (4-Chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 96 화합물을 수득하였다(수율=56%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 96 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 3.3(s, 3H). MASS= 312.07 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H), 3.3 (s, 3 H). MASS = 312.07

합성예 97 : N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 97: N- (4-Chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 97 화합물을 수득하였다(수율=56%).1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 97 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 3.3(s, 2H), 2.83(s, 3H). MASS= 326.08 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, IH), 6.97 (dd, IH), 3.3 (s, 2H), 2.83 (s, 3H). MASS = 326.08

합성예 118 : N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation 118: N- (4-Fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 118 화합물을 수득하였다(수율=52%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 118 (yield = 52%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51(dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H). MASS= 282.08 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H). MASS = 282.08

합성예 119 : N-(4-플루오로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 119: N- (4-Fluorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드 (1mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 119 화합물을 수득하였다(수율=47%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 119 (yield = 47%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 3.3(s, 3H). MASS= 296.10 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H), 3.3 (s, 3 H). MASS = 296.10

합성예 120 : 1-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 120: 1-Ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 120 화합물을 수득하였다(수율=45%).1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 120 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51(dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 4.28(s, 2H), 3.3(s, 3H). MASS= 310.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, IH), 6.97 (dd, IH), 4.28 (s, 2H), 3.3 (s, 3H). MASS = 310.11

합성예 121 : 1-((2H-피롤-3-일)메틸)-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로 퀴놀린-3-카르복사마이드Synthesis Example 121: Synthesis of 1 - ((2H-pyrrol-3-yl) methyl) -N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-

1-((2H-피롤-3-일)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 121 화합물을 수득하였다(수율=48%)1 - ((2H-pyrrol-3-yl) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 121 (yield = 48%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (m, 3H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.06(s, 1H), 4.28(s, 2H), 3.63(s, 2H), 2.0(s, 1H). MASS=361.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (m, 3H), 7.36 (d, 2H), 7.31 ( 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.06 (s, IH), 4.28 (s, 2H), 3.63 (s, 2H), 2.0 (s, MASS = 361.12

합성예 125: N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 125: N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 125 화합물을 수득하였다(수율= 50%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 125 (yield = 50%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51(m, 3H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.06(s, 1H), 4.28(s, 2H), 3.63(s, 2H), 2.0(s, 1H). MASS= 361.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (m, 3H), 7.36 (d, 2H), 7.31 ( 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.06 (s, IH), 4.28 (s, 2H), 3.63 (s, 2H), 2.0 (s, MASS = 361.12

합성예 126 : N-(4-에틸페닐)-1-9m틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 126: N- (4-ethylphenyl) -1-9methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 126 화합물을 수득하였다(수율=47%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 126 (yield = 47%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 3.3(s, 3H), 2.60(s, 2H), 1.25(s, 3H). MASS= 306.14 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H), 2.60 (s, 2H), 1.25 MASS = 306.14

합성예 127 : 1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 127: 1-Ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 127 화합물을 수득하였다(수율=43%).1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 127 (yield = 43%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51(dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 3.3(s, 3H), 2.60(s, 2H), 2.3(s, 2H), 1.25(s, 3H). MASS= 320.15 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( 2H), 1.25 (s, 3H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H), 2.60 (s, 2H). MASS = 320.15

합성예 128 : 1-(2-(2H-피롤-3-일)에틸)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 128: Synthesis of 1- (2- (2H-pyrrol-3-yl) ethyl) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(2H-피롤-3-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 128 화합물을 수득하였다(수율=45%).1- (2- (2H-pyrrol-3-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 128 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.50(s, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.06(s, 1H), 3.60(s, 2H), 2.60(s, 2H), 1.25(s, 3H). MASS=385.18 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.50 ( 2H), 2.60 (s, 2H), 1.25 (s, 1H), 7.31 (t, , 3H). MASS = 385.18

합성예 133 : N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 133: N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(2 mmol), 4-아미노페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 133 화합물을 수득하였다(수율=42%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (2 mmol), 4-aminophenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 133 (yield = 42%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.35(s, 1H, -OH). MASS=280.08 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, IH), 6.97 (dd, IH), 5.35 (s, IH, -OH). MASS = 280.08

합성예 134 (N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 134 (N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide)

합성예 28 화합물(1mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-아미노페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 134 화합물을 수득하였다(수율= 49%).Synthesis Example 28 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-aminophenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 134 (yield = 49%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.35(s, 1H, -OH), 3.2(s, 3H). MASS=294.10 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.35 (s, IH, -OH), 3.2 (s, 3H). MASS = 294.10

합성예 135 : 1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 135: 1-Ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

합성예 29 화합물(1mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 135 화합물을 수득하였다(수율=46%).Synthesis Example 29 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-aminophenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 135 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H), 5.35(s, 1H, -OH), 4.3(s, 2H), 3.2(s, 3H). MASS=308.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.35 (s, IH, -OH), 4.3 (s, 2H), 3.2 (s, 3H). MASS = 308.12

합성예 136 : N-(4-하이드록시페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 136: N- (4-hydroxyphenyl) -2-oxo-1- (2- (thiophen-2-yl) ethyl) -1,2-dihydroquinoline-

2-옥소-1-(2-(티오펜-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 136 화합물을 수득하였다(수율=56%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-aminophenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 136 (yield = 56%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.40(s, 1H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 7.12(s, 1H), 6.97(m, 2H), 5.35(s, 1H, -OH), 4.3(s, 2H), 4.22(s, 2H), 3.83(s, 2H). MASS= 390.10 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.40 (s, 1H), 7.36 ( 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (s, 4.22 (s, 2 H), 3.83 (s, 2 H). MASS = 390.10

합성예 140 : N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 140: Synthesis of N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-니트로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 140 화합물을 수득하였다(수율=59%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-nitroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 140 (yield = 59%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.97(dd, 1H). MASS=309.07 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H). MASS = 309.07

합성예 143 : N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 143: Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노-N,N-디메틸벤젠설폰아미드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 143 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 143 (yield = 49%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 2.66(m, 6H). MASS=371.09 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 2.66 (m, 6H). MASS = 371.09

합성예 144 : N-(4-(N,N-디메틸설파모일)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 144: Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-

합성예 28 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노-N,N-디메틸벤젠설폰아미드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 144 화합물을 수득하였다(수율=62%).Synthesis Example 28 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 144 (yield = 62%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7 14(t, 1H), 3.4(s, 3H), 2.66(m, 6H). MASS=385.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (s, 3H), 2.66 (m, 6H). MASS = 385.11

합성예 145 : N-(4-(N,N-디메틸설파모일)페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 145: Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-

합성예 29 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노-N,N-디메틸벤젠설폰아미드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 145 화합물을 수득하였다(수율=67%).Synthesis Example 29 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 145 (yield = 67%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 3.4(s, 3H), 2.8(s, 2H), 2.66(m, 6H). MASS=399.13 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 3.4 (s, 3H), 2.8 (s, 2H), 2.66 (m, 6H). MASS = 399.13

합성예 146 : 1-(사이클로헥실메틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 146: 1- (Cyclohexylmethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-

1-(사이클로헥실메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노-N,N-디메틸벤젠설폰아미드(1.5 mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 146 화합물을 수득하였다(수율= 62%).1- (Cyclohexylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 146 (yield = 62%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14 (t, 1H), 3.98(s, 2H), 2.66(m, 6H), 2.06(s, 1H), 1.43(m, 5H). MASS=467.19 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 2H), 7.36 (d, 2H), 7.36 (t, IH), 7.14 (t, IH), 3.98 (s, 2H), 2.66 1.43 (m, 5 H). MASS = 467.19

합성예 147 : 1-(2-사이클로헥실에틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 147: Synthesis of 1- (2-cyclohexylethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-

1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노-N,N-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 147 화합물을 수득하였다(수율= 49%).1-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 147 (yield = 49%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 3.98(s, 2H), 3.46(s, 3H), 2.66(m, 6H), 2.06(s, 1H), 1.43(m, 5H). MASS=481.20 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 2H), 7.36 (d, 2H), 7.36 (t, 1H), 7.14 (t, 2.06 (s, 1 H), 1.43 (m, 5 H). MASS = 481.20

합성예 148 : N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 148: N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 148 화합물을 수득하였다(수율= 58%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-aminophenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 148 (yield = 58%).

1H NMR (400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH). MASS=294.10 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.61 (m, 2H), 3.65 (s, MASS = 294.10

합성예 149 : N-(4-(하이드록시메틸)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 149: N- (4- (hydroxymethyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-

합성예 28 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 149 화합물을 수득하였다(수율=56%).Synthesis Example 28 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-aminophenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 149 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.3(s, 3H). MASS=308.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.61 (m, 2H), 3.65 3H). MASS = 308.12

합성예 150 : 1-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 150: 1-Ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-

합성예 29 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 150 화합물을 수득하였다(수율=56%).Synthesis Example 29 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-aminophenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 150 (yield = 56%).

1HNMR(400MHz,CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.4(s, 2H), 3.3(s, 3H). MASS=322.13 1 HNMR (400MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.61 (m, 2H), 3.65 ), 3.3 (s, 3H). MASS = 322.13

합성예 151 : 1-(사이클로펜틸메틸)-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 151: 1- (Cyclopentylmethyl) -N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-

1-(사이클로펜틸메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(52 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 151 화합물을 수득하였다(수율=65%).1- (Cyclopentylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (52 mL). DIPEA (3 mmol), (4-aminophenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 151 (yield = 65%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.98(s, 2H), 3.65(s, 1H, -OH), 1.64(m, 8H). MASS=322.13 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 2H), 7.36 (d, 2H), 7.36 (t, 1H), 7.14 (t, OH), &lt; / RTI &gt; 1.64 (m, 8H). MASS = 322.13

합성예 152: 2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 152: Synthesis of 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-비닐아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 152 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-vinyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 152 (yield = 53%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H). MASS=290.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 MASS = 290.11

합성예 153 : 1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 153: Synthesis of 1-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

합성예 28 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-비닐아닐린(1.5 mmol) 및 PyBop (1 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 153 화합물을 수득하였다(수율= 56%).Synthesis Example 28 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-vinyl aniline (1.5 mmol) and PyBop (1 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 153 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 3.12(s, 3H). MASS=304.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 3.12 (s, 3 H). MASS = 304.12

합성예 154 : 1-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 154: Synthesis of 1-ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

합성예 29 화합물(1mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-비닐아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 154 화합물을 수득하였다(수율=64%).Synthesis Example 29 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-vinyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 154 (yield = 64%).

1H NMR(400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 3.4(s, 2H), 3.12(s, 3H). MASS=318.14 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 3.4 (s, 2H), 3.12 (s, 3H). MASS = 318.14

합성예 155 : 1-(2-사이클로펜틸에틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 155: Synthesis of 1- (2-cyclopentylethyl) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

1-(2-사이클로펜틸에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-비닐아닐린(1.5 mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 155 화합물을 수득하였다(수율=48%).1- (2-Cyclopentylethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-vinyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 155 (yield = 48%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 3.98(s, 2H), 3.75(s, 2H), 1.46(m, 8H). MASS=386.20 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 3.98 (s, 2H), 3.75 (s, 2H), 1.46 (m, 8H). MASS = 386.20

합성예 165 : N-벤질-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation 165: N-Benzyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 165 화합물을 수득하였다(수율= 57%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenylmetamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 165 (yield = 57%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0 (s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.34(m, 2H). MASS=278.11 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.34 (m, 2H). MASS = 278.11

합성예 166 : N-벤질-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 166: N-Benzyl-1-methyl-2-oxo-1,2-dihydroquinoline-3-

합성예 28 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민(1.5 mmol) 및 PyBop (1 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 166 화합물을 수득하였다(수율= 56%).Synthesis Example 28 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenyl methanamine (1.5 mmol) and PyBop (1 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 166 (yield = 56%).

1H NMR (400MHz,CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.3 (s, 3H). MASS= 292.12 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.34 (m, 2H), 3.3 (s, 3H). MASS = 292.12

합성예 167 : N-벤질-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 167: N-benzyl-1-ethyl-2-oxo-1,2-dihydroquinoline-3-

합성예 29 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 167 화합물을 수득하였다(수율= 59%).Synthesis Example 29 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenylmetamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 167 (yield = 59%).

1H NMR (400MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, 1H), 7.14(t, 1H), 4.34(m, 2H), 3.8(s, 2H), 3.3(s, 3H). MASS=306.14 1 H NMR (400MHz, CDCl 3 ) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 4.34 (m, 2H), 3.8 (s, 2H), 3.3 (s, MASS = 306.14

합성예 179 : 2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 179: Synthesis of 2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 179 화합물을 수득하였다(수율=56%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 179 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40(dd, 2H), 7.29(dd, 2H), 7.27(t, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.55(m, 2H), 2.83(m, 2H). MASS=292.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H) , 7.29 (d, 2H), 7.27 (t, IH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 292.12

합성예 180 : 1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 180: 1- (4-Methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

합성예 26 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 180 화합물을 수득하였다(수율= 52%).Synthesis Example 26 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 180 (yield = 52%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.40(dd, 2H), 7.29(m, 4H), 7.27(m, 3H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.55(m, 2H), 3.3(s, 2H), 2.95(s, 3H), 2.83(m, 2H). MASS=412.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H) 2H), 7.29 (m, 4H), 7.27 (m, 3H), 7.36 (d, 2.95 (s, 3H), 2.83 (m, 2H). MASS = 412.18

합성예 181 : 2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 181: 2-Oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-

합성예 27 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 181 화합물을 수득하였다(수율=49%)Synthesis Example 27 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at ambient temperature for 3 hours at ambient temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 181 (yield = 49%).

1H NMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40(dd, 2H), 7.29(m, 4H), 7.27(m, 3H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H). MASS=466.15 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H) 2H), 7.29 (m, 4H), 7.27 (m, 3H), 7.36 (d, 2.83 (m, 2H). MASS = 466.15

합성예 182 : 1-(2-(4-메톡시-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 182: Synthesis of 1- (2- (4-methoxy-2,3-dihydro-1H-inden-2-yl) ethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline- 3-carboxamide

1-(2-(4-메톡시-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 182 화합물을 수득하였다(수율=56%).2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 182 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40(dd, 2H), 7.29(dd, 2H), 7.27(m, 3H), 7.36(m, 2H), 7.31(t, 1H), 7.14(t, 1H), 3.55(m, 4H), 2.83(m, 4H), 2.6(m, 8H). MASS=466.23 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H) , 7.29 (d, 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, 2.6 (m, 8H). MASS = 466.23

합성예 183 : 2-옥소-N-펜에틸-1-(2-(4-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 183: Synthesis of 2-oxo-N-phenethyl-1- (2- (4- (trifluoromethoxy) -2,3-dihydro- Dihydroquinoline-3-carboxamide

2-옥소-1-(2-(4-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 183 화합물을 수득하였다(수율= 53%).Dihydro-1H-inden-2-yl) ethyl) -1,2-dihydroquinoline-3-carboxylic acid (2-oxo- (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 183 (yield = 53%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40(dd, 2H), 7.29(dd, 2H), 7.27(m, 3H), 7.36(m, 2H), 7.31(t, 1H), 7.14(t, 1H), 3.55(m, 4H), 2.83(m, 4H), 2.6(m, 5H). MASS=520.20 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H) , 7.29 (d, 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, 2.6 (m, 5 H). MASS = 520.20

합성예 191 : 2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 191: Synthesis of 2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-페닐프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 191 화합물을 수득하였다(수율= 56%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-phenylpropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 191 (yield = 56%).

1HNMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 7.40(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.29(dd, 2H), 7.27(t, 1H), 7.14(t, 1H), 3.18(m, 2H), 2.62(m, 2H), 2.09(m, 2H). MASS=306.14 1 HNMR (400MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (t , 7.29 (d, 2H), 7.27 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 2.62 (m, 2H), 2.09 (m, 2H). MASS = 306.14

합성예 192 : 1-(4-메톡시벤질)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 192: 1- (4-Methoxybenzyl) -2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-

합성예 26 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-페닐프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 192 화합물을 수득하였다(수율= 63%).Synthesis Example 26 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-phenylpropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 192 (yield = 63%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 7.40 (dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.29(m, 4H), 7.27(t, 1H), 7.14(m, 3H), 3.18(m, 2H), 3.3(s, 2H), 2.62(m, 2H), 2.09(m, 2H) 1.62(s, 3H). MASS=426.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 ( 2H), 2.62 (m, 2H), 2.09 (m, 2H), 7.29 (m, 2H) , &Lt; / RTI &gt; 2H) 1.62 (s, 3H). MASS = 426.19

합성예 193 : 1-(2-(5-포르밀-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 193: 1- (2- (5-Formyl-2,3-dihydro-1H-inden-2-yl) ethyl) Dihydroquinoline-3-carboxamide

1-(2-(5-포르밀-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-페닐프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 193 화합물을 수득하였다(수율= 46%).2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-phenylpropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 193 (yield = 46%).

1H NMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 7.40 (dd, 2H), 7.36(d, 1H), 7.31(m, 2H), 7.29(dd, 2H), 7.27(t, 1H), 7.14(m, 3H), 3.3(s, 2H), 3.18(m, 4H), 2.97(s, 2H), 2.62(m, 2H), 2.09(m, 7H), 1.29(s, 1H). MASS=478.23 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 ( 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 (s, 2H), 3.18 , 2H), 2.09 (m, 7H), 1.29 (s, 1H). MASS = 478.23

합성예 194 : (1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 194: (1- (2- (5- (Methylthio) -2,3-dihydro-1H-inden-2-yl) ethyl) , 2-dihydroquinoline-3-carboxamide)

1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-페닐프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 194 화합물을 수득하였다(수율=46%).2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1 (2- (5- (methylthio) -2,3-dihydro- mmol) were dissolved in DMF (2 mL). DIPEA (3 mmol), 3-phenylpropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 194 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 7.40 (dd, 2H), 7.36(d, 1H), 7.31(m, 2H), 7.29(dd, 2H), 7.27(t, 1H), 7.14(m, 3H), 3.3(s, 2H), 3.18(m, 4H), 2.97(s, 2H), 2.62(m, 2H), 2.09(m, 7H), 1.29(s, 3H). MASS=496.22 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 ( 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 (s, 2H), 3.18 , 2H), 2.09 (m, 7H), 1.29 (s, 3H). MASS = 496.22

합성예 195 : N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 195: N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨일메타나민(1.2 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 195 화합물을 수득하였다(수율= 46%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-toluyl methanamine (1.2 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 195 (yield = 46%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.11(m, 4H), 7.14(d, 1H), 4.34(m, 2H), 2.34(s, 3H). MASS=292.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 1H), 7.31 (t, IH), 7.11 (m, 4H), 7.14 (d, IH), 4.34 (m, 2H), 2.34 (s, 3H). MASS = 292.12

합성예 196 : 1-(4-메톡시벤질)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 196: 1- (4-Methoxybenzyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-

합성예 26 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 196 화합물을 수득하였다(수율= 54%)Synthesis Example 26 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-Tolyl methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 196 (yield = 54%).

1H NMR (400MHz, CDCl3)δ8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.11(m, 4H), 7.14(d, 1H), 4.34(m, 2H), 3.3(s, 2H), 2.34(s, 3H), 1.67(s, 3H). MASS=412.18 1 H NMR (400MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH) 8.03 (s, IH, -NH), 8.0 , 7.31 (m, 3H), 7.11 (m, 4H), 7.14 (d, IH), 4.34 (m, 2H), 3.3 (s, 2H), 2.34 (s, 3H), 1.67 MASS = 412.18

합성예 197 : N-(4-메틸벤질)-2-옥소-1-(3-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 197: Synthesis of N- (4-methylbenzyl) -2-oxo-1- (3- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-

2-옥소-1-(3-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 197 화합물을 수득하였다(수율=45%).2-oxo-1- (3- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-Tolyl methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 197 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.11(m, 6H), 7.14(m, 3H), 4.34(m, 2H), 3.78(s, 2H), 2.76(s, 2H), 2.34(s, 3H). MASS=480.17 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 2H), 2.76 (s, 2H), 2.34 (s, 3H), 7.31 (m, 2H). MASS = 480.17

합성예 198 : 1-(3-시아노펜에틸)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로 퀴놀린-3-카르복사마이드Synthesis Example 198: 1- (3-Cyanophenethyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-

1-(3-시아노펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-톨일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 198 화합물을 수득하였다(수율=59%).1- (3-cyanophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-Tolyl methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 198 (yield = 59%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.11(m, 6H), 7.14(m, 3H), 4.34(m, 2H), 3.78(s, 2H), 2.76(s, 2H), 2.34 (s, 3H). MASS= 421.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 2H), 2.76 (s, 2H), 2.34 (s, 3H), 7.31 (m, 2H). MASS = 421.18

합성예 199 : N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation 199: N- (4-Methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(p-톨일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 199 화합물을 수득하였다(수율=45%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (p-tolyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 199 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.34(s, 3H). MASS=306.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, MASS = 306.14

합성예 200 : 1-(4-(하이드록시메틸)벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 200: Synthesis of 1- (4- (hydroxymethyl) benzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(하이드록시메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(p-톨일)에타나민 (1.5. mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 200 화합물을 수득하였다(수율= 56%).1 - (4- (hydroxymethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (p-tolyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 200 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.34(s, 3H). MASS=426.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, MASS = 426.19

합성예 201 : 1-(4-에틸벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 201: Synthesis of 1- (4-ethylbenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(3 mL)에 용해시켰다. DIPEA(3 mmol), 2-(p-톨일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 201 화합물을 수득하였다(수율=56%).1- (4-Ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (3 mL). DIPEA (3 mmol), 2- (p-tolyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 201 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.34(s, 3H), 2.14(s, 2H), 1.67(s, 6H). MASS= 424.22 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (d, 2H), 7.14 (t, IH), 6.98 (dd, 2H) 2.14 (s, 2 H), 1.67 (s, 6 H). MASS = 424.22

합성예 202 : 1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 202: 1- (4-Methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-

합성예 26 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(p-톨일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 202 화합물을 수득하였다(수율=68%).Synthesis Example 26 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (p-tolyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 202 (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.34(s, 3H). MASS= 426.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, MASS = 426.19

합성예 205 : N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 205: Preparation of N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-메톡시페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 205 화합물을 수득하였다(수율=68%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-methoxyphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 205 (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H), 3.83(s, 3H). MASS=308.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H), 3.83 (s, 3H). MASS = 308.12

합성예 206 : 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 206: 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) Dihydroquinoline-3-carboxamide

1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-메톡시페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 206 화합물을 수득하였다(수율=62%).2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of 1- Was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-methoxyphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 206 (yield = 62%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, H), 7.14(m, 3H), 6.87(dd, 2H), 6.27(s, -NH2, -2H), 4.34(m, 2H), 3.83(s, 3H), 3.3(s, 2H), 3.18(s, 2H), 2.64(m, 5H). MASS= 467.22 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, 1H), 7.25 (m, H), 7.14 (m, 3H), 6.87 (dd, 2H), 6.27 , 3H), 3.3 (s, 2H), 3.18 (s, 2H), 2.64 (m, 5H). MASS = 467.22

합성예 207 : 1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 207: 1- (2- (5-Ethyl-2,3-dihydro-1H-inden-2-yl) Dihydroquinoline-3-carboxamide

1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-메톡시페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 207 화합물을 수득하였다(수율=68%).2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of Was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-methoxyphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 207 (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, H), 7.14(m, 3H), 6.87(dd, 2H), 4.34(m, 2H), 3.83(s, 3H), 3.3(s, 2H), 3.18(s, 2H), 2.64(m, 7H), 1.64(s, 3H). MASS= 480.24 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, 1H), 7.25 (m, 3H), 7.14 (m, 3H), 6.87 (dd, 2H) 3.18 (s, 2H), 2.64 (m, 7H), 1.64 (s, 3H). MASS = 480.24

합성예 208 : N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 208: N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-메톡시페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 208 화합물을 수득하였다(수율=63%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-methoxyphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 208 (yield = 63%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS= 322.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (d, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 322.13

합성예 209 : 1-(4-메톡시벤질)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 209: 1- (4-Methoxybenzyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-메톡시페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 209 화합물을 수득하였다(수율= 68%)1- (4-Methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-methoxyphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 209 (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(m, 3H), 6.94(m, 4H), 3.83(s, 3H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H) 2.54(s, 3H). MASS=442.19 1 H NMR (400MHz, CDCl 3 ) δ 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H) , 7.14 (m, 3H), 6.94 (m, 4H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, MASS = 442.19

합성예 210 : 1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 210: Synthesis of l- (2- (5-hydroxy-2,3-dihydro-1H-inden-2-yl) ethyl) -N- (4-methoxyphenethyl) 2-dihydroquinoline-3-carboxamide

1-(2-(5-(하이드록시메틸)-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 2-(p-톨일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 210 화합물을 수득하였다(수율=63%).Dihydro-1H-inden-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (prepared by reacting 1- (5- (hydroxymethyl) 1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (p-tolyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 210 (yield = 63%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 3H), 7.14(t, 1H), 6.94(m, 4H), 3.83(s, 3H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 4H), 2.64(m, 5H). MASS= 482.22 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 3H), 7.14 (t, IH), 6.94 (m, 4H) 2.83 (m, 4 H), 2.64 (m, 5 H). MASS = 482.22

합성예 211 : 1-((2,3-디하이드로-1H-인덴-5-일)메틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 211: Synthesis of 1 - ((2,3-dihydro-1H-inden-5-yl) methyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- - carboxamide

1-(나프탈렌-2-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-메톡시페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 211 화합물을 수득하였다(수율=60%).1- (Naphthalen-2-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-methoxyphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 211 (yield = 60%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(m, 4H), 6.94 (dd, 2H), 4.94(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 2H), 2.80(m, 5H). MASS= 452.21 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (m, 4H), 6.94 (dd, 2H) 2.83 (m, 2 H), 2.80 (m, 5 H). MASS = 452.21

합성예 212 : 1-(2-(2,3-디하이드로-1H-인덴-5-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 212: Synthesis of 1- (2- (2,3-dihydro-1H-inden-5-yl) ethyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide

1-(2-(2,3-디하이드로-1H-인덴-5-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-메톡시페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 212 화합물을 수득하였다(수율=68%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 ml_) ). DIPEA (3 mmol), 2- (4-methoxyphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 212 (yield = 68%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 3H), 7.14(t, 1H), 6.94(m, 4H), 4.94(s, 2H), 4.27(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 7H). MASS= 466.23 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 3.83 (s, 3H), 7.31 (t, IH), 7.18 (m, 3H), 7.14 3.55 (m, 2H), 2.83 (m, 7H). MASS = 466.23

합성예 215 : N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 215: N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-브로모페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 215 화합물을 수득하였다(수율=61%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-bromophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 215 (yield = 61%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H). MASS=356.02 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 356.02

합성예 216 : 1-벤조일-N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 216: 1-Benzoyl-N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-

2-옥소-1-(2-옥소-2-페닐에틸)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-브로모페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 216 화합물을 수득하였다(수율=39%).2-oxo-1- (2-oxo-2-phenylethyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-bromophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 216 (yield = 39%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, 4H), 7.14(m, 4H), 6.87(dd, 2H), 4.34(m, 2H), MASS=460.04 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (m, 4H), 7.14 (m, 4H), 6.87 (dd, 2H), 4.34

합성예 217 : N-(4-브로모벤질)-1-(4-메톡시벤조일).2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 217: N- (4-Bromobenzyl) -1- (4-methoxybenzoyl). 2-oxo-1,2-dihydroquinoline-

1-(2-(4-메톡시페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), (4-브로모페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 217 화합물을 수득하였다(수율= 63%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-bromophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 217 (yield = 63%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, 4H), 7.14(m, 4H), 6.87(dd, 2H), 4.34(m, 2H), 3.27(s, 3H) MASS=490.05 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, IH), 7.25 (m, 4H), 7.14 (m, 4H), 6.87 (dd, 2H), 4.34

합성예 218 : N-(4-브로모펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 218: N- (4-Bromophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-브로모페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 218 화합물을 수득하였다(수율=66%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-bromophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 218 (yield = 66%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=370.03 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 370.03

합성예 219 : N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 219: Synthesis of N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-메톡시페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-브로모페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 219 화합물을 수득하였다(수율=60%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-bromophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 219 (yield = 60%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.3(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS=490.05 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.3 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 490.05

합성예 220 : N-(4-브로모펜에틸)-2-옥소-1-(4-(트리플루오로메톡시)벤조일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 220: N- (4-Bromophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzoyl) -1,2-dihydroquinoline-

2-옥소-1-(2-옥소-2-(4-(트리플루오로메톡시)페닐)에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-브로모페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 202 화합물을 수득하였다(수율=68%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and a solution of 2- &Lt; / RTI &gt; DIPEA (3 mmol), 2- (4-bromophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 202 (yield = 68%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=558.04 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 558.04

합성예 222 : N-(4-클로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 222: N- (4-chlorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide [

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-클로로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 222 화합물을 수득하였다(수율=46%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-chlorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 222 (yield = 46%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H). MASS=312.07 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 312.07

합성예 223 : N-(4-클로로벤질)-1-(4-에틸벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 223: N- (4-Chlorobenzyl) -1- (4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline-

1-(4-에틸벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-클로로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 223 화합물을 수득하였다(수율=56%).1- (4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-chlorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 223 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, 4H), 7.14(m, 3H), 6.87(dd, 2H), 4.34(m, 2H), 2.78(s, 2H), 1.28(s, 3H). MASS=444.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (m, 4H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H), 2.78 (s, 2H), 1.28 MASS = 444.12

합성예 224 : N-(4-클로로벤질)-1-(4-하이드록시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 224: N- (4-Chlorobenzyl) -1- (4-hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-

1-(4-하이드록시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-클로로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 224 화합물을 수득하였다(수율=58%).1- (4-Hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-chlorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 224 (yield = 58%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(m, 4H), 7.14(m, 3H), 6.87(dd, 2H), 4.34(m, 2H). MASS=432.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (m, 4H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 432.09

합성예 225 : N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 225: N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 225 화합물을 수득하였다(수율=67%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 225 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94 (dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=326.08 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 326.08

합성예 226 : N-(4-클로로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 226: N- (4-Chlorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 226 화합물을 수득하였다(수율=57%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 226 (yield = 57%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H), 1.78(s, 3H). MASS=446.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 1.78 (s, 3 H). MASS = 446.14

합성예 227 : 1-(4-클로로벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 227: 1- (4-Chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-클로로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(1.5 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 227 화합물을 수득하였다(수율= 65%).1- (4-Chlorobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (1.5 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 227 (yield = 65%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=464.07 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 464.07

합성예 228 : N-(4-클로로펜에틸)-1-(4-아이오도벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 228: Synthesis of N- (4-chlorophenethyl) -1- (4-iodobenzoyl) -2-oxo-1,2-dihydroquinoline-

1-(4-아이오도벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 228 화합물을 수득하였다(수율=67%).1- (4-Iodobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 228 (yield = 67%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=556.01 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 556.01

합성예 229 : N-(4-클로로펜에틸)-1-(4-니트로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 229: Synthesis of N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo-1,2-dihydroquinoline-

1-(4-니트로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 229 화합물을 수득하였다(수율=56%).1- (4-Nitrobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 229 (yield = 56%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=475.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 475.09

합성예 230 : 1-(4-아미노벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 230: 1- (4-Aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-아미노벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 230 화합물을 수득하였다(수율=45%).1- (4-aminobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 230 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.94 (dd, 2H), 4.28(s, -NH2,2H),3.55(m,2H),2.83(m,2H).MASS=445.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 4.28 (s, -NH 2, 2H), 3.55 (m, 2H), 2.83 (m , 2H). MASS = 445.12

합성예 232 : N-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 232: N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-플루오로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 232 화합물을 수득하였다(수율=59%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-fluorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 232 (yield = 59%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H). MASS= 296.10 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 296.10

합성예 233 : N-(4-플루오로벤질)-1-(4-포르밀벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 233: N- (4-Fluorobenzyl) -1- (4-formylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-

1-(4-포르밀벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-플루오로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 233 화합물을 수득하였다(수율=49%).1- (4-formylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-fluorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 233 (yield = 49%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 2.78 (s, 1H). MASS= 428.12 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 , 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H), 2.78 MASS = 428.12

합성예 234 : 1-(4-시아노벤조일)-N-(4-플루오로벤질)-2-옥소-1,2-디하이드로 퀴놀린-3-카르복사마이드Synthesis Example 234: 1- (4-Cyanobenzoyl) -N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-

1-(4-시아노벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-플루오로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 234 화합물을 수득하였다(수율=59%).1- (4-cyanobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-fluorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 234 (yield = 59%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H). MASS=425.12 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 , 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 425.12

합성예 235 (N-(4-플루오로벤질)-1-(4-(메틸티오)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 235 Synthesis of (N- (4-fluorobenzyl) -1- (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(메틸티오)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-플루오로페닐)메타나민 (1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 235 화합물을 수득하였다(수율=56%).1 - (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-fluorophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 235 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H). MASS= 446.11 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 , 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 446.11

합성예 236 : N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 236: N- (4-Fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide [

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 236 화합물을 수득하였다(수율=65%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 236 (yield = 65%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS= 310.11 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 310.11

합성예 237 : N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 237: N- (4-Fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

합성예 26 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 상온에서 교반하고 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 237 화합물을 수득하였다(수율=66%).Synthesis Example 26 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours at room temperature and the residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 237 (yield = 66%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=430.17 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 430.17

합성예 238 : 1-(4-(디플루오로메틸)벤조일)-N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 238: 1- (4- (difluoromethyl) benzoyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(디플루오로메틸)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 238 화합물을 수득하였다(수율=67%).1 - (4- (difluoromethyl) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 238 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(t, 1H), 6.94(m, 4H), 3.55(m, 2H), 2.83(m, 2H), 1.78(s, 1H). MASS=464.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (m, 4H), 3.55 (m, 2H), 2.83 (m, 2H), 1.78 MASS = 464.13

합성예 239 : N-(4-플루오로펜에틸)-1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 239: Synthesis of N- (4-fluorophenethyl) -1- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 239 화합물을 수득하였다(수율=68%)1 - (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 239 (yield = 68%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.18(dd, 2H), 7.14(t, 1H), 6.94 (dd, 2H), 3.55(m, 5H), 2.83(m, 4H). MASS=458.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H) , 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 5H), 2.83 (m, 4H). MASS = 458.16

합성예 240 : N-(4-플루오로펜에틸)-2-옥소-1-(2-(4-(트리플루오로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 240: Synthesis of N- (4-fluorophenethyl) -2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline- Mide

2-옥소-1-(2-(4-(트리플루오로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예240 화합물을 수득하였다(수율=63%)(2 mmol) of 2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 240 (yield = 63%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(t, 1H), 6.94(m, 4H), 3.55(m, 2H), 2.83(m, 4H). MASS=512.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (m, 4H), 3.55 (m, 2H), 2.83 (m, 4H). MASS = 512.14

합성예 241: N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 241: Synthesis of N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민 (1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 241 화합물을 수득하였다(수율= 55%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 241 (yield = 55%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS=306.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 1.60 (m, 2H), 7.31 (m, 2H), 7.18 (d, 2H). MASS = 306.14

합성예 242 : N-(4-에틸벤질)-1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 242: Synthesis of N- (4-ethylbenzyl) -1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 242 화합물을 수득하였다(수율=67%).(1 mmol) of 1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 242 (yield = 67%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(m, 3H), 7.18(m, 4H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS=440.17 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 2.60 (m, 2H), 1.25 (m, 2H), 7.14 (m, 2H) (m, 3 H). MASS = 440.17

합성예 243 : N-(4-에틸벤질)-1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 243: Synthesis of N- (4-ethylbenzyl) -1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 243 화합물을 수득하였다(수율=46%).(1 mmol) of 1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 243 (yield = 46%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(m, 3H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(m, 3H), 6.98(dd, 2H), 4.34(m, 2H), 3.3(s, 2H), 2.60(m, 4H), 1.25(m, 6H). MASS= 452.21 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 2H), 7.31 (d, IH), 7.18 (d, 2H), 7.14 (m, 3H), 6.98 (dd, 2H) (m, 6 H). MASS = 452.21

합성예 244 : N-(4-에틸벤질)-1-(2-(4-플루오로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 244: Synthesis of N- (4-ethylbenzyl) -1- (2- (4-fluorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-플루오로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 244 화합물을 수득하였다(수율=46%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 244 (yield = 46%).

1HNMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(m, 3H), 7.18(m, 4H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS=442.17 1 HNMR (400MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 7.31 2H), 2.60 (m, 2H), 1.25 (m, 2H), 7.18 (m, 2H) m, 3H). MASS = 442.17

합성예 245 : 1-(2-(4-클로로페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 245: 1- (2- (4-Chlorophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-클로로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민 (1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 245 화합물을 수득하였다(수율=49%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 245 (yield = 49%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(m, 3H), 7.18(m, 4H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS= 458.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 2.60 (m, 2H), 1.25 (m, 2H), 7.14 (m, 2H) (m, 3 H). MASS = 458.14

합성예 246 : N-(4-에틸벤질)-1-(2-(4-아이오도페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 246: Synthesis of N- (4-ethylbenzyl) -1- (2- (4-iodophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-아이오도페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 246 화합물을 수득하였다(수율=67%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 246 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(m, 3H), 7.18(m, 4H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS=550.08 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 2.60 (m, 2H), 1.25 (m, 2H), 7.14 (m, 2H) (m, 3 H). MASS = 550.08

합성예 247 : N-(4-에틸벤질)-1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 247: Synthesis of N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 247 화합물을 수득하였다(수율=44%).1 - (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 247 (yield = 44%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s. 1H, NH), 7.36(d, 1H), 7.31(m, 3H), 7.18(m, 4H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS= 469.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 2.60 (m, 2H), 1.25 (m, 2H), 7.14 (m, 2H) (m, 3 H). MASS = 469.16

합성예 248 : 1-(2-(4-아미노페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 248: 1- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-아미노페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-에틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 248 화합물을 수득하였다(수율=56%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-ethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 248 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 4.2 (s, -NH2, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H). MASS= 439.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), (M, 2H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 ), 2.60 (m, 2H), 1.25 (m, 3H). MASS = 439.19

합성예 249 : N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 249: Synthesis of N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 249 화합물을 수득하였다(수율=45%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 249 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.98(dd, 2H), 4.34(m, 2H), 3.60(m, 2H), 2.60(m, 2H), 1.25(s, 3H). MASS=320.15 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 3.60 (m, 2H), 2.60 (m, 2H), 1.25 (d, (s, 3 H). MASS = 320.15

합성예 250 : N-(4-에틸펜에틸)-1-(2-(4-포르밀페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 250: Synthesis of N- (4-ethylphenethyl) -1- (2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-포르밀페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 250 화합물을 수득하였다(수율=44%).(1 mmol) of 1- (2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 250 (yield = 44%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.98 (dd, 2H), 4.34(m, 2H), 3.60(m, 4H), 2.60(m, 3H), 1.25(s, 3H). MASS= 466.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 3.60 (m, 4H), 2.60 (m, 3H), 1.25 (m, (s, 3 H). MASS = 466.19

합성예 251 : 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 251: Synthesis of 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-시아노페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 251 화합물을 수득하였다(수율=56%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 251 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.98(dd, 2H), 4.34(m, 2H), 3.60(m, 4H), 2.60(m, 2H), 1.25(s, 3H). MASS=463.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 3.60 (m, 2H), 3.60 (m, 2H), 3.60 (m, 2H) (s, 3 H). MASS = 463.19

합성예 252 : N-(4-에틸펜에틸)-1-(2-(4-(메틸티오)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 252: Synthesis of N- (4-ethylphenethyl) -1- (2- (4- (methylthio) phenyl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-(메틸티오)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 25 화합물을 수득하였다(수율=57%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 25 (yield = 57%).

1HNMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.98(dd, 2H), 4.34(m, 2H), 3.60(m, 4H), 2.60(m, 2H), 1.25(s, 6H). MASS= 484.18 1 HNMR (400MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 7.31 (m, 2H), 3.60 (m, 2H), 3.60 (m, 2H) s, 6H). MASS = 484.18

합성예 253 : 1-(2-(4-(디플루오로메틸)페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 253: Synthesis of 1- (2- (4- (difluoromethyl) phenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-(디플루오로메틸)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 252 화합물을 수득하였다(수율=42%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 252 (yield = 42%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H), 7.14(m, 3H), 6.98(dd, 2H), 4.34(m, 2H), 3.60(m, 4H), 2.60(m, 2H), 1.25(s, 4H). MASS=488.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, NH), 7.36 (d, 1H), 2H), 3.60 (m, 2H), 3.60 (m, 2H), 3.60 (m, 2H) (s, 4 H). MASS = 488.19

합성예 254 : N-(4-하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 254: N- (4-Hydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 254 화합물을 수득하였다(수율=66%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 254 (yield = 66%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 5.35(s, 1H, -OH), 4.34(m, 2H). MASS= 294.10 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 5.35 (s, IH, -OH), 4.34 (m, 2H). MASS = 294.10

합성예 255 : N-(4-하이드록시벤질)-1-(4-(메틸티오)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 255: N- (4-Hydroxybenzyl) -1- (4- (methylthio) benzyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(메틸티오)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 4-(아미노메틸)페놀(1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수족한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 255 화합물을 수득하였다(수율=64%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 255 (yield = 64%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 5.35(s, 1H, -OH), 3.3(S, 2H), 4.34(m, 5H). MASS=430.14 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 1H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 5H). MASS = 430.14

합성예 256 : N-(4-하이드록시벤질)-1-(4-(메틸티오)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 256: N- (4-Hydroxybenzyl) -1- (4- (methylthio) phenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(메틸티오)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 256 화합물을 수득하였다(수율=68%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain 256 compounds of synthesis example (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 5.35(s, 1H, -OH), 3.3(s, 2H), 2.87(s, 2H), 4.34(m, 5H). MASS=444.15 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 , 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H) 2H), 4.34 (m, 5H). MASS = 444.15

합성예 257 : N-(4-하이드록시벤질)-2-옥소-1-(4-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 257: Synthesis of N- (4-hydroxybenzyl) -2-oxo-1- (4- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-

2-옥소-1-(4-(트리플루오로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드 (1mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 257 화합물을 수득하였다(수율=72%).2-oxo-1- (4- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 257 (yield = 72%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 5.35(s, 1H, -OH), 3.3(S, 2H), 2.87(s, 2H), 4.34(m, 2H). MASS=482.15 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 1H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 2H), 4.34 (m, 2H). MASS = 482.15

합성예 258 : N-(4-하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 258: Synthesis of N- (4-hydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 258 화합물을 수득하였다(수율=70%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 258 (yield = 70%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 5.35(s, 1H, -OH), 3.55(m, 2H), 2.83(m, 2H). MASS=308.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 1H), 7.31 (t, IH), 7.18 (d, 2H), 7.14 (t, IH), 6.94 (dd, 2H) 2H). MASS = 308.12

합성예 259 : N-(4-하이드록시펜에틸)-1-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 259: Synthesis of N- (4-hydroxyphenethyl) -1- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)페놀 (1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 259 화합물을 수득하였다(수율=47%).1- (4-Methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 259 (yield = 47%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 5.35(s, 1H, -OH), 3.55(m, 2H), 3.3(s, 2H), 2.97(s, 2H), 2.83(m, 5H). MASS=442.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H) 2H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 2H), 2.97 (s, 2H), 2.83 (m, 5H). MASS = 442.19

합성예 260 : N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation Example 260: Preparation of N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-니트로페닐)메타나민(1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 260 화합물을 수득하였다(수율=59%).Synthesis Example 25 (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-nitrophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 260 (yield = 59%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H). MASS= 323.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 323.09

합성예 261 : 1-(4-아이오도벤질)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 261: 1- (4-Iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-

1-(4-아이오도벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-니트로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 261 화합물을 수득하였다(수율=67%).1- (4-Iodobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-nitrophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 261 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H), 4.34(m, 2H), 3.3(s, 2H). MASS=539.03 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 , 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H). MASS = 539.03

합성예 262 : 1-(4-아이오도펜에틸)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 262: 1- (4-Iodophenethyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-

1-(4-아이오도펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-니트로페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 262 화합물을 수득하였다(수율=47%).1- (4-Iodophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-nitrophenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 262 (yield = 47%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H), 2.8 (s, 2H). MASS= 553.05 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 2H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H), 2.8 MASS = 553.05

합성예 263 : N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 263: Synthesis of N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-니트로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 263 화합물을 수득하였다(수율=45%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-nitrophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 263 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=337.11 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 337.11

합성예 264 : 1-(4-포르밀벤질)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 264: 1- (4-Formylbenzyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-포르밀벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 2-(4-니트로페닐)에타나민(1.5. mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 264 화합물을 수득하였다(수율=46%).1- (4-formylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-nitrophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 264 (yield = 46%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7,31(m, 3H), 7.18(dd, 2H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 3H). MASS=455.15 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H) (D, 2H), 7.31 (d, 2H), 7.14 (d, 2H) ). MASS = 455.15

합성예 265 : 1-(4-포르밀펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 265: 1- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-포르밀펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-니트로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 265 화합물을 수득하였다(수율=44%).1- (4-formylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-nitrophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 265 (yield = 44%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(t, 1H), 7.18(m, 4H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 4H), 2.83(m, 5H). MASS=469.06 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 4H), 2.83 (m, 5H). MASS = 469.06

합성예 266 : 1-(4-(디플루오로메틸)펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 266: 1- (4- (difluoromethyl) phenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-(디플루오로메틸)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 2-(4-니트로페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 266 화합물을 수득하였다(수율=59%).(1 mmol) of 1- (4- (difluoromethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-nitrophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 266 (yield = 59%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(m, 3H), 7.31(t, 1H), 7.18(m, 4H), 7.14(t, 1H), 6.94(dd, 2H), 3.55(m, 4H), 2.83(m, 4H), 1.37(s, 1H). MASS=491.17 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H) , 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 4H), 2.83 (m, 4H), 1.37 MASS = 491.17

합성예 267 : N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 267: Synthesis of N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)-N,N-디메틸벤젠설폰아미드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 267 화합물을 수득하였다(수율=47%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) -N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 267 (yield = 47%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 7.74 (dd, 2H), 7.51(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 4.34(m, 2H), 2.66(m, 6H). MASS=385.11 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 ( (d, IH), 7.31 (t, IH), 7.14 (t, IH), 4.34 (m, 2H), 2.66 (m, 6H). MASS = 385.11

합성예 268 : 1-(4-(디플루오로메틸)벤질)-N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 268: Synthesis of 1- (4- (difluoromethyl) benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline- Copymade

1-(4-(디플루오로메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)-N,N-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 268 화합물을 수득하였다 (수율=57%).1 - (4- (difluoromethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) -N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 268 (yield = 57%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (m, 4H), 7.36 (m, 3H), 7.31 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.3 (s, 2H), 2.66 (m, 6H), 1.78 (s, 1H). MASS= 525.15 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (m, 4H), 7.36 ( 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.3 (s, 2H), 2.66 (m, 6H), 1.78 MASS = 525.15

합성예 269 (N-(4-(N,N-디메틸설파모일)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 269 Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)-N,N-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 269 화합물을 수득하였다(수율=46%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) -N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 269 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 2.83 (m, 2H), 2.66 (m, 6H). MASS= 399.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 ( (d, IH), 7.31 (t, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.83 (m, 2H), 2.66 (m, 6H). MASS = 399.13

합성예 270 : N-(4-(하이드록시메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 270: N- (4- (hydroxymethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물을 DMF(5 mL)d[ 용해시켰다. DIPEA(0.5 mL, 2.7 mmol), (4-(아미노메틸)페닐)메탄올(1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 270 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound was dissolved in DMF (5 mL). DIPEA (0.5 mL, 2.7 mmol), (4- (aminomethyl) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 270 (yield = 49%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36(d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.61 (s, 2H), 4.34 (m, 2H), 3.65 (s, 1H, -OH). MASS= 308.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 ( 1H), 7.31 (t, IH), 7.14 (t, IH), 4.61 (s, 2H), 4.34 (m, 2H), 3.65 MASS = 308.12

합성예 271 : N-(4-(하이드록시메틸)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 271: N- (4- (hydroxymethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 271 화합물을 수득하였다(수율=46%).Synthesis Example 25 (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 271 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 7.74 (dd, 2H), 7.51(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.65(s, 1H, -OH), 3.55(m, 2H), 2.83(m, 2H). MASS=322.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 ( 1H), 7.31 (t, IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 322.13

합성예 272 : 2-옥소-N-(4-비닐벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 272: Synthesis of 2-oxo-N- (4-vinylbenzyl) -1,2-dihydroquinoline-3-carboxamide

합성예 25 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-비닐페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 272 화합물을 수득하였다(수율=56%).Synthesis Example 25 (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-vinylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 272 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 4.34 (m, 2H). MASS= 304.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H) 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 4.34 (m, 2H). MASS = 304.12

합성예 273 : 2-옥소-N-(4-비닐펜에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 273: Synthesis of 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-비닐페닐)에타나민(1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 273 화합물을 수득하였다(수율=62%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-vinylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at ambient temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 273 (yield = 62%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 4.34(m, 2H), 2.83(m, 2H). MASS= 318.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H) 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 4.34 (m, 2 H), 2.83 (m, 2 H). MASS = 318.14

합성예 274 : N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 274: N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸아닐린(1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 274 화합물을 수득하였다(수율=66%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 274 (yield = 66%).

1H NMR(400MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H). MASS= 278.11 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 ( (d, IH), 7.31 (t, IH), 7.19 (t, IH), 7.14 (t, IH), 3.44 (s, 3H). MASS = 278.11

합성예 275 : 1-(2,3-디하이드로-1H-인덴-2-카르보닐)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 275: 1- (2,3-Dihydro-1H-indene-2-carbonyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-

1-(2,3-디하이드로-1H-인덴-2-카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 275 화합물을 수득하였다(수율=64%).2-carbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL) . DIPEA (3 mmol), N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 275 (yield = 64%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 2.67(m, 5H). MASS=422.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 (s, 3H), 2.67 (m, 5H). MASS = 422.16

합성예 276 : 1-(2-(2,3-디하이드로-1H-인덴-2-일)아세틸)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 276: 1- (2- (2,3-Dihydro-1H-inden-2-yl) acetyl) -N- Carboxamide

1-(2-(2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피를 정제하여 합성예 276 화합물을 수득하였다(수율=58%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL ). DIPEA (3 mmol), N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the silica gel column chromatography was purified to obtain the compound of Synthesis Example 276 (yield = 58%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81(dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 5H). MASS= 436.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 MASS = 436.18

합성예 277 : 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 277: 1- (3- (2,3-Dihydro-1H-inden-2-yl) propanoyl) -N- 3-carboxamide

1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸아닐린(1.5 mmol) 및 PyBop(3 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 277 화합물을 수득하였다(수율=59%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (1 mmol) 2 mL). DIPEA (3 mmol), N-methylaniline (1.5 mmol) and PyBop (3 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 277 (yield = 59%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31 (m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.89(s, 2H), 2.67(m, 5H). MASS=450.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.69 (s, 2H), 2.67 (m, 3H), 7.31 (m, 3H) , 5H). MASS = 450.19

합성예 278 : N-에틸-1-(2-(5-메톡시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 278: Synthesis of N-ethyl-1- (2- (5-methoxy-2,3-dihydro-1H- Hydroquinoline-3-carboxamide

1-(2-(5-메톡시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 278 화합물을 수득하였다(수율=72%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 278 (yield = 72%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 5H). MASS=480.20 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 5H). MASS = 480.20

합성예 279 : N-에틸-1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 279: N-ethyl-1- (2- (5- (methylthio) -2,3-dihydro-1H-inden-2-yl) acetyl) Dihydroquinoline-3-carboxamide &lt; / RTI &gt;

1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 279 화합물을 수득하였다(수율=56%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 (2- (5- methylthio) mmol) were dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Then, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 279 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 5H). MASS=496.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 5H). MASS = 496.18

합성예 280 : N-에틸-2-옥소-N-페닐-1-(2-(5-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 280: Synthesis of N-ethyl-2-oxo-N-phenyl-1- (2- (5- (trifluoromethoxy) -2,3-dihydro- , 2-dihydroquinoline-3-carboxamide

2-옥소-1-(2-(5-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 280 화합물을 수득하였다(수율=56%).Dihydro-1H-inden-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid (2-oxo- (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 280 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS=534.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 534.18

합성예 281 : N-에틸-1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 281: Synthesis of N-ethyl-1- (2- (5-hydroxy-2,3-dihydro-1H- Hydroquinoline-3-carboxamide

1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피를 정제하여 합성예 281 화합물을 수득하였다(수율=58%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the silica gel column chromatography was purified to obtain the compound of Synthesis Example 281 (yield = 58%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS=466.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 466.19

합성예 282 : N-에틸-1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 282: Synthesis of N-ethyl-1- (2- (5-ethyl-2,3-dihydro-1H-inden-2-yl) acetyl) Quinoline-3-carboxamide

1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 282 화합물을 수득하였다(수율= 67%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 282 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(m, 4H), 2.67(m, 7H), 2.43(m, 5H). MASS=478.23 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( (m, 2H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 , 5H). MASS = 478.23

합성예 283 : N-에틸-1-(2-(5-플루오로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 283: N-ethyl-1- (2- (5-fluoro-2,3-dihydro-1H- Hydroquinoline-3-carboxamide

1-(2-(5-플루오로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 283 화합물을 수득하였다(수율=48%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 283 (yield = 48%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS=468.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 468.18

합성예 284 : 1-(2-(5-클로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 284: 1- (2- (5-Chloro-2,3-dihydro-1H-inden-2-yl) acetyl) -N- Quinoline-3-carboxamide

1-(2-(5-클로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 284 화합물을 수득하였다(수율= 47%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 284 (yield = 47%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14(t, 1H), 3.44 (s, 3H), 3.18(s, 2H), 2.67 (m, 7H), 2.43 (m, 2H). MASS= 484.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 484.16

합성예 285 : N-에틸-1-(2-(5-아이오도-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 285: Synthesis of N-ethyl-1- (2- (5-iodo-2,3-dihydro-1H- Hydroquinoline-3-carboxamide

1-(2-(5-아이오도-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 285 화합물을 수득하였다(수율=56%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 285 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS=576.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 576.09

합성예 286 : N-에틸-1-(2-(5-니트로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 286: Synthesis of N-ethyl-1- (2- (5-nitro-2,3-dihydro-1H-inden-2-yl) acetyl) Quinoline-3-carboxamide

1-(2-(5-니트로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예286 화합물을 수득하였다(수율=55%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 286 (yield = 55%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS=495.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.67 (m, 7H), 2.43 (m, 2H), 7.31 (m, 3H), 7.19 (t, , 2H). MASS = 495.16

합성예 287 : 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 287: 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) acetyl) -N- Quinoline-3-carboxamide

1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 287 화합물을 수득하였다(수율=68%).2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was added to a solution of Was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 287 (yield = 68%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 4.28(s, -NH2, 2H), 3.44(s, 3H), 3.18(s, 2H), 2.67(m, 7H), 2.43(m, 2H). MASS= 465.21 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 7.38 (s, 3H), 7.31 (s, 3H), 7.19 (t, 2.67 (m, 7 H), 2.43 (m, 2 H). MASS = 465.21

합성예 288 : N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 288: N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 288 화합물을 수득하였다(수율=45%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 288 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.19(t, 1H), 7.14(t, 1H), 4.28(m, 2H), 1.31(s, 3H). MASS=292.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 ( (d, IH), 7.31 (t, IH), 7.19 (t, IH), 7.14 (t, IH), 4.28 (m, 2H), 1.31 (s, 3H). MASS = 292.12

합성예 289 : 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 289: 1- (3- (2,3-Dihydro-1H-inden-2-yl) propanoyl) -N- 3-carboxamide

1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 289 화합물을 수득하였다(수율=50%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (1 mmol) 2 mL). DIPEA (3 mmol), N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 289 (yield = 50%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, 1H), 7.31(m, 3H), 7.19(t, 1H), 7.14(t, 1H), 4.28(m, 2H), 2.68(m, 7H), 2.37(m, 2H), 1.31(s, 3H). MASS=464.21 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 ( 2H), 2.37 (m, 2H), 1.31 (m, 2H), 7.31 (m, 2H) , 3H). MASS = 464.21

합성예 292 : N-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 292: N-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N,4-디메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 292 화합물을 수득하였다(수율=54%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N, 4-dimethylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 292 (yield = 54%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (m, 3H), 7.21(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 3.44(s, 3H), 2.34(s, 3H). MASS=292.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.21 (dd, 2H), 7.31 ( t, 1 H), 7.14 (t, 1 H), 3.44 (s, 3 H), 2.34 (s, 3 H). MASS = 292.12

합성예 295 : N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 295: N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 295 화합물을 수득하였다(수율=54%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 295 (yield = 54%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.21(dd, 2H), 7.14(t, 1H), 4.28(m, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=306.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 ( t, 1 H), 7.21 (dd, 2H), 7.14 (t, IH), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H). MASS = 306.14

합성예 296 : N-에틸-2-옥소-1-(4-(페닐티오)벤질)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 296: Synthesis of N-ethyl-2-oxo-1- (4- (phenylthio) benzyl) -N- (p-tolyl) -1,2-dihydroquinoline-

2-옥소-1-(4-(페닐티오)벤질)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 296 화합물을 수득하였다(수율=57%).2-oxo-1- (4- (phenylthio) benzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 296 (yield = 57%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 3.3 (s, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=504.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( 2H), 2.34 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H). MASS = 504.19

합성예 297 : N-에틸-2-옥소-1-(4-페녹시벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 297: Synthesis of N-ethyl-2-oxo-1- (4-phenoxybenzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-

2-옥소-1-(4-페녹시벤조일)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 297 화합물을 수득하였다(수율=58%).2-oxo-1- (4-phenoxybenzoyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 297 (yield = 58%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=502.19 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( t, 1 H), 7.21 (m, 7H), 7.14 (t, IH), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H). MASS = 502.19

합성예 298 : N-에틸-2-옥소-1-(4-(페닐티오)벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 298: Synthesis of N-ethyl-2-oxo-1- (4- (phenylthio) benzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-

2-옥소-1-(4-(페닐티오)벤조일)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 298 화합물을 수득하였다(수율=58%).2-oxo-1- (4- (phenylthio) benzoyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 298 (yield = 58%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=518.17 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( t, 1 H), 7.21 (m, 7H), 7.14 (t, IH), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H). MASS = 518.17

합성예 299 : N-에틸-2-옥소-1-(2-(4-(페닐티오)페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 299: Synthesis of N-ethyl-2-oxo-1- (2- (4- (phenylthio) phenyl) acetyl) -N- (p-tolyl) -1, 2-dihydroquinoline-

2-옥소-1-(2-(4-(페닐티오)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 299 화합물을 수득하였다(수율=69%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 299 (yield = 69%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21 (m, 7H), 7.14(t, 1H), 4.28(m, 2H), 3.7(s, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=532.18 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( 2H), 2.34 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H). MASS = 532.18

합성예 300 : N-에틸-2-옥소-1-(2-(4-페녹시페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 300: Synthesis of N-ethyl-2-oxo-1- (2- (4-phenoxyphenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-

2-옥소-1-(2-(4-페녹시페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 300 화합물을 수득하였다(수율=74%).2-oxo-1- (2- (4-phenoxyphenyl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain a compound of Synthesis Example 300 (yield = 74%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 3.70(s, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=516.20 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( 2H), 3.70 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H). MASS = 516.20

합성예 301 : 1-(2-(4-벤질페닐)아세틸)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 301: Synthesis of 1- (2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

1-(2-(4-벤질페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 301 화합물을 수득하였다(수율=55%).1 - (2- (4-benzylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 301 (yield = 55%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 3.70(s, 2H), 2.78(s, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=514.23 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( 2H), 2.70 (s, 3H), 2.31 (s, 3H), 1.31 (m, 2H) , 3H). MASS = 514.23

합성예 302 : 1-(4-벤질벤조일)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 302: 1- (4-benzylbenzoyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

1-(4-벤질벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 302 화합물을 수득하였다(수율=74%).1- (4-Benzylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 302 (yield = 74%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(m, 6H), 7.31(t, 1H), 7.21(m, 7H), 7.14(t, 1H), 4.28(m, 2H), 3.70(s, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=500.21 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 ( 2H), 3.70 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H). MASS = 500.21

합성예 303 : N-(4-메톡시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 303: Synthesis of N- (4-methoxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-메톡시-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 303 화합물을 수득하였다(수율=44%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-methoxy-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 303 (yield = 44%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (s, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.21 (dd, 2H), 7.14(t, 1H), 4.28(s, 3H), 3.83(s, 3H). MASS=308.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 ( t, 1 H), 7.21 (dd, 2H), 7.14 (t, IH), 4.28 (s, 3H), 3.83 (s, 3H). MASS = 308.12

합성예 304 : N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 304: Synthesis of N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-메톡시아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 304 화합물을 수득하였다(수율=73%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-methoxyaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 304 (yield = 73%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23(s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.93 (s, 3H), 1.31 (s, 3H). MASS= 322.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.93 (s, 3H), 1.31 (s, 3H). MASS = 322.13

합성예 306 : N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 306: N- (4-Bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop (2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 306 화합물을 수득하였다(수율=56%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 306 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H). MASS= 356.02 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1 H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H). MASS = 356.02

합성예 307 : N-(4-브로모페닐)-1-(사이클로펜타-1,3-디엔카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 307: Synthesis of N- (4-bromophenyl) -1- (cyclopenta-1,3-dienecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(사이클로펜타-1,3-디엔카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 307 화합물을 수득하였다(수율=64%).1,3-dienecarbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 307 (yield = 64%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.78(m, 6H). MASS=448.04 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H). MASS = 448.04

합성예 308 : N-(4-브로모페닐)-N-메틸-2-옥소-1-(2H-피롤-3-카르보닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 308: Synthesis of N- (4-bromophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-3-carbonyl) -1,2-dihydroquinoline-

2-옥소-1-(2H-피롤-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 308 화합물을 수득하였다(수율=67%).2-oxo-1- (2H-pyrrole-2-carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 308 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.78(m, 5H). MASS=449.04 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 5H). MASS = 449.04

합성예 309 : N-(4-브로모페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 309: Synthesis of N- (4-bromophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-

2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 309 화합물을 수득하였다(수율=67%).2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 309 (Yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.78(m, 6H). MASS= 466.00 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H). MASS = 466.00

합성예 310 : (N-(4-브로모페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 310: (N- (4-Bromophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(퓨란-2-카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 310 화합물을 수득하였다(수율=63%).L- (Furan-2-carbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 310 (yield = 63%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.78(m, 6H). MASS=450.02 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H). MASS = 450.02

합성예 311 : N-(4-브로모페닐)-N-메틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 311: Synthesis of N- (4-bromophenyl) -N-methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline- Mide

2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2mL)에 용해시켰다. DIPEA(3mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 311 화합물을 수득하였다(수율=55%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 311 (yield = 55%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(s, 2H), 2.78(m, 6H). MASS=480.01 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H). MASS = 480.01

합성예 312 : N-(4-브로모페닐)-1-(2-(퓨란-2-일)아세틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 312: Synthesis of N- (4-bromophenyl) -1- (2- (furan-2-yl) acetyl) -N- methyl-2-oxo-1,2-dihydroquinoline-

1-(2-(퓨란-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 312 화합물을 수득하였다(수율=56%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 312 (yield = 56%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(s, 2H), 2.78(m, 6H). MASS=464.04 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H). MASS = 464.04

합성예 313 : 1-(2-(2H-피롤-2-일)아세틸)-N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 313: 1- (2- (2H-Pyrrol-2-yl) acetyl) -N- (4-bromophenyl) -N- methyl-2-oxo-1,2-dihydroquinoline- Copymade

1-(2-(2H-피롤-5-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-브로모-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 313 화합물을 수득하였다(수율=45%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 313 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(s, 2H), 2.78(m, 6H). MASS=473.05 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H). MASS = 473.05

합성예 314 : N-(4-브로모페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 314: N- (4-Bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 314 화합물을 수득하였다(수율=67%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 314 (yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 1.31(s, 3H). MASS=370.03 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H). MASS = 370.03

합성예 315 : N-(4-브로모페닐)-1-(사이클로헥산카르보닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 315: Synthesis of N- (4-bromophenyl) -1- (cyclohexanecarbonyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

1-(사이클로헥산카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모-N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 315 화합물을 수득하였다(수율=45%).L- (cyclohexanecarbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromo-N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 315 (yield = 45%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 1.98(m, 10H), 1.31(s, 3H). MASS=480.10 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.98 (m, 10H), 1.31 (s, 3H). MASS = 480.10

합성예 316 : N-(4-브로모페닐)-1-(3-사이클로헥실프로파노일)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 316: N- (4-Bromophenyl) -1- (3-cyclohexylpropanoyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

1-(3-사이클로헥실프로파노일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), R 4-브로모-N-에틸아닐린3-NH2(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피를 정제하여 합성예 316 화합물을 수득하였다(수율=42%)1- (3-Cyclohexylpropanoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), R 4-bromo-N-ethylaniline 3 -NH 2 (1.5 mmol) and PyBop ( 2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the silica gel column chromatography was purified to obtain the compound of Synthesis Example 316 (yield = 42%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 2.79(s, 2H), 2.54(s, 2H), 1.98(m, 10H), 1.31(s, 3H). MASS=508.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( 2H), 1.31 (s, 3H), 7.21 (d, 2H), 4.28 (m, 2H), 2.79 (s, 2H), 2.54 MASS = 508.14

합성예 318 : N-(4-클로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 318: N- (4-Chlorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 318 화합물을 수득하였다(수율=64%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 318 (yield = 64%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H). MASS= 312.07 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1 H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H). MASS = 312.07

합성예 319 : N-(4-클로로페닐)-1-(사이클로펜탄카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 319: Synthesis of N- (4-chlorophenyl) -1- (cyclopentanecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(사이클로프로판카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 319 화합물을 수득하였다(수율=56%).L- (Cyclopropanecarbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 319 (yield = 56%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(m, 8H). MASS=408.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 8H). MASS = 408.12

합성예 320 : N-(4-클로로페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 320: N- (4-Chlorophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(퓨란-3-카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 320 화합물을 수득하였다(수율=73%).1- (Furan-3-carbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 320 (yield = 73%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(m, 3H). MASS= 406.07 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H). MASS = 406.07

합성예 321 : N-(4-클로로페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 321: Synthesis of N- (4-chlorophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-

2-옥소-1-(티오펜-3-카르보닐)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-메틸아닐린 (2 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 321 화합물을 수득하였다(수율=56%).2-oxo-1- (thiophene-3-carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (2 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 321 (yield = 56%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.98(m, 3H). MASS=422.05 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H). MASS = 422.05

합성예 322 : N-(4-클로로페닐)-N-메틸-2-옥소-1-(2H-피롤-2-카르보닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 322: Synthesis of N- (4-chlorophenyl) -N-methyl-2-oxo-1- (2H- pyrrole-2-carbonyl) -1,2-dihydroquinoline-

2-옥소-1-(2H-피롤-5-카르보닐)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-클로로-N-메틸아닐린(1.5 mmol) 및 PyBop(3 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 322 화합물을 수득하였다(수율=57%).2-oxo-1- (2H-pyrrole-5-carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (1.5 mmol) and PyBop (3 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 322 (yield = 57%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21 (dd, 2H), 4.28(s, 3H), 2.98(m, 3H). MASS=405.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H). MASS = 405.09

합성예 323 : N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 323: N- (4-Chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 323 화합물을 수득하였다(수율=58%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 323 (yield = 58%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 1.31(s, 3H). MASS=326.08 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H). MASS = 326.08

합성예 324 : N-(4-클로로페닐)-1-(2-사이클로펜틸아세틸)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 324: Synthesis of N- (4-chlorophenyl) -1- (2-cyclopentyl acetyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

1-(2-사이클로펜틸아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-에틸아닐린(1.5. mmol) 및 PyBop(0.9 mg, 1.8 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 324 화합물을 수득하였다.1- (2-Cyclopentyl acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-ethyl aniline (1.5 mmol) and PyBop (0.9 mg, 1.8 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 324.

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 3.45(m, 2H), 2.87(m, 8H), 1.31(s, 3H). MASS=436.16 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( (m, 2H), 3.45 (m, 2H), 2.87 (m, 8H), 1.31 (s, 3H). MASS = 436.16

합성예 325 : N-(4-클로로페닐)-N-에틸-1-(2-(퓨란-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 325: Synthesis of N- (4-chlorophenyl) -N-ethyl-1- (2- (furan-2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(퓨란-3-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 4-클로로-N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 325 화합물을 수득하였다(수율=45%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 325 (yield = 45%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 3.45(m, 2H), 2.87(m, 3H), 1.31(s, 3H). MASS=434.10 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( (m, 2H), 2.45 (m, 3H), 2.31 (s, 3H). MASS = 434.10

합성예 326 : N-(4-클로로페닐)-N-에틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 326: Synthesis of N- (4-chlorophenyl) -N-ethyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-

2-옥소-1-(2-(티오펜-3-일)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 326 화합물을 수득하였다(수율=66%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-ethyl aniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 326 (yield = 66%).

1H NMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 3.45(m, 2H), 2.87(m, 3H), 1.31(s, 3H). MASS=450.08 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( (m, 2H), 2.45 (m, 3H), 2.31 (s, 3H). MASS = 450.08

합성예 327 : 1-(2-(2H-피롤-2-일)아세틸)-N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 327: Synthesis of 1- (2- (2H-pyrrol-2-yl) acetyl) -N- (4- chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- Mide

1-(2-(2H-피롤-5-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 327 화합물을 수득하였다(수율=46%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 327 (yield = 46%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 3.45(m, 2H), 2.87(m, 3H), 1.31(s, 3H). MASS=433.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( (m, 2H), 2.45 (m, 3H), 2.31 (s, 3H). MASS = 433.12

합성예 328 : N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 328: N- (4-Fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 328 화합물을 수득하였다(수율=58%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 328 (yield = 58%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H). MASS= 296.10 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, 1 H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H). MASS = 296.10

합성예 329 : N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-페닐에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 329: Synthesis of N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2-oxo-2-phenylethyl) -1,2-dihydroquinoline-

2-옥소-1-(2-페닐아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 329 화합물을 수득하였다(수율=67%).2-oxo-1- (2-phenylacetyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 329 (Yield = 67%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H). MASS=414.14 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 414.14

합성예 330 : N-(4-플루오로페닐)-1-(2-(4-메톡시페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 330: Synthesis of N- (4-fluorophenyl) -1- (2- (4-methoxyphenyl) -2-oxoethyl) -N-methyl-2-oxo-1,2-dihydroquinolin- - carboxamide

1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 330 화합물을 수득하였다(수율=67%).1 - (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 330 (yield = 67%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H), 1.35(s, 3H). MASS=444.15 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H), 1.35 (s, 3H). MASS = 444.15

합성예 331 : N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-(4-(트리플루오로메톡시)페닐)에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 331: Synthesis of N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2- Hydroquinoline-3-carboxamide

2-옥소-1-(2-(4-(트리플루오로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 331 화합물을 수득하였다(수율=65%).(2 mmol) of 2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 331 (yield = 65%).

1H NMR (400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79 (s, 2H). MASS= 498.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 498.12

합성예 332 : N-(4-플루오로페닐)-N-메틸-1-(2-(4-니트로페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 332: Synthesis of N- (4-fluorophenyl) -N-methyl-1- (2- (4-nitrophenyl) -2-oxoethyl) -2-oxo-1,2-dihydroquinolin- Carboxamide

1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 332 화합물을 수득하였다(수율=76%).1 - (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 332 (yield = 76%).

1H NMR(400MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H). MASS= 459.12 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 459.12

합성예 333 : N-(4-플루오로페닐)-1-(2-(4-하이드록시페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 333: Synthesis of N- (4-fluorophenyl) -1- (2- (4-hydroxyphenyl) -2-oxoethyl) -N-methyl-2-oxo-1,2-dihydroquinoline- - carboxamide

1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)를 DMF(2mL)에 용해시켰다. DIPEA(3mmol), 4-플루오로-N-메틸아닐린(1.5mmol) 및 PyBop(2mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 333 화합물을 수득하였다(수율=76%).(1 mmol) of 1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at ambient temperature for 3 hours at room temperature. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 333 (yield = 76%).

1H NMR (400MHz,CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H). MASS=430.13 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 430.13

합성예 334 : N-(4-플루오로페닐)-1-(2-(4-플루오로페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 334: N- (4-Fluorophenyl) -1- (2- (4-fluorophenyl) -2-oxoethyl) - carboxamide

1-(2-(4-플루오로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 334 화합물을 수득하였다(수율=78%)2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 334 (yield = 78%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 432.13 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 432.13

합성예 335 : 1-(2-(4-에틸페닐)-2-옥소에틸)-N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 335: 1- (2- (4-Ethylphenyl) -2-oxoethyl) -N- (4- fluorophenyl) -N- Carboxamide

1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-플루오로-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 335 화합물을 수득하였다(수율=73%).(1 mmol) of 1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 335 (yield = 73%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34(m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.97(m, 2H), 2.79(s, 2H), 1.35(s, 3H). MASS = 442.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 3H), 2.97 (s, 3H), 2.97 (s, 2H). MASS = 442.17

합성예 336 : 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 336: Synthesis of 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(2-(4-클로로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 336 화합물을 수득하였다(수율=76%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 336 (yield = 76%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H). MASS=448.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 448.10

합성예 337 : N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 337: N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 337 화합물을 수득하였다(수율=71%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 337 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 1.31(s, 3H). MASS=310.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H). MASS = 310.11

합성예 338 : 1-(2-(4-아미노페닐)-2-옥소에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 338: 1- (2- (4-aminophenyl) -2-oxoethyl) -N-ethyl-N- (4-fluorophenyl) Carboxamide

1-(2-(4-아미노페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 338 화합물을 수득하였다(수율=76%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 338 (yield = 76%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 4.05(s, -NH2, -2H), 2.79(s, 2H). MASS=443.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 4.05 (s, -NH 2, -2H), 2.79 (s, 2H). MASS = 443.16

합성예 339 : 1-(2-(4-시아노페닐)-2-옥소에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 339: Synthesis of 1- (2- (4-cyanophenyl) -2-oxoethyl) -N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinolin- - carboxamide

1-(2-(4-시아노페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 339 화합물을 수득하였다(수율=43%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 339 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 2.79(s, 2H). MASS=453.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 453.15

합성예 340 : N-에틸-N-(4-플루오로페닐)-1-(2-(4-(메틸티오)페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 340: Synthesis of N-ethyl-N- (4-fluorophenyl) -1- (2- (4- (methylthio) phenyl) -2-oxoethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide

1-(2-(4-(메틸티오)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-플루오로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 340 화합물을 수득하였다(수율=42%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 340 (yield = 42%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s, 3H), 3.30(s, 3H), 2.79(s, 2H). MASS=474.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 3.30 (s, 3H), 2.79 (s, 2H). MASS = 474.14

합성예 341 : N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 341: N- (4-Ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N,4-디에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 341 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N, 4-diethylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 341 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.27(dd, 2H), 7.14(t, 1H), 3.44(s, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=306.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.27 (d, 2H), 7.14 (t, IH), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 (s, 3H). MASS = 306.14

합성예 342 : 1-(2,4-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 342: 1- (2,4-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(2,4-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N,4-디에틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 342 화합물을 수득하였다(수율=76%).L- (2,4-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N, 4-diethylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 342 (yield = 76%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 6H), 2.60(m, 2H), 1.25(s, 3H). MASS=424.22 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H). MASS = 424.22

합성예 343 : 1-(2,4-디메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 343: 1- (2,4-Dimethylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(2,4-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 343 화합물을 수득하였다(수율=70%)1- (2,4-Dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 343 (yield = 70%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 6H), 2.60(m, 2H), 1.25(s, 3H). MASS=438.22 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H). MASS = 438.22

합성예 344 : N-(4-에틸페닐)-1-(4-하이드록시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 344: Synthesis of N- (4-ethylphenyl) -1- (4-hydroxy-2-methylbenzyl) -N- methyl-2-oxo-1,2-dihydroquinoline-

1-(4-하이드록시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 344 화합물을 수득하였다(수율=53%).1- (4-Hydroxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 344 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=426.19 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H). MASS = 426.19

합성예 345 : N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 345: Synthesis of N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-

1-(2-메틸-4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 345 화합물을 수득하였다(수율=67%).1- (2-Methyl-4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 345 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=455.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H). MASS = 455.18

합성예 346 : 1-(4-에틸-2-메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 346: 1- (4-Ethyl-2-methylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(4-에틸-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드)(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 346 화합물을 수득하였다(수율=43%)L- (4-ethyl-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid) (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 346 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 6H), 2.60(m, 4H), 1.25(s, 3H). MASS=452.25 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H). MASS = 452.25

합성예 347 : N-(4-에틸페닐)-1-(4-하이드록시-2-메틸펜에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드SYNTHESIS EXAMPLE 347 Synthesis of N- (4-ethylphenyl) -1- (4-hydroxy-2-methylphenethyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(4-하이드록시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 347 화합물을 수득하였다(수율=38%).1- (4-Hydroxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 347 (yield = 38%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=440.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H). MASS = 440.21

합성예 348 : N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 348: Synthesis of N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-

1-(2-메틸-4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 348 화합물을 수득하였다(수율=67%).1- (2-Methyl-4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 348 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=469.20 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H). MASS = 469.20

합성예 349 : 1-(4-에틸-2-메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 349: 1- (4-Ethyl-2-methylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(4-에틸-2-메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 349 화합물을 수득하였다(수율=45%).Methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol) was dissolved in DMF ( 2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 349 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 6H), 2.60(m, 2H), 1.25(s, 3H). MASS = 438.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H). MASS = 438.23

합성예 350 : 1-(2,3-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 350: 1- (2,3-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(2,3-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 350 화합물을 수득하였다(수율=45%).1- (2,3-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 350 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.41 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.27(m, 3H), 7.14(t, 1H), 3.44(s, 3H), 3.28(s, 2H), 2.80(m, 6H), 2.60(m, 2H), 1.25(s, 3H). MASS=424.22 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H). MASS = 424.22

합성예 352 : N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 352: N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 352 화합물을 수득하였다(수율=76%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 352 (yield = 76%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (dd, 2H), 7.29(t, 1H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=320.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 (s, 3H). MASS = 320.15

합성예 353 : 1-(2,5-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 353: 1- (2,5-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2,5-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 353 화합물을 수득하였다(수율=45%).1- (2,5-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 353 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8(m, 2H), 2.60(m, 8H), 1.25(s, 3H). MASS=438.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H). MASS = 438.23

합성예 354 : 1-(3,4-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 354: 1- (3,4-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

1-(3,4-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 354 화합물을 수득하였다(수율=45%).L- (3,4-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 354 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8(m, 2H), 2.60(m, 8H), 1.25(s, 3H). MASS=438.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H). MASS = 438.23

합성예 355 : 1-(2,6-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이로퀴놀린-3-카르복사마이드Synthesis Example 355: 1- (2,6-Dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2,6-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 355 화합을 수득하였다(수율=76%).1- (2,6-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the desired compound (yield = 76%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8(m, 2H), 2.60(m, 8H), 1.25(s, 3H). MASS=438.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H). MASS = 438.23

합성예 356 : N-에틸-N-(4-에틸페닐)-2-옥소-1-(2,4,6-트리메틸벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 356: Synthesis of N-ethyl-N- (4-ethylphenyl) -2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydroquinoline-

2-옥소-1-(2,4,6-트리메틸벤질)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 356 화합물을 수득하였다(수율=45%).2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 356 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41(m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8 (m, 2H), 2.60(m, I1H), 1.25(s, 3H). MASS = 452.25 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 1H), 1.25 (s, 3H). MASS = 452.25

합성예 357 : 1-(4-(디플루오로메틸)-2-메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 357: Synthesis of 1- (4- (difluoromethyl) -2-methylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- Copymade

1-(4-(디플루오로메틸)-2-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 357 화합물을 수득하였다(수율=45%).2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 357 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8(m, 2H), 2.60(m, 5H), 1.25(m, 4H). MASS=474.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 5H), 1.25 (m, 4H). MASS = 474.12

합성예 358 : (E)-1-(2-(4-(디플루오로메틸)-2-메틸사이클로헥사-2,4-디엔-1-일리덴)에틸)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 358: (E) -1- (2- (4- (difluoromethyl) -2-methylcyclohexa-2,4-dien-1-ylidene) ethyl) 4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

(E)-1-(2-(4-(디플루오로메틸)-2-메틸사이클로헥사-2,4-디엔-1-일리덴)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 358 화합물을 수득하였다(수율=45%).(E) -1- (2- (4- (difluoromethyl) -2-methylcyclohexa-2,4-dien-1-ylidene) ethyl) -2-oxo-1,2-dihydroquinoline -3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 358 (yield = 45%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41(m, 4H), 7.29(m, 2H), 7.27(dd, 2H), 4.28(m, 2H), 3.44(s, 3H), 2.8 (m, 2H), 2.60(m, 5H), 1.25(m, 5H). MASS=488.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 5H), 1.25 (m, 5H). MASS = 488.23

합성예 359 : N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 359: Synthesis of N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸-N-메틸아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 359 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 359 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 3.44(s, 3H). MASS=294.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, IH), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 3.44 (s, 3H). MASS = 294.10

합성예 360 : N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 360: Synthesis of N- (4-hydroxyphenyl) -1- (4-methoxy-2-methylbenzyl) -N- methyl-2-oxo-1,2-dihydroquinoline-

1-(4-메톡시-2-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(메틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하고 실리카겔 크로마토그래프로 정제하여 합성예 360 화합물을 수득하였다(수율=45%).L- (4-Methoxy-2-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (methylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water and purified by silica gel chromatography to obtain a compound of Synthesis Example 360 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.44(m, 9H). MASS=428.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.44 (m, 9H). MASS = 428.17

합성예 361 : N-(4-하이드록시페닐)-N-메틸-2-옥소-1-(2,3,4,5,6-펜타메틸벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 361: Synthesis of N- (4-hydroxyphenyl) -N-methyl-2-oxo-1- (2,3,4,5,6-pentamethylbenzyl) -1,2-dihydroquinolin- Carboxamide

2-옥소-1-(2,3,4,5,6-펜타메틸벤질)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(메틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 361 화합물을 수득하였다(수율=45%).2-oxo-1- (2,3,4,5,6-pentamethylbenzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (methylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 361 (yield = 45%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.44(m, 18H). MASS=454.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.44 (m, 18H). MASS = 454.23

합성예 363 : N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 363: Synthesis of N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 363 화합물을 수득하였다(수율=45%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 363 (yield = 45%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 1.31(s, 3H). MASS=308.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, IH), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 1.31 MASS = 308.12

합성예 364 : N-에틸-N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 364 Synthesis of N-ethyl-N- (4-hydroxyphenyl) -1- (4-methoxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-

1-(4-메톡시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 364 화합물을 수득하였다(수율=47%).1- (4-Methoxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 364 (yield = 47%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.87(m, 4H), 1.31(m, 9H). MASS=456.20 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H). MASS = 456.20

합성예 365 : 1-(2,3-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 365: 1- (2,3-Dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2,3-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 365 화합물을 수득하였다(수율=43%).1- (2,3-Dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 365 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.87(m, 4H), 1.31(m, 9H). MASS=440.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H). MASS = 440.21

합성예 366 : 1-(2,5-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 366: 1- (2,5-Dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2,5-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 366 화합물을 수득하였다(수율=43%).1- (2,5-Dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 366 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.87(m, 4H), 1.31(m, 9H). MASS=440.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H). MASS = 440.21

합성예 367 : 1-(2,6-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 367: 1- (2,6-Dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

1-(2,6-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 367 화합물을 수득하였다(수율=43%).1- (2,6-Dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 367 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.87(m, 4H), 1.31(m, 9H). MASS=442.20 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H). MASS = 442.20

합성예 368 : N-에틸-N-(4-하이드록시페닐)-2-옥소-1-(2,4,6-트리메틸펜에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 368: Synthesis of N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1- (2,4,6-trimethylphenethyl) -1,2-dihydroquinoline-

2-옥소-1-(2,4,6-트리메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(에틸아미노)페놀(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 368 화합물을 수득하였다(수율=43%).2-oxo-1- (2,4,6-trimethylphenethyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 368 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(m, 2H), 7.31(m, 2H), 7.14(m, 2H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 4.28(s, 2H), 3.87(m, 4H), 1.31(m, 12H). MASS=454.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 MASS = 454.23

합성예 369 : N-메틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 369: Synthesis of N-methyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸-4-니트로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 369 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-methyl-4-nitroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 369 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (ss, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 3.44(s, 3H). MASS=323.09 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.93 (dd, 2 H), 3.44 (s, 3 H). MASS = 323.09

합성예 370: N-메틸-N-(4-니트로페닐)-2-옥소-1-(2,3,4,5,6-펜타메틸펜에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 370: Synthesis of N-methyl-N- (4-nitrophenyl) -2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) -1,2-dihydroquinolin- Carboxamide

2-옥소-1-(2,3,4,5,6-펜타메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸-4-니트로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 370 화합물을 수득하였다(수율=49%).2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-methyl-4-nitroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 370 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (ss, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 4.87(m, 4H), 3.44(s, 3H), 3.12(m, 15H). MASS=497.23 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 4.87 (m, 4H), 3.44 (s, 3H), 3.12 (m, 15H). MASS = 497.23

합성예 371 : N-에틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 371: N-ethyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-니트로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 371 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-nitroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 371 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.86(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 4.28(s, 2H), 1.31 (s, 3H). MASS=337.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, IH), 6.93 (dd, 2H), 4.28 (s, 2H), 1.31 (s, 3H). MASS = 337.11

합성예 372 : N-(4-(N,N-디메틸설파모일)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 372: Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸-4-니트로아닐린(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 371 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-nitroaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 371 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (ss, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 3.44(s, 3H), 2.66(m, 6H). MASS=385.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1 H), 7.14 (t, IH), 6.93 (dd, 2H), 3.44 (s, 3H), 2.66 (m, 6H). MASS = 385.11

합성예 373 : N-(4-(N,N-디메틸설파모일)페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 373: Synthesis of N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N,N-디메틸-4-(메틸아미노)벤젠설폰아미드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 373 화합물을 수득하였다(수율=51%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N, N-dimethyl-4- (methylamino) benzenesulfonamide (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 373 (yield = 51%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (ss, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 3.44(s, 3H), 2.66(m, 6H), 1.31(s, 3H). MASS=399.13 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 3.44 (s, 3H), 2.66 (m, 6H), 1.31 MASS = 399.13

합성예 374 : N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 374: N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 374 화합물을 수득하였다(수율=59%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 374 (yield = 59%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (dd, 2H), 7.36(d, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H). MASS=308.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 4.61 (m, 2H), 3.65 (s, IH, -OH), 3.44 (s, 3H). MASS = 308.12

합성예 375 : 1-(4-(1H-피라졸-1-일)벤질)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 375: 1- (4- (1H-Pyrazol-1-yl) benzyl) -N- (4- (hydroxymethyl) phenyl) -N- -3-carboxamide

1-(4-(1H-피라졸-1-일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 375 화합물을 수득하였다(수율=63%).Benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 375 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (m, 3H), 7.36(m, 2H), 7.34(m, 3H), 7.31(m, 2H), 7.14(t, 1H), 4.61(m, 2H), 4.28(s, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.87(m, 3H). MASS=464.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (s, 3H), 7.31 (m, 2H), 7.14 (t, IH), 4.61 (m, 2H), 4.28 , &Lt; / RTI &gt; 2.87 (m, 3H). MASS = 464.18

합성예 376 : 1-(4-(1H-피라졸-1-일)벤조일)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 376: 1- (4- (1H-Pyrazol-1-yl) benzoyl) -N- (4- (hydroxymethyl) phenyl) -N- -3-carboxamide

1-(4-(1H-피라졸-1-일)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 376 화합물을 수득하였다(수율=43%).1-yl) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 376 (yield = 43%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39(m, 3H), 7.36(m, 2H), 7.34(m, 3H), 7.31(m, 2H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.87(m, 3H). MASS=478.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (m, 3H), 7.31 (m, 2H), 7.14 (t, IH), 4.61 (m, 2H), 3.65 . MASS = 478.16

합성예 377 : 1-(2,2-디페닐아세틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 377: 1- (2,2-Diphenylacetyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(2,2-디페닐아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 377 화합물을 수득하였다(수율=59%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 377 (yield = 59%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (dd, 2H), 7.36(m, 6H), 7.34(m, 5H), 7.31(m, 4H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.80(s, 1H). MASS=502.19 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 (s, 3H), 2.80 (s, IH), 3.61 (m, 2H) . MASS = 502.19

합성예 378 : 1-(2,2-디페닐에틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 378: 1- (2,2-Diphenylethyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-

1-(2,2-디페닐에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 378 화합물을 수득하였다(수율=73%).1- (2,2-diphenylethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 378 (yield = 73%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (dd, 2H), 7.36(m, 6H), 7.34(m, 5H), 7.31(m, 4H), 7.14(t, 1H), 4.61(m, 2H), 4.23(s, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.80(s, 1H). MASS=488.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 2H), 3.65 (s, 2H), 3.65 (s, 3H), 3.45 (s, 3H) , 2.80 (s, 1 H). MASS = 488.21

합성예 381 : N-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 381: N-ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 381 화합물을 수득하였다(수율=72%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 381 (yield = 72%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39(dd, 2H), 7.36(d, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 4.28(m, 2H), 4.61(m, 2H), 3.65(s, 1H, -OH), 1.31(s, 3H). MASS=322.13 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (s, 3H), 3.31 (s, 3H), 2.40 (s, 3H) . MASS = 322.13

합성예 382 : N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 382: N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 382 화합물을 수득하였다(수율=46%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 382 (yield = 46%).

1H NMR(400 MHz, CDCl3)δ 9.23(dd, 2H), 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.88(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H). MASS=304.12 1 H NMR (400 MHz, CDCl 3) δ 9.23 (dd, 2H), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH). MASS = 304.12

합성예 384 : N-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 384: N-Ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-(메틸아미노)페닐)메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 384 화합물을 수득하였다(수율=77%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 384 (yield = 77%).

1H NMR(400 MHz, CDCl3)δ 9.23(dd, 2H), 8.28(d, 1H), 8.14(d, 1H), 8.0(s, 1H), 7.88(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18 (s, 1H), 4.28(m, 2H), 1.31(s, 3H). MASS=318.14 1 H NMR (400 MHz, CDCl 3) δ 9.23 (dd, 2H), 8.28 (d, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.88 (dd, 2H), 7.31 (t, 1H), 7.14 (s, 1H), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH), 4.28 (m, MASS = 318.14

합성예 385 : N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 385: N-Ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 385 화합물을 수득하였다(수율=79%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 385 (yield = 79%).

1H NMR(400MHz,CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.21(m, 2H), 1.04(s, 3H). MASS=216.09 1 H NMR (400MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.14 (t, IH), 3.21 (m, 2H), 1.04 (s, 3H). MASS = 216.09

합성예 389: N-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 389: N- (Methoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 메톡시메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 389 화합물을 수득하였다(수율=79%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), methoxymethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 389 (yield = 79%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.30(s, 3H). MASS=232.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.30 (s, 3H). MASS = 232.08

합성예 390: N-(브로모메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 390: N- (Bromomethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 브로모메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 390 화합물을 수득하였다(수율=69%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), bromomethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 390 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H). MASS= 232.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H). MASS = 232.08

합성예 391 : N-(클로로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 391: N- (Chloromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 클로로메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 391 화합물을 수득하였다(수율=69%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), chloromethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 391 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H). MASS = 236.04 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H). MASS = 236.04

합성예 392 : N-(플루오로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 392: N- (fluoromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 플루오로메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 392 화합물을 수득하였다(수율=43%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), fluoromethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 392 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H). MASS= 220.06 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H). MASS = 220.06

합성예 393 : N-(하이드록시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 393: N- (hydroxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아미노메탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 393 화합물을 수득하였다(수율=56%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), aminomethanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 393 (yield = 56%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.56(s, 1H, -OH). MASS=218.07 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.56 (s, IH, -OH). MASS = 218.07

합성예 394 : N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 394: N- (Nitromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 니트로메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 394 화합물을 수득하였다(수율=43%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), nitromethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 394 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H). MASS= 247.06 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H). MASS = 247.06

합성예 396 : N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 396: N- (2-Hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-아미노에탄올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 396 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-aminoethanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 396 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.47 (m, 2H), 3.61 (m, 2H), 3.65 (s, 1H, -OH). MASS = 232.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.47 (m, 2H), 3.61 (m, 2H), 3.65 (s, MASS = 232.08

합성예 397 : 2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 397: 2-Oxo-N-propyl-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 397 화합물을 수득하였다(수율= 44%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), propan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 h. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 397 (yield = 44%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.47(m, 2H), 3.61(m, 2H), 3.65(s, 3H). MASS = 230.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.47 (m, 2H), 3.61 (m, 2H), 3.65 (s, 3H). MASS = 230.11

합성예 399 : (E)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 399: (E) -2-Oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (E)-프로프-1-엔-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 399 화합물을 수득하였다(수율= 53%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). Amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 399 (yield = 53%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H, -NH), 8.14(d, 1H), 8.0(s, 2H, -HH), 7.31(t, 1H), 7.14(t, 1H), 7.11(s, 1H), 5.13(s, 1H), 2.05(s, 1H). MASS= 228.09 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.0 (s, 2H, -HH), 7.31 (t, 1H), 7.14 (t, 1H ), 7.11 (s, 1 H), 5.13 (s, 1 H), 2.05 (s, 1 H). MASS = 228.09

합성예 402 : N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation Example 402: Preparation of N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-메톡시에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 402 화합물을 수득하였다(수율=59%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-methoxyethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 402 (yield = 59%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.04(m, 2H), 3.30(s, 3H). MASS=246.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 (m, 2H), 3.30 (s, 3H). MASS = 246.10

합성예 403 : N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 403: N- (2-Bromoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-브로모에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 403 화합물을 수득하였다(수율= 63%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-bromoethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 403 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.04(m, 2H). MASS=294.00 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 (m, 2H). MASS = 294.00

합성예 405 : N-(2-클로로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 405: N- (2-Chloroethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-클로로에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 405 화합물을 수득하였다(수율=63%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-chloroethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 405 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.04(m, 2H). MASS=250.05 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 (m, 2H). MASS = 250.05

합성예 406 : N-(2-플루오로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 406: N- (2-Fluoroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-플루오로에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 406 화합물을 수득하였다(수율= 49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-fluoroethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 406 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.04(m, 2H). MASS=234.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 (m, 2H). MASS = 234.08

합성예 407 : N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 407: N- (2-Hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-아미노에탄올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 407 화합물을 수득하였다(수율=72%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-aminoethanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 407 (yield = 72%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.65(s, 1H, -OH), 3.04(m, 2H). MASS=232.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.65 (s, IH, -OH), 3.04 (m, 2H). MASS = 232.08

합성예 408 : N-(2-니트로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 408: N- (2-Nitroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-니트로에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 408 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-nitroetanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 408 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.76(m, 2H), 3.04(m, 2H). MASS=261.07 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 (m, 2H). MASS = 261.07

합성예 409 : N-(3-하이드록시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 409: Synthesis of N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-아미노프로판-1-올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 409 화합물을 수득하였다(수율= 43%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-aminopropane-1-ol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 409 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s,. 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.65(s, 1H, -OH), 3.50 (m, 2H), 3.18(m, 2H), 1.58(m, 2H). MASS=246.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s ,. 1H, -NH), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H). MASS = 246.10

합성예 410 : (E)-2-옥소-N-(펜트-3-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis 410: (E) -2-Oxo-N- (pent-3-en-1-yl) -1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (E)-펜트-3-엔-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 410 화합물을 수득하였다(수율= 71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (E) -pent-3-en-1 -amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 410 (yield = 71%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 5.48(m, 2H), 3.20(m, 2H), 2.22(m, 2H), 2.05(s, 3H). MASS=256.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 5.48 (m, 2H), 3.20 (m, 2H), 2.22 (m, 2H), 2.05 (s, 3H). MASS = 256.12

합성예 411 : N-부틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 411: N-Butyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 부탄-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 411 화합물을 수득하였다(수율=49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), butan-1-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 411 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.18(m, 2H), 1.51(m, 2H), 1.31(m, 2H), 0.90(s, 3H). MASS=244.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 1.31 (m, 2H), 0.90 (s, 3H). MASS = 244.12

합성예 412 : N-(3-메톡시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 412: Synthesis of N- (3-methoxypropyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-메톡시프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 412 화합물을 수득하였다(수율= 56%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-methoxypropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at ambient temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 412 (yield = 56%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.30(s, 3H), 3.18(m, 2H), 1.51(m, 2H), 1.31(m, 2H). MASS=260.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.30 (s, 3H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 260.12

합성예 413 : N-(3-브로모프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 413: N- (3-Bromopropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-브로모프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 413 화합물을 수득하였다(수율= 81%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-bromopropane-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 413 (yield = 81%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.18(m, 2H), 1.51(m, 2H), 1.31(m, 2H). MASS=308.02 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 308.02

합성예 414 : N-(3-클로로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis 414: N- (3-Chloropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-클로로프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 414 화합물을 수득하였다(수율=81%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-chloropropane-1-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain Synthesis Example 414 (yield = 81%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.18(m, 2H), 1.51 (m, 2H), 1.31(m, 2H). MASS=264.07 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 264.07

합성예 415 : N-(3-플루오로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 415: N- (3-Fluoropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-플루오로프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 415 화합물을 수득하였다(수율= 49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-fluoropropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 415 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.18(m, 2H), 1.51(m, 2H), 1.31(m, 2H). MASS=248.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 248.10

합성예 416 : (E)-N-(헥스-4-엔-1-일)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 416: (E) -N- (hex-4-en-1-yl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (E)-헥스-4-엔-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 416 화합물을 수득하였다(수율= 71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (E) -hex-4-en-1 -amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 416 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H, -NH), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.31(t, 1H), 7.14(t, 1H), 5.48(d, 2H), 3.18(m, 2H), 2.18(m, 2H), 2.05(s, 3H), 1.69(m, 2H). MASS = 270.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.31 ( 2H), 2.18 (m, 2H), 2.05 (s, 3H), 1.69 (m, 2H). MASS = 270.14

합성예 417 : N-(3-하이드록시프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 417: N- (3-Hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-아미노프로판-1-올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 417 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-aminopropane-1-ol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 417 (yield = 71%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65(s, 1H, -OH), 3.50(m, 2H), 3.18(m, 2H), 1.58(m, 2H). MASS= 246.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H). MASS = 246.10

합성예 418 : N-(3-니트로프로필)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 418: N- (3-Nitropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-니트로프로판-1-아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 418 화합물을 수득하였다(수율=46%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-nitropropan-l-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 418 (yield = 46%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.50(m, 2H), 3.18(m, 2H), 1.58(m, 2H). MASS=275.09 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H). MASS = 275.09

합성예 419 : N-(4-하이드록시부틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 419: N- (4-Hydroxybutyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-아미노부탄-1-올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 419 화합물을 수득하였다(수율= 68%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-aminobutan-1-ol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 419 (yield = 68%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.65(s, 1H, -OH), 3.50(s, 2H), 3.18(m, 2H), 1.53(m, 2H), 1.52(m, 2H). MASS = 260.12 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 1.53 (m, 2H), 1.52 (m, 2H), 7.31 (t, , 2H). MASS = 260.12

합성예 420 : N-(3,4-디하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 420: Synthesis of N- (3,4-dihydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(아미노메틸)벤젠-1,2-디올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 420 화합물을 수득하였다(수율= 49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (aminomethyl) benzene-1,2-diol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 420 (yield = 49%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.80(s, 1H), 6.75 (d, 1H), 6.66(d, 1H), 5.35(m, 2H, -OH). MASS=310.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 6.80 (s, IH), 6.75 (d, IH), 6.66 (d, IH), 5.35 (m, 2H, -OH). MASS = 310.10

합성예 421 : N-(3,4-디에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 421: Synthesis of N- (3,4-diethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (5,6,7,8-테트라하이드로나프탈렌-2-일)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 420 화합물을 수득하였다(수율=67%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (5,6,7,8-tetrahydronaphthalen-2-yl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 420 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 7.12(d, 1H), 7.11(s, 1H), 7.00(d, 1H), 2.60(m, 4H), 1.25(s, 6H). MASS=334.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (d, . MASS = 334.17

합성예 422 : N-(3,4-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 422: N- (3,4-Dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (3,4-디메틸페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 422 화합물을 수득하였다(수율= 71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (3,4-dimethylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 422 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.99(d, 1H), 6.98 (s, 1H), 6.92(d, 1H), 4.34(m, 2H), 2.34(s, 6H). MASS=306.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 6.99 (d, IH), 6.98 (s, IH) . MASS = 306.14

합성예 423 : N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 423: N- (3,4-Dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)벤젠-1,2-디올(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 423 화합물을 수득하였다(수율= 63%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) benzene-1,2-diol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 423 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.86(s, 1H), 6.68(d, 1H), 6.73(d, 1H), 5.35(s, 2H, -OH), 3.55(m, 2H), 2.83(m, 2H). MASS=324.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 6.86 (s, IH), 6.68 (d, IH) , &Lt; / RTI &gt; 2H), 2.83 (m, 2H). MASS = 324.11

합성예 428 : N-(3,4-디에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 428: N- (3,4-diethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(3,4-디에틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 428 화합물을 수득하였다(수율= 57%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (3,4-diethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 428 (yield = 57%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.19(d, 1H), 7.17(s, 1H), 7.14(t, 1H), 3.55(m, 2H), 2.83(m, 2H), 2.60(m, 4H), 1.25(m, 6H). MASS=348.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.19 (d, IH), 7.17 (s, IH), 7.14 (m, 2H) , &Lt; / RTI &gt; 1.25 (m, 6H). MASS = 348.18

합성예 429 : N-(3,4-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 429: Synthesis of N- (3,4-dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(3,4-디메틸페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 429 화합물을 수득하였다(수율=62%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (3,4-dimethylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 429 (yield = 62%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 7.06(d, 1H), 7,04(s, 1H), 6.79(d, 1H), 3.55(m, 2H), 2.83(m, 2H), 2.34(s, 6H). MASS = 320.15 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 7.36 (t, 1H), 7.06 (d, 1H), 7.04 (s, 1H), 6.79 (d, 1H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 MASS = 320.15

합성예 430 : N-(벤조[d][1,3]디옥솔-5-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 430: Synthesis of N- (benzo [d] [1,3] dioxol-5-ylmethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 벤조[d][1,3]디옥솔-5-일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 430 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), benzo [d] [1,3] dioxol-5-ylmethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 430 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 7.03(s, 1H), 6.81(d, 1H), 6.76(d, 1H), 6.07(s, 2H), 4.34(m, 2H). MASS=322.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 4.34 (m, 2H), 7.31 (d, IH), 7.31 (s, . MASS = 322.10

합성예 431 : N-(2-(벤조[d][1,3]디옥솔-5-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 431: Synthesis of N- (2- (benzo [d] [1,3] dioxol-5-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(벤조[d][1,3]디옥솔-5-일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 431 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (benzo [d] [1,3] dioxol-5-yl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours . The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 431 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 7.03(s, 1H), 6.81(d, 1H), 6.76(d, 1H), 6.07(s, 2H), 4.34(m, 2H), 3.4(m, 2H). MASS=336.11 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 4.34 (m, 2H), 7.31 (d, IH), 7.31 (s, , &Lt; / RTI &gt; 3.4 (m, 2H). MASS = 336.11

합성예 432 : N-(나프탈렌-2-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 432: Synthesis of N- (naphthalen-2-ylmethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 나프탈렌-2-일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 432 화합물을 수득하였다(수율=43%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), naphthalene-2-ylmethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 432 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.01 (d, 1H), 8.0(s, 1H, -NH), 7.97(d, 1H), 7.94 (d, 1H), 7.58(t, 1H), 7.55 (t, 1H), 7.46(d, 1H), 7.36 (d, 1H), 7.31(t, 1H), 7.18(d, 1H), 7.14(t, 1H), 4.45(m, 2H) MASS = 328.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH ), 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH), 7.55 , 7.18 (d, IH), 7.14 (t, IH), 4.45 (m, 2H) MASS = 328.12

합성예 433 : N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 433: Synthesis of N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(나프탈렌-2-일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 433 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (naphthalen-2-yl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 433 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.01(d, 1H), 8.0(s, 1H, -NH), 7.97(d, 1H), 7.94(d, 1H), 7.58(t, 1H), 7.55(t, 1H), 7.46(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.18(d, 1H), 7.14(t, 1H), 3.55 (m, 2H), 2.94(m, 2H). MASS=342.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH ), 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH), 7.55 , 7.18 (d, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.94 (m, 2H). MASS = 342.14

합성예 437 : N-([1,1'-비페닐]-4-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 437: Synthesis of N - ([1,1'-biphenyl] -4-ylmethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), [1,1'-비페닐]-4-일메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 437 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), [1,1'-biphenyl] -4-yl methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 437 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55(m, 4H), 7.41(t, 1H), 7.36(d, 1H), 7.33(m, 3H), 7.29(dd, 2H), 7.14(t, 1H), 4.34(m, 2H). MASS=354.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H ), 7.41 (t, IH), 7.36 (d, IH), 7.33 (m, 3H), 7.29 (dd, 2H), 7.14 (t, MASS = 354.14

합성예 438 : N-(2-([1,1'-비페닐]-4-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 438: Synthesis of N- (2 - ([1,1'-biphenyl] -4-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-([1,1'-비페닐]-4-일)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 438 화합물을 수득하였다(수율=53%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2 - ([1,1'-biphenyl] -4-yl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 438 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55(m, 4H), 7.41(t, 1H), 7.36(d, 1H), 7.33(m, 3H), 7.29(dd, 2H), 7.14(t, 1H), 4.34(m, 2H), 3.2(m, 2H). MASS = 368.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 2H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H) . MASS = 368.15

합성예 439: N-(4-벤질벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthetic Example 439: N- (4-benzylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-벤질페닐)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 439 화합물을 수득하였다(수율=71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-benzylphenyl) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 439 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.55(m, 4H), 7.41(t, 1H), 7.36(d, 1H), 7.33(m, 3H), 7.29(dd, 2H), 7.14(t, 1H), 4.34(m, 2H), 2.94(m, 2H). MASS=368.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 2H), 4.94 (m, 2H), 2.94 (m, 2H), 7.41 (t, . MASS = 368.15

합성예 440 : N-(4-벤질펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 440: Synthesis of N- (4-benzylphenethyl) -2-oxo-1,2-dihydroquinoline-3-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-벤질페닐)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 440 화합물을 수득하였다(수율= 64%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-benzylphenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 440 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55(m, 4H), 7.41(t, 1H), 7.36(d, 1H), 7.33(m, 3H), 7.29(dd, 2H), 7.14(t, 1H), 4.34(m, 2H), 3.1(m, 2H), 2.94(m, 2H). MASS=382.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 1H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H) , &Lt; / RTI &gt; 2.94 (m, 2H). MASS = 382.17

합성예 441: N-(에톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 441: N- (Ethoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 에톡시메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 441 화합물을 수득하였다(수율= 52%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), ethoxymethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 441 (yield = 52%).

1H NMR 400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.5(m, 2H), 1.10(s, 3H). MASS=246.10 1 H NMR 400 MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS = 246.10

합성예 442 : N-((에틸티오)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 442: Synthesis of N - ((ethylthio) methyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (에틸티오)메타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하고 실리카 겔 크로마토그래프로 정제하여 합성예 442 화합물을 수득하였다(수율= 71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (ethylthio) methanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water and purified by silica gel chromatography to obtain the compound of Synthesis Example 442 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.5(m, 2H), 1.10(s, 3H). MASS=262.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS = 262.08

합성예 443 : N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 443: N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-메톡시에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 443 화합물을 수득하였다(수율= 62%)Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-methoxyethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 443 (yield = 62%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.5(m, 2H), 1.10(s, 3H). MASS=246.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS = 246.10

합성예 444 : N-((에틸아미노)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 444: N - ((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸메탄디아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 444 화합물을 수득하였다(수율= 71%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethylmethanediamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 444 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.5(m, 2H), 2.0(s, 1H, -NH), 1.10(s, 3H). MASS=245.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 2.0 (s, IH, -NH), 1.10 (s, MASS = 245.12

합성예 445 : N-(2-(메틸티오)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 445: Synthesis of N- (2- (methylthio) ethyl) -2-oxo-1,2-dihydroquinoline-

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(메틸티오)에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 445 화합물을 수득하였다(수율= 49%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (methylthio) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 445 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H), 3.5(m, 2H), 1.10(s, 3H). MASS=262.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS = 262.08

합성예 446 : N-(2-(메틸아미노)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 446: N- (2- (Methylamino) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide

합성예 25 화합물(1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N1-메틸에탄-1,2-디아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 446 화합물을 수득하였다(수율=61%).Synthesis Example 25 The compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N1-methylethane-1,2-diamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 446 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS= 245.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H). MASS = 245.12

단계(f-6)의 일반적 과정General procedure of step (f-6)

브롬(0.65 mL, 12.73 mmol) 브롬을 피리딘(15 mL)으로 용해시킨 5번 화합물의 산 현탄액(1.49 g, 6.36 mmol)에 0℃에서 적상하고, 혼합물을 110℃에서 40분간 교반하였다. 짙은 갈색의 용액을 상온까지 냉각시키고 1NHCl(50mL)에 부었다. 침전물을 수집하여 1NHCl로 세척하고 다시 물로 세척한 뒤 건조시켜 6번 화합물을 수득하였다.Bromine (0.65 mL, 12.73 mmol) was bubbled into an acidic suspension (1.49 g, 6.36 mmol) of compound No. 5 in which bromine was dissolved in pyridine (15 mL) at 0 ° C and the mixture was stirred at 110 ° C for 40 minutes. The dark brown solution was cooled to room temperature and poured into 1 N HCl (50 mL). The precipitate was collected, washed with 1N HCl, again washed with water, and dried to obtain compound No. 6.

합성예 7 : 3-브로모퀴놀린-2(1H)-온Synthesis Example 7: 3-Bromoquinolin-2 (1H) -one

브롬(0.65 mL, 12.73 mmol)을 0℃에서 피리딘(15 mL)에 용해된 2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드 현탄액(1.49 g, 6.36 mmol)에 적상하고, 혼합물을 110℃에서 40분간 교반하였다(수율=61%).Bromo (0.65 mL, 12.73 mmol) was added dropwise to a solution of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid acid (1.49 g, 6.36 mmol) dissolved in pyridine (15 mL) The mixture was stirred at 110 &lt; 0 &gt; C for 40 minutes (yield = 61%).

1H NMR(400 MHz, CDCl3) 8.14(d, 1H), 8.0(s, 1H, -NH), 7.81(s, 1H), 7.36 (d, 1H), 7.31(t, 1H), 7.14(t, 1H). MASS=222.96 1 H NMR (400 MHz, CDCl 3) 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 ( t, 1 H). MASS = 222.96

합성예 8 : 3,5-디브로모퀴놀린-2(1H)-온Synthesis Example 8: 3,5-Dibromoquinolin-2 (1H) -one

브롬(0.65 mL, 12.73 mmol)을 0℃에서 피리딘(15 mL)에 용해시킨 5-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1.49 g, 6.36 mmol) 현탄액에 적상하고 혼합물을 110℃에서 40분간 교반하였다(수율=64%).Bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1.49 g, 6.36 mmol) dissolved in pyridine (15 mL) at 0 & And the mixture was stirred at 110 캜 for 40 minutes (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 8.08(d, 1H), 8.0(s, 1H, -NH), 7.81(s, 1H), 7.29 (d, 1H), 7.05(t, 1H). MASS=300.87 1 H NMR (400 MHz, CDCl 3 )? 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.29 (d, 1H), 7.05 MASS = 300.87

합성예 9 : 3,6-디브로모퀴놀린-2(1H)-온Synthesis Example 9: Synthesis of 3,6-dibromoquinolin-2 (1H) -one

브롬(0.65 mL, 12.73 mmol)을 0℃에서 피리딘(15 mt)에 용해시킨 6-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드 현탄액(1.49g, 6.36 mmol)에 적상하고 혼합물을 110℃에서 40분간 교반하였다(수율=66%).Bromo-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid salt solution (1.49 g, 6.36 mmol) in which bromine (0.65 mL, 12.73 mmol) was dissolved in pyridine (15 mt) ) And the mixture was stirred at 110 DEG C for 40 minutes (yield = 66%).

1H NMR(400 MHz, CDCl3)δ8.0 (s, 1H, -NH), 7.81(s, 1H), 7.55(d, 1H), 7.53 (d, 1H), 7.46(d, 1H). MASS=300.87 1 H NMR (400 MHz, CDCl 3) δ8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H). MASS = 300.87

합성예 10 : 3,7-디브로모퀴놀린-2(1H)-온Synthesis Example 10: Synthesis of 3,7-dibromoquinolin-2 (1H) -one

브롬(0.65 mL, 12.73 mmol)을 0℃에서 피리딘(15 mL)에 용해시킨 7-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드 현탄액(1.49 g, 6.36 mmol)에 적상하고 혼합물을 110℃에서 40분간 교반하였다(수율=62%).Bromo-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid acid solution (1.49 g, 6.36 mmol) in which bromine (0.65 mL, 12.73 mmol) was dissolved in pyridine ) And the mixture was stirred at 110 DEG C for 40 minutes (yield = 62%).

1H NMR (400 MHz, CDCl3)δ 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.81 (s, 1H), 7.29 (d, 1H), 7.25 (d, 1H). MASS= 300.87 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.81 (s, 1H), 7.29 (d, 1H), 7.25 (d, 1H). MASS = 300.87

단계(g-7)의 일반적 과정General procedure of step (g-7)

둥근바닥 플라스크에 Pd(OAC)2(3.6mg, 0.1mmol), 잔포스(4.7mg, 0.05mmol), 고형 반응물(1.0 mmol 보호기 결합 퀴놀리논, 1.5 mmol 아민) 및 Cs2CO3(104mg,2mmol)을 채워 넣었다. 둥근바닥 플라스크를 고무마개로 막고 비운 뒤 질소를 다시 채워 넣었다. 이러한 비우기/채우기를 한번 더 반복하였다. 액상 반응물 및 1,4-디옥산(1mL)을 마개를 통해 주입하였다. 플라스크를 밀봉하고 혼합물을 100℃에서 10시간 동안 교반하였다. 수득한 현탄액을 상온까지 냉각시키고 여과한 후 농축하여 실리카겔 컬럼크로마토그래피로 정제하여 7번 화합물을 수득하였다.A round bottom flask was charged with Pd (OAC) 2 (3.6 mg, 0.1 mmol), Zafos (4.7 mg, 0.05 mmol), solid reactant (1.0 mmol protecting group bound quinolinone, 1.5 mmol amine) and Cs 2 CO 3 2mmol). The round bottom flask was closed with a rubber boot and emptied of nitrogen. This emptying / filling was repeated once more. Liquid reaction product and 1,4-dioxane (1 mL) were injected through the stopper. The flask was sealed and the mixture was stirred at 100 &lt; 0 &gt; C for 10 hours. The obtained current tan solution was cooled to room temperature, filtered, concentrated, and purified by silica gel column chromatography to obtain Compound No. 7.

합성예 447 : 3-(페닐아미노)퀴놀린-2(1H)-온Synthesis Example 447: 3- (Phenylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 447 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), aniline (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 447 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH). MASS=236.09 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 236.09

합성예 448 : 3-(p-톨일아미노)퀴놀린-2(1H)-온Synthesis Example 448: Synthesis of 3- (p-tolylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), p-톨루이딘(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 448 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), p-toluidine (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 448 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH), 2.3(s, 3H). MASS=250.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, MASS = 250.11

합성예 449 : 3-((4-메톡시페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 449: Synthesis of 3 - ((4-methoxyphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-메톡시아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 449 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-methoxyaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 449 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH), 2.5(s, 3H). MASS=266.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, IH), 6.43 (dd, 2H), 4.0 (s, IH, -NH), 2.5 (s, 3H). MASS = 266.11

합성예 450 : 3-((4-브로모페닐)아미노)퀴놀린-2(1H)-온Synthesis 450: 3 - ((4-Bromophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-브로모아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 450 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-bromoaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain a compound of Synthesis Example 450 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH). MASS=314.01 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 314.01

합성예 451 : 3-((4-클로로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 451: 3 - ((4-Chlorophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2 (0.15 mmol), 4-클로로아닐린 (1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 451 화합물을 수득하였다(수율=49%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-chloroaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 451 (yield = 49%).

1H NMR (400 MHz, CDCl3)δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH). MASS = 270.06 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 270.06

합성예 452 : 3-((4-플루오로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 452: 3 - ((4-Fluorophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-플루오로아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 452 화합물을 수득하였다(수율=43%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-fluoroaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 452 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH). MASS=254.09 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 254.09

합성예 453 : 3-((4-에틸페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 453: Synthesis of 3 - ((4-ethylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산 (2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-에틸아닐린 (1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 453 화합물을 수득하였다(수율=49%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-ethyl aniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 453 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH), 2.6(m, 2H), 1.25(s, 3H). MASS=264.13 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.6 (m, 2H), 1.25 MASS = 264.13

합성예 454 : 3-((4-하이드록시페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 454: Synthesis of 3 - ((4-hydroxyphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-아미노페놀(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 454 화합물을 수득하였다(수율=53%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-aminophenol (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 454 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH). MASS=252.09 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 252.09

합성예 455 : 3-((4-니트로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 455: Synthesis of 3 - ((4-nitrophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-니트로아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 455 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-nitroaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 455 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH). MASS=281.08 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.81 (t, 1 H), 6.43 (dd, 2 H), 4.0 (s, 1 H, -NH). MASS = 281.08

합성예 456 : 3-((4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 456: Synthesis of 3 - ((4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (4-아미노페닐)메탄올(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 456 화합물을 수득하였다(수율=49%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). To the reaction mixture was added Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), (4-aminophenyl) methanol (1.3 mmol) and Zanphor (0.15 mmol) Respectively. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 456 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH), 2.6(m, 2H). MASS=266.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, IH), 6.43 (dd, 2H), 4.0 (s, IH, -NH), 2.6 (m, 2H). MASS = 266.11

합성예 457 : 3-((4-비닐페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 457: Synthesis of 3 - ((4-vinylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-비닐아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 457 화합물을 수득하였다(수율=41%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-vinyl aniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 457 (yield = 41%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.63(s, 1H), 6.43(dd, 2H), 5.61(s, 1H), 5.18(s, 1H), 4.0(s, 1H, -NH). MASS=262.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (s, 1H), 6.63 (s, 1H), 6.43 (sd, 2H) . MASS = 262.11

합성예 458 : N,N-디메틸-4-((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)벤젠설폰아미드Synthesis Example 458: Synthesis of N, N-dimethyl-4 - ((2-oxo-1,2-dihydroquinolin-3-yl) amino) benzenesulfonamide

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-아미노-N,N-디메틸벤젠 설폰아미드(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 458 화합물을 수득하였다(수율=63%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). To the reaction mixture was added Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-amino-N, N-dimethylbenzenesulfonamide (1.3 mmol) Lt; / RTI &gt; for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 458 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.81(t, 1H), 6.63(s, 1H), 6.43(dd, 2H), 4.0(s, 1H, -NH), 2.66(m, 6H). MASS=343.10 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (s, 1H), 6.63 (s, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, MASS = 343.10

합성예 459 : 3-(벤질아미노)퀴놀린-2(1H)-온Synthetic example 459: 3- (Benzylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 에틸벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 459 화합물을 수득하였다(수율=41%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), ethylbenzene (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 459 (yield = 41%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=250.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 250.11

합성예 460 : 3-((4-메틸벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 460: Synthesis of 3 - ((4-methylbenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-에틸-4-메틸벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 460 화합물을 수득하였다(수율=68%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- ethyl-4-methylbenzenesulfonate (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 460 (yield = 68%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10 (s, 1H), 3.92(m, 2H), 2.34(s, 3H), 2.0(s, 1H, -NH). MASS=264.13 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 3H), 2.02 (s, 1H, -NH), 7.26 (t, 1H), 7.14 . MASS = 264.13

합성예 461 : 3-((4-메톡시벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 461: Synthesis of 3 - ((4-methoxybenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-에틸-4-메톡시벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 461 화합물을 수득하였다(수율=65%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- ethyl-4-methoxy-benzene was added (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 461 (yield = 65%).

1H NMR (400 MHz, CDCl3)δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.3 (s, 3H), 2.0 (s, 1H, -NH). MASS = 280.12 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, . MASS = 280.12

합성예 462 : 3-((4-브로모벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 462: 3 - ((4-Bromobenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-브로모-4-에틸벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 462 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- bromo-4-ethylbenzene, a (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 462 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=328.02 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 328.02

합성예 463 : 3-((4-클로로벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 463: 3 - ((4-Chlorobenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-클로로-4-에틸벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 463 화합물을 수득하였다(수율=60%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- chloro-4-ethylbenzene (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain Synthesis Example 463 (yield = 60%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=284.07 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 284.07

합성예 464 : 3-((4-플루오로벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 464: 3 - ((4-fluorobenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-에틸-4-플루오로벤젠(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 464 화합물을 수득하였다(수율=68%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- ethyl-4-fluoro-benzene (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and by 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 464 (yield = 68%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=268.10 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 268.10

합성예 465 : 3-((4-에틸벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 465: 3 - ((4-Ethylbenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1,4-디에틸벤젠(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 465 화합물을 수득하였다(수율=42%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 1,4-diethylbenzene (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C. for 10 hours Respectively. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain Synthesis Example 465 (yield = 42%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.6(m, 2H), 2.0(s, 1H, -NH), 1.25(s, 3H). MASS=278.14 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 2H), 7.26 (t, 1H), 7.14 (t, IH), 6.10 (s, IH), 3.92 (m, , 1.25 (s, 3 H). MASS = 278.14

합성예 466 : 3-((4-하이드록시벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 466: 3 - ((4-Hydroxybenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (4-에틸페닐)메탄올(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 466 화합물을 수득하였다(수율= 61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), (4- ethylphenyl) methanol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and stirred at 100 for 10 ℃ sigan Respectively. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 466 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=266.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 266.11

합성예 467 : 3-((4-니트로벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 467: 3 - ((4-nitrobenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-에틸-4-니트로벤젠(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 467 화합물을 수득하였다(수율= 61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- ethyl-4-nitrobenzene (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 467 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH). MASS=295.10 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (d, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 295.10

합성예 468 : N,N-디메틸-4-(((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)메틸)벤젠설폰아미드Synthesis Example 468: Synthesis of N, N-dimethyl-4 - (((2-oxo-1,2-dihydroquinolin-3-yl) amino) methyl) benzenesulfonamide

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-(아미노메틸)-N,N-디메틸벤젠 설폰아미드(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 468 화합물을 수득하였다(수율=64%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). To the reaction mixture was added Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4- (aminomethyl) -N, N-dimethylbenzenesulfonamide (1.3 mmol) And stirred at 100 &lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 468 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.33 (dd, 2H), 7.31(t, 1H), 7.23(dd, 2H), 7.26(t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.66(m, 6H), 2.0(s, 1H, -NH). MASS=357.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (m, 2H), 2.66 (m, 6H), 2.0 (s, IH, -NH), 7.26 (t, . MASS = 357.11

합성예 469 : 3-((4-(하이드록시메틸)벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 469: Synthesis of 3 - ((4- (hydroxymethyl) benzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (4-에틸페닐)메탄올(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 469 화합물을 수득하였다(수율= 53%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), (4- ethylphenyl) methanol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and stirred at 100 for 10 ℃ sigan Respectively. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 469 (yield = 53%).

1H NMR (400 MHz, CDCl3)δ8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(m, 2H), 7.16(dd, 2H), 7.14(t, 1H), 7.11(dd, 2H), 4.61(m, 2H), 3.65(s, 1H, -OH), 2.0 (s, 1H, -NH). MASS=280.12 1 H NMR (400 MHz, CDCl 3) δ8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 2H), 7.16 (dd, 2H), 7.14 (t, 1H), 2H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 2.0 (s, 1H, MASS = 280.12

합성예 470 : 3-((4-비닐벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 470: Synthesis of 3 - ((4-vinylbenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 1-에틸-4-비닐벤젠(1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 470 화합물을 수득하였다(수율=63%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 1- ethyl-4-vinyl-benzene (1.3 mmol) and the balance force added (0.15 mmol) to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 470 (yield = 63%).

1H NMR(400 MHz, CDCl3) δ8.14(d, 1H), 8.0(s, 1H, -NH), 7.59(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.18(dd, 2H), 7.14(t, 1H), 6.63(s, 1H), 6.1(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 3.92(m, 2H). MASS=276.13 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.59 (dd, 2H), 7.36 1H), 7.18 (s, 1H), 6.92 (s, 1H), 7.18 (s, 1H). MASS = 276.13

합성예 471 : 3-(메틸(페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 471: Synthesis of 3- (methyl (phenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol,)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 471 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), N-methylaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 471 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 3.44(s, 3H). MASS=250.11 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 3.44 (s, 3H). MASS = 250.11

합성예 472 : 3-(에틸(페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 472: Synthesis of 3- (ethyl (phenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-에틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 472 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), N-ethyl aniline (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 472 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 1.31(s, 3H). MASS=264.13 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H), 1.31 MASS = 264.13

합성예 473 : 3-(에틸(p-톨일)아미노)퀴놀린-2(1H)-온Synthesis Example 473: Synthesis of 3- (ethyl (p-tolyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-에틸-4-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 473 화합물을 수득하였다(수율=60%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- ethyl-4-methyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 473 (yield = 60%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=278.14 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, MASS = 278.14

합성예 474 : 3-(메틸(p-톨일)아미노)퀴놀린-2(1H)-온Synthesis Example 474: Synthesis of 3- (methyl (p-tolyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N,4-디메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 474 화합물을 수득하였다(수율=52%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), N, 4-dimethylaniline (1.3 mmol) and Zafos (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours . The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 474 (yield = 52%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 7.01(dd, 2H), 6.83(s, 1H), 6.13(dd, 2H), 3.44(s, 3H), 2.34(s, 3H). MASS=264.13 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (d, 2H), 6.83 (s, 1H), 6.13 (dd, 2H), 3.44 (s, 3H), 2.34 (s, 3H). MASS = 264.13

합성예 475 : 3-((4-메톡시페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 475: Synthesis of 3 - ((4-methoxyphenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-메톡시-N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 475 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- methoxy -N- methyl-aniline was added (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 475 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(d, 1H), 7.14(t, 1H), 6.83(s, 1H), 6.77(dd, 2H), 6.71(dd, 2H), 3.83(s, 3H), 3.44(s, 3H). MASS=280.12 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (t, 1H), 6.83 (s, 1 H), 6.77 (dd, 2H), 6.71 (dd, 2H), 3.83 (s, 3H), 3.44 (s, 3H). MASS = 280.12

합성예 476 : 3-(에틸(4-메톡시페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 476: Synthesis of 3- (ethyl (4-methoxyphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-에틸-4-메톡시아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 476 화합물을 수득하였다(수율= 67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- ethyl-4-methoxyaniline was added (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 476 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H), 1.31(s, 3H). MASS=294.14 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, MASS = 294.14

합성예 477 : 3-((4-브로모페닐)(에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 477: 3 - ((4-Bromophenyl) (ethyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-브로모-N-에틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 477 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- bromo -N- ethyl-aniline was added (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 477 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34(s, 3H). MASS = 342.04 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 MASS = 342.04

합성예 478 : 3-((4-브로모페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 478: Synthesis of 3 - ((4-bromophenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-브로모-N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 478 화합물을 수득하였다(수율=63%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- bromo -N- methyl-aniline was added (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 478 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56 (m, 2H). MASS = 328.02 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 328.02

합성예 479 : 3-((4-클로로페닐)(에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 479: Synthesis of 3 - ((4-chlorophenyl) (ethyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-클로로-N-에틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 479 화합물을 수득하였다(수율=31%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- chloro -N- ethyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 479 (Yield = 31%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H). MASS=298.09 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 MASS = 298.09

합성예 480 : 3-((4-클로로페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 480: Synthesis of 3 - ((4-chlorophenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-클로로-N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 480 화합물을 수득하였다(수율= 61%)3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- chloro -N- methyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 480 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56 (m, 2H). MASS=284.07 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 284.07

합성예 481 : 3-((4-플루오로페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 481: 3 - ((4-Fluorophenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-플루오로-N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 481 화합물을 수득하였다(수율= 46%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), was added -N- methyl aniline (1.3 mmol) and the balance force (0.15 mmol) 4-fluoro to the reaction mixture 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 481 (yield = 46%).

1H NMR(400 MHz, CDCl3) δ8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H). MASS=268.10 1 H NMR (400 MHz, CDCl 3) δ8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 2H), 7.14 (t, 1H), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 268.10

합성예 482 : 3-(에틸(4-플루오로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 482: Synthesis of 3- (ethyl (4-fluorophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2 (0.15 mmol), N-에틸-4-플루오로아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 482 화합물을 수득하였다(수율=67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- ethyl-4-fluoro aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and by 10 hours at 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 482 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H). MASS=282.12 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 MASS = 282.12

합성예 483 : 3-(에틸(4-에틸페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 483: Synthesis of 3- (ethyl (4-ethylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N,4-디에틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 483 화합물을 수득하였다(수율=67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). To the reaction mixture was added Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), N, 4-diethylaniline (1.3 mmol) Respectively. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 483 (yield = 67%).

1H NMR(400 MHz, CDCl3) 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.60(m, 2H), 1.25(s, 3H), 2.34(s, 3H). MASS=292.16 1 H NMR (400 MHz, CDCl 3) 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 ( 2H), 2.60 (m, 2H), 1.25 (s, 3H), 2.34 (s, , 3H). MASS = 292.16

합성예 484 : 3-((4-에틸페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 484: Synthesis of 3 - ((4-ethylphenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-에틸-N-메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 484 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- ethyl -N- methyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 484 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 2.60(m, 2H), 1.25(s, 3H), 2.34(s, 3H). MASS=278.14 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 2.60 (m, 2H), 1.25 MASS = 278.14

합성예 485 : 3-(에틸(4-하이드록시페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 485: Synthesis of 3- (ethyl (4-hydroxyphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2 (0.15 mmol), 4-(에틸아미노)페놀(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 485 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- ( ethylamino) phenol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and stirred at 100 for 10 ℃ sigan Respectively. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 485 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H). MASS=280.12 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 MASS = 280.12

합성예 486 : 3-((4-하이드록시페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 486: Synthesis of 3 - ((4-hydroxyphenyl) (methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-(메틸아미노)페놀(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 486 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- ( dimethylamino) phenol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and stirred at 100 for 10 ℃ sigan Respectively. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 486 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H). MASS=266.11 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 266.11

합성예 487 : 3-(메틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 487: 3- (Methyl (4-nitrophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-메틸-4-니트로아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 487 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). (0.1 mmol) of Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), N-methyl-4-nitroaniline (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture, Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 487 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H). MASS=295.10 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 295.10

합성예 488 : 3-(에틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 488: Synthesis of 3- (ethyl (4-nitrophenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-에틸-4-니트로아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 488 화합물을 수득하였다(수율=63%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- ethyl-4-nitroaniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 488 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H). MASS=309.11 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 MASS = 309.11

합성예 489 : 3-(에틸(4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 489: Synthesis of 3- (ethyl (4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2 (0.15 mmol), (4-(에틸아미노)페닐)메탄올(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 489 화합물을 수득하였다(수율=67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). In the Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), (4- ( ethyl) phenyl) methanol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and 100 ℃ 10 Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 489 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.61(m, 2H), 4.56(m, 2H), 2.34(s, 3H). MASS=294.14 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 3H), 6.63 (s, 3H), 6.63 (s, 3H). MASS = 294.14

합성예 490 : 3-((4-(하이드록시메틸)페닐)(메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 490: 3 - ((4- (hydroxymethyl) phenyl) (methyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (4-(메틸아미노)페닐)메탄올(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 490 화합물을 수득하였다(수율=67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). In the Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), (4- ( methyl) phenyl) methanol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and 100 ℃ 10 Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain Synthesis Example 490 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(t, 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.61(m, 2H), 2.34(s, 3H). MASS=280.12 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.61 (m, 2H), 2.34 MASS = 280.12

합성예 491 : 3-(메틸(4-비닐페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 491: Synthesis of 3- (methyl (4-vinylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-메틸-4-비닐아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 491 화합물을 수득하였다(수율=43%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- vinyl-4-methyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 491 (yield = 43%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.02(dd, 2H), 8.0(s, 1H, -NH), 7.68(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H). MASS=276.13 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH). MASS = 276.13

합성예 492 : 3-(에틸(4-비닐페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 492: 3- (Ethyl (4-vinylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), N-에틸-4-비닐아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 492 화합물을 수득하였다(수율=60%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), N- ethyl-4-vinyl aniline (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture at 100 for 10 ℃ sigan Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 492 (yield = 60%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.02(dd, 2H), 8.0(s, 1H, -NH), 7.68(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.63(s, 1H), 5.61(s, 1H), 5.18(s, 1H), 1.31(s, 3H). MASS=290.14 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (s, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, MASS = 290.14

합성예 493 : 3-((3,4-디메틸페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 493: 3 - ((3,4-Dimethylphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 3,4-디메틸아닐린(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 493 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 3,4-dimethylaniline (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours . The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 493 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.86(d, 1H), 6.24(m, 1H), 6.19(d, 1H), 4.0(s, 1H, -NH), 2.34(m, 6H). MASS=264.13 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, IH), 6.24 (m, IH), 6.19 (d, IH), 4.0 (s, IH, -NH), 2.34 (m, 6H). MASS = 264.13

합성예 494 : 3-((3,4-디메틸벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 494: 3 - ((3,4-Dimethylbenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (3,4-디메틸페닐)메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 494 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). (0.1 mmol) of Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), (3,4-dimethylphenyl) methanamine (1.3 mmol) Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 494 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.86(d, 1H), 6.24(m, 1H), 6.19(d, 1H), 4.0(s, 1H, -NH), 3.2(m, 2H), 2.34(m, 6H). MASS=278.14 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, IH), 6.24 (m, IH), 6.19 (d, IH), 4.0 (s, IH, -NH), 3.2 (m, 2H), 2.34 (m, 6H). MASS = 278.14

합성예 495 : 3-((3,4-디하이드록시페닐)아미노)퀴놀린-2(1H)-온Synthesis Example 495: Synthesis of 3 - ((3,4-dihydroxyphenyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-아미노벤젠-1,2-디올(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 495 화합물을 수득하였다(수율=69%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 from the CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4- amino-benzene-1,2-diol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and 100 ℃ 10 Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 495 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.53(d, 1H), 5.97(m, 1H), 5.83(d, 1H). MASS=268.08 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, 1 H), 5.97 (m, 1 H), 5.83 (d, 1 H). MASS = 268.08

합성예 496 : 3-((3,4-디하이드록시벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 496: Synthesis of 3 - ((3,4-dihydroxybenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 4-(아미노메틸)벤젠-1,2-디올(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 496 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 4- ( aminomethyl) benzene-1,2-diol (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and 100 Lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 496 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.53(d, 1H), 5.97(m, 1H), 5.83(d, 1H), 3.2(m, 2H). MASS = 282.10 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, IH), 5.97 (m, IH), 5.83 (d, IH), 3.2 (m, 2H). MASS = 282.10

합성예 497 : 3-((벤조[d][1,3]디옥솔-5-일메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 497: 3 - ((benzo [d] [1,3] dioxol-5-ylmethyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 벤조[d][1,3]디옥솔-5-일메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 497 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), benzo [d] [1,3] dioxol-5-yl meth namin (1.3 mmol) and the balance force (0.15 mmol) the reaction mixture And the mixture was stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 497 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H) 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 7.03(m, 1H), 6.81(d, 1H), 6.76(d, 1H), 6.10(s, 1H), 6.07(m, 2H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=294.10 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 ( 2H), 6.92 (d, 1H), 6.76 (d, 1H), 6.10 (s, 1H), 6.07 (m, 2H), 3.92 (m, 2H), 2.0 (s, 1H, MASS = 294.10

합성예 498 : 3-((2-(벤조[d][1,3]디옥솔-5-일)에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 498: Synthesis of 3 - ((2- (benzo [d] [1,3] dioxol-5-yl) ethyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 2-(벤조[d][1,3]디옥솔-5-일)에타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 498 화합물을 수득하였다(수율=60%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). (1.3 mmol) and Zanphor (0.15 mmol) of Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol) ) Were added to the reaction mixture and stirred at 100 &lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 498 (yield = 60%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H) 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 7.03(m, 1H), 6.81(d, 1H), 6.76(d, 1H), 6.10(s, 1H), 6.07(m, 2H), 3.92(m, 2H), 3.02(m, 2H), 2.0(s, 1H, -NH). MASS=308.12 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 ( 2H), 3.92 (m, 2H), 3.02 (m, 2H), 2.0 (s, , 1H, -NH). MASS = 308.12

합성예 499 : 3-((나프탈렌-2-일메틸)아미노)퀴놀린-2(1H)-온Synthesis 499: 3 - ((Naphthalen-2-ylmethyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 나프탈렌-2-일메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 499 화합물을 수득하였다(수율=43%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), naphthalene-2-yl meth namin (1.3 mmol) and the balance force (0.15 mmol) was added to the reaction mixture and stirred at 100 for 10 ℃ sigan Respectively. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 499 (yield = 43%).

H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.01(d, 1H), 8.0(s, 1H, -NH), 7.97 (d, 1H), 7.94(d, 1H), 7.58(t, 1H), 7.55(t, 1H), 7.46(m, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.18(d, 1H), 7.14(t, 1H), 6.10(s, 1H), 4.03(m, 2H), 2.0(s, 1H, -NH). MASS=300.13 H NMR (400 MHz, CDCl 3 ) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 ( (t, 1H), 7.55 (t, 1H), 7.46 (m, IH), 7.36 (d, IH), 7.31 , &Lt; / RTI &gt; 1H), 4.03 (m, 2H), 2.0 (s, 1H, MASS = 300.13

합성예 500 : 3-((2-(나프탈렌-2-일)에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 500: Synthesis of 3 - ((2- (naphthalen-2-yl) ethyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 2-(나프탈렌-2-일)에타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 500 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). (0.1 mmol) of Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 2- (naphthalen-2-yl) ethanamine Stir for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 500 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.01(d, 1H), 8.0(s, 1H, -NH), 7.97 (d, 1H), 7.94(d, 1H), 7.58(t, 1H), 7.55(t, 1H), 7.46(m, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.18(d, 1H), 7.14(t, 1H), 6.10(s, 1H), 4.03(m, 2H), 3.02(m, 2H), 2.0(s, 1H, -NH). MASS=314.14 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, IH), 7.46 (m, IH), 7.36 (d, IH), 7.31 (s, 1H), 4.03 (m, 2H), 3.02 (m, 2H), 2.0 (s, 1H, MASS = 314.14

합성예 501 : 3-(([1,1'-비페닐]-4-일메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 501: Synthesis of 3 - (([1,1'-biphenyl] -4-ylmethyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), [1,1'-비페닐]-4-일메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 501 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Was added Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), [1,1'- biphenyl] -4-yl meth namin (1.3 mmol) and the balance force (0.15 mmol) to the reaction mixture And stirred at 100 &lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 501 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ8.14(d, 1H), 8.0(s, 1H, -NH), 7.52(dd, 2H), 7.51(dd, 2H), 7.41(m, 1H), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.29(dd, 2H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.0(s, 1H, -NH). MASS=326.14 1 H NMR (400 MHz, CDCl 3) δ8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 2H), 7.39 (d, 2H), 7.31 (d, 2H), 7.31 (d, (s, 1 H, -NH). MASS = 326.14

합성예 502 : 3-((2-([1,1'-비페닐]-4-일)에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 502: Synthesis of 3 - ((2 - ([1,1'-biphenyl] -4-yl) ethyl) amino) quinolin-

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 2-([1,1'-비페닐]-4-일)에타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 502 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 2 - ([1,1'- biphenyl] -4-yl) ethanone namin (1.3 mmol) and the balance force (0.15 mmol) of Was added to the reaction mixture and stirred at 100 &lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 502 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.52(dd, 2H), 7.51(dd, 2H), 7.41(m, 1H), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.29(dd, 2H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 3.6(m, 2H), 2.0(s, 1H, -NH). MASS=340.16 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 1H), 7.32 (d, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 m, 2 H), 2.0 (s, 1 H, -NH). MASS = 340.16

합성예 503 : 3-((4-벤질펜에틸)아미노)퀴놀린-2(1H)-온Synthesis Example 503: Synthesis of 3 - ((4-benzylphenethyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 3-([1,1'-비페닐]-4-일)프로판-1-아민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 503 화합물을 수득하였다(수율=67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), 3 - ([1,1'- biphenyl] -4-yl) propan-1-amine (1.3 mmol) and the balance force (0.15 mmol) were added to the reaction mixture and stirred at 100 &lt; 0 &gt; C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 503 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.52(dd, 2H), 7.51(dd, 2H), 7.41(m, 1H), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.29(dd, 2H), 7.14(t, 1H), 6.10(s, 1H), 3.92 (m, 2H), 3.6(m, 2H), 2.8(m, 2H), 2.0(s, 1H, -NH). MASS=354.17 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 1H), 7.32 (d, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 m, 2 H), 2.8 (m, 2 H), 2.0 (s, 1 H, -NH). MASS = 354.17

합성예 504 : 3-((4-벤질벤질)아미노)퀴놀린-2(1H)-온Synthesis Example 504: Synthesis of 3 - ((4-benzylbenzyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (4-벤질페닐)메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 504 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), (4- benzylphenyl) meth namin (1.3 mmol) and the balance force for (0.15 mmol) for 10 hours was added to the reaction mixture and 100 ℃ Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 504 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.52(dd, 2H), 7.51(dd, 2H), 7.41(m, 1H), 7.36(d, 1H), 7.33(dd, 2H), 7.31(t, 1H), 7.29(dd, 2H), 7.14(t, 1H), 6.10(s, 1H), 3.92(m, 2H), 2.8(m, 2H), 2.0(s, 1H, -NH). MASS = 340.16 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, IH), 7.33 (d, 2H), 7.31 (t, IH), 7.29 (dd, 2H), 7.14 m, 2 H), 2.0 (s, 1 H, -NH). MASS = 340.16

합성예 505 : 3-(에틸아미노)퀴놀린-2(1H)-온Synthesis Example 505: 3- (ethylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 에타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 505 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), etanamine (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 505 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10(s, 1H), 2.73(m, 2H), 2.0(s, 1H, -NH), 0.84 (s, 3H). MASS = 188.09 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.0 (s, 1H, -NH), 0.84 (s, 3H). MASS = 188.09

합성예 506 : 3-(프로필아미노)퀴놀린-2(1H)-온Synthesis Example 506: 3- (Propylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 프로판-1-아민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 506 화합물을 수득하였다(수율=53%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), propane-1 -amine (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 506 (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.10(s, 1H), 2.73(m, 2H), 2.32(m, 2H), 2.0(s, 1H, -NH), 0.84(s, 3H). MASS=202.11 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.32 (m, 2H), 2.0 (s, 1H, MASS = 202.11

합성예 507 : 3-(부틸아미노)퀴놀린-2(1H)-온Synthesis Example 507: 3- (Butylamino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)을 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 부탄-1-아민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 507 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), butan-1 -amine (1.3 mmol) and Zanphor (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain the compound of Synthesis Example 507 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.10(s, 1H), 2.73(m, 2H), 2.0(s, 1H, -NH), 1.52(m, 2H), 1.31(m, 2H), 0.9(s, 3H). MASS=216.13 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.0 (s, 1H, -NH), 1.52 (m, 2H), 1.31 (m, 2H), 0.9 (s, MASS = 216.13

합성예 508 : 3-((에톡시메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 508: 3 - ((Ethoxymethyl) amino) quinolin-2 (1H) -one

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), 에톡시메타나민(1.3 mmol) 및 잔포스(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 508 화합물을 수득하였다(수율= 67%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Was added Cs 2 CO 3 (2 mmol) , Pd (OAC) 2 (0.15 mmol), ethoxy meta namin (1.3 mmol) and the balance force (0.15 mmol) the reaction mixture was stirred at 100 ℃ for 10 hours. The residue obtained was extracted with ethyl acetate and water. And then purified by silica gel chromatography to obtain a compound of Synthesis Example 508 (yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.50(m, 2H), 2.0(s, 1H, -NH), 3.28(m, 2H), 1.10(s, 3H). MASS=218.11 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 3.50 (m, 2H), 2.0 (s, 1H, -NH), 3.28 (m, 2H), 1.10 (s, 3H). MASS = 218.11

합성예 509 : 3-(((에틸티오)메틸)아미노)퀴놀린-2(1H)-온Synthesis Example 509: Synthesis of 3 - (((ethylthio) methyl) amino) quinolin-2 (1H)

3-브로모퀴놀린-2(1H)-온(1 mmol)를 1,4-디옥산(2 mL)에 용해시켰다. Cs2CO3(2 mmol), Pd(OAC)2(0.15 mmol), (에틸티오)메타나민(1.3 mmol) 및 잔포스(잔포스)(0.15 mmol)를 반응 혼합물에 첨가하고 100℃에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 509 화합물을 수득하였다(수율=61%).3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL). (0.1 mmol) of Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), (ethylthio) methanamine (1.3 mmol) and Zanphos Lt; / RTI &gt; The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 509 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.10(s, 1H), 3.50(m, 2H), 2.0(s, 1H, -NH), 3.28(m, 2H), 1.10(s, 3H). MASS=234.08 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 3.50 (m, 2H), 2.0 (s, 1H, -NH), 3.28 (m, 2H), 1.10 (s, 3H). MASS = 234.08

단계(e-5, h-8)의 일반적 과정General procedure of steps (e-5, h-8)

4번 또는 7번 화합물, (430mg, 0.7mmol), DIPEA(0.2mL, 1.1mmol) 및 R4-CO-Cl(0.1mL,0.8mmol)를 CH2Cl2(20mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 5번 또는 8번 화합물을 수득하였다.Compound 4 or 7 (430 mg, 0.7 mmol), DIPEA (0.2 mL, 1.1 mmol) and R 4 -CO-Cl (0.1 mL, 0.8 mmol) were stirred in CH 2 Cl 2 (20 mL) . Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the product was purified by silica gel column chromatography to obtain Compound No. 5 or Compound No. 8.

합성예 80 : 5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 80: Synthesis of 5-benzamido-2-oxo-N-phenyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5mmol) 및 벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 80 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were dissolved in CH 2 Cl 2 (2 mL) Lt; / RTI &gt; for 15 minutes. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 80 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(dd, 2H), 8.0(s, 1H, -NH), 7.88(dd, 2H), 7.7(t, 2H), 7.63(dd, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.19(t, 1H). MASS=383.13 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.63 (dd, 2H), 7.96 (dd, 2H). MASS = 383.13

합성예 81 : 5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 81: Synthesis of 5-benzamido-2-oxo-N-phenyl-1,2-dihydroquinoline-3-

1-((2H-피롤-2-일)메틸)-5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세타이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 81 화합물을 수득하였다(수율=64%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol), and N, N'- And benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3 tight. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 81 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(dd, 2H), 8.0(s, 1H, -NH), 7.88(dd, 2H), 7.7(t, 2H), 7.63(dd, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.19(t, 1H). MASS=383.13 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.63 (dd, 2H), 7.96 (dd, 2H). MASS = 383.13

합성예 82 : 5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 82: Synthesis of 5- (4-methylbenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5mmol) 및 4-메틸벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 82 화합물을 수득하였다(수율=64%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-methylbenzoyl chloride (1.2 mmol) were dissolved in CH 2 Cl 2 (2 mL) for 15 minutes. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 82 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(dd, 2H), 8.0(s, 1H, -NH), 7.88(dd, 2H), 7.7(t, 2H), 7.63(dd, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.19(t, 1H), 2.34(s, 3H). MASS=397.14 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.41 (dd, 2H), 7.88 (dd, 2H), 7.87 (d, 2H) , 3H). MASS = 397.14

합성예 83 : 1-(2-(2H-피롤-2-일)에틸)-5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 83: Synthesis of 1- (2- (2H-pyrrol-2-yl) ethyl) -5- (4-methylbenzamido) Carboxamide

1-(2-(2H-피롤-2-일)에틸)-5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-메틸벤조일 클로라이드(1.2 mmol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 83 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol), N-methyl-2- mmol) and 4-methylbenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 83 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.25(s, 1H), 8.03(dd, 2H), 7.88(d, 1H), 7.70(s, 1H), 7.61(m, 4H), 7.50(s, 1H), 7.43 (dd, 2H), 7.39(d, 1H), 7.29(t, 1H), 7.19(s, 1H), 5.68(s, 1H), 5.16(s, 1H), 3.3(s, 3H), 3.1(s, 2H), 2.9(s, 2H), 2.0(s, 1H). MASS=490.20 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H 2H), 7.39 (d, 1H), 7.29 (t, 1H), 7.19 (s, 1H) , 5.68 (s, IH), 5.16 (s, IH), 3.3 (s, 3H), 3.1 (s, 2H), 2.9 (s, 2H), 2.0 (s, MASS = 490.20

합성예 84 : 5-(4-브로모벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 84: 5- (4-Bromobenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 4-브로모벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 84 화합물을 수득하였다(수율= 49%).A 5-amino-2-oxo -N- phenyl-1,2-dihydro-quinoline-3-carboxamide (1mmol), DIPEA (1.5mmol) and 4-bromo-benzoyl chloride (1.2mmol) CH 2 Cl 2 (2 mL) for 15 minutes. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 84 (yield = 49%).

1H NMR (400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(dd, 2H), 8.0(s, 1H, -NH), 7.88(dd, 2H), 7.7(t, 2H), 7.63(dd, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.19(t, 1H). MASS=461.04 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.63 (dd, 2H), 7.96 (dd, 2H). MASS = 461.04

합성예 88 : 5-(4-클로로벤즈아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 88: Synthesis of 5- (4-chlorobenzamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

5-아미노-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-클로로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 88 화합물을 수득하였다(수율= 47%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-chlorobenzoyl chloride (1.2 mmol) were added to a solution of 5-amino- Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 88 (yield = 47%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 7.97(dd, 2H), 7.88(m, 2H), 7.67(dd, 2H), 7.29(t, 1H), 7.21(dd, 2H), 7.17 (dd, 2H), 2.34(s, 3H). MASS=431.10 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.67 (dd, 2H), 7.29 (t, IH), 7.21 (dd, 2H), 7.17 (dd, 2H), 2.34 (s, 3H). MASS = 431.10

합성예 90 : 5-(4-플루오로벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 90: 5- (4-Fluorobenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-

5-아미노-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 4-플루오로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 90 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-fluorobenzoyl chloride (1.2 mmol) mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Then, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 90 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.12(d, 1H), 7.88(m, 2H), 7.51(dd, 2H), 7.42(dd, 2H), 6.97(dd, 2H), 3.83 (s, 3H). MASS=431.13 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 3.83 (s, 3H). MASS = 431.13

합성예 91 : 5-(4-에틸벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 91: Synthesis of 5- (4-ethylbenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-에틸벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 91 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-ethylbenzoyl chloride (1.2 mmol ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 91 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.12(d, 1H), 7.88(m, 2H), 7.51(dd, 2H), 7.42(dd, 2H), 6.97(dd, 2H), 3.83 (s, 3H), 2.60(s, 2H), 1.25(s, 3H). MASS=441.17 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 3.83 (s, 3H), 2.60 MASS = 441.17

합성예 93 : N-(4-브로모페닐)-2-옥소-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 93: Synthesis of N- (4-bromophenyl) -2-oxo-5- (4-vinylbenzamido) -1,2-dihydroquinoline-

5-아미노-N-(4-브로모페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-비닐벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 93 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-vinylbenzoyl chloride (1.2 mmol ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 93 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.12(d, 1H), 7.88(m, 2H), 7.51(dd, 2H), 7.42(dd, 2H), 6.97(dd, 2H), 6.63 (s, 1H), 5.61(s, 1H), 5.18(s, 1H). MASS=487.05 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 6.63 (s, MASS = 487.05

합성예 94 : N-(4-브로모페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 94: Synthesis of N- (4-bromophenyl) -2-oxo-1- (2- (thiophen- Hydroquinoline-3-carboxamide

5-아미노-N-(4-브로모페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-비닐벤조일 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 94 화합물을 수득하였다(수율=61%).2-yl) ethyl) -1,2-dihydroquinoline-3-carboxamide (1 mmol) was added to a solution of 5-amino-N- (4-bromophenyl) ), DIPEA (1.5 mmol) and 4-vinylbenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 94 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.25(s, 1H), 8.03(dd, 2H), 7.88(d, 1H), 7.70(s, 1H), 7.61(m, 4H), 7.50 (s, 1H), 7.43 (dd, 2H), 7.39(d, 1H), 7.29(t, 1H), 5.68(s, 1H), 5.16(s, 1H), 3.3(s, 2H), 3.1(m, 3H), 2.9(s, 2H), 2.0(s, 1H). MASS=597.07 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H 2H), 7.39 (d, 1H), 7.29 (t, 1H), 5.68 (s, 1H) , 5.16 (s, 1H), 3.3 (s, 2H), 3.1 (m, 3H), 2.9 (s, 2H), 2.0 (s, 1H). MASS = 597.07

합성예 98 : N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 98: N- (4-chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 98 화합물을 수득하였다(수율= 71%).(1 mmol), DIPEA (1.5 mmol) and 4-nitrobenzoyl chloride (1.2 mmol) were added to a solution of 5-amino-N- (4- chlorophenyl) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 98 (yield = 71%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H). MASS=462.07 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H). MASS = 462.07

합성예 99 : N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 99: N- (4-Chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 99 화합물을 수득하였다(수율= 42%).2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- nitrobenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 99 (yield = 42%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H), 3.2(s, 3H). MASS=476.09 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.2 (s, 3H). MASS = 476.09

합성예 100 : N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 100: Synthesis of N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 100 화합물을 수득하였다(수율=61%).2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- nitrobenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 100 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H), 3.2(s, 2H), 2.83(s, 3H). MASS = 490.10 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, MASS = 490.10

합성예 101 : 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 101: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline-3-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-브로모벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 101 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-bromobenzoyl chloride (1.2 mmol ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 101 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H). MASS=495.00 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H). MASS = 495.00

합성예 102 : 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 102: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-브로모벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 102 화합물을 수득하였다(수율=73%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-bromobenzoyl chloride Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Then, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 102 (yield = 73%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H), 3.3(s, 3H). MASS=509.01 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, MASS = 509.01

합성예 103 : 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 103: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-브로모벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 103 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-bromobenzoyl chloride Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 103 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(m, 2H), 7.75(dd, 1H), 7.47(dd, 2H), 7.29 (t, 1H), 3.3(s, 2H), 2.8(s, 3H). MASS=523.03 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.3 (s, 2H), 2.8 (s, MASS = 523.03

합성예 104 : N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 104: Synthesis of N- (4-chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-(하이드록시메틸)벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 104 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- (hydroxymethyl) benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 104 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H), 3.65(s, 1H, -OH). MASS=447.10 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , 1H, -OH). MASS = 447.10

합성예 105 : N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 105: Synthesis of N- (4-chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-(하이드록시메틸)벤조일클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 105 화합물을 수득하였다(수율= 58%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- (hydroxy- Methyl) benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 105 (yield = 58%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H), 3.65(s, 1H, -OH), 3.2(s, 3H). MASS= 461.11 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , &Lt; / RTI &gt; 1H, -OH), 3.2 (s, 3H). MASS = 461.11

합성예 106 : N-(4-클로로페닐)-1-에틸-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 106: Synthesis of N- (4-chlorophenyl) -1-ethyl-5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-(하이드록시메틸)벤조일클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 106 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol), and 4- (hydroxy-2-oxo- Methyl) benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 106 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H), 3.65(s, 1H, -OH), 3.2(s, 2H), 2.7 (s, 3H). MASS=475.13 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , 1H, -OH), 3.2 (s, 2H), 2.7 (s, 3H). MASS = 475.13

합성예 107 : N-(4-클로로페닐)-1-(퓨란-2-일메틸)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 107: Synthesis of N- (4-chlorophenyl) -1- (furan-2-ylmethyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline -3-carboxamide

5-아미노-N-(4-클로로페닐)-1-(퓨란-2-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 4-(하이드록시메틸)벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 107 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1mmol), DIPEA (1.5mmol) and diisopropylethylamine were added to a solution of 5-amino-N- (4- chlorophenyl) And 4- (hydroxymethyl) benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 107 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.65(s, 1H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 6.42(m, 2H), 4.61(s, 2H), 4.07(s, 2H), 3.65(s, 1H, -OH). MASS=527.12 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.65 , 2H), 4.61 (s, 2H), 4.07 (s, 2H), 3.65 (s, MASS = 527.12

합성예 108 : N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 108: N- (4-Chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 108 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and 4-nitrobenzoyl chloride (1.2 mmol) were added to a solution of 5-amino-N- (4- chlorophenyl) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 108 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H). MASS=462.07 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 MASS = 462.07

합성예 109 : N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 109: Synthesis of N- (4-chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 109 화합물을 수득하였다(수율=61%).2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- nitrobenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Then, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 109 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H), 3.2(s, 3H). MASS=476.09 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 , 3H). MASS = 476.09

합성예 110 : N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 110: Synthesis of N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 110 화합물을 수득하였다(수율= 64%).2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4- nitrobenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 110 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 4.61(s, 2H), 3.2(s, 2H), 2.94(s, 3H). MASS=490.10 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 , &Lt; / RTI &gt; 2H), 2.94 (s, 3H). MASS = 490.10

합성예 111 : N-(4-클로로페닐)-1-(2-(퓨란-2-일)에틸)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 111: Synthesis of N- (4-chlorophenyl) -1- (2- (furan-2-yl) ethyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline -3-carboxamide

5-아미노-N-(4-클로로페닐)-1-(2-(퓨란-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 111 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), 5-amino-N- (4-chlorophenyl) DIPEA (1.5 mmol) and 4-nitrobenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 111 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.58(s, 1H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, 1H), 6.6(m, 2H), 4.61(s, 2H), 2.66(s, 2H). MASS=556.11 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.58 , 2H), 4.61 (s, 2H), 2.66 (s, 2H). MASS = 556.11

합성예 112 : N-(4-클로로페닐)-2-옥소-5-(2-페닐아세트아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 112: N- (4-Chlorophenyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-페닐아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 112 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-phenylacetyl chloride (1.2 mmol) were added to a solution of 5-amino- Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 112 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2H), 7.47(dd, 2H), 7.33(dd, 2H), 7.29(m, 2H), 7.26(t, 1H), 7.23(dd, 2H). MASS=431.10 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 7.26 (t, IH), 7.23 (dd, 2H). MASS = 431.10

합성예 113 : 5-벤즈아미도-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 113: Synthesis of 5-benzamido-N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예113 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were added to a solution of 5-amino- ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 113 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2H), 7.47(dd, 2H), 7.33(dd, 2H), 7.29(m, 2H), 7.26(t, 1H), 7.23(dd, 2H), 3.3(s, 3H). MASS=431.10 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 3.3 (s, 3H). MASS = 431.10

합성예 114 : (5-벤즈아미도-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 114: (5-benzamido-N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예114 화합물을 수득하였다(수율= 64%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were added to a solution of 5-amino- ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 114 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2H), 7.47(dd, 2H), 7.33(dd, 2H), 7.29(m, 2H), 7.26(t, 1H), 7.23(dd, 2H), 3.3(s, 2H), 2.9(s, 3H). MASS=445.12 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 3.3 (s, 2H), 2.9 (s, 3H). MASS = 445.12

합성예 115 : N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 115: N- (4-Chlorophenyl) -5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-에틸벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 115 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 4-ethylbenzoyl chloride (1.2 mmol) were added to a solution of 5-amino-N- (4-chlorophenyl) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 115 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2H), 7.47(dd, 2H), 7.33(dd, 2H), 7.29(m, 2H), 2.60(s, 2H), 1.25(s, 3H). MASS=445.12 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 2.60 (s, 2H), 1.25 (s, 3H). MASS = 445.12

합성예 116 : N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 116: Synthesis of N- (4-chlorophenyl) -5- (4-ethylbenzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-에틸벤조일 클로라이드(1.2 mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 116 화합물을 수득하였다(수율=67%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-ethylbenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 116 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2H), 7.47(dd, 2H), 7.33(dd, 2H), 7.29(m, 2H), 3.3(s, 3H), 2.60(s, 2H), 1.25(s, 3H). MASS=459.13 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 (s, 2H), 1.25 (s, 3H). MASS = 459.13

합성예 117 (N-(4-클로로페닐)-1-에틸-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 117 (Synthesis of N- (4-chlorophenyl) -1-ethyl-5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 4-에틸벤조일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 117 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-ethylbenzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 117 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 (m, 5H), 1.25 (s, 3H). MASS= 473.15 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 (m, 5H), 1.25 (s, 3H). MASS = 473.15

합성예 122 : N-(4-플루오로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 122: Synthesis of N- (4-fluorophenyl) -2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-

5-아미노-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(p-톨일)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 122 화합물을 수득하였다(수율=61%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (p-toluoyl) -2-oxo-1,2-dihydroquinoline- Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 122 (Yield = 61%).

1H NMR (400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.29(t, 1H), 7.22(dd, 2H), 7.11(m, 4H), 2.34(s, 3H). MASS = 429.15 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 2.34 (s, 3H). MASS = 429.15

합성예 123 : N-(4-플루오로페닐)-1-메틸-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 123: Synthesis of N- (4-fluorophenyl) -1-methyl-2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-

5-아미노-N-(4-플루오로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(p-톨일)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 123 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (p (2-hydroxyphenyl) -Tolyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 123 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.29(t, 1H), 7.22(dd, 2H), 7.11(m, 4H), 3.2(s, 3H), 2.34 (s, 3H). MASS=443.16 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 3H), 2.34 (s, 3H). MASS = 443.16

합성예 124 : 1-에틸-N-(4-플루오로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 124: Synthesis of 1-ethyl-N- (4-fluorophenyl) -2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-

5-아미노-1-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(p-톨일)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 124 화합물을 수득하였다(수율= 63%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (p -Tolyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 124 compound (Yield = 63%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.29(t, 1H), 7.22(dd, 2H), 7.11(m, 4H), 3.2(s, 2H), 2.8 (s, 3H), 2.34(s, 3H). MASS=457.18 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 2H), 2.8 (s, 3H), 2.34 (s, 3H). MASS = 457.18

합성예 129 : 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 129: 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 129 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-bromophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 129 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 3.90 (s, 2H), 2.60 (s, 2H), 1.25 (s, 3H). MASS = 503.08 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , &Lt; / RTI &gt; 2H), 1.25 (s, 3H). MASS = 503.08

합성예 130 : 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1-(티오펜-2-일메틸)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 130: 5- (2- (4-Bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo- 1- (thiophen- Dihydroquinoline-3-carboxamide

5-아미노-N-(4-에틸페닐)-2-옥소-1-(티오펜-2-일메틸)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 130 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol), N, N-dimethylformamide mmol) and 2- (4-bromophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 130 compound (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.85(dd, 2H), 7.63(dd, 2H), 7.40(s, 1H), 7.29(s, 1H), 7.27 (dd, 2H), 7.23(s, 1H, -NH), 7.12(m, 3H), 6.93(s, 1H), 4.22(s, 2H), 3.90(s, 2H), 2.60(s, 2H), 1.25(s, 3H). MASS = 599.09 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.40 (s, IH), 7.29 (s, IH), 7.27 (dd, 2H), 7.23 , 4.25 (s, 2H), 2.60 (s, 2H), 2.60 (s, 2H). MASS = 599.09

합성예 131 : 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 131: 5- (2- (4-Bromophenyl) acetamido) -N- (4-ethylphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- Mide

5-아미노-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 131 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-bromophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 131 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.85(dd, 2H), 7.63(dd, 2H), 7.29(s, 1H), 7.27(dd, 2H), 7.23(s, 1H, -NH), 7.12(dd, 2H), 3.90(s, 2H), 3.3(s, 3H), 2.60(s, 2H), 1.25 (s, 3H). MASS = 517.10 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , 3H), 2.60 (s, 2H), 1.25 (s, 3H). MASS = 517.10

합성예 132 : 5-(2-(4-브로모페닐)아세트아미도)-1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 132: Synthesis of 5- (2- (4-bromophenyl) acetamido) -1-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- Mide

5-아미노-1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 132 화합물을 수득하였다(수율= 67%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-ethylphenyl) Bromophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 132 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.85(dd, 2H), 7.63(dd, 2H), 7.29(s, 1H), 7.27(dd, 2H), 7.23(s, 1H, -NH), 7.12(dd, 2H), 3.90(s, 2H), 3.3(s, 2H), 2.60(m, 5H), 1.25 (s, 3H). MASS=531.12 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , 2H), 2.60 (m, 5H), 1.25 (s, 3H). MASS = 531.12

합성예 137 : 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 137: 5- (2- (4-Chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA (1.5 mmol) 및 2-(4-클로로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 137 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 137 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.45(dd, 2H), 7.41(dd, 2H), 7.37(dd, 2H), 7.29(t, 1H), 6.93(dd, 2H), 5.35 (s, 1H, -OH), 3.90(s, 2H). MASS=447.10 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 3.90 (s, 2H). MASS = 447.10

합성예 138 : 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 138: Synthesis of 5- (2- (4-chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- Mide

5-아미노-N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-클로로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 138 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) -Chlorophenyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 138 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.45(dd, 2H), 7.41(dd, 2H), 7.37(dd, 2H), 7.29(t, 1H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 3.90(s, 2H), 3.3(s, 3H). MASS=461.11 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (d, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 3.90 (s, 2H), 3.3 (s, MASS = 461.11

합성예 139 : 5-(2-(4-클로로페닐)아세트아미도)-1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 139: Synthesis of 5- (2- (4-chlorophenyl) acetamido) -1-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline- Mide

5-아미노-1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-클로로페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 139 화합물을 수득하였다(수율=66%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) -Chlorophenyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 139 (Yield = 66%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.45(dd, 2H), 7.41(dd, 2H), 7.37(dd, 2H), 7.29(t, 1H), 6.93(dd, 2H), 5.35(s, 1H, -OH), 3.90(s, 2H), 3.3(s, 2H), 2.73(s, 3H). MASS = 475.13 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (d, 2H), 7.29 (t, 1H), 6.93 (s, 3H) . MASS = 475.13

합성예 141 : 5-(2-(4-플루오로페닐)아세트아미도)-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 141: Synthesis of 5- (2- (4-fluorophenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA (1.5 mmol) 및 2-(4-플루오로페닐)아세틸 클로라이드(1.2 mmol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 141 화합물을 수득하였다(수율= 64%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 141 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 6.93 (dd, 2H), 3.90 (s, 2H). MASS = 460.12 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 3.90 (s, 2H). MASS = 460.12

합성예 142 : 5-(2-(4-에틸페닐)아세트아미도)-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 142: Synthesis of 5- (2- (4-ethylphenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-에틸페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 142 화합물을 수득하였다(수율= 67%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-ethylphenyl) acetyl Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 142 (Yield = 67%).

1H NMR (400 MHz, CDCl3)δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H). MASS = 470.16 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H). MASS = 470.16

합성예 156 : 5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 156: Synthesis of 5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

5-아미노-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-하이드록시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 156 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) -1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 156 compound (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61 (s, 1H), 5.35(s, 1H, -OH), 5.18(s, 1H), MASS=439.15 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), MASS = 439.15 (s,

합성예 157 : 5-(2-(4-하이드록시페닐)아세트아미도)-1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 157: Synthesis of 5- (2- (4-hydroxyphenyl) acetamido) -1-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- Mide)

5-아미노-1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-하이드록시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 157 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-vinylphenyl) -1,2-dihydroquinoline- Hydroxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 157 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61(s, 1H), 5.35(s, 1H, -OH), 5.18(s, 1H), 3.3(s, 3H). MASS=453.17 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , 3H). MASS = 453.17

합성예 158 : 1-에틸-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 158: Synthesis of 1-ethyl-5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- Mide

5-아미노-1-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-하이드록시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 158 화합물을 수득하였다(수율= 49%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) Hydroxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 158 (yield = 49%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61(s, 1H), 5.35(s, 1H, -OH), 5.18(s, 1H), 3.3(s, 2H), 2.8(s, 3H). MASS=467.18 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , &Lt; / RTI &gt; 2H), 2.8 (s, 3H). MASS = 467.18

합성예 159 : 1-((2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 159: Synthesis of 1 - ((2,3-dihydro-1H-inden-2-yl) methyl) -5- (2- (4-hydroxyphenyl) acetamido) Vinylphenyl) -1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-하이드록시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 159 화합물을 수득하였다(수율=61%).Dihydro-1H-inden-2-yl) methyl) -2-oxo-N- (4-vinylphenyl) (1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 159 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(m, 5H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61(s, 1H), 5.35(s, 1H, -OH), 5.18(s, 1H), 3.98(s, 2H), 2.66(m, 5H). MASS=569.23 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (m, 5H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.98 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , &Lt; / RTI &gt; 2H), 2.66 (m, 5H). MASS = 569.23

합성예 160 : 5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 160: Synthesis of 5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

5-아미노-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 160 화합물을 수득하였다(수율= 66%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-nitrophenyl) acetyl Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthetic Example 160 (Yield = 66%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61 (s, 1H), 5.18(s, 1H). MASS = 468.14 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1 H, -NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, MASS = 468.14

합성예 161 : 1-메틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 161: Synthesis of 1-methyl-5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

5-아미노-1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 161 화합물을 수득하였다(수율= 62%)(1 mmol), DIPEA (1.5 mmol) and 2- (4-vinylphenyl) -1,2-dihydroquinoline- Nitrophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 161 (Yield = 62%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61 (s, 1H), 5.18(s, 1H), 3.3(s, 3H). MASS=482.16 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (d, 2H), 6.63 (s, 3H), 5.61 (s, 1H), 5.18 (s, 1H), 3.3 (s, 3H). MASS = 482.16

합성예 162 : 1-에틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 162: Synthesis of 1-ethyl-5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

5-아미노-1-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 162 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) Nitrophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 162 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(dd, 2H), 6.63(m, 3H), 5.61 (s, 1H), 5.18(s, 1H), 3.3(s, 2H), 2.76(s, 3H). MASS=496.17 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (d, 2H), 6.63 (s, 3H), 5.61 (s, 1H), 5.18 (s, . MASS = 496.17

합성 예 163 : 1-((4-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 163: Synthesis of 1 - ((4-methoxy-2,3-dihydro-1H-inden-2-yl) methyl) -N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((4-메톡시-2,3,3a,7a-테트라하이드로-1H-인덴-1-일)메틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 163 화합물을 수득하였다(수율= 63%).1-yl) methyl) -2-oxo-N- (4-vinylphenyl) -1, Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-nitrophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) . The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 163 (Yield = 63%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(m, 3H), 6.63(m, 4H), 5.61 (s, 1H), 5.18(s, 1H), 3.83(s, 3H), 2.79(s, 2H), 2.46(m, 5H). MASS=628.23 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H), 3.63 (s, 3H), 2.79 (s, 2H) , &Lt; / RTI &gt; 2.46 (m, 5H). MASS = 628.23

합성예 164 : 1-((5-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 164: Synthesis of 1 - ((5-methoxy-2,3-dihydro-1H-inden-2-yl) methyl) -N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide

55-아미노-1-((6-메톡시-2,3,3a,7a-테트라하이드로-1H-인덴-1-일) 메틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 164 화합물을 수득하였다(수율= 67%).Methyl-2-oxo-N - (4-vinylphenyl) -1, 5-dihydro- Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-nitrophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) . The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 164 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, 1H,-NH), 7.06(m, 3H), 6.63(m, 4H), 5.61(s, 1H), 5.18(s, 1H), 3.83(s, 3H), 2.79(s, 2H), 2.46(m, 5H). MASS=628.23 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H), 3.63 (s, 3H), 2.79 (s, 2H) , &Lt; / RTI &gt; 2.46 (m, 5H). MASS = 628.23

합성예 168 : 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 168: Synthesis of 5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-메톡시페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 168 화합물을 수득하였다(수율= 69%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 168 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.19(t, 1H), 7.12(dd, 2H), 6.87(dd, 2H), 3.9(m, 2H), 3.83(s, 3H). MASS = 427.15 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 3.83 (s, 3H), 7.43 (d, 2H), 7.29 (t, . MASS = 427.15

합성예 169 : 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 169: 1- ((5-Ethyl-2,3-dihydro-1H-inden-2-yl) methyl) Phenyl-l, 2-dihydroquinoline-3-carboxamide

5-아미노-1-((2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-메톡시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 169 화합물을 수득하였다(수율= 66%).Methyl-2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide (1 mmol) , DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 169 (Yield = 66%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(m, 2H), 7.19(t, 1H), 7.12 (dd, 2H), 6.87(m, 3H), 3.9(m, 2H), 3.83(m, 6H), 2.83(s, 2H), 2.76(s, 2H), 2.46(m, 5H). MASS=585.26 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H (M, 2H), 7.43 (d, 2H), 7.29 (m, 2H), 7.19 , 2.83 (s, 2 H), 2.76 (s, 2 H), 2.46 (m, 5 H). MASS = 585.26

합성예 170 : 1-((5-플루오로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 170: Synthesis of 1 - ((5-fluoro-2,3-dihydro-1H-inden-2-yl) methyl) Oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-플루오로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-메톡시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 170 화합물을 수득하였다Yl) methyl) -2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carbaldehyde (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 170

(수율= 61%).(Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(m, 3H), 7.43(dd, 2H), 7.29(t, 1H), 7.19(t, 1H), 7.12 (dd, 2H), 6.87(m, 3H), 3.9(m, 2H), 3.83(s, 3H), 2.79(s, 2H), 2.46(m, 5H). MASS=575.22 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H 3H), 3.83 (s, 3H), 2.27 (d, 2H) , 2.79 (s, 2 H), 2.46 (m, 5 H). MASS = 575.22

합성예 171 : 1-((5-클로로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 171: 1 - ((5-Chloro-2,3-dihydro-1H-inden-2-yl) methyl) Phenyl-l, 2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-클로로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-메톡시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 171 화합물을 수득하였다(수율=69%).Synthesis of 5-amino-1 - ((5-chloro-2,3-dihydro-1H-inden-2-yl) methyl) -2-oxo-N-phenyl-1,2-dihydroquinoline- (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 171 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(m, 3H), 7.43(dd, 2H), 7.29(t, 1H), 7.19(t, 1H), 7.12(dd, 2H), 6.87(m, 3H), 3.9(m, 2H), 3.83(s, 3H), 2.79(s, 2H), 2.46(m, 5H). MASS=591.19 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H 3H), 3.83 (s, 3H), 2.27 (d, 2H) , 2.79 (s, 2 H), 2.46 (m, 5 H). MASS = 591.19

합성예 172 : 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 172: Synthesis of 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-

55-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-(하이드록시메틸)페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 172 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4- (hydroxymethyl) phenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 172 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.19(t, 1H), 7.16 (dd, 2H), 7.11(dd, 2H), 4.61(m, 2H), 3.90(m, 2H), 3.65(s, 1H, -OH). MASS= 427.15 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (d, 2H), 4.61 (m, 2H), 3.90 (m, 2H), 7.19 (t, , 3.65 (s, 1 H, -OH). MASS = 427.15

합성예 173 : 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-아이오도-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 173: 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1- (5-iodo-2,3-dihydro- -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-아이오도-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-(하이드록시메틸)페닐)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 173 화합물을 수득하였다(수율= 61%).2-yl) methyl) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carbaldehyde (1 mmol), DIPEA (1.5 mmol) and 2- (4- (hydroxymethyl) phenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 173 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.19(m, 2H), 7.16 (dd, 2H), 7.11(m, 3H), 4.61(m, 2H), 3.90(m, 2H), 3.65(s, 1H, -OH), 3.3 (s, 2H), 2.46(m, 5H). MASS=683.13 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 7.19 (m, 2H), 7.19 (m, 2H), 7.19 (m, , 3.65 (s, IH, -OH), 3.3 (s, 2H), 2.46 (m, 5H). MASS = 683.13

합성예 174 : 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-니트로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 174: 5- (2- (4- (Hydroxymethyl) phenyl) acetamido) -1 - ((5-nitro-2,3-dihydro- 2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-니트로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-(하이드록시메틸)페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 174 화합물을 수득하였다(수율= 61%).Methyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxaldehyde (1 mmol), DIPEA (1.5 mmol) and 2- (4- (hydroxymethyl) phenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 174 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.19(m, 2H), 7.16 (dd, 2H), 7.11(m, 3H), 4.61(m, 2H), 3.90(m, 2H), 3.65(s, 1H, -OH), 3.3(s, 2H), 2.46(m, 5H). MASS=602.22 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 7.19 (m, 2H), 7.19 (m, 2H), 7.19 (m, , 3.65 (s, IH, -OH), 3.3 (s, 2H), 2.46 (m, 5H). MASS = 602.22

합성예 175 : 2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Preparation 175: 2-Oxo-N-phenyl-5- (3-phenylpropanamido) -1,2-dihydroquinoline-3-carboxamide

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5mmol) 및 3-페닐프로파노일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 175 화합물을 수득하였다(수율= 64%).5-amino-2-oxo -N- phenyl-1,2-dihydro-quinoline-3-carboxamide (1 mmol), DIPEA (1.5mmol ) and 3-phenyl-propanoyl chloride (1.2mmol) CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 175 (yield = 64%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.19(t, 1H), 2.9(m, 2H), 2.83(m, 2H). MASS= 411.16 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 1H), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 , &Lt; / RTI &gt; 2H), 2.83 (m, 2H). MASS = 411.16

합성예 176 : 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 176: 1 - ((5-Ethyl-2,3-dihydro-1H-inden-2-yl) methyl) , 2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 3-페닐프로파노일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 176 화합물을 수득하였다(수율=61%).Methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxaldehyde (1 mmol), DIPEA (1.5 mmol) and 3-phenylpropanoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 176 (yield = 61%).

1H NMR (400 MHz, CDCl3) δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.40(dd, 2H), 7.29(m, 4H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.19(m, 3H), 3.3(m, 5H), 2.9(m, 7H), 2.83(m, 4H), 2.64(s, 5H). MASS = 569.27 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H ), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 , 5H), 2.9 (m, 7H), 2.83 (m, 4H), 2.64 (s, 5H). MASS = 569.27

합성예 177 : 5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 177: 5- (2- (4-ethylphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5mmol) 및 2-(4-에틸페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 177 화합물을 수득하였다(수율= 62%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-ethylphenyl) acetyl chloride (1.2 mmol) were added to a solution of 5-amino- Was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 177 (Yield = 62%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(dd, 2H), 6.98(dd, 2H), 3.90(m, 2H), 2.60(m, 2H), 1.25(s, 3H). MASS= 425.17 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 3.90 (m, 2H), 2.60 (m, 2H), 7.43 (dd, 2H), 7.29 , &Lt; / RTI &gt; 2H), 1.25 (s, 3H). MASS = 425.17

합성예 178 : 1-(2-(2,3-디하이드로-1H-인덴-2-일)에틸)-5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 178: 1- (2- (2,3-Dihydro-1 H-inden-2-yl) ethyl) -5- (2- (4-ethylphenyl) acetamido) Phenyl-1,2-dihydroquinoline-3-carboxamide

55-아미노-1-((2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 벤조일 클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 178 화합물을 수득하였다(수율= 61%)Methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide (1 mmol) , DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 178 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H), 7.29(m, 2H), 7.23(s, 1H, -NH), 7.18(m, 4H), 6.98(dd, 2H), 3.90(m, 6H), 2.60(m, 7H), 1.25(s, 3H). MASS= 569.27 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 7.23 (s, 1H, -NH), 7.18 (m, 4H), 6.98 (dd, 2H), 3.90 (m, 6H), 2.60 , &Lt; / RTI &gt; 7H), 1.25 (s, 3H). MASS = 569.27

합성예 184 : 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 184: 5- (2- (4-Methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-메톡시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 184 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were added to a solution of 5-amino-2-oxo-N-phenethyl-1,2-dihydroquinoline- mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 184 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12 (dd, 2H), 6.87(dd, 2H), 3.90(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS= 455.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (dd, 2H), 6.87 (dd, 2H) , 3.55 (m, 2H), 2.83 (m, 2H). MASS = 455.18

합성예 185 : 1-(4-메톡시벤질)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 185: Synthesis of 1- (4-methoxybenzyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinolin- Carboxamide

5-아미노-1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-메톡시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 185 화합물을 수득하였다(수율=63%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxybenzyl) 4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 185 (Yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12(m, 4H), 6.87(m, 4H), 3.90(s, 2H), 3.83(s, 3H), 3.55(m, 4H), 2.83(m, 5H). MASS= 575.24 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (s, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H) , 3.55 (m, 4H), 2.83 (m, 5H). MASS = 575.24

합성예 186 : 1-((4-하이드록시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 186: 1- ((4-Hydroxy-2,3-dihydro-1H-inden-2-yl) methyl) Oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide

55-아미노-1-((2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-메톡시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 186 화합물을 수득하였다(수율=67%).Methyl-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 186 (Yield = 67%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12(m, 4H), 6.87(m, 3H), 3.90(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H), 2.68(m, 5H). MASS = 601.26 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) , 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H). MASS = 601.26

합성예 187 : 1-((4-포르밀-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 187: Synthesis of 1 - ((4-formyl-2,3-dihydro-1H-inden-2-yl) methyl) Oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide

5-아미노-2-옥소-N-펜에틸-1-((5-비닐-2,3-디하이드로-1H-인덴-2-일)메틸)-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-메톡시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로추출하였다. 이후 실리카겔컬럼크로마토그래피로 정제하여 합성예 187 화합물을 수득하였다(수율= 61%).Dihydro-1H-inden-2-yl) methyl) -1,2-dihydroquinoline-3-carbaldehyde (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 187 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88(m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12(m, 4H), 6.87(m, 3H), 3.90(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H), 2.68(m, 5H), 1.27(s, 1H). MASS=613.26 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) , 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H), 1.27 (s, MASS = 613.26

합성예 188 : 1-((4-시아노-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 188: Synthesis of 1- ((4-cyano-2,3-dihydro-1H-inden-2-yl) methyl) Oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide

5-아미노-1-((5-시아노-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-메톡시페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 188 화합물을 수득하였다(수율= 62%)Dihydro-1H-inden-2-yl) methyl) -2-oxo-N-phenethyl-1,2-dihydroquinolin- Carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 188 (yield = 62%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12(m, 4H), 6.87(m, 3H), 3.90(s, 2H), 3.83(s, 3H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H), 2.68(m, 5H). MASS=610.26 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) , 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H). MASS = 610.26

합성예 189 : 5-(2-(4-브로모페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 189: 5- (2- (4-Bromophenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

5-아미노-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 189 화합물을 수득하였다(수율=53%)(1 mmol), DIPEA (1.5 mmol) and 2- (4-bromophenyl) acetyl chloride (1.2 mmol) were added to a solution of 5-amino-2-oxo-N-phenethyl-1,2-dihydroquinoline- mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 189 (Yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H, -NH), 7.12(dd, 2H), 6.87(dd, 2H), 3.90(m, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=503.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (d, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 7.27 (t, , &Lt; / RTI &gt; 2.83 (m, 2H). MASS = 503.08

합성예 190 : 5-(2-(4-브로모페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 190: 5- (2- (4-bromophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinolin- Carboxamide

5-아미노-1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 190 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-methoxybenzyl) 4-bromophenyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 190 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 (m, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(m, 3H), 7.23(s, 1H, -NH), 7.12(m, 4H), 6.87(dd, 2H), 3.90(m, 2H), 3.55(m, 4H), 2.83(m, 2H). MASS=623.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (d, 2H), 3.90 (m, 2H), 3.55 (m, 4H), 7.27 (m, 3H) , &Lt; / RTI &gt; 2.83 (m, 2H). MASS = 623.14

합성예 203 : 5-(2-(4-클로로페닐)아세트아미도)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 203: 5- (2- (4-Chlorophenyl) acetamido) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-(4-클로로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 203 화합물을 수득하였다(수율=66%).(1 mmol), DIPEA (1.5 mmol) and 2- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 203 (Yield = 66%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41(dd, 2H), 7.37(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(dd, 2H), 6.98(dd, 2H), 3.90(m, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.34(m, 2H). MASS=473.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H 2H), 7.39 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H) , &Lt; / RTI &gt; 2H), 2.83 (m, 2H), 2.34 (m, 2H). MASS = 473.15

합성예 204 : 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis 204: 5- (2- (4-Chlorophenyl) acetamido) -1- (4-methoxybenzyl) -N- Quinoline-3-carboxamide

5-아미노-1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 2-(4-클로로페닐)아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔컬럼크로마토그래피로 정제하여 합성예 204 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol), and N, N-dimethylaniline And 2- (4-chlorophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 204 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41(dd, 2H), 7.37(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(m, 4H), 6.98(m, 4H), 3.90(m, 2H), 3.55(m, 2H), 3.3(s, 2H), 2.83(m, 2H), 2.34(m, 2H), 1.67(s, 3H). 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H (M, 2H), 7.37 (d, 2H), 7.29 (t, 1H), 7.23 , 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.34 (m, 2H), 1.67 (s, 3H).

합성예 213 : 5-(2-(4-플루오로페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 213: 5- (2- (4-Fluorophenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-

55-아미노-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-플루오로페닐)아세틸 클로라이드(1.2 mmol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 213 화합물을 수족하였다(수율= 61%)2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-fluoro Phenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to elute the compound of Synthesis Example 213 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34(dd, 2H), 7.29(t, 1H), 7.18(dd, 2H), 7.12(dd, 2H), 6.94 (dd, 2H), 3.90(m, 2H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS=473.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H 2H), 3.90 (m, 2H), 3.83 (s, 3H), 3.55 (d, 2H) , &Lt; / RTI &gt; 2.83 (m, 2H). MASS = 473.18

합성예 214 : 5-(2-(4-에틸페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 214: 5- (2- (4-Ethylphenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-에틸페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 214 화합물을 수득하였다(수율= 63%)(1 mmol), DIPEA (1.5 mmol) and 2- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- ) Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 214 (yield = 63%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.27(s, 1H, -NH), 7.18(m, 4H), 6.98(m, 4H), 3.83(s, 3H), 3.55(m, 2H), 2.83(m, 2H), 2.60(d, 2H), 1.25(s, 3H). MASS=483.22 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 2.83 (m, 2H), 2.60 (m, 2H), 7.27 (s, , &Lt; / RTI &gt; 2H), 1.25 (s, 3H). MASS = 483.22

합성예 221 : N-(4-브로모펜에틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 221: Synthesis of N- (4-bromophenethyl) -5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-브로모펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-하이드록시페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 221 화합물을 수득하였다(수율= 61%)(1 mmol), DIPEA (1.5 mmol) and 2- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline- ) Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 221 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.92(dd, 2H), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(dd, 2H), 7.06 (dd, 2H), 6.63(dd, 2H), 5.35(s, 1H, -OH), 3.90(m, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=519.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H 1H), 7.29 (t, IH), 7.23 (s, IH, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H) 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 519.08

합성예 231 : N-(4-클로로펜에틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 231: Synthesis of N- (4-chlorophenethyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 231 화합물을 수득하였다(수율= 61%)(1 mmol), DIPEA (1.5 mmol) and 2- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline- Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 231 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.92(dd, 2H), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(dd, 2H), 7.06 (dd, 2H), 6.63(dd, 2H), 3.90(m, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=504.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H ), 7.29 (t, IH), 7.23 (s, IH, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H), 6.63 , &Lt; / RTI &gt; 2H), 2.83 (m, 2H). MASS = 504.12

합성예 290 : N-에틸-2-옥소-N-페닐-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 290: N-ethyl-2-oxo-N-phenyl-5-propionamido-1,2-dihydroquinoline-

5-아미노-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 프로피오닐클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 290 화합물을 수득하였다(수율= 69%).5-amino-2-oxo -N- -N- phenyl-a-1,2-dihydroquinoline-3-carboxamide (1mmol), DIPEA (1.5mmol) and propionyl chloride (1.2mmol) CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 290 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.81 (dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.19(t, 1H), 4.28(m, 2H), 2.45(m, 2H), 1.31(s, 3H), 1.02(s, 3H). MASS=363.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 1.31 (s, 3H), 1.02 (s, 3H), 7.23 (s, 1H) . MASS = 363.16

합성예 291 : 5-부티라미도-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 291: 5-Butyramido-N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-

5-아미노-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 부티릴클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 291 화합물을 수득하였다(수율= 61%).5-amino-2-oxo -N- -N- phenyl-a-1,2-dihydroquinoline-3-carboxamide (1mmol), DIPEA (1.5mmol) and butyryl chloride (1.2mmol) CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 291 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.81 (dd, 2H), 7.43(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.19(t, 1H), 4.28(m, 2H), 2.45(m, 2H), 1.31(s, 3H), 1.02(m, 2H), 0.90(s, 3H). MASS=377.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 1.31 (s, 3H), 1.02 (m, 2H), 7.28 (m, , 0.90 (s, 3 H). MASS = 377.17

합성예 293 : N-에틸-2-옥소-5-펜탄아미도-N-(p-톨일)-1,2-디하이드로 퀴놀린-3-카르복사마이드Synthesis Example 293: N-ethyl-2-oxo-5-pentanamido-N- (p-tolyl) -1,2-dihydroquinoline-

5-아미노-N=에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 펜타노일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 293 화합물을 수득하였다(수율= 62%).(1 mmol), DIPEA (1.5 mmol) and pentanoyl chloride (1.2 mmol) were added to a solution of 5-amino-N = ethyl-2-oxo- Was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 293 (Yield = 62%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 2.39(m, 2H), 2.34(s, 3H), 1.63(m, 2H), 1.31(m, 5H), 0.90(s, 3H). MASS=405.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.63 (m, 2H), 1.31 (m, 5H), 2.32 , 0.90 (s, 3 H). MASS = 405.21

합성예 294 : N-에틸-5-(2-메톡시아세트아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 294: N-ethyl-5- (2-methoxyacetamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-

5-아미노-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-메톡시아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 294 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-methoxyacetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 294 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34(dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 2.39 (m, 2H), 2.34(s, 3H), 1.63(m, 2H), 0.90(s, 3H). MASS=393.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.63 (s, 3H), 1.63 (m, 2H), 7.21 (d, 2H) . MASS = 393.17

합성예 305 : 5-(2-브로모아세트아미도)-N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 305: Synthesis of 5- (2-bromoacetamido) -N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-브로모아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 305 화합물을 수득하였다(수율=69%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-bromo-4-methoxyphenyl) Acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 305 (yield = 69%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 4.24 (m, 2H), 3.93 (s, 3H), 1.31 (s, 3H). MASS = 457.06 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.31 (s, 3H), 7.21 (d, 2H), 4.28 (m, 2H). MASS = 457.06

합성예 317 : N-(4-브로모페닐)-5-(2-클로로아세트아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 317: N- (4-Bromophenyl) -5- (2-chloroacetamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-브로모페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-클로로아세틸 클로라이드(1.2 mmol)를 CH2Cl2에서 15분 간 교반하였다(2mL). 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 317 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-chloroacetyl chloride The chloride (1.2 mmol) was stirred in CH 2 Cl 2 for 15 min (2 mL). The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 317 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(m, 2H), 4.24(m, 2H), 1.31(s, 3H). MASS=461.01 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 4.24 (m, 2H), 1.31 (s, 3H). MASS = 461.01

합성예 351 : N-(4-에틸페닐)-5-(2-플루오로아세트아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 351: Synthesis of N- (4-ethylphenyl) -5- (2-fluoroacetamido) -N-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-플루오로아세틸 클로라이드(1.2 mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 351 화합물을 수득하였다(수율= 69%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-fluoroacetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 351 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.41 (dd, 2H), 7.29(t, 1H), 7.27(dd, 2H), 7.23(s, 1H, -NH), 5.03(m, 2H), 3.44(s, 3H), 2.60(m, 2H), 1.25(s, 3H). MASS=381.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (d, 2H), 7.23 (s, 1H, -NH), 5.03 (m, 2H), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 MASS = 381.15

합성예 362 : (E)-5-(부트-2-엔아미도)-N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 362: Synthesis of (E) -5- (but-2-enamido) -N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- Mide

5-아미노-N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 (E)-부트-2-에노일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 362 화합물을 수득하였다(수율= 69%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and (E) - But-2-enoyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 362 (Yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.86 (s, 2H), 7.38(s, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.93(dd, 2H), 6.62(s, 1H), 5.35(s, 1H, -OH), 3.44(s, 3H), 2.05(s, 1H). MASS=377.14 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (s, 2H), 7.38 (s, 1H), 7.36 (s, 3H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H) , 2.05 (s, 1 H). MASS = 377.14

합성예 379 : N-(4-(하이드록시메틸)페닐)-5-(3-하이드록시프로판아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 379: Synthesis of N- (4- (hydroxymethyl) phenyl) -5- (3-hydroxypropanamido) -N-methyl-2-oxo-1,2-dihydroquinoline-

5-아미노-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 3-하이드록시 프로파노일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 379 화합물을 수득하였다(수율= 61%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 3 &lt; RTI ID = 0.0 & -Hydroxypropanoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 379 (Yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (dd, 2H), 7.36(d, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.91(m, 2H), 3.65(m, 2H, -OH), 3.44(s, 3H), 2.42(m, 2H). MASS=395.15H 1 NMR (400 MHz, 3 CDCl) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (m, 2H), 3.65 (m, 2H), 3.45 (s, 3H) , &Lt; / RTI &gt; 2.42 (m, 2H). MASS = 395.15

합성예 380 : N-(4-(하이드록시메틸)페닐)-N-메틸-5-(2-니트로아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 380: Synthesis of N- (4- (hydroxymethyl) phenyl) -N-methyl-5- (2-nitroacetamido) -2-oxo-1,2-dihydroquinoline-

55-아미노-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-니트로아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 380 화합물을 수득하였다(수율= 69%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2 &lt; RTI ID = 0.0 &gt; -Nitroacetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 380 (yield = 69%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.39 (dd, 2H), 7.36(d, 1H), 7.34(dd, 2H), 7.31(t, 1H), 7.14(t, 1H), 4.61(m, 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.42(m, 2H). MASS=410.12 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (s, 3H), 2.42 (m, 2H), 7.31 (t, 1H), 7.14 . MASS = 410.12

합성예 383 : (E)-5-(부트-2-엔아미도)-N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 383: (E) -5- (But-2-enamido) -N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-

5-아미노-N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 (E)-부트-2-에노일 클로라이드(1.2 mmol)를 CH2Cl2 2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 383 화합물을 수득하였다(수율= 61%).(1 mmol), DIPEA (1.5 mmol) and (E) -butoxyl-N-methyl- -2-enoyl chloride (1.2 mmol) was stirred in 2 mL of CH 2 Cl 2 for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 383 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 10.12(s, 1H, -NH), 9.23(dd, 2H), 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 4H), 7.29(t, 1H), 6.63(s, 1H), 6.62(s, 1H), 6.26(d, 1H), 5.61(s, 1H), 5.18(s, 1H), 3.44(s, 3H), 2.05(s, 3H). MASS=387.16 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, 1 H, -NH), 9.23 (dd, 2H), 8.28 ), 7.29 (s, IH), 6.63 (s, IH), 6.62 (s, IH), 6.26 , 2.05 (s, 3 H). MASS = 387.16

합성예 386 : 5-벤즈아미도-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 386: 5-Benzamido-N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

5-아미노-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 386 화합물을 수득하였다(수율= 66%).(1 mmol), DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were dissolved in CH 2 Cl 2 (2 mL) The mixture was stirred for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 386 (Yield = 66%).

1H NMR (400 MHz, CDCl3)δ 9.15(s, 1H, -NH), 8.28(s, 1H, -NH), 8.03(m, 3H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.70(t, 1H), 7.63(dd, 2H), 7.29(t, 1H), 3.21(m, 2H), 1.04(s, 3H). MASS=355.13 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H, -NH), 8.03 (m, 3H, -NH), 8.0 (s, 1H, -NH) , 7.88 (m, 2H), 7.70 (t, 1H), 7.63 (dd, 2H), 7.29 (t, 1H), 3.21 (m, 2H), 1.04 (s, 3H). MASS = 355.13

합성예 387 : (5-(3,4-디하이드록시벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 387: (5- (3,4-Dihydroxybenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide)

5-아미노-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 3,4-디하이드록시벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 387 화합물을 수득하였다(수율= 61%)Dihydroxyquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 3,4-dihydroxybenzoyl chloride (1.2 mmol) were dissolved in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 387 (Yield = 61%).

1H NMR (400 MHz, CDCl3)δ 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.42(d, 1H), 7.37(s, 1H), 7.29(t, 1H), 7.16(d, 1H), 5.35(m, 2H, -OH), 3.21(m, 2H), 1.04(s, 3H). MASS=367.12 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 ( 2H), 7.42 (d, 1H), 7.37 (s, IH), 7.29 (t, IH), 7.16 1.04 (s, 3 H). MASS = 367.12

합성예 388 : 5-(3,4-디메틸벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 388: 5- (3,4-Dimethylbenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

5-아미노-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1mmol), DIPEA(1.5mmol) 및 3,4-디메틸벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 388 화합물을 수득하였다(수율= 61%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 3,4-dimethylbenzoyl chloride (1.2 mmol) were dissolved in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 388 (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 9.15(s, 1H, -NH), 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.42(d, 1H), 7.37(s, 1H), 7.29(t, 1H), 7.16(d, 1H), 3.21(m, 2H), 2.34(s, 6H), 1.04(s, 3H). MASS=363.16 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 ( (m, 2H), 7.42 (d, IH), 7.37 (s, IH), 7.29 (t, IH), 7.16 , 3H). MASS = 363.16

합성예 395 : 5-(2-(벤조[d][1,3]디옥솔-5-일)아세트아미도)-N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 395: 5- (2- (Benzo [d] [1,3] dioxol-5-yl) acetamido) -N- (nitromethyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide

5-아미노-N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(벤조[d][1,3]디옥솔-5-일)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 395 화합물을 수득하였다(수율= 65%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (benzo [d] [1,3 ] Dioxol-5-yl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 395 (Yield = 65%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 6.9(s, 1H), 6.68(d, 1H), 6.76(d, 1H), 6.08(m, 2H), 6.07(m, 2H), 3.90(m, 2H). MASS=424.10 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 6.07 (m, 2H), 3.90 (m, 2H), 7.23 (s, , 2H). MASS = 424.10

합성예 398 (5-(3-(벤조[d][1,3]디옥솔-5-일)프로판아미도)-2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 398 Synthesis of (5- (3- (benzo [d] [1,3] dioxol-5-yl) propanamido) -2-oxo-N-propyl-l, 2-dihydroquinoline- Copy maid)

5-아미노-2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 3-(벤조[d][1,3]디옥솔-5-일)프로파노일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 398 화합물을 수득하였다(수율=53%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 3- (benzo [d] [1,3] dioxol 5-yl) propanoyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 398 (yield = 53%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.83 (d, 1H), 6.77 (s, 1H), 6.74 (d, 1H), 3.18 (m, 2H), 2.9 (m, 2H), 2.84 (m, 2H), 1.60 (m, 2H), 0.9 (s, 3H). MASS = 421.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H ), 7.23 (s, IH, -NH), 6.83 (d, IH), 6.77 (s, IH) , 2H), 1.60 (m, 2H), 0.9 (s, 3H). MASS = 421.16

합성예 400 : ((E)-5-(3-(나프탈렌-2-일)프로판아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 400: Synthesis of (E) -5- (3- (naphthalen-2-yl) propanamido) -2-oxo-N- (prop-1-en-1-yl) Hydroquinoline-3-carboxamide)

(E)-5-아미노-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 3-(나프탈렌-2-일)프로파노일 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 400 화합물을 수득하였다(수율= 61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and N, N-dimethylformamide And 3- (naphthalen-2-yl) propanoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 400 (yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.01(d, 1H), 8.0(s, 2H, -NH), 7.97(d, 1H), 7.94(d, 1H), 7.88(m, 2H), 7.58(t, 1H), 7.55(t, 1H), 7.46(s, 1H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(d, 1H), 7.11(s, 1H), 5.13(s, 1H), 3.01 (m, 2H), 2.84(m, 2H), 2.05(s, 3H). MASS=425.17 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (t, 1H), 7.58 (t, 1H), 7.46 (s, 1H), 7.29 , 7.01 (s, IH), 5.13 (s, IH), 3.01 (m, 2H), 2.84 (m, 2H), 2.05 (s, 3H). MASS = 425.17

합성예 401 : (E)-5-(2-(나프탈렌-2-일)아세트아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 401: Synthesis of (E) -5- (2- (naphthalen-2-yl) acetamido) -2-oxo-N- (prop-1-en-1-yl) Quinoline-3-carboxamide

(E)-5-아미노-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(나프탈렌-2-일)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 401 화합물을 수득하였다(수율=58%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and N, N-dimethylformamide And 2- (naphthalen-2-yl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to obtain the compound of Synthesis Example 401 (yield = 58%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.01(d, 1H), 8.0(s, 2H, -NH), 7.97 (d, 1H), 7.94(d, 1H), 7.88(m, 2H), 7.58(t, 1H), 7.55(t, 1H), 7.46(s, 1H), 7.29(t, 1H), 7.23(s, 1H, -NH), 7.18(d, 1H), 7.11(s, 1H), 5.13(s, 1H), 2.84 (m, 2H), 2.05(s, 3H). MASS=411.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (t, 1H), 7.58 (t, 1H), 7.46 (s, 1H), 7.29 , 7.11 (s, 1 H), 5.13 (s, 1 H), 2.84 (m, 2 H), 2.05 (s, 3 H). MASS = 411.16

합성예 404 : 5-(2-([1,1'-비페닐]-4-일)아세트아미도)-N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 404: Synthesis of 5- (2 - ([1,1'-biphenyl] -4-yl) acetamido) -N- (2-bromoethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide

5-아미노-N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-([1,1'-비페닐]-4-일)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 404 화합물을 수득하였다(수율= 61%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- ([l, l ' -Biphenyl] -4-yl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the synthetic example 404 compound (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.52(dd, 2H), 7.51(dd, 2H), 7.41(s, 1H), 7.33(dd, 2H), 7.29(m, 3H), 7.23(s, 1H, -NH), 4.22(m, 2H), 3.90(m, 2H), 3.72(m, 2H). MASS=503.08 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.52 (dd, 2H ), 7.51 (dd, 2H), 7.41 (s, IH), 7.33 (dd, 2H), 7.29 , &Lt; / RTI &gt; 2H), 3.72 (m, 2H). MASS = 503.08

합성예 424 : 5-(2-(4-벤질페닐)아세트아미도)-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 424: Synthesis of 5- (2- (4-benzylphenyl) acetamido) -N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline- Mide)

5-아미노-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(4-벤질페닐)아세틸 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 424 화합물을 수득하였다(수율=61%).Dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-amino- -Benzylphenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 424 (yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.33(dd, 2H), 7.26(t, 1H), 7.23(dd, 2H), 7.11(m, 4H), 6.86(s, 1H), 6.73(d, 1H), 6.68(d, 1H), 5.35(s, 2H, -OH), 3.96(m, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=547.21 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H ), 7.33 (d, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 7.11 (m, 4H) , 5.35 (s, 2H, -OH), 3.96 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 547.21

합성예 425 : N-(3,4-디하이드록시펜에틸)-2-옥소-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 425: Synthesis of N- (3,4-dihydroxyphenethyl) -2-oxo-5-propionamido-1,2-dihydroquinoline-

5-아미노-N=(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 프로피오닐클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 425 화합물을 수득하였다(수율=69%)Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and propionyl chloride (1 mmol) were added to a solution of 5-amino- 1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 425 (Yield = 69%).

1H NMR (400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 6.86(s, 1H), 6.68(d, 1H), 6.73(d, 1H), 5.35(s, 2H, -OH), 3.55(m, 2H), 2.83(m, 2H), 2.45(m, 2H), 1.02 (s, 3H). MASS = 395.15 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2.83 (m, 2H), 2.45 (m, 2H), 1.02 (s, 3H). MASS = 395.15

합성예 426 : 5-부티라미도-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 426: Synthesis of 5-butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 부티릴클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 426 화합물을 수득하였다(수율=61%).Dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and butyryl chloride 1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 426 compound (Yield = 61%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 6.86(s, 1H), 6.68(d, 1H), 6.73 (d, 1H), 5.35(s, 2H, -OH), 3.55(m, 2H), 2.83(m, 2H), 2.39(m, 2H), 1.78(m, 2H), 0.9(s, 3H). MASS=409.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2.83 (m, 2H), 2.39 (m, 2H), 1.78 (m, 2H), 0.9 (s, 3H). MASS = 409.16

합성예 427 : N-(3,4-디하이드록시펜에틸)-2-옥소-5-펜탄아미도-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 427: Synthesis of N- (3,4-dihydroxyphenethyl) -2-oxo-5-pentanamido-1,2-dihydroquinoline-

5-아미노-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 펜타노일 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 427 화합물을 수득하였다 (수율=66%).(1 mmol), DIPEA (1.5 mmol) and pentanoyl chloride (1 mmol) were added to a solution of 5-amino-N- (3,4-dihydroxyphenylethyl) -2-oxo-1,2-dihydroquinoline- 1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 427 (yield = 66%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H, -NH), 7.88(m, 2H), 7.29(t, 1H), 7.23(s, 1H, -NH), 6.86(s, 1H), 6.68(d, 1H), 6.73(d, 1H), 5.35(s, 2H, -OH), 3.55(m, 2H), 2.83(m, 2H), 2.39(m, 2H), 1.63(m, 2H), 1.31(m, 2H), 0.9(s, 3H). MASS= 423.18 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2.83 (m, 2H), 2.39 (m, 2H), 1.63 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H). MASS = 423.18

합성예 434 : 5-(2-(에틸티오)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 434: 5- (2- (Ethylthio) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 3-(메틸티오)프로파노일 클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 434 화합물을 수득하였다(수율=61%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 3- (2-amino- Methylthio) propanoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 434 (Yield = 61%).

1H NMR (400 MHz, CDCl3)δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 (d, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 3.55 (m, 2H), 3.51 (m, 2H), 2.94 (m, 2H), 2.48 (m, 2H), 1.25 (s, 3H). MASS = 459.16 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H ), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 (M, 2H), 3.55 (m, 2H), 2.94 (m, 2H), 2.48 (m, 2H), 1.25 (s, 3H). MASS = 459.16

합성예 435 : 5-(2-(에틸아미노)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 435: Synthesis of 5- (2- (ethylamino) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-(에틸아미노)아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 435 화합물을 수득하였다(수율= 62%).Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- ( Ethylamino) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 435 (Yield = 62%).

1H NMR(400 MHz, CDCl3)δ 8.28(s, 1H), 8.03(s, 1H, -NH), 8.01(d, 1H), 8.0 (s, 1H, -NH), 7.97(m, 2H), 7.88(m, 2H), 7.55(m, 2H), 7.46(s, 1H), 7.29 (t, 1H), 7.23(s, 1H, -NH), 7.18(d, 1H), 3.55(m, 2H), 3.27(m, 2H), 2.94(m, 2H), 2.59(m, 2H), 2.0(s, 1H, -NH), 1.02 (s, 3H). MASS=442.20 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (m, 2H 1H), 7.18 (d, 1H), 3.55 (m, 2H), 7.88 (m, 2H) 2H), 3.27 (m, 2H), 2.94 (m, 2H), 2.59 (m, 2H), 2.0 (s, MASS = 442.20

합성예 436 : 5-(2-에톡시아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 436: Synthesis of 5- (2-ethoxyacetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드(1 mmol), DIPEA(1.5 mmol) 및 2-에톡시아세틸클로라이드(1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 436 화합물을 수득하였다.Dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-ethoxy-2- (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 436.

1H NMR(400 MHz, CDCl3)δ 8.42(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.57(s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H), 6.57 (s, 1 H)

Figure 112016031927621-pct00011
Figure 112016031927621-pct00011

단계(a-0)의 일반적 과정General procedure of step (a-0)

출발물질(500 mg, 2.13 mmol)을 무수 1,4-디옥산(25 mL)에 용해시켰다. R1(50mL)를 용액에 첨가하였다. 혼합물을 12시간 동안 상온에서 교반하고 기화시켜 9번 화합물을 수득하였다.The starting material (500 mg, 2.13 mmol) was dissolved in anhydrous 1,4-dioxane (25 mL). R 1 (50 mL) was added to the solution. The mixture was stirred at ambient temperature for 12 hours and evaporated to give compound No. 9.

합성예 72 : 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 클로라이드Synthesis Example 72: Synthesis of 2-oxo-1,2-dihydroquinoline-3-carbonyl chloride

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol) 를 무수 1,4-디옥산(2mL)에 용해시켰다. Cl2(2mL)를 용액에 첨가하였다. 혼합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예72 화합물을 수득하였다(수율=80%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL). Cl 2 (2 mL) was added to the solution. The mixture was stirred at room temperature for 12 hours and evaporated to give the compound of Synthesis Example 72 (yield = 80%).

1HNMR(400MHz,CDCl3)δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H). MASS = 207.01 1 H NMR (400 MHz, CDCl 3 )? 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , 1H). MASS = 207.01

합성예 73 : 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 브로마이드Synthesis Example 73: Synthesis of 2-oxo-1,2-dihydroquinoline-3-carbonylbromide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 무수 1,4-디옥산 (2 mL)에 용해시켰다. 이후 Br2(2mL)를 용액에 첨가하였다. 혼합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예 73 화합물을 수득하였다(수율=82%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL). Br 2 (2 mL) was then added to the solution. The mixture was stirred at room temperature for 12 hours and evaporated to give the compound of Synthesis Example 73 (yield = 82%).

1H NMR (400 MHz, CDCl3)δ 8.37(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H). MASS=250.96 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H). MASS = 250.96

합성예 74 : 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 플로라이드Synthesis Example 74: 2-oxo-1,2-dihydroquinoline-3-carbonyl fluoride

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 무수 1,4-디옥산(2 mL)에 용해시켰다. F2(2mL)를 용액에 첨가하였다. 혼합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예74 화합물을 수득하였다(수율=64%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL). F 2 (2 mL) was added to the solution. The mixture was stirred at room temperature for 12 hours and evaporated to give the compound of Synthesis Example 74 (yield = 64%).

1HNMR(400MHz,CDCl3)δ 8.37(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H). MASS = 191.04 1 H NMR (400 MHz, CDCl 3 )? 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , 1H). MASS = 191.04

합성예 75 : 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 아이오다이드Synthesis Example 75: 2-oxo-1,2-dihydroquinoline-3-carbonyl iodide

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 무수 1,4-디옥산(2 mL)에 용해시켰다. I2(2mL)를 용액에 첨가하였다. 혼합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예 75 화합물을 수득하였다(수율=71%).2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL). I 2 (2 mL) was added to the solution. The mixture was stirred at room temperature for 12 hours and evaporated to give the compound of Synthesis Example 75 (yield = 71%).

1HNMR(400MHz,CDCl3)δ 8.37(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14(t, 1H). MASS=298.94 1 H NMR (400 MHz, CDCl 3 )? 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , 1H). MASS = 298.94

단계(b-10)의 일반적 과정General procedure of step (b-10)

R2(0.65mL, 12.73mmol)를 0℃에서 피리딘(15mL)에 용해된 산 현탄액(1.49g, 6.36mmol)에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고 ,1NHCl(50mL)를 첨가하고 물로 세척하여 10번 화합물을 수득하였다.R 2 (0.65 mL, 12.73 mmol) was added to an acid suspension (1.49 g, 6.36 mmol) dissolved in pyridine (15 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 h, 1N HCl (50 mL) was added and washed with water to give compound 10.

합성예 11 : 3-클로로퀴놀린-2(1H)-온)Synthesis Example 11: 3-Chloroquinolin-2 (1 H) -one)

Cl2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 11 화합물을 수득하였다(수율=97%).Cl 2 ( 2 mmol) was added to an acidic suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 11 (Yield = 97%).

1HNMR(400MHz, CDCl3)δ 8.0 (s, 1H, -NH), 8.14 (d, 1H), 7.54 (s, 1H), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (d, 1H). MASS = 179.01 1 H NMR (400 MHz, CDCl 3 )? 8.0 (s, IH, -NH), 8.14 (d, IH), 7.54 (s, IH), 7.36 , 1H). MASS = 179.01

합성예 12 (3,5-디클로로퀴놀린-2(1H)-온)Synthesis Example 12 (3,5-Dichloroquinolin-2 (1H) -one)

Cl2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 5-클로로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 12 화합물을 수득하였다(수율= 90%).Cl 2 ( 2 mmol) was added to an acidic suspension of 5-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 12 (Yield = 90%).

1HNMR(400MHz, CDCl3)δ 8.02(d, 1H), 8.0(s, -NH, 1H), 7.54(s, 1H), 7.25 (t, 1H), 7.18(s, 1H). MASS=212.97 1 H NMR (400 MHz, CDCl 3 )? 8.02 (d, 1H), 8.0 (s, -NH, 1H), 7.54 (s, 1H), 7.25 (t, 1H), 7.18 (s, 1H). MASS = 212.97

합성예 13 : 3-클로로-6-플루오로퀴놀린-2(1H)-온Synthesis Example 13: 3-Chloro-6-fluoroquinolin-2 (1H) -one

Cl2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 6-플루오로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 13 화합물을 수득하였다(수율=92%).Cl 2 ( 2 mmol) was added to an acidic suspension of 6-fluoro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine . The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 13 (Yield = 92%).

1HNMR(400MHz, CDCl3) δ 8.0(s, 1H, -NH), 7.74(d, 1H), 7.54(s, 1H), 7.10 (d, 1H), 6.94(d, 1H). MASS=197.00 1 H NMR (400 MHz, CDCl 3 )? 8.0 (s, IH, -NH), 7.74 (d, IH), 7.54 (s, IH), 7.10 (d, MASS = 197.00

합성예 14 : 3-클로로-7-플루오로퀴놀린-2(1H)-온Synthesis Example 14: Synthesis of 3-chloro-7-fluoroquinolin-2 (1H) -one

Cl2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 7-플루오로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예14 화합물을 수득하였다 (수율=83%).Cl 2 ( 2 mmol) was added to an acidic suspension of 7-fluoro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine . The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 14 (yield = 83%).

1HNMR (400MHz, CDCl3)δ 8.0(s, 1H, -NH), 7.70(d, 1H), 7.54(s, 1H), 7.54 (s, 1H), 7.34(d, 1H), 6.93(d, 1H). MASS=197.00 1 HNMR (400MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.70 (d, 1H), 7.54 (s, 1H), 7.54 (s, 1H), 7.34 (d, 1H), 6.93 (d , 1H). MASS = 197.00

합성예 15 : 3-아이오도퀴놀린-2(1H)-온Synthesis Example 15: 3-Iodoquinolin-2 (1H) -one

I2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 15 화합물을 수득하였다(수율=94%).I 2 ( 2 mmol) was added to an acidic suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give Synthesis Example 15 compound (Yield = 94%).

1HNMR (400MHz, CDCl3)δ 8.17(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.34(t, 1H), 7.14(t, 1H). MASS=270.95 1 H NMR (400 MHz, CDCl 3 )? 8.17 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , 1H). MASS = 270.95

합성예 16 : 3,5-디아이오도도퀴놀린-2(1H)-온Synthesis Example 16: 3,5-Diiodoquinolin-2 (1H) -one

I2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 5-아이오도-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl (1mL)를 첨가하고 물로 세척하여 10번 화합물을 수득하였다(수율= 92%).I 2 ( 2 mmol) was added to an acid suspension of 5-iodo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C . The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 h, 1N HCl (1 mL) was added and washed with water to give compound 10 (yield = 92%).

1HNMR(400MHz, CDCl3)δ 8.17(s, 1H), 8.1(d, 1H), 8.0(s, 1H, -NH), 7.47(d, 1H), 7.08(t, 1H). MASS=396.85 1 H NMR (400 MHz, CDCl 3 )? 8.17 (s, IH), 8.1 (d, IH), 8.0 (s, IH, -NH), 7.47 (d, IH), 7.08 (t, IH). MASS = 396.85

합성예 17 : 3-아이오도-5-메틸퀴놀린-2(1H)-온Synthesis Example 17: 3-Iodo-5-methylquinolin-2 (1H) -one

I2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 5-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 10번의 화합물을 수득하였다(수율=92%).I 2 ( 2 mmol) was added to an acid suspension of 5-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 h, 1N HCl (1 mL) was added and washed with water to give 10 compounds (yield = 92%).

1HNMR(400MHz, CDCl3)δ 8.17(s, 1H), 8.0(s, 1H, -NH), 7.95(d, 1H), 7.19 (t, 1H), 6.75(d, 1H), 2.48(s, 3H). MASS=284.87 1 HNMR (400MHz, CDCl 3) δ 8.17 (s, 1H), 8.0 (s, 1H, -NH), 7.95 (d, 1H), 7.19 (t, 1H), 6.75 (d, 1H), 2.48 (s , 3H). MASS = 284.87

합성예 18 : 3-메틸퀴놀린-2(1H)-온Synthesis Example 18: 3-Methylquinolin-2 (1H) -one

(CH3)2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 18 화합물을 수득하였다(수율=48%).(CH 3 ) 2 ( 2 mmol) was added to an acid suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 18 (yield = 48%).

1HNMR (400MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(d, 1H), 2.43(s, 3H). MASS=159.07 1 HNMR (400MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (d, 1H), 2.43 (s , 3H). MASS = 159.07

합성예 19 : 3-메틸-6-(메틸티오)퀴놀린-2(1H)-온Synthesis Example 19: Synthesis of 3-methyl-6- (methylthio) quinolin-2 (1H)

(CH3)2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 6-(메틸티오)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 19 화합물을 수득하였다(수율=49%).(CH 3) dissolving the 2 (2mmol) at 0 ℃ in pyridine (0.1mL) 6- (methylthio) of acid 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1mmol) I was hit by the current deposit. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 h, 1N HCl (1 mL) was added and washed with water to give the compound of Synthetic Example 19 (yield = 49%).

1HNMR(400MHz, CDCl3)δ 8.0(s, 1H, -NH), 7.72(d, 1H), 7.66(s, 1H), 7.14 (s, 1H), 6.87(d, 1H), 2.53(s, 3H), 2.43(s, 3H). MASS=205.06 1 HNMR (400MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.72 (d, 1H), 7.66 (s, 1H), 7.14 (s, 1H), 6.87 (d, 1H), 2.53 (s , &Lt; / RTI &gt; 3H), 2.43 (s, 3H). MASS = 205.06

합성예 20 : 3-메톡시퀴놀린-2(1H)-온Synthesis Example 20: Synthesis of 3-methoxyquinolin-2 (1H) -one

(OCH3)2(2mmol)를 0℃에서 피리딜(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 20 화합물을 수득하였다(수율=94%).(OCH 3) acid in which 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1mmol) was dissolved 2 (2mmol) at 0 ℃ to pyridyl (0.1mL) was dropwise to the suspension. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 20 (Yield = 94%).

1HNMR(400MHz, CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.29(s, 1H), 3.80(s, 3H). MASS=175.06 1 HNMR (400MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.29 (s , &Lt; / RTI &gt; 1H), 3.80 (s, 3H). MASS = 175.06

합성예 21 : 3,7-디메톡시퀴놀린-2(1H)-온Synthesis Example 21: Synthesis of 3,7-dimethoxyquinolin-2 (1H) -one

(OCH3)2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 7-메톡시-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 21 화합물을 수득하였다(수율=76%)(OCH 3) was 7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid suspension of metallic acid (1mmol) was dissolved 2 (2mmol) at 0 ℃ in pyridine (0.1mL) Respectively. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthetic Example 21 (Yield = 76%

1HNMR(400MHz, CDCl3)δ8.0(s, 1H, -NH), 7.31(s, 1H), 7.25(d, 1H), 6.68 (d, 1H), 6.29(s, 1H), 3.8(s, 3H), 3.83(s, 3H). MASS=205.07 1 HNMR (400MHz, CDCl 3) δ8.0 (s, 1H, -NH), 7.31 (s, 1H), 7.25 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 3.8 ( s, 3H), 3.83 (s, 3H). MASS = 205.07

합성예 22 : 3-아미노퀴놀린-2(1H)-온Synthesis Example 22: Synthesis of 3-aminoquinolin-2 (1H) -one

(NH2)2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 22 화합물을 수득하였다(수율=73%).(NH 2) 2 (2mmol) of the acid that 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1mmol) was dissolved at 0 ℃ in pyridine (0.1mL) was dropwise to the suspension. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give Synthesis Example 22 compound (yield = 73%).

1HNMR (400MHz,CDCl3)δ 8.56(s, 2H,-NH2), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.10(s, 1H). MASS=160.06 1 HNMR (400MHz, CDCl 3) δ 8.56 (s, 2H, -NH2), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H), 6.10 (s, 1 H). MASS = 160.06

합성예 23 : 3-아미노-1-(4-플루오로벤질)퀴놀린-2(1H)-온Synthesis Example 23: 3-Amino-1- (4-fluorobenzyl) quinolin-2 (1H)

(NH2)2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 1-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 23 화합물을 수득하였다(수율=92%).(NH 2) 1- dissolving 2 (2mmol) at 0 ℃ in pyridine (0.1mL) (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1mmol ), Respectively. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 23 (yield = 92%).

1HNMR (400MHz, CDCl3)δ 8.56(s, 1H, -NH2), 7.65(d, 1H), 7.39(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 7.12(dd, 2H), 4.94(s, 2H). MASS=268.10 1 HNMR (400MHz, CDCl 3) δ 8.56 (s, 1H, -NH 2), 7.65 (d, 1H), 7.39 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 ( t, 1 H), 7.12 (dd, 2 H), 4.94 (s, 2 H). MASS = 268.10

합성예 24 : 3-플루오로퀴놀린-2(1H)-온Synthesis Example 24: 3-Fluoroquinolin-2 (1H) -one

F2(2mmol)를 0℃에서 피리딘(0.1mL)에 용해시킨 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1mmol)의 산 현탄액에 적상하였다. 혼합물을 110℃에서 3시간 동안 상온까지 냉각시키고, 1NHCl(1mL)를 첨가하고 물로 세척하여 합성예 24 화합물을 수득하였다(수율= 90%).F 2 ( 2 mmol) was added to an acidic suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) dissolved in pyridine (0.1 mL) at 0 ° C. The mixture was cooled to room temperature at 110 &lt; 0 &gt; C for 3 hours, 1N HCl (1 mL) was added and washed with water to give the compound of Synthesis Example 24 (Yield = 90%).

1HNMR(400MHz,CDCl3)δ 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.14(t, 1H), 6.96(s, 1H). MASS=163.04 1 HNMR (400MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.96 (s , 1H). MASS = 163.04

단계(c-11)의 일반적 과정General procedure of step (c-11)

출발물질(230 mg, 0.8 mmol)을 LiOH(15 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 11번 화합물을 수득하였다.The starting material (230 mg, 0.8 mmol) was refluxed in LiOH (15 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to give compound No. 11.

합성예 1 : 퀴놀린-2(1H)-온Synthesis Example 1: Synthesis of quinolin-2 (1H) -one

2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 LiOH(0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 1 화합물을 수득하였다(수율=92%).2-Oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to obtain the compound of Synthesis Example 1 (yield = 92%).

1HNMR(400MHz, CDCl3)δ 8.42(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.57(s, 1H). MASS=145.05 1 H NMR (400 MHz, CDCl 3 )? 8.42 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, , &Lt; / RTI &gt; 1H), 6.57 (s, 1H). MASS = 145.05

합성예 2 : 1-메틸퀴놀린-2(1H)-온Synthesis Example 2: 1-Methylquinolin-2 (1H) -one

1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭 애시드(1 mmol)를 LiOH(0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 2 화합물을 수득하였다(수율=93%).1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to obtain the compound of Synthesis Example 2 (yield = 93%).

1HNMR(400MHz,CDCl3)δ 8.42(s, 1H), 7.65(d, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.57(s, 1H), MASS=159.07 1 HNMR (400MHz, CDCl 3) δ 8.42 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H) , MASS = 159.07

합성예 3 : 1-에틸퀴놀린-2(1H)-온Synthesis Example 3: 1-Ethylquinolin-2 (1H) -one

1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 LiOH(0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 3 화합물을 수득하였다(수율=90%).1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to obtain the compound of Synthesis Example 3 (yield = 90%).

1HNMR(400MHz, CDCl3)δ 8.42(s, 1H), 7.65(t, 1H), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 6.57(s, 1H), 4.28(s, 2H), 1.31(s, 3H). MASS=173.08 1 HNMR (400MHz, CDCl 3) δ 8.42 (s, 1H), 7.65 (t, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H) , 4.28 (s, 2 H), 1.31 (s, 3 H). MASS = 173.08

합성예 4 : 5-브로모퀴놀린-2(1H)-온Synthesis Example 4: Synthesis of 5-bromoquinolin-2 (1H) -one

5-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)를 LiOH (0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 4 화합물을 수득하였다(수율=96%).5-Bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to obtain the compound of Synthesis Example 4 (yield = 96%).

1HNMR(400MHz,CDCl3)δ 8.42(s, 1H), 8.08(d, 1H), 8.0(s, 1H, -NH), 7.29 (d, 1H), 7.05(t, 1H), 6.57(s, 1H). MASS=222.96 1 HNMR (400MHz, CDCl 3) δ 8.42 (s, 1H), 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.29 (d, 1H), 7.05 (t, 1H), 6.57 (s , 1H). MASS = 222.96

합성예 5 : 6-브로모퀴놀린-2(1H)-온Synthesis Example 5: 6-bromoquinolin-2 (1H) -one

6-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)을 LiOH (0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 5 화합물을 수득하였다 (수율=92%).6-Bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to give the compound of Synthesis Example 5 (yield = 92%).

1HNMR (400MHz,CDCl3)δ 8.42(s, 1H), 8.0(s, 1H, -NH), 7.55(d, 1H), 7.53 (d, 1H), 7.46(d, 1H), 6.57(s, 1H). MASS=222.96 1 HNMR (400MHz, CDCl 3) δ 8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 6.57 (s , 1H). MASS = 222.96

합성예 6 : 7-브로모퀴놀린-2(1H)-온Synthesis Example 6: 7-Bromoquinolin-2 (1H) -one

7-브로모-2-옥소-1,2-디하이드로퀴놀린-3-카복실릭애시드(1 mmol)을 LiOH (0.1 mL)에 두시간 동안 환류하였다. 혼합물을 1N HCl로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 6 화합물을 수득하였다 (수율= 86%).7-Bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was refluxed in LiOH (0.1 mL) for two hours. The mixture was acidified with 1N HCl and filtered. The filtration residue was washed with water to obtain the compound of Synthesis Example 6 (yield = 86%).

1HNMR(400MHz,CDCl3)δ8.42(s, 1H), 8.0(s, 1H, -NH), 7.82(d, 1H), 7.29 (d, 1H), 7.25(d, 1H), 6.57(s, 1H). MASS=222.96 1 HNMR (400MHz, CDCl 3) δ8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.29 (d, 1H), 7.25 (d, 1H), 6.57 ( s, 1H). MASS = 222.96

합성예 511: 5-클로로-2-옥소-N-페네틸-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드Synthesis Example 511: 5-Chloro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-

5-클로로-2-옥소-엔-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-(트라이플루오로메톡시)벤질브로마이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=61%).5-chloro-2-oxo-ene-phenethyl-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4- (trifluoromethoxy) benzyl bromide, 18- , And potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield: 61%).

1H NMR (400MHz, CDCl3) δ9.77(s, 1H), 9.45(s,1H), 7.51-7.45(m, 1H), 7.36(s, 1H), 7.32-7.14(m, 8H), 5.57(s, 1H), 3.73(dd, 2H), 2.95(t, 1H), MASS=500.29 1 H NMR (400MHz, CDCl 3 ) δ9.77 (s, 1H), 9.45 (s, 1H), 7.51-7.45 (m, 1H), 7.36 (s, 1H), 7.32-7.14 (m, 8H), 5.57 (s, IH), 3.73 (dd, 2H), 2.95 (t, IH), MASS =

합성예 512: 5-클로로-1-(4-에틸벤질)-2-옥소-N-페네틸-1,2-다이하이드로퀴놀린-3-카프복스아미드Synthesis Example 512: Synthesis of 5-chloro-l- (4-ethylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline-

5-클로로-2-옥소-엔-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-에틸 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=63%)After 5-chloro-2-oxo-ene-phenethyl-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-ethylbenzyl chloride, 18-crown- And the mixture was stirred at room temperature for 12 hours (yield: 63%).

1H NMR (400MHz, CDCl3) δ 9.86(s, 1H), 9.43(s, 1H), 7.43(t, 1H), 7.43-7.21(m, 7H), 7.14(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.75-3.69(m, 2H), 2.95(t, 2H), 2.59(dd, 2H), 1.18(t, 3H), MASS=444.51 1 H NMR (400MHz, CDCl 3 ) δ 9.86 (s, 1H), 9.43 (s, 1H), 7.43 (t, 1H), 7.43-7.21 (m, 7H), 7.14 (d, 2H), 7.06 (d 2H), 5.55 (s, IH), 3.75-3.69 (m, 2H), 2.95 (t, 2H), 2.59 (dd, 2H)

합성예 513: 5-클로로-1-(4-아이소프로필벤질)-2-옥소-N-페네틸-1,2-다이하이드로퀴놀린-3-카르복스아미드Synthesis Example 513: 5-chloro-l- (4-isopropylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline-

5-클로로-1-메틸-2-옥소-엔-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-아이소프로필 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=66%).1-methyl-2-oxo-ene-phenethyl-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, and 4-isopropylbenzyl chloride, 18-crown- , And potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield = 66%).

1H NMR(400MHz, CDCl3) δ 9.87(s, 1H), 9.43(s, 1H), 9.44(t, 1H), 7.34-7.21(m, 7H), 7.16(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.72 (dd, 2H), 2.95(t, 2H), 2.89-2.82(m, 1H), 1.19(d, 6H), MASS=458.59 1 H NMR (400MHz, CDCl 3 ) δ 9.87 (s, 1H), 9.43 (s, 1H), 9.44 (t, 1H), 7.34-7.21 (m, 7H), 7.16 (d, 2H), 7.06 (d 2H), 5.55 (s, IH), 3.72 (dd, 2H), 2.95 (t, 2H), 2.89-2.82

합성예 514: 5-클로로-1-(4-나이트로벤질)-2-옥소-N-페네틸-1,2-다이하이드로퀴놀린-3-카르복스아미드Synthesis Example 514: 5-Chloro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-

5-클로로-2-옥소-엔-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-나이트로 벤질 브로마이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=64%).5-chloro-2-oxo-ene-phenethyl-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-nitrobenzylbromide, 18- And the mixture was stirred at room temperature for 12 hours (yield = 64%).

1H NMR (400MHz, CDCl3) δ 9.67 (s, 1H), 9.47 (s, 1H), 8.19 (d, 1H), 7.46 (t, 1H), 7.38 (d, 1H), 7.33-7.21 (m, 7H), 7.08 (d, 1H), 5.66 (s, 1H), 3.73 (dd, 2H), 2.95 (t, 2H), MASS=461.39 1 H NMR (400MHz, CDCl 3 ) δ 9.67 (s, 1H), 9.47 (s, 1H), 8.19 (d, 1H), 7.46 (t, 1H), 7.38 (d, 1H), 7.33-7.21 (m , 7.08 (d, IH), 5.66 (s, IH), 3.73 (dd, 2H), 2.95 (t, 2H), MASS = 461.39

합성예 515: 5-클로로-1-(4-메톡시벤질)-2-옥소-N-페네틸-1,2-다이하이드로퀴놀린-3-카르복스아미드Synthesis Example 515: Synthesis of 5-chloro-l- (4-methoxybenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline-

5-클로로-2-옥소-엔-페네틸-1,2-디하이드로퀴놀린-3-카르복스 아미드를 디메틸포름아미드에 녹인 후, 4-메톡시 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=51%).5-chloro-2-oxo-ene-phenethyl-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-methoxybenzyl chloride, 18- And the mixture was stirred at room temperature for 12 hours (yield = 51%).

1H NMR(400MHz, CDCl3) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H), 7.34-7.21(m, 7H), 7.10(d, 2H), 6.84(d, 2H), 5.52(s, 2H), 3.76-3.70(m, 5H), 2.96(t, 2H), MASS=446.55 1 H NMR (400MHz, CDCl 3 ) δ 9.85 (s, 1H), 9.42 (s, 1H), 7.44 (t, 1H), 7.34-7.21 (m, 7H), 7.10 (d, 2H), 6.84 (d 2H), 5.52 (s, 2H), 3.76-3.70 (m, 5H), 2.96 (t, 2H), MASS = 446.55

합성예 516: 5-클로로-1-(4-에틸벤질)-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카프복스아미드)Synthesis Example 516: Synthesis of 5-chloro-1- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-

5-클로로-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-에틸 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=67%)(4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-ethylbenzyl chloride, 18- 6, and potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield: 67%).

1H NMR (400MHz, CDCl3) δ 9.86(s, 1H), 9.43(s, 1H), 7.43(t, 1H), 7.43-7.21(m, 6H), 7.14(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.75-3.69(m, 2H), 2.95(t, 2H), 2.59(dd, 2H), 1.18(t, 3H), MASS=462.85 1 H NMR (400MHz, CDCl 3 ) δ 9.86 (s, 1H), 9.43 (s, 1H), 7.43 (t, 1H), 7.43-7.21 (m, 6H), 7.14 (d, 2H), 7.06 (d 2H), 5.55 (s, 1H), 3.75-3.69 (m, 2H), 2.95 (t, 2H), 2.59 (dd, 2H)

합성예 517: 5-클로로-N-(4-플루오로페네틸)-1-(4-아이소프로필벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드Synthesis Example 517: 5-Chloro-N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -2-oxo-1,2-dihydroquinoline-

5-클로로-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-아이소프로필 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=63%)5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, and 4-isopropylbenzyl chloride, 18- -6, and potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield: 63%).

1H NMR (400MHz, CDCl3) δ 9.87(s, 1H), 9.43(s, 1H), 9.44(t, 1H), 7.34-7.21(m, 6H), 7.16(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.72 (dd, 2H), 2.95(t, 2H), 2.89-2.82(m, 1H), 1.19 (d, 6H), MASS= 476.55 1 H NMR (400MHz, CDCl 3 ) δ 9.87 (s, 1H), 9.43 (s, 1H), 9.44 (t, 1H), 7.34-7.21 (m, 6H), 7.16 (d, 2H), 7.06 (d 2H), 5.55 (s, 1H), 3.72 (dd, 2H), 2.95 (t, 2H), 2.89-2.82

합성예 518: 5-클로로-N-(4-플루오로페네틸)-1-(4-나이트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드Synthesis Example 518: 5-Chloro-N- (4-fluorophenethyl) -1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-

5-클로로-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-나이트로 벤질 브로마이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=73%).After the 5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-nitrobenzyl bromide, 18- -6, and potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield: 73%).

1H NMR(400MHz, CDCl3) δ 9.67(s, 1H), 9.47(s, 1H), 8.19(d, 1H), 7.46(t, 1H), 7.38(d, 1H), 7.33-7.21(m, 6H), 7.08(d, 1H), 5.66(s, 1H), 3.73(dd, 2H), 2.95(t, 2H), MASS=479.23 1 H NMR (400MHz, CDCl 3 ) δ 9.67 (s, 1H), 9.47 (s, 1H), 8.19 (d, 1H), 7.46 (t, 1H), 7.38 (d, 1H), 7.33-7.21 (m (D, 2H), 3.95 (d, 2H), 7.08 (d,

합성예 519: 5-클로로-N-(4-플루오로페네틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드Synthesis Example 519: 5-Chloro-N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

5-클로로-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드를 디메틸포름아미드에 녹인 후, 4-메톡시 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=77%).5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, and 4-methoxybenzyl chloride, 18- -6, and potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield = 77%).

1H NMR (400MHz, CDCl3) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H), 7.34-7.21(m, 6H), 7.10(d, 2H), 6.84(d, 2H), 5.52(s, 2H), 3.76-3.70(m, 5H), 2.96(t, 2H), MASS=464.87 1 H NMR (400MHz, CDCl 3 ) δ 9.85 (s, 1H), 9.42 (s, 1H), 7.44 (t, 1H), 7.34-7.21 (m, 6H), 7.10 (d, 2H), 6.84 (d 2H), 5.52 (s, 2H), 3.76-3.70 (m, 5H), 2.96 (t, 2H), MASS = 464.87

합성예 520: 5-클로로-N-(4-플루오로페네틸)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드Synthesis Example 520: Synthesis of 5-chloro-N- (4-fluorophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-

5-클로로-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드를디메틸포름아미드에 녹인 후, 4-메톡시 벤질 클로라이드, 18-크라운-6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다(수율=69%).5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, and 4-methoxybenzyl chloride, 18- -6, and potassium carbonate were added thereto, followed by stirring at room temperature for 12 hours (yield = 69%).

1H NMR (400MHz, CDCl3) δ 9.77(s, 1H), 9.45(s, 1H), 7.51-7.45 (m, 1H), 7.36(s, 1H), 7.32-7.14(m, 7H), 5.57(s, 1H), 3.73(dd, 2H), 2.95(t, 1H), MASS=518.36. 1 H NMR (400MHz, CDCl 3 ) δ 9.77 (s, 1H), 9.45 (s, 1H), 7.51-7.45 (m, 1H), 7.36 (s, 1H), 7.32-7.14 (m, 7H), 5.57 (s, 1 H), 3.73 (dd, 2H), 2.95 (t, 1 H), MASS = 518.36.

합성예 521: 1-(4-에틸벤질)-N-(4-플루오로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 521: 1- (4-Ethylbenzyl) -N- (4-fluorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-

1-(4-에틸벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다(수율=53%).1- (4-Ethylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain LDD1870 compound (yield = 53%).

1H NMR(400 MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(t, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.29(dd, 2H), 7.18(dd, 2H), 6.98(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.60(m, 2H), 1.25(s, 3H) MASS=473.18 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (t, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 1.25 (s, 3H), 2.38 (m, 2H) ) MASS = 473.18

합성예 522: N-(4-플루오로펜에틸)-1-(4-이소프로필벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 522: N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-

1-(4-이소프로필벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하고 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다(수율=67%).1- (4-Isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, it was purified by silica gel chromatography to obtain LDD1870 compound (Yield = 67%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.46(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 4.94(s, 2H), 3.55 (m, 2H), 2.87(m, 1H), 2.83(m, 2H), 1,20(s, 6H). MASS=487.19 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.46 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.12 (d, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.87 ). MASS = 487.19

합성예 523: N-(4-플루오로펜에틸)-5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 523: Synthesis of N- (4-fluorophenethyl) -5-nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-

5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다(수율=69%).5-Nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain LDD1870 compound (yield = 69%).

1H NMR (400 MHz, CDCl3)δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), MASS=490.13 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.12 (dd, 2H), 4.94

합성예 524: 5-아미노-N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 524: 5-Amino-N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-브로모페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1422 화합물을 수득하였다(수율=59%).5-Amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-bromophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain LDD1422 compound (yield = 59%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 6.27(s, 1H, -NH2), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS=505.10 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) 2H), 7.29 (d, 2H), 7.12 (dd, 2H), 6.27 (s, 2H). MASS = 505.10

합성예 525: 1-(4-메톡시벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 525: 1- (4-Methoxybenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1422 화합물을 수득하였다(수율=67%).1- (4-Methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain LDD1422 compound (yield = 67%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS=457.16 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.55 MASS = 457.16

합성예 526: N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 526: Synthesis of N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-

1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1802 화합물을 수득하였다(수율=69%).1- (4-Methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain LDD1802 compound (yield = 69%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). MASS=475.15 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (dd, 2H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 475.15

합성예 527: 5-니트로-2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 527: 5-Nitro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-

5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토 그래프로 정제하여 LDD1843 화합물을 수득하였다(수율=69%).5-Nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the residue obtained was extracted with ethyl acetate and water. Thereafter, the product was purified by silica gel chromatography to obtain LDD1843 compound (yield = 69%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=511.14 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 511.14

합성예 528: (N-(4-플루오로펜에틸)-5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드)Synthesis Example 528: Synthesis of N- (4-fluorophenethyl) -5-nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline- Mide)

5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로 퀴놀린-3-카르복실릭애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다 (수율=70%).5-Nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Subsequently, the product was purified by silica gel chromatography to obtain LDD1870 compound (yield = 70%).

1HNMR (400MHz,CDCl3)δ 8.52(s, 1H), 8.00(d, 1H), 7.95(d, 1H), 7.51(t, 1H), 7.40(dd, 2H), 7.33(dd, 2H), 7.29(dd, 2H), 7.22(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.87(m, 1H), MASS=529.13 1 HNMR (400MHz, CDCl 3) δ 8.52 (s, 1H), 8.00 (d, 1H), 7.95 (d, 1H), 7.51 (t, 1H), 7.40 (dd, 2H), 7.33 (dd, 2H) , 7.29 (d, 2H), 7.22 (m, 1H), 7.12 (dd, 2H), 4.94

합성예 529: 1-(4-이소프로필벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드Synthesis Example 529: 1- (4-Isopropylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-

1-(4-이소프로필벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다(수율=73%).1- (4-Isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the residue obtained was extracted with ethyl acetate and water. Subsequently, the product was purified by silica gel chromatography to obtain LDD1870 compound (yield = 73%).

1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.87(m, 1H), 2.83(m, 2H), 1.20(s, 6H). MASS=469.20 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 1.20 (s, 6 H). MASS = 469.20

합성된 화합물의 구조 및 분광학 데이터 (합성예 1-510)Structure and spectroscopic data of the synthesized compound (Synthesis Example 1-510) 번호number 구조rescue 명칭designation NMRNMR 분자량Molecular Weight 1One

Figure 112017032706954-pct00105
Figure 112017032706954-pct00105
퀴놀린-2(1H)-온Quinolin-2 (lH) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H), 6.57 (s, 1 H) 145.05145.05 22
Figure 112017032706954-pct00106
Figure 112017032706954-pct00106
 1-메틸퀴놀린-2(1H)-온1-methylquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H) 159.07159.07 33
Figure 112017032706954-pct00107
Figure 112017032706954-pct00107
 1-에틸퀴놀린-2(1H)-온1-ethylquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.65 (t, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 7.65 (t, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.57 (s, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 173.08173.08 44
Figure 112017032706954-pct00108
Figure 112017032706954-pct00108
 5-브로모퀴놀린-2(1H)-온5-bromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.29 (d, 1H), 7.05 (t, 1H), 6.57 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.29 (d, 1H), 7.05 (t, 1H), 6.57 (s, 1 H) 222.96222.96 55
Figure 112017032706954-pct00109
Figure 112017032706954-pct00109
 6-브로모퀴놀린-2(1H)-온6-bromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 6.57 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 6.57 (s, 1 H) 222.96222.96 66
Figure 112017032706954-pct00110
Figure 112017032706954-pct00110
 7-브로모퀴놀린-2(1H)-온7-bromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.29 (d, 1H), 7.25 (d, 1H), 6.57 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.42 (s, 1H), 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.29 (d, 1H), 7.25 (d, 1H), 6.57 (s, 1 H) 222.96222.96 77
Figure 112017032706954-pct00111
Figure 112017032706954-pct00111
 3-브로모퀴놀린-2(1H)-온3-Bromoquinolin-2 (1H) -one 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 222.96222.96 88
Figure 112017032706954-pct00112
Figure 112017032706954-pct00112
 3,5-디브로모퀴놀린-2(1H)-온3,5-dibromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.29 (d, 1H), 7.05 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.29 (d, 1H), 7.05 (t, 1H) 300.87300.87 99
Figure 112017032706954-pct00113
Figure 112017032706954-pct00113
 3,6-디브로모퀴놀린-2(1H)-온3,6-dibromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.55 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 300.87300.87 1010
Figure 112017032706954-pct00114
Figure 112017032706954-pct00114
 3,7-디브로모퀴놀린-2(1H)-온3,7-dibromoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.81 (s, 1H), 7.29 (d, 1H), 7.25 (d, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.81 (s, 1H), 7.29 (d, 1H), 7.25 (d, 1H) 300.87300.87 1111
Figure 112017032706954-pct00115
Figure 112017032706954-pct00115
 3-클로로퀴놀린-2(1H)-온3-chloroquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H, -NH), 8.14 (d, 1H), 7.54 (s, 1H), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (d, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 8.14 (d, 1H), 7.54 (s, 1H), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (d, 1 H) 179.01179.01 1212
Figure 112017032706954-pct00116
Figure 112017032706954-pct00116
 3,5-디클로로퀴놀린-2(1H)-온3,5-Dichloroquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.02 (d, 1H), 8.0 (s, -NH, 1H), 7.54 (s, 1H), 7.25 (t, 1H), 7.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3 )? 8.02 (d, 1H), 8.0 (s, -NH1 1H), 7.54 (s, 212.97212.97 1313
Figure 112017032706954-pct00117
Figure 112017032706954-pct00117
 3-클로로-6-플로로퀴놀린-2(1H)-온3-chloro-6-fluoroquinolin-2 (1H) -one 8.0 (s, 1H, -NH), 7.74 (d, 1H), 7.54 (s, 1H), 7.10 (d, 1H), 6.94 (d, 1H)1H), 7.94 (d, 1H), 7.54 (s, 1H), 7.10 (d, 197.00197.00 1414
Figure 112017032706954-pct00118
Figure 112017032706954-pct00118
 3-클로로-7-플로로퀴놀린-2(1H)-온3-chloro-7-fluoroquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H, -NH), 7.70 (d, 1H), 7.54 (s, 1H), 7.54 (s, 1H), 7.34 (d, 1H), 6.93 (d, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.70 (d, 1H), 7.54 (s, 1H), 7.54 (s, 1H), 7.34 (d, 1H), 6.93 (d, 1 H) 197197 1515
Figure 112017032706954-pct00119
Figure 112017032706954-pct00119
 3-아이오도퀴놀린-2(1H)-온3-iodoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.34 (t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.17 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.34 (t, 1H), 7.14 (t, 1 H) 270.95270.95 1616
Figure 112017032706954-pct00120
Figure 112017032706954-pct00120
 3,5-디아이오도퀴놀린-2(1H)-온Diiodoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.1 (d, 1H), 8.0 (s, 1H, -NH), 7.47 (d, 1H), 7.08 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.17 (s, 1H), 8.1 (d, 1H), 8.0 (s, 1H, -NH), 7.47 (d, 1H), 7.08 (t, 1H) 396.85396.85 1717
Figure 112017032706954-pct00121
Figure 112017032706954-pct00121
 3-아이오도-5-메틸퀴놀린-2(1H)-온3-iodo-5-methylquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.0 (s, 1H, -NH), 7.95 (d, 1H), 7.19 (t, 1H), 6.75 (d, 1H), 2.48 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.17 (s, IH), 8.0 (s, IH, -NH), 7.95 (s, 3 H) 284.87284.87 1818
Figure 112017032706954-pct00122
Figure 112017032706954-pct00122
 3-메틸퀴놀린-2(1H)-온3-methylquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (d, 1H), 2.43 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 3 H) 159.07159.07 1919
Figure 112017032706954-pct00123
Figure 112017032706954-pct00123
 3-메틸-6-(메틸티오)퀴놀린-2(1H)-온Methyl-6- (methylthio) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.0 (s, 1H, -NH), 7.72 (d, 1H), 7.66 (s, 1H), 7.14 (s, 1H), 6.87 (d, 1H), 2.53 (s, 3H), 2.43 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.0 (s, 1H, -NH), 7.72 (d, 1H), 7.66 (s, 1H), 7.14 (s, 1H), 6.87 (d, 1H), 2.53 (s, 3 H), 2.43 (s, 3 H) 205.06205.06 2020
Figure 112017032706954-pct00124
Figure 112017032706954-pct00124
 3-메톡시퀴놀린-2(1H)-온3-methoxyquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.29 (s, 1H), 3.80 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1 H), 3.80 (s, 3 H) 175.06175.06 2121
Figure 112017032706954-pct00125
Figure 112017032706954-pct00125
 3,7-디메톡시퀴놀린-2(1H)-온3,7-dimethoxyquinolin-2 (1H) -one 8.0 (s, 1H, -NH), 7.31 (s, 1H), 7.25 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 3.8 (s, 3H), 3.83 (s, 3H)(S, 3H), 3.83 (s, 3H), 8.08 (s, 1H, -NH), 7.31 ) 205.07205.07 2222
Figure 112017032706954-pct00126
Figure 112017032706954-pct00126
 3-아미노퀴놀린-2(1H)-온3-Aminoquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 2H,-NH2), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.56 (s, 2H, -NH2), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H ), 7.14 (t, IH), 6.10 (s, IH) 160.06160.06 2323
Figure 112017032706954-pct00127
Figure 112017032706954-pct00127
 3-아미노-1-(4-플로로벤질)퀴놀린-2(1H)-온Amino-1- (4-fluorobenzyl) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H, -NH2), 7.65 (d, 1H), 7.39 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (dd, 2H), 4.94 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.56 (s, 1H, -NH 2), 7.65 (d, 1H), 7.39 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H), 7.12 (dd, 2 H), 4.94 (s, 2 H) 268.10268.10 2424
Figure 112017032706954-pct00128
Figure 112017032706954-pct00128
 3-플로로퀴놀린-2(1H)-온3-fluoroquinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.96 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.96 (s, 1 H) 163.04163.04 2525
Figure 112017032706954-pct00129
Figure 112017032706954-pct00129
 2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 11.0 (s, 1H, -OH), 8.14 (d, 1H), 8.34 (s, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) 1 H (400 MHz, CDCl 3 )? 11.0 (s, IH, -OH), 8.14 (d, IH), 8.34 (t, 1 H) 189.04189.04 2626
Figure 112017032706954-pct00130
Figure 112017032706954-pct00130
 1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 3.83 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 3.83 (s, 2H) 309.10309.10 2727
Figure 112017032706954-pct00131
Figure 112017032706954-pct00131
 2-옥소-1-(4-(트리플로로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), &lt; / RTI &gt; 6.87 (dd, 2H) 363.07363.07 2828
Figure 112017032706954-pct00132
Figure 112017032706954-pct00132
 1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H) 203.06203.06 2929
Figure 112017032706954-pct00133
Figure 112017032706954-pct00133
 1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.65 (d,1H), 7.36 (d,. 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.34 (s, IH), 7.65 (d, IH), 7.36 , &Lt; / RTI &gt; 2H), 1.31 (s, 3H) 217.07217.07 3030
Figure 112017032706954-pct00134
Figure 112017032706954-pct00134
 2-옥소-1-프로필l-1,2-디하이드로퀴놀린-3-카르복실릭 애시드2-oxo-1-propyl l-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.65 (d,1H), 7.36 (d,. 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.28 (s, 2H), 3.6 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.34 (s, IH), 7.65 (d, IH), 7.36 , 2H), 3.6 (s, 2H), 1.31 (s, 3H) 231.09231.09 3131
Figure 112017032706954-pct00135
Figure 112017032706954-pct00135
 1-아세틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-acetyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 8.25 (d, 1H), 7.59 (t, 1H), 7.36 (s, 1H), 7.14 (t, 1H), 2.66 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 8.25 (d, 1H), 7.59 (t, 1H), 7.36 (s, 1H), 7.14 (t, 1H), 2.66 (s, 3H) 231.05231.05 3232
Figure 112017032706954-pct00136
Figure 112017032706954-pct00136
 5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 11.0 (s, 1H, -OH), 8.34 (s, 1H), 8.0 (s, 1H, - NH), 7.5 (d, 1H), 7.06 (t, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2) 1 H (400 MHz, CDCl 3 )? 11.0 (s, IH, -OH), 8.34 (s, ), 6.32 (d, 1 H), 6.27 (s, 2H, -NH 2 ) 204.05204.05 3333
Figure 112017032706954-pct00137
Figure 112017032706954-pct00137
 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.25 (dd, 2H), 7.06 (t, 1H), 7.01 (d, 1H), 6.87 (dd, 2H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.25 (dd, 2H), 7.06 (t, 1H), 7.01 (d, 1H), 6.87 (dd, 2H), 6.32 (d, 1H), 6.27 (s, 2H , -NH 2), 3.83 (s, 3H) 324.11324.11 3434
Figure 112017032706954-pct00138
Figure 112017032706954-pct00138
 5-아미노-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-Amino-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3 H) 218.07218.07 3535
Figure 112017032706954-pct00139
Figure 112017032706954-pct00139
 5-아미노-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-amino-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 4.28 (s, 2H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 4.28 (s, 2 H), 3.44 (s, 3 H) 232.08232.08 3636
Figure 112017032706954-pct00140
Figure 112017032706954-pct00140
 1-아세틸-5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-acetyl-5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3 H) 246.06246.06 3737
Figure 112017032706954-pct00141
Figure 112017032706954-pct00141
 5-아미노-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-Amino-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 4.28 (s, 2H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 4.28 (s, 2 H), 3.44 (s, 3 H) 260.08260.08 3838
Figure 112017032706954-pct00142
Figure 112017032706954-pct00142
 5-아미노-1-(메톡시카르보닐)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-amino-1- (methoxycarbonyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2), 3.44 (s, 3 H) 262.06262.06 3939
Figure 112017032706954-pct00143
Figure 112017032706954-pct00143
 5-아미노-1-(사이클로펜타-1,3-디엔-1-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Synthesis of 5-amino-1- (cyclopenta-1,3-dien-1-ylmethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.50 (d, 1H), 6.40 (m, 2H), 6.32 (d, 1H), 6.27 (s, 2H, -NH2), 3.63 (s, 2H), 2.9 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.34 (s, 1H), 7.06 (t, 1H), 7.01 (d, 1H), 6.50 (d, 1H), 6.40 (m, 2H), 6.32 (d, 1H), 6.27 (s, 2H , -NH 2), 3.63 (s, 2H), 2.9 (s, 1H) 282.10282.10 4040
Figure 112017032706954-pct00144
Figure 112017032706954-pct00144
 5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 11.0 (s, 1H, -OH), 8.63 (s, 1H), 8.53 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 11.0 (s, 1H, -OH), 8.63 (s, 1H), 8.53 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H) 234.03234.03 4141
Figure 112017032706954-pct00145
Figure 112017032706954-pct00145
 1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.25 (dd, 2H), 6.87 (dd, 2H), 4.94 (s, 2H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.25 (dd, 2H), 6.87 (dd, 2H), 4.94 (s, 2H), 3.83 (s, 3H) 354.09354.09 4242
Figure 112017032706954-pct00146
Figure 112017032706954-pct00146
 1-(4-메톡시펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1- (4-methoxyphenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.18 (dd, 2H), 6.94 (dd, 2H), 4.62 (s, 2H), 3.83 (s, 3H), 3.09 (s, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.18 (dd, 2H), 6.94 (dd, 2H), 4.62 (s, 2H), 3.83 (s, 3H), 3.09 368.10368.10 4343
Figure 112017032706954-pct00147
Figure 112017032706954-pct00147
 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (s, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.63 (s, IH), 8.04 (s, IH), 7.95 248.04248.04 4444
Figure 112017032706954-pct00148
Figure 112017032706954-pct00148
 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 262.06262.06 4545
Figure 112017032706954-pct00149
Figure 112017032706954-pct00149
 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 1.31 (s, 3H) 276.04276.04 4646
Figure 112017032706954-pct00150
Figure 112017032706954-pct00150
 5-니트로-2-옥소-1-프로피오닐-1,2-디하이드로퀴놀린-3-카르복실릭 애시드5-Nitro-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.64 (d, 1H), 7.95 (s, 1H), 7.57 (t, 1H), 2.32 (s, 2H), 1.02 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.64 (d, 1H), 7.95 (s, 1H), 7.57 (t, 1H), 2.32 (s, 2H), 1.02 (s, 3H) 290.05290.05 4747
Figure 112017032706954-pct00151
Figure 112017032706954-pct00151
 1-(메톡시카르보닐)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드1- (methoxycarbonyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.64 (d, 1H), 7.95 (s, 1H), 7.57 (t, 1H), 1.02 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.64 (d, 1H), 7.95 (s, 1H), 7.57 (t, 1H), 1.02 (s, 3H) 292.03292.03 4848
Figure 112017032706954-pct00152
Figure 112017032706954-pct00152
 1-(사이클로펜타-1,3-디엔-1-일메틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실릭 애시드Synthesis of 1- (cyclopenta-1,3-dien-1-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 6.5 (d, 1H), 6.4 (m, 2H), 3.63 (s, 2H), 2.9 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.63 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 6.5 (d, 1H), 6.4 (m, 2H), 3.63 (s, 2H), 2.9 (s, IH) 312.07312.07 4949
Figure 112017032706954-pct00153
Figure 112017032706954-pct00153
 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (t, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.18 (dd, 2H), 6.98 (dd, 2H), 7.27 (m, 1H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (t, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, (M, 2H), 2.60 (m, 2H), 2.38 (d, 2H) ), 1.25 (s, 3H) 455.18455.18 5050
Figure 112017032706954-pct00154
Figure 112017032706954-pct00154
 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.05 (m, 4H), 4.62 (s, 2H), 3.55 (s, 2H), 3.09 (s, 2H), 2.83 (s, 2H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, IH), 7.05 (m, 4H), 4.62 (s, 2H), 3.55 (s, 2H), 3.09 ), 1.25 (s, 3H) 469.20469.20 5151
Figure 112017032706954-pct00155
Figure 112017032706954-pct00155
 1-(4-플로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 445.14445.14 5252
Figure 112017032706954-pct00156
Figure 112017032706954-pct00156
 1-(4-플로로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (dd, 2H), 7.19 (dd, 2H), 4.62 (s, 2H), 3.55 (m, 2H), 3.09 (s, 2H), 2.83 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (d, 2H), 7.27 (dd, 2H), 7.19 (dd, 2H), 4.62 s, 2H) 459.16459.16 5353
Figure 112017032706954-pct00157
Figure 112017032706954-pct00157
 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드L- (4-chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 461.11461.11 5454
Figure 112017032706954-pct00158
Figure 112017032706954-pct00158
 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 472.14472.14 5555
Figure 112017032706954-pct00159
Figure 112017032706954-pct00159
 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 6.27 (s, 2H, -NH2), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 6.27 m, 2H), 442.16442.16 5656
Figure 112017032706954-pct00160
Figure 112017032706954-pct00160
 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.27 (m, 1H), 7.12 (dd, 2H) 452.15452.15 5757
Figure 112017032706954-pct00161
Figure 112017032706954-pct00161
 1-(나프탈렌-2-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (naphthalen-2-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 (m, 4H), 7.42 (m, 3H), 7.32 (dd, 2H), 7.29 (m, 5H), 4.99 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 2H), 2.83 (m, 2H), 2.40 (m, 2H), 2.45 (m, 2H) 477.17477.17 5858
Figure 112017032706954-pct00162
Figure 112017032706954-pct00162
 1-([1,1'-비페닐]-4-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1 - ([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (m, 4H), 7.42 (m, 3H), 7.33 (dd, 2H), 7.29 (m, 5H), 4.99 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 7.29 (m, 2H) 503.18503.18 5959
Figure 112017032706954-pct00163
Figure 112017032706954-pct00163
 1-(4-벤질벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드L- (4-benzylbenzyl) -5-nitro-2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 (m, 4H), 7.42 (m, 3H), 7.32 (dd, 2H), 7.29 (m, 5H), 4.99 (s, 2H), 4.76 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.51 2H), 2.83 (m, 2H), 2.39 (m, 2H), 2.70 (m, 2H) 517.20517.20 6060
Figure 112017032706954-pct00164
Figure 112017032706954-pct00164
 5-니트로-2-옥소-N-펜에틸-1-(4-페녹시벤질)-1,2-디하이드로퀴놀린-3-카복사마이드Nitro-2-oxo-N-phenethyl-l- (4-phenoxybenzyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (m, 4H), 7.42 (m, 3H), 7.33 (dd, 2H), 7.29 (m, 5H), 4.99 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.52 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 7.29 (m, 2H) 519.18519.18 6161
Figure 112017032706954-pct00165
Figure 112017032706954-pct00165
 1-(4-클로로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-Chlorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 (s, 2H), 3.09 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.57 (s, IH), 8.04 (d, IH), 8.03 (s, IH, -NH), 7.95 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 m, 2H) 475.13475.13 6262
Figure 112017032706954-pct00166
Figure 112017032706954-pct00166
 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 6.27 (s, 2H, -NH2), 4.62 (s, 2H), 3.09 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.57 (s, IH), 8.04 (d, IH), 8.03 (s, IH, -NH), 7.95 (dd, 2H), 7.40 ( dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 6.27 (s, 2H, -NH 2), 4.62 (s, 2H), 3.09 (s, 2H ), 3.55 (m, 2H), 2.83 (m, 2H) 456.18456.18 6363
Figure 112017032706954-pct00167
Figure 112017032706954-pct00167
 1-(4-시아노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 (s, 2H), 3.09 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.57 (s, IH), 8.04 (d, IH), 8.03 (s, IH, -NH), 7.95 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 m, 2H) 466.16466.16 6464
Figure 112017032706954-pct00168
Figure 112017032706954-pct00168
 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -NH), 7.95 (d, 1H), 7.57 (t, 1H), 7.44 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 (s, 2H), 3.09 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.57 (s, IH), 8.04 (d, IH), 8.03 (s, IH, -NH), 7.95 (dd, 2H), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.23 (dd, 2H), 4.62 m, 2H) 486.15486.15 6565
Figure 112017032706954-pct00169
Figure 112017032706954-pct00169
 메틸 7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.24 (s, 1H), 8.0 (s, 1H, -NH), 7.95 (d, 1H), 7.62 (s, 1H), 3.77 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.69 (s, IH), 8.24 (s, IH), 8.0 (s, 3 H) 248.04248.04 6666
Figure 112017032706954-pct00170
Figure 112017032706954-pct00170
 메틸 1-(2-(사이클로펜타-1,3-디엔-1-일)에틸)-7-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 1- (2- (cyclopenta-1,3-dien-1-yl) ethyl) -7-nitro-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.24 (s, 1H), 7.95 (d, 1H), 7.62 (d, 1H), 6.5 (d, 1H), 6.4 (d, 1H), 6.28 (s, 1H), 3.77 (s, 3H), 3.00 (s, 2H), 2.9 (s, 1H), 2.22 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.69 (s, 1H), 8.24 (s, 1H), 7.95 (d, 1H), 7.62 (d, 1H), 6.5 (d, 1H), 6.4 (d, 2H), 2.9 (s, 3H), 2.32 (s, 2H) 340.11340.11 6767
Figure 112017032706954-pct00171
Figure 112017032706954-pct00171
 메틸 5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.76 (s, 1H), 7.92 (dd, 1.2, 1H), 7.77 (t, 1H), 7.64 (d, 1H), 3.80 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.76 (s, 1H), 7.92 (dd, 1.2, 1H), 7.77 (t, 1H), 7.64 (d, 1H), 3.80 (s, 3H) 248.04248.04 6868
Figure 112017032706954-pct00172
Figure 112017032706954-pct00172
 메틸 1-에틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 3.77 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 4.28 (s, 2H), 3.77 (s, 3H), &lt; / RTI &gt; 1.31 (s, 3H) 276.07276.07 6969
Figure 112017032706954-pct00173
Figure 112017032706954-pct00173
 메틸 1-메틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H) 262.06262.06 7070
Figure 112017032706954-pct00174
Figure 112017032706954-pct00174
 메틸 1-아세틸-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 3.77 (s, 3H), 1.31 (s, 3H) 290.05290.05 7171
Figure 112017032706954-pct00175
Figure 112017032706954-pct00175
 메틸 2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.77 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H), 3.77 (s, 3 H) 203.06203.06 7272
Figure 112017032706954-pct00176
Figure 112017032706954-pct00176
 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 클로라이드2-oxo-1,2-dihydroquinoline-3-carbonyl chloride 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H) 207.01207.01 7373 l
Figure 112017032706954-pct00177
l
Figure 112017032706954-pct00177
 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 브로마이드2-oxo-1,2-dihydroquinoline-3-carbonyl bromide 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H) 250.96250.96 7474
Figure 112017032706954-pct00178
Figure 112017032706954-pct00178
 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 플로라이드2-oxo-1,2-dihydroquinoline-3-carbonyl fluoride 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H) 191.04191.04 7575
Figure 112017032706954-pct00179
Figure 112017032706954-pct00179
 2-옥소-1,2-디하이드로퀴놀린-3-카르보닐 아이오다이드2-oxo-1,2-dihydroquinoline-3-carbonyl iodide 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.37 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1 H) 298.94298.94 7676
Figure 112017032706954-pct00180
Figure 112017032706954-pct00180
 2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19(t, 1H), 7.14 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.19 (t, IH), 7.14 264.09264.09 7777
Figure 112017032706954-pct00181
Figure 112017032706954-pct00181
 1-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, 1H), 7.19 (m, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (t, IH), 7.31 (t, IH), 7.19 (m, IH) 278.11278.11 7878
Figure 112017032706954-pct00182
Figure 112017032706954-pct00182
 1-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, 1H), 7.19 (m, 1H), 7.14 (t, 1H), 4.28 (s, 2H), 3.44 (s, 3H), 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, IH), 7.19 (m, IH), 7.14 292.12292.12 7979
Figure 112017032706954-pct00183
Figure 112017032706954-pct00183
 1-아세틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1-acetyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, 1H), 7.31 (t, 1H), 7.19 (m, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (t, IH), 7.31 (t, IH), 7.19 (m, IH) 306.10306.10 8080
Figure 112017032706954-pct00184
Figure 112017032706954-pct00184
 5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5-benzamido-2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.7 (t, 2H), 7.63 (dd, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.19 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.63 (dd, 2H), 7.96 (dd, 2H) 383.13383.13 8181
Figure 112017032706954-pct00185
Figure 112017032706954-pct00185
 1-((2H-피롤-2-일)메틸)-5-벤즈아미도-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5-benzamido-2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H), 7.70 (s, 1H), 7.61 (m, 4H), 7.50 (s, 1H), 7.43 (dd, 2H), 7.39 (d, 1H), 7.29 (t, 1H), 7.19 (s, 1H), 5.68 (s, 1H), 5.16 (s, 1H), 3.1 (s, 2H), 2.0 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H 2H), 7.39 (d, 1H), 7.29 (t, 1H), 7.19 (s, 1H) , 5.68 (s, IH), 5.16 (s, IH), 3.1 (s, 2H), 2.0 462.17462.17 8282
Figure 112017032706954-pct00186
Figure 112017032706954-pct00186
 5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-methylbenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.7 (t, 2H), 7.63 (dd, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.19 (t, 1H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.41 (dd, 2H), 7.88 (dd, 2H), 7.87 (d, 2H) , 3H) 397.14397.14 8383
Figure 112017032706954-pct00187
Figure 112017032706954-pct00187
 1-(2-(2H-피롤-2-일)에틸)-5-(4-메틸벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-benzamido) -2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H), 7.70 (s, 1H), 7.61 (m, 4H), 7.50 (s, 1H), 7.43 (dd, 2H), 7.39 (d, 1H), 7.29 (t, 1H), 7.19 (s, 1H), 5.68 (s, 1H), 5.16 (s, 1H), 3.3 (s, 3H), 3.1 (s, 2H), 2.9 (s, 2H), 2.0 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H 2H), 7.39 (d, 1H), 7.29 (t, 1H), 7.19 (s, 1H) 2H), 2.0 (s, 1H), 5.68 (s, 1H), 5.16 (s, 490.20490.20 8484
Figure 112017032706954-pct00188
Figure 112017032706954-pct00188
 5-(4-브로모벤즈아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-bromobenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.7 (t, 2H), 7.63 (dd, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.19 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (dd, 2H), 8.0 (s, 1H 2H), 7.63 (dd, 2H), 7.96 (dd, 2H) 461.04461.04 8585
Figure 112017032706954-pct00189
Figure 112017032706954-pct00189
 2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d, IH), 7.36 (d, 2H), 7.17 (dd, 2H), 7.14 (t, 278.11278.11 8686
Figure 112017032706954-pct00190
Figure 112017032706954-pct00190
 1-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드1-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 3.44 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (d, 2H), 7.17 (d, 2H), 7.14 (t, 292.12292.12 8787
Figure 112017032706954-pct00191
Figure 112017032706954-pct00191
 1-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드1-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.17 (dd, 2H), 7.14 (t, 1H), 4.23 (s, 2H), 3.44 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.21 (d, 2H), 7.17 (d, 2H), 7.14 (s, 3H) 306.14306.14 8888
Figure 112017032706954-pct00192
Figure 112017032706954-pct00192
 5-(4-클로로벤즈아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-chlorobenzamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 7.97 (dd, 2H), 7.88 (m, 2H), 7.67 (dd, 2H), 7.29 (t, 1H), 7.21 (dd, 2H), 7.17 (dd, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, 2H), 7.17 (dd, 2H), 2.34 (s, 3H), 7.27 431.10431.10 8989
Figure 112017032706954-pct00193
Figure 112017032706954-pct00193
 N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH), 3.83 294.10294.10 9090
Figure 112017032706954-pct00194
Figure 112017032706954-pct00194
 5-(4-플로로벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-fluorobenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.12 (d, 1H), 7.88 (m, 2H), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 431.13431.13 9191
Figure 112017032706954-pct00195
Figure 112017032706954-pct00195
 5-(4-에틸벤즈아미도)-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-ethylbenzamido) -N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.12 (d, 1H), 7.88 (m, 2H), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 3.83 (s, 3H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, 2H), 1.25 (s, 3H), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H) 441.17441.17 9292
Figure 112017032706954-pct00196
Figure 112017032706954-pct00196
 N-(4-브로모페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H) 342.00342.00 9393
Figure 112017032706954-pct00197
Figure 112017032706954-pct00197
 N-(4-브로모페닐)-2-옥소-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -2-oxo-5- (4-vinylbenzamido) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.12 (d, 1H), 7.88 (m, 2H), 7.51 (dd, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, ), 7.51 (d, 2H), 7.42 (dd, 2H), 6.97 (dd, 2H), 6.63 487.05487.05 9494
Figure 112017032706954-pct00198
Figure 112017032706954-pct00198
 N-(4-브로모페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-5-(4-비닐벤즈아미도)-1,2-디하이드로퀴놀린-3-카복사마이드Yl) ethyl) -5- (4-vinylbenzamido) -1,2-dihydroquinolin-3 - carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H), 7.70 (s, 1H), 7.61 (m, 4H), 7.50 (s, 1H), 7.43 (dd, 2H), 7.39 (d, 1H), 7.29 (t, 1H), 5.68 (s, 1H), 5.16 (s, 1H), 3.3 (s, 2H), 3.1 (m, 3H), 2.9 (s, 2H), 2.0 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.25 (s, 1H), 8.03 (dd, 2H), 7.88 (d, 1H 2H), 7.39 (d, 1H), 7.29 (t, 1H), 5.68 (s, 1H) , 5.16 (s, IH), 3.3 (s, 2H), 3.1 (m, 3H) 597.07597.07 9595
Figure 112017032706954-pct00199
Figure 112017032706954-pct00199
 N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H) 298.05298.05 9696
Figure 112017032706954-pct00200
Figure 112017032706954-pct00200
 N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 312.07312.07 9797
Figure 112017032706954-pct00201
Figure 112017032706954-pct00201
 N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 2H), 2.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH) 326.08326.08 9898
Figure 112017032706954-pct00202
Figure 112017032706954-pct00202
 N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 462.07462.07 9999
Figure 112017032706954-pct00203
Figure 112017032706954-pct00203
 N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.2 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1 H), 7.47 (dd, 476.09476.09 100100
Figure 112017032706954-pct00204
Figure 112017032706954-pct00204
 N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.2 (s, 2H), 2.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H 2H), 7.83 (d, 2H), 7.88 (m, 2H), 7.75 (dd, 490.10490.10 101101
Figure 112017032706954-pct00205
Figure 112017032706954-pct00205
 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-bromobenzamido) -N- (4-chlorophenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 495.00495.00 102102
Figure 112017032706954-pct00206
Figure 112017032706954-pct00206
 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-bromobenzamido) -N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1 H), 7.47 (dd, 509.01509.01 103103
Figure 112017032706954-pct00207
Figure 112017032706954-pct00207
 5-(4-브로모벤즈아미도)-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (4-bromobenzamido) -N- (4-chlorophenyl) -l-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.3 (s, 2H), 2.8 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H ), 7.88 (m, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H) 523.03523.03 104104
Figure 112017032706954-pct00208
Figure 112017032706954-pct00208
 N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , 1H, -OH) 447.10447.10 105105
Figure 112017032706954-pct00209
Figure 112017032706954-pct00209
 N-(4-클로로페닐)-5-(4-(하이드록시메틸)벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -l-methyl-2-oxo-l, 2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H), 3.65 (s, 1H, -OH), 3.2 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , 1H, -OH), 3.2 (s, 3H) 461.11461.11 106106
Figure 112017032706954-pct00210
Figure 112017032706954-pct00210
 N-(4-클로로페닐)-1-에틸-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H), 3.65 (s, 1H, -OH), 3.2 (s, 2H), 2.7 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.65 (dd, 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 , 1H, -OH), 3.2 (s, 2H), 2.7 (s, 3H) 475.13475.13 107107
Figure 112017032706954-pct00211
Figure 112017032706954-pct00211
 N-(4-클로로페닐)-1-(퓨란-2-일메틸)-5-(4-(하이드록시메틸)벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드2-ylmethyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinolin-3-car Copymade 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.65 (s, 1H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 6.42 (m, 2H), 4.61 (s, 2H), 4.07 (s, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.65 2H), 4.61 (s, 2H), 4.07 (s, 2H), 3.65 527.12527.12 108108
Figure 112017032706954-pct00212
Figure 112017032706954-pct00212
 N-(4-클로로페닐)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H) 462.07462.07 109109
Figure 112017032706954-pct00213
Figure 112017032706954-pct00213
 N-(4-클로로페닐)-1-메틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-methyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H), 3.2 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 , 3H) 476.09476.09 110110
Figure 112017032706954-pct00214
Figure 112017032706954-pct00214
 N-(4-클로로페닐)-1-에틸-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1-ethyl-5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 4.61 (s, 2H), 3.2 (s, 2H), 2.94 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 2H), 7.88 (d, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 , &Lt; / RTI &gt; 2H), 2.94 (s, 3H) 490.10490.10 111111
Figure 112017032706954-pct00215
Figure 112017032706954-pct00215
 N-(4-클로로페닐)-1-(2-(퓨란-2-일)에틸)-5-(4-니트로벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Yl) ethyl) -5- (4-nitrobenzamido) -2-oxo-1,2-dihydroquinolin-3-car Copymade 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.58 (s, 1H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, 1H), 6.6 (m, 2H), 4.61 (s, 2H), 2.66 (s, 2H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.58 , 2H), 4.61 (s, 2H), 2.66 (s, 2H) 556.11556.11 112112
Figure 112017032706954-pct00216
Figure 112017032706954-pct00216
 N-(4-클로로페닐)-2-옥소-5-(2-페닐아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 7.26 (t, 1H), 7.23 (dd, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (m, 2H), 7.26 (t, IH), 7.23 (dd, 2H) 431.10431.10 113113
Figure 112017032706954-pct00217
Figure 112017032706954-pct00217
 5-벤즈아미도-N-(4-클로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzamido-N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 7.26 (t, 431.10431.10 114114
Figure 112017032706954-pct00218
Figure 112017032706954-pct00218
 5-벤즈아미도-N-(4-클로로페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5-benzamido-N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 3.3 (s, 2H), 2.9 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 2H), 7.29 (d, 2H), 7.29 (m, 2H), 7.26 (t, 445.12445.12 115115
Figure 112017032706954-pct00219
Figure 112017032706954-pct00219
 N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 2.60 (s, 2H), 1.25 445.12445.12 116116
Figure 112017032706954-pct00220
Figure 112017032706954-pct00220
 N-(4-클로로페닐)-5-(4-에틸벤즈아미도)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -5- (4-ethylbenzamido) -l-methyl-2-oxo-l, 2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 459.13459.13 117117
Figure 112017032706954-pct00221
Figure 112017032706954-pct00221
 N-(4-클로로페닐)-1-에틸-5-(4-에틸벤즈아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -l-ethyl-5- (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (dd, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 (m, 5H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.47 (dd, 2H), 7.33 (d, 2H), 7.29 (m, 2H), 3.3 (s, 3H), 2.60 473.15473.15 118118
Figure 112017032706954-pct00222
Figure 112017032706954-pct00222
 N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H) 282.08282.08 119119
Figure 112017032706954-pct00223
Figure 112017032706954-pct00223
 N-(4-플로로페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 296.10296.10 120120
Figure 112017032706954-pct00224
Figure 112017032706954-pct00224
 1-에틸-N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 4.28 (s, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH), 4.28 310.11310.11 121121
Figure 112017032706954-pct00225
Figure 112017032706954-pct00225
 1-((2H-피롤-3-일)메틸)-N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1 - ((2H-pyrrol-3-yl) methyl) -N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (m, 3H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 5.06 (s, 1H), 4.28 (s, 2H), 3.63 (s, 2H), 2.0 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (m, 3H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.06 (s, IH), 4.28 361.12361.12 122122
Figure 112017032706954-pct00226
Figure 112017032706954-pct00226
 N-(4-플로로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -2-oxo-5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H), 7.22 (dd, 2H), 7.11 (m, 4H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 2.34 (s, 3H) 429.15429.15 123123
Figure 112017032706954-pct00227
Figure 112017032706954-pct00227
 N-(4-플로로페닐)-1-메틸-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 3H) 443.16443.16 124124
Figure 112017032706954-pct00228
Figure 112017032706954-pct00228
 1-에틸-N-(4-플로로페닐)-2-옥소-5-(2-(p-톨일)아세트아미도)-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (p-tolyl) acetamido) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 2H), 2.8 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H 2H), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 457.18457.18 125125
Figure 112017032706954-pct00229
Figure 112017032706954-pct00229
 N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 2H), 1.25 (s, 3H), 7.17 (d, IH) 292.12292.12 126126
Figure 112017032706954-pct00230
Figure 112017032706954-pct00230
 N-(4-에틸페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, IH), 6.97 (dd, IH) 306.14306.14 127127
Figure 112017032706954-pct00231
Figure 112017032706954-pct00231
 1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 3.3 (s, 3H), 2.60 (s, 2H), 2.3 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, IH), 6.97 (dd, IH), 3.3 (s, 3H), 2.60 (s, 2H) 320.15320.15 128128
Figure 112017032706954-pct00232
Figure 112017032706954-pct00232
 1-(2-(2H-피롤-3-일)에틸)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(2- (2H-pyrrol-3-yl) ethyl) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.50 (s, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 5.06 (s, 1H), 3.60 (s, 2H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.50 (s, 2H), 2.60 (s, 2H), 1.25 (s, 1H), 7.31 (t, s, 3H) 385.18385.18 129129
Figure 112017032706954-pct00233
Figure 112017032706954-pct00233
 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 3.90 (s, 2H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , &Lt; / RTI &gt; 2H), 1.25 (s, 3H) 503.08503.08 130130
Figure 112017032706954-pct00234
Figure 112017032706954-pct00234
 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-2-옥소-1-(티오펜-2-일메틸)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -2-oxo-1- (thiophen-2-ylmethyl) -1,2-dihydroquinoline- 3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H), 7.63 (dd, 2H), 7.40 (s, 1H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 (s, 1H, -NH), 7.12 (m, 3H), 6.93 (s, 1H), 4.22 (s, 2H), 3.90 (s, 2H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.40 (s, IH), 7.29 (s, IH), 7.27 (dd, 2H), 7.23 2H), 2.60 (s, 2H), 1.25 (s, 3H) 599.09599.09 131131
Figure 112017032706954-pct00235
Figure 112017032706954-pct00235
 5-(2-(4-브로모페닐)아세트아미도)-N-(4-에틸페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 3.90 (s, 2H), 3.3 (s, 3H), 2.60 (s, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , 3H), 2.60 (s, 2H), 1.25 (s, 3H) 517.10517.10 132132
Figure 112017032706954-pct00236
Figure 112017032706954-pct00236
 5-(2-(4-브로모페닐)아세트아미도)-1-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Acetylamino) -1- ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 3.90 (s, 2H), 3.3 (s, 2H), 2.60 (m, 5H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.85 (dd, 2H ), 7.63 (dd, 2H), 7.29 (s, 1H), 7.27 (dd, 2H), 7.23 , 2H), 2.60 (m, 5H), 1.25 (s, 3H) 531.12531.12 133133
Figure 112017032706954-pct00237
Figure 112017032706954-pct00237
 N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 5.35 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH), 5.35 280.08280.08 134134
Figure 112017032706954-pct00238
Figure 112017032706954-pct00238
 N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 5.35 (s, 1H, -OH), 3.2 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH), 5.35 294.10294.10 135135
Figure 112017032706954-pct00239
Figure 112017032706954-pct00239
 1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H), 5.35 (s, 1H, -OH), 4.3 (s, 2H), 3.2 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, IH), 6.97 (dd, IH), 5.35 308.12308.12 136136
Figure 112017032706954-pct00240
Figure 112017032706954-pct00240
 N-(4-하이드록시페닐)-2-옥소-1-(2-(티오펜-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1- (2- (thiophen-2- yl) ethyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.40 (s, 1H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (s, 1H), 6.97 (m, 2H), 5.35 (s, 1H, -OH), 4.3 (s, 2H), 4.22 (s, 2H), 3.83 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.40 (s, 1H), 7.36 (s, 2H), 7.31 (t, 1H), 7.14 (s, 1H), 7.12 (s, , 4.22 (s, 2 H), 3.83 (s, 2 H) 390.10390.10 137137
Figure 112017032706954-pct00241
Figure 112017032706954-pct00241
 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 3.90 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (d, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 5.35 447.10447.10 138138
Figure 112017032706954-pct00242
Figure 112017032706954-pct00242
 5-(2-(4-클로로페닐)아세트아미도)-N-(4-하이드록시페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 3.90 (s, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (d, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 5.35 461.11461.11 139139
Figure 112017032706954-pct00243
Figure 112017032706954-pct00243
 5-(2-(4-클로로페닐)아세트아미도)-1-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Acetylamino) -1- ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 3.90 (s, 2H), 3.3 (s, 2H), 2.73 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (d, 2H), 7.29 (t, 1H), 6.93 (s, 3H) 475.13475.13 140140
Figure 112017032706954-pct00244
Figure 112017032706954-pct00244
 N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H) 309.07309.07 141141
Figure 112017032706954-pct00245
Figure 112017032706954-pct00245
 5-(2-(4-플로로페닐)아세트아미도)-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 6.93 (dd, 2H), 3.90 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.45 (dd, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, IH), 6.93 (dd, 2H), 3.90 460.12460.12 142142
Figure 112017032706954-pct00246
Figure 112017032706954-pct00246
 5-(2-(4-에틸페닐)아세트아미도)-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.97 (dd, 1 H) 470.16470.16 143143
Figure 112017032706954-pct00247
Figure 112017032706954-pct00247
 N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H ), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 371.09371.09 144144
Figure 112017032706954-pct00248
Figure 112017032706954-pct00248
 N-(4-(N,N-디메틸설파모일)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 3.4 (s, 3H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H ), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 385.11385.11 145145
Figure 112017032706954-pct00249
Figure 112017032706954-pct00249
 N-(4-(N,N-디메틸설파모일)페닐)-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 3.4 (s, 3H), 2.8 (s, 2H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 2H), 7.36 (d, 2H), 7.36 (t, 1H), 7.14 (t, 399.13399.13 146146
Figure 112017032706954-pct00250
Figure 112017032706954-pct00250
 1-(사이클로헥실메틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(Cyclohexylmethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 3.98 (s, 2H), 2.66 (m, 6H), 2.06 (s, 1H), 1.43 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 2H), 7.36 (d, 2H), 7.36 (t, IH), 7.14 (t, IH), 3.98 (s, 2H), 2.66 , &Lt; / RTI &gt; 1.43 (m, 5H) 467.19467.19 147147
Figure 112017032706954-pct00251
Figure 112017032706954-pct00251
 1-(2-사이클로헥실에틸)-N-(4-(N,N-디메틸설파모일)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 3.98 (s, 2H), 3.46 (s, 3H), 2.66 (m, 6H), 2.06 (s, 1H), 1.43 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 2H), 7.36 (d, 2H), 7.36 (t, 1H), 7.14 (t, , 2.06 (s, 1 H), 1.43 (m, 5 H) 481.20481.20 148148
Figure 112017032706954-pct00252
Figure 112017032706954-pct00252
 N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 294.10294.10 149149
Figure 112017032706954-pct00253
Figure 112017032706954-pct00253
 N-(4-(하이드록시메틸)페닐)-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, , 3H) 308.12308.12 150150
Figure 112017032706954-pct00254
Figure 112017032706954-pct00254
 1-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.4 (s, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, , &Lt; / RTI &gt; 2H), 3.3 (s, 3H) 322.13322.13 151151
Figure 112017032706954-pct00255
Figure 112017032706954-pct00255
 1-(사이클로펜틸메틸)-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (Cyclopentylmethyl) -N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.98 (s, 2H), 3.65 (s, 1H, -OH), 1.64 (m, 8H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, -OH), &lt; / RTI &gt; 1.64 (m, 8H) 322.13322.13 152152
Figure 112017032706954-pct00256
Figure 112017032706954-pct00256
 2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 290.11290.11 153153
Figure 112017032706954-pct00257
Figure 112017032706954-pct00257
 1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 3.12 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, , 3.12 (s, 3H) 304.12304.12 154154
Figure 112017032706954-pct00258
Figure 112017032706954-pct00258
 1-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드1-ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 3.4 (s, 2H), 3.12 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, , 3.4 (s, 2 H), 3.12 (s, 3 H) 318.14318.14 155155
Figure 112017032706954-pct00259
Figure 112017032706954-pct00259
 1-(2-사이클로펜틸에틸)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드1- (2-cyclopentylethyl) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 3.98 (s, 2H), 3.75 (s, 2H), 1.46 (m, 8H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 1H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, , 3.98 (s, 2H), 3.75 (s, 2H), 1.46 (m, 8H) 386.20386.20 156156
Figure 112017032706954-pct00260
Figure 112017032706954-pct00260
 5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.35 (s, 1H, -OH), 5.18 (s, 1H), 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, IH, - NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 439.15439.15 157157
Figure 112017032706954-pct00261
Figure 112017032706954-pct00261
 5-(2-(4-하이드록시페닐)아세트아미도)-1-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.35 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , 3H) 453.17453.17 158158
Figure 112017032706954-pct00262
Figure 112017032706954-pct00262
 1-에틸-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드(4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.35 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 2H), 2.8 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.3 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , &Lt; / RTI &gt; 2H), 2.8 (s, 3H) 467.18467.18 159159
Figure 112017032706954-pct00263
Figure 112017032706954-pct00263
 1-((2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) ) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (m, 5H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.35 (s, 1H, -OH), 5.18 (s, 1H), 3.98 (s, 2H), 2.66 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (m, 5H), 7.23 (s, 1H, -OH), 5.18 (s, 1H), 3.98 (s, 1H, -NH), 7.06 (dd, 2H), 6.63 , 2H), 2.66 (m, 5H) 569.23569.23 160160
Figure 112017032706954-pct00264
Figure 112017032706954-pct00264
 5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, IH, -NH), 7.06 (dd, 2H), 6.63 (m, 3H) 468.14468.14 161161
Figure 112017032706954-pct00265
Figure 112017032706954-pct00265
 1-메틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드(4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.18 (s, 1H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (d, 2H), 6.63 (s, 3H), 5.61 (s, 1H), 5.18 (s, 482.16482.16 162162
Figure 112017032706954-pct00266
Figure 112017032706954-pct00266
 1-에틸-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드(4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.18 (s, 1H), 3.3 (s, 2H), 2.76 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (d, 2H), 6.63 (s, 3H), 5.61 (s, 1H), 5.18 (s, 496.17496.17 163163
Figure 112017032706954-pct00267
Figure 112017032706954-pct00267
 1-((4-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드(4-methoxy-2,3-dihydro-1H-inden-2-yl) methyl) 4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (m, 3H), 6.63 (m, 4H), 5.61 (s, 1H), 5.18 (s, 1H), 3.83 (s, 3H), 2.79 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H), 3.63 (s, 3H), 2.79 (s, 2H) , 2.46 (m, 5 H) 628.23628.23 164164
Figure 112017032706954-pct00268
Figure 112017032706954-pct00268
 1-((5-메톡시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- ( 4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H,-NH), 7.06 (m, 3H), 6.63 (m, 4H), 5.61 (s, 1H), 5.18 (s, 1H), 3.83 (s, 3H), 2.79 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H), 3.63 (s, 3H), 2.79 (s, 2H) , 2.46 (m, 5 H) 628.23628.23 165165
Figure 112017032706954-pct00269
Figure 112017032706954-pct00269
 N-벤질-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-benzyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H ), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 278.11278.11 166166
Figure 112017032706954-pct00270
Figure 112017032706954-pct00270
 N-벤질-1-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzyl-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H ), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 292.12292.12 167167
Figure 112017032706954-pct00271
Figure 112017032706954-pct00271
 N-벤질-1-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzyl-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.8 (s, 2H), 3.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H 2H), 7.36 (d, 2H), 7.3 (t, 1H), 7.14 (t, 306.14306.14 168168
Figure 112017032706954-pct00272
Figure 112017032706954-pct00272
 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.19 (t, 1H), 7.12 (dd, 2H), 6.87 (dd, 2H), 3.9 (m, 2H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 3.83 (s, 3H), 7.43 (d, 2H), 7.29 (t, 427.15427.15 169169
Figure 112017032706954-pct00273
Figure 112017032706954-pct00273
 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenyl -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (m, 2H), 7.19 (t, 1H), 7.12 (dd, 2H), 6.87 (m, 3H), 3.9 (m, 2H), 3.83 (m, 6H), 2.83 (s, 2H), 2.76 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H (M, 2H), 7.43 (d, 2H), 7.29 (m, 2H), 7.19 , 2.83 (s, 2H), 2.76 (s, 2H), 2.46 (m, 5H) 585.26585.26 170170
Figure 112017032706954-pct00274
Figure 112017032706954-pct00274
 1-((5-플로로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo- [Lambda] / - Phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.19 (t, 1H), 7.12 (dd, 2H), 6.87 (m, 3H), 3.9 (m, 2H), 3.83 (s, 3H), 2.79 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H 3H), 3.83 (s, 3H), 2.27 (d, 2H) , 2.79 (s, 2 H), 2.46 (m, 5 H) 575.22575.22 171171
Figure 112017032706954-pct00275
Figure 112017032706954-pct00275
 1-((5-클로로-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenyl -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.19 (t, 1H), 7.12 (dd, 2H), 6.87 (m, 3H), 3.9 (m, 2H), 3.83 (s, 3H), 2.79 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (m, 3H 3H), 3.83 (s, 3H), 2.27 (d, 2H) , 2.79 (s, 2 H), 2.46 (m, 5 H) 591.19591.19 172172
Figure 112017032706954-pct00276
Figure 112017032706954-pct00276
 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드(2- (4- (hydroxymethyl) phenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (t, 1H), 7.16 (dd, 2H), 7.11 (dd, 2H), 4.61 (m, 2H), 3.90 (m, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (d, 2H), 4.61 (m, 2H), 3.90 (m, 2H), 7.19 (t, , 3.65 (s, 1 H, -OH) 427.15427.15 173173
Figure 112017032706954-pct00277
Figure 112017032706954-pct00277
 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-아이오도-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1 - ((5-Iodo-2,3-dihydro-1 H-inden-2-yl) methyl) -2-oxo- Phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (m, 2H), 7.16 (dd, 2H), 7.11 (m, 3H), 4.61 (m, 2H), 3.90 (m, 2H), 3.65 (s, 1H, -OH), 3.3 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 7.19 (m, 2H), 7.19 (m, 2H), 7.19 (m, , 3.65 (s, IH, -OH), 3.3 (s, 2H), 2.46 (m, 5H) 683.13683.13 174174
Figure 112017032706954-pct00278
Figure 112017032706954-pct00278
 5-(2-(4-(하이드록시메틸)페닐)아세트아미도)-1-((5-니트로-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1 - ((5-Nitro-2,3-dihydro-1H-inden-2-yl) methyl) -2-oxo- N-phenyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (m, 2H), 7.16 (dd, 2H), 7.11 (m, 3H), 4.61 (m, 2H), 3.90 (m, 2H), 3.65 (s, 1H, -OH), 3.3 (s, 2H), 2.46 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 7.19 (m, 2H), 7.19 (m, 2H), 7.19 (m, , 3.65 (s, IH, -OH), 3.3 (s, 2H), 2.46 (m, 5H) 602.22602.22 175175
Figure 112017032706954-pct00279
Figure 112017032706954-pct00279
 2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N-phenyl-5- (3-phenylpropanamido) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (t, 1H), 2.9 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 1H), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 , &Lt; / RTI &gt; 2H), 2.83 (m, 2H) 411.16411.16 176176
Figure 112017032706954-pct00280
Figure 112017032706954-pct00280
 1-((5-에틸-2,3-디하이드로-1H-인덴-2-일)메틸)-2-옥소-N-페닐-5-(3-페닐프로판아미도)-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-N-phenyl-5- (3-phenylpropanamido) -1,2-di Hydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (m, 3H), 3.3 (m, 5H), 2.9 (m, 7H), 2.83 (m, 4H), 2.64 (s, 5H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H ), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 , 5H), 2.9 (m, 7H), 2.83 (m, 4H), 2.64 569.27569.27 177177
Figure 112017032706954-pct00281
Figure 112017032706954-pct00281
 5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-ethylphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (dd, 2H), 6.98 (dd, 2H), 3.90 (m, 2H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 3.90 (m, 2H), 2.60 (m, 2H), 7.43 (dd, 2H), 7.29 , &Lt; / RTI &gt; 2H), 1.25 (s, 3H) 425.17425.17 178178
Figure 112017032706954-pct00282
Figure 112017032706954-pct00282
 1-(2-(2,3-디하이드로-1H-인덴-2-일)에틸)-5-(2-(4-에틸페닐)아세트아미도)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) ethyl) -5- (2- (4-ethylphenyl) acetamido) -2-oxo- 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (m, 2H), 7.23 (s, 1H, -NH), 7.18 (m, 4H), 6.98 (dd, 2H), 3.90 (m, 6H), 2.60 (m, 7H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.61 (dd, 2H 2H), 7.23 (s, 1H, -NH), 7.18 (m, 4H), 6.98 (dd, 2H), 3.90 (m, 6H), 2.60 , &Lt; / RTI &gt; 7H), 1.25 (s, 3H) 569.27569.27 179179
Figure 112017032706954-pct00283
Figure 112017032706954-pct00283
 2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (t, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H 2H), 7.27 (t, 1H), 7.36 (d, 1H), 7.31 (t, 292.12292.12 180180
Figure 112017032706954-pct00284
Figure 112017032706954-pct00284
 1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 (m, 3H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 3.3 (s, 2H), 2.95 (s, 3H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H 1H), 7.29 (m, 2H), 7.27 (m, 3H), 7.36 (d, , 2.95 (s, 3 H), 2.83 (m, 2 H) 412.18412.18 181181
Figure 112017032706954-pct00285
Figure 112017032706954-pct00285
 2-옥소-N-펜에틸-1-(4-(트리플로로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 (m, 3H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H 1H), 7.29 (m, 2H), 7.27 (m, 3H), 7.36 (d, , 2.83 (m, 2 H) 466.15466.15 182182
Figure 112017032706954-pct00286
Figure 112017032706954-pct00286
 1-(2-(4-메톡시-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Dihydro-1 H-inden-2-yl) ethyl) -2-oxo-N-phenethyl-1, 2-dihydroquinoline- Mide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 4H), 2.83 (m, 4H), 2.6 (m, 8H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, , 2.6 (m, 8H) 466.23466.23 183183
Figure 112017032706954-pct00287
Figure 112017032706954-pct00287
 2-옥소-N-펜에틸-1-(2-(4-(트리플로로메톡시)-2,3-디하이드로-1H-인덴-2-일)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드Dihydro-1H-inden-2-yl) ethyl) -1,2-dihydroquinoline- 3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H), 7.29 (dd, 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 4H), 2.83 (m, 4H), 2.6 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.40 (dd, 2H 2H), 7.27 (m, 3H), 7.36 (m, 2H), 7.31 (t, , 2.6 (m, 5H) 520.20520.20 184184
Figure 112017032706954-pct00288
Figure 112017032706954-pct00288
 5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 6.87 (dd, 2H), 3.90 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (dd, 2H), 6.87 (dd, 2H) , 3.55 (m, 2 H), 2.83 (m, 2 H) 455.18455.18 185185
Figure 112017032706954-pct00289
Figure 112017032706954-pct00289
 1-(4-메톡시벤질)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H), 6.87 (m, 4H), 3.90 (s, 2H), 3.83 (s, 3H), 3.55 (m, 4H), 2.83 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (s, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H) , 3.55 (m, 4 H), 2.83 (m, 5 H) 575.24575.24 186186
Figure 112017032706954-pct00290
Figure 112017032706954-pct00290
 1-((4-하이드록시-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo- [Lambda] / - Phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H), 6.87 (m, 3H), 3.90 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H), 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) 2H), 2.83 (m, 2H), 2.83 (m, 2H) 601.26601.26 187187
Figure 112017032706954-pct00291
Figure 112017032706954-pct00291
 1-((4-포르밀-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo- [Lambda] / - Phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H), 6.87 (m, 3H), 3.90 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H), 1.27 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) 2H), 2.83 (m, 2H), 3.58 (m, 2H) 613.26613.26 188188
Figure 112017032706954-pct00292
Figure 112017032706954-pct00292
 1-((4-시아노-2,3-디하이드로-1H-인덴-2-일)메틸)-5-(2-(4-메톡시페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo- [Lambda] / - Phenethyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (m, 4H), 6.87 (m, 3H), 3.90 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.68 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.12 (m, 4H) (M, 2H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 610.26610.26 189189
Figure 112017032706954-pct00293
Figure 112017032706954-pct00293
 5-(2-(4-브로모페닐)아세트아미도)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-bromophenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (t, 1H), 7.23 (s, 1H, -NH), 7.12 (dd, 2H), 6.87 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (d, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 7.27 (t, , 2.83 (m, 2 H) 503.08503.08 190190
Figure 112017032706954-pct00294
Figure 112017032706954-pct00294
 5-(2-(4-브로모페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-bromophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (m, 3H), 7.27 (m, 3H), 7.23 (s, 1H, -NH), 7.12 (m, 4H), 6.87 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 4H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 (m, 2H), 7.40 (dd, 2H), 7.29 (d, 2H), 3.90 (m, 2H), 3.55 (m, 4H), 7.27 (m, 3H) , 2.83 (m, 2 H) 623.14623.14 191191
Figure 112017032706954-pct00295
Figure 112017032706954-pct00295
 2-옥소-N-(3-페닐프로필l)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.27 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 2.62 (m, 2H), 2.09 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.29 (m, 2H), 7.29 (m, 2H) 306.14306.14 192192
Figure 112017032706954-pct00296
Figure 112017032706954-pct00296
 1-(4-메톡시벤질)-2-옥소-N-(3-페닐프로필l)-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-methoxybenzyl) -2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.29 (m, 4H), 7.27 (t, 1H), 7.14 (m, 3H), 3.18 (m, 2H), 3.3 (s, 2H), 2.62 (m, 2H), 2.09 (m, 2H) 1.62 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 2H), 2.62 (m, 2H), 2.09 (m, 2H), 7.29 (m, 2H) m, 2 H) 1.62 (s, 3 H) 426.19426.19 193193
Figure 112017032706954-pct00297
Figure 112017032706954-pct00297
 1-(2-(5-포르밀-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필l)-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) ethyl) -2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline -3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (m, 2H), 7.29 (dd, 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 (s, 2H), 3.18 (m, 4H), 2.97 (s, 2H), 2.62 (m, 2H), 2.09 (m, 7H), 1.29 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 2H), 7.29 (d, 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 m, 2 H), 2.09 (m, 7 H), 1.29 (s, 1 H) 478.23478.23 194194
Figure 112017032706954-pct00298
Figure 112017032706954-pct00298
 1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)에틸)-2-옥소-N-(3-페닐프로필l)-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) ethyl) -2-oxo-N- (3-phenylpropyl) -1,2-di Hydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 (m, 2H), 7.29 (dd, 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 (s, 2H), 3.18 (m, 4H), 2.97 (s, 2H), 2.62 (m, 2H), 2.09 (m, 7H), 1.29 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.40 (dd, 2H), 7.36 (d, 1H), 7.31 2H), 7.29 (d, 2H), 7.27 (t, 1H), 7.14 (m, 3H), 3.3 m, 2H), 2.09 (m, 7H), 1.29 (s, 3H) 496.22496.22 195195
Figure 112017032706954-pct00299
Figure 112017032706954-pct00299
 N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.11 (m, 4H), 7.14 (d, 1H), 4.34 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) , 7.31 (t, 1 H), 7.11 (m, 4 H), 7.14 (d, 292.12292.12 196196
Figure 112017032706954-pct00300
Figure 112017032706954-pct00300
 1-(4-메톡시벤질)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-methoxybenzyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline- 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.11 (m, 4H), 7.14 (d, 1H), 4.34 (m, 2H), 3.3 (s, 2H), 2.34 (s, 3H), 1.67 (s, 3H) 1H), 8.21 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, 2H), 2.34 (s, 3H), 1.67 (s, 3H) 412.18412.18 197197
Figure 112017032706954-pct00301
Figure 112017032706954-pct00301
 N-(4-메틸벤질)-2-옥소-1-(3-(트리플로로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methylbenzyl) -2-oxo-1- (3- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.11 (m, 6H), 7.14 (m, 3H), 4.34 (m, 2H), 3.78 (s, 2H), 2.76 (s, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) 8.28 δ (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, 1H), 7.11 (m, 6H), 7.14 (m, 3H), 4.34 (m, 2H) 480.17480.17 198198
Figure 112017032706954-pct00302
Figure 112017032706954-pct00302
 1-(3-시아노펜에틸)-N-(4-메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (3-cyanophenethyl) -N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.11 (m, 6H), 7.14 (m, 3H), 4.34 (m, 2H), 3.78 (s, 2H), 2.76 (s, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H) 2H), 7.31 (t, 1H), 7.11 (m, 6H), 7.14 (m, 3H), 4.34 (m, 2H) 421.18421.18 199199
Figure 112017032706954-pct00303
Figure 112017032706954-pct00303
 N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 2.34 (s, 3H), 2.40 (s, 3H), 2.45 (s, 3H) 306.14306.14 200200
Figure 112017032706954-pct00304
Figure 112017032706954-pct00304
 1-(4-(하이드록시메틸)벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4- (hydroxymethyl) benzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 2.34 (s, 3H), 2.40 (s, 3H), 2.45 (s, 3H) 426.19426.19 201201
Figure 112017032706954-pct00305
Figure 112017032706954-pct00305
 1-(4-에틸벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-ethylbenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (s, 3H), 2.14 (s, 2H), 1.67 (s, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 2.34 (s, 3H), 2.40 (s, 3H), 2.45 (s, 3H) , 2.14 (s, 2 H), 1.67 (s, 6 H) 424.22424.22 202202
Figure 112017032706954-pct00306
Figure 112017032706954-pct00306
 1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s. 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 2.34 (s, 3H), 2.40 (s, 3H), 2.45 (s, 3H) 426.19426.19 203203
Figure 112017032706954-pct00307
Figure 112017032706954-pct00307
 5-(2-(4-클로로페닐)아세트아미도)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-chlorophenyl) acetamido) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (dd, 2H), 6.98 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H 2H), 7.39 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H) , 2H), 2.83 (m, 2H), 2.34 (m, 2H) 473.15473.15 204204
Figure 112017032706954-pct00308
Figure 112017032706954-pct00308
 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinolin-3- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.37 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (m, 4H), 6.98 (m, 4H), 3.90 (m, 2H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 2.34 (m, 2H), 1.67 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H (M, 2H), 7.37 (d, 2H), 7.29 (t, 1H), 7.23 2H), 1.67 (s, 3H), 2.32 (m, 2H) 593.21593.21 205205
Figure 112017032706954-pct00309
Figure 112017032706954-pct00309
 N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 3.83 (s, 3H), 7.31 (t, 1H), 7.25 (dd, 2H) 308.12308.12 206206
Figure 112017032706954-pct00310
Figure 112017032706954-pct00310
 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Dihydro-1 H-inden-2-yl) ethyl) -N- (4-methoxybenzyl) -2-oxo- 3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, H), 7.14 (m, 3H), 6.87 (dd, 2H), 6.27 (s, -NH2, -2H), 4.34 (m, 2H), 3.83 (s, 3H), 3.3 (s, 2H), 3.18 (s, 2H), 2.64 (m, 5H), 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (t, 1H), 7.25 (m, H), 7.14 (m, 3H), 6.87 (dd, 2H), 6.27 (s, 3H), 3.3 (s, 2H), 3.18 (s, 2H), 2.64 467.22467.22 207207
Figure 112017032706954-pct00311
Figure 112017032706954-pct00311
 1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) ethyl) -N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.83 (s, 3H), 3.3 (s, 2H), 3.18 (s, 2H), 2.64 (m, 7H), 1.64 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 3.83 (s, 3H), 3.3 (s, 2H), 7.31 (m, 2H) , 3.18 (s, 2H), 2.64 (m, 7H), 1.64 (s, 3H) 480.24480.24 208208
Figure 112017032706954-pct00312
Figure 112017032706954-pct00312
 N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H) 322.13322.13 209209
Figure 112017032706954-pct00313
Figure 112017032706954-pct00313
 1-(4-메톡시벤질)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-methoxybenzyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (m, 3H), 6.94 (m, 4H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H) 2.54 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H 2H), 2.83 (m, 2H), 2.54 (s, 3H), 2.27 (m, 2H) 442.19442.19 210210
Figure 112017032706954-pct00314
Figure 112017032706954-pct00314
 1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Dihydro-lH-inden-2-yl) ethyl) -N- (4-methoxyphenethyl) -2-oxo- Quinolin-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 3H), 7.14 (t, 1H), 6.94 (m, 4H), 3.83 (s, 3H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 4H), 2.64 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 3H), 7.14 (t, IH), 6.94 (m, 4H) , 2.83 (m, 4 H), 2.64 (m, 5 H) 482.22482.22 211211
Figure 112017032706954-pct00315
Figure 112017032706954-pct00315
 1-((2,3-디하이드로-1H-인덴-5-일)메틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Yl) methyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (m, 4H), 6.94 (dd, 2H), 4.94 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H), 2.80 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.83 (s, 3H), 3.55 (m, 2H), 3.40 (d, , 2.83 (m, 2 H), 2.80 (m, 5 H) 452.21452.21 212212
Figure 112017032706954-pct00316
Figure 112017032706954-pct00316
 1-(2-(2,3-디하이드로-1H-인덴-5-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Yl) ethyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carbaldehyde Copymade 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 3H), 7.14 (t, 1H), 6.94 (m, 4H), 4.94 (s, 2H), 4.27 (s, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 7H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.83 (s, 3H), 7.31 (t, IH), 7.18 (m, 3H), 7.14 , 3.55 (m, 2H), 2.83 (m, 7H) 466.23466.23 213213
Figure 112017032706954-pct00317
Figure 112017032706954-pct00317
 5-(2-(4-플로로페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-fluorophenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.18 (dd, 2H), 7.12 (dd, 2H), 6.94 (dd, 2H), 3.90 (m, 2H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H 2H), 3.90 (m, 2H), 3.83 (s, 3H), 3.55 (d, 2H) , 2.83 (m, 2 H) 473.18473.18 214214
Figure 112017032706954-pct00318
Figure 112017032706954-pct00318
 5-(2-(4-에틸페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-ethylphenyl) acetamido) -N- (4- methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.27 (s, 1H, -NH), 7.18 (m, 4H), 6.98 (m, 4H), 3.83 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H), 2.60 (d, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 2.83 (m, 2H), 2.60 (m, 2H), 7.27 (s, , &Lt; / RTI &gt; 2H), 1.25 (s, 3H) 483.22483.22 215215
Figure 112017032706954-pct00319
Figure 112017032706954-pct00319
 N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (t, IH), 7.25 (dd, 2H), 7.14 356.02356.02 216216
Figure 112017032706954-pct00320
Figure 112017032706954-pct00320
 1-벤조일-N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzoyl-N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, 4H), 7.14 (m, 4H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 4.34 (m, 2H), 7.31 (m, 2H) 460.04460.04 217217
Figure 112017032706954-pct00321
Figure 112017032706954-pct00321
 N-(4-브로모벤질)-1-(4-메톡시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromobenzyl) -1- (4-methoxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, 4H), 7.14 (m, 4H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.27 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 7.31 (t, IH), 7.25 (m, 4H), 7.14 (m, 4H), 6.87 (dd, 2H) 490.05490.05 218218
Figure 112017032706954-pct00322
Figure 112017032706954-pct00322
 N-(4-브로모펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.51 (m, 2H), 2.83 (m, 2H), 7.31 (t, 370.03370.03 219219
Figure 112017032706954-pct00323
Figure 112017032706954-pct00323
 N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.3 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 490.05490.05 220220
Figure 112017032706954-pct00324
Figure 112017032706954-pct00324
 N-(4-브로모펜에틸)-2-옥소-1-(4-(트리플로로메톡시)벤조일)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzoyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 558.04558.04 221221
Figure 112017032706954-pct00325
Figure 112017032706954-pct00325
 N-(4-브로모펜에틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드2- (4-hydroxyphenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H), 6.63 (dd, 2H), 5.35 (s, 1H, -OH), 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H 1H), 7.29 (t, IH), 7.23 (s, IH, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H) 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 519.08519.08 222222
Figure 112017032706954-pct00326
Figure 112017032706954-pct00326
 N-(4-클로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (t, IH), 7.25 (dd, 2H), 7.14 312.07312.07 223223
Figure 112017032706954-pct00327
Figure 112017032706954-pct00327
 N-(4-클로로벤질)-1-(4-에틸벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorobenzyl) -1- (4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, 4H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H), 2.78 (s, 2H), 1.28 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 2.78 (s, 2H), 1.28 (s, 3H), 7.31 (m, 2H) 444.12444.12 224224
Figure 112017032706954-pct00328
Figure 112017032706954-pct00328
 N-(4-클로로벤질)-1-(4-하이드록시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorobenzyl) -1- (4-hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (m, 4H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 4.34 (m, 2H), 7.31 (m, 2H) 432.09432.09 225225
Figure 112017032706954-pct00329
Figure 112017032706954-pct00329
 N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.51 (m, 2H), 2.83 (m, 2H), 7.31 (t, 326.08326.08 226226
Figure 112017032706954-pct00330
Figure 112017032706954-pct00330
 N-(4-클로로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 2H), 1.78 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) , 1.78 (s, 3 H) 446.14446.14 227227
Figure 112017032706954-pct00331
Figure 112017032706954-pct00331
 1-(4-클로로벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-Chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 464.07464.07 228228
Figure 112017032706954-pct00332
Figure 112017032706954-pct00332
 N-(4-클로로펜에틸)-1-(4-아이오도벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenethyl) -1- (4-iodobenzoyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 556.01556.01 229229
Figure 112017032706954-pct00333
Figure 112017032706954-pct00333
 N-(4-클로로펜에틸)-1-(4-니트로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H) 475.09475.09 230230
Figure 112017032706954-pct00334
Figure 112017032706954-pct00334
 1-(4-아미노벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03(s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 4.28 (s, -NH2, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, 1H) , 7.18 (m, 4H), 7.14 (m, 3H), 6.94 (dd, 2H), 4.28 (s, -NH 2, 2H), 3.55 (m, 2H), 2.83 ( m, 2H) 445.12445.12 231231
Figure 112017032706954-pct00335
Figure 112017032706954-pct00335
 N-(4-클로로펜에틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenethyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H), 6.63 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.92 (dd, 2H), 7.88 (m, 2H ), 7.29 (t, IH), 7.23 (s, IH, -NH), 7.18 (dd, 2H), 7.06 (dd, 2H), 6.63 , &Lt; / RTI &gt; 2H), 2.83 (m, 2H) 504.12504.12 232232
Figure 112017032706954-pct00336
Figure 112017032706954-pct00336
 N-(4-플로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (t, IH), 7.25 (dd, 2H), 7.14 296.10296.10 233233
Figure 112017032706954-pct00337
Figure 112017032706954-pct00337
 N-(4-플로로벤질)-1-(4-포르밀벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorobenzyl) -1- (4-formylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 2.78 (s, 1H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 428.12428.12 234234
Figure 112017032706954-pct00338
Figure 112017032706954-pct00338
 1-(4-시아노벤조일)-N-(4-플로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-cyanobenzoyl) -N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 425.12425.12 235235
Figure 112017032706954-pct00339
Figure 112017032706954-pct00339
 N-(4-플로로벤질)-1-(4-(메틸티오)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorobenzyl) -1- (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 446.
11446.
11 236236
Figure 112017032706954-pct00340
Figure 112017032706954-pct00340
 N-(4-플로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.51 (m, 2H), 2.83 (m, 2H), 7.31 (t, 310.11310.11 237237
Figure 112017032706954-pct00341
Figure 112017032706954-pct00341
 N-(4-플로로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.51 (m, 2H), 2.83 (m, 2H), 7.31 (t, 430.17430.17 238238
Figure 112017032706954-pct00342
Figure 112017032706954-pct00342
 1-(4-(디플로로메틸)벤조일)-N-(4-플로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4- (Dipropromethyl) benzoyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (t, 1H), 6.94 (m, 4H), 3.55 (m, 2H), 2.83 (m, 2H), 1.78 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (m, 4H) 464.13464.13 239239
Figure 112017032706954-pct00343
Figure 112017032706954-pct00343
 N-(4-플로로펜에틸)-1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenethyl) -1- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 5H), 2.83 (m, 4H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 ), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, 458.16458.16 240240
Figure 112017032706954-pct00344
Figure 112017032706954-pct00344
 N-(4-플로로펜에틸)-2-옥소-1-(2-(4-(트리플로로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenethyl) -2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (t, 1H), 6.94 (m, 4H), 3.55 (m, 2H), 2.83 (m, 4H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, 512.14512.14 241241
Figure 112017032706954-pct00345
Figure 112017032706954-pct00345
 N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 1.25 (m, 3H), 7.31 (d, 306.14306.14 242242
Figure 112017032706954-pct00346
Figure 112017032706954-pct00346
 N-(4-에틸벤질)-1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 3.40 (m, 2H), 3.40 (s, , 1.25 (m, 3H) 440.17440.17 243243
Figure 112017032706954-pct00347
Figure 112017032706954-pct00347
 N-(4-에틸벤질)-1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (m, 3H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (m, 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H), 2.60 (m, 4H), 1.25 (m, 6H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 2H), 6.60 (d, 2H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 , 1.25 (m, 6H) 452.21452.21 244244
Figure 112017032706954-pct00348
Figure 112017032706954-pct00348
 N-(4-에틸벤질)-1-(2-(4-플로로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -1- (2- (4-fluorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 3.40 (m, 2H), 3.40 (s, , 1.25 (m, 3H) 442.17442.17 245245
Figure 112017032706954-pct00349
Figure 112017032706954-pct00349
 1-(2-(4-클로로페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (2- (4-chlorophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 3.40 (m, 2H), 3.40 (s, , 1.25 (m, 3H) 458.14458.14 246246
Figure 112017032706954-pct00350
Figure 112017032706954-pct00350
 N-(4-에틸벤질)-1-(2-(4-아이오도페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -1- (2- (4-iodophenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 3.40 (m, 2H), 3.40 (s, , 1.25 (m, 3H) 550.08550.08 247247
Figure 112017032706954-pct00351
Figure 112017032706954-pct00351
 N-(4-에틸벤질)-1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 2.60 (m, 2H), 3.40 (m, 2H), 3.40 (s, , 1.25 (m, 3H) 469.16469.16 248248
Figure 112017032706954-pct00352
Figure 112017032706954-pct00352
 1-(2-(4-아미노페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 4.2 (s, -NH2, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H ), 7.31 (m, 3H), 7.18 (m, 4H), 7.14 (t, IH), 6.98 (dd, 2H), 4.34 , 2H), 2.60 (m, 2H), 1.25 (m, 3H) 439.19439.19 249249
Figure 112017032706954-pct00353
Figure 112017032706954-pct00353
 N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 2H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) 8.28 δ (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 3.60 (m, 2H), 3.60 (m, 2H), 3.60 (d, , 1.25 (s, 3H) 320.15320.15 250250
Figure 112017032706954-pct00354
Figure 112017032706954-pct00354
 N-(4-에틸펜에틸)-1-(2-(4-포르밀페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenethyl) -1- (2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 3H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 3.60 (m, 4H), 2.60 (m, 3H), 7.31 (m, 2H) , 1.25 (s, 3H) 466.19466.19 251251
Figure 112017032706954-pct00355
Figure 112017032706954-pct00355
 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 3.60 (m, 4H), 2.60 (m, 2H), 7.31 (m, 2H) , 1.25 (s, 3H) 463.19463.19 252252
Figure 112017032706954-pct00356
Figure 112017032706954-pct00356
 N-(4-에틸펜에틸)-1-(2-(4-(메틸티오)페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4- (methylthio) phenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 2H), 1.25 (s, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 3.60 (m, 4H), 2.60 (m, 2H), 7.31 (m, 2H) , 1.25 (s, 6H) 484.18484.18 253253
Figure 112017032706954-pct00357
Figure 112017032706954-pct00357
 1-(2-(4-(디플로로메틸)페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (m, 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 2H), 1.25 (s, 4H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s. 1H, -NH), 7.36 (d, 1H 2H), 3.60 (m, 4H), 2.60 (m, 2H), 7.31 (m, 2H) , 1.25 (s, 4H) 488.19488.19 254254
Figure 112017032706954-pct00358
Figure 112017032706954-pct00358
 N-(4-하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 5.35 (s, 1H, -OH), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 1H), 7.31 (t, IH), 7.25 (dd, 2H), 7.14 (t, IH), 6.87 (dd, 2H) 294.10294.10 255255
Figure 112017032706954-pct00359
Figure 112017032706954-pct00359
 N-(4-하이드록시벤질)-1-(4-(메틸티오)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxybenzyl) -1- (4- (methylthio) benzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 5.35 (s, 1H, -OH), 3.3 (S, 2H), 4.34 (m, 5H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 1H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 , 5H) 430.14430.14 256256
Figure 112017032706954-pct00360
Figure 112017032706954-pct00360
 N-(4-하이드록시벤질)-1-(4-(메틸티오)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxybenzyl) -1- (4- (methylthio) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 5.35 (s, 1H, -OH), 3.3 (S, 2H), 2.87 (s, 2H), 4.34 (m, 5H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 1H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 , &Lt; / RTI &gt; 2H), 4.34 (m, 5H) 444.15444.15 257257
Figure 112017032706954-pct00361
Figure 112017032706954-pct00361
 N-(4-하이드록시벤질)-2-옥소-1-(4-(트리플로로메톡시)펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxybenzyl) -2-oxo-1- (4- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 5.35 (s, 1H, -OH), 3.3 (S, 2H), 2.87 (s, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 1H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 , &Lt; / RTI &gt; 2H), 4.34 (m, 2H) 482.15482.15 258258
Figure 112017032706954-pct00362
Figure 112017032706954-pct00362
 N-(4-하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 5.35 (s, 1H, -OH), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 5.35 , 2H) 308.12308.12 259259
Figure 112017032706954-pct00363
Figure 112017032706954-pct00363
 N-(4-하이드록시펜에틸)-1-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenethyl) -1- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 5.35 (s, 1H, -OH), 3.55 (m, 2H), 3.3 (s, 2H), 2.97 (s, 2H), 2.83 (m, 5H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 1H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 , 2H), 2.97 (s, 2H), 2.83 (m, 5H) 442.19442.19 260260
Figure 112017032706954-pct00364
Figure 112017032706954-pct00364
 N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, ), 7.31 (t, IH), 7.25 (dd, 2H), 7.14 323.09323.09 261261
Figure 112017032706954-pct00365
Figure 112017032706954-pct00365
 1-(4-아이오도벤질)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-Iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 539.03539.03 262262
Figure 112017032706954-pct00366
Figure 112017032706954-pct00366
 1-(4-아이오도펜에틸)-N-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-Iodophenethyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H), 2.8 (s, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 7.31 (m, 3H), 7.25 (d, 2H), 7.14 553.05553.05 263263
Figure 112017032706954-pct00367
Figure 112017032706954-pct00367
 N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.51 (m, 2H), 2.83 (m, 2H), 7.31 (t, 337.11337.11 264264
Figure 112017032706954-pct00368
Figure 112017032706954-pct00368
 1-(4-포르밀벤질)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-formylbenzyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 3.3 (s, 2H), 2.83 (m, 3H), 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 2H), 7.31 (m, 3H), 7.18 (d, 2H), 7.14 , 455.15455.15 265265
Figure 112017032706954-pct00369
Figure 112017032706954-pct00369
 1-(4-포르밀펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 4H), 2.83 (m, 5H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (dd, 2H) 469.06469.06 266266
Figure 112017032706954-pct00370
Figure 112017032706954-pct00370
 1-(4-(디플로로메틸)펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (t, 1H), 7.18 (m, 4H), 7.14 (t, 1H), 6.94 (dd, 2H), 3.55 (m, 4H), 2.83 (m, 4H), 1.37 (s, 1H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 ), 7.31 (t, IH), 7.18 (m, 4H), 7.14 (t, IH), 6.94 (dd, 2H) 491.17491.17 267267
Figure 112017032706954-pct00371
Figure 112017032706954-pct00371
 N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 4.34 (m, 2H), 2.66 385.11385.11 268268
Figure 112017032706954-pct00372
Figure 112017032706954-pct00372
 1-(4-(디플로로메틸)벤질)-N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (m, 4H), 7.36 (m, 3H), 7.31 (t, 1H), 7.14 (t, 1H), 4.34 (m, 2H), 3.3 (s, 2H), 2.66 (m, 6H), 1.78 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (m, 4H), 7.36 2H), 2.66 (m, 6H), 1.78 (s, IH), 7.31 (m, 2H) 525.15525.15 269269
Figure 112017032706954-pct00373
Figure 112017032706954-pct00373
 N-(4-(N,N-디메틸설파모일)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 2.83 (m, 2H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.83 399.13399.13 270270
Figure 112017032706954-pct00374
Figure 112017032706954-pct00374
 N-(4-(하이드록시메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36(d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 4.61 (s, 2H), 4.34 (m, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 4.61 (s, 2H), 4.34 308.12308.12 271271
Figure 112017032706954-pct00375
Figure 112017032706954-pct00375
 N-(4-(하이드록시메틸)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65 (s, 1H, -OH), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 3.65 322.13322.13 272272
Figure 112017032706954-pct00376
Figure 112017032706954-pct00376
 2-옥소-N-(4-비닐벤질)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N- (4-vinylbenzyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H ), 7.36 (d, IH), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 , &Lt; / RTI &gt; 4.34 (m, 2H) 304.12304.12 273273
Figure 112017032706954-pct00377
Figure 112017032706954-pct00377
 2-옥소-N-(4-비닐펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드Oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 4.34 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.59 (dd, 2H ), 7.36 (d, IH), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 , 4.34 (m, 2 H), 2.83 (m, 2 H) 318.14318.14 274274
Figure 112017032706954-pct00378
Figure 112017032706954-pct00378
 N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.19 (t, IH), 7.14 278.11278.11 275275
Figure 112017032706954-pct00379
Figure 112017032706954-pct00379
 1-(2,3-디하이드로-1H-인덴e-2-카르보닐)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드1- (2,3-dihydro-1H-indene e-2-carbonyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 2.67 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 422.16422.16 276276
Figure 112017032706954-pct00380
Figure 112017032706954-pct00380
 1-(2-(2,3-디하이드로-1H-인덴-2-일)아세틸)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드Yl) acetyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 436.18436.18 277277
Figure 112017032706954-pct00381
Figure 112017032706954-pct00381
 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxaldehyde Mide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.89 (s, 2H), 2.67 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 5H) 450.19450.19 278278
Figure 112017032706954-pct00382
Figure 112017032706954-pct00382
 N-에틸-1-(2-(5-메톡시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-1- (2- (5-methoxy-2,3-dihydro- - carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 5H) 480.20480.20 279279
Figure 112017032706954-pct00383
Figure 112017032706954-pct00383
 N-에틸-1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline -3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 5H) 496.18496.18 280280
Figure 112017032706954-pct00384
Figure 112017032706954-pct00384
 N-에틸-2-옥소-N-페닐-1-(2-(5-(트리플로로메톡시)-2,3-디하이드로-1H-인덴-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드Dihydro-1H-inden-2-yl) acetyl) - 1, 2-di (2-oxo- Hydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 534.18534.18 281281
Figure 112017032706954-pct00385
Figure 112017032706954-pct00385
 N-에틸-1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinolin-3 - carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 466.19466.19 282282
Figure 112017032706954-pct00386
Figure 112017032706954-pct00386
 N-에틸-1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-1- (2- (5-ethyl-2,3-dihydro- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (m, 4H), 2.67 (m, 7H), 2.43 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 5H) 478.23478.23 283283
Figure 112017032706954-pct00387
Figure 112017032706954-pct00387
 N-에틸-1-(2-(5-플로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinolin-3 - carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 468.18468.18 284284
Figure 112017032706954-pct00388
Figure 112017032706954-pct00388
 1-(2-(5-클로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinolin-3- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 484.16484.16 285285
Figure 112017032706954-pct00389
Figure 112017032706954-pct00389
 N-에틸-1-(2-(5-아이오도-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinolin-3 - carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 576.09576.09 286286
Figure 112017032706954-pct00390
Figure 112017032706954-pct00390
 N-에틸-1-(2-(5-니트로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-1- (2- (5-nitro-2,3-dihydro- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 m, 2H) 495.16495.16 287287
Figure 112017032706954-pct00391
Figure 112017032706954-pct00391
 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-yl) acetyl) -N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinolin-3- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 4.28 (s, -NH2, 2H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 4.28 (s, , 2.67 (m, 7 H), 2.43 (m, 2 H) 465.21465.21 288288
Figure 112017032706954-pct00392
Figure 112017032706954-pct00392
 N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (t, 1H), 7.14 (t, 1H), 4.28 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.19 (t, IH), 7.14 292.12292.12 289289
Figure 112017032706954-pct00393
Figure 112017032706954-pct00393
 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-N-phenyl-l, 2-dihydroquinoline-3-carboxaldehyde Mide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, 1H), 7.31 (m, 3H), 7.19 (t, 1H), 7.14 (t, 1H), 4.28 (m, 2H), 2.68 (m, 7H), 2.37 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 (m, 3H), 7.19 (t, IH), 7.14 (t, IH), 4.28 (m, 2H), 2.68 s, 3H) 464.21464.21 290290
Figure 112017032706954-pct00394
Figure 112017032706954-pct00394
 N-에틸-2-옥소-N-페닐-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-N-phenyl-5-propionamido-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (t, 1H), 4.28 (m, 2H), 2.45 (m, 2H), 1.31 (s, 3H), 1.02 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 1.31 (s, 3H), 1.02 (s, 3H), 7.23 (s, 1H) 363.16363.16 291291
Figure 112017032706954-pct00395
Figure 112017032706954-pct00395
 5-butyramido-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드5-butyramido-N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.19 (t, 1H), 4.28 (m, 2H), 2.45 (m, 2H), 1.31 (s, 3H), 1.02 (m, 2H), 0.90 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.81 (dd, 2H), 7.43 (dd, 2H), 7.29 2H), 1.31 (s, 3H), 1.02 (m, 2H), 7.28 (m, , 0.90 (s, 3H) 377.17377.17 292292
Figure 112017032706954-pct00396
Figure 112017032706954-pct00396
 N-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.21 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 3.44 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.21 (dd, 2H), 7.31 (t, 1 H), 7.14 (t, 1 H), 3.44 (s, 3 H), 2.34 292.12292.12 293293
Figure 112017032706954-pct00397
Figure 112017032706954-pct00397
 N-에틸-2-옥소-5-펜탄아미도-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-2-oxo-5-pentanamido-N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 2.39 (m, 2H), 2.34 (s, 3H), 1.63 (m, 2H), 1.31 (m, 5H), 0.90 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.63 (m, 2H), 1.31 (m, 5H), 2.32 , 0.90 (s, 3H) 405.21405.21 294294
Figure 112017032706954-pct00398
Figure 112017032706954-pct00398
 N-에틸-5-(2-메톡시아세트아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-5- (2-methoxyacetamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 2.39 (m, 2H), 2.34 (s, 3H), 1.63 (m, 2H), 0.90 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.63 (s, 3H), 1.63 (m, 2H), 7.21 (d, 2H) 393.17393.17 295295
Figure 112017032706954-pct00399
Figure 112017032706954-pct00399
 N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.14 (t, 1H), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.21 (d, 2H), 7.14 (s, 3H) 306.14306.14 296296
Figure 112017032706954-pct00400
Figure 112017032706954-pct00400
 N-에틸-2-옥소-1-(4-(페닐티오)벤질)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-1- (4- (phenylthio) benzyl) -N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 3.3 (s, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H) 504.19504.19 297297
Figure 112017032706954-pct00401
Figure 112017032706954-pct00401
 N-에틸-2-옥소-1-(4-페녹시벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-2-oxo-1- (4-phenoxybenzoyl) -N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (t, 1H), 7.21 (m, 7H), 7.14 (t, 502.19502.19 298298
Figure 112017032706954-pct00402
Figure 112017032706954-pct00402
 N-에틸-2-옥소-1-(4-(페닐티오)벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-1- (4- (phenylthio) benzoyl) -N- (p-tolyl) -1, 2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (t, 1H), 7.21 (m, 7H), 7.14 (t, 518.17518.17 299299
Figure 112017032706954-pct00403
Figure 112017032706954-pct00403
 N-에틸-2-옥소-1-(2-(4-(페닐티오)페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드Acetyl) -N- (p-tolyl) -1, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 3.7 (s, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 2H), 2.34 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H) 532.18532.18 300300
Figure 112017032706954-pct00404
Figure 112017032706954-pct00404
 N-에틸-2-옥소-1-(2-(4-페녹시페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드(2- (4-phenoxyphenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 3.70 (s, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 2H), 3.70 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H) 516.20516.20 301301
Figure 112017032706954-pct00405
Figure 112017032706954-pct00405
 1-(2-(4-벤질페닐)아세틸)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드(2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 3.70 (s, 2H), 2.78 (s, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 2H), 2.34 (s, 3H), 2.31 (s, 3H), 2.31 (s, 3H) s, 3H) 514.23514.23 302302
Figure 112017032706954-pct00406
Figure 112017032706954-pct00406
 1-(4-벤질벤조일)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드1- (4-benzylbenzoyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (m, 6H), 7.31 (t, 1H), 7.21 (m, 7H), 7.14 (t, 1H), 4.28 (m, 2H), 3.70 (s, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 2H), 3.70 (s, 3H), 1.31 (s, 3H), 7.21 (m, 2H) 500.21500.21 303303
Figure 112017032706954-pct00407
Figure 112017032706954-pct00407
 N-(4-메톡시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-methoxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.21 (dd, 2H), 7.14 (t, 1H), 4.28 (s, 3H), 3.83 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s, 1H), 7.34 (dd, 2H), 7.31 (s, 3H), 7.21 (d, 2H), 7.14 (t, 308.12308.12 304304
Figure 112017032706954-pct00408
Figure 112017032706954-pct00408
 N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.93 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.31 (s, 3H), 2.32 (s, 3H) 322.13322.13 305305
Figure 112017032706954-pct00409
Figure 112017032706954-pct00409
 5-(2-브로모아세트아미도)-N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 4.24 (m, 2H), 3.93 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 3.31 (s, 3H), 2.31 (s, 3H) 457.06457.06 306306
Figure 112017032706954-pct00410
Figure 112017032706954-pct00410
 N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 356.02356.02 307307
Figure 112017032706954-pct00411
Figure 112017032706954-pct00411
 N-(4-브로모페닐)-1-(사이클로펜타-1,3-디엔e카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -1- (cyclopenta-1,3-diene e carbonyl) -N- methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 448.04448.04 308308
Figure 112017032706954-pct00412
Figure 112017032706954-pct00412
 N-(4-브로모페닐)-N-메틸-2-옥소-1-(2H-피롤-3-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-3-carbonyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 449.04449.04 309309
Figure 112017032706954-pct00413
Figure 112017032706954-pct00413
 N-(4-브로모페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 466.00466.00 310310
Figure 112017032706954-pct00414
Figure 112017032706954-pct00414
 N-(4-브로모페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.78 450.02450.02 311311
Figure 112017032706954-pct00415
Figure 112017032706954-pct00415
 N-(4-브로모페닐)-N-메틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 2H), 2.78 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 480.01480.01 312312
Figure 112017032706954-pct00416
Figure 112017032706954-pct00416
 N-(4-브로모페닐)-1-(2-(퓨란-2-일)아세틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 2H), 2.78 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 464.04464.04 313313
Figure 112017032706954-pct00417
Figure 112017032706954-pct00417
 1-(2-(2H-피롤-2-일)아세틸)-N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Yl) acetyl) -N- (4-bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 2H), 2.78 (s, 3H), 2.98 (s, 2H), 2.78 (m, 6H) 473.05473.05 314314
Figure 112017032706954-pct00418
Figure 112017032706954-pct00418
 N-(4-브로모페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 370.03370.03 315315
Figure 112017032706954-pct00419
Figure 112017032706954-pct00419
 N-(4-브로모페닐)-1-(사이클로헥산카르보닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -1- (cyclohexanecarbonyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.98 (m, 10H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H), 7.21 (dd, 2H), 4.28 (m, 2H), 1.98 480.10480.10 316316
Figure 112017032706954-pct00420
Figure 112017032706954-pct00420
 N-(4-브로모페닐)-1-(3-사이클로헥실프로파노일)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -1- (3-cyclohexylpropanoyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 2.79 (s, 2H), 2.54 (s, 2H), 1.98 (m, 10H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 1.31 (s, 1H), 7.21 (d, 2H), 4.28 (m, 2H), 2.79 508.14508.14 317317
Figure 112017032706954-pct00421
Figure 112017032706954-pct00421
 N-(4-브로모페닐)-5-(2-클로로아세트아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-bromophenyl) -5- (2-chloroacetamido) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88(m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 4.24 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 7.21 (d, 2H), 4.28 (m, 2H) 461.01461.01 318318
Figure 112017032706954-pct00422
Figure 112017032706954-pct00422
 N-(4-클로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 312.07312.07 319319
Figure 112017032706954-pct00423
Figure 112017032706954-pct00423
 N-(4-클로로페닐)-1-(사이클로펜탄카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1- (cyclopentanecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 8H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 408.12408.12 320320
Figure 112017032706954-pct00424
Figure 112017032706954-pct00424
 N-(4-클로로페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-Chlorophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 406.07406.07 321321
Figure 112017032706954-pct00425
Figure 112017032706954-pct00425
 N-(4-클로로페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -N-methyl-2-oxo-1- (thiophene-2- carbonyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 422.05422.05 322322
Figure 112017032706954-pct00426
Figure 112017032706954-pct00426
 N-(4-클로로페닐)-N-메틸-2-옥소-1-(2H-피롤-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -N-methyl-2-oxo-1- (2H-pyrrole- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.98 405.09405.09 323323
Figure 112017032706954-pct00427
Figure 112017032706954-pct00427
 N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 326.08326.08 324324
Figure 112017032706954-pct00428
Figure 112017032706954-pct00428
 N-(4-클로로페닐)-1-(2-사이클로펜틸아세틸)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-chlorophenyl) -1- (2-cyclopentyl acetyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.45 (m, 2H), 2.87 (m, 8H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (m, 2H), 3.45 (m, 2H), 2.87 (m, 8H), 1.31 (s, 3H) 436.16436.16 325325
Figure 112017032706954-pct00429
Figure 112017032706954-pct00429
 N-(4-클로로페닐)-N-에틸-1-(2-(퓨란-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-1- (2- (furan-2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.45 (m, 2H), 2.87 (m, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 2.31 (s, 3H), 2.28 (m, 2H) 434.10434.10 326326
Figure 112017032706954-pct00430
Figure 112017032706954-pct00430
 N-(4-클로로페닐)-N-에틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.45 (m, 2H), 2.87 (m, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 2.31 (s, 3H), 2.28 (m, 2H) 450.08450.08 327327
Figure 112017032706954-pct00431
Figure 112017032706954-pct00431
 1-(2-(2H-피롤-2-일)아세틸)-N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Acetyl) -N- (4-chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 3.45 (m, 2H), 2.87 (m, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 3H), 2.31 (s, 3H), 2.28 (m, 2H) 433.12433.12 328328
Figure 112017032706954-pct00432
Figure 112017032706954-pct00432
 N-(4-플로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H) 296.10296.10 329329
Figure 112017032706954-pct00433
Figure 112017032706954-pct00433
 N-(4-플로로페닐)-N-메틸-2-옥소-1-(2-옥소-2-페닐에틸)-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-1- (2-oxo-2-phenylethyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 414.14414.14 330330
Figure 112017032706954-pct00434
Figure 112017032706954-pct00434
 N-(4-플로로페닐)-1-(2-(4-메톡시페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -1- (2- (4-methoxyphenyl) -2-oxoethyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H), 1.35 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 3H), 2.79 (s, 2H), 1.35 (s, 3H) 444.15444.15 331331
Figure 112017032706954-pct00435
Figure 112017032706954-pct00435
 N-(4-플로로페닐)-N-메틸-2-옥소-1-(2-옥소-2-(4-(트리플로로메톡시)페닐)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드(2-oxo-2- (4- (trifluoromethoxy) phenyl) ethyl) -1,2-dihydroquinolin-3 - carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 498.12498.12 332332
Figure 112017032706954-pct00436
Figure 112017032706954-pct00436
 N-(4-플로로페닐)-N-메틸-1-(2-(4-니트로페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-1- (2- (4-nitrophenyl) -2-oxoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 459.12459.12 333333
Figure 112017032706954-pct00437
Figure 112017032706954-pct00437
 N-(4-플로로페닐)-1-(2-(4-하이드록시페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -1- (2- (4-hydroxyphenyl) -2-oxoethyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 430.13430.13 334334
Figure 112017032706954-pct00438
Figure 112017032706954-pct00438
 N-(4-플로로페닐)-1-(2-(4-플로로페닐)-2-옥소에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-fluorophenyl) -1- (2- (4-fluorophenyl) -2-oxoethyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 432.13432.13 335335
Figure 112017032706954-pct00439
Figure 112017032706954-pct00439
 1-(2-(4-에틸페닐)-2-옥소에틸)-N-(4-플로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드2- (4-ethylphenyl) -2-oxoethyl) -N- (4-fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.97 (m, 2H), 2.79 (s, 2H), 1.35 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 3H), 2.97 (s, 2H), 2.32 (s, 2H) 442.17442.17 336336
Figure 112017032706954-pct00440
Figure 112017032706954-pct00440
 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 448.10448.10 337337
Figure 112017032706954-pct00441
Figure 112017032706954-pct00441
 N-에틸-N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 310.11310.11 338338
Figure 112017032706954-pct00442
Figure 112017032706954-pct00442
 1-(2-(4-아미노페닐)-2-옥소에틸)-N-에틸-N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4-aminophenyl) -2-oxoethyl) -N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 4.05 (s, -NH2, -2H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 4.05 (s, -NH 2, -2H), 2.79 (s, 2H) 443.16443.16 339339
Figure 112017032706954-pct00443
Figure 112017032706954-pct00443
 1-(2-(4-시아노페닐)-2-옥소에틸)-N-에틸-N-(4-플로로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 453.15453.15 340340
Figure 112017032706954-pct00444
Figure 112017032706954-pct00444
 N-에틸-N-(4-플로로페닐)-1-(2-(4-(메틸티오)페닐)-2-옥소에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-fluorophenyl) -1- (2- (4- (methylthio) phenyl) -2-oxoethyl) -2-oxo-1,2-dihydroquinoline- Copymade 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 3.30 (s, 3H), 2.79 (s, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 3H), 2.79 (s, 2H), 4.28 (s, 3H) 474.14474.14 341341
Figure 112017032706954-pct00445
Figure 112017032706954-pct00445
 N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.27 (dd, 2H), 7.14 (t, 1H), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.27 (d, 2H), 7.14 (t, 306.14306.14 342342
Figure 112017032706954-pct00446
Figure 112017032706954-pct00446
 1-(2,4-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (2,4-dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 6H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H) 424.22424.22 343343
Figure 112017032706954-pct00447
Figure 112017032706954-pct00447
 1-(2,4-디메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (2,4-dimethylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s,, 2H), 2.80 (m, 6H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 3 H) 438.22438.22 344344
Figure 112017032706954-pct00448
Figure 112017032706954-pct00448
 N-(4-에틸페닐)-1-(4-하이드록시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H) 426.19426.19 345345
Figure 112017032706954-pct00449
Figure 112017032706954-pct00449
 N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-1- (2-methyl-4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H) 455.18455.18 346346
Figure 112017032706954-pct00450
Figure 112017032706954-pct00450
 1-(4-에틸-2-메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 6H), 2.60 (m, 4H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H) 452.25452.25 347347
Figure 112017032706954-pct00451
Figure 112017032706954-pct00451
 N-(4-에틸페닐)-1-(4-하이드록시-2-메틸펜에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H) 440.21440.21 348348
Figure 112017032706954-pct00452
Figure 112017032706954-pct00452
 N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-1- (2-methyl-4-nitrophenethyl) -2-oxo-1,2- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 s, 3H) 469.20469.20 349349
Figure 112017032706954-pct00453
Figure 112017032706954-pct00453
 1-(4-에틸-2-메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 6H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H) 438.23438.23 350350
Figure 112017032706954-pct00454
Figure 112017032706954-pct00454
 1-(2,3-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드1- (2,3-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, 1H), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 (m, 6H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.41 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.27 (m, 3H), 7.14 (t, IH), 3.44 (s, 3H), 3.28 (s, 2H), 2.80 s, 3H) 424.22424.22 351351
Figure 112017032706954-pct00455
Figure 112017032706954-pct00455
 N-(4-에틸페닐)-5-(2-플로로아세트아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -5- (2-fluoroacetamido) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (dd, 2H),7.23 (s, 1H, -NH), 5.03 (m, 2H), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (s, 3H), 2.63 (s, 3H), 2.60 (m, 2H) 381.15381.15 352352
Figure 112017032706954-pct00456
Figure 112017032706954-pct00456
 N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.60 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (dd, 2H), 7.29 (t, 1H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H) 320.15320.15 353353
Figure 112017032706954-pct00457
Figure 112017032706954-pct00457
 1-(2,5-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 438.23438.23 354354
Figure 112017032706954-pct00458
Figure 112017032706954-pct00458
 1-(3,4-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H),2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 438.23438.23 355355
Figure 112017032706954-pct00459
Figure 112017032706954-pct00459
 1-(2,6-디메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 8H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 438.23438.23 356356
Figure 112017032706954-pct00460
Figure 112017032706954-pct00460
 N-에틸-N-(4-에틸페닐)-2-옥소-1-(2,4,6-트리메틸벤질)-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-N- (4-ethylphenyl) -2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 11H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 452.25452.25 357357
Figure 112017032706954-pct00461
Figure 112017032706954-pct00461
 1-(4-(디플로로메틸)-2-메틸벤질)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Methylphenyl) -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 5H), 1.25 (m, 4H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 474.21474.21 358358
Figure 112017032706954-pct00462
Figure 112017032706954-pct00462
 (E)-1-(2-(4-(디플로로메틸)-2-메틸사이클로헥사-2,4-디엔-1-일리덴)에틸)-N-에틸-N-(4-에틸페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(E) -1- (2- (4- (Dipropromethyl) -2-methylcyclohexa-2,4-dien-1-ylidene) ethyl) ) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (dd, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 (m, 2H), 2.60 (m, 5H), 1.25 (m, 5H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.41 (m, 4H), 7.29 (m, 2H), 7.27 (d, 2H), 4.28 (m, 2H), 3.44 (s, 3H), 2.8 488.23488.23 359359
Figure 112017032706954-pct00463
Figure 112017032706954-pct00463
 N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H), 5.35 294.10294.10 360360
Figure 112017032706954-pct00464
Figure 112017032706954-pct00464
 N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4-methoxy-2-methylbenzyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.44 (m, 9H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 428.17428.17 361361
Figure 112017032706954-pct00465
Figure 112017032706954-pct00465
 N-(4-하이드록시페닐)-N-메틸-2-옥소-1-(2,3,4,5,6-펜타메틸벤질)-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -N-methyl-2-oxo-1- (2,3,4,5,6-pentamethylbenzyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.44 (m, 18H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, IH), 6.93 (dd, 2H), 5.35 454.23454.23 362362
Figure 112017032706954-pct00466
Figure 112017032706954-pct00466
 (E)-5-(부트-2-에나미도)-N-(4-하이드록시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(E) -5- (but-2-enamido) -N- (4-hydroxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (s, 2H), 7.38 (s, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 6.62 (s, 1H), 5.35 (s, 1H, -OH), 3.44 (s, 3H), 2.05 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (s, 2H), 7.38 (s, 1H), 7.36 (s, 3H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H) , 2.05 (s, 1 H) 377.14377.14 363363
Figure 112017032706954-pct00467
Figure 112017032706954-pct00467
 N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, IH), 6.93 (s, 3H) 308.12308.12 364364
Figure 112017032706954-pct00468
Figure 112017032706954-pct00468
 N-에틸-N-(4-하이드록시페닐)-1-(4-메톡시-2-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(4-methoxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (m, 4H), 1.31 (m, 9H) 456.20456.20 365365
Figure 112017032706954-pct00469
Figure 112017032706954-pct00469
 1-(2,3-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (m, 4H), 1.31 (m, 9H) 440.21440.21 366366
Figure 112017032706954-pct00470
Figure 112017032706954-pct00470
 1-(2,5-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (m, 4H), 1.31 (m, 9H) 440.21440.21 367367
Figure 112017032706954-pct00471
Figure 112017032706954-pct00471
 1-(2,6-디메틸펜에틸)-N-에틸-N-(4-하이드록시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 9H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (m, 4H), 1.31 (m, 9H) 442.20442.20 368368
Figure 112017032706954-pct00472
Figure 112017032706954-pct00472
 N-에틸-N-(4-하이드록시페닐)-2-옥소-1-(2,4,6-트리메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1- (2,4,6-trimethylphenethyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 1H, -OH), 4.28 (s, 2H), 3.87 (m, 4H), 1.31 (m, 12H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m, 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, 454.23454.23 369369
Figure 112017032706954-pct00473
Figure 112017032706954-pct00473
 N-메틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H), 3.44 323.09323.09 370370
Figure 112017032706954-pct00474
Figure 112017032706954-pct00474
 N-메틸-N-(4-니트로페닐)-2-옥소-1-(2,3,4,5,6-펜타메틸펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-N- (4-nitrophenyl) -2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 4.87 (m, 4H), 3.44 (s, 3H), 3.12 (m, 15H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 4.87 (m, 4H) 497.23497.23 371371
Figure 112017032706954-pct00475
Figure 112017032706954-pct00475
 N-에틸-N-(4-니트로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 4.28 (s, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.86 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 2H), 1.31 (s, 3H), 7.13 (d, IH) 337.11337.11 372372
Figure 112017032706954-pct00476
Figure 112017032706954-pct00476
 N-(4-(N,N-디메틸설파모일)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 3.44 (s, 3H), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.93 (dd, 2H), 3.44 385.11385.11 373373
Figure 112017032706954-pct00477
Figure 112017032706954-pct00477
 N-(4-(N,N-디메틸설파모일)페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 3.44 (s, 3H), 2.66 (m, 6H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.86 (ss, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.93 (dd, 2H), 3.44 (s, 3H) 399.13399.13 374374
Figure 112017032706954-pct00478
Figure 112017032706954-pct00478
 N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 1H), 3.44 (s, 3H), 3.65 (s, 2H) 308.12308.12 375375
Figure 112017032706954-pct00479
Figure 112017032706954-pct00479
 1-(4-(1H-피라졸-1-일)벤질)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde Copymade 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (m, 3H), 7.31 (m, 2H), 7.14 (t, 1H), 4.61 (m, 2H), 4.28 (s, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.87 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (s, 3H), 7.31 (m, 2H), 7.14 (t, IH), 4.61 (m, 2H), 4.28 , 2.87 (m, 3H) 464.18464.18 376376
Figure 112017032706954-pct00480
Figure 112017032706954-pct00480
 1-(4-(1H-피라졸-1-일)벤조일)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드Benzoyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde Copymade 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (m, 3H), 7.31 (m, 2H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.87 (m, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (m, 3H), 7.36 (m, 2H), 7.34 (m, 3H), 7.31 (m, 2H), 7.14 (t, IH), 4.61 (m, 2H), 3.65 478.16478.16 377377
Figure 112017032706954-pct00481
Figure 112017032706954-pct00481
 1-(2,2-디페닐아세틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 (m, 5H), 7.31 (m, 4H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.80 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 (s, 3H), 2.80 (s, IH), 3.61 (m, 2H) 502.19502.19 378378
Figure 112017032706954-pct00482
Figure 112017032706954-pct00482
 1-(2,2-디페닐에틸)-N-(4-(하이드록시메틸)페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 (m, 5H), 7.31 (m, 4H), 7.14 (t, 1H), 4.61 (m, 2H), 4.23 (s, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.80 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (m, 6H), 7.34 2H), 3.65 (s, 2H), 3.65 (s, 3H), 3.45 (s, 3H) , 2.80 (s, 1 H) 488.21488.21 379379
Figure 112017032706954-pct00483
Figure 112017032706954-pct00483
 N-(4-(하이드록시메틸)페닐)-5-(3-하이드록시프로판아미도)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4- (hydroxymethyl) phenyl) -5- (3-hydroxypropanamido) -N-methyl-2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.91 (m, 2H), 3.65 (m, 2H, -OH), 3.44 (s, 3H), 2.42 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (m, 2H), 3.65 (m, 2H), 3.45 (s, 3H) , &Lt; / RTI &gt; 2.42 (m, 2H) 395.15395.15 380380
Figure 112017032706954-pct00484
Figure 112017032706954-pct00484
 N-(4-(하이드록시메틸)페닐)-N-메틸-5-(2-니트로아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-5- (2-nitroacetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.42 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (s, 3H), 2.42 (m, 2H), 7.31 (t, 1H), 7.14 410.12410.12 381381
Figure 112017032706954-pct00485
Figure 112017032706954-pct00485
 N-에틸-N-(4-(하이드록시메틸)페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 4.28 (m, 2H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.39 (dd, 2H), 7.36 (d, 1H), 7.34 (s, 3H), 3.31 (s, 3H), 2.40 (s, 3H) 322.13322.13 382382
Figure 112017032706954-pct00486
Figure 112017032706954-pct00486
 N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 9.23 (dd, 2H), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 9.23 (dd, 2H), 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.88 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (s, IH), 6.63 304.12304.12 383383
Figure 112017032706954-pct00487
Figure 112017032706954-pct00487
 (E)-5-(부트-2-에나미도)-N-메틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드(E) -5- (but-2-enamido) -N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H, -NH), 9.23 (dd, 2H), 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m, 4H), 7.29 (t, 1H), 6.63 (s, 1H), 6.62 (s, 1H), 6.26 (d, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 3.44 (s, 3H), 2.05 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 10.12 (s, 1 H, -NH), 9.23 (dd, 2H), 8.28 ), 7.29 (s, IH), 6.63 (s, IH), 6.62 (s, IH), 6.26 , 2.05 (s, 3H) 387.16387.16 384384
Figure 112017032706954-pct00488
Figure 112017032706954-pct00488
 N-에틸-2-옥소-N-(4-비닐페닐)-1,2-디하이드로퀴놀린-3-카복사마이드Ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 9.23 (dd, 2H), 8.28 (d, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.88 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 4.28 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 9.23 (dd, 2H), 8.28 (d, 1H), 8.14 (d, 1H), 8.0 (s, 1H), 7.88 (dd, 2H), 7.31 (t, 1H), 7.14 (s, 1H), 6.63 (s, 1H), 5.61 (s, 318.14318.14 385385
Figure 112017032706954-pct00489
Figure 112017032706954-pct00489
 N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.21 (m, 2H), 1.04 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.21 (m, 2H), 1.04 216.09216.09 386386
Figure 112017032706954-pct00490
Figure 112017032706954-pct00490
 5-벤즈아미도-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5-benzamido-N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H, -NH), 8.03 (m, 3H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.70 (t, 1H), 7.63 (dd, 2H), 7.29 (t, 1H), 3.21 (m, 2H), 1.04 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H, -NH), 8.03 (m, 3H, -NH), 8.0 (s, 1H, -NH) , 7.88 (m, 2H), 7.70 (t, 1H), 7.63 (dd, 2H), 7.29 355.13355.13 387387
Figure 112017032706954-pct00491
Figure 112017032706954-pct00491
 5-(3,4-디하이드록시벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (3,4-dihydroxybenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.42 (d, 1H), 7.37 (s, 1H), 7.29 (t, 1H), 7.16 (d, 1H), 5.35 (m, 2H, -OH), 3.21 (m, 2H), 1.04 (s, 3H). 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 ( 2H), 7.42 (d, 1H), 7.37 (s, IH), 7.29 (t, IH), 7.16 1.04 (s, 3 H). 367.12367.12 388388
Figure 112017032706954-pct00492
Figure 112017032706954-pct00492
 5-(3,4-디메틸벤즈아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (3,4-dimethylbenzamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.42 (d, 1H), 7.37 (s, 1H), 7.29 (t, 1H), 7.16 (d, 1H), 3.21 (m, 2H), 2.34 (s, 6H), 1.04 (s, 3H). 1 H NMR (400 MHz, CDCl 3) δ 9.15 (s, 1H, -NH), 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 ( (m, 2H), 7.42 (d, IH), 7.37 (s, IH), 7.29 (t, IH), 7.16 , 3H). 363.16363.16 389389
Figure 112017032706954-pct00493
Figure 112017032706954-pct00493
 N-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (methoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.30 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.30 232.08232.08 390390
Figure 112017032706954-pct00494
Figure 112017032706954-pct00494
 N-(브로모메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (bromomethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H) 232.08232.08 391391
Figure 112017032706954-pct00495
Figure 112017032706954-pct00495
 N-(클로로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (chloromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H) 236.04236.04 392392
Figure 112017032706954-pct00496
Figure 112017032706954-pct00496
 N-(플로로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (fluoromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H) 220.06220.06 393393
Figure 112017032706954-pct00497
Figure 112017032706954-pct00497
 N-(하이드록시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (hydroxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.56 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.56 218.07218.07 394394
Figure 112017032706954-pct00498
Figure 112017032706954-pct00498
 N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (Nitromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H) 247.06247.06 395395
Figure 112017032706954-pct00499
Figure 112017032706954-pct00499
 5-(2-(벤조[d][1,3]디옥솔-5-일)아세트아미도)-N-(니트로메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5-yl) acetamido) -N- (nitromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxaldehyde Mide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.9 (s, 1H), 6.68 (d, 1H), 6.76 (d, 1H), 6.08 (m, 2H), 6.07 (m, 2H), 3.90 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 6.07 (m, 2H), 3.90 (m, 2H), 7.23 (s, , 2H) 424.10424.10 396396
Figure 112017032706954-pct00500
Figure 112017032706954-pct00500
 N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.47 (m, 2H), 3.61 (m, 2H), 3.65 (s, 1H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.47 (m, 2H), 3.61 232.08232.08 397397
Figure 112017032706954-pct00501
Figure 112017032706954-pct00501
 2-옥소-N-프로필-1,2-디하이드로퀴놀린-3-카복사마이드2-oxo-N-propyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.47 (m, 2H), 3.61 (m, 2H), 3.65 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.47 (m, 2H), 3.61 230.11230.11 398398
Figure 112017032706954-pct00502
Figure 112017032706954-pct00502
 5-(3-(벤조[d][1,3]디옥솔-5-일)프로판아미도)-2-옥소-N-프로필l-1,2-디하이드로퀴놀린-3-카복사마이드Propanoyl) -2-oxo-N-propyl-l, 2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.83 (d, 1H), 6.77 (s, 1H), 6.74 (d, 1H), 3.18 (m, 2H), 2.9 (m, 2H), 2.84 (m, 2H), 1.60 (m, 2H), 0.9 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H ), 7.23 (s, IH, -NH), 6.83 (d, IH), 6.77 (s, IH) , 2H), 1.60 (m, 2H), 0.9 (s, 3H) 421.16421.16 399399
Figure 112017032706954-pct00503
Figure 112017032706954-pct00503
 (E)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드(E) -2-oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.0 (s, 2H, -NH), 7.31 (t, 1H), 7.14 (t, 1H), 7.11 (s, 1H), 5.13 (s, 1H), 2.05 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.0 (s, 2H, -NH), 7.31 (t, 1H), 7.14 (t, 1H ), 7.11 (s, 1 H), 5.13 (s, 1 H), 2.05 (s, 228.09228.09 400400
Figure 112017032706954-pct00504
Figure 112017032706954-pct00504
 (E)-5-(3-(나프탈렌-2-일)프로판아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드(E) -5- (3- (naphthalen-2-yl) propanamido) -2-oxo-N- (prop-1-en-1-yl) -1,2- dihydroquinolin- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (s, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 7.11 (s, 1H), 5.13 (s, 1H), 3.01 (m, 2H), 2.84 (m, 2H), 2.05 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (t, 1H), 7.58 (t, 1H), 7.46 (s, 1H), 7.29 2H), 2.05 (s, 3H), 2.28 (m, IH) 425.17425.17 401401
Figure 112017032706954-pct00505
Figure 112017032706954-pct00505
 (E)-5-(2-(나프탈렌-2-일)아세트아미도)-2-옥소-N-(프로프-1-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드(E) -5- (2- (naphthalen-2-yl) acetamido) -2-oxo-N- (prop-1-en-1-yl) -1,2- dihydroquinolin- Carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (s, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 7.11 (s, 1H), 5.13 (s, 1H), 2.84 (m, 2H), 2.05 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.01 (d, 1H), 8.0 (s, 2H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (t, 1H), 7.58 (t, 1H), 7.46 (s, 1H), 7.29 2H), 2.05 (s, 3H), 2.28 (s, 3H) 411.16411.16 402402
Figure 112017032706954-pct00506
Figure 112017032706954-pct00506
 N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.04 (m, 2H), 3.30 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.04 246.10246.10 403403
Figure 112017032706954-pct00507
Figure 112017032706954-pct00507
 N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-bromoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.04 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 294.00294.00 404404
Figure 112017032706954-pct00508
Figure 112017032706954-pct00508
 5-(2-([1,1'-비페닐]-4-일)아세트아미도)-N-(2-브로모에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(2-bromoethyl) -2-oxo-1,2-dihydroquinoline-3-carbaldehyde Copymade 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (s, 1H), 7.33 (dd, 2H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 4.22 (m, 2H), 3.90 (m, 2H), 3.72 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.52 (dd, 2H ), 7.51 (dd, 2H), 7.41 (s, IH), 7.33 (dd, 2H), 7.29 , &Lt; / RTI &gt; 2H), 3.72 (m, 2H) 503.08503.08 405405
Figure 112017032706954-pct00509
Figure 112017032706954-pct00509
 N-(2-클로로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-chloroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.04 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 250.05250.05 406406
Figure 112017032706954-pct00510
Figure 112017032706954-pct00510
 N-(2-플로로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-fluoroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.04 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 234.08234.08 407407
Figure 112017032706954-pct00511
Figure 112017032706954-pct00511
 N-(2-하이드록시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-hydroxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31(t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.65 (s, 1H, -OH), 3.04 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 2H), 3.65 232.08232.08 408408
Figure 112017032706954-pct00512
Figure 112017032706954-pct00512
 N-(2-니트로에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-nitroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.76 (m, 2H), 3.04 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.76 (m, 261.07261.07 409409
Figure 112017032706954-pct00513
Figure 112017032706954-pct00513
 N-(3-하이드록시프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s,. 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65 (s, 1H, -OH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s ,. 1H, -NH), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.50 (m, 2H), 3.18 246.10246.10 410410
Figure 112017032706954-pct00514
Figure 112017032706954-pct00514
 (E)-2-옥소-N-(펜트-3-엔-1-일)-1,2-디하이드로퀴놀린-3-카복사마이드(E) -2-oxo-N- (pent-3-en-1-yl) -1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 5.48 (m, 2H), 3.20 (m, 2H), 2.22 (m, 2H), 2.05 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 2.20 (m, 2H), 2.05 (s, 3H), 7.31 (t, 256.12256.12 411411
Figure 112017032706954-pct00515
Figure 112017032706954-pct00515
 N-부틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N-butyl-2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H), 0.90 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 1.31 (m, 2H), 0.90 (s, 3H), 7.31 (t, 244.12244.12 412412
Figure 112017032706954-pct00516
Figure 112017032706954-pct00516
 N-(3-메톡시프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-methoxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.30 (s, 3H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.30 (s, 3H), 3.18 (m, 2H), 1.51 260.12260.12 413413
Figure 112017032706954-pct00517
Figure 112017032706954-pct00517
 N-(3-브로모프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-bromopropyl l) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (m, 2H), 1.31 (m, 308.02308.02 414414
Figure 112017032706954-pct00518
Figure 112017032706954-pct00518
 N-(3-클로로프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-chloropropyl l) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (m, 2H), 1.31 (m, 264.07264.07 415415
Figure 112017032706954-pct00519
Figure 112017032706954-pct00519
 N-(3-플로로프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-fluoropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (m, 2H), 1.31 (m, 248.10248.10 416416
Figure 112017032706954-pct00520
Figure 112017032706954-pct00520
 (E)-N-(hex-4-엔-1-일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드(E) -N- (hex-4-en-1-yl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.31 (t, 1H), 7.14 (t, 1H), 5.48 (d, 2H), 3.18 (m, 2H), 2.18 (m, 2H), 2.05 (s, 3H), 1.69 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H, -NH), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.31 ( 2H), 2.18 (m, 2H), 2.05 (s, 3H), 1.69 (m, 2H) 270.14270.14 417417
Figure 112017032706954-pct00521
Figure 112017032706954-pct00521
 N-(3-하이드록시프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65 (s, 1H, -OH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 1H), 7.31 (t, IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.50 (m, 2H), 3.18 246.10246.10 418418
Figure 112017032706954-pct00522
Figure 112017032706954-pct00522
 N-(3-니트로프로필l)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3-nitropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 3.18 (m, 2H), 1.58 (m, 2H), 7.31 (t, 275.09275.09 419419
Figure 112017032706954-pct00523
Figure 112017032706954-pct00523
 N-(4-하이드록시부틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-hydroxybutyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65 (s, 1H, -OH), 3.50 (s, 2H), 3.18 (m, 2H), 1.53 (m, 2H), 1.52 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, 2H), 1.53 (m, 2H), 1.52 (m, 2H), 7.31 (t, , 2H) 260.12260.12 420420
Figure 112017032706954-pct00524
Figure 112017032706954-pct00524
 N-(3,4-디하이드록시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dihydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.80 (s, 1H), 6.75 (d, 1H), 6.66 (d, 1H), 5.35 (m, 2H, -OH) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 7.31 (t, 1H), 7.14 (t, IH), 6.80 (s, IH), 6.75 (d, 310.10310.10 421421
Figure 112017032706954-pct00525
Figure 112017032706954-pct00525
 N-(3,4-디에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-diethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (d, 1H), 7.11 (s, 1H), 7.00 (d, 1H), 2.60 (m, 4H), 1.25 (s, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.12 (d, 334.17334.17 422422
Figure 112017032706954-pct00526
Figure 112017032706954-pct00526
 N-(3,4-디메틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.99 (d, 1H), 6.98 (s, 1H), 6.92 (d, 1H), 4.34 (m, 2H), 2.34 (s, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 6.99 (d, IH), 6.98 (s, IH) 306.14306.14 423423
Figure 112017032706954-pct00527
Figure 112017032706954-pct00527
 N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (s, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 5.35 (s, 2H, -OH), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 6.86 (s, IH), 6.68 (d, IH) , &Lt; / RTI &gt; 2H), 2.83 (m, 2H) 324.11324.11 424424
Figure 112017032706954-pct00528
Figure 112017032706954-pct00528
 5-(2-(4-벤질페닐)아세트아미도)-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (4-benzylphenyl) acetamido) -N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.33 (dd, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 7.11 (m, 4H), 6.86 (s, 1H), 6.73 (d, 1H), 6.68 (d, 1H), 5.35 (s, 2H, -OH), 3.96 (m, 2H), 3.55 (m, 2H), 2.83 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H ), 7.33 (d, 2H), 7.26 (t, 1H), 7.23 (dd, 2H), 7.11 (m, 4H) , 5.35 (s, 2H, -OH), 3.96 (m, 2H), 3.55 547.21547.21 425425
Figure 112017032706954-pct00529
Figure 112017032706954-pct00529
 N-(3,4-디하이드록시펜에틸)-2-옥소-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dihydroxyphenyl) -2-oxo-5-propionamido-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.86 (s, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 5.35 (s, 2H, -OH), 3.55 (m, 2H), 2.83 (m, 2H), 2.45 (m, 2H), 1.02 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2.83 (m, 2H), 2.45 (m, 2H), 1.02 (s, 3H) 395.15395.15 426426
Figure 112017032706954-pct00530
Figure 112017032706954-pct00530
 5-butyramido-N-(3,4-디하이드록시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5-butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.86 (s, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 5.35 (s, 2H, -OH), 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m, 2H), 1.78 (m, 2H), 0.9 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2H), 2.39 (m, 2H), 1.78 (m, 2H), 0.9 (s, 3H) 409.16409.16 427427
Figure 112017032706954-pct00531
Figure 112017032706954-pct00531
 N-(3,4-디하이드록시펜에틸)-2-옥소-5-펜탄아미도-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dihydroxyphenyl) -2-oxo-5-pentanamido-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 6.86 (s, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 5.35 (s, 2H, -OH), 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m, 2H), 1.63 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.88 (m, 2H), 7.29 (t, 1H 2H), 7.23 (s, 1H, -NH), 6.86 (s, IH), 6.68 (d, 2H), 1.39 (m, 2H), 1.63 (m, 2H) 423.18423.18 428428
Figure 112017032706954-pct00532
Figure 112017032706954-pct00532
 N-(3,4-디에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-diethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (d, 1H), 7.17 (s, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 2.83 (m, 2H), 2.60 (m, 4H), 1.25 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.19 (d, IH), 7.17 (s, IH), 7.14 (m, 2H) , 1.25 (m, 6H) 348.18348.18 429429
Figure 112017032706954-pct00533
Figure 112017032706954-pct00533
 N-(3,4-디메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (3,4-dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.06 (d, 1H), 7.04 (s, 1H), 6.79 (d, 1H), 3.55 (m, 2H), 2.83 (m, 2H). 2.34 (s, 6H) 1 H NMR (400 MHz, CDCl 3 )? 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 7.36 (t, IH), 7.06 (d, IH), 7.04 (s, IH), 6.79 (d, IH), 3.55 (m, 2H), 2.83 (m, 2H). 2.34 (s, 6H) 320.15320.15 430430
Figure 112017032706954-pct00534
Figure 112017032706954-pct00534
 N-(벤조[d][1,3]디옥솔-5-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (benzo [d] [1,3] dioxol-5-ylmethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 (s, 1H), 6.81 (d, 1H), 6.76 (d, 1H), 6.07 (s, 2H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 4.34 (m, 2H), 7.31 (d, IH), 7.31 (s, 322.10322.10 431431
Figure 112017032706954-pct00535
Figure 112017032706954-pct00535
 N-(2-(벤조[d][1,3]디옥솔-5-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2- (benzo [d] [1,3] dioxol-5-yl) ethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 (s, 1H), 6.81 (d, 1H), 6.76 (d, 1H), 6.07 (s, 2H), 4.34 (m, 2H), 3.4 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H 2H), 4.34 (m, 2H), 7.31 (d, IH), 7.31 (s, , 3.4 (m, 2H) 336.11336.11 432432
Figure 112017032706954-pct00536
Figure 112017032706954-pct00536
 N-(나프탈렌-2-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (naphthalen-2-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (d, 1H), 7.14 (t, 1H), 4.45 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH ), 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH), 7.55 , 7.18 (d, 1 H), 7.14 (t, 1 H), 4.45 (m, 2 H) 328.12328.12 433433
Figure 112017032706954-pct00537
Figure 112017032706954-pct00537
 N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (d, 1H), 7.14 (t, 1H), 3.55 (m, 2H), 2.94 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH ), 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH), 7.55 , 7.18 (d, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.94 342.14342.14 434434
Figure 112017032706954-pct00538
Figure 112017032706954-pct00538
 5-(2-(에틸티오)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 (d, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 3.55 (m, 2H), 3.51 (m, 2H), 2.94 (m, 2H), 2.48 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H ), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 2H), 2.25 (s, 3H), 2.45 (m, 2H) 459.16459.16 435435
Figure 112017032706954-pct00539
Figure 112017032706954-pct00539
 5-(2-(에틸아미노)아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드5- (2- (ethylamino) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (m, 2H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 (s, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 3.55 (m, 2H), 3.27 (m, 2H), 2.94 (m, 2H), 2.59 (m, 2H), 2.0 (s, 1H, -NH), 1.02 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (m, 2H 1H), 7.18 (d, 1H), 3.55 (m, 2H), 7.88 (m, 2H) 2H), 3.27 (m, 2H), 2.94 (m, 2H), 2.59 442.20442.20 436436
Figure 112017032706954-pct00540
Figure 112017032706954-pct00540
 5-(2-에톡시아세트아미도)-N-(2-(나프탈렌-2-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 (d, 1H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.18 (d, 1H), 3.55 (m, 2H), 3.51 (m, 2H), 2.94 (m, 2H), 2.48 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H ), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 (m, 2H), 7.46 2H), 2.25 (s, 3H), 2.45 (m, 2H) 443.18443.18 437437
Figure 112017032706954-pct00541
Figure 112017032706954-pct00541
 N-([1,1'-비페닐]-4-일메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N - ([1,1'-biphenyl] -4-ylmethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H), 7.14 (t, 1H), 4.34 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H ), 7.41 (t, IH), 7.36 (d, IH), 7.33 (m, 3H), 7.29 (dd, 2H) 354.14354.14 438438
Figure 112017032706954-pct00542
Figure 112017032706954-pct00542
 N-(2-([1,1'-비페닐]-4-일)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2 - ([1,1'-biphenyl] -4- yl) ethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H), 7.14 (t, 1H), 4.34 (m, 2H), 3.2 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 2H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H) 368.15368.15 439439
Figure 112017032706954-pct00543
Figure 112017032706954-pct00543
 N-(4-벤질벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-benzylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H), 7.14 (t, 1H), 4.34 (m, 2H), 2.94 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 2H), 4.94 (m, 2H), 2.94 (m, 2H), 7.41 (t, 368.15368.15 440440
Figure 112017032706954-pct00544
Figure 112017032706954-pct00544
 N-(4-벤질펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (4-benzylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H), 7.14 (t, 1H), 4.34 (m, 2H), 3.1 (m, 2H), 2.94 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.55 (m, 4H 1H), 7.41 (t, 1H), 7.36 (d, 1H), 7.33 (m, 3H), 7.29 (dd, 2H) , &Lt; / RTI &gt; 2.94 (m, 2H) 382.17382.17 441441
Figure 112017032706954-pct00545
Figure 112017032706954-pct00545
 N-(에톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (ethoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 246.10246.10 442442
Figure 112017032706954-pct00546
Figure 112017032706954-pct00546
 N-((에틸티오)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N - ((ethylthio) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 262.08262.08 443443
Figure 112017032706954-pct00547
Figure 112017032706954-pct00547
 N-(2-메톡시에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 246.10246.10 444444
Figure 112017032706954-pct00548
Figure 112017032706954-pct00548
 N-((에틸아미노)메틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N - ((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 2.0 (s, 1H, -NH), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 2H), 3.5 245.12245.12 445445
Figure 112017032706954-pct00549
Figure 112017032706954-pct00549
 N-(2-(메틸티오)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2- (methylthio) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 262.08262.08 446446
Figure 112017032706954-pct00550
Figure 112017032706954-pct00550
 N-(2-(메틸아미노)에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드N- (2- (methylamino) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ), 7.31 (t, IH), 7.14 (t, IH), 3.59 (m, 245.12245.12 447447
Figure 112017032706954-pct00551
Figure 112017032706954-pct00551
 3-(페닐아미노)퀴놀린-2(1H)-온3- (phenylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 236.09236.09 448448
Figure 112017032706954-pct00552
Figure 112017032706954-pct00552
 3-(p-톨일아미노)퀴놀린-2(1H)-온3- (p-Tolylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.3 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H) 250.11250.11 449449
Figure 112017032706954-pct00553
Figure 112017032706954-pct00553
 3-((4-메톡시페닐)아미노)퀴놀린-2(1H)-온3 - ((4-methoxyphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.5 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H) 266.11266.11 450450
Figure 112017032706954-pct00554
Figure 112017032706954-pct00554
 3-((4-브로모페닐)아미노)퀴놀린-2(1H)-온3 - ((4-bromophenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 314.01314.01 451451
Figure 112017032706954-pct00555
Figure 112017032706954-pct00555
 3-((4-클로로페닐)아미노)퀴놀린-2(1H)-온3 - ((4-chlorophenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 270.06270.06 452452
Figure 112017032706954-pct00556
Figure 112017032706954-pct00556
 3-((4-플로로페닐)아미노)퀴놀린-2(1H)-온3 - ((4-fluorophenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 254.09254.09 453453
Figure 112017032706954-pct00557
Figure 112017032706954-pct00557
 3-((4-에틸페닐)아미노)퀴놀린-2(1H)-온3 - ((4-ethylphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.6 (m, 2H), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H) 264.13264.13 454454
Figure 112017032706954-pct00558
Figure 112017032706954-pct00558
 3-((4-하이드록시페닐)아미노)퀴놀린-2(1H)-온3 - ((4-hydroxyphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 252.09252.09 455455
Figure 112017032706954-pct00559
Figure 112017032706954-pct00559
 3-((4-니트로페닐)아미노)퀴놀린-2(1H)-온3 - ((4-nitrophenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (d, 2H), 4.0 (s, IH, - NH), 6.81 (t, 281.08281.08 456456
Figure 112017032706954-pct00560
Figure 112017032706954-pct00560
 3-((4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온3 - ((4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.6 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.43 (dd, 2H) 266.11266.11 457457
Figure 112017032706954-pct00561
Figure 112017032706954-pct00561
 3-((4-비닐페닐)아미노)퀴놀린-2(1H)-온3 - ((4-vinylphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.63 (s, 1H), 6.43 (dd, 2H), 5.61 (s, 1H), 5.18 (s, 1H), 4.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (s, 1H), 6.63 (s, 1H), 6.43 (sd, 2H) 262.11262.11 458458
Figure 112017032706954-pct00562
Figure 112017032706954-pct00562
 N,N-디메틸-4-((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)벤젠설폰아미드N, N-dimethyl-4 - ((2-oxo-1,2-dihydroquinolin-3- yl) amino) benzenesulfonamide 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, 1H), 6.63 (s, 1H), 6.43 (dd, 2H), 4.0 (s, 1H, -NH), 2.66 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.81 (t, IH), 6.63 (s, IH), 6.43 (dd, 2H) 343.10343.10 459459
Figure 112017032706954-pct00563
Figure 112017032706954-pct00563
 3-(벤질아미노)퀴놀린-2(1H)-온3- (Benzylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 250.11250.11 460460
Figure 112017032706954-pct00564
Figure 112017032706954-pct00564
 3-((4-메틸벤질)아미노)퀴놀린-2(1H)-온3 - ((4-methylbenzyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.34 (s, 3H), 2.0 (s, 1H, -NH), 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 3H), 2.02 (s, 1H, -NH), 7.26 (t, 1H), 7.14 , 264.13264.13 461461
Figure 112017032706954-pct00565
Figure 112017032706954-pct00565
 3-((4-메톡시벤질)아미노)퀴놀린-2(1H)-온3 - ((4-methoxybenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.3 (s, 3H), 2.0 (s, 1H, -NH), 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, , 280.12280.12 462462
Figure 112017032706954-pct00566
Figure 112017032706954-pct00566
 3-((4-브로모벤질)아미노)퀴놀린-2(1H)-온3 - ((4-bromobenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 328.02328.02 463463
Figure 112017032706954-pct00567
Figure 112017032706954-pct00567
 3-((4-클로로벤질)아미노)퀴놀린-2(1H)-온3 - ((4-chlorobenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 284.07284.07 464464
Figure 112017032706954-pct00568
Figure 112017032706954-pct00568
 3-((4-플로로벤질)아미노)퀴놀린-2(1H)-온3 - ((4-fluorobenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 268.10268.10 465465
Figure 112017032706954-pct00569
Figure 112017032706954-pct00569
 3-((4-에틸벤질)아미노)퀴놀린-2(1H)-온3 - ((4-ethylbenzyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.6 (m, 2H), 2.0 (s, 1H, -NH), 1.25 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 2H), 7.26 (t, 1H), 7.14 (t, IH), 6.10 (s, IH), 3.92 (m, , 1.25 (s, 3H) 278.14278.14 466466
Figure 112017032706954-pct00570
Figure 112017032706954-pct00570
 3-((4-하이드록시벤질)아미노)퀴놀린-2(1H)-온3 - ((4-hydroxybenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 266.11266.11 467467
Figure 112017032706954-pct00571
Figure 112017032706954-pct00571
 3-((4-니트로벤질)아미노)퀴놀린-2(1H)-온3 - ((4-nitrobenzyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (s, 1H, -NH), 7.26 (t, 1H), 7.14 (t, 295.10295.10 468468
Figure 112017032706954-pct00572
Figure 112017032706954-pct00572
 N,N-디메틸-4-(((2-옥소-1,2-디하이드로퀴놀린-3-일)아미노)메틸)벤젠설폰아미드N, N-dimethyl-4 - (((2-oxo-1,2-dihydroquinolin-3- yl) amino) methyl) benzenesulfonamide 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.66 (m, 6H), 2.0 (s, 1H, -NH), 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (m, 2H), 2.66 (m, 6H), 2.0 (s, IH, -NH), 7.26 (t, , 357.11357.11 469469
Figure 112017032706954-pct00573
Figure 112017032706954-pct00573
 3-((4-(하이드록시메틸)벤질)아미노)퀴놀린-2(1H)-온3 - ((4- (hydroxymethyl) benzyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 2H), 7.16 (dd, 2H), 7.14 (t, 1H), 7.11 (dd, 2H), 4.61 (m, 2H), 3.65 (s, 1H, -OH), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (m, 2H), 7.16 (dd, 2H), 7.14 (t, 1H), 7.11 (d, 2H), 4.61 (m, 2H), 3.65 (s, 280.12280.12 470470
Figure 112017032706954-pct00574
Figure 112017032706954-pct00574
 3-((4-비닐벤질)아미노)퀴놀린-2(1H)-온3 - ((4-vinylbenzyl) amino) quinolin-2 (1H) 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (t, 1H), 6.63 (s, 1H), 6.1 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 3.92 (m, 2H)1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, ), 6.63 (s, IH), 6.1 (s, IH), 5.61 (s, IH) 276.13276.13 471471
Figure 112017032706954-pct00575
Figure 112017032706954-pct00575
 3-(메틸(페닐)아미노)퀴놀린-2(1H)-온3- (methyl (phenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 3.44 250.11250.11 472472
Figure 112017032706954-pct00576
Figure 112017032706954-pct00576
 3-(에틸(페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (phenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 264.13264.13 473473
Figure 112017032706954-pct00577
Figure 112017032706954-pct00577
 3-(에틸(p-톨일)아미노)퀴놀린-2(1H)-온3- (ethyl (p-tolyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34(s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H) 278.14278.14 474474
Figure 112017032706954-pct00578
Figure 112017032706954-pct00578
 3-(메틸(p-톨일)아미노)퀴놀린-2(1H)-온3- (methyl (p-tolyl) amino) quinolin-2 (lH) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.01 (dd, 2H), 6.83 (s, 1H), 6.13 (dd, 2H), 3.44 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (d, 2H), 6.83 (s, 1H), 6.13 (dd, 2H), 3.44 264.13264.13 475475
Figure 112017032706954-pct00579
Figure 112017032706954-pct00579
 3-((4-메톡시페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-methoxyphenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (dd, 2H), 6.71 (dd, 2H), 3.83 (s, 3H), 3.44 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (d, 1H), 7.14 (t, 1H), 6.83 (s, 3H), 3.44 (s, 3H), 2.28 (m, IH) 280.12280.12 476476
Figure 112017032706954-pct00580
Figure 112017032706954-pct00580
 3-(에틸(4-메톡시페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-methoxyphenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H) 294.14294.14 477477
Figure 112017032706954-pct00581
Figure 112017032706954-pct00581
 3-((4-브로모페닐)(에틸)아미노)퀴놀린-2(1H)-온3 - ((4-bromophenyl) (ethyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34(s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (m, 2H), 2.34 (s, 3H), 6.83 (d, IH) 342.04342.04 478478
Figure 112017032706954-pct00582
Figure 112017032706954-pct00582
 3-((4-브로모페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-bromophenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 328.02328.02 479479
Figure 112017032706954-pct00583
Figure 112017032706954-pct00583
 3-((4-클로로페닐)(에틸)아미노)퀴놀린-2(1H)-온3 - ((4-chlorophenyl) (ethyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (m, 2H), 2.34 (s, 3H), 6.83 (d, IH) 298.09298.09 480480
Figure 112017032706954-pct00584
Figure 112017032706954-pct00584
 3-((4-클로로페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-chlorophenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 284.07284.07 481481
Figure 112017032706954-pct00585
Figure 112017032706954-pct00585
 3-((4-플로로페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-fluorophenyl) (methyl) amino) quinolin-2 (1H) 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H)2H), 7.14 (t, 1H), 6.83 (s, 1H, &lt; RTI ID = 0.0 & ), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 268.10268.10 482482
Figure 112017032706954-pct00586
Figure 112017032706954-pct00586
 3-(에틸(4-플로로페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-fluorophenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (m, 2H), 2.34 (s, 3H), 6.83 (d, IH) 282.12282.12 483483
Figure 112017032706954-pct00587
Figure 112017032706954-pct00587
 3-(에틸(4-에틸페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-ethylphenyl) amino) quinolin-2 (1H) -one 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.60 (m, 2H), 1.25 (s, 3H), 2.34 (s, 3H)2H), 7.14 (t, 1H), 6.83 (s, 1H, &lt; RTI ID = 0.0 & 2H), 2.60 (m, 2H), 1.25 (s, 3H), 2.34 (s, 3H) 292.16292.16 484484
Figure 112017032706954-pct00588
Figure 112017032706954-pct00588
 3-((4-에틸페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-ethylphenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 2.60 (m, 2H), 1.25 (s, 3H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, 1H), 6.83 (s, 1H), 6.77 (s, 2H) 278.14278.14 485485
Figure 112017032706954-pct00589
Figure 112017032706954-pct00589
 3-(에틸(4-하이드록시페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-hydroxyphenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (m, 2H), 2.34 (s, 3H), 6.83 (d, IH) 280.12280.12 486486
Figure 112017032706954-pct00590
Figure 112017032706954-pct00590
 3-((4-하이드록시페닐)(메틸)아미노)퀴놀린-2(1H)-온3 - ((4-hydroxyphenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 266.11266.11 487487 3-(메틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온3- (methyl (4-nitrophenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 295.10295.10 488488
Figure 112017032706954-pct00592
Figure 112017032706954-pct00592
 3-(에틸(4-니트로페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-nitrophenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (m, 2H), 2.34 (s, 3H), 6.83 (d, IH) 309.11309.11 489489
Figure 112017032706954-pct00593
Figure 112017032706954-pct00593
 3-(에틸(4-(하이드록시메틸)페닐)아미노)퀴놀린-2(1H)-온(Ethyl (4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.61 (m, 2H), 4.56 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 3H), 6.83 (d, IH), 6.83 (d, IH) 294.14294.14 490490
Figure 112017032706954-pct00594
Figure 112017032706954-pct00594
 3-((4-(하이드록시 메틸) 페닐)(메틸) 아미노)퀴놀린-2(1H)-온3 - ((4- (hydroxymethyl) phenyl) (methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.61 (m, 2H), 2.34 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 3H), 6.70 (d, IH), 6.83 (d, IH) 280.12280.12 491491
Figure 112017032706954-pct00595
Figure 112017032706954-pct00595
 3-(메틸(4-비닐페닐) 아미노)퀴놀린-2(1H)-온3- (methyl (4-vinylphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 276.13276.13 492492
Figure 112017032706954-pct00596
Figure 112017032706954-pct00596
 3-(에틸(4-비닐페닐)아미노)퀴놀린-2(1H)-온3- (ethyl (4-vinylphenyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H), 1.31 (s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H, -NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, IH), 7.14 (s, IH), 6.63 (s, IH), 5.61 290.14290.14 493493
Figure 112017032706954-pct00597
Figure 112017032706954-pct00597
 3-((3,4-디메틸페닐)아미노)퀴놀린-2(1H)-온3 - ((3,4-dimethylphenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, 1H), 6.24 (m, 1H), 6.19 (d, 1H), 4.0 (s, 1H, -NH), 2.34 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, IH), 6.24 (m, IH), 6.19 (d, IH) 264.13264.13 494494
Figure 112017032706954-pct00598
Figure 112017032706954-pct00598
 3-((3,4-디메틸벤질)아미노)퀴놀린-2(1H)-온3 - ((3,4-dimethylbenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, 1H), 6.24 (m, 1H), 6.19 (d, 1H), 4.0 (s, 1H, -NH), 3.2 (m, 2H), 2.34 (m, 6H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.86 (d, IH), 6.24 (m, IH), 6.19 (d, IH), 4.0 (s, 278.14278.14 495495
Figure 112017032706954-pct00599
Figure 112017032706954-pct00599
 3-((3,4-디하이드록시페닐)아미노)퀴놀린-2(1H)-온3 - ((3,4-dihydroxyphenyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, 1H), 5.97 (m, 1H), 5.83 (d, 1H), 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, IH), 5.97 (m, IH), 5.83 (d, IH) 268.08268.08 496496
Figure 112017032706954-pct00600
Figure 112017032706954-pct00600
 3-((3,4-디하이드록시벤질)아미노)퀴놀린-2(1H)-온3 - ((3,4-dihydroxybenzyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, 1H), 5.97 (m, 1H), 5.83 (d, 1H), 3.2 (m, 2H) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.53 (d, IH), 5.97 (m, IH), 5.83 (d, IH), 3.2 282.10282.10 497497
Figure 112017032706954-pct00601
Figure 112017032706954-pct00601
 3-((벤조[d][1,3] 디옥솔-5-일메틸) 아미노)퀴놀린-2(1H)-온3 - ((benzo [d] [1,3] dioxol-5-ylmethyl) amino) quinolin- 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 (m, 1H), 6.81 (d, 1H), 6.76 (d, 1H), 6.10 (s, 1H), 6.07 (m, 2H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 ( 2H), 3.92 (m, 2H), 2.0 (s, 1H, -NH), 6.81 (d, 294.10294.10 498498
Figure 112017032706954-pct00602
Figure 112017032706954-pct00602
 3-((2-(벤조[d][1,3]디옥솔-5-일)에틸)아미노)퀴놀린-2(1H)-온Ethyl) amino) quinolin-2 (1 H) -one, 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 (m, 1H), 6.81 (d, 1H), 6.76 (d, 1H), 6.10 (s, 1H), 6.07 (m, 2H), 3.92 (m, 2H), 3.02 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H) 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 7.03 ( 2H), 3.92 (m, 2H), 3.02 (m, 2H), 2.0 (s, , 1H, -NH) 308.12308.12 499499
Figure 112017032706954-pct00603
Figure 112017032706954-pct00603
 3-((나프탈렌-2-일메틸)아미노)퀴놀린-2(1H)-온3 - ((naphthalen-2-ylmethyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (m, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (d, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 4.03 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, IH), 7.46 (m, IH), 7.36 (d, IH), 7.31 s, 1 H), 4.03 (m, 2H), 2.0 (s, 1 H, -NH) 300.13300.13 500500
Figure 112017032706954-pct00604
Figure 112017032706954-pct00604
 3-((2-(나프탈렌-2-일)에틸)아미노)퀴놀린-2(1H)-온3 - ((2- (naphthalen-2-yl) ethyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, 1H), 7.46 (m, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (d, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 4.03 (m, 2H), 3.02 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.58 (t, 1H), 7.55 (t, IH), 7.46 (m, IH), 7.36 (d, IH), 7.31 (m, 2H), 3.02 (m, 2H), 2.0 (s, 1H, 314.14314.14 501501
Figure 112017032706954-pct00605
Figure 112017032706954-pct00605
 3-(([1,1'-비페닐]-4-일메틸)아미노)퀴놀린-2(1H)-온3 - (([1,1'-biphenyl] -4-ylmethyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 2H), 7.31 (d, 1H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 s, 1H, -NH) 326.14326.14 502502
Figure 112017032706954-pct00606
Figure 112017032706954-pct00606
 3-((2-([1,1'-비페닐]-4-일)에틸)아미노)퀴놀린-2(1H)-온3 - ((2 - ([1,1'-biphenyl] -4-yl) ethyl) amino) quinolin- 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 3.6 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 1H), 7.32 (d, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 m, 2H), 2.0 (s, 1 H, -NH) 340.16340.16 503503
Figure 112017032706954-pct00607
Figure 112017032706954-pct00607
 3-((4-벤질펜에틸)아미노)퀴놀린-2(1H)-온3 - ((4-benzylphenethyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 3.6 (m, 2H), 2.8 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 1H), 7.32 (d, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 m, 2H), 2.8 (m, 2H), 2.0 (s, 1H, 354.17354.17 504504
Figure 112017032706954-pct00608
Figure 112017032706954-pct00608
 3-((4-벤질벤질)아미노)퀴놀린-2(1H)-온3 - ((4-benzylbenzyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.29 (dd, 2H), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.8 (m, 2H), 2.0 (s, 1H, -NH) 1 H NMR (400 MHz, CDCl 3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.52 (dd, 2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, IH), 7.33 (d, 2H), 7.31 (t, IH), 7.29 (dd, 2H), 7.14 m, 2H), 2.0 (s, 1 H, -NH) 340.16340.16 505505
Figure 112017032706954-pct00609
Figure 112017032706954-pct00609
 3-(에틸아미노)퀴놀린-2(1H)-온3- (ethylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 2.73 (m, 2H), 2.0 (s, 1H, -NH), 0.84 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.0 (s, 188.09188.09 506506
Figure 112017032706954-pct00610
Figure 112017032706954-pct00610
 3-(프로필l아미노)퀴놀린-2(1H)-온3- (propylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 2.73 (m, 2H), 2.32 (m, 2H), 2.0 (s, 1H, -NH), 0.84 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.32 (m, 2H) 202.11202.11 507507
Figure 112017032706954-pct00611
Figure 112017032706954-pct00611
 3-(부틸아미노)퀴놀린-2(1H)-온3- (Butylamino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 2.73 (m, 2H), 2.0 (s, 1H, -NH), 1.52 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 2.73 (m, 2H), 2.0 (s, 216.13216.13 508508
Figure 112017032706954-pct00612
Figure 112017032706954-pct00612
 3-((에톡시메틸)아미노)퀴놀린-2(1H)-온3 - ((ethoxymethyl) amino) quinolin-2 (1H) -one 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.50 (m, 2H), 2.0 (s, 1H, -NH), 3.28 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 3.50 (m, 2H), 2.0 (s, 218.11218.11 509509
Figure 112017032706954-pct00613
Figure 112017032706954-pct00613
 3-(((에틸티오)메틸)아미노)퀴놀린-2(1H)-온3 - (((ethylthio) methyl) amino) quinolin-2 (1H) 1H NMR (400 MHz, CDCl3) δ 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 6.10 (s, 1H), 3.50 (m, 2H), 2.0 (s, 1H, -NH), 3.28 (m, 2H), 1.10 (s, 3H) 1 H NMR (400 MHz, CDCl 3 )? 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, (s, 1H), 3.50 (m, 2H), 2.0 (s, 234.08234.08 510510
Figure 112017032706954-pct00614
Figure 112017032706954-pct00614
 메틸 5-아미노-2-옥소-1,2-디하이드로퀴놀린-3-카르복실레이트Methyl 5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate 1H NMR (400 MHz, CDCl3) δ 11.62 (s, 1H), 8.21 (s, 1H, -NH), 7.17 (t, 1H), 6.33 (dd, 1H), 6.22 (s, 1H), 3.77 (s, 1H). 1 H NMR (400 MHz, CDCl 3 )? 11.62 (s, IH), 8.21 (s, IH, -NH), 7.17 (s, 1 H). 218.07218.07

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합성된 화합물의 구조 및 분광학 데이터 (합성예 511-529)Structure and spectroscopic data of the synthesized compound (Synthesis Example 511-529) 번호number 구조rescue 명칭designation NMRNMR 분자량Molecular Weight 511511

Figure 112017032706954-pct00615
Figure 112017032706954-pct00615
5-클로로-2-옥소-N-페네틸-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드Chloro-2-oxo-N-phenethyl-l- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3- carboxamide 1H NMR (400MHz, CDCl3) δ9.77(s, 1H), 9.45(s,1H), 7.51-7.45(m, 1H), 7.36(s, 1H), 7.32-7.14(m, 8H), 5.57(s, 1H), 3.73(dd, 2H), 2.95(t, 1H). 1 H NMR (400MHz, CDCl 3 ) δ9.77 (s, 1H), 9.45 (s, 1H), 7.51-7.45 (m, 1H), 7.36 (s, 1H), 7.32-7.14 (m, 8H), 5.57 (s, 1 H), 3.73 (dd, 2 H), 2.95 (t, 1 H). 500.29500.29 512512
Figure 112017032706954-pct00616
Figure 112017032706954-pct00616
 5-클로로-1-(4-에틸벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카프복스아미드5-chloro-l- (4-ethylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR (400MHz, CDCl3) δ 9.86(s, 1H), 9.43(s, 1H), 7.43(t, 1H), 7.43-7.21(m, 7H), 7.14(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.75- 3.69(m, 2H), 2.95(t, 2H), 2.59(dd, 2H), 1.18(t, 3H). 1 H NMR (400MHz, CDCl 3 ) δ 9.86 (s, 1H), 9.43 (s, 1H), 7.43 (t, 1H), 7.43-7.21 (m, 7H), 7.14 (d, 2H), 7.06 (d 2H), 5.55 (s, 1H), 3.75-3.69 (m, 2H), 2.95 (t, 2H), 2.59 (dd, 2H), 1.18 (t, 3H). 444.51444.51 513513
Figure 112017032706954-pct00617
Figure 112017032706954-pct00617
 5-클로로-1-(4-아이소프로필벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드5-chloro-l- (4-isopropylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR(400MHz, CDCl3) δ 9.87(s, 1H), 9.43(s, 1H), 9.44(t, 1H), 7.34-7.21(m, 7H), 7.16(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.72 (dd, 2H), 2.95(t, 2H), 2.89- 2.82(m, 1H), 1.19(d, 6H) 1 H NMR (400MHz, CDCl 3 ) δ 9.87 (s, 1H), 9.43 (s, 1H), 9.44 (t, 1H), 7.34-7.21 (m, 7H), 7.16 (d, 2H), 7.06 (d (D, 2H), 5.55 (s, 1H), 3.72 (dd, 2H), 2.95 458.59458.59 514514
Figure 112017032706954-pct00618
Figure 112017032706954-pct00618
 5-클로로-1-(4-나이트로벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드5-chloro-l- (4-nitrobenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR (400MHz, CDCl3) δ 9.67(s, 1H), 9.47(s, 1H), 8.19(d, 1H), 7.46(t, 1H), 7.38(d, 1H), 7.33-7.21(m, 7H), 7.08(d, 1H), 5.66(s, 1H), 3.73(dd, 2H), 2.95(t, 2H), 1 H NMR (400MHz, CDCl 3 ) δ 9.67 (s, 1H), 9.47 (s, 1H), 8.19 (d, 1H), 7.46 (t, 1H), 7.38 (d, 1H), 7.33-7.21 (m , 7.08 (d, IH), 5.66 (s, IH), 3.73 (dd, 2H), 2.95 461.39461.39 515515
Figure 112017032706954-pct00619
Figure 112017032706954-pct00619
 5-클로로-1-(4-메톡시벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드 5-chloro-l- (4-methoxybenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline- 1H NMR(400MHz, CDCl3) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H), 7.34-7.21(m, 7H), 7.10(d, 2H), 6.84(d, 2H), 5.52(s, 2H), 3.76- 3.70(m, 5H), 2.96(t, 2H), 1 H NMR (400MHz, CDCl 3 ) δ 9.85 (s, 1H), 9.42 (s, 1H), 7.44 (t, 1H), 7.34-7.21 (m, 7H), 7.10 (d, 2H), 6.84 (d 2H), 5.52 (s, 2H), 3.76-3.70 (m, 5H), 2.96 446.55 446.55 516516
Figure 112017032706954-pct00620
Figure 112017032706954-pct00620
 5-클로로-1-(4-에틸벤질)-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카프복스아미드)5-chloro-1- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400MHz, CDCl3) δ 9.86(s, 1H), 9.43(s, 1H), 7.43(t, 1H), 7.43-7.21(m, 6H), 7.14(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.75- 3.69(m, 2H), 2.95(t, 2H), 2.59(dd, 2H), 1.18(t, 3H) 1 H NMR (400MHz, CDCl 3 ) δ 9.86 (s, 1H), 9.43 (s, 1H), 7.43 (t, 1H), 7.43-7.21 (m, 6H), 7.14 (d, 2H), 7.06 (d 2H), 5.55 (s, IH), 3.75-3.69 (m, 2H), 2.95 462.85 462.85 517517
Figure 112017032706954-pct00621
Figure 112017032706954-pct00621
 5-클로로-N-(4-플루오로페네틸)-1-(4-아이소프로필벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드5-chloro-N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400MHz, CDCl3) δ 9.87(s, 1H), 9.43(s, 1H), 9.44(t, 1H), 7.34-7.21(m, 6H), 7.16(d, 2H), 7.06(d, 2H), 5.55(s, 1H), 3.72 (dd, 2H), 2.95(t, 2H), 2.89-2.82(m, 1H), 1.19 (d, 6H). 1 H NMR (400MHz, CDCl 3 ) δ 9.87 (s, 1H), 9.43 (s, 1H), 9.44 (t, 1H), 7.34-7.21 (m, 6H), 7.16 (d, 2H), 7.06 (d 2H), 5.55 (s, 1H), 3.72 (dd, 2H), 2.95 (t, 2H), 2.89-2.82 (m, 476.55476.55 518518
Figure 112017032706954-pct00622
Figure 112017032706954-pct00622
 5-클로로-N-(4-플루오로페네틸)-1-(4-나이트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드(4-fluorobenzyl) -1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3- carboxamide 1H NMR(400MHz, CDCl3) δ 9.67(s, 1H), 9.47(s, 1H), 8.19(d, 1H), 7.46(t, 1H), 7.38(d, 1H), 7.33-7.21(m, 6H), 7.08(d, 1H), 5.66(s, 1H), 3.73(dd, 2H), 2.95(t, 2H) 1 H NMR (400MHz, CDCl 3 ) δ 9.67 (s, 1H), 9.47 (s, 1H), 8.19 (d, 1H), 7.46 (t, 1H), 7.38 (d, 1H), 7.33-7.21 (m 2H), 2.95 (t, 2H), 3.70 (d, 2H) 479.23479.23 519519
Figure 112017032706954-pct00623
Figure 112017032706954-pct00623
 5-클로로-N-(4-플루오로페네틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드5-chloro-N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400MHz, CDCl3) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H), 7.34-7.21(m, 6H), 7.10(d, 2H), 6.84(d, 2H), 5.52(s, 2H), 3.76-3.70(m, 5H), 2.96(t, 2H), 1 H NMR (400MHz, CDCl 3 ) δ 9.85 (s, 1H), 9.42 (s, 1H), 7.44 (t, 1H), 7.34-7.21 (m, 6H), 7.10 (d, 2H), 6.84 (d 2H), 5.52 (s, 2H), 3.76-3.70 (m, 5H), 2.96 464.87464.87 520520
Figure 112017032706954-pct00624
Figure 112017032706954-pct00624
 5-클로로-N-(4-플루오로페네틸)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드(4-fluorophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3- carboxamide 1H NMR (400MHz, CDCl3) δ 9.77(s, 1H), 9.45(s, 1H), 7.51-7.45 (m, 1H), 7.36(s, 1H), 7.32-7.14(m, 7H), 5.57(s, 1H), 3.73(dd, 2H), 2.95(t, 1H). 1 H NMR (400MHz, CDCl 3 ) δ 9.77 (s, 1H), 9.45 (s, 1H), 7.51-7.45 (m, 1H), 7.36 (s, 1H), 7.32-7.14 (m, 7H), 5.57 (s, 1 H), 3.73 (dd, 2 H), 2.95 (t, 1 H). 518.36518.36 521521
Figure 112017032706954-pct00625
Figure 112017032706954-pct00625
 1-(4-에틸벤질)-N-(4-플루오로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드1- (4-Ethylbenzyl) -N- (4-fluorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline- 1H NMR(400 MHz, CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(t, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.29(dd, 2H), 7.18(dd, 2H), 6.98(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H), 2.60(m, 2H), 1.25(s, 3H) 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (t, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.29 (dd, 2H), 1.25 (s, 3H), 2.38 (m, 2H) ) 473.18473.18 522522
Figure 112017032706954-pct00626
Figure 112017032706954-pct00626
 N-(4-플루오로펜에틸)-1-(4-이소프로필벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline- 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 4.94(s, 2H), 3.55 (m, 2H), 2.87(m, 1H), 2.83(m, 2H), 1.20(s, 6H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (dd, 2H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.87 (m, 487.19487.19 523523
Figure 112017032706954-pct00627
Figure 112017032706954-pct00627
 N-(4-플루오로펜에틸)-5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드N- (4-fluorophenethyl) -5-nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline- 1H NMR (400 MHz, CDCl3)δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (dd, 2H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 1 H NMR (400 MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H), 7.29 (d, 2H), 7.12 (d, 2H), 4.94 490.13490.13 524524
Figure 112017032706954-pct00628
Figure 112017032706954-pct00628
 5-아미노-N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드)(4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide) 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 6.27(s, 1H, -NH2), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) 2H), 7.29 (d, 2H), 7.12 (dd, 2H), 6.27 (s, 2H). 505.10505.10 525525
Figure 112017032706954-pct00629
Figure 112017032706954-pct00629
 1-(4-메톡시벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드1- (4-methoxybenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.55 457.16457.16 526526
Figure 112017032706954-pct00630
Figure 112017032706954-pct00630
 N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline- 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.12(dd, 2H), 4.94(s, 2H), 3.98(s, 3H), 3.55(m, 2H), 2.83(m, 2H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (dd, 2H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). 475.15475.15 527527
Figure 112017032706954-pct00631
Figure 112017032706954-pct00631
 5-니트로-2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드Nitro-2-oxo-N-phenethyl-l- (4- (trifluoromethoxy) benzyl) - l, 2-dihydroquinoline- 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.83(m, 2H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H). 511.14511.14 528528
Figure 112017032706954-pct00632
Figure 112017032706954-pct00632
 (N-(4-플루오로펜에틸)-5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드)(4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide) 1HNMR (400MHz,CDCl3)δ 8.52(s, 1H), 8.00(d, 1H), 7.95(d, 1H), 7.51(t, 1H), 7.40(dd, 2H), 7.33(dd, 2H), 7.29(dd, 2H), 7.22(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.87(m, 1H), 1 HNMR (400MHz, CDCl 3) δ 8.52 (s, 1H), 8.00 (d, 1H), 7.95 (d, 1H), 7.51 (t, 1H), 7.40 (dd, 2H), 7.33 (dd, 2H) , 7.29 (d, 2H), 7.22 (m, 1H), 7.12 (dd, 2H), 4.94 529.13529.13 529529
Figure 112017032706954-pct00633
Figure 112017032706954-pct00633
 1-(4-이소프로필벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드1- (4-isopropylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline- 1HNMR(400MHz,CDCl3)δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H), 7.57(t, 1H), 7.40(dd, 2H), 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, 1H), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.87(m, 1H), 2.83(m, 2H), 1.20 (s, 6H). 1 HNMR (400MHz, CDCl 3) δ 8.57 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1H), 7.40 (dd, 2H), 7.39 (dd, 2H) , 7.29 (d, 2H), 7.24 (m, 1H), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 1.20 (s, 6 H). 469.20469.20

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합성의 일반적인 과정General process of synthesis

: 단계(e-5, h-8)의 일반적 과정과 같음: Same as the general procedure of step (e-5, h-8)

합성예 530 : 메틸 1-(4-메톡시벤질)-2-옥소-5-(3-페닐프로파나미노)-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 530: Synthesis of methyl 1- (4-methoxybenzyl) -2-oxo-5- (3-phenylpropanamino) -1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 하이드로시나모일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 530 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and hydrocinnamoyl chloride (1.2 mmol) were added to a stirred solution of methyl 5-amino-1- (4-methoxybenzyl) And stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 530 (yield = 61%).

1H NMR (400 MHz, CDCl3) δ 9.22 (s, 1H), 7.56 (s, 1H), 7.36 (t, J = 12.0 Hz, 1H), 7.21-7.15 (m, 4H), 6.90 (d, J = 12.0 Hz, 1H), 6.84-6.77 (m, 4H), 6.58 (d, J = 12.0 Hz, 1H), 5.48 (s, 2H), 3.96 (s, 3H), 3.75 (s, 3H), 3.18-3.01 (m, 4H). MASS = 470.18 1 H NMR (400 MHz, CDCl 3) δ 9.22 (s, 1H), 7.56 (s, 1H), 7.36 (t, J = 12.0 Hz, 1H), 7.21-7.15 (m, 4H), 6.90 (d, J = 12.0 Hz, 1H), 6.84-6.77 (m, 4H), 6.58 (d, J = 12.0 Hz, 1H), 5.48 (s, 2H), 3.96 (s, 3H), 3.75 (s, 3H), 3.18-3.01 (m, 4H). MASS = 470.18

합성예 531 : 메틸 5-(3-사이클로펜틸프로파나미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 531: Synthesis of methyl 5- (3-cyclopentylpropanamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 사이클로펜테인프로피오닐 클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 531 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and cyclopentanepropionyl chloride (1.2 mmol) were added to a solution of methyl 5-amino-1- (4- methoxybenzyl) ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 531 (yield = 61%).

1H NMR (400 MHz, MeOH-d4) 9.25 (s, 1H), 7.78 (s, 1H), 7.47 (t, J = 12.0 Hz, 1H), 7.15 (d, J = 12.0 Hz, 2H), 7.04 (d, J = 12.0 Hz, 1H), 6.84 (d, J = 12.0 Hz, 2H), 6.78 (d, J = 12.0 Hz, 1H), 5.53 (s, 2H), 3.93 (s, 3H), 3.74 (s, 3H), 2.23-2.18 (m, 9H) MASS=462.22 1 H NMR (400 MHz, MeOH -d4) 9.25 (s, 1H), 7.78 (s, 1H), 7.47 (t, J = 12.0 Hz, 1H), 7.15 (d, J = 12.0 Hz, 2H), 7.04 (d, J = 12.0 Hz, 1H), 6.84 (d, J = 12.0 Hz, 2H), 6.78 (d, J = 12.0 Hz, 1H), 5.53 (s, 2H), 3.93 (s, 3H), 3.74 (s, 3H), 2.23-2.18 (m, 9H) MASS = 462.22

합성예 532 : 메틸 1-(4-메톡시벤질)-2-옥소-5-(2-페닐아세타미도)-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 532: Synthesis of methyl 1- (4-methoxybenzyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 페닐아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 532 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and phenylacetyl chloride (1.2 mmol) were dissolved in CH (CH3CN) 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 532 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.19 (s, 1H), 7.55-7.38 (m, 5H), 7.14-7.10 (m, 3H), 6.78 (d, J = 8.4 Hz, 3H), 5.45 (s, 2H), 3.94 (s, 3H), 3.73(s, 3H), 2.16 (s, 2H) MASS=456.17 1 H NMR (400MHz, CDCl 3 ) δ 8.19 (s, 1H), 7.55-7.38 (m, 5 H), 7.14-7.10 (m, 3 H), 6.78 (d, J = 8.4 Hz, 3H), 5.45 (s, 2 H), 3.94 (s, 3 H), 3.73 (s, 3H), 2.16 (s, 2H) MASS = 456.17

합성예 533 : 메틸 5-벤즈아미도-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 533: Methyl 5-benzamido-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 벤조일클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 533 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and benzoyl chloride (1.2 mmol) were dissolved in CH 2 &lt; RTI ID = 0.0 &gt; Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 533 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 8.24 (s, 1H), 7.97 (d, J = 8.0 Hz, 2H), 7.64-7.58 (m, 1H), 7.57-7.49 (m, 4H), 7.24-7.20 (m, 1H), 7.16 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.46 (s, 2H), 3.91 (s, 3H), 3.73 (s, 3H) MASS=442.15 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 8.24 (s, 1H), 7.97 (d, J = 8.0 Hz, 2H), 7.64-7.58 (m, 1H), 7.57-7.49 (m , 4H), 7.24-7.20 (m, 1H), 7.16 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.46 (s, 2H), 3.91 (s, 3H) , 3.73 (s, 3 H) MASS = 442.15

합성예 534 : 메틸 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 534: Methyl 5- (2- (4-chlorophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

에틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 4-클로로페닐아세틸클로라이드(1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 534 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and 4-chlorophenylacetyl chloride (1.2 mmol) were added to a solution of ethyl 5-amino-1- (4- methoxybenzyl) ) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 534 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.31 (s, 1H), 7.51-7.37 (m, 6H), 7.17-7.11 (m, 3H), 6.80 (d, J = 8.0 Hz, 2H), 5.45 (s, 2H), 3.94 (s, 3H), 3.84 (s, 2H), 3.74 (s, 3H) MASS=490.13 1 H NMR (400MHz, CDCl 3 ) δ 8.31 (s, 1H), 7.51-7.37 (m, 6H), 7.17-7.11 (m, 3H), 6.80 (d, J = 8.0 Hz, 2H), 5.45 (s 2H), 3.94 (s, 3H), 3.84 (s, 2H), 3.74

합성예 535 : 메틸 5- (아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 535: Synthesis of methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 535 화합물을 수득하였다(수율=61%).(1 mmol) of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate, DIPEA (1.5 mmol) and adamantane- (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 535 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=500.23 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS = 500.23

합성예 536 : 메틸 5-(3,5-디메틸아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 536: Synthesis of methyl 5- (3,5-dimethyladamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 디메틸아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 536 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and dimethyladamantane-1-carbonyl (1 mmol) were added to a solution of methyl 5-amino- Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 536 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 6H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 2H) MASS=528.26 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( 2H, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 2.07 (s, 4H), 1.80 (s, 2H) MASS = 528.26

합성예 537 : 메틸 5-(3-브로모아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 537: Methyl 5- (3-bromoadamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 브로모아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 537 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and bromoadamanthane-1-carbonyl (1 mmol) were added to a solution of methyl 5-amino- Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 537 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 3H), 1.80 (s, 4H) MASS=578.14 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 3 H), 1.80 (s, 4 H) MASS = 578.14

합성예 538 : 메틸 1-(4-메톡시벤질)-5-(3-메틸아다만테인-1-카복시아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 538: Synthesis of methyl 1- (4-methoxybenzyl) -5- (3-methyladamantane-1-carboxyamido) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 메틸아다만테인-1-카보닐클로라이드 (1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 538 화합물을 수득하였다(수율=61%).(1 mmol) of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate, DIPEA (1.5 mmol) and methyladamantane- Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 538 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 3H) MASS=514.25 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 3H) MASS = 514.25

합성예 539 : 메틸 5-(2-(아다만테인-1-일)아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트Synthesis Example 539: Synthesis of methyl 5- (2- (adamantan-1-yl) amido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 1-아다만테인아세틸클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 539 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and 1-adamantane acetyl chloride (1.2 mmol) were added to a solution of methyl 5-amino-1- (4-methoxybenzyl) mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 539 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1H), 1.79-1.63 (m, 9H) MASS=514.25 1 H NMR (400MHz, CDCl 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H ), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1 H), 1.79-1.63 (m, 9H) MASS = 514.25

합성예 540 : 메틸 5-(2-(3,5-디메틸아다만테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이하이드록시퀴놀린-3-카복실레이트Synthesis Example 540: Synthesis of methyl 5- (2- (3,5-dimethyladamanthen-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroxy Quinoline-3-carboxylate

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 디메틸-1-아다만테인아세틸 클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 540 화합물을 수득하였다(수율=61%)(1 mmol) of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate, DIPEA (1.5 mmol) and dimethyl-1-adamantaneacetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 540 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 6H), 3.76 (s, 6H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1H), 1.79-1.63 (m, 7H) MASS=542.28 1 H NMR (400MHz, CDCl 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H ), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 6H), 3.76 (s, 6H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1 H), 1.79-1.63 (m, 7 H) MASS = 542.28

합성예 541 : 메틸 5-(2-(3-브로모메테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 541: Methyl 5- (2- (3-bromometh-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinolin- Carboxylate

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 브로모-1-아다만테인아세틸클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 541 화합물을 수득하였다(수율=61%).A mixture of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate (1 mmol), DIPEA (1.5 mmol) and bromo-1-adamantane acetyl Chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 541 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1H), 1.79-1.63 (m, 8H) MASS=592.16 1 H NMR (400MHz, CDCl 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H ), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1 H), 1.79-1.63 (m, 8 H) MASS = 592.16

합성예 542 : 메틸 1-(4-메톡시벤질)-5-(2-(3-메틸아다만테인-1-일)아세트아미도)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 542: Synthesis of methyl 1- (4-methoxybenzyl) -5- (2- (3-methyladamanthen-1-yl) acetamido) -2-oxo-1,2-dichloroquinolin- Carboxylate

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 메틸-1-아다만테인아세틸 클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 542 화합물을 수득하였다(수율=61%).(1 mmol) of methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate, DIPEA (1.5 mmol) and methyl-1-adamantaneacetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 542 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 6H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1H), 1.79-1.63 (m, 8H) MASS=528.26 1 H NMR (400MHz, CDCl 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, J = 8.0 Hz, 2H ), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.96 (s, 3H), 3.76 (s, 6H), 2.24 (s, 2H), 2.18 (s, 1H), 2.04 (s, 1 H), 1.79-1.63 (m, 8 H) MASS = 528.26

합성예 543 : 메틸 5-(2-사이크로헥실아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 543: Synthesis of methyl 5- (2-cyclohexylacetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 사이클로헥실아세틸클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 543 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and cyclohexyl acetyl chloride (1.2 mmol) were added to a solution of methyl 5-amino-1- (4-methoxybenzyl) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 543 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52(s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 2.36 (s, 2H), 1.98-1.62 (m, 11H) MASS=462.22 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 2.36 (s, 2H), 1.98-1.62

합성예 544 : 메틸 5-(사이클로헥센카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 544: Synthesis of methyl 5- (cyclohexecarboxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 사이클로헥산카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 544 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and cyclohexanecarbonyl chloride (1.2 mmol) were added to a solution of methyl 5-amino-1- (4-methoxybenzyl) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 544 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52(s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 1.98-1.62 (m, 11H) MASS=448.20 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 1.98-1.62

합성예 545 : 메틸 5-(아다만테인-1-카복시아미도)-1-(4-에틸벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 545: Synthesis of methyl 5- (adamantane-1-carboxyamido) -1- (4-ethylbenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트 (1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 545 화합물을 수득하였다(수율=61%).(1 mmol) of methyl 5-amino-1- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate, 1.5 mmol of DIPEA and adamantane- 1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 545 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52(s, 2H), 3.97 (s, 3H), 3.76 (m, 5H), 1.98-1.62 (m, 11H) MASS= 498.25 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.97 (s, 3H), 3.76 (m, 5H), 1.98-1.62

합성예 546 : 메틸 5-(아다만테인-1-카복시아미도)-1-(3-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 546: Synthesis of methyl 5- (adamantane-1-carboxyamido) -1- (3-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(3-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트 (1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 546 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and adamantane-1-carbonyl chloride (1 mmol) were added to a solution of methyl 5-amino- 1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 546 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52(s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 1.98-1.62 (m, 11H) MASS= 500.23 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.97 (s, 3H), 3.76 (s, 3H), 1.98-1.62

합성예 547 : 메틸 5-(아다만테인-1-카복시아미도)-1-(4-나이트로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 547: Synthesis of methyl 5- (adamantane-1-carboxyamido) -1- (4-nitrobenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-나이트로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트 (1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 547 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and adamantane-1-carbonyl chloride (1 mmol) were added to a solution of methyl 5-amino- 1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain Synthetic Example 547 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.71 (d, J = 16 Hz, 1H), 8.15 (d, J = 8 Hz, 2H), 7.37 (dd, J = 4 Hz, J = 4 Hz, 2H), 6.51 (d, J = 4 Hz, 1H), 6.48-6.44 (m, 1H), 5.59 (s, 2H), 3.98 (s, 3H). MASS=515.21 1 H NMR (400MHz, CDCl 3 ) δ 8.71 (d, J = 16 Hz, 1H), 8.15 (d, J = 8 Hz, 2H), 7.37 (dd, J = 4 Hz, J = 4 Hz, 2H) , 6.51 (d, J = 4 Hz, 1H), 6.48-6. 44 (m, 1H), 5.59 (s, 2H), 3.98 (s, 3H). MASS = 515.21

합성예 548 : 메틸 5-(아다만테인-1-카복시아미도)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 548: Methyl 5- (adamantane-1-carboxyamido) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dichloroquinoline-

메틸 5-아미노-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디클로로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 548 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol), and adamantane-l- (4-fluorophenoxy) benzyl) -1,2-dichloroquinoline- Carbonyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain the compound of Synthesis Example 548 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.68 (s, 1H), 7.57-7.51 (m, 2H), 7.42 (s, 1H), 7.24 (s, 1H), 7.14 (d, J = 8 Hz, 1H), 7.10 -7.07 (m, 2H), 5.54 (s, 2H), 3.95 (s, 3H), 2.26-1.63 (m, 15H) MASS=554.20 1 H NMR (400MHz, CDCl 3 ) δ 8.68 (s, 1H), 7.57-7.51 (m, 2H), 7.42 (s, 1H), 7.24 (s, 1H), 7.14 (d, J = 8 Hz, 1H 2H), 3.95 (s, 3H), 2.26-1.63 (m, 15H) MASS = 554.20

합성예 549 : 메틸 5-(아다만테인-1-카복소아미도)-1-(4-사이아노벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 549: Synthesis of methyl 5- (adamantane-1-carboxamido) -1- (4-cyanobenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-사이아노벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트 (1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 549 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and adamantane-1-carbonyl chloride (1.5 mmol) were added to a solution of methyl 5-amino- (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain Synthetic Example 549 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J= 8.0 Hz, 2H), 5.52(s, 2H), 3.76 (s, 3H), 1.98-1.62 (m, 11H) MASS=495.22 1 H NMR (400MHz, CDCl 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, J = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52 (s, 2H), 3.76 (s, 3H), 1.98-1.62 (m, 11H) MASS = 495.22

합성예 550 : 메틸 5-(아다만테인-1-카복시아미도)-1-(4-플루오로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 550: Synthesis of methyl 5- (adamantane-1-carboxyamido) -1- (4-fluorobenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-아미노-1-(4-플루오로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트(1mmol), DIPEA(1.5mmol) 및 아다만테인-1-카보닐클로라이드(1.2mmol)를 CH2Cl2 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCO3로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 550 화합물을 수득하였다(수율=61%).(1 mmol), DIPEA (1.5 mmol) and adamantane-1-carbonyl chloride (1 mmol) were added to a solution of methyl 5-amino-l- (4- fluorobenzyl) 1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 min. Residue was extracted with ethyl acetate and saturated NaHCO 3. Thereafter, the residue was purified by silica gel column chromatography to obtain a compound of Synthesis Example 550 (yield = 61%).

1H NMR (400MHz, CDCl3) δ 8.53(s, 1H), 7.55(s, 1H), 7.53-7.43 (m, 2H), 7.21-7.17(m, 1H), 7.11-7.09(m, 1H), 6.97(t, J=8Hz, 1H), 5.52 (s, 2H), 4.42(s, 1H), 3.98(s, 3H), 2.17-1.74(m, 15H) MASS= 488.21 1 H NMR (400MHz, CDCl 3 )? 8.53 (s, IH), 7.55 (s, IH), 7.53-7.43 (m, 2H), 7.21-7.17 , 6.97 (t, J = 8Hz , 1H), 5.52 (s, 2H), 4.42 (s, 1H), 3.98 (s, 3H), 2.17-1.74 (m, 15H) MASS = 488.21

합성의 일반적인 과정General process of synthesis

: 단계(c-2)의 일반적인 과정과 같음: Same as the general procedure of step (c-2)

합성예 551 : 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실릭엑시드Synthesis Example 551: Synthesis of 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

메틸 5-(아다만테인-1-카복시아마이드)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트를 MeOH(200mL)에 용해시킨 10% KOH로 12시간 동안 80℃에서 교반하고, 혼합물을 여과 후 여과물을 H2O로 세척하여 합성예 551 화합물을 수득하였다(수율=70%).A solution of methyl 5- (adamantane-1-carboxyamide) -l- (4-methoxybenzyl) -2-oxo-l, 2-dihydroquinoline-3-carboxylate in 10% after the mixture was stirred at 80 ℃ for 12 hours with KOH, and filtered to give the filtrate washed synthesis example 551 compound with H 2 O (yield = 70%).

1H NMR (400MHz, CDCl3) δ 8.55(s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=486.22 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( 2H, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.76 (s, 1.80 (s, 4 H) MASS = 486.22

합성의 일반적인 과정General process of synthesis

: 단계(d-3, h-8)의 일반적 과정과 같음: Same as the general procedure of step (d-3, h-8)

합성예 552 : 에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 552: Ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 에탄올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 552 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), ethanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 552 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15(t, J = 8 Hz, 3H), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS=514.25 1 H NMR (400MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 ( t, J = 8 Hz, 3H ), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H ), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS = 514.25

합성예 553 : 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N-메틸-2-옥소-1,2-디클로로퀴놀린-3-카복시아미도Synthesis Example 553: Synthesis of 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N-methyl-2-oxo-1,2-dichloroquinoline-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 메틸아민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 553 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), methylamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 553 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 4H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=499.25 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 4H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS = 499.25

합성예 554 : 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N,N-디메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복시아마이드Synthesis Example 554: Synthesis of 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N, N-dimethyl-2-oxo-1,2-dihydroquinoline-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 디메틸아민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 554 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), dimethylamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 554 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=513.26 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4 H), 1.80 (s, 4 H) MASS = 513.26

합성예 555 : 프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 555: Synthesis of propyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 1-프로판올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 555 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), 1-propanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 555 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.51 (s, 1H), 7.56 (b, s, 1H), 7.52-7.44 (m, 2H), 7.17-7.14 (m, 3H), 6.82-6.80 (m, 2H), 5.51 (b, s, 1H), 4.35 (t, J = 8 Hz, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.07-2.06 (m, 6H), 1.85-1.80 (m, 8H), 1.08 (t, J = 8 Hz, 3H) MASS=528.26 1 H NMR (400MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.56 (b, s, 1H), 7.52-7.44 (m, 2H), 7.17-7.14 (m, 3H), 6.82-6.80 (m, 2H), 5.51 (b, s, 1 H), 4.35 (t, J = 8 Hz, 2H), 3.76 (s, 3H), 2.15 -1.80 (m, 8H), 1.08 (t, J = 8 Hz, 3H) MASS = 528.26

합성예 556 : 아이소프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트Synthesis Example 556: Synthesis of isopropyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 2-프로판올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 556 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), 2-propanol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 556 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=528.26 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 6H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4 H), 1.80 (s, 4 H) MASS = 528.26

합성예 557 : N-(1-(4-메톡시벤질)-3-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복시아마이드Synthesis Example 557: Synthesis of N- (1- (4-methoxybenzyl) -3- (methoxymethyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 아세트알데하이드 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 557 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), acetaldehyde (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 557 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 (t, J = 8 Hz, 3H), 6.80(d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 4H), 3.74 (s, 3H), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS=486.25 1 H NMR (400MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 ( t, J = 8 Hz, 3H ), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 4H), 3.74 (s, 3H), 2.06 (s, 6H ), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS = 486.25

합성예 558 : N-(3-(에톡시메틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복시아마이드Synthesis Example 558: Synthesis of N- (3- (ethoxymethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol), 프로피온알데하이드(1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 558 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), propionaldehyde (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. The residue was purified by silica gel chromatography to obtain the compound of Synthesis Example 558 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41(d, J=4 Hz, 1H), 7.15(t, J=8 Hz, 3H), 6.80(d, J=8 Hz, 2H), 5.48(s, 2H), 4.45-4.39(m, 4H), 3.74(s, 3H), 2.14(s, 3H), 2.06(s, 6H), 1.80-1.79(m, 6H), 1.43-1.39(m, 3H) MASS=500.27 1 H NMR (400MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 ( t, J = 8 Hz, 3H ), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 4H), 3.74 (s, 3H), 2.14 (s, 3H ), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS =

합성예 559: S-메틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트Synthesis Example 559: Synthesis of S-methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 메테인싸이올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 559 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), methanesulfon (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 559 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 4H) MASS=516.22 1 H NMR (400MHz, CDCl 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 ( t, J = 8.0 Hz, 2H ), 6.81 (d, J = 12.0 Hz, 2H), 5.47 (s, 2H), 3.98 (s, 3H), 3.76 (s, 3H), 2.17 (s, 3H), 2.07 (s, 4 H), 1.80 (s, 4 H) MASS = 516.22

합성예 560 : S-에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트Synthesis Example 560: Synthesis of S-ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate

5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 에테인싸이올 (1.5 mmol) 및 PyBop(2 mmol)를 반응 혼합물에 첨가하였다. 혼합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 560 화합물을 수득하였다(수율=63%).Carboxylic acid (1 mmol) was dissolved in DMF (2 mL) and DMF (2 mL) was added to a solution of 5- (adamantane- 1-carboxyamido) ). DIPEA (3 mmol), ethanethiol (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Thereafter, the residue was purified by silica gel chromatography to obtain a compound of Synthesis Example 560 (yield = 63%).

1H NMR (400MHz, CDCl3) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 (t, J = 8 Hz, 3H), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS=530.22 1 H NMR (400MHz, CDCl 3 ) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 ( t, J = 8 Hz, 3H ), 6.80 (d, J = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H ), 2.06 (s, 6H), 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS = 530.22

[표 3][Table 3]

Figure 112016031927621-pct00090
Figure 112016031927621-pct00090

Figure 112016031927621-pct00091
Figure 112016031927621-pct00091

Figure 112016031927621-pct00092
Figure 112016031927621-pct00092

Figure 112016031927621-pct00093
Figure 112016031927621-pct00093

Figure 112016031927621-pct00094
Figure 112016031927621-pct00094

Figure 112016031927621-pct00095
Figure 112016031927621-pct00095

합성의 일반적인 과정General process of synthesis

: 단계(a)의 일반적 과정: General procedure of step (a)

출발물질(10.0 g, 52.58 mmol)을 무수 DMF(100 mL)에 용해시켰다. 4-메톡시벤질 클로라이드 (17g, 78.87mmol), K2CO3 (14g, 105.16 mmol), 18-크라운-6 (2.7g, 10.51 mmol)을 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼크로마토그래피로 정제하여 9번 화합물을 수득하였다.The starting material (10.0 g, 52.58 mmol) was dissolved in anhydrous DMF (100 mL). 4-methoxybenzyl chloride (17 g, 78.87 mmol), K 2 CO 3 (14 g, 105.16 mmol) and 18-crown-6 (2.7 g, 10.51 mmol) were added to the solution. The mixture was stirred for 12 hours at room temperature, which was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and concentrated in vacuo. The residue was purified by column chromatography to obtain Compound No. 9.

합성예 561 : 1-(4-메톡시벤질)-5-나이트로퀴놀린-2(1H)-온Synthesis Example 561: 1- (4-Methoxybenzyl) -5-nitroquinolin-2 (1H)

5-나이트로퀴놀린-2(1H)-온 (1 mmol)을 무수 DMF(2 mL)에 용해시켰다. 4-메톡시벤질 클로라이드 (1.5 mmol), K2CO3 (2 mmol), 18-크라운-6 (0.2 mmol)을 용액에 첨가하였다. 혼합물을 상온에서 12시간 동안 교반하고, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다. (수율 = 80%)5-Nitroquinolin-2 (1H) -one (1 mmol) was dissolved in anhydrous DMF (2 mL). 4-Methoxybenzyl chloride (1.5 mmol), K 2 CO 3 (2 mmol) and 18-crown-6 (0.2 mmol) were added to the solution. The mixture was stirred for 12 hours at room temperature, which was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and concentrated in vacuo. Purification by column chromatography gave the desired compound. (Yield = 80%)

1H NMR (400MHz, CDCl3) δ 8.36 (d, J = 12 Hz, 1H), 7.78 (dd, J = 8 Hz, 1.6 Hz, 1H), 7.58 (d, J = 8 Hz, 1H), 7.54 (t, J = 8Hz, 1H), 7.15 (d, J = 8 Hz, 2H), 7.00 (d, J = 8 Hz, 1H), 6.87-6.84 (m, 2H), 5.54 (b, s, 2H), 3.77 (s, 3H) MASS=310.30 1 H NMR (400MHz, CDCl 3 ) δ 8.36 (d, J = 12 Hz, 1H), 7.78 (dd, J = 8 Hz, 1.6 Hz, 1H), 7.58 (d, J = 8 Hz, 1H), 7.54 (t, J = 8Hz, 1H ), 7.15 (d, J = 8 Hz, 2H), 7.00 (d, J = 8 Hz, 1H), 6.87-6.84 (m, 2H), 5.54 (b, s, 2H ), 3.77 (s, 3 H) MASS = 310.30

합성의 일반적인 과정General process of synthesis

: 단계(b)의 일반적 과정: General procedure of step (b)

9 번 화합물 (118mg, 0.36mmol)을 에탄올 (10ml)에 용해시킨 후, SnCl2 (245mg, 1.08mmol)를 용액에 첨가한다. 상온에서 30분간 교반 시키고 브린 (brine)과 에틸아세테이트로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 10번 화합물을 수득하였다.Compound No. 9 (118 mg, 0.36 mmol) is dissolved in ethanol (10 ml) and SnCl 2 (245 mg, 1.08 mmol) is added to the solution. The mixture was stirred at room temperature for 30 minutes and extracted with brine and ethyl acetate. Dry the combined organic layer over anhydrous Na 2 SO 4, and concentrated in vacuo. The residue was purified by column chromatography to obtain Compound No. 10.

합성예 562 : 5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온Synthesis Example 562: 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H)

1-(4-메톡시벤질)-5-나이트로퀴놀린-2(1H)-온 (0.36 mmol) 에탄올(10 ml)에 용해시킨 후, SnCl2 (245mg, 1.08mmol)를 용액에 첨가한다. 상온에서 30분간 교반 시키고 브린 (brine)과 에틸아세테이트로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하였다. 컬럼크로마토그래피로 정제하여 목적 화합물을 수득하였다. (수율 = 70%)Is added to the, SnCl 2 (245mg, 1.08mmol) was dissolved in one (0.36 mmol) in ethanol (10 ml) solution of - 1- (4-methoxybenzyl) -5-nitro-quinolin -2 (1H). The mixture was stirred at room temperature for 30 minutes and extracted with brine and ethyl acetate. Dry the combined organic layer over anhydrous Na 2 SO 4, and concentrated in vacuo. Purification by column chromatography gave the desired compound. (Yield = 70%)

1H NMR (400MHz, CDCl3) δ 7.81 (d, J = 8 Hz, 1H), 7.22 (t, J = 8 Hz, 1H), 7.17 (d, J = 8 Hz, 2H), 6.83-6.81 (m, 2H), 6.73 (d, J = 8 Hz, 2H), 6.51 (d, J = 8 Hz, 1H), 5.46 (b, s, 2H), 4.11 (b, s, 2H), 3.76 (s, 3H) MASS=280.32 1 H NMR (400MHz, CDCl 3 ) δ 7.81 (d, J = 8 Hz, 1H), 7.22 (t, J = 8 Hz, 1H), 7.17 (d, J = 8 Hz, 2H), 6.83-6.81 ( (m, 2H), 6.73 (d, J = 8 Hz, 2H), 6.51 (d, J = 8 Hz, 1H), 5.46 , 3H) MASS = 280.32

합성의 일반적인 과정General process of synthesis

: 단계(d)의 일반적 과정: General procedure of step (d)

10 번 화합물 (8.2mg, 0.01 mmol)을 농축된 HCl과 물에 녹이고 교반한다. 30분이 지난 뒤, 물에 녹여진 NaNO2 (2.21mg, 0.01mmol)를 용액에 첨가한다. 30분 후, SnCl2 (18.86 mg, 0.05mmol) 을 첨가하고 상온에서 12시간 교반시킨다. 1 노르말 HCl로 산화시켜 얻어진 여과물을 여과하여 물로 씻은 후 12번 화합물을 수득하였다.Compound No. 10 (8.2 mg, 0.01 mmol) was dissolved in concentrated HCl and water and stirred. After 30 minutes, NaNO 2 (2.21 mg, 0.01 mmol) dissolved in water is added to the solution. After 30 minutes, SnCl 2 (18.86 mg, 0.05 mmol) was added and the mixture was stirred at room temperature for 12 hours. 1 The filtrate obtained by oxidation with normal HCl was filtered and washed with water to obtain compound No. 12.

합성예 563 : 5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온Synthesis Example 563: Synthesis of 5-hydrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H)

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (8.2mg, 0.01 mmol)을 농축된 HCl과 물에 녹이고 교반한다. 30분이 지난 뒤, 물에 녹여진 NaNo2(2.21mg, 0.01mmol)를 용액에 첨가한다. 30분 후, SnCl2 (18.86 mg, 0.05mmol) 을 첨가하고 상온에서 12시간 교반시킨다. 1 노르말 HCl로 산화시켜 얻어진 여과물을 여과하여 물로 씻은 후 목적 화합물을 수득하였다. (수율 = 85%)5-Amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (8.2 mg, 0.01 mmol) was dissolved in concentrated HCl and water and stirred. After 30 minutes, NaNo2 (2.21 mg, 0.01 mmol) dissolved in water is added to the solution. After 30 minutes, SnCl 2 (18.86 mg, 0.05 mmol) was added and the mixture was stirred at room temperature for 12 hours. 1 The filtrate obtained by oxidation with normal HCl was filtered and washed with water to obtain the target compound. (Yield = 85%)

1H NMR (400MHz, MeOH) δ 8.12 (d, J = 8Hz, 1H), 7.52 (t, J = 8 Hz, 1H), 7.22(d, J = 8 Hz, 1H), 7.13 (d, J = 8 Hz, 2H), 6.84(d, J = 8 Hz, 2H), 6.78 - 6.75 (m, 2H) 5.53 (b, s, 2H) 3.72 (s, 3H) MASS=295.34 1 H NMR (400MHz, MeOH) δ 8.12 (d, J = 8Hz, 1H), 7.52 (t, J = 8 Hz, 1H), 7.22 (d, J = 8 Hz, 1H), 7.13 (d, J = (M, 2H), 6.84 (d, J = 8 Hz, 2H), 6.78-6.75

합성의 일반적인 과정General process of synthesis

: 단계(c)의 일반적 과정: General procedure of step (c)

10 번 화합물 (7.1mg, 0.02mmol)을 CH2Cl2 (0.75ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), R-아다만테인-1-카르보닐 클로라이드 (6.03mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 11, 13 화합물을 수득하였다.The compound 10 (7.1 mg, 0.02 mmol) was dissolved in CH 2 Cl 2 (0.75 ml) and then DIPEA (7.8λ, 0.03 mmol) and R-adamantane-1-carbonyl chloride (6.03 mg, 0.02 mmol) Stir at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and concentrated in vacuo purified by column chromatography to obtain 11 and 13 compound.

합성예 564 : N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드Synthesis Example 564: Synthesis of N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (7.1mg, 0.02mmol)을 CH2Cl2 (0.75ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 아다만테인-1-카르보닐 클로라이드 (6.03mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 45%)After dissolving 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (7.1 mg, 0.02 mmol) in CH 2 Cl 2 (0.75 ml), DIPEA (7.8λ, 0.03 mmol) Butane-1-carbonyl chloride (6.03 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 45%)

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.08-2.05 (m, 6H), 1.88-1.73 (m, 7H) MASS=442.55 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 (B, s, 3H), 2.15 (b, s, 3H), 2.08- 2.05 (m, 6H), 1.88-1.73 (m, 7H) MASS = 442.55

합성예 565 : N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카복사마이드Synthesis Example 565: Synthesis of N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 3-메틸아다만테인-1-카르보닐 클로라이드 (5.99 mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 50%).After dissolving 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) in CH 2 Cl 2 (1 ml), DIPEA (7.8λ, 0.03 mmol) Adamantane-1-carbonyl chloride (5.99 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, to give the desired compound was obtained by concentration in vacuo was purified by column chromatography (yield = 50%).

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) 0.89 (s, 3H) MASS=456.58 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 (B, s, 3H), 2.15 (b, s, 3H), 2.08- 2.05 (m, 5H), 1.88-1.73 (m, 7H) 0.89 (s, 3H) MASS = 456.58

합성예 566 : N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-다이메킬아다만테인-1-카복사마이드Synthesis Example 566: Synthesis of N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethoxyadamantane-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 3-디메틸아다만테인-1-카르보닐 클로라이드 (6.34 mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 50%).After dissolving 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) in CH 2 Cl 2 (1 ml), DIPEA (7.8λ, 0.03 mmol) Adamantane-1-carbonyl chloride (6.34 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, to give the desired compound was obtained by concentration in vacuo was purified by column chromatography (yield = 50%).

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.08-2.05 (m, 4H), 1.88-1.73 (m, 7H), 0.89 (s, 6H) MASS=470.6 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 (B, s, 3H), 2.15 (b, s, 3H), 2.08- 2.05 (m, 4H), 1.88-1.73 (m, 7H), 0.89 (s, 6H) MASS = 470.6

합성예 567 : 3-브로모-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드Synthesis Example 567: Synthesis of 3-bromo-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 3-브로모아다만테인-1-카르보닐 클로라이드 (7.77mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 63%)After dissolving 5-amino-l- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) in CH 2 Cl 2 (1 ml), DIPEA (7.8λ, 0.03 mmol) 1-carbonyl chloride (7.77 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 63%)

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS=521.45 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 (B, s, 3H), 2.15 (b, s, 3H), 2.08- 2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS = 521.45

합성예 568 : 3-클로로-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드Synthesis Example 568: Synthesis of 3-chloro-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 3-클로로아다만테인-1-카르보닐 클로라이드 (6.52mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 60%)After dissolving 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) in CH 2 Cl 2 (1 ml), DIPEA (7.8λ, 0.03 mmol) Adamantane-1-carbonyl chloride (6.52 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 60%)

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS=477.00 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 (B, s, 3H), 2.15 (b, s, 3H), 2.08- 2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS = 477.00

합성예 569 : 2-(아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드Synthesis Example 569: Synthesis of 2- (adamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 2-(아드만탄-1-일)아세틸 클로라이드 (5.95mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 70%)5-amino-1- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.02mmol) with DIPEA (7.8λ, 0.03mmol) was dissolved in CH 2 Cl 2 (1ml), 2- ( Adamantan-1-yl) acetyl chloride (5.95 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 70%)

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.09 (s, 2H) 2.08-2.05 (m, 6H), 1.88-1.73 (m, 7H) MASS=456.58 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 3H), 2.15 (b, s, 3H), 2.09 (m, 2H) s, 2H) 2.08-2.05 (m, 6H), 1.88-1.73 (m, 7H) MASS = 456.58

합성예 570 : N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세트아마이드Synthesis Example 570: Synthesis of N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -2- (3-methyladamantan-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 2-(3-메틸아드만탄-1-일)아세틸 클로라이드 (6.33mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다(수율 = 71%).5-amino-1- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.02mmol) with DIPEA (7.8λ, 0.03mmol) was dissolved in CH 2 Cl 2 (1ml), 2- ( 3-methyladomantan-1-yl) acetyl chloride (6.33 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 71%).

1H NMR (400MHz, CDCl3) δ 7.73(d, J =8 Hz, 1H), 7.47(b, s, 1H), 7.42-7.36(m, 2H), 7.18(dd, J=8 Hz, 4 Hz, 1H), 7.14-7.11(m, 2H), 6.83-6.80(m, 3H), 5.50(b, s, 2H), 3.76(s, 3H), 2.15 (b, s, 3H), 2.09(s, 2H) 2.08-2.05(m, 5H), 1.88-1.73(m, 7H) 0.89(s, 3H) MASS=470.61 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 3H), 2.15 (b, s, 3H), 2.09 (m, 2H) s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) 0.89 (s, 3H) MASS = 470.61

합성예 571 : 2-(3,5-디메틸아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드Synthesis Example 571: 2- (3,5-Dimethyladamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Acetamide

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 2-(3,5-디메틸아드만탄-1-일)아세틸 클로라이드 (6.74mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 66%)5-amino-1- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.02mmol) with DIPEA (7.8λ, 0.03mmol) was dissolved in CH 2 Cl 2 (1ml), 2- ( 3,5-dimethyladimantan-1-yl) acetyl chloride (6.74 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 66%)

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.09 (s, 2H) 2.08-2.05 (m, 4H), 1.88-1.73 (m, 7H) 0.89 (s, 6H) MASS=484.64 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 3H), 2.15 (b, s, 3H), 2.09 (m, 2H) s, 2H) 2.08-2.05 (m, 4H), 1.88-1.73 (m, 7H) 0.89 (s, 6H) MASS = 484.64

합성예 572 : 2-(3-브로모아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드Synthesis Example 572: 2- (3-Bromoadamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.02mmol)을 CH2Cl2(1 ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 2-(3-브로모메틸아드만탄-1-일)아세틸 클로라이드 (8.16mg, 0.02mmol)을 상온에 서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 64%).After dissolving 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) in CH 2 Cl 2 (1 ml), DIPEA (7.8λ, 0.03 mmol) (3-bromomethyladomantan-1-yl) acetyl chloride (8.16 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 64%).

1H NMR (400MHz, CDCl3) δ 7.73(d, J = 8 Hz, 1H), 7.47(b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.09 (s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS=535.48 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 3H), 2.15 (b, s, 3H), 2.09 (m, 2H) s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS = 535.48

합성예 573 : 2-(3-클로로아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드Synthesis Example 573: 2- (3-Chloroadamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-

5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온 (10mg, 0.02mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (7.8λ, 0.03mmol), 2-(3-클로로메틸아드만탄-1-일)아세틸 클로라이드 (6.92mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다(수율 = 66%).5-amino-1- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.02mmol) with DIPEA (7.8λ, 0.03mmol) was dissolved in CH 2 Cl 2 (1ml), 2- ( 3-chloromethyladomantan-1-yl) acetyl chloride (6.92 mg, 0.02 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 66%).

1H NMR (400MHz, CDCl3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 Hz, 1H), 7.14-7.11 (m, 2H), 6.83-6.80 (m, 3H), 5.50 (b, s, 2H), 3.76 (s, 3H), 2.15 (b, s, 3H), 2.09 (s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS=491.02 1 H NMR (400MHz, CDCl 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, J = 8 Hz, 4 3H), 2.15 (b, s, 3H), 2.09 (m, 2H) s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS = 491.02

합성예 574 : N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드Synthesis Example 574: Synthesis of N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 아다만테인-1-아세틸 클로라이드(5.94mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다(수율 = 66%).After dissolving 5-hydrazinyl-l- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.03 mmol) in CH 2 Cl 2 (1 ml), DIPEA (11.7λ, 0.04 mmol) Butane-1-acetyl chloride (5.94 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 66%).

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38(b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H) ), 2.05-2.00 (m, 6H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=457.57 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H), 2.05-2.00 (m, 6H), 1.90-1.85 m, 7H) MASS = 457.57

합성예 575 : N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카르보하이드라자이드SYNTHESIS EXAMPLE 575 Synthesis of N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carbohydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 3-메틸아다만테인-1-아세틸 클로라이드 (5.94mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 70%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 3 -Methyl adamantane-1-acetyl chloride (5.94 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 70%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H) ), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H), 0.89 (s, 3H) MASS=471.06 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H), 2.05-2.00 (m, 5H), 1.90-1.85 m, 7H), 0.89 (s, 3H) MASS = 471.06

합성예 576 : N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-디메틸아다만테인-1-카르보하이드라자이드Synthesis Example 576: Synthesis of N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyladamantane- Zaid

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 3,5-디메틸아다만테인-1-아세틸 클로라이드 (6.80mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 71%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 3 , And 5-dimethyladamantane-1-acetyl chloride (6.80 mg, 0.03 mmol) were stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 71%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13(d, J = 8 Hz, 2H), 6.87(d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H), 0.89 (s, 6H) MASS=485.62 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H), 2.05-2.00 (m, 5H), 1.90-1.85 m, 7H), 0.89 (s, 6H) MASS = 485.62

합성예 577 : 3-브로모-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드Synthesis Example 577: Synthesis of 3-bromo-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 3-브로모아다만테인-1-아세틸 클로라이드 (8.32mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 75%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 3 - bromoimantane-1-acetyl chloride (8.32 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 75%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H) ), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=536.47 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H), 2.05-2.00 (m, 5H), 1.90-1.85 m, 7H) MASS = 536.47

합성예 578 : 3-클로로-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드Synthesis Example 578: Synthesis of 3-chloro-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 3-브로모아다만테인-1-아세틸 클로라이드 (6.99mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 75%).5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 3 (6.99 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, to give the desired compound was obtained by concentration in vacuo was purified by column chromatography (yield = 75%).

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H) ), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=492.01 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H), 2.05-2.00 (m, 5H), 1.90-1.85 m, 7H) MASS = 492.01

합성예 579 : 2-(아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드Synthesis Example 579: Synthesis of 2- (adamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 2-(아다만탄-1-일)아세틸 클로라이드 (6.38mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%).5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 2 - (adamantan-1-yl) acetyl chloride (6.38 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 77%).

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 6H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=471.60 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) 2H), 2.05-2.00 (m, 6H), 1.90-1.85 (m, 3H), 4.14 (dd, J = 8 Hz, J = 3H), 1.80-1.65 (m, 7H) MASS = 471.60

합성예 580 : N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세토하이드라자이드Synthesis Example 580: Synthesis of N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Hydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 2-(3-메틸아다만탄-1-일)아세틸 클로라이드 (6.80mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 2 - (3-methyladamantan-1-yl) acetyl chloride (6.80 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 77%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H), 0.89 (s, 3H) MASS=485.62 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H)), 2.09 (s, 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H), 0.89 (s, 3H) MASS = 485.62

합성예 581 : 2-(3,5-디메틸아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드Synthesis Example 581: Synthesis of 2- (3,5-dimethyladamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- ) Acetohydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 2-(3,5-디메틸아다만탄-1-일)아세틸 클로라이드 (7.21mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 2 - (3,5-dimethyladamantan-1-yl) acetyl chloride (7.21 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 77%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 4H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H), 0.89 (s, 6H) MASS=499.65 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) 2H), 2.05-2.00 (m, 4H), 1.90-1.85 (m, 3H), 4.14 (dd, J = 8 Hz, J = 3H), 1.80-1.65 (m, 7H), 0.89 (s, 6H) MASS = 499.65

합성예 582 : 2-(3-브로모아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드Synthesis Example 582: Synthesis of 2- (3-bromoamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Hydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 2-(3-브로모아다만탄-1-일)아세틸 클로라이드 (8.74mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 80%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 2 - (3-bromoamantan-1-yl) acetyl chloride (8.74 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 80%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=550.49 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75-3.73 3H), 1.80-1.65 (m, 7H) MASS = 550.49

합성예 583 : 2-(3-클로로아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드Synthesis Example 583: 2- (3-Chloroadamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Hydrazide

5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온(10mg, 0.03mmol)을 CH2Cl2 (1ml)에 용해한 후 DIPEA (11.7λ, 0.04mmol), 2-(3-클로로아다만탄-1-일)아세틸 클로라이드 (7.41mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 H2O로 추출하였다. 합쳐진 유기층을 무수 Na2SO4로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 82%)5-hydrazide possess l- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.03mmol) with DIPEA (11.7λ, 0.04mmol) was dissolved in CH 2 Cl 2 (1ml), 2 - (3-chloroadamantan-1-yl) acetyl chloride (7.41 mg, 0.03 mmol) was stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and H 2 O. Dry the combined organic layer over anhydrous Na 2 SO 4, and were concentrated in vacuo purified by column chromatography to give the desired compound (yield = 82%)

1H NMR (400MHz, CDCl3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70(d, J = 8 Hz, 1H), 6.63(d, J = 8 Hz, 1H), 5.45(b, s, 2H), 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS=506.04 1 H NMR (400MHz, CDCl 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, J = 12 Hz, 1H), 6.81 ( d, J = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H) , 4.14 (dd, J = 8 Hz, J = 8 Hz, 1H), 3.75 -3.73 (m, 3H)), 2.09 (s, 2H), 2.05-2.00 (m, 5H), 1.90-1.85 (m, 3H), 1.80-1.65 (m, 7H) MASS = 506.04

[표 4][Table 4]

Figure 112016031927621-pct00096
Figure 112016031927621-pct00096

Figure 112016031927621-pct00097
Figure 112016031927621-pct00097

Figure 112016031927621-pct00098
Figure 112016031927621-pct00098

Figure 112016031927621-pct00099
Figure 112016031927621-pct00099

Figure 112016031927621-pct00100
Figure 112016031927621-pct00100

Figure 112016031927621-pct00101
Figure 112016031927621-pct00101

실험예Experimental Example

IL-2 억제활성의 측정Measurement of IL-2 inhibitory activity

본 발명자들은 퀴놀린 화합물들의 면역억제 활성을 조사하기 위해 ELISA를 통해 IL-2의 생성을 측정하였다. Jurkat T 림프구(1x106 cells/ml)를 24-웰 플레이트에 씨딩하였다. 각 웰의 세포들에 10μM 또는 1μM의 최종농도로 시험 화합물을 처리하고 500nM 이노마이신 및 5n MPMA를 처리하여 세포를 자극하였다. 세포들은 37℃에서 13시간 동안 배양하고 4800rpm으로 2분 동안 원심분리한 뒤 각 웰의 상등액을 수집하였다. IL-2 발현량을 항-인간 IL-2 항체를 포집항체로, 바이오틴화 된 항-인간 IL-2 항체를 검출항체로 한 ELISA를 통해 측정하였다.The present inventors measured the production of IL-2 through ELISA to investigate the immunosuppressive activity of quinoline compounds. Jurkat T lymphocytes (1x10 6 cells / ml) were seeded in 24-well plates. Cells in each well were treated with test compounds at a final concentration of 10 [mu] M or 1 [mu] M and treated with 500 nM inomycin and 5 n MPMA to stimulate the cells. The cells were incubated at 37 ° C for 13 hours and centrifuged at 4800 rpm for 2 minutes and the supernatant of each well was collected. The amount of IL-2 expression was measured by ELISA using anti-human IL-2 antibody as a collection antibody and biotinylated anti-human IL-2 antibody as a detection antibody.

[표 5][Table 5]

Figure 112016031927621-pct00102
Figure 112016031927621-pct00102

IL-1β 억제활성의 측정Measurement of IL-1? Inhibitory activity

자가면역 질환에 관련되는 중요한 사이토카인 중 하나로 알려진 인터루킨-1β(Interleukin-1β, IL-1β)는 인터루킨 1 범주에 속하며 활성화된 마크로파지(macrophages)에 의해 생성된다. 이 사이토카인은 면역반응에서 매우 중요한 인자로 알려져 있고 다양한 세포활성과 관련이 된다. 예를 들어 세포 활성, 세포 생장, 분화, 자멸사 와 연관되며 이는 또한 콕스2(COX2)에 의해 유도된다. 관련 질환으로는 큰 범주의 자가면역 질환, 염증성 통증 및 세포독성 스트레스(cytotoxic stressed)와도 관련된다. 이에, 본 발명자들은 퀴놀리논 화합물들의 면역억제 활성을 조사하기 위해 ELISA를 통해 IL-1β의 생성을 측정하였다Interleukin-1β (Interleukin-1β, IL-1β), known as one of the important cytokines involved in autoimmune diseases, is a member of the interleukin 1 category and is produced by activated macrophages. This cytokine is known to be a very important factor in the immune response and is associated with various cellular activities. For example, cell activation, cell growth, differentiation, apoptosis, which is also induced by Cox2 (COX2). Related diseases are also associated with large categories of autoimmune diseases, inflammatory pain, and cytotoxic stress. Thus, the inventors measured the production of IL-1 [beta] through ELISA to examine the immunosuppressive activity of quinolinone compounds

[표 6][Table 6]

Figure 112016031927621-pct00103
Figure 112016031927621-pct00103

hP2XhP2X 77 -발현 HEK293 세포에서의 에티듐(Ethidium) 축적- Ethidium accumulation in expressing HEK293 cells

자가면역 질환의 중요한 타킷으로 알려져 있는 P2X7 수용체에서의 길항적인(antagonistic) 활성을 알아보기 위해 EtBr 업테이크 분석을 진행하였다. P2X7 수용체는 자가면역 질환에 관련되는 중요한 사이토카인 IL-1β와 관련된 중요한 수용체이다. 2'(3')-O-(4-벤조일벤조일)-ATP(BzATP)은 hP2X 7-발현 HEK293 세포에서 에티듐 이온 축적을 촉진한다. 재조합 인간 P2X7 은 안정적으로 형질전환된 인간 HEK293 세포에서 기능적으로 발현된다. 합성된 퀴놀리논 유도체들을 각각 96-웰 플레이트(바닥이 투명한 검은색)에 첨가하였다. HP2X7-발현 HEK293 세포를 2.5 x 106 cells/ml로 에티듐브로마이드 0.1 mM, 에틸렌디아민 테트라아세틱애시드(EDTA) 1 mM, 글루코스 5 mM, HEPES 20 mM 및 염화칼륨 140 mM(pH 7.4)을 포함하는 HEPES-완충 염 용액에서 재부유하였다. 96-웰 플레이트에 세포 부유물을 처리하고 BzATP를 첨가하였다. 플레이트를 37℃에서 120분 간 배양하고, 에티듐의 세포 축적을 형광 플레이트 리더로 측정하였다(530/20 여기 필터 및 590/20 발광필터).EtBr uptake analysis was performed to determine the antagonistic activity of the P2X7 receptor, which is known to be an important target of autoimmune disease. The P2X7 receptor is an important receptor associated with the important cytokine IL-1β involved in autoimmune disease. 2 '(3') - O- (4-benzoylbenzoyl) -ATP (BzATP) promotes the accumulation of ethidium ions in hP2X 7 -expressing HEK293 cells. Recombinant human P2X 7 are functionally expressed in a stable transfection of human HEK293 cells. The synthesized quinolinone derivatives were each added to a 96-well plate (bottom clear black). HP2X 7 - expressing HEK293 cells to 2.5 x 10 ethidium on a 6 cells / ml bromide, 0.1 mM, ethylene diamine tetra acetic acid (EDTA) 1 mM, including glucose, 5 mM, HEPES 20 mM, and potassium chloride 140 mM (pH 7.4) &Lt; / RTI &gt; HEPES-buffered saline solution. Cell suspensions were treated in 96-well plates and BzATP was added. Plates were incubated for 120 min at 37 ° C and cell accumulation of ethidium was measured with a fluorescent plate reader (530/20 excitation filter and 590/20 excitation filter).

[표 7][Table 7]

Figure 112016031927621-pct00104
Figure 112016031927621-pct00104

이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아닌 점은 명백하다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항과 그의 등가물에 의하여 정의된다고 할 것이다.While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the same is by way of illustration and example only and is not to be construed as limiting the scope of the present invention. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.

Claims (11)

삭제delete 삭제delete 삭제delete 삭제delete 다음 중 어느 하나의 화학식으로 표시되는 퀴놀리논(quinolinone) 유도체 또는 이의 약제학적으로 허용되는 염:
(1) 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(2) 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(3) 1-(4-플루오로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(4) 1-(4-플루오로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(5) 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(6) 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(7) 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(8) 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(9) 1-(나프탈렌-2-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(10) 1-([1,1'-비페닐]-4-일메틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(11) 1-(4-벤질벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(12) 5-니트로-2-옥소-N-펜에틸-1-(4-페녹시벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;
(13) 1-(4-클로로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(14) 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(15) 1-(4-시아노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(16) 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(152) 1-(4-(하이드록시메틸)벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(153) 1-(4-에틸벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(154) 1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(155) 5-(2-(4-클로로페닐)아세트아미도)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(156) 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-N-(4-메틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(157) N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(158) 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(159) 1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(160) N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(161) 1-(4-메톡시벤질)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(162) 1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(163) 1-((2,3-디하이드로-1H-인덴-5-일)메틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(164) 1-(2-(2,3-디하이드로-1H-인덴-5-일)에틸)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(165) 5-(2-(4-플루오로페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(166) 5-(2-(4-에틸페닐)아세트아미도)-N-(4-메톡시펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(167) N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(168) 1-벤조일-N-(4-브로모벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(169) N-(4-브로모벤질)-1-(4-메톡시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(170) N-(4-브로모펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(171) N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(172) N-(4-브로모펜에틸)-2-옥소-1-(4-(트리플루오로메톡시)벤조일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(173) N-(4-브로모펜에틸)-5-(2-(4-하이드록시페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(174) N-(4-클로로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(175) N-(4-클로로벤질)-1-(4-에틸벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(176) N-(4-클로로벤질)-1-(4-하이드록시벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(177) N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(178) N-(4-클로로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(179) 1-(4-클로로벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(180) N-(4-클로로펜에틸)-1-(4-아이오도벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(181) N-(4-클로로펜에틸)-1-(4-니트로벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(182) 1-(4-아미노벤조일)-N-(4-클로로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(183) N-(4-클로로펜에틸)-5-(2-(4-니트로페닐)아세트아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(184) N-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(185) N-(4-플루오로벤질)-1-(4-포르밀벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(186) 1-(4-시아노벤조일)-N-(4-플루오로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(187) N-(4-플루오로벤질)-1-(4-(메틸티오)벤조일)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(188) N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(189) N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(190) 1-(4-(디플루오로메틸)벤조일)-N-(4-플루오로펜에틸)-2-옥소-1,2-디하이드로 퀴놀린-3-카복사마이드;
(191) N-(4-플루오로펜에틸)-1-(2-(4-메톡시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(192) N-(4-플루오로펜에틸)-2-옥소-1-(2-(4-(트리플루오로메톡시)페닐)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(193) N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(194) N-(4-에틸벤질)-1-(2-(4-하이드록시페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(195) N-(4-에틸벤질)-1-(2-(4-에틸페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(196) N-(4-에틸벤질)-1-(2-(4-플루오로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(197) 1-(2-(4-클로로페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(198) N-(4-에틸벤질)-1-(2-(4-아이오도페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(199) N-(4-에틸벤질)-1-(2-(4-니트로페닐)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(200) 1-(2-(4-아미노페닐)아세틸)-N-(4-에틸벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(216) 1-(4-포르밀벤질)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(217) 1-(4-포르밀펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(218) 1-(4-(디플루오로메틸)펜에틸)-N-(4-니트로펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(219) N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(220) 1-(4-(디플루오로메틸)벤질)-N-(4-(N,N-디메틸설파모일)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(221) N-(4-(N,N-디메틸설파모일)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(222) N-(4-(하이드록시메틸)벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(223) N-(4-(하이드록시메틸)펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(224) 2-옥소-N-(4-비닐벤질)-1,2-디하이드로퀴놀린-3-카복사마이드;
(225) 2-옥소-N-(4-비닐펜에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(226) N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(227) 1-(2,3-디하이드로-1H-인덴-2-카르보닐)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(228) 1-(2-(2,3-디하이드로-1H-인덴-2-일)아세틸)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(229) 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-메틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(230) N-에틸-1-(2-(5-메톡시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(231) N-에틸-1-(2-(5-(메틸티오)-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(232) N-에틸-2-옥소-N-페닐-1-(2-(5-(트리플루오로메톡시)-2,3-디하이드로-1H-인덴-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(233) N-에틸-1-(2-(5-하이드록시-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(234) N-에틸-1-(2-(5-에틸-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(235) N-에틸-1-(2-(5-플루오로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(236) 1-(2-(5-클로로-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(237) N-에틸-1-(2-(5-아이오도-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(238) N-에틸-1-(2-(5-니트로-2,3-디하이드로-1H-인덴-2-일)아세틸)-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(239) 1-(2-(5-아미노-2,3-디하이드로-1H-인덴-2-일)아세틸)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(240) N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(241) 1-(3-(2,3-디하이드로-1H-인덴-2-일)프로파노일)-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(242) N-에틸-2-옥소-N-페닐-5-프로피온아미도-1,2-디하이드로퀴놀린-3-카복사마이드;
(243) 5-부티라미도-N-에틸-2-옥소-N-페닐-1,2-디하이드로퀴놀린-3-카복사마이드;
(244) N-메틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(245) N-에틸-2-옥소-5-펜탄아미도-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(246) N-에틸-5-(2-메톡시아세트아미도)-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(247) N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(248) N-에틸-2-옥소-1-(4-(페닐티오)벤질)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(249) N-에틸-2-옥소-1-(4-페녹시벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(250) N-에틸-2-옥소-1-(4-(페닐티오)벤조일)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(251) N-에틸-2-옥소-1-(2-(4-(페닐티오)페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(252) N-에틸-2-옥소-1-(2-(4-페녹시페닐)아세틸)-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(253) 1-(2-(4-벤질페닐)아세틸)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(254) 1-(4-벤질벤조일)-N-에틸-2-옥소-N-(p-톨일)-1,2-디하이드로퀴놀린-3-카복사마이드;
(255) N-(4-메톡시페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(256) N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(257) 5-(2-브로모아세트아미도)-N-에틸-N-(4-메톡시페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(258) N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(259) N-(4-브로모페닐)-1-(사이클로펜타-1,3-디엔카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(260) N-(4-브로모페닐)-N-메틸-2-옥소-1-(2H-피롤-3-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;
(261) N-(4-브로모페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;
(262)N-(4-브로모페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(263) N-(4-브로모페닐)-N-메틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(264) N-(4-브로모페닐)-1-(2-(퓨란-2-일)아세틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(265) 1-(2-(2H-피롤-2-일)아세틸)-N-(4-브로모페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(266) N-(4-브로모페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(267) N-(4-브로모페닐)-1-(사이클로헥산카르보닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(268) N-(4-브로모페닐)-1-(3-사이클로헥실프로파노일)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(269) N-(4-브로모페닐)-5-(2-클로로아세트아미도)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(270) N-(4-클로로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(271) N-(4-클로로페닐)-1-(사이클로펜탄카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(272) N-(4-클로로페닐)-1-(퓨란-2-카르보닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(273) N-(4-클로로페닐)-N-메틸-2-옥소-1-(티오펜-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;
(274) N-(4-클로로페닐)-N-메틸-2-옥소-1-(2H-피롤-2-카르보닐)-1,2-디하이드로퀴놀린-3-카복사마이드;
(275) N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(276) N-(4-클로로페닐)-1-(2-사이클로펜틸아세틸)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(277) N-(4-클로로페닐)-N-에틸-1-(2-(퓨란-2-일)아세틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(278) N-(4-클로로페닐)-N-에틸-2-옥소-1-(2-(티오펜-2-일)아세틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(279) 1-(2-(2H-피롤-2-일)아세틸)-N-(4-클로로페닐)-N-에틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(280) N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(281) N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-페닐에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(282) N-(4-플루오로페닐)-1-(2-(4-메톡시페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(283) N-(4-플루오로페닐)-N-메틸-2-옥소-1-(2-옥소-2-(4-(트리플루오로메톡시)페닐)에틸)-1,2-디하이드로퀴놀린-3-카복사마이드;
(284) N-(4-플루오로페닐)-N-메틸-1-(2-(4-니트로페닐)-2-옥소-에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(285) N-(4-플루오로페닐)-1-(2-(4-하이드록시페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(286) N-(4-플루오로페닐)-1-(2-(4-플루오로페닐)-2-옥소-에틸)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(287) 1-(2-(4-에틸페닐)-2-옥소-에틸)-N-(4-플루오로페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(288) 1-(2-(4-시아노페닐)아세틸)-N-(4-에틸펜에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(289) N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(290) 1-(2-(4-아미노페닐)-2-옥소-에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(291) 1-(2-(4-시아노페닐)-2-옥소-에틸)-N-에틸-N-(4-플루오로페닐)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(292) N-에틸-N-(4-플루오로페닐)-1-(2-(4-(메틸티오)페닐)-2-옥소-에틸)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(293) N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(294) 1-(2,4-디메틸벤질)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(295) 1-(2,4-디메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(296) N-(4-에틸페닐)-1-(4-하이드록시-2-메틸벤질)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(297) N-(4-에틸페닐)-N-메틸-1-(2-메틸-4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(298) 1-(4-에틸-2-메틸펜에틸)-N-(4-에틸페닐)-N-메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복사마이드;
(463) 5-클로로-2-옥소-N-페네틸-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드;
(464) 5-클로로-1-(4-에틸벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카프복스아미드;
(465) 5-클로로-1-(4-아이소프로필벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;
(466) 5-클로로-1-(4-나이트로벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;
(467) 5-클로로-1-(4-메톡시벤질)-2-옥소-N-페네틸-1,2-디하이드로퀴놀린-3-카르복스아미드;
(468) 5-클로로-1-(4-에틸벤질)-N-(4-플루오로페네틸)-2-옥소-1,2-디하이드로퀴놀린-3-카프복스아미드;
(469) 5-클로로-N-(4-플루오로페네틸)-1-(4-아이소프로필벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;
(470) 5-클로로-N-(4-플루오로페네틸)-1-(4-나이트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;
(471) 5-클로로-N-(4-플루오로페네틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복스아미드;
(472) 5-클로로-N-(4-플루오로페네틸)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복스아미드;
(473) 1-(4-에틸벤질)-N-(4-플루오로펜에틸)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르톡사마이드;
(474) N-(4-플루오로펜에틸)-1-(4-이소프로필벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드);
(475) N-(4-플루오로펜에틸)-5-니트로-1-(4-니트로벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드;
(476) 5-아미노-N-(4-브로모펜에틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드);
(477) 1-(4-메톡시벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드;
(478) N-(4-플루오로펜에틸)-1-(4-메톡시벤질)-5-니트로-2-옥소-1,2-디하이드로퀴놀린-3-카르복사마이드;
(479) 5-니트로-2-옥소-N-펜에틸-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드;
(480) N-(4-플루오로펜에틸)-5-니트로-2-옥소-1-(4-(트리플루오로메톡시)벤질)-1,2-디하이드로퀴놀린-3-카르복사마이드;
(481) 1-(4-이소프로필벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카르복사마이드;
(482) 메틸 1-(4-메톡시벤질)-2-옥소-5-(3-페닐프로파나미노)-1,2-디하이드로퀴놀린-3-카복실레이트;
(483) 메틸 5-(3-사이클로펜틸프로파나미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(484) 메틸 1-(4-메톡시벤질)-2-옥소-5-(2-페닐아세타미도)-1,2-디하이드로퀴놀린-3-카복실레이트;
(485) 메틸 5-벤즈아미도-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(486) 메틸 5-(2-(4-클로로페닐)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(487) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(488) 메틸 5-(3,5-디메틸아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(489) 메틸 5-(3-브로모아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(490) 메틸 1-(4-메톡시벤질)-5-(3-메틸아다만테인-1-카복시아미도)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(491) 메틸 5-(2-(아다만테인-1-일)아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카복실레이트;
(492) 메틸 5-(2-(3,5-디메틸아다만테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이하이드록시퀴놀린-3-카복실레이트;
(493) 메틸 5-(2-(3-브로모메테인-1-일)아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(494) 메틸 1-(4-메톡시벤질)-5-(2-(3-메틸아다만테인-1-일)아세트아미도)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(495) 메틸 5-(2-사이크로헥실아세트아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(496) 메틸 5-(사이클로헥센카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(497) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-에틸벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(498) 메틸 5-(아다만테인-1-카복시아미도)-1-(3-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(499) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-나이트로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(500) 메틸 5-(아다만테인-1-카복시아미도)-2-옥소-1-(4-(트라이플루오로메톡시)벤질)-1,2-디클로로퀴놀린-3-카복실레이트:
(501) 메틸 5-(아다만테인-1-카복소아미도)-1-(4-사이아노벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(502) 메틸 5-(아다만테인-1-카복시아미도)-1-(4-플루오로벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(503) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-다이클로로퀴놀린-3-카복실릭엑시드;
(504) 에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(505) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N-메틸-2-옥소-1,2-디클로로퀴놀린-3-카복시아미도;
(506) 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-N,N-디메틸-2-옥소-1,2-디하이드로퀴놀린-3-카복시아마이드;
(507) 프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린-3-카복실레이트;
(508) 아이소프로필 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디클로로퀴놀린끈-카복실레이트;
(509) N-(1-(4-메톡시벤질)-3-(메톡시메틸)-2-옥소-1,2-디하이드로퀴놀린 -5-일)아다만테인-1-카복시아마이드;
(510) N-(3-(에톡시메틸)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린 -5-일)아다만테인-1-카복시아마이드;
(511) S-메틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트;
(512) S-에틸 5-(아다만테인-1-카복시아미도)-1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-3-카보싸이오에이트;
(513) 1-(4-메톡시벤질)-5-나이트로퀴놀린-2(1H)-온;
(514) 5-아미노-1-(4-메톡시벤질)퀴놀린-2(1H)-온;
(515) 5-하이드라지닐-1-(4-메톡시벤질)퀴놀린-2(1H)-온;
(516) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테 인-1-카복사마이드;
(517) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카복사마이드;
(518) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-디메틸아다만테인-1-카복사마이드;
(519) 3-브로모-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드;
(520) 3-클로로-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카복사마이드;
(521) 2-(아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로 퀴놀린-5-일)아세트아마이드;
(522) N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세트아마이드;
(523) 2-(3,5-디메틸아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;
(524) 2-(3-브로모아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;
(525) 2-(3-클로로아다만탄-1-일)-N-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세트아마이드;
(526) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;
(527) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3-메틸아다만테인-1-카르보하이드라자이드;
(528) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-3,5-디메틸아다만테인-1-카르보하이드라자이드;
(529) 3-브로모-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;
(530) 3-클로로-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아다만테인-1-카르보하이드라자이드;
(531) 2-(아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드;
(532) N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)-2-(3-메틸아다만탄-1-일)아세토하이드라자이드;
(533) 2-(3,5-디메틸아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드;
(534) 2-(3-브로모아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드; 및
(535) 2-(3-클로로아다만탄-1-일)-N'-(1-(4-메톡시벤질)-2-옥소-1,2-디하이드로퀴놀린-5-일)아세토하이드라자이드.
A quinolinone derivative represented by any one of the following formulas or a pharmaceutically acceptable salt thereof:
(1) 1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(2) 1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(3) 1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(4) 1- (4-Fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(5) 1- (4-Chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(6) 5-Nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(7) 1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(8) 1- (4-Cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(9) 1- (Naphthalen-2-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(10) 1 - ([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(11) 1- (4-Benzylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(12) 5-Nitro-2-oxo-N-phenethyl-1- (4-phenoxybenzyl) -1,2-dihydroquinoline-3-carboxamide;
(13) 1- (4-Chlorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(14) 1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(15) 1- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(16) 5-Nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(152) 1- (4- (hydroxymethyl) benzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(153) 1- (4-Ethylbenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(154) 1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(155) 5- (2- (4-Chlorophenyl) acetamido) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(156) 5- (2- (4-chlorophenyl) acetamido) -1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide;
(157) N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(158) 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) Hydroquinoline-3-carboxamide;
(159) 1- (2- (5-Ethyl-2,3-dihydro-1H-inden-2-yl) ethyl) -N- (4-methoxybenzyl) Hydroquinoline-3-carboxamide;
(160) N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(161) 1- (4-methoxybenzyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(162) 1- (2- (5-Hydroxy-2,3-dihydro-1H-inden-2-yl) ethyl) -N- (4-methoxyphenethyl) Dihydroquinoline-3-carboxamide;
Yl) methyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinolin-3- Carboxamide;
Yl) ethyl) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide;
(165) 5- (2- (4-Fluorophenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(166) 5- (2- (4-ethylphenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(167) N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(168) 1-Benzoyl-N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(169) N- (4-bromobenzyl) -1- (4-methoxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(170) N- (4-bromophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(171) N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(172) N- (4-Bromophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzoyl) -1,2-dihydroquinoline-3-carboxamide;
(173) N- (4-bromophenethyl) -5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(174) N- (4-chlorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(175) N- (4-chlorobenzyl) -1- (4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(176) N- (4-chlorobenzyl) -1- (4-hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(177) N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(178) N- (4-chlorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(179) 1- (4-Chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(180) N- (4-chlorophenethyl) -1- (4-iodobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(181) N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(182) 1- (4-aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(183) N- (4-chlorophenethyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(184) N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(185) N- (4-fluorobenzyl) -1- (4-formylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(186) 1- (4-cyanobenzoyl) -N- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(187) N- (4-fluorobenzyl) -1- (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(188) N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(189) N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(190) 1- (4- (difluoromethyl) benzoyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(191) N- (4-fluorophenethyl) -1- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(192) Synthesis of N- (4-fluorophenethyl) -2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1,2-dihydroquinoline- ;
(193) N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(194) N- (4-ethylbenzyl) -1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(195) N- (4-ethylbenzyl) -1- (2- (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(196) N- (4-ethylbenzyl) -1- (2- (4-fluorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(197) 1- (2- (4-Chlorophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(198) N- (4-ethylbenzyl) -1- (2- (4-iodophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(199) N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(200) 1- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(216) 1- (4-formylbenzyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(217) 1- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(218) 1- (4- (difluoromethyl) phenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(219) N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(220) 1- (4- (difluoromethyl) benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline- Mide;
(221) N- (4- (N, N-dimethylsulfamoyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(222) N- (4- (hydroxymethyl) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(223) N- (4- (hydroxymethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(224) 2-oxo-N- (4-vinylbenzyl) -1,2-dihydroquinoline-3-carboxamide;
(225) 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide;
(226) N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;
(227) 1- (2,3-Dihydro-1H-indene-2-carbonyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;
Yl) acetyl) -N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carbaldehyde (228) Copymade;
(229) 1- (3- (2,3-dihydro-1H-inden-2-yl) propanoyl) -N-methyl- - carboxamide;
(230) Synthesis of N-ethyl-1- (2- (5-methoxy-2,3-dihydro-1H- Quinolin-3-carboxamide;
(231) Synthesis of N-ethyl-1- (2- (5- (methylthio) -2,3-dihydro- Dihydroquinoline-3-carboxamide;
(232) N-ethyl-2-oxo-N-phenyl-1- (2- (5- (trifluoromethoxy) -2,3- dihydro- 2-dihydroquinoline-3-carboxamide;
(233) Synthesis of N-ethyl-1- (2- (5-hydroxy-2,3-dihydro-1H- Quinolin-3-carboxamide;
2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline (234) -3-carboxamide;
(235) Synthesis of N-ethyl-1- (2- (5-fluoro-2,3-dihydro-1H- Quinolin-3-carboxamide;
(236) 1- (2- (5-Chloro-2,3-dihydro-1H-inden-2-yl) acetyl) -N- -3-carboxamide;
(237) Synthesis of N-ethyl-1- (2- (5-iodo-2,3-dihydro-1H- Quinolin-3-carboxamide;
(238) Synthesis of N-ethyl-1- (2- (5-nitro-2,3-dihydro-1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline -3-carboxamide;
(239) 1- (2- (5-Amino-2,3-dihydro-1H-inden-2-yl) acetyl) -N- -3-carboxamide;
(240) N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;
(241) Synthesis of 1- (3- (2,3-dihydro-1H-inden-2-yl) propanoyl) -N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinolin- - carboxamide;
(242) N-ethyl-2-oxo-N-phenyl-5-propionamido-1,2-dihydroquinoline-3-carboxamide;
(243) 5-Butyramido-N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;
(244) N-methyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(245) N-ethyl-2-oxo-5-pentanamido-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(246) N-ethyl-5- (2-methoxyacetamido) -2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(247) N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(248) N-ethyl-2-oxo-1- (4- (phenylthio) benzyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(249) N-ethyl-2-oxo-1- (4-phenoxybenzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(250) N-ethyl-2-oxo-1- (4- (phenylthio) benzoyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(251) N-ethyl-2-oxo-1- (2- (4- (phenylthio) phenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(252) N-ethyl-2-oxo-1- (2- (4-phenoxyphenyl) acetyl) -N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(253) 1- (2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(254) 1- (4-benzylbenzoyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide;
(255) N- (4-methoxyphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(256) N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(257) 5- (2-Bromoacetamido) -N-ethyl-N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(258) N- (4-bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(259) N- (4-bromophenyl) -1- (cyclopenta-1,3-dienecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(260) N- (4-bromophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-3-carbonyl) -1,2-dihydroquinoline-3-carboxamide;
(261) N- (4-bromophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;
(262) N- (4-bromophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(263) Synthesis of N- (4-bromophenyl) -N-methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline- ;
(264) N- (4-bromophenyl) -1- (2- (furan-2-yl) acetyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(265) 1- (2- (2H-pyrrol-2-yl) acetyl) -N- (4-bromophenyl) Mide;
(266) N- (4-bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(267) N- (4-bromophenyl) -1- (cyclohexanecarbonyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(268) N- (4-bromophenyl) -1- (3-cyclohexylpropanoyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(269) N- (4-bromophenyl) -5- (2-chloroacetamido) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(270) N- (4-chlorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(271) N- (4-Chlorophenyl) -1- (cyclopentanecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(272) N- (4-Chlorophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(273) N- (4-chlorophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;
(274) N- (4-chlorophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide;
(275) N- (4-chlorophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(276) N- (4-chlorophenyl) -1- (2-cyclopentyl acetyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(277) N- (4-Chlorophenyl) -N-ethyl-1- (2- (furan-2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(278) N- (4-chlorophenyl) -N-ethyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxamide;
(279) 1- (2- (2H-pyrrol-2-yl) acetyl) -N- (4- chlorophenyl) -N- ;
(280) N- (4-fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(281) N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2-oxo-2-phenylethyl) -1,2-dihydroquinoline-3-carboxamide;
(282) N- (4-fluorophenyl) -1- (2- (4-methoxyphenyl) -2-oxo-ethyl) - carboxamide;
(283) N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2- Quinolin-3-carboxamide;
(284) N- (4-fluorophenyl) -N-methyl-1- (2- (4- nitrophenyl) Carboxamide;
(285) N- (4-fluorophenyl) -1- (2- (4-hydroxyphenyl) -2-oxo-ethyl) - carboxamide;
(286) N- (4-fluorophenyl) -1- (2- (4-fluorophenyl) -2-oxo-ethyl) - carboxamide;
(287) 1- (2- (4-Ethylphenyl) -2-oxo-ethyl) -N- (4-fluorophenyl) Carboxamide;
(288) 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(289) N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(290) 1- (2- (4-aminophenyl) -2-oxo-ethyl) Carboxamide;
(291) 1- (2- (4-cyanophenyl) -2-oxo-ethyl) -N-ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinolin- - carboxamide;
(292) N-Ethyl-N- (4-fluorophenyl) -1- (2- (4- (methylthio) phenyl) -2-oxo-ethyl) -2-oxo-1,2-dihydroquinoline -3-carboxamide;
(293) N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(294) 1- (2,4-Dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(295) 1- (2,4-Dimethylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(296) N- (4-ethylphenyl) -1- (4-hydroxy-2-methylbenzyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(297) N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(298) 1- (4-ethyl-2-methylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(463) 5-chloro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;
(464) 5-Chloro-1- (4-ethylbenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(465) 5-Chloro-l- (4-isopropylbenzyl) -2-oxo-N-phenethyl-l, 2-dihydroquinoline-3-carboxamide;
(466) 5-Chloro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(467) 5-Chloro-1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(468) 5-Chloro-1- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(469) 5-Chloro-N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(470) 5-Chloro-N- (4-fluorophenethyl) -1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(471) 5-Chloro-N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(472) 5-chloro-N- (4-fluorophenethyl) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;
(473) 1- (4-Ethylbenzyl) -N- (4-fluorophenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carotoxamide;
(474) N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide);
(475) N- (4-fluorophenethyl) -5-nitro-1- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(476) 5-Amino-N- (4-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(477) 1- (4-methoxybenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(478) N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(479) 5-Nitro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;
(480) N- (4-Fluorophenethyl) -5-nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;
(481) 1- (4-Isopropylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(482) Methyl 1- (4-methoxybenzyl) -2-oxo-5- (3-phenylpropanamino) -1,2-dihydroquinoline-3-carboxylate;
(483) Methyl 5- (3-cyclopentylpropanamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(484) Methyl 1- (4-methoxybenzyl) -2-oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline-3-carboxylate;
(485) Methyl 5-benzamido-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(486) Methyl 5- (2- (4-chlorophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(487) Methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(488) Methyl 5- (3,5-dimethyladamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(489) Methyl 5- (3-bromoadamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(490) Methyl 1- (4-methoxybenzyl) -5- (3-methyladamantane-1-carboxyamido) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(491) Methyl 5- (2- (adamantan-1-yl) amido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(492) Methyl 5- (2- (3,5-dimethyladamantan-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroxyquinoline -3-carboxylate;
(493) Methyl 5- (2- (3-bromometh-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline- Rate;
(494) Methyl 1- (4-methoxybenzyl) -5- (2- (3-methyladamantan-1- yl) acetamido) -2-oxo-1,2-dichloroquinoline- Rate;
(495) Methyl 5- (2-cyclohexylacetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(496) Methyl 5- (cyclohexecarboxamidoido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(497) Methyl 5- (adamantane-1-carboxyamido) -1- (4-ethylbenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(498) Methyl 5- (adamantane-1-carboxyamido) -1- (3-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(499) Methyl 5- (adamantane-1-carboxyamido) -1- (4-nitrobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(500) Methyl 5- (adamantane-1-carboxyamido) -2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2- dichloroquinoline-
(501) Methyl 5- (adamantane-1-carboxamido) -1- (4-cyanobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(502) Methyl 5- (adamantane-1-carboxyamido) -1- (4-fluorobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(503) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid;
(504) Ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(505) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N-methyl-2-oxo-1,2-dichloroquinoline-3-carboxamido;
(506) 5- (Adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -N, N-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(507) propyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(508) isopropyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-carboxylate;
(509) N- (1- (4-methoxybenzyl) -3- (methoxymethyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxyamide;
(510) N- (3- (ethoxymethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxyamide;
(511) S-Methyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate;
(512) S-ethyl 5- (adamantane-1-carboxyamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate;
(513) 1- (4-methoxybenzyl) -5-nitroquinolin-2 (1H) -one;
(514) 5-Amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one;
(515) 5-hydrazinyl-l- (4-methoxybenzyl) quinolin-2 (lH) -one;
(516) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;
(517) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carboxamide;
(518) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyladamantane-1-carboxamide;
(519) 3-Bromo-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;
(520) 3-Chloro-N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;
(521) 2- (Adamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;
(522) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -2- (3-methyladamantan-1-yl) acetamide;
(523) 2- (3,5-Dimethyladamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Amide;
(524) 2- (3-Bromo-adamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;
(525) 2- (3-Chloroadamantan-1-yl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide;
(526) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;
(527) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carbohydrazide;
(528) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyladamantane-1-carbohydrazide ;
(529) 3-Bromo-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;
(530) 3-Chloro-N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;
(531) 2- (Adamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetohydrazide;
(532) N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Draazide;
(533) 2- (3,5-Dimethyladamantan-1-yl) -N '- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Acetohydrazide;
(534) 2- (3-Bromo-adamantan-1-yl) -N '- (1- (4- methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Draazide; And
(535) 2- (3-Chloroadamantan-1-yl) -N '- (1- (4- methoxybenzyl) -2-oxo-1,2-dihydroquinolin- Drazide.
제 5 항에 있어서, 상기 퀴놀리논 유도체는
(1) 1-(4-에틸벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(2) 1-(4-에틸펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(3) 1-(4-플루오로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(4) 1-(4-플루오로펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(5) 1-(4-클로로벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(6) 5-니트로-1-(4-니트로벤질)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(7) 1-(4-아미노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(8) 1-(4-시아노벤질)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드;
(14) 1-(4-아미노펜에틸)-5-니트로-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드; 및
(16) 5-니트로-1-(4-니트로펜에틸)-2-옥소-N-펜에틸-1,2-디하이드로퀴놀린-3-카복사마이드
로 구성된 군으로부터 선택되는 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염.6. The method of claim 5, wherein the quinolinone derivative is
(1) 1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(2) 1- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(3) 1- (4-fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(4) 1- (4-Fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(5) 1- (4-Chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(6) 5-Nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(7) 1- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(8) 1- (4-Cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(14) 1- (4-Aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide; And
(16) Synthesis of 5-nitro-1- (4-nitrophenethyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-
&Lt; / RTI &gt; or a pharmaceutically acceptable salt thereof. 삭제delete 제 5 항의 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 염증성 질환 또는 자가면역 질환의 예방 또는 치료용 조성물.A composition for preventing or treating an inflammatory disease or autoimmune disease comprising the quinolinone derivative of claim 5 or a pharmaceutically acceptable salt thereof as an active ingredient. 제 8 항에 있어서, 상기 염증성 질환은 만성폐쇄성 폐질환(chronic obstructive pulmonary disease), 기도 과민성 질환(airways hyper-responsiveness), 폐혈성 쇼크(septic shock), 사구체 신염, 염증성 장질환, 크론병(Crohn's disease), 궤양잘록창자염(ulcerative colitis), 아테롬성 동맥경화증, 골수아구 세포성 백혈병(myoblastic leukaemia), 당뇨, 화상, 허혈성 심장질환, 뇌졸중, 수막염 및 정맥류로 구성된 군으로부터 선택되는 질환인 것을 특징으로 하는 조성물.9. The method of claim 8, wherein the inflammatory disease is selected from the group consisting of chronic obstructive pulmonary disease, airways hyper-responsiveness, septic shock, glomerulonephritis, inflammatory bowel disease, Crohn's disease characterized in that it is a disease selected from the group consisting of ulcerative colitis, ulcerative colitis, atherosclerosis, myoblastic leukemia, diabetes, burn, ischemic heart disease, stroke, meningitis and varicose veins / RTI &gt; 제 8 항에 있어서, 상기 자가면역 질환은 류마티스 관절염, 건선, 알러지성 피부염, 다발성 경화증, 루프스 및 천식으로 구성된 군으로부터 선택되는 질환인 것을 특징으로 하는 조성물.The composition according to claim 8, wherein the autoimmune disease is a disease selected from the group consisting of rheumatoid arthritis, psoriasis, allergic dermatitis, multiple sclerosis, lupus and asthma. 제 8 항에 있어서, 상기 조성물은 IL-2(Interleukin-2) 활성을 억제하는 것을 특징으로 하는 조성물.9. The composition of claim 8, wherein said composition inhibits IL-2 (Interleukin-2) activity.
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CN106146464A (en) * 2015-04-10 2016-11-23 复旦大学 Quinolinones compound and its production and use
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991007401A1 (en) * 1989-11-13 1991-05-30 Schering Corporation 3-substituted-1-(aryl or arylalkyl)-2(1h)-quinolinones
US20050222194A1 (en) 2001-12-14 2005-10-06 Daniel Dube Quinolinones as prostaglandin receptor ligands
US20120184548A1 (en) 2011-01-19 2012-07-19 Romyr Dominique Carboxylic acid aryl amides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991007401A1 (en) * 1989-11-13 1991-05-30 Schering Corporation 3-substituted-1-(aryl or arylalkyl)-2(1h)-quinolinones
US20050222194A1 (en) 2001-12-14 2005-10-06 Daniel Dube Quinolinones as prostaglandin receptor ligands
US20120184548A1 (en) 2011-01-19 2012-07-19 Romyr Dominique Carboxylic acid aryl amides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Anticancer Research, 2010, 30, 4883-4890*

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