WO2015050379A1 - Novel quinolinone derivative and use thereof - Google Patents

Novel quinolinone derivative and use thereof Download PDF

Info

Publication number
WO2015050379A1
WO2015050379A1 PCT/KR2014/009272 KR2014009272W WO2015050379A1 WO 2015050379 A1 WO2015050379 A1 WO 2015050379A1 KR 2014009272 W KR2014009272 W KR 2014009272W WO 2015050379 A1 WO2015050379 A1 WO 2015050379A1
Authority
WO
WIPO (PCT)
Prior art keywords
oxo
carboxamide
dihydroquinoline
ethyl
methyl
Prior art date
Application number
PCT/KR2014/009272
Other languages
French (fr)
Korean (ko)
Inventor
김용철
고효진
곽승화
김민정
이소덕
Original Assignee
광주과학기술원
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 광주과학기술원 filed Critical 광주과학기술원
Priority to KR1020167008791A priority Critical patent/KR101731102B1/en
Publication of WO2015050379A1 publication Critical patent/WO2015050379A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to novel quinolinone derivatives and their preventive and therapeutic uses for diseases associated with excessive IL-2 activity.
  • Interleukin-2 also called T-cel growth factor, plays an important role in T-cell dependent immune response.
  • IL-2 is ⁇ eojin which the 15kDa in size with four bundled with helical protein is produced and secreted by ⁇ cells: not only involved in the proliferation and activation of ⁇ cell differentiation, and other like ⁇ cells and macrophages It is an important cytokine that also affects the activation of immune cells.
  • IL-2 binds to high-affinity receptors consisting of IL-2R a (CD25), IL-2RP (CD122) and IL-2R ⁇ (CD132) subunits of target cell membranes, of which both IL-2RP and IL-2R Y plays an important role in intracellular signaling, and IL-2R a has a short intracellular domain that is not involved in signaling but increases receptor affinity by 10-100 fold.
  • Gene expression encoding IL ⁇ 2 is regulated by electronic regulators such as NF-AT, AP-1, NF- ⁇ ⁇ and Oct, which are rarely expressed in normal, but rapidly when the immune system is activated. However, expression is induced for a limited time so that the protein is synthesized and secreted.
  • the inventors of the present invention sought extensive research to develop compositions for the prevention or treatment of various' inflammatory diseases and autoimmune diseases by discovering effective antagonists of inflammatory cytokines IL-2, which play an important role in the development of immunomodulatory diseases. As a result, the present invention has been completed by discovering that the novel quinolinone derivatives of the present invention inhibit the activity of IL-2 very effectively.
  • Another object of the present invention to provide a composition for inhibiting the activity of IL-2 (Inter leukin-2).
  • Still another object of the present invention is to provide a composition for preventing or treating an inflammatory disease or an autoimmune disease.
  • the invention is represented by the following formula (1) Quinolinone (qui no 1 inone) provides pharmaceutically acceptable salts thereof:
  • Ri, 3 ⁇ 4 and 3 ⁇ 4 are each independently hydrogen, nitro,
  • m is an integer from 0-2) or CrCs alkyl; Cr? Alkoxy; Unsubstituted or C r C 3 alkoxy, dC 5 alkyl, hydroxy, halogen, nitro, NH 2, formyl, cyano, CrCs alkylthio, phenoxy, phenylthio, phenyl-dC 3 alkyl, or substituted pyrazolo Phenyl; Furan; Thiophene; Blood; C 5 -C 6 cycloalkyl; Dihydroindene unsubstituted or substituted with ( ⁇ ): 5 alkyl, d-Cs alkoxy, halogen, nitro, hydroxy, d-Cs alkylthio or -NH 2 ; or diphenylmethyl; and q are each independently an integer from 0-2); R 5 is hydrogen, d—Cs alkoxy dC 3 alkyl, —NA 4 A 5 (A 4 ′ and A 5 are each
  • the present inventors made diligent research efforts to develop a composition for preventing or treating various inflammatory diseases and autoimmune diseases by discovering an effective antagonist of inflammatory cytokine IL ⁇ 2 which plays an important role in the development of immunomodulatory related diseases.
  • the novel quinolinone derivative represented by Chemical Formula 1 was found to effectively inhibit the activity of IL-2.
  • alkyl refers to a straight or branched saturated hydrocarbon group, and includes, for example, methyl, ethyl propyl, isobutyl or pentyl and the like.
  • CPC 5 alkyl means an alkyl group having an alkyl unit having 1 to 5 carbon atoms, and when dC 5 alkyl is substituted, the carbon number of the substituent is not included.
  • dC 5 alkyl is specifically dC 3 alkyl.
  • halogen refers to a halogen group element and includes, for example, fluoro, chloro, bromo and iodo.
  • alkenyl refers to an unsaturated hydrocarbon group including a double bond, and when C 2 -C 5 alkenyl is substituted, carbon number of the substituent is not included. .
  • alkoxy refers to a radical formed by the removal of hydrogen from an alcohol, where dC 3 alkoxy is substituted, the carbon number of the substituent is It is not included.
  • aryl refers to a substituted or unsubstituted monocyclic or polycyclic carbon ring which is wholly or partially unsaturated and has aromatic (aromat i c i ty).
  • alkylthio means a radical formed by removing hydrogen from thio (thio 1), and when C-C 5 alkylthio is substituted, the carbon number of the substituent is not included.
  • arylalkyl refers to alkyl substituted with an aryl group.
  • Aryl (: 4 ( alkyl) means an alkyl unit having 1 to 4 carbon atoms substituted with an aryl group.
  • phenylthio refers to a radical formed by the removal of hydrogen from thiophenol (thiophenol).
  • the quinolinone derivatives of the present invention may be used in the form of pharmaceutically acceptable salts, and as salts, acid addition salts formed by pharmaceutically acceptable free acids may be used.
  • Acid addition salts include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid, aliphatic mono and dicarboxylates, phenyl-substituted alkanoates, hydroxy alkanoates and alkanes.
  • Acid addition salts according to the present invention are conventional methods, for example, a warfare product formed by dissolving a derivative of Formula 1 in an organic solvent, for example methane, ethanol, acetone, methylene chloride, acetonitrile, and adding an organic or inorganic acid.
  • an organic solvent for example methane, ethanol, acetone, methylene chloride, acetonitrile, and adding an organic or inorganic acid.
  • the solvent may be prepared by filtration, drying, or by distillation under reduced pressure of the solvent and excess acid, followed by drying or crystallization under an organic solvent.
  • Bases can also be used to make pharmaceutically acceptable metal salts.
  • Alkali metal or alkaline earth metal salts are obtained, for example, by dissolving the compound in an excess of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is pharmaceutically suitable to prepare sodium, potassium or calcium salt as the metal salt.
  • Corresponding silver salts are also obtained by reacting an alkali or alkaline earth metal salt with a suitable negative salt (eg silver nitrate).
  • the present invention includes not only the quinolinone derivative represented by Formula 1 and a pharmaceutically acceptable salt thereof, but also possible solvates, hydrates, stereoisomers, and the like that can be prepared therefrom. According to a specific embodiment of the invention, the formula 1 of the present invention.
  • R 2 and 3 ⁇ 4 are each independently hydrogen, nitro, halogen, -N3 ⁇ 4, hydrazino or (Phenyl unsubstituted or substituted with dC 3 alkyl, halogen, C 2 -C 3 alkenyl, nitro, hydroxy, hydroxy dC 3 alkyl, d—C 3 alkoxy or phenyl; naphthalyl; unsubstituted or halogen, DC 3 alkyl substituted with nitro, C 2 _C 3 alkenyl; c 5 -c 6 cycloalkyl; adamantane, unsubstituted or substituted with halogen or methyl; Ci-C 3 alkoxy; CrCs alkylthio; or benzodioxol N is 0-2 Is an integer).
  • R4 of formula 1 of the present invention is hydrogen, dC 3 alkyl, c (A 2 is unsubstituted or halogen, dC 3 alkyl, C ⁇ C 3 alkoxy, nitro, —N3 ⁇ 4, dC 3 Phenyl substituted with alkylthio, phenyl, phenyl (: ⁇ (: 3 alkyl, phenoxy, cyano, hydroxy, hydroxy CrC 3 alkyl, formyl, phenylthio or pyrazole; naphthalyl; cyclopentadiene; blood Furan; thiophene; C 5 -C 6 cycloalkyl; unsubstituted or d—C 3 alkyl, dC 3 alkoxy, halogen, nitro, cyano hydroxy, formyl, C ⁇ C 3 alkylthio or —NH 2 ; Substituted dihydroindene;
  • 3 ⁇ 4 of formula 1 of the present invention is hydrogen, d-Cs alkoxy C ⁇ C 2 alkyl, -NA 4 A 5 (A 4 and A 5 are each independently hydrogen; unsubstituted or phenyl , dihydro-indene, naphthyl talril, dC dC 3 3 alkoxy or alkyl, dC 3 alkyl substituted by alkylthio; unsubstituted or dC 3 alkyl, halogen, hydroxy dC 3 alkyl, C 2 -C 3 alkenyl, sulfonamide, Phenyl substituted with CrC 3 alkoxy, hydroxy or nitro) or [A 6 is dC 3 alkoxy, halogen hydroxy, c ⁇ C 2 alkylthio or —NA 7 A 8 (A 7 and A 8 are each independently hydrogen; unsubstituted or substituted with phenyl, nitro,
  • the present invention is a composition for inhibiting the activity of IL-2 (Int er eukin-2) comprising a quinolinone derivative disclosed in the present invention or a pharmaceutically acceptable salt thereof as an active ingredient To provide.
  • IL-2 Int er eukin-2
  • the present invention provides a prophylactic method for preventing a disease associated with IL-2 overexpression or IL-2 overactivity comprising a quinolinone derivative disclosed herein or a pharmaceutically acceptable salt thereof as an active ingredient. Or a therapeutic composition.
  • the pharmaceutical composition of the present invention includes a pharmaceutically acceptable carrier.
  • Pharmaceutically acceptable carriers contained in the pharmaceutical composition of the present invention are those commonly used in the preparation, lactose, textose, sucrose, sorbbi, manny, starch, acacia rubber, phosphate, alginate, Gelatin Calcium Silicate, Microcrystalline Cellulose, Polyvinylpyridone, Cellulose, Water, Syrup, Methyl Cellulose, Methylhydroxybenzoate, Propylhydroxybenzoate, Talc, Magnesium Stearate and Mineral Oil One is not limited thereto.
  • the pharmaceutical composition of the present invention may further include a lubricant, a humectant, a sweetener, a flavoring agent, an emulsifier, a suspending agent, a preservative, and the like, in addition to the above components.
  • a lubricant e.g., talc, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mannitol, mann
  • the pharmaceutical composition of the present invention may be administered orally or parenterally, and in the case of parenteral administration, it may be administered by intravenous injection, subcutaneous injection, intramuscular injection, intraperitoneal injection, transdermal administration, or the like.
  • Suitable dosages of the pharmaceutical compositions of the present invention may be prescribed in various ways depending on factors such as the method of formulation, the mode of administration, the age of the patient, body weight, sex, morbidity, food, time of administration, route of excretion and response sensitivity. Can be.
  • the daily dose of the pharmaceutical composition of the present invention is, for example, 0.001-100 mg / kg.
  • the pharmaceutical compositions of the present invention may be prepared in unit dose form by formulating with a pharmaceutically acceptable carrier and / or excipient according to methods which can be easily carried out by those skilled in the art. Or may be prepared by incorporation into a multi-dose container.
  • the formulation may be in the form of solutions, suspensions, syrups or emulsions in oil or aqueous media, or may be in the form of axes, powders, powders, granules, tablets or accelerators, and may further comprise dispersants or stabilizers.
  • the disease associated with IL-2 overexpression or IL-2 overactivity treated with the composition of the invention is an inflammatory disease or an autoimmune disease.
  • the inflammatory disease is chronic obstructive pulmonary disease (chroni c obstructive pulmonary disease, airways hyper- responsiveness, septic shock, glomerulonephritis, inflammatory bowel disease, Crohn's disease, ulcerat ive colitis, atherosclerosis And myoblastic leukaemia, diabetes, burns, ischemic heart disease, stroke, meningitis and varicose veins.
  • the autoimmune disease is a disease selected from the group consisting of rheumatoid arthritis, psoriasis, allergic dermatitis, multiple sclerosis, lupus and asthma.
  • the present invention provides a method for treating an inflammatory disease or an autoimmune disease comprising administering to a subject a composition comprising a quinolinone derivative of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient.
  • a composition comprising a quinolinone derivative of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the quinolinone derivative compounds used in the present invention and the inflammatory diseases or autoimmune diseases that can be prevented or treated with the compositions of the present invention have already been described above, and the description thereof is omitted to avoid excessive redundancy.
  • the present invention provides various novel quinolinone derivative compounds and compositions for inhibiting IL-2 activity comprising them as active ingredients.
  • the present invention can be usefully used for the prevention or treatment of various diseases associated with excessive expression or activity of IL-2, namely chronic inflammatory disease, inflammatory pain or autoimmune disease.
  • Quinolinone is a natural product derived from plants and is known to have various biological activities.
  • quinolinone has a chemical structure and shows the possibility of hydrogen bonding to the lactam moiety contained therein. Based on these facts, a large amount of quinolinone compounds was efficiently synthesized to investigate the biological activity of quinolinones.
  • IL-2 ELISA analysis explored the potential as an immunosuppressant in Jurkat T cells and confirmed that certain substances have a high potential as immunosuppressants.
  • IL-2 is produced primarily in T cells but also in killer (NK) cells.
  • T cell NK cells cytokine networks.
  • IL-2 gene knockout mice are known to develop inflammatory bowel disease and hemolytic anemia. It is also known to increase the production of IgGl, IgE, and IL-2 plays an important role in maintaining the balance of T H 1 / T H 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to: various novel quinolinone derivative compounds; and a composition for inhibiting IL-2 activity, containing the same as an active ingredient. The present invention can be useful for prevention or treatment of various diseases related to the excessive expression/activity of IL-2, that is, chronic inflammatory diseases or autoimmune diseases.

Description

【명세서】  【Specification】
【발명의 명칭】  [Name of invention]
신규한 퀴놀리논 유도체 및 이의 용도  Novel quinolinone derivatives and uses thereof
【기술 분야】 [Technical field]
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 preventive and therapeutic uses for diseases associated with excessive IL-2 activity.
【배경 기슬】 [Background]
T-세포 성장인자 (T-cel l growth factor )라고도 불리우는 인터루킨 -2 ( Inter leukin-2 , IL-2)는 T-세포 의존성 면역반웅에서 증요한 역할을 한다. IL-2는 4개의 번들로 15kDa 크기의 이로어진 α -나선 단백질로, Τ 세포에서 생성 및 분비되며, : Τ 세포의 증식 및 활성화와 분화에 관여할 뿐만 아니라， Β 세포나 대식세포 등과 같은 다른 면역세포들의 활성화에도 영향을 미치는 중요한 사이토카인 (cytokine)이다. IL-2는 타겟 세포막의 IL-2R a (CD25) , IL-2RP (CD122) 및 IL— 2R γ (CD132) 서브유닛으로 이루어진 고-친화도 수용체와 결합하며， 이중 IL-2RP 및 IL-2R Y는 세포 내 신호전달에 중요한 역할을 하고， IL-2R a는 세포질내 도메인이 짧아 신호전달에 관여하지는 않지만 수용체와친화도를 10-100배 증가시킨다. Interleukin-2 (IL-2), also called T-cel growth factor, plays an important role in T-cell dependent immune response. IL-2 is α eojin which the 15kDa in size with four bundled with helical protein is produced and secreted by Τ cells: not only involved in the proliferation and activation of Τ cell differentiation, and other like Β cells and macrophages It is an important cytokine that also affects the activation of immune cells. IL-2 binds to high-affinity receptors consisting of IL-2R a (CD25), IL-2RP (CD122) and IL-2R γ (CD132) subunits of target cell membranes, of which both IL-2RP and IL-2R Y plays an important role in intracellular signaling, and IL-2R a has a short intracellular domain that is not involved in signaling but increases receptor affinity by 10-100 fold.
ILᅳ 2를 코딩하는 유전자 발현은 NF-AT, AP-1 , NF- κ Β, Oct 등의 전자조절인자들에 의하여 조절되며, 평상시에는 거의 발현되지 않다가， 면역체계가 활성화될 경우에 급격히 그러나 한시적으로 발현이 유도되어 단백질이 합성 및 분비된다.  Gene expression encoding IL ᅳ 2 is regulated by electronic regulators such as NF-AT, AP-1, NF-κ Β and Oct, which are rarely expressed in normal, but rapidly when the immune system is activated. However, expression is induced for a limited time so that the 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 (사이클로 sporin A) , F 506 등의 화합물은 부작용이 심해 많은 만성 질환들을 포함하는 염증 및 조절되지 않은 면역 반웅관련 질환에 있어 장기 투여가 불가능했으며， 이에 보다 효율적이며 안전하고 단순한 기전을 가지는 IL-2 저해훼의 개발이 절실한 상황이다. 본 명세서 전체에 걸쳐 다수의 논문 및 특허문헌이 참조되고 0— 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. On the other hand, excessive expression of IL-2 causes various immune system diseases, including inflammation and autoimmune diseases. Thus, interfering with the biological activity of IL-2 or inhibiting the interaction between IL-2 and each subunit of the IL-2 receptor is an effective approach to the treatment of diseases due to excessive expression and activity of IL-2. Will be. Compounds such as cyclosporin A (cyclosporin A) and F 506, which have been suggested as IL-2 inhibitors until now, have severe side effects and many chronic Long-term administration was not possible in inflammatory and uncontrolled immune response-related diseases including diseases, and there is an urgent need for the development of IL-2 inhibitors with a more efficient, safe and simple mechanism. Throughout this specification many papers and patent documents are referenced and 0— citations are indicated. The disclosures of cited papers and patent documents are incorporated herein by reference in their entirety, and the level of the technical field to which the present invention belongs and the contents of the present invention are more clearly explained.
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】  [Technical problem]
본 발명자 "은 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 활성올 매우 효과적으로 억제함을 발견함으로써, 본 발명을 완성하게 되었다.  The inventors of the present invention sought extensive research to develop compositions for the prevention or treatment of various' inflammatory diseases and autoimmune diseases by discovering effective antagonists of inflammatory cytokines IL-2, which play an important role in the development of immunomodulatory diseases. As a result, the present invention has been completed by discovering that the novel quinolinone derivatives of the present invention inhibit the activity of IL-2 very effectively.
따라서 본 발명의 목적은 신규한 퀴놀리논 유도체를 제공하는 데 있다.  It is therefore an object of the present invention to provide novel quinolinone derivatives.
본 발명의 다른 목적은 IL-2( Inter leukin-2)의 활성 억제용 조성물을 제공하는 데 있다.  Another object of the present invention to provide a composition for inhibiting the activity of IL-2 (Inter leukin-2).
본 발명의 또 다른 목적은 염증성 질환 또는 자가면역 질환의 예방 또는 치료용 조성물을 제공하는 데 있다. 본 발명의 다른 목적 및 이점은 하기의 발명의 상세한 설명， 청구범위 및 도면에 의해 보다 명확하게 된다.  Still another object of the present invention is to provide a composition for preventing or treating an inflammatory disease or an autoimmune disease. Other objects and advantages of the present invention will become apparent from the following detailed description, claims and drawings.
【기술적 해결방법】 Technical Solution
본 발명의 일 양태에 따르면, 본 발명은 다음의 화학식 1로 표시되는 퀴놀리논 (qui no 1 inone ) 이의 약제학적으로 허용되는 염을 제공한다: According to one aspect of the invention, the invention is represented by the following formula (1) Quinolinone (qui no 1 inone) provides pharmaceutically acceptable salts thereof:
화학식 1  Formula 1
Figure imgf000004_0001
Figure imgf000004_0001
상기 화학식에서, Ri, ¾ 및 ¾는 각각 독립적으로 수소， 니트로，  In the above formula, Ri, ¾ and ¾ are each independently hydrogen, nitro,
할로겐， -NH2 , 하이드라지노 또는
Figure imgf000004_0002
( 은 비치환되거나 CrQ 알킬， 할로겐， C2-C5 알케닐， 니트로, 하이드록시, 하이드록시 d-C5 알킬， C厂 C3 알콕시 또는'페닐로 치환된 C6-C10 아릴; 비치환되거나 할로겐， 니트로， C2-C5알케닐로 치환된 d-C5 알킬 ; C5-C6 사이클로알킬 ; 비치환되거나 할로겐 또는 (：厂¾ 알킬로 치환된 아다만테인; C3 알콕시; C厂 C5 알킬티오; 또는 이고; n은 0-2의 정수이다)이고; R4는 수소， d-Cs 알킬,
Figure imgf000004_0003
Halogen, -NH 2 , hydrazino or
Figure imgf000004_0002
(C 6 -C 10 aryl unsubstituted or substituted with CrQ alkyl, halogen, C 2 -C 5 alkenyl, nitro, hydroxy, hydroxy dC 5 alkyl, C 厂 C 3 alkoxy or ' phenyl; unsubstituted or DC 5 alkyl substituted with halogen, nitro, C 2 -C 5 alkenyl; C 5 -C 6 cycloalkyl; adamantane, unsubstituted or substituted with halogen or (： 厂 ¾ alkyl; C 3 alkoxy; C 厂 C 5 alkylthio; or; n is an integer from 0-2), R 4 is hydrogen, d-Cs alkyl,
Figure imgf000004_0003
rfev (A2는 비치환되거나 할로겐， d-Cs 알킬， Cr~C3 알콕시， 니트로, -rfev (A 2 is unsubstituted or halogen, d-Cs alkyl, Cr-C 3 alkoxy, nitro,-
N¾ , C1-C5 알킬티오， 페닐， 페닐 Ci-C5 알킬， 페녹시, 시아노， 하이드록시, 하이드록시 CrC5 알킬， 포르밀, 페닐티오 또는 피라졸로 치환된 C6-C10 아릴; 사이클로펜타디엔； 피롤; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 Ci-C5 알킬, Cr"C3 알콕시， 할로겐， 니트로， 시아노， 하이드록시 , 포르밀， Ci-C5 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; C 6 -C 10 aryl substituted with N¾, C1-C5 alkylthio, phenyl, phenyl Ci-C 5 alkyl, phenoxy, cyano, hydroxy, hydroxy CrC 5 alkyl, formyl, phenylthio or pyrazole; Cyclopentadiene; pyrrole; Furan; Thiophene; C 5 -C 6 cycloalkyl; Dihydroindene unsubstituted or substituted with Ci-C 5 alkyl, Cr "C 3 alkoxy, halogen, nitro, cyano, hydroxy, formyl, Ci-C 5 alkylthio or -NH 2 ; or diphenylmethyl ego;
m은 0-2의 정수이다) 또는
Figure imgf000004_0004
CrCs 알킬; Cr ? 알콕시 ; 비치환되거나 Cr C3 알콕시, d-C5 알킬， 하이드록시， 할로겐， 니트로， NH2 , 포르밀， 시아노, CrCs 알킬티오， 페녹시 , 페닐티오， 페닐 d— C3 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피를; C5-C6 사이클로알킬; 비치환되거나 (：厂(：5 알킬, d-Cs 알콕시 , 할로겐， 니트로， 하이드록시 , d-Cs 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p 및 q는 각각 독립적으로 0-2의 정수이다)이고; R5는 수소， d—Cs 알콕시 d-C3 알킬, -NA4A5(A4 '및 A5는 각각 독립적으로 수소; 비치환되거나 페닐， 디하이드로인덴， 나프탈릴， d-C3 알콕시 또는 d-Q 알킬티오로 치환된 d-m is an integer from 0-2) or
Figure imgf000004_0004
CrCs alkyl; Cr? Alkoxy; Unsubstituted or C r C 3 alkoxy, dC 5 alkyl, hydroxy, halogen, nitro, NH 2, formyl, cyano, CrCs alkylthio, phenoxy, phenylthio, phenyl-dC 3 alkyl, or substituted pyrazolo Phenyl; Furan; Thiophene; Blood; C 5 -C 6 cycloalkyl; Dihydroindene unsubstituted or substituted with (厂): 5 alkyl, d-Cs alkoxy, halogen, nitro, hydroxy, d-Cs alkylthio or -NH 2 ; or diphenylmethyl; and q are each independently an integer from 0-2); R 5 is hydrogen, d—Cs alkoxy dC 3 alkyl, —NA 4 A 5 (A 4 ′ and A 5 are each independently hydrogen; unsubstituted or phenyl, dihydroindene, naphthalyl, dC 3 alkoxy or dQ alkyl D- substituted by thio
C5 알킬; 비치환되거나 C厂 C5 알킬， 할로겐, 하이드록시 d-Cs 알킬， C2-C5 알케닐， 설폰아마이드， d-Cs 알콕시， 하이드록시 또는 니트로로 치환된 페닐이다) 또는
Figure imgf000005_0001
[A6는 d-C3 알콕시， 할로겐， 하이드록시， d-Cs 알킬티오 또는 -NA7A8(A7 및 ^은 각각 독립적으로 수소; 비치환되거나 페닐， 니트로, 하이드록시, 할로겐, 디하이드로인덴， 나프탈릴, d-C3 알콕시， - C3 알킬아민 또는 d-Cs 알킬티오로 치환된 CrC5 알킬; C2-C5 알케닐; 비치환되거나 d-Cs 알킬， 할로겐， 하이드록시 d— C5 알킬， C2-C5 알케닐， 설폰아마이드， Cr"C3 알콕시， 하이드록시 또는 니트로로 치환된 페닐이다) ] 이다. C 5 alkyl; Unsubstituted or C厂C 5 alkyl, halogen, hydroxy, d-Cs-alkyl, C 2 -C 5 alkenyl, sulfonamide, d-Cs alkoxy, hydroxy nitro or phenyl substituted with) or
Figure imgf000005_0001
[A 6 is dC 3 alkoxy, halogen, hydroxy, d-Cs alkylthio or -NA 7 A 8 (A 7 and ^ are each independently hydrogen; unsubstituted or phenyl, nitro, hydroxy, halogen, dihydroin Den, naphthalyl, dC 3 alkoxy, CrC 5 alkyl substituted with C 3 alkylamine or d-Cs alkylthio; C 2 -C 5 alkenyl; unsubstituted or d-Cs alkyl, halogen, hydroxy d—C 5 alkyl, C 2 -C 5 alkenyl, sulfonamide, Cr ″ C 3 alkoxy, hydroxy or nitro substituted phenyl).
본 발명자들은 면역조절 관련 질환의 발병에 중요한 역할을 하는 염증성 사이토카인인 ILᅳ 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 발견함으로쎄 본 발명을 완성하게 되었다.  The present inventors made diligent research efforts to develop a composition for preventing or treating various inflammatory diseases and autoimmune diseases by discovering an effective antagonist of inflammatory cytokine IL ᅳ 2 which plays an important role in the development of immunomodulatory related diseases. As a result, the novel quinolinone derivative represented by Chemical Formula 1 was found to effectively inhibit the activity of IL-2.
본 명세서에서 용어 "알킬" 은 직쇄 또는 분쇄의 포화 탄화수소기를 의미하며， 예를 들어， 메틸， 에틸ᅳ 프로필， 이소부틸 또는 펜틸 등을 포함한다. CPC5 알킬은 탄소수 1 내지 5의 알킬 유니트를 가지는 알킬기를 의미하며， d-C5 알킬이 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다. 화학식 1에서， d-C5알킬은 구체적으로는 d-C3알킬이다. 본 명세서에서 용어 "할로겐" 은 할로겐족 원소를 나타내며， 예컨대， 플루오로， 클로로, 브로모 및 요오도를 포함한다. As used herein, the term "alkyl" refers to a straight or branched saturated hydrocarbon group, and includes, for example, methyl, ethyl propyl, isobutyl or pentyl and the like. CPC 5 alkyl means an alkyl group having an alkyl unit having 1 to 5 carbon atoms, and when dC 5 alkyl is substituted, the carbon number of the substituent is not included. In Formula 1, dC 5 alkyl is specifically dC 3 alkyl. 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. . As used herein, the term "alkenyl" refers to an unsaturated hydrocarbon group including a double bond, and when C 2 -C 5 alkenyl is substituted, carbon number of the substituent is not included. .
본 명세서에서 용어 "알콕시" 는 알코올에서 수소가 제거되어 형성된 라디칼을 의미하며， d-C3 알콕시가 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다. As used herein, the term "alkoxy" refers to a radical formed by the removal of hydrogen from an alcohol, where dC 3 alkoxy is substituted, the carbon number of the substituent is It is not included.
본 명세서에서 용어 "아릴 " 은 전체적으로 또는 부분적으로 불포화 되고 방향성 (aromat i c i ty)를 가지는 치환 또는 비치환된 모노사이클릭 또는 폴리사이클릭 탄소 고리를 의미한다.  As used herein, the term "aryl" refers to a substituted or unsubstituted monocyclic or polycyclic carbon ring which is wholly or partially unsaturated and has aromatic (aromat i c i ty).
본 명세서에서 용어 "알킬티오" 은 티을 (티오 1 )에서 수소가 제거되어 형성된 라디칼올 의미하며， C— C5 알킬티오가 치환된 경우 치환체의 탄소수는 포함되지 않은 것이다. As used herein, the term "alkylthio" means a radical formed by removing hydrogen from thio (thio 1), and when C-C 5 alkylthio is substituted, the carbon number of the substituent is not included.
본 명세서에서 용어 "아릴알킬" 은 아릴기로 치환된 알킬을 의미한다. 아릴 (：广(：4 알킬은 아릴기로 치환된 탄소수 1 내지 4의 알킬 유니트를 의미한다. As used herein, the term "arylalkyl" refers to alkyl substituted with an aryl group. Aryl (： 4 ( alkyl) means an alkyl unit having 1 to 4 carbon atoms substituted with an aryl group.
본 명세서 서 용어 "페닐티오" 는 티오페놀 (티오페놀)에서 수소가 제거되어 형성된 라디칼을 의미한다. 본 발명의 퀴놀리논 유도체는 약학적으로 허용 가능한 염의 형태로 사용될 수 있으며， 염으로는 약학적으로 허용 가능한 유리산 ( free ac i d)에 의해 형성된 산 부가염올 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， 글루콘 '산， 메탄설폰산, 4-를루엔설폰산, 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， 프로피을레이트, 옥살레이트， 말로'네이트， 석시네이트， 수베레이트, 세바케이트, 푸마레이트, 말리에이트, 부틴 -1 , 4-디오에이트， 핵산 -1 ,6- 디오에이트, 벤조에이트， 클로로벤조에이트， 메틸벤조에이트， 디니트로 벤조에이트， 하이드록시벤조에이트， 메록시벤조에이트， 프탈레이트, 테레프탈레이트， 밴젠설포네이트， 를루엔설포네이트， 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. As used herein, the term "phenylthio" refers to a radical formed by the removal of hydrogen from thiophenol (thiophenol). The quinolinone derivatives of the present invention may be used in the form of pharmaceutically acceptable salts, and as salts, acid addition salts formed by pharmaceutically acceptable free acids may be used. Acid addition salts include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid, aliphatic mono and dicarboxylates, phenyl-substituted alkanoates, hydroxy alkanoates and alkanes. video obtained from the maleate, aromatic acids, aliphatic and aromatic sulfonic acids with non-toxic organic acid, acetic acid, benzoic acid, citric acid, lactic acid, maleic acid, gluconic "acid, methanesulfonic acid, organic acid, such as the 4-sulfonic acid, tartaric acid, fumaric acid, such as toluene . In a non-toxic salts such as pharmaceutically sulfate, fatigue sulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate,. Monohydrogen phosphate, dihydrogen phosphate, metaphosphate, pyrophosphate chloride, bromide, iodide, fluoride, acetate, propionate, decanoate, caprylate, acrylate, formate, isobutyrate, cape rate, heptanoate, peuropieul rate, oxalate, words, carbonate, succinate, suberate, sebacate, fumarate, maleate, butyne-1, 4-audio maleate, acid-1, 6-video benzoate, benzoin Ate, chlorobenzoate, methyl benzoate, dinitro benzoate, hydroxy benzoate, hydroxy benzoate, phthalate, Terephthalate, bansensulfonate, toluenesulfonate, chlorobenzenesulfonate, xylenesulfonate, phenylacetate, phenylpropionate, phenylbutyrate, citrate, lactate β—hydroxybutyrate, glycolate, malate, tart Latex, methanesulfonate, propanesulfonate, naphthalene-1-sulfonate, naphthalene-2-sulfonate or mandelate.
본 발명에 따른 산 부가염은 통상의 방법， 예를 들면， 화학식 1의 유도체를 유기용매， 예를 들면 메탄을， 에탄올， 아세톤， 메틸렌클로라이드， 아세토니트릴 등에 녹이고 유기산 또는 무기산을 가하여 생성된 참전물을 여과, 건조하여 제조되거나, 용매와 과량의 산을 감압 증류한 후 건조하거나 유기용매 하에서 결정화시켜셔 제조할 수 있다.  Acid addition salts according to the present invention are conventional methods, for example, a warfare product formed by dissolving a derivative of Formula 1 in an organic solvent, for example methane, ethanol, acetone, methylene chloride, acetonitrile, and adding an organic or inorganic acid. The solvent may be prepared by filtration, drying, or by distillation under reduced pressure of the solvent and excess acid, followed by drying or crystallization under 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 칼슘염올 제조하는 것이 제약상 적합하다. 또한， 이에 대응하는 은염은 알칼리 금속 또는 알칼리 토금속 염을 적당한 음염 (예， 질산은)과 반웅시켜 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. 본 발명의 구체적인 구현예에 따르면 , 본 발명의 화학식 1의 . R2 및 ¾는 각각 독립적으로 수소, 니트로， 할로겐， -N¾ , 하이드라지노 또는
Figure imgf000007_0001
( 은 비치환되거나 d-C3 알킬， 할로겐， C2-C3알케닐, 니트로, 하이드록시， 하이드록시 d-C3 알킬， d— C3 알콕시 또는 페닐로 치환된 페닐; 나프탈릴; 비치환되거나 할로겐， 니트로， C2_C3알케닐로 치환된 d-C3 알킬; c5-c6 사이클로알킬; 비치환되거나 할로겐 또는 메틸로 치환된 아다만테인; Ci-C3 알콕시; CrCs 알킬티오; 또는 벤조디옥솔이고; n은 0-2의 정수이다)이다. 본 발명의 구체적인 구현예에 따르면, 본 발명의 화학식 1의 R4는 수소， d-C3 알킬, 시 (A2는 비치환되거나 할로겐， d-C3 알킬， C广 C3 알콕시， 니트로， -N¾ , d-C3 알킬티오， 페닐, 페닐 (：厂(：3 알킬， 페녹시， 시아노， 하이드록시, 하이드록시 CrC3 알킬， 포르밀， 페닐티오 또는 피라졸로 치환된 페닐; 나프탈릴; 사이클로펜타디엔; 피를; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 d— C3 알킬, d-C3 알콕시， 할로겐， 니트로， 시아노 하이드록시， 포르밀, C厂 C3 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; m은 0-2의 정수이다) 또는
Figure imgf000008_0001
(A3는 Ci-C3 알킬; C C3 알콕시 ; 비치환되거나 Ci-C3 알콕시， d-C3 알킬， 하이드록시， 할로겐， 니트로， -N¾ , 포르밀， 시아노， d-Cs 알킬티오, 페녹시, 페닐티오, 페닐 d-Cs 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피를; C5— C6 사이클로알킬; 비치환되거나 d-Cg 알킬， d-C3 알콕시， 할로겐， 니트로, 하이드록시, d-Cs 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p는 0이며 q는 0-2의 정수이다)이다. 본 발명의 구체적인 구현예에 따르면, 본 발명의 화학식 1의 ¾는 수소， d-Cs 알콕시 C厂 C2 알킬， -NA4A5(A4 및 A5는 각각 독립적으로 수소; 비치환되거나 페닐, 디하이드로인덴, 나프탈릴， d-C3 알콕시 또는 d-C3 알킬티오로 치환된 d-C3 알킬; 비치환되거나 d-C3 알킬， 할로겐, 하이드록시 d-C3 알킬， C2-C3 알케닐， 설폰아마이드， CrC3 알콕시， 하이드록시 또는 니트로로 치환된 페닐이다) 또는
Figure imgf000008_0002
[A6는 d-C3 알콕시, 할로겐 하이드특시, c厂 C2 알킬티오 또는 -NA7A8(A7 및 A8은 각각 독립적으로 수소; 비치환되거나 페닐, 니트로， 하이드록시， 할로겐， 디하이드로인덴， 나프탈릴， d-C3 알콕시, Cr"C3 알킬아민 또는 C -C2 알킬티오로 치환된 d— C3 알킬; C2-C3 알케닐; 비치환되거나 d-C3 알킬， 할로겐， 하이드록시 d-C3 알킬， C2-C3알케닐， 설폰아마이드, d-Cs 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다) ]이다. 본 발명의 보다 구체적인 구현예에 따르면, 본 발명의 퀴놀리논 유도체는 Bases can also be used to make pharmaceutically acceptable metal salts. Alkali metal or alkaline earth metal salts are obtained, for example, by dissolving the compound in an excess of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is pharmaceutically suitable to prepare sodium, potassium or calcium salt as the metal salt. Corresponding silver salts are also obtained by reacting an alkali or alkaline earth metal salt with a suitable negative salt (eg silver nitrate). In addition, the present invention includes not only the quinolinone derivative represented by Formula 1 and a pharmaceutically acceptable salt thereof, but also possible solvates, hydrates, stereoisomers, and the like that can be prepared therefrom. According to a specific embodiment of the invention, the formula 1 of the present invention. R 2 and ¾ are each independently hydrogen, nitro, halogen, -N¾, hydrazino or
Figure imgf000007_0001
(Phenyl unsubstituted or substituted with dC 3 alkyl, halogen, C 2 -C 3 alkenyl, nitro, hydroxy, hydroxy dC 3 alkyl, d—C 3 alkoxy or phenyl; naphthalyl; unsubstituted or halogen, DC 3 alkyl substituted with nitro, C 2 _C 3 alkenyl; c 5 -c 6 cycloalkyl; adamantane, unsubstituted or substituted with halogen or methyl; Ci-C 3 alkoxy; CrCs alkylthio; or benzodioxol N is 0-2 Is an integer). According to a specific embodiment of the present invention, R4 of formula 1 of the present invention is hydrogen, dC 3 alkyl, c (A 2 is unsubstituted or halogen, dC 3 alkyl, C 广 C 3 alkoxy, nitro, —N¾, dC 3 Phenyl substituted with alkylthio, phenyl, phenyl (： 厂 (： 3 alkyl, phenoxy, cyano, hydroxy, hydroxy CrC 3 alkyl, formyl, phenylthio or pyrazole; naphthalyl; cyclopentadiene; blood Furan; thiophene; C 5 -C 6 cycloalkyl; unsubstituted or d—C 3 alkyl, dC 3 alkoxy, halogen, nitro, cyano hydroxy, formyl, C 厂 C 3 alkylthio or —NH 2 ; Substituted dihydroindene; or diphenylmethyl; m is an integer from 0-2) or
Figure imgf000008_0001
(A 3 is Ci-C 3 alkyl; CC 3 alkoxy; unsubstituted or Ci-C 3 alkoxy, dC 3 alkyl, hydroxy, halogen, nitro, -N¾, formyl, cyano, d-Cs alkylthio, phenoxy Phenyl substituted by phenylthio, phenyl d-Cs alkyl or pyrazole; furan; thiophene; blood; C 5 — C 6 cycloalkyl; unsubstituted or d-Cg alkyl, dC 3 alkoxy, halogen, nitro, hydr Dihydroxyindene substituted with oxy, d-Cs alkylthio or —NH 2 ; or diphenylmethyl; p is 0 and q is an integer from 0-2). According to a specific embodiment of the present invention, ¾ of formula 1 of the present invention is hydrogen, d-Cs alkoxy C 厂 C 2 alkyl, -NA 4 A 5 (A 4 and A 5 are each independently hydrogen; unsubstituted or phenyl , dihydro-indene, naphthyl talril, dC dC 3 3 alkoxy or alkyl, dC 3 alkyl substituted by alkylthio; unsubstituted or dC 3 alkyl, halogen, hydroxy dC 3 alkyl, C 2 -C 3 alkenyl, sulfonamide, Phenyl substituted with CrC 3 alkoxy, hydroxy or nitro) or
Figure imgf000008_0002
[A 6 is dC 3 alkoxy, halogen hydroxy, c 厂 C 2 alkylthio or —NA 7 A 8 (A 7 and A 8 are each independently hydrogen; unsubstituted or substituted with phenyl, nitro, hydroxy, halogen, di D—C 3 alkyl substituted with hydroindene, naphthalyl, dC 3 alkoxy, Cr ”C 3 alkylamine or C-C 2 alkylthio; C 2 -C 3 alkenyl; unsubstituted or dC 3 alkyl, Halogen, hydroxy dC 3 alkyl, C 2 -C 3 alkenyl, sulfonamide, d-Cs alkoxy, hydroxy or phenyl substituted with nitro). According to a more specific embodiment of the present invention, the quinolinone derivative of the present invention
( 1) 1ᅳ(4ᅳ에틸벤질)ᅳ 5-니트로 -2-옥소 -N-펜에틸 -1，2ᅳ디하이드로퀴놀린 -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-펜에릴 -1 , 2-디하이드로퀴놀린 -3- 카복사마이드;  (2) 1- (4-ethylphenethyl) -5-nitro-2-oxo—N-pheneryl-1, 2-dihydroquinoline-3-carboxamide;
(3) 1ᅳ(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) 1ᅳ(4ᅳ플루오로펜에틸) -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 -IB¬ 카복사마이드; (5) 1- (4-chlorobenzyl) -5-nitro-2-oxo -N- phenethyl-1,2-dihydroquinoline -IB ¬ 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 -2ᅳ옥소—N-펜에틸 -1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (7) 1- (4-aminobenzyl) -5-nitro-2ioxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
(8) 1-(4-시아노벤질 )ᅳ5-니트로 -2-옥소 -N-펜에틸 -1 , 2-디하이드로퀴놀린ᅳ 3- 카복사마이드; (8) 1- (4-cyanobenzyl) ᅳ 5-nitro-2-oxo-N-phenethyl-1, 2-dihydroquinoline® 3-carboxamide;
(9) 1- (나프탈렌— 2-일메틸 )-5ᅳ니트로—2-옥소 -Nᅳ펜에틸 -1，2—디하이드로퀴놀 린 -3-카복사마이드;  (9) 1- (naphthalene- 2-ylmethyl) -5mnitro-2-oxo-Nkphenethyl-1,2-dihydroquinoline-3-carboxamide;
( 10) 1-( [ 1ᅳ 1 '—비페닐] -4-일메틸) -5ᅳ니트로ᅳ 2-옥소 -Nᅳ펜에틸 -1， 2-디하이드 로퀴놀린 -3-카복사마이드;  (10) 1-([1′1′—biphenyl] -4-ylmethyl) -5′nitrojan 2-oxo-N ᅳ 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-옥소ᅳ N-펜에틸 -1ᅳ(4-페녹시벤질 )ᅳ1， 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; W (13) 1- (4-chlorophenethyl) -5-nitro-2—oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide; W
( 14) l-(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-펜에틸ᅳ1，2-디하이드로퀴놀린- 3-카복사마이드; ,  (16) 5-nitro-1- (4-nitrophenethyl) —2-oxo-N-phenethyl 펜 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-옥소ᅳ 1，2ᅳ 디하이드로퀴놀린 -3-카르복실레이트;  (18) methyl 1— (2- (cyclopenta-1,3-diene-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 -1,2ᅳ디하이드로퀴놀린 -3-카르복실레이트; (20) methyl 1-ethyl-5-nitro-2-oxo-1,2'dihydroquinoline-3-carboxylate;
(21) 메틸 1-메틸 -5-니트로ᅳ2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카르복실레이트;(21) methyl 1-methyl-5-nitrojan2-oxo-1,2′dihydroquinoline-3-carboxylate;
(22) 메틸 1-아세틸 -5ᅳ니트로—2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실레이 트; ' (22) methyl 1-acetyl-5vinytro-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) 2ᅳ옥소 -1， 2-딩하이드로퀴놀린 -3-카르보닐 클로라이드;  (24) 2ioxo-1, 2-dinghydroquinoline-3-carbonyl chloride;
(25) 2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3ᅳ카르보닐 브로마이드;  (25) 2-oxo-1'2-dihydroquinoline-3'carbonyl bromide;
(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) 2ᅳ옥소 -N-페닐 -1,2-디하이드로퀴놀린— 3-카복사마이드;  (28) 2ioxo-N-phenyl-1,2-dihydroquinoline— 3-carboxamide;
(29) 1-메틸 -2-옥소 -N-페닐ᅳ 1， 2-디하이드로퀴놀린 -3-카복사마이드;  (29) 1-methyl-2-oxo-N-phenyl ᅳ 1, 2-dihydroquinoline-3-carboxamide;
(30) 1-에틸 -2-옥소 -N-페닐ᅳ 1 , 2-디하이드로퀴놀린 -3-카복사마이드；  (30) 1-ethyl-2-oxo-N-phenyl ᅳ 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; (33) 1-((2H-피를 -2-일)메틸)ᅳ 5-벤즈아미도— 2ᅳ옥소 -N-페닐 -1,2-디하이드로 퀴놀린 -3-카복사마이드;  (32) 5-benzamido-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide; (33) 1-((2H-Py-2--2-yl) methyl) '5-benzamido—2ioxo-N-phenyl-1,2-dihydro quinoline-3-carboxamide;
(34) 5— (4ᅳ메틸벤즈아미도 )-2-옥소— N-페닐— 1， 2ᅳ디하이드로퀴놀린— 3-카복사 마이드;  (34) 5— (4′methylbenzamido) -2-oxo—N-phenyl—1,2′dihydroquinoline—3-carboxamide;
(35) 1-(2-(2Η-피를 -2-일)에틸) -5ᅳ(4—메틸벤즈아미도) -2—옥소 -N—페닐 -1,2- 디하이드로퀴놀린 -3ᅳ카복사마이드;  (35) 1- (2- (2Η-blood-2-yl) ethyl) -5 ᅳ (4—methylbenzamido) -2—oxo-N—phenyl-1,2-dihydroquinoline-3 Copyamide;
(36) 5-(4-브로모벤즈아미도) -2-옥소 -N—페닐 -1，2-디하이드로퀴놀린 -3-카복 사마이드;：' (36) 5- (4-bromobenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxy Amide ;： '
(37) 2-옥소 -N-(p-를일 )-1， 2-디하이드로퀴놀린— 3—카복사마이드；  (37) 2-oxo-N- (p-ylyl) -1, 2-dihydroquinoline— 3—carboxamide;
(38) 1-메틸 -2-옥소 -N-(p-를일 )-1， 2—디하이드로퀴놀린 -3-카복사마이드； (38) 1-methyl-2-oxo-N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(39) 1ᅳ에틸 -2-옥소 -N-(p-를일 )-1， 2-디하이드로퀴놀린 -3—카복사마이드； (40) 5-(4-클로로벤즈아미도) -2-옥소 -N-(p-를일) -1，2ᅳ디하이드로퀴놀린 -3- 카복사마이드; (39) 1 ᅳ ethyl-2-oxo-N- (p-ylyl) -1, 2-dihydroquinoline-3—carboxamide; (40) 5- (4-chlorobenzamido) -2-oxo -N- (p-ylyl) -1- 1,2-dihydroquinoline-3-carboxamide;
(41) N-(4-메톡시페닐) -2-옥소ᅳ 1，2—디하이드로퀴놀린 -3ᅳ카복사마이드; , (41) N- (4-methoxyphenyl) -2-oxo ᅳ 1,2-dihydroquinoline-3'carboxamide; ,
(42) 5ᅳ(4ᅳ플루오로벤즈아미도) -N-(4-메톡시페닐 )-2ᅳ옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (42) 5 ′ (4′fluorobenzamido) -N- (4-methoxyphenyl) -2 ᅳ oxo-1, 2-dihydro quinoline-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-(4ᅳ브로모페닐 )-2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3-카복사마이드； (44) N- (4'bromophenyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide;
(45) N-(4-브로모페닐 )ᅳ2-옥소 -5-(4-비닐벤즈아미도 )—1， 2-디하이드로퀴놀린 -3-카복사마이드; (45) N- (4-bromophenyl) ᅳ 2-oxo-5 (4-vinylbenzamido) —1, 2-dihydroquinoline-3-carboxamide;
(46) N— (4-브^모페닐 )-2—옥소 -1ᅳ (2- (티오펜 -2ᅳ일)에틸) -5-(4-비닐벤즈 아미도 )-1， 2-디하이드로퀴놀린 -3-카복사마이드； (46) N— (4-brokenmophenyl) -2—oxo-1 ′ (2- (thiophen-2-2-yl) ethyl) -5- (4-vinylbenz amido) -1,2-dihydro Quinoline-3-carboxamide;
(47) N-(4ᅳ클로로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (47) N- (4 ᅳ chlorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(48) N-(4-클로로페닐) -1ᅳ메틸— 2-옥소— 1， 2-디하이드로퀴놀린 -3—카복사 마이드; (48) N- (4-chlorophenyl) -1 ᅳ methyl- 2-oxo- 1, 2-dihydroquinoline-3-carboxamide;
(49) N-(4-클로로페닐) -1-에틸 -2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복사 마이드; (49) N- (4-chlorophenyl) -1-ethyl-2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(50) N-(4-클로로페닐) -5-(4-니트로벤즈아미도) 2-옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드;  (50) N- (4-chlorophenyl) -5 (4-nitrobenzamido) 2-oxo-1,2-dihydroquinoline-3-carboxamide;
(51) N-(4-클로로페닐 )-1-메틸 -5ᅳ(4ᅳ니트로벤즈아미도) -2-옥소 -1， 2-디하이 드로퀴놀린 -3—카 ^사마이드;  (51) N- (4-chlorophenyl) -1-methyl-5 ′ (4′nitrobenzamido) -2-oxo-1, 2-dihydrodroquinoline-3—car ^ amide;
(52) N-(4-클로로페닐) -1-에틸— 5ᅳ(4ᅳ니트로벤즈아미도)ᅳ 2ᅳ옥소 1 , 2-디하이 드로퀴놀린 -3-카복사마이드;  (52) N- (4-chlorophenyl) -1-ethyl—5 ′ (4′nitrobenzamido) ᅳ 2oxo 1, 2-dihydrodroquinoline-3-carboxamide;
(53) 5-(4-브로모벤즈아미도) -N-(4—클로로페닐) -2-옥소 -1 , 2—디하이드로 퀴놀린 -3-카복사마이드;  (53) 5- (4-bromobenzamido) -N- (4—chlorophenyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(54) 5-(4-브로모벤즈아미도)ᅳ N-(4-클로로페닐) -1-메틸 -2-옥소 -1 , 2-디하이 드로퀴놀린— 3-카복사마이드； (55) 5-(4-브로모벤즈아미도) -N— (4—클로로페닐) -1-에틸 -2-옥소 -1 , 2-디하이 드로퀴놀린 -3-카복사마이드； (54) 5- (4-bromobenzamido) 'N- (4-chlorophenyl) -1-methyl-2-oxo-1, 2-dihydrodroquinoline—3-carboxamide; (55) 5- (4-bromobenzamido) -N— (4—chlorophenyl) -1-ethyl-2-oxo-1,2-dihydrodroquinoline-3-carboxamide;
(56) Nᅳ (4-클로로페닐) -5-(4- (하이드톡시메틸)벤즈아미도) -2-옥소 -1 , 2- 디하이드로퀴놀린^ -카복사마이드;  (56) N '(4-chlorophenyl) -5- (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline ^ -carboxamide;
(57) N-(4-클로로페닐) -5-(4- (하이드록시메틸)벤즈아미도 )ᅳ1ᅳ메틸 -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카복사마이드; (57) N- (4-chlorophenyl) -5 (4- (hydroxymethyl) benzamido) ᅳ 1 ᅳ methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(58) N-(4-클로로페닐 )-1—에틸 -5-(4ᅳ (하이드록시메틸)벤즈아미도) -2-옥소- 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (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). N- (4-chlorophenyl) — 1— (furan-2-ylmethyl) — 5- (4- (hydroxymethyl) benzamido) -2-oxo-1, 2-dihydroquinoline-3-car Copyamide;
(60) N-(4—클로로페닐) -5_(4-니트로벤즈아미도) 2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (60) N- (4—chlorophenyl) -5_ (4-nitrobenzamido) 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(61) N-(4-클로로페닐 )— 1-메틸 -5-(4ᅳ니트로벤즈아미도) -2-옥소 -1， 2-디하이 드로퀴놀린 -3-카복사마이드；  (61) N- (4-chlorophenyl) —1-methyl-5- (4nitrobenzamido) -2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(62) N-(4—클로로페닐) -1-에틸— 5-(4ᅳ니트로벤즈아미도 )-2-옥소 -1 , 2-디하이 드로퀴놀린 -3ᅳ카복사마이드； (62) N- (4—chlorophenyl) -1-ethyl—5- (4nitrobenzamido) -2-oxo-1,2-dihedroquinoline-3′carboxamide;
(63) N-(4-클로로페닐) -1-(2- (퓨란 -2-일)에틸) 5-(4-니트로벤즈아미도) -2- 옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (63) N- (4-chlorophenyl) -1- (2- (furan-2-yl) ethyl) 5- (4-nitrobenzamido) -2-oxo-1, 2-dihydroquinoline-3 Decacaramide;
(64) N-(4-클로로페닐 )-2-옥소 -5ᅳ(2—페닐아세트아미도 )-1， 2—디하이드로 퀴놀린 -3-카복사마이드;  (64) N- (4-chlorophenyl) -2-oxo-5 '(2-phenylacetamido) -1, 2-dihydro quinoline-3-carboxamide;
(65) 5-벤즈아미도 -N-(4-클로로페닐 )ᅳ1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린- 3-카복사마이드;  (65) 5-benzamido-N- (4-chlorophenyl) ᅳ 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(66) 5—벤즈아미도 -N-(4-클로로페닐) -1_에틸 -2-옥소 -1， 2-디하이드≤퀴놀린- 3-카복사마이드;  (66) 5—benzamido-N- (4-chlorophenyl) -1_ethyl-2-oxo-1,2-dihydro ≦ quinoline-3-carboxamide;
(67) N-(4-클로로페닐) -5-(4-에틸벤즈아미도) -2ᅳ옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드; (67) N- (4-chlorophenyl) -5 (4-ethylbenzamido) -2oxoo-1,2-dihydroquinoline-3-carboxamide;
(68) N-(4-클로로페닐 )-5— (4-에틸벤즈아미도) -1-메틸ᅳ 2-옥소 -1， 2-디하이드 로퀴놀린 -3-카복사마이드;  (68) N- (4-chlorophenyl) -5— (4-ethylbenzamido) -1-methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(69) N-(4-클로로페닐) -1-에틸— 5-(4-에틸벤즈아미도 )ᅳ2-옥소 -1，2-디하이드 로퀴놀린 -3-카복사마이드;  (69) N- (4-chlorophenyl) -1-ethyl— 5- (4-ethylbenzamido) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxamide;
(70) N-(4-플루오로페닐 )-2-옥소— 1， 2-디하이드로퀴놀린 -3-카복사마이드； (71) N-(4-플루오로페닐 )-1-메틸— 2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드; (70) N- (4-fluorophenyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide; (71) N- (4-fluorophenyl) -1-methyl- 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(72) 1-에틸 -N-(4—플루오로페닐 )-2-옥소ᅳ 1 , 2-디하이드로퀴놀린 -3-카복사 마이드;  (72) 1-ethyl-N- (4—fluorophenyl) -2-oxoxo 1, 2-dihydroquinoline-3-carboxamide;
(73) 1ᅳ ( (2H-피를 -3-일)메틸) -N-(4ᅳ플루오로페닐) -2ᅳ옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (73) 1 ′ ((2H-Pyrid-3-yl) methyl) -N- (4 ᅳ fluorophenyl) -2ioxoo-1, 2-dihydro quinoline-3-carboxamide;
(74) N-(4-플루오로페닐 )— 2-옥소 5-(2-(p-를일 )아세트아미도)ᅳ 1， 2-디하이드 로퀴놀린 -3-카복사마이드;  (74) N- (4-fluorophenyl) —2-oxo 5- (2- (p-ylyl) acetamido) # 1, 2-dihydroquinoline-3-carboxamide;
(75) N-(4-플루오로페닐 )ᅳ1-메틸 -2-옥소 -5-(2-(p-를일)아세트아미도 )— 1ᅳ 2- 디하이드로퀴놀린 -3-카복사마이드;  (75) N- (4-fluorophenyl) ᅳ 1-methyl-2-oxo-5- (2- (p-ylyl) acetamido) —1 ′ 2-dihydroquinoline-3-carboxamide;
(76) 1-에틸 -Nᅳ (4-플루오로페닐 )ᅳ2-옥소— 5-(2-(p—틀일)아세트아미도 )-1，2- 디하이드로퀴놀린 -3—카복사마이드;  (76) 1-ethyl-N ᅳ (4-fluorophenyl) ᅳ 2-oxo—5- (2- (p-tyl) acetamido) -1,2-dihydroquinoline-3—carboxamide;
(77) N-(4-에틸페 ^ )— 2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드；  (77) N- (4-ethylfe ^) — 2-oxo-1, 2'dihydroquinoline-3-carboxamide;
(78) N-(4-에틸페닐) -1-메틸 -2—옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드; (79) 1-에틸 -N-(4-에틸페닐) -2—옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;(78) N- (4-ethylphenyl) -1-methyl-2—oxo-1, 2-dihydroquinoline—3-carboxamide; (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-디하이드로 퀴놀린 -3-카복사마이드; (80) 1- (2— (2H-pyrrole— 3-yl) ethyl) -N- (4—ethylphenyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(81) 5— (2-(4-브로모페닐 )아세트아미도) -N-(4-에틸페닐 )-2ᅳ옥소 -1， 2-디하이 드로퀴놀린 -3ᅳ카복사마이드；  (81) 5— (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2ioxo-1, 2-dihydrodroquinoline-3'carboxamide;
(82) 5-(2-(4-브로모페닐)아세트아미도) -N-(4-에틸페닐) -2ᅳ옥소 -1- (티오펜- 2-일메틸) -1， 2-디하이드로퀴놀린 -3-카복사마이드； (82) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2ioxo-1- (thiophen-2-ylmethyl) -1,2-di Hydroquinoline-3-carboxamide;
(83) 5-(2-(4-브로모페닐)아세트아미도) -N- -에틸페닐 )-1-메틸 -2-옥소- 1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드；  (83) 5- (2- (4-bromophenyl) acetamido) -N-ethylphenyl) -1-methyl-2-oxo-1,2'dihydroquinoline-3-carboxamide;
(84) 5— (2— (4-브로모페닐)아세트아미도 )—1-에틸— N-(4-에틸페닐) -2-옥소- 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (84) 5— (2— (4-bromophenyl) acetamido) —1-ethyl— N- (4-ethylphenyl) -2-oxo-1, 2-dihydroquinoline-3′carboxamide;
(85) N-(4—하이드록시페닐 )-2-옥소ᅳ1， 2-디하이드로퀴놀린— 3ᅳ카복사마이드； (85) N- (4—hydroxyphenyl) -2-oxo'1, 2-dihydroquinoline- 3'carboxamide;
(86) N— (4-하이드록시페닐 )-1-메틸ᅳ 2ᅳ옥소 -1 , 2—디하이드로퀴놀린 -3- 카복사마이드; (86) N— (4-hydroxyphenyl) -1-methyl ᅳ 2 ᅳ oxo-1, 2-dihydroquinoline-3-carboxamide;
(87) 1-에틸 -N-(4—하이드록시페닐 )— 2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3—카복사 마이드;  (87) 1-ethyl -N- (4—hydroxyphenyl) — 2-oxo-1 ′ 2-dihydroquinoline-3—carboxamide;
(88) N— (4ᅳ하이드록시페닐) -2ᅳ옥소 -1-(2ᅳ (티오펜 -2-일)에틸) -1， 2-디하이드 로퀴놀린 -3ᅳ카복사마이드; (88) N— (4'hydroxyphenyl) -2 ᅳ oxo-1- (2 '(thiophen-2-yl) ethyl) -1,2-dihydro Roquinoline-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) 5ᅳ(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—3-carboxamide ;
(91) 5ᅳ(2-(4—클로로페닐)아세트아미도 )— 1—에틸ᅳ N-(4—하이드록시페닐 )-2ᅳ 옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (91) 5 ′ (2- (4—chlorophenyl) acetamido) — 1—ethyl ᅳ N- (4—hydroxyphenyl) -2 ′ oxo-1, 2-dihydroquinoline-3-carboxamide ;
(92) N-(4-니트로페닐) -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복사마이드;  (92) N- (4-nitrophenyl) -2-oxoxo 1, 2-dihydroquinoline-3-carboxamide;
(93) 5-(2-(4-플루오로페닐)아세트아미도) -N-(4-니트로페닐 )-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 )-2ᅳ옥소 -1， 2—디하이 드로퀴놀린 -3-카복사마이드;  (94) 5- (2— (4-ethylphenyl) acetamido) -N- (4-nitrophenyl) -2ioxo-1,2-dihydrodroquinoline-3-carboxamide;
(95) N-(4-(N , N-디메틸설파모일)페닐) -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3ᅳ 카복사마이드; (95) N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2'dihydroquinoline-3'carboxamide;
(96) N-(4-(N , N-디메틸설파모일)페닐 )ᅳ1—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— 2ᅳ옥소 -1， 2—디하이드로 퀴놀린 -3-카복사마이드;  (97) N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-ethyl- 2ioxo-1, 2-dihydro quinoline-3-carboxamide;
(98) 1- (사이클로핵실메틸) -N- ( 4ᅳ ( N , N-디메틸설파모일)페닐) -2-옥소 - 1 , 2- 디하이드로퀴놀린 -3-카복사마이드;  (98) 1- (cyclonucleosilmethyl) -N- (4 ′ (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(99) 1-(2-사이클로핵실에틸) -Ν-(4— (Ν , Ν—디메틸설파모일)페닐) -2-옥소 -1，2ᅳ 디하이드로퀴놀린— 3-카복사마이드;  (99) 1- (2-cyclonucleosilethyl) -Ν- (4— (Ν, Ν—dimethylsulfamoyl) phenyl) -2-oxo-1,2 ′ dihydroquinoline—3-carboxamide;
( 100) Ν-(4- (하이드특시메틸)페닐 )-2-옥소 -1 , 2-디하이드로퀴놀린ᅳ 3-카복사 마이드;  (100) Ν- (4- (hydrospecificmethyl) phenyl) -2-oxo-1, 2-dihydroquinoline® 3-carboxamide;
( 101) Ν-(4- (하이드록시메틸)페닐) -1-메틸 -2—옥소 -1，2ᅳ디하이드로퀴놀린 -3- 카복사마이드; (101) Ν- (4- (hydroxymethyl) phenyl) -1-methyl-2—oxo-1,2′dihydroquinoline-3-carboxamide;
( 102) 1-에틸— Ν-(4- (하이드록시메틸)페닐 )ᅳ2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (102) 1-ethyl- Ν- (4- (hydroxymethyl) phenyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 103) 1- (사이클로펜틸메틸) -Νᅳ (4- (하이드록시메틸)페닐) -2-옥소— 1，2- 디하이드로퀴놀린— 3-카복사마이드;  (103) 1- (cyclopentylmethyl) -Ν ᅳ (4- (hydroxymethyl) phenyl) -2-oxo— 1,2-dihydroquinoline—3-carboxamide;
( 104) 2-옥소 -Ν-(4-비닐페닐) -1， 2—디하이드로퀴놀린 -3-카복사마이드； ( 105) 1-메틸 -2-옥소 -N- (4-비닐페닐 )—1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；(104) 2-oxo-Ν- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide; (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 )ᅳ2—옥소 -N— (4-비닐페닐 )ᅳ1， 2-디하이드로 퀴놀린 -3-카복사마이드; (107) 1- (2-cyclopentylethyl) ᅳ 2—oxo-N— (4-vinylphenyl) ᅳ 1, 2-dihydro quinoline-3-carboxamide;
( 108) 5-(2-(4-하이드록시페닐)아세트아미도 )-2-옥소 -N-(4-비닐페닐) -1 , 2- 다하이드로퀴놀린 -3-카복사마이드; (108) 5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1, 2- polyhydroquinoline-3-carboxamide;
(109) 5— (2-(4-하이드록시페닐)아세트아미도 )-1-메틸ᅳ 2-옥소 -N-(4—비닐페닐) -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (109) 5— (2- (4-hydroxyphenyl) acetamido) -1-methyl ᅳ 2-oxo-N- (4—vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide ;
( 110) 1-에틸 -5-(2-(4-하이드록시페닐)아세트아미도)ᅳ 2-옥소— N-(4-비닐페닐) -1 , 2-디하이드로퀴 '놀린—3-카복사마이드;  (110) 1-ethyl-5- (2- (4-hydroxyphenyl) acetamido) 도 2-oxo—N- (4-vinylphenyl) -1,2-dihydroqui 'noline—3-car Copyamide;
( 111) 1-( (2，3一디하이드로ᅳ 1Hᅳ인덴 -2-일)메틸 )ᅳ5-(2— (4—하이드록시페닐 ) 아세트아미도 )-2-옥소 -N- (4-비닐페닐) -1， 2-디하이드로퀴놀린 -3-카복사마이  (111) 1-((2,3didihydro 1H ᅳ inden-2-yl) methyl) ᅳ 5- (2— (4—hydroxyphenyl) acetamido) -2-oxo-N- ( 4-vinylphenyl) -1,2-dihydroquinoline-3-carboxami
( 112) 5-(2-(4-니트로페닐)아세트아미도 )-2-옥소 -N— (4-비닐페닐 )ᅳ1 ,2- 디하이드로퀴놀린 -3-카복사마이드; (112) 5- (2- (4-nitrophenyl) acetamido) -2-oxo-N— (4-vinylphenyl) ᅳ 1,2-dihydroquinoline-3-carboxamide;
( 113) 1-메틸 -5-(2-(4-니트로페닐)아세트아미도) -2-옥소— N-(4ᅳ비닐페닐) - 1ᅳ 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 -3ᅳ카복사마이드；  (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-111-인덴-2ᅳ일)메틸)—5-(2—(4-니트로 페닐)아세트아미도) -2-옥소 -N- (4—비닐페닐 )-1， 2-디하이드로퀴놀린 -3ᅳ카복사 마이드; (115) 1— ((4-methoxy-2, 3-dihydro-111-inden-2 ylyl) methyl) —5- (2— (4-nitrophenyl) acetamido) -2-oxo-N (4—vinylphenyl) -1, 2-dihydroquinoline-3′carboxamide;
( 116) 1-( (5-메록시 -2 , 3-디하이드로 -1H-인덴 -2-일 )메틸 )-5-(2-(4-니트로 페닐 )아세트아미도 )-2-옥소 -N-(4-비닐페닐)— 1 , 2ᅳ디하이드로퀴놀린 -3—카복사 마이드;  (116) 1-((5-Methoxy-2,3-dihydro-1H-inden-2-yl) methyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo- 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 -2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (119) N-benzyl-1-ethyl-2-hexoxo-1, 2-dihydroquinoline-3-carboxamide;
( 120) 5_(2-(4-메록시페닐)아세트아미도 )-2-옥소 -N-페닐 -1ᅳ 2-디하이드로 퀴놀린 -3-카복사마이드;  (120) 5_ (2- (4-methoxyphenyl) acetamido) -2-oxo-N-phenyl-1'2-dihydro quinoline-3-carboxamide;
( 121) 1-( (5-에틸 -2，3-디하이드로-111-인덴-2-일)메틸)ᅳ5-(2-(4-01ᅵ특시페닐) 아세트아미도 )-2-옥소 -N—페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드；(121) 1-((5-ethyl-2,3-dihydro-111-inden-2-yl) methyl) ᅳ 5- (2- (4- 0 1Specific phenyl) Acetamido) -2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
( 122) 1-( (5-풀루오로 -2， 3-디하이드로 -1Hᅳ인덴 -2-일 )메틸 )-5— (2-(4-메톡시 페닐)아세트아미도 )—2-옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드；(122) 1- ((5-Pluoro-2, 3-dihydro-1H ᅳ inden-2-yl) methyl) -5— (2- (4-methoxyphenyl) acetamido) —2 -Oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
( 123) 1ᅳ( (5-클로로 -2， 3-디하이드로 -1H-인덴 -2-일 )메틸 )-5-(2_(4-메록시페닐 ) 아세트아미도 )-2-옥소 -N-페닐 -1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드；(123) 1 '((5-chloro-2,3-dihydro-1H-inden-2-yl) methyl) -5- (2_ (4-methoxyphenyl) acetamido) -2-oxo-N -Phenyl-1, 2'dihydroquinoline-3-carboxamide;
( 124) 5-(2-(4— (하이드록시메틸)페닐 )아세트아미도 )-2-옥소 페닐— 1， 2- 디하이드로퀴놀린 -3-카복사마이드； (124) 5- (2- (4— (hydroxymethyl) phenyl) acetamido) -2-oxophenyl—1,2-dihydroquinoline-3-carboxamide;
( 125) 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )-1-( (5-아이오도ᅳ 2，3ᅳ 디하이드로 -1H-인델-2-일 )메틸 )-2ᅳ옥소 -N-페닐 -1， 2-디하이드로퀴놀린ᅳ 3ᅳ 카복사마이드;  (125) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1-((5-iodo ᅳ 2,3'dihydro-1H-indel-2-yl) methyl)- 2 ᅳ oxo-N-phenyl-1, 2-dihydroquinoline ᅳ 3′carboxamide;
( 126) 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )-1-( (5-니트로ᅳ2，3- 디하이드로 -1H—인덴 -2-일 )메틸 )ᅳ2ᅳ옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3ᅳ 카복사마이드;  (126) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1-((5-nitrojan2,3-dihydro-1H—inden-2-yl) methyl) ᅳ 2 Gioxo-N-phenyl-1, 2-dihydroquinoline-3'carboxamide;
( 127) 2-옥소 -N-페닐ᅳ 5-(3ᅳ페닐프로판아미도 )-1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (127) 2-oxo-N-phenyl ᅳ 5- (3 ᅳ phenylpropaneamido) -1, 2-dihydroquinoline-3-carboxamide;
( 128) 1-( (5-에틸 -2，3-디하이드로 -1H-인덴 -2—일)메틸) -2-옥소ᅳ N-페닐 -5-(3_ 페닐프로판아미도) -1 , 2ᅳ디하이드로퀴놀린— 3-카복사마이드；  (128) 1-((5-ethyl-2,3-dihydro-1H-inden-2-2-yl) methyl) -2-oxoze N-phenyl-5- (3_phenylpropaneamido) -1, 2 Shendihydroquinoline—3-carboxamide;
( 129) 5ᅳ(2-(4-에틸페닐)아세트아미도 )-2-옥소 -N-페닐 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (129) 5 ′ (2- (4-ethylphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;
( 130) 1- ( 2- ( 2 , 3ᅳ디하이드로 - 1H-인덴 -2—일)에틸) -5— ( 2ᅳ ( 4-에틸페닐)아세트 아미도 )-2-옥소 -N—페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (130) 1- (2- (2, 3'dihydro-1H-indene-2-yl) ethyl) -5- (2 '(4-ethylphenyl) acetamido) -2-oxo-N-phenyl- 1, 2-dihydroquinoline-3-carboxamide;
( 131) 2-옥소 -N-펜에틸ᅳ 1， 2-디하이드로퀴놀린 -3-카복사마이드；  (131) 2-oxo-N-phenethyl ᅳ 1, 2-dihydroquinoline-3-carboxamide;
( 132) 1— (4-메록시벤질 ) -2-옥소ᅳ N-펜에틸 -1 , 2-디하이드로퀴놀린 -3—카복사 마이드；  (132) 1— (4-Methoxybenzyl) -2-oxoxo N-phenethyl-1, 2-dihydroquinoline-3—carboxamide;
( 133) 2ᅳ옥소 -N-펜에틸 -1-(4— (트리플루오로메톡시)벤질)ᅳ 1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (133) 2ioxo-N-phenethyl-1- (4— (trifluoromethoxy) benzyl) ᅳ 1, 2-dihydro quinoline-3-carboxamide;
( 134) 1- ( 2- ( 4—메록시 -2， 3-디하이드로 - 1H-인덴 -2-일)에틸) -2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (134) 1- (2- (4—Methoxy-2, 3-dihydro-1H-inden-2-yl) ethyl) -2-oxo-N-phenethyl-1, 2-dihydroquinoline ᅳ 3 -Carboxamide;
( 135) 2ᅳ옥소 -N—펜에틸 -1— (2-(4- (트리플루오로메특시) -2，3—디하이드로-lH- 인덴 -2-일)에틸) -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (135) 2oxo-N-phenethyl-1— (2- (4- (trifluoromepoxy) -2,3—dihydro-lH-inden-2-yl) ethyl) -1,2- Dihydroquinoline-3-carboxamide;
( 136) 5- ( 2- (4-메록시페닐)아세트아미도 ) -2ᅳ옥소 -N-펜에틸 - 1， 2-디하이드로 퀴놀린 -3-카복사마이드; (136) 5- (2- (4- methoxyphenyl) acetamido) -2 ioxo-N-phenethyl -1, 2-dihydro Quinoline-3-carboxamide;
(137) 1ᅳ(4-메특시벤질) -5-(2-(4ᅳ메특시페닐)아세트아미도 )-2-옥소 -N- 펜에틸 -1，2-디하이드로퀴놀린ᅳ 3-카복사마이드； (137) 1 '(4-Methoxybenzyl) -5- (2- (4'methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline® 3 -car Radiation amide;
(138) 1ᅳ((4-하이드록시 -2，3-디하이드로-lH-인덴-2-일)메틸)-5-(2-(4- 메톡시페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린ᅳ 3-카복 사마이드;  (138) 1 '((4-hydroxy-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2-oxo -N-phenethyl-1, 2-dihydroquinoline® 3-carboxamide;
( 139) 1-( (4ᅳ포르밀ᅳ2，3-디하이드로ᅳ 1H-인덴ᅳ 2-일 )메틸 )-5-(2-(4-메특시 페닐)아세트아미도) -2ᅳ옥소 -Nᅳ펜에틸ᅳ 1， 2-디하이드로퀴놀린ᅳ 3ᅳ카복사마이드； (139) 1-((4'formyl ᅳ 2,3-dihydro 하이드 1H-indenyl 2-yl) methyl) -5- (2- (4-methoxyphenyl) acetamido) -2oxo -N "phenethyl" 1,2-dihydroquinoline "3" carboxamide;
(140) 1-((4-시아노ᅳ2,3-디하이드로—1}1-인덴-2-일)메틸)-5-(2-(4-메톡시 페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1， 2ᅳ디하이드로퀴놀린 -3ᅳ카복사마이드；(140) 1-((4-cyano ᅳ 2,3-dihydro—1} 1-inden-2-yl) methyl) -5- (2- (4-methoxy phenyl) acetamido) -2 -Oxo-N-phenethyl-1, 2'dihydroquinoline-3'carboxamide;
(141) 5-(2-(4-브로모페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1,2ᅳ디하이드로 퀴놀린 -3ᅳ카복사마이드; (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， 2ᅳ디하이드로퀴놀린ᅳ 3-카복사마이드；  (142) 5- (2- (4-bromophenyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2'dihydroquinoline ᅳ 3-carbox Amide;
(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-메특시벤질) -2-옥소 -N-(3-페닐프로필) -1,2-디하이드로퀴놀린ᅳ 3- 카복사마이드;  (144) 1- (4-mesoxybenzyl) -2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline® 3-carboxamide;
(145) 1- ( 2ᅳ (^포르밀 -2， 3ᅳ디하이드로 - 1H-인덴 -2-일)에틸) -2-옥소ᅳ N- ( 3- 페닐프로필 )-1， 2—디하이드로퀴놀린 -3-카복사마이드；  (145) 1- (2 '(^ formyl-2, 3'dihydro-1H-inden-2-yl) ethyl) -2-oxoquin N- (3-phenylpropyl) -1, 2-dihydroquinoline -3-carboxamide;
(146) 1-(2-(5- (메틸티오) -2,3-디하이드로-lH-인덴-2-일)에틸)ᅳ2ᅳ옥소-Nᅳ (3-페닐프로필)—l， 2-디하이드로퀴놀린 -3-카복사마이드； (146) 1- (2- (5- (methylthio) -2,3-dihydro-lH-inden-2-yl) ethyl) ᅳ 2 ᅳ oxo-N ᅳ (3-phenylpropyl) —l, 2 -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-메록시벤질) -N-(4-메틸벤질)— 2ᅳ옥소 -1,2ᅳ디하이드로퀴놀린 -3- 카복사마이드;  (148) 1- (4-methoxybenzyl) -N- (4-methylbenzyl) —2oxo-l, 2'dihydroquinoline-3-carboxamide;
(149) N-(4-메틸벤질)— 2-옥소— 1ᅳ(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; ( 153) l-(4-에틸벤질 )-N-(4ᅳ메틸펜에틸) -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3- 카복사마이드; (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—메록시벤질) -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—메록시벤질) -N-(4-메틸펜 에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (156) 5- (2- (4-chlorophenyl) acetamido) -1- (4—methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline -3 ᅳ carboxamide;
( 157) N-(4-메록시벤질)—2ᅳ옥소—1 , 2-디하이드로퀴놀린 -3-카복사마이드; ( 158) 1-(2-(5-아미노 -2 , 3-디하이드로— 1H-인덴 -2—일)에틸) -N-(4-메톡시 벤질) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (157) N- (4-methoxybenzyl) —2hexoxo-1, 2-dihydroquinoline-3-carboxamide; (158) 1- (2- (5-amino-2, 3-dihydro— 1H-inden-2-2-yl) ethyl) -N- (4-methoxybenzyl) -2-oxo-1,2-di Hydroquinoline-3-carboxamide;
( 159) 1-(2-(5-에틸 -2 , 3-디하이드로 -1H-인덴 -2-일)에틸 )-N-(4ᅳ메톡시벤질) - (159) 1- (2- (5-ethyl-2, 3-dihydro-1H-inden-2-yl) ethyl) -N- (4 ᅳ methoxybenzyl)-
2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 160) N-(4-메록시펜에틸 )-2—옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； ( 161) 1-(4-메록시벤질) -N-(4-메톡시펜에틸 )ᅳ2—옥소 -1，2-디하이드로퀴놀린- (160) N- (4-methoxyphenethyl) -2—oxo-1, 2-dihydroquinoline-3-carboxamide; (161) 1- (4-methoxybenzyl) -N- (4- Methoxyphenethyl) ᅳ 2—oxo-1,2-dihydroquinoline-
3-카복사마이드; 3-carboxamide;
( 162) 1-(2-(5-하이드록시 -2 , 3-디하이드로— 1H-인덴 -2-일 )에틸 ) -N-(4-메톡시 펜에틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (162) 1- (2- (5-hydroxy-2, 3-dihydro— 1H-inden-2-yl) ethyl) -N- (4-methoxy phenethyl) -2-oxo-1, 2 Dihydroquinoline-3-carboxamide;
( 163) 1-( (2，3-디하이드로 -1H-인덴 -5-일 )메틸 )— N-(4-메특시펜에틸) -2-옥소- 1， 2-디하이드로퀴놀린 -3-카복사마이드；  (163) 1-((2,3-dihydro-1H-inden-5-yl) methyl) —N- (4-mesotsiphenethyl) -2-oxo-1,2-dihydroquinoline-3- Carboxamide;
( 164) 1- ( 2— ( 2 , 3-디하이드로 - 1H-인덴 -5-일)에틸) -N- ( 4-메록시펜에틸 ) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (164) 1- (2— (2, 3-dihydro-1H-inden-5-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 -1ᅳ 2-디하이드로퀴놀린 -3-카복사 마이드; (168) 1-benzoyl -N- (4—bromobenzyl) -2—oxo-1 ′ 2-dihydroquinoline-3-carboxamide;
( 169) N-(4-브로모벤질) -1— (4-메톡시벤조일 )ᅳ2-옥소 -1 , 2-디하이드로퀴놀린- 3-카복사마이드; ( 170) N-(4-브로모펜에틸 )-2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복사마이드;(169) N- (4-bromobenzyl) -1— (4-methoxybenzoyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide; (170) N- (4-bromophenethyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(171) N- -브로모펜에틸) -1-(4-메록시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린- 3-카복사마이드; (171) N-bromophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
( 172) N-(4-브로모펜에틸 )-2ᅳ옥소 -1ᅳ(4ᅳ (트리플루오로메톡시)벤조일)ᅳ 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 , 2ᅳ디하이드로퀴놀린 -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-디하이드로 퀴놀린 -3-카복사마이드;  (176) N- (4-chlorobenzyl) -1- (4-hydroxybenzoyl) -2-oxo-1, 2-dihydro quinoline-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-디하이드로퀴놀란— 3-카복사마이드; (178) N- (4-chlorophenethyl) -1- (4-methoxybenzyl) — 2-oxo-1, 2-dihydroquinolan— 3-carboxamide;
( 179) 1-(4-클로로벤조일 )— N-(4ᅳ클로로펜에틸 )-2-옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (179) 1- (4-chlorobenzoyl) —N- (4 ᅳ chlorophenethyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
( 180) N-(4-클로로펜에틸 )-1-(4ᅳ아이오도벤조일) 2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (180) N- (4-chlorophenethyl) -1- (4 ᅳ iodobenzoyl) 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(181) N-(4-클로로펜에틸 )-1-(4-니트로벤조일 )-2-옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드； . (181) N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
(182) 1-(4ᅳ아미노벤조일 )-Nᅳ (4-클로로펜에틸 )-2-옥소 -1， 2-디하이드로 퀴놀린 -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 )-1ᅳ(4—포르밀벤조일 )-2—옥소 -1，2-디하이드로 퀴놀린ᅳ 3-카복사마이드; (185) N- (4-fluorobenzyl) -1 ′ (4—formylbenzoyl) -2—oxo-1,2-dihydro quinoline ᅳ 3-carboxamide;
( 186) 1-(4ᅳ시아노벤조일) N-(4-플루오로벤질 )-2—옥소 -1 , 2-디하이드로 퀴놀린ᅳ3-카복사마이드;  (186) 1- (4 ᅳ cyanobenzoyl) N- (4-fluorobenzyl) -2—oxo-1, 2-dihydro quinoline ᅳ 3-carboxamide;
(187) N-(4-플투오로벤질 )-1-(4— (메틸티오)벤조일 )-2-옥소 -1 , 2ᅳ디하이드로 퀴놀린 -3-카복사마이드; (187) N- (4-Fluorobenzyl) -1- (4— (methylthio) benzoyl) -2-oxo-1, 2'dihydro Quinoline-3-carboxamide;
( 188) N-(4-플루오로펜에틸)— 2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드； (188) N- (4-fluorophenethyl) — 2oxoo-1, 2-dihydroquinoline-3-carboxamide;
( 189) N— (4ᅳ플루오로펜에틸)ᅳ1-(4-메특시벤질) -2ᅳ옥소—1 , 2ᅳ디하이드로 퀴놀린 -3-카복사마이드; (189) N— (4′fluorophenethyl) ᅳ 1- (4-mesoxybenzyl) -2-hexoxo-1, 2 ᅳ dihydro quinoline-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-dihydro quinoline-3-carboxamide;
( 191) N-(4-플루오로펜에틸)ᅳ 1-(2— (4-메특시페닐)아세틸 )-2-옥소 -1 , 2- 디하이드로퀴놀린— 3-카복사마이드；  (191) N- (4-fluorophenethyl) ᅳ 1- (2— (4-methoxyphenyl) acetyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxamide;
( 192) N-(4-플루오로펜에틸) -2ᅳ옥소 -1-(2— (4— (트리플루오로메특시)페닐) 아세틸 )-1， 2-디하이드로퀴놀린 -3-카복사마이드;  (192) N- (4-fluorophenethyl) -2-ioxo-1- (2— (4— (trifluoromepoxy) phenyl) acetyl) -1,2-dihydroquinoline-3-carbox Amide;
( 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-디하이 드로퀴놀린— 3-카복사마이드； (194) N- (4-ethylbenzyl) -1- (2- (4—hydroxyphenyl) acetyl) -2-oxo-1, 2-dihydrodroquinoline—3-carboxamide;
( 195) N-(4—에틸벤질 )-1— (2— (4ᅳ에틸페닐)아세틸 )-2-옥소— 1 , 2-디하이드로 퀴놀린—3-카복사마이드;  (195) N- (4—ethylbenzyl) -1— (2— (4 ᅳ ethylphenyl) acetyl) -2-oxo—1, 2-dihydro quinoline—3-carboxamide;
( 196) N-(4-에틸벤질 )-1-(2-(4-플루오로페닐)아세틸 )-2-옥소— 1， 2-디하이 드로퀴놀린 -3-카복사마이드;  (196) N- (4-ethylbenzyl) -1- (2- (4-fluorophenyl) acetyl) -2-oxo— 1, 2-dihydrodroquinoline-3-carboxamide;
( 197) 1-(2-(4-클로로페닐)아세틸) -Nᅳ (4ᅳ에틸벤질) 2—옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (197) 1- (2- (4-chlorophenyl) acetyl) -N '(4'ethylbenzyl) 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
( 198) N-(4-에틸벤질) -1-(2-(4-아이오도페닐)아세틸 )-2-옥소 -1，2-디하이 드로퀴놀린 -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， 2ᅳ디하이드로 퀴놀린 -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-디하이드로 퀴놀린 -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 -3ᅳ카복사마이드； (201) N- (4-ethylphenethyl) -2-oxo-1, 2-dihydroquinoline-3'carboxamide;
(202) N-(4-에틸펜에틸) -1-(2— (4—포르밀페닐)아세틸 )— 2-옥소ᅳ 1 , 2-디하이드 로퀴놀린 -3-카복사마이드； (202) N- (4-ethylphenethyl) -1- (2— (4—formylphenyl) acetyl) — 2-oxoze 1, 2-dihydroquinoline-3-carboxamide;
(203) 1-(2-(4-시아노페닐 )아세틸 )-N-(4—에틸펜에틸 )-2-옥소— 1， 2-디하이드 로퀴놀린 -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 )ᅳ2-옥소 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드; (204) N- (4-ethylphenethyl) -1- (2— (4- (methylthio) phenyl) acetyl) ᅳ 2-oxo-1, 2- Dihydroquinoline-3-carboxamide;
(205) 1-(2-(4- (디플루오로메틸)페닐)아세틸 )-Nᅳ (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 )-2ᅳ옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드； (207) N-(4-하이드록시벤질) -1-(4- (메틸티오)벤질) 2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (206) N- (4-hydroxybenzyl) -2 ᅳ oxo-1, 2-dihydroquinoline— 3-carboxamide; (207) N- (4-hydroxybenzyl) -1- (4- ( Methylthio) benzyl) 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(208) N-(4-하이드록시벤질)— 1-(4- (메틸티오)펜에틸 )-2-옥소ᅳ 1 , 2-디하이드 로퀴놀린 -3-카복사마이드;  (208) N- (4-hydroxybenzyl) — 1- (4- (methylthio) phenethyl) -2-oxoxin 1, 2-dihydroquinoline-3-carboxamide;
(209) N-(4-하이드록시벤질) -2-옥소 -1— (4- (트리플루오로메톡시)펜에틸 )-1，2 -디하이드로퀴놀린 -3ᅳ카복사마이드;  (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-카복사마이  (210) N- (4-hydroxyphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
(211) N-(4-하이드록시펜에틸 )— 1ᅳ(4-메특시펜에틸 )-2—옥소— 1 , 2-디하이드로 퀴놀린—3-카복사마이드; (211) N- (4-hydroxyphenethyl) —1 ′ (4-mesoxifenethyl) -2—oxo—1, 2-dihydro quinoline—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， 2ᅳ디하이드로퀴놀린- 3-카복사마이드; (213) 1— (4—iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1, 2'dihydroquinoline-3-carboxamide;
(214) 1-(4-아이오도펜에틸)ᅳ N-(4-니트로벤질) 2-옥소— 1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (214) 1- (4-iodophenethyl) ᅳ N- (4-nitrobenzyl) 2-oxo— 1, 2-dihydro quinoline-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-(4ᅳ포르밀펜에틸) -N-(4-니트로펜에틸 )-2—옥소 -1，2-디하이드로 퀴놀린 -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-옥소ᅳ 1 , 2-디하 이드로퀴놀린 -3-카복사마이드; (218) 1- (4- (difluoromethyl) phenethyl) -N- (4—nitrophenethyl) -2-oxoxin 1, 2-dihydroquinoline-3-carboxamide;
(219) N— (4— (Ν,Ν-디메틸설파모일)벤질)—2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복사마이드;  (219) N— (4— (Ν, Ν-dimethylsulfamoyl) benzyl) —2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(220) 1-(4- (디플루오로메틸)벤질) Ν-(4-(Ν,Ν-디메틸설파모일)벤질)—2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (220) 1- (4- (difluoromethyl) benzyl) Ν- (4- (Ν, Ν-dimethylsulfamoyl) benzyl) —2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(221) Ν- ( 4- ( Ν， Ν-디메틸설파모일)펜에틸 ) -2-옥소 - 1， 2-디하이드로퀴놀린 -3- 카복사마이드; (221) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenethyl) -2-oxo-1, 2-dihydroquinoline-3- Carboxamide;
(222) Nᅳ (4- (하이드록시메틸)벤질 )— 2-옥소 -1， 2ᅳ디하이드로퀴놀린 3ᅳ카복사 마이드;  (222) N '(4- (hydroxymethyl) benzyl) —2-oxo-1,2'dihydroquinoline 3'carboxamide;
(223) N-(4- (하이드록시메틸)펜에틸 )-2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카복 사마이드;  (223) N- (4- (hydroxymethyl) phenethyl) -2 ᅳ oxo-1, 2-dihydroquinoline-3-carboxamide;
(224) 2-옥소ᅳ N— (4-비닐벤질 )-1 , 2-디하이드로퀴놀린ᅳ 3-카복사마이드； (224) 2-oxozone N— (4-vinylbenzyl) -1, 2-dihydroquinoline® 3-carboxamide;
(225) 2-옥소ᅳ N-(4-비닐펜에틸) -1 , 2-디하이드로퀴놀린 -3-카복사마이드;(225) 2-oxoze N- (4-vinylphenethyl) -1, 2-dihydroquinoline-3-carboxamide;
(226) N-메틸ᅳ 2-옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (226) N-methyl ᅳ 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
(227) 1-(2 , 3—디하이드로 -1H-인덴— 2ᅳ카르보닐 )-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) 1ᅳ ( 2- ( 2 , 3-디하이드로 - 1H-인덴 -2-일)아세틸) -N-메틸 -2ᅳ옥소 -N-페닐- 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (228) 1 '(2- (2,3-dihydro-1H-inden-2-yl) acetyl) -N-methyl-2 ᅳ oxo-N-phenyl-1,2-dihydroquinoline-3 ᅳ carbox Amide;
(229) 1-(3_(2 , 3-디하이드로 -1H-인덴 -2—일)프로파노일 )-N—메틸ᅳ2-옥소 -N- 페닐 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (229) 1- (3_ (2,3-dihydro-1H-inden-2-2-yl) propanoyl) -N-methyl ᅳ 2-oxo-N-phenyl-1,2-dihydroquinoline ᅳ 3- Carboxamide;
(230) N-에틸 -1-(2— (5-메특시 -2， 3-디하이드로 1H-인덴 -2-일)아세틸 )-2-옥소 -N-페닐 -1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드； (230) N-ethyl-1- (2— (5-methoxy-2, 3-dihydro 1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1, 2'dihydroquinoline- 3-carboxamide;
(231) N-에틸 -1-(2-(5- (메틸티오 )ᅳ2ᅳ 3-디하이드로 -1H-인덴 -2-일)아세틸 )-2- 옥소 -N-페닐— 1， 2—디하이드로퀴놀린 -3—카복사마이드；  (231) N-ethyl-1- (2- (5- (methylthio) ᅳ 2 ′ 3-dihydro-1H-inden-2-yl) acetyl) -2-oxo-N-phenyl— 1, 2— Dihydroquinoline-3—carboxamide;
(232) 1^-에틸-2-옥소—^페닐-1-(2-(5-(트리플루오로메톡시)-2 , 3-디하이드로 -1H-인덴 -2-일)아세틸 )-1， 2-디하이드로퀴놀린 -3-카복사마이드；  (232) 1 ^ -ethyl-2-oxo- ^ phenyl-1- (2- (5- (trifluoromethoxy) -2, 3-dihydro-1H-inden-2-yl) acetyl) -1, 2-dihydroquinoline-3-carboxamide;
(233) N-에틸-1-(2-(5-하이드록시 -2， 3—디하이드로ᅳ 1H-인덴 -2-일)아세틸 )-2- 옥소 -Nᅳ페닐 -1 , 2—디하이드로퀴놀린 -3-카복사마이드；  (233) N-ethyl-1- (2- (5-hydroxy-2, 3—dihydroox 1H-inden-2-yl) acetyl) -2-oxo-N ᅳ phenyl-1, 2-dihydro Quinoline-3-carboxamide;
(234) N-에틸— 1-(2-(5ᅳ에틸 -2 , 3-디하이드로 -1Hᅳ인덴 -2-일 )아세틸 )-2-옥소- N-페닐ᅳ1 , 2—디하이드로퀴놀린 -3-카복사마이드；  (234) N-ethyl— 1- (2- (5 ᅳ ethyl-2, 3-dihydro-1H ᅳ inden-2-yl) acetyl) -2-oxo-N-phenyl ᅳ 1, 2-dihydro Quinoline-3-carboxamide;
(235) N-에틸 -1-(2-(5_플루오로ᅳ 2 , 3-디하이드로-lH-인덴ᅳ2-일)아세틸)-2ᅳ 옥소-N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드； (235) N-ethyl-1- (2- (5_fluoro ᅳ 2, 3-dihydro-lH-indenx-2-yl) acetyl) -2 ′ oxo-N-phenyl-1, 2-dihydro Quinoline-3-carboxamide;
(236) 1-(2-(5-클로로 2 , 3ᅳ디하이드로 -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—ethyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3 -Carboxamide;
(237) N-에틸 -1-(2-(5-아이오도ᅳ 2 ,3-디하이드로 -1H-인덴ᅳ 2-일 )아세틸) -2- 옥소 -Nᅳ페닐 -1， 2-디하이드로퀴놀린— 3-카복사마이드；  (237) N-ethyl-1- (2- (5-iodoze 2,3-dihydro-1H-indenyl 2-yl) acetyl) -2-oxo-N ᅳ phenyl-1,2-dihydro Quinoline—3-carboxamide;
(238) N-에틸 -1-(2-(5-니트로— 2， 3-디하이드로 -1H-인덴 -2-일)아세틸 )-2-옥소 -N-페닐 -1， 2-디하 드로퀴놀린— 3-카복사마이≡； (238) N-ethyl-1- (2- (5-nitro— 2, 3-dihydro-1H-inden-2-yl) acetyl) -2-oxo -N-phenyl-1, 2-dihadroquinoline—3-carboxamid;
(239) 1-(2-(5-아미노 -2ᅳ 3-디하이드로 -1Hᅳ인덴 -2-일)아세틸 )— Νᅳ에틸 -2—옥소 -Ν-페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (239) 1- (2- (5-amino-2 ′ 3-dihydro-1H ᅳ inden-2-yl) acetyl) —Nethylethyl-2—oxo-Ν-phenyl-1,2-dihydro Quinoline-3-carboxamide;
(240) Ν-에틸 -2-옥소 -Ν-페닐 -1， 2—디하이드로퀴놀린 -3—카복사마이드；  (240) Ν-ethyl-2-oxo-Ν-phenyl-1, 2-dihydroquinoline-3-carboxamide;
(241) 1-(3-(2，3-디하이드로 -1Η-인덴 -2-일)프로파노일) -Ν-에틸 -2-옥소 -Ν- 페닐— 1， 2-디하이드로퀴놀린 -3-카복사마이드； (241) 1- (3- (2,3-dihydro-1Η-inden-2-yl) propanoyl) -Ν-ethyl-2-oxo-Ν-phenyl— 1, 2-dihydroquinoline-3 -Carboxamide;
(242) Ν-에틸 -2-옥소 -Ν-페닐 -5—프로피온아미도 -1 , 2—디하이드로퀴놀린 -3-카 복사마이드;  (242) N-ethyl-2-oxo-N-phenyl-5-propionamido-1,2-dihydroquinoline-3-carboxamide;
(243) 5-부티라미도 -Νᅳ에틸 -2-옥소 -Ν—페닐 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (243) 5-butyramido-Ν ᅳ ethyl-2-oxo-Ν-phenyl-1, 2-dihydroquinoline-3-carboxamide;
(244) Ν-메틸 -2-옥'소 -Ν-(ρ-를일) 1 , 2-디하이드로퀴놀린 -3-카복사마이드；(244) Ν- methyl-2-oxide, bovine -Ν- (ρ- reulil) 1, 2-dihydro-quinoline-3-carboxamide;
(245) Ν-에틸 -2-옥소 -5-펜탄아미도— Ν-(ρ-를일 )—1， 2-디하이드로퀴놀린 -3一카 복사마이드; (245) Ν-ethyl-2-oxo-5-pentaneamido—N- (ρ-ylyl) —1, 2-dihydroquinoline-3 ylcar radiamide;
(246) Ν-에틸— 5-(2—메톡시아세트아미도 )-2—옥소 -Νᅳ (ρ—를일 )_1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (246) Ν-ethyl— 5- (2—methoxyacetamido) -2—oxo-Ν ᅳ (ρ—ylyl) _1, 2-dihydro quinoline-3-carboxamide;
(247) Ν-에틸 -2-옥소 -Ν-(ρ-를일 )—1， 2-디하이드로퀴놀린 -3-카복사마이드； (247) Ν-ethyl-2-oxo-Ν- (ρ-ylyl) —1, 2-dihydroquinoline-3-carboxamide;
(248) Ν—에틸 -2—옥소 -1-(4— (페닐티오)벤질) -Ν-(ρ-를일) 1，2-디하이드로 퀴놀린 -3-카복사마이드; (248) N—ethyl-2-2 oxo-1- (4— (phenylthio) benzyl) -Ν- (ρ-ylyl) 1,2-dihydro quinoline-3-carboxamide;
(249) Ν-에틸 -2-옥소ᅳ1-(4-페녹시벤조일) -Ν-(ρ-를일) -1 , 2-디하이드로퀴놀린 -3—카복사마이드;  (249) Ν-ethyl-2-oxo'1- (4-phenoxybenzoyl) -Ν- (ρ- ylyl) -1, 2-dihydroquinoline-3—carboxamide;
(250) Ν-에틸 -2 옥소 -1-(4— (페닐티오)벤조일 )-Ν-(ρ-를일 )-1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (250) Ν-ethyl-2 oxo-1- (4— (phenylthio) benzoyl) -Ν- (ρ-ylyl) -1, 2-dihydro quinoline-3-carboxamide;
(251) Ν-에틸 -2-옥소 -1— (2-(4- (페닐티오)페닐)아세틸) -Ν-(ρ—를일 )_1，2—디하 이드로퀴놀린 -3-카복사마이드; '  (251) Ν-ethyl-2-oxo-1— (2- (4- (phenylthio) phenyl) acetyl) -Ν- (ρ—ylyl) _1,2—dihydroquinoline-3-carboxamide; '
(252) Ν-에틸 -2-옥소 -1-(2— (4—페녹시페닐)아세틸) -Ν-(ρ-를일) -1 , 2-디하이드 로퀴놀린— 3-카복사마이드; (252) N-ethyl-2-oxo-1- (2— (4—phenoxyphenyl) acetyl) -Ν- (ρ-ylyl) -1, 2-dihydroquinoline—3-carboxamide;
(253) 1-(2-(4-벤질페닐)아세틸) -Ν-에틸 -2-옥소— Ν-(ρ—를일) 1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (253) 1- (2- (4-benzylphenyl) acetyl) -Ν-ethyl-2-oxo— Ν- (ρ—ylyl) 1, 2-dihydro quinoline-3-carboxamide;
(254) 1-(4—벤질벤조일 )— Ν—에틸 -2-옥소 -Ν-(ρ-를일 )—1， 2-디하이드로퀴놀린- 3-카복사마이드;  (254) 1- (4—benzylbenzoyl) —N—ethyl-2-oxo-Ν- (ρ-ylyl) —1, 2-dihydroquinoline-3-carboxamide;
(255) Ν-(4-메록시페닐) -Ν-메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이 (256) N-에틸 -N-(4-메특시페닐 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3—카복사마이 (255) Ν- (4-methoxyphenyl) -Ν-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (256) N-ethyl-N- (4-methoxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxami
(257) 5-(2-브로모아세트아미도)— N-에틸 -N-(4-메특시페닐 )— 2-옥소— 1，2-디하 이드로퀴놀린 -3-카복사마이드; (257) 5- (2-bromoacetamido) —N-ethyl-N- (4-methoxyphenyl) —2-oxo—1,2-dihydroquinoline-3-carboxamide;
(258) N-(4-브로모페닐) 메틸 -2-옥소 -1 , 2—디하이드로퀴놀린 -3-카복사마 이드；  (258) N- (4-bromophenyl) 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— 2ᅳ옥소 -1-(2H-피를 -3—카르보닐) -1 , 2-디하이 드로퀴놀린 -3-카복사마이드; (260) N- (4-bromophenyl) -N-methyl- 2ioxo--1- (2H-pyr -3-carbonyl) -1, 2-dihedroquinoline-3-carboxamide;
(261) N-(4-브로모페닐 )-Nᅳ메틸 -2-옥소 -1- (티오펜 -2-카르보닐 )_1， 2-디하이 드로퀴놀린 -3-카복사마이드；  (261) N- (4-bromophenyl) -N ᅳ methyl-2-oxo-1- (thiophene-2-carbonyl) _1, 2-dihydrodroquinoline-3-carboxamide;
(262) N-(4-브로모페닐 )-1- (퓨란ᅳ 2—카르보닐 )-N-메틸 -2—옥소 -1， 2- 디하이드로퀴놀린 -3-카복사마이드;  (262) N- (4-bromophenyl) -1- (furanskene 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-디 하이드로퀴놀린 -3-카복사마이드;  (263) N- (4-bromophenyl) -N-methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1, 2-dihydroquinoline-3-carboxamide ;
(264) N-(4-브로모페닐 )-1-(2- (퓨란 -2-일)아세틸 )-N_메틸 -2-옥소 -1，2-디하 이드로퀴놀린 -3—카복사마이드；  (264) N- (4-bromophenyl) -1- (2- (furan-2-yl) acetyl) -N_methyl-2-oxo-1,2-dihydroquinoline-3—carboxamide;
(265) 1-(2— (2Hᅳ피를ᅳ2ᅳ일 )아세틸) -N-(4-브로모페닐) -N-메틸— 2-옥소 -1，2- 디하이드로퀴놀린 -3-카복사마이드； (265) 1- (2— (2H ᅳ pyrrole2 ᅳ yl) acetyl) -N- (4-bromophenyl) -N-methyl- 2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(266) N-(4-브로모페닐) -N-에틸 -2—옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이  (266) N- (4-bromophenyl) -N-ethyl-2—oxo-1, 2-dihydroquinoline-3-carboxamide
(267) Ν-(4-브로모페닐 )-1- (사이클로핵산카르보닐) -Ν-에틸 -2-옥소 -1， 2-디하 이드로퀴놀린 -3-카복사마이드; (267) Ν- (4-bromophenyl) -1- (cyclonucleocarbonyl) -Ν-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(268) Ν-(4-브로모페닐) -1-(3-사이클로핵실프로파노일) -Ν-에틸 -2-옥소— 1，2- 디하이드로퀴놀린 -3-카복사마이드;  (268) Ν- (4-bromophenyl) -1- (3-cyclonucleosilpropanoyl) -Ν-ethyl-2-oxo— 1,2-dihydroquinoline-3-carboxamide;
(269) Ν-(4-브로모페닐 )-5-(2-클로로아세트아미도) -Νᅳ에틸 -2-옥소 -1，2—디하 이드로퀴놀린 -3-카복사마이드；  (269) Ν- (4-bromophenyl) -5- (2-chloroacetamido) -Ν ᅳ ethyl-2-oxo-1,2—dihydroquinoline-3-carboxamide;
(270) Ν-(4-클로 페닐) -Ν-메틸— 2—옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이 (271) N-(4-클로로페닐 )-1- (사이클로펜탄카르보닐 )— N-메틸— 2—옥소 -1，2-디하 이드로퀴놀린 -3-카복사마이드; (270) Ν- (4-chlorophenyl) -Ν-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- -클로로페닐 )-1ᅳ (퓨란 2-카르보닐 )-N-메틸— 2—옥소— 1， 2-디하이드 로퀴놀린 -3-카복사마이드；  (272) N- -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-디하이 드로퀴놀린 -3-카복사마이드； (273) N- (4-chlorophenyl) -N-methyl-2-oxo-1— (thiophene-2-carbonyl) -1, 2-dihydrodroquinoline-3-carboxamide;
(274) N-(4-클로로페닐) -N-메틸— 2ᅳ옥소 -1-(2H-피를 -2-카르보닐) -1 , 2-디하이 드로퀴놀린 -3-카복사마이드;  (274) N- (4-chlorophenyl) -N-methyl- 2ioxo--1- (2H-pyr-2-carbonyl) -1, 2-dihydrodroquinoline-3-carboxamide;
(275) N-(4-클로^페닐 )-N-에틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이 드;  (275) N- (4-chloro ^ phenyl) -N-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(276) N-(4—클로로페닐 )-1-(2—사이클로펜틸아세틸 )-N-에틸 -2—옥소 -1， 2-디하 이드로퀴놀린 -3-카복사마이드；  (276) N- (4—chlorophenyl) -1- (2—cyclopentylacetyl) -N-ethyl-2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(277) N- -클로로페닐 )-N-에틸ᅳ 1-( 2— (퓨란 -2-일)아세틸)— 2—옥소— 1， 2-디하 이드로퀴놀린 -3-카복사마이드;  (277) N-chlorophenyl) -N-ethyl ᅳ 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-디 하이드로퀴놀린 -3-카복사마이드； (278) N- (4—chlorophenyl) -N-ethyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) -1,2-di hydroquinoline-3-carboxamide;
(279) 1-(2-(2Η—피롤ᅳ 2-일)아세틸) -N-(4-클로로페닐) N-에틸 -2-옥소 -1 , 2-디 하이드로퀴놀린 -3-카복사마이드;  (279) 1- (2- (2Η—Pyrrolen 2-yl) acetyl) -N- (4-chlorophenyl) N-ethyl-2-oxo-1, 2-di hydroquinoline-3-carboxamide;
(280) N-(4-플루오로페닐 )-N-메틸 -2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복사마 이드;  (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-디하 이드로퀴놀린 -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) -N-methyl-2-oxo— 1, 2-dihydroquinoline-3 Carboxamide;
(283) N-(4-플루오로페닐) -N-메틸— 2—옥소— 1— (2-옥소 -2— (4- (트리플루오로 메특시)페닐)에틸) -1，2-디하이드로퀴놀린 -3-카복사마이드; (283) N- (4-fluorophenyl) -N-methyl— 2—oxo— 1— (2-oxo-2 — (4- (trifluoro meso) phenyl) ethyl) -1,2-di Hydroquinoline-3-carboxamide;
(284) N-(4-플루오로페닐 )-N-메틸ᅳ 1— (2-(4—니트로페닐 )-2-옥소-에틸 )-2- 옥소 -1， 2-디하이드로퀴놀린— 3-카복사마이드；  (284) N- (4-fluorophenyl) -N-methyl ᅳ 1— (2- (4—nitrophenyl) -2-oxo-ethyl) -2-oxo-1, 2-dihydroquinoline— 3- Carboxamide;
(285) N-(4-플루'오로페닐) -1-(2-(4—하이드록시페닐 )-2-옥소—에틸) -N-메틸- 2ᅳ옥소 -1，2—디하이드로퀴놀린 -3-카복사마이드;  (285) N- (4-Flu'orophenyl) -1- (2- (4—hydroxyphenyl) -2-oxo-ethyl) -N-methyl-2 ioxo-1,2-dihydroquinoline- 3-carboxamide;
(286) N-(4-플루오로페닐 )-1-(2-(4-플루오로페닐 )-2-옥소-에틸) -Nᅳ메틸 -2- /옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (286) N- (4-fluorophenyl) -1- (2- (4-fluorophenyl) -2-oxo-ethyl) -N ᅳ methyl-2- / Oxo-1, 2-dihydroquinoline-3-carboxamide;
(287) 1-(2-(4-에'틸페닐 )-2-옥소-에틸) -N-(4—플루오로페닐)— N-메틸 -2-옥소- 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드;  (287) 1- (2- (4-Ethylphenyl) -2-oxo-ethyl) -N- (4—fluorophenyl)-N-methyl-2-oxo- 1, 2-dihydroquinoline- 3 ᅳ carboxamide;
(288) 1-(2-(4-시아노페닐)아세틸)— N-(4-에틸펜에틸)ᅳ 2ᅳ옥소 -1 , 2-디하이드 로퀴놀린— 3-카흑사마이드;  (288) 1- (2- (4-cyanophenyl) acetyl) —N- (4-ethylphenethyl) ᅳ 2ioxo-1, 2-dihydroquinoline—3-carbamide;
(289) N-에틸 -N-(4-플루오로페닐 )-2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3-카복사 마이드;  (289) N-ethyl -N- (4-fluorophenyl) -2-oxo-1, 2'dihydroquinoline-3-carboxamide;
(290) 1-(2-(4-아미노페닐 )ᅳ2-옥소-에틸 )-N-에틸 -N— (4-플루오로페닐 )ᅳ2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (290) 1- (2- (4-aminophenyl) ᅳ 2-oxo-ethyl) -N-ethyl-N— (4-fluorophenyl) ᅳ 2-oxo-1,2-dihydroquinoline-3- Carboxamide;
(291) 1-(2-(4-시아노페닐)ᅳ 2-옥소-에틸) 에틸 -N-(4-플루오로페닐 )ᅳ2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (291) 1- (2- (4-cyanophenyl) ᅳ 2-oxo-ethyl) ethyl-N- (4-fluorophenyl) ᅳ 2-oxo-1,2-dihydroquinoline-3-carbox Amide;
(292) N-에틸 -N-..(4ᅳ플루오로페닐)ᅳ 1-(2-(4- (메틸티오)페닐) 2-옥소-에틸) - 2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드；  (292) N-ethyl-N-.. (4 ᅳ fluorophenyl) ᅳ 1- (2- (4- (methylthio) phenyl) 2-oxo-ethyl)-2-oxo-1, 2-dihydro Quinoline-3′carboxamide;
(293) N-(4-에틸페닐 )-N-메틸 -2-옥소 -1 , 2ᅳ디하이드로퀴놀린—3—카복사마이드； (294) 1-(2 , 4—디메틸벤질) -N-(4-에틸페닐) -N-메틸 -2-옥소 -1 , 2—디하이드로 퀴놀린 _3-카복사마이드;  (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-dihydro quinoline _3-carboxamide;
(295) 1-(2， 4-디메틸펜에틸 )-N-(4-에틸페닐)— N—메틸ᅳ2—옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (295) 1- (2, 4-dimethylphenethyl) -N- (4-ethylphenyl) —N—methyl ᅳ 2—oxo-1, 2-dihydro quinoline-3-carboxamide;
(296) N-(4-에틸페닐 )-1ᅳ (4-하이드록시 -2-메틸벤질) -N-메틸 -2-옥소 -1， 2- 디하이드로퀴놀란 -3-카복사마이드;  (296) N- (4-ethylphenyl) -1 '(4-hydroxy-2-methylbenzyl) -N-methyl-2-oxo-1,2-dihydroquinolan-3-carboxamide;
(297) N-(4-에틸페닐) 메틸 -1-(2-메틸ᅳ 4-니트로벤질) -2-옥소 -1 , 2-디하이 드로퀴놀린ᅳ 3_카복사마이드; (297) N- (4-ethylphenyl) methyl-1- (2-methyl ᅳ 4-nitrobenzyl) -2-oxo-1, 2-dihydrodroquinoline 3 _carboxamide;
(298) 1-(4-에틸 -2-메틸펜에틸 )— N-(4-에틸페닐) 메틸 -2-옥소 -1， 2-디하이 드로퀴놀린 -3-카복사마이드；  (298) 1- (4-ethyl-2-methylphenethyl) —N- (4-ethylphenyl) methyl-2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(299) N-(4-에틸페닐) -1-(4-하이드록시— 2-메틸펜에틸) N-메틸ᅳ 2-옥소 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드；  (299) N- (4-ethylphenyl) -1- (4-hydroxy- 2-methylphenethyl) N-methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(300) N-(4—에틸페닐 )-N—메틸 -1-(2ᅳ메틸 -4ᅳ니트로펜에틸 )-2-옥소 -1，2-디하 이드로퀴놀린 -3-카복사마이드；  (300) N- (4—ethylphenyl) -N-methyl-1- (2 ᅳ 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-디하이 드로퀴놀린ᅳ 3-카복사마이드;  (301) 1- (4-ethyl-2-methylbenzyl) -N— (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydrodroquinolin ᅳ 3-carboxamide;
(302) 1ᅳ(2， 3-디메틸벤질 )— N-(4—에틸페닐 )-N_메틸 -2-옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드; (302) 1 '(2, 3-dimethylbenzyl) — N- (4—ethylphenyl) -N_methyl-2-oxo-1, 2-dihydro Quinoline-3-carboxamide;
(303) N- -에틸페닐) -5-(2-플루오로아세트아미도) -N-메틸 -2-옥소 -1 , 2ᅳ디하 이드로퀴놀린 -3-카복사마이드;  (303) N-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； (305) 1-(2 , 5-디메틸벤질) -N—에틸— N-(4-에틸페닐) -2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (304) N-ethyl-N- (4-ethylphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (305) 1- (2, 5-dimethylbenzyl) -N— Ethyl—N- (4-ethylphenyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(306) 1-(3， 4-디메틸벤질)— N-에틸 -N— (4-에틸페닐 )-2-옥소 -1， 2-디하이드로 퀴놀린 -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-디하이드로 퀴놀린 -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-디하이 드로퀴놀린— 3-카복'사마이드； (308) N-ethyl -N- (4-ethylphenyl) -2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydrodroquinoline— 3-carboxy ' amide;
(309) 1— (4- (디플루오로메틸) -2-메틸벤질,) -Nᅳ에틸 -N-(4-에틸페닐)ᅳ 2-옥소- 1， 2-디하이드로퀴놀린 -3-카복사마이드；  (309) 1— (4- (difluoromethyl) -2-methylbenzyl,) -N ᅳ ethyl-N- (4-ethylphenyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-car Radiation amide;
(310) (E)-l-(2-(4- (디플루오로메틸)— 2-메틸사이클로핵사 -2 , 4-디엔 -1- 일리딘)에틸) -N-에틸 -N-(4-에틸페닐) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복 사마이드; (310) (E) -l- (2- (4- (difluoromethyl) — 2-methylcyclonucleus -2, 4-diene-1-ylidine) ethyl) -N-ethyl-N- (4 -Ethylphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(311) N-(4-하이드록시페닐) -N-메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드;  (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) ^(4-하이드록시페닐)-^메틸-2-옥소ᅳ1-(2，3，4，5，6_펜타메틸벤질)- 1， 2-디하이드로퀴놀린 -3-카복사마이드;  (313) ^ (4-hydroxyphenyl)-^ methyl-2-oxo ᅳ 1- (2,3,4,5,6_pentamethylbenzyl) -1,2-dihydroquinoline-3-carboxamide ;
(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— 3-carboxamide ;
(315) N-에틸 -N— (4-하이드록시페닐 )— 2—옥소— 1， 2-디하이드로퀴놀린— 3—카복사 마이드;  (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 -3ᅳ카복사마이드；  (316) N-ethyl— N- (4—hydroxyphenyl) -1- (4-methoxy-2-methylphenethyl) 2-oxo-1, 2-dihydroquinoline-3′carboxamide;
(317) 1-(2ᅳ 3—디메틸펜에틸 )-N-에틸 -N-(4-하이드록시페닐 )-2-옥소 -1， 2—디하 이드로퀴놀린 -3-카복사마이드； (318) l-(2， 5-디메틸펜에틸) -N—에틸— N-(4-하이드록시페닐 )ᅳ2-옥소 -1， 2ᅳ디하 이드로퀴놀린 -3-카복사마이드; (317) 1- (2 ′ 3—dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (318) l- (2, 5-dimethylphenethyl) -N—ethyl—N- (4-hydroxyphenyl) ᅳ 2-oxo-1, 2'dihydroquinoline-3-carboxamide;
(319) 1-(2， 6-디메틸펜에틸) -N-에틸 -N-(4-하이드록시페닐)ᅳ 2-옥소 -1， 2ᅳ디하 이드로퀴놀린 -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)ᅳ1，2- 다하이드로퀴놀린 -3-카복사마이드; (320) N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1- (2,4,6-trimethylphenethyl) ᅳ 1,2- polyhydroquinoline-3-carboxamide;
(321) N-메틸 -N-(4-니트로페닐 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이  (321) N-methyl-N- (4-nitrophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
(322) ^메틸 -(4-니트로페닐)-2-옥소—1-(2，3 , 4 , 5，6-펜타메틸펜에틸)ᅳ1 , 2- 디하이드로퀴놀린 -3-카복사마이드; (322) ^ methyl- (4-nitrophenyl) -2-oxo—1- (2,3,4,5,6-pentamethylphenethyl) ᅳ 1, 2-dihydroquinoline-3-carboxamide;
(323) N-에틸 -N- .4-니트로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린— 3-카복사마이  (323) N-ethyl-N-.4-nitrophenyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxamy
(324) Ν-(4-(Ν ,Ν—디메틸설파모일)페닐 )-Ν-메틸 -2-옥소 -1 , 2-디하이드로퀴놀 린 -3-카복사마이드; (324) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -Ν-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(325) Ν-(4-(Ν,Ν-디메틸설파모일)페닐) -Ν-에틸 -2-옥소 -1 , 2—디하이드로퀴놀 린 -3-카복사마이드; (325) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -Ν-ethyl-2-oxo-1,2—dihydroquinoline-3-carboxamide;
(326) Ν-(4- (하이드록시메틸)페닐 )-Ν-메틸 -2—옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (326) Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(327) 1-(4-( 1Hᅳ피라졸 -1-일 )벤질) -Ν-(4- (하이드록시메틸)페닐) -Ν-메틸 -2- 옥소— 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드;  (327) 1- (4- (1H ᅳ pyrazol-1-yl) benzyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-2-oxo— 1,2-dihydroquinoline- 3 ᅳ carboxamide;
(328) 1-(4-( 1Η-피라졸 -1-일)벤조일) -Ν-(4- (하이드록시메틸)페닐) -Ν-메틸- 2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3—카복사마이드；  (328) 1- (4- (1Η-pyrazol-1-yl) benzoyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl- 2-oxo-1,2'dihydroquinoline-3 —Carboxamide;
(329) 1-(2， 2—디페닐아세틸) -Ν-(4- (하이드록시메틸)페닐 ) -Ν-메틸ᅳ 2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (329) 1- (2, 2-diphenylacetyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(330) 1-(2 , 2-디페닐에틸 )-Ν-(4— (하이드록시메틸)페닐 )-Ν_메틸 -2-옥소 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드; (330) 1- (2, 2-diphenylethyl) -Ν- (4— (hydroxymethyl) phenyl) -Ν_methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(331) Ν— (4- (하이드록시메틸)페닐 )-5-(3-하이드록시프로판아미도) -Ν-메틸- 2-옥소— 1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (331) Ν— (4- (hydroxymethyl) phenyl) -5- (3-hydroxypropaneamido) -Ν-methyl-2-oxo— 1,2-dihydroquinoline® 3-carboxamide;
(332) Ν-(4- (하이드록시메틸)페닐 )-Ν-메틸 -5-(2-니트로아세트아미도) -2- 옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드;  (332) Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-5 (2-nitroacetamido) -2-oxo-1,2-dihydroquinoline-3′carboxamide;
(333) Ν-에틸 -Ν-(4- (하이드록시메틸)페닐 )-2-옥소 -1 , 2—디하이드로퀴놀린 -3- 카복사마이드; (333) Ν-ethyl-Ν- (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-디하이 드로퀴놀린 -3-카복사마이드； (335) (E) -5- (but 2-enamido) -N-methyl- 2-oxo-N_ (4-vinylphenyl) -1, 2-dihydrodroquinoline-3-carboxamide;
(336) N-에틸ᅳ 2-옥소ᅳ N-(4-비닐페닐) -1，2—디하이드로퀴놀란 -3-카복사마이드;(336) N-ethyl ᅳ 2-oxo ᅳ N- (4-vinylphenyl) -1,2-dihydroquinolan-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-디하이드로 퀴놀린 -3-카복사마이드; (339) 5- (3, 4-dihydroxybenzamido) -N-ethyl-2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(340) 5-(3，4-디메틸벤즈아미도)ᅦ-에틸-2-옥소-1，2-디하이드로퀴놀린-3- 카복사마이드; (340) 5- (3,4-dimethylbenzamido) '-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(341) N- (메록시메틸 )ᅳ2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (341) N- (methoxymethyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(342) N- (브로모메틸 )ᅳ2-옥소 -1， 2-디하이드로퀴놀린— 3-카복사마이드；  (342) N- (bromomethyl) ᅳ 2-oxo-1, 2-dihydroquinoline— 3-carboxamide;
(343) N- (클로로메틸 )ᅳ2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (343) N- (chloromethyl) ᅳ 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)ᅳ 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-dihydroquinoline-3 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-프'로필 -1 , 2—디하이드로퀴놀린 -3-카복사마이드; 349 2-oxo -N- program "ropil-1,2-dihydro-quinoline-3-carboxamide;
(350) 5-(3- (벤조 [d] [ 1，3]디옥솔 -5-일 )프로판아미도 )— 2—옥소 -N-프로필 -1ᅳ 2- 디하이드로퀴놀린 -3-카복사마이드;  (350) 5- (3- (benzo [d] [1,3] dioxol-5-yl) propaneamido) — 2—oxo-N-propyl-1′2-dihydroquinoline-3-carbox Amide;
(351) (E)-2-옥소 -N- (프로프 -1-엔 -1-일) -1 , 2-디하이드로퀴놀린 -3-카복사 마이드;  (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) (E) -5- (2- (naphthalen-2-yl) acetamido) — 2—oxo— N- (prop-1-en-1-yl) -1, 2-dihydroquinoline -3-carboxamide;
(354) N-(2-메특시에틸) -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； (356) 5-(2-( [ 1 , 1 ' -비페닐 ] -4-일)아세트아미도)— 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'-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-(2ᅳ플루오로에틸 )-2—옥소— 1 , 2—디하이드로퀴놀린— 3-카복사마이드； (359) N-(2-하이드록시에틸) -2-옥소 -1 , 2—디하이드로퀴놀린 -3-카복사마이드;(358) N- (2′fluoroethyl) -2—oxo— 1, 2—dihydroquinoline— 3-carboxamide; (359) N- (2-hydroxyethyl) -2-oxo-1, 2—dihydroquinoline-3-carboxamide;
(360) N-(2ᅳ니트로에틸 )-2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드;(360) N- (2 ᅳ nitroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(361) N-(3-하이드록시프로필) -2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이 (361) N- (3-hydroxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
(362) (Ε)-2-옥소 -Ν- (펜트 -3-엔— 1-일 )-1 , 2-디하이드로퀴놀린 -3—카복사마이 드; (362) (Ε) -2-oxo-Ν- (pent-3-ene— 1-yl) -1, 2-dihydroquinoline-3—carboxamide;
(363) Ν-부틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (363) N-butyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(364) Ν-(3-메톡시프로필 )-2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3-카복사마이드； (364) Ν- (3-methoxypropyl) -2-oxo-1'2-dihydroquinoline-3-carboxamide;
(365) Ν-(3-브로모프로필 )-2-옥소 -1， 2-디하이드로퀴놀린 -3—카복사마이드；(365) Ν- (3-bromopropyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide;
(366) Ν— (3-클로로프로필 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3—카복사마이드； (367) Ν-(3ᅳ플루오로프로필) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;(366) Ν— (3-chloropropyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide; (367) Ν- (3 ᅳ fluoropropyl) -2-oxo-1, 2 Dihydroquinoline-3-carboxamide;
(368) (Ε)-Ν- (핵스 -4-엔 -1-일 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드; (368) (Ε) -Ν- (nux-4-en-1-yl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(369) Ν-(3ᅳ하이드록시프로필 )— 2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드;  (369) Ν- (3′hydroxypropyl) —2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(370) Ν-(3-니트로프로필 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;(370) Ν- (3-nitropropyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(371) Ν-(4-하이드록시부틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；(371) Ν- (4-hydroxybutyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(372) Ν-(3， 4-디하이드록시벤질 )-2-옥소— 1， 2-디하이드로퀴놀린 -3-카복사 마이드； (372) Ν- (3, 4-dihydroxybenzyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(373) Ν-(3 , 4-디에틸벤질) -2-옥소 -1，2-디하이드로퀴놀린 -3—카복사마이드; (374) Ν-(3 , 4-디메틸벤질) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (373) Ν- (3, 4-diethylbenzyl) -2-oxo-1,2-dihydroquinoline-3—carboxamide; (374) Ν- (3, 4-dimethylbenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(375) Ν-(3 , 4-디하이드록시펜에틸) -2-옥소— 1， 2-디하이드로퀴놀린 -3—카복사 마이드; (375) Ν- (3, 4-dihydroxyphenethyl) -2-oxo— 1, 2-dihydroquinoline-3—carboxamide;
(376) 5-(2-(4-벤질페닐)아세트아미도) -Ν-(3 , 4-디하이드록시펜에틸 )-2-옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드;  (376) 5- (2- (4-benzylphenyl) acetamido) -Ν- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline— 3-carboxamide ;
(377) Ν-(3 , 4-디하이드록시펜에틸 )—2-옥소 -5-프로피온아미도 -1， 2-디하이드 로퀴놀린 -3-카복사마이드; (378) 5-부티라미도 -N-(3 ,4-디하이드록시펜에틸 )-2-옥소 -1ᅳ 2-디하이드로 퀴놀린 -3-카복사마이드; (377) Ν- (3, 4-dihydroxyphenethyl) —2-oxo-5-propionamido-1, 2-dihydroquinoline-3-carboxamide; (378) 5-butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1'2-dihydro quinoline-3-carboxamide;
(379) N-(3， 4-디하이드록시펜에틸 )—2-옥소 -5-펜탄아미도 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (379) N- (3, 4-dihydroxyphenethyl) —2-oxo-5-pentaneamido-1, 2-dihydroquinoline-3-carboxamide;
(380) N-(3 , 4-디에틸펜에틸 )-2ᅳ옥소—1 , 2-디하이드로퀴놀린 -3-카복사마이드;(380) N- (3, 4-diethylphenethyl) -2 ᅳ oxo—1, 2-dihydroquinoline-3-carboxamide;
(381) N-(3， 4-디메틸펜에틸) -2ᅳ옥소—1， 2-디하이드로퀴놀린 -3-카복사마이드；(381) N- (3, 4-dimethylphenethyl) -2oxo--1, 2-dihydroquinoline-3-carboxamide;
(382) N- (벤조 [d] [ 1，3]디옥솔ᅳ 5-일메틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드; (382) N- (benzo [d] [1,3] dioxol-2-5-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-카복사 마이드; (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-옥소ᅳ 1，2- 디하이드로퀴놀린 -3-카복사마이드;  (388) 5- (2-ethoxyacetamido) -N- (2- (naphthalene-2-yl) ethyl) -2-oxoxin 1,2-dihydroquinoline-3-carboxamide;
(389) ^( [ 1，1 ' -비페닐]-4-일메틸)-2-옥소-1，2—디하이드로퀴놀린-3- 카복사마이드; (389) ^ ([1,1'-biphenyl] -4-ylmethyl) -2-oxo-1,2—dihydroquinoline-3-carboxamide;
(390) Ν-(2-( [ 1 , 1 ' -비페닐 ] -4-일)에틸) -2-옥소 -1 , 2—디하이드로퀴놀린— 3- 카복사마이드;  (390) Ν- (2-([1,1'-biphenyl] -4-yl) ethyl) -2-oxo-1,2—dihydroquinoline—3-carboxamide;
(391) Ν-(4-벤질벤질) -2-옥소— 1， 2-디하이드로퀴놀린 -3-카복사마이드；  (391) Ν- (4-benzylbenzyl) -2-oxo—1,2-dihydroquinoline-3-carboxamide;
(392) Ν-(4—벤질펜에틸) 2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드; (392) Ν- (4—benzylphenethyl) 2-oxo-1,2-dihydroquinoline-3-carboxamide;
(393) Ν- (에록시메틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3—카복사마이드；  (393) Ν- (ethoxymethyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide;
(394) Ν- ( (에틸티오)메틸 )-2-옥소-1， 2-디하이드로퀴놀린 -3-카복사마이드； (394) Ν- ((ethylthio) methyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(395) Ν-(2-메록시에틸 )-2-옥소 -1， 2-디하이드로퀴놀린— 3-카복사마이드；(395) Ν- (2-methoxyethyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxamide;
(396) Ν- ( (에틸아미노)메틸) -2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드; (397) Ν-(2- (메틸티오)에틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3—카복사마이드;(396) Ν- ((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide; (397) Ν- (2- (methylthio) ethyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide;
(398) Ν-(2- (메 아미노)에틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이 r: · (398) Ν- (2- (methamino) ethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide r: ·
(399) 3-( ：페닐아미노)퀴놀린 -2(1H)ᅳ온;  (399) 3- (: phenylamino) quinoline-2 (1H) benzoone;
(400) 3-( ： p-를일아미노)퀴놀린 -2(1H)-온;  (400) 3-(: p-ylylamino) quinolin-2 (1H) -one;
(401) 3-( :(4-메록시페닐)아미노)퀴놀린 -2CLH)-온;  (401) 3- (: (4-methoxyphenyl) amino) quinolin-2CLH) -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) Ν,Ν-디메틸 -4-((2ᅳ옥소 -1,2ᅳ디하이드로퀴놀린 -3-일)아미노)벤젠 설폰 ^ >H- ~ -，  (410) Ν, Ν-dimethyl-4-((2 ᅳ oxo-1,2 ᅳ dihydroquinolin-3-yl) amino) benzene sulfone ^> H- ~-，
(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 -2CLH)-은;  (414) 3- (: (4-bromobenzyl) amino) quinoline-2CLH) -silver;
(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 -2UH)-온; (417) 3- ( : (4-ethylbenzyl) amino) quinolin-2UH) -one;
(418) 3-( :(4-하이드록시벤질)아미노)퀴놀린 -2(1H)ᅳ온;  (418) 3- (: (4-hydroxybenzyl) amino) quinoline-2 (1H) xion;
(419) 3-( :(4-니트로벤질)아미노)퀴놀린 -2(1H)—온;  (419) 3- (: (4-nitrobenzyl) amino) quinolin-2 (1H) —one;
(420) Ν,Ν-디메틸 -4-(( (2-옥소 -1,2-디하이드로퀴놀린 -3ᅳ일)아미노)메틸) 벤젠설폰(아미드; (420) Ν, Ν-dimethyl-4-(((2-oxo-1,2-dihydroquinolin-3xyl) amino) methyl) benzenesulfon ( amide;
(421) 3-( :(4— (하이드톡시메틸)벤질)아미노)퀴놀린 -2(1Η)-온; (421) 3- ( : (4— (hydroxymethyl) benzyl) amino) quinolin-2 (1Η) -one;
(422) 3-( :(4-비닐벤질)아미노)퀴놀린 -2(1Η)—은; (422) 3- ( : (4-vinylbenzyl) amino) quinoline-2 (1Η) —silver;
(423) 3- ：메틸 (페닐)아미노)퀴놀린 -2(1Η)-온;  (423) 3-: methyl (phenyl) amino) quinolin-2 (1Η) -one;
(424〕 3- ：에틸 (페닐)아미노)퀴놀린—2(1Η)ᅳ온;  (424) 3- ： ethyl (phenyl) amino) quinoline—2 (1Η) benzoone;
(425) 3-< ：에틸 (Ρ-를일)아미노)퀴놀린 2(1Η)-온;  (425) 3-<: ethyl (Ρ-ylyl) amino) quinolin 2 (1Η) -one;
(426) 3- ：메틸 (Ρ-를일)아미노)퀴놀린 -2(1Η)-온; (427) 3- :(4-메톡시페닐) (메틸)아미노)퀴놀린 -2(1H)—온; (426) 3-: methyl (Ρ-ylyl) amino) quinolin-2 (1Η) -one; (427) 3-: (4-methoxyphenyl) (methyl) amino) quinolin-2 (1H) —one;
(428) 3- ：에틸 (4-메록시페닐)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)퀴놀린ᅳ 2(1H)-온;  (432) 3-: (4-chlorophenyl) (ethyl) amino) quinolin ᅳ 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)아미노)퀴놀린ᅳ 2(1H)_온;  (434) 3-: ethyl (4-fluorophenyl) amino) quinolin ᅳ 2 (1H) _one;
(435) 3- ：에틸 (4ᅳ엥틸페닐)아미노)퀴놀린 _2(1H)—온; (435) 3-: ethyl ( 4 ᅳ entylphenyl) amino) quinoline — 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)퀴놀된 -2(1H)_온;  (439) 3-: methyl (4-nitrophenyl) amino) quinolated -2 (1H) _one;
(440) 3-( ：에틸 (4-니트로페닐)아미노)퀴놀린—2(1H)-은; (440) 3- ( ： ethyl (4-nitrophenyl) amino) quinoline—2 (1H) -silver;
(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- (하이드톡시메틸)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][l,3]디옥솔 -5-일메틸)아미노)퀴놀린 -2(1H)-온; (449) 3-: (benzo [d] [l, 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-2 (1H) -one
(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; (458) 3- (프로필아미노)퀴놀린 -2( 1H)-온; (457) 3-(： ethylamino) quinolin-2 (1H) —one; (458) 3- (propylamino) quinolin-2 (1H) -one;
(459) 3- (부틸아미노)퀴놀린 -2( 1H)-온;  (459) 3- (butylamino) quinolin-2 (1H) -one;
(460) 3- ( (에록시메틸)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 -2ᅳ옥소 -N-페네틸 1-(4- (트라이플루오로메록시)벤질) -1 , 2- 디하이드로퀴놀린 -3-카르복스아미드;  (463) 5—chloro-2-hexoxo-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-capboxamide;
(465) 5-클로로 1-(4-아이소프로필벤질) -2-옥소 -N-페네틸 -1，2-디하이드로 퀴놀린 -3-카르복스아미드； (465) 5-chloro 1- (4-isopropylbenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide;
(466) 5-클로로 -1-(4-나이트로벤질) -2-옥소 -Nᅳ페네틸 -1ᅳ 2-디하이드로퀴놀린 -3-카르복스아미드;  (466) 5-chloro-1- (4-nitrobenzyl) -2-oxo-N -phenethyl-1'2-dihydroquinoline-3-carboxamide;
(467) 5- "로로 -1-(4-메록시벤질 )-2—옥소 -N-페네틸 -1， 2-디하이드로퀴놀린- 3—카르복스아미드;  (467) 5- "Loro-1- (4-methoxybenzyl) -2—oxo-N-phenethyl-1, 2-dihydroquinoline-3—carboxamide;
(468) 5-클로로 -1- -에틸벤질 )-N— (4—플루오로페네틸 )-2-옥소 -1 , 2-디하이 드로퀴놀린 -3-카프복스아미드；  (468) 5-chloro-1--ethylbenzyl) -N— (4—fluorophenethyl) -2-oxo-1, 2-dihydrodroquinoline-3-capboxamide;
(469) 5-클로로 N-(4ᅳ플루오로페네틸 )-1-(4-아이소프로필벤질) -2-옥소— 1， 2- 디하이드로퀴놀린 3-카르복스아미드；  (469) 5-chloro N- (4 ᅳ fluorophenethyl) -1- (4-isopropylbenzyl) -2-oxo— 1, 2-dihydroquinoline 3-carboxamide;
(470) 5-클로로 -N-(4-플루오로페네틸) -1-(4-나이트로벤질 )— 2-옥소 -1，2-디하 이드로퀴놀린 -3-카르복스아미드； (470) 5-chloro-N- (4-fluorophenethyl) -1- (4-nitrobenzyl) — 2-oxo-1,2-dihydroquinoline-3-carboxamide;
(471) 5-클로로 -N-(4ᅳ플루오로페네틸 )-1-(4-메톡시벤질 )-2-옥소 -1， 2-디하이 드로퀴놀린— 3-카르복스아미드；  (471) 5-chloro-N- (4 ᅳ fluorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1, 2-dihydrodroquinoline—3-carboxamide;
(472) 5-클로로 -N— (4ᅳ플루오로페네틸) -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-디하이드 로퀴놀린 -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-니트로— 2—옥소 -1 , 2- 디하이드로퀴놀린」 3—카르복사마이드)；  (474) N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitro— 2—oxo-1, 2-dihydroquinoline 3—carboxamide);
(475) N-(4-플루오로펜에틸) -5-니트로 1-(4-니트로벤질) -2-옥소 -1，2-디하이 드로퀴놀린 -3-카르복사마이드； (476) 5-아미노 -N-(4-브로모펜에틸 )-1-(4-메톡시벤질)ᅳ 2-옥소ᅳ 1， 2—디하이드 로퀴놀린 -3-카르복사마이드) ; (475) N- (4-fluorophenethyl) -5-nitro 1- (4-nitrobenzyl) -2-oxo-1,2-dihydrodroquinoline-3-carboxamide; (476) 5-amino-N- (4-bromophenethyl) -1- (4-methoxybenzyl) '2-oxo' 1, 2-dihydroquinoline-3-carboxamide);
(477) 1-(4-메록시벤질 )-5—니트로ᅳ 2—옥소 -N-펜에틸 -1， 2—디하이드로퀴놀린 -3 —카르복사마이드;  (477) 1- (4-methoxybenzyl) -5-nitrosene 2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
(478) N-(4-플루오로펜에틸)— 1-(4ᅳ메톡시벤질 )-5-니트로 -2ᅳ옥소 -1 , 2-디하이 드로퀴놀린 -3-카르복사마이드; (478) N- (4-fluorophenethyl) — 1- (4'methoxybenzyl) -5-nitro-2phenoxo-1, 2-dihydrodroquinoline-3-carboxamide;
(479) 5-니트로 -2-옥소 -N-펜에틸 1-(4- (트리플루오로메특시)벤질) -1 , 2-디하 이드로퀴놀린 -3-카르복사마이드;  (479) 5-nitro-2-oxo-N-phenethyl 1- (4- (trifluoromepoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide;
(480) N-(4-플루오로펜에틸 )ᅳ5-니트로 2-옥소 -1-(4- (트리플루오로메톡시) 벤질) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드;  (480) N- (4-fluorophenethyl) ᅳ 5-nitro 2-oxo-1- (4- (trifluoromethoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide;
(481) 1-(4-이소프로필벤질) -5-니트로— 2-옥소ᅳ Nᅳ펜에틸 -1 , 2-디하이드로퀴놀 린 -3-카르복사마이드;  (481) 1- (4-isopropylbenzyl) -5-nitro— 2-oxoox N-phenphenethyl-1, 2-dihydroquinoline-3-carboxamide;
(482) 메틸 1-(4ᅳ메톡시벤질 )-2—옥소 -5-(3-페닐프로파나미노) -1 , 2-디하이드 로퀴놀린 -3-카복실레이트;  (482) methyl 1- (4'methoxybenzyl) -2—oxo-5 (3-phenylpropanamino) -1, 2-dihydroquinoline-3-carboxylate;
(483) 메틸 5-(3ᅳ사이클로펜틸프로파나미도 )ᅳ1-(4-메톡시벤질)ᅳ 2-옥소 -1，2- 디하이드로퀴놀린 -3-카복실레이트； (483) methyl 5- (3′cyclopentylpropanamido) ᅳ 1- (4-methoxybenzyl) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxylate;
(484) 메틸 1-(4-메록시벤질) 2-옥소 -5-(2-페닐아세타미도) -1，2-디하이드로 퀴놀린 -3-카복실레이트;  (484) methyl 1- (4-methoxybenzyl) 2-oxo-5 (2-phenylacetamido) -1,2-dihydro quinoline-3-carboxylate;
(485) 메틸 5-벤' S아미도 -1-(4-메특시벤질)—2-옥소 -1 , 2—디하이드로퀴놀린- 3-카복실레이트; (485) Methyl 5-Ben 'S amido-l- (4-meteuk) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(486) 메틸 5-(2-(4-클로로페닐)아세트아미도 )-1-(4-메특시벤질) -2ᅳ옥소- 1， 2ᅳ디하이드로퀴놀린 -3-카복실레이트；  (486) methyl 5- (2- (4-chlorophenyl) acetamido) -1- (4-mesoxybenzyl) -2 ioxo-1,2 ᅳ dihydroquinoline-3-carboxylate;
(487) 메틸 5- (아다만테인 -1-카복시아미도 )ᅳ1_(4—메록시벤질) -2-옥소 -1 , 2- 디하이드로퀴놀린 -3-카복실레이트;  (487) methyl 5- (adamantane-1-carboxyxamido) 도 1_ (4—methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylate;
(488) 메틸 5-(3ᅳ 5—디메틸아다만테인 -1-카복시아미도 )-1-(4-메록시벤질) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복실레이트； (488) methyl 5- (3 ′ 5—dimethyladamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(489) 메틸 5-(3-브로모아다만테인 -1-카복시아미도 )— 1_(4-메록시벤질 )ᅳ2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카복실레이트;  (489) methyl 5- (3-bromoadamantane-1-carboxamido) — 1_ (4-methoxybenzyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxylate;
(490) 메틸 1-(4ᅳ'메톡시벤질) -5-(3—메틸아다만테인 -1-카복시아미도 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3—카복실레이트; (490) methyl 1- (4 ′ ′ methoxybenzyl) -5 (3—methyladamantane-1-carboxyxamido) -2-oxo-1, 2-dihydroquinoline-3—carboxylate;
(491) 메틸 5-(2- (아다만테인ᅳ 1-일)아미도 )-1-(4-메특시벤질) -2-옥소— 1，2- 디하이드로퀴놀린 -3-카복실레이트； (491) Methyl 5- (2- (adamantane ᅳ 1-yl) amido) -1- (4-mesoxybenzyl) -2-oxo— 1,2- Dihydroquinoline-3-carboxylate;
(492) 메틸 5-(2-(3，5-디메틸아다만테인— 1ᅳ일)아세트아미도 )-1-(4-메특시 벤질) -2-옥소 -1， 2-다이하이드록시퀴놀린 -3-카복실레이트；  (492) Methyl 5- (2- (3,5-dimethyladamantane—1hexyl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroxyquinoline- 3-carboxylate;
(493) 메틸 5— (2-(3ᅳ브로모메테인 -1-일)아세트아미도 )-1-(4-메록시벤질) -2- 옥소 -1 , 2-디클로로퀴놀린 -3-카복실레이트;  (493) Methyl 5— (2- (3 ᅳ bromomethane-1-yl) acetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxyl Rate;
(494) 메틸 1ᅳ(4ᅳ메특시벤질 )— 5-(2-(3—메틸아다만테인 -1-일)아세트아미도) - 2-옥소 -1， 2-디클로로퀴놀린 -3—카복실레이트；  (494) Methyl 1 '(4'memethoxybenzyl) — 5- (2- (3-methyladamantane-1-yl) acetamido)-2-oxo-1, 2-dichloroquinoline-3-carboxyl Rate;
(495) 메틸 5-(2-사이크로핵실아세트아미도 )-1-(4-메록시벤질) -2-옥소 -1 , 2- 디클로로퀴놀린 -3-카복실레이트；  (495) methyl 5- (2-cyclonucleosilacetamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(496) 메틸 5- (사이클로핵센카복시아미도 )ᅳ1-(4-메록시밴질) -2-옥소 -1，2- 디클로로퀴놀린 -3ᅳ카복실레이트; (496) methyl 5- (cyclonuclesencarboxamido) ᅳ 1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3'carboxylate;
(497) 메틸 5ᅳ (아다만테인 -1—카복시아미도 )-1-(4ᅳ에틸벤질 )ᅳ2-옥소ᅳ 1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (497) methyl 5 '(adamantane-1-carboxyxamido) -1- (4'ethylbenzyl)' 2-oxo '1, 2-dichloroquinoline-3-carboxylate;
(498) 메틸 5- (아다만테인ᅳ 1-카복시아미도 )-1-(3-메특시벤질) -2-옥소 -1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (498) methyl 5- (adamantane ᅳ 1-carboxyxamido) -1- (3-mesoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate;
(499) 메틸 5ᅳ (아다만테인 -1-카복시아미도 )-1-(4-나이트로벤질 )— 2ᅳ옥소 -1 , 2 ᅳ디클로로퀴놀린 -3-카복실레이트;  (499) methyl 5 '(adamantane-1-carboxyxamido) -1- (4-nitrobenzyl) —2oxo-l, 2'dichloroquinoline-3-carboxylate;
(500) 메틸 5- (아다만테인 -1-카복시아미도 )-2-옥소 -1-(4- (트라이플루오로 메록시)벤질) -1， 2-디클로로퀴놀린 -3-카복실레이트；  (500) methyl 5- (adamantane-1-carboxyxamido) -2-oxo-1- (4- (trifluoro methoxy) benzyl) -1, 2-dichloroquinoline-3-carboxylate;
(501 ) 메틸 5- (아다만테인 -1-카복소아미도 )-1-(4ᅳ사이아노벤질) -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 )-1ᅳ(4-플루오로벤질 )-2-옥소- 1 , 2-디클로로퀴놀린 -3-카복실레이트;  (502) methyl 5- (adamantane-1-carboxyxamido) -1 ′ (4-fluorobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(503) 5-(아다만테인 -1-카복시아미도 )-1-(4-메록시벤질 )-2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭액시드;  (503) 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid;
(504) 에틸 5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤질)ᅳ 2-옥소— 1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (504) ethyl 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) ᅳ 2-oxo—1, 2-dichloroquinoline-3-carboxylate;
(505) 5- (아다만테인 -1-카복시아미도 )-1-(4-메특시벤질 )-N-메틸 -2-옥소 -1 , 2 -디클로로퀴놀린 -3-카복시아미도;  (505) 5- (adamantane-1-carboxyxamido) -1- (4-mesoxybenzyl) -N-methyl-2-oxo-1,2-dichloroquinoline-3-carboxyxamido;
(506) 5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤질) -Ν , Ν-디메틸 -2- 옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복시아마이드; (507) 프로필 5- (아다만테인 -1-카복시아미도 )-1ᅳ(4—메톡시벤질) -2-옥소- 1， 2-디클로로퀴놀린 -3-카복실레이트; (506) 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -Ν, Ν-dimethyl-2-oxo-1,2-dihydroquinoline® 3-carboxamide; (507) propyl 5- (adamantane-1-carboxyxamido) -1 ′ (4—methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(508) 아이소프로필 5- (아다만테인— 1-카복시아미도 )— 1-(4-메톡시벤질 )ᅳ2- ：옥소 -1， 2-디클로로퀴놀린 -3-카복실레이트;  (508) isopropyl 5- (adamantane— 1-carboxyxamido) — 1- (4-methoxybenzyl) ᅳ 2-: oxo-1, 2-dichloroquinoline-3-carboxylate;
(509) N-(l-(4-메톡시벤질) -3- (메톡시메틸 )-2-옥소 -1 ,2ᅳ디하이드로퀴놀린 - 5ᅳ일)아다만테인 -1-카복시아마이드； (509) N- (l- (4-methoxybenzyl) -3- (methoxymethyl) -2-oxo-1,2'dihydroquinolin-5xyl) adamantane-1-carboxamide;
(510) N— (3- (에록시메틸 )-1-(4ᅳ메톡시벤질 )-2-옥소— 1ᅳ 2ᅳ디하이드로퀴놀린 - 5-일)아다만테인 -1—카복시아마이드;  (510) N— (3- (ethoxymethyl) -1- (4 ᅳ methoxybenzyl) -2-oxo—1 ᅳ 2 ᅳ dihydroquinolin-5-yl) adamantane-1—carboxamide;
(511) S-메틸 5- (아다만테인 -1-카복시아미도 )ᅳ1-(4-메톡시밴질) -2-옥소 -1 ,2 -디하이드로퀴놀린 -3ᅳ카보싸이오에이트;  (511) S-methyl 5- (adamantane-1-carboxyxamido) ᅳ 1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3 ᅳ carbothioate;
(512) S-에틸 5- (아다만테인 -1-카복시아미도 )— 1ᅳ(4-메톡시벤질) -2-옥소 -1，2 -디하이드로퀴놀린 -3ᅳ카보싸이오에이트;  (512) S-ethyl 5- (adamantane-1-carboxyxamido) —1 ′ (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3′carbothioate;
(513) 1-(4-메록시벤질) -5-나이트로퀴놀린 -2( 1H)ᅳ은;  (513) 1- (4-methoxybenzyl) -5-nitroquinoline-2 (1H) ᅳ silver;
(514) 5-아미노 -1ᅳ(4-메톡시벤질)퀴놀린 -2( 1H)-은;  (514) 5-amino-1 ′ (4-methoxybenzyl) quinoline-2 (1H) -silver;
(515) 5-하이드라지닐 -1-(4-메톡시벤질)퀴놀린 -2(1H)-온; (515) 5-hydrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H) -one;
(516) N— ( 1-(4-메록시벤질) -2—옥소 -1，2—디하이드로퀴놀린 -5-일)아다만테 인 ᅳ 1ᅳ카복사마이드;  (516) N— (1- (4-methoxybenzyl) -2—oxo-1,2—dihydroquinolin-5-yl) adamantane ᅳ 1 ᅳ carboxamide;
(517) N-( 1-(4—메'톡시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -5-일 )-3ᅳ메틸아다 만테인 -1-카복사마이드;  (517) N- (1- (4—methoxybenzyl) -2-oxo-1, 2-dihydroquinolin-5-yl) -3 ᅳ methyladamantane-1-carboxamide;
(518) N-(l-(4-메록시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -5-일) -3 ,5-디메틸 아다만테인 -1-카복사마이드； (518) N- (l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3,5-dimethyl adamantane-1-carboxamide;
(519) 3-브로모 -N-(l-(4-메특시벤질) -2ᅳ옥소 -1， 2ᅳ디하이드로퀴놀린 -5-일) 아다만테인 -1-카복사마이드;  (519) 3-bromo-N- (l- (4-methoxybenzyl) -2 ioxo-1,2 ᅳ dihydroquinolin-5-yl) adamantane-1-carboxamide;
(520) 3-클로로 -N-( 1-(4-메록시벤질 )— 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-( l— (4ᅳ메톡시벤질 )-2—옥소 -1，2-디하이드로 퀴놀 린 -5-일)아세트아마이드;  (521) 2— (adamantane-1-yl) -N- (l— (4′methoxybenzyl) -2—oxo-1,2-dihydroquinolin-5-yl) acetamide;
(522) N-( 1-(4-메록시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -5-일 )-2-(3-메틸 아다만탄 -1-일)아세트아마이드;  (522) N- (1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinolin-5-yl) -2- (3-methyl adamantan-1-yl) acetamide;
(523) 2-(3，5—디메틸아다만탄 -1-일) -N-( l-(4—메록시벤질)— 2-옥소 -1 ,2- 디하이드로퀴놀린 -5-일)아세트아마이드; (524) 2-(3-브로모아다만탄— 1-일 )-N-( 1-(4-메톡시벤질 )-2ᅳ옥소ᅳ 1 , 2-디하이 드로퀴놀린 -5-일)아세트아마이드; (523) 2- (3,5—dimethyladamantane-1-yl) -N- (l- (4—methoxybenzyl) — 2-oxo-1,2-dihydroquinolin-5-yl) acet Amides; (524) 2- (3-bromoadamantane— 1-yl) -N- (1- (4-methoxybenzyl) -2ioxoxol 1, 2-dihydrodroquinolin-5yl) acetamide ;
(525) 2ᅳ(3-클로로아다만탄— 1-일 )-Ν-(1-(4-메특시벤질 ) -2ᅳ옥소 1 ,2-디하이 드로퀴놀린 -5-일)아세트아마이드;  (525) 2 ′ (3-Chloroadamantane— 1-yl) -N— (1- (4-mesoxybenzyl) -2 소 oxo 1,2-dihedroquinolin-5-yl) acetamide;
(526) N' -(l-(4-메특시벤질)—2-옥소 -1 ,2-디하이드로퀴놀린 -5-일)아다만테인 -1-카르보하이드라자이드； (526) N '-(l- (4-mesoxybenzyl) —2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;
(527) N ' -( 1ᅳ(4-메특시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린— 5-일 )ᅳ3- 메틸아다만테인 -1-카르보하이드라자이드;  (527) N ′-(1 ′ (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin—5-yl) ᅳ 3-methyladamantane-1-carbohydrazide;
(528) ^' -(1-(4-메록시벤질)ᅳ2-옥소-1ᅳ2-디하이드로퀴놀린-5-일)-3，5- 디메틸아다만테인 -1-카르보하이드라자이드; (528) ^ '-(1- (4-methoxybenzyl) ᅳ 2-oxo-1 ᅳ 2-dihydroquinolin-5-yl) -3,5-dimethyladamantane-1-carbohydrazide ;
(529) 3-브로모 -N' -( l-(4-메톡시벤질) -2-옥소 -1 , 2-디하이드로퀴놀린ᅳ 5-일) 아다만테인 -1-카르보하이드라자이드；  (529) 3-bromo-N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolinyl 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' -( l— (4-메록시벤질) -2-옥소 -1，2-디하이드로 퀴놀린ᅳ5-일)아세토하이드라자이드; (531) 2- (adamantane-1-yl) -N '-(l— (4-methoxybenzyl) -2-oxo-1,2-dihydro quinolin ᅳ 5-yl) acetohydrazide;
(532) N' -( l-(4-맹록시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -5-일) -2-(3-메틸 아다만탄 -1-일)아세토하이드라자이드;  (532) N '-(l- (4-monoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -2- (3-methyl adamantane-1-yl) acetohai Dragazide;
(533) 2-(3 ,5-디메틸아다만탄 -1-일) -Ν'— (1-(4-메록시벤질) -2-옥소 -1 ,2- 디하이드로퀴놀린ᅳ 5-일)아세토하이드라자이드；  (533) 2- (3,5-dimethyladamantane-1-yl) -Ν'— (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin ᅳ 5-yl) Acetohydrazide;
(534) 2-(3-브로모아다만탄 -1—일 )-Ν'— ( 1-(4-메특시벤질) -2-옥소 -1 ,2-디하이 드로퀴놀린 -5-일)아세토하이드라자이드； 및  (534) 2- (3-bromoadamantane-1-yl) -Ν'— (1- (4-methoxybenzyl) -2-oxo-1,2-dihedroquinolin-5-yl) aceto Hydrazide; and
(535) 2-(3-클로로아다만탄 -1-일) -N' -(l-(4ᅳ메톡시벤질 )-2-옥소 -1 , 2-디하이 드로퀴놀린 -5-일)아세토하이드라자이드  (535) 2- (3-Chloroadamantane-1-yl) -N '-(l- (4 벤 methoxybenzyl) -2-oxo-1, 2-dihedroquinolin-5-yl) acetohai Drazide
로 구성된 군으로부터 선택된다. 본 발명의 보다 더 구체적인 구현예에 따르면 본 발명의 퀴놀리논 유도체는 It is selected from the group consisting of. According to a more specific embodiment of the present invention the quinolinone derivative of the present invention
(1) 1-(4-에틸벤질 )—5-니트로— 2-옥소 펜에틸 -1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (1) 1- (4-ethylbenzyl) -5-nitro- 2-oxophenethyl-1, 2-dihydroquinoline-3-carboxamide;
(2) 1-(4ᅳ에틸펜에틸 )-5—니트로 -2-옥소 -Ν-펜에틸 -1，2-디하이드로퀴놀린 -3- 카복사마이드; (2) 1- (4 ᅳ ethylphenethyl) -5—nitro-2-oxo-Ν-phenethyl-1,2-dihydroquinoline-3- Carboxamide;
(3) 1-(4-플루오로벤질 )—5-니트로 -2ᅳ옥소 -N-펜에틸ᅳ 1 , 2-디하이드로퀴놀린- 3-카복사마이드;  (3) 1- (4-fluorobenzyl) —5-nitro-2oxo-N-phenethyl ᅳ 1, 2-dihydroquinoline-3-carboxamide;
(4) 1ᅳ(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—옥소ᅳ N-펜에틸 -1， 2-디하이드로퀴놀린ᅳ 3- 카복사마이드;  (5) 1- (4-chlorobenzyl) -5-nitro-2—oxozone N-phenethyl-1,2-dihydroquinoline® 3-carboxamide;
(6) 5-니트로 -1-(4—니트로벤질 )-2-옥소 -N—펜에틸 -1 , 2-디하이드로퀴놀린ᅳ 3- 카복사마이드；  (6) 5-nitro-1- (4-nitrobenzyl) -2-oxo-N-phenethyl-1, 2-dihydroquinoline® 3-carboxamide;
(7) 1-(4-아미노벤질) -5-니트로 -2ᅳ옥소—N-펜에틸 -1 , 2-디하이드로퀴놀린ᅳ 3- 카복사마이드; (7) 1- (4-aminobenzyl) -5-nitro-2 ᅳ oxo-N-phenethyl-1, 2-dihydroquinoline® 3-carboxamide;
(8) 1-(4-시아노벤질) -5-니트로 -2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린ᅳ 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 -1ᅳ(4-니트로펜에틸) -2-옥소 -N-펜에틸ᅳ 1 , 2-디하이드로퀴놀린- 3-카복사마이드  (16) 5-nitro-1 '(4-nitrophenethyl) -2-oxo-N-phenethyl ᅳ 1, 2-dihydroquinoline-3-carboxamide
로 구성된 군으로부터 선택된다. It is selected from the group consisting of.
본 발명에 따르면， 상기 나열한 10가지 화합물은 동일한 농도 ( ΙΟ μ Μ)를 투여하였을 때 ILᅳ 2에 대해 매우 높은 억제율 (% Inhibi t i on)을 가짐이 확인되었다. 따라서 이들은 과도한 IL-2 활성과 관련된 다양한 질환의 효과적인 치료 조성물로 이용될 수 있다. 본 발명의 다른 양태에 따르면， 본 발명은 본 발명에서 개시하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 IL-2 ( Int er l eukin-2)의 활성 억제용 조성물을 제공한다. 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. 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， 텍스트로스， 수크로스, 솔비를, 만니를, 전분, 아카시아 고무, 인산 칼슴， 알기네이트， 젤라틴 규산 칼슘， 미세결정성 셀를로스， 폴리비닐피를리돈, 셀를로스， 물， 시럽， 메틸 셀를로스, 메틸히드록시벤조에이트， 프로필히드톡시벤조에이트， 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. According to the present invention, it was confirmed that the ten compounds listed above have a very high inhibition rate (% Inhibi ti on) for ILV2 when the same concentration (ΙΟμΜ) was administered. Thus they can be used as effective therapeutic compositions for various diseases associated with excessive IL-2 activity. According to another aspect of the invention, the present invention is a composition for inhibiting the activity of IL-2 (Int er eukin-2) comprising a quinolinone derivative disclosed in the present invention or a pharmaceutically acceptable salt thereof as an active ingredient To provide. According to another aspect of the present invention, the present invention provides a prophylactic method for preventing a disease associated with IL-2 overexpression or IL-2 overactivity comprising a quinolinone derivative disclosed herein or a pharmaceutically acceptable salt thereof as an active ingredient. Or a therapeutic composition. When the composition of the present invention is made into a pharmaceutical composition, the pharmaceutical composition of the present invention includes a pharmaceutically acceptable carrier. Pharmaceutically acceptable carriers contained in the pharmaceutical composition of the present invention are those commonly used in the preparation, lactose, textose, sucrose, sorbbi, manny, starch, acacia rubber, phosphate, alginate, Gelatin Calcium Silicate, Microcrystalline Cellulose, Polyvinylpyridone, Cellulose, Water, Syrup, Methyl Cellulose, Methylhydroxybenzoate, Propylhydroxybenzoate, Talc, Magnesium Stearate and Mineral Oil One is not limited thereto. The pharmaceutical composition of the present invention may further include a lubricant, a humectant, a sweetener, a flavoring agent, an emulsifier, a suspending agent, a preservative, and the like, 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 may be administered orally or parenterally, and in the case of parenteral administration, it may be administered by intravenous injection, subcutaneous injection, intramuscular 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 감웅성과 같은 요인들에 의해 다양하게 처방될 수 있다. 본 발명의 약제학적 조성물의 1일 투여량은 예컨대 0.001-100 mg/kg이다. 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 액스제, 산제， 분말제， 과립제, 정제 또는 갑셀제 형태일 수도 있으며， 분산제 또는 안정화제를 추가적으로 포함할 수 있다. 본 발명의 구체적인 구현예에 따르면， 본 발명의 조성물로 치료되는 IL-2 과발현 또는 IL-2 과다활성과 관련된 질환은 염증성 질환 또는 자가면역 질환이다.  Suitable dosages of the pharmaceutical compositions of the present invention may be prescribed in various ways depending on factors such as the method of formulation, the mode of administration, the age of the patient, body weight, sex, morbidity, food, time of administration, route of excretion and response sensitivity. Can be. The daily dose of the pharmaceutical composition of the present invention is, for example, 0.001-100 mg / kg. The pharmaceutical compositions of the present invention may be prepared in unit dose form by formulating with a pharmaceutically acceptable carrier and / or excipient according to methods which can be easily carried out by those skilled in the art. Or may be prepared by incorporation into a multi-dose container. The formulation may be in the form of solutions, suspensions, syrups or emulsions in oil or aqueous media, or may be in the form of axes, powders, powders, granules, tablets or accelerators, and may further comprise dispersants or stabilizers. According to a specific embodiment of the invention, the disease associated with IL-2 overexpression or IL-2 overactivity treated with the composition of the invention is an inflammatory disease or an autoimmune disease.
보다 구체적으로 상기 염증성 질환은 만성폐쇄성 폐질환 (chroni c obstructive pulmonary disease) , 기도 과민성 질환 (airways hyper- responsiveness) , 폐혈성 쇼크 (septic shock), 사구체 신염， 염증성 장질환, 크론병 (Crohn's disease), 궤양잘록창자염 (ulcerat ive colitis), 아테롬성 동맥경화증， 골수아구 세포성 백혈병 (myoblastic leukaemia), 당뇨, 화상, 허혈성 심장질환， 뇌졸증, 수막염 및 정맥류로 구성된 군으로부터 선택된다. 보다 구체적으로， 상기 자가면역 질환은 류마티스 관절염， 건선， 알러지성 피부염， 다발성 경화증, 루프스 및 천식으로 구성된 군으로부터 선택되는 질환이다. 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 증복을 피하기 위하여 그 기재를 생략한다. More specifically, the inflammatory disease is chronic obstructive pulmonary disease (chroni c obstructive pulmonary disease, airways hyper- responsiveness, septic shock, glomerulonephritis, inflammatory bowel disease, Crohn's disease, ulcerat ive colitis, atherosclerosis And myoblastic leukaemia, diabetes, burns, ischemic heart disease, stroke, meningitis and varicose veins. More specifically, the autoimmune disease is a disease selected from the group consisting of rheumatoid arthritis, psoriasis, allergic dermatitis, multiple sclerosis, lupus and asthma. According to another aspect of the present invention, the present invention provides a method for treating an inflammatory disease or an autoimmune disease comprising administering to a subject a composition comprising a quinolinone derivative of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient. Provide prevention or treatment. The quinolinone derivative compounds used in the present invention and the inflammatory diseases or autoimmune diseases that can be prevented or treated with the compositions of the present invention have already been described above, and the description thereof is omitted to avoid excessive redundancy.
【유리한 효과】 Advantageous Effects
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 compositions for inhibiting IL-2 activity comprising them as active ingredients.
(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, namely chronic inflammatory disease, inflammatory pain or autoimmune disease.
【발명의 실시를 위한 형태】 [Form for implementation of invention]
이하， 실시예를 통하여 본 발명올 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. 실시예 후보 화합물의 스크리닝 Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention in more detail, and the scope of the present invention is not limited by these examples in accordance with the gist of the present invention. It will be apparent to those of ordinary skill in the art. Example Screening 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 T세포 NK세포에서 인터페론 γ생산의 유도는 시토카인 네트워크 형성에도 중요한 위치를 차지한다. T세포나 인터페론 γ생산의 유도는 시토카인 네트워크 형성에도 중요한 위치를 차지한다. IL— 2유전자의 녹아웃 마우스로는 염증성 장질환， 용혈성 빈혈의 발생이 알려져 있다. IgGl , IgE의 생산을 증가시키는 것도 알려져 있으며， IL-2는 TH1/TH2의 균형 유지에 중요한 기능을 담당하고 있다. Quinolinone is a natural product derived from plants and is known to have various biological activities. In addition, quinolinone has a chemical structure and shows the possibility of hydrogen bonding to the lactam moiety contained therein. Based on these facts, a large amount of quinolinone compounds was efficiently synthesized to investigate the biological activity of quinolinones. Based on the synthesized quinolinone materials, IL-2 ELISA analysis explored the potential as an immunosuppressant in Jurkat T cells and confirmed that certain substances have a high potential as immunosuppressants. IL-2 is produced primarily in T cells but also in killer (NK) cells. It acts as a progression factor to advance the cell cycle, producing neutrophils of tumor necrosis factor, production of transforming growth factor from macrophages, production of IL-8, production of TNF, production of IL-5 from T cells. Although the induction of interferon γ production in T cell NK cells occupies an important position in the formation of cytokine networks. Induction of T cells or interferon γ production also plays an important role in the formation of cytokine networks. IL-2 gene knockout mice are known to develop inflammatory bowel disease and hemolytic anemia. It is also known to increase the production of IgGl, IgE, and IL-2 plays an important role in maintaining the balance of T H 1 / T H 2.
Figure imgf000042_0001
이하 실시예에서 기재하는 화합물 번호， 반웅과정 및 치환기는 상기 합성 모식도 상의 화합물 번호， 반응과정 및 치환기를 의미한다. 일반적 합성과정
Figure imgf000042_0001
Compound numbers, reaction reactions and substituents described in the Examples below refer to compound numbers, reaction procedures and substituents on the above synthetic schematic diagram. General Synthesis Process
단계 (a)의 일반적 '과정 General ' process of step (a)
출발물질 (10.0 g, 60.2 隱 ol)을 무수 MeOHUOO mL)에 용해시켰다. 디메틸 말로네이트 (20.7 mL, 180.6 mmol) 및 CH30Na(13.0g, 240.8圍 ol)를 용액에 첨가하였다. 흔합물을 상온에서 12시간 동안 교반하고, 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다. 합성예 65 ： 메틸 7-니트로 -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실레이트 Starting material (10.0 g, 60.2 μl) was dissolved in anhydrous MeOHUOO mL). Dimethyl malonate (20.7 mL, 180.6 mmol) and CH 3 0Na (13.0 g, 240.8 μl ol) were added to the solution. The mixture was stirred at room temperature for 12 hours, after filtration the filtrate was washed with MeOH to afford the desired compound. Synthesis Example 65: Methyl 7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate
2-아미노 -4-니트로벤즈알데하이드 (1 隱 01)를 무수 Me0H(2 mL)에 용해시켰다. 디메틸말로네이트 (3 mmol) 및 CH30Na(4mmol )를 용액에 첨가하였다. 흔합물을 상온에서 12시간 동안 교반하고， 여과 후 여과물을 MeOH로 세척하여 혹적 화합물을 수득하였다 (수율 =85%). 2-amino-4-nitrobenzaldehyde (1 × 0 1) was dissolved in anhydrous Me0H (2 mL). Dimethylmalonate (3 mmol) and CH 3 0Na (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 = 85%).
¾薩 (400MHz, CDC13)6 8.69 (s, 1H), 8.24 (s, 1Η)' 8.0 (s, 1H, - NH), 7.95 (d, 1H), 7.62 (s, 1H), 3.77 (s, 3H). MASS = 248.04 합성예 67 ： 메틸 5-니트로ᅳ2-옥소 -1， 2—디하이드로퀴놀린 -3-카르복실레이트 ¾ 薩 (400MHz, CDC1 3 ) 6 8.69 (s, 1H), 8.24 (s, 1Η) '8.0 (s, 1H,-NH), 7.95 (d, 1H), 7.62 (s, 1H), 3.77 (s , 3H). MASS = 248.04 Synthesis Example 67 ： Methyl 5-nitropin2-oxo-1, 2—dihydroquinoline-3-carboxylate
2-아미노 -6ᅳ니트로벤즈알데하이드 (1 mmol)를 무수 Me0H(2 mL)로 용해시켰다. 디메틸말로네이트 (3 mmol) 및 C¾0Na(4瞧 ol )를 용액에 첨가하였다.흔합물을 상온에서 12시간 동안 교반하고， 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다 (수율 =78%)  2-Amino-6nitrobenzaldehyde (1 mmol) was dissolved in anhydrous Me0H (2 mL). Dimethylmalonate (3 mmol) and C¾0Na (4x ol) 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 desired compound (yield = 78%). )
¾ 丽 (400MHz, CDCls) 58.76(s, 1H), 7.92 (dd, 1.2, 1H), 7.77(t, ¾ δ (400 MHz, CDCls) 58.76 (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-카르복실레이트 1H), 7.64 (d, 1H) ' , 3.80 (s, 3H). MASS = 248.04 Synthesis Example 71: Methyl 2-oxo-1,2-dihydroquinoline-3-carboxylate
2-아미노벤즈알데하이드 (1 mmol)를 무수 MeOH (2 mL)에 용해시켰다. 디메틸 말로네이트 (3 隱 ol) 및 CH30Na(4隱 ol)를 용액에 첨가하였다. 흔합물을 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 'ol) and CH 3 0 Na (4' ol) were added to the solution. The mixture was stirred at room temperature for 12 hours, after filtration the filtrate with MeOH Washing gave the desired compound (yield = 82%).
^NMRC 400MHz, CDC13)5 8.37(s, IH)， 8.14(d, IH), 8.0(s, IH, -NH), 7.36 (d, IH), 7.31(t, IH), 7.14(t, IH), 3.77(s, 3H). MASS = 203.06 합성예 510 ： 메탈 5-아미노 -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실레이트^ NMRC 400 MHz, CDC1 3 ) 5 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 3.77 (s, 3 H). MASS = 203.06 Synthesis Example 510: Metal 5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate
2ᅳ 6ᅳ디아미노벤즈알데하이드 (1 瞧 ol)를 무수 MeOH(2 mL)에 용해시켰다. 디메틸 말로네이트 (3 瞧 ol) 및 C¾0Na(4瞧 ol)를 용액에 첨가하였다. 흔합물을 상온에서 12시간 동안 교반하고， 여과 후 여과물을 MeOH로 세척하여 목적 화합물을 수득하였다 (수율 =77%). 2x6'diaminobenzaldehyde (1xol) was dissolved in anhydrous MeOH (2 mL). Dimethyl malonate (3dl ol) and C¾0Na (4dl ol) 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 afford the desired compound (yield = 77%).
¾ NMR (400MHz , CDC13) S11.62(s, 1H)， 8.21(s, IH, -NH)， 7.17(t, IH), 6.33 (dd, IH) , 6.22(s, IH), 3.77(s, IH). MASS=218.07 ¾ NMR (400 MHz, CDC1 3 ) S11.62 (s, 1H), 8.21 (s, IH, -NH), 7.17 (t, IH), 6.33 (dd, IH), 6.22 (s, IH), 3.77 ( s, IH). MASS = 218.07
단계 (b-2)의 일반적 과정 General process of step (b-2)
1번 화합물 (7.0g,32.0隱 ol)을 DMF(230mL)에 용해시켰다. Cs2C03 Compound 1 (7.0 g, 32.0 μl) was dissolved in DMF (230 mL). Cs2C0 3
(12.5g, 38.½mol) 및 R2-CI 또는 R2_Br(5.2niL, 38.4瞧01)를 반웅 흔합물에 첨가하고 22시간 동안 교반한 뒤， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 브린 (brine)으로세척하고 무수 Na2S04로 건조시키고, 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 2번 화합물을 수득하였다. 합성예 66 ： 메틸 1-(2- (사이클로펜타 -1,3-디엔 -1-일)에틸 )ᅳ7-니트로 -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카르복실레이트 (12.5g, 38.½mol) and the R2-CI or R 2 _Br (5.2niL, 38.4瞧 0 1) was added to a common compound banung and extracted with a rear, ethyl acetate and ¾0 stirred for 22 hours. The combined organic layers were washed with brine, dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography yielded compound 2. Synthesis Example 66 Methyl 1- (2- (cyclopenta-1,3-diene-1-yl) ethyl) ᅳ 7-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate
합성예 65의 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. Cs2C03(l. mol) 및 5-(2-클로로에틸)사이클로펜타 -1,3-디엔 (1.2mmol)를 반웅 흔합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 ¾0로 추출하였다.합쳐진 유기층을 브린 (brine)으로세척하고 무수 Na2S04로 건조시키고， 진공에서 농축하였다.컬럼 크로마토그래피로 정제하여 합성예 66의 화합물을 수득하였다 (수율 =67%). Compound (1 mmol) of Synthesis Example 65 was dissolved in DMF (2 mL). Cs 2 C0 3 (l.mol) and 5- (2-chloroethyl) cyclopenta-1,3-diene (1.2 mmol) were added to the reaction mixture, stirred for 22 hours, extracted with ethyl acetate and ¾0. 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 66 (yield = 67%).
¾ NMR (400MHz, CDC13 )δ 8.69 (s, IH), 8.24 (s, IH), 7.95 (d, IH) , ¾ NMR (400 MHz, CDC13) δ 8.69 (s, IH), 8.24 (s, IH), 7.95 (d, IH),
7.62 (d, IH), 6.5 (d, IH), 6.4 (d, IH), 6.28 (s, IH) , 3.77 (s, 3H) , 3.00 (sᅳ 2H), 2.9 (s, 1H) , 2.22 (s, 2H). MASS = 340.11 합성예 68 ： 메틸 1-에틸— 5-니트로 -2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3- 카르복실레이트 7.62 (d, IH), 6.5 (d, IH), 6.4 (d, IH), 6.28 (s, IH), 3.77 (s, 3H), 3.00 (s ᅳ 2H), 2.9 (s, 1H), 2.22 (s, 2H). MASS = 340.11 Synthesis 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. Cs2C03 Synthesis Example 67, compound (1 mmol) was dissolved in DMF (2 mL). Cs 2 C0 3
(1.2inmol) 및 클로로에탄 (1.2画 ol)를 반응 흔합물에 첨가한 뒤 22시간동안 교반하고, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 브린 (brine)으로 세척하고 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 68 화합물을 수득하였다 (수율 =67%). (1.2inmol) and chloroethane (1.2 画 ol) were added to the reaction mixture, stirred for 22 hours, and extracted with ethyl acetate and ¾0. The combined organic layers were washed with brine, dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography afforded Synthesis Example 68 compound (yield = 67%).
¾ NM (400MHz, CDC13)5 8.66 (s, 1H)， 8.04 (d, 1H) , 7.95 (d, 1H) ,¾ NM (400 MHz, CDC1 3 ) 5 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 합성예 69 ： 메틸 1-메틸 -5-니트로 -2-옥소 -1,2—디하이드로퀴놀린 -3-카르 복실레이트 7.57 (t, 1 H), 4.28 (s, 2 H), 3.77 (s, 3 H), 1.31 (s, 3 H). MASS = 276.07 Synthesis 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. Cs2C03 Synthesis Example 67 , compound (1 mmol) was dissolved in DMF (2 mL). Cs 2 C0 3
(1.2麵01) 및 클로로메탄 (1.2画 οί)을 반응 흔합물에 첨가한 뒤 22시간 동안 교반하고, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 브린 (brine)으로 세척하고 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 69 화합물을 수득하였다 (수율 =65%). (1.2 麵0 1) and chloromethane (1.2 画 οί) were added to the reaction mixture, stirred for 22 hours, and extracted with ethyl acetate and ¾0. The combined organic layers were washed with brine, dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography afforded Synthesis 69 compound (yield = 65%).
¾ NMR (400MHz, CDC13)8 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H) ,¾ NMR (400 MHz, CDC1 3 ) 8 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- 카르복실레이트 7.57 (t, 1 H), 3.77 (s, 3 H), 1.31 (s, 3 H). MASS = 262.06 Synthesis Example 70 ： Methyl 1-acetyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate
합성예 67 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. Cs2C03 (1.2 mmol) 및 아세틸클로라이드 (1.2隱 ol)를 반웅 흔합물에 첨가한 뒤 22시간 동안 교반 하고, 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 브린 (brine)으로 세척하고 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 합성예 70의 화합물을 수득하였다 (수율 =63%). Synthesis Example 67 (1 μL) was dissolved in DMF (2 mL). Cs 2 CO 3 (1.2 mmol) and acetyl chloride (1.2 μl) were added to the reaction mixture, stirred for 22 hours, and extracted with ethyl acetate and zero. 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 70 (yield = 63%).
¾ 匪 R (400腿 z, CDC13)6 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 과정 ¾ 匪 R (400 腿 z, CDC1 3 ) 6 8.66 (s, 1H), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, 1 H), 3.77 (s, 3 H), 1.31 (s, 3 H). MASS = 290.05 General procedure in step (c-3)
2번 화합물 (2.4g, 7.0mmol) 을 MeOH(200mL)에 용해시킨 10¾> K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 3번 화합물을 수득하였다. 합성예 25 ： 2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 Compound 2 (2.4 g, 7.0 mmol) was stirred at 80 ° C. for 12 hours with 10¾> K0H dissolved in MeOH (200 mL), and the mixture was filtered and the filtrate was washed with ¾0 to obtain compound 3. . Synthesis Example 25: 2-oxo-1,2-dihydroquinoline-3-carboxylic acid
합성예 71 화합물을 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고, 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 25 화합물을 수득하였다 (수율 =88%). Synthesis Example 71 The compound was stirred with 10% K0H dissolved in MeOH (200 mL) at 80 ° C. for 12 hours, and the mixture was filtered and the filtrate was washed with ¾0 to give Synthesis Example 25 compound (yield = 88%). ).
¾ 證 (400MHz, CDC13)5 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 합성예 26 ： l- -메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ 證 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 26: l- -Methoxybenzyl) -2-oxo-l, 2-dihydroquinoline-3-carboxylic acid
메틸 1-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3—카르복실레이 트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 0로 세척하여 합성예 26 화합물올 수득하였다 ( 율 =90%). Methyl 1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C, After filtering the mixture, the filtrate was washed with 0 to obtain a Synthesis Example 26 compound (yield = 90%).
¾ NMR( 400MHz, CDC13)8 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 합성예 27 ： 2-옥손-1-(4- (트리플루오로메록시)벤질)—1,2-디하이드로퀴놀린- 3-카복실릭 애시드 ¾ NMR (400 MHz, CDC1 3 ) 8 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 Synthesis Example 27: 2-oxone-1- (4- (trifluoromethoxy) benzyl) —1,2-dihydroquinoline-3-carboxylic acid
메틸 2-옥소 -1-(4- (트리플루오로메록시)벤질 )-1， 2-디하이드로퀴놀린- 3-카르복실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물올 여과후 여과물을 ¾0로 세척하여 합성예 27 화합물을 수득하였다 (수율 =87%). Methyl-2-oxo-1- (4- (trifluoromethoxy hydroxyethyl) benzyl) -1, 2-dihydroquinoline-3-carboxylate to MeOH (200mL) was 80 ° C for 12 hours in 10% K0H dissolved in After stirring at, the mixture was filtered and the filtrate was washed with ¾0 to give Synthesis Example 27 compound (yield = 87%).
¾ NMR (400MHz, CDC13 )δ 8.34 (s, 1H)ᅳ 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 할성예 28 ： 1-메틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ NMR (400 MHz, CDC13) δ 8.34 (s, 1H) ᅳ 7.65 (d, 1H), 7.36 (d, 1H), 7.31 (t, 1 H), 7.25 (dd, 2 H), 7.14 (t, 1 H), 6.87 (dd, 2H). MASS = 363.07 Substance 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 용해시 ¾ 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 0로 세척하여 합성예 28 화합물을 수득하였다 (수율 =67%). Methyl 1-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) and stirred at ¾ 10% K0H at 80 ° C for 12 hours, and the mixture was filtered. The filtrate was washed with 0 to afford Synthesis Example 28 compound (yield = 67%).
¾ 醒 (400MHz, CDC13)8 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 합성예 29 ： 1-에틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ 醒 (400 MHz, CDC1 3 ) 8 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 Synthesis Example 29 1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
메틸 1ᅳ에틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카르복실레이트를 MeOH (200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 29 화합물을 수득하였다 (수율 =88%). Methyl 1 ᅳ ethyl-2-oxo-1, 2-dihydroquinoline-3 ᅳ carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C, and the mixture was filtered and then filtered. Water was washed with ¾0 to give Synthesis Example 29 Compound (Yield = 88%).
¾ NMR (400顧 z, CDC13)6 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 애시드 ¾ NMR (400 顧 z, CDC1 3 ) 6 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 Synthesis Example 30 ： 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% K0H로 12시간 동안 80°C에서 교반하고， 흔합물올 여과후 여과물을 ¾0로 세척하여 합성예 30 화합물을 수득하였다 (수율 =90%). Methyl 2-oxo-1-propyl-1, 2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C. Was washed with ¾0 to give the Synthesis Example 30 compound (yield = 90%).
¾ NMR (400MHz, CDC13)5 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 애시드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis 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% K0H로 12시간 동안 80°C에서 교반하고, 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 31 화합물을 수득하였다 (수율 =98%). Methyl 1-acetyl— 2-oxo-1, 2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C., the mixture was filtered and then filtered Water was washed with ¾0 to give Synthesis 31 Compound (Yield = 98%).
¾ 匪 R (400MHz, CDC13)6 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 합성예 32 ： 5-아미노 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 8.34 (s, 1H), 8.25 (d, 1H), 7.59 (t, 1H), 7.36 (s, 1 H), 7.14 (t, 1 H), 2.66 (s, 3 H). MASS = 231.05 Synthesis Example 32 ： 5-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
합성예 51Q의 화합물을 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예Synthesis Example 51Q The compound of 51Q was dissolved in MeOH (200 mL) and stirred at 80 ° C. for 12 hours with 10% K0H. The mixture was filtered and the filtrate was washed with ¾0.
32 화합물을 수득하였다 (수율 =88%). 32 compound was obtained (Yield = 88%).
¾ NMR(400MHz,CDCl3)5 11.0(s, 1H, -OH), 8.34(s, 1H), 8.0(s, 1H,¾ NMR (400 MHz, CDCl 3 ) 5 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).-NH), 7.5 (d, 1H), 7.06 (t, 1H), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2 ).
MASS=204.05 합성예 33 ： 5-아미노 -l-(4-메록시벤질) -2-옥소 -1,2ᅳ디하이드로퀴놀린 -3- 카복실릭 애시드 MASS = 204.05 Synthesis Example 33: 5-Amino-l- (4-methoxybenzyl) -2-oxo-l, 2'dihydroquinoline-3-carboxylic acid
메틸 5_아미노 ᅱ；^메특시벤질) _2_옥소 _1>2ᅳ디하이드로퀴놀린 _3_ 카르복실레이트를 Me0H(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 33 화합물을 수득하였다 (수율 =87%). Methyl 5 _amino ᅱ; ^ mexi benzyl) _ 2 _ oxo _ 1> 2 ᅳ dihydroquinoline _ 3 _ carboxylate was dissolved in Me0H (200 mL) with 10% K0H for 12 hours at 80 ° C., The mixture was filtered and the filtrate was washed with ¾0 to give Synthesis 33 Compound (Yield = 87%).
¾ 證 (400MHz, CDC13)6 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. 합성예 34 ： 5-아미노 _1-메틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ 證 (400 MHz, CDC1 3 ) 6 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 Preparative example 34: 5-amino _1--2-oxo-1,2-dihydroquinoline-3-carboxylic Acid
메틸 5-아미노 -1—메틸ᅳ 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복실 레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고, 흔합물을 여과후 여과물을 0로 세척하여 합성예 34 화합물을 수득하였다 (수율 =90¾). Methyl 5-amino-1—methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxylate was stirred at 80 ° C. for 12 hours with 10% K0H dissolved in MeOH (200 mL), the mixture The filtrate was washed with zero after filtration to give the synthesis example 34 compound (yield = 90¾).
¾ NMR (400MHz, CDC13)6 8.34(s, 1Η)' 7.06(1;， 1Η) , 7.01(d, 1Η)( 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.44(s, 3H) .MASS=218.07 합성예 35 ： 5-아미노 -1-에틸 -2-옥소— 1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 메틸 5-아미노 -1-에틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실레이 트를 MeOH (200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 35 화합물을 수득하였다 (수율 =78%). ¾ NMR (400 MHz, CDC1 3 ) 6 8.34 (s, 1Η) '7.06 (1 ;， 1Η), 7.01 (d, 1Η) ( 6.32 (d, 1H), 6.27 (s, 2H, -NH 2 ), 3.44 (s, 3H) .MASS = 218.07 Synthesis Example 35: 5-Amino-1-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid Methyl 5-amino-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylate was stirred at 80 ° C. for 12 hours with 10% K0H dissolved in MeOH ( 2 00 mL), The mixture was filtered and the filtrate was washed with ¾0 to give Synthesis Example 35 Compound (Yield = 78%).
¾ 匪 R (40(MHz, CDC13)6 8.34(s, IH), 7.06(t, IH), 7.01(d, IH) ,¾ 匪 R (40 (MHz, CDC1 3 ) 6 8.34 (s, IH), 7.06 (t, IH), 7.01 (d, IH),
6.32(d, IH), 6.27(s, 2H, -NH2) , 4.28(s, 2H), 3.44(s, 3H) .MASS=232.08 합성예 36 ： 1-아세틸—5—아미노 -2—옥소— 1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 6.32 (d, IH), 6.27 (s, 2H, -NH 2 ), 4.28 (s, 2H), 3.44 (s, 3H) .MASS = 232.08 Synthesis Example 36: 1-Acetyl-5 amino-2-2-oxo — 1, 2-dihydroquinoline-3-carboxylic acid
메틸 1ᅳ아세틸 -5-아미노 -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실 레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 0로 세척하여 합성예 36 화합물을 수득하였다 (수율 =88%).  Methyl 1 ᅳ acetyl-5-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C., the mixture The filtrate was washed with zero after filtration to give the synthesis example 36 compound (yield = 88%).
¾ NMR (4d(fflHz, CDC13)6 8.34(s, IH), 7.06(t, IH) , 7.01(d, IH), 6.32(d, IH), 6.27(s, 2H, -NH2), 3.44(s, 3H) MASS-246.06 합성예 37 ： 5-아미노 -2-옥소— 1-프로피오닐 -1,2-디하이드로퀴놀린 -3-카복실 릭 애시드 ¾ NMR (4d (fflHz, CDC1 3 ) 6 8.34 (s, IH), 7.06 (t, IH), 7.01 (d, IH), 6.32 (d, IH), 6.27 (s, 2H, -NH 2 ), 3.44 (s, 3H) MASS-246.06 Synthesis Example 37: 5-amino-2-oxo- 1-propionyl-1,2-dihydroquinoline-3-carboxylic acid
메틸 5-아미노 -2-옥소— 1-프로피오닐 -1， 2-디하이드로퀴놀린 -3-카르복 실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고, 흔합물을 여과후 여과물을 0로 세척하여 합성예 37 화합물을 수득하였다 (수율 =66%).  Methyl 5-amino-2-oxo- 1-propionyl-1, 2-dihydroquinoline-3-carboxylate was stirred at 80 ° C. for 12 hours with 10% K0H dissolved in MeOH (200 mL), The mixture was filtered and the filtrate was washed with 0 to give Synthesis Example 37 compound (yield = 66%).
¾ NMR( 400MHz, CDC13) δ 8.34(s, IH), 7.06(t, IH), 7.01(d, IH), 6.32(d, IH), 6.27 (s, 2H, -NH2), 4.28(s,2H) ,3.44(s,3H) .MASS=260.08 합성예 38 ： 5-아미노 -1- (메톡시카르보닐) -2-옥소 -1,2-디하이드로퀴놀린ᅳ 3- 카복실릭 애시드 ¾ NMR (400 MHz, CDC1 3 ) δ 8.34 (s, IH), 7.06 (t, IH), 7.01 (d, IH), 6.32 (d, IH), 6.27 (s, 2H, -NH 2 ), 4.28 ( s, 2H), 3.44 (s, 3H) .MASS = 260.08 Synthesis Example 38 ： 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% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 0로 세척하여 합성예 38 화합물을 수득하였다 (수율 =90%).  Dimethyl 5-amino-2-oxoquinoline-1,3 (2H) _dicarboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C, and the mixture was filtered and filtered. Water was washed with 0 to give Synthesis Example 38 compound (yield = 90%).
¾ 賺 (400MHz, CDC13)6 8.34(s, IH), 7.06(t, IH), 7.01(d, IH), 6.32(d, 1H), 6.27(s, 2H, -NH2), 3.44(s, 3H). MASS=262.06 합성예 39 ： 5-아미노 -1- (사이클로펜타ᅳ 1， 3-디엔— 1-일메틸 )-2-옥소 -1,2-디하 이드로퀴놀린 -3-카복실릭 애시드 ¾ 賺 (400 MHz, CDC1 3 ) 6 8.34 (s, IH), 7.06 (t, IH), 7.01 (d, IH), 6.32 (d, 1H), 6.27 (s, 2H, -NH 2 ), 3.44 (s, 3H). MASS = 262.06 Synthesis Example 39 ： 5-Amino-1- (cyclopentata 1,3-diene-1-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid
메틸 5-아미노 -1- (사이클로펜타 -1， 3-디엔 -1-일메틸 )ᅳ2-옥소 -1,2-디하 이드로퀴놀린 -3-카르복실레이트를 MeOH(200mL)에 용해시킨 10¾ K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 0로 세척하여 합성예 39 화합물을 수득하였다 (수율 =89%). Methyl 5-amino-1- (cyclopenta-1,3-diene-1-ylmethyl) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxylate dissolved in MeOH (200 mL) 10¾ K0H After stirring for 12 hours at 80 ° C., the mixture was filtered and the filtrate was washed with 0 to give a Synthesis Example 39 compound (yield = 89%).
¾ 應 R (400MHz, CDC13) 8.34(s, 1H)ᅳ 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 합성예 40 ： 5-니트로 -2-옥소 -1,2-디하이드로퀴놀린 -3—카복실릭 애시드 ¾ 應 R (400 MHz, CDC1 3 ) 8.34 (s, 1H) ᅳ 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 Synthesis Example 40 ： 5-nitro-2-oxo-1,2-dihydroquinoline-3—carboxylic acid
합성예 67 '화합물을 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 801：에서 교반하고, 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 40 화합물을 수득하였다 (수율 =78%^  Synthesis Example 67 The compound was stirred in 801: for 12 hours with 10% K0H dissolved in MeOH (200 mL), and the mixture was filtered and the filtrate was washed with ¾0 to give Synthesis Example 40 compound (yield = 78%). ^
¾ 匪 R (400MHz, CDC13)6 11.0(s, 1H, -OH), 8.63(s, 1H), 8.53(d,¾ 匪 R (400 MHz, CDC1 3 ) 6 11.0 (s, 1H, -OH), 8.63 (s, 1H), 8.53 (d,
1H), 7.95(d, 1H), 7.57(t, 1H). MASS= 234.03 합성예 41 ： l-(4-메특시벤질) -5-니트로 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실릭 애시드 1H), 7.95 (d, 1 H), 7.57 (t, 1 H). MASS = 234.03 Synthesis Example 41: l- (4-Methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
메틸 1-(4-메톡시벤질 )ᅳ5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카 르복실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 41 화합물을 수득하였다 (수율 =78%) Methyl 1- (4-methoxybenzyl) eu 5-nitro-2-oxo -1, 80 ° for 2-dihydroquinoline-3-car le 12 hours carboxylate in 10% K0H was dissolved in MeOH (200mL) After stirring at C, the mixture was filtered and the filtrate was washed with ¾0 to give the Synthesis Example 41 compound (yield = 78%).
¾ MR (400MHzᅳ CDC13)6 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 ： 1ᅳ(4-메록시펜에틸 )-5-니트로 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실릭 애시드 메틸 l-(4-메특시펜에틸 )-5ᅳ니트로 -2ᅳ옥소 -1,2-디하이드로퀴놀린 -3- 카르복실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고, 흔합물을 여과후 여과물을 ◦로 세척하여 합성예 42 화합물을 수득하였다 (수율 = )%). ¾ MR (400MHz ᅳ CDC1 3 ) 6 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, 2 H), 3.83 (s, 3 H). MASS = 354.09 Synthesis Example 42: 1 '(4-Methoxyphenethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylic acid Methyl l- (4-methoxyphenethyl) -5mnitro-2oxoo-1,2-dihydroquinoline-3-carboxylate dissolved in MeOH (200 mL) at 80 ° for 12 hours with 10% K0H After stirring at C, the mixture was filtered and the filtrate was washed with o to give the Synthesis Example 42 compound (yield =)%).
¾ NMR (400MHz ,CDC1 a )δ 8.63(s, 1H), 8.04(d, 1H), 7.95(d, 1H) , ¾ NMR (400MHz, CDC1 a) 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， 2ᅳ디하이드로퀴놀린 -3-카복실릭 애시 드 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 Synthesis Example 43: 1-Methyl-5-nitro-2-oxo-1, 2'dihydroquinoline-3-carboxylic acid
메틸 1-메틸 -5-니트로 -2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카르복실레 이트를 Me0H(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 43 화합물을 수득하였다 (수율 =78%).  Methyl 1-methyl-5-nitro-2-hexoxo-1, 2-dihydroquinoline-3-carboxylate was dissolved in Me0H (200 mL) with 10% K0H for 12 hours at 80 ° C, The mixture was filtered and the filtrate was washed with ¾0 to give Synthesis 43 Compound (Yield = 78%).
¾ NMR (400MHz, CDC13)5 8.63(s, 1H), 8.04(s, 1H), 7.95(d, 1H),¾ NMR (400 MHz, CDC1 3 ) 5 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 -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애 시드 7.57 (t, 1 H), 3.44 (s, 3 H). MASS = 248.04 Synthesis Example 44: 1-ethyl-5-nitro-2-hexoxo-1,2-dihydroquinoline-3-carboxylic acid
메틸 1-에틸 -5-니트로 -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복실레이 트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 H반하고, 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 44 화합물을 수득하였다 (수율 =68%).  H at 80 ° C. for 12 hours with 10% K0H dissolved in methyl 1-ethyl-5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxylate in MeOH (200 mL), The mixture was filtered and the filtrate was washed with ¾0 to give Synthesis 44 Compound (Yield = 68%).
¾ 證 (400MHz, CDC13)6 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 -2ᅳ옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 ¾ 證 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 45 ： 1-Acetyl-5-nitro-2-hexoxo-1,2-dihydroquinoline-3-carboxylic acid
메틸 ι_아세틸 -5-니트로 -2-옥소 -1 , 2-디하이드로퀴놀린— 3—카르복실레 이트를 MeOH(200mL)에 용해시킨 1 K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 45 화합물을 수득하였다 (수율 =7OT). Methyl ι_acetyl-5-nitro-2-oxo-1, 2-dihydroquinoline- 3—carboxylate was dissolved in MeOH (200 mL) with 1 K0H for 12 h at 80 ° C. The filtrate was washed with ¾0 after filtration to give the compound of Synthesis 45. (Yield = 7 OT).
¾ 匪 R( 400MHz, CDC13)6 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-카복실 릭 애시드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthetic Example 46: 5-nitro-2-oxo-1-propionyl-1,2-dihydroquinoline-3-carboxylic acid
메틸 5-니트로 -2-옥소 -1-프로피오닐— 1， 2—디하이드로퀴놀린ᅳ3- 카르복실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 46 화합물을 수득하였다 (수율 =67%). Methyl 5-nitro-2-oxo-1-propionyl— 1, 2—dihydroquinoline ᅳ 3-carboxylate was dissolved in MeOH (200 mL) with 10% K0H for 12 hours at 80 ° C. The mixture was filtered and the filtrate was washed with ¾0 to give Synthesis 46 Compound (Yield = 67%).
¾ 匪 R(400MHz, CDC13)5 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- (메특시카르보닐) -5-니트로 -2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3- 카복실릭 애시드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 47: 1- (methoxycarbonyl) -5-nitro-2-oxo-1′2-dihydroquinoline-3-carboxylic acid
디메틸 5-니트로 -2-옥소퀴놀린 -1,3(2H)-디카르복실레이트를 Dimethyl 5-nitro-2-oxoquinoline-1,3 (2H) -dicarboxylate
MeOH(200mL)에 용해시킨 10% K0H로 12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 47 화합물을 수득하였다 (수율 =70%). The mixture was stirred at 80 ° C. for 10 hours with 10% K0H dissolved in MeOH (200 mL), and the mixture was filtered and the filtrate was washed with ¾0 to give Synthesis 47 Compound (Yield = 70%).
¾ 匪 R(400MHz, CDC13)8 8.63(s, 1H)ᅳ 8.64(d, 1H), 7.95(s, 1H),¾ 匪 R (400 MHz, CDC1 3 ) 8 8.63 (s, 1H) ᅳ 8.64 (d, 1H), 7.95 (s, 1H),
7.57(t, 1H), 1.02(s, 3H). MASS= 292.03 합성예 48 ： 1- (사이클로펜타 -1,3—디엔 -1-일메틸 )-5-니트로—2-옥소 -1,2-디하 이드로퀴놀린 -3-키 ^복실릭 애시드 7.57 (t, 1 H), 1.02 (s, 3 H). MASS = 292.03 Synthesis Example 48 ： 1- (cyclopenta-1,3—diene-1-ylmethyl) -5-nitro-2-2-oxo-1,2-dihydroquinoline-3-key ^ cyclolic acid
메틸 1- (사이클로펜타 -1,3-디엔 -1-일메틸 )-5-니트로 -2-옥소 -1,2-디하 이드로퀴놀린—3—카르복실레이트를 MeOH(200mL)에 용해시킨 10% K0H로 10% of methyl 1- (cyclopenta-1,3-diene-1-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3 carboxylate dissolved in MeOH (200 mL) With K0H
12시간 동안 80°C에서 교반하고， 흔합물을 여과후 여과물을 ¾0로 세척하여 합성예 47 화합물을 수득하였다 (수율 =78%). After stirring for 12 hours at 80 ° C., the mixture was filtered and the filtrate was washed with ¾0 to give the Synthesis 47 compound (yield = 78%).
¾ NMR(400MHz, CDC13)6 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=¾ NMR (400 MHz, CDC1 3 ) 6 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 단계 (d-4)의 일반적 과정 312.07 General process of step (d-4)
3번 화합물 (450mg, 0.9麵01)을 DMF(5mL)에 용해시켰다. DIPEA(0.5mL, 2.7mmol), ¾-N¾(0.2mL, 1.3麵 οθ 및 ? 801)(0.911 ，1.8隱01)을 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 4번 화합물을 수득하였다. 합성예 49 ： 1-(4-에틸벤질) -5-니트로 -2-옥소 -N-펜에틸 -1，2-디하이드로 퀴놀린 -3-카르복사마이드 Compound 3 (450 mg, 0.9 麵0 1) was dissolved in DMF (5 mL). DIPEA (0.5 mL, 2.7 mmol), ¾-N¾ (0.2 mL, 1.3 麵 θ and? 801 ) (0.911, 1.8 隱 01) 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. After purification by silica gel column chromatography to obtain compound 4. Synthesis Example 49 1- (4-ethylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-에틸벤질 )-5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- 페닐에타나민 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에^ 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 麵 ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 49 (yield = 56%).
¾赚(40( [¾, )(:13)8 8.57(s, 1H) , 8.04(dᅳ 1H) , 7.95(1; , 1Η) , 7.57(t, 1H), 7.40(dd, 2Η), 7.29(dd, 2Η), 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 합성예 50 ： l-(4-에틸펜에틸) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린—3-카르복사마이드 40 ([¾,) (: 1 3 ) 8 8.57 (s, 1H), 8.04 (d ᅳ 1H), 7.95 (1;, 1Η), 7.57 (t, 1H), 7.40 (dd, 2Η) , 7.29 (dd, 2Η), 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 Synthesis Example 50: l- (4-ethylphenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydro Quinoline—3-carboxamide
1-(4-에틸펜에틸 )-5—니트로 -2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- 페닐에타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 50 (yield = 56%).
¾赚(400腿 z,CDCl3)S 8.57(s, 1H)， 8.04(d, 1H)， 7.95(d, 1H)，¾ (400 腿 z, CDCl 3 ) S 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 합성예 51 ： 플루오로벤질 )-5-니트로 -2-옥소 -N-펜에틸 -1， 2-디하이드로 퀴놀린 -3-카르복사마이드 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 Synthesis Example 51 fluorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-플루오로벤질 )-5-니트로— 2—옥소 -1， 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), 2- 페닐에타나민 (1.5 隱 ol) 및 PyBop(2誦 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 μL) was dissolved in DMF (2 mL). DIPEAC3 隱 ol), 2- phenylethanamine (1.5 隱 ol) and PyBop (2 誦 ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 51 (Yield = 60%)
¾ NMR (400MHz, CDC13 )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 합성예 52 ： l-(4-플루오로펜에틸) -5-니트로 -2-옥소— N-펜에틸 -1， 2-디하이 드로퀴놀린 -3-카르복사마이드  ¾ NMR (400 MHz, CDC13) 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 Synthesis Example 52: l- (4-fluorophenethyl) -5-nitro-2-oxo-N-phenethyl-1, 2-dihydrodroquinoline-3-carboxamide
1-(4-플루오로펜에틸) -5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1 瞧 01)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2- 페닐에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 × 0 1) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- phenylethanamine (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 52 (yield = 60%).
¾ NMR ( 400MHz, CDC13 )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, ¾ NMR (400MHz, CDC13) 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).2H), 7.19 (dd, 2H), 4.62 (s, 2H), 3.55 (m, 2H), 3.09 (s, 2H), 2.83 (s, 2H).
MASS=459.16 합성예 53 ： 1ᅳ(4-클로로벤질) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 MASS = 459.16 Synthesis Example 53 ： 1 ′ (4-chlorobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4ᅳ클로로벤질 )-5-니트로 -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-페닐에타나민 (1.5 醒 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다/ 이후 실리카겔 크로마토그래프로 정제하여 합성예 53 화합물을 수득하였다 (수율 =58%). 1- (4 ᅳ chlorobenzyl) -5-nitro-2-oxo ᅳ 1, 2-dihydroquinoline-3-carboxylic Acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-phenylethanamine (1.5 μl ol) and PyBop (2 μl ol) 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 give Synthesis Example 53 compound (yield = 58%).
¾醒 R(400匪 z,CDCl3)S 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=461.11 합성예 54 ： 5-니트로 -l-(4-니트로벤질) -2-옥소— N-펜에틸—1， 2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ 醒 R (400 匪 z, CDCl 3 ) S 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 = 461.11 Synthesis Example 54: 5-nitro-l- (4-nitrobenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
5-니트로 -1-(4-니트로벤질) -2-옥소 -1 ,2—디하이드로퀴놀린— 3-카복실릭 애시드 (1 誦 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2- 페닐에타나민 (1.5 '隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 μL) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- phenylethanamine (1.5 '隱 ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 54 (yield = 64%).
¾ NMR( 400MHz ,CDC1 a )δ 8.57 (s, 1Η), 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 합성예 55 ： l-(4-아미노벤질) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린 -3-카르복사마이드  ¾ NMR (400MHz, CDC1 a) δ 8.57 (s, 1Η), 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 Synthesis Example 55: l- (4-aminobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1ᅳ (4-아미노벤질 )-5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- 페닐에타나민 (1.5 mmol) 및 PyBop(3 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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' ol) was dissolved in DMF (2 mL). DIPEA (3 μL), 2-phenylethanamine (1.5 mmol) and PyBop (3 mmol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 55 (yield = 57%).
¾ NMR (400MHz, CDC13)5 8.57(s, 1H)， 8.04(d, 1H), 7.95(d, 1H),¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 56 ： ： ( 4-시아노벤질) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 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 Synthesis Example 56 ： (4-Cyanobenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-시아노벤질 )-5ᅳ니트로 -2—옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 匪 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2- 페닐에타나민 (1.5 瞧 ol) 및 PyBop(2 誦 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제 하여 합성예 56 화합물을 수득하였다 (수율 =48%).  1- (4-cyanobenzyl) -5mnitro-2—oxo-1, 2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- phenylethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 56 compound (yield = 48%).
¾ 蘭 R (400MHz, CDC13)S 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), 4.9 (s, 2H), 3.55(m, 2H), 2.83(m, 2H). MASS=452.15 합성예 57 ： 1- (나프탈렌 -2-일메틸 )-5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 蘭 R (400 MHz, CDC1 3 ) S 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), 4.9 (s, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 452.15 Synthesis Example 57 1- (naphthalen-2-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1- (나프탈렌 -2-일메틸) -5-니트로 -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3- 카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 2- 페닐에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 'ol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 57 (yield = 50%).
¾ 匪 R (40p腿 z, CDC13)6 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 합성예 58 ： l-( [1,1 '-비페닐 ]-4-일메틸 )-5-니트로 -2-옥소— N-펜에틸 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (40p 腿 z, CDC1 3 ) 6 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 Synthesis Example 58: l-([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carbox Copyamide
1_( [ 1， 1 ' -비페닐] -4-일메틸) -5—니트로 -2-옥소 -1 , 2-디하이드로퀴놀린- 1 _ ([1,1'-biphenyl] -4-ylmethyl) -5-nitro-2-oxo-1,2-dihydroquinoline-
3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 2-페닐에타나민 (1.5 瞧 ol) 및 PyBop(2 瞧 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 58 화합물을 수득하였다 (수율 = 60%) . 3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 μ ol), 2-phenylethanamine (1.5 μl ol) and PyBop (2 μl ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 58 compound (yield = 60%).
^NMR OCMHz DCl^S 8.57 (s, IH), 8.04 (dᅳ IH), 8.03 (s, IH, - ^ NMR OCMHz DCl ^ S 8.57 (s, IH), 8.04 (d ᅳ IH), 8.03 (s, IH,-
NH), 7.95(d, IH), 7.57(t, IH), 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 합성예 59 ： l-(4-벤질벤질) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린—3-카르복사마이드 NH), 7.95 (d, IH), 7.57 (t, IH), 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 Synthesis Example 59: l- (4-benzylbenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline—3-carboxamide
1— (4-벤질벤질) -5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 誦 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- 페닐에타나민 (1.5 醒 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물올 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 —로 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 誦 ol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 2-phenylethanamine (1.5 μl ol) 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 —. Subsequent purification with silica gel chromatography gave the compound of Synthesis 59 (yield = 46%).
¾匪 R(40( Hz,CDCl3)S 8.57(s, IH), 8.04(d, IH), 8.03(sᅳ IH, -NH),¾ 匪 R (40 (Hz, CDCl 3 ) S 8.57 (s, IH), 8.04 (d, IH), 8.03 (s ᅳ IH, -NH),
7.95(d, IH), .7.57(t, IH)ᅳ 7.51(m, 4H), 7.42 (mᅳ 3H) , 7.32 (dd, 2H),7.95 (d, IH),. 7.57 (t, IH) ᅳ 7.51 (m, 4H), 7.42 (m ᅳ 3H), 7.32 (dd, 2H),
7.29(m, 5H), 4.99(s, 2H), 4.763.55(m, 2H), 2.83(m, 2H). MASS= 517.20 합성예 60 ： 5-니트로 -2-옥소 -N-펜에틸 -l-(4-페녹시벤질) -1， 2-디하이드로 퀴놀린 -3-카르복사마이드 7.29 (m, 5H), 4.99 (s, 2H), 4.763.55 (m, 2H), 2.83 (m, 2H). MASS = 517.20 Synthesis Example 60: 5-nitro-2-oxo-N-phenethyl-1-(4-phenoxybenzyl) -1, 2-dihydroquinoline-3-carboxamide
5-니트로 -2-옥소 -1-(4-페녹시벤질) -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2ᅳ 페닐에타나민 (1.5 '瞧 ol) 및 PyBop (2隱 ol)를 반웅 혼합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 (1xol) was dissolved in DMF (2 mL). DIPEA (3 ′ ol), 2 ′ phenylethanamine (1.5 ′ ′ ol) and PyBop (2 ′ ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 60 compound (yield = 48%).
Figure imgf000057_0001
8.57 (s, 1Η)' 8.04(d, IH), 8.03(s, IH, -NH), 7.95(d, IH), 7.57(t, IH) , 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 합성예 61 ： 1-(4-클로로펜에틸 )-5-니트로 -2-옥소— N-펜에틸 -1， 2-디하이드로 퀴놀린 -3-카르복사마이드
Figure imgf000057_0001
8.57 (s, 1Η) '' 8.04 (d, IH), 8.03 (s, IH, -NH), 7.95 (d, IH), 7.57 (t, IH), 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 Synthesis Example 61 1- (4-Chlorophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-클로로펜에틸 )-5-니트로—2ᅳ옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPE/ 3 隱 ΰΐ), 2- 페닐에타나민 (1.5 隱 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 61 화합물을 수득하였다 (수율 =59%).  1- (4-Chlorophenethyl) -5-nitro-2 ioxo-1,2 ᅳ dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). DIPE / 3 隱)), 2- phenylethanamine (1.5 隱 ol) and PyBop (2 瞧 ol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 61 (Yield = 59%).
¾ NMR (400MHz ,CDC13)5 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, ―¾ NMR (400MHz, CDC1 3 ) 5 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 합성예 62 ： l-(4-아미노펜에틸 )— 5-니트로 -2-옥소 -N-펜에틸 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 62: l- (4-Aminophenethyl) —5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-아미노펜에틸 )-5-니트로 -2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- 페닐에타나민 (1.5 画 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 62 화합물을 수득하였다 (수율 =47%).  1- (4-Aminophenethyl) -5-nitro-2oxoxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 62 (yield = 47%).
¾ NMR (400MHz ,CDC13)6 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, -¾ NMR (400MHz, CDC1 3 ) 6 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, _N ), 4.62(s, 2H)， 3.09(s, 2H), 3.55(m,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) , _N), 4.62 (s, 2H), 3.09 (s, 2H), 3.55 (m,
2H), 2.83(m, 2H). MASS= 456.18 합성예 63 ： l-(4-시아노펜에틸 )-5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 2H), 2.83 (m, 2H). MASS = 456.18 Synthesis Example 63 l- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
1-(4-시아노펜에틸) -5-니트로 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 2-페닐 에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 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 瞧 ol), 2-phenyl Etanamine (1.5 mmol) and PyBop (2 μL ol) 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 63 (yield = 52%).
¾ NMR (40pMHz, CDC13)5 8.57(s, 1H), 8.04(d, 1H), 8.03(s, 1H, - H), 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 합성예 64 ： 5-니트로ᅳ l-(4-니트로펜에틸 )-2ᅳ옥소 -N-펜에틸 -1,2ᅳ디하이드로 퀴놀린 -3-카르복사마이드 ¾ NMR (40pMHz, CDC1 3 ) 5 8.57 (s, 1H), 8.04 (d, 1H), 8.03 (s, 1H, -H), 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 Synthesis Example 64: 5-nitrojan l- (4-nitrophenethyl) -2ioxo-N-phenethyl-1,2′dihydroquinoline-3-carboxamide
5ᅳ니트로 니트로펜에틸 )ᅳ2ᅳ옥소 -1ᅳ 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 睡 ol), 2- 페닐에타나민 (1.5 議 ol) 및 PyBop(2 賺 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 64 화합물을 수득하였다 (수율 = 43%).  5 nnitro nitrofenethyl) 2 oxo-1 2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 64 (yield = 43%).
¾ 證 (400MHz ,CDC13 )δ 8.57(sᅳ 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 합성예 76 ： 2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드  ¾ 證 (400MHz, CDC13) δ 8.57 (s ᅳ 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 Synthesis Example 76: 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide
2-옥소 -1，2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 賺 ol), 페닐메타나민 (1.5 mmol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 76 화합물을 수득하였다 (수율 =42%).  2-oxo-l, 2'dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), phenylmethanamin (1.5 mmol) and PyBop (2 μl ol) 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 76 (yield = 42%).
賺 (400MHz ,CDC13 )δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 400 (400MHz, CDC13) 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, IH), 7.14(t, IH). MASS=264.09 합성예 77 ： 1—메틸 -2-옥소 -N-페닐 -1,2-디하이드로퀴놀린 -3-카르복사마이드)1H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (t, IH), 7.14 (t, IH). MASS = 264.09 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. DIPE 3 隱 ol), 아닐린 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 牟득한 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). DIPE 3'ol), aniline (1.5 mmol) and PyBop (2'ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 77 (yield = 44%).
¾ NMR (400MHz ,CDC13 )δ 10.12 (s, IH, -NH), 8.28 (s, IH), 7.65 (d IH), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, IH)， 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， 2ᅳ디하이드로퀴놀린 -3-카르복사마이드 1-에틸 -2-옥소 -1,2-디하이드로퀴놀린 -3—카복실릭 애시드 (1 隱 ol)를 ¾ NMR (400 MHz, CDC13) δ 10.12 (s, IH, -NH), 8.28 (s, IH), 7.65 (d IH), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s, IH ), 7.31 (t, IH), 7.19 (m IH), 7.14 (t, IH), 3.44 (s, 3H). MASS = 278.11 Synthesis Example 78 ： 1-ethyl—2-oxo-N-phenyl-1,2′dihydroquinoline-3-carboxamide 1-ethyl-2-oxo-1,2-dihydroquinoline-3—carboxyl Rick Acid (1 隱 ol)
DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아닐린 (1.5隱 ol) 및 PyBop (2麵 ol)를 반웅 ^합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출 하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 78 화합물 을 수득하였다 (수율 =45%) Dissolved in DMF (2 mL). DIPEA (3 mmol), aniline (1.5 'ol) and PyBop (2' ol) 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. Then purified by silica gel column chromatography to obtain the Synthesis Example 78 compound (yield = 45%)
¾ NMR (400MHz, CDC13)5 10.12(s, IH, -NH), 8.28(s, IH), 7.65(d, IH), 7.61 (dd, 2H), 7.43(dd, 2H), 7.36(s, IH), 7.31(t, IH), 7.19(m, IH), 7.14(t, IH), 4.28(s, 2H), 3.44(s, 3H). MASS=292.12 합성예 79: 1-아세틸 -2-옥소 -N-페닐 -1，2-디하이드로퀴놀린 -3-카르복사마이드¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 7.65 (d, IH), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.36 (s , IH), 7.31 (t, IH), 7.19 (m, IH), 7.14 (t, IH), 4.28 (s, 2H), 3.44 (s, 3H). MASS = 292.12 Synthesis Example 79: 1-Acetyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
1-아세틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 아닐린 (1.5誦 ol) 및 PyBop (2mmol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 79 화합물을 수득하였다 (수율 =50%). Ή 匪 R (400MHz, CDC13)6 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 합성예 85 (2-옥소 -N-(p-틀일) -1,2-디하이드로퀴놀린 -3-카르복사마이드)1-acetyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), aniline (1.5 μl ol) 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. Then purified by silica gel column chromatography to give the compound of Synthesis 79 (yield = 50%). 匪 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 85 ( 2 -Oxo-N- (p-framework) ) -1,2-dihydroquinoline-3-carboxamide)
2-옥소ᅳ 1, 디하이드로퀴놀린 -3ᅳ카복실릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), p-를루이딘 (1.5 mmol) 및 PyBop(2 i ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 85 화합물을 수득하였다 (수율 = 48%). 2-oxoxol 1, dihydroquinoline-3xcarboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), p-lluidine (1.5 mmol) and PyBop (2 i ol) 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 85 (yield = 48%).
蘭 R (400MHz, CDC13)6 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—를일) -1， 2-디하이드로퀴놀린 -3ᅳ카르복사 마이드 蘭 R (400MHz, CDC1 3 ) 6 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 Synthesis Example 86 1-methyl-2-oxo-N- (p-yl) -1,2-dihydroquinoline-3′carboxamide
1-메틸 -2-옥소 -1，2-디하이드로퀴놀린ᅳ 3ᅳ카복실릭 애시드 (1 瞧 οί)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-를루이딘 (1.5麵 ol) 및 PyBop (2mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래파로 정제하여 합성예 86 화합물을 수득하였다 (수율 =52%).  1-Methyl-2-oxo-1- 1,2-dihydroquinoline 3 ′ carboxylic acid (1 1 οί) was dissolved in DMF (2 mL). DIPEA (3 mmol), p-lurudine (1.5 μl ol) 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. Then purified by silica gel column chromatography to give the compound of Synthesis 86 (yield = 52%).
¾ NMR (400MHz, CDC13)5 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-를일) -1，2-디하이드로퀴놀린 -3- 카르복사마이드) ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 87 1-ethyl-2-oxo-N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide)
1-에틸 -2-옥소 -1,2—디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 1-ethyl-2-oxo-1,2—dihydroquinoline-3-carboxylic acid (1 μl)
DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), p-를루이딘 (1.5 mmol) 및 PyBop (2 画 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 87 화합물을 수득하였다 (수율 =46%). Dissolved in DMF (2 mL). DIPEA (3 mmol), p-lluidine (1.5 mmol) and PyBop (2 μl ol) was 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. Then purified by silica gel chromatography to give the compound of Synthesis 87 (yield = 46%).
¾ NMR( 400MHz, CDC13)6 10.12 (s IH, -NH), 8.28 (s, 1H), 7.65 (d¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s IH, -NH), 8.28 (s, 1H), 7.65 (d
IH), 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 합성예 89 ： N-(4-메록시페닐) -2-옥소 -1，2-디하이드로퀴놀린— 3- 카르복사마이드 IH), 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, 3 H). MASS = 306.14 Synthesis Example 89 ： N- (4-methoxyphenyl) -2-oxo-1,2-dihydroquinoline— 3-carboxamide
2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 匪 ol)를 DMF (2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-메톡시아닐린 (1.5 睡 ol) 및 PyBop (2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크.로마토그래프로 정제하여 합성예 89 화합물을 수득하였다 (수을 =43%).  2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-methoxyaniline (1.5' ol) 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. Purification with silica gel chromatograph then gave Synthesis Example 89 compound (number = 43%).
¾ 匪 R(400MHz, CDC13)5 10.12(s, IH, -NH), 8.28(s, IH), 7.65(d, IH), 7.36 (d, IH), 7.31(t, IH), 7.21(dd, 2H), 7.17(dd, 2H), 7.14(t, IH), 4.23(s, 2H), 3.44(s, 3H), 2.34(s, 3H). MASS= 306.14 합성예 92: N-(4-브로모페닐) -2-옥소— 1，2-디하이드로퀴놀린 -3-카르복사마이 ¾ 匪 R (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 7.65 (d, IH), 7.36 (d, IH), 7.31 (t, IH), 7.21 ( dd, 2H), 7.17 (dd, 2H), 7.14 (t, IH), 4.23 (s, 2H), 3.44 (s, 3H), 2.34 (s, 3H). MASS = 306.14 Synthesis Example 92: N- (4-Bromophenyl) -2-oxo— 1,2-dihydroquinoline-3-carboxymai
2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-브로모아닐린 (1.5醒 ol ) 및 PyBop (2mmol)를 반웅 합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-bromoaniline (1.5 μl ol) 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. After purification by silica gel column chromatography to obtain the compound of Synthesis 92 (Yield = 48%).
¾ 匿 ( 400MHz, CDC13 )δ 10.12(s, IH, -NH), 8.28(s, IH), 8.14(d, IH), 7.51 (dd, 2H), 7.36(d, 2H), 7.31(t, IH)， 7.14(t, IH), 6.97(dd, IH). MASS= 342.00 합성예 95 ： N-(4-클로로페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마 이드 ¾ 匿 (400MHz, CDC13) δ 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d, IH), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH). MASS = 342.00 Synthesis Example 95: N- (4-chlorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 4-클로로아닐린 (1.5 瞧 ol) 및 PyBop (2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 95 화합물을 수득하였다 (수율 =42%).  2-oxo-l, 2'dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-chloroaniline (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to give the Synthesis Example 95 compound (yield = 42%).
¾ NMR (400MHz, CDC13 )δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d,¾ NMR (400 MHz, CDC1 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). MASS= 298.05 합성예 96 ： N-(4-클로로페닐) -1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H). MASS = 298.05 Synthesis Example 96 N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
1-메틸 -2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 隱 ol)
DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-클로로아닐린 (1.5 画 ol) 및Dissolved in DMF (2 mL). DIPEA (3 隱 ol), 4-chloroaniline (1.5 画 ol) and
PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 96 화합물을 수득하였다 (수율 =56%). PyBop (2 μL ol) was 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. Then purified by silica gel chromatography to obtain the Synthesis Example 96 compound (yield = 56%).
¾ NMR (400MHz, CDC13)6 10.12(s, 1H, -NH) , 8.28(s, 1H), 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 6 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), 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 합성예 97 ： N-(4-클로로페닐) -1-에틸 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 1H), 3.3 (s, 3H). MASS = 312.07 Synthesis Example 97: N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
1-에틸— 2-옥소— 1， 2-디하이드로퀴놀린 -3—카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 mmol), 4-클로로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 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 μL) was dissolved in DMF (2 mL). DIPEAC3 mmol), 4-chloroaniline (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 97 (yield = 56%).
¾ 證 (400MHz, CDC13)5 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, 1H), 7.51 (ddᅳ 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 합성예 118 ： N-(4-플루오로페닐 )ᅳ2-옥소 -1，2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ 證 (400MHz, CDC1 3 ) 5 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d, 1H), 7.51 (dd ᅳ 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 Synthesis Example 118 ： N- (4-fluorophenyl) ᅳ 2-oxo-1-, 2-dihydroquinoline-3-carboxamide
2-옥소ᅳ 1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3画 ol), 4-플루오로아닐린 (1.5 mmol) 및 PyBop 2-oxo® 1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 ′ ol), 4-fluoroaniline (1.5 mmol) and PyBop
(2 議 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 118 화합물을 수득하였다 (수율 =5¾). (2 μl ol) was 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. Subsequent purification with silica gel chromatography gave the compound of Synthesis 118 (yield = 5¾).
¾ NMR ( 400MHz, CDC13 )δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, ¾ NMR (400 MHz, CDC13) 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) .1H), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t, 1H), 7.14 (t, 1H), 6.97 (dd, 1H).
MASS= 282.08 합성예 119 ： N— (4-플루오로페닐 )-1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 MASS = 282.08 Synthesis Example 119 ： N— (4-fluorophenyl) -1-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide
1-메틸 -2-옥소ᅳ 1ᅳ 2-디하이드로퀴놀린— 3-카복실릭 애시드 (1瞧01)를 1-methyl-2-oxoze 1 ′ 2-dihydroquinoline— 3-carboxylic acid (1 瞧 01)
DMF(2 mL)에 용해시켰다. DIPEM3 画 ol), 4-플루오로아닐린 (1.5 mmol) 및Dissolved in DMF (2 mL). DIPEM3 画 ol), 4-fluoroaniline (1.5 mmol) and
PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. '수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 119 화합물을 수득하였다 (수율 =47%). PyBop (2 mmol) was 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 purified by silica gel chromatography to give the compound of Synthesis Example 119 (yield = 47%).
¾ NMR ( 400MHz, CDC1 a )δ 10.12(s, 1H, -NH), 8.28(s, 1H), 8.14(d, ¾ NMR (400 MHz, CDC1 a) 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), 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 합성예 120 ： 1-에틸 -N-(4-플루오로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 1H), 3.3 (s, 3H). MASS = 296.10 Synthesis Example 120: 1-ethyl-N- (4-fluorophenyl) -2-oxo-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), 4-플루오로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 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 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 120 (yield = 45%).
¾ 薩 (400MHz, CDC13)6 10.12(s, IH, - H) , 8.28(s, IH) , 8.14(d, IH), 7.51(dd, 2H), 7.36(d, 2H), 7.31(t, IH), 7.14(t, IH)， 6.97(dd, IH) , 4.28(s, 2H), 3.3(s, 3H). MASS: 310.11 합성예 121 ： 1-((2H-피를 -3-일)메틸) -N-(4-플루오로페닐 )-2-옥소 -1,2-디하 이드로 퀴놀린 -3-7]·르복사마이드 ¾ 薩 (400 MHz, CDC1 3 ) 6 10.12 (s, IH, -H), 8.28 (s, IH), 8.14 (d, IH), 7.51 (dd, 2H), 7.36 (d, 2H), 7.31 (t , IH), 7.14 (t, IH), 6.97 (dd, IH), 4.28 (s, 2H), 3.3 (s, 3H). MASS : 310.11 Synthesis Example 121: 1-((2H-Pyridyl-3-yl) methyl) -N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-7] Leboxamide
1-( (2H-피를 -3-일 )메될)—2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4ᅳ플루오로 아닐린 (1.5 睡 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 121 화합물을 수득하였다 (수율 =48%)  1- ((2H-Pyridyl-3-yl) methyl) —2-oxoxo 1, 2-dihydroquinoline-3-carboxylic acid (1 × ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4'fluoro aniline (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 121 (Yield = 48%)
¾ NMR (400MHz, CDC13)5 10.12(s, IH, -NH), 8.28(s, IH) , 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d,
IH), 7.51 (m, 3H), 7.36(d, 2H), 7.31(t, IH), 7.14(t, IH) , 6.97(dd, IH) ,IH), 7.51 (m, 3H), 7.36 (d, 2H), 7.31 (t, IH), 7.14 (t, IH), 6.97 (dd, IH),
5.06(s, IH), 4.28(s, 2H)， 3.63(s, 2H), 2.0(s, IH). MASS=361.12 합성예 125: N-(4-에틸페닐) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPE/ 3隱 ol), 4-에틸아닐린 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 125 화합물을 수득하였다 (수율 = 50%) . 5.06 (s, IH), 4.28 (s, 2H), 3.63 (s, 2H), 2.0 (s, IH). MASS = 361.12 Synthesis Example 125: N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide 2-oxo-1,2'dihydroquinoline-3-carboxylic acid ( 1 μl) was dissolved in DMF (2 mL). DIPE / 3 ′ ol), 4-ethylaniline (1.5 mmol) and PyBop (2 ′ ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis 125 (Yield = 50%).
¾ 匪 R(400MHz, CDC13)6 10.12(s, IH, -NH), 8.28(s, IH), 8.14(d, 1H), 7.51(111， 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 합성예 126 ： N-(4-에틸페닐) -1-메틸 -2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카르복 사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d, 1H), 7.51 (111, 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 Synthesis Example 126: N- (4-ethylphenyl) -1-methyl-2-oxo-1,2'dihydroquinoline-3-carboxamide
1-메틸 -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEAO 隱 ol), 4-에틸아닐린 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 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-l, 2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEAO 隱 ol), 4-ethylaniline (1.5 隱 ol) and PyBop (2 画 ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 126 (yield = 47%).
¾ 匪 R (400MHz, CDC13)5 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 합성예 127 ： 1-에틸 -N— (4-에틸페닐) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 127: 1-ethyl-N— (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-에틸 -2-옥소ᅳ 1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 國 ol)를 DMF(2 niL)에 용해시켰다. DIPEA(3 mmol), 4ᅳ에틸아닐린 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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-oxoze 1,2-dihydroquinoline-3-carboxylic acid (1 ol) was dissolved in DMF (2 niL). DIPEA (3 mmol), 4'ethylaniline (1.5'ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 127 (yield = 43%).
¾ NMR (400MHz ,CDC13 )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 합성예 128 ： l-(2-(2H-피를 -3-일)에틸) -N-(4-에틸페닐) -2-옥소 -1，2-디하이 드로퀴놀린ᅳ 3-카르복사마이드 ¾ NMR (400MHz, CDC1 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), 2.3 (s, 2H), 1.25 (s, 3H). MASS = 320.15 Synthesis Example 128: l- (2- (2H-Pyridyl-3-yl) ethyl) -N- (4-ethylphenyl) -2-oxo-1,2-dihydrodroquinolinone 3-car Copyamide
1-(2-(2Η-피를 -3-일)에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸아닐린 (1.5 瞧 ol) 및 PyBop(2 画 ol)를 반웅 혼합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 128 화합물을 수득하였다 (수율 =45%). 1- (2- (2Η-blood to 3-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 μL) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethylaniline (1.5 μs ol) and PyBop (2 μs ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 128 (yield = 45%).
¾ NMR (400MHz, CDC13)5 10.12(s, 1H, -NH) , 8.28(s, 1H), 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 133 ： N-(4-하이드록시페닐) -2-옥소 -1,2-디하이드로퀴놀린— 3-카르복 사마이드 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 Synthesis Example 133: N- (4-hydroxyphenyl) -2-oxo-1,2-dihydro Quinoline— 3-carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(2 隱 ol), 4-아미노페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (2 μL), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 133 (yield = 42%).
¾ 賺 ( 400MHz, CDC13 )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 합성예 134 (N-(4-하이드록시페닐) -1-메틸 -2-옥소 -1,2-디하이드로퀴놀린ᅳ 3- 카르복사마이드)  ¾ 賺 (400 MHz, CDC13) 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 Synthesis Example 134 (N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline® 3-carboxamide)
합성예 28 화합물 (1隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3mmol ) , 4—아미노페놀 (1.5 mmol) 및 PyBop(2 睡 ol)를 반응 흔합물에 첨가하였다. 흔합물을 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 Compound (1'ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4—aminophenol (1.5 mmol) and PyBop (2 μl ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 134 compound (yield = 49%).
¾ NMR ( 400MHz, CDC13 )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 합성예 135 ： 1-에될 -N-(4-하이드록시페닐) -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 MHz, CDC13) 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 Synthesis Example 135: 1-Esyl-N- (4-hydroxyphenyl) -2oxoo-1,2-dihydroquinoline-3-carboxamide
합성예 29 화합물 (lmmol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), 4ᅳ아미노페놀 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 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 Compound (lmmol) was dissolved in DMF (2 mL). DIPEAC3 'ol), 4'aminophenol (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis 135 (Yield = 46%).
¾ NMR(400MHz, CDC13)6 10.12(s, 1H, - H) , 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 합성예 136 ： N-(4ᅳ하이드록시페닐) -2-옥소 -1— (2- (티오펜 -2-일)에틸) -1,2- 디하이드로퀴놀린ᅳ 3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -H), 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 Synthesis Example 136 ： N- (4'hydroxyphenyl) -2-oxo-1- (2- (thiophen-2-yl) ethyl) -1,2-dihydroquinoline® 3-carboxamide
2-옥소 -1-(2- (티오펜ᅳ 2-일)에틸) -1，2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4- 아미노페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 136 화합물을 수득하였다 (수율 =56%).  2-oxo-1- (2- (thiophene-2-yl) ethyl) -1,2'dihydroquinoline-3-carboxylic acid (1xol) 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 136 (yield = 56%).
¾ NMR ( 400MHz, CDC13)5 10.12(s, 1H, -NH) , 8.28(s, 1H) , 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d,
1H), 7.51 (dd, 2H), 7.40(s, 1H), 7.36(dᅳ 2H) , 7.31(t, 1H), 7.14(t, 1H) ,1H), 7.51 (dd, 2H), 7.40 (s, 1H), 7.36 (d ᅳ 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),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 합성예 140 ： N-(4-니트로페닐) -2-옥소 -1,2-디하이드로퀴놀린— 3-카르복사마 이드 3.83 (s, 2 H). MASS-390.10 Synthesis Example 140 ： N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline—3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-니트로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토 그래프로 정제하여 합성예 140 화합물을 수득하였다 (수율 =59%). Ή 匿 (400腿 z, CDC13)5 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)ᅳ 6.97(dd, 1H). MASS=309.07 합성예 143 ： N-(4-(N,N-디메틸설파모일)페닐) -2-옥소 -1，2-디하이드로퀴놀린 -3-카르복사마이드 Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-nitroaniline (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to give the Synthesis Example 140 compound (yield = 59%). 腿 腿 (400 腿 z, CDC1 3 ) 5 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) ᅳ 6.97 (dd, 1H). MASS = 309.07 Synthesis Example 143 ： N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 麵 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-아미노 -Ν,Ν-디메틸벤젠설폰아미드 (1.5 画 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 143 (yield = 49%).
¾ NMR (400MHz, CDC13)5 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(1;， 1H), 2.66(m, 6H). MASS=371.09 합성예 144 ： N-(4-(N,N-디메틸설파모일)페닐) -1ᅳ메틸 2-옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 (1 ;; 1H), 2.66 (m, 6H). MASS = 371.09 Synthesis Example 144 ： N- (4- (N, N-dimethylsulfamoyl) phenyl) -1 ᅳ methyl 2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 28 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 4-아미노 -Ν,Ν-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 144 (yield = 62%).
¾ 匪 R OOMHz, CDC13)6 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 합성예 145 ： N-(4-(N,N-디메틸설파모일)페닐) -1-에틸ᅳ2-옥소 -1,2—디하이드 로퀴놀린 -3-카르복사마이드 ¾ 匪 R OOMHz, CDC1 3 ) 6 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 Synthesis Example 145: N- (4- (N, N-dimethylsulfamoyl) phenyl) -1-ethyl ᅳ 2-oxo-1,2—dihydroquinoline-3-carboxamide
합성예 29 화합물 (1 讓 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), 4-아미노 -Ν,Ν-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 讓 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 145화합물을 수득하였다 (수율 =67%).Synthesis Example 29 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 145 compound (yield = 67%).
' ¾ NMR (400MHz, CDC13)6 10.12(s, IH, ᅳ NH)， 8.28(s, IH), 8.14(d, IH), 8.0 (s, IH, -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- (사이클로핵실메틸) -N-(4-(N,N-디메틸설파모일)페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 '' ¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, IH, ᅳ NH), 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -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 Synthesis Example 146 ： 1- (cyclonucleosilmethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1- (사이클¾핵실메틸 )-2—옥소 -1,2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mniol), 4-아미노 -Ν,Ν- 디메틸벤젠설폰아미드 (1.5 隱 ol) 및 PyBop(2mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 146 화합물을 수득하였다 (수율 = 62%) .  1- (Cycle¾ Nucleylmethyl) -2—oxo-1,2-dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mniol), 4-amino-N, N-dimethylbenzenesulfonamide (1.5 μl ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 146 compound (yield = 62%).
¾ NMR (400MHz, CDC13)8 10.12(s, IH, -NH), 8.28(s, IH), 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 8 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d,
IH), 8.0(s, IH, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, IH), 7.14 (t, IH), 3.98(s, 2H), 2.66(m, 6H), 2.06(s, IH), 1.43(m, 5H) . MASS=467.19 합성예 147 ： l-(2-사이클로핵실에틸) -N-(4-(N,N -디메틸설파모일)페닐) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 IH), 8.0 (s, IH, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 3.98 ( s, 2H), 2.66 (m, 6H), 2.06 (s, IH), 1.43 (m, 5H). MASS = 467.19 Synthesis Example 147: l- (2-cyclonucleosilethyl) -N- (4- (N, N-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carbox Maid
1-에틸 -N-(4-에틸페닐 )-2ᅳ옥소 -1 ,2—디하이드로퀴놀린ᅳ 3—카르복사마이 드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 4ᅳ아미노 -N,N_ 디메틸벤젠설폰아미드 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 147 화합물을 수득하였다 (수율 = 49%) .  1-ethyl-N- (4-ethylphenyl) -2ioxo-1,2-dihydroquinoline® 3-carboxamide (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4'amino-N, N_dimethylbenzenesulfonamide (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 147 (yield = 49%).
¾ 匪 R (400MHz, CDC13)S 10.12(s, IH, -NH), 8.28(s, IH), 8.14(d, IH), 8.0 (s, IH, -NH), 7.84(d, 2H), 7.64(d, 2H), 7.36(d, 2H), 7.3(t, IH), 7.14(t, IH), 3.98(s, 2H), 3.46(s, 3H), 2.66(mᅳ 6H), 2.06(s, IH), 1.43(m, 5H). MASS=481.20 합성예 148 ： N-(4- (하이드록시메틸)페닐) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) S 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.84 (d, 2H) , 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, IH), 7.14 (t, IH), 3.98 (s, 2H), 3.46 (s, 3H), 2.66 (m ᅳ 6H), 2.06 (s, IH), 1.43 (m, 5H). MASS = 481.20 Synthesis Example 148 N- (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄을 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여..합성예 148 화합물을 수득하였다 (수율 = 58%) .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-aminophenyl) methane (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography. Synthesis Example 148 A compound was obtained (yield = 58%).
¾ 匪 R ( 400MHz, CDC13)8 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 합성예 149 ： N-(4- (하이드록시메틸)페닐) -1-메틸 -2-옥소 -1， 2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ 匪 R (400MHz, CDC1 3 ) 8 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 Synthesis Example 149: N- (4- (hydroxymethyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 28 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐)메탄을 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물올 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-aminophenyl) methane (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 149 (yield = 56%).
¾ NMR(400MHz, CDC13)6 10.12(s, 1H, -NH) , 8.28(s, 1H)ᅳ 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 8.28 (s, 1H) ᅳ 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 합성예 150 ： 1-에틸 -N— (4- (하이드록시메틸)페닐) -2-옥소 -1，2-디하이드로 퀴놀린 -3-카르복사마이드 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 Synthesis Example 150: 1-ethyl-N— (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 29 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 mmol), (4-아미노페닐)메탄을 (1.5 mmol) 및 PyBop(2 画 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테아트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 150 화합물을 수득하였다 (수율 =56%). ¾匪1(40()1\1¾，0)(:13½ 10.12(s, IH, ᅳ NH), 8.28(s, IH), 8.14(d, IH)ᅳ 8.0 (s, IH, -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, IH, -OH), 3.4(s, 2H), 3.3(s, 3H). MASS=322.13 합성예 151 ： 1- (사이클로펜틸메틸) -N-(4- (하이드록시메틸)페닐) -2-옥소- 1， 2-디하이드로퀴 린 -3-카르복사마이드 Synthesis Example 29 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEAC3 mmol), (4-aminophenyl) methane (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 150 compound (yield = 56%). ¾ 匪 1 (40 () 1 \ 1¾ ， 0) (: 1 3 ½ 10.12 (s, IH, ᅳ NH), 8.28 (s, IH), 8.14 (d, IH) ᅳ 8.0 (s, IH, -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, IH, -OH), 3.4 (s, 2H), 3.3 (s, 3H) MASS = 322.13 Synthesis Example 151: 1- (cyclopentylmethyl) -N- (4- (hydroxymethyl) phenyl) -2-oxo- 1, 2-dihydroquirin-3-carboxamide
1- (사이클로펜틸메틸 )-2-옥소 -1,2—디하이드로퀴놀린 -3-카복실릭 애시 드 (1 麵 ol)를 DMF(52 mL)에 용해시켰다. DIPEA(3 mmol), (4-아미노페닐) 메탄을 (1.5 麵 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (52 mL). DIPEA (3 mmol), (4-aminophenyl) methane (1.5 dl ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 151 (yield = 65%).
¾ NMR (400顧 z, CDC13)8 10.12(s, 1Hᅳ -NH), 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, -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), 3.98(s, 2H), 3.65(s, IH, -OH), 1.64(m, 8H). MASS=322.13 합성예 152: 2-옥소 -N-(4-비닐페닐)— 1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 麵 ol)을 DMF(2 mL)에 용해시켰다. DIPE/ 3 謹 ol), 4-비닐아닐린 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가 하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 152 화합물올 수득하였다 (수율 =53%). ¾ NMR (400 顧 z, CDC1 3 ) 8 10.12 (s, 1H ᅳ -NH), 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -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), 3.98 (s, 2H), 3.65 (s, IH, -OH), 1.64 (m, 8 H). MASS = 322.13 Synthesis Example 152: 2-oxo-N- (4-vinylphenyl) — 1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 A compound (1 麵 ol) was dissolved in DMF (2 mL) I was. DIPE / 3 謹 ol), 4-vinylaniline (1.5 mmol) and PyBop (2 睡 ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 152 (yield = 53%).
¾ NMR (400MHz, CDC13)6 10.12(s, IH, -NH), 8.28(s, IH), 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, IH, -NH), 8.28 (s, IH), 8.14 (d,
IH), 8.0 (s, IH, -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(s, IH). MASS=290.11 합성예 153 ： 1-메틸 -2-옥소 -N— (4-비닐페닐) -1,2-디하이드로퀴놀린 -3- 카르복사마이드 IH), 8.0 (s, IH, -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 (s, IH). MASS = 290.11 Synthesis Example 153 ： 1-Methyl-2-oxo-N— (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
합성예 28 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEA (3讓 ol), 4-비닐아닐린 (1.5 mmol) 및 PyBop (1 睡 ol)를 반웅 혼합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 153 화합물을 수득하였다 (수율 = 56%) . Synthesis Example 28 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-vinylaniline (1.5 mmol) and PyBop (1' ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 153 (yield = 56%).
¾ NMR( 400MHz, CDC13)5 10.12(s, 1H, — NH), 8.28(s, 1H), 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 154 ： 1-에틸 -2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린ᅳ 3-카르복 사마이드 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 Synthesis Example 154: 1-ethyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
합성예 29 화합물 (1麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-비닐아닐린 L5 mmol) 및 PyBop(2 i碰 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 154 화합물을 수득하였다 (수율 =64%).  Synthesis Example 29 Compound (1'ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-vinylaniline L5 mmol) and PyBop (2 i 碰 ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 154 (yield = 64%).
¾ NMR( 400MHz, CDC13)8 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(sᅳ 1H), 5.18(s, 1H), 3.4(s, 2H), 3.12(s, 3H). MASS=318.14 합성예 155 ： l-(2-사이클로펜틸에틸) -2-옥소 -N-(4-비닐페닐) -1，2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 8 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 ᅳ 1H), 5.18 (s, 1H), 3.4 (s, 2 H), 3.12 (s, 3 H). MASS = 318.14 Synthesis Example 155: l- (2-cyclopentylethyl) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
1ᅳ(2-사이클로펜틸에틸 )ᅳ2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- 비닐아닐린 (1.5 mmol) 및 PyBop(2瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 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 'ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-vinylaniline (1.5 mmol) and PyBop (2' ol) 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 purified by silica gel chromatography to give the compound of Synthesis Example 155 (yield = 48%).
¾ MR (400MHz, CDC13)5 10.12(s, 1H, -NH) , 8.28(s, 1H), 8.14(d,¾ MR (400 MHz, CDC1 3 ) 5 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 합성예 165 ： N-벤질— 2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 165 ： N-benzyl— 2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 編 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민 (1.5 画 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔 "물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 165 화합물을 수득하였다 (수율 = 57%) . Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), phenylmethanamin (1.5 μl ol) and PyBop (2 mmol) were added to the reaction mixture. Common "of water was stirred at room temperature for 3 hours to give the the obtained residue was extracted with ethyl acetate and water. After synthesis by purified by silica gel chromatography Example 165 compound (yield = 57%).
¾ NMR (400MHz, CDC13)S 10.12(s, 1H, -NH) , 8.28(s, 1H) , 8.14(d,¾ NMR (400 MHz, CDC1 3 ) S 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)ᅳ 7.14(t, 1H), 4.34(m, 2H). MASS=278.11 합성예 166 ： N-벤질 -1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린— 3-카르복사마이드 합성예 28 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 페닐메타나민 (1.5 mmol) 및 PyBop (1 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 166 화합물을 수득하였다 (수율 = 56%) . 1H), 8.0 (s, 1H, -NH), 7.84 (d, 2H), 7.64 (d, 2H), 7.36 (d, 2H), 7.3 (t, 1H) ᅳ 7.14 (t, 1H), 4.34 ( m, 2H). MASS = 278.11 Synthesis Example 166 N-benzyl-1-methyl-2-oxo-1,2-dihydroquinoline—3-carboxamide Synthesis Example 28 A compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), phenylmethanamin (1.5 mmol) and PyBop (1 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. Then purified by silica gel chromatography to obtain the Synthesis Example 166 compound (yield = 56%).
¾ NMR (400MHz, CDC13)6 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.14 (d,¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 167 ： N-벤질 -1-에틸 -2-옥소ᅳ1， 2-디하이드로퀴놀린 -3-카르복사마이드 합성예 29 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 페닐메타나민 (1.5 mmol) 및 PyBop(2 議 οί)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프 로 정제하여 합성예 167 화합물을 수득하였다 (수율 = 59%). 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 Synthesis Example 167: N-benzyl-1-ethyl-2-oxox1, 2-dihydroquinoline-3-carboxamide Synthesis Example 29 A compound (1xol) was dissolved in DMF (2 mL). . DIPEA (3 mmol), phenylmethanamin (1.5 mmol) and PyBop (2 議 οί) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 167 (yield = 59%).
¾ NMR (400MHz, CDC13)6 10.12(s, 1H, ᅳ NH), 8.28(s, 1H) , 8.14(d,¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, ᅳ 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, 3H). MASS=306.14 합성예 179 ： 2-옥소— N-펜에틸 -1,2-디하이드로퀴놀린 -3-카르복사마이드 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, 3H). MASS = 306.14 Synthesis Example 179: 2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 2ᅳ페닐에타나민 (1.5麵 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 179화합물을 수득하였다 (수율 =56%)/ Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2'phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 179 (yield = 56%) /
¾ NMR (400丽 z, CDC13)6 8.28(s, IH) , 8.14(d, IH) , 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.40(dd, 2H), 7.29(dd, 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 ： l-(4-메록시벤질) -2-옥소 -N-펜에틸 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 δ z, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.40 (dd, 2H ), 7.29 (dd, 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 . Synthesis Example 180: l- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
합성예 26 화합물 (1 讓 ol)을 DMF(2 mL)에 용해시찼다. DIPEA(3 画 ol), 2-페닐에타나민 (1.5 画 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프 로 정제하여 합성예 180 화합물을 수득하였다 (수율 = 52%) .  Synthesis Example 26 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 2-phenylethanamine (1.5 μl ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 180 compound (yield = 52%).
¾ NMR (400MHz, CDC13 )δ 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - ¾ NMR (400 MHz, CDC13) δ 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-
NH), 8.0(s, 1H' -NH), 7.40(dd, 2H), 7.29(m, 4H), 7.27(m, 3H), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 3.55(m, 2H), 3.3(s, 2H) , 2.95(s, 3H), 2.83(ni, 2H). MASS=412.18 합성예 181 ： 2-옥소 -N-펜에틸 -l-(4- (트리플루오로메록시)벤질 )-1ᅳ2- 디하이드로퀴놀린 -3-카르복사마이드 NH), 8.0 (s, 1H'-NH), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 (m, 3H), 7.36 (d, IH), 7.31 (t, IH), 7.14 ( t, IH), 3.55 (m, 2H), 3.3 (s, 2H), 2.95 (s, 3H), 2.83 (ni, 2H). MASS = 412.18 Synthesis Example 181: 2-oxo-N-phenethyl-1-(4- (trifluoromethoxy) benzyl) -1'2-dihydroquinoline-3-carboxamide
합성예 27 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), 2-페닐에타나민 (1.5麵 ol) 및 PyBop(2讓 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하였다. 수득 한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 181 화합물을 수득하였다 (수율 =49%) ¾ NMR( 400MHz, CDC 13 )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(mᅳ 2H). MASS=466:15 합성예 182 ： l-(2-(4-메록시 -2,3-디하이드로 -1H-인덴 -2-일)에틸) -2-옥소 -N- 펜에틸 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 Synthesis Example 27 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 181 (yield = 49%) ¾ NMR (400 MHz, CDC 13) 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 ᅳ 2H). MASS = 466: 15 Synthesis Example 182: l- (2- (4-methoxy-2,3-dihydro-1H-inden-2-yl) ethyl) -2-oxo-N-phenethyl-1, 2 -Dihydroquinoline-3-carboxamide
1- (2-(4ᅳ메톡시 -2,3-디하이드로-111-인덴-2ᅳ일)에틸)-2-옥소ᅳ1，2-디하 이드로퀴놀린 -3ᅳ카복실릭 애시드 (1 隱 οΠ를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 2ᅳ페닐에타나민 (1.5 画 ol) 및 PyBop(2 麵 ol)를 반웅 흔합물 에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마 토그래프로 정제하여 합성예 182 화합물을 수득하였다 (수율 =56%).  1- (2- (4 ᅳ methoxy-2,3-dihydro-111-inden-2 ylyl) ethyl) -2-oxo ᅳ 1,2-dihydroquinoline-3 ᅳ carboxylic acid (1 隱 οο DMF (2 mL) DIPEA (3 麵 ol), 2 ᅳ phenylethanamine (1.5 画 ol) and PyBop (2 麵 ol) 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 chromatograph to give Synthesis Example 182 compound (yield = 56%).
¾ 匪 R (400MHz, CDC13)5 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 합성예 183 ： 2—옥소 -N-펜에틸 -1— (2-(4- (트리플루오로메톡시) -2，3-디하이 드로 -1H-인덴 -2-일)에틸 )ᅳ1，2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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, 8 H). MASS = 466.23 Synthesis Example 183 ： 2—Oxo-N-phenethyl-1— (2- (4- (trifluoromethoxy) -2,3-dihydro-1H-inden-2-yl) ethyl) ᅳ 1,2-dihydroquinoline-3-carboxamide
2-옥소 -1-(2-(4ᅳ (트리플루오로메특시 )ᅳ2，3-디하이드로 -1Hᅳ인덴 -2-일 ) 에틸 )ᅳ1, 2—디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEM3 顏 ol), 2-페닐에타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol) 를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 183 화합물을 수득하였다 (수율 = 53%) .  2-oxo-1- (2- (4 '(trifluoromete)) ᅳ 2,3-dihydro-1H ᅳ inden-2-yl) ethyl) ᅳ 1,2—dihydroquinoline-3-carboxyl Rick acid (1 μl) was dissolved in DMF (2 mL). DIPEM3 'ol), 2-phenylethanamine (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 183 compound (yield = 53%).
¾ 丽 (400MHz, CDC13)6 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 합성예 191 ： 2-옥소 -N-(3-페닐프로필) -1,2-디하이드로퀴놀린 -3-카르복사마 이드 ¾ δ (400 MHz, CDC1 3 ) 6 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, 5 H). MASS = 520.20 Synthesis Example 191: 2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 3-페닐프로판 -1-아민 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토 그래프로 정제하여 합성예 191 화합물을 수득하였다 (수율: = 56%) .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 3-phenylpropane-1-amine (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the Synthesis Example 191 compound (yield: = 56%).
1H MR(400MHz,CDCl3)6 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 합성예 192 ： l-(4-메톡시벤질 )ᅳ2-옥소 -N-(3-페닐프로필) -1,2-디하이드로 퀴놀린 -3-카르복사마이드 1H MR (400MHz, CDCl 3 ) 6 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 Synthesis Example 192: l- (4-methoxybenzyl) ᅳ 2-oxo-N- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide
합성예 26 화합물 (1 讓 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), 3-페닐프로판 -1-아민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 192 화합물을 수득하였다 (수율 = 63%).  Synthesis Example 26 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 3-phenylpropane-1-amine (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 192 compound (yield = 63%).
¾ NM ( 400MHz, CDC13)5 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(iii, 3H), 3.18(m, 2H), 3.3(s, 2H), 2.62(m, 2H), 2.09(m, 2H) 1.62(s, 3H). MASS=426.19 합성예 193 ： l-(2-(5-포르밀 -2,3-디하이드로-lH-인덴-2-일)에틸)-2—옥소-N- (3-페닐프로필) -1,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NM (400MHz, CDC1 3 ) 5 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 (iii, 3H), 3.18 (m, 2H), 3.3 (s, 2H), 2.62 (m, 2H), 2.09 (m, 2H) 1.62 (s, 3H). MASS = 426.19 Synthesis Example 193: l- (2- (5-formyl-2,3-dihydro-lH-inden-2-yl) ethyl) -2—oxo-N- (3-phenylpropyl) -1 , 2-dihydroquinoline-3-carboxamide
1-(2— (5-포르밀 -2，3-디하이드로 -1H—인덴 -2-일)에틸 )— 2-옥소 -1， 2-디하 이드로퀴놀린 -3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. 1- (2— (5-formyl-2,3-dihydro-1H—inden-2-yl) ethyl) — 2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 mmol) Was dissolved in DMF (2 mL).
DIPEAC3 闘 ol), 3ᅳ페닐프로판ᅳ1—아민 (1.5 画 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 193 화합물을 수득하였다 (수율 = 46%) . Ή NMR(400MHz,CDCl3)5 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 합성예 194 ： (l-(2-(5— (메틸티오) -2,3-디하이드로 -1H—인덴— 2-일)에틸) -2- 옥소 -N-(3-페닐프로필) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드) DIPEAC3 闘 ol), 3'phenylpropane ᅳ 1-amine (1.5 画 ol) and PyBop (2 mmol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 193 (yield = 46%). NMR (400MHz, CDCl 3 ) 5 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 Synthesis Example 194: (l- (2- (5— (methylthio) -2,3-dihydro-1H—indene-2-yl) ethyl) -2-oxo-N- (3-phenylpropyl ) -1, 2-dihydroquinoline-3-carboxamide)
1-(2-(5- (메틸티오) -2 ,3-디하이드로 -1H-인덴 -2ᅳ일)에틸 )-2-옥소ᅳ 1 ,2- 디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 醒 ol), 3-페닐프로판 -1-아민 (1.5 睡 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득힌 : 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 194 화합물을 수득하였다 (수율 =46%) · 1- (2- (5- (methylthio) -2,3-dihydro-1H-inden-2-2-yl) ethyl) -2-oxoze 1,2- dihydroquinoline 3- 3-carboxylic acid (1 隱ol) was dissolved in DMF (2 mL). DIPEAC3 醒 ol), 3-phenylpropane-1-amine (1.5 睡 ol) and PyBop (2 隱 ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. Obtained : The residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 194 compound (yield = 46%).
¾ 匪 R(400MHz, CDC13)5 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,¾ 匪 R (400MHz, CDC1 3 ) 5 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),1H), 7.14 (m, 3H), 3.3 (s, 2H), 3.18 (m, 4H), 2.97 (s, 2H), 2.62 (m, 2H),
2.09(iri, 7H), 1.29(s, 3H). MASS=496.22 합성예 195 ： N-(4-메틸벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드 2.09 (iri, 7 H), 1.29 (s, 3 H). MASS = 496.22 Synthesis Example 195 ： N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 隱 ol), P-를일메타나민 (1.2 画 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 195 화합물을 수득하였다 (수율 = 46%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEM3 隱 ol), P-ylmethanamin (1.2 画 ol) and PyBop (2 醒 ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 195 (yield = 46%).
¾ 薩 R ( 400MHz, CDC13 )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 합성예 196 ： l-(4-메록시벤질) -N— (4-메틸벤질) -2-옥소 -1,2—디하이드로퀴놀 린 -3-카르복사마이드 합성예 26 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), p-를일메타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 196 화합물을 수득하였다 (수율 = 54%) ¾ 薩 R (400 MHz, CDC13) 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 Synthesis Example 196: l- (4-Methoxybenzyl) -N— (4-methylbenzyl) -2-oxo-1,2—dihydroquinoline-3-carboxamide Synthesis Example 26 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), p-ylmethanamin (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 196 (yield = 54%)
¾ 證 (400MHz, CDCl3)58.28(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 합성예 197 ： N-(4-메틸벤질) -2-옥소 -1-(3ᅳ (트리플루오로메특시)펜에틸 )-1，2¾ 證 (400 MHz, CDCl 3 ) 58.28 (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 Synthesis Example 197 N- (4-methylbenzyl) -2-oxo-1- (3 '(trifluorome special) phenethyl) -1,2
-디하이드로퀴놀린 -3—카르복사마이드 -Dihydroquinoline-3—carboxamide
2-옥소 -1-(3- (트리플루오로메록시 )펜에틸 )-1， 2-디하이드로퀴놀린 -3ᅳ 카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), p- 를일메타나민 (1.5 :画 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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' ol) was dissolved in DMF (2 mL). DIPEAC3 'ol), p-ylmethanamin (1.5 :' ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 197 (yield = 45%).
¾ NMR( 400MHz, CDC13)6 8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, -NH)¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 198 ： l-(3-시아노펜에틸)— N-(4-메틸벤질) -2-옥소 -1，2-디하이드로 퀴 놀린 -3-카르복사마이드 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 Synthesis Example 198: l- (3-cyanophenethyl) —N- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(3-시아노펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), p-를일메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 μl ol), p-ylmethanamin (1.5 mmol) and PyBop (2 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 198 (yield = 59%).
¾ NMR( 400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H) 8.03(s, 1H, ᅳ NH): ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (s, 1H) 8.03 (s, 1H, ᅳ 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 합성예 199 ： N— (4-메틸펜에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드 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 Synthesis Example 199 ： N— (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2-(p-를일)에타나민 (1.5 醒 ol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 199 화합물을 수득하였다 (수율 =45%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), 2- (p-ylyl) ethanamine (1.5 醒 ol) and PyBop (2 睡 ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 199 (yield = 45%).
¾ NMR (400MHz, CDC13 )δ 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 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(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 합성예 200 ： l-(4- (하이드록시메틸)벤질) -N-(4-메틸펜에틸) 2-옥소— 1，2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 200: l- (4- (hydroxymethyl) benzyl) -N- (4-methylphenethyl) 2-oxo— 1,2-dihydroquinoline-3-carboxamide
1-(4- (하이드록시메틸)벤질 )ᅳ2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(p-를일) 에타나민 (1.5. mmol) 및 PyBop(2 讓 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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) ᅳ 2-oxo— 1, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (p-ylyl) ethanamine (1.5. Mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis 200 (Yield = 56%).
¾ NMR (400MHz, CDC13)6 8.28(s. 1H) , 8.14(d, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 6 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,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 합성예 201 ： l-(4-에틸벤질)— N-(4-메틸펜에틸) -2-옥소 -1,2-디하이드로퀴놀 린 -3-카르복사마이드 1H), 6.98 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.34 (s, 3H). MASS = 426.19 Synthesis Example 201: l- (4-ethylbenzyl) —N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-에틸벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(3 mL)에 용해시켰다. DIPEA(3 薩 ol), 2-(p-를일)에타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반응 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (3 mL). DIPEA (3 'ol), 2- (p-ylyl) ethanamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. The residue obtained was ethyl acetate and Extracted with water. Then purified by silica gel chromatography to give the compound of Synthesis Example 201 (yield = 56%).
¾ NMR( 400MHz, CDC13)6 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 합성예 202 ： l-(4-메록시벤질) -N-(4-메틸펜에틸) -2-옥소 -1,2ᅳ디하이드로 퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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, 2 H), 1.67 (s, 6 H). MASS = 424.22 Synthesis Example 202: l- (4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide
합성예 26 화합물 (1 讓 ol)을 DMF(2 mL)에 용해시켰다. DIPEA Synthesis Example 26 Compound (1xol) was dissolved in DMF (2 mL). DIPEA
(3瞧 ol), 2-(p-틀일)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 202 화합물을 수득하였다 (수율 =68%). (3 ′ ol), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 202 (yield = 68%).
¾ MR (400MHz, CDC13)6 8.28(s. 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ MR (400MHz, CDC1 3 ) 6 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 합성예 205 ： N-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드 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 Synthesis Example 205: N- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
2-옥소 -1,2ᅳ디하이드로퀴놀린 -3—카복실릭 애시드 (1 隱 ol)를 DM 2 mL)에 용해시켰다. DIPEA(3mmol), (4ᅳ메록시페닐)메타나민 (1.5 mmol) 및 PyBop(2 mmol)를 '반웅 흔합물에 첨가하였다. 흔합물을 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 'ol) was dissolved in 2 mL of DM). Of DIPEA (3mmol), (4 eume hydroxyphenyl) meth namin (1.5 mmol) and PyBop (2 mmol) 'was added to banung common compound. The mixture was stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 205 (yield = 68%).
¾ NMR( 400MHz, CDC13)8 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 합성예 206 ： l-(2-(5-아미노 -2,3-디하이드로 -IH-인덴 -2-일)에틸) -N-(4- 메특시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 8 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 Synthesis Example 206: l- (2- (5-amino-2,3-dihydro-IH-inden-2-yl) ethyl) -N- (4- Mesoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
1-(2— (5-아미노 -2， 3-디하이드로 -1H-인덴ᅳ 2ᅳ일)에틸 )ᅳ2—옥소ᅳ 1， 2-디하 이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 niL)에 용해시켰다. DIPEA(3瞧 ol), (4-메록시페닐)메타나민 (1.5 瞧 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득 한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 206 화합물을 수득하였다 (수율 =62%).  1- (2— (5-amino-2, 3-dihydro-1H-indensyl 2xyl) ethyl) ᅳ 2—oxo® 1, 2-dihydroquinoline-3-carboxylic acid (1 x ol) Dissolved in DMF (2 niL). DIPEA (3 'ol), (4-methoxyphenyl) methamine (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 206 (yield = 62%).
¾ 醒 R (400MHz, CDC13)5 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 합성예 207 ： l-(2-(5-에틸 -2，3-디하이드로 -1H-인덴 -2-일)에틸) _N-(4-메록시 벤질) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 醒 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 207: l- (2- (5-ethyl-2,3-dihydro-1H-inden-2-yl) ethyl) _N- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
1-(2— (5-에틸ᅳ 2，3-디하이드로 -1H-인덴ᅳ 2-일)에틸 )-2-옥소 -1 ,2—디하이 드로퀴놀린 -3ᅳ카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3賺 ol), (4-메록시페닐)메타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 207 화합물을 수득하였다 (수율 =68%).  1- (2— (5-ethyl ᅳ 2,3-dihydro-1H-indensyl 2-yl) ethyl) -2-oxo-1,2—dihedroquinoline-3 ᅳ carboxylic acid (1 mmol) Was dissolved in DMF (2 mL). DIPEA (3 ′ ol), (4-methoxyphenyl) methamine (1.5 mmol) and PyBop (2 ′ ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 207 (yield = 68%).
¾ 丽 R OOMHz, CDC13)6 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 합성예 208 ： N-(4-메록시펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ δ R OOMHz, CDC1 3 ) 6 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, 2 H), 2.64 (m, 7 H), 1.64 (s, 3 H). MASS = 480.24 Synthesis Example 208 ： N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
2ᅳ옥소 -1,2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3瞧 ol), 2ᅳ(4-메톡시페닐)에타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 208 화합물을 수득하였다 (수율 =63%). 2 ioxo-1,2 ᅳ dihydroquinoline-3-carboxylic acid (1 麵 ol) was dissolved in DMF (2 mL). DIPEA (3 ′ ol), 2 ′ (4-methoxyphenyl) ethanamine (1.5 mmol) and PyBop (2 ′ ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 208 (yield = 63%).
¾ 證 (400MHz, CDC13 )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 합성예 209 ： l-(4-메톡시벤질) N-(4-메록시펜에틸 )-2-옥소 -1，2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ 證 (400 MHz, CDC1 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 (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 Synthesis Example 209: l- (4-methoxybenzyl) N- (4-methoxyphenethyl) -2-oxo-1-, 2-dihydroquinoline-3-carboxamide
1-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 D F(2 mL)에 용해시켰다. DIPE/ 3瞧 ol), 2- (4- 메톡시페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 麵 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물 을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프 로 정제하여 합성예 209 화합물을 수득하였다 (수율 = 68%)  1- (4-Methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in D F (2 mL). DIPE / 3 ′ ol), 2- (4-methoxyphenyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 209 (yield = 68%)
¾ NMR(400MHz, CDC13)5 8.03(sᅳ 1H, -NH), 8.0(s, 1H, -NH), 7.36(d,¾ NMR (400 MHz, CDC1 3 ) 5 8.03 (s ᅳ 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(iii, 2H), 3.3(s, 2H), 2.83(m, 2H) 2.54(s, 3H). MASS=442.19 합성예 210 ： l-(2-(5-하이드록시 -2,3-디하이드로-lH-인덴-2-일)에틸)ᅳN-(4- 메록시펜에틸 )-2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카르복사마이드 1H), 7.31 (t, 1H), 7.18 (dd, 2H), 7.14 (m, 3H), 6.94 (m, 4H) '3.83 (s, 3H), 3.55 (iii, 2H), 3.3 (s, 2H ), 2.83 (m, 2 H) 2.54 (s, 3 H). MASS = 442.19 Synthesis Example 210: l- (2- (5-hydroxy-2,3-dihydro-lH-inden-2-yl) ethyl) ᅳ N- (4-methoxyphenethyl) -2-oxo -1,2 ᅳ dihydroquinoline-3-carboxamide
1-(2-(5- (하이드록시메틸) -2， 3-디하이드로 -1H-인덴 -2-일 )에틸 )-2- 옥소 -1,2-디하이드 '로퀴놀린 -3-카복실릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3睡 ol), 2-(p-를일)에타나민 (1.5 讓 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 210 화합물을 수득하였다 (수율 =63%). 1- (2- (5- (hydroxymethyl) -2,3-dihydro-1H-inden-2-yl) ethyl) -2-oxo-1,2-dihydro ' roquinoline-3-carboxylic Acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 ′ ol), 2- (p-ylyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 210 (Yield = 63%).
¾ 丽 R (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ δ R (400MHz, CDC1 3 ) 6 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),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 합성예 211 ： 1-((2，3-디하이드로 -1Hᅳ인덴 -5-일)메틸) -N-(4ᅳ메특시펜에틸) - 2-옥소 1， 2-디하이드로퀴놀린 -3-카르복사마이드 2.64 (m, 5 H). MASS = 482.22 Synthesis Example 211: 1-((2,3-dihydro-1H'inden-5-yl) methyl) -N- (4'mesophenifeneethyl)-2-oxo 1, 2-dihydroquinoline-3 Carboxamide
1- (나프탈렌 -2-일메틸 )-2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 匪 ol)를 DMF(2 mL)에 용해시켰다. DIPEM3隱 ol), 2-(4-메특시페닐) 에타나민 (1.5 隱 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 × ol) was dissolved in DMF (2 mL). DIPEM3 'ol), 2- (4-methoxyphenyl) ethanamine (1.5 隱 ol) and PyBop (2 醒 ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 211 (yield = 60%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 212 ： 1-(2-(2，3-디하이드로 -IH-인덴 -5-일)에틸) -N-(4-메톡시펜에틸)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 Synthesis Example 212: 1- (2- (2,3-Dihydro-IH-indene-5-yl) ethyl) -N- (4-methoxyphenethyl)
-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(2， 3—디하이드로 -1Hᅳ인덴 -5-일)에틸 )-2-옥소-1 , 2-디하이드로퀴 놀린 -3-카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA 1- (2- (2,3—dihydro-1H ᅳ inden-5-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 讓 ol) was added to DMF. (2 mL). DIPEA
(3隱 ol), 2-(4-메톡시페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 212 화합물을 수득하였다 (수율 =68%). (3 ′ ol), 2- (4-methoxyphenyl) ethanamine (1.5 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 212 (yield = 68%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 6 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, IH), 6.94(m, 4H) , 4.94(s, 2H) , 4.27(s, 2H), 3.83(s, 3H), 3.55(m, 2H),NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (m, 3H), 7.14 (t, IH), 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 합성예 215 ： N-(4-브로모벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드 2.83 (m, 7 H). MASS = 466.23 Synthesis Example 215: N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
2—옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭. 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3麵 οί), (4-브로모페닐)메타나민 (1.5 画 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 麵 οί), (4-bromophenyl) methanamine (1.5 画 ol) and PyBop (2 mmol) was 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 215 (yield = 61%).
¾ 匪 R (400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ 匪 R (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H,-
NH), 8.0 (s, 1H, — NH), 7.36(d, iH), 7.31(t, 1H) , 7.25(dd, 2H), 7.14(t, 1H), 6.87(dd, 2H) , 4.34(m, 2H). MASS=356.02 합성예 216 ： 1ᅳ벤조일 -N-(4-브로모벤질) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 NH), 8.0 (s, 1H, — NH), 7.36 (d, iH), 7.31 (t, 1H), 7.25 (dd, 2H), 7.14 (t, 1H), 6.87 (dd, 2H), 4.34 ( m, 2H). MASS = 356.02 Synthesis Example 216 ： 1′benzoyl-N- (4-bromobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
2-옥소 -1-(2-옥소 -2-페닐에틸)ᅳ 1， 2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3隱 ol), (4-브로모페닐) 메타나민 (1.5 麵 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 로 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' ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), (4-bromophenyl) metanamin (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 216 (yield = 39%).
¾ 醒 R (400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ 醒 R (400 MHz, CDC1 3 ) 5 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,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 합성예 217 ： N-(4—브로모벤질) -l-(4-메록시벤조일 ).2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 4H), 6.87 (dd, 2H), 4.34 (m, 2H), MASS = 460.04. Synthesis Example 217: N- (4-bromobenzyl) -l- (4-methoxybenzoyl). 2-oxo-1, 2-dihydroquinoline-3-carboxamide
1ᅳ (2-(4-메록시페닐) -2—옥소에틸 )ᅳ2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3瞧 ol), (4- 브로모페닐)메타나민 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 217 화합물을 수득하였다 (수율 = 63%) .  1 '(2- (4-Methoxyphenyl) -2-oxoethyl)' 2'oxo-1,2-dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). . DIPEA (3 ′ ol), (4-bromophenyl) methamine (1.5 mmol) and PyBop (2 ′ ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 217 (yield = 63%).
¾ NMR (400丽 z,CDCl3)S 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, ᅳ NH), 8.0 (s, 1H, -NH), 7.36(d, 1H)ᅳ 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 합성예 218 ： N- -브로모펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 δ z, CDCl 3 ) S 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, ᅳ NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H ᅳ 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 Synthesis Example 218: N-bromophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMFC2 mL)에 용해시켰다. DIPEA(3隱 ol), 2— (4-브로모페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 218 화합물을 수득하였다 (수율 =66%).  2-oxo-l, 2-dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in 2 mL of DMFC. DIPEA (3 ′ ol), 2— (4-bromophenyl) ethanamine (1.5 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 218 (yield = 66%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H) , 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 219 ： N-(4-브로모펜에틸 )-l-(4ᅳ메록시벤질 )-2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 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 Synthesis Example 219 N- (4-bromophenethyl) -l- (4 ᅳ methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1- (2-(4-메톡시페닐 )ᅳ2-옥소에틸) -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3- 카복실릭 애시드 (1 讓 01)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol ) , (4- 브로모페닐)메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토 그래프로 정제하여 합성예 219 화합물을 수득하였다 (수율 =60%). Was dissolved in 1- (2- (4-methoxyphenyl) eu 2-oxoethyl) -2-oxo-1, 2 eudi dihydro-quinoline-3-carboxylic acid (1讓0 1) of DMF (2 mL) . DIPEA (3 mmol), (4-bromophenyl) methamine (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 219 (yield = 60%).
¾ 蘭 R(400MHz, CDC13) 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 합성예 220 ： N-(4-브로모펜에틸 )-2—옥소 -l-(4- (트리플루오로메특시)벤조일) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 蘭 R (400MHz, CDC1 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), 3..3 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). MASS-490.05 Synthesis Example 220: N- (4-bromophenethyl) -2—oxo-l- (4- (trifluoromepoxy) benzoyl) -1,2-dihydroquinoline-3-carboxamide
2-옥소 -1ᅳ (2-옥소 -2-(4- (트리플루오로메톡시 )페닐)에틸) -1， 2ᅳ디하이 드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3醒 ol), 2-(4—브로모페닐)에타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득 한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 202 화합물을 수득하였다 (수율 =68«. 2-oxo-1 '(2-oxo-2- (4- (trifluoromethoxy) phenyl) ethyl) -1,2'dihydrodroquinoline-3-carboxylic acid (1' ol) was added to DMF (2 mL). )). DIPEA (3 ′ ol), 2- (4—bromophenyl) ethanamine (1.5 mmol) and PyBop (2 ′ ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. purchase One residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 202 (yield = 68 «.
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14 3， 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 합성예 222 ： N-(4-클로로벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드) ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 3, 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 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 麵 οθ, (4-클로로페닐)메타나민 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 麵 οθ, (4-chlorophenyl) methamine (1.5 mmol) and PyBop (2 睡 ol) were added to the reaction mixture, the mixture was stirred at room temperature for 3 hours. Extraction with acetate and water then purification with silica gel chromatography gave Synthesis Example 222 compound (yield = 46%).
¾ 應 R (400MHz, CDC13)6 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 합성예 223 ： N-(4-클로로벤질 )-1ᅳ(4-에틸벤조일) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾應R (400MHz, CDC1 3 ) 6 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 Synthesis Example 223 N- (4-chlorobenzyl) -1 '(4-ethylbenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-에틸벤조일) -2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (4-클로로페닐) 메타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 'ol), (4-chlorophenyl) metanamin (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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 223 (yield = 56%).
¾ 丽 R (400MHz, CDC13)6 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 합성예 224 ： N-(4-클로로벤질) -l-(4-하이드록시벤조일) -2-옥소— 1,2-디하이 드로퀴놀린 -3-카르복사마이드 l-(4-하이드록시벤조일) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애 시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), (4-클로로페닐) 메타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 224 화합물을 수득하였다 (수율 =58%). ¾ δ R (400MHz, CDC1 3 ) 6 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 Synthetic Example 224: N- (4-chlorobenzyl) -l- (4-hydroxybenzoyl) -2-oxo- 1,2-dihydrodroquinoline-3-carboxamide 1- (4-hydroxybenzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), (4-chlorophenyl) metanamin (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 224 (yield = 58%).
¾ NMR (400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H) , 8.03(s, 1H, - NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.31(1;， 1H) , 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-카르복사 마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H,-NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (1; 1H), 7.25 (m, 4H), 7.14 (m, 3H), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 432.09 Synthesis 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 隱 ol), 2-(4-클로로페닐)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하 다. 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 mmol) are 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 225 (yield = 67%).
¾ NMR( 400MHz, CDC13)5 8.28(sᅳ 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)ᅳ 2.83(m, 2H). MASS=326.08 합성예 226 ： N-(4-클로로펜에틸 )-l-(4ᅳ메록시벤질 )-2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s ᅳ 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) ᅳ 2.83 (m, 2H). MASS = 326.08 Synthesis Example 226 N- (4-chlorophenethyl) -l- (4 ᅳ methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 薩 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 Compound (1xol) 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 226 (yield = 57%).
¾ 匪 R OOMHz, CDC13)5 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 합성예 227 ： l-(4-클로로벤조일) -N-(4-클로로펜에틸 )-2-옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 匪 R OOMHz, CDC1 3 ) 5 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, 3 H). MASS = 446.14 Synthetic Example 227: l- (4-chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-클로로벤조일 )-2-옥소 -1，2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 1- (4-chlorobenzoyl) -2-oxo-1- 1,2-dihydroquinoline-3-carboxylic acid
(1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(1.5 薩 ol), 2- (4- 클로로페닐)에타나민 (1.5 麵 ol) 및 PyBop(2 腿 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 227 화합물을 수득하였다 (수율 = 65%) . (1 μl) was dissolved in DMF (2 mL). DIPEA (1.5 μl ol), 2- (4-chlorophenyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 227 (yield = 65%).
¾ 賺 (400MHz, CDC13)6 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 합성예 228 ： N-(4-클로로펜에틸 )-1ᅳ(4-아이오도벤조일) -2-옥소 -1,2-디하이 드로퀴놀린 -3-카르^사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 228 ： N- (4-chlorophenethyl) -1 '(4-iodobenzoyl) -2-oxo-1,2-dihydrodroquinoline-3-car ^ amide
1- (4-아이오도벤조일 )-2-옥소-1， 2-디하이드로퀴놀린 -3ᅳ카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2-(4-클로로 페닐)에타나민 (1.5 麵 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제 하여 합성예 228 화합물을 수득하였다 (수율 =67%).  1- (4-iodobenzoyl) -2-oxo-1, 2-dihydroquinoline-3'carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-chloro phenyl) ethanamine (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 228 (yield = 67%).
¾ NMR (400MHz, CDC13)6 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 합성예 229 ： N-(4-클로로펜에틸 )-l-(4-니트로벤조일 )-2-옥소 -1,2-디하이드 로퀴놀린 -3ᅳ카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 229: N- (4-chlorophenethyl) -l- (4-nitrobenzoyl) -2-oxo-1,2-dihydroquinoline-3'carboxamide
1-(4-니트로벤조일 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 2-(4-클로로페닐) 에타나민 (1.5 隨 ol) 및 PyBop(2 薩 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-chlorophenyl) ethanamine (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 229 (yield = 56%).
¾ 薩 (400MHz, CDC13)6 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 합성예 230 ： l-(4-아미노벤조일) -N-(4-클로로펜에틸 )-2-옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 薩 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 230: l- (4-aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-아미노벤조일 )-2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복실릭 애시드 1- (4-aminobenzoyl) -2-oxo-1,2 ᅳ dihydroquinoline-3-carboxylic acid
(1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-클로로페닐) 에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 230 화합물을 수득하였다 (수율 =45%). (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-chlorophenyl) ethanamine (1.5 mmol) and PyBop (2 μL ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis 230 (Yield = 45%).
¾ NMR (400MHz, CDC13)6 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 합성예 232 ： N-(4-풀루오로벤질 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 232: N- (4-Pluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 醒 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), (4ᅳ플루오로페닐)메타나민 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 '정제하여 합성예 232 화합물을 수득하였다 (수율 =59%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), (4'fluorophenyl) methamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture. The mixture was stirred at silver for 3 hours. The obtained residue was extracted with ethyl acetate and water. After silica gel chromatography 'purified to give the compound of Synthesis Example 232 (yield = 59%).
¾ 匪 R (400MHz, CDC13)5 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 합성예 233 ： N-(4-폴루오로벤질 )-l-(4-포르밀벤조일 )-2-옥소 -1，2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 233: N- (4-fluorobenzyl) -l- (4-formylbenzoyl) -2-oxo-1,2-dihydro Loquinoline-3-carboxamide
1-(4-포르밀벤조일 )-2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 議 ol), (4-풀루오로페닐) 메타나민 (1.5 麵 ol) 및 PyBop(2 麵 ol)를 반웅 혼합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물론 추출하였다. 이후 실리카겔 크로마토그래프로 정제하 여 합성예 233 화합물을 수득하였다 (수율 =49%).  1- (4-formylbenzoyl) -2-oxo-1, 2-dihydroquinoline® 3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), (4-fulurophenyl) metanamin (1.5' ol) and PyBop (2 'ol) 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 of course. Then purified by silica gel chromatography to give the compound of Synthesis Example 233 (yield = 49%).
¾ 匪 R(400MHz, CDC13)6 8.28 (s, 1H), 8.14 (s, 1H) , 8.03 (s, 1H, -NH), 8.0 (sᅳ 1H, -NH), 7.36 (in, 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 합성예 234 ： l-(4-시아노벤조일) -N-(4-플루오로벤질 )— 2ᅳ옥소 -1,2-디하이드 로 퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s ᅳ 1H, -NH), 7.36 (in, 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 Synthesis Example 234: l- (4-cyanobenzoyl) -N- (4-fluorobenzyl) — 2oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-시아노벤조일 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPE 3 麵 ol), (4-플루오로페닐) 메타나민 (1.5 瞧 ql) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제 하여 합성예 234 화합물을 수득하였다 (수율 =59%). 1- (4-cyanobenzoyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPE 3 麵 ol), (4-fluorophenyl) metanamin (1.5 瞧q l) and PyBop (2 睡 ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 234 (yield = 59%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 6 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,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 합성예 235 (N-(4-풀루오로벤질 )-l-(4- (메틸티오)벤조일 )-2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드) 1H), 6.87 (dd, 2H), 4.34 (m, 2H). MASS = 425.12 Synthesis Example 235 (N- (4-Pluorobenzyl) -l- (4- (methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide)
1ᅳ(4- (메틸티오)벤조일 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애 시드 (1 謹 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (4-플루오로페닐) 메타나민 (1.5醒 ol) 및 PyBop(2 娜 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 235 화합물을 수득하였다 (수율 =56%). ¾ NMR( 400MHz, CDC13) 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 합성예 236 ： N-(4-플루오로펜에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드) 1 '(4- (Methylthio) benzoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1' ol) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), (4-fluorophenyl) metanamin (1.5 醒 ol) and PyBop (2 ol ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 235 (yield = 56%). ¾ NMR (400 MHz, CDC1 3 ) 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 Synthesis Example 236: N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide)
합성예 25'화합물(1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에타나민 (1.5 画 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 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 ' Compound (1 ' ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 236 (yield = 65%)
¾ NMR( 400MHz, CDC13)5 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 합성예 237 ： N-(4-플루오로펜에틸) -l-(4-메톡시벤질) -2ᅳ옥소 -1，2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 237: N- (4-fluorophenethyl) -l- (4-methoxybenzyl) -2oxoo-1,2-dihydroquinoline-3-carboxamide
합성예 26 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), 2-(4-플루오로페닐)에타나민 (1.5隱 ol) 및 PyBop(2讓 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 상온에서 교반하고 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 237 화합물을 수득하였다 (수율 =66%).  Synthesis Example 26 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-fluorophenyl) ethanamine (1.5' ol) and PyBop (2 'ol) 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. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 237 (yield = 66%).
¾ NMR( 400MHz, CDC13)6 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(1;， 1H), 6.94(dd, 2H), 3.55(m, 2H), 2.83(m, 2H) . MASS=430.17 합성예 238 ： l-(4- (디플루오로메틸)벤조일) -N-(4-플루오로펜에틸) -2-옥소- 1 ,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 (1 ;; 1H), 6.94 (dd, 2H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 430.17 Synthetic Example 238: l- (4- (difluoromethyl) benzoyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4- (디플루오로메틸)벤조일 )-2ᅳ옥소-1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 讓 ol)를 DMF(2mL)에 용해시켰다. DIPEA(3 麵 ol), 2— (4- 플루오로페닐)에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하 여 합성예 238 화합물을 수득하였다 (수율 =67%). 1- (4- (difluoromethyl) benzoyl) -2 ᅳ oxo-1, 2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 麵 ol), 2— (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture. Add and stir for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 238 (yield = 67%).
¾ 賺 (400MHz, CDC13)8 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 합성예 239 ： N-(4-플루오로펜에틸) -l-(2-(4-메록시페닐)아세틸 )-2-옥소 -1,2 ᅳ디하이드로퀴놀린 -3-카르복사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 8 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 Synthesis Example 239: N- (4-fluorophenethyl) -l- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2 ᅳ dihydroquinoline-3-carboxamide
1-(2-(4-메록시페닐)아세틸 )-2-옥소 -1，2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 2-(4-플루 오로페닐)에타나민 (1.5 画 ol) 및 PyBop(2 闘 ol)를 반웅 흔합물에 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 瞧 ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-fluorophenyl) ethanamine (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 239 (yield = 68%).
¾ NMR (400MHz, CDC13)5 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 합성예 240 ： N-(4-플루오로펜에틸) -2ᅳ옥소 -l-(2-(4- (트리플루오로메록시) 페닐 )아세틸 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 240: N- (4-fluorophenethyl) -2-hexoxo-l- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1, 2-dihydroquinoline-3 Carboxamide
2-옥소 -1-(2-(4- (트리플루오로메특시)페닐)아세틸 )-1，2-디하이드로 퀴놀린 -3-카복실릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), 2-(4-플루오로페닐)에타나민 (1.5睡 ol) 및 PyBop(2隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피 로 정제하여 합성예 240 화합물을 수득하였다 (수율 =63%)  Dissolve 2-oxo-1- (2- (4- (trifluoromepoxy) phenyl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid (1 画 ol) in DMF (2 mL) I was. DIPEA (3xol), 2- (4-fluorophenyl) ethanamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography to obtain the compound of Synthesis 240 (Yield = 63%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, - NH), 8.0 (s, 1H， - NH), 7.36(d, 1H) , 7.31(1:， 1H), 7.18(m, 4H), 7.14(t, 1H), 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-카르복사마이드 합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), (4-에틸페닐)메타나민 (1.5匪 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 241 화합물을 수득하였다 (수율 = 55%) . ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-NH), 8.0 (s, 1H,-NH), 7.36 (d, 1H), 7.31 (1 :， 1H), 7.18 (m, 4H), 7.14 (t, 1H), 6.94 (m, 4H), 3.55 (m, 2H), 2.83 (m, 4H). MASS = 512.14 Synthesis Example 241 N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 A compound (1 'ol) was dissolved in DMF (2 mL). DIPEA (3xol), (4-ethylphenyl) methamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 241 (yield = 55%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, - NH), 8.0 (s. ΙΗ,,ΝΗ), 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 합성예 242 ： N-(4-에틸벤질) -l-(2-(4-하이드록시페닐)아세틸 )-2-옥소 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-NH), 8.0 (s.ΙΗ ,, ΝΗ), 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 Synthesis Example 242: N- (4-ethylbenzyl) -l- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4-하이드록시페닐)아세틸) -2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3- 카복실릭 애시드 (1 瞧 01)를 DMF(2 mL)에 용해시켰다. DIPEAC3 画 ol), (4- 에틸페닐)메타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 242 화합물을 수득하였다 (수율 =67%). 1- (2- (4-hydroxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline® 3- carboxylic acid (1 × 0 1) was dissolved in DMF (2 mL). DIPEAC3 画 ol), (4-ethylphenyl) methamine (1.5 隱 ol) and PyBop (2 隱 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 242 (yield = 67%).
¾ 醒 R (400MHz, CDC13)5 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 합성예 243 ： N-(4-에틸벤질) -l-(2— (4-에틸페닐)아세틸 )-2ᅳ옥소 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 ¾ 醒 R (400 MHz, CDC1 3 ) 5 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 Synthetic Example 243: N- (4-ethylbenzyl) -1- (2— (4-ethylphenyl) acetyl) -2ioxo-1,2-dihydrodroquinoline-3 Carboxamide
1ᅳ(2-(4-에틸페닐)아세틸) -2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (4-에틸페닐) 메타나민 (1.5 瞧이) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 243 화합 물을 수득하였다 (수율 =46%). ¾ NMR (400MHz, CDC 13 )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 합성예 244 ： N-(4-에틸벤질) -l-(2-(4-플루오로페닐)아세틸 )-2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 1 '(2- (4-ethylphenyl) acetyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxylic acid (1' ol) was dissolved in DMF (2 mL). DIPEA (3 IX ol), (4-ethylphenyl) metanamin (1.5 IX) and PyBop (2 IX ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 243 (yield = 46%). ¾ NMR (400 MHz, CDC 1 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, 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, 6 H). MASS = 452.21 Synthesis Example 244: N- (4-ethylbenzyl) -l- (2- (4-fluorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1_(2-(4-플루오로페닐)아세틸 )— 2-옥소ᅳ 1 , 2-디하이드로퀴놀린 -3-카복 실릭애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3誦 ol), (4-에틸 페닐)메타나민 (1.5 讓 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 244 화합물을 수득하였다 (수율 =46%).  1_ (2- (4-fluorophenyl) acetyl)-2-oxoxol 1, 2-dihydroquinoline-3-carboxy silic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), (4-ethyl phenyl) methamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 244 (yield = 46%).
¾NMR( 400MHz, CDC13 )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), ¾NMR (400MHz, CDC13) 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(tn, 3H).6.98 (dd, 2H), 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (tn, 3H).
MASS=442.17 합성예 245 ： l-(2-(4-클로로페닐)아세틸) -Nᅳ (4-에틸벤질) -2-옥소 -1,2-디하 이드로퀴놀린 -3-카르복사마이드 MASS = 442.17 Synthetic Example 245: l- (2- (4-chlorophenyl) acetyl) -N '(4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1— (2-(4-클로로페닐)아세틸 )-2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3ᅳ 카복실릭 애시드 (1 隱01)를 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), (4- 에틸페닐)메타나민 (1.5隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 245 화합물을 수득하였다 (수율 =49%). 1— (2- (4-Chlorophenyl) acetyl) -2-oxo-1, 2-dihydroquinoline® 3 ′ carboxylic acid (1 × 0 1) was dissolved in DMF (2 mL). DIPEA (3xol), (4-ethylphenyl) methamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 245 (yield = 49%).
¾ NMR(400MHz, CDC13)5 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)ᅳ 6.98(dd, 2H)., 4.34(m, 2H), 3.4(s, 2H), 2.60(m, 2H), 1.25(m, 3H). MASS= 458.14 합성예 246 ： N-(4-에틸벤질) -1-(2-(4-아이오도페닐)아세틸 )-2-옥초 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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) ᅳ 6.98 (dd, 2H)., 4.34 (m, 2H), 3.4 (s, 2H), 2.60 (m, 2H), 1.25 (m, 3 H). MASS = 458.14 Synthesis Example 246: N- (4-ethylbenzyl) -1- (2- (4-iodophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4ᅳ아이오도페닐)아세틸 )-2ᅳ옥소 -1 , 2ᅳ디하이드로퀴놀린 -3-카복 실릭애시드 (1 難 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), (4-에틸 페닐)메타나민 (1.5 隱 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 246 화합물을 수득하였다 (수율 =67%).  1- (2- (4'iodophenyl) acetyl) -2ioxo-1,2'dihydroquinoline-3-carboxy silic acid (1 'ol) was dissolved in DMF (2 mL). DIPEAC3 隱 ol), (4-ethyl phenyl) methamine (1.5 隱 ol) and PyBop (2 醒 ol) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 246 (yield = 67%).
¾ 蘭 (400丽 z, CDC13)6 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 합성예 247 ： N-(4-에틸벤질) -l-(2-(4-니트로페닐)아세틸 )-2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ 400 (400 d z, CDC1 3 ) 6 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, 3 H). MASS = 550.08 Synthesis Example 247 N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4-니트로페닐)아세틸) -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), (4- 에틸페닐)메타나민 (1.5 mmol) 및 PyBop(2 誦 ol)를 반웅 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 에틸 아세테이트 및 물로 추출하였다 · '' 이후 실리카겔 크로마토그래프로 정제하여 합성예 247 화합물을 수득하였다 (수율 =44%). ' 1- (2- (4-nitrophenyl) acetyl) -2-oxoox 1, 2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), (4-ethylphenyl) methamine (1.5mmol) and PyBop (2xol) 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 then purified by silica gel chromatography to give Synthesis Example 247 compound (Yield = 44%). '
¾ NMR( 400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, ᅳ 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 합성예 248 ： l-(2-(4-아미노페닐)아세틸) -N-(4-에틸벤질) -2-옥소 -1,2-디하 이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, ᅳ 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 Synthetic Example 248: l- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4-아미노페닐)아세틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), (4- 에틸페닐)메타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에탈 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 248 화합물을 수득하였다 (수율 =56¾ . 1- (2- (4-aminophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 画 ol) was dissolved in DMF (2 mL). DIPEA (3 讓 ol), (4-ethylphenyl) methamine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture Stir at room temperature for 3 hours. The obtained residue was extracted with ethal acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 248 (yield = 56¾.
¾ 丽 (400MHz, CDC13)5 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 합성예 249 ： N-(4-에틸펜에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마 이드 ¾ δ (400MHz, CDC1 3 ) 5 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, 2 H), 1.25 (m, 3 H). MASS = 439.19 Synthesis Example 249: N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隠 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에타나민 (1.5 睡 ol) 및 PyBop(2 國 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 μl ol) and PyBop (2 ol ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 249 (yield = 45%).
¾ 匪 R OOMHz, CDC13)5 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 합성예 250 ： N-(4-에틸펜에틸) -l-(2-(4-포르밀페닐)아세틸 )-2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R OOMHz, CDC1 3 ) 5 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, 3 H). MASS = 320.15 Synthesis Example 250: N- (4-ethylphenethyl) -1-(2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4-포르밀페닐 )아세틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4- 에틸페닐)에타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 250 화합물을 수득하였다 (수율 =44%).  1- (2- (4-formylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3'carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph to give the compound of Synthesis 250 (yield = 44%).
¾ NMR (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, 一 丽)， 8.0 (s. 1H, NH), 7.36(d, 1H), 7.31(t, 1H), 7.18(m, 4H) , 7.14(m,¾ NMR (400MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, 一 丽), 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 합성예 251 ： l-(2-(4-시아노페닐)아세틸) -N-(4-에틸펜에틸) -2-옥소 -1,2-디 하이드로퀴놀린— 3ᅳ카르복사마이드 3H), 6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 3H), 1.25 (s, 3H). MASS = 466.19 Synthesis Example 251: l- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline—3′carboxamide
1-(2-(4-시아노페닐)아세틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- (4- 에틸페닐)에타나민 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 251 화합물을 수득하였다 (수율 =56%).  1- (2- (4-cyanophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-ethylphenyl) ethanamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 251 (yield = 56%).
¾ NMR( 400MHz, CDC13)6 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 합성예 252 ： N-(4-에틸펜에틸) 1— (2-(4- (메틸티오)페닐)아세틸 )-2-옥소-¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 252: N- (4-ethylphenethyl) 1— (2- (4- (methylthio) phenyl) acetyl) -2-oxo-
1 , 2-디하이드로퀴놀린ᅳ 3-카르복사마이드 1,2-dihydroquinoline ᅳ 3-carboxamide
1-(2-(4- (메틸티오)페닐)아세틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2- (4-에틸페닐)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크 S마토그래프로 정제하여 합성예 25 화합물을 수득하였다 (수을 =57%).  1- (2- (4- (methylthio) phenyl) acetyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1xol) 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 obtained residue was extracted with ethyl acetate and water. Subsequently, the silica gel was purified by S-graphograph to obtain a compound of Synthesis Example 25 (number = 57%).
¾NMR(400MHz, CDC13)5 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),¾NMR (400MHz, CDC1 3 ) 5 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) .6.98 (dd, 2H), 4.34 (m, 2H), 3.60 (m, 4H), 2.60 (m, 2H), 1.25 (s, 6H).
MASS= 484.18 합성예 253 ： l-(2-(4- (디플루오로메틸)페닐)아세틸) -N-(4-에틸펜에틸) -2- 옥소 -1,2-디하이드로퀴놀린 -3ᅳ카르복사마이드 MASS = 484.18 Synthesis Example 253: l- (2- (4- (difluoromethyl) phenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3 ' Carboxamide
1-(2-(4- (디플루오로메틸)페닐)아세틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-에틸페닐)에하나민 (1.5 画 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제 하여 합성예 252 화합물을 수득하였다 (수율 =42%). 1- (2- (4- (difluoromethyl) phenyl) acetyl) -2-oxo-1, 2-dihydroquinoline 3-Carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-ethylphenyl) ananamin (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the Synthesis Example 252 compound (yield = 42%).
¾ NMR( 400MHz, CDC13)5 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 합성예 254 N-(4-하이드록시벤질) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 254 N- (4-hydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 讓 ol)올 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), 4- (아미노메틸)페놀 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1'ol) ol was dissolved in DMF (2 mL). DIPEAC3 隱 ol), 4- (aminomethyl) phenol (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 254 (yield = 66%).
NMR( 400MHz, CDC13)5 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 합성예 255 ： N-(4-하이드록시벤질) -l-(4- (메틸티오)벤질) -2-옥소 -1,2-디하 이드로퀴놀린 -3-카르복사마이드) NMR (400MHz, CDC1 3 ) 5 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 Synthesis Example 255: N- (4-hydroxybenzyl) -l- (4- (methylthio) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide)
1-(4- (메틸티오)벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시 드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3議 ol), 4- (아미노메틸) 페놀 (1.5画 ol) 및 PyBop(2 mmol)를 반웅 혼합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 255 화합물을 수득하였다 (수율 =64%).  1- (4- (Methylthio) benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4- (aminomethyl) phenol (1.5' ol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 255 (yield = 64%).
¾ 匪 R (400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, ᅳ¾ 匪 R (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H, ᅳ
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, 1Hᅳ -OH), 3.3(S, 2H), 4.34(m, 5H) . MASS= 430.14 합성예 256 ： N-(4-하이드록시벤질) -1-(4ᅳ (메틸티오)펜에틸 )-2-옥소 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 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 ᅳ -OH), 3.3 (S, 2H), 4.34 (m, 5H). MASS = 430.14 Synthesis Example 256: N- (4-hydroxybenzyl) -1- (4 '(methylthio) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1- ( 4- (메틸티오)펜에틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애 시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 醒 ol), 4— (아미노메틸) 페놀 (1.5 mmol) 및 PyBop(2 麵 ol)를 반응 흔합물에 첨가하고 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 256 화합물을 수득하였다 (수율 =68%).  1- (4- (methylthio) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEAC3 醒 ol), 4— (aminomethyl) phenol (1.5 mmol) and PyBop (2 麵 ol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 256 compound (yield = 68%).
¾ 匪 R(400MHz, CDC13)6 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 합성예 257 ： N-(4-하이드록시벤질)— 2-옥소 -l-(4- (트리플루오로메톡시)펜 에틸) -1 , 2-디하이드로퀴놀린 -3ᅳ카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 257 N- (4-hydroxybenzyl)-2-oxo-l- (4- (trifluoromethoxy) phenethyl) -1,2-dihydroquinoline-3'carboxamide
2-옥소 -1-(4- (트리플루오로메록시 )펜에틸 )-1， 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1讓 ol)를 DMF(2 mL)에 용해시켰다. DIPE 3 醒 ol), 4- 2-oxo-1- (4- (trifluoromethoxy) phenethyl) -1, 2-dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPE 3 醒 ol), 4-
(아미노메틸)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 에틸 아세테이트 및 물로 추출하였다. ' 이후 실리카 겔 크로마토그래프로 정제하여 합성예 257 화합물을 수득하였다 (수율 =72%). (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. 'Then purified by silica gel chromatography to give the compound of Synthesis Example 257 (yield = 72%).
¾ 蘭 (400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ 蘭 (400 MHz, CDC1 3 ) 5 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 합성예 258 ： Nᅳ (4-하이드록시펜에틸) -2-옥소 -1，2-디하이드로퀴놀린 -3- 카르복사마이드 합성예 25 화합물 (1 薩 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸)페놀 (1.5 誦 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에탈 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 258 화합물을 수득하였다 (수율 =70%). 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 Synthesis Example 258: N '(4-hydroxyphenethyl) -2-oxo -1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) phenol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethal acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 258 (yield = 70%).
¾ 匿 R(400MHz, CDC13)6 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 합성예 259 ： N-(4-하이드톡시펜에틸) -l-(4-메록시펜에틸 )-2-옥소 -1，2- 디하이드로퀴놀린 -3—카르복사마이드 ¾ 匿 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 259: N- (4-hydroxyphenethyl) -1- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3—carboxamide
1- ( 4-메특 J펜에틸 ) -2-옥소 - 1 , 2-디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2- 아미노에틸)페놀 (1.5 mmol) 및 PyBop (2扁 ol)를 반웅 흔합물에 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-Methope J-phenethyl) -2-oxo-1, 2-dihydroquinoline® 3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) phenol (1.5 mmol) and PyBop (2 ′ ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 259 (yield = 47%).
¾ 蘭 R(400MHz, CDC13)6 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, IH, -OH), 3.55(m, 2H) , 3.3(s, 2H), 2.97(s, 2H), 2.83(m, 5H) . MASS=442.19 합성예 260 ： N-(4-니트로벤질) -2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카르복사마 이드 ¾ 蘭 R (400MHz, CDC1 3 ) 6 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, IH, -OH), 3.55 (m, 2H), 3.3 (s, 2H), 2.97 (s, 2H), 2.83 (m, 5H). MASS = 442.19 Synthesis Example 260: N- (4-nitrobenzyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide
합성예 25(1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3讓 ol), (4- 니트로페닐)메타나민 (1.5 mmol) 및 PyBop (2瞧 ol)를 반웅 흔합물에 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 μL) was dissolved in DMF (2 mL). DIPEAC3 ′ ol), (4-nitrophenyl) methamine (1.5 mmol) and PyBop (2 ′ ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 260 (yield = 59%).
¾ NM ( 00MHz, CDC13)5 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, -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 합성예 261 ： l-(4-아이오도벤질) -N-(4-니트로벤질) -2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ NM (00 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH, -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 Synthesis Example 261: l- (4-iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-아이오도벤질 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 薩 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), (4- 니트로페닐)메타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하 고 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 薩 ol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), (4-nitrophenyl) methamine (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. Then purified by silica gel chromatography to give the compound of Synthesis Example 261 (yield = 67%).
¾ 蘭 (400MHz, CDC13)6 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 합성예 262 ： l-(4-아이오도펜에틸) -N-(4-니트로벤질) -2-옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 蘭 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 262: l- (4-iodophenethyl) -N- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-아이오도펜에틸) -2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카복실릭 애시 드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4- 니트로페닐)메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 'ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4-nitrophenyl) methamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 262 (yield = 47%).
¾ 證 (400丽 z, CDC13)6 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) ,¾ 400 (400 d z, CDC1 3 ) 6 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) .7.14 (t, 1 H), 6.87 (dd, 2H), 4.34 (m, 2H), 3.3 (s, 2H) ( 2.8 (s, 2H).
MASS: 553.05 합성예 263 ： N-(4-니트로펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 MASS : 553.05 Synthesis Example 263: N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-니트로페닐)에타나민 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 263 화합물을 수득하였다 (수율 =45%). Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-nitrophenyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 263 (yield = 45%).
¾ 腿 (400MHz, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, -¾ 腿 (400 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-
NH), 8.0 (s, IH, -NH), 7.36(d, IH), 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 ： 1ᅳ(4-포르밀벤질) -N-(4-니트로펜에틸 )-2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 NH), 8.0 (s, IH, -NH), 7.36 (d, IH), 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 Synthesis Example 264 ： 1 ′ (4-formylbenzyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-포르밀벤질 )-2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3—카복실릭 애시드 ( 1 匪 ol)를 DMF(2 mL)에 용해시켰다. DIPEM3誦 ol), 2-(4-니트로페닐) 에타나민 (1.5. mmol) 및 PyBop(2讀 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 히후 실리카 겔 크로마토그래프로 정제하여 합성예 264 화합물을 수득하였다 (수율 =46%).  1- (4-formylbenzyl) -2-oxo-1, 2'dihydroquinoline-3—carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEM3 'ol), 2- (4-nitrophenyl) ethanamine (1.5. Mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Purification by Hihu silica gel chromatography gave the Synthesis Example 264 compound (yield = 46%).
¾ NMR ( 400MHz, CDC13 )δ 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(m, 3H), 7.31(m, 3H), 7.18(dd, 2H), 7.14(t, IH), 6.94(dd, 2H) , 3.55(m, 2H) ' 3.3(s, 2H) , 2.83(m, 3H). MASS=455.15 합성예 265 ： l-(4-포르밀펜에틸) -N-(4-니트로펜에틸 )-2-옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드  ¾ NMR (400MHz, CDC13) δ 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (m, 3H), 7.31 (m, 3H), 7.18 (dd, 2H), 7.14 (t, IH), 6.94 (dd, 2H), 3.55 (m, 2H) '3.3 (s, 2H), 2.83 (m, 3H). MASS = 455.15 Synthetic Example 265: l- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-포르밀펜에틸 )-2-옥소— 1,2-디하이드로퀴놀린ᅳ 3ᅳ카복실릭 애시드 1- (4-formylphenethyl) -2-oxo— 1,2-dihydroquinoline ᅳ 3 ᅳ carboxylic acid
(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4ᅳ니트로페닐) 에타나민 (1.5 讓 οί) 및 PyBop(2 讓 ol)를 반웅 흔합물에 첨가하고 상온에서(1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4 ᅳ nitrophenyl) ethanamine (1.5 讓 οί) and PyBop (2 讓 ol) were added to the reaction mixture at room temperature
3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 265 화합물을 수득하였다 (수율 =44%). Stir for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 265 (yield = 44%).
¾ 醒 (400MHz, CDC13)6 8.28(s, IH) , 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(m, 3H) , 7.31(t, IH) , 7.18(m, 4H), 7.14(t,¾ 醒 (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -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-카르복사마이드 IH), 6.94 (dd, 2H), 3.55 (m, 4H), 2.83 (m, 5H). MASS = 469.06 Synthesis Example 266: 1- (4- (difluoromethyl) phenethyl) -N- (4-nitrophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4- (디플루오로메틸)펜에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 隨 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3匪 ol), 2- (4- 니트로페닐)에타니 :민 (1.5 麵 ol) 및 PyBop(2 睡 ol)를 반웅 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- (4- (difluoromethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 ′ ol), 2- (4-nitrophenyl) ethanani : min (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 266 (yield = 59%).
¾ NMR( 400MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 5 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)ᅳ 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 합성예 267 ： N-(4-(N,N-디메틸설파모일)벤질) -2ᅳ옥소 -1,2ᅳ디하이드로 퀴놀린 -3-카르복사마이드 NH), 8.0 (s, 1H, -NH), 7.36 (m, 3H), 7.31 (t, 1H) ᅳ 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 Synthesis Example 267: N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-ioxo-1,2'dihydroquinoline-3-carboxamide
합성예 25'화합물 (1 麵 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 4- (아미노메틸)— Ν,Ν-디메틸벤젠설폰아미드 (1.5 画 ol) 및 PyBop(2 mmol)를 반응 흔합물에 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 ' Compound (1Xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4- (aminomethyl) —N, N-dimethylbenzenesulfonamide (1.5' ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 267 (yield = 47%).
¾ NMR( 400MHz, CDC13)5 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 5 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,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 합성예 268 ： l-(4- (디플루오로메틸)벤질) -N-(4-(N,N-디메틸설파모일)벤질) - 2-옥소 -1， 2-디하아드로퀴놀린 -3-카르복사마이드 1H), 4.34 (m, 2H), 2.66 (m, 6H). MASS = 385.11 Synthesis Example 268: l- (4- (difluoromethyl) benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihadroquinoline -3-carboxamide
1ᅳ (4— (디플루오로메틸)벤질 )ᅳ2-옥소 -1,2-디하이드로퀴놀린 -3ᅳ카복 실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 誦 ol), 4- (아미노메틸) -Ν,Ν-디메틸벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 賺 ol)를 반웅 흔합물에 첨가하고 상은에서 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'ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4- (aminomethyl) -N, N-dimethylbenzenesulfonamide (1.5 mmol) and PyBop (2'ol) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethyl acetate and water. Since silica gel Purification by chromatography gave Compound 268 (Yield = 57%).
¾ 醒 (400腿 z, CDC13)5 8.28 (s, 1H), 8.14 (s, 1Η), 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 합성예 269 (N-(4-(N,N-디메틸설파모일)펜에틸 )-2-옥소 -1，2-디하이드로 퀴놀린 -3-카르복사마이드) ¾ 醒 (400 腿 z, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (s, 1Η), 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 Synthesis Example 269 (N- (4- (N, N-dimethylsulfamoyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide)
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-(2-아미노에틸) -Ν,Ν-디메틸벤젠설폰아미드 (1.5 顏 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4- (2-aminoethyl) -Ν, Ν-dimethylbenzenesulfonamide (1.5 顏 ol) and PyBop (2 隱 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 269 (yield = 46%).
¾ 匪 R(400MHz, CDC13)6 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 합성예 270 ： N-(4- (하이드록시메틸)벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis 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)메탄을 (1.5醒 ol) 및 PyBop(2 讓 ol)를 반웅 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 270 화합물올 수득하였다 (수율 =49¾>).  Synthesis Example 25 The compound was dissolved in DMF (5 mL) d [. DIPEA (0.5 mL, 2.7 mmol), (4- (aminomethyl) phenyl) methane (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 270 compound (yield = 49¾>).
¾ MR(400MHz, CDC13)5 8.28 (s, 1H), 8.14 (s, 1H) , 8.03 (s, 1H,¾ MR (400 MHz, CDC1 3 ) 5 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 합성예 271 ： N-(4- (하이드록시메틸)펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린- 3-카르복사마이드 -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 Synthesis Example 271: N- (4- (hydroxymethyl) phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPE/ 3 隱 ol), 4- (2-아미노에틸)페놀 (1.5 醒 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 μL) was dissolved in DMF (2 mL). DIPE / 3 隱 ol), 4- (2-aminoethyl) phenol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 271 (yield = 46%).
¾ 賺 (400MHz, CDC13)6 8.28(s, IH), 8.14(s, IH), 8.03(s, IH, -¾ 賺 (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (s, IH), 8.03 (s, IH,-
ΝΉ), 7.74 (dd, 2H) , 7.51(dd, 2H), 7.36(d, IH) , 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-카르복사마 이드 ΝΉ), 7.74 (dd, 2H), 7.51 (dd, 2H), 7.36 (d, IH), 7.31 (t ( IH), 7.14 (t, IH), 3.65 (s, IH, -OH), 3.55 ( m, 2H), 2.83 (m, 2H) MASS = 322.13 Synthesis Example 272: 2-oxo-N- (4-vinylbenzyl) -1, 2-dihydroquinoline-3-carboxamide
합성예 25 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. D應 (3 隱 ol), (4- 비닐페닐)메타나민 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 272 화합물을 수득하였.다 (수율 =56%). Synthesis Example 25 (1 μL) was dissolved in DMF (2 mL). D '(3' ol), (4-vinylphenyl) methamine (1.5 'ol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 272 . (Yield = 56%).
¾ 匿 (400MHz, CDC13)6 8.28 (s, 1H)， 8.14 (dᅳ IH) , 8.03 (s, IH, -NH), 8.0 (s, IH, -NH), 7.59 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH)， 7.18 (dd, 2H), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH), 4.34 (m, 2H). MASS= 304.12 합성예 273 ： 2-옥소 -N-(4-비닐펜에틸) -1,2-디하이드로퀴놀린 -3_카르복사 마이드 ¾ 匿 (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d ᅳ IH), 8.03 (s, IH, -NH), 8.0 (s, IH, -NH), 7.59 (dd, 2H), 7.36 (d, IH), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH), 4.34 (m, 2 H). MASS = 304.12 Synthesis Example 273 ： 2-oxo-N- (4-vinylphenethyl) -1,2-dihydroquinoline-3_carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 2-(4-비닐페닐)에타나민 (1.5 画 ol) 및 PyBop (2瞧 ol)를 반웅 흔합물에 첨가하^ 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 273 화합물을 수득하였다 (수율 =62%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 2- (4-vinylphenyl) ethanamine (1.5xol) and PyBop (2xol) were added to the reaction mixture ^ and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 273 (yield = 62%).
¾ 圈 R(400MHz, CDC13)5 8.28(s, IH), 8.14(d, IH) , 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.59(dd, 2H), 7.36(d, IH), 7.31(t, IH), 7.18(dd, 2H), 7.14(t, IH), 6.63(s, IH), 5.61(s, IH), 5.18(s, IH), 4.34(m, 2H), 2.83(m, 2H). MASS= 318.14 합성예 274 ： N-메틸 -2-옥소 -N-페닐 -1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-메틸아닐린 (1.5 瞧 ol) 및 PyBop (2画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 274 화합물을 수득하였다 (수율 =66%). ¾ 圈 R (400 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.59 (dd, 2H) , 7.36 (d, IH), 7.31 (t, IH), 7.18 (dd, 2H), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s, IH), 5.18 (s, IH), 4.34 (m, 2 H), 2.83 (m, 2 H). MASS = 318.14 Synthesis Example 274: N-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 A compound (1 'ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-methylaniline (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 274 (yield = 66%).
¾證 (400MHz, CDC13)6 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 합성예 275 ： l-(2,3-디하이드로 -1H—인덴— 2-카르보닐)— N-메틸— 2-옥소— N- 페닐 -1， 2-디하이드로퀴놀린 -3—카르복사마이드 ¾ 證 (400MHz, CDC1 3 ) 6 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 Synthesis Example 275: l- (2,3-dihydro-1H—indene—2-carbonyl) —N-methyl—2-oxo—N-phenyl-1,2-dihydroquinoline-3—car Copyamide
1-(2 , 3-디하이드로 -1H-인덴— 2-카르보닐)— 2-옥소 -1 , 2-디하이드로퀴놀 린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3隱 ol)， 1- (2, 3-dihydro-1H-indene— 2-carbonyl) — 2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) in DMF (2 mL) Dissolved. DIPEA (3 隱 ol) ，
N-메틸아닐린 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. . 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 275 화합물을 수득하였다 (수율 =64¾>). N-methylaniline (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. . The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 275 (yield = 64¾>).
¾ 匪 R(400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH),¾ 匪 R (400 MHz, CDC1 3 ) 6 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),7.81 (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 합성예 276 ： 1-(2-(2，3-디하이드로-111-인덴-2-일)아세틸)-^메틸-2-옥소—^ 페닐 -1,2-디하이드로퀴놀린 -3-카르복사마이드 7.14 (t, 1 H), 3.44 (s, 3 H), 2.67 (m, 5 H). MASS = 422.16 Synthesis Example 276: 1- (2- (2,3-Dihydro-111-inden-2-yl) acetyl) -methyl-2-oxo- ^ phenyl-1,2-dihydroquinoline-3 Carboxamide
1-(2-(2, 3—디하이드로 -1H-인덴 -2-일)아세틸) -2-옥소 -1， 2-디하이드로 퀴놀린—3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N-메틸아닐린 (1.5隱 ol) 및 PyBop(2隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피 를 정제하여 합성예 276 화합물을 수득하였다 (수율 =58%). Ή丽 (400MHz, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, -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(m, 5H). MASS= 436.18 합성예 277. ： 1-(3-(2，3-디하이드로-111-인덴-2-일)프로파노일)-^메틸-2- 옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 1- (2- (2, 3—dihydro-1H-inden-2-yl) acetyl) -2-oxo-1, 2-dihydro quinoline-3-carboxylic acid (1 隱 ol) was added to DMF (2 mL). DIPEA (3xol), N-methylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then silica gel column chromatography was purified to give the compound of Synthesis Example 276 (yield = 58%). Ή 丽 (400MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -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 (m, 5H). MASS = 436.18 Synthesis Example 277 . ： 1- (3- (2,3-Dihydro-111-inden-2-yl) propanoyl)-^ methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carbox Maid
1-(3-(2,3-디하이드로 -1Hᅳ인덴 -2-일)프로파노일) -2-옥소 -1,2-디하이 드로퀴놀린 -3-카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), Nᅳ메틸아닐린 (1.5隱 ol) 및 PyBop(3瞧 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정계 하여 합성예 277 화합물을 수득하였다 (수율 =59%).  1- (3- (2,3-dihydro-1H ᅳ inden-2-yl) propanoyl) -2-oxo-1,2-dihydrodroquinoline-3-carboxylic acid (1 讓 ol) Was dissolved in DMF (2 mL). DIPEA (3 mmol), N ᅳ methylaniline (1.5 隱 ol) and PyBop (3 瞧 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Subsequently, silica gel chromatography was used to obtain the Synthesis Example 277 compound (yield = 59%).
¾ NMR(400顧 z, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, -NH), 7.81 (dd, 2H), 7.43(m, 4H), 7.36(d, IH), 7.31 Cm, 3H), 7.19(t, IH), 7.14(t, IH), 3.44(S) 3H), 3.18(s, 2H), 2.89(s, 2H), 2.67(m, 5H). MASS=450.19 합성예 278 ： N-에틸 -l-(2-(5-메록시 2,3-디하이드로-lH-인덴-2-일)아세틸)- 2_옥소_N_페닐 , 2_디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 顧 z, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.81 (dd, 2H), 7.43 (m, 4H), 7.36 (d, IH), 7.31 Cm, 3H), 7.19 (t, IH), 7.14 (t, IH), 3.44 ( S) 3H), 3.18 (s, 2H), 2.89 (s, 2H), 2.67 (m , 5H). MASS = 450.19 Synthesis Example 278: N- ethyl -l- (2- (5- hydroxy-2,3-dihydro-methoxy -lH- inden-2-yl) acetyl) - 2-oxo-_ _ _ N-phenyl, 2 _ D Hydroquinoline- 3 -carboxamide
1-(2-(5-메록시 -2，3-디하이드로 -1Η-인덴 -2-일)아세틸 )— 2ᅳ옥소 -1,2- 디하이드로퀴놀린 -3-카복실릭 애시드 (1 娜 ol)를 DMF(2 ITIL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린 (1.5瞧 ol) 및 PyBop(2讓 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 278 화합물을 수득하였다 (수율 =72%).  1- (2- (5-methoxy-2,3-dihydro-1Η-inden-2-yl) acetyl) — 2ioxo-1,2-dihydroquinoline-3-carboxylic acid (1 ole ol) ) Was dissolved in DMF (2 ITIL). DIPEA (3 mmol), N-ethylaniline (1.5 Pa ol) and PyBop (2 Pa ol) were added to the reaction mixture and stirred at room temperature for 3 hours at silver. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography to give the compound of Synthesis Example 278 (yield = 72%).
¾ 匪 R OOMHz, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, -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(m, 7H), 2.43(m, 5H). MASS=480.20 합성예 279 ： N—에틸ᅳ l-(2-(5- (메틸티오) -2,3-디하이H로-lH-인덴-2- 일)아세틸 )-2-옥소 -N-페닐 -1，2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R OOMHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -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 (m, 7H), 2.43 (m, 5H). MASS = 480.20 Synthesis Example 279: N-ethyl ᅳ -l- (2- (5- (methylthio) -2,3-dihi-lH-indene-2- Yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
1-(2-(5- (메틸티오) -2， 3-디하이드로 -1H-인덴 -2-일)아세틸 )-2-옥소- 1,2-디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N-에틸아닐린 (1.5隱 ol) 및 PyBop(2隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 279 화합물을 수훅하였다 (수율 =56%).  1- (2- (5- (methylthio) -2,3-dihydro-1H-inden-2-yl) acetyl) -2-oxo- 1,2-dihydroquinoline® 3-carboxylic acid (1醒 ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography, the compound of Synthesis Example 279 was hooked (yield = 56%).
¾ 證 (400MHz, CDC13)5 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 합성예 280 ： N—에틸 -2-옥소 -N-페닐 -l-(2-(5- (트리플루오로메특시) -2,3- 디하이드로 -1H—인덴 -2-일)아세틸 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드 2-옥소ᅳ 1-(2-(5- (트리플루오로메톡시 )-2， 3-디하이드로 -1H-인덴 -2- 일)아세틸 )-1,2-디하이드로퀴놀린— 3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N-에틸아닐린 (1.5隱 ol ) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 280 화합물을 수득하였다 (수율 =56%). ¾ 證 (400 MHz, CDC1 3 ) 5 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 ( MASS = 496.18 Synthesis Example 280 ： N—Ethyl-2-oxo-N-phenyl-l- (2- (5- (trifluoromespecial) -2,3-dihydro-1H—indene-2 -Yl) acetyl) -1, 2-dihydroquinoline-3-carboxamide 2-oxoze 1- (2- (5- (trifluoromethoxy) -2, 3-dihydro-1H-indene-2 -Yl) acetyl) -1,2-dihydroquinoline—3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL) DIPEA (3' ol), N-ethylaniline (1.5 'ol) And PyBop (2 μL ol) 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 then purified by silica gel chromatography to obtain Synthesis Example 280 compound ( Yield = 56%).
¾ 匪 R(400丽 z, CDC13)5 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 ¾ 匪 R (400 d z, CDC1 3 ) 5 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, 2 H). MASS = 534.18
'..  '..
합성예 281 ： N-에틸 -l-(2-(5-하이드록시 -2,3-디하이드로-111-인덴-2-일) 아세틸 )-2-옥소 -N—페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 Synthesis Example 281: N-ethyl -l- (2- (5-hydroxy-2,3-dihydro-111-inden-2-yl) acetyl) -2-oxo-N-phenyl-1, 2-di Hydroquinoline-3-carboxamide
1-(2-(5—하이드록시 -2， 3-디하이드로 -1Hᅳ인덴 -2-일 )아세틸 )-2-옥소- 1ᅳ 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 ιτ )에 용해시켰다. DIPEAC3 隱 ol), N-에틸아닐린 (1.5mmol) 및 PyBop(2画 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피를 정제하여 합성예 281 화합물을 수득하였다 (수율 =58%). 1- (2- (5—hydroxy-2, 3-dihydro-1H ᅳ inden-2-yl) acetyl) -2-oxo-1 ′ 2-dihydroquinoline-3-carboxylic acid (1 瞧ol) was dissolved in DMF (2 τ). DIPEAC3 'ol), N-ethylaniline (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Silica gel column chromatography was then purified to give Synthesis Example 281 compound (yield = 58%).
¾ NMR( 400MHz, CDC13)6 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.i9 합성예 282 ： N-에틸 -l-(2-(5-에틸 -2，3-디하이드로 _1H-인덴 -2-일)아세틸 )-2- 옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3—카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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.i9 Synthesis Example 282: N-ethyl -l- (2- (5-ethyl-2,3-dihydro _1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1, 2-dihydroquinoline-3—carboxamide
1-(2-(5-에틸 -2 3-디하이드로 -1H-인덴— 2 아세틸) -2ᅳ옥소 -1 2- 디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 誦 ol), N-에틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 282 화합물을 수득하였다 (수율 = 67%).  1- (2- (5-ethyl-2 3-dihydro-1H-indene- 2 acetyl) -2 ioxo-1 -2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF (2 mL). DIPEA (3 x ol), N-ethylaniline (1.5 mmol) and PyBop (2 x ol) were added to the reaction mixture and stirred for 3 hours at room temperature. Extraction with water then purification with silica gel chromatography gave Synthesis Example 282 compound (Yield = 67%).
¾ NMR(400MHz, CDC13)6 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 합성예 283 ： N-에틸 -l-(2-(5-폴루오로 -2,3-디하이드로-111—인덴-2-일)아세틸)¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 283: N-ethyl -l- (2- (5-polouro-2,3-dihydro-111—inden-2-yl) acetyl)
-2-옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide
1-(2— (5-플루오로 -2 3-디하이드로 -1H—인덴 -2-일)아세틸) -2-옥소 -1 ,2- 디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), N-에틸아닐린 (1.5讓 ol) 및 PyBop(2mmol )를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피 로 정제하여 합성예 283 화합물을 수득하였다 (수율 =48%).  1- (2— (5-fluoro-2 3-dihydro-1H—inden-2-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 隱 ol) Was dissolved in DMF (2 mL). DIPEAC3 'ol), N-ethylaniline (1.5' ol) 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. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 283 (yield = 48%).
¾ 賺 (400MHz, CDC13)6 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),¾ 賺 (400 MHz, CDC1 3 ) 6 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 합성예 284 ： l-(2ᅳ (5-클로로 -2,3-디하이드로— 1H-인덴 -2-일)아세틸) -N-에틸- 2-옥소ᅳ N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H). MASS = 468.18 Synthesis Example 284: l- (2 '(5-Chloro-2,3-dihydro-lH-inden-2-yl) acetyl) -N-ethyl- 2-oxoze N-phenyl -1, 2 -Dihydroquinoline-3-carboxamide
1-(2-(5ᅳ클로로 -2，3—디하이드로-lH-인덴ᅳ2-일)아세틸)-2ᅳ옥소-l，2- 디하이드로퀴놀린-3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3醒 ol), N-에틸아닐린 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 284 화합물을 수득하였다 (수율 = 47%).  1- (2- (5 ᅳ chloro-2,3—dihydro-lH-indenyl2-yl) acetyl) -2oxo-l, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) Was dissolved in DMF (2 mL). DIPEA (3xol), N-ethylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 284 (yield = 47%).
¾ 匪 R(400丽 z, CDC13)6 8.28(s, 1H) , 8.14(d, 1Η), 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 합성예 285 ： N-에틸 -l-(2— (5-아이오도 -2 ,3-디하이드로 -IH-인덴 -2-일)아세틸)¾ 匪 R (400 d z, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1Η), 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, 2 H). MASS = 484.16 Synthesis Example 285: N-ethyl -l- (2— (5-iodo-2,3-dihydro-IH-inden-2-yl) acetyl)
-2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide
1-(2— (5-아이오도 -2， 3-디하이드로 -1H-인덴 -2-일 )아세틸 )-2—옥소 -1 , 2- 디하이드로퀴놀린 -3-카복실릭 애시드 (1 誦 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N-에틸아닐린 (1.5隱 ol) 및 PyBop(2mmol )를 반웅 혼합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 285 화합물을 수득하였다 (수율 =56%).  1- (2— (5-iodo-2, 3-dihydro-1H-inden-2-yl) acetyl) -2—oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 誦 ol ) Was dissolved in DMF (2 mL). DIPEA (3xol), N-ethylaniline (1.5xol) and PyBop (2mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 285 (yield = 56%).
¾ NMR( 400MHz, CDC13)S 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),¾ NMR (400 MHz, CDC1 3 ) S 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=7.14 (t, 1H), 3.44 (s, 3H), 3.18 (s, 2H), 2.67 (m, 7H), 2.43 (m, 2H). MASS =
576.09 합성예 286 ： N-에틸 -l-(2-(5-니트로 -2,3—디하이드로— 1H-인덴 -2-일)아세틸) - 2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 576.09 Synthesis Example 286: N-ethyl -l- (2- (5-nitro-2,3—dihydro—1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1,2-di Hydroquinoline-3-carboxamide
1-(2-(5-니트로 -2， 3-디하이드로 -1H-인덴 -2-일)아세틸) -2-옥소 -1， 2- 디하이드로퀴놀린 -3-카복실릭 애시드 (1 匪 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸아닐린 (1.5隱 ol) 및 PyBop(2隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및. 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피 로 정제하여 합성예 286 화합물을 수득하였다 (수율 =55%). 1- (2- (5-nitro-2, 3-dihydro-1H-inden-2-yl) acetyl) -2-oxo-1, 2- Dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethylaniline (1.5 Pa ol) and PyBop (2 Pa ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was ethyl acetate and. Extracted with water. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 286 (yield = 55%).
¾ NMR(40(MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, ᅳ 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 합성예 287 ： l-(2— (5ᅳ아미노 -2, 3-디하이드로 -1H-인덴 -2-일)아세틸) -N-에틸-¾ NMR (40 (MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, ᅳ 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 Synthesis Example 287: l- (2— (5′-amino-2-, 3-dihydro-1H-inden-2-yl) acetyl) -N-ethyl-
2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide
1-(2-(5-아미노 -2 , 3-디하이드로ᅳ 1H-인덴 -2-일)아세틸 )-2-옥소 -1 , 2- 디하이드로퀴놀린 -,3-카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 瞧 ol), N-에틸아닐린 (1.5mmol) 및 PyBop(2mmol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피 로 정제하여 합성예 287 화합물을 수득하였다 (수율 =68%).  1- (2- (5-amino-2, 3-dihydro 하이드 1H-inden-2-yl) acetyl) -2-oxo-1, 2-dihydroquinoline-, 3-carboxylic acid (1 醒 ol ) Was dissolved in DMF (2 mL). DIPEAC3xol), N-ethylaniline (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. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 287 (yield = 68%).
¾ NMR( 400MHz, CDC13)5 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),¾ NMR (400 MHz, CDC1 3 ) 5 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),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 합성예 288 ： N-에틸 -2-옥소 -N-페닐 -1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N-에틸아닐린 (1.5 顏 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 288 화합물을 수득하였다 (수율 =45 . 2.43 (m, 2 H). MASS = 465.21 Synthesis Example 288: N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 A compound (1 'ol) was dissolved in DMF (2 mL). . DIPEA (3 x ol), N-ethylaniline (1.5 x ol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 288 (yield = 45.
¾ 賺 (400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH),¾ 賺 (400 MHz, CDC1 3 ) 6 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 합성예 289 ： l-(3-(2,3-디하이드로 -1H-인덴 -2-일)프로파노일) -N-에틸 -2- 옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 7.81 (dd, 2H), 7.43 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.19 (t, 1H), 7.14 (t, 1 H), 4.28 (m, 2 H), 1.31 (s, 3 H). MASS = 292.12 Synthesis Example 289: l- (3- (2,3-dihydro-1H-inden-2-yl) propanoyl) -N-ethyl-2-oxo-N-phenyl-1, 2-di Hydroquinoline-3-carboxamide
1-(3-(2，3-디하이드로ᅳ 1H-인덴 -2-일)프로파노일) -2-옥소 -1,2-디하이 드로퀴놀린ᅳ 3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3 画 ol), N-에틸아닐린 (1.5麵 ol) 및 PyBop(2隱 ol)를 반응 흔합물에 첨가하 고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 289 화합물을 수득하였다 (수율 =50%).  1- (3- (2,3-dihydro ᅳ 1H-inden-2-yl) propanoyl) -2-oxo-1,2-dihydrodroquinolin ᅳ 3-carboxylic acid (1 隱 ol) Dissolved in DMF (2 mL). DIPEA (3xol), N-ethylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 289 (yield = 50%).
¾ NMR(400MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, ᅳ 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 ( ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, ᅳ 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 (
합성예 292 ： N-메틸 -2-옥소 -N-(p-를일) -1， 2-디하이드로퀴놀린— 3-카르복사마 이드 Synthesis Example 292: N-methyl-2-oxo-N- (p-ylyl) -1, 2-dihydroquinoline— 3-carboxamide
합성예 25 화합물 (1 ᅵ誦 ol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 瞧 ol), N, 4-디메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 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 Compound (1 lOl) was dissolved in DMF (2 mL). DIPEAC3xol), N, 4-dimethylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 292 (yield = 54%).
¾ NMR( 400MHz, CDC13)6 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 합성예 295 ： Nᅳ에틸 -2-옥소 -N-(p-톨일) -1,2-디하이드로퀴놀린 -3-카르복사마 이드 ' ¾ NMR (400MHz, CDC1 3 ) 6 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 Synthesis Example 295: N ᅳ ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide '
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), N—에틸 -4-메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then with silica gel chromatograph Purification gave the compound of Synthesis Example 295 (yield = 54%).
¾ NMR( 400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36 (sᅳ 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 합성예 296 ： N-에틸 -2-옥소 -l-(4- (페닐티오)벤질) -N-(p-를일) -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (s ᅳ 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 Synthesis Example 296: N-ethyl- 2-oxo-l- (4- (phenylthio) benzyl) -N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide
2-옥소 -1ᅳ(4- (페닐티오)벤질) -1，2-디하이드로퀴놀린— 3-카복실릭애시 드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N-에틸— 4-메틸 아닐린 (1.5 隱 ol) 및 PyBop(2 瞧 ol)를 반웅 혼합물에 첨가하고 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 296 화함물을 수득하 였다 (수율 =57%).  2-oxo-1 '(4- (phenylthio) benzyl) -1,2-dihydroquinoline—3-carboxylic acid (1' ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl- 4-methyl aniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 296 (yield = 57%).
¾ 匪 R(400MHz, CDC13)6 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 합성예 297 ： N-에틸 -2-옥소 -1ᅳ (4-페녹시벤조일) -N-(p-를일) -1,2-디하이드로 퀴놀린ᅳ3—카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 297: N-ethyl-2-oxo-1 '(4-phenoxybenzoyl) -N- (p-ylyl) -1,2-dihydroquinoline # 3—carboxamide
2-옥소 -1ᅳ(4—페녹시벤조일 )-1， 2-디하이드로퀴놀린 -3—카복실릭애시드 2-oxo-1 '(4—phenoxybenzoyl) -1, 2-dihydroquinoline-3-carboxylic acid
(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEAO 誦 ol), N-에틸 -4- 메틸아닐린 (1.5 隱 ol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 297 화합물을 수득하였다 (수율 =58%). (1 mmol) was dissolved in DMF (2 mL). DIPEAO 誦 ol), N-ethyl-4-methylaniline (1.5 隱 ol) and PyBop (2 睡 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 297 (yield = 58%).
NMR(400丽 z,CDCl3)S 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 합성예 298 ： N—에틸 -2-옥소 -l- - (페닐티오)벤조일) -N-(pᅳ를일 )— 1，2- 디하이드로퀴놀린 -3-카르복사마이드 2-옥소 -l-(4- (페닐티오)벤조일 )-1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 讓 ol), N-에틸 -4- 메틸아닐린 (1.5 mmol) 및 PyBop(2 麵 ol)를 반응 흔합물에 첨가하고 상은에서 3시간 등안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 298 화합물을 수득하였다 (수율 =58%). NMR (400 z, CDCl 3 ) S 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 Synthesis Example 298: N—ethyl-2-oxo-l-(phenylthio) benzoyl) -N- (p-yl) — 1,2-dihydroquinoline-3-carboxamide 2-oxo-l- (4- (phenylthio) benzoyl) -1,2-dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-methylaniline (1.5mmol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 298 (yield = 58%).
¾丽 R(40()MHz, CDC13)5 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 합성예 299 ： N-에틸ᅳ 2-옥소 -1-(2-(4ᅳ (페닐티오)페닐)아세틸) -N-(p-를일)一 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 丽 R (40 () MHz, CDC1 3 ) 5 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 Synthesis Example 299 ： N-ethyl ᅳ 2-oxo-1- (2- (4 '(phenylthio) phenyl) acetyl) -N- (p-ylyl) 1 1, 2-dihydroquinoline-3- Carboxamide
2-옥소 -1-(2-(4- (페닐티오)페닐)아세틸 )-1， 2ᅳ디하이드로퀴놀린 -3ᅳ 카복실릭 애시드 Q 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N- 에틸 -4-메틸아닐린 (1.5 mmol) 및 PyBop(2 薩 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 299 화합물을 수득하였다 (수율 =69 .  2-oxo-1- (2- (4- (phenylthio) phenyl) acetyl) -1,2'dihydroquinoline-3'carboxy acid Q 隱 ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 299 (yield = 69.
¾ 丽 R OOMHz, CDC13)6 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 합성예 300 ： N-에틸 -2-옥소 -l-(2-(4-페녹시페닐)아세틸) -N-(p-를일) -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ δ R OOMHz, CDC1 3 ) 6 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 Synthesis Example 300: N-ethyl-2-oxo-l- (2- (4-phenoxyphenyl) acetyl) -N- (p-ylyl) -1,2-dihydroquinoline-3-carbox Maid
2-옥소 -1-(2ᅳ(4-페녹시페닐)아세틸 )-1,2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 誦 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), N-에틸 -4- 메틸아닐린 (1.5 mmol) 및 PyBop(2 隨 ol)를 반웅 흔합물에 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 ′ ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 300 compound (yield = 74%).
¾ 匪 R(400MHz, CDC13)6 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 합성예 301 ： l-(2-(4-벤질페닐)아세틸) -N-에틸 -2-옥소 -N-(p-틀일) -1,2-디하 이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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, 3 H), 1.31 (s, 3 H). MASS = 516.20 Synthesis Example 301: l- (2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-tolyl) -1,2-dihydroquinoline-3-carboxamide
1—(2-(4-벤질페닐)아세틸 )-2-옥소— 1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 麵 ol), N-에틸 -4- 메틸아닐린 (1.5 讓 ol) 및 PyBop(2 讓 ol)를 반웅 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 μl) was dissolved in DMF (2 mL). DIPEAC3 麵 ol), N-ethyl-4-methylaniline (1.5 讓 ol) and PyBop (2 讓 ol) were added to the reaction mixture and stirred for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 301 (yield = 55%).
¾ 匪 R( 400MHz, CDC13)6 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 합성예 302 ： l-(4-벤질벤조일) -N-에틸 -2-옥소 -N— (p-를일) -1，2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ 匪 R (400MHz, CDC1 3 ) 6 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 Synthesis Example 302: l- (4-benzylbenzoyl) -N-ethyl-2-oxo-N— (p-ylyl) -1,2-dihydroquinoline-3-carboxamide
1-(4-벤질벤조일 )ᅳ2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), N-에틸 -4-메틸아닐린 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 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) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 302 (yield = 74%). ,
¾匪 R(400MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1Hᅳ -NH),¾ 匪 R (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H ᅳ -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 합성예 303 ： N-(4-메톡시페닐)—N-메틸 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 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, 3 H), 1.31 (s, 3 H). MASS = 500.21 Synthesis Example 303: N- (4-methoxyphenyl) —N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), 4-메톡시 -N—메틸아닐린 (1.5 !Timol) 및 PyBop(2 國 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 醒 ol), 4-methoxy-N—methylaniline (1.5! Timol) and PyBop (2 ol ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 303 (yield = 44%)
¾ NMR( 400MHz, CDC13)8 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -NH)¾ NMR (400 MHz, CDC1 3 ) 8 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H, -NH)
7.36 (s, IH), 7.34(dd, 2H), 7.3i(t, 1H), 7.21 (dd, 2H) , 7.14(t, 1H) , 4.28(s, 3H), 3.83(s, 3H). MASS=308.12 합성예 304 ： N-에틸 -N-(4-메톡시페닐 )ᅳ2-옥소 -1,2-디하이드로퀴놀린 -3-카르 복사마이드 7.36 (s, IH), 7.34 (dd, 2H), 7.3i (t, 1H), 7.21 (dd, 2H), 7.14 (t, 1H), 4.28 (s, 3H), 3.83 (s, 3H). MASS = 308.12 Synthesis Example 304 ： N-ethyl-N- (4-methoxyphenyl) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N-에틸 -4-메특시아닐린 (1.5 薩 ol) 및 PyBop(2 國 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 304 화합물을 수득하였다 (수율 =73%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), N-ethyl-4-methoxianyline (1.5 薩 ol) and PyBop (2 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate water. Then purified by silica gel chromatography to obtain the Synthesis Example 304 compound (yield = 73%).
匪 R OOMHz, CDC13)6 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-카르 복사마이드 R OOMHz, CDC1 3 ) 6 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 Synthesis Example 306: N- (4-bromophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 4-브로모ᅳ N-메틸아닐린 (1.5 mmol) 및 PyBop (2國 ol)를 반응 흔합물에 첨가하^ 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 306 화합물을 수득하였다 (수율 =56%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-bromochet N-methylaniline (1.5 mmol) and PyBop (2 ol ol) were added to the reaction mixture ^ and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 306 (yield = 56%).
¾ 丽 R (400MHz ,CDC13)5 8.28(sᅳ 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(sᅳ 3H). MASS- 356.02 합성예 307 ： N-(4-브로모페닐) -1- (사이클로펜타 -1,3-디엔카르보닐) -N-메틸- 2-옥소 -1， 2-디하이드로퀴놀린 -3—카르복사마이드 ¾ δ R (400MHz, CDC1 3 ) 5 8.28 (s ᅳ 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 ᅳ 3H). MASS- 356.02 Synthesis Example 307: N- (4-bromophenyl) -1- (cyclopenta-1,3-dienecarbonyl) -N-methyl- 2-oxo-1, 2-dihydroquinoline-3-carboxamide
1- (사이클로펜타 -1 , 3-디엔카르보닐 ) -2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1.瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- 브로모 -N-메틸아닐린 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 307 화합물을 수득하였다 (수율 =64%).  1- (cyclopenta-1, 3-dienecarbonyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1.'ol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-bromo-N-methylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 307 (yield = 64%).
¾ 證 (400MHz, CDC13)6 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-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 308 N- (4-bromophenyl) -N-methyl-2-oxo-1- (2H-pyrrole-3-carbonyl) -1,2-dihydroquinoline-3-carbox Maid
2-옥소 -1-(2H-피를 -2-카르보닐) -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-브로모 -N- 메틸아닐린 (1.5 瞧 ol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 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-blood was 2-carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-bromo-N-methylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 308 (yield = 67%).
¾ NMR( 400MHz, CDC13) 8.28(s, 1H)， 8.0(s, 1H, -NH), 7.88(m, 2H),¾ NMR (400MHz, CDC1 3 ) 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-카르복사마이드 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 Synthesis Example 309 ： N- (4-bromophenyl) —N-methyl-2-oxo-1— (thiophene-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide
2-옥소 -1- (티오펜 -2-카르보닐) -1， 2-디하이드로퀴놀린 -3—카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-브로모 -N- 메틸아닐린 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 309 화합물을 수득하였다 (수율 =67%). ¾ NMR( 400MHz， CDC13)6 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) 2-oxo-1- (thiophene-2-carbonyl) -1, 2-dihydroquinoline-3—carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-bromo-N-methylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 309 (yield = 67%). ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 310: (N- (4-bromophenyl) -1- (furan 2-carbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide)
1- (퓨란 -2-카르보닐) -2ᅳ옥소—1， 2-디하이드로퀴놀린 -3-카복실릭애시드 (1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-브로모 -N- 메틸아닐린 (1.5 麵 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 310 화합물을 수득하였다 (수율 =63%).  1- (furan-2-carbonyl) -2oxo-l, 2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-bromo-N-methylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 310 (Yield = 63%).
¾ 画 R( 400MHz, CDC13)6 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 -l-(2— (티오펜 -2-일)아세틸) - 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 画 R (400MHz, CDC1 3 ) 6 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 Synthesis Example 311: N- (4-bromophenyl) -N-methyl-2-oxo-l- (2— (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3 Carboxamide
2-옥소ᅳ 1-(2- (티오펜 -2-일)아세틸 )-1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2mL)에 용해시켰다. DIPEA(3隱 ol), 4-브로모 -N- 메틸아닐린 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 311 화합물을 수득하였다 (수율 =55%).  2-oxoox 1- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-bromo-N-methylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 311 (yield = 55%).
¾ 丽 R(400MHz, CDC13)5 8.28(s, 1H) , 8.0(s, 1H, -NH), 7.88(m, 2H); ¾ δ R (400 MHz, CDC1 3 ) 5 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) -l-(2- (퓨란 -2-일)아세틸) -N-메틸 -2-옥소ᅳ1，2 —디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 312: N- (4-bromophenyl) -l- (2- (furan-2-yl) acetyl) -N-methyl-2-oxox 1,2, -dihydroquinoline-3- Carboxamide
1-(2- (퓨란 -2-일)아세틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEM3瞧 ol), 4-브로모 메틸아닐린 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 312 화합물을 수득하였다 (수율 =56%). 1- (2- (furan-2-yl) acetyl) -2-oxo-1, 2-dihydroquinoline-3 ᅳ carboxyl Acid (1 μl) was dissolved in DMF (2 mL). DIPEM3 'ol), 4-bromo methylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis 312 (yield = 56%).
¾ 丽 (400MHz, CDC13)6 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 ： l-(2-(2H-피를ᅳ 2-일)아세틸) -N-(4-브로모페닐) -N-메틸 -2-옥소-¾ δ (400 MHz, CDC1 3 ) 6 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 Synthesis Example 313: l- (2- (2H-Pyryl-2-yl) acetyl) -N- (4-bromophenyl) -N-methyl-2-oxo-
1， 2-디하이드로퀴놀린 -3—카르복사마이드 1, 2-dihydroquinoline-3—carboxamide
1-(2-(2Η-피를 -5-일)아세틸) -2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복 실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3mmol ) , 4-브로모 1- (2- (2Η-blood-5-yl) acetyl) -2-oxo-1,2'dihydroquinoline-3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3mmol), 4-bromo
-N-메틸아닐린 (1.5 醒 ol) 및 PyBop(2 匪 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 313 화합물을 수득하였다 (수율 =45%). -N-methylaniline (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 313 (yield = 45%).
¾ NMR(400MHz, CDC13)5 8.28(s, 1H) , 8.0(s, 1H, -NH) , 7.88(m, 2H)¾ NMR (400 MHz, CDC1 3 ) 5 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- 카르복사마이드 , 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 Synthesis Example 314: N- (4-bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide,
합성예 25 화합물 (1 隱 ol)올 DMF(2 mL)에 용해시켰다. DIPEA(3 睡 ol), 4-브로모 -N-에틸아닐린 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 불로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 314 화합물을 수득하였다 (수율 =67%).  Synthesis Example 25 Compound (1'ol) ol was dissolved in DMF (2 mL). DIPEA (3xol), 4-bromo-N-ethylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and fire. Then purified by silica gel chromatography to give the compound of Synthesis Example 314 (yield = 67%).
¾ 賺 (400MHz, CDC13)6 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,¾ 賺 (400 MHz, CDC1 3 ) 6 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- (사이클로핵산카르보닐) -N-에틸 -2—옥소- 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 2H), 1.31 (s, 3H). MASS = 370.03 Synthesis example 315: N- (4-bromophenyl) -1- (cyclonucleic acid carbonyl) -N-ethyl- 2-oxo- 1, 2-dihydroquinoline-3-carboxamide
1- (사이클로헥산카르보닐) -2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 ol), 4-브로모 -N- 에틸아닐린 (1.5 醒 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 315 화합물을 수득하였다 (수율 =45%).  1- (Cyclohexanecarbonyl) -2oxoo-1, 2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEAC3 'ol), 4-bromo-N-ethylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 315 (yield = 45%).
¾ NMR( 400MHz, CDC13)5 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m, 2H),¾ NMR (400 MHz, CDC1 3 ) 5 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) -l-(3-사이클로핵실프로파노일) -N-에틸 -2- 옥소 -1,2-디하이드로퀴놀린— 3-카르복사마이드 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 Synthesis Example 316: N- (4-Bromophenyl) -l- (3-cyclonucleosilpropanoyl) -N-ethyl-2-oxo-1,2-dihydroquinoline— 3-carboxamide
1-(3ᅳ사이클로핵실프로파노일 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), R 4- 브로모 -N-에틸아닐린 3-NH2(1.5mmol) 및 PyBop(2隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피 를 정제하여 합성예 316 화합물을 수득하였다 (수율 =42%) 1- (3′cyclonucleosilpropanoyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), R 4-bromo-N-ethylaniline 3 -NH 2 (1.5mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then silica gel column chromatography was purified to give the compound of Synthesis Example 316 (yield = 42%)
¾ NMR ( 400MHz, CDC1 a )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 합성예 318 ： N-(4-클로로페닐) -N-메틸 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드  ¾ NMR (400 MHz, CDC1 a) 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 Synthesis Example 318 N- (4-chlorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로 -Ν—메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 318 화합물을 수득하였다 (수율 =64%). Synthesis Example 25 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N—methylaniline (1.5 mmol) and PyBop (2 μL) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethyl acetate and water. Then with silica gel chromatograph Purification gave Synthesis Example 318 compound (Yield = 64%).
¾ NMR (4Q0MHz,CDCl3)6 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 합성예 319 ： N-(4-클로로페닐) -1- (사이클로펜탄카르보닐) -N-메틸 -2-옥소-¾ NMR (4Q0 MHz, CDCl 3 ) 6 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 Synthesis Example 319: N- (4-chlorophenyl) -1- (cyclopentanecarbonyl) -N-methyl-2-oxo-
1， 2-디하이드로퀴놀린 -3-카르복사마이드 1, 2-dihydroquinoline-3-carboxamide
1- (사이클로프로판카르보닐 )ᅳ2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복실 릭 애시드 (1 誦 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4ᅳ클로로- N-메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온 에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 319 화합 물을 수득하였다 (수율 =56%).  1- (cyclopropanecarbonyl) 닐 2-oxo-1, 2 ᅳ dihydroquinoline-3-carboxylic acid (11 ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4'chloro-N-methylaniline (1.5 mmol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 319 (yield = 56%).
¾ NMR (40( Ηζ,α)(:13)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,¾ NMR (40 (Ηζ, α) (: 1 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-카르복사마이드 3H), 2.98 (m, 8H). MASS = 408.12 Synthesis Example 320: N- (4-chlorophenyl) -1- (furan-2-carbonyl) -N-methyl-2-oxo— 1,2-dihydroquinoline-3-carboxamide
1— (퓨란 -3-카르보닐) -2-옥소 -1 , 2-디하이드로퀴놀린— 3ᅳ카복실릭애시드 1— (furan-3-carbonyl) -2-oxo-1, 2-dihydroquinoline— 3 ᅳ carboxylic acid
(1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-클로로 메틸 아닐린 (1.5 隱 ol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 320 화합 물을 수득하였다 (수율 =73%). (1 μl) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro methyl aniline (1.5 μl ol) 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. Then purified by silica gel chromatography to obtain the synthesis Example 320 compound (yield = 73%).
¾ NMR ( 400MHz, CDC13 )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-카르복사마아드 2-옥소 -1- (티오펜 -3-카르보닐)— 1 , 2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 瞧 ol)를 DMP(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-클로로 _N- 메틸아닐린 (2 醒 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출 하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 321 화합물을 수득하였다 (수율 =56%). ¾ NMR (400 MHz, CDC13) 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 Synthesis Example 321: N- (4-chlorophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1,2-dihydroquinoline—3-carboxamide 2-oxo-1- (thiophene-3-carbonyl) — 1, 2-dihydroquinoline-3-carboxylic acid (1 ′ ol) was dissolved in DMP (2 mL). DIPEA (3xol), 4-chloro_N-methylaniline (2xol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 321 (yield = 56%).
¾ NMR ( 400MHz, CDC13 )δ 8.28(s, 1H)ᅳ 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-피를 -2-카르보닐) -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400MHz, CDC13) δ 8.28 (s, 1H) ᅳ 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 Synthesis Example 322 N- (4-chlorophenyl) -N-methyl-2-oxo- 1- (2H-Pyryl-2-carbonyl) -1,2-dihydroquinoline-3-carboxamide
2-옥소 -1-(2H-피를 -5ᅳ카르보닐) -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3隱 ol), 4-클로로 -N- 메틸아닐린 (1.5 隱 ol) 및 PyBop(3 咖 ol)를 반웅 흔합물에 첨가하고 상온 에서 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-Pi-5-5carbonyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-chloro-N-methylaniline (1.5' ol) and PyBop (3 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 322 (yield = 57%).
¾ NMR (400MHz, CDC13)6 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),¾ NMR (400 MHz, CDC1 3 ) 6 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- 카르복사마이드 4.28 (s, 3 H), 2.98 (m, 3 H). MASS = 405.09 Synthesis Example 323 ： N- (4-chlorophenyl) -N-ethyl-2-oxo—1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-클로로—N-에틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-chloro-N-ethylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 323 (yield = 58%).
¾ NMR (400MHz, CDC13)8 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 8 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) -l-(2-사이클로펜틸아세틸)— N-에틸 -2-옥소- 1， 2-디하이드로퀴놀린ᅳ 3-카르복사마이드 2H), 7.34 (dd, 2H), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2 H), 1.31 (s, 3 H). MASS = 326.08 Synthesis Example 324 ： N- (4-chlorophenyl) -l- (2-cyclopentylacetyl) —N-ethyl-2-oxo-1,2-dihydroquinoline 놀 3-carboxamide
1-(2-사이클로펜틸아세틸 )-2-옥소— 1， 2-디하이드로퀴놀린ᅳ 3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-클로로 -N- 에틸아닐린 (1.5. 瞧 ol) 및 PyBop(0.9 mg, 1.8 画 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 324 화합물을 수득하였다.  1- (2-cyclopentylacetyl) -2-oxo— 1, 2-dihydroquinoline® 3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 4-chloro-N-ethylaniline (1.5. Μl ol) and PyBop (0.9 mg, 1.8 μl ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 324.
¾ 丽 R (400丽 z, CDC13)6 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(iii, 2H), 3.45(m, 2H), 2.87(m, 8H) , 1.31(s, 3H). MASS=436.16 합성예 325 ： N-(4-클로로페닐) -N-에틸 -l-(2- (퓨란 -2—일)아세틸 )-2-옥소 -1,2 -디하이드로퀴놀린 -3-카르복사마이드 ¾丽R (400丽z, CDC1 3) 6 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 (iii, 2H), 3.45 (m, 2H), 2.87 (m, 8H), 1.31 (s, 3H). MASS = 436.16 Synthesis Example 325: N- (4-Chlorophenyl) -N-ethyl -l- (2- (furan-2 -yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carbox Copyamide
1- (2- (퓨란 -3-일 )아세틸) -2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3瞧 ol), 4-클로로 -N- 에틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온 에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 325 화합물을 수득하였.다 (수율 =45%). 1- (2- (furan-3-yl) acetyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-chloro-N-ethylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 325 (yield = 45 %).
¾ MR (400MHz, CDC13)3 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 합성예 326 ： N-(4-클로로페닐) -N-에틸 -2-옥소 -l-(2- (티오펜 -2-일)아세틸) - 1， 2-디하이드로퀴놀린— 3-카르복사마이드 ¾ MR (400MHz, CDC1 3 ) 3 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 Synthesis Example 326: N- (4-Chlorophenyl) -N-ethyl-2-oxo-l- (2- (thiophen-2-yl) acetyl) -1,2-dihydroquinoline-3 Carboxamide
2-옥소 -1-(2- (티오펜 -3-일)아세틸) -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 謹 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4—클로로 -N- 에틸아닐린 (1.5 醒 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다/ 이후 실리카겔 크로마토그래프로 정제하여 합성예 326 화합물을 수득하였다 (수율 =66¾ . 2-oxo-1- (2- (thiophen-3-yl) acetyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4—chloro-N-ethylaniline (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and Stir at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water / after purified by silica gel chromatography to give the synthesis example 326 compound (yield = 66¾.
¾ 醒 R(400腿 z,CDCl3)S 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 합성예 327 ： 1— (2-(2H-피롤 -2—일)아세틸) -N-(4-클로로페닐) N-에틸 -2-옥소- 1,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 醒 R (400 腿 z, CDCl 3 ) S 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 Synthesis Example 327 ： 1— (2- (2H-pyrrole-2-yl) acetyl) -N- (4-chlorophenyl) N-ethyl-2-oxo- 1,2-dihydroquinoline-3- Carboxamide
1-(2-(2Η-피롤 -5-일)아세틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4- 클로로 -N-메틸아닐'린 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 쎄틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 327 화합물을 수득하였다 (수율 =46%). 1- (2- (2Η-pyrrole-5-yl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-chloro-N-methylaniyl ' lean (1.5 mmol) and PyBop (2 μL) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with cetyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 327 (yield = 46%).
¾ NMR( 400MHz, CDC13)5 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 합성예 328 ： N-(4-플루오로페닐) -N-메틸 -2-옥소 -1， 2—디하이드로퀴놀린 -3-카 르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 328: N- (4-fluorophenyl) -N-methyl-2-oxo-1,2—dihydroquinoline-3-carboxamide
합성예 25'·화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 4-플루오로 -N-메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 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 ' Compound (1 ' ol) was dissolved in DMF (2 mL). DIPEA (3 μL), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 328 (yield = 58%).
¾ 證 (400MHz ,CDC13)6 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 합성예 329 ： N-(4-플루오로페닐) -Nᅳ메틸 -2-옥소 -l-(2-옥소 -2-페닐에틸) - 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 329: N- (4-fluorophenyl) -N ᅳ methyl-2-oxo-l- (2-oxo-2-phenylethyl)- 1, 2-dihydroquinoline-3-carboxamide
2-옥소 -1-(2-페닐아세틸) -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 ( 1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-플루오로 -N-메틸 아닐린 (1.5 誦 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 329 화합 물을 수득하였다 (수율 =67%).  2-oxo-1- (2-phenylacetyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-fluoro-N-methyl aniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph to give the Synthesis Example 329 compound (yield = 67%).
¾ 匪 R(400MHz, CDC13)5 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 ᅳ 합성예 330 ： N-(4-플루오로페닐 )-l-(2-(4-메특시페닐) -2-옥소에틸) -N-메틸-¾ 匪 R (400 MHz, CDC1 3 ) 5 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 ᅳ Synthesis Example 330: N- (4-fluorophenyl) -l- (2- (4-methoxyphenyl) -2-oxoethyl) -N-methyl-
2一옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 2 ioxo-1, 2-dihydroquinoline-3-carboxamide
1- (2-(4-메톡시페닐)아세틸 )ᅳ2—옥소 -1， 2-디하이드로퀴놀린— 3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- 플루오로 -N-메틸아닐린 (1.5 醒 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 330 화합물을 수득하였다 (수율 =67¾ .  1- (2- (4-methoxyphenyl) acetyl) ᅳ 2—oxo-1, 2-dihydroquinoline—3-carboxylic acid (1 × ol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 4-fluoro-N-methylaniline (1.5 μl ol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 330 (yield = 67¾.
¾ NMR (400MHz, CDC13)6 8.28(s, 1H) , 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m,
4H), 7.34 (m, 310， 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 -l-(2-옥소 -2-(4- (트리플루 오로메톡시 )페닐)에틸) -1， 2-디하이드로퀴놀린 -3-카르복사마이드 4H), 7.34 (m, 310, 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H), 1.35 (s MASS = 444.15 Synthesis Example 331: N- (4-fluorophenyl) -N-methyl-2-oxo-l- (2-oxo-2- (4- (trifluomethoxy) phenyl) Ethyl) -1,2-dihydroquinoline-3-carboxamide
2-옥소 -1-(2-(4- (트리플루오로메록시 )페닐)아세틸 )-1 , 2—디하이드로 퀴놀린—3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 4-플루오로ᅳ N-메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 331 화합물을 수득하였다 (수율 =65%). ¾ NM (400MHz, CDC13)6 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 -l-(2-(4-니트로페닐) -2-옥소에틸) - 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-1- (2- (4- (trifluoromethoxy) phenyl) acetyl) -1, 2-dihydro quinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). . DIPEA (3 'ol), 4-fluoro' N-methylaniline (1.5 mmol) and PyBop (2 'ol) were added to the reaction mixture and stirred for 3 hours at phase silver. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 331 (yield = 65%). ¾ NM (400 MHz, CDC1 3 ) 6 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 Synthesis Example 332: N- (4-fluorophenyl) -N-methyl-l- (2- (4-nitrophenyl) -2-oxoethyl)-2-oxo-1, 2-dihydroquinoline -3-carboxamide
1-(2-(4-니트로페닐)아세틸 )-2-옥소 -1，2ᅳ디하이드로퀴놀린ᅳ 3- 카복실릭 애시드 (1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 4- 플루오로 -N-메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 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 ᅳ 3-carboxylic acid (1 'ol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-fluoro-N-methylaniline (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 332 (yield = 76%).
¾ NMR(400顧 z, CDC13)6 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 )-l-(2-(4-하이드록시페닐) -2-옥소에틸) -N- 메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3—카르복사마이드 ¾ NMR (400 顧 z, CDC1 3 ) 6 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 Synthesis Example 333: N- (4-fluorophenyl) -l- (2- (4-hydroxyphenyl) -2-oxoethyl) -N-methyl-2-oxo-1, 2-dihydro Quinoline-3—carboxamide
1-(2— (4-하이드록시페닐 )아세틸 )-2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3- 카르복실릭애시드 (lmmol)를 DMF(2mL)에 용해시켰다. DIPEM3画 ol), 4- 플루오로 -N-메틸아닐린 (1.5醒 ol) 및 PyBop(2隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 상온에서 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 333 화합물을 수득하였다 (수율 =76%).  1- (2— (4-hydroxyphenyl) acetyl) -2-oxoox 1, 2-dihydroquinoline-3-carboxylic acid (lmmol) was dissolved in DMF (2 mL). DIPEM3 'ol), 4-fluoro-N-methylaniline (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 333 (yield = 76%).
¾ NMR ( 400MHz, CDC13 )δ 8.28(s, 1H) , 8.0(s, 1H, -NH), 7.88(m, 4H), ¾ NMR (400MHz, CDC13) 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) ,7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (s, 3H),
2.79(sᅳ 2H). MASS=430.13 합성예 334 ： N-(4-플루오로페닐 )-1ᅳ (2-(4-플루오로페닐 )-2—옥소에틸) -N- 메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 2.79 (s ᅳ 2H). MASS = 430.13 Synthetic Example 334: N- (4-fluorophenyl) -1 '(2- (4-fluorophenyl) -2—oxoethyl) -N-methyl-2-oxo-1,2-dihydro Quinoline-3-carboxamide
1-(2-(4-플^오로페닐)아세틸 )-2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 mntol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- 플루오로 -N-메틸아닐린 (1.5 醒 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 334 화합물을 수득하였다 (수율 =78%) 1- (2- (4-ple ^ ophenyl) acetyl) -2-oxo 옥 1, 2-dihydroquinoline-3-carboxy Cilic acid (1 mntol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), 4-fluoro-N-methylaniline (1.5 μl ol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 334 (yield = 78%)
¾ MR (400 MHz, CDC13)5 8.28 (sᅳ iH) , 8.0 (s, 1Η, -NH) , 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 (s, 1H, ᅳ 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-카르복사마이드 ¾ MR (400 MHz, CDC1 3 ) 5 8.28 (s ᅳ iH), 8.0 (s, 1Η, -NH), 7.88 (m, 4H), 7.34 (m, 3H), 7.29 (m, 3H), 7.23 ( s, 1H, ᅳ NH), 7.21 (dd, 2H), 4.28 (s, 3H), 2.79 (s, 2H). MASS = 432.13 Synthesis Example 335: 1— (2— (4—ethylphenyl) -2-oxoethyl) -N- (4-fluorophenyl) -N-methyl-2-oxo-1,2-dihydroquinoline -3-carboxamide
1-(2ᅳ(4-에틸페닐)아세틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4ᅳ플루오로- 1- (2 ′ (4-ethylphenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4'fluoro-
N-메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 335 화합물을 수득하였다 (수율 =73%). N-methylaniline (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. Then purified by silica gel chromatography to give the compound of Synthesis Example 335 (yield = 73%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 336 ： l-(2-(4-시아노페닐)아세틸) -N-(4-에틸펜에틸) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 336: l- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2ᅳ (4-클로로페닐 )아세틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 睡 ol), ^에¾_4- 플루오로아닐린 (1.5 mmol) 및 PyBop(2 讓 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 336 화합물을 수득하였다 (수율 =76%).  1- (2 '(4-Chlorophenyl) acetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1' ol) was dissolved in DMF (2 mL). DIPEA (3 睡 ol), ¾ / 4-fluoroaniline (1.5 mmol) and PyBop (2 讓 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 336 (yield = 76%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 6 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, 2Η).'· MASS=448.10 합성예 337 ： N-에틸 -N-(4-플루오로페닐 )-2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 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, 2Η). 'MASS = 448.10 Synthesis Example 337: N-ethyl -N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 誦 ol), N-에틸 -4-플루오로아닐린 (1.5 mmol) 및 PyBop(2 國 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 Pa ol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (Dol ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 337 (yield = 71%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.0(s, 1H( -NH) , 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.0 (s, 1H ( -NH), 7.88 (m,
2H), 7.34 (dd, '2Η), 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 ： l-(2-(4—아미노페닐) -2—옥소에틸) -N-에틸 -N-(4—플루오로페닐) - 2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카르복사마이드 2H), 7.34 (dd, '2Η), 7.29 (t, 1H), 7.23 (s, 1H, -NH), 7.21 (dd, 2H), 4.28 (m, 2H), 1.31 (s, 3H). MASS = 310.11 Synthesis Example 338: l- (2- (4-aminophenyl) -2-oxoethyl) -N-ethyl-N- (4-fluorophenyl)-2-oxo-l, 2'dihydroquinoline- 3-carboxamide
1-(2-(4-아미노페닐)아세틸 )ᅳ2—옥소 -1， 2—디하이드로퀴놀린 -3-카복실 릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸 -4- 플루오로아닐린 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 338 화합물을 수득하였,다 (수율 =76%).  1- (2- (4-aminophenyl) acetyl) # 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 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 338 (yield = 76%).
¾ NMR(400 MHz, CDC13)5 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m,
4H), 7.34 Cm, 3H) , 7.29(m, 3H), 7.23(s, 1H, — NH), 7.21(dd, 2H), 4.28(s,4H), 7.34 Cm, 3H), 7.29 (m, 3H), 7.23 (s, 1H, — NH), 7.21 (dd, 2H), 4.28 (s,
3H), 4.05(s, -N¾, -2H), 2.79(s, 2H). MASS=443.16 합성예 339 ： l-(2-(4-시아노페닐) -2-옥소에틸) -N-에틸 -N-(4-플루오로페닐) - 2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카르복사마이드 3H), 4.05 (s, -N¾, -2H), 2.79 (s, 2H). MASS = 443.16 Synthesis Example 339: l- (2- (4-cyanophenyl) -2-oxoethyl) -N-ethyl -N- (4-fluorophenyl)-2-oxo-1, 2-dihydro Quinoline-3 ᅳ carboxamide
1-(2— (4-시아노페닐)아세틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N-에틸 -4- 플루오로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 등안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 339 화합물을 수득하였다 (수율 =43%). 1- (2— (4-cyanophenyl) acetyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 × ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N-ethyl-4-fluoroaniline (1.5 mmol) and PyBop (2 mu ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The residue obtained was ethyl acetate and Extracted with water. Then purified by silica gel chromatography to give the compound of Synthesis 339 (yield = 43%).
¾ NMR(400 MHz, CDC13)6 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 ： Nᅳ에틸 -N-(4-플루오로페닐 )-l-(2-(4- (메틸티오)페닐) -2-옥소 에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 (s3H), 2.79 (s, 2H) MASS = 453.15 Synthesis Example 340: N ᅳ ethyl -N- (4-fluorophenyl) -l -(2- (4- (methylthio) phenyl) -2-oxoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-(4- (메틸티오)페닐)아세틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3ᅳ카 복실릭애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), N- 에틸 -4-플루오로이 ^닐린 (1.5 讓 ol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 340 화합물을 수득하였다 (수율 =42%).  1- (2- (4- (methylthio) phenyl) acetyl) -2-oxo-1, 2-dihydroquinoline-3 ᅳ ca cyclolic acid (1 讓 ol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethyl-4-fluoroyniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 340 (yield = 42%).
¾ MR(400 MHz, CDC13)5 8.28(s, 1H), 8.0(s, 1Hᅳ -NH), 7.88(m,¾ MR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.0 (s, 1H ᅳ -NH), 7.88 (m,
4H), 7.34 (m, 3H), 7.29(m, 3H), 7.23(s, 1H, -NH), 7.21(dd, 2H), 4.28(s4H), 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-카르복 사마이드 3H), 3.30 (s, 3H), 2.79 (s, 2H). MASS-474.14 Synthesis Example 341: N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 '화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N, 4-디에틸아닐린 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 ' Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), N, 4-diethylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 341 (yield = 53%).
¾ NMR(400 MHz, CDC13)6 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 합성예 342 ： l-(2, 4-디메틸벤질) -Nᅳ (4-에틸페닐) -N-메틸 -2-옥소 -1,2-디하이 드로퀴놀린— 3-카르복사마이드 l-(2， 4-디메틸벤질 )-2-옥소 -1ᅳ 2ᅳ디하이드로퀴놀린— 3-카복실릭애시드 (1 隱 οθ를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), N,4- 디에틸아닐린 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 342 화합물을 수득하였다 (수율 =76%). ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 342: l- (2,4-dimethylbenzyl) -N '(4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydrodroquinoline—3-carboxamide l- (2,4-dimethylbenzyl) -2-oxo-1'2'dihydroquinoline—3-carboxylic acid (1 隱 οθ was dissolved in DMF (2 mL). DIPEA (3 隱 ol), N, 4-diethylaniline (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred for 3 hours at room temperature The resulting residue was extracted with ethyl acetate and water, then purified by silica gel chromatography. To give Synthesis Example 342 compound (yield = 76%).
¾ NMR(400 MHz, CDC13)6 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 합성예 343 ： 1-(2,4-디메틸펜에틸) -(4-에틸페닐)->卜메틸ᅳ2-옥소-1，2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 343: 1- (2,4-dimethylphenethyl)-(4-ethylphenyl)-> 卜 methyl 卜 2-oxo-1,2-dihydroquinoline-3-carboxamide
1— (2,4-디메틸펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 4ᅳ에틸 -N—메틸 아닐린 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 343 화합물을 수득하였다 (수율 =7OT)  1— (2,4-dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3xol), 4xethyl-N-methyl aniline (1.5xol) 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. After purification by silica gel chromatography to obtain the compound of Synthesis Example 343 (Yield = 7OT)
¾ 匿 (400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ 匿 (400 MHz, CDC1 3 ) 6 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 합성예 344 ： N-(4-에틸페닐) -l-(4-하이드록시ᅳ2-메틸벤질) -N-메틸 -2-옥소-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 Synthesis Example 344: N- (4-ethylphenyl) -1-(4-hydroxy ᅳ 2-methylbenzyl) -N-methyl-2-oxo-
1,2-디하이드로퀴놀린 -3—카르복사마이드 1,2-dihydroquinoline-3—carboxamide
1-(4-하이드록시 -2-메틸펜에틸 )-2-옥소 -1，2-디하이드로퀴놀린 -3—카복 실릭애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-에틸- 1- (4-hydroxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3—carboxy cilic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), 4-ethyl-
N-메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다/ 이후 실리카겔 크로마토그래프로 정제하여 합성예 344 화합물을 수득하였다 (수율 =53%). N-methylaniline (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 / then purified by silica gel chromatography to synthesize Example 344 Compound obtained (yield = 53%).
¾ 丽 (400 MHz, CDC13)5 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 합성예 345 ： N-(4-에틸페닐)ᅳ N-메틸 -l-(2-메틸 -4-니트로벤질) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ δ (400 MHz, CDC1 3 ) 5 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 Synthesis Example 345: N- (4-ethylphenyl) ᅳ N-methyl-l- (2-methyl-4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2-메틸 -4-니트로펜에틸 )— 2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를' DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-에틸 -N- 메틸아닐린 (1.5 mmol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 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 隱 ol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 345 (yield = 67%).
¾ NMRC400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ NMRC400 MHz, CDC1 3 ) 6 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 합성예 346 ： 1-C4-에틸 -2-메틸펜에틸) -N-(4-에틸페닐) -N-메틸 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 346: 1-C4-ethyl-2-methylphenethyl) -N- (4-ethylphenyl ) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-에틸 -2-메틸펜에틸) -2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3ᅳ카복실락 애시드 )(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4—에틸 -N- 메틸아닐린 (1.5 mmol) 및 PyBop(2 議 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 346 화합물을 수득하였다 (수율 =43%)  1- (4-Ethyl-2-methylphenethyl) -2-oxo-1'2-dihydroquinoline-3'carboxylate acid) (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 346 (yield = 43%)
¾ NMR(400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 5 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.?8(s, 2H) , 2.80(m, 6H)， 2.60(m, 4H)， 1.25(s, 3H).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.?8 ( s, 2H), 2.80 (m, 6H), 2.60 (m, 4H), 1.25 (s, 3H).
MASS=452.25 합성예 347 ： N-(4-에틸페닐)— 1— (4-하이드록시 -2-메틸펜에틸) -N-메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 MASS = 452.25 Synthesis Example 347: N- (4-ethylphenyl) -1— (4-hydroxy-2-methylphenethyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-하이드록시 -2-메틸펜에틸) -2-옥소— 1， 2—디하이드로퀴놀린 -3-카복 실릭애시드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4—에틸- N—메틸아닐린 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 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 (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-ethyl-N-methylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 347 (yield = 38%).
¾ 画 R(400' MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ 画 R (400 ' MHz, CDC1 3 ) 5 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 합성예 348 ： N-(4-에틸페닐) -N-메틸 -l-(2—메틸 -4-니트로펜에틸 )-2-옥소ᅳ 1，2NH), 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 Synthesis Example 348: N- (4-ethylphenyl) -N-methyl-l- (2—methyl-4-nitrophenethyl) -2-oxobenzo 1,2
-디하이드로퀴놀린 -3-카르복사마이드 -Dihydroquinoline-3-carboxamide
1-(2-메틸 -4-니트로펜에틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 讓 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸 -N- 메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 쯩안 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 X ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 mmol) and PyBop (2 Pa ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 348 (yield = 67%).
¾ NMRC400 MHz, CDC13) 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ NMRC400 MHz, CDC1 3 ) 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).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 합성예 349 ： 1— (4-에틸 -2-메틸벤질) -N— (4-에틸페닐) -N-메틸— 2-옥소 -1,2- 디하이드로퀴놀린 -3ᅳ카르복사마이드 MASS = 469.20 Synthesis Example 349 ： 1— (4-ethyl-2-methylbenzyl) -N— (4-ethylphenyl) -N-methyl—2-oxo-1,2-dihydroquinoline-3′carboxamide
1— (4ᅳ에틸 -2—메틸벤질) -N-(4-에틸페닐 )-Nᅳ메틸 -2-옥소 -1 , 2-디하이드 로퀴놀린 -3-카르복사마이드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 麵 ol), 4-에틸 -N-메틸아닐린 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 349 화합물을 수득하였다 (수율 =45%). 1— (4 ᅳ ethyl-2—methylbenzyl) -N- (4-ethylphenyl) -N ᅳ methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (1 隱 ol) Dissolved in DMF (2 mL). DIPEA (3 Xol), 4-ethyl-N-methylaniline (1.5 x ol) and PyBop (2 x ol) were added to the reaction mixture and stirred for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 349 (yield = 45%).
¾ MR(400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ MR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H,-
ΝΉ), 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 합성예 350 ： 1- ，3-디메틸벤질) -N-(4-에틸페닐) -N-메틸 -2-옥소 -1，2-디하이 드로퀴놀린 -3-카르복사마이드 ΝΉ), 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 Synthesis Example 350: 1-, 3-dimethylbenzyl) -N- (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydrodroquinoline-3-carboxamide
1-(2， 3-디메틸벤질 )-2-옥소— 1 , 2-디하이드로퀴놀린— 3-카복실릭애시드 1- (2, 3-dimethylbenzyl) -2-oxo— 1, 2-dihydroquinoline— 3-carboxylic acid
(1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEAC3 誦 ol), 4ᅳ에틸 -N-메틸 아닐린 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 350 화합물을 수득하였다 (수율 =45%). (1 μl) was dissolved in DMF (2 mL). DIPEAC3 誦 ol), 4 ᅳ ethyl-N-methyl aniline (1.5 隱 ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 350 compound (yield = 45%).
¾ 匪 R(400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ 匪 R (400 MHz, CDC1 3 ) 5 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).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 합성예 352 ： N-에틸 -N-(4-에틸페닐) -2ᅳ옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 MASS = 424.22 Synthesis Example 352: N-ethyl -N- (4-ethylphenyl) -2oxo-l, 2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸 -N—메틸아닐린 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 352 화합물올 수득하였다 (수율 =76%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N—methylaniline (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 352 (yield = 76%).
¾ 匿 (40O MHz, CDC13)5 8.28(s, 1H), 8.0(s, 1H, -NH)， 7.88(m,¾ 匿 (40O MHz, CDC1 3 ) 5 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 합성예 353 ： 1-(2，5-디메틸벤질) -Nᅳ에틸 -N-(4-에틸페닐) -2—옥소 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 353 ： 1- (2,5-Dimethylbenzyl) -N ᅳ ethyl-N- (4-ethylphenyl) -2—oxo-1,2-dihydroquinoline-3-carboxamide
1-(2， 5-디메틸벤질) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭애시드 1- (2, 5-dimethylbenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid
(1 匪 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), 4ᅳ에틸 -N-메틸 아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이 실리카겔 크로마토그래프로 정제하여 합성예 353 화합 물을 수득하였다 (수율 =45%). (1 μl) was dissolved in DMF (2 mL). DIPEA (3xol), 4xethyl-N-methyl aniline (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. Purification with this silica gel chromatography gave the synthesis example 353 compound (yield = 45%).
¾ 丽 R(400 MHz, CDC13)S 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(111， 2H), 2.60(m, 8H), 1.25(s, 3H). ASS=438.23 합성예 354 ： 1— (3， 4-디메틸벤질) -N-에틸— N-(4-에틸페닐) -2-옥소 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 ¾ δ R (400 MHz, CDC1 3 ) S 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 (111, 2H), 2.60 (m, 8H), 1.25 (s, 3H). ASS = 438.23 Synthesis Example 354 1- (3,4-dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(3， 4-디메틸벤질 )-2-옥소 -1， 2-디하이드로퀴놀린— 3—카복실릭애시드 1- (3, 4-dimethylbenzyl) -2-oxo-1, 2-dihydroquinoline— 3—carboxylic acid
(1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-에틸 -N-메틸 아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 354 화합물을 수득하였다 (수율 =45%). (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), 4-ethyl-N-methyl aniline (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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 354 (yield = 45%).
¾ NMR OO MHz, CDC13)6 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR OO MHz, CDC1 3 ) 6 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 합성예 355 ： 1-(2，6—디메틸벤질) -N-에틸 -N-(4-에틸페닐) -2-옥소 -1,2-디하이 로퀴놀린 -3-카르복사마이드 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, 3 H). MASS = 438.23 Synthesis Example 355: 1- (2,6-Dimethylbenzyl) -N-ethyl -N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2， 6-디메틸벤질 )-2—옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭애시드 (1 謹 ol)를 DMF( mL)에 용해시켰다. DIPEA(3 画 ol), 4-에틸— N—메틸 아닐린 (1.5 醒 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 355 화합 을 수득하였다 (수율 =76%). 1- (2, 6-dimethylbenzyl) -2—oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 謹 ol) was dissolved in DMF (mL). DIPEA (3 画 ol), 4-ethyl- N—methyl aniline (1.5 醒 ol) and PyBop (2 隱 ol) were added to the reaction mixture and at room temperature Stir for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 355 compound (yield = 76%).
¾ NM (400 MHz, CDC13)6 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(iii, 2H), 2.60(m, 8H), i.25(s, 3H). MASS=438.23 합성예 356 ： N-에틸 -N-(4-에틸페닐) -2-옥소 -1-(2，4,6-트리메틸벤질 )-1，2- 디하이드로퀴놀린— 3-카르복사마이드 ¾ NM (400 MHz, CDC1 3 ) 6 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 (iii, 2H), 2.60 (m, 8H), i.25 (s, 3H). MASS = 438.23 Synthesis Example 356 ： N-ethyl -N- (4-ethylphenyl) -2-oxo-1- (2,4,6-trimethylbenzyl) -1,2-dihydroquinoline—3-carboxamide
2-옥소 -1ᅳ(2，4，6-트리메틸벤질 )-1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 睡 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸 -N- 메틸아닐린 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 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' ol) 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 356 (yield = 45%).
¾ 讓 R(400 MHz, CDCls) 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). MASS = 452.25 합성예 357 ： l-(4- (디플루오로메틸) -2-메틸벤질) -N-에틸 -N-(4—에틸페닐) -2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 讓 R (400 MHz, CDCls) 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) .MASS = 452.25 Synthesis Example 357: l- ( 4- (difluoromethyl) -2-methylbenzyl) -N-ethyl-N- (4—ethylphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
1-(4- (디플루오로메틸) -2—메틸벤질) -2—옥소ᅳ 1,2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1 隱 01)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- 에틸— Nᅳ메틸아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 357 화합물을 수득하였다 (수율 =45%). 1- (4- (difluoromethyl) -2—methylbenzyl) -2—oxo ᅳ 1,2-dihydroquinoline-3-carboxylic acid (1 隱0 1) was dissolved in DMF (2 mL). . DIPEA (3 'ol), 4-ethyl-N'methylaniline (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 357 (yield = 45%).
¾ NMRC400 丽 z' CDC13)5 8.28(s, 1H), 8.0(s, 1H, -NH)， 7.88(m,¾ NMRC400 liza z 'CDC1 3 ) 5 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m,
2H), 7.41 (in, 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 합성예 358 ： (E)-l-(2-(4- (디플루오로메틸) 2-메틸사이클로핵사 -2,4-디엔- 1-일리덴)에틸) -N-에틸 -N-(4-에틸페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 2H), 7.41 (in, 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 Synthesis Example 358: (E) -l- (2- (4- (difluoromethyl) 2-methylcyclonucleus-2,4-diene-1-ylidene) ethyl) -N-ethyl-N- (4 -Ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
(E)-l-(2-(4- (디플루오로메틸 ) -2-메틸사이클로핵사— 2， 4-디엔 -1-일리 덴)에틸)—2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 圍 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-에틸— N-메틸아닐린 (1.5 画 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 '정제하여 합성예 358 화합물을 수득하였다 (수율 =45%). (E) -l- (2- (4- (difluoromethyl) -2-methylcyclonucleus— 2,4-diene-1-ylidene) ethyl) —2-oxo-1,2-dihydroquinoline 3-Carboxylic acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3xol), 4-ethyl-N-methylaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Subsequently, silica gel chromatography was used for purification to obtain the compound of Synthesis Example 358 (yield = 45%).
¾ NMR (400 MHz, CDC13)5 8.28(s, 1H) , 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.0 (s, 1H, -NH), 7.88 (m,
2H), 7.41(ITI, 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 합성예 359 ： N-(4-하이드록시페닐) -N-메틸 -2-옥소— 1， 2-디하이드로퀴놀린 -3- 카르복사마이드 2H), 7.41 (ITI, 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, 5 H). MASS = 488.23 Synthesis Example 359: N- (4-hydroxyphenyl) -N-methyl-2-oxo—1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 醒 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 4-에틸 -N-메틸아닐린 (1.5 麵 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 4-ethyl-N-methylaniline (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 359 (yield = 49%).
¾ NMR(400 MHz, CDC13)6 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 합성예 360 ： N-(4-하이드록시페닐) -l-(4-메톡시 -2-메틸벤질) -N-메틸 -2-옥소¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 360: N- (4-hydroxyphenyl) -1-(4-methoxy-2-methylbenzyl) -N-methyl-2-oxo
-1 , 2-디하이드로퀴놀린 -3-카르복사마이드 -1,2-dihydroquinoline-3-carboxamide
1-(4-메톡시 -2-메틸벤질 )-2-옥소 -1 , 2—디하이드로퀴놀린— 3-카복실릭 애시드 (1 醒 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- (메틸 아미노)페놀 (1.5 '隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하고 실리카겔 크로마토그래프로 정제하여 합성예 360 화합물을 수득하였다 (수율 =4¾). 1- (4-methoxy-2-methylbenzyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxylic acid (1 醒 ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4- (methyl amino) phenol (1.5''ol) 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 Synthesis Example 360 compound. Obtained (yield = 4¾).
¾ NMR(400 MHz, CDC13)6 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 합성예 361 ： N-(4-하이드록시페닐) -N-메틸 -2-옥소 -1-(2,3ᅳ4，5，6-펜타메틸 벤질) -1， 2—디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 361: N- (4-hydroxyphenyl) -N-methyl-2-oxo-1- (2,3 ᅳ 4,5,6-pentamethyl benzyl) -1,2-dihydroquinoline -3-carboxamide
2-옥소-1-(2，3，4，5,6-펜타메틸벤질)-1，2ᅳ디하이드로퀴놀린-3—카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- (메틸아 미노)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 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 隱 ol) was dissolved in DMF (2 mL). DIPEA (3xol), 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 361 (yield = 45%).
¾ NMR (400 MHz, CDC13)6 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 합성예 363 ： N-에틸 -N-(4-하이드록시페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 363: N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4- (에틸아미노)페놀 (1.5 mmol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis 363 (yield = 45%).
¾ 丽 R(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H) , 8.0(s, 1H)，¾ δ R (400 MHz, CDC1 3 ) 6 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 합성예 364 ： Ν에틸 -N-(4-하이드톡시페닐) -l-(4-메특시 -2-메틸펜에틸) -2- 옥소 -1， 2-디하이드로퀴놀린 -3—카르복사마이드 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, 3 H). MASS = 308.12 Synthesis Example 364: N-ethyl-N- (4-hydroxyphenyl) -1- (4-methoxy-2-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carr Copyamide
1-(4-메톡시 -2-메틸펜에틸 )-2—옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4-1- (4-methoxy-2-methylphenethyl) -2—oxo-1, 2-dihydroquinoline-3-carboxylic Acid (1 μl) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), 4-
(에틸아미노)페놀 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 364 화합물을 수득하였다 (수율 =47%). (Ethylamino) 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. Then purified by silica gel chromatography to give the compound of Synthesis 364 (yield = 47%).
¾ 證 (400 MHz, CDC13)5 8.28(s, IH), 8.14(ci, IH)， 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-디쩨틸펜에틸) -N-에틸 -N-(4-하이드록시페닐) -2-옥소-¾ 證 (400 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (ci, IH), 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 Synthesis Example 365: 1- (2,3-Dipentylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-
1,2-디하이드로퀴놀린 -3-카르복사마이드 1,2-dihydroquinoline-3-carboxamide
1-(2， 3-디메틸펜에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3—카복실릭애시 드 (1 瞧 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 4- (에틸아미노) 페놀 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔아물을 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 μl) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4- (ethylamino) phenol (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis 365 (yield = 43%).
¾ 證 (400 丽 z, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.0(s, IH),¾ 證 (400 d z, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH),
7.86(dd, 2H), 7.36(m, 2H)， 7.31(mᅳ 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-7.86 (dd, 2H), 7.36 (m, 2H), 7.31 (m ᅳ 2H), 7.14 (m, 2H), 6.93 (dd, 2H), 5.35 (s, IH, -OH), 4.28 (s, 2H ), 3.87 (m, 4 H), 1.31 (m, 9 H). MASS = 440.21 Synthesis Example 366 ： 1- (2,5-Dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-
1， 2-디하이드로퀴놀린— 3—카르복사마이드 1, 2-dihydroquinoline— 3—carboxamide
1-(2， 5-디메틸펜에틸) -2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3—카복실릭애시 드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4— (에틸아미노) 페놀 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 1- (2, 5-Dimethylphenethyl) -2-oxo-1 '2-dihydroquinoline-3-carboxylic acid (1' ol) was dissolved in DMF (2 mL). DIPEA (3 隱 ol), 4— (ethylamino) phenol (1.5 隱 ol) and PyBop (2 隱 ol) were added to the reaction mixture at room temperature
3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 366 화합물을 수득하였'다 (수율 =43%). Stir for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph to give the compound of Synthesis Example 366 ' (yield = 43%).
¾ 醒 (400 MHzᅳ CDC13)5 8.28(s, IH), 8.14(d, IH)ᅳ 8.0(s, IH),¾ 400 (400 MHz ᅳ CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH) ᅳ 8.0 (s, IH),
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 합성예 367 ： 1-(2，6-디메틸펜에틸) -N-에틸 -N-(4-하이드록시페닐) -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 367: 1- (2,6-dimethylphenethyl) -N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(2 , 6-디메틸펜에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭애시 드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol)ᅳ 4- (에틸아미노) 페놀 (1.5 隱 ol) 및 PyBop(2 匪 ol)를 반웅 흔합물에 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 麵 ol) was dissolved in DMF (2 mL). DIPEA (3 'ol)' 4- (ethylamino) phenol (1.5 'ol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 367 (yield = 43%).
¾ NMR(400 MHz, CDC13)5 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 합성예 368 ： N-에틸 -N-(4-하이드록시페닐) -2-옥소 -1-(2，4,6ᅳ트리메틸펜에틸) -1 , 2ᅳ디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 368: N-ethyl-N- (4-hydroxyphenyl) -2-oxo-1- (2,4,6'trimethylphenethyl) -1,2'dihydroquinoline-3-carbox Maid
2-옥소 -1-(2，4，6-트리메틸펜에 ¾)-1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 議 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 4- 2-oxo-1- (2,4,6-trimethylphene ¾) -1,2-dihydroquinoline-3-carboxylic acid (1 議 ol) was dissolved in DMF (2 mL). DIPEA (3 画 ol), 4-
(에틸아미노)페놀 (1.5 画 ol) 및 PyBop(2 匪 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 368 화합물을 수득하였다 (수율 =43 . (Ethylamino) phenol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 368 (yield = 43.
¾ NMRC400 MHz, CDC13)5 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 합성예 369 ： N-메틸 -N-(4-니트로페닐) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMRC400 MHz, CDC1 3 ) 5 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 Synthesis Example 369 ： N-methyl-N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25''화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), N—메틸 -4-니트로아닐린 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 '' Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), N-methyl-4-nitroaniline (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained Extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 369 (yield = 49%).
¾ 證 (400 丽 z, CDC13)6 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 합성예 370: N-메틸 -N-(4-니트로페닐) -2-옥소 -1-(2，3，4,5，6-펜타메틸펜에틸) -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 400 (400 d z, CDC1 3 ) 6 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 Synthesis Example 370: N-methyl-N- (4-nitrophenyl) -2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) -1,2-dihydroquinoline -3-carboxamide
2-옥소 -1-(2 ,3,4,5, 6-펜타메틸펜에틸 )ᅳ1， 2-디하이드로퀴놀린 -3-카복 실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N-메틸- 4-니트로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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) x1, 2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), N-methyl-4-nitroaniline (1.5 mmol) and PyBop (2 μl ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 370 (yield = 49%).
¾ NMRC400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, ―¾ NMRC400 MHz, CDC1 3 ) 6 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) -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 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, 15 H). MASS = 497.23 Synthesis Example 371: N-ethyl-N- (4-nitrophenyl) -2ioxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 誦 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 mmol), N_에틸— 4-니트로아닐린 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEM 3 mmol), N_ethyl—4-nitroaniline (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 371 (yield = 53%).
¾ 讓 R(400 MHz, CDC13)8 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 합성예 372 ： N-(4-(N,N-디메틸설파모일)페닐) -N-메틸 -2-옥소 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), N—에틸 -4-니트로아닐린 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 371 화합물을 수득하였다 (수율 =53%). ¾ 讓 R (400 MHz, CDC1 3 ) 8 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 Synthesis Example 372: N- (4- (N, N-dimethylsulfamoyl) phenyl) -N-methyl-2-oxo-1,2-dihydrodroquinoline-3-carboxamide Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), N—ethyl-4-nitroaniline (1.5 μl ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 371 (yield = 53%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H) , 8.0(s, iH, - 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 합성예 373 ： N— (4-(N,N-디메틸설파모일)페닐) N-에틸 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, iH,-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 Synthesis Example 373 ： N— (4- (N, N-dimethylsulfamoyl) phenyl) N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 誦 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), Ν,Ν-디메틸 -4- (메틸아미노)벤젠설폰아미드 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), Ν, Ν-dimethyl-4- (methylamino) benzenesulfonamide (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 373 (yield = 51%).
¾ 匿 (400 MHz, CDC13)5 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(1:, 1H)， 6.93(dd, 2H), 3.44(s, 3H), 2.66(m, 6H), 1.31(s, 3H). MASS=399.13 합성예 374 ： N-(4- (하이드록시메틸)페닐) -Nᅳ메틸 -2-옥소 -1,2-디하이드로 퀴놀린 -3—카르복사마이드 ¾ 匿 (400 MHz, CDC1 3 ) 5 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 (1 :, 1H), 6.93 (dd, 2H), 3.44 (s, 3H), 2.66 (m, 6H), 1.31 (s, 3H). MASS = 399.13 Synthesis Example 374: N- (4- (hydroxymethyl) phenyl) -N ᅳ methyl-2-oxo-1,2-dihydroquinoline-3—carboxamide
합성예 25 화합물 (1 腿 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4- (메틸아미노)페닐)메탄을 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methane (1.5 mmol) and PyBop (2 μL) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 374 (yield = 59%).
¾ 匿 (400' MHz, CDC13)5 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 합성예 375 ： 1-(4-(1Η-피라졸 1-일)벤질) -N-(4- (하이드록시메틸)페닐) -N- 메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匿 (400 'MHz, CDC1 3 ) 5 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 Synthesis Example 375: 1- (4- (1Η-pyrazol 1-yl) benzyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo-1,2-dihydroquinoline- 3-carboxamide
1-(4-( 1H-피라졸 -1ᅳ일 )벤질 )-2ᅳ옥소ᅳ1， 2ᅳ디하이드로퀴놀린 -3-카복실 릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4- (메틸아미노)페닐)메탄올 (1.5 隱 ol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 375 화합물을 수득하였다 (수율 =63%).  1- (4- (1H-pyrazol-1xyl) benzyl) -2 ᅳ oxox1,2'dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4- (methylamino) phenyl) methanol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 375 (yield = 63%).
¾ NMR(400 MHz, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, - 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), 4.28(s, 2H), 3.65(s, IH, -OH), 3.44(s, 3H), 2.87(m, 3H). MASS=464.18 합성예 376 ： 1-(4-(1Η-피라졸 -1-일)벤조일) -N— (4- (하이드록시메틸)페닐) -N— 메틸— 2-옥소 -1,2-디하이드로퀴놀린— 3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH,-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), 4.28 (s, 2H), 3.65 (s, IH, -OH), 3.44 (s, 3H), 2.87 (m, 3 H). MASS = 464.18 Synthesis Example 376 ： 1- (4- (1Η-pyrazol-1-yl) benzoyl) -N— (4- (hydroxymethyl) phenyl) -N— methyl— 2-oxo-1,2- Dihydroquinoline— 3-carboxamide
1-(4-( 1H-피라졸 -1ᅳ일)벤조일 )ᅳ2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복실릭 애시드 (1麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3隱 ol)ᅳ (4- (메틸아미노)페닐)'메탄올 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 376 화합물을 수득하였다 (수율 =43%).  1- (4- (1H-pyrazol-1xyl) benzoyl) x2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1x ol) was dissolved in DMF (2 mL). DIPEA (3 'ol)' (4- (methylamino) phenyl) 'methanol (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 376 (yield = 43%).
¾ NMR (400 MHz, CDC13)8 8.28(s, IH), 8.14(d, IH), 8.0(s, IH, - 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(s, IH, -OH), 3.44(s, 3H) , 2.87(m, 3H). MASS=478.16 합성예 377 ： 1-(2，2-디페닐아세틸) -N-(4- (하이드록시메틸)페닐) -N-메틸ᅳ 2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 8 8.28 (s, IH), 8.14 (d, IH), 8.0 (s, IH,-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 (s, IH, -OH), 3.44 (s, 3H), 2.87 (m, 3H). MASS = 478.16 Synthesis Example 377: 1- (2,2-diphenylacetyl) -N- (4- (hydroxymethyl) phenyl) -N-methyl '2-oxo-1, 2-dihydroquinoline-3- Carboxamide
1-(2 , 2-디페닐아세틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (4- (메틸아미노)페닐)메탄올 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 377 화합물을 수득하였다 (수율 =59%). 1- (2,2-diphenylacetyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), (4- (methylamino) phenyl) methanol (1.5mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was ethyl Extracted with acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 377 (yield = 59%).
¾ NMR(400 MHz, CDG13)5 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(111， 2H), 3.65(s, 1H, -OH), 3.44(s, 3H), 2.80(s, 1H). MASS=502.19 합성예 378 ： l-(2,2-디페닐에틸) -N-(4- (하이드록시메틸)페닐) -Nᅳ메틸 -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDG1 3 ) 5 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 (111, 2H), 3.65 (s, 1H, -OH), 3.44 (s, 3H), 2.80 (s, 1H). MASS = 502.19 Synthesis Example 378 ： l- (2,2-diphenylethyl) -N- (4- (hydroxymethyl) phenyl) -N ᅳ methyl-2-oxo-1,2-dihydroquinoline-3- Carboxamide
1-(2, 2-디페닐에틸) -2—옥소 -1， 2-디하이드로퀴놀린 -3- 카복실릭애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 οΠ, (4- (메틸아미노)페닐)메탄올 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물올 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 378 화합물을 수득하였다 (수율 =7 ).  1- (2, 2-diphenylethyl) -2—oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). DIPEA (3 瞧 οΠ, (4- (methylamino) phenyl) methanol (1.5 隱 ol) and PyBop (2 画 ol) were added to the reaction mixture and stirred for 3 hours at room temperature. Extraction with water was followed by purification with silica gel chromatography to give Synthesis Example 378 compound (yield = 7).
¾ NMR(400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H) , 8.0(s, 1H, -¾ NMR (400 MHz, CDC1 3 ) 5 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 '.. 합성예 381 ： N-에틸 -N— (4- (하이드록시메틸)페닐) -2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 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 '. . Synthesis Example 381 ： N-ethyl-N— (4- (hydroxymethyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (4- (메틸아미노)페닐)메탄을 (1.5 mmol) 및 PyBop(2 闘 ol)를 반응 흔합물에 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), (4- (methylamino) phenyl) methane (1.5mmol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 381 (yield = 72%).
¾ 賺 (400 顧 z, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, - NH), 7.39(dd, 2HX, 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 합성예 382 ： N—메틸 -2-옥소 -N-(4-비닐페닐) -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 400 (400 顧 z, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.0 (s, 1H,-NH), 7.39 (dd, 2HX, 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 Synthesis Example 382 N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3- Carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 醒 ol), (4- (메틸아미노)페닐)메탄올 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), (4- (methylamino) phenyl) methanol (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 382 (yield = 46%).
¾ NMR(400 MHz, CDC13)6 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 합성예 384 ： N-에틸 -2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 384: N-ethyl 2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 匪 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (4— (메틸아미노)페닐)메탄올 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (4— (methylamino) phenyl) methanol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 384 (yield = 77%).
¾ NMRC400 MHz, CDC13)5 9.23(dd, 2H), 8.28(d, 1H), 8.14(d, 1H), 8.0(sᅳ 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 합성예 385 ： N-에틸 -2-옥소— 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMRC400 MHz, CDC1 3 ) 5 9.23 (dd, 2H), 8.28 (d, 1H), 8.14 (d, 1H), 8.0 (s ᅳ 1H), 7.88 (dd, 2H), 7.31 (t, 1H), 7.14 (t, 1 H), 6.63 (s, 1 H), 5.61 (s, 1 H), 5.18 (s, 1 H), 4.28 (m, 2 H), 1.31 (s, 3 H). MASS = 318.14 Synthesis Example 385 ： N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 隱 ol), 에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 쎄틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 385 화합물을 수득하였다 (수율 =79%).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEM3 隱 ol), ethanamine (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with cetyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 385 (yield = 79%).
¾ 匪 R(400MHz,CDCl3)S 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 합성예 389: N- (메톡시메틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 메록시메타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 389 화합물을 수득하였다 (수율 =79¾>). ¾ 匪 R (400MHz, CDCl 3 ) S 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 Synthesis Example 389: N- (methoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), methoxymethamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 389 (yield = 79¾>).
¾ NMRC400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, iH, - 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 합성예 390: N- (브로모메틸 )-2-옥소 -1，2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol)ᅳ 브로모메타나민 (1.5 瞧 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 390 화합물을 수득하였다 (수율 =69%) ¾ NMRC400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, iH,-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 Synthesis Example 390: N- (bromomethyl) -2-oxo-1,2 -Dihydroquinoline-3-carboxamide Synthesis Example 25 Compound (1 'ol) was dissolved in DMF (2 mL) DIPEA (3' ol) 'bromomethamine (1.5' ol) and PyBop (2 ') ol) was added to the reaction mixture and stirred for 3 hours at room temperature The obtained residue was extracted with ethyl acetate and water and then purified by silica gel chromatography to give Synthesis Example 390 compound (yield = 69%).
¾ 賺(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, - NH), 8.0 (s, ΙΗ,,-ΝΗ), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.59(m, 2H). MASS= 232.08 합성예 391 ： N- (클로로메틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ 400 (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-NH), 8.0 (s, ΙΗ ,,-ΝΗ), 7.36 (d, 1H ), 7.31 (t, 1 H), 7.14 (t, 1 H), 3.59 (m, 2 H). MASS = 232.08 Synthesis Example 391: N- (chloromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (l mmol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 議 ol)ᅳ 클로로메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (l mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol)' chloromethamine (1.5 mmol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 391 (yield = 69%).
¾ NMR(400 MHz, CDC13)6 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 합성예 392 ： N- (플루오로메틸) -2—옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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, 1 H), 7.14 (t, 1 H), 3.59 (m, 2 H). MASS = 236.04 Synthesis Example 392: N- (fluoromethyl) -2—oxo-1,2-dihydroquinoline-3-carbox Maid
합성예 25 화합물 (1 腿 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 플루오로메타나민 (1.5 隱 ol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), fluoromethanamin (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 392 (yield = 43%).
¾ 匪 R(400'丽 z, CDC13)6 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 합성예 393 ： N- (하이드록시메틸) -2—옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ 匪 R (400 ' z, CDC1 3 ) 6 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 Synthesis Example 393 ： N- (hydroxymethyl) -2—oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 mmol), 아미노메탄을 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEM 3 mmol), aminomethane (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 393 (yield = 56%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 394 ： N- (니트로메틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthetic Example 394: N- (nitromethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 腿 ol), 니트로메타나민 (1.5 mmol) 및 PyBop(2 誦 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 μl ol), nitromethanamin (1.5 mmol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 394 (yield = 43%).
¾ NMR(400 MHz, CDC13)5 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 합성예 396 ： N-(2-하이드록시에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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, 1 H), 7.14 (t, 1 H), 3.59 (m, 2 H). MASS = 247.06 Synthesis Example 396: N- (2-hydroxyethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-아미노에탄을 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-aminoethane (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 396 (yield = 49%).
¾賺 (400 MHz, CDC13)5 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 합성예 397 ： 2-옥소 -N-프로필 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 397 ： 2-oxo-N-propyl-1, 2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 프로판 -1-아민 (1.5 mmol) 및 PyBop(2 隱 όΐ)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), propane-1-amine (1.5 mmol) and PyBop (2 2 όΐ) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 397 (yield = 44%).
¾ 画 R(400 MHz, CDC13)8 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, - NH), 8.0 (sᅳ 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 합성예 399 ： (E)-2-옥소 -N- (프로프 -1-엔 -1-일) -1，2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 画 R (400 MHz, CDC1 3 ) 8 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-NH), 8.0 (s ᅳ 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 Synthesis Example 399: (E) -2-oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 醒 ol), (E)-프로프 -1—엔 -1-아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEAC3 醒 ol), (E) -prop-1-en-1-amine (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 399 (yield = 53%)
¾ NM (400 腿 z, CDC13)6 8.28(s, 1H, -NH), 8.14(d, 1H), 8.0(s,¾ NM (400 Hz, CDC1 3 ) 6 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). MASS= 228.09 합성예 402 ： N-(2-메록시에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 2H, -NH), 7.31 (t, 1H), 7.14 (t, 1H), 7.11 (s, 1H), 5.13 (s, 1H), 2.05 (s, 1H). MASS = 228.09 Synthesis Example 402: N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-메톡시에타나민 (1.5 薩 ol) 및 PyBop(2 瞧 ol)를 반웅 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-methoxyethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 402 (yield = 59%).
NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -NMR (400 MHz, CDC1 3 ) 6 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 합성예 403 ： N-(2-브로모에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 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 Synthesis Example 403: N- (2-bromoethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 匪 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 로모에타나민 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이토 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 403 화합물을 수득하였다 (수율 = 63%) .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), lomoethanamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 403 compound (yield = 63%).
¾ 匪 R(400 MHz, CDC13)6 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 합성예 405 ： N-(2—클로로에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 405: N- (2—Chloroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25,.화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2—클로로에타나민 (1.5 mmol) 및 PyBop(2 醒 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 405 화합물을 수득하였다 (수율 =63%). ¾ 賺 (400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, ᅳ 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 합성예 406 ： N-(2-플루오로에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 Synthesis Example 25. Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2—chloroethanamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 405 (yield = 63%). ¾ 賺 (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, ᅳ NH), 8.0 (s, 1H,-NH), 7.36 (d, 1H) , 7.31 (t, 1 H), 7.14 (t, 1 H), 3.76 (m, 2 H), 3.04 (m, 2H). MASS = 250.05 Synthesis Example 406 ： N- (2-fluoroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25:화합물 (1 mmol)을 DMF(2 mL)에 용해시찼다. DIPEA(3 瞧 ol), 2-플루오로에타나민 (1.5 醒 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 -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: Compound (1 mmol) was dissolved in DMF (2 mL). DIPEA (3xol), 2-fluoroethanamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 406 (yield = 49%).
¾ 匪 R(400 MHz, CDC13)6 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 합성예 407 ： N-(2-하이드록시에틸) -2-옥소 -1， 2—디하이드로퀴놀린 -3-카르복 사마이드 , ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 407: N- (2-hydroxyethyl) -2-oxo -1, 2—dihydroquinoline-3-carboxamide,
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPE 3 誦 ol), 2-아미노에탄을 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPE 3 x ol), 2-aminoethane (1.5 mmol) and PyBop (2 x ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 407 (yield = 72%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, ᅳ 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 합성예 408 ： , N-(2-니트로에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, ᅳ 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 Synthesis Example 408:, N- (2-nitroethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPE/ 3 mmol), 2-니트로에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPE / 3 mmol), 2-nitroethanamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained was ethyl Extracted with acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 408 (yield = 71%).
賺 (400 MHz, CDC13)6 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 합성예 409 ： N—C3-하이드록시프로필) -2—옥소 -1,2-디하이드로퀴놀린 -3-카르 복사마이드 400 (400 MHz, CDC1 3 ) 6 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, 1 H), 7.14 (t, 1 H), 3.76 (m, 2 H), 3.04 (m, 2H). MASS = 261.07 Synthesis Example 409 ： N—C3-hydroxypropyl) -2—oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 3-아미노프로판 -1ᅳ올 (1.5 隱 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 3-aminopropane-1xol (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 409 (yield = 43%).
¾ 匪 R(400 MHz, CDC13)6 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)ᅳ 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-카르 복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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) ᅳ 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H). MASS = 246.10 Synthesis Example 410: (E) -2-oxo-N- (pent-3-en-1-yl) -1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF 2 mL)에 용해시켰다. DIPEAC3 隱 ol), (E)-펜트 -3-엔 -1-아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 410 화합물을 수득하였다 (수율 = 71%) .  Synthesis Example 25 Compound (1xol) was dissolved in 2 mL of DMF). DIPEAC3 'ol), (E) -pent-3-ene-1-amine (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 410 compound (yield = 71%).
¾ NMR (400 MHz, CDC13)5 8.28(s, 1H) , 8.14(d, 1H)， 8.03(s, 1H, ―¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 411 ： N-부틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 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, 2 H), 2.05 (s, 3 H). MASS = 256.12 Synthesis Example 411: N-butyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), 부탄 -1-아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 瞧 ol), butane-1-amine (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture Stir at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 411 (yield = 49%).
¾ NMR(400 MHz, CDC13)6 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 합성예 412 ： N-(3-메록시프로필 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 412 ： N- (3-methoxypropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 inL)에 용해시켰다. DIPEAC3 瞧 ol), 3-메톡시프로판ᅳ1-아민 (1.5 mmol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 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 'ol) was dissolved in DMF (2 inL). DIPEAC3 'ol), 3-methoxypropane # 1-amine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 412 (yield = 56%).
¾ 匪 R(400 MHz, CDC13)6 8.28(s, 1H) , 8.14(d, 1H), 8.03(s, 1H, -¾ 匪 R (400 MHz, CDC1 3 ) 6 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 합성예 413 ： N-(3-브로모프로필 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마아드 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, 2 H), 1.31 (m, 2 H). MASS-260.12 Synthesis Example 413: N- (3-bromopropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEM3 隱 ol), 3-브로모프로판 -1-아민 (1.5 隱 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 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 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEM3 'ol), 3-bromopropane-1-amine (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 413 (yield = 81%).
¾ 腿 (400 MHz, CDC13)5 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 합성예 414 : N-(3-클로로프로필 )—2-옥소 -1， 2-디하이드로퀴놀린— 3-카르복사 마이드 합성예 25 화합물 (1 議 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 mmol), 3-클로로프로판 -1-아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 414 화합물을 수득하였다 (수율 =81%). ¾ 腿 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 414 N- (3-chloropropyl) —2-oxo-1, 2-dihydroquinoline—3-carboxamide Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEM 3 mmol), 3-chloropropane-1-amine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 414 (yield = 81%).
¾ NMR(400,MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 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-카르복 사마이드 ¾ NMR (400, MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH ), 7.31 (t, IH), 7.14 (t, IH), 3.18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 264.07 Synthetic Example 415: N- (3-fluoropropyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEM3 画 ol), 3-플루오로프로판— 1-아민 (1.5 mmol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEM3 画 ol), 3-fluoropropane—1-amine (1.5 mmol) and PyBop (2 睡 ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 415 (yield = 49%).
¾ NMR OO MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 7.31(t, IH) , 7.14(1:， IH), 3,18(m, 2H), 1.51(m, 2H), 1.31(m, 2H). MASS=248.10 합성예 416 ： (E)-N- (핵스 -4—엔 -1-일) -2-옥소 -1，2-디하이드로퀴놀린 -3-카르 복사마이드 ¾ NMR OO MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (1 :， IH), 3,18 (m, 2H), 1.51 (m, 2H), 1.31 (m, 2H). MASS = 248.10 Synthesis Example 416: (E) -N- (nux-4—en-1-yl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol)ᅳ (E)-핵스 -4-엔ᅳ 1-아민 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 혼합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제 하여 합성예 416 화합물을 수득하였다 (수율 = 71%) .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 ′ ol) ′ (E) -nux-4-en-1-amine (1.5 mmol) and PyBop (2 ′ ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 416 (yield = 71%).
¾ 匿 (400 MHz, CDC13)5 8.28(s, IH, -NH), 8.14(d, IH), 8.03(s, IH, -NH), 8.0(s, IH, -NH), 7.31(t, IH), 7.14(t, IH), 5.48(d, 2H), 3.18(m, 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—카르 복사마이드 ¾ 匿 (400 MHz, CDC1 3 ) 5 8.28 (s, IH, -NH), 8.14 (d, IH), 8.03 (s, IH, -NH), 8.0 (s, IH, -NH), 7.31 (t , IH), 7.14 (t, IH), 5.48 (d, 2H), 3.18 (m, 2H), 2.18 (m, 2H), 2.05 (s, 3H), 1.69 (m, 2H). MASS = 270.14 Synthesis Example 417: N- (3-hydroxypropyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 mmol), 3-아미노프로판 -1-올 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 417 화합물을 수득하였다 (수율 =71%).  Synthesis Example 25 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEAC3 mmol), 3-aminopropan-1-ol (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 417 (yield = 71%).
¾ NMR (400 MHz, CDC13)5 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H - H), 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 합성예 418 ： N-(3-니트로프로필 )-2-옥소 -1， 2-디하이드로퀴놀린 _3-카르복사 마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H-H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1 H), 7.14 (t, 1 H), 3.65 (s, 1 H, -OH), 3.50 (m, 2H), 3.18 (m, 2H), 1.58 (m, 2H). MASS = 246.10 Synthesis Example 418: N- (3-nitropropyl) -2-oxo-1, 2-dihydroquinoline _3-carboxamide
합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 3-니트로프로판 -1-아민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mu ol), 3-nitropropane-1-amine (1.5 mmol) and PyBop (2 mmol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 418 (yield = 46%).
¾ 丽 (400 MHz, CDC13)6 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 합성예 419 ： N-(4-하이드특시부틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ δ (400 MHz, CDC1 3 ) 6 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 Synthesis Example 419: N- (4-Hydroxybutyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 醒 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 誦 ol), 4-아미노부탄ᅳ 1-올 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에탈 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 419 화합물을 수득하였다 (수율 = 68%)  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 4-aminobutane' 1-ol (1.5 mmol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethal acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 419 (yield = 68%).
¾ MR (400 MHz, CDC13)8 8.28(s, 1H), 8.14(s, 1H), 8.03(s, 1H, -¾ MR (400 MHz, CDC1 3 ) 8 8.28 (s, 1H), 8.14 (s, 1H), 8.03 (s, 1H,-
NH), 8.0(s, 1Hᅳ -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H), 3.65(s, IH, -OH), 3.50(s, 2H), 3.18(m, 2H), 1.53(m, 2H) , 1.52(m, 2H). MASS = 260.12 합성예 420 ： N-(3, 4-디하이드록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 NH), 8.0 (s, 1H ᅳ -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H), 3.65 (s, IH, -OH), 3.50 (s, 2H), 3.18 (m, 2H), 1.53 (m, 2H), 1.52 (m, 2H). MASS = 260.12 Synthesis Example 420: N- (3,4-dihydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 :화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol)ᅳ 4- (아미노메틸)벤젠 -1,2-디올 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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: Compound (1瞧ol) was dissolved in DMF (2 mL). DIPEA (3'ol) '4- (aminomethyl) benzene-1,2-diol (1.5'ol) and PyBop (2'ol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 420 (yield = 49%).
¾ 匿 (400 MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - H), 8.0(s, IH, -NH), 7.36(d, IH), 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-카르복사 마이드 ¾ 匿 (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH, -H), 8.0 (s, IH, -NH), 7.36 (d, IH) 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 Synthetic Example 421: N- (3,4-diethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 醒 ol)올 DMF(2 tnL)에 용해시켰다. DIPEA(3 隱 ol), (5，6,7，8-테트라하이드로나프탈렌 -2-일)메타나민 (1.5 mmol) 및 PyBop(2薩 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 420화합물을 수득하였다 (수율 =67%).  Synthesis Example 25 Compound (1'ol) ol was dissolved in DMF (2 tnL). DIPEA (3 隱 ol), (5,6,7,8-tetrahydronaphthalen-2-yl) methanamine (1.5 mmol) and PyBop (2 薩 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. It was. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 420 compound (yield = 67%).
¾ 匪 R(400 MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 7.12(d, IH), 7.11(s, IH), 7.00 1， IH), 2.60(m, 4H), 1.25(s, 6H). MASS=334.17 합성예 422 ： N-(3, 4-디메틸벤질)—2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH ), 7.31 (t, IH), 7.14 (t, IH), 7.12 (d, IH), 7.11 (s, IH), 7.00 1, IH), 2.60 (m, 4H), 1.25 (s, 6H). MASS = 334.17 Synthesis Example 422: N- (3,4-dimethylbenzyl) —2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 醒 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), (3，4-디메틸페닐)메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), (3,4-dimethylphenyl) methamine (1.5 mmol) and PyBop (2 μL) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Silica gel chromatography Purification gave the compound of Synthesis Example 422 (yield = 71%).
¾ NMR(400 MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0(s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 6.99(d, IH), 6.98 (s, IH), 6.92(d, IH), 4.34(m, 2H), 2.34(s, 6H). MASS=306.14 합성예 423 ： N-(3, 4-디하이드록시펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH) , 7.31 (t, IH), 7.14 (t, IH), 6.99 (d, IH), 6.98 (s, IH), 6.92 (d, IH), 4.34 (m, 2H), 2.34 (s, 6H). MASS = 306.14 Synthesis Example 423: N- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 圍 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 4— (2-아미노에틸)벤젠 -1，2-디올 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 423 (yield = 63%).
¾ 應 R( 400 MHz, CDC13)6 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 6.86(s, IH), 6.68(d, IH), 6.73(d, IH) , 5.35(s, 2H, -OH), 3.55(m, 2H), 2.83(m, 2H). MASS=324.11 '： 합성예 428 ： N-(3, 4-디에틸펜에틸 )-2—옥소 -1,2-디하이드로퀴놀린 -3—카르복 사마이드 ¾ 應 R (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH ), 7.31 (t, IH), 7.14 (t, IH), 6.86 (s, IH), 6.68 (d, IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), 3.55 (m , 2H), 2.83 (m, 2H). MASS = 324.11 ' : Synthesis example 428: N- (3,4-diethylphenethyl) -2—oxo-1,2-dihydroquinoline-3—carboxamide
합성예 25 화합물 (1 画 ol)을 DMF(2 niL)에 용해시켰다. DIPE 3 隱 ol)ᅳ 2-(3,4-디에틸페닐)에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1 μL) was dissolved in DMF (2 niL). DIPE 3 'ol)' 2- (3,4-diethylphenyl) ethanamine (1.5 mmol) and PyBop (2 'ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 428 (yield = 57%).
¾ NMR(400 MHz, CDC13)8 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, -¾ NMR (400 MHz, CDC1 3 ) 8 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-
NH), 8.0 (sᅳ ΙΗ,' -NH), 7.36(d, IH), 7.31(t, IH), 7.19(d, IH) , 7.17(s, IH), 7.14(t, IH), 3.55(m, 2H)， 2.83(m, 2H), 2.60(m, 4H), 1.25(m, 6H). MASS=348.18 합성예 429 ： N-(3, 4-디메틸펜에틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 합성예 25 화합물 (1 翻 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(3,4-디메틸페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 mmol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. Λ 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 429 화합물을 수득하였다 (수율 =62%). NH), 8.0 (s ᅳ ΙΗ, ' -NH), 7.36 (d, IH), 7.31 (t, IH), 7.19 (d, IH), 7.17 (s, IH), 7.14 (t, IH), 3.55 (m, 2H), 2.83 (m, 2H), 2.60 (m, 4H), 1.25 (m, 6H). MASS = 348.18 Synthesis Example 429 ： N- (3,4-dimethylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (3,4-dimethylphenyl) ethanamine (1.5 μl) and PyBop (2 mmol) were added to the reaction mixture and stirred at room temperature for 3 hours. Λ The residue obtained was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 429 (yield = 62%).
¾ NMR (400 MHz, CDC13)68.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH¾ NMR (400 MHz, CDC1 3 ) 68.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH
-NH), 7.36(d, IH), 7.31(t, IH), 7.14(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). MASS = 320.15 합성예 430 ： N- (벤조 [d] [1,3]디옥솔 -5-일메틸 )-2-옥소 -12—디하이드로 퀴놀린 -3-카르복사마이드 -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (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). MASS = 320.15 Synthesis Example 430: N- (benzo [d] [1,3] dioxol-5-ylmethyl) -2-oxo-12-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 議 ol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 mmol), 벤조 [d][l, 3]디옥솔 -5-일메타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아^테이트 및 물로 추출하였다. 이후 실리카겔 크로마토 그래프로 정제하여 합성예 430 화합물을 수득하였다 (수율 =기¾).  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEAC 3 mmol), benzo [d] [l, 3] dioxol-5-ylmethanamin (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 430 (yield = group ¾).
¾ 丽(400 MHz, CDC13)5 8.28(s, IH), 8.14(d, IH), 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 7.03(s, IH), 6.81(d, IH), 6.76(d, IH), 6.07(s, 2H), 4.34(m, 2H). MASS=322.10 합성예 431 ： N-(2- (벤조 [d][l,3]디옥솔 -5-일)에틸) 2-옥소 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ δ (400 MHz, CDC1 3 ) 5 8.28 (s, IH), 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH) , 7.31 (t, IH), 7.14 (t, IH), 7.03 (s, IH), 6.81 (d, IH), 6.76 (d, IH), 6.07 (s, 2H), 4.34 (m, 2H). MASS = 322.10 Synthesis Example 431: N- (2- (benzo [d] [l, 3] dioxol-5-yl) ethyl) 2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 画 οθ을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2- (벤조 [d][l,3]디옥솔 -5-일)에타나민 (1.5 麵 ol) 및 . PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1 画 οθ was dissolved in DMF (2 mL) DIPEA (3 mmol), 2- (benzo [d] [l, 3] dioxol-5-yl) ethanamine (1.5 麵 ol) PyBop (2 μL ol) was added to the reaction mixture and stirred for 3 hours at room temperature The obtained residue was extracted with ethyl acetate and water, and then purified by silica gel chromatography to obtain the Synthesis Example 431 compound. (Yield = 53%).
¾ NMR(400 MHz, CDC13)5 8.28(s, IH) 8.14(d, IH) , 8.03(s, IH, - NH), 8.0 (s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t IH) , 7.03(s, IH), 6.81(d, IH), 6.76(d, IH), 6.07(s, 2H) , 4.34(m, 2H), 3.4(m, 2H). MASS=336.11 합성예 432 ： N- (나프탈렌— 2-일메틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 8.28 (s, IH) 8.14 (d, IH), 8.03 (s, IH,-NH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t IH), 7.03 (s, IH), 6.81 (d, IH), 6.76 (d, IH), 6.07 (s, 2H), 4.34 (m, 2H), 3.4 ( m, 2H). MASS = 336.11 Synthesis Example 432: N- (naphthalene- 2-ylmethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 01)， 나프탈렌:2-일메타나민 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3x01), naphthalene : 2-ylmethamine (1.5xol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 432 (yield = 43%).
¾ 丽 R(400 MHz, CDC13)5 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 합성예 433 ： N-(2- (나프탈렌 -2-일)에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ δ R (400 MHz, CDC1 3 ) 5 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, 1 H), 7.14 (t, 1 H), 4.45 (m, 2 H). MASS = 328.12 Synthesis Example 433: N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 隱 ol)올 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), 2- (나프탈렌 -2-일)에타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반응 흔합물에 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 Compound (1'ol) ol was dissolved in DMF (2 mL). DIPEA (3xol), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 433 (yield = 71%).
¾ NMR(400 MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, - NH), 8.01(d, 1H), 8.0(s, lH, -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 합성예 437 ： Ν-ί[1,1'-비페닐 ]-4-일메틸 )-2-옥소 -1,2-디하이드로퀴놀린 _3ᅳ 카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-NH), 8.01 (d, 1H), 8.0 (s, lH, -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, 1 H), 7.14 (t, 1 H), 3.55 (m, 2 H), 2.94 (m, 2H). MASS = 342.14 Synthesis Example 437 Ν-ί [1,1'-biphenyl] -4-ylmethyl) -2-oxo-1,2-dihydroquinoline _3'carboxamide
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 mmol), 비페닐 ]-4-일메타나민 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEAC3 mmol), biphenyl] -4-ylmethanamin (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Silica gel chromatography Purification gave Synthesis Example 437 compound (yield = 71%).
¾ 證 (400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, 一 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 ¾ 證 (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H, one 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
,  ,
합성예 438 ： N— (2-([1，1'_비페닐] -4-일)에틸) -2-옥소 _1，2-디하이드로 퀴놀린 -3-카르복사마이드 Synthesis Example 438: N— (2-([1,1'_biphenyl] -4-yl) ethyl) -2-oxo _1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 睡 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-([1，1'-비페닐 ]-4-일)에타나민 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-([1,1'-biphenyl] -4-yl) ethanamine (1.5 mmol) and PyBop (2 瞧 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. . The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 438 (yield = 53%).
¾ 麵 R(400 MHz, CDC13)5 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 합성예 439: N-(4-벤질벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 睡 ol), (4-벤질페닐)메타나민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 439 화합물을 수득하였다 (수율 =71%). ¾ 麵 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 439: N- (4-benzylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 Dissolving compound (1 瞧 ol) in DMF (2 mL) I was. DIPEA (3 'ol), (4-benzylphenyl) methamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 439 (yield = 71%).
¾ 匪 R(400 MHz, CDC13)6 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 합성예 440 ： N-(4-벤질펜에틸) -2-옥소 -1，2-디하이드로퀴놀린 -3-카르복사마 이드 ' ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 440: N- (4-benzylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide '
합성예 25 화합물 (1 隱 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2— (4-벤질페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2— (4-benzylphenyl) ethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The residue obtained Extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 440 compound (yield = 64%).
¾ 匪 R(400 MHz, CDC13)5 8.28(sᅳ 1H), 8.14(d, 1H), 8.03(sᅳ 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. Km, 2H), 2.94(m, 2H). MASS=382.17 합성예 441: N- (에특시메틸 )-2-옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 합성예 25 화합물 (1 画 ol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 隱 01)， 에특시메타나민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 441 화합물을 수득하였다 (수율 = 52%). ¾ 匪 R (400 MHz, CDC1 3 ) 5 8.28 (s ᅳ 1H), 8.14 (d, 1H), 8.03 (s ᅳ 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. Km, 2H) , 2.94 (m, 2 H). MASS = 382.17 Synthesis Example 441: N- (ethoxymethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide Synthesis Example 25 A compound (1 'ol) was dissolved in DMF (2 mL). . DIPEAC3 隱 01), especialimethanamine (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. Then purified by silica gel chromatography to give the compound of Synthesis Example 441 (yield = 52%).
¾ NMR 400 MHz, CDC13)5 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(sᅳ 3H). MASS=246.10 합성예 442 ： N- ((에틸티오)메틸) _2-옥소 -1，2-디하이드로퀴놀린 -3—카르복 사마이드 ¾ NMR 400 MHz, CDC1 3 ) 5 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 ᅳ 3H). MASS = 246.10 Synthesis Example 442: N-((ethylthio) methyl) _2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 誦 ol)올 DMF(2 mL)에 용해시켰다. DIPEA(3 隱 ol), (에틸티오)메타나민 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 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 Compound (1'ol) ol was dissolved in DMF (2 mL). DIPEA (3xol), (ethylthio) methamine (1.5mmol) and PyBop (2xol) 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 give Synthesis Example 442 compound (Yield = 71%).
¾ 圈 R(400,.MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.03(s, 1H, -¾ 圈 R (400, .MHz, CDC1 3 ) 6 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 합성예 443 ： N-(2-메톡시에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 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 Synthesis Example 443: N- (2-methoxyethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 誦 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-메톡시에타나민 (1.5 画 ol) 및 PyBop(2 画 ol)를 반응 흔합물에 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 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2-methoxyethanamine (1.5 μl ol) and PyBop (2 μl ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 443 (yield = 62%).
¾ NMRC400 ' MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H) , 8.03(s, 1H, -¾ NMRC400 ' MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.14 (d, 1H), 8.03 (s, 1H,-
NH), 8.0 (s, 1H, -NH), 7.36(d, 1H), 7.3i(t, 1H), 7.14(t, 1H), 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-카르복 사마이드 NH), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.3i (t, 1H), 7.14 (t, 1H), 3.59 (m, 2H), 3.5 (m, 2H), 1.10 (s, 3 H). MASS = 246.10 Synthesis Example 444: N-((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 瞧 ol), N-에틸메탄디아민 (1.5 醒 ol) 및 PyBop(2 睡 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 4 화합물을 수득하였다 (수율 = 71%) .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), N-ethylmethanediamine (1.5xol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 4 (yield = 71%).
¾ NMRC400 MHz, CDC13)6 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 합성예 445 ： N-(2— (메틸티오)에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카르복 사마이드 ¾ NMRC400 MHz, CDC1 3 ) 6 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 Synthesis Example 445: N- (2— (methylthio) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
합성예 25 화합물 (1 mmol)을 DMF(2 mL)에 용해시켰다. DIPEAC3 瞧 01) ， 2- (메틸티오)에타나민 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하고 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 볼로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 445 화합물을 수득하였다 (수율 = 49%) .  Synthesis Example 25 Compound (1 mmol) was dissolved in DMF (2 mL). DIPEAC3 瞧 01), 2- (methylthio) ethanamine (1.5 mmol) and PyBop (2 瞧 ol) were added to the reaction mixture and stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and balls. Then purified by silica gel chromatography to obtain the Synthesis Example 445 compound (yield = 49%).
¾ 赚 (400 MHz, CDC13)5 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 합성예 446 ： N-(2- (메틸아미노)에틸) -2—옥소 -l,2-디하이드로퀴놀린 -3-카르 복사마이드 ¾ 赚 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 446: N- (2- (methylamino) ethyl) -2—oxo-l, 2 -dihydroquinoline-3-car Copyamide
합성예 25 화합물 (1 瞧 ol)을 DMF(2 mL)에 용해시켰다. DIPEA(3 腿 ol), N1-메틸에탄 -1,2-디아민 (1.5 mmol) 및 PyBop(2 醒 ol)를 반웅 흔합물에 첨가하 상은에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 446 화합물을 수득하였다 (수율 =61¾ .  Synthesis Example 25 Compound (1xol) was dissolved in DMF (2 mL). DIPEA (3xol), N1-methylethane-1,2-diamine (1.5 mmol) and PyBop (2xol) were added to the reaction mixture and stirred for 3 hours at silver phase. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 446 (yield = 61¾.
¾ NMR(400 MHz, CDC13)5 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 단계 (f-6)의 일반적 과정 ¾ NMR (400 MHz, CDC1 3 ) 5 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 General procedure of steps (f-6)
브롬 (0.65 mL, 12.73 mmol) 브롬을 피리딘 (15 mL)으로 용해시킨 5번 화합물의 산 현탄액 (1.49 g, 6.36 画 ol)에 0°C에서 적상하고， 흔합물을 110°C에서 40분간, 교반하였다. 질은 갈색의 용액을 상온까지 냉각시키고 lNHCl(50mL)에 부었다. 침전물을 수집하여 1NHC1로 세척하고 다시 물로 세척한 뒤 건조시켜 6번 화합물을 수득하였다. 합성예 7 ： 3-브로모퀴놀린 -2(1H)-은 Bromine (0.65 mL, 12.73 mmol) was added dropwise to acid suspension (1.49 g, 6.36, ol) of compound 5 in which bromine was dissolved in pyridine (15 mL) at 0 ° C., and the mixture was stirred at 110 ° C. for 40 minutes. And stirred. The vagina was cooled to room temperature and poured into lNHCl (50 mL). The precipitate was collected, washed with 1NHC1, washed again with water and dried to afford compound 6. Synthesis Example 7: 3-bromoquinoline-2 (1H) -silver
브롬 (0.65 mL, 12.73 讓 ol)을 0°C에서 피리딘 (15 mL)에 용해된 2- 옥소 -1,2-디하이드로퀴놀린 -3-카복실릭애시드 현탄액 (1.49 g, 6.36 隱 ol)에 적상하고， 흔합물을 110°C에서 40분간 교반하였다 (수율 =61%).  Bromine (0.65 mL, 12.73 μl ol) was dissolved in 2-oxo-1,2-dihydroquinoline-3-carboxylic acid suspension (1.49 g, 6.36 μl ol) dissolved in pyridine (15 mL) at 0 ° C. Dropped and the mixture was stirred at 110 ° C. for 40 minutes (yield = 61%).
¾ NMR(400 MHz, CDC13) 8.14(d, 1H), 8.0(s, 1H, -NH), 7.8Ks, 1H)， 7.36 (d, 1H), 7.31(t, 1H) , 7.14(t, 1H) . MASS=222.96 합성예 8 ： 3,5-디브로모퀴놀린-2(111)-은 ¾ NMR (400 MHz, CDC1 3 ) 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.8Ks, 1H), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H). MASS = 222.96 Synthesis Example 8 3,5-dibromoquinoline-2 (111) -silver
브롬 (0.65 mL, 12.73 隱 ol)을 0°C에서 피리딘 (15 mL)에 용해시킨 5- 브로모 -2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭 애시드 (1.49 g, 6.36 mmol) 현탄액에 적상하고 흔합물을 1KTC에서 40분간 교반하였다 (수율 =64%).  5-bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1.49 g, 6.36 mmol) dissolved in bromine (0.65 mL, 12.73 μl ol) in pyridine (15 mL) at 0 ° C. ) Was suspended in suspension and the mixture was stirred at 1 KTC for 40 minutes (yield = 64%).
¾ 醒 R(400 MHz, CDC13)5 8.08(d, 1H), 8.0(s, 1H, -NH), 7.81(s, 1H), 7.29 (d, 1H)， 7.05(t, 1H). MASS=300.87 합성예 9 ： 3，6-디브로모퀴놀린-2(111)-온 ¾ 醒 R (400 MHz, CDC1 3 ) 5 8.08 (d, 1H), 8.0 (s, 1H, -NH), 7.81 (s, 1H), 7.29 (d, 1H), 7.05 (t, 1H). MASS = 300.87 Synthesis Example 9: 3,6-dibromoquinolin-2 (111) -one
브롬 (0.65 mL, 12.73 麵 ol)을 0°C에서 피리딘 (15 mL)에 용해시킨 6- 브로모 -2-옥소 -1,2-디하이드로퀴놀린— 3—카복실릭애시드 현탄액 (1.49g, 6.36 讓 ol)에 적상하고 '흔합물을 1KTC에서 40분간 교반하였다 (수율 =66%). 6-bromo-2-oxo-1,2-dihydroquinoline—3—carboxylic acid suspension (1.49 g,) in bromine (0.65 mL, 12.73 μl) dissolved in pyridine (15 mL) at 0 ° C.讓6.36 ol) was dropwise and the "common stirring the compound in 1KTC 40 minutes (yield = 66%).
¾ 賺 (400 MHz, CDC13)68.0 (s, 1H, -NH)， 7.81(s, 1H), 7.55(d,¾ 賺 (400 MHz, CDC1 3 ) 68.0 (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(111)-온 1H), 7.53 (d, 1H), 7.46 (d, 1H). MASS = 300.87 Synthesis Example 10: 3,7-dibromoquinolin-2 (111) -one
브롬 (0.65 mL, 12.73 画 ol)을 0°C에서 피리딘 (15 mL)에 용해시킨 7- 브로모 -2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭애시드 현탄액 (1.49 g, 6.36 mmol)에 적상하고 흔합물을 1KTC에서 40분간 교반하였다 (수율 =62%) . 7-bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid suspension (1.49 g,) in which bromine (0.65 mL, 12.73 μl) was dissolved in pyridine (15 mL) at 0 ° C. 6.36 mmol) and the mixture was stirred at 1KTC for 40 minutes (yield = 62%).
¾匿 R (400 MHz, CDC13)6 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 과정 ¾ 匿 R (400 MHz, CDC1 3 ) 6 8.0 (s, 1H, -NH), 7.82 (d, 1H), 7.81 (s 1H), 7.29 (d, 1H), 7.25 (d, 1H). General procedure of MASS = 300.87 steps (g-7)
등근바닥 플라스크에 Pd(0AC)2(3.6mg, O. imol), 잔포스 (4.7mg, 0.05隱 ol), 고형 반웅물 (1.0 mmol 보호기 결합 퀴놀리논， 1.5 画 ol 아민) 및 Cs2C03(104mg,2mmol)을 채워 넣었다. 등근바닥 플라스크를 고무마개로 막고 비운 뒤 질소를 다시 채워 넣었다. 이러한 비우기 /채우기를 한번 더 반복하였다. 액상 반웅물 및 1,4-디옥산 (lmL)을 마개를 통해 주입하였다. 플라스크를 밀봉하고 흔합물을 1(XTC에서 10시간 동안 교반하였다, 수득한 현탄액을 상온까지 넁각시키고 여과한 후 농축하여 실리카겔 컬럼크로마토그래피로 정제하여 7번 화합물을 수득하였다. 합성예 447 ： 3- (페닐아미노)퀴놀린 -2(1H)-은 Pd (0AC) 2 (3.6 mg, O. imol), xantose (4.7 mg, 0.05 μl), solid reaction product (1.0 mmol protecting group-binding quinolinone, 1.5 μl amine) and Cs 2 C0 3 (104 mg, 2 mmol) was charged. The back bottom flask was sealed with a rubber stopper and emptied with nitrogen. This emptying / filling was repeated once more. Liquid half water and 1,4-dioxane (lmL) were injected via a stopper. The flask was sealed and the mixture was stirred at XTC for 10 hours. The obtained suspension was stirred to room temperature, filtered and concentrated to purified by silica gel column chromatography to give compound 7. Synthesis Example 447: 3 -(Phenylamino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 画 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 mmol), 아닐린 (1.3 mmol) 및 잔포스 (0.15 誦 ol)를 반웅 흔합물에 첨가하고 100°C에서 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 μ ol) 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 xantose (0.15 μl ol) were added to the reaction mixture and stirred at 100 ° C. for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 447 (yield = 61%).
¾ NMR(400 MHz, CDC13)5 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 합성예 448 ： 3-(i>-를일아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 448: 3- (i> -ylylamino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 睡 ol)를 1,4-디옥산 (2 mL)에 용해시 ¾다. Dissolve 3-bromoquinolin-2 (1H) -one (1 μl) in 1,4-dioxane (2 mL).
Cs2C03(2 mmol), Pd(0AC)2(0.15 画 ol), p-를루이딘 (1.3 睡 ol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 448 화합물올 수득하였다 (수율 =61%). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 μl ol), p-lluidine (1.3 μl ol) and xantose (0.15 mmol) were added to the reaction mixture and 10 h at 100 ° C. Was stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound 448 Synthesis (yield = 61%).
¾ 匪 R (400 MHz, CDC13)5 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 합성예 449 ： 3-((4-메특시페닐)아미노)퀴놀린 -2(1H)-온 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 449: 3-((4-Methoxyphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)_온 (1 睡 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), 4-메톡시아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), 4-methoxyaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. It was. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 449 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 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 합성예 450 ： 3-((4-브로모페닐)아미노)퀴놀린 -2(1H)-은 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 450: 3-((4-bromophenyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)를 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 mmol), 4—브로모아닐린 (1.3 隱 ol) 및 잔포스 (0.15 麵 ol)를 반웅 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 mmol), 4—bromoaniline (1.3 隱 ol) and xanphos (0.15 麵 ol) were added to the reaction mixture and 10 at 100 ° C. Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph Synthesis Example 450 compound Obtained (yield = 61%).
¾ 醒 R(400 MHz, CDC13)8 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 합성예 451 ： 3-((4-클로로페닐)아미노)퀴놀린 -2(1H)-온 ¾ 醒 R (400 MHz, CDC1 3 ) 8 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 Synthesis Example 451: 3-((4-chlorophenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-은 (1 睡 ol)를 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2 (0.15 誦 ol)ᅳ 4-클로로아닐린 (1.3 讓 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 451 화합물을 수득하였다 (수율 =49%). 3-bromoquinoline-2 (1H) -silver (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 誦 ol) ᅳ 4-chloroaniline (1.3 讓 ol) and xanphos (0.15 隱 ol) were added to the reaction mixture and 10 h at 100 ° C. Was stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 451 compound (yield = 49%).
¾腿 R (400 MHz, CDC13) 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 합성예 452 ： 3-((4-플루오로페닐)아미노)퀴놀린 -2(1H)-온 ¾ 腿 R (400 MHz, CDC1 3 ) 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 Synthesis Example 452: 3-((4-fluorophenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 讓 ol)을 1，4-디옥산 (2 mL)에 용해시켰,다. Cs2C03(2 画 ol), Pd(0AC)2(0.15 mmol), 4-플루오로아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10CTC에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 452 화합물을 수득하였다 (수율 =43%) . 3-Bromoquinoline-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 μL), Pd (0AC) 2 (0.15 mmol), 4-fluoroaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 10 CTC for 10 hours. . The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 452 compound (yield = 43%).
¾ NMRC400 MHz, CDC13)5 8.14(d, 1H), 8.0(s, 1H, -NH) , 7.3(m, 2H), 7.21 (m, 2H), 7 4(t, 1H), 6.83(s, 1H) , 6.81(t, 1H), 6.43(dd, 2H) 4.0(s, 1Hᅳ -NH). MASS=254.09 합성예 453 ： 3-((4-에틸페닐)아미노)퀴놀린 -2(1H)-은 ¾ NMRC400 MHz, CDC1 3 ) 5 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7 4 (t, 1H), 6.83 (s , 1H), 6.81 (t, 1H), 6.43 (dd, 2H) 4.0 (s, 1H ᅳ -NH). MASS = 254.09 Synthesis Example 453: 3-((4-ethylphenyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 画 ol)를 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 mmol), 4-에틸아닐린 (1.3 瞧 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), 4-ethylaniline (1.3 瞧 ol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. Stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 453 (yield = 49%).
¾ NMR(400'MHz, CDC13)6 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.i3 합성예 454 ： 3-((4-하이드록시페닐)아미노)퀴놀린 -2(1H)—은 ¾ NMR (400'MHz, CDC1 3 ) 6 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.i3 Synthesis Example 454: 3-((4-hydroxyphenyl) amino) quinoline-2 (1H) —silver
3-브로모퀴놀린 -2(1H)ᅳ온 (1 mmol)를 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), 4-아미노페놀 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10CTC에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 454 화합물을 수득하였다 (수율 =53%). 3-bromoquinoline-2 (1H) xion (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 μL), Pd (0AC) 2 (0.15 mmol), 4-aminophenol (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 10 CTC for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 454 (yield = 53%).
匪 R(400 MHz, CDC13)5 8.14(d, 1H) , 8.0(s, 1H, -NH), 7.3(m, 2H),匪 R (400 MHz, CDC1 3 ) 5 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.3 (m, 2H),
7.21 Cm, 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 합성예 455 ： 3-((4-니트로페닐)아미노)퀴놀린 -2(1H)-온 7.21 Cm, 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 Synthesis Example 455: 3-((4-nitrophenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1ᅳ 4-디옥산 (2 mL)에 용해시켰다. 3-Bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1x 4-dioxane (2 mL).
Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), 4-니트로아닐린 (1.3 mmol) 및 잔포스 (0.15 隱 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 455 화합물을 수득하였다 (수율 =61%). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), 4-nitroaniline (1.3 mmol) and xanphos (0.15 隱 ol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. Stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 455 (yield = 61%).
¾ NMR(400 MHz, CDC13)5 8.14(d, 1H), 8.0(s, 1Hᅳ -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 합성예 456 ： 3-((4- (하이드록시메틸)페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 5 8.14 (d, 1H), 8.0 (s, 1H ᅳ -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 Synthesis Example 456: 3-((4- (hydroxymethyl) phenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 麵 ol)을 1ᅳ 4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), (4-아미노페닐)메탄을 (1.3 隱 ol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로미 "토그래프로 정제하여 합성예 456 화합물을 수득하였다 (수율 =49%). 3-bromoquinolin-2 (1H) -one (1 μl) was dissolved in 1 ′ 4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), (4-aminophenyl) methane (1.3 隱 ol) and xantose (0.15 mmol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromi "tograph to give the compound of Synthesis Example 456 (yield = 49%).
¾ NMR(400 MHz, CDCl3)8 8.14(d, 1H), 8.0(s, iH, -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 합성예 457 ： 3-((4-비닐페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDCl 3 ) 8 8.14 (d, 1H), 8.0 (s, iH, -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 Synthesis Example 457: 3-((4-vinylphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), 4-비닐아닐린 (1.3 mmol) 및 잔포스 (0.15 瞧 ol)를 반웅 흔합물에 첨가하고 10CTC에서 10시간 동안 교반하였다. 수득 1한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 457 화합물을 수득하였다 (수율 =41%). 3-bromoquinolin-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), 4-vinylaniline (1.3 mmol) and xantose (0.15 μl ol) were added to the reaction mixture and stirred at 10 CTC for 10 hours. The residue obtained 1 was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 457 (yield = 41%).
¾ NMR(400 MHz, CDC13)5 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, IH, -NH). MASS=262.11 합성예 458 ： Ν,Ν-디메틸 -4-((2-옥소 -1,2-디하이드로퀴놀린— 3-일)아미노) 벤젠설폰아미드 ¾ NMR (400 MHz, CDC1 3 ) 5 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, 1H), 6.63 (s, 1H), 6.43 (dd, 2H), 5.61 (s, 1H), 5.18 (s, 1H), 4.0 (s, IH, -NH). MASS = 262.11 Synthesis Example 458: Ν, Ν-dimethyl-4-((2-oxo-1,2-dihydroquinolin-3 -yl) amino) benzenesulfonamide
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol); Pd(0AC)2(0.15 醒 ol), 4-아미노 -Ν,Ν -디메틸벤젠 설폰아미드 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol); Pd (0AC) 2 (0.15 μl ol), 4-amino-Ν, Ν-dimethylbenzene sulfonamide (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C. for 10 hours. . The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 458 (yield = 63%).
¾ NMRC400 MHz, CDC13)5 8.14(d, IH), 8.0(s, IH, -NH) , 7.3(m, 2H), 7.21 (m, 2H), 7.14(t, IH), 6.83(s, IH), 6.81(t, IH), 6.63(s, IH) , 6.43(dd, 2H), 4.0(s, IH, -NH), 2.66(111， 6H). MASS=343.10 합성예 459 ： 3- (벤질아미노)퀴놀린 -2(1H)-온 ¾ NMRC400 MHz, CDC1 3 ) 5 8.14 (d, IH), 8.0 (s, IH, -NH), 7.3 (m, 2H), 7.21 (m, 2H), 7.14 (t, IH), 6.83 (s, IH), 6.81 (t, IH), 6.63 (s, IH), 6.43 (dd, 2H), 4.0 (s, IH, -NH), 2.66 (111, 6H). MASS = 343.10 Synthesis Example 459: 3- (benzylamino) quinolin-2 (1H) -one
3-브로모퀴 린 -2(1H)-온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. 3-bromoquilin-2 (1H) -one (1 μ ol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol), 에틸벤젠 (1.3 画 ol) 및 잔포스 (0.15 醒 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 459 화합물을 수득하였다 (수율 =41%). Cs 2 C0 3 (2 μl ol), Pd (0AC) 2 (0.15 μl ol), ethylbenzene (1.3 μl ol) and xantose (0.15 μl ol) were added to the reaction mixture and the mixture was stirred at 100 ° C. for 10 hours. Stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 459 compound (yield = 41%).
¾ 證 (400 MHz, CDC13)6 8.14(d, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.33(dd, 2H), 7.31(t , IH)， 7.23(dd, 2H), 7.26(t, IH), 7.14(t, IH), 6.10(s, IH), 3.92(m, 2H), 2.0(s, IH, -NH). MASS=250.11 합성예 460 ： 3-((4-메틸벤질)아미노)퀴놀린 -2(1H)-온 ¾ 證 (400 MHz, CDC1 3 ) 6 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.33 (dd, 2H), 7.31 (t, IH), 7.23 ( dd, 2H), 7.26 (t, IH), 7.14 (t, IH), 6.10 (s, IH), 3.92 (m, 2H), 2.0 (s, IH, -NH). MASS = 250.11 Synthesis Example 460: 3-((4-Methylbenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-은 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 隱 οί), 1-에틸 -4—메틸벤젠 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 460 화합물을 수득하였다 (수율 =68 . 3-bromoquinoline-2 (1H) -silver (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 隱 οί), 1-ethyl-4-methylbenzene (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 460 (yield = 68.
¾ 醒 R(400 MHz, CDC13)6 8.14(d, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.33(dd, 2H) , 7.31(t, IH), 7.23(dd, 2H) , 7.26(t, IH), 7.14(t, IH), 6.10 (s, IH), 3.92(m, 2H), 2.34(s, 3H), 2.0(s, IH, -NH). MASS=264.13 합성예 461 ： 3—((4-메록시벤질)아미노)퀴놀린 2(1H)-온 ¾ 醒 R (400 MHz, CDC1 3 ) 6 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.33 (dd, 2H), 7.31 (t, IH), 7.23 (dd, 2H), 7.26 (t, IH), 7.14 (t, IH), 6.10 (s, IH), 3.92 (m, 2H), 2.34 (s, 3H), 2.0 (s, IH, -NH) . MASS = 264.13 Synthesis Example 461 ： 3 — ((4-methoxybenzyl) amino) quinolin 2 (1H) -one
3-브로모퀴놀린 2(1H)_온 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 醒 ol), 1-에틸 -4-메톡시벤젠 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 461 화합물을 수득하였다 (수율 =65%). 3-Bromoquinoline 2 (1H) _one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 醒 ol), 1-ethyl-4-methoxybenzene (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 100 ° Stir at C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 461 (yield = 65%).
¾匪 R (400 MHz, CDC13)6 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d,¾ 匪 R (400 MHz, CDC1 3 ) 6 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d,
IH), 7.33 (dd, 2H), 7.31 (t, IH) , 7.23 (dd, 2H), 7.26 (t, IH), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.3 (s, 3H), 2.0 (s, 1H, -NH). MASS = 280.12 합성예 462 ： 3-((4-브로모벤질)아미노)퀴놀린 -2(1H)-은 IH), 7.33 (dd, 2H), 7.31 (t, IH), 7.23 (dd, 2H), 7.26 (t, IH), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.3 (s, 3H), 2.0 (s, 1H, -NH). MASS = 280.12 Synthesis Example 462: 3-((4-bromobenzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 画 ol), Pd(0AC)2(0.15 mmol), 1-브로모 -4-에틸벤젠 (1.3 隱 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 462 화합물을 수득하였다 (수율 =61%). Cs 2 C0 3 (2 画 ol), Pd (0AC) 2 (0.15 mmol), 1-bromo-4-ethylbenzene (1.3 隱 ol) and xantose (0.15 隱 ol) were added to the reaction mixture and 100 Stir at 10 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 462 (yield = 61%).
¾ NMR (400 MHz, CDC13) 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 합성예 463 ： 3-((4-클로로벤질)아미노)퀴놀린 -2(1H)-은 ¾ NMR (400 MHz, CDC1 3 ) 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 Synthesis Example 463: 3-((4-chlorobenzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 匪 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), 1-클로로 -4-에틸벤젠 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), 1-chloro-4-ethylbenzene (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 463 (yield = 60%).
¾ 画 R(400 MHz, CDC13)6 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(tn, 2H), 2.0(s, 1H, -NH). MASS=284.07 합성예 464 ： 3-((4-플루오로벤질)아미노)퀴놀린 -2(1H)-온 ¾ 画 R (400 MHz, CDC1 3 ) 6 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 (tn, 2H), 2.0 (s, 1H, -NH). MASS = 284.07 Synthesis Example 464: 3-((4-fluorobenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 麵 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 隱 ol), 1-에틸 -4-플루오로벤젠 (1.3 誦 ol) 및 잔포스 (0.15 画 ol)를 반웅 흔합물에 첨가하고 10()°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (OAC) 2 (0.15 隱 ol), 1-ethyl-4-fluorobenzene (1.3 誦 ol) and xantose (0.15 画 ol) were added to the reaction mixture and 10 Stir at () ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph Synthesis Example 464 compound Obtained (yield = 68%).
¾ 匪 R(400 MHz, CDC13)6 8.14(d, 1H)， 8.0(s, 1H, -NH), 7.36(d¾ 匪 R (400 MHz, CDC1 3 ) 6 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 합성예 465 ： 3-((4-에틸벤질)아미노)퀴놀린 -2(1H)-온 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H) ; 7.26 (t, 1 H), 7.14 (t 1 H), 6.10 (s, 1 H), 3.92 (m, 2H), 2.0 (s, 1H, -NH). MASS = 268.10 Synthetic Example 465: 3-((4-ethylbenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 腿 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(OAC)2(0.15 隱 ol), 1,4-디에틸벤젠 (1.3 睡 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 465 화합물을 수득하였다 (수율 =4¾). 3-bromoquinolin-2 (1H) -one (1 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (OAC) 2 (0.15 隱 ol), 1,4-diethylbenzene (1.3 睡 ol) and xantose (0.15 mmol) were added to the reaction mixture and 100 ° C Stirred for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 465 (yield = 4¾).
¾ 醒 (400 MHz, CDC13)6 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 합성예 466 ： 3-((4-하이드록시벤질)아미노)퀴놀린 -2(1H)-온 ¾ 醒 (400 MHz, CDC1 3 ) 6 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, 3 H). MASS = 278.14 Synthetic Example 466: 3-((4-hydroxybenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 瞧 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 誦 ol), Pd(OAC)2(0.15 mmol), (4-에틸페닐)메탄을 (1.3 誦 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10CTC에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 誦 ol), Pd (OAC) 2 (0.15 mmol), (4-ethylphenyl) methane (1.3 誦 ol) and xantose (0.15 mmol) were added to the reaction mixture and 10 at 10 CTC Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 466 (yield = 61%).
¾ 醒 R(400 MHz, CDC13)6 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d,¾ 醒 R (400 MHz, CDC1 3 ) 6 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). ASS=266.11 합성예 467 ： 3-((4-니트로벤질)아미노)퀴놀린 -2(1H)-온 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). ASS = 266.11 Synthesis Example 467: 3-((4-nitrobenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 画 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 醒 ol), Pd(0AC)2(0.15 瞧 ol), 1—에틸 -4-니트로벤젠 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 1001에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 醒 ol), Pd (0AC) 2 (0.15 瞧 ol), 1—ethyl-4-nitrobenzene (1.3 mmol) and Xanthose (0.15 mmol) was added to the reaction mixture and stirred at 1001 for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 467 (yield = 61%).
¾ 丽 (400 MHz, CDC13)6 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d,¾ δ (400 MHz, CDC1 3 ) 6 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, iH), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H), 2.0 (s, 1H, -NH). MASS = 295.10 합성예 468 ： Ν,Ν—디메틸 -4-(((2-옥소 -1,2-디하이드로퀴놀린 -3-일)아미노) 메틸)벤젠설폰아미드 1H), 7.33 (dd, 2H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.26 (t, iH), 7.14 (t, 1H), 6.10 (s, 1H), 3.92 (m, 2H ), 2.0 (s, 1H, -NH). MASS = 295.10 Synthesis Example 468: Ν, Ν—Dimethyl-4-(((2-oxo-1,2-dihydroquinolin-3-yl) amino) methyl) benzenesulfonamide
3-브로모퀴놀린 -2(1H)—온 (1 睡 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol)ᅳ Pd(OAC)2(0.15 醒 ol), 4- (아미노메틸)ᅳ Ν,Ν-디메틸벤젠 설폰아미드 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10CTC에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol) ᅳ Pd (OAC) 2 (0.15 醒 ol), 4- (aminomethyl) ᅳ Ν, Ν-dimethylbenzene sulfonamide (1.3 mmol) and xanthose (0.15 mmol) The mixture was added and stirred at 10 CTC for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 468 (yield = 64% ).
¾ NMR(400 MHz, CDC13)6 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 합성예 469 ： 3-((4- (하이드록시메틸)벤질)아미노)퀴놀린 -2(1H)-은 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 469: 3-((4- (hydroxymethyl) benzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)ᅳ온 (1 誦 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 麵 ol), Pd(0AC)2(0.15 睡 ol), (4-에틸페닐)메탄을 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 469 화합물을 수득하였다 (수율 = 53%) . 3-Bromoquinoline-2 (1H) ᅳ one (1 誦 ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 麵 ol), Pd (0AC) 2 (0.15 睡 ol), (4-ethylphenyl) methane (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 100 ° C Stirred for 10 h. The obtained residue was extracted with ethyl acetate and water. After purification by silica gel chromatography to obtain the compound of Synthesis Example 469 (yield = 53%).
¾ NMR (400 MHz, CDC13)68.14(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 합성예 470 ： 3-((4-비닐벤질)아미노)퀴놀린 -2(1H)-은 ¾ NMR (400 MHz, CDC1 3 ) 68.14 (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 Synthesis Example 470: 3-((4-vinylbenzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴½린-2(111)-온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), 1—에틸 -4-비닐벤젠 (1.3 隱 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 470 화합물을 수득하였다 (수율 =63%). 3-bromoqui½rin-2 (111) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), 1—ethyl-4-vinylbenzene (1.3 隱 ol) and xantose (0.15 隱 ol) were added to the reaction mixture and 100 ° Stir at C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 470 (yield = 63%).
¾ 匪 R(400 MHz, CDCls) 58.14(d, 1H), 8.0(s, 1H, -NH), 7.59(dd, 2H), 7.36(d, 1H), 7.31(t, 1H), 7.18(ddᅳ 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 합성예 471 ： 3- (베틸 (페닐)아미노)퀴놀린 -2(1H)-온  ¾ 匪 R (400 MHz, CDCls) 58.14 (d, 1H), 8.0 (s, 1H, -NH), 7.59 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1H), 7.18 (dd ᅳ 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 Synthesis Example 471 ： 3- (Betyl (phenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4ᅳ디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), N_메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 471 화합물을 수득하였다 (수율 =61%). 3-Bromoquinoline-2 (1H) -one (1 μl) was dissolved in 1,4 ᅳ dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), N_methylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. . The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 471 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 8.14(d, 1H), 8.0(s, 1H, -NH) , 7.36(d,¾ NMR (400 MHz, CDC1 3 ) 6 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),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 합성예 472 ： 3- (에틸 (페닐)아미노)퀴놀린 -2(1H)-은 6.60 (dd, 2H), 3.44 (s, 3H). MASS = 250.11 Synthesis Example 472: 3- (Ethyl (phenyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1，4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 mmol), Pd(0AC)2(0.15 隱 ol), Nᅳ에틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 472 화합물을 수득하였다 (수율 =61 . Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 隱 ol), N ᅳ ethylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and stirred at 100 ° C for 10 hours. It was. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 472 (yield = 61.
¾ 羅 (400 MHz, CDC13)5 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 합성예 473 ： 3- (에틸 (p-를일)아미노)퀴놀린 -2(1H)-은 ¾ ERA (400 MHz, CDC1 3 ) 5 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, 3 H). MASS = 264.13 Synthesis Example 473: 3- (Ethyl (p-ylyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린ᅳ 2(1H)-은 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinoline ᅳ 2 (1H) -silver (1 隱 ol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), N—에틸 -4-메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 画 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 473 화합물을 수득하였다 (수율 =60%). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), N-ethyl-4-methylaniline (1.3 mmol) and xantose (0.15 画 ol) were added to the reaction mixture and 100 ° C Stirred for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 473 (yield = 60%).
¾ 賺 (400 MHz, CDC13)6 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 합성예 474 ： 3- (메틸 (p-를일)아미노)퀴놀린 -2(1H)-온 ¾ 賺 (400 MHz, CDC1 3 ) 6 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 Synthetic Example 474: 3- (methyl (p-ylyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), N,4-디메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 l(XrC에서 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 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), N, 4-dimethylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and l (XrC for 10 hours) The residue obtained was extracted with ethyl acetate and water and then purified by silica gel chromatography to give Synthesis Example 474 compound (yield = 52%).
¾ 證 (400 MHz, CDC13)5 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 합성예 .475 ： 3-((4-메톡시페닐) (메틸)아미노)퀴놀린 -2(1H)-온 ¾ 證 (400 MHz, CDC1 3 ) 5 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 Synthetic Example .475: 3-((4-methoxyphenyl) (methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)_온 (1 匪 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 誦 ol), 4-메특시 -N-메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Add Cs 2 C0 3 (2 μl ol), Pd (0AC) 2 (0.15 μl ol), 4-methoxy-N-methylaniline (1.3 mmol) and xantose (0.15 mmol) to the reaction mixture and add 100 ° Stir at C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph Synthesis Example 475 compound Obtained (yield = 61%).
¾賺 (400 MHz, CDC13)68.14(d, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.31 (d, IH), 7.14(t, IH), 6.83(S) IH), 6.77(dd, 2H) , 6.71(dd, 2H), 3.83(s, 3H), 3.44(s, 3H). MASS=280.12 합성예 476 ： 3- (에틸 (4-메록시페닐)아미노)퀴놀린 -2(1H)—은 ¾ 賺 (400 MHz, CDC1 3 ) 68.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (d, IH), 7.14 (t, IH), 6.83 ( S ) IH), 6.77 (dd, 2H), 6.71 (dd, 2H), 3.83 (s, 3H), 3.44 (s, 3H). MASS = 280.12 Synthesis Example 476: 3- (Ethyl (4-methoxyphenyl) amino) quinoline-2 (1H) —silver
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), N_에틸 -4—메록시아닐린 (1.3 隱 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 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 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), N_ethyl-4—meroxyaniline (1.3 隱 ol) and xantose (0.15 隱 ol) were added to the reaction mixture and 100 ° Stir at C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 476 (yield = 67%).
¾ NMR(400'顧 z, CDC13)6 8.14(t, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.23(dd, 2H), 7.14(t, IH), 6.83(s, IH), 6.77(t, IH), 6.60(dd, 2H), 4.56(m, 2H) , 2.34(s, 3H), 1.31(s, 3H). MASS=294.14 합성예 477 ： 3-((4-브로모페닐) (에틸)아미노)퀴놀린 2(1H)_온 ¾ NMR (400 '顧 z, CDC1 3 ) 6 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.23 (dd, 2H), 7.14 (t, IH), 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H), 1.31 (s, 3H). MASS = 294.14 Synthesis Example 477: 3-((4-bromophenyl) (ethyl) amino) quinolin 2 (1H) _one
3-브로모퀴놀린 -2(1H)-온 (1隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15隱 ol), 4-브로모 -N-에틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 477 화합물을 수득하였다 (수율 =61%). 3-Bromoquinoline-2 (1H) -one (1 'ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (OAC) 2 (0.15 隱 ol), 4-bromo-N-ethylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 100 ° C Stirred for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 477 (yield = 61%).
¾ NMR (400 MHz, CDC13) δ 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.23 (dd, 2H), 7.14 (t, IH)ᅳ 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34(s, 3H). MASS - 342.04 합성예 478 ： 3— ((4—브로모페닐) (메틸)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) δ 8.14 (t, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.23 (dd, 2H), 7.14 ( t, IH) ᅳ 6.83 (s, IH), 6.77 (t, IH), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H). MASS-342.04 Synthesis Example 478: 3— ((4—Bromophenyl) (methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 mmol), 4-브로모—N-메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 mmol), 4-bromo—N-methylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 100 ° C. For 10 hours at Stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 478 (yield = 63%).
¾ NMR(400 MHz, CDC13)6 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 합성예 479 ： 3-((4-클로로페닐) (에틸)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 479: 3-((4-chlorophenyl) (ethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1，4—디옥산 (2 mL)에 용해시켰다.  3-bromoquinoline-2 (1H) -one (1 mmol) was dissolved in 1,4-dioxane (2 mL).
7  7
Cs2C03(2 mmol), Pd(0AC)2(0.15 隱 ol)ᅳ 44—클로로 -N-에틸아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 1001：에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로하토그래프로 정제하여 합성예 479 화합물을 수득하였다 (수율 =31%) . Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 隱 ol) ᅳ 44—chloro-N-ethylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 1001: to 10 Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then, the silica gel was purified by chromatograph to obtain a Synthesis Example 479 compound (yield = 31%).
¾ 證 (400 MHz, CDC13)6 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d,¾ 證 (400 MHz, CDC1 3 ) 6 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)ᅳ 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H)， 2.34(s, 3H). MASS=298.09 합성예 480 ： 3-((4-클로로페닐) (메틸)아미노)퀴놀린 -2(1H)-온 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1H), 6.83 (s, 1H) ᅳ 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H) ), 2.34 (s, 3H). MASS = 298.09 Synthesis Example 480 ： 3-((4-chlorophenyl) (methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)_온 (1 讓 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) _one (1 μl) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), 4-클로로ᅳ N—메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 瞧 ol)를 반웅 흔합물에 첨가하고 10CTC에서 10시간 동안 교반하였다. 수복한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 480 화합물을 수득하였다 (수율 = 61%) Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), 4-chloro ᅳ N—methylaniline (1.3 mmol) and xantose (0.15 瞧 ol) were added to the reaction mixture and 10 h at 10 CTC. Was stirred. The recovered residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 480 (yield = 61%)
¾ 應 R(400 MHz, α 13)δ 8.14(t, 1H), 8.0(s, 1Hᅳ -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 합성예 481 ： 3-((4-플루오로페닐) (메틸)아미노)퀴놀린 -2(111)_온 ¾ 應 R (400 MHz, α 1 3 ) δ 8.14 (t, 1H), 8.0 (s, 1H ᅳ -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t, 1 H), 6.83 (s, 1 H), 6.77 (t, 1 H), 6.60 (dd, 2H), 4.56 (m, 2H). MASS = 284.07 Synthesis Example 481: 3-((4-fluorophenyl) (methyl) amino) quinolin-2 (111) _one
3-브로모퀴놀린 -2(1H)_온 (1 誦 ol)을 1，4-디옥산(2^)에 용해시켰다. Cs2C03(2 醒 ol), Pd(0AC)2(0.15 mmol), 4-플루오로 -N-메틸아닐린 (1.3 隱 ol) 및 잔포스 (0.15 ιηηιοΐ)를 반웅 혼합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 481 화합물을 수득하였다 (수율 = 46%) . 3-bromoquinoline-2 (1H) _one (1 mu ol) was dissolved in 1,4-dioxane (2 ^). Cs 2 C0 3 (2 醒 ol), Pd (0AC) 2 (0.15 mmol), 4-fluoro-N-methylaniline (1.3 隱 ol) and xantose (0.15 ιηηιοΐ) were added to the reaction mixture and 100 ° C Stirred for 10 h. The obtained residue was extracted with ethyl acetate and water. Subsequent purification with silica gel chromatography gave the compound of Synthesis 481 (yield = 46%).
¾ NMR(400 MHz, CDCls) 58.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31 (t, 1H), 7.23(dd, 2H), 7.14(tᅳ 1H), 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(πι, 2H) . MASS=268.10 합성예 482 ： 3- (에틸 (4-플루오로페닐)아미노)퀴놀린 -2(1H)-온  ¾ NMR (400 MHz, CDCls) 58.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H), 7.14 (t ᅳ 1H), 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (πι, 2H). MASS = 268.10 Synthesis Example 482: 3- (Ethyl (4-fluorophenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2 (0.15 mmol), N-에틸 -4-풀루오로아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 혼합물에 첨가하고 100°C에서 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 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), N-ethyl-4-fuluroaniline (1.3 mmol) and xantose (0.15 mmol) are added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 482 (yield = 67%).
¾ NMR(400 MHz, CDC13)5 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.23(dd, 2H)ᅳ 7.14(t, 1H)ᅳ 6.83(s, 1H), 6.77(t, 1H), 6.60(dd, 2H), 4.56(m, 2H), 2.34(s, 3H) . MASS=282.12 합성예 483 ： 3- (에틸 (4-에틸페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 5 8.14 (t, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.23 (dd, 2H) ᅳ 7.14 ( t, 1H) ᅳ 6.83 (s, 1H), 6.77 (t, 1H), 6.60 (dd, 2H), 4.56 (m, 2H), 2.34 (s, 3H). MASS = 282.12 Synthesis Example 483: 3- (ethyl (4-ethylphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)—온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol), N, 4-디에틸아닐린 (1.3 画 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10C C에서 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 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 隱 ol), N, 4-diethylaniline (1.3 画 ol) and xantose (0.15 mmol) were added to the reaction mixture and at 10 C C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 483 (yield = 67%).
¾ NMR(400 MHz, CDC13) 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 합성예 484 ： 3-((4-에틸페닐) (메틸)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 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 Synthesis Example 484: 3-((4-ethylphenyl) (methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 瞧 ol), 4-에틸 -N-메틸아닐린 (1.3 醒 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 lCXrC에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 瞧 ol), 4-ethyl-N-methylaniline (1.3 醒 ol) and xantose (0.15 隱 ol) were added to the reaction mixture and Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 484 (yield = 61%).
¾ 匿 (400 MHz, CDC13)5 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 합성예 485 ： 3- (에틸 (4-하이드록시페닐)아미노)퀴놀린—2(1H)-온 ¾ 匿 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 485 ： 3- (Ethyl (4-hydroxyphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 瞧 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2 (0.15 mmol), 4- (에틸아미노)페놀 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), 4- (ethylamino) phenol (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 485 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 8.14(t, 1H), 8.0(s, 1H, -NH), 7.36(d,¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 486 : 3-((4-하이드록시페닐) (메틸)아미노)퀴놀린 -2(1H)-은 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, 3 H). MASS = 280.12 Synthesis Example 486: 3-((4-hydroxyphenyl) (methyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 瞧 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) -one (1 μ ol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 隱 ol), Pd(0AC)2(0.15 mmol), 4- (메틸아미노)페놀 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 486 화합물을 수득하였다 (수율 =61%) . Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 mmol), 4- (methylamino) phenol (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 486 (yield = 61%).
¾ NMRC400 顧 z, CDC13) 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 합성예 487 ： 3- (메틸 (4-니트로페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMRC400 顧 z, CDC1 3 ) 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 Synthesis Example 487: 3- (methyl (4-nitrophenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) -one (1 μ ol) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 mmol), Pd(0AC)2(0.15 隱 ol), N—메틸— 4—니트로아닐린 (1.3 画 ol) 및 잔포스 (0.15 瞧 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 487 화합물을 수득하였다 (수율 =61%). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 隱 ol), N—methyl— 4—nitroaniline (1.3 画 ol) and xantose (0.15 瞧 ol) were added to the reaction mixture and 100 ° Stir at C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 487 (yield = 61%).
¾ 丽 (400 MHz, CDC13)6 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 합성예 488 ： 3- (에틸 (4-니트로페닐)아미노)퀴놀린 -2(1H)-은 ¾ (400 MHz, CDC1 3 ) 6 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 Synthesis Example 488: 3- (Ethyl (4-nitrophenyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)_온 (1 隱 ol)을 1ᅳ 4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 mmol), N—에틸 -4-니트로아닐린 (1.3 mmol) 및 잔포스 (0.15 瞧 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 488 화합물을 수득하였다 (수율 =63%). 3-Bromoquinoline-2 (1H) _one (1 'ol) was dissolved in 1' 4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 mmol), N—ethyl-4-nitroaniline (1.3 mmol) and xantose (0.15 μl ol) were added to the reaction mixture and at 100 ° C. Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis 488 (yield = 63%).
¾ NMR 00, MHz, CDC13)8 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 합성예 489 ： 3- (에틸 (4— (하이드록시메틸)페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR 00 , MHz, CDC1 3 ) 8 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 Synthesis Example 489: 3- (ethyl (4— (hydroxymethyl) phenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 瞧 οΠ을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2 (0.15 mmol), (4— (에틸아미노)페닐)메탄을 (1.3 mmol) 및 잔포스 (0.15 睡 ol)를 반웅 흔합물에 첨가하고 100°C에서 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 1 οΠ was dissolved in 1,4-dioxane (2 mL) Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 mmol) , (4— (ethylamino) phenyl) methane (1.3 mmol) and xantose (0.15 μl) were added to the reaction mixture and stirred for 10 hours at 100 ° C. The obtained residue was diluted with ethyl acetate and water. Subsequently, the compound was purified by silica gel chromatography to obtain Synthesis Example 489. Obtained (yield = 67%).
¾ 醒 R(400,.匪 z, CDC13)6 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 합성예 490 ： 3-((4- (하이드록시메틸)페닐) (메틸)아미노)퀴놀란 -2(1H)-온 ¾醒R (400,.匪 z, CDC1 3) 6 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 Synthesis Example 490 ： 3-((4- (hydroxymethyl) phenyl) (methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1，4—디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol), (4- (메틸아미노)페닐)메탄올 (1.3 隱 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 490 화합물을 수득하였다 (수율 = 7¾ . 3-Bromoquinoline-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 隱 ol), (4- (methylamino) phenyl) methanol (1.3 隱 ol) and xantose (0.15 mmol) were added to the reaction mixture, Stir at 100 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 490 compound (yield = 7¾.
¾ NMR(400 MHz, CDC13)5 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 합성예 491 ： 3— (메틸 (4-비닐페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 491 ： 3— (Methyl (4-vinylphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-은 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 mmol), N-메틸 -4-비닐아닐린 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 491 화합물을 수득하였다 (수율 =43%). 3-bromoquinoline-2 (1H) -silver (1 mmol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 mmol), N-methyl-4-vinylaniline (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph to give the Synthesis Example 491 compound (yield = 43%).
¾ 丽 R(400 MHz, CDC13)6 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 합성예 492 ： 3- (에틸 (4-비닐페닐)아미노)퀴놀린 -2(1H)-온 ¾ δ R (400 MHz, CDC1 3 ) 6 8.14 (d, 1H), 8.02 (dd, 2H), 8.0 (s, 1H,-NH), 7.68 (dd, 2H), 7.36 (d, 1H), 7.31 (t, 1 H), 7.14 (t, 1 H), 6.63 (s, 1 H), 5.61 (s, 1 H), 5.18 (s, 1 H). MASS = 276.13 Synthesis Example 492: 3- (ethyl (4-vinylphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 2(1H)—온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol)ᅳ N-에틸 -4-비닐아닐린 (1.3 醒 ol) 및 잔포스 (0.15 隱 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 로마토그래프로 정제하여 합성예 492 화합물을 수득하였 다 (수율 =60%). 3-Bromoquinoline 2 (1H) —one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 隱 ol) ᅳ N-ethyl-4-vinylaniline (1.3 醒 ol) and xantose (0.15 隱 ol) were added to the reaction mixture and 100 For 10 hours at ° C Stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel romantograph to obtain a Synthesis Example 492 compound (yield = 60%).
¾ NMR(400 MHz, CDC13)6 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 합성예 493 ： 3-((3，4-디메틸페닐)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthetic Example 493: 3-((3,4-dimethylphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)—온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 画 ol), 3，4-디메틸아닐린 (1.3 mmol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 H로마토그래프로 정제하여 합성예 493 화합물을 수득하였다 (수율 =61%). 3-bromoquinolin-2 (1H) —one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 画 ol), 3,4-dimethylaniline (1.3 mmol) and xantose (0.15 隱 ol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel H-romatograph to give the compound of Synthesis Example 493 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 8.14(d, 1H), 8.0(s, 1H, -NH) , 7.36(d,¾ NMR (400 MHz, CDC1 3 ) 6 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d,
1H), 7.31 (t, 1H), 7.14(t, 1H)ᅳ 6.86(d, 1H), 6.24(m, 1H), 6.19(d, 1H), 4.0(s, 1H, -NH), 2.34(m, 6H) . MASS=264.13 합성예 494 ： 3-((3,4-디메틸벤질)아미노)퀴놀린 -2(1H)-은 1H), 7.31 (t, 1H), 7.14 (t, 1H) ᅳ 6.86 (d, 1H), 6.24 (m, 1H), 6.19 (d, 1H), 4.0 (s, 1H, -NH), 2.34 ( m, 6H). MASS = 264.13 Synthesis Example 494: 3-((3,4-dimethylbenzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)_온 (1 mmol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 mmol), (3，4-디메틸페닐)메타나민 (1.3 議 ol) 및 잔포스 (0.15 瞧 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 494 화합물을 수득하였다 (수율 =61¾ . 3-bromoquinoline-2 (1H) _one (1 mmol) was dissolved in 1,4-dioxane (2 mL). Add Cs 2 C0 3 (2 mmol), Pd (OAC) 2 (0.15 mmol), (3,4-dimethylphenyl) methamine (1.3 議 ol) and xantose (0.15 瞧 ol) to the reaction mixture and add 100 Stir at 10 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 494 compound (yield = 61¾.
¾ 匿 (400 MHz, CDC13)5 8.14(d, 1H), 8.0(s, 1H, -NH), 7.36(d, 1H), 7.31(t, 1H), 7.14(t, 1H)ᅳ 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 합성예 495 ： 3-((3，4-디하이드록시페닐)아미노)퀴놀린 -2(1H)-온 ¾ 400 (400 MHz, CDC1 3 ) 5 8.14 (d, 1H), 8.0 (s, 1H, -NH), 7.36 (d, 1H), 7.31 (t, 1H), 7.14 (t, 1H) ᅳ 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 Synthetic Example 495: 3-((3,4-dihydroxyphenyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 麵 ol), 4-아미노벤젠 -1,2-디을 (1.3 隱 ol) 및 잔포스 (0.15 瞧 ol')를 반웅 흔합물에 첨가하고 100°C에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 麵 ol), 4-aminobenzene-1,2-di (1.3 隱 ol) and xanphos (0.15 瞧 ol ') were added to the reaction mixture. Add and stir at 100 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatograph to give the Synthesis Example 495 compound (yield = 69%).
¾ 匿 (400 MHz, CDC13)6 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 합성예 496 ： 3-((3，4-디하이드록시벤질)아미노)퀴놀린 -2(1H)-온 ¾ 匿 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 496 ： 3-((3,4-Dihydroxybenzyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)_온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 01) ， ： Pd(0AC)2(0.15 隱 ol), 4- (아미노메틸)벤젠— 1,2-디을 (1.3 隱 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 496 화합물을 수득하였다 (수율 =61%). 3-Bromoquinoline-2 (1H) _one (1 mu ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱0 1), ： Pd (0AC) 2 (0.15 隱 ol), 4- (aminomethyl) benzene— 1,2-di (1.3 隱 ol) and xanphos (0.15 隱 ol) The reaction mixture was added and stirred at 100 ° C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 496 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 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 합성예 497 ： 3- ((벤조 [d][l,3]디옥솔 -5-일메틸)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 497: 3- ((benzo [d] [l, 3] dioxol-5-ylmethyl) amino) quinolin-2 (1H) -one
3-브로모퀴 린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 醒 ol), Pd(OAC)2(0.15 隱 ol), 벤조 [d] [1,3]디옥솔 -5-일메타나민 (1.3 醒 ol) 및 잔포스 (0.15 隱 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 497 화합물을 수득하였다 (수율 =61%). 3-Bromoquilin-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 醒 ol), Pd (OAC) 2 (0.15 隱 ol), benzo [d] [1,3] dioxol-5-ylmethanamin (1.3 醒 ol) and xanthose (0.15 隱 ol) ) Was added to the reaction mixture and stirred at 100 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 497 (yield = 61%).
¾ 丽 R(400 MHz, CDC13)6 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 합성예 498 ： 3_((2— (벤조 [d][l,3]디옥솔 -5-일)에틸)아미노)퀴놀린 -2(1H)-온¾ δ R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 498: 3 _ ((2— (benzo [d] [l, 3] dioxol-5-yl) ethyl) amino) quinolin-2 (1H) -one
3-브로모퀴^린 -2(1H)-온 (1 mmol)을 1,4—디옥산 (2 mL)에 용해시켰다. Cs2C03(2 醒 ol), Pd(0AC)2(0.15 瞧 ol), 2- (벤조 [d] [1，3]디옥솔 -5- 일)에타나민 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 498 화합물을 수득하였다 (수율 =60%). 3-bromoqui ^ rin-2 (1H) -one (1 mmol) was dissolved in 1,4—dioxane (2 mL). Cs 2 C0 3 (2 醒 ol), Pd (0AC) 2 (0.15 瞧 ol), 2- (benzo [d] [1,3] dioxol-5-yl) ethanamine (1.3 mmol) and xanthose ( It was added to 0.15 mmol) in common banung compound and stirred at 100 ° C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 498 (yield = 60%).
¾ NMR(400 MHz, CDC13)5 8.14(d, 1H) 8.0(s, lH, -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 합성예 499 ： 3— ((나프탈렌—2—일메틸)아미노)퀴놀린 -2(1H)-온 ¾ NMR (400 MHz, CDC1 3 ) 5 8.14 (d, 1H) 8.0 (s, lH, -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 Synthesis Example 499 ： 3— ((naphthalene-2-2-ylmethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(0AC)2(0.15 圍 ol), 나프탈렌 -2-일메타나민 (1.3 mmol) 및 잔포스 (0.15 mmol)를 반응 흔합물에 첨가하고 100°C에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 μl), naphthalen- 2- ylmethanamin (1.3 mmol) and xantose (0.15 mmol) were added to the reaction mixture and 10 at 100 ° C. Stir for hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 499 (yield = 43%).
H NMR(400 MHz, CDC13)6 8.14(d, 1H), 8.01(d, IH), 8.0(s, 1H, -NH),H NMR (400 MHz, CDC1 3 ) 6 8.14 (d, 1H), 8.01 (d, IH), 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 합성예 500 ： 3-((2- (나프탈렌 -2-일)에틸)아미노)퀴놀린 -2(1H)-온 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 Synthesis Example 500: 3-((2- (naphthalen-2-yl) ethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)ᅳ온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 瞧 ol)ᅳ 2- (나프탈렌 -2-일)에타나민 (1.3 醒 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 500 화합물을 수득하였다 (수율 =61%). ¾ 證 (400 MHz, CDC13)6 8.14(d, 1H), 8.01(d, 1H), 8.0(s, 1H, - NH), 7.97 (d, lH), 7.94(d, 1H), 7.58(t, 1H), 7.55(t, 1H)ᅳ 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 합성예 501 ： 3-(([1,1'-비페닐 ]-4-일메틸)아미노)퀴놀린 -2(1H)-온 3-Bromoquinoline-2 (1H) ᅳ one (1 隱 ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 瞧 ol) ᅳ 2- (naphthalen-2-yl) ethanamine (1.3 醒 ol) and xanthose (0.15 mmol) are added to the reaction mixture And stirred at 100 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the Synthesis Example 500 compound (yield = 61%). ¾ 證 (400 MHz, CDC1 3 ) 6 8.14 (d, 1H), 8.01 (d, 1H), 8.0 (s, 1H,-NH), 7.97 (d, lH), 7.94 (d, 1H), 7.58 ( t, 1H), 7.55 (t, 1H) ᅳ 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 Synthetic Example 501: 3-(([1,1'-biphenyl] -4-ylmethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4ᅳ디옥산 (2 mL)에 용해시켰다. 3-Bromoquinoline-2 (1H) -one (1 μl) was dissolved in 1,4 ᅳ dioxane (2 mL).
Cs2C03(2 mmol), Pd(0AC)2(0.15 隱 ol), [1，1'-비페닐 ]_4-일메타나민 (1.3Cs 2 C0 3 (2 mmol), Pd (0AC) 2 (0.15 隱 ol), [1,1'-biphenyl] _4-ylmethamine (1.3
■ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 KX C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 501 화합물을 수득하였다 (수율 =61¾ . Ol) and xantose (0.15 μl ol) were added to the reaction mixture and stirred at KX C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the Synthesis Example 501 compound (yield = 61¾.
¾ 醒 R(400 MHz, CDCl3)68.14(d, 1H), 8.0(s, 1H, — NH), 7.52(dd,¾ 醒 R (400 MHz, CDCl 3 ) 68.14 (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).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, 1 H), 3.92 (m, 2 H), 2.0 (s, 1 H, -NH).
MASS=326.14 합성예 502 ： 3-((2-([1，1'-비페닐 ]-4-일)에틸)아미노)퀴놀린 -2(1H)-온 MASS = 326.14 Synthetic Example 502: 3-((2-([1,1'-biphenyl] -4-yl) ethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 醒 ol), Pd(0AC)2(0.15 mmol), 2-([1，1'-비페닐 ]-4-일)에타나민 (1.3 mmol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 醒 ol), Pd (0AC) 2 (0.15 mmol), 2-([1,1'-biphenyl] -4-yl) ethanamine (1.3 mmol) and xanthose (0.15 隱 ol ) Was added to the reaction mixture and stirred at 100 ° C for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 502 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 8.14(d, 1H) , 8.0(s, 1H, -NH), 7.52(dd,¾ NMR (400 MHz, CDC1 3 ) 6 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),2H), 7.51 (dd, 2H), 7.41 (m, 1H), 7.36 (d, 1H), 7.33 (dd, 2H), 7.31 (t, 1H),
7.29(ddᅳ 2H), 7.14(t, 1H) , 6.10(s, 1H) , 3.92(m, 2H)， 3.6(m, 2H), 2.0(s,7.29 (dd ᅳ 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 합성예 503 ： 3-((4-벤질펜에틸)아미노)퀴놀린 -2(1H)-온 1H, -NH). MASS = 340.16 Synthesis Example 503: 3-((4-benzylphenethyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)_온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 醒 ol), Pd(OAC)2(0.15 誦 ol), 3-( [1ᅳ 1'-비페닐 ]-4-일)프로판 -1- 아민 (1.3 隱 ol) % 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한、 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 503 화합물올 수득하였다 (수율 =67%). 3-bromoquinolin-2 (1H) _one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 醒 ol), Pd (OAC) 2 (0.15 誦 ol), 3- ([1'1'-biphenyl] -4-yl) propane-1-amine (1.3 隱 ol)% glass Force (0.15 μl ol) was added to the reaction mixture and stirred at 100 ° C. for 10 hours. The resulting residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 503 (yield = 67%).
¾ 匪 R( 400 MHz, CDC13)6 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(sᅳ 1H), 3.92 On' 2H), 3.6(m, 2H), 2.8(m, 2H), 2.0(s, 1H, -NH). MASS=354.17 합성예 504 ： 3-((4-벤질벤질)아미노)퀴놀린 -2(1H)-은 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 ᅳ 1H), 3.92 On '2H), 3.6 (m , 2H), 2.8 (m, 2H), 2.0 (s, 1H, -NH). MASS = 354.17 Synthetic Example 504: 3-((4-benzylbenzyl) amino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 画 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 隱 ol), (4-벤질페닐)메타나민 (1.3 隱 ol) 및 잔포스 (0.15 mmol)를 반웅 흔합물에 첨가하고 10CTC에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 隱 ol), (4-benzylphenyl) methanamin (1.3 隱 ol) and xanthose (0.15 mmol) were added to the reaction mixture at 10 CTC Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 504 (yield = 61%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 505 ： 3- (에틸아미노)퀴놀린 -2(1H)-온 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 505: 3- (ethylamino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 隱 ol)을 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 隱 ol), 에타나민 (1.3 mmol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하하고 10CTC에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 CO 3 (2 mmol), Pd (OAC) 2 (0.15 μl ol), ethanamine (1.3 mmol) and xantose (0.15 μl ol) were added to the reaction mixture and stirred at 10 CTC for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 505 (yield = 61%).
¾ 匪 R(400 MHz, CDC13)6 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 합성예 506 ： 3- (프로필아미노)퀴놀린 -2(1H)-은 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 506: 3- (propylamino) quinoline-2 (1H) -silver
3-브로모퀴놀린 -2(1H)-온 (1 瞧 ol)을 1，4—디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol), 프로판 -1-아민 (1.3 隱 ol) 및 잔포스 (0.15 瞧 ol)를 반웅 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 506 화합물을 수득하였다 (수율 =53%). 3-Bromoquinoline-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 隱 ol), Pd (0AC) 2 (0.15 隱 ol), propane-1-amine (1.3 隱 ol) and xanphos (0.15 瞧 ol) were added to the reaction mixture and at 100 ° C Stir for 10 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 506 (yield = 53%).
¾ 匿 (400 MHz, CDC13)6 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 합성예 507 ： 3- (부틸아미노)퀴놀린 -2(1H)-온 ¾ 匿 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 507: 3- (butylamino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)—온 (1 隱 ol)을 1，4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 隱 ol), Pd(0AC)2(0.15 隱 ol), 부탄— 1—아민 (1.3 隱 ol) 및 잔포스 (0.15 隱 ol)를 반웅 흔합물에 첨가하고 10CTC에서 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 μ ol) was dissolved in 1,4-dioxane (2 mL). Cs 2 C0 3 (2 μl ol), Pd (0AC) 2 (0.15 μl ol), butane— 1—amine (1.3 μl ol) and xantose (0.15 μl ol) were added to the reaction mixture and 10 h at 10 CTC. Was stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 507 (yield = 61.
¾ NMR(400 MHz, CDC13)6 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)ᅳ 2.73(m, 2H) , 2.0(s, 1H, - NH), 1.52(m, 2H) , 1.31(m, 2H), 0.9(s, 3H). MASS=216.13 합성예 508 ： 3- ((에톡시메틸)아미노)퀴놀린 -2(111)_온 ¾ NMR (400 MHz, CDC1 3 ) 6 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) ᅳ 2.73 (m, 2H), 2.0 (s, 1H,-NH), 1.52 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H). MASS = 216.13 Synthetic Example 508: 3-((ethoxymethyl) amino) quinolin-2 (111) _one
3-브로모퀴놀린 -2(1H)-온 (1 瞧 ol)를 1，4-디옥산 (2 mL)에 용해시켰다. 3-bromoquinolin-2 (1H) -one (1 μl) was dissolved in 1,4-dioxane (2 mL).
Cs2C03(2 瞧 ol), Pd(0AC)2(0.15 mmol), 에특시메타나민 (1.3 画 ol) 및 잔포스 (0.15 画 ol)를 반응 흔합물에 첨가하고 100°C에서 10시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 합성예 508 화합물을 수득하였다 (수율 = 67%)· Cs 2 C0 3 (2 瞧 ol), Pd (0AC) 2 (0.15 mmol), ecsimethanamin (1.3 画 ol) and xanthose (0.15 画 ol) were added to the reaction mixture and 10 h at 100 ° C. Was stirred. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 508 (yield = 67%)
¾ 匪 R(400 MHz, CDC13)6 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, -¾ 匪 R (400 MHz, CDC1 3 ) 6 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 합성예 509 ： 3-(( (에틸티오)메틸)아미노)퀴놀린 -2(1H)-온 NH), 3.28 (m, 2 H), 1.10 (s, 3 H). MASS = 218.11 Synthesis Example 509: 3-(((ethylthio) methyl) amino) quinolin-2 (1H) -one
3-브로모퀴놀린 -2(1H)-온 (1 mmol)를 1,4-디옥산 (2 mL)에 용해시켰다. Cs2C03(2 mmol), Pd(OAC)2(0.15 隱 ol), (에틸티오)메타나민 (1.3 画 ol) 및 잔포스 (잔포스 )(0.15 mmol)를 반웅 흔합물에 첨가하고 100°C에서 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). Cs 2 C0 3 (2 mmol), Pd (OAC) 2 (0.15 隱 ol), (ethylthio) methanamin (1.3) ol) and zanfos (zanfos) (0.15 mmol) were added to the reaction mixture and 100 Stir at 10 ° C for 10 h. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the compound of Synthesis Example 509 (yield = 61%).
■ ¾ 醒 (400 MHz, CDC13)5 8.14(d, 1H), 8.0(s, 1Hᅳ -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 단계 (e-5, h-8)의 '일반적 과정 ■ ¾ 醒 (400 MHz, CDC1 3 ) 5 8.14 (d, 1H), 8.0 (s, 1H ᅳ -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 Step (e-5, h-8 ) in the "general procedure
4번 또는 7번 화합물, (430mg, 0.7隱01)， DIPEA(0.2mL, l. imol) 및 1?4-∞-(：1(0.1^，0.8隱01)를 0¾(：12(20|1 )에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 5번 또는 8번 화합물을 수득하였다. 합성예 80 ： 5-벤즈아미도 -2—옥소— N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 Compound 4 or 7, (430mg, 0.7 隱 01), DIPEA (0.2mL, l.imol) and 1? 4-∞-(： 1 (0.1 ^, 0.8 隱 01) were converted to 0¾ (： 1 2 (20 (1) was stirred for 15 minutes The residue was extracted with ethyl acetate and saturated NaHC0 3 and then purified by silica gel column chromatography to obtain compound 5 or 8. Synthesis Example 80: 5-benzamido- 2—oxo— N-phenyl-1, 2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3—카르복사마이드 ( 1 隱 01)， DIPEA 1.5醒 ol) 및 벤조일클로라이드 (1.2隱 ol )를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 80 화합물을 수득하였다 (수율 =61%). 5-amino-2-oxo-N-phenyl-1, 2-dihydroquinoline-3—carboxamide (1 隱 01), DIPEA 1.5 醒 ol) and benzoylchloride (1.2 隱 ol) were converted to CH 2 Cl 2 ( 2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 80 compound (yield = 61%).
¾ 匪 R(400 MHz, CDC13)6 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 합성예 81 ： 5-벤즈아미도— 2-옥소 -N-페닐 -1,2-디하이드로퀴놀린 -3-카르복사 마이드 l-( (2H-피롤 -2-일 )메틸 )-5-아미노ᅳ 2-옥소 -Nᅳ페닐 -1， 2—디하이드로퀴 놀린 -3-카르복사마이드 (1 隱 ol), DIPEAC1.5 瞧 ol) 및 벤조일 클로라이드 (1.2 瞧 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테 이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 81 화합물을 수득하였다 (수율 =64%). ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 81 5-5-benzamido—2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide l- ((2H-pyrrole-2-yl) methyl) -5-amino ᅳ 2-oxo-N ᅳ phenyl-1, 2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEAC1.5瞧 ol) and benzoyl chloride (1.2 瞧 ol) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 81 compound (yield = 64%).
¾ 匿 (400 MHz, CDC13)5 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 합성예 82 ： 5-(4-메틸벤즈아미도) -2-옥소 -N-페닐 -1，2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 匿 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 82: 5- (4-Methylbenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -2 옥소 페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1 瞧 ol), DIPEA .5隱 ol) 및 4-메틸벤조일클로라이드 (1.2隱 ol )를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 82 화합물을 수득하였다 (수율 =64%). 5-amino-2 oxo phenyl-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA .5' ol) and 4-methylbenzoylchloride (1.2 'ol) were selected from CH 2 C1 2 ( 2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to give the compound of Synthesis 82 (yield = 64%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 83 ： l-(2-(2H-피를 -2-일)에틸) -5-(4-메틸벤즈아미도) -2-옥소 -N- 페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 MASS = 397.14 Synthesis Example 83: l- (2- (2H-Py-2-yl) ethyl) -5- (4-methylbenzamido) -2-oxo-N-phenyl-1; 2-dihydroquinoline-3-carboxamide
1-(2-(2Η-피롤 -2-일)에틸 )-5-아미노 -2-옥소 -N-페닐— 1， 2-디하이드로 퀴놀린 -3-카르복사마이드 (1 麵 ol), DIPEA(1.5 薩 ol) 및 4—메틸벤조일 클로라이드 (1.2 隱 ol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 83 화합물을 수득하였다 (수율 =61%). 1- (2- (2Η-pyrrole-2-yl) ethyl) -5-amino-2-oxo-N-phenyl— 1, 2-dihydro quinoline-3-carboxamide (1 麵 ol), DIPEA ( 1.5 μs ol) and 4—methylbenzoyl chloride (1.2 μs ol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to give the compound of Synthesis Example 83 (yield = 61%).
¾ NMRC400 MHz, CDC13)5 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 합성예 84 ： 5-(4-브로모벤즈아미도) -2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린- 3-카르복사마이드 ¾ NMRC400 MHz, CDC1 3 ) 5 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 Synthesis Example 84: 5- (4-Bromobenzamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소ᅳ N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 (lmmol), DIPE 1.5薩 ol) 및 4-브로모벤조일클로라이드 (1.2議 ol )를 C C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 84 화합물을 수득하였다 (수율 = 49%) . 5-amino-2-oxo-eu N- phenyl-1,2-dihydro-quinoline-3-carboxamide (lmmol), DIPE薩1.5 ol) and 4-bromobenzoyl chloride (1.2議ol) the C 2 C1 Stir at (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 84 (yield = 49%).
¾ 匪 R (400 MHz, CDC13)6 10.12(s, 1H, - H) , 9.15(s, 1H, - H) , 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 합성예 88 ： 5-(4-클로로벤즈아미도) -2-옥소 -N-(p-를일) -1，2-디하이드로 퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -H), 9.15 (s, 1H, -H), 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 Synthesis Example 88: 5- (4-chlorobenzamido) -2-oxo-N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -2_옥소 N-(p-를일 )-i， 2-디하이드로퀴놀린 _3_카르복사마이드 5-amino-2-oxo-_ N - (p- reulil) -i, 2-dihydro-quinoline-3 _ _ carboxamide
(1 瞧 ol), DIPEA(1.5 瞧 ol) 및 4-클로로벤조일 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 88 화합물을 수득하였다 (수율 = 47%) . (1 μl), DIPEA (1.5 μl) and 4-chlorobenzoyl chloride (1.2 mmol) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 88 compound (yield = 47%).
¾ NMR(400, MHz, CDC13)5 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 합성예 90 ： 5-(4-플루오로벤즈아미도) -N-(4-메톡시페닐) -2—옥소 -1，2-디하이 드로퀴놀린 -3-카르복사마이드 ¾ NMR (400, MHz, CDC1 3 ) 5 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 Synthesis Example 90: 5- (4-fluorobenzamido) -N- (4-methoxyphenyl) -2—oxo-1,2-dihydrodroquinoline-3-carboxamide
5-아미노 (4-메특시페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 隱 ol), DIPEAU.5 誦 ol) 및 4-플루오로벤조일 클로라이드 L2 讓 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 90 화합물을 수득하였다 (수율 =61%). 5-amino (4-methoxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEAU.5' ol) and 4-fluorobenzoyl chloride L2 'ol ) Was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After silica gel column Purification by chromatography gave Synthesis Example 90 compound (yield = 61%).
¾ 蘭 R(400. MHz, CDC13)6 10.12(s, 1H, -NH), 9.15(s, 1H, ᅳ 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 합성예 91 ： 5-(4-에틸벤즈아미도) -N-(4-메특시페닐) -2-옥소— 1,2-디하이드로 퀴놀린—3-카르복사마이드 ¾ 蘭 R (400. MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 9.15 (s, 1H, ᅳ 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 Synthesis Example 91: 5- (4-ethylbenzamido) -N- (4-methoxyphenyl) -2-oxo- 1,2-dihydroquinoline-3-carboxamide
5-아미노 -Nᅳ (4-메록시페닐)ᅳ 2-옥소— 1， 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 mmol), DIPEA(1.5 mmol) 및 4-에틸벤조일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화5-amino-N ᅳ (4-methoxyphenyl) ᅳ 2-oxo— 1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-ethylbenzoyl chloride (1.2 隱ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue is ethyl acetate and saturated
NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 91 화합물을 수득하였다 (수율 =61%). Extracted with NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 91 (Yield = 61%).
¾ 匿 (400 MHz, CDC13)5 10.12(s, 1H, -NH), 9.15(s, 1H, -NH) ,¾ 匿 (400 MHz, CDC1 3 ) 5 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 합성예 93 ： N-(4-브로모페닐) -2-옥소 -5-(4-비닐벤즈아미도) -1,2-디하이드로 퀴놀린 -3-카르복사마이드 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, 2 H), 1.25 (s, 3 H). MASS-441.17 Synthesis Example 93 ： N- (4-bromophenyl) -2-oxo-5- (4-vinylbenzamido) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -N- -브로모페닐) -2-옥소 -1， 2—디하이드로퀴놀린 -3-카르복사 마이드 (1 誦 ol), DIPEA(1.5 mmol) 및 4-비닐벤조일 클로라이드 (1.2 國 ol)를 5 -amino-N-bromophenyl) -2-oxo-1,2—dihydroquinoline-3-carboxamide (1 誦 ol), DIPEA (1.5 mmol) and 4-vinylbenzoyl chloride (1.2 countries ol )
C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화Stir for 15 min in C¾Cl 2 (2 mL). The residue is ethyl acetate and saturated
NaHC03로 추출하 다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 93 화합물을 수득하였다 (수율 =61%). Extract with NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 93 (Yield = 61%).
¾ NMR(400 MHz, CDC13)5 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),¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 94 ： N-(4-브로모페닐) -2-옥소 -l-(2- (티오펜 -2-일)에틸) -5-(4-비닐 벤즈아미도) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 6.97 (dd, 2H), 6.63 (s, 1H), 5.61 (s, 1H), 5.18 (s, 1H). MASS = 487.05 Synthesis Example 94: N- (4-bromophenyl) -2-oxo-1-(2- (thiophen-2-yl) ethyl) -5 (4-vinylbenzamido) -1, 2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-브로모페닐) -2-옥소 -1-(2- (티오펜 -2—일)에틸) -1， 2-디 하이드로퀴놀린 -3—카르복사마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 4- 비닐벤조일 출로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 '정제하여 합성예 94 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-bromophenyl) -2-oxo-1- (2- (thiophen-2-2-yl) ethyl) -1, 2-dihydroquinoline-3-carboxamide (1 隱ol), DIPEA (1.5 mmol) and 4- Vinylbenzoyl fluorolide (1.2 μl) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Subsequently, silica gel column chromatography was used to obtain ' synthesis 94 ' (yield = 61%).
¾ NMR(400 MHz, CDC13)8 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. Km, 3H) , 2.9(s, 2H), 2.0(s, 1H). MASS=597.07 합성예 98 ： N-(4-클로로페닐) -5-(4-니트로벤즈아미도) -2-옥소 -1，2-디하이드 로퀴놀린— 3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 8 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.Km, 3H), 2.9 (s, 2H), 2.0 (s, 1H). MASS = 597.07 Synthesis Example 98: N- (4-chlorophenyl) -5 (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline—3-carboxamide
5-아미노 -N-(4-클로로페닐 )-2—옥소— 1， 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 mmol), DIPEAC1.5 mmol) 및 4-니트로벤조일 클로라이드 (1.2 mmol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 98 화합물을 수득하였다 (수율 = 71%). 5-amino-N- (4-chlorophenyl) -2—oxo— 1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEAC1.5 mmol) and 4-nitrobenzoyl 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 NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 98 compound (yield = 71%).
¾ NMR(400 MHz, CDC13)6 10.12(s, 1H, -NH)ᅳ 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—카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH) ᅳ 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 Synthesis Example 99 N- (4-chlorophenyl) -1-methyl-5— (4-nitrobenzamido) -2—oxo-1,2-dihydroquinoline-3carboxamide
5-아미노 -N-(4ᅳ클로로페닐 )-1-메틸 -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 '· 隱 01)， DIPEA(1.5 mmol) 및 4—니트로벤조일 클로라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 99 화합물을 수득하였다 (수율 = 42%) . ¾ 丽(400 MHz, CDC13)5 10.12(s, 1H, -NH), 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H), 8.11(dd, 2H), 7.88(111， 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-카르복사마이드 5-amino-N- (4 ᅳ chlorophenyl) -1-methyl-2-oxo ᅳ 1, 2-dihydroquinoline-3-carboxamide (1 ′隱0 1), DIPEA (1.5 mmol) and 4 —Nitrobenzoyl chloride (1.2 μl) was stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 99 compound (yield = 42%). ¾ (400 MHz, CDC1 3 ) 5 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H), 8.11 (dd, 2H) , 7.88 (111, 2H), 7.75 (dd, 1H), 7.47 (dd, 2H), 7.29 (t, 1H), 3.2 (s, 3H). MASS-476.09 Synthesis Example 100: N- (4-chlorophenyl) -1-ethyl-5 (4-nitrobenzamido) -2-oxo-1,2- Dihydroquinoline-3-carboxamide
5-아미노 -Nr(4-클로로페닐) -1-에틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 隱 01) ， DIPEAC1.5 隱 ol) 및 4-니트로밴조일 클로라이드 (1.2 腿 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아 세테이트 및 포화 NaHC¾로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 100 화합물올 수득하였다 (수율 =61%). 5-amino-Nr (4-chlorophenyl) -1-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱0 1), DIPEAC1.5 隱 ol) and 4-nitro Banjoyl chloride (1.2 cc ol) was stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC¾. Then purified by silica gel column chromatography to obtain a Synthesis Example 100 compound (yield = 61%).
¾ NMR(400 MHz, CDC13)5 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 합성예 101 ： 5-(4-브로모벤즈아미도) -N-(4-클로로페닐) -2—옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 101: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -2—oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐 )-2—옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 瞧 ol), DIPEA(1.5 mmol) 및 4-브로오벤조일 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 101 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -2—oxo-1, 2-dihydroquinoline-3-carboxamide (1 瞧 ol), DIPEA (1.5 mmol) and 4-broobenzoyl chloride (1.2 mmol) was stirred in C¾Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 101 compound (yield = 61%).
¾ NMR(400 MHz, CDC13)5 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-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 102: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4—클로로페닐 )-1—메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 隱 01) ， DIPEA(1.5 mmol) 및 4-브로모벤조일 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크 로마토그래피로 정제하여 합성예 102 화합물을 수득하였다 (수율 =73%). 5-amino-N- (4—chlorophenyl) -1—methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱0 1), DIPEA (1.5 mmol) and 4-bro Mobenzoyl chloride (1.2 mmol) was stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to obtain the compound of Synthesis 102 (yield = 73%).
¾ NMRC400 MHz, CDC13)8 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 합성예 103 ： 5-(4-브로모벤즈아미도) -N-(4-클로로페닐) -1-에틸 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMRC400 MHz, CDC1 3 ) 8 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 Synthesis Example 103: 5- (4-Bromobenzamido) -N- (4-chlorophenyl) -1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐 )-1-에틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 醒 ol), DIPEA(1.5 mmol) 및 4-브로모벤조일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테 이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 103 화합물을 수득하였다 (수율 =61%). 5 -amino-N- (4-chlorophenyl) -1-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 醒 ol), DIPEA (1.5 mmol) and 4-bromo Benzoyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 103 (Yield = 61%).
¾ 匪 R(400 MHz, CDC13)6 10.12(s, 1H, -NH) , 9.15(s, 1H, -NH), 8.44(dd, 2H), 8.28(s, 1H)ᅳ 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 합성예 104 ： N-(4-클로로페닐) -5-(4- (하이드록시메틸)벤즈아미도) -2-옥소- 1， 2-디하이드로퀴놀린— 3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 9.15 (s, 1H, -NH), 8.44 (dd, 2H), 8.28 (s, 1H) ᅳ 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 Synthesis Example 104: N- (4-chlorophenyl) -5 (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline—3-carboxamide
5-아미노 -N-(4-클로로페닐 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 画 ol), DIPEA 1.5 mmol) 및 4- (하이드록시메틸)벤조일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세 테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피 로 정제하여 합성예 104 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 画 ol), DIPEA 1.5 mmol) and 4- (hydroxymethyl) benzoyl chloride (1.2 Pa ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 104 (yield = 61%).
¾ NMR(400 MHz, CDC13)6 10.12(s, 1H, -NH)， 9.15(s, 1H, -NH),¾ NMR (400 MHz, CDC1 3 ) 6 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 합성예 105 ： N-(4-클로로페닐) -5-(4- (하이드록시메틸)벤즈아미도) -1-메틸- 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 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, 1 H), 4.61 (s, 2 H), 3.65 (s, 1 H, -OH). MASS = 447.10 Synthesis Example 105: N- (4-chlorophenyl) -5 (4- (hydroxymethyl) benzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-3-car Copyamide
5-아미노 -N-(4-클로로페닐 )-1-메틸 -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 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 105 화합물올 수득하였다 (수율 = 58%) . Έ 匪 R(400MHz, CDC13)8 10.12(s, IH, -NH), 9.15(s, IH, -NH), 8.28(s, IH), 8.OC3, IH, -NH) , 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, IH), 4.61(s, 2H), 3.65(s, IH, -OH), 3.2(s, 3H). MASS= 461.11 합성예 106 ： N-(4-클로로페닐) -1-에틸 -5-(4- (하이드록시메틸)벤즈아미도) - 5 -amino-N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA 1.5 mmol) and 4- (hydroxymethyl ) Benzoyl chloride (1.2 mmol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain a compound of Synthesis Example 105 (yield = 58%). R (400 MHz, CDC1 3 ) 8 10.12 (s, IH, -NH), 9.15 (s, IH, -NH), 8.28 (s, IH), 8.OC3, IH, -NH), 7.96 (dd , 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H), 7.29 (t, IH), 4.61 (s, 2H), 3.65 (s, IH, -OH), 3.2 (s, 3H). MASS = 461.11 Synthesis Example 106: N- (4-chlorophenyl) -1-ethyl-5 (4- (hydroxymethyl) benzamido)-
2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-1, 2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐) -1-에틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 醒 ol), DIPEAU.5 隱 ol) 및 4— (하이드록시메틸)벤조일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 :정제하여 합성예 106 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -1-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEAU.5' ol) and 4— ( Hydroxymethyl) benzoyl chloride (1.2 μl ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After silica gel column chromatography : Purification to give the Synthesis Example 106 compound (yield = 61%).
¾ NMR(400 MHz, CDC13)5 10.12(s, IH, -NH), 9.15(s, IH, -NH),¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 9.15 (s, IH, -NH),
8.28(s, IH), 8.0(s, IH, -NH) , 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.54(dd, 2H), 7.47(dd, 2H)， 7.29(t, IH), 4.61(s, 2H), 3.65(s, IH, -OH),8.28 (s, IH), 8.0 (s, IH, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.54 (dd, 2H), 7.47 (dd, 2H) ), 7.29 (t, IH), 4.61 (s, 2H), 3.65 (s, IH, -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-카르복사마이드 3.2 (s, 2H), 2.7 (s, 3H). MASS = 475.13 Synthesis Example 107 ： 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-디하이드 로퀴놀린 -3—카르복사마이드 (1隱 ol), DIPE 1.5隱 ol) 및 4- (하이드록시메틸) 벤조일클로라이드 (1.2画 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 107 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -1- (furan-2-ylmethyl) -2-oxo— 1, 2-dihydroquinoline-3—carboxamide (1 ′ ol), DIPE 1.5隱 ol) and 4- (hydroxymethyl) benzoylchloride (1.2 画 ol) were stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 107 (Yield = 61%).
¾ NMR(400 MHz, CDC13)8 10.12(s, IH, -NH) , 9.15(sᅳ IH, -NH) ,¾ NMR (400 MHz, CDC1 3 ) 8 10.12 (s, IH, -NH), 9.15 (s ᅳ IH, -NH),
8.28(s, IH), 8.0(s, IH, -NH), 7.96(dd, 2H), 7.88(m, 2H), 7.75(dd, 2H), 7.65(sᅳ IH), 7.54(dd, 2H), 7.47(dd, 2H), 7.29(t, IH), 6.42(m, 2H), 4.61(s, 2H), 4.07(s, 2H) , 3.65(s, IH, -OH). MASS=527.12 합성예 108 ： N-(4-클로로페닐) -5-(4-니트로벤즈아미도) -2-옥소 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 5-아미노 -N-(4-클로로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이드 (1.2 讓 ol)를 C¾Cl2(2mi:)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 108 화합물을 수득하였다 (수율二 61%). 8.28 (s, IH), 8.0 (s, IH, -NH), 7.96 (dd, 2H), 7.88 (m, 2H), 7.75 (dd, 2H), 7.65 (s ᅳ IH), 7.54 (dd, 2H ), 7.47 (dd, 2H), 7.29 (t, IH), 6.42 (m, 2H), 4.61 (s, 2H), 4.07 (s, 2H), 3.65 (s, IH, -OH). MASS = 527.12 Synthesis Example 108: N- (4-chlorophenyl) -5 (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide 5-amino-N- (4-chlorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEA (1.5 mmol) and 4-nitrobenzoyl chloride (1.2 讓ol) was stirred in C¾Cl 2 (2mi :) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 108 (Yield 2 61%).
¾ NMR(400 MHz, CDC13)5 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 합성예 109 ： N-(4-클로로페닐) -1-메틸 -5-(4-니트로벤즈아미도) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 109 ： N- (4-chlorophenyl) -1-methyl-5 (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide
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 誦 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아 세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 109 화합물올 수득하였다 (수율 =61%). 5-amino -N- (4-chlorophenyl) -1-methyl-2-oxo, 1,2-dihydro-quinoline-3-carboxamide (1, mmol), DIPEA 1.5 mmol) and 4-nitrobenzoyl Chloride (1.2 μl) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 109 (yield = 61%).
¾ NMR(400 MHz, CDC13)5 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 합성예 110 ： N-(4-클로로페닐) -1-에틸 -5-(4-니트로벤즈아미도) -2-옥소 -1,2- 디하이드로퀴놀린」 3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 110: N- (4-chlorophenyl) -1-ethyl-5 (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline 3-carboxamide
5-아미노 -N-(4-클로로페닐 )-1-에틸 -2-옥소— 1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 4-니트로벤조일 클로라이 드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 110 화합물을 수득하였다 (수율 = 64%) . 5-amino-N- (4-chlorophenyl) -1-ethyl-2-oxo— 1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 4-nitrobenzoyl chloride Ride (1.2 μl) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 110 compound (yield = 64%).
¾ 證(400 MHz, CDC13)6 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 합성예 111 ： N-(4클로로페닐) -l-(2- (퓨란 -2-일)에틸) -5-(4-니트로벤즈아미 도) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 400 (400 MHz, CDC1 3 ) 6 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, 3 H). MASS = 490.10 Synthesis Example 111 N- (4chlorophenyl) -1- (2- (furan-2-yl) ethyl) -5 (4-nitrobenzamido) -2-oxo-1,2-di Hydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐 ) -1-(2- (퓨란 -2-일 )에틸 )-2-옥소 -1， 2-디하 이드로퀴놀린 -3-카르복사마이드 (1 睡 ol), DIPEA(1.5 mmol) 및 4-니트로 벤조일클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 111 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -1- (2- (furan-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1 'ol) , DIPEA (1.5 mmol) and 4-nitro benzoylchloride (1.2 μl) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 111 (Yield = 61%).
¾ NMR(400 MHz, CDC13)5 10.12(s, 1H, -NH), 9.15(s, 1H, -NH),¾ NMR (400 MHz, CDC1 3 ) 5 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 합성예 112 ： N-(4-클로로페닐) -2-옥소 -5-(2-페닐아세트아미도) -1，2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 112: N- (4-chlorophenyl) -2-oxo-5 (2-phenylacetamido) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 mmol), DIPEACL5 mmol) 및 2-페닐아세틸 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 112 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEACL5 mmol) and 2-phenylacetyl chloride (1.2 mmol) were dissolved in C¾Cl. Stir at 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis 112 (Yield = 61%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 113 ： 5-벤즈아미도 -N-(4-클로로페닐) -1-메틸 -2-옥소 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 113: 5-benzamido-N- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐) -1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 讓 ol), DIPEM1.5 mmol) 및 벤조일 클로라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 113 화합물을 수득하였다 (수율 =61%). 5-amino-N- (4-chlorophenyl) -1-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 讓 ol), DIPEM1.5 mmol) and benzoyl chloride (1.2隱 ol) was stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography Synthesis Example 113 The compound was obtained (yield = 61%).
¾ 匿 (400 MHz, CDC13)6 10.12(s, 1H, -NH), 8.28(s, 1H), 7.88(m, 2H), 7.75(dd, 2 , 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 합성예 114 ： (5-벤즈아미도 -N-(4-클로로페닐) -1-에틸 _2-옥소 -12-디하이드 로퀴놀린 -3-카르복사마이드) ¾ 匿 (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 2H), 7.75 (dd, 2, 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 Synthesis Example 114: (5-benzamido-N- (4 -Chlorophenyl) -1-ethyl _2-oxo-12-dihydroquinoline-3-carboxamide)
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 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 114 화합물을 수득하였다 (수율 = 64%) . 5-amino-N- (4-chlorophenyl) -1—ethyl-2-oxo-1 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA 1.5 mmol) and benzoyl chloride (1.2 mmol) Stir for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 114 (yield = 64%).
¾ 画 R(400 MHz CDC13)6 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 합성예 115 ： N-(4-클로로페닐) -5-(4-에틸벤즈아미도) -2—옥소 -1,2-디하이드 로퀴놀린 -3-카르복사마이드 ¾ 画 R (400 MHz CDC1 3 ) 6 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 Synthesis Example 115: N- (4-chlorophenyl) -5 (4-ethylbenzamido) -2—oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-클로로페닐) -2-옥소 -1 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 隱 ol), DIPEA 1.5 mmol) 및 4-에틸벤조일 클로라이드 (1.2 隱 ol)를 5-amino-N- (4-chlorophenyl) -2-oxo-1 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5 mmol) and 4-ethylbenzoyl chloride (1.2' ol) To
CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화Stir for 15 min in CH 2 Cl 2 (2 mL). The residue is ethyl acetate and saturated
NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 115 화합물을 수득하였다 (수율 = 61%). Extraction with NaHC0 3 and purification by silica gel column chromatography gave the compound of Synthesis 115 (yield = 61%).
¾ 證(400 MHz, CDC13)6 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,¾ 證 (400 MHz, CDC1 3 ) 6 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 합성예 116 ： N-(4-클로로페닐) -5-(4-에틸벤즈아미도)— 1-메틸 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 2H), 1.25 (s, 3H). MASS = 445.12 Synthesis Example 116 N- (4-chlorophenyl) -5 (4-ethylbenzamido)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4—클로로페닐) -1-메틸 -2—옥소 -1 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 mmol), DIPEA 1.5 瞧 ol) 및 4-에틸벤조일 클로라이드 (1.2 醒 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예5-amino-N- (4—chlorophenyl) -1-methyl-2—oxo-1 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA 1.5 瞧 ol) and 4-ethylbenzoyl chloride ( 1.2 醒 ol) was stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography.
116 화합물을 수득,하였다 (수율 =67%) . 116 compound was obtained (yield = 67%).
¾ 賺 (400 MHz, CDC13)6 10.12(s, 1H, - H), 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 합성예 117 (N-(4-클로로페닐) -1-에틸 -5-(4-에틸벤즈아미도) -2-옥소 -1，2- 디하이드로퀴놀린 -3-카르복사마이드) ¾ 賺 (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -H), 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 Synthesis Example 117 (N- (4-chlorophenyl) -1-ethyl-5 (4-ethylbenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide)
5-아미노 -N-(4-클로로페닐) -1ᅳ에틸 -2-옥소— 1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 隱 01)ᅳ DIPEA 1.5 瞧 ol) 및 4-에틸벤조일 클로라이드 (1.2 画 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예5-amino-N- (4-chlorophenyl) -1 ᅳ ethyl-2-oxo—1,2-dihydroquinoline-3-carboxamide (1 隱0 1) ᅳ DIPEA 1.5 瞧 ol) and 4-ethyl Benzoyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography.
117 화합물을 수득하였다 (수율 = 61%). 117 compound was obtained (Yield = 61%).
¾ NMR (400 MHz, CDC13)6 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88
Cm, 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 합성예 122 ： N-(4-플루오로페닐 )-2_옥소— 5-(2-(p-를일)아세트아미도 )-1,2- 디하이드로퀴놀린 -3_카르복사마이드 Cm, 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 Synthesis Example 122: N- (4-fluorophenyl) -2_oxo—5- (2- (p-ylyl) acetamido) -1,2-dihydroquinoline-3_carboxamide
5-아미노 -N-(4-플루오로페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복 사마이드 (1 隱 01)， DIPEAC1.5 隱 ol) 및 2-(p-를일)아세틸클로라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 122 화합물을 수득하였다 (수율 =61%) 5-amino-N- (4-fluorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱0 1), DIPEAC1.5 隱 ol) and 2- (p -Yl) acetylchloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 122 (yield = 61%).
¾ 匪 R (400 MHz, CDC13)6 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-를일)아세트아미도) -1， 2-디하이드로퀴놀린 -3-카르복사마이드 5-아미노 -N-(4-플루오로페닐 )-1—메틸 -2-옥소— 1， 2-디하이드로퀴놀린- 3-카르복사마이드 (1 隱 oO, DIPEA(1.5 mmol) 및 2-(p-를일)아세틸 클로라 이드 (1.2 隱01)를: CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 123 화합물을 수득하였다 (수율 = 61%). ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 123: N- (4-fluorophenyl) -1-methyl-2-oxo-5- (2— (p-ylyl) acetamido) -1,2-dihydroquinoline-3- Carboxamide 5-amino-N- (4-fluorophenyl) -1—methyl-2-oxo— 1, 2-dihydroquinoline-3-carboxamide (1 隱 oO, DIPEA (1.5 mmol) and 2- (p - reulil) acetyl chloride fried (1.2隱0 1) a: CH 2 Cl 2 (2mL) at and stirred for 15 minutes moieties synthetic example 123 was extracted with ethyl acetate and saturated NaHC0 3, and purified by silica gel column chromatography to give Compound obtained (yield = 61%).
¾ 丽 R(400 MHz, CDC13)5 10.12(s, 1H, -NH), 8.28(s, 1H)' 8.0(s' 1H, -NH), 7.88(111， 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-를일)아세트아미도) -1， 2-디하이드로퀴놀린 -3-카르복사마이드： ¾ δ R (400 MHz, CDC1 3 ) 5 10.12 (s, 1H, -NH), 8.28 (s, 1H) '8.0 (s' 1H, -NH), 7.88 (111, 4H), 7.29 (t, 1H ), 7.22 (dd, 2H), 7.11 (m, 4H), 3.2 (s, 3H), 2.34 (s, 3H). MASS = 443.16 Synthesis Example 124: 1-ethyl-N- (4-fluorophenyl) -2-oxo-5 (2- (p-ylyl) acetamido) -1,2-dihydroquinoline-3- Carboxamide ：
5-아미노 -1-에틸 -N-(4-풀루오로페닐 )-2-옥소 -1， 2-디하이드로퀴놀린- 3-카르복사마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 2-(p-를일)아세틸 클로라 이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 124 화합물을 수득하였다 (수율 = 63%) . 5 -amino-1-ethyl-N- (4-fluorofluorophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5 mmol) and 2- (p-ylyl) acetyl chloride (1.2 μl ol) was stirred for 15 min 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 Synthesis Example 124 compound (Yield = 63%).
¾ 腿 (400 MHz, CDC13)6 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-¾ 腿 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 129: 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo-
1， 2-디하이드로퀴놀린 -3-카르복사마이드 1, 2-dihydroquinoline-3-carboxamide
5 -아미노— Nᅳ (4_에틸페닐 )_2_옥소 ， 2_디하이드로퀴놀린 _3_카르복사마 이드 (1 mmol), DIPEAU.5 mmol) 및 2-(4—브로모페닐)아세틸 클로라이드 (1.2 匪 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 5 -amino— N ᅳ (4 _ethylphenyl) _ 2 _ oxo, 2 _dihydroquinoline _ 3 _carboxamide (1 mmol), DIPEAU.5 mmol) and 2- (4—bromophenyl) acetyl chloride (1. 2匪ol) followed by stirring for 15 minutes at C¾Cl 2 (2mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography.
129 화합물을 수득하였다 (수율 = 61%). 129 compound was obtained (Yield = 61%).
¾ NMR (400 MHz, CDC13)6 10.12 (s, 1H, -NH), 8.28 (s, 1H), 8.0¾ NMR (400 MHz, CDC1 3 ) 6 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,(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 합성예 130 ： 5— (2-(4-브로모페닐)아세트아미도) -N-(4—에틸페닐) -2-옥소 -1- (티오펜 -2-일메틸 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드 2H), 1.25 (s, 3H). MASS = 503.08 Synthesis Example 130: 5— (2- (4-bromophenyl) acetamido) -N- (4—ethylphenyl) -2-oxo-1- (thiophen-2-ylmethyl) -1, 2- Dihydroquinoline-3-carboxamide
5-아미노 - (4-에틸페닐 )-2-옥소 -1- (티오펜 -2-일메틸 )-1， 2-디하이드 로퀴놀린 -3-카르복사마이드 (1 隱 ol), DIPEA 1.5 mmol) 및 2_(4-브로모 페닐)아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 130 화합물을 수득하였다 (수율 = 61%). 5-amino- (4-ethylphenyl) -2-oxo-1- (thiophen-2-ylmethyl) -1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5 mmol ) And 2_ (4-bromo phenyl) acetyl chloride (1.2 μl ol) were stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 130 (yield = 61%).
¾ 賺 (400 MHz, CDC13)6 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 합성예 131 ： 5-(2-(4-브로모페닐)아세트아미도) -N-(4-에틸페닐) -1-메틸 -2- 옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 131: 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3 Carboxamide
5 -아미노 _N_(4_에틸페닐 )_2_옥소 , 2—디하이드로퀴놀린 _3_카르복사마 이드 (1 隱 ol), DIPEA 1.5 mmol) 및 2— (4-브로모페닐)아세틸 클로라이드 (L2 隱 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 131 화합물을 수득하였다 (수율 = 61%). 5-amino-N _ _ (_ 4-ethylphenyl) _ _ 2-oxo, 2-dihydro-quinoline-3 _ _ carboxamide Village id (1隱ol), DIPEA 1.5 mmol) and 2- (4-bromophenyl) acetyl Chloride (L2xol) was stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 131 (Yield = 61%).
¾ 圈 R(400 MHz, CDC13)6 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 합성예 132 ： 5-(2-(4-브로모페닐)아세트아미도 )-1-에틸 -N-(4-에틸페닐) -2一 옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 圈 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 132: 5- (2- (4-Bromophenyl) acetamido) -1-ethyl -N- (4-ethylphenyl) -2o oxo -1, 2-dihydroquinoline-3 Carboxamide
5-아미노— 1—에틸— N-(4-에틸페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카 르복사마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 2— (4-브로모페닐)아세틸 클로라이드 (1.2 瞧 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 132 화합물을수득하였다 (수율 = 67%) . 5-amino— 1—ethyl— N- (4-ethylphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEA (1.5 mmol) and 2— ( 4-bromophenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography. The purification yielded Compound 132 (Synthesis Example 132).
¾ 腿 (400 MHz, CDC13)6 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 합성예 137 ： 5-(2-(4-클로로페닐)아세트아미도) -N-(4-하이드록시페닐) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 腿 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 137: 5- (2- (4-chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-하이드록시페닐 )-2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3—카르 복사마이드 (1 隱 ol), DIPEA (1.5 mmol) 및 2— (4-클로로페닐)아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 137 화합물을 수득하였다 (수율 = 61%) . 5-amino-N- (4-hydroxyphenyl) -2-oxo-1, 2'dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5 mmol) and 2— (4-chlorophenyl) Acetyl chloride (1.2 μl ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 137 compound (yield = 61%).
¾ 匪 R OO fflz, CDC13)6 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 합성예 138 ： 5-(2-(4-클로로페닐)아세트아미도) -N-(4-하이드록시페닐) -1- 메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R OO fflz, CDC1 3 ) 6 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 Synthesis Example 138: 5- (2- (4-chlorophenyl) acetamido) -N- (4-hydroxyphenyl) -1-methyl-2-oxo-1,2-dihydroquinoline-3 Carboxamide
5-아미노 -N-(4-하이드록시페닐) -1-메틸 -2—옥소 -1， 2—디하이드로퀴놀린 5-amino-N- (4-hydroxyphenyl) -1-methyl-2—oxo-1, 2—dihydroquinoline
-3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-(4-클로로페닐)아세틸 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 138 화합물을 수득하였다 (수율 = 61%) . -3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4-chlorophenyl) acetyl chloride (1.2 mmol) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 138 compound (yield = 61%).
¾ NMR(400 MHz, CDC13)S 10.12(s, 1H, -NH) , 8.28(s, 1H) , 7.88(m,¾ NMR (400 MHz, CDC1 3 ) S 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 합성예 139 ： 5-(2-(4-클로로페닐)아세트아미도 )-1—에틸 -N-(4-하이드톡시 페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 139: 5- (2- (4-Chlorophenyl) acetamido) -1—ethyl-N- (4-hydroxyphenyl) -2-oxo-1,2-dihydroquinoline-3 Carboxamide
5-아미노ᅳ 1ᅳ에틸 -N-(4-하이드록시페닐 )-2ᅳ옥소 -1， 2- 디하이드로퀴놀린 -3-카르복사마이드 (1 瞧 ol), DIPEA(1.5 隱 ol) 및 2ᅳ (4- 클로로페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 139 화합물을 수득하였다 (수율 = 66%). 5-amino ᅳ 1 ᅳ ethyl-N- (4-hydroxyphenyl) -2 ᅳ oxo-1, 2- Dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5' ol) and 2 '(4-chlorophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. . The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 139 (Yield = 66%).
¾ NMRC400 腿 z, CDC13)6 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 합성예 141 ： 5-(2-(4-플루오로페닐)아세트아미도) -N-(4-니트로페닐) -2-옥소 -1,2-디하이드로퀴놀린ᅳ 3-카르복사마이드 ¾ NMRC400 腿 z, CDC1 3 ) 6 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 Synthesis Example 141: 5- (2- (4-fluorophenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-니트로페닐 )_2_옥소 _；[， 2_디하이드로퀴놀린— 3-카르복 사마이드 (1 瞧 01)， DIPEA (1.5 mmol) 및 2-(4-플루오로페닐)아세틸 클로 라이드 (1.2 mmol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 141 화합물을 수득하였다 (수율 = 64%) . 5 -amino- N- (4-nitrophenyl) _ 2 _oxo _; [， 2 _dihydroquinoline— 3-carboxamide (1 瞧0 1), DIPEA (1.5 mmol) and 2- (4- Fluorophenyl) acetyl chloride (1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 141 compound (yield = 64%).
¾ 賺 (400 丽 z, CDC13)8 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 합성예 142 ： 5-(2-(4-에틸페닐)아세트아미도) -N— (4-니트로페닐) 2—옥소- 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 400 (400 δ z, CDC1 3 ) 8 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 Synthesis Example 142: 5- (2- (4-ethylphenyl) acetamido) -N— (4-nitrophenyl) 2—oxo-1, 2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4—니트로페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사 마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 2-(4—에틸페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mU에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 142 화합물을 수득하였다 (수율 = 67%). 5-amino-N- (4—nitrophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEA (1.5 mmol) and 2- (4—ethylphenyl) Acetyl chloride (1.2 mmol) was stirred for 15 min at CH 2 Cl 2 (2mU. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 142 (yield = 67%). ).
¾ 證 (400 MHz, CDC13)6 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 합성예 156 ： 5-(2-(4-하이드록시페닐)아세트아미도 )-2-옥소 -N-(4- 비닐페닐) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 6 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 Synthesis Example 156: 5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 -N-(4-비닐페닐 )ᅳ1， 2-디하이드로퀴놀린 -3-카르복사마 이드 (1 隱 ol), DIPEA(1.5 麵 ol) 및 2-(4-하이드록시페닐)아세틸 클로라 이드 (1.2 mmol)를'. CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 156 화합물을 수득하였다 (수율 = 61%) . 5-amino-2-oxo-N- (4-vinylphenyl) ᅳ 1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5' ol) and 2- (4-hydride Oxyphenyl) acetyl chloride (1.2 mmol) ' . Stir for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 156 compound (Yield = 61%).
¾ NMR(400 MHz, CDC13)5 10.12(s, 1H, -NH) , 8.28(s, 1H) , 7.88(m, 4H), 7.61(dd, 2H)， 7.29(t, 1H), 7.23(s, ΙΗ,-ΝΗ), 7.06(dd, 2H)， 6.63(m, 3H), 5.61 (s, 1H), 5.35(s, 1H, -OH), 5.18(s, 1H) , MASS=439.15 합성예 157 ： 5-(2-(4-하아드록시페닐)아세트아미도 )-1-메틸 -2-옥소 -N-(4— 비닐페닐 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드 ) ¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, 1H, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, ΙΗ, -ΝΗ), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.35 (s, 1H, -OH), 5.18 (s, 1H), MASS = 439.15 Example 157: 5- (2- (4-hydroxyphenyl) acetamido) -1-methyl-2-oxo-N- (4—vinylphenyl) -1, 2-dihydroquinoline-3-carbox Amide)
5-아미노 -1-메틸ᅳ 2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3-카 르복사마이드 (1 隱 ol), DIPEA 1.5 mmol) 및 2-(4—하이드록시페닐)아세틸 클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 157 화합물을 수득하였다 (수율 = 61%). 5-amino-1-methyl ᅳ 2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEA 1.5 mmol) and 2- (4 —Hydroxyphenyl) acetyl chloride (1.2 mmol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 157 compound (Yield = 61%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 158 ： 1-에틸 -5-(2-(4—하이드록시페닐)아세트아미도 )-2-옥소 -N-(4- 비닐페닐) -1,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 158: 1-ethyl-5 (2- (4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3 Carboxamide
5ᅳ아미노 -1-에틸 -2—옥소 -N-(4—비닐페닐) -1 , 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 隱 ol), DIPEA 1.5 mmol) 및 2-(4-하이드톡시페닐)아세틸 클로라이드 (1.2 麵 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 158 화합물을 수득하였다 (수율 = 49%). 5'Amino-1-ethyl-2-2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5 mmol) and 2- (4- Hydroxyphenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 158 compound (Yield = 49%).
¾ NMR(400 MHz, CDC13)6 10.12(s, 1H, -NH), 8,28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H), 7.23(s, ΙΗ,-ΝΗ), 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 합성예 159 ： 1-((2，3—디하이드로 -1H-인덴 -2—일)메틸) -5-(2-(4- 하이드록시페닐 ) 세트아미도) -2-옥소 -N-(4-비닐페닐 )-1， 2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 10.12 (s, 1H, -NH), 8,28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 (s, ΙΗ, -ΝΗ), 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 Synthesis Example 159: 1-((2,3—Dihydro-1H-inden-2-2-yl) methyl) -5 (2- (4-hydroxyphenyl) setamido) -2-oxo- N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide
5-아미노 -1-( (2 , 3-디하이드로 -1H-인덴 -2-일)메틸) 2-옥소 -N-(4-비닐 페닐) -1,2-디하이드로퀴놀린 -3-카르복사마이드 (1醒 ol), DIPEM1.5隱 ol) 및 2-(4-하이드록시페닐)아세틸클로라이드 (1.2隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 159 화합물을 수득하였다 (수율 = 61%) . 5-amino-1- ((2, 3-dihydro-1H-inden-2-yl) methyl) 2-oxo-N- (4-vinyl phenyl) -1,2-dihydroquinoline-3-carbox Amide (1 'ol), DIPEM 1.5' ol) and 2- (4-hydroxyphenyl) acetylchloride (1.2 'ol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 159 compound (yield = 61%).
¾ 匪 R(400 MHz, CDC13)6 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, ΐΆ)' 5.35(s, 1H, -OH), 5.18(s, 1H)ᅳ 3.98(s, 2H), 2.66(m, 5H). MASS=569.23 합성예 160 ： 5-(2-(4-니트로페닐)아세트아미도 )-2-옥소 -N— (4-비닐페닐) - 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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, ΆΆ) '5.35 (s, 1H, -OH), 5.18 (s, 1H) ᅳ 3.98 (s , 2H), 2.66 (m, 5H). MASS = 569.23 Synthesis Example 160: 5- (2- (4-nitrophenyl) acetamido) -2-oxo-N— (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 -N-(4-비닐페닐 )-1， 2-디하이드로퀴놀린 -3-카르복사마 이드 (1 瞧 ol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드 (1.2 mmol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 160 화합물을 수득하였다 (수율 = 66%). 5-amino-2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 瞧 ol), DIPEA (1.5 mmol) and 2- (4-nitrophenyl Acetyl chloride (1.2 mmol) was stirred for 15 minutes in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 160 compound (yield = 66%).
¾ NMR OO' MHz, CDC13)6 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 합성예 161 ： 1-메틸— 5-(2-(4-니트로페닐)아세트아미도 )-2-옥소 -N-(4- 비닐페닐) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 5-아미노— 1ᅳ메틸 -2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 瞧 01), DIPEA(1.5 瞧 ol) 및 2— (4-니트로페닐)아세틸 클로라이드 (1.2 麵 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 1.61 화합물을 수득하였다 (수율 = 62%) ¾ NMR OO ' MHz, CDC1 3 ) 6 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 Synthesis Example 161: 1-methyl- 5- (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3- Carboxamide 5-amino— 1 ᅳ methyl-2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 瞧0 1), DIPEA (1.5 瞧 ol) and 2— (4-nitrophenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 1.61 (yield = 62%).
¾ 丽 (400 MHz, CDC13)6 10.12(s, iH, -NH), 8.28(s, 1H), 7.88(m, 4H), 7.61(dd, 2H), 7.29(t, 1H) , 7.23(s, ΙΗ,-ΝΗ), 7.06(dd, 2H), 6.63(m, 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-카르복사마이드 ¾ δ (400 MHz, CDC1 3 ) 6 10.12 (s, iH, -NH), 8.28 (s, 1H), 7.88 (m, 4H), 7.61 (dd, 2H), 7.29 (t, 1H), 7.23 ( s, ΙΗ, -ΝΗ), 7.06 (dd, 2H), 6.63 (m, 3H), 5.61 (s, 1H), 5.18 (s, 1H), 3.3 (s, 3H). MASS = 482.16. Synthesis Example 162: 1-ethyl-5 (2- (4-nitrophenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -1-에틸 -2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3-카 르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-(4-니트로페닐)아세틸 클로라이드 (1.2 麵 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 162 화합물을 수득하였다 (수율 = 61%) . 5-amino-1-ethyl-2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4 -Nitrophenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 162 (yield = 61%).
¾ NMR(400 MHz, CDC13)S 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，ᅳ 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 ¾ NMR (400 MHz, CDC1 3 ) S 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, ᅳ 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
' - 합성예 163 ： l-((4-메톡시 -2,3-디하이드로 -IH-인덴 -2-일)메틸) -5-(2-(4- 니트로페닐)아세트아미도 )-2-옥소 -N- -비닐페닐 )-1 , 2-디하이드로퀴놀린 -3- 카르복사마이드  Synthesis Example 163 l-((4-methoxy-2,3-dihydro-IH-inden-2-yl) methyl) -5 (2- (4-nitrophenyl) acetamido) -2 -Oxo-N--vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -1-((4-메특시 -2，3，33,73_테트라하이드로-111-인덴—1ᅳ일)메틸) -2-옥소 -N-(4-비닐페닐) -1，2-디하이드로퀴놀린— 3-카르복사마이드 (1 隱 ol), DIPEAC1.5 mmol) 및 2-(4-니트로페닐)아세틸클로라이드 (1.2 mmol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 163 화합물을 수득하였다 (수율 = 63%). 5-amino-1-((4-methoxy-2,3,33,73_tetrahydro-111-indene-1 ylyl) methyl) -2-oxo-N- (4-vinylphenyl) -1,2 -Dihydroquinoline—3-carboxamide (1 隱 ol), DIPEAC1.5 mmol) and 2- (4-nitrophenyl) acetylchloride (1.2 mmol) were stirred in CH 2 C1 2 (2 mL) for 15 minutes. . The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 163 (Yield = 63%).
¾ 讓 R(400 MHz, CDC13)5 10.12(s, IH, -NH) , 8.28(s, IH), 7.88(m,¾ 讓 R (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 7.88 (m,
4H), 7.61 (dd, 2H), 7.29(t, IH), 7.23(s, ΙΗ,-ΝΗ), 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 합성예 164 ： l-((5-메록시 -2，3-디하이드로-lH-인덴-2-일)메틸)-5-(2-(4- 니트로페닐)아세트아미도 )-2-옥소 -N-(4-비닐페닐 )-1， 2-디하이드로퀴놀린 -3- 카르복사마이드 4H), 7.61 (dd, 2H), 7.29 (t, IH), 7.23 (s, ΙΗ, -ΝΗ), 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 Synthesis Example 164: l-((5-methoxy-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4-nitrophenyl) acetamido)- 2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide
55-아미노ᅳ1-((6-메톡시ᅳ 2，3，33，7£1ᅳ테트라하이드로ᅳ111-인덴ᅳ1-일) 메 틸) -2-옥소 -N-(4-비닐페닐 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1 腿 ol), DIPEA 1.5 mmol) 및 2-(4-니트로페닐)아세틸클로라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 164 화합물을 수득하였다 (수율 = 67%) . 55-amino ᅳ 1-((6-methoxy ᅳ 2,3,33,7 £ 1 ᅳ tetrahydro ᅳ 111-inden ᅳ 1-yl) methyl) -2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide (1 腿 ol), DIPEA 1.5 mmol) and 2- (4-nitrophenyl) acetylchloride (1.2 隱 ol) for 15 minutes in C¾Cl 2 (2 mL) Stirred. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 164 (yield = 67%).
¾ 證 (400 MHz, CDC13)5 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 합성예 168 ： 5_(2-(4-메록시페닐)아세트아미도 )— 2-옥소 -N-페닐 -1,2-디하 이드로퀴놀린 -3-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 5 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, 5 H). MASS = 628.23 Synthesis Example 168 ： 5_ (2- (4-methoxyphenyl) acetamido) — 2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 페닐 -1， 2ᅳ디하이드로퀴놀린 -3-카르복사마이드 ( 1 mmol), DIPEAU.5 mmol) 및 2-(4—메톡시페닐)아세틸 클로라이드 (1.2 讓 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 168 화합물을 수득하였다 (수율 = 69%). 5-amino-2-oxophenyl-1,2'dihydroquinoline-3-carboxamide (1 mmol), DIPEAU.5 mmol) and 2- (4—methoxyphenyl) acetyl chloride (1.2 讓 ol) Stirred in 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 168 (yield = 69%).
¾ NMR(400' MHz, CDC13)6 10.12(s, 1H, -NH) , 8.28(s, 1H), 8.0(s,¾ NMR (400 ' MHz, CDC1 3 ) 6 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(sᅳ 3H). MASS = 427.15 합성예 169 ： l-((5ᅳ에틸 -2，3-디하이드로-lH-인덴-2-일)메틸)-5-(2-(4- 메록시페닐)아세트아미도 )-2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3— 카르복사마이드 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 Synthesis Example 169: l-((5 ᅳ ethyl-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4- methoxyphenyl) acetamido)- 2-oxo-N-phenyl-1, 2-dihydroquinoline-3 Carboxamide
5-아미노 -1-((2，3-디하이드로 -1H-인덴ᅳ 2-일)메틸) 2ᅳ옥소 -N-페닐 -1,2 -디하이드로퀴놀란 -3ᅳ카르복사마이드 (1瞧 01)， DIPEA 1.5讓 ol) 및 2-(4- 메특시페닐)아세틸 '클로라이드 (1.2難 ol)를 C¾Cl2(2mL)에서 15분 간 교반 하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 169 화합물을 수득하였다 (수율 = 66%) . 5-amino-1-((2,3-dihydro-1H-indene 2-yl) methyl) 2oxo-N-phenyl-1,2-dihydroquinolan-3'carboxamide (1 ' 0 1), DIPEA 1.5 讓 ol) and 2- (4-methoxyphenyl) acetyl ' chloride (1.2 難 ol) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 169 compound (Yield = 66%).
¾ NMR(400 MHz, CDC13)5 10.12(s, 1H, - H), 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 합성예 170 ： l-((5-플루오로 -2,3-디하이드로-lH-인덴-2-일)메틸)-5-(2-(4- 메록시페닐)아세트아미도 )-2-옥소 -N-페닐 -1，2ᅳ디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, 1H,-H), 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 Synthesis Example 170: l-((5-fluoro-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4- methoxyphenyl) acetamido) 2-oxo-N-phenyl-1- 1,2-dihydroquinoline-3-carboxamide
5-아미노— 1— ( (5-폴루오로 -2， 3-디하이드로 -1H-인덴 -2-일)메틸) -2-옥소 5-amino— 1— ((5-polouro-2, 3-dihydro-1H-inden-2-yl) methyl) -2-oxo
-N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1隱 01 )， DIPEA( 1.5画 ol ) 및 2-(4-메록시페닐)아세틸클로라이드 (1.2mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 170 화합물을 수득하였다 (수율 = 61%) . -N-phenyl-1, 2-dihydroquinoline-3-carboxamide (1 隱 01), DIPEA (1.5 画 ol) and 2- (4-methoxyphenyl) acetylchloride (1.2mmol) were dissolved in C¾Cl 2 ( 2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 170 compound (yield = 61%).
¾ 匪 R(400 MHz, CDCl3)a 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 합성예 171 ： l-((5-클로로 -2,3-디하이드로 -1H-인덴 -2-일)메틸) -5-(2-(4-메 톡시페닐)아세트아미도 )-2-옥소 -N-페닐 -1，2-디하이드로퀴놀린 -3-카르복사마 이드 ¾ 匪 R (400 MHz, CDCl 3 ) a 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, 2 H), 2.46 (m, 5 H). MASS ^ 575.22 Synthesis Example 171: l-((5-chloro-2,3-dihydro-1H-inden-2-yl) methyl) -5 (2- (4-methoxyphenyl) acetamido)- 2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -1ᅳ( (5-클로로 -2 ,3-디하이드로 -1H-인덴 -2-일)메틸) -2—옥소- N-페닐 -1,2-디하이드로퀴놀린 -3-카르복사마이드 (1薩 ol), DIPE 1.5隱 ol) 및 2-(4-메톡시페닐)아세틸클로라이드 (1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 171 화합물을 수득하였다 (수율 = 69%) . , 5-amino-1 '((5-chloro-2,3-dihydro-1H-inden-2-yl) methyl) -2—oxo-N-phenyl-1,2-dihydroquinoline-3-carbox Amide (1 'ol), DIPE 1.5' ol) and 2- (4-methoxyphenyl) acetylchloride (1.2 mmol) in CH 2 Cl 2 (2 mL) for 15 minutes. Stirred. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 171 compound (yield = 69%). ,
¾ 醒 R(400 MHz, CDC13)5 10.12(s, IH, -NH), 8.28(s, IH), 8.0(s, IH, -NH), 7.88(m, 2H) , 7.61(m, 3H), 7.43(dd, 2H), 7.29(t, IH), 7.19(t, IH), 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 합성예 172 ： 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )-2-옥소 -N-페닐- 1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 醒 R (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 8.0 (s, IH, -NH), 7.88 (m, 2H), 7.61 (m, 3H ), 7.43 (dd, 2H), 7.29 (t, IH), 7.19 (t, IH), 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 Synthesis Example 172: 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
55-아미노 -2-옥소ᅳ N-페닐 -1 , 2—디하이드로퀴놀린 -3-카르복사마이드 ( 1 謹 ol), DIPEA(1.5 mmol) 및 2— (4- (하이드록시메틸)페닐)아세틸 클로라이드 (1.2 讓 ol)를 CH2Ql2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테 이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 172 화합물을 수득하였다 (수율 = 61%). 55-amino-2-oxoxo N-phenyl-1, 2—dihydroquinoline-3-carboxamide (1 謹 ol), DIPEA (1.5 mmol) and 2— (4- (hydroxymethyl) phenyl) acetyl Chloride (1.2 μl) was stirred in CH 2 Ql 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 172 (yield = 61%).
¾ NMR(400 MHz, CDC13)5 10.12(s, IH, -NH) , 8.28(s, IH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H) , 7.29(t, IH), 7.23(s, IH, -NH), 7.19(t, IH), 7.16 (dd, 2H), 7.11(dd, 2H), 4.61(m, 2H), 3.90(m, 2H), 3.65(s, IH, -OH). MASS= 427.15 합성예 173 ： 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )_l-((5-아이오도- 2 ,3-디하이드로 -1H—인덴 -2-일 )메틸) -2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 10.12 (s, IH, -NH), 8.28 (s, IH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 ( t, IH), 7.23 (s, IH, -NH), 7.19 (t, IH), 7.16 (dd, 2H), 7.11 (dd, 2H), 4.61 (m, 2H), 3.90 (m, 2H), 3.65 (s, IH, -OH). MASS = 427.15 Synthesis Example 173: 5- (2- (4- (hydroxymethyl) phenyl) acetamido) _l-((5-iodo-2,3-dihydro-1H—inden-2-yl) Methyl) -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 麵 ol), DIPEA(1.5 mmol) 및 2-(4- (하이드록시메틸)페닐)아세틸클로라이드 (1.2 画 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 173 화합물을 수득하였다 (수율 = 61%). 5-amino-1- ((5-iodo-2, 3-dihydro-1H-inden-2-yl) methyl) -2-oxo-N-phenyl-1,2-dihydroquinoline-3-carbox Copyamide (1 'ol), DIPEA (1.5 mmol) and 2- (4- (hydroxymethyl) phenyl) acetylchloride (1.2' ol) were stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 173 compound (Yield = 6 1%).
匪 R(400 MHz, CDC13)6 10.12(s, IH, -NH) , 8.28(s, IH), 7.88(m,匪 R (400 MHz, CDC1 3 ) 6 10.12 (s, IH, -NH), 8.28 (s, IH), 7.88 (m,
2H), 7.61(dd, 2H)， 7.43(dd, 2H), 7.29(t, IH), 7.23(s, IH, -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 합성예 174 ： 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )-l-((5-니트로- 2， 3-디하이드로 -1H-인덴 -2-일 )메틸) -2-옥소 -Nᅳ페닐 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, IH), 7.23 (s, IH, -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 Synthesis Example 174: 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -l-((5-nitro-2, 3-dihydro-1H-inden-2-yl) Methyl) -2-oxo-N ᅳ phenyl-1, 2-dihydroquinoline-3-carboxamide
5-아미노 -1-( (5-니트로 -2， 3-디하이드로 -1H-인덴 -2-일 )메틸 )ᅳ2-옥소- N-페닐 -1,2-디하이드로퀴놀린 -3ᅳ카르복사마이드 (1隱 ol), DIPEA 1.5画 ol) 및 5-amino-1- ((5-nitro-2, 3-dihydro-1H-inden-2-yl) methyl) ᅳ 2-oxo-N-phenyl-1,2-dihydroquinoline-3 -carbox Amide (1 'ol), DIPEA 1.5' ol) and
2- (4- (하이드록시메틸)페닐)아세틸클로라이드 (1.2隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 174 화합물을 수득하였다 (수율 = 61%). 2- (4- (hydroxymethyl) phenyl) acetylchloride (1.2 μl) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 174 compound (Yield = 61%).
¾ NMR(400 MHz, CDC13)S 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)ᅳ 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 합성예 175 ： 2-옥소 -N-페닐 -5-(3-페닐프로판아미도) -1,2-디하이드로퀴놀린-¾ NMR (400 MHz, CDC1 3 ) S 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) ᅳ 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 Synthesis Example 175 ： 2-oxo-N-phenyl-5 (3-phenylpropaneamido) -1,2-dihydroquinoline-
3-카르복사마이드 3-carboxamide
5-아미노— 2ᅳ옥소 -N—페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1 醒 ol), DIPEA 1.5麵 ol) 및 3-페닐프로파노일클로라이드 (1.2瞧 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테아트 및 포화 NaHC03로 추출하고 실리카 컬럼크로마토그래피로 정제하여 합성예 175 화합물을 수득하였다 (수율 = 64%). 5-amino- 2oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5' ol) and 3-phenylpropanoylchloride (1.2 'ol) Stir for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica column chromatography to give Synthesis Example 175 compound (Yield = 64%).
¾ 匪 R(400 MHz, CDC13)5 10.12(s, 1H, -NH), 8.28(s, 1H), 8.0(s,¾ 匪 R (400 MHz, CDC1 3 ) 5 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(iii, 2H). MASS= 411.16 합성예 176 ： l-((5-에틸 -2，3—디하이드로-lH-인덴-2-일)메틸)-2-옥소-N- 페닐-5-(3-페닐프로판아미도)-l， 2-디하이드로퀴놀린 -3-카르복사마이드 5-아미노 -l-( (5-에틸 -2 , 3-디하이드로 -1H-인덴 -2-일)메틸 )-2ᅳ옥소 -N- 페닐 -1,2-디하이드'로퀴놀린 -3-카르복사마이드 (1議 ol), DIPEA(l. imol) 및 3-페닐프로파노일클로라이드 (1.2麵 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였 다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 176 화합물을 수득하였다 (수율 =61%). 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 (iii, 2H). MASS = 411.16 Synthesis Example 176: l-((5-ethyl-2,3—dihydro-lH-inden-2-yl) methyl) -2-oxo-N-phenyl-5- (3-phenylpropaneamido ) -l, 2-dihydroquinoline-3-carboxamide 5-Amino-l-((5-ethyl-2,3-dihydro-1H-inden-2-yl) methyl) -2oxo-N-phenyl-1,2-dihydro ' roquinoline-3- Carboxamide (1 'ol), DIPEA (l. Imol) and 3-phenylpropanoylchloride (1.2' ol) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the Synthesis Example 176 compound (yield = 61%).
¾ MR (400 MHz, CDC13) δ i0.12(s, IH, -NH), 8.28(s, IH), 8.0 (s, IH, -NH), 7.88(m, 2H) , 7.61(dd, 2H), 7.43(dd, 2H), 7.40(dd, 2H) , 7.29(m, 4H), 7.27(t, IH), 7.23(s, IH, -NH), 7.19(m, 3H) , 3.3(m, 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-디하이 드로퀴놀린 -3-카르복사마이드 ¾ MR (400 MHz, CDC1 3 ) δ i0.12 (s, IH, -NH), 8.28 (s, IH), 8.0 (s, IH, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.40 (dd, 2H), 7.29 (m, 4H), 7.27 (t, IH), 7.23 (s, IH, -NH), 7.19 (m, 3H), 3.3 ( m, 5H), 2.9 (m, 7H), 2.83 (m, 4H), 2.64 (s, 5H). MASS-569.27 Synthesis Example 177 5- (2- (4-ethylphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydrodroquinoline-3-carboxamide
5-아미노 -2-옥소 페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1 隱 ol), DIPEM1.5腿 ol) 및 2-(4-에틸페닐)아세틸클로라이드 (1.2mmol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 177 화합물을 수득하였다 (수율 = 62%). 5-amino-2-oxophenyl-1, 2-dihydroquinoline-3-carboxamide (1 1 ol), DIPEM1.5 腿 ol) and 2- (4-ethylphenyl) acetylchloride (1.2mmol) Stir for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 177 (Yield = 62%).
¾ NMR OO MHz, CDC13)6 10.12(s, IH, -NH), 8.28(s, IH), 8.0(s, IH, -NH), 7.88(m, 2H), 7.61(dd, 2H), 7.43(dd, 2H) , 7.29(t, IH), 7.23(s, IH, -NH), 7.18(dd, 2H), 6.98(dd, 2H), 3.90(m, 2H), 2.60(m, 2H)， 1.25(s, 3H). MASS= 425.17 합성예 Γ78 ： 1-(2-(2，3-디하이드로 -IH-인덴 -2-일)에틸 )ᅳ5-(2-(4-에틸페닐) 아세트아미도 )-2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR OO MHz, CDC1 3 ) 6 10.12 (s, IH, -NH), 8.28 (s, IH), 8.0 (s, IH, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (t, IH), 7.23 (s, IH, -NH), 7.18 (dd, 2H), 6.98 (dd, 2H), 3.90 (m, 2H), 2.60 (m, 2H ), 1.25 (s, 3H). MASS = 425.17 Synthesis Example Γ 78: 1- (2- (2,3-Dihydro-IH-inden-2-yl) ethyl) ᅳ 5- (2- (4-ethylphenyl) acetamido) -2-oxo -N-phenyl-1, 2-dihydroquinoline-3-carboxamide
55-아미노 -1-((2，3-디하이드로 -1H-인덴 -2-일)메틸) -2-옥소 -N-페닐- 55-amino-1-((2,3-dihydro-1H-inden-2-yl) methyl) -2-oxo-N-phenyl-
1，2-디하이드로퀴놀린 -3-카르복사마이드 (1讓 ol), DIPEM1.5瞧 ol) 및 벤조일 클로라이드 (1.2隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 178화합물을 수득하였다 (수율 = 61%) 1,2-dihydroquinoline-3-carboxamide (1 ′ ol), DIPEM1.5 ′ ol) and benzoyl chloride (1.2 ′ ol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 178 (yield = 61%).
¾ 醒 R(400 MHz, CDC13)6 10.12(s, IH， - NH), 8.28(s, IH) , 8.0(s,¾ 醒 R (400 MHz, CDC1 3 ) 6 10.12 (s, IH,-NH), 8.28 (s, IH), 8.0 (s,
IH, -NH), 7.88(m, 2H) , 7.61(dd, 2H) , 7.43(dd, 2H), 7.29(m, 2H), 7.23(s, 1H, -NH), 7.18(mr 4H), 6.98(dd, 2H), 3.90(m, 6H), 2.60(m, 7H), 1.25(s 3H). MASS= 569.27 합성예 184 ： 5-(2-(4-메록시페닐)아세트아미도 )-2—옥소— N-펜에틸 -1，2- 디하이드로퀴놀린 -3-카르복사마이드 IH, -NH), 7.88 (m, 2H), 7.61 (dd, 2H), 7.43 (dd, 2H), 7.29 (m, 2H), 7.23 (s, 1H, -NH), 7.18 (mr 4H), 6.98 (dd, 2H), 3.90 (m, 6H), 2.60 (m, 7H), 1.25 (s 3H). MASS = 569.27 Synthesis Example 184: 5- (2- (4-Moxyphenyl) acetamido) -2—oxo—N-phenethyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 -N-펜에틸 -1， 2ᅳ디하이드로퀴놀린 -3-카르복사마이드 ( 1 瞧 ol), DIPEA(1.5 mmol) 및 2-(4-메특시페닐)아세틸 클로라이드 (1.2 瞧 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 184 화합물을 수득하였다 (수율 = 61%) . 5-amino-2-oxo-N-phenethyl-1, 2'dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2瞧 ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 184 (yield = 61%).
¾ 賺 (400,. MHz, CDC13)6 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 합성예 185 ： l-(4-메특시벤질) -5-(2-(4-메특시페닐)아세트아미도) _2-옥소- N-펜에틸 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 賺 (400, .MHz, CDC1 3 ) 6 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 Synthesis Example 185: l- (4-Methoxybenzyl) -5 (2- (4-methoxyphenyl) acetamido) _2 -Oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
5-아미노- (4-메톡시벤질)—2—옥소 -N-펜에틸 -1,2-디하이드로퀴놀린- 3-카르복사마이드 (1 讓 ol), DIPEA 1.5 mmol) 및 2— (4-메록시페닐)아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다, 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 185 화합물을 수득하였다 (수율 =63%). 5-amino- ( 4 -methoxybenzyl) —2—oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide (1 讓 ol), DIPEA 1.5 mmol) and 2— (4- Methoxyphenyl) acetyl chloride (1.2 x ol) was stirred for 15 min in CH 2 Cl 2 (2 mL), the residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 185. (Yield = 63%).
¾ 匪 R(400 MHz, CDC13)5 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 합성예 186 ： l-((4-하이드록시 -2,3-디하이드로-lH-인덴-2-일)메틸)-5-(2- (4-메록시페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 5 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, 4 H), 2.83 (m, 5 H). MASS = 575.24 Synthesis Example 186: l-((4-hydroxy-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4-hydroxyphenyl) acetamido) 2-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 誦 01)， DIPEA(1.5 mmol) 및 2- (4-메록시페닐)아세틸 클로라이드 (1.2 画 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 186 화합물을 수득하였다 (수율 =67%). 55-amino-1-((2,3-dihydro-1H—inden-2-yl) methyl) -2-oxo-N-phenethyl- 1,2-dihydroquinoline-3-carboxamide (1 誦0 1), DIPEA (1.5 mmol) and 2- (4-methoxyphenyl) acetyl chloride (1.2 画 ol) were CH 2 Cl 2 (2 mL) Stirred 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 186 compound (yield = 67%).
¾ NMR(400 MHz, CDC13)8 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s,¾ NMR (400 MHz, CDC1 3 ) 8 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s,
1H), 7.88 Cm, 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 합성예 187 ： l-((4-포르밀 -2，3-디하이드로-lH-인덴-2—일)메틸)-5-(2-(4- 메록시페닐)아세트아미도) -2-옥소 -N-펜에틸— 1 , 2-디하이드로퀴놀린 -3- 카르복사마이드 1H), 7.88 Cm, 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 Synthesis Example 187: l-((4-formyl-2,3-dihydro-lH-inden-2-yl) methyl) -5- (2- (4- methoxyphenyl) acetamido) -2-oxo-N-phenethyl— 1, 2-dihydroquinoline-3-carboxamide
5-아미노 -2-옥소 펜에틸 -1— ( (5-비닐 -2 , 3-디하이드로 -1H-인덴 -2- 일 )메틸) -1 , 2-디하이드로퀴놀린 -3—카르복사마이드 ( 1隱 ol ) , DIPEA(1.5瞧 ol ) 및 2-(4—메록시페닐)아세틸클로라이드 (1.2画 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔컬럼크로마토그래피로 정제하여 합성예 187 화합물을 수득하였다 (수율 = 61%) . 5-amino-2-oxophenethyl-1 — ((5-vinyl-2, 3-dihydro-1H-inden-2-yl) methyl) -1, 2-dihydroquinoline-3—carboxamide ( 1 'ol), DIPEA (1.5' ol) and 2- (4-methoxyphenyl) acetylchloride (1.2 'ol) were stirred for 15 minutes in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 187 (yield = 61%).
¾ 醒 R (400 MHz, CDC13)6 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 합성예 188 l-((4-시아노 -2,3-디하이드로 -1H-인덴 -2-일)메틸) -5-(2-(4- 메록시페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ 醒 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 188 l-((4-Cyano-2,3-dihydro-1H-inden-2-yl) methyl) -5 (2- (4- methoxyphenyl) acetamido)- 2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide
5-아미노 -1-( (5ᅳ시아노 -2，3-디하이드로 -1H—인덴 -2-일)메틸) -2-옥소- N-펜에틸 -1，2-디하이드로퀴놀린 -3-카르복사마이드 (1隱 ol), DIPEA(1.5隱 ol) 및 2-(4-메특시페닐)아세틸클로라이드 (1.2醒 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 3로마토그래피로 정제하여 합성예 188 화합물을 수득하였다 (수율 = 62%) 5-amino-1-((5xyano-2,3-dihydro-1H—inden-2-yl) methyl) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3- Carboxamide (1 'ol), DIPEA (1.5' ol) and 2- (4-methoxyphenyl) acetylchloride (1.2 'ol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column 3 chromatography to synthesize the Synthesis Example 188 compound Obtained (yield = 62%)
¾ 賺 (400 MHz, CDC13)6 8.28(s, 1H), 8.03(s, 1H, ᅳ 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 합성예 189 ： 5-(2-(4-브로모페닐)아세트아미도 )-2-옥소 -N-펜에틸 -1,2-디하 이드로퀴놀린 -3-카르복사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.03 (s, 1H, ᅳ 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 Synthesis Example 189 ： 5- (2- (4-Bromophenyl) acetamido) -2-oxo-N-phenethyl-1,2-dihydroquinoline-3-carboxamide
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 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예5-amino-2-oxo-N—phenethyl-1, 2-dihydroquinoline-3—carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (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 NaHC0 3 and purified by silica gel column chromatography.
189 화합물을 수득하였다 (수율 =53« 189 compound was obtained (Yield = 53 «.
¾ 匪 R(400 MHz, CDC13)5 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 Cm, 2H), 7.40(dd, 2H), 7.29(m, 3H), 7.27(t, 1H), 7.23(s, 1H,¾ 匪 R (400 MHz, CDC1 3 ) 5 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 Cm, 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,-NH), 7.12 (dd, 2H), 6.87 (dd, 2H), 3.90 (m, 2H), 3.55 (m, 2H), 2.83 (m,
2H). MASS=503.08 합성예 190 ： 5-(2-(4-브로모페닐)아세트아미도 )-l-(4-메록시벤질) 2-옥소- N-펜에틸 -1,2-디하'이드로퀴놀린 -3-카르복사마이드 2H). MASS = 503.08 Synthesis Example 190: 5- (2- (4-bromophenyl) acetamido) -l- (4-methoxybenzyl) 2-oxo-N-phenethyl-1,2-diha'droquinoline -3-carboxamide
5-아미노 -1-(4-메톡시벤질) -2-옥소 -N-펜에틸 -1， 2—디하이드로퀴놀린ᅳ 3-카르복사마이드 (1 醒 ol), DIPEA 1.5 mmol) 및 2-(4-브로모페닐)아세틸 클로라이드 (1.2 麵 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 190 화합물을 수득하였다 (수율 = 61%). 5-amino-1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1,2—dihydroquinoline® 3-carboxamide (1 'ol), DIPEA 1.5 mmol) and 2- ( 4-bromophenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 190 (Yield = 61%).
匪 R(400 MHz, CDC13)6 8.28(s, 1H), 8.03(s, 1H, -NH), 8.0(s, 1H), 7.88 Cm, 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 匪 R (400 MHz, CDC1 3 ) 6 8.28 (s, 1H), 8.03 (s, 1H, -NH), 8.0 (s, 1H), 7.88 Cm, 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, 2 H). MASS = 623.14
'. '.
합성예 203 ： 5-(2-(4-클로로페닐)아세트아미도) -N-(4-메틸펜에틸) -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 Synthesis Example 203: 5- (2- (4-chlorophenyl) acetamido) -N- (4-methylphenethyl) -2-oxo- 1,2-dihydroquinoline-3-carboxamide
5-아미노 -Νᅳ (4-메틸펜에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 画 01)， DIPEM1.5 瞧 ol) 및 2ᅳ(4-클로로페닐)아세틸 클로라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 203 화합물을 수득하였다 (수율 =66%). 5-amino-N- (4-methylphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 画0 1), DIPEM1.5 瞧 ol) and 2 ᅳ (4- Chlorophenyl) acetyl chloride (1.2 cc ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 203 (yield = 66%).
¾ 證 (400 MHz, CDC13)6 8.28(s, IH) , 8.03(s, IH, -NH), 8.0(s, IH, -NH), 7.88(m, 2H), 7.41(dd, 2H) , 7.37(dd, 2H), 7.29(t, IH), 7.23(s, IH, -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 합성예 204 ： 5-(2-(4—클로로페닐)아세트아미도 )-l-(4-메톡시벤질) -N-(4- 메틸펜에틸 )ᅳ2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.03 (s, IH, -NH), 8.0 (s, IH, -NH), 7.88 (m, 2H), 7.41 (dd, 2H) , 7.37 (dd, 2H), 7.29 (t, IH), 7.23 (s, IH, -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 Synthesis Example 204: 5- (2- (4—Chlorophenyl) acetamido) -l- (4-methoxybenzyl) -N- (4-methylphenethyl) ᅳ 2-oxo-1, 2 -Dihydroquinoline® 3-carboxamide
5-아미노 -1ᅳ(4-메특시벤질 )-N-(4-메틸펜에틸 )-2-옥소 -1， 2-디하이드로 퀴놀린 -3-카르복사마이드 (1腿 ol), DIPEAU.5隱 ol) 및 2ᅳ(4—클로로페닐) 아세틸클로라이드 (1.2麵 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔컬럼 크로마토그래피로 정제하여 합성예 204화합물을 수득하였다 (수을 = 61%) . 5-Amino-1 '(4-methoxybenzyl) -N- (4-methylphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1' ol), DIPEAU.5 Xol) and 2x (4—chlorophenyl) acetylchloride (1.2xol) were stirred for 15 minutes in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 204 compound (number = 61%).
¾ NMR (4Q0 MHz, CDC13)6 8.28(s, IH), 8.03(s, IH, — NH), 8.0(s, IH, -NH), 7.88(m, 2H), 7.41(dd, 2H), 7.37(dd, 2H) , 7.29(t, IH), 7.23(s,¾ NMR (4Q0 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.03 (s, IH, — NH), 8.0 (s, IH, -NH), 7.88 (m, 2H), 7.41 (dd, 2H) , 7.37 (dd, 2H), 7.29 (t, IH), 7.23 (s,
IH, -NH), 7.18(m, 4H), 6.98(m, 4H), 3.90(m, 2H), 3.55(m, 2H), 3.3(s,IH, -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). 합성예 213 ： 5-(2-(4-플루오로페닐)아세트아미도) -N-(4-메록시펜에틸 )-2- 옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 2H), 2.83 (m, 2H), 2.34 (m, 2H), 1.67 (s, 3H). Synthesis Example 213: 5- (2- (4-fluorophenyl) acetamido) -N- (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
55-아미노 -N-(4-메록시펜에틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르 복사마이드 (1 醒 01)， DIPEA 1.5 隱 ol) 및 2-(4-플루오로페닐)아세틸 클로 라이드 (1.2 醒 ol) 를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 푸화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 213 화합물을 수득하였다 (수율 = 61%) 55-amino -N- (4-hydroxy-methoxy-phenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide (1醒0 1), DIPEA隱1.5 ol) and 2- (4- Fluorophenyl) acetyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and fused NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 213 compound (Yield = 61%).
匪 400 MHz, CDC13)6 8.28(s, IH), 8.03(s, IH, -NH), 8.0(s, IH, -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 합성예 214 ： 5— (2-(4-에틸페닐)아세트아미도) -N— (4-메록시펜에틸 )-2-옥소- 1， 2-디하이드로퀴놀린 -3-카르복사마이드 MHz 400 MHz, CDC1 3 ) 6 8.28 (s, IH), 8.03 (s, IH, -NH), 8.0 (s, IH, -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 Synthesis Example 214: 5— (2- (4-ethylphenyl) acetamido) -N— (4-methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carbox Maid
5-아미노 -N-(4-메톡시펜에틸)— 2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카르복 사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2— (4-에틸페닐)아세틸 클로라 이드 (1.2 議 ol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 214 화합물을 수득하였다 (수율 = 63%) 5-amino-N- (4-methoxyphenethyl) — 2ioxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2— (4-ethyl Phenyl) acetyl chloride (1.2 μl ol) was stirred for 15 minutes in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 214 compound (Yield = 63%).
¾ NMRC400 MHz, CDC13)6 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 합성예 221 ： N-(4-브로모펜에틸 )-5-(2-(4-하이드록시페닐)아세트아미도 )-2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMRC400 MHz, CDC1 3 ) 6 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, 3 H). MASS = 483.22 Synthesis Example 221 N- (4-bromophenethyl) -5- (2- (4-hydroxyphenyl) acetamido) -2-oxo-1,2-dihydroquinoline-3-carbox Maid
5-아미노 -N ; 4ᅳ브로모펜에틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 瞧 01)， DIPEA(1.5 mmol) 및 2-(4-하이드특시페닐)아세틸 클로라이드 (1.2 醒 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 221 화합물을 수득하였다 (수율 = 61%) 5-amino-N; 4'bromophenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 瞧0 1), DIPEA (1.5 mmol) and 2- (4-hydrospecificphenyl) acetyl chloride ( 1.2 μl ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 221 (Yield = 61%).
¾ 画 R(400 MHz, CDC13)5 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 합성예 231 ： ^(4-클로로펜에틸 )-5-(2-(4-니트로페닐)아세트아미도 )-2_옥 소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 画 R (400 MHz, CDC1 3 ) 5 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 Synthesis Example 231: ^ (4-Chlorophenethyl) -5- (2- (4-nitrophenyl) acetamido) -2_oxo-1,2-dihydroquinoline-3-carboxamide
5—아미노 -N-(4ᅳ클로로펜에틸)— 2-옥소— 1， 2-디하이드로퀴놀린 -3-카르복 사마이드 (1 瞧 ol), DIPEA 1.5 mmol) 및 2-(4—니트로페닐)아세틸 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이 트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 231 화합물을 수득하였다 (수율 = 61%) 5—amino-N- (4 ᅳ chlorophenethyl) — 2-oxo— 1, 2-dihydroquinoline-3-carbox Samid (1 'ol), DIPEA 1.5 mmol) and 2- (4—nitrophenyl) acetyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis Example 231 (yield = 61%).
¾證 (400 MHz, CDC13)6 8.28(s, 1H), 8.03(s, 1H, -NH) , 8.0(s, 1H¾ 證 (400 MHz, CDC1 3 ) 6 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 합성예 290 ： N-에틸 -2-옥소 -N-페닐 -5-프로피은아미도 -1,2-디하이드로 퀴놀린 -3-카르복사마이드 -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 Synthesis Example 290: N-ethyl-2-oxo-N-phenyl-5-propynamido-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-메틸 -2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카르복사마 이드 (1瞧 ol), DIPEA 1.5画 ol) 및 프로피오닐클로라이드 (1.2隱 ol )를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHCC로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 290 화합물을 수득하였다 (수율 = 69 . 5-amino-N-methyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5' ol) and propionylchloride (1.2 'ol) Was stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHCC and purified by silica gel column chromatography to give the synthesis example 290 compound (yield = 69.
¾ NMR OO MHz, CDC13)5 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 합성예 291 ： 5—부티라미도 -N-에틸 -2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR OO MHz, CDC1 3 ) 5 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 Synthesis Example 291 ： 5—Butyramido-N-ethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-메틸 -2-옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카르복사 마이드 (1隱 ol), DIPEA 1.5難 ol) 및 부티릴클로라이드 (1.2難 ol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 291 화합물을 수득하였다 (수율 = '6 . 5-amino-N-methyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5' ol) and butyryl chloride (1.2 'ol) Stir for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 291 compound (yield = '6.
¾ 賺 (400 MHz, CDC13)6 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 합성예 293 ： N-에틸 -2-옥소 -5-펜탄아미도 -N-(p-를일) -1,2-디하이드로 퀴놀 린 -3-카르복사마이드 ¾ 賺 (400 MHz, CDC1 3 ) 6 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, 3 H). MASS = 377.17 Synthesis Example 293: N-ethyl-2-oxo-5-pentaneamido-N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-에틸 -2-옥소 -N-(p-를일) -1，2-디하이드로퀴놀린 -3- 카르복사마이드 (1醒 ol), DIPEA(1.5mmol) 및 펜타노일클로라이드 (1.2mmol)를 C¾Cl2(2mL)에서 1,5분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 293 화합물을 수득하였다 (수율 = 62%) . 5-amino-N-ethyl-2-oxo-N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5 mmol) and pentanoyl chloride (1.2 mmol) was stirred in C¾Cl 2 (2 mL) for 1,5 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 293 compound (Yield = 62%).
¾ NMR(400 MHz, CDC13)8 8.28(s, 1H), 8.0(s, 1H, -NH), 7.88(m,¾ NMR (400 MHz, CDC1 3 ) 8 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 합성예 294 ： N-에틸 -5—(2-메특시아세트아미도 )-2-옥소 -N-(p-를일) _1，2- 디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 294: N-ethyl-5- (2-mesoxiacetamido) -2-oxo-N- (p-ylyl) _1,2-dihydroquinoline-3-carboxamide
5-아미노 - 에틸 -2-옥소 -N-(p—를일) -1，2-디하이드로퀴놀린 -3-카르복 사마이드 (1 隱 ol), DIPEA(1.5 mmol) 및 2-메록시아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 294 화합물을 수득하였다 (수율 =61%). 5 -Amino-ethyl-2-oxo-N- (p-yl) -1,2-dihydroquinoline-3-carboxamide (1 隱 ol), DIPEA (1.5 mmol) and 2-methoxyacetyl chloride (1.2 Pa ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 294 compound (yield = 61%).
¾ NMR (400 MHz, CDC13)5 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 합성예 305 ： 5-(2-브로모아세트아미도) -N-에틸 -N-(4-메록시페닐) -2-옥소- 1,2-디하이드로퀴 린 -3-카르복사마이드) ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 305: 5- (2-Bromoacetamido) -N-ethyl -N- (4-methoxyphenyl) -2-oxo- 1,2-dihydroquiline-3-carbox Amide)
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 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 305 화합물을 수득하였다 (수율 =69¾ . 5 -amino-N-ethyl-N- (4-methoxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-bromo Acetyl chloride (1.2 μl ol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography. Purification gave the compound of Synthesis Example 305 (yield = 69¾.
¾ NM (400 MHz, CDC13)6 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 합성예 317 ： N:(4-브로모페닐) -5-(2-클로로아세트아미도) -N-에틸 -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NM (400 MHz, CDC1 3 ) 6 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 Synthesis Example 317: N : (4-Bromophenyl) -5 (2-chloroacetamido) -N-ethyl-2-oxo-l, 2-dihydroquinoline-3-carboxamide
5-아미노 -N-(4-브로모페닐 )— N-에틸 -2-옥소 -1 ,2-디하이드로퀴놀린 -3- 카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-클로로아세틸 클로 라이드 (1.2 隱 ol)를 C C12에서 15분 간 교반하였다 (2mL). 잔기는 에틸아 세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 317 화합물을 수득하였다 (수율 = 61%). 5-amino-N- (4-bromophenyl) —N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-chloroacetyl Chloride (1.2 μl) was stirred for 15 min at C C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 317 (Yield = 61%).
¾ NMR(400 MHz, CDC13)6 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-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 351: N- (4-ethylphenyl) -5 (2-fluoroacetamido) -N-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-메틸 -2-옥소ᅳ N-(p-를일 )-1ᅳ 2-디하이드로퀴놀린 -3-카르복 사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-플루오로아세틸 클로라이드 (1.2 mmol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 351 화합물을 수득하였다 (수율 = 69%) 5-amino-N-methyl-2-oxoze N- (p-ylyl) -1 ′ 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2-fluoroacetyl Chloride (1.2 mmol) was stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to obtain the compound of Synthesis Example 351 (yield = 69%)
¾ NMR(400 MHz, CDC13)5 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(sᅳ 3H). MASS=381.15 합성예 362 ： (E)-5- (부트 -2-엔아미도) -N-(4-하이드록시페닐) -N-메틸ᅳ 2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 ᅳ 3H). MASS = 381.15 Synthesis Example 362: (E) -5- (But-2-enamido) -N- (4-hydroxyphenyl) -N-methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3 Carboxamide
5-아미노 -N-(4-하이드록시페닐 )-N-메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 5-amino-N- (4-hydroxyphenyl) -N-methyl-2-oxo-1, 2-dihydroquinoline
-3-카르복사마이드 (1 隱 ol), DIPEAU.5 mmol) 및 (E)-부트— 2-에노일 클로 라이드 (1.2 隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 362 화합물을 수득하였다 (수율 = 69%) -3-carboxamide (1 'ol), DIPEAU.5 mmol) and (E) -but- 2-enoyl claw Ride (1.2 μl) was stirred for 15 min in C¾Cl2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHCO 3 and purified by silica gel column chromatography to give Synthesis Example 362 compound (Yield = 69%)
¾ NMR(400 MHz, CDC13)8 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 합성예 379 ： N-(4- (하이드록시메틸)페닐)— 5-(3—하이드록시프로판아미도) -N- 메틸 -2-옥소— 1,2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 8 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, 1 H). MASS = 377.14 Synthesis Example 379 ： N- (4- (hydroxymethyl) phenyl) —5- (3—hydroxypropaneamido) -N-methyl-2-oxo— 1,2-dihydroquinoline-3- Carboxamide
5-아미노 -N-(4- (하이드록시메틸)페닐) -N-메틸 -2—옥소 -1， 2-디하이드로 퀴놀린 -3-카르복사마이드 (1 麵 ol), DIPEA(1.5 隱 ol) 및 3-하이드록시 프로파노일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 379 화합물을 수득하였다 (수율 = 61%)5-amino-N- (4- (hydroxymethyl) phenyl) -N-methyl-2—oxo-1,2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA (1.5' ol) And 3-hydroxy propanoyl chloride (1.2 μl ol) were stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 379 (Yield = 61%).
¾ NMR (40b MHz, CDC13)6 8.28(s, 1H), 8.14(d, 1H), 8.0(s, 1H, -¾ NMR (40b MHz, CDC1 3 ) 6 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,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,1H), 4.61 (m, 2H), 3.91 (m, 2H), 3.65 (m, 2H, -OH), 3.44 (s, 3H), 2.42 (m,
2H). MASS=395.15 합성예 380 : N-(4— (하이드록시메틸)페닐) -N-메틸 -5-(2-니트로아세트아미도)2H). MASS = 395.15 Synthesis Example 380: N- (4— (hydroxymethyl) phenyl) -N-methyl-5 (2-nitroacetamido)
-2-옥소 -1， 2-디하이드로퀴놀¾-3-카르복사마이드 2-oxo-1, 2-dihydroquinol¾-3-carboxamide
55-아미노 -N-(4- (하이드록시메틸)페닐) -N-메틸 -2-옥소— 1 , 2-디하이드 로퀴놀린— 3-카르복사마이드 (1 画 ol), DIPEA(1.5 誦 ol) 및 2-니트로아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 H반하였다. 잔기는 에틸아세테이트 및. 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 380 화합물을 수득하였다 (수율 = 69%). 55-amino-N- (4- (hydroxymethyl) phenyl) -N-methyl-2-oxo— 1, 2-dihydroquinoline— 3-carboxamide (1 画 ol), DIPEA (1.5 誦 ol ) And 2-nitroacetyl chloride (1.2 μl ol) were incubated for 15 min in CH 2 Cl 2 (2 mL). The residue is ethyl acetate and . Extraction with saturated NaHC0 3 and purification by silica gel column chromatography gave Synthesis Example 380 compound (Yield = 69%).
¾ 匪 R( 400 MHz, CDC13)5 8.28(s, 1H), 8.14(d, 1H) , 8.0(s, 1H, -¾ 匪 R (400 MHz, CDC1 3 ) 5 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).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 합성예 383 ： (E)-5- (부트 -2-엔아미도) -N-메틸 -2-옥소 -N-(4-비닐페닐) -1,2- 디하이드로퀴놀린 -3-카르복사마이드 MASS = 410.12 Synthesis Example 383: (E) -5- (but-2-enamido) -N-methyl-2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-메틸 -2-옥소 -N-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 隱 01)， DIPEA(1.5 mmol) 및 (E)-부트 -2-에노일 클로라이드 (1.2 隱 ol)를 CH2C12 2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 383 화합물을 수득하였다 (수율 = 61%). 5-amino-N-methyl-2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide 隱0 1), DIPEA (1.5 mmol) and (E) -boot 2-Enoyl chloride (1.2 μl ol) was stirred for 15 min in CH 2 C1 2 2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 383 compound (Yield = 61%).
¾ NMR(400.MHz, CDC13)5 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 합성예 386 ： 5-벤즈아미도— N—에틸 -2-옥소 -1,2-디하이드로퀴놀린 -3- 카르복사마이드 ¾ NMR (400. MHz, CDC1 3) 5 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 Synthesis Example 386 ： 5-Benzamido—N—ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-에틸 -2-옥소— 1 , 2—디하이드로퀴놀린 -3—카르복사마이드 ( 1 瞧 ol), DIPEA 1.5隱 ol) 및 벤조일클로라이드 (1.2隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 386 화합물을 수득하였다 (수율 = 66%) . 5-amino-N-ethyl-2-oxo- 1, 2-dihydroquinoline-3-carboxamide (1 'ol), DIPEA 1.5' ol) and benzoyl chloride (1.2 'ol) were dissolved in C¾Cl 2 (2 mL). Stirred 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 386 compound (Yield = 66%).
¾ 匪 R (400 MHz, CDC13)6 9.15(s, 1H, -NH), 8.28(sᅳ 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—디하이드 로퀴놀린 -3—카르복사마이드) ¾ 匪 R (400 MHz, CDC1 3 ) 6 9.15 (s, 1H, -NH), 8.28 (s ᅳ 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 Synthesis Example 387: (5- (3,4-Dihydroxybenzamido) -N-ethyl-2-oxo _1,2-dihydroquinoline-3-carboxamide)
5_아미노 -N—에틸 _2_옥소— i， 2 디하이드로퀴놀린 _3_카르복사마이드(丄 誦 ol), DIPEA 1.5麵 ol) 및 3ᅳ 4-디하이드록시벤조일클로라이드 (1.2隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 387 화합물을 수득하였다 (수율 = 61%) ¾ 匿 (400 MHz, CDC13)6 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(1;， 1H), 7.16(d, 1H) , 5.35(m, 2H, —OH), 3.21(m, 2H), 1.04(s, 3H). MASS=367.12 , 합성예 388 ： 5-(3, 4-디메틸벤즈아미도) -N-에틸 -2-옥소 -1,2-디하이드로 퀴놀린—3-카르복사마이드 5 _amino-N—ethyl _ 2 _oxo- i, 2 dihydroquinoline _ 3 _ carboxamide (DIPEA 1.5 麵 ol) and 3 '4-dihydroxybenzoyl chloride (1.2' ol) Was stirred in CH 2 Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 387 (yield = 61%). ¾ 匿 (400 MHz, CDC1 3 ) 6 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 (1 ;， 1H), 7.16 (d, 1H), 5.35 (m, 2H, —OH), 3.21 (m, 2H), 1.04 (s, 3 H). MASS = 367.12 , Synthesis 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 ( 1 隱 ol), DIPEAC1.5薩 ol) 및 3，4ᅳ디메틸벤조일클로라이드 (1.2隱 ol )를 C¾C12 (2mL)에서 15분간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 388 화합물을 수득하였다 (수율 = 61%) 5—amino—N—ethyl-2-oxo-1, 2-dihydroquinoline— 3-carboxamide (1 'ol), DIPEAC1.5' ol) and 3,4'dimethylbenzoylchloride (1.2 'ol) Was stirred in C¾Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 388 (Yield = 61%).
¾ NMR(400 MHz, CDC13)5 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 합성예 395 ： 5-(2- (벤조 [d] [1,3]디옥솔 -5-일)아세트아미도) -N- (니트로메틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 395: 5- (2- (Benzo [d] [1,3] dioxol-5-yl) acetamido) -N- (nitromethyl) -2-oxo-1,2-di Hydroquinoline-3-carboxamide
5-아미노 -N- (니트로메틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3—카르복사마 이드 (1 mmol), DIPEAC1.5 mmol) 및 2- (벤조 [d] [1，3]디옥솔 -5-일)아세틸클로 라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸 아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제 하여 합성예 395 화합물을 수득하였다 (수율 = 65%) . 5-amino-N- (nitromethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEAC1.5 mmol) and 2- (benzo [d] [1, 3] dioxol-5-yl) acetyl chloride (1.2 μl ol) was stirred for 15 min 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 Synthesis Example 395 compound (Yield = 65%).
¾ NMR (400 MHz, CDC13)8 8.28(s, 1H) , 8.03(s, 1H, -NH), 8.0(s,¾ NMR (400 MHz, CDC1 3 ) 8 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 합성예 398 (5-(3- (벤조 [d][l,3]디옥솔 -5-일)프로판아미도 )-2-옥소 -N- 프로필 -1 , 2-디하이드로퀴놀린— 3-카르복사마이드 ) 5-아미노 -2-옥소 -N-프로필 -1， 2-디하이드로퀴놀린 -3-카르복사마이드 ( 1 mmol), DIPEAC1.5 mmol) 및 3- (벤조 [d] [1，3]디옥솔ᅳ5-일)프로파노일 클로라 이드 (1.2 讓 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세 테이트 및 포화 Na}lC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 398 화합물을 수득하였다 (수율 =53%). 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 Synthesis Example 398 (5- (3- (benzo [d] [l, 3] dioxol-5-yl) propaneamido) -2-oxo-N-propyl-1, 2-dihydroquinoline— 3-carboxamide) 5-amino-2-oxo-N-propyl-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEAC1.5 mmol) and 3- (benzo [d] [1,3] dioxol ᅳ 5-yl) propanoyl chloride (1.2 讓 ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated Na} lCO 3 and purified by silica gel column chromatography to give the compound of Synthesis 398 (yield = 53%).
¾ NMR (400 MHz, CDC13)5 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 합성예 400 ： ((E)-5-(3- (나프탈렌 -2-일)프로판아미도 )-2-옥소 -N- (프로프 -1- 엔 -1-일 )-1， 2-디하이드로퀴놀린 -3-카르복사마이드) ¾ NMR (400 MHz, CDC1 3 ) 5 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 Synthesis Example 400: ((E) -5- (3- (naphthalen-2-yl) propaneamido) -2-oxo-N- (prop-1-en-1-yl) -1, 2-dihydroquinoline-3-carboxamide)
(E)-5—아미노 -2-옥소 -N- (프로프 -1-엔 -1-일) -1， 2-디하이드로퀴놀린 -3- 카르복사마이드 (1 ,隱 ol), DIPEA L5 mmol) 및 3- (나프탈렌 -2-일)프로파노일 클로라이드 (1.2 mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 400 화합물을 수득하였다 (수율 = 61%) . (E) -5—Amino-2-oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline-3-carboxamide (1 ,隱 ol), DIPEA L5 mmol ) And 3- (naphthalen-2-yl) propanoyl chloride (1.2 mmol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 400 compound (yield = 61%).
¾ 匪 R (400 MHz, CDC13)6 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(dᅳ 1H), 7.11(s, 1H), 5.13(s, 1H), 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-카르복사마이드 ¾ 匪 R (400 MHz, CDC1 3 ) 6 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 ᅳ 1H) , 7.11 (s, 1H), 5.13 (s, 1H), 3.01 (m, 2H), 2.84 (m, 2H), 2.05 (s, 3H) .MASS = 425.17 Synthesis Example 401: (E) -5- ( 2- (naphthalen-2-yl) acetamido) -2-oxo-N- (prop-1-en-1-yl) -1,2—dihydroquinoline-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 画 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 401 화합물을 수득하였다 (수율 =58%). (E) -5-amino-2-oxo— N— (prop-1-en-1-yl) -1,2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) And 2- (naphthalen-2-yl) acetyl chloride (1.2 μl ol) were stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the Synthesis Example 401 compound (yield = 58%).
¾ 丽 (400 MHz, CDC13)6 8.28(s, 1H), 8.01(d, 1H), 8.0(s, 2H, -¾ δ (400 MHz, CDC1 3 ) 6 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(1;， 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 합성예 404 ： 5-(우-([1，1'-비페닐 ]-4-일)아세트아미도) -N-(2-브로모에틸) -2- 옥소 -1,2-디하이드로퀴놀린 -3-카르복사마이드 NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.58 (1 ;， 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 Synthesis Example 404: 5- (Rh-([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 L.5 mmol) 및 2-([1，1'-비페닐]-4- 일)아세틸 클로라이드 (1.2 麵 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 404 화합물을 수득하였다 (수율 = 61%)5-amino-N- (2-bromoethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA L.5 mmol) and 2-([1,1 '-Biphenyl] -4-yl) acetyl chloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 404 (Yield = 61%).
¾ NMRC400 MHz, CDC13)6 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 합성예 424 ： 5ᅳ(2-(4-벤질페닐)아세트아미도) -N-(3,4-디하이드록시펜에틸) -¾ NMRC400 MHz, CDC1 3 ) 6 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, 2 H). MASS = 503.08 Synthesis Example 424: 5 ′ (2- (4-benzylphenyl) acetamido) -N- (3,4-dihydroxyphenethyl)-
2-옥소 -1，2-디하이드로퀴놀린 -3-카르복사마이드) 2-oxo-1,2-dihydroquinoline-3-carboxamide)
5-아미노 -Ν-(3 , 4-디하이드록시펜에틸) -2-옥소 -1， 2-디하이드로퀴놀린- 5-amino-Ν- (3,4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-
3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2-(4ᅳ벤질페닐)아세틸 클로라이드 (1.2 麵 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 424 화합물을 수득하였다 (수율 =61%). 3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (4 ᅳ benzylphenyl) acetyl chloride (1.2 麵 ol) were stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 424 (yield = 61%).
¾ 画 R(400 MHz, CDC13)6 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 합성예 425 ： N-(3 ,4-디하이드록시펜에틸 )-2-옥소 _5-프로피온아미도 -1,2- 디하이드로퀴놀린 -3ᅳ카르복사마이드 ¾ 画 R (400 MHz, CDC1 3 ) 6 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 Synthesis Example 425 ： N- (3,4-dihydroxyphenethyl) -2-oxo_5-propionamido-1,2-dihydroquinoline-3'carboxamide
5-아미노 -Ν-(3 , 4-디하이드록시펜에틸)— 2-옥소 -1 , 2-디하이드로퀴놀린- 5-amino-Ν- (3, 4-dihydroxyphenethyl) — 2-oxo-1, 2-dihydroquinoline-
3-카르복사마이드 (1 麵 ol), DIPEAU.5 隱 ol) 및 프로피오닐클로라이드 (1.2 mmol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 425 화합물을 수득하였다 (수율 =69%) 3-carboxamide (1 'ol), DIPEAU.5' ol) and propionylchloride (1.2 mmol) was stirred in C¾Cl 2 (2 mL) for 15 min. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the compound of Synthesis 425 (yield = 69%).
¾ 匪 R (40,0 MHz, CDC13)6 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 합성예 426 ： 5ᅳ부티라미도 -N-(3, 4-디하이드록시펜에틸 )-2-옥소 -1,2ᅳ 디하이드로퀴놀린 -3-카르복사마이드 ¾ 匪 R (40,0 MHz, CDC1 3 ) 6 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 Synthesis Example 426 ： 5'-butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1,2'-dihydroquinoline-3-carboxamide
5-아미노 -N-(3， 4-디하이드특시펜에틸 )-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 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 426 화합물올 수득하였다 (수율 =61%). 5-amino-N- (3,4-dihydrisophenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and butyrylchloride (1.2 mmol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give Synthesis Example 426 compound (yield = 61%).
¾ NMR(400 MHz, CDC13)6 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 합성예 427 ： N—(3, 4-디하이드록시펜에틸 )-2-옥소 -5-펜탄아미도 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis Example 427: N— (3,4-dihydroxyphenethyl) -2-oxo-5-pentaneamido-1,2-dihydrodroquinoline-3-carboxamide
5_아미노ᅳ N-(3， 4ᅳ다하이드록시펜에틸) -2-옥소ᅳ 1， 2-디하이드로퀴놀린- 3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 펜타노일 클로라이드 (1.2 隱 οθ를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 427 화합물을 수득하였다 (수율 =66%) . 5-amino-eu _ N - (3, 4 euda-hydroxy-phenethyl) -2-oxo-eu 1, 2-dihydro-quinoline-3-carboxamide (1 mmol), DIPEA (1.5 mmol) and pentanoyl chloride (1.2隱 θ was stirred for 15 min in C¾Cl 2 (2 mL) The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 427 compound (yield = 66%).
¾ NMR (400 MHz, CDC13)6 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 합성예 434 ： 5-(2- (에틸티오)아세트아미도) -N-(2- (나프탈렌 -2-일)에틸) -2- 옥소 -1 , 2-디하이드로퀴놀린ᅳ 3-카르복사마이드 ¾ NMR (400 MHz, CDC1 3 ) 6 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 Synthesis example 434: 5- (2- (ethylthio) acetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide
5-아미노 -N:(2- (나프탈렌 -2—일)에틸) -2-옥소— 1ᅳ 2—디하이드로퀴놀린- 3-카르복사마이드 (1 誦 ol), DIPEA(1.5 mmol) 및 3- (메틸티오)프로파노일 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토그래피로 정제하여 합성예 434 화합물을 수득하였다 (수율 =61%). 5-amino-N : (2- (naphthalene-2—yl) ethyl) -2-oxo— 1 ′ 2—dihydroquinoline-3-carboxamide (1 誦 ol), DIPEA (1.5 mmol) and 3- (Methylthio) propanoyl chloride (1.2 μl) was stirred 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 Synthesis Example 434 (yield = 61%).
¾ NMR (400 MHz, CDC13)S 8.28 (s, 1H), 8.03 (s, 1Hᅳ -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (m, 2H), 7.55 Cm, 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 합성예 435 ： 5— (2- (에틸아미노)아세트아미도) -N-(2- (나프탈렌 -2-일)에틸) -¾ NMR (400 MHz, CDC1 3 ) S 8.28 (s, 1H), 8.03 (s, 1H ᅳ -NH), 8.01 (d, 1H), 8.0 (s, 1H, -NH), 7.97 (d, 1H) , 7.94 (d, 1H), 7.88 (m, 2H), 7.55 Cm, 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 Synthesis Example 435: 5— (2- (ethylamino) acetamido) -N- (2- (naphthalen-2-yl) ethyl)-
2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복사마이드 2-oxo-1,2-dihydroquinoline-3-carboxamide
5-아미노 -N-(2- (나프탈렌 -2-일)에틸 )-2-옥소 -1， 2ᅳ디하이드로퀴놀린-5-Amino- N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2'dihydroquinoline-
3-카르복사마이드 (1 mmol), DIPEA(1.5 mmol) 및 2- (에틸아미노) 아세 ¾클로라이드 (1.2 画 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하고 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 435 화합물을 수득하였다 (수율 = 62%) . 3-carboxamide (1 mmol), DIPEA (1.5 mmol) and 2- (ethylamino) ace ¾chloride (1.2 dl) were stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 and purified by silica gel column chromatography to give the synthesis example 435 compound (yield = 62%).
¾ 證 (400 MHz, CDC13)5 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 합성예 436 ： 5ᅳ(2-에록시아세트아미도) -N-(2- (나프탈렌 -2-일)에틸) -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카르복사마이드 ¾ 證 (400 MHz, CDC1 3 ) 5 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 Synthesis Example 436 ： 5 ′ (2-Erooxyacetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carbox Maid
5—아미노 -N— (2- (나프탈렌 -2—일)에틸)ᅳ 2-옥소 -1 ,2-디하이드로퀴놀린- 5—Amino-N— (2- (naphthalene-2—yl) ethyl) ᅳ 2-oxo-1,2-dihydroquinoline-
3-카르복사마이드 (1 讓 ol), DIPEA(1.5 mmol) 및 2-에록시아세틸 클로라이드 (1.2 隱 ol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 436 화합불을 수득하였다. 3-carboxamide (1 μ ol), DIPEA (1.5 mmol) and 2-ethoxyacetyl Chloride (1.2 μl) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to obtain the synthesis example 436 compound fire.
¾ NMR OO MHz, CDC13)8 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) ¾ NMR OO MHz, CDC1 3 ) 8 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)
Figure imgf000225_0001
Figure imgf000225_0001
Reqgent： A) ,, dioxane, 12h B) R2, pyridine, 3h C) LiOH 0.5min H20, 100°C, 12h Reqgent: A) ,, dioxane, 12h B) R 2 , pyridine, 3h C) LiOH 0.5min H 2 0, 100 ° C, 12h
단계 (a一 0)의 일반적 과정  General process of step (a 一 0)
출발물질 (500 mg, 2.13 隱 ol)을 무수 1,4-디옥산 (25 mL)에 용해시켰다. ¾(50π )를 용액에 첨가하였다. 흔합물을 12시간 동안 상온에서 교반하고 기화시켜 9번 화합물을 수득하였다. 합성예 72 ： 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르보닐 클로라이드  Starting material (500 mg, 2.13 μl ol) was dissolved in anhydrous 1,4-dioxane (25 mL). ¾ (50 [pi]) was added to the solution. The mixture was stirred at room temperature for 12 hours and evaporated to afford compound 9. Synthesis Example 72: 2-oxo-1, 2-dihydroquinoline-3-carbonyl chloride
2-옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol) 를 무수 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 隱 ol)
1,4-디옥산 (2mL)에 용해시켰다. Cl2(2mL)를 용액에 첨가하였다. 흔합물을 12시간 동안 상^'에서 교반하고 기화시켜 합성예 72 화합물을 수득하였다 (수율 =80%). Dissolved in 1,4-dioxane (2 mL). Cl 2 (2 mL) was added to the solution. The mixture was stirred and evaporated in phase ^ ' for 12 h to afford Synthesis Example 72 compound (yield = 80%).
¾NMR( 400MHz, CDC13 )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 합성예 73 ： 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르보닐 브로마이드 ¾NMR (400 MHz, CDC1 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, 1H). MASS = 207.01 Synthesis Example 73: 2-oxo-1, 2-dihydroquinoline-3-carbonyl bromide
2ᅳ옥소 -1,2-디하이드로퀴놀린 -3-카복실릭 애시드 (1 隱 ol)를 무수 1,4-디옥산 (2 mL)에 용해시켰다. 이후 Br2(2mL)를 용액에 첨가하였다. 흔합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예 73 화합물을 수득하였다 (수율 =82%). 2oxo-1,2-dihydroquinoline-3-carboxylic acid (11 ol) Dissolved in 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 yield Synthesis Example 73 Compound (Yield = 82%).
¾ NMR (400 MHz, CDC13)6 8.37(s, IH), 8.14(d, IH), 8.0(s, IH, - NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH). MASS=250.96 합성예 74 ： 2-옥소 -1， 2-디하이드로퀴놀린 -3-카르보닐 플로라이드 ¾ NMR (400 MHz, CDC1 3 ) 6 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH,-NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 ( t, IH). MASS = 250.96 Synthesis Example 74: 2-oxo-1, 2-dihydroquinoline-3-carbonyl fluoride
2-옥소 -1，2-디하이드로퀴놀린 -3—카복실릭 애시드 (1 mmol)를 무수 2-oxo-1,2-dihydroquinoline-3—carboxylic acid (1 mmol)
1,4-디옥산 (2 mL)에 용해시켰다. F2(2mL)를 용액에 첨가하였다. 흔합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예 74 화합물을 수득하였다 (수율 =64%). Dissolved in 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 yield Synthesis Example 74 compound (yield = 64%).
1HNMR(400MHz,CDCl3)6 8.37(s, IH), 8.14(d, IH), 8.0(s, IH, -NH) , 1 HNMR (400 MHz, CDCl 3 ) 6 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH),
7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH). MASS = 191.04 합성예 75 ： 2-옥 -1， 2ᅳ디하이드로퀴놀린 -3-카르보닐 아이오다이드 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH). MASS = 191.04 Synthesis Example 75: 2-Oc-1, 2'dihydroquinoline-3-carbonyl iodide
2-옥소 -1,2-디하이드로퀴놀린— 3-카복실릭 애시드 (1 腿 ol)를 무수 2-oxo-1,2-dihydroquinoline—anhydrous 3-carboxylic acid (1 腿 ol)
1,4-디옥산 (2 mL)에 용해시켰다. I2(2mL)를 용액에 첨가하였다. 흔합물을 12시간 동안 상온에서 교반하고 기화시켜 합성예 75 화합물을 수득하였다 (수율 =71¾ . Dissolved in 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 afford the Synthesis Example 75 compound (yield = 71¾.
1HNMR(400MHz,CDCl3)5 8.37(s, IH), 8.14(d, IH), 8.0(s, IH, -NH),1 HNMR (400 MHz, CDCl 3 ) 5 8.37 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH),
7.36 (d, IH), 7.31(t, IH), 7.14(t, IH). MASS=298.94 단계 (b-10)의 일반적 과정 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH). MASS = 298.94 General procedure of step (b-10)
R2(0.65mL, 12.73mmol)를 0°C에서 꾀리딘 (15mL)에 용해된 산 현탄액 (1.49g, 6. 6隱01)에 적상하였다. 흔합물을 110°C에서 3시간 동안 상온까지 냉각시키고 ，1^(：1(5 1 )를 첨가하고 물로 세척하여 10번 화합물을 수득하였다. 합성예 11 ： 3-클로로퀴놀린 -2(1H)-은) R 2 (0.65 mL, 12.73 mmol) was added dropwise to an acid suspension (1.49 g, 6.6 × 01) dissolved in zuridine (15 mL) at 0 ° C. The mixture was cooled to room temperature at 110 ° C. for 3 hours, 1 ^ ( : 1) was added and washed with water to obtain compound 10. Synthesis Example 11 3-chloroquinoline-2 (1H) -silver)
Cl2(2画 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였다. 흔합물을 1K C에서 3시간 동안 상온까지 넁각시키고, INHCKlmL)를 첨가하고 물로 세척하여 합성예 11 화합물을 수득하였다 (수율 =97%). Dropped onto acid suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 'ol) in which Cl 2 (2' ol) was dissolved in pyridine (O.lmL) at 0 ° C. It was. The mixture was cooled to room temperature for 3 hours at 1 K C, INHCKlmL) was added and washed with water to give Synthesis Example 11 compound (yield = 97%).
證(400¾1 ， CDC13)5 8.0 (s, IH, -NH) , 8.14 (d, IH), 7.54 (s, IH), 7.36 (d, IH), 7.31 (d, IH), 7.14 (d, IH). MASS = 179.01 합성예 12 (3，5-디클로로퀴놀린-2(111)—온) 400 (400¾1, CDC1 3 ) 5 8.0 (s, IH, -NH), 8.14 (d, IH), 7.54 (s, IH), 7.36 (d, IH), 7.31 (d, IH), 7.14 (d, IH). MASS = 179.01 Synthesis Example 12 (3,5-dichloroquinolin-2 (111) -one)
Cl2(2瞧 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 5-클로로 -2-옥소- 1,2-디하이드로퀴놀린 -3-카르복실릭애시드 (lmmol)의 산 현탄액에 적상하였다. 흔합물을 11CTC에서 3시간 동안 상온까지 냉각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 12 화합물을 수득하였다 (수율 = 90%).Acid suspension of 5-chloro-2-oxo- 1,2-dihydroquinoline-3-carboxylic acid (lmmol) in which Cl 2 (2 ′ ol) was dissolved in pyridine (O.lmL) at 0 ° C. It was suitable for. The mixture was cooled to room temperature at 11 CTC for 3 hours, INHCKlmL) was added and washed with water to give Synthesis Example 12 compound (yield = 90%).
lNMR^OOMHz, CDC13)6 8.02(d, IH), 8.0(s, -NH, IH), 7.54(s, IH), 7.25 (t, IH), 7.18(s, IH). MASS=212.97 합성예 13 ： 3-클≤로ᅳ 6-플루오로퀴놀린— 2(1H)-은 l NMR ^ OO MHz, CDC1 3 ) 6 8.02 (d, IH), 8.0 (s, -NH, IH), 7.54 (s, IH), 7.25 (t, IH), 7.18 (s, IH). MASS = 212.97 Synthesis Example 13 3-Cl ≦ Login 6-fluoroquinoline—2 (1H) -silver
Cl2(2醒 ol)를 0°C에서 피리딘 (O.lmL)에 용해시칸 6-플루오로 -2-옥소- 1,2-디하이드로퀴놀린 -3-카르복실릭애시드 (lmmol)의 산 현탄액에 적상하였다. 흔합물을 110°C에서 3시간 동안 상온까지 냉각시키고， 1NHC1 UmL)를 첨가하고 물로 세척하여 합성예 13 화합물을 수득하였다 (수율 =92%). Cl 2 (2醒ol) to 0 ° C in a column of 6-fluoro when dissolved in pyridine (O.lmL) -2- oxo-1,2-dihydroquinoline-3-carboxylic acid of the metallic acid (lmmol) It was wound up in suspension. The mixture was cooled to 110 ° C. for 3 hours at room temperature, 1NHC1 UmL) was added and washed with water to give Synthesis 13 Compound (Yield = 92%).
1HNMR(400MHz, CDC13) δ 8.0(s, IH, -NH), 7.74(d, IH), 7.54(s, IH),1 HNMR (400 MHz, CDC1 3 ) δ 8.0 (s, IH, -NH), 7.74 (d, IH), 7.54 (s, IH),
7.10 (d, IH), 6.94(d, IH) . MASS=197.00 합성예 14 ： 3-클로로 -7-플루오로퀴놀린 -2(1H)-온 7.10 (d, IH), 6.94 (d, IH). MASS = 197.00 Synthesis Example 14 3-chloro-7-fluoroquinolin-2 (1H) -one
Cl2(2隱 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 7-플루오로 -2-옥소- 1,2-디하이드로퀴놀린ᅳ 3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였 다. 흔합물을 110T：에서 3시간 동안 상온까지 냉각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 14화합물을 수득하였다 (수율 =83%). Of 7-fluoro-2-oxo- 1,2-dihydroquinoline® 3-carboxylic acid (1 'ol) in which Cl 2 (2' ol) was dissolved in pyridine (O.lmL) at 0 ° C. It was loaded onto acid suspension. The mixture was cooled to room temperature at 110T: for 3 hours, INHCKlmL) was added and washed with water to give Synthesis 14 Compound (Yield = 83%).
¾醒 R (400MHz, CDC13)6 8.0(s, IH, -NH), 7.70(d, IH), 7.54(s, IH), 7.54 (s, IH), 7.34(d, IH), 6.93(d, IH). MASS=197.00 합성예 15 ： 3-아이오도퀴놀린 -2(1H)-온 I2(2麵 o 를 0°C에서 피리딘 (O.lmL)에 용해시킨 2-옥소 -1，2- 디하이드로퀴놀린ᅳ 3-카르복실릭애시드 (1画 ol)의 산 현탄액에 적상하였다. 흔합물을 1K C에서 3시간 동안 상온까지 냉각시키고， lNHCl(lmL)를 첨가하고 물로 세척하여 합성예 15화합물을 수득하였다 (수율 =94%). ¾ 醒 R (400MHz, CDC1 3 ) 6 8.0 (s, IH, -NH), 7.70 (d, IH), 7.54 (s, IH), 7.54 (s, IH), 7.34 (d, IH), 6.93 ( d, IH). MASS = 197.00 Synthesis Example 15: 3-iodoquinolin-2 (1H) -one I 2 (2V o was loaded onto an acid suspension of 2-oxo-1,2-dihydroquinoline 3 3-carboxylic acid (1X ol) dissolved in pyridine (O.lmL) at 0 ° C. The mixture was cooled to room temperature for 3 hours at 1 K C, lNHCl (lmL) was added and washed with water to give Synthesis 15 Compound (Yield = 94%).
¾讓 (400MHz, CDC13)6 8.17(s, 1H) , 8.14(d, 1H), 8.0(s, 1H, -NH) ,¾ 讓 (400MHz, CDC1 3 ) 6 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 합성예 16 ： 3, 5-디아이오도도퀴놀린 -2( 1H)-온 7.36 (d, 1 H), 7.34 (t, 1 H), 7.14 (t, 1 H). MASS = 270.95 Synthesis Example 16 3,5-Diiododoquinolin-2 (1H) -one
12(2誦 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 5-아이오도 -2-옥소- 1，2-디하이드로퀴놀린 -3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였 다. 흔합물을 110°C에서 3시간 동안 상온까지 냉각시키고， 1NHC1 (lmL)를 첨가하고 물로 세척하여 10번 화합물을 수득하였다 (수율 = 92%) . · Of 5-iodo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 'ol) in which 1 2 (2' ol) was dissolved in pyridine (O.lmL) at 0 ° C. It was loaded onto acid suspension. The mixture was cooled to 110 ° C. at room temperature for 3 hours, 1NHC1 (lmL) was added and washed with water to afford compound 10 (yield = 92%). ·
匪 R OOMHz, CDC13)6 8.17(s, 1H), 8.1(d, 1H), 8.0(s, 1H, -NH), 7.47(d, 1H), 7.08(t, 1H). ASS=396.85 합성예 17 ： 3-아이오도 -5-메틸퀴놀린 -2(1H)_온 匪 R OO MHz, CDC1 3 ) 8.17 (s, 1H), 8.1 (d, 1H), 8.0 (s, 1H, -NH), 7.47 (d, 1H), 7.08 (t, 1H). ASS = 396.85 Synthesis Example 17: 3-iodo-5-methylquinolin-2 (1H) _one
12(2隱 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 5-메틸ᅳ 2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복실릭애시드 (lmmol)와 산 현탄액에 적상하였다. 흔합물을 1K C에서 3시간 동안 상온까지 냉각시키고， INHCKlmL)를 첨가하고 물로 세척하여 10번의 화합물을 수득하였다 (수율 =92%).5-methyl ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (lmmol) and acid suspension in which 1 2 (2 'ol) was dissolved in pyridine (O.lmL) at 0 ° C. It was suitable for. The mixture was cooled to room temperature for 3 hours at 1 K C, INHCKlmL) was added and washed with water to give 10 compounds (yield = 92%).
NMR(400MHz, CDC13)5 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)-온 NMR (400MHz, CDC1 3 ) 5 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 Synthesis Example 18 ： 3.-Methylquinolin-2 (1H) -one
(C¾)2(2mmol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 2ᅳ옥소ᅳ1，2- 디하이드로퀴놀린 -3-카르복실릭애시드 (1誦 ol)의 산 현탄액에 적상하였다. 흔합물을 11CTC에서 3시간 동안 상온까지 냉각시키고, lNHCl(lmL)를 첨가하고 물로 세척하여 합성예 18 화합물을 수득하였다 (수율 =48%). (C¾) 2 (2mmol) is dissolved in pyridine (O.lmL) at 0 ° C in acid suspension of 2-ioxox1,2-dihydroquinoline-3-carboxylic acid (1x ol). It was. The mixture was cooled to room temperature at 11 CTC for 3 hours, lNHCl (lmL) was added and washed with water to give Synthesis Example 18 compound (yield = 48%).
¾腿 (400MHz , CDC13)5 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)-온 ¾ 腿 (400MHz, CDC1 3 ) 5 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 Synthesis Example 19: 3-methyl-6- (methylthio) quinolin-2 (1H) -one
(C¾)2(2睡 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 6- (메틸티오) -2- 옥소 -1，2-디하이드로퀴놀린 -3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였다. 흔합물을 110°C에서 3시간 동안 상온까지 넁각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 19 화합물을 수득하였다 (수율 =49%). 6- (methylthio) -2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1) in which (C¾) 2 (2 睡 ol) was dissolved in pyridine (O.lmL) at 0 ° C.隱 ol) was added to the acid suspension. The mixture was allowed to stand at room temperature for 3 hours at 110 ° C., INHCKlmL) was added and washed with water to give Synthesis Example 19 compound (yield = 49%).
匪 R(400MHz, CDC13)6 8.0(s, IH, -NH) , 7.72(dᅳ IH), 7.66(s, IH), 7.14 (s, IH), 6.87(d, IH) , 2.53(s, 3H), 2.43(s, 3H). MASS=205.06 합성예 20 ： 3-메특시퀴놀린 -2(1H)-온 匪 R (400MHz, CDC1 3 ) 6 8.0 (s, IH, -NH), 7.72 (d ᅳ IH), 7.66 (s, IH), 7.14 (s, IH), 6.87 (d, IH), 2.53 (s , 3H), 2.43 (s, 3H). MASS = 205.06 Synthesis Example 20: 3-methoxyquinolin-2 (1H) -one
(0CH3)2(2隱 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 2-옥소 -1，2- 디하이드로퀴놀린— 3-카르복실릭애시드 (lmmol)의 산 현탄액에 적상하였다. 흔합물을 11( C에서 3시간 동안 상온까지 넁각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 20 화합물을 수득하였다 (수율 =94%). (0CH 3 ) 2 (2 ′ ol) in an acid suspension of 2-oxo-1,2-dihydroquinoline—3-carboxylic acid (lmmol) dissolved in pyridine (O.lmL) at 0 ° C. It was good. The mixture was stirred at room temperature for 3 hours at C, INHCKlmL, and washed with water to give Synthesis Example 20 compound (yield = 94%).
1HNMR(400MHz, CDC13)6 8.14(d, IH), 8.0(s, IH, -NH), 7.36(d, 10，1 HNMR (400 MHz, CDC1 3 ) 6 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, 10,
7.31 (t, IH), 7.14(t, IH), 6.29(s, IH), 3.80(s, 3H). MASS=175.06 합성예 21 ： 3，7-디메톡시퀴놀린-2(111)-온 7.31 (t, IH), 7.14 (t, IH), 6.29 (s, IH), 3.80 (s, 3H). MASS = 175.06 Synthesis Example 21 ： 3,7-Dimethoxyquinolin-2 (111) -one
(0CH3)2(2瞧 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 7-메톡시 -2- 옥소 -1,2-디하이드로퀴놀린 -3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였다. 흔합물을 110°C에서 3시간 동안 상온까지 냉각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 21 화합물을 수득하였다 (수율 =76%) (0CH 3 ) 2 (2 ′ ol) dissolved in pyridine (O.lmL) at 0 ° C. 7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1 ° ol) was added dropwise to the acid suspension. The mixture was cooled to 110 ° C. at room temperature for 3 hours, INHCKlmL) was added and washed with water to give Synthesis Example 21 compound (yield = 76%).
¾NMR(400MHz, CDCl3)58.0(s, IH, -NH), 7.31(s, IH), 7.25(d, IH), 6.68 (dᅳ IH), 6.29(s, IH) , 3.8(s, 3H), 3.83(s, 3H). MASS=205.07 합성예 22 ： 3-아미노퀴놀린 -2(1H)-은 ¾NMR (400 MHz, CDCl 3 ) 58.0 (s, IH, -NH), 7.31 (s, IH), 7.25 (d, IH), 6.68 (d ᅳ IH), 6.29 (s, IH), 3.8 (s, 3H ), 3.83 (s, 3 H). MASS = 205.07 Synthesis Example 22: 3-Aminoquinoline-2 (1H) -silver
(N¾)2(2麵 ol)를 0°C에서 피리딘 (O.lmL)에 용해시킨 2-옥소 -1,2- 디하이드로퀴놀린— 3-카르복실릭애시드 (1隱 ol)의 산 현탄액에 적상하였다. 흔합물을 110°C에서 3시간 동안 상온까지 냉각시키고， INHCKlmL)를 첨가하고 물로 세척하여 합성예 22 화합물을 수득하였다 (수율 =73%). ¾腿 (400MHz, CDC 13 )δ 8.56(s, 2H，ᅳ NH2), 8.14(d, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 6.10(s, IH). MASS=160.06 합성예 23 ： 3-아미노 -l-(4-플루오로벤질)퀴놀린 -2(1H)-은 2-oxo-1,2-dihydroquinoline—an acid suspension of 3-carboxylic acid (1 隱 ol) with (N¾) 2 (2 麵 ol) dissolved in pyridine (O.lmL) at 0 ° C It was suitable for. The mixture was cooled to 110 ° C. for 3 hours at room temperature, INHCKlmL) was added and washed with water to give the compound of Synthesis 22 (yield = 73%). ¾ 腿 (400MHz, CDC 13) δ 8.56 (s, 2H, ᅳ NH2), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH). MASS = 160.06 Synthesis Example 23: 3-Amino-l- (4-fluorobenzyl) quinoline-2 (1H) -silver
(N¾)2(2赚 ΰΐ)를 0°C에서 피리딘 (O.lmL)에 용해시킨 1-(4- 플루오로벤질 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카르복실릭애시드 ( lmmol)의 산 현탄액에 적상하였다. 흔합물을 1KTC에서 3시간 동안 상온까지 냉각시키고, lNHCl(lmL)를 첨가하고 물로 세척하여 합성예 23 화합물을 수득하였다 (수율 =92%). 1- (4-fluorobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylic, in which (N¾) 2 (2 ΰΐ) was dissolved in pyridine (O.lmL) at 0 ° C. It was dropwise added to an acid suspension of acid (lmmol). The mixture was cooled to room temperature for 3 hours at 1 KTC, lNHCl (lmL) was added and washed with water to give Synthesis Example 23 compound (yield = 92%).
¾賺 (400丽 z, CDC13)6 8.56(s, IH, -NH2), 7.65(d, IH) , 7.39(dd,¾賺(400丽z, CDC1 3) 6 8.56 (s, IH, -NH 2), 7.65 (d, IH), 7.39 (dd,
2H), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 7.12(dd, 2H) , 4.94(s, 2H). MASS=268.10 합성예 24 ： 3-플루오로퀴놀린 -2(1H)ᅳ온 2H), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 7.12 (dd, 2H), 4.94 (s, 2H). MASS = 268.10 Synthesis Example 24: 3-fluoroquinolin-2 (1H)
F2(2隱 ol)를. 0°C에서 피리딘 (O.lmL)에 용해시킨 2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복실릭애시드 (1睡 ol)의 산 현탄액에 적상하였다. 흔합물을 1KTC에서 3시간 동안 상온까지 냉각시키고, INHCKlmL)를 첨가하고 물로 세척하여 합성예 24 화합물을 수득하였다 (수율 = 90%) . F 2 (2 ′ ol). It was dropwise added to the acid suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1x ol) dissolved in pyridine (O.lmL) at 0 ° C. The mixture was cooled to room temperature for 3 hours at 1 KTC, INHCKlmL) was added and washed with water to give Synthesis Example 24 compound (yield = 90%).
¾證(400腿 z,CDCl3)S 8.14(d, IH), 8.0(s, IH, -NH), 7.36(d, IH), 7.31 (t, IH), 7.14(t, IH), 6.96(s, IH). MASS=163.04 단계 (c-11)의 일반적 과정 ¾ (400 腿 z, CDCl 3 ) S 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 6.96 (s, IH). MASS = 163.04 General process of step (c-11)
출발물질 (230 mg, 0.8 mmol)을 LiOH(15 mL)에 두시간 환류하였다. 흔합물을 IN HC1로 산성화시키고 여과하였다.  The starting material (230 mg, 0.8 mmol) was refluxed in LiOH (15 mL) for 2 hours. The mixture was acidified with IN HC1 and filtered.
잔여물을 물로 세첨하여 11번 화합물을 수득하였다. 합성예 1 ： 퀴놀린 -2(1H)-온 The residue was triturated with water to afford compound 11. Synthesis Example 1 quinolin-2 (1H) -one
2-옥소 -1，2-디하이드로퀴놀린 -3-카복실릭애시드 (1 讓 ol)를 Li0H(0.1 mL)에 두시간 동안 환류하였다. 흔합물을 IN HCI로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 1 화합물을 수득하였다 (수율 =9¾). ¾NMR(400MHz, CDC13)S 8.42(s, IH), 8.14(d, IH), 8.0(s, IH, -NH), 7.36 (dᅳ IH), 7.31(t, IH), 7.14(t, IH), 6.57(s, IH). MASS=145.05 합성예 2 ： 1-메틸퀴놀린 -2(1H)-은 2-oxo-l, 2-dihydroquinoline-3-carboxylic acid (1xol) was refluxed in Li0H (0.1 mL) for 2 hours. The mixture was acidified with IN HCI and filtered. The filter residue was washed with water to give Synthesis Example 1 compound (yield = 9¾). ¾NMR (400MHz, CDC1 3 ) S 8.42 (s, IH), 8.14 (d, IH), 8.0 (s, IH, -NH), 7.36 (d ᅳ IH), 7.31 (t, IH), 7.14 (t, IH), 6.57 (s, IH). MASS = 145.05 Synthesis Example 2 1-methylquinoline-2 (1H) -silver
1-메틸 -2-옥소ᅳ 1,2-디하이드로퀴놀린 -3ᅳ카복실릭애시드 (1 mniol)를 1-methyl-2-oxo ᅳ 1,2-dihydroquinoline-3 -carboxylic acid (1 mniol)
Li0H(0.1 mL)에 두시간 동안 환류하였다. 흔합물을 IN HC1로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 2 화합물을 수득하였다 (수율 =93%). Reflux to Li0H (0.1 mL) for 2 hours. The mixture was acidified with IN HC1 and filtered. The filtration residue was washed with water to give Synthesis Example 2 compound (yield = 93%).
醒 R(400MHz,CDCl3)S 8.42(s, 1H)ᅳ 7.65(d, IH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 6.57(s, IH). MASS=159.07 합성예 3 ： 1-에틸퀴놀린 -2(1H)-온 醒 R (400 MHz, CDCl 3 ) S 8.42 (s, 1H) ᅳ 7.65 (d, IH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 6.57 (s, IH) . MASS = 159.07 Synthesis Example 3 1-ethylquinolin-2 (1H) -one
1-에틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실릭애시드 ( 1 腿 01 )를 Li0H(0.1 mL)에 두시간 동안 환류하였다. 흔합물올 IN HC1로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 3 화합물을 수득하였다 (수율 =90 .  1-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1x01) was refluxed in Li0H (0.1 mL) for 2 hours. The mixture was acidified with IN HC1 and filtered. The filter residue was washed with water to give Synthesis Example 3 compound (yield = 90.
^NMR OOMHz, CDC13)5 8.42(s, IH), 7.65(t, IH), 7.36(d, IH), 7.31(t, IH), 7.14(t, IH), 6.57(s, IH), 4.28(s, 2H), 1.31(s, 3H). MASS=173.08 합성예 4 ： 5-브로모퀴놀린 -2(1H)-온 ^ NMR OOMHz, CDC1 3 ) 5 8.42 (s, IH), 7.65 (t, IH), 7.36 (d, IH), 7.31 (t, IH), 7.14 (t, IH), 6.57 (s, IH), 4.28 (s, 2 H), 1.31 (s, 3 H). MASS = 173.08 Synthesis Example 4 5-Bromoquinolin-2 (1H) -one
5—브로모 -2-옥소 -1 , 2-디하이드로퀴놀린— 3-카복실릭애시드 ( 1 隱 ol )를 LiOH (0.1 mL)에 두시간 동안 환류하였다. 흔합물올 IN HC1로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 4 화합물을 수득하였다 (수율 =96%).  5—Bromo-2-oxo-1, 2-dihydroquinoline— 3-carboxylic acid (1 × ol) was refluxed in LiOH (0.1 mL) for 2 hours. The mixture was acidified with IN HC1 and filtered. The filtration residue was washed with water to give Synthesis Example 4 compound (yield = 96%).
1HNMR(400MHz,CDCl3)6 8.42(s, IH), 8.08(d, IH), 8.0(s, IH, -NH), 7.29 (d, IH), 7.050 , IH)， 6.57(s, IH). MASS=222.96 합성예 5 ： 6-브로모퀴놀린 -2(1H)-온 1 HNMR (400MHz, CDCl 3 ) 6 8.42 (s, IH), 8.08 (d, IH), 8.0 (s, IH, -NH), 7.29 (d, IH), 7.050, IH), 6.57 (s, IH ). MASS = 222.96 Synthesis Example 5 6-bromoquinolin-2 (1H) -one
6ᅳ브로모 -2—옥소— 1，2-디하이드로퀴놀린 -3—카복실릭애 ᅵ드 (1 隱 ol)을 6-bromo-2—oxo—1,2-dihydroquinoline-3—carboxylic acid (1 隱 ol)
LiOH (0.1 mL)에 두시간 동안 환류하였다. 흔합물을 IN HC1로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 5 화합물을 수득하였다 (수율 =92%). It was refluxed in LiOH (0.1 mL) for 2 hours. The mixture to IN HC1 Acidified and filtered. The filter residue was washed with water to give Synthesis Example 5 compound (yield = 92%).
¾應 R (400MHz, CDC13 )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)-온 ¾ 應 R (400MHz, CDC1 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). MASS = 222.96 Synthesis Example 6 7-Bromoquinolin-2 (1H) -one
7-브로모 -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복실릭애시드 ( 1 隱 01 )을 LiOH (0.1 mL)에 두시간 동안 환류하였다. 흔합물을 IN HC1로 산성화시키고 여과하였다. 여과 잔여물을 물로 세척하여 합성예 6 화합물을 수득하였다 (수율 = 86%).  7-Bromo-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1x01) was refluxed in LiOH (0.1 mL) for 2 hours. The mixture was acidified with IN HC1 and filtered. The filter residue was washed with water to give Synthesis Example 6 compound (yield = 86%).
¾匪1 (40( ¾, )(:13)38.42(3, 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 -l-(4- (트라이플루오로메특시)벤질) - 1,2—디하이드로퀴놀린 -3-카르복스아미드 ¾ 匪 1 (40 (¾,) ( : 1 3 ) 38.42 (3, 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 Synthesis Example 511: 5-Chloro-2-oxo-N-phenethyl-1- (4- (trifluoromepoxy) benzyl) -1,2-dihydro Quinoline-3-carboxamide
5-클로로 -2-옥소 -엔-페네틸 -1,2—디하이드로퀴놀린ᅳ 3-카르복스아미 드를 디메틸포름아미드에 녹인 후， 4- (트라이플루오로메톡시)벤질 브로마이드, 18-크라운 -6， 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =61%).  5-Chloro-2-oxo-ene-phenethyl-1,2—dihydroquinoline ᅳ 3-Carboxamide in dimethylformamide, 4- (trifluoromethoxy) benzyl bromide, 18-crown- 6, Potassium carbonate was added together and stirred at room temperature for 12 hours (yield = 61%).
H NMR (400MHz, CDC13) S9.77(s, 1H), 9.45(s,lH), 7.51-7.45(m, 1H),H NMR (400 MHz, CDC1 3 ) S9.77 (s, 1H), 9.45 (s, lH), 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 합성예 512: 5-클로로 -l-(4-에틸벤질)— 2-옥소— N-페네틸 -1ᅳ 2-다이하이 드로퀴놀린 -3-카프복스아미드 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 Synthesis Example 512: 5-chloro-l- (4-ethylbenzyl)-2-oxo- N-phenethyl-1 '2-dihydricroquinoline-3-capboxamide
5-클로로 -2 옥소-엔―페네틸 -1， 2-디하이드로퀴놀린 -3- 카르복스아미드를 디메틸포름아미드에 녹인 후， 4-에틸 벤질 클로라이드， 18-크라운ᅳ 6, 포타슴 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =63%)  Dissolve 5-chloro-2-oxo-en-phenethyl-1,2-dihydroquinoline-3-carboxamide in dimethylformamide, and then add 4-ethyl benzyl chloride, 18-crown 6, and formate carbonate. Put and stirred at room temperature for 12 hours (yield = 63%)
¾ NMR (400MHz, CDCI3) δ 9.86(s, 1H), 9.43(s, 1H), 7.43(t, 1H), ¾ NMR (400 MHz, CDCI3) 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 합성예 513: 5-클로로 -l-(4-아이소프로필벤질) -2-옥소 -N-페네틸 -1,2-다이 하이드로퀴놀린 -3-카르복스아미드 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 Synthesis Example 513: 5-chloro-l- (4-isopropylbenzyl) -2-oxo-N -Phenethyl-1,2-dihydroquinoline-3-carboxamide
5-클로로 -1-메틸 -2-옥소-엔ᅳ페네틸 -1， 2-디하이드로퀴놀린 -3-카르 복스아미드를 디메틸포름아미드에 녹인 후， 4ᅳ아이소프로필 벤질 클로라이드， 18-크라운 -6， 포타슴 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =66%).  After dissolving 5-chloro-1-methyl-2-oxo-enfephenethyl-1,2-dihydroquinoline-3-carboxamide in dimethylformamide, 4'isopropyl benzyl chloride, 18-crown-6 , Potassium carbonate was added together and stirred at room temperature for 12 hours (yield = 66%).
¾ 丽 R(40()MHz, CDCls) 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 합성예 514: 5-클로로ᅳ1-(4-나이트로벤질 )—2-옥소 -N-페네틸 -1，2-다이하이 드로퀴놀린 -3-카르복스아미드  ¾ δ R (40 () MHz, CDCls) 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 Synthesis Example 514: 5-chloro ᅳ 1- (4-nitrobenzyl) —2-oxo-N-phenethyl-1,2-dihydrodroquinoline-3-carboxamide
5-클로로 -2-옥소-엔ᅳ페네틸 -1， 2ᅳ디하이드로퀴놀린 -3ᅳ  5-Chloro-2-oxo-enfephenethyl-1, 2'dihydroquinoline-3 '
카르복스아미드를 디메틸포름아미드에 녹인 후， 4-나이트로 벤질 브로마이드， 18-크라운 -6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =64%). After dissolving the carboxamide in dimethylformamide, 4-nitrobenzyl bromide, 18-crown-6, and potassium carbonate were added together and stirred at room temperature for 12 hours (yield = 64%).
¾ NMR (400MHz, CDC13) 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 (111, 7H), 7.08 (d, 1H), 5.66 (s( 1H), 3.73 (dd, 2H), 2.95 (t, 2H)， MASS=461.39 합성예 515: 5-클로로 -l-(4-메록시벤질) -2-옥소 -N-페네틸 -1，2-다이하이 드로퀴놀린 -3-카르복스아미드 ¾ NMR (400 MHz, CDC1 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 (111, 7H), 7.08 (d, 1H), 5.66 (s ( 1H), 3.73 (dd, 2H), 2.95 (t, 2H), MASS = 461.39 Synthesis Example 515: 5-chloro-l- (4-methoxybenzyl ) -2-oxo-N-phenethyl-1,2-dihydrodroquinoline-3-carboxamide
5-클로로 -2-옥소 -엔ᅳ페네틸 -1,2-디하이드로퀴놀린 -3-카르복스 아미 드를 디메틸포름아미드에 녹인 후， 4-메록시 벤질 클로라이드， 18-크라운 -6， 포타슴 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =51%).  Dissolve 5-chloro-2-oxo-enfephenethyl-1,2-dihydroquinoline-3-carboxamide in dimethylformamide, 4-methoxy benzyl chloride, 18-crown-6, fortam The carbonates were put together and stirred at room temperature for 12 hours (yield = 51%).
¾ 匪 R(400MHz, CDCI3) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H), 7.34-7.21 (in, 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 -l-(4-에틸벤질) -N-(4-플루오로페네틸) -2-옥소 -1,2- 디하이드로퀴놀린 -3—카프복스아미드) ¾ 匪 R (400 MHz, CDCI3) δ 9.85 (s, 1H), 9.42 (s, 1H), 7.44 (t, 1H), 7.34-7.21 (in, 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 Synthesis Example 516: 5-Chloro-l- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3—capboxamide)
5-클로로 -N ; 4ᅳ플루오로페네틸) -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3ᅳ 카르복스아미드를 디메틸포름아미드에 녹인 후， 4-에틸 벤질 클로라이드， 18-크라운 -6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =67%)  5-chloro-N; 4'fluorophenethyl) -2-oxo '1, 2-dihydroquinoline-3' carboxamide was dissolved in dimethylformamide, 4-ethyl benzyl chloride, 18-crown-6 and potassium carbonate were added together. Stir at room temperature for 12 hours (yield = 67%)
¾ NM (400MHz, CDC13) 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 합성예 517: 5-클로로 -N-(4-플루오로페네틸) -l-(4ᅳ아이소프로필벤질 )-2- 옥소 -1 , 2-디하이드로퀴놀린 -3ᅳ카르복스아미드 ¾ NM (400 MHz, CDC1 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), 1.18 (t, 3H), MASS = 462.85 Synthesis Example 517: 5-chloro -N- (4-fluorophenethyl) -l- (4'isopropylbenzyl) -2-oxo-1,2-dihydroquinoline-3'carboxamide
5-클로로 -N-(4-플루오로페네틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ 카르복스아미드를 디메틸포름아미드에 녹인 후， 4—아이소프로필 벤질 클로라이드, 18—크라운—6， 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =63%)  After dissolving 5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3'carboxamide in dimethylformamide, 4—isopropyl benzyl chloride, 18—crown —6 ， Potassium carbonate was added together and stirred at room temperature for 12 hours (yield = 63%).
¾ NMR (400MHz, CDC13) 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)ᅳ 1.19 (d, 6H), MASS= 476.55 합성예 518: 5-클로로 -N-(4-플루오로페네틸) -l-(4-나이트로벤질 )-2-옥소- 1， 2-디하이드로퀴놀린 -3-카르복스아미드 ¾ NMR (400 MHz, CDC1 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, 1H) ᅳ 1.19 (d, 6H), MASS = 476.55 Synthesis Example 518: 5-chloro -N- (4-fluorophenethyl) -l- (4-nitrobenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide
5-클로로 -N-(4-플루오로페네틸) -2-옥소— 1， 2-디하이드로퀴놀린 -3- 카르복스아미드를 ' 디메 ¾포름아미드에 녹인 후, 4ᅳ나이트로 벤질 브로마이드， 18-크라운ᅳ 6， 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =73%). 5-Chloro-N- (4-fluorophenethyl) -2-oxo—1,2-dihydroquinoline-3-carboxamide in ' dimetha¾formamide, followed by 4' nitrobenzyl bromide, 18 Crown 6 and potassium carbonate were added together and stirred at room temperature for 12 hours (yield = 73%).
¾ NMR( 400MHz, CDCI3) 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 합성예 519: 5-클로로 -N-(4-플루오로페네틸) -l-(4-메록시벤질) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복스아미드 ¾ NMR (400 MHz, CDCI 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, 6H), 7.08 (d, 1H), 5.66 (s, 1H), 3.73 (dd, 2H), 2.95 (t, 2H), MASS = 479.23 Synthesis Example 519: 5-chloro-N- (4-fluorofe Netyl) -l- (4-methoxybenzyl) -2-oxo-1,2- Dihydroquinoline-3-carboxamide
5-클로로 -N-(4-플루오로페네틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복스아미드를 디메틸포름아미드에 녹인 후， 4-메특시 벤질 클로라이드， 5-chloro-N- (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide was dissolved in dimethylformamide, 4-methoxybenzyl chloride,
18-크라운 -6, 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =77%). 18-crown-6 and potassium carbonate were added together and stirred at room temperature for 12 hours (yield = 77%).
Έ NM (400MHz, CDC13) δ 9.85(s, 1H), 9.42(s, 1H), 7.44(t, 1H),M NM (400 MHz, CDC1 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 )ᅳ2-옥소 -l-(4- (트라이플루오 로메특시 )벤질) -1， 2-디하이드로퀴놀린 -3-카르복스아미드 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 Synthesis Example 520; 5-Chloro-N- (4-fluorophenethyl) ᅳ 2-oxo-l- (4- (trifluoromepoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide
5-클로로 -N—( 4-플루오로페네틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복스아미드를 메틸포름아미드에 녹인 후, 4-메특시 벤질 클로라이드， 18-크라운 -6， 포타슘 카보네이트를 같이 넣고 실온에서 12시간 교반하였다 (수율 =69¾ .  5-Chloro-N— (4-fluorophenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide in methylformamide, then 4-methoxybenzyl chloride, 18-crown -6, potassium carbonate was added together and stirred for 12 hours at room temperature (yield = 69¾.
¾ NMR (400MHz, CDC13) 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. 합성예 521: l-(4-에틸벤질) -N-(4ᅳ플루오로펜에틸)ᅳ 5-니트로 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 ¾ NMR (400 MHz, CDC1 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, 1H), 3.73 (dd, 2H), 2.95 (t ( 1H), MASS = 518.36. Synthesis Example 521: l- (4-ethylbenzyl) -N- (4'fluorophenethyl) ᅳ 5-nitro 2-oxo-1,2-dihydroquinoline-3-carboxamide
1-(4-에틸벤질 )-5—니트로 -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카르복실릭 애시드 (1 誦 ol)를' DMF(2 mL)에 용해시켰다. DIPEAO 瞧 ol), 2- (4- 플루오로페닐)에탄아민 (1.5 隱 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 등안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다 (수율 =53%). 1- (4-ethylbenzyl) -5-nitro-2ioxo-1,2-dihydroquinoline-3-carboxylic acid (1xol) was dissolved in ' DMF (2 mL). DIPEAO 瞧 ol), 2- (4-fluorophenyl) ethanamine (1.5 隱 ol) and PyBop (2 瞧 ol) were added to the reaction mixture. The mixture was stirred for 3 hours at room temperature. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1870 compound (yield = 53%).
¾ NMR(400 MHz, CDC13)6 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(sᅳ 2H), 3.55(m, 2H), 2.83(m, 2H), 2.60(m, 2H), 1.25(s, 3H) MASS=473.18 합성예 522: N-(4-풀루오로펜에틸) -1— (4-이소프로필벤질) -5-니트로 -2—옥소- 1， 2-디하이드로퀴놀린 -3-카르복사마이드) ¾ NMR (400 MHz, CDC1 3 ) 6 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 ᅳ 2H), 3.55 (m, 2H), 2.83 (m, 2H), 2.60 (m, 2H), 1.25 (s, 3H) MASS = 473.18 Synthesis Example 522: N- (4-Pluorofenethyl) -1— (4-isopropylbenzyl) -5-nitro-2—oxo-1,2-dihydroquinoline-3-carboxamide)
1-(4-이소프로필벤질 )-5-니트로 -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3- 카르복실릭 애시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 2-(4-플루오로페닐)에탄아민 (1.5 mmol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하고 흔합물을 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-2ioxo-l, 2-dihydroquinoline-3-carboxylic acid (1 mmol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1870 compound (yield = 67%).
1HNMR(400MHz,CDCl3)8 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H),1 HNMR (400 MHz, CDCl 3 ) 8 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) . MASS=487.19 합성예 523: N-(4-플루오로펜에틸) -5-니트로 -l-(4-니트로벤질) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 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) MASS = 487.19 Synthesis Example 523: N- (4-fluorophenethyl) -5-nitro-l- (4-nitrobenzyl) 2-oxo-1,2-dihydroquinoline-3-carboxamide
5-니트로 -1-(4-니트로벤질) -2-옥소 -1， 2-디하이드로퀴놀린— 3-카르복 실릭애시드 (1 画 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 画 ol), 2- (4- 플루오로페닐)에탄아민 (1.5 mmol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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 (ol) was dissolved in DMF (2 mL). DIPEA (3 'ol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2' ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the resulting residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1870 compound (yield = 69)).
¾ 匪 R (400 MHz, CDC13)5 8,57 (s, 1H), 8.04 (d, 1H), 7.95 (d,¾ 匪 R (400 MHz, CDC1 3 ) 5 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 합성예 524: 5-아미노 -N-(4-브로모펜에틸 )ᅳ1-(4-메톡시벤질) -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드) 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 Synthesis Example 524: 5-amino-N- (4-bromophenethyl) ᅳ 1- (4-methoxybenzyl) -2-oxo-1,2-dihydro Quinoline-3-carboxamide)
5-아미노 -1-(4-메톡시벤질) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카르복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 薩 ol), 2-(4-브로모페닐)에탄아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1422화합물을 수득하였다 (수율 =59%). 5-amino-1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 隱 ol) was dissolved in DMF (2 mL). DIPEA (3 薩 ol), 2- (4-bromophenyl) ethanamine (1.5 mmol) and PyBop (2 隱 ol) were added to the reaction mixture. Added. The mixture was stirred at room temperature for 3 hours and the resulting residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1422 compound (yield = 59%).
1HNMR(400MHz,CDCl3)6 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 합성예 525: l-(4-메톡시벤질) -5-니트로 -2-옥소 -N-펜에틸 -1,2-디하이 드로퀴놀린 -3-카르복사마이드 1 HNMR (400MHz, CDCl 3 ) 6 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 Synthesis Example 525: l- (4-methoxybenzyl) -5-nitro-2-oxo-N-phenethyl-1,2-dihydrodroquinoline-3-carboxamide
1-(4-메특시벤질 )-5-니트로ᅳ 2—옥소 -1 , 2-디하이드로퀴놀린 -3- 카르복실릭 애시드 (1 画 ol)를 DMF(2 iiiL)에 용해시켰다. DIPEA(3 隱 ol), 페닐에타나민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 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-nitrosene 2—oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 × ol) was dissolved in DMF (2 iiiL). DIPEA (3 μL ol), Phenylethanamine (1.5 mmol) and PyBop (2 μL ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the resulting residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1422 compound (yield = 67%).
¾匪 ( 400MHz ,CDC13 )δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H)，¾ 匪 (400MHz, CDC1 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), 7.24(m, 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 * 합성예 526: N-(4-플루오로펜에틸) -l-(4-메록시벤질) -5-니트로 -2-옥소 -1,2- 디하이드로퀴놀린 -3-카르복사마이드 7.12 (dd, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.55 (m, 2H), 2.83 (m, 2H). MASS = 457.16 Synthesis Example 526 N- (4-fluorophenethyl) -1- (4-methoxybenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide
1ᅳ (4-메록시벤질 )-5-니트로 -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3- 카르복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 睡 ol), 2-(4-플루오로페닐)에탄아민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1802화합물을 수득하였다 (수율 =69%).  1 '(4-Moxybenzyl) -5-nitro-2-oxox 1, 2-dihydroquinoline-3-carboxylic acid (1x ol) was dissolved in DMF (2 mL). DIPEA (3 mu ol), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1802 compound (yield = 69%).
¾NMR (400MHz, CDC13 )δ 8.57(s, 1H), 8.04(d, 1H), 7.95(d, 1H),¾NMR (400MHz, CDC1 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 -l-(4- (트리플루오로메특시)벤질) - 1， 2-디하이드로퀴놀린 -3-카르복사마이드 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 Synthesis Example 527: 5-Nitro-2-oxo-N-phenethyl-1-(4- (trifluoromepoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide
5-니트로 -2-옥소ᅳ1-(4- (트리플루오로메특시)벤질) -1,2—디하이드로퀴 놀린 -3-카르복실릭애시드 (1 瞧 ol)를 DMF(2 iiiL)에 용해시켰다. DIPEA(3 隱 ol), 2ᅳ페닐에타나민 (1.5 誦 ol) 및 PyBop(2 瞧 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토 그래프로 정제하여 LDD1843 ^합물을 수득하였다 (수율 =6») .  5-nitro-2-oxoXl- (4- (trifluoromepoxy) benzyl) -1,2-dihydroquinoline-3-carboxylic acid (1xol) was added to DMF (2 iiiL). Dissolved. DIPEA (3 'ol), 2'phenylethanamine (1.5' ol) and PyBop (2 'ol) were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and the resulting residue was extracted with ethyl acetate and water. Purification was then performed by silica gel chromatography to give the LDD1843 ^ complex (yield = 6 »).
匪 R(400MHz,CDCl3)5 - 8.57(s, IH), 8.04(d, 1H), 7.95(d, 1H) , 7.57(t, IH), 7.40(dd, 2H) , 7.39(dd, 2H), 7.29(dd, 2H), 7.24(m, IH), 7.12(dd, 2H), 4.94(s, 2H)ᅳ 3.55(m, 2H), 2.83(m, 2H). MASS=511.14 합성예 528: (N-(4-플루오로펜에틸) -5-니트로 -2-옥소 -l-(4- (트리플루오로 메톡시)벤질) -1，2-디하이드로퀴놀린 -3-카르복사마이드) (R (400MHz, CDCl 3 ) 5-8.57 (s, IH), 8.04 (d, 1H), 7.95 (d, 1H), 7.57 (t, IH), 7.40 (dd, 2H), 7.39 (dd, 2H ), 7.29 (dd, 2H), 7.24 (m, IH), 7.12 (dd, 2H), 4.94 (s, 2H) ᅳ 3.55 (m, 2H), 2.83 (m, 2H). MASS = 511.14 Synthesis Example 528: (N- (4-fluorophenethyl) -5-nitro-2-oxo-l- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline 3-carboxamide)
5-니트로 -2-옥소 -1-(4- (트리플루오로메록시 )벤질 ) -1， 2-디하이드로 퀴 놀린 -3ᅳ카르복실릭애시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEM3 麵 ol), 2-(4-플루오로페닐)에타나민 (1.5 隱 ol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하 다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다 (수율 =7»).  Dissolve 5-nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3'carboxylic acid (1 'ol) in DMF (2 mL) I was. DIPEM3 麵 ol), 2- (4-fluorophenyl) ethanamine (1.5 隱 ol) and PyBop (2 mmol) are 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. Then purified by silica gel chromatography to give the LDD1870 compound (yield = 7 »).
¾讓 ( 400MHz, CDC13 )δ 8.52(s, 1H)， 8.00(d, IH), 7.95(d, IH) , 7.51(t, IH), 7.40(dd, 2H), 7.33(dd, 2H), 7.29(dd, 2H), 7.22(m, IH), 7.12(dd, 2H), 4.94(s, 2H), 3.55(m, 2H), 2.87(m, IH), MASS=529.13 합성예 529: l-(4-이소프로필벤질) -5-니트로 -2-옥소 -N-펜에틸 -1，2-디하이 드로퀴놀린 -3-카르복사마이드  ¾ 讓 (400MHz, CDC13) δ 8.52 (s, 1H), 8.00 (d, IH), 7.95 (d, IH), 7.51 (t, IH), 7.40 (dd, 2H), 7.33 (dd, 2H), 7.29 (dd, 2H), 7.22 (m, IH), 7.12 (dd, 2H), 4.94 (s, 2H), 3.55 (m, 2H), 2.87 (m, IH), MASS = 529.13 Synthesis Example 529: l -(4-isopropylbenzyl) -5-nitro-2-oxo-N-phenethyl-l, 2-dihydrodroquinoline-3-carboxamide
1-(4-이소프로필벤질 )-5—니트로ᅳ 2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카르복실릭 애시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA(3 mmol), 2-(4-플루오로페닐)에탄아민 (1.5 mmol) 및 PyBop(2 麵 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하고 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카 겔 크로마토그래프로 정제하여 LDD1870화합물을 수득하였다 (수율 =73%). 1- (4-isopropylbenzyl) -5—nitrosene 2-oxo-1, 2-dihydroquinoline-3-carboxylic acid (1 × ol) was dissolved in DMF (2 mL). DIPEA (3 mmol), 2- (4-fluorophenyl) ethanamine (1.5 mmol) and PyBop (2 μL) were added to the reaction mixture. Added. The mixture was stirred at room temperature for 3 hours and the resulting residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to give the LDD1870 compound (yield = 73%).
1HNMR(400MHz,CDCl3)6 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 ) 6 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, 6 H). MASS = 469.20
【표 1】 Table 1
합성된 화합물의 구조 및 분광학 데이터 (합성예 1-510)  Structure and Spectroscopy Data of Synthesized Compound (Synthesis Example 1-510)
Figure imgf000239_0001
Figure imgf000240_0001
Figure imgf000241_0001
Figure imgf000239_0001
Figure imgf000240_0001
Figure imgf000241_0001
Figure imgf000242_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7
Figure imgf000242_0001
// : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000243_0001
Figure imgf000243_0001
l-(4-메톡시펜에틸) - XH NMR (400 MHz, CDCI3) δ 8.63 (s, 368.10 5-니트로 -2-옥소 -1,2- IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, 디하이드로퀴놀린ᅳ 3- IH), 7.18 (dd, 2ᅢ), 6.94 (dd, 2H), 4.62 카르복실릭 애시드 (s, 2H), 3.83 (s, 3H), 3.09 (s, 2H), l- (4-methoxyphenethyl) -X H NMR (400 MHz, CDCI 3 ) δ 8.63 (s, 368.10 5-nitro-2-oxo-1,2-IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, dihydroquinoline® 3-IH), 7.18 (dd, 2 ′), 6.94 (dd, 2H), 4.62 carboxylic acid (s, 2H), 3.83 (s, 3H ), 3.09 (s, 2H),
Figure imgf000244_0001
Figure imgf000244_0001
1-머 | ¾-5-니트로 -2- JH NMR (400 MHz, CDCI3) δ 8.63 (s, 248.041-mer | ¾-5-nitro-2- J H NMR (400 MHz, CDCI 3 ) δ 8.63 (s, 248.04
H fYN¾ 옥소 -1,2- IH), 8.04 (s, IH), 7.95 (d, IH), 7.57 (t, ax 디하이드로퀴놀린 -3- IH), 3.44 (s, 3H) H fY N¾ oxo-1,2-IH), 8.04 (s, IH), 7.95 (d, IH), 7.57 (t, ax dihydroquinoline-3- IH), 3.44 (s, 3H)
카르복실릭 애시드  Carboxylic Acid
H  H
1-에릴 -5—니트로 -2- !H NMR (400 MHz, CDCI3) δ 8.63 (s, 262.06 니人 옥소 -1,2- IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, 1-Eryl-5—Nitro-2- ! H NMR (400 MHz, CDCI3) δ 8.63 (s, 262.06 niogen oxo-1,2-IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t,
디하이드로퀴놀린 -3- IH), 4.28 (s, 2H), 1.31 (s, 3H)  Dihydroquinoline-3-IH), 4.28 (s, 2H), 1.31 (s, 3H)
ox 카르복실릭 애시드 ox carboxylic acid
H  H
1—아세릴 -5-니트로- lH NMR (400 MHz, CDCI3) δ 8.63 (s, 276.041—Aceryl-5-nitro- l H NMR (400 MHz, CDCI3) δ 8.63 (s, 276.04
2-옥소— 1,2- IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, 디하이드로퀴놀린 -3- IH), 4.28 (s, 2H), 1.31 (s, 3H) 2-oxo— 1,2-IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, dihydroquinoline-3- IH), 4.28 (s, 2H), 1.31 (s, 3H )
카르복실릭 애시드  Carboxylic Acid
H H
5-니트로 -2-옥소 -1- :H NMR (400 MHz, CDCI3) δ 8.63 (s, 290.05 프로피오닐 -1,2- IH), 8.64 (d, IH), 7.95 (s, IH), 7.57 (t, 디하이드로퀴놀린 -3- IH), 2.32 (s, 2H), 1.02 (5, 3H) 5-nitro-2-oxo-1- : H NMR (400 MHz, CDCI3) δ 8.63 (s, 290.05 propionyl-1,2-IH), 8.64 (d, IH), 7.95 (s, IH), 7.57 (t, dihydroquinoline-3-IH), 2.32 (s, 2H), 1.02 (5, 3H)
카르복실릭 애시드  Carboxylic Acid
H  H
1- (메톡시카르보닐) - JH NMR (400 MHz, CDCI3) δ 8.63 (s, 292.03 5-니트로 -2-옥소 -1,2- IH), 8.64 (d, IH), 7.95 (s, IH), 7.57 (t, 디하이드로퀴놀린 -3- IH), 1.02 (s, 3H) 1- (methoxycarbonyl) -J H NMR (400 MHz, CDCI3) δ 8.63 (s, 292.03 5-nitro-2-oxo-1,2-IH), 8.64 (d, IH), 7.95 (s, IH), 7.57 (t, dihydroquinoline-3-IH), 1.02 (s, 3H)
카르복실릭 애시드  Carboxylic Acid
1- (사이클로펜타 -1,3- JH NMR (400 MHz, CDCI3) δ 8.63 (s, 312.07 디엔 -1-일메틸 )-5- IH), 8.04 (d, IH), 7.95 (d, IH), 7.57 (t, 니트로 -2-옥소 -1,2- IH), 6.5 (d, IH), 6.4 (m, 2H), 3.63 (s, 디하이드로퀴놀린 -3- 2H), 2.9 (s, IH) 1- (cyclopenta-1,3- J H NMR (400 MHz, CDCI3) δ 8.63 (s, 312.07 diene-1-ylmethyl) -5-IH), 8.04 (d, IH), 7.95 (d, IH ), 7.57 (t, nitro-2-oxo-1,2-IH), 6.5 (d, IH), 6.4 (m, 2H), 3.63 (s, dihydroquinoline-3- 2H), 2.9 (s, IH)
카르복실릭 애시드 Carboxylic Acid
Figure imgf000244_0002
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7
Figure imgf000244_0002
// : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000245_0001
Figure imgf000245_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000246_0001
Figure imgf000246_0001
Z/-S00/:S2MI>d/ 6/.SS0SS OZAV. Z / -S00 / : S2MI > d / 6 / .SS0SS OZAV.
Figure imgf000247_0001
Figure imgf000247_0001
Figure imgf000248_0001
Figure imgf000248_0001
8½ 8½
Figure imgf000249_0001
Figure imgf000249_0001
ZLZ600/ lOZW^/13d 6.C0S0/ST0i ΟΛ\
Figure imgf000250_0001
ZLZ600 / lOZW ^ / 13d 6.C0S0 / ST0i ΟΛ \
Figure imgf000250_0001
Figure imgf000251_0001
Figure imgf000251_0001
Figure imgf000252_0001
Figure imgf000252_0001
/ z/-soo1s§/:ll>d 6/.SS/ O0SSZAV7 / z / -s oo1 s§ / : l l > d 6 / .SS / O0 S S Z A V7
Figure imgf000253_0001
Figure imgf000253_0001
-s//uoonosMld/ 6/.SS0SSZ OAV -s // uoon o sMld / 6 / .S S0S S Z OAV
Figure imgf000254_0001
Figure imgf000254_0001
Figure imgf000255_0001
Figure imgf000255_0001
iz-so//uotssMd/.SS0SSZ OAV iz -so // uo t ss M d / .S S0S S Z OA V
Figure imgf000256_0001
Figure imgf000256_0001
Figure imgf000257_0001
Figure imgf000257_0001
Figure imgf000258_0001
Figure imgf000258_0002
Figure imgf000258_0001
Figure imgf000258_0002
/ zz-sooSOS/Mld 6/.S/ OS0SSZAV / zz-sooS O S / M ld 6 / .S / OS0SSZAV
Figure imgf000259_0001
Figure imgf000259_0001
z/-soo/:¾l>d-SS/ O0S10ZAV z / -soo / : ¾l> d-SS / O0S10ZAV
Figure imgf000260_0001
Figure imgf000260_0001
/:/ O K-Z6001S2M>d 6/.SS0SSZAV7 / : / O K-Z600 1 S2M> d 6 / .S S0 SSZAV 7
Figure imgf000261_0001
Figure imgf000261_0001
//:/ O Ζ/.Ζ6001Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O Ζ / .Ζ600 1Ϊ 02ΜΙ><ί 6 / .S S0 SSZAV 7
Figure imgf000262_0001
Figure imgf000262_0001
Figure imgf000263_0001
Figure imgf000263_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000264_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000266_0001
992 992
Figure imgf000267_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7
Figure imgf000267_0001
// : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000268_0001
Figure imgf000268_0001
892 892
Figure imgf000269_0001
/.ζ6001Ϊ02Μ/ O,SS0Ssi7
Figure imgf000269_0001
/ . ζ6001Ϊ 02Μ / O , S S0S s i7
Figure imgf000270_0001
Figure imgf000270_0001
//:/ O1Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O 1Ϊ 02ΜΙ>< ί 6 / .SS0SSZAV 7
Figure imgf000271_0001
Figure imgf000271_0001
z/.z60//:0is2Ml><i/ 6/.ssoss£ OAV z / .z60 // : 0 i s2Ml ><i / 6 / .ssoss £ OAV
Figure imgf000272_0001
Figure imgf000272_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000273_0001
Figure imgf000273_0001
//:/ O Ζ/.Ζ6001Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O Ζ / .Ζ600 1Ϊ 02ΜΙ><ί 6 / .SS0SSZAV 7
Figure imgf000274_0001
Figure imgf000274_0001
Figure imgf000275_0001
Figure imgf000275_0002
Figure imgf000275_0001
Figure imgf000275_0002
Figure imgf000276_0001
Figure imgf000276_0001
9LZ 9LZ
Figure imgf000277_0001
/ Ζ/.Ζ600Η02Ή/:1><Ι-S/ OS0S10ZAV
Figure imgf000277_0001
/ Ζ / .Ζ600Η 0 2Ή / : 1>< Ι-S / OS0S10ZA V
Figure imgf000278_0001
Figure imgf000278_0001
//:/ O Ζ/.Ζ6001Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O Ζ / .Ζ600 1Ϊ 02ΜΙ><ί 6 / .SS0SSZAV 7
Figure imgf000279_0001
Figure imgf000279_0001
Figure imgf000280_0001
Figure imgf000280_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000281_0001
Figure imgf000281_0001
(s, (s,
(s, (s,
Figure imgf000282_0001
//:/ O K-Z6001S2MI>d 6/.SS0SSZAV7 (s, (s,
Figure imgf000282_0001
// : / O K-Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000283_0001
Figure imgf000283_0001
Figure imgf000284_0001
Figure imgf000284_0001
//: Z/-Z6001S2MI>d/ O 6/.SS0SSZAV7 // : Z / -Z600 1 S2MI > d / O 6 / .SS0SSZAV 7
Figure imgf000285_0001
Figure imgf000285_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000286_0001
Figure imgf000286_0001
Figure imgf000287_0001
Figure imgf000287_0001
//:/ O1Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O 1Ϊ 02ΜΙ>< ί 6 / .S S0S S Z A V7
Figure imgf000288_0001
Figure imgf000288_0001
// O1Ϊ02Μ 6/.SS0SSZAV7 // O 1Ϊ 02Μ 6 / .S S0S S Z A V7
Figure imgf000289_0001
Figure imgf000289_0001
682 682
Figure imgf000290_0001
Figure imgf000290_0001
's) 8S.89 (HDQD 'ΖΗ1ΛΙ OOt^) ¾ΙΛΙΝ HT -(iii¾Iltab-9¾-T 's) 8S.89 (HDQD' Ζ Η1ΛΙ OOt ^) ¾ΙΛΙΝ H T - (iii¾Iltab-9¾-T
ZLZ600/ lOZ ^/13d 6Z.£0S0/S10Z OAV ZLZ600 / LOZ ^ / 13d 6Z. £ 0S0 / S10Z OAV
/ O-SS0SSZAV//:d iz600302¾l> / OS S0 SSZAV // : d iz6003 0 2¾ l >
Figure imgf000291_0001
Figure imgf000291_0001
//:/ O1Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O 1Ϊ 02ΜΙ>< ί 6 / .SS0 S S Z A V7
Figure imgf000292_0001
Figure imgf000292_0001
//:/ O1Ϊ02ΜΙ><ί 6/.SS0SSZAV7 //: / O 1Ϊ 02ΜΙ>< ί 6 / .SS0SSZAV 7
Figure imgf000293_0001
Figure imgf000293_0001
Figure imgf000294_0001
V6Z
Figure imgf000294_0001
V6Z
Figure imgf000295_0001
Figure imgf000296_0001
Figure imgf000297_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7
Figure imgf000295_0001
Figure imgf000296_0001
Figure imgf000297_0001
// : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000298_0001
Figure imgf000298_0001
N-(3,4-디에틸벤질) - XH NMR (400 MHz, CDCI3) δ 8.28 (s, 334.17 N- (3,4-diethylbenzyl) -X H NMR (400 MHz, CDCI 3 ) δ 8.28 (s, 334.17
2-옥소 -1,2- IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 2-oxo-1,2-IH), 8.14 (d, IH), 8.03 (s, IH, -NH),
421 디하이드로퀴놀린 -3- 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t, 421 dihydroquinoline-3-8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t,
카복사마이드 IH), 7.14 (t, IH), 7.12 (d, IH), 7.11 (s, Carboxamide IH), 7.14 (t, IH), 7.12 (d, IH), 7.11 (s,
H , H,
IH), 7.00 (d, IH), 2.60 (m, 4H), 1.25 (s, 6H)  IH), 7.00 (d, IH), 2.60 (m, 4H), 1.25 (s, 6H)
N-(3,4-디메틸1벤질) - H NMR (400 MHz, CDCI3) δ 8.28 (s, 306.14 2-옥소 -1,2- IH), 8.14 (d, IH), 8.03 (s, IH, -NH), 디하이드로퀴놀린 -3- 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t,N- (3,4-dimethyl 1 benzyl) -H NMR (400 MHz, CDCI3) δ 8.28 (s, 306.14 2-oxo-1,2-IH), 8.14 (d, IH), 8.03 (s, IH, -NH), dihydroquinoline-3-8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t,
422 422
카복사마이드 IH), 7.14 (t, IH), 6.99 (d, IH), 6.98 (s,  Carboxamide IH), 7.14 (t, IH), 6.99 (d, IH), 6.98 (s,
IH), 6.92 (d, IH), 4.34 (m, 2H), 2.34 (s, 6H)  IH), 6.92 (d, IH), 4.34 (m, 2H), 2.34 (s, 6H)
N-(3,4- JH NMR (400 MHz, CDCI3) δ 8.28 (s, 324.11 디하이드록시펜에틸) IH), .8.14 (d, IH), 8.03 (s, IH, -NH), -2—옥소 -1,2- 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t,N- (3,4- J H NMR (400 MHz, CDCI3) δ 8.28 (s, 324.11 dihydroxyphenethyl) IH), .8.14 (d, IH), 8.03 (s, IH, -NH),- 2—oxo-1,2- 8.0 (s, IH, -NH), 7.36 (d, IH), 7.31 (t,
423 423
디하이드로퀴놀린 -3- IH), 7.14 (t, IH), 6.86 (s, IH), 6.68 (d, 카복사마이드 IH), 6.73 (d, IH), 5.35 (s, 2H, -OH),  Dihydroquinoline-3-IH), 7.14 (t, IH), 6.86 (s, IH), 6.68 (d, carboxamide IH), 6.73 (d, IH), 5.35 (s, 2H, -OH),
3.55 (m, 2H), 2.83 (m, 2H)  3.55 (m, 2H), 2.83 (m, 2H)
5-(2-(4- l NMR (400 MHz, CDCI3) δ 8.28 (s, 547.21 벤질페닐)아세트아미 IH), 8.03 (s, IH, -NH), 8.0 (s, IH, - 도) -N-(3,4- NH), 7.88 (m, 2H), 7.29 (t, IH), 7.33 ᄂ ■= 디하이드록시펜에릴) (dd, 2H), 7.26 (t, IH), 7.23 (dd, 2H),5- (2- (4- L NMR (400 MHz, CDCI3) δ 8.28 (s, 547.21 benzylphenyl) acetami IH), 8.03 (s, IH, -NH), 8.0 (s, IH,-degrees)- N- (3,4-NH), 7.88 (m, 2H), 7.29 (t, IH), 7.33 b dihydroxypheneryl) (dd, 2H), 7.26 (t, IH), 7.23 ( dd, 2H),
424 424
-2-옥소—1,2- 7.11 (m, 4H), 6.86 (s, IH), 6.73 (d, 디하이드로퀴놀린 -3- IH), 6.68 (d, IH), 5.35 (s, 2H, -OH), 카복사마이드 3.96 (m, 2H), 3.55 (m, 2H), 2.83 (m,  2-oxo—1,2- 7.11 (m, 4H), 6.86 (s, IH), 6.73 (d, dihydroquinoline-3- IH), 6.68 (d, IH), 5.35 (s, 2H,- OH), carboxamide 3.96 (m, 2H), 3.55 (m, 2H), 2.83 (m,
2H)  2H)
N-(3,4- JH NMR (400 MHz, CDCI3) δ 8.28 (s, 395.15 디하이드록시펜에릴) IH), 8.03 (s, IH, -NH), 8.0 (s, IH, - -2-옥소 -5- NH), 7.88 (m, 2H), 7.29 (t, IH), 7.23N- (3,4- J H NMR (400 MHz, CDCI3) δ 8.28 (s, 395.15 dihydroxypheneryl) IH), 8.03 (s, IH, -NH), 8.0 (s, IH,-- 2-oxo-5- NH), 7.88 (m, 2H), 7.29 (t, IH), 7.23
425 프로피온아미도 -1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 (d, 425 propionamido-1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 (d,
디하이드로퀴놀린 -3- IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), 카복사마이드 3.55 (m, 2H), 2.83 (m, 2H), 2.45 (m,  Dihydroquinoline-3-IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), carboxamide 3.55 (m, 2H), 2.83 (m, 2H), 2.45 (m,
2H), 1.02 (s, 3H)  2H), 1.02 (s, 3H)
5-butyramido-N- JH NMR (400 MHz, CDCI3) δ 8.28 (s, 409.16 (3,4- IH), 8.03 (s, IH, -NH), 8.0 (s, IH, - 디하이드록시펜에릴) NH), 7.88 (m, 2H), 7.29 (t, IH), 7.235-butyramido-N- J H NMR (400 MHz, CDCI3) δ 8.28 (s, 409.16 (3,4-IH), 8.03 (s, IH, -NH), 8.0 (s, IH, -dihydroxyphen Aryl) NH), 7.88 (m, 2H), 7.29 (t, IH), 7.23
426 -2-옥소 -1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 (d, 426-2-oxo-1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 (d,
디하이드로퀴놀린 -3- IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), 카복사마이드 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m,  Dihydroquinoline-3-IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), carboxamide 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m,
2H), 1.78 (m, 2H), 0.9 (s, 3H)  2H), 1.78 (m, 2H), 0.9 (s, 3H)
N-(3,4- JH NMR (400 MHz, CDCI3) δ 8.28 (s, 423.18 디하이드록시펜에릴) IH), 8.03 (s, IH, -NH), 8.0 (s, IH, - -2—옥소 -5— NH), 7.88 (m, 2H), 7.29 (t, IH), 7.23 펜탄아미도 -1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 (d,N- (3,4- J H NMR (400 MHz, CDCI3) δ 8.28 (s, 423.18 dihydroxypheneryl) IH), 8.03 (s, IH, -NH), 8.0 (s, IH,-- 2—oxo-5—NH), 7.88 (m, 2H), 7.29 (t, IH), 7.23 pentanamido -1,2- (s, IH, -NH), 6.86 (s, IH), 6.68 ( d,
427 427
디하이드로퀴놀린 -3- IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), 카복사마이드 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m,  Dihydroquinoline-3-IH), 6.73 (d, IH), 5.35 (s, 2H, -OH), carboxamide 3.55 (m, 2H), 2.83 (m, 2H), 2.39 (m,
2H), 1.63 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H)
Figure imgf000300_0001
2H), 1.63 (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H)
Figure imgf000300_0001
Figure imgf000301_0001
Figure imgf000301_0001
IOC IOC
Figure imgf000302_0001
20C
Figure imgf000302_0001
20C
Figure imgf000303_0001
Figure imgf000303_0001
ZLZ600/ lOZW^/lDd 6.εθ£0/£ΤΟΙ ΟΛ\
Figure imgf000304_0001
ZLZ600 / lOZW ^ / lDd 6.εθ £ 0 / £ ΤΟΙ ΟΛ \
Figure imgf000304_0001
Figure imgf000305_0001
Figure imgf000305_0001
Figure imgf000306_0001
90C
Figure imgf000306_0001
90C
Figure imgf000307_0001
Figure imgf000308_0001
0 ' 3- (에틸 (4— JH NMR (400 MHz, CDCI3) δ 8.14 (d, 290그4' 비닐패닐)아미노)쿠 1 IH), 8.02 (dd, 2H), 8.0 (s, IH, -NH), 놀린 -2(1H)-온 7.68 (dd, 2H), 7.36 (d, IH), 7.31 (t,
Figure imgf000307_0001
Figure imgf000308_0001
0 3- (ethyl (4- J H NMR (400 MHz , CDCI 3) δ 8.14 (d, 290 that 4 'paenil vinyl) amino) Pico 1 IH), 8.02 (dd, 2H), 8.0 (s, IH , -NH), Nolin -2 (1H) -one 7.68 (dd, 2H), 7.36 (d, IH), 7.31 (t,
IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s,  IH), 7.14 (t, IH), 6.63 (s, IH), 5.61 (s,
H IH), 5.18 (s, IH), 1.31 (s, 3H)  H IH), 5.18 (s, IH), 1.31 (s, 3H)
H H
0 3-((3,4- !H NMR (400 MHz, CDCI3) δ 8.14 (d, 264.13 디메릴페닐)아미노) IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 퀴놀린 -2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.86 (d, IH), 0 3-((3,4- ! H NMR (400 MHz, CDCI3) δ 8.14 (d, 264.13 dimerylphenyl) amino) IH), 8.0 (s, IH, -NH), 7.36 (d, IH), Quinolin-2 (1H) -one 7.31 (t, IH), 7.14 (t, IH), 6.86 (d, IH),
6.24 (m, IH), 6.19 (d, IH), 4.0 (s, IH,  6.24 (m, IH), 6.19 (d, IH), 4.0 (s, IH,
H  H
-NH), 2.34 (m, 6H)  -NH), 2.34 (m, 6H)
3-((3,4- XH NMR (400 MHz, CDCI3) δ 8.14 (d, 278.14 디메틸벤질)아미노) IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 퀴놀린 -2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.86 (d, IH), 3-((3,4- X H NMR (400 MHz, CDCI3) δ 8.14 (d, 278.14 dimethylbenzyl) amino) IH), 8.0 (s, IH, -NH), 7.36 (d, IH), quinoline- 2 (1H) -on 7.31 (t, IH), 7.14 (t, IH), 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)  6.24 (m, IH), 6.19 (d, IH), 4.0 (s, IH, -NH), 3.2 (m, 2H), 2.34 (m, 6H)
3-((3,4- !H NMR (400 MHz, CDCI3) δ 8.14 (d, 268.08 디하이드록시페닐)아 IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 미노)퀴놀린 -2(1H)-은 7.31 (t, IH), 7.14 (t, IH), 6.53 (d, IH), 3-((3,4- ! H NMR (400 MHz, CDCI3) δ 8.14 (d, 268.08 dihydroxyphenyl) a IH), 8.0 (s, IH, -NH), 7.36 (d, IH), mino ) Quinoline-2 (1H)-is 7.31 (t, IH), 7.14 (t, IH), 6.53 (d, IH),
5.97 (m, IH), 5.83 (d, IH),  5.97 (m, IH), 5.83 (d, IH),
H  H
3-((3,4- XH NMR (400 MHz, CDCI3) δ 8.14 (d, 282.10 디하이드록시벤질)아 IH), 8.0 (s, IH, -NH), 7.36 (d, IH), 미노)퀴놀린— 2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.53 (d, IH), 3-((3,4- X H NMR (400 MHz, CDCI3) δ 8.14 (d, 282.10 dihydroxybenzyl) aH), 8.0 (s, IH, -NH), 7.36 (d, IH), mino ) Quinoline — 2 (1H) -one 7.31 (t, IH), 7.14 (t, IH), 6.53 (d, IH),
5.97 (m, IH), 5.83 (d, IH), 3.2 (m, 2H)  5.97 (m, IH), 5.83 (d, IH), 3.2 (m, 2H)
H  H
3- ((벤조 [d][l,3] !H NMR (400 MHz, CDCI3)' δ 8그 4 (d, 294.10 디옥솔 -5-일메릴) IH) 8.0 (s, IH, -NH), 7.36 (d, IH), 아미노)퀴놀린 -2(1H)- 7.31 (t, IH), 7.14 (t, IH), 7.03 (m, IH), l l 온 6.81 (d, IH), 6.76 (d, IH), 6.10 (s, IH), 3- ((benzo [d] [l, 3] ! H NMR (400 MHz, CDCI3) ' δ 8G 4 (d, 294.10 dioxol-5-ylmeryl) IH) 8.0 (s, IH, -NH) , 7.36 (d, IH), amino) quinoline-2 (1H)-7.31 (t, IH), 7.14 (t, IH), 7.03 (m, IH), ll on 6.81 (d, IH), 6.76 (d , IH), 6.10 (s, IH),
N上 O H N 上 O H
H 6.07 (m, 2H), 3.92 (m, 2H), 2.0 (s, IH,  H 6.07 (m, 2 H), 3.92 (m, 2 H), 2.0 (s, IH,
-NH)  -NH)
3-((2- H NMR (400 MHz, CDCI3) δ 8.14 (d, 308.12 3-((2-H NMR (400 MHz, CDCI3) δ 8.14 (d, 308.12
(벤조 [d][l,3]디옥솔- IH) 8.0 (s, IH, -NH), 7.36 (d, IH), 5- 7.31 (t, IH), 7.14 (t, IH), 7.03 (m, IH),(Benzo [d] [l, 3] dioxol-IH) 8.0 (s, IH, -NH), 7.36 (d, IH), 5- 7.31 (t, IH), 7.14 (t, IH), 7.03 ( m, IH),
H 일)에릴)아미노)퀴놀 6.81 (d, IH), 6.76 (d, IH), 6.10 (s, IH), Hyl) eryl) amino) quinol 6.81 (d, IH), 6.76 (d, IH), 6.10 (s, IH),
린 -2(1H)-온 6.07 (m, 2H), 3.92 (m, 2H), 3.02 (m,  Lean-2 (1H) -one 6.07 (m, 2H), 3.92 (m, 2H), 3.02 (m,
2H), 2.0 (s, IH, -NH)  2H), 2.0 (s, IH, -NH)
3- ((나프탈롄 -2- XH NMR (400 MHz, CDCI3) δ 8.14 (d, 300.13 일메릴)아미노)퀴놀 IH), 8.01 (d, IH), 8.0 (s, IH, -NH), 린 -2(1H)-온 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH), 3 - ((naphthyl talryen -2- X H NMR (400 MHz, CDCI3) δ 8.14 (d, 300.13 il Merrill) amino) quinol IH), 8.01 (d, IH ), 8.0 (s, IH, -NH), Lean-2 (1H) -one 7.97 (d, IH), 7.94 (d, IH), 7.58 (t, IH),
7.55 (t, IH), 7.46 (m, IH), 7.36 (d,  7.55 (t, IH), 7.46 (m, IH), 7.36 (d,
H IH), 7.31 (t, IH), 7.18 (d, IH), 7.14 (t, IH), 6.10 (s, IH), 4.03 (m, 2H), 2.0 (s, IH, NH) //: i/-soo1s2Ml>d/ O 6/.SS0SSZAV7 H IH), 7.31 (t, IH), 7.18 (d, IH), 7.14 (t, IH), 6.10 (s, IH), 4.03 (m, 2H), 2.0 (s, IH, NH) // : i / -soo 1 s2Ml > d / O 6 / .S S0 SSZAV 7
Figure imgf000310_0001
Figure imgf000310_0001
3- JH NMR (400 MHz, CDCI3) δ 8.14 (d, 216.13 3- J H NMR (400 MHz, CDCI 3 ) δ 8.14 (d, 216.13
(부릴아미노)퀴놀린- IH), 8.0 (s, IH, -NH), 7.36 (d, IH), (Burylamino) quinoline-IH), 8.0 (s, IH, -NH), 7.36 (d, IH),
507 2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH), 507 2 (1H) -on 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH),
2.73 (m, 2H), 2.0 (s, IH, -NH), 1.52  2.73 (m, 2H), 2.0 (s, IH, -NH), 1.52
H  H
(m, 2H), 1.31 (m, 2H), 0.9 (s, 3H)  (m, 2H), 1.31 (m, 2H), 0.9 (s, 3H)
3- JH NMR (400 MHz, CDCI3) δ 8.14 (d, 218.113- J H NMR (400 MHz, CDCI3) δ 8.14 (d, 218.11
((에톡시메릴)아미노) IH), 8.0 (s, IH, -NH), 7.36 (d, IH),((Ethoxymeryl) amino) IH), 8.0 (s, IH, -NH), 7.36 (d, IH),
508 퀴놀린— 2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH), 508 Quinoline—2 (1H) -on 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH),
3.50 (m, 2H), 2.0 (s, IH, -NH), 3.28  3.50 (m, 2H), 2.0 (s, IH, -NH), 3.28
H  H
(m, 2H), 1.10 (s, 3H)  (m, 2H), 1.10 (s, 3H)
3- l NMR (400 MHz, CDCI3) δ 8.14 (d, 234.083- l NMR (400 MHz, CDCI3) δ 8.14 (d, 234.08
( ((에틸티오)메릴)아미 IH), 8.0 (s, IH, -NH), 7.36 (d, IH),(((Ethylthio) meryl) ami IH), 8.0 (s, IH, -NH), 7.36 (d, IH),
509 노)퀴놀린 -2(1H)-온 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH), 509 no) quinoline-2 (1H) -one 7.31 (t, IH), 7.14 (t, IH), 6.10 (s, IH),
3.50 (m, 2H), 2.0 (s, IH, -NH), 3.28  3.50 (m, 2H), 2.0 (s, IH, -NH), 3.28
H  H
(m, 2H), 1.10 (s, 3H)  (m, 2H), 1.10 (s, 3H)
NH2 0 메털 S-아미노 -2- NMR (400 MHz, CDCI3) δ 11.62 (s, 218.07 옥소 -1,2- IH), 8.21 (s, IH, -NH), 7.17 (t, IH),NH 2 0 metal S-amino-2-NMR (400 MHz, CDCI3) δ 11.62 (s, 218.07 oxo-1,2-IH), 8.21 (s, IH, -NH), 7.17 (t, IH),
510 디하이드로퀴놀린 -3- 6.33 (dd, IH), 6.22 (s, IH), 3.77 (s,510 dihydroquinoline-3- 6.33 (dd, IH), 6.22 (s, IH), 3.77 (s,
ᄂ N人 0 카르복실레이트 IH). N human 0 carboxylate IH).
H  H
【표 2】 Table 2
합성된 화합물의 구조 및 분광학 데이터 (합성예 511-529)  Structure and Spectroscopy Data of Synthesized Compound (Synthesis Example 511-529)
Figure imgf000311_0001
Figure imgf000312_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7
Figure imgf000311_0001
Figure imgf000312_0001
// : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000313_0001
Figure imgf000313_0001
Figure imgf000314_0001
Figure imgf000314_0001
합성의 일반적인 과정 General process of synthesis
： 단계 (e-5, h-8)의 일반적 과정과 같음 합성예 530 ： 메틸 1-(4-메특시벤질) -2-옥소 -5-(3-페닐프로파나미노) -1,2- 디하이드로퀴놀린 -3-카복실레이트  : Same as general procedure of step (e-5, h-8) Synthesis Example 530: Methyl 1- (4-methoxybenzyl) -2-oxo-5- (3-phenylpropanamino) -1,2- Dihydroquinoline-3-carboxylate
메틸 5-아미노ᅳ 1-(4ᅳ메특시벤질 )-2-옥소 -1， 2—디하이드로퀴놀린 -3- 카복실레이트 (lmmol), DIPEA 1.5画 ol) 및 하이드로시나모일클로라이드 (1.2隱01)를 C¾Cl' 2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 530 화합물을 수득하였다 (수율 =61%). Methyl 5-amino ᅳ 1- (4 ᅳ mesotoxybenzyl) -2-oxo-1, 2—dihydroquinoline-3-carboxylate (lmmol), DIPEA 1.5 画 ol) and hydrocinamoylchloride (1.2 隱0 1 ) Was stirred for 15 min in 2 mL C¾Cl '. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 530 (yield = 61%).
¾ 匪 R (400 MHz, CDCls) 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, / = 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 ¾ 匪 R (400 MHz, CDCls) 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, / = 12.0 Hz, 1H), 5.48 (s, 2H), 3.96 (s, 3H), 3.75 (s, 3 H), 3.18-3.01 (m, 4 H). MASS = 470.18
합성예 531 ： 메틸 5-(3-사이클로펜틸프로파나미도 )-l-(4-메록시벤질) -2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카복실레이트 Synthesis Example 531: Methyl 5- (3-cyclopentylpropanamido) -l- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylate
메틸 5-아미노 -1-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEA 1.5隱 ol) 및 사이클로펜테인프로피오닐 클로라이드 (1.2隱 ol)를 C¾Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 531 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate (1 'ol), DIPEA 1.5' ol) and cyclopentanepropionyl chloride ( 1.2 μl) was stirred in C¾Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 531 (yield = 61%).
¾匪 R (400 MHz, MeOH-d4) 9.25 (s, 1H), 7.78 (s, 1H), 7.47 (t, J ¾ 匪 R (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, / = 12.0 Hz, 1H), 5.53 (s, 2H), 3.93 (s, 3H), 3.74 (s, 3H) , 2.23-2.18 Cm, 9H) MASS=462.22 합성예 532 ： 메틸 l-(4-메톡시벤질) -2—옥소 -5-(2-페닐아세타미도) -1,2- 디하이드로퀴놀린— 3-카복실레이트 = 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, / = 12.0 Hz, 1H), 5.53 (s, 2H), 3.93 (s, 3H), 3.74 (s, 3H), 2.23-2.18 Cm, 9H) MASS = 462.22 Synthesis Example 532: Methyl l- (4-methoxybenzyl) -2 —Oxo-5- (2-phenylacetamido) -1,2-dihydroquinoline—3-carboxylate
메틸 5- 미노 -1-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실레이트 (1醒 ol), DIPEA 1.5隱 ol) 및 페닐아세틸클로라이드 (1.2隱 ol)를 Methyl 5-mino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate (1 'ol), DIPEA 1.5' ol) and phenylacetylchloride (1.2 'ol )
CH2Cl2(2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예Stir for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . Synthesis Example by Purification by Silica Gel Column Chromatography
532 화합물을 수득하였다 (수율 =61%). 532 compound was obtained (Yield = 61%).
¾ NMR (400丽 z, CDCls) δ 8.19 (s, 1H), 7.55-7.38 (m, Ά\) , 7.14- ¾ NMR (400 δ z, CDCls) δ 8.19 (s, 1H), 7.55-7.38 (m, Ά \), 7.14-
7.10 (m, 3A), 6.78 (d, 8.4 Hz, 3H), 5.45 (s, 2 ) , 3.94 (s, 0，7.10 (m, 3A), 6.78 (d, 8.4 Hz, 3H), 5.45 (s, 2), 3.94 (s, 0,
3.73(s, 3H), 2.16 (s, 2H) MASS=456.17 합성예 533 ： 메틸 5-벤즈아미도 -l-(4-메톡시벤질) -2-옥소 -1,2- 디하이드로퀴놀린」 3-카복실레이트 3.73 (s, 3H), 2.16 (s, 2H) MASS = 456.17 Synthesis Example 533: Methyl 5-benzamido -l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline '' 3 Carboxylate
메틸 5-아미노 -1-(4-메톡시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린— 3- 카복실레이트 (1瞧 ol), DIPEA 1.5隱 ol) 및 벤조일클로라이드 (1.2隱 ol )를 CH2Cl2(2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 533 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxylate (1 'ol), DIPEA 1.5' ol) and benzoylchloride (1.2 'ol) Was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue is ethyl acetate and saturated Extracted with NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 533 (yield = 61%).
¾ NMR (400MHz, CDC13) 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 합성예 534 ： 메틸 5-(2-(4—클로로페닐)아세트아미도 )-l-(4-메록시벤질) -2- 옥소 -1， 2-디하이드로퀴놀린— 3-카복실레이트 ¾ NMR (400 MHz, CDC1 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, 3H) MASS = 442.15 Synthesis Example 534: Methyl 5- (2- (4-chlorophenyl) acetamido) -l- (4-methoxybenzyl) -2-oxo-1,2-dihydro Quinoline— 3-carboxylate
메틸 5-아미노ᅳ1-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEA 1.5隱 ol) 및 4-클로로페닐아세틸클로라이드 (1.2mmol)를 CH2Cl2(2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 534 화합물을 수득하였다 (수율 =61%). Methyl 5-amino ᅳ 1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate (1 隱 ol), DIPEA 1.5 隱 ol) and 4-chlorophenylacetylchloride ( 1.2 mmol) was stirred in CH 2 Cl 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to obtain the compound of Synthesis Example 534 (yield = 61%).
¾ NMR (400MHz, CDCI3) 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 합성예 535 ： 메틸 5- (아다만테인 -1-카복시아미도 )— 1-(4-메톡시벤질) -2-옥 소 -1,2-디하이드로퀴놀린 -3-카복실레이트 ¾ NMR (400 MHz, CDCI3) 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 Synthesis Example 535: Methyl 5- (adamantane-1-carboxyxamido) — 1- (4-meth Oxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate
메틸 5-아미노^- ᅳ메특시벤질 )_2_옥소 ^ , 2ᅳ디하이드로퀴놀린 _3- 카복실레이트 (1隱 01)， DIPEA(1.5mmol) 및 아다만테인 -1—카보닐클로라이드 (1.2miol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 535 화합물을 수득하였다 (수율 =61%). Methyl 5 -amino ^-ᅳ mexoxybenzyl) _ 2 _oxo ^, 2 ᅳ dihydroquinoline _ 3 -carboxylate (1 隱0 1), DIPEA (1.5 mmol) and adamantane-1—carbonylchloride (1.2 miol) was stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 535 (yield = 61%).
¾ NMR (400MHz, CDCI3) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), Z.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 (sᅳ 4H) MASS=500.23 합성예 536 ： 메틸 5-(3，5-디메틸아다만테인— 1-카복시아미도 )-l-(4-메톡시벤 질 )-2-옥소 -1， 2-디하이드로퀴놀린 _3-카복실레이트 ¾ NMR (400 MHz, CDCI 3 ) δ 8.55 (s, 1H), 7.58 (s, 1H), 7.51 (t, J = 8.0 Hz, 1H), Z.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 ᅳ 4H) MASS = 500.23 Synthesis Example 536: Methyl 5- (3,5-dimethyladamantane— 1-carboxyxamido) -l- (4-methoxybene 2-) oxo-1, 2-dihydroquinoline _3-carboxylate
메틸 5-아미노 -1-(4-메특시벤질) -2-옥소— 1,2-디하이드로퀴놀린 -3- 카복실레이트 (1睡 01)， DIPEA 1.5議 ol) 및 디메틸아다만테인 -1-카보닐 클로라이드 (1.2麵 ol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 536 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-mesoxybenzyl) -2-oxo— 1,2-dihydroquinoline-3-carboxylate (1 睡0 1), DIPEA 1.5 議 ol) and dimethyladamantane-1 Carbonyl chloride (1.2 μl ol) was stirred for 15 min in C¾C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 536 (yield = 61%).
¾匪 R (400MHz, CDC13) 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 합성예 537 ： 메틸 5-(3-브로모아다만테인 -1-카복시아미도 )-l-(4-메록시벤 질) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실레이트 ¾ 匪 R (400MHz, CDC1 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, 6H), 2.17 (s, 3H), 2.07 (s, 4H), 1.80 (s, 2H) MASS = 528.26 Synthesis Example 537: Methyl 5- (3-bromoadamantane-1-carboxyxamido) -l- (4-methoxybenzyl) -2 -Oxo-1, 2-dihydroquinoline-3-carboxylate
메틸 5-아미노 -1— (4-메특시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -IB¬ 카복실레이트 (lmmol), DIPEA 1.5隱 ol) 및 브로모아다만테인 -1-카보닐 클로라이드 (1.2醒 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 537 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-meteuk when benzyl) -2-oxo-1,2-dihydroquinoline -IB ¬ carboxylate (lmmol), DIPEA隱1.5 ol) and bromo collected just octane-1-carbonyl Chloride (1.2 μl) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate saturated NaHC0 3 . Then purified by silica gel column chromatography to give the compound of Synthesis Example 537 (yield = 61%).
¾ NMR (400MHz, CDC13) 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),¾ NMR (400 MHz, CDC1 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) ,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 합성예 538 ： 메틸 l-(4-메특시벤질) -5-(3-메틸아다만테인 -1-카복시아미도) - 2-옥소 -1,2-디하이드로퀴놀린 -3-카복실레이트 2.17 (s, 3H), 2.07 (s, 3H), 1.80 (s, 4H) MASS = 578.14 Synthesis Example 538: Methyl l- (4-methoxybenzyl) -5 (3-methyladamantane-1- Carboxyxamido)-2-oxo-1,2-dihydroquinoline-3-carboxylate
메틸 5-아미노 -1-(4ᅳ메톡시벤질 )-2—옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실레이트 (1麵 ol), DIPEA(1.5mmol) 및 메틸아다만테인 -1- 카보닐클로라이드 (1.2醒01)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 538 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4'methoxybenzyl) -2—oxo-1, 2-dihydroquinoline-3-carboxylate (1 'ol), DIPEA (1.5 mmol) and methyladamantane-1-carbo a carbonyl chloride (1.2醒0 1) was stirred for 15 min in CH 2 C1 2 (2mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to give the compound of Synthesis Example 538 (yield = 61%).
¾ 匪 R (400MHz, CDCI3) 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 )-l-(4_메톡시벤질) -2-옥소 -1，2-디하이드로퀴,놀린 -3-카복실레이트 ¾ 匪 R (400 MHz, CDCI 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 Synthesis Example 539 ： Methyl 5- (2- (adamantane- 1-yl) amido) -l- (4_methoxybenzyl) -2-oxo-1,2-dihydroqui, noline-3-carboxylate
메틸 5ᅳ아미노 -1-(4-메특시벤질 )-2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEAU.5誦 ol) 및 1-아다만테인아세틸클로라이드 (1.2瞧 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 539 화합물올 수득하였다 (수율 =61%). Methyl 5 'amino-1- (4-mesoxybenzyl) -2-oxo' 1, 2-dihydroquinoline-3-carboxylate (1 'ol), DIPEAU.5' ol) and 1-adamantaneacetyl Chloride (1.2 μl) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then purified by silica gel column chromatography to give the compound of Synthesis Example 539 (yield = 61%).
¾ NMR (400MHz, CDC13) 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 합성예 540 ： 메틸 5-(2-(3，5-디메틸아다만테인 -1-일)아세트아미도 )-l-(4-메 특시벤질 )-2-옥소 -1 , 2-다이하이드록시퀴놀린 -3-카복실레이트 ¾ NMR (400 MHz, CDC1 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, 1H), 1.79-1.63 (m, 9H) MASS = 514.25 Synthesis Example 540: Methyl 5- (2- (3,5-dimethyladamantane-1-yl) acetamido) -l- (4- Mesoxybenzyl) -2-oxo-1,2-dihydroxyquinoline-3-carboxylate
메틸 5ᅳ아미노 메톡시벤질) _2_옥소 ，2ᅳ디하이드로퀴놀린 -3ᅳ 카복실레이트 (1隱 ol), DIPEA 1.5隱 ol) 및 디메틸 -1-아다만테인아세틸 클로라이드 (1.2隱 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토 그래피로 정제하여 합성예 540 화합물을 수득하였다 (수율 =61%) Methyl 5 ᅳ amino methoxybenzyl) _ 2 _ oxo, 2 ᅳ dihydroquinoline- 3 ᅳ carboxylate (1 隱 ol), DIPEA 1.5 및 ol) and dimethyl-1-adamantaneacetyl chloride (1.2 隱 ol) Stirred at 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 540 (yield = 61%)
¾ 匪 R (400MHz, CDCI3) δ 8.64 (s, 1H) , 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, 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 합성예 541 ： 메틸 5-(2-(3-브로모메테인 -1-일)아세트아미도 )-l-(4-메록시벤 질) -2-옥소 -1， 2-디클로로퀴놀린 -3-카복실레이트 ¾ 匪 R (400 MHz, CDCI 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, 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 Synthesis Example 541: Methyl 5- (2- (3-bromomethane-1-yl) acetamido) -l- (4-hydroxyben Vagin) -2-oxo-1,2-dichloroquinoline-3-carboxylate
메틸 5-아미노— 1-(4-메톡시벤질 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEA(l.¾ ol) 및 브로모 -1-아다만테인아세틸 클로라이드 (1.2瞧 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 541 화합물을 수득하였다 (수율 =61%). Methyl 5-amino— 1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3- Carboxylate (1 'ol), DIPEA (1. 3 ol) and bromo-1-adamantaneacetyl chloride (1.2' ol) were stirred in CH 2 C1 2 (2 mL) for 15 minutes. The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 541 (yield = 61%).
¾ NMR (400丽 z, CDC13) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35¾ NMR (400 δ z, CDC1 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, 1H), 1.79-1.63 (m, 8H) MASS=592.16 합성예 542 ： 메틸 l-(4-메특시벤질) -5-(2-(3-메틸아다만테인 -1-일)아세트아 미도) -2-옥소 -1 , 2—디클로로퀴놀린 -3-카복실레이트 (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 Synthesis Example 542 ： Methyl l- (4- Mesoxybenzyl) -5- (2- (3-methyladamantane-1-yl) acetamido) -2-oxo-1,2—dichloroquinoline-3-carboxylate
메틸 5-아미노 -1-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복실레이트 (1睡 ol), DIPEA(1.5mmol) 및 메틸 -1-아다만테인아세틸 클로라이드 (1.2隱 ol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 '정제하여 합성예 542 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate (1 'ol), DIPEA (1.5 mmol) and methyl-1-adamantane Acetyl chloride (1.2 μl ol) was stirred for 15 minutes in C¾Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . Then silica gel column chromatography 'purified to give the Synthesis Example 542 compound (yield = 61%).
¾ NMR (400MHz, CDC13) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, / = 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 합성예 543 ： 메틸 5-(2-사이크로핵실아세트아미도 )— 1-(4-메톡시벤질) -2-옥 소 -1 , 2-디클로로퀴놀린 -3-카복실레이트 ¾ NMR (400 MHz, CDC1 3 ) δ 8.64 (s, 1H), 7.54-7.49 (m, 2H), 7.35 (s, 1H), 7.26 (s, 1H), 7.17 (d, / = 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 Synthesis Example 543: Methyl 5- (2-cyclonucleosilacetamido) — 1- (4-methoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate
메틸 5-아미노 -1-(4—메톡시벤질) -2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol)ᅳ DIPEA 1.5隱 ol) 및 사이클로핵실아세틸클로라이드 Methyl 5-amino-1- (4—methoxybenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylate (1 'ol)' DIPEA 1.5 'ol) and cyclonuxylacetylchloride
(1.2醒01)를 CH2C1'2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 543 화합물을 수득하였다 (수율 =61%). A (1.2醒0 1) was stirred for 15 min in CH 2 C1 '2 (2mL) . The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 543 (yield = 61%).
¾ NMR (400MHz, CDCI3) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, / = 8.0 Hz, 3H), 6.82 (d, J = 8.0 Hz, 2H), 5.52(s,¾ NMR (400 MHz, CDCI 3 ) δ 8.62 (s, 1H), 7.55 -7.49 (m, 1H), 7.40 (s, 1H), 7.17 (d, / = 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 합성예 544 ： 메틸 5- (사이클로핵센카복시아미도) -1-(4-메특시벤질) -2-옥소- 1,2—디클로로퀴놀린 -3-카복실레이트 2H), 3.97 (s, 3H), 3.76 (s, 3H), 2.36 (s, 2H), 1.98-1.62 (m, 11H) MASS = 462.22 Synthesis Example 544 ： Methyl 5- (cyclonuclesencarboxylamido) -1- (4-methoxybenzyl) -2-oxo- 1,2-dichloroquinoline-3-carboxylate
메틸 5-아미노 -1ᅳ (4-메톡시벤질) -2-옥소 -1， 2—디하이드로퀴놀린 -3- 카복실레이트 (1瞧 oO, DIPEA(1.5mmol) 및 사이클로핵산카보닐클로라이드 (1.2瞧 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 544 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1 '(4-methoxybenzyl) -2-oxo-1,2—dihydroquinoline-3-carboxylate (1'oO, DIPEA (1.5mmol) and cyclonucleocarbonylchloride (1.2') ol) was stirred for 15 min in CH 2 C1 2 (2 mL) The residue was extracted with ethyl acetate and saturated NaHC0 3 and then purified by silica gel column chromatography to give the compound of Synthesis 544 (yield = 61%). .
¾ 匪 R (400MHz, CDCls) δ 8.62 (s, 1H), 7.55 -7.49 On, 1H), 7.40 ¾ 匪 R (400 MHz, CDCls) δ 8.62 (s, 1H), 7.55 -7.49 On, 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 합성예 545 ： 메틸 5- (아다만테인 -1-카복시아미도 )-l-(4-에틸벤질) -2-옥소- 1， 2-디클로로퀴놀린 -3-카복실레이트 (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 Synthesis Example 545: Methyl 5- (adamantane-1-carboxyxamido) -l- (4-ethylbenzyl) -2-oxo-1, 2-dichloroquinoline 3-carboxylate
메틸 ᅳ아미노 -1-(4-에틸벤질 )-2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3- 카복실레이트 (1画 ol), DIPEAU.5隱 ol) 및 아다만테인 -1-카보닐클로라이드 (1.2隱 ol)를 CH2C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 545 화합물을 수득하였다 (수율 =61%). Methyl ᅳ amino-1- (4-ethylbenzyl) -2-oxo ᅳ 1, 2-dihydroquinoline-3-carboxylate (1 画 ol), DIPEAU.5. Ol) and adamantane-1-carbonyl Chloride (1.2 μl) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 545 compound (yield = 61%).
¾ NMR (400MHz, CDCI3) 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 (111， 11H) MASS= 498.25 합성예 546 ： 메틸 5- (아다만테인 -1-카복시아미도 )-l-(3-메톡시벤질) -2-옥소 ¾ NMR (400 MHz, CDCI3) 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 (111, 11H) MASS = 498.25 Synthesis Example 546: Methyl 5- (adamantane-1) -Carboxyxamido) -l- (3-methoxybenzyl) -2-oxo
-1， 2-디클로로퀴놀1린 -3-카복실레이트 -1, 2-dichloroquinol 1 lean-3-carboxylate
메틸 5-아미노 -1-(3-메톡시벤질) -2-옥소 -1， 2-디클로로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEAU.5瞧 ol) 및 아다만테인ᅳ 1ᅳ카보닐클로라이드 Methyl 5-amino-1- (3-methoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate (1 'ol), DIPEAU.5' ol) and adamantane® 1'carbo Nyl chloride
(1.2瞧01)를 CH2C12 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHCOs로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 546 화합물을 수득하였다 (수율 =61%). Ή 匪 R (400MHz, CDCI3) 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 합성예 547 ： 메틸 5- (아다만테인 -1-카복시아미도 )-l-(4-나이트로벤질 )—2-옥 소 -1 , 2-디클로로퀴놀린 -3-카복실레이트 (1.2 瞧0 1) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHCOs. After purification by silica gel column chromatography to obtain the compound of Synthesis Example 546 (yield = 61%). 匪 匪 R (400 MHz, CDCI 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 (m, 11H) MASS = 500.23 Synthesis Example 547: Methyl 5- (adamantane -1-carboxyxamido) -l- (4-nitrobenzyl) —2-oxo-1,2-dichloroquinoline-3-carboxylate
메틸 5-아미노 -1-(4-나이트로벤질) -2-옥소 -1， 2-디클로로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEA(l. mol) 및 아다만테인 -1ᅳ카보닐클로라이드 (1.2睡01)를 CH2C12 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 547 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-nitrobenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate (1 隱 ol), DIPEA (l.mol) and adamantane-1 ᅳ carbo Nylchloride (1.2 × 10 1) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 547 (yield = 61%).
¾ MR (400MHz, CDC13) δ 8.71 (d, J = 16 Hz, 1H) , 8.15 (d, J = 8 Hz, 2H), 7.37 (dd, J = 4 Hz, / = 4 Hz, 2H) , 6.51 (d, / = 4 Hz, 1H), 6.48-6.44 (m, 1H) , 5.59 (s, 2H), 3.98 (s, 3H) . MASS=515.21 ¾ MR (400 MHz, CDC1 3 ) δ 8.71 (d, J = 16 Hz, 1H), 8.15 (d, J = 8 Hz, 2H), 7.37 (dd, J = 4 Hz, / = 4 Hz, 2H), 6.51 (d, / = 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 -l-(4- (트라이플루 오로메톡시 )벤질) -1， 2-디클로로퀴놀린 -3-카복실레이트 Synthesis Example 548: Methyl 5- (adamantane-1-carboxyxamido) -2-oxo-1-(4- (trifluoromethoxy) benzyl) -1, 2-dichloroquinoline-3-carboxylate
메틸 5-아미노 -2-옥소— 1-(4- (트라이플루오로메록시)벤질) -1,2- 디클로로퀴놀린 -3-카복실레이트 (1瞧 ol), DIPEA(1.5mmol) 및 아다만테인 -1- 카보닐클로라이드 (1.2隱 ol)를 CH2Cl2 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 548 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-2-oxo— 1- (4- (trifluoromethoxy) benzyl) -1,2-dichloroquinoline-3-carboxylate (1 'ol), DIPEA (1.5 mmol) and adamantane- 1-carbonylchloride (1.2 μl ol) was stirred for 15 min in CH 2 Cl 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 548 (yield = 61%).
¾ NMR (400丽 z, CDCls) 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 합성예 549 ： 메틸 5- (아다만테인 -1-카복소아미도 )-l-(4-사이아노벤질) -2-옥 소 -1， 2—디클로로퀴놀린 -3-카복실레이트  ¾ NMR (400 z, CDCls) 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 Synthesis Example 549: Methyl 5- (adamantane-1- Carboxamido) -l- (4-cyanobenzyl) -2-oxo-1,2—dichloroquinoline-3-carboxylate
메틸 5-아미노 -1-(4-사이아노벤질 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEA 1.5隱 ol) 및 아다만테인 -1-카보닐 클로라이드 (1.2隱 ol)를 C¾C12 (2mL)에서 15분 간 교반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼 크로마토그래피로 정제하여 합성예 549 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-cyanobenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxylate (1 ′ ol), DIPEA 1.5 ′ ol) and adamantane-1-carbo Neil chloride (1.2 μl ol) was stirred for 15 min in C¾Cl 2 (2 mL). The residue is Extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the compound of Synthesis Example 549 (yield = 61%).
¾ NMR (400MHz, CDC13) δ 8.62 (s, 1Η), 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 )-l-(4-플루오로벤질 )-2-옥 소 -1， 2-디클로로퀴놀린 -3-카복실레이트 ¾ NMR (400 MHz, CDC1 3 ) δ 8.62 (s, 1Η), 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 Synthesis Example 550: Methyl 5- (adamantane-1-carboxyxamido)- l- (4-fluorobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate
메틸 5-아미노 -1-(4-플루오로벤질 )-2-옥소 -1， 2-디클로로퀴놀린 -3- 카복실레이트 (1隱 ol), DIPEAC1.5隱 ol) 및 아다만테인 -1—카보닐클로라이드 (1.2瞧01)를 CH2C12 (2mL)에서 15분 간 교 반하였다. 잔기는 에틸아세테이트 및 포화 NaHC03로 추출하였다. 이후 실리카겔 컬럼크로마토그래피로 정제하여 합성예 550 화합물을 수득하였다 (수율 =61%). Methyl 5-amino-1- (4-fluorobenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate (1 ′ ol), DIPEAC1.5 ′ ol) and adamantane-1—carbo Nylchloride (1.2 × 10 1) was stirred for 15 min in CH 2 C1 2 (2 mL). The residue was extracted with ethyl acetate and saturated NaHC0 3 . After purification by silica gel column chromatography to obtain the Synthesis Example 550 compound (yield = 61%).
¾ NMR (400MHz, CDC13) δ 8.53(s, 1H), 7.55(s, 1H), 7.53-7.43 (m, 2H), 7.21-7.17(m; 1H), 7. ll-7.09(m, 1H), 6.97(t, 8Hz , 1H)， 5.52 (s, 2H), 4.42(s, 1H), 3.98(s, 3H), 2.17-1.74(m, 15H) MASS= 488.21 합성의 일반적안 과정 ¾ NMR (400 MHz, CDC1 3 ) δ 8.53 (s, 1H), 7.55 (s, 1H), 7.53-7.43 (m, 2H), 7.21-7.17 (m; 1H), 7.ll-7.09 (m, 1H ), 6.97 (t, 8Hz, 1H), 5.52 (s, 2H), 4.42 (s, 1H), 3.98 (s, 3H), 2.17-1.74 (m, 15H) MASS = 488.21 General Design Process of Synthesis
： 단계 (c-2)의 일반적인 과정과 같음 합성예 551 ： 5- (아다만테인 -1-카복시아미도 )-1-(4-메특시벤질) -2-옥소 -1,2- 디클로로퀴놀린 -3-카복실릭액시드  : As in the general procedure of step (c-2) Synthesis Example 551: 5- (adamantane-1-carboxyxamido) -1- (4-mesoxybenzyl) -2-oxo-1,2-dichloroquinoline -3-carboxylic acid
메틸 5— (아다만테인 -1-카복시아마이드) -1-(4-메툭시벤질) -2-옥소- 1,2-디하이드로퀴놀린 -3-카복실레이트를 MeOH(200mL)에 용해시킨 1OT K0H로 12시간 동안 8(rc에서 교반하고， 흔합물을 여과 후 여과물을 0로 세척하여 합성예 551 화합물을 수득하였다 (수율 =70%).  Methyl 5— (adamantane-1-carboxamide) -1- (4-Metuxibenzyl) -2-oxo- 1,2-dihydroquinoline-3-carboxylate dissolved in MeOH (200 mL) 1OT K0H After stirring for 12 hours at 8 (rc, the mixture was filtered and the filtrate was washed with 0 to obtain a Synthesis Example 551 compound (yield = 70%).
¾ 匪 R (400MHz, CDCI3) 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, 8.0 Hz, 2H) , 6.81 (d, / = 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 합성의 일반적인 과정 ¾ 匪 R (400 MHz, CDCI 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, 8.0 Hz, 2H), 6.81 (d, / = 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 General process of synthesis
： 단계 (d-3, h-8)의 일반적 과정과 같음 합성예 552 ： 에틸 5- (아다만테인 -1-카복시아미도 )-1-(4-메톡시벤질) -2-옥소 -1,2-디클로로퀴놀린 -3-카복실레이트  : Same as general procedure of step (d-3, h-8) Synthesis Example 552: Ethyl 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1 , 2-dichloroquinoline-3-carboxylate
5- (아다만테인 -1-카복시아미도)ᅳ 1-(4-메특시벤질 )-2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭액시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 에탄올 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 552 화합물을 수득하였다 (수율 =63%).  5- (adamantane-1-carboxyxamido) ᅳ 1- (4-mesoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylic acid (1 mmol) was added to DMF (2 mL). DIPEA (3 'ol), ethanol (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 552 (yield = 63%).
¾ NMR (40(MHz, CDC13) 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, / = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H), 2.06 (s, mi, 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-옥 소 -1 , 2-디클로로퀴놀린 -3-카복시아미도 ¾ NMR (40 (MHz, CDC1 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, / = 8 Hz, 2H), 5.48 (s, 2H), 4.45-4.39 (m, 2H), 3.74 (s, 3H), 2.14 (s, 3H), 2.06 (s, mi, 1.80-1.79 (m, 6H), 1.43-1.39 (m, 3H) MASS = 514.25 Synthesis Example 553: 5- (adamantane-1-carboxyboxido) -1— ( 4-methoxybenzyl) -N-methyl-2-oxo-1,2-dichloroquinoline-3-carboxyxamido
5- (아다만테인 -1-카복시아미도 )— 1-(4-메특시벤질 )— 2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭엑시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 메틸아민 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 553 화합물을 수득하였다 (수율 =63%).  5- (adamantane-1-carboxyxamido) — 1- (4-mesoxybenzyl) — 2-oxo-1, 2-dichloroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF ( 2 mL). DIPEA (3 'ol), methylamine (1.5 mmol) and PyBop (2' ol) 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. Then purified by silica gel chromatograph to give the compound of Synthesis Example 553 (yield = 63%).
¾ NMR (400MHz, CDCI3) δ 8.55 (s, 1H) , 7.58 (s, 1H)， 7.51 (t, J¾ NMR (400 MHz, CDCI 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, / = 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 )-l-(4-메록시벤질) -Ν,Ν-디메틸- 2-옥소 -1， 2-디하이드로퀴놀린 -3-카복시아마이드 5- (아다만테인 -1-카복시아미도 )-i-(4-메록시벤질) -2-옥소 -1,2-다이클 로로퀴놀린 -3-카복실릭엑시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 디메틸아민 (1.5 mmol) 및 PyBop(2 mmol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 554 화합물을 수득하였다 (수율 =63%). = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 2H), 6.81 (d, / = 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 Synthesis Example 554: 5- (adamantane— 1- Carboxylamido) -l- (4-methoxybenzyl) -Ν, Ν-dimethyl- 2-oxo-1,2-dihydroquinoline-3-carboxamide 5- (adamantane-1-carboxyxamido) -i- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF ( 2 mL). DIPEA (3 ′ ol), 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 obtained residue was extracted with ethyl acetate and water. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 554 (yield = 63%).
¾ NMR (400MHz, CDC13) 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, 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 합성예 555 ： 프로필 5- (아다만테인 -1-카복시아미도 )-l-(4-메특시벤질) -2-옥 소 -1， 2-디클로로퀴놀린 -3-카복실레이트 ¾ NMR (400 MHz, CDC1 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, 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 Synthesis Example 555: Propyl 5- (adamantane-1-carboxyxamido) -l- (4-methoxybenzyl) -2-oxo-1, 2 -Dichloroquinoline-3-carboxylate
5- (아다만테인 -1-카복시아미도 )-1-(4-메특시벤질 )-2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭액시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 1-프로판올 L5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 555 화합물을 수득하였다 (수율 =63 .  5- (adamantane-1-carboxyxamido) -1- (4-mesoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF ( 2 mL). DIPEA (3 mmol), 1-propanol L5 mmol) and PyBop (2 μL ol) 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. After purification by silica gel chromatography to obtain the Synthesis Example 555 compound (yield = 63.
¾ 匪 R (400MHz, CDCI3) δ 8.51 (s, 1H)， 7.56 (b, s, 1H), 7.52-¾ 匪 R (400 MHz, CDCI 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, 1H), 4.35 (t, / = 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 합성예 556 ： 아 소프로필 5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤 질) -2-옥소 -1， 2-디클로로퀴놀린 -3-카복실레이트 7.44 (m, 2H), 7.17-7.14 (m, 3H), 6.82-6.80 (m, 2H), 5.51 (b, s, 1H), 4.35 (t, / = 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 Synthesis Example 556 ： Aso Propyl 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate
5- (아다만테인 -1-카복시아미도 )-1-(4-메톡시벤질 )-2-옥소 -1， 2—다이클 로로퀴놀린 -3-카복실릭엑시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3mmol), 2-프로판올 (1.5 mmol) 및 PyBop(2 隱 ol)를 반응 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 556 화합물을 수득하였다 (수율 =63 . 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF ( 2 mL). DIPEA (3 mmol), 2-propanol (1.5 mmol) and PyBop (2 μL ol) 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. Silica gel chromatography Purification gave Synthesis Example 556 compound (Yield = 63.
¾醒 R (400MHz, CDCls) 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 합성예 557 ： N—(l-(4-메록시벤질) -3- (메톡시메틸 )-2-옥소 -1,2-디하이드로퀴 놀린 -5-일)아다만테인 -1-카복시아마이드  ¾ 醒 R (400MHz, CDCls) 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 Synthesis Example 557: N— (l- (4-methoxybenzyl) -3- (methoxymethyl) -2-oxo-1,2-dihydroqui Nolin-5-yl) adamantane-1-carboxamide
5- (아다만테인—1-카복시아미도 )-1-(4-메톡시벤질) -2-옥소 -1,2-다이클 로로퀴놀린 -3-카복실릭액시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 아세트알데하이드 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 557 화합물을 수득하였다 (수율 =63%).  5- (adamantane—1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid (1 隱 ol) was added to DMF ( 2 mL). DIPEA (3xol), acetaldehyde (1.5xol) and PyBop (2xol) 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. Then purified by silica gel chromatography to give the compound of Synthesis Example 557 (yield = 63%).
¾ NMR (400MHz, CDCI3) δ 8.51 (s, 1H), 7.56 (s, 1H), 7.48 (t, J¾ NMR (400 MHz, CDCI 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, / = 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- (에록시메틸 )-l-(4-메록시벤질) -2-옥소 -1，2-디하이드로퀴 놀린 -5—일)아다만테인 -1-카복시아마이드 = 8 Hz, 1H), 7.41 (d, J = 4 Hz, 1H), 7.15 (t, / = 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 Synthesis Example 558 ： N_ (3 (Ethoxymethyl) -l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide
5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤질 )-2-옥소 -1ᅳ 2-다이클 로로퀴놀린 -3—카복실릭액시드 (1 隱 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3瞧 ol), 프로피온알데하이드 (1.5 隱 ol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 558 화합물을 수득하였다 (수율 =6 ).  5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1 '2-dichloroquinoline-3-carboxylic acid (1' ol) was added to DMF ( 2 mL). DIPEA (3 'ol), propionaldehyde (1.5' ol) and PyBop (2 'ol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 558 (yield = 6).
¾ 賺 (400MHz, CDCI3) 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 합성예 559: S-메틸 5- (아다만테인 -1-카복시아미도 )-l-(4-메톡시벤질) -2-옥 소 -1 , 2-디하이드로퀴놀린 -3-카보싸이오에이트 ¾ 賺 (400 MHz, CDCI 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 = 500.27 Synthesis Example 559: S-methyl 5- (adamantane-1-carboxyxamido) -l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate
5- (아다만테인 -1-카복시아미도 )-1— (4-메톡시벤질 ) -2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭액시드 (1 mmol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 메테인싸이올 (1.5 画 ol) 및 PyBop(2 画 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 559 화합물올 수득하였다 (수율 =63%).  5- (adamantane-1-carboxyxamido) -1— (4-methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylic acid (1 mmol) was added to DMF (2 mL). DIPEA (3xol), methanethiol (1.5xol) and PyBop (2xol) 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. Then purified by silica gel chromatography to obtain the compound of Synthesis Example 559 (yield = 63%).
¾ NMR (400MHz, CDC13) δ 8.55 (s, 1H), 7.58 (s, 1H) , 7.51 (t, J¾ NMR (400MHz, CDC1 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 (sᅳ 4H), 1.80 (s, 4H) MASS=516.22 합성예 560 ： S-에틸 5- (아다만테인 -1-카복시아미도 )-l-(4-메톡시벤질) -2_옥 소 -1， 2-디하이드로퀴놀린 -3-카보싸이오에이트 = 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 ᅳ 4H), 1.80 (s, 4H) MASS = 516.22 Synthesis Example 560 ： S-ethyl 5- (adamantane) -1-carboxyxamido) -l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carbothioate
5- (아다만테인 -1—카복시아미도 )-1-(4—메특시벤질 )-2-옥소ᅳ 1， 2-다이클 로로퀴놀린 -3-카복실릭액시드 (1 麵 ol)를 DMF(2 mL)에 용해시켰다. DIPEA (3隱 ol), 에테인싸이올 (1.5 mmol) 및 PyBop(2 隱 ol)를 반웅 흔합물에 첨가하였다. 흔합물을 상온에서 3시간 동안 교반하였다. 수득한 잔여물을 에틸 아세테이트 및 물로 추출하였다. 이후 실리카겔 크로마토그래프로 정제하여 합성예 560 화합물을 수득하였다 (수율 =63%).  5- (adamantane-1—carboxyxamido) -1- (4—mesoxybenzyl) -2-oxox 1, 2-dichloroquinoline-3-carboxylic acid (1 x ol) was added to DMF ( 2 mL). DIPEA (3x ol), ethanethiol (1.5 mmol) and PyBop (2x ol) 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. Then purified by silica gel chromatography to obtain the Synthesis Example 560 compound (yield = 63%).
¾丽 R (400丽 z, CDC13) 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, / = 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 ¾ 丽 R (400 丽 z, CDC1 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, / = 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
합성된 화합물의 구조 및 분광학 데이터 (합성예 530-560) ' //:/ O K-Z6001S2MI>d 6/.SS0SSZAV7 Structure and Spectroscopy Data of Synthesized Compound (Synthesis Example 530-560) '' // : / O K-Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000327_0001
Figure imgf000327_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI> d 6 / .SS0SSZAV 7
Figure imgf000328_0001
Figure imgf000328_0001
Figure imgf000329_0001
Figure imgf000329_0001
Figure imgf000330_0001
Figure imgf000330_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000331_0001
Figure imgf000331_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000333_0001
Figure imgf000333_0001
Reagents and condition： a) PMBCI, 18-crown-6, DMF, RT, overnight; b) SnCI2. BOH, 80°C, 30min; c) R-adamantane-1- carbonyl chloride, DIPEA, CH2CI2, RT, 4hr; d) HCl, H20, NaN02, SnCI2, RT, overnight; e) R-adamantane-1-carbonyl chloride, DIPEA, CH2CI2, RT, 4hr 합성의 일반적인 과정 Reagents and condition ： a) PMBCI, 18-crown-6, DMF, RT, overnight; b) SnCI 2 . BOH, 80 ° C., 30 min; c) R-adamantane-1- carbonyl chloride, DIPEA, CH 2 CI 2 , RT, 4 hr; d) HCl, H 2 O, NaNO 2 , SnCI 2 , RT, overnight; e) general procedure for the synthesis of R-adamantane-1-carbonyl chloride, DIPEA, CH 2 CI 2 , RT, 4hr
： 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, 78.87瞧 ol), 2C03 (14g, 105.16 隱 ol)ᅳ 18- 크라운—6 (2.7g, 10.51 mmol)을 용액에 첨가하였다. 흔합물을 상온에서 12시간 동안 교반하고， 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 9번 화합물을 수득하였다. 합성예 561 ： 1-(4-메록시벤질) -5-나이트로퀴놀린 -2(1H)-온 Starting material (10.0 g, 52.58 mmol) was dissolved in anhydrous DMF (100 mL). 4-methoxybenzyl chloride (17 g, 78.87 瞧 ol), 2 CO 3 (14 g, 105.16 隱 ol) ᅳ 18-crown-6 (2.7 g, 10.51 mmol) was added to the solution. The mixture was stirred at room temperature for 12 hours and extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography afforded compound 9. Synthesis Example 561: 1- (4-methoxybenzyl) -5-nitroquinolin-2 (1H) -one
5-나이트로퀴놀린— 2(1H)-온 (1 隱 ol)을 무수 DMF(2 mL)에 용해시켰다. 5-nitroquinoline—2 (1H) -one (1 μL) was dissolved in anhydrous DMF (2 mL).
4-메록시벤질 클로라이드 (1.5 mmol), K2C03 (2 醒 ol), 18-크라운 _6 (0.2 mmol)을 용액에 첨가하였다. 흔합물을 상온에서 12시간 동안 교반하고， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다. (수율 = 80%) 4-methoxybenzyl chloride (1.5 mmol), K 2 CO 3 (2 μl ol), 18-crown — 6 (0.2 mmol) were added to the solution. The mixture was stirred at room temperature for 12 hours and extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography gave the desired compound. (Yield = 80%)
¾ 匪 R (400MHz, CDCI3) 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, / = 8 Hz, 1H),¾ 匪 R (400 MHz, CDCI 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, / = 8 Hz, 1H),
7.15 (d, / = 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 합성의 일반적인 과정 7.15 (d, / = 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 General procedure of synthesis
： 단계 (b)의 일반적 과정 ： General process of step (b)
9 번 화합물 (118mg, 0.36隱01)을 에탄올 (10ml)에 용해시킨 후,After dissolving compound 9 (118 mg, 0.36 隱0 1) in ethanol (10 ml),
SnCl2 (245mg, 1.08隱 ol)를 용액에 첨가한다. 상온에서 30분간 교반 시키고 브린 (brine)과 에틸아세테이트로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 10번 화합물을 수득하였다. 합성예 562 ： 5-아미노 -1-(4-메록시벤질)퀴놀린 -2(1H)-온 SnCl 2 (245 mg, 1.08 μl ol) is added to the solution. The mixture was stirred at room temperature for 30 minutes and extracted with brine and ethyl acetate. The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography gave compound 10. Synthesis Example 562: 5-Amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one
1-(4-메록 ᅵ벤질 )-5-나이트로퀴놀린 -2(1H)-온 (0.36 瞧 ol) 에탄을 (10 ml)에 용해시킨 후， SnCl2 (245mg, 1.08隱 ol)를 용액에 첨가한다. 상은에서 30분간 교반 시키고 브린 (brine)과 에틸아세테이트로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하였다. 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다. (수율 = 70%) Dissolve 1- (4-merox Benzyl) -5-nitroquinolin-2 (1H) -one (0.36 瞧 ol) ethane in (10 ml), and then add SnCl 2 (245 mg, 1.08 隱 ol) to the solution. Add. The phases were stirred for 30 minutes and extracted with brine and ethyl acetate. The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated in vacuo. Purification by column chromatography gave the desired compound. (Yield = 70%)
¾ NMR (400丽 z, CDCls) 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  ¾ NMR (400 z, CDCls) 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
합성의 일반적인 과정 General process of synthesis
： 단계 (d)의 일반적 과장 ： General exaggeration of step (d)
10 번 화합물 (8.2mg, 0.01 mmol)을 농축된 HC1과 물에 녹이고 교반한다. 30분이 지난 뒤， 물에 녹여진 NaN02 (2.21mg, 0.01隱01)를 용액에 첨가한다. 30분 후， SnCl2 (18.86 mg, 0.05mmol) 을 첨가하고 상온에서 12시간 교반시킨다. 1 노르말 HC1로 산화시켜 얻어진 여과물을 여과하여 물로 씻은 후 12번 화합물을 수득하였다. 합성예 563 ： 5-하이드라지닐 -1-(4-메특시벤질)퀴놀린 -2(1H)-온Compound 10 (8.2 mg, 0.01 mmol) is dissolved in concentrated HC1 and water and stirred. After 30 minutes, NaN0 2 (2.21mg, 0.01 隱0 1) dissolved in water is added to the solution. After 30 minutes, SnCl 2 (18.86 mg, 0.05 mmol) is added and stirred at room temperature for 12 hours. The filtrate obtained by oxidizing with 1 normal HC1 was filtered and washed with water to obtain compound 12. Synthesis example 563: 5-hydrazinyl-1- (4-mesoxybenzyl) quinolin-2 (1H) -one
5-아미노 -1— (4-메톡시벤질)퀴놀린 -2(1H)-온 (8.2mg, 0.01 誦 ol)을 농축된 HC1과 물에 녹이고 교반한다. 30분이 지난 뒤， 물에 녹여진 NaNo2 (2.21mg, 0.이瞧01)를 용액에 첨가한다. 30분 후, SnCl2 (18.86 mg, 0.05麵 ol) 을 첨가하고 상은에서 12시간 교반시킨다. 1 노르말 HC1로 산화시켜 얻어진 여과물을 여과하여 물로 씻은 후 목적 화합물을 수득하였다. (수율 = 85%) 5-Amino-l— (4-methoxybenzyl) quinolin-2 (1H) -one (8.2 mg, 0.01 μL) is dissolved in concentrated HC1 and water and stirred. After 30 minutes, NaNo 2 (2.21 mg, 0.01) dissolved in water is added to the solution. After 30 minutes, SnCl 2 (18.86 mg, 0.05 μl ol) is added and stirred for 12 hours at silver. 1 The filtrate obtained by oxidation with normal HC1 was filtered and washed with water to obtain the target compound. (Yield = 85%)
¾ NMR (400MHz, MeOH) δ 8.12 (d, J = 8 Hz, 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 합성의 일반적인 과정  ¾ NMR (400 MHz, MeOH) δ 8.12 (d, J = 8 Hz, 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 General procedure of synthesis
： 단계 (c)의 일반적 과정 ： General process of step (c)
10 번 화합물 (7.1mg, 0.02隨 ol)을 C¾C12 (0.75ml)에 용해한 후Compound 10 (7.1mg, 0.02 隨 ol) was dissolved in C¾C1 2 (0.75ml)
DIPEA (7.8λ , 0.03隱01)， R-아다만테인 -1-카르보닐 클로라이드 (6.03mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 11， 13 화합물을 수득하였다. 합성예 564 ： N-(l-(4—메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -5-일)아다 만테인 -1—카복 Λ1 "마.이드 DIPEA (7.8λ, 0.03x01) and R-adamantane-1-carbonyl chloride (6.03 mg, 0.02 mmol) are stirred at room temperature for 4 hours. Then extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give 11, 13 compound. Synthesis Example 564 ： N- (l- (4—methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1—carboxy Λ 1 "maide
5-아미노 -1-(4-메록시벤질)퀴놀린 -2(1Η)-온 (7.1mg, 0.02画 ol)을 5 -amino-1- (4-methoxybenzyl) quinolin-2 (1Η) -one (7.1 mg, 0.02 μl)
CH2C12 (0.75ml)에 용해한 후 DIPEA (7.8λ , 0.03麵 ol), 아다만테인 -1- 카르보닐 클로라이드 (6.03mg, 0.02隱 ol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수After dissolving in CH 2 C1 2 (0.75 ml), DIPEA (7.8λ, 0.03dl ol), adamantane-1-carbonyl chloride (6.03 mg, 0.02dl ol) are stirred at room temperature for 4 hours. Then extracted with ethyl acetate and ¾0. The combined organic layer is anhydrous
N S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 45%) Dry over N S0 4 , concentrate in vacuo and purify by column chromatography to give the desired compound (Yield = 45%).
¾ NMR (400MHz, CDC13) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H)， 7.18 (dd, / = 8 Hz, 4 Hz, 1H) , 7.14-7.11 (m.,¾ NMR (400 MHz, CDC1 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, / = 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 합성예 565 ： N— (l-(4-메록시벤질) _2—옥소 -1,2-디하이드로퀴놀린 -5-일) -3-메 틸아다만테인 -1-카복사마이드 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 Synthesis Example 565: N— (l- (4-hydroxybenzyl) _2—oxo-1,2-dihydroquinoline-5 (1) -3-Methyl adamantane-1-carboxamide
5-아미노 -1-(4-메특시밴질)퀴놀린 -2(1H)-온 (10mg, 0.02mmol)을 5-amino-1- (4-mesoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol)
CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03睡01)， 3-메틸아다만테인 -1- 카르보닐 클로라이드 (5.99 mg, 0.02瞧01)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 50%) . After dissolving in CH 2 C1 2 (1 ml), DIPEA (7.8λ, 0.03 睡0 1), 3-methyladamantane-1-carbonyl chloride (5.99 mg, 0.02 瞧 01) are stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 50%).
¾ NM (400MHz, CDC13) 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 Cm, 5H), 1.88-1.73 Cm, 7H) 0.89 (s, 3H) MASS=456.58 합성예 566 ： N-(l— (4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -5—일) -3,5- 다이메킬아다만테인 -1-카복사마이드 ¾ NM (400 MHz, CDC1 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 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 Cm, 5H), 1.88-1.73 Cm, 7H) 0.89 (s, 3H) MASS = 456.58 Synthesis Example 566: N- (l— (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 5—Sun) -3,5- Dimethaladamantane-1-carboxamide
5-아미노 -1— (4-메톡시벤질)퀴놀린 -2(1H)-은 (10mgᅳ 0.02睡 ol)을 CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03瞧 ol), 3-디메틸아다만테인 -1- 카르보닐 클로라이드 (6.34 mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키'고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 50%). 5-amino-1— (4-methoxybenzyl) quinoline-2 (1H) -silver (10mg ᅳ 0.02 睡 ol) was dissolved in CH 2 C1 2 (1ml) and then DIPEA (7.8λ, 0.03 瞧 ol), 3 Dimethyladamantane-1-carbonyl chloride (6.34 mg, 0.02 mmol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. Dry the combined organic layer over anhydrous Na 2 S0 4 'high, and concentrated in vacuo purified by column chromatography to give the desired compound (yield = 50%).
¾ NMR (400MHz, CDCI3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, / = 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 합성예 567 ： 3-브로모 -N-(l-(4-메록시벤질) -2-옥소— 1,2-디하이드로퀴놀린- 5-일)아다만테인 -1-카복사마이드  ¾ NMR (400 MHz, CDCI3) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, / = 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 Synthesis Example 567: 3-bromo-N- (l- (4-methoxybenzyl) -2-oxo—1 , 2-dihydroquinolin-5-yl) adamantane-1-carboxamide
5-아미노 -1-(4ᅳ메특시벤질)퀴놀린 -2(1H)-온 (10mg, 0.02瞧 ol)을 CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03麵01)， 3—브로모아다만테인 -1- 카르보닐 클로라이드 (7.77mg, 0.02画01)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 63%) 5 -Amino-1- (4'mesomeoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 'ol) After dissolving in CH 2 C1 2 (1 ml), DIPEA (7.8λ, 0.03 麵0 1) and 3—bromoadamantane-1-carbonyl chloride (7.77mg, 0.02 画0 1) are stirred at room temperature for 4 hours. . Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 63%).
¾ NMR (400MHz, CDC13) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H)， 7.18 (ddᅳ 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 (mᅳ 5H), 1.88-1.73 (m, 7H) MASS=521.45 합성예 568 ： 3- 로로 -N-(l-(4-메록시벤질) -2-옥소 -1，2-디하이드로퀴놀린- 5-일)아다만테인 -1-카복사마이드 ¾ NMR (400 MHz, CDC1 3 ) δ 7.73 (d, J = 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd ᅳ 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 ᅳ 5H), 1.88-1.73 (m, 7H) MASS = 521.45 Synthesis Example 568: 3-Loro-N- (l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 5-day) adamantane-1-carboxamide
5-아미노 _L-(4-메특시벤질)퀴놀린— 2(iH)-온 (10mg, 0.02隱01)을 CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03瞧 ol), 3-클로로아다만테인 -1- 카르보닐 클로라이드 (6.52mg, 0.02瞧 ol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 60%) 5 -Amino_L- ( 4 -methoxybenzyl) quinolin—2 (iH) -one (10 mg, 0.02'01) is dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (7.8λ, 0.03 'ol), 3- Chloroadamantane-1-carbonyl chloride (6.52 mg, 0.02dl ol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 60%).
¾ NMR (400MHz, CDC13) 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 합성예 569 ： 2- (아다만탄 -1-일) -N-(l-(4-메톡시벤질) -2-옥소 -1,2—디하이드 로퀴놀린 -5-일)아세트아마이드 ¾ NMR (400 MHz, CDC1 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 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 Synthesis Example 569: 2- (adamantane-1-yl) -N- (l- (4-methoxybenzyl) -2-oxo- 1,2-dihydroquinolin-5-yl) acetamide
5-아미노 -1-(4-메특시벤질)퀴놀린 -2(1H)-온 (10mg, 0.02讓 ol)을 5-amino-1- (4-mesoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 μl)
CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03隱01) ， 2- (아드만탄 -1- 일)아세틸 클로라이드 (5.95mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 70%) Ή NMR (400MHz, CDC13) 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 합성예 570 ： N-(l-(4-메록시벤질) -2-옥소 -1,2—디하이드로퀴놀린 -5-일) -2- (3-메틸아다만탄 -1-일)아세트아마이드 After dissolving in CH 2 C1 2 (1 ml), DIPEA (7.8λ, 0.03x01) and 2- (admantan-1-yl) acetyl chloride (5.95mg, 0.02mmol) are stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 70%). NMR (400 MHz, CDC1 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 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 Synthesis Example 570: N- (l- (4-methoxybenzyl) -2-oxo-1,2—dihydro Quinolin-5-yl) -2- (3-methyladamantane-l-yl) acetamide
5-아미노 -1-(4-메록시벤질)퀴놀린 -2(1H)—온 (10mg, 0.02mmol)을 CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ , 0.03隱01)， 2-(3_메틸아드만탄 -1- 일)아세틸 클로라이드 (6.33mg, 0.02瞧 ol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 N S04로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 71%). 5-amino-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.02 mmol) was dissolved in CH 2 C1 2 (1 ml) and then DIPEA (7.8λ, 0.03 隱0 1), 2 -(3_methyladmantan-1-yl) acetyl chloride (6.33 mg, 0.02dl ol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous N SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 71%).
¾ 醒 (400MHz, CDC13) δ 7.73(d, /=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 합성예 571 ： 2-(3，5-디메틸아다만탄 -1-일) -N-(l-(4-메톡시벤질) 2-옥소- 1,2-디하이드로퀴놀린 -5-일)아세트아마이드 ¾ 醒 (400 MHz, CDC1 3 ) δ 7.73 (d, / = 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 Synthesis Example 571: 2- (3,5-dimethyladamantane-1-yl) -N -(l- (4-methoxybenzyl) 2-oxo- 1,2-dihydroquinolin-5-yl) acetamide
5-아미노 -1-(4-메톡시벤질)퀴놀린 -2(1H)—온 (10mg, 0.02mmol)을 CH2C12 (1ml)에 ' 용해한 후 DIPEA (7.8λ , 0.03隱 ol), 2-(3,5- 디메틸아드만탄 -1-일)아세틸 클로라이드 (6.7½g, 0.02隱 ol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 66%) 5-amino-1- (4-methoxybenzyl) quinolin -2 (1H) - one (10mg, 0.02mmol), the CH 2 C1 2 was dissolved 'in (1ml) DIPEA (7.8λ, 0.03隱ol), 2 -(3,5-dimethyladmantan-1-yl) acetyl chloride (6.7½ g, 0.02 cc ol) is stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 66%).
¾ 匪 R (400MHz, CDCI3) δ 7.73 (d, J - 8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H)， 7.18 (dd, / = 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 합성예 572 ： 2-(3—브로모아다만탄 -1-일) -N-(l-(4-메특시벤질) -2-옥소 -1，2- 디하이드로퀴놀린 -5-일)아세트아마이드 ¾ 匪 R (400 MHz, CDCI 3 ) δ 7.73 (d, J-8 Hz, 1H), 7.47 (b, s, 1H), 7.42-7.36 (m, 2H), 7.18 (dd, / = 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 Synthesis example 572: 2- (3-bromoadamantane-1-yl) -N- (l- (4-methoxybenzyl) -2-oxo-l, 2-dihydroquinolin-5-yl) acetamide
5-아미노 - 1- ( 4-메특시벤질)퀴놀린 -2 ( 1H ) -온 ( lOmg， 0.02mmo 1 )을 CH2C12(1 ml)에 용해한 후 DIPEA (7.8λ , 0.03隱01)， 2-(3-브로모메틸아드 만탄 -1-일)아세틸 클로라이드 (8.16mg, 0.02mmol)을 상온에 서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 64%). 5-amino-1- (4-methoxybenzyl) quinoline-2 (1H) -one (lOmg, 0.02mmo 1) was dissolved in CH 2 C1 2 (1 ml) and then DIPEA (7.8λ, 0.03 隱0 1) , 2- (3-bromomethyladmantan-1-yl) acetyl chloride (8.16 mg, 0.02 mmol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 64%).
¾ NMR (400MHz, CDC13) δ 7.73 (d, / = 8 Hz, 1H) , 7.47 (b, s,¾ NMR (400 MHz, CDC1 3 ) δ 7.73 (d, / = 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 합성예 573 ： 2-(3-클로로아다만탄 -1-일) -N-(l-(4-메록시벤질) -2—옥소 -1,2- 디하이드로퀴놀린 -5-일 )아세트아마이드 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 Synthesis Example 573 ： 2- (3-chloroadamantane-1-yl) -N- (l- (4-methoxybenzyl) -2—oxo-1,2-dihydroquinolin-5-yl) acetamide
5-아미노 _L-(4-메톡시벤질)퀴놀린 2(1H)-온 (lOmg, 0.02mmol)을 5 -amino-L- (4-methoxybenzyl) quinolin 2 (1H) -one (lOmg, 0.02 mmol)
CH2C12 (1ml)에 용해한 후 DIPEA (7.8λ， 0.03讓01)， 2-(3-클로로메틸 아드만탄 -1-일)아세틸 클로라이드 (6.92mg, 0.02mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 N S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토 그래피로 정제하여''목적 화합물을 수득하였다 (수율 = 66%) . After dissolving in CH 2 C1 2 (1ml), DIPEA (7.8λ, 0.03 讓0 1), 2- (3-chloromethyl admantan-1-yl) acetyl chloride (6.92mg, 0.02mmol) were added at room temperature for 4 hours. Stir. Then extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous NSO 4 , concentrated in vacuo and purified by column chromatography to afford the `` target compound (yield = 66%).
¾ NMR (400MHz, CDC13) δ 7.73 (d, J - 8 Hz, 1H), 7.47 (b, s,¾ NMR (400 MHz, CDC1 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 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),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 합성예 574 ： N'-(l-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -5-일)아다 만테인 -1-카르보하이드라자이드 2.09 (s, 2H) 2.08-2.05 (m, 5H), 1.88-1.73 (m, 7H) MASS = 491.02 Synthesis Example 574: N '-(l- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide
5-하이드라지닐 -1-(4-메톡시벤질)퀴놀린 -2(1H)-온 (lOmg, 0.03國01)을 5-hydrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H) -one (lOmg, 0.03 國 01)
CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.0½mol), 아다만테인 -1-아세틸 클로라이드 (5.9½g, 0.03画01)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 66%) . DIPEA (11.7λ, 0.0½mol), Adamantane-1-acetyl after dissolving in CH 2 C1 2 (1ml) Chloride (5.9½ g, 0.03x01) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 66%).
¾ NMR (400MHz, CDC13) 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 합성예 575 ： ^ 1-(4-메록시벤질)-2-옥소-1，2-디하이드로퀴놀린-5-일)-3- 메틸아다만테인 -1-카르보하이드라자이드 ¾ NMR (400 MHz, CDC1 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, 3H), 1.80-1.65 (m , 7H) MASS = 457.57 Synthesis Example 575: ^ 1- (4-Methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carbohai Drazide
5-하이드라지닐 -1-(4-메특시벤질)퀴놀린 -2(1H)-온 (10mg, 0.03瞧01)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7入， 0.04誦 01)， 3-메틸아다만테인 -1- 아세틸 클로라이드 (5.94mg, 0.03醒 ol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층올 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 70%) 5-Hydrazinyl-1- (4-mesoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.03 瞧 01) was dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (11.7 入 ， 0.04 誦0 1 ), 3-methyladamantane-1-acetyl chloride (5.94mg, 0.03dl ol) is stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 70%).
¾ NMR (400MHz, CDC13) δ 7.89 ,(d, / = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, / = 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, / = 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 합성예 576 ： ^-(1-(4-메록시벤질)-2-옥소-1，2-디하이드로퀴놀린-5-일)- 3， 5-디메틸아다만테인 -1-카르보하이드라자이드 ¾ NMR (400 MHz, CDC1 3 ) δ 7.89, (d, / = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, / = 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, / = 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 Synthesis Example 576: ^-(1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3, 5- Dimethyladamantane-1-carbohydrazide
5-하이드라지닐 -1— (4-메록시벤질)퀴놀린 -2(1H)-온 (10mg, 0.03mmol)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.04mmol), 3,5- 디메틸아다만테인 -1-아세틸 클로라이드 (6.80mg, 0.03隱01)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 71%) 5-Hydrazinyl-1— (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.03 mmol) was dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (11.7λ, 0.04 mmol), 3 , 5-Dimethyladamantane-1-acetyl chloride (6.80mg, 0.03x01) is stirred at room temperature for 4 hours. Then extracted with ethyl acetate and ¾0. Combined The organic layer was dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 71%).
賺 (400MHz, CDCls) 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, 7 = 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 합성예 577 ： 3-브로모 -N'-(l-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린- 5-일)아다만테인 -i-카르보하이드라자이드  400 (400 MHz, CDCls) 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, 7 = 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 Synthesis Example 577: 3-Bromo-N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5yl) Adamantane-i-carbohydrazide
5-하이드라지닐 - 1- ( 4—메록시벤질)퀴놀린 -2 ( 1H ) -온' (10mg， 0.03隱 o 1 )을 CH2C12 (lml)에 용해한 후 DIPEA (11.7λ , 0.0½mol), 3-브로모아다만테인- 1-아세틸 클로라이드 (8.32mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고, 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 75%) 5-Hyrazinyl- 1- (4- hydroxybenzyl) quinoline-2 (1H) -one ' (10mg, 0.03 隱 o 1) is dissolved in CH 2 C1 2 (lml), then DIPEA (11.7λ, 0.0½mol ), 3-bromoadamantane-1-acetyl chloride (8.32 mg, 0.03 mmol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 75%).
¾ NMR (400MHz, CDCI3) δ 7.89 ,(d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H) , 6.87 (d, / = 12 Hz, 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, / = 8 Hz, 1H), 6.63 (d, / = 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 합성예 578 ： 3-클로로 -N'-(l-(4-메톡시벤질) -2-옥소 -1,2-디하이드로퀴놀린- 5-일)아다만테인 -1-카르보하이드라자이드  ¾ NMR (400 MHz, CDCI3) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H), 6.87 (d, / = 12 Hz , 1H), 6.81 (d, J = 8 Hz, 2H), 6.70 (d, / = 8 Hz, 1H), 6.63 (d, / = 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 Synthesis Example 578 ： 3-Chloro-N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5 yl) adamantane-1-car Bohydrazide
5-하이드라지닐 -1-(4-메특시벤질)퀴놀린 -2(1H)—온 (lOing, 0.03隱01)올 CH2C12 (lml)에 용해한 후 DIPEA (11.7λ , 0.0½mol), 3-브로모아다만테인- 1-아세틸 클로라이드 (6.99mg, 0.03隱01)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 75%). Ή NMR (400MHz' CDC13) δ 7.89 ,(d, / = 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, / = 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 합성예 579 ： 2- (아다만탄 -1-일) -N'-(l-(4-메록시벤질) -2-옥소 -1,2-디하이드 로퀴놀린 -5-일)아세토하이드라자이드 5-hydrazinyl-1- (4-mesoxybenzyl) quinolin-2 (1H) -one (lOing, 0.03x01) ol dissolved in CH 2 C1 2 (lml), followed by DIPEA (11.7λ, 0.0½mol), 3-Bromoadamantane-1-acetyl chloride (6.99 mg, 0.03x01) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 75%). MR NMR (400 MHz 'CDC1 3 ) δ 7.89, (d, / = 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, / = 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 Synthesis Example 579: 2- (adamantane-1-yl) -N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline -5-day) acetohydrazide
5-하이드라지닐 -1-(4-메록시벤질)퀴놀린 -2(1H)-온 (10mg, 0.03mmol)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.04隱 ol), 2- (아다만탄 -1- 일)아세틸 클로라이드 (6.38mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%). 5-Hyrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.03 mmol) was dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (11.7 λ, 0.04 μ ol), 2- (adamantane-1-yl) acetyl chloride (6.38 mg, 0.03 mmol) is stirred at room temperature for 4 hours. Thereafter, the mixture was extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 77%).
¾ NMR (400MHz, CDC13) δ 7.89 ,(d, / = 8 Hz, 1H), 7.38 (b, s,¾ NMR (400 MHz, CDC1 3 ) δ 7.89, (d, / = 8 Hz, 1H), 7.38 (b, s,
1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 12 Hz, 1H), 6.81 (d, / = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, / = 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 합성예 580 ： N'-(l— (4-메특시벤질) 2-옥소— 1，2-디하이드로퀴놀린 -5-일) -2- (3-메틸아다만탄 -1-일)아세토하이드라자이드 1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 12 Hz, 1H), 6.81 (d, / = 8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H) , 6.63 (d, / = 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 Synthesis Example 580 ： N '-(l— (4-method) Benzyl) 2-oxo— 1,2-dihydroquinolin-5-yl) -2- (3-methyladamantane-1-yl) acetohydrazide
5-하이드라지닐 -1— (4-메특시벤질)퀴놀린 -2(1H)-온 (10mg, 0.03睡01)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.04難 ol), 2-(3—메틸아다만탄 -1- 일)아세틸 클로라이드 (6.80mg, 0.03mmol)을 상온에서 4시간 동안 교반한다. 그 후, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수5-Hydrazinyl-l— (4-methoxybenzyl) quinolin-2 (1H) -one (10 mg, 0.03'01) was dissolved in CH 2 C1 2 (1 ml) and then DIPEA (11.7λ, 0.04 'ol) , 2- (3-methyladamantan-1-yl) acetyl chloride (6.80 mg, 0.03 mmol) is stirred at room temperature for 4 hours. Then extracted with ethyl acetate and ¾0. The combined organic layer is anhydrous
Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%) Dried over Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 77%).
¾ 匪 R (400MHz , CDCI3) δ 7.89 ,(d, J = 8 Hz , 1H), 7.38 (b, s,¾ 匪 R (400 MHz, CDCI 3 ) δ 7.89, (d, J = 8 Hz, 1H), 7.38 (b, s,
1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 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)ᅦ'-(1-(4ᅳ메톡시벤질)-2-옥소- 1，2-디하이드로퀴놀린 -5-일)아세토하이드라자이드 1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 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 Synthesis Example 581: 2- (3,5-dimethyladamantan-1-yl) ''-(1- (4'methoxybenzyl) -2-oxo-1,2-di Hydroquinolin-5-yl) acetohydrazide
5-하이드라지닐 -1-(4ᅳ메특시벤질)퀴놀린 -2(1H)ᅳ온 (lOmg, 0.03隱01)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.0½mol), 2-(3，5- 디메틸아다만탄-： h일)아세틸 클로라이드 (7.21mg, 0.03隱 ol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 77%) 5-Hyrazinyl-l- (4'methoxybenzyl) quinoline-2 (1H) thion (lOmg, 0.03'01) was dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (11.7λ, 0.0½mol), 2 -(3,5-Dimethyladamantane-: hyl) acetyl chloride (7.21 mg, 0.03dl ol) is stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 SO 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 77%).
¾ NMR (400MHz, CDC13) δ 7.89 ,(d, / = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 12 Hz, 1H), 6.81 (d, J = S Hz, 2H), 6.70 (d, J = S Hz, 1H) , 6.63 (d, / = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, / = 8 Hz, / = 8 Hz, 1H), 3.75 -3.73 (m, 3H) ), 2.09 (s, 2H), 2.05-2.00 (m, 4H) , 1.90-1.85 (111， 3H), 1.80-1.65 (m, 7H), 0.89 (s, 6H) MASS=499.65 합성예 582 ： 2-(3-브로모아다만탄 -1-일) -N'-(l-(4-메록시벤질) -2-옥소 -1ᅳ2ᅳ 디하이드로퀴놀린 -5-일 )아세토하이드라자이드 ¾ NMR (400 MHz, CDC1 3 ) δ 7.89, (d, / = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, / = 8 Hz, 2H), 6.87 (d, / = 12 Hz, 1H), 6.81 (d, J = S Hz, 2H), 6.70 (d, J = S Hz, 1H), 6.63 (d, / = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, / = 8 Hz, / = 8 Hz, 1H), 3.75 -3.73 (m, 3H), 2.09 (s, 2H), 2.05-2.00 (m, 4H), 1.90-1.85 (111, 3H ), 1.80-1.65 (m, 7H), 0.89 (s, 6H) MASS = 499.65 Synthesis Example 582: 2- (3-Bromoadamantan-1-yl) -N '-(l- (4-methoxy Benzyl) -2-oxo-1 ᅳ 2 ᅳ dihydroquinolin-5-yl) acetohydrazide
5-하이드라지닐 -1-(4-메록시벤질)퀴놀린 -2(1H)-온 (lOmg, 0.03mmol)을 5-hydrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H) -one (lOmg, 0.03 mmol)
CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.04讓 ol), 2-(3-브로모아다만탄- 1-일)아세틸 클로라이드 (8.74mg, 0.03隱 ol)을 상온에서 4시간 동안 교반한다. 그 후， 에틸아세테이트 및 0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 80%) CH 2 C1 2 DIPEA (11.7λ, 0.04讓ol), 2- (3- bromo collected adamantan-1-1) was dissolved in (1ml) of acetyl chloride (8.74mg, 0.03隱ol) at room temperature for 4 hours Stir. Thereafter, the mixture was extracted with ethyl acetate and zero. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 80%).
¾ NMR (400MHz, CDC13) δ 7.89 ,(d, / = 8 Hz, 1H) , 7.38 (b, s, 1H), 7.13 (d, / = 8 Hz, 2H) , 6.87 (d, J = 12 Hz, 1H), 6.81 (d, J = 8¾ NMR (400 MHz, CDC1 3 ) δ 7.89, (d, / = 8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, / = 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, / = 8 Hz, / = 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 합성예 583 ： 2-(3-클로로아다만탄 -1-일) -N'-(l-(4-메톡시벤질) -2-옥소 -1,2- 디하이드로퀴놀린 -5-일)아세토하이드라자이드 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, J = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, / = 8 Hz, / = 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 Synthesis Example 583: 2- (3-chloroadamantane-1-yl) -N '-(l- (4-methoxybenzyl) -2 -Oxo-1,2-dihydroquinolin-5-yl) acetohydrazide
5-하이드라지닐 -1-(4ᅳ메록시벤질)퀴놀린 -2(1H)_온 (10mg, 0.03隱 ol)을 CH2C12 (1ml)에 용해한 후 DIPEA (11.7λ , 0.04顏 ol), 2-(3-클로로아다만탄- 1-일)아세틸 클로라이드 (7.41mg, 0.03隱01)을 상온에서 4시간 동안 교반한다. 그 후，, 에틸아세테이트 및 ¾0로 추출하였다. 합쳐진 유기층을 무수 Na2S04로 건조시키고， 진공에서 농축하여 컬럼 크로마토그래피로 정제하여 목적 화합물을 수득하였다 (수율 = 82%) 5-Hydrinyl-1- (4 ᅳ hydroxybenzyl) quinolin-2 (1H) _one (10 mg, 0.03 隱 ol) was dissolved in CH 2 C1 2 (1 ml), followed by DIPEA (11.7λ, 0.04 顏 ol), 2- (3-chloro-adamantane-1- yl) acetyl chloride (7.41mg, 0.03隱0 1) and stirred at room temperature for 4 hours. Then, extracted with ethyl acetate and ¾0. The combined organic layers were dried over anhydrous Na 2 S0 4 , concentrated in vacuo and purified by column chromatography to give the desired compound (yield = 82%).
¾ 匪 R (400MHz, CDC13) δ 7.89 ,(d, / - 8 Hz, 1H) , 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H); 6.87 (d, / = 12 Hz, 1H)， 6.81 (d, J = .8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, / = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, / = 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 (in, 7H) MASS=506.04 [표 4】 „ ¾ 匪 R (400 MHz, CDC1 3 ) δ 7.89, (d, /-8 Hz, 1H), 7.38 (b, s, 1H), 7.13 (d, J = 8 Hz, 2H) ; 6.87 (d, / = 12 Hz, 1H), 6.81 (d, J = .8 Hz, 2H), 6.70 (d, J = 8 Hz, 1H), 6.63 (d, / = 8 Hz, 1H), 5.45 (b, s, 2H), 4.14 (dd, / = 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 (in, 7H) MASS = 506.04 [Table 4] „
합성된 화합물의 구조 및 분광학 데이터 (합성예 561-583)  Structure and Spectroscopy Data of Synthesized Compound (Synthesis Example 561-583)
Figure imgf000344_0001
Figure imgf000344_0001
Figure imgf000345_0001
Figure imgf000345_0001
JZ.J600M0ZaM/X3d 6.C0S0/Sl0i OAV //:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 JZ.J600M0ZaM / X3d 6.C0S0 / Sl0i OAV // : / OZ / -Z600 1 S2MI > d 6 / .SS0SSZAV 7
Figure imgf000346_0001
Figure imgf000346_0001
//:/ O Z/-Z6001S2MI>d 6/.SS0SSZAV7 // : / OZ / -Z600 1 S2MI > d 6 / .S S0 SSZAV 7
Figure imgf000347_0001
Figure imgf000347_0001
/ zz-soono/zHMld/.SS0 OSSZAV / zz-soono / zHM ld / .SS0 O S S Z A V
Figure imgf000348_0001
Figure imgf000348_0001
8 8
Figure imgf000349_0001
Figure imgf000349_0001
ZLZ600/nOZ yi/L3d 6Z.C0S0/S10Z OAV 실험예 ZLZ600 / nOZ yi / L3d 6Z.C0S0 / S10Z OAV Experimental Example
IL-2 억제활성의 측정  Measurement of IL-2 Inhibitory Activity
본 발명자들은 퀴놀린 화합물들의 면역억제 활성을 조사하기 위해 ELISA를 통해 IL-2의 생성을 측정하였다. Jurkat T 림프구 (lxlO6 cells/ml)를 24ᅳ웰 플레이트에 씨딩하였다. 각 웰의 세포들에 ΙΟμΜ또는 ΙμΜ의 최종농도로 시험 화합물을 처리하고 500nlvl 이노마이신 및 5η ΜΡΜΑ를 처리하여 세포를 자극하였다. 세포들은 37°C에서 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. We measured the production of IL-2 via ELISA to investigate the immunosuppressive activity of quinoline compounds. Jurkat T lymphocytes (lxlO 6 cells / ml) were seeded in 24-well well plates. Cells in each well were treated with test compounds at a final concentration of ΙΟμΜ or ΙμΜ and treated with 500 nlvl inomycin and 5η ΜΡΜΑ to stimulate the cells. Cells were incubated at 37 ° C. for 13 hours and centrifuged at 4800 rpm for 2 minutes to collect the supernatant of each well. The amount of IL-2 expression was measured by ELISA using anti-human IL-2 antibody as a capture antibody and biotinylated anti-human IL-2 antibody as a detection antibody.
[표 5】 TABLE 5
각 화합물의 10 μΜ농도에서의 IL-2 억제활성 IL-2 inhibitory activity at 10 μΜ concentration of each compound
Figure imgf000350_0001
Figure imgf000350_0001
IL-2 (Jurkat cell) //10μΜ % inhibition A ： 60 % < activity < 100 % B ： 30 % < activity < 60 % IL-2 (Jurkat cell) // 10μΜ% inhibition A: 60% <activity <100% B ： 30% <activity <60%
C ： 0 % < activity < 30 %  C: 0% <activity <30%
IL-Ιβ 억제활성의 측정 Measurement of IL-Ιβ Inhibitory Activity
자가면역 질환에 관련되는 중요한 사이토카인 중 하나로 알려진 인터루킨-113(11 61"16'0 11-113， IL-Ιβ)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 콕스 2 C0X2)에 의해 유도된다. 관련 질환으로는 큰 범주와 자가면역 질환， 염증성 통증 및 세포독성 스트레스 (cytotoxic stressed)와도 관련된 다. 이에， 본 발명자들은 퀴놀리논 화합물들의 면역억제 활성을 조사하기 위해 ELISA를 통해 IL-Ιβ의 생성을 측정하였다 【표 6】 Interleukin-113 (11 61 " 16'0 11-113, IL-Ιβ), known as one of the important cytokines involved in autoimmune diseases, belongs to the Interleukin 1 category and is produced by activated macrophages. Is an important factor in the immune response and is associated with a variety of cellular activities, for example cell activity, cell growth, differentiation and apoptosis, which are also induced by Cox 2 C0X2). It is also associated with the categories and autoimmune diseases, inflammatory pain and cytotoxic stressed, and we measured the production of IL-Ιβ through ELISA to investigate the immunosuppressive activity of quinolinone compounds. 6]
화합물 530-583의 10 μΜ 농도에서의 ILᅳ 1β 억제활성  IL ᅳ 1β Inhibitory Activity at 10 μΜ Concentration of Compound 530-583
Figure imgf000351_0001
Figure imgf000351_0001
Ιί-1β//10μΜ % inhibition  Ιί-1β // 10μΜ% inhibition
A ： 60 % < activity < 100 %  A: 60% <activity <100%
B ： 30 % < activity < 60 %  B ： 30% <activity <60%
C ： 0 % < activity < 30 % hP2X7-발현 HEK293세포에서의 에티듐 (Ethidhun) 축적 C ： 0% <activity <30% Ethidhun accumulation in hP2X 7 -expressing HEK293 cells
자가면역 질환의 중요한 타킷으로 알려져 있는 P2X7 수용체에서의 길항적인 (antagonistic) 활성을 알아보기 위해 EtBr 업테이크 분석을 진행 하였다. P2X7 수용체는 자가면역 질환에 관련되는 중요한 사이토카인 IL- 1β와 관련된 중요한 수용체이다. 2，(3')-0-(4-벤조일벤조일 )-^?(82^?)은 Λ/ ^발현 ΗΕΚ293 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. HP2X그발현 HEK293 세포를 2.5 x 106 eel ls/ml로 에티듐 브로마이드 0.1 mM, 에틸렌디아민 테트라아세틱애시드 (EDTA) 1 mM, 글루코스 5 mM, HEPES 20 mM 및 염화칼륨 140 mM(pH 7.4)을 포함하는 HEPES-완층 염 용액에서 재부유하였다. 96-웰 플레이트에 세포 부유물을 처리하고 BzATP를 첨가하였다. 플레이트를 37°C에서 120분 간 배양하고， 에티듐의 세포 축적을 형광 플레이트 리더로 측정하였다 (530/20 여기 필터 및 590/20 발광필터). EtBr uptake assays were performed to investigate the antagonistic activity of P2X7 receptors, which is an important target for autoimmune diseases. P2X7 receptors are important receptors associated with IL-1β, an important cytokine involved in autoimmune diseases. 2, (3 ')-0- (4-benzoylbenzoyl)-^? (82 ^?) Promotes ethidium ion accumulation in Λ / ^ expression ΗΕΚ293 cells. Recombinant human P2X 7 is functionally expressed in stably transformed human HEK293 cells. The synthesized quinolinone derivatives were each added to 96-well plates (black with clear bottom). HP2XGexpressing HEK293 cells contain 2.5 mM x 10 6 eel ls / ml of 0.1 mM ethidium bromide, 1 mM ethylenediamine tetraacetic acid (EDTA), glucose 5 mM, HEPES 20 mM and potassium chloride 140 mM (pH 7.4). Resuspended in HEPES-buffered salt solution. Cell suspensions were treated in 96-well plates and BzATP was added. Plates were incubated at 37 ° C. for 120 minutes and cell accumulation of ethidium was measured with a fluorescent plate reader (530/20 excitation filter and 590/20 luminescence filter).
【표 7】 Table 7
화합물 530— 560의 10 μΜ 농도에서의 EtBr 업테이크 분석결과  EtBr Uptake Assay at 10 μΜ Concentration of Compounds 530—560
Figure imgf000352_0001
Figure imgf000352_0001
EtBr //ΙΟ Μ % inhibition  EtBr // ΙΟ Μ% inhibition
Α '： 60 % < activity < 100 % Α ': 60% <activity < 100%
B ： 30 % < activity < 60 %  B ： 30% <activity <60%
C ： 0 % < activity < 30 % 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.  C: The specific part of the present invention has been described in detail with 0% <activity <30% or more. For those skilled in the art, this specific technology is merely a preferred embodiment, and the scope of the present invention is limited. It is obvious that it is not. Accordingly, the substantial scope of the invention will be defined by the appended claims and equivalents thereof.

Claims

【특허청구범위】  [Patent Claims]
【청구항 1】  [Claim 1]
다음의 화학식 1로 표시되는 퀴놀리논 (quinol inone) 유도체 또는 이의 약제학적으로 허용되는 염:  Quinol inone derivative represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
1  One
Figure imgf000353_0001
Figure imgf000353_0001
상기 화학식에서， Ri, 2 및 ¾는 각각 독립적으로 수소， 니트로， In the above formula, Ri, 2 and ¾ are each independently hydrogen, nitro,
할로겐, -NH2 , 하이드라지노 또는
Figure imgf000353_0002
( 은 비치환되거나 d— C5 알킬， 할로겐， C2-C5 알케닐, 니트로， 하이드록시， 하이드록시 d-C5 알킬, d-C3 알콕시 또는 페닐로 치환된 C6-C10 아릴; 비치환되거나 할로겐, 니트로， C2- C5 알케닐로 치환된 d-Cs 알킬; C5-C6 사이클로알킬; 비치환되거나 할로겐 또는 d-Cs 알킬로 치환된 아다만테인; d-Cs 알콕시; d-C5 알킬티오; 또는 벤조디옥솔이고; 'n은 0-2의 정수이다)이고; R4는 수소， C厂 C5 알킬, 騎 2 (A2는 비치환되거나 할로겐, C厂 C5 알킬， C ;3 알콕시， 니트로， ― H2 ( C1-C5 알킬티오， 페닐， 페닐 Ci-C5 알킬， 페녹시， 시아노， 하이드록시， 하이드록시 d-Cs 알킬, 포르밀， 페닐티오 또는 피라졸로 치환된 C6-C10 아릴; 사이클로펜타디엔; 피롤; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 Ci-C5 알킬, d-C3 알콕시, 할로겐， 니트로， 시아노, 하이드록시, 포르밀， d-C5 알킬티오 또는 -N¾로 치환된 디하이드로인덴; 또는 디페닐메틸이고; in은 0-2의 정수이다) 또는 ! ^ (A3는 d-Cs 알킬 ; d-C3 알콕人 비치환되거나 d-Cs 알콕시， d-Cs 알킬, 하이드록시 , 할로겐， 니트로， -NH2 , 포르밀, 시아노, d-C5 알킬티오， 페녹시， 페닐티오, 페닐 C厂 C3 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피롤; C5-C6 사이클로알킬; 비치환되거나 d-C5 알킬, d- s 알콕시， 할로겐, 니트로， 하이드록시, d-C5 알킬티오 또는 -N¾로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p 및 q는 각각 독립적으로 0-2의 정수이다)이고; R5는 수소, C厂 C5 알콕시 C -C3 알킬， -NA4A5(A4 및 A5는 각각 독립적으로 수소; 비치환되거나 페닐， 디하이드로인덴 나프탈릴， d-Cs 알콕시 또는 d-C3 알킬티오로 치환된 d- C5 알킬; 비치환되거나 d-C5 알킬， 할로겐, 하이드록시 d-C5 알킬, C2-C5 알케닐, 설폰아마이드 C C3 알콕시， 하이드록시 또는 니트로로 치환된 페닐이다) 또는 '^ [A6는 d-C3 알콕시, 할로겐, 하이드록시, d-C3 알킬티오 또는 -NA7A8(A7 및 A8은 각각 독립적으로 수소; 비치환되거나 페닐, 니트로， 하이드특시， 할로겐， 디하이드로인덴， 나프탈릴， C— C3 알콕시, d- C3 알킬아민 또는 C厂 C3 알킬티오로 치환된 C厂 C5 알킬; C2-C5 알케닐; 비치환되거나 d-C5 알킬， 할로겐， 하이드록시 d-Cs 알킬, C2_C5 알케닐， 설폰아마이드， 알콕시， 하이드톡시 또는 니트로로 치환된 페닐이다) ] 이다. Halogen, -NH 2 , hydrazino or
Figure imgf000353_0002
(C 6 -C 10 aryl unsubstituted or substituted with d— C 5 alkyl, halogen, C 2 -C 5 alkenyl, nitro, hydroxy, hydroxy dC 5 alkyl, dC 3 alkoxy or phenyl; D-Cs alkyl substituted with halogen, nitro, C 2 -C 5 alkenyl; C 5 -C 6 cycloalkyl; adamantane unsubstituted or substituted with halogen or d-Cs alkyl; d-Cs alkoxy; dC 5 Alkylthio, or benzodioxol, 'n is an integer from 0-2); R 4 is hydrogen, C 厂 C 5 alkyl, 騎2 (A 2 is unsubstituted or halogen, C 厂 C 5 alkyl, C; 3 alkoxy, nitro, —H 2 ( C1-C5 alkylthio, phenyl, phenyl Ci- C 5 alkyl, phenoxy, cyano, hydroxy, hydroxy-d-Cs-alkyl, formyl, phenylthio or pyrazolo-substituted C 6 -C 10 aryl; dicyclopentadiene; pyrrole; furan; thiophene; C 5 -C 6 cycloalkyl; dihydroindene unsubstituted or substituted with Ci-C 5 alkyl, dC 3 alkoxy, halogen, nitro, cyano, hydroxy, formyl, dC 5 alkylthio or -N¾; or diphenyl Methyl; in is an integer from 0-2) or ! ^ (A 3 is d-Cs alkyl; dC 3 alkoxyne unsubstituted or d-Cs alkoxy, d-Cs alkyl, hydroxy, halogen, nitro, -NH 2, formyl, cyano, dC 5 alkylthio, phenoxy, phenylthio, phenyl-C 3 alkyl or C厂pyrazolo substituted phenyl; furan; thiophene; pyrrole; C 5 -C 6 cycloalkenyl ; Unsubstituted or dC 5 alkyl, d- s alkoxy, halogen, nitro, hydroxy, dC 5 Dihydroindene substituted with alkylthio or -N¾; Or diphenylmethyl; p and q are each independently integers of 0-2); R 5 is hydrogen, C 厂 C 5 alkoxy C-C 3 alkyl, -NA 4 A 5 (A 4 and A 5 are each independently hydrogen; unsubstituted or phenyl, dihydroindene naphthalyl, d-Cs alkoxy or d-C 5 alkyl substituted with dC 3 alkylthio; phenyl unsubstituted or substituted with dC 5 alkyl, halogen, hydroxy dC 5 alkyl, C 2 -C 5 alkenyl, sulfonamide CC 3 alkoxy, hydroxy or nitro Or ' ^ [A 6 is dC 3 alkoxy, halogen, hydroxy, dC 3 alkylthio or -NA 7 A 8 (A 7 and A 8 are each independently hydrogen; unsubstituted or substituted with phenyl, nitro, Or C 厂 C 5 alkyl substituted with halogen, dihydroindene, naphthalyl, C—C 3 alkoxy, d-C 3 alkylamine or C 厂 C 3 alkylthio; C 2 -C 5 alkenyl; unsubstituted or phenyl substituted with dC 5 alkyl, halogen, hydroxy d-Cs alkyl, C 2 _C 5 alkenyl, sulfonamide, alkoxy, hydroxy or nitro ))
15. 【청구항 2】 15. Claim 2
제 1 항에 있어서， 상기 , R2및 ¾는 각각 독립적으로 수소， 니트로， According to claim 1, wherein, R 2 And ¾ are each independently hydrogen, nitro,
할로겐, -NH2 , 하이드라지노 또는
Figure imgf000354_0001
(A은 비치환되거나 C厂 C3 알킬, 할로겐， C2-C3 알케닐， 니트로， 하이드록시， 하이드록시 d-C3 알킬， C厂 C3 알콕시 또는 페닐로 치환된 페닐; 나프탈릴; 비치환되거나 할로겐， 20 니트로， C2-C3 알케닐로 치환된 C厂 C3 알킬; C5-C6 사이클로알킬; 비치환되거나 할로겐 또는 메틸로 치환된 아다만테인; CrC3 알콕시; d-C3 알킬티오; 또는 벤조디옥솔이고; n은 0-2의 정수이다)인 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염. Halogen, -NH 2 , hydrazino or
Figure imgf000354_0001
(A is unsubstituted or C厂C 3 alkyl, halogen, C 2 -C 3 alkenyl, nitro, hydroxy, hydroxy-dC 3 alkyl, phenyl substituted by C厂C 3 alkoxy, or phenyl; naphthyl talril; unsubstituted C 3 alkyl substituted or substituted with halogen, 20 nitro, C 2 -C 3 alkenyl; C 5 -C 6 cycloalkyl; adamantane, unsubstituted or substituted with halogen or methyl; CrC 3 alkoxy; dC 3 alkyl Thio; or benzodioxol; n is an integer of 0-2). A quinolinone derivative or a pharmaceutically acceptable salt thereof.
25 【청구항 3】 제 1 항에 있어서， 상기 R4는 수소， 알킬, 솨 m (A2는 비치환되거나 할로겐， 알킬， d— C3 알콕시， 니트로, -NH2 , C1-C3 알킬티오， 페닐， 페닐 d- j 알킬, 페녹시， 시아노, 하이드록시， 하이드록시 Ci-C3 알킬, 포르밀， 페닐티오 또는 피라졸로 치환된 페닐; 나프탈릴; 사이클로펜타디엔; 피를; 퓨란; 티오펜; C5-C6 사이클로알킬; 비치환되거나 C厂 C3 알킬， C厂 C3 알콕시， 할로겐, 니트로, 시아노， 하이드록시， 포르밀， d-C3 알킬티오 또는 -NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; 25. The method of claim 1, wherein R4 is hydrogen, alkyl, 솨 m (A 2 is unsubstituted or halogen, alkyl, d—C 3 alkoxy, nitro, —NH 2 , C1-C3 Phenyl substituted with alkylthio, phenyl, phenyl d-j alkyl, phenoxy, cyano, hydroxy, hydroxy Ci-C 3 alkyl, formyl, phenylthio or pyrazole; Naphthalyl; Cyclopentadiene; Blood; Furan; Thiophene; C 5 -C 6 cycloalkyl; Dihydroindene unsubstituted or substituted with C 厂 C 3 alkyl, C 厂 C 3 alkoxy, halogen, nitro, cyano, hydroxy, formyl, dC 3 alkylthio or -NH 2 ; Or diphenylmethyl;
tn은 0-2의 정수아다) 또는
Figure imgf000355_0001
(Α3는 C广 C3 알킬; d-C3 알콕시 ; 비치환되거나 d— C3 알콕시， d-C3 알킬， 하이드록시， 할로겐， 니트로， ᅳ N¾ , 포르밀, 시아노， d-Cs 알킬티오， 페녹시 , 페닐티오， 페닐 d-C3 알킬 또는 피라졸로 치환된 페닐; 퓨란; 티오펜; 피를; C5-C6 사이클로알킬; 비치환되거나 d-C3 알킬， d-C3 알콕시ᅳ 할로겐， 니트로， 하이드록시 , d-C3 알킬티오 또는 — NH2로 치환된 디하이드로인덴; 또는 디페닐메틸이고; p는 0이며 q는 0-2의 정수이다)인 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염. 【청구항 4】 tn is an integer from 0-2) or
Figure imgf000355_0001
(Α 3 is C 广 C 3 alkyl; dC 3 alkoxy; unsubstituted or d—C 3 alkoxy, dC 3 alkyl, hydroxy, halogen, nitro, ᅳ N¾, formyl, cyano, d-Cs alkylthio ， phenoxy Phenyl substituted by phenylthio, phenyl dC 3 alkyl or pyrazole; furan; thiophene; phyfen; c 5 -C 6 cycloalkyl; unsubstituted or dC 3 alkyl, dC 3 alkoxy ᅳ halogen, nitro, hydroxy, dC 3 alkylthio or —dihydroindene substituted with NH 2 ; or diphenylmethyl; p is 0 and q is an integer from 0-2). Salt. [Claim 4]
제 1 항에' 있어서, 상기 ¾는 수소， CrCs 알콕시 dᅳ C2 알킬， - NA4A5(A4 및 A5는 각각 독립적으로 수소; 비치환되거나 페닐， 디하이드로인덴， 나프탈릴， 알콕시 또는 C厂 C3 알킬티오로 치환된 d— C3 알킬; 비치환되거나 d-Cs 알킬， 할로겐， 하이드록시 d-C3 알킬, C2-C3 알케닐, 설폰 ， Ci-C3 알콕시， 하이드록시 또는 니트로로 치환된 페닐이다) 또는
Figure imgf000355_0002
[A6는 d-C3 알콕시 , 할로겐, 하이드록시， d-Cz 알킬티오 또는 - NA7A8(A7 및 A8은 각각 독립적으로 수소; 비치환되거나 페닐， 니트로, 하이드록시， 할로겐， 디하이드로인덴, 나프탈릴, Ci-C3 알콕시， 알킬아민 또는 d-C2 알킬티오로 치환된 d-C3 알킬; C2-C3 알케닐; 비치환되거나 d-( 3 알킬， 할로겐, 하이드록시 C厂 C3 알킬, C2-C3 알케닐， 설폰아마이드, d-C3 알콕시, 하이드록시 또는 니트로로 치환된 페닐이다) ]인 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염. 【청구항 5】 According to claim 1 ', wherein ¾ is hydrogen, CrCs alkoxy d eu C 2 alkyl, - NA 4 A 5 (A 4 and A 5 are each independently hydrogen, unsubstituted or substituted phenyl, dihydro-indene, naphthyl talril, D—C 3 alkyl substituted with alkoxy or C 厂 C 3 alkylthio; unsubstituted or d-Cs alkyl, halogen, hydroxy dC 3 alkyl, C 2 -C 3 alkenyl, sulfone, Ci-C 3 alkoxy, hydroxy Phenyl substituted by oxy or nitro) or
Figure imgf000355_0002
[A 6 is dC 3 alkoxy, halogen, hydroxy, d-Cz alkylthio or —NA 7 A 8 (A 7 and A 8 are each independently hydrogen; unsubstituted or phenyl, nitro, hydroxy, halogen, dihydro DC 3 alkyl substituted with indene, naphthalyl, Ci-C 3 alkoxy, alkylamine or dC 2 alkylthio; C 2 -C 3 alkenyl; unsubstituted or d- ( 3 alkyl, halogen, hydroxy C 厂 C 3 alkyl, C 2 -C 3 alkenyl, sulfonamide, dC 3 alkoxy, hydroxy or phenyl substituted with nitro)]. A quinolinone derivative or a pharmaceutically acceptable salt thereof. [Claim 5]
제 1 항에 있어서, 상기 퀴놀리논 유도체는  According to claim 1, wherein the quinolinone derivative is
( 1) 1-(4-에틸벤질 )-5ᅳ니트로 -2-옥소 -N-펜에틸 -1 , 2-디하이드로퀴놀린ᅳ 3- 카복사마이드;  (1) 1- (4-ethylbenzyl) -5mnitro-2-oxo-N-phenethyl-1, 2-dihydroquinoline® 3-carboxamide;
(2) 1-(4-에틸펜에틸) -5-니트로 2-옥소— N-펜에틸 -1，2-디하이드로퀴놀린ᅳ3- 카복사마이드;  (2) 1- (4-ethylphenethyl) -5-nitro 2-oxo—N-phenethyl-1,2-dihydroquinoline ᅳ 3-carboxamide;
(3) 1-(4-플루오로벤질 )-5-니트로 -2-옥소 -Nᅳ펜에틸— 1， 2-디하이드로퀴놀린- 3-카복사마이드;  (3) 1- (4-fluorobenzyl) -5-nitro-2-oxo-N ᅳ phenethyl— 1, 2-dihydroquinoline-3-carboxamide;
(4) 1-(4-플루오로펜에틸) -5-니트로 -2-옥소ᅳ N-펜에틸 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (4) 1- (4-fluorophenethyl) -5-nitro-2-oxoox 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 -1ᅳ(4-니트로벤질 )-2-옥소 -N-펜에틸 -1ᅳ 2-디하이드로퀴놀린 -3- 카복사마이드;  (6) 5-nitro-1 '(4-nitrobenzyl) -2-oxo-N-phenethyl-1' 2-dihydroquinoline-3-carboxamide;
(7) 1-(4ᅳ아미노벤질) -5-니트로 -2-옥소 -N-¾에틸 -1 , 2-디하이드로퀴놀린 -3- 카복사마이드; , (7) 1- (4′aminobenzyl) -5-nitro-2-oxo-N-¾ethyl-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-디하이드로퀴놀 린 -3-카복사마이드; (9) 1- (naphthalen-2-ylmethyl) -5-nitro-2-oxo—N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
( 10) 1— ( [ 1，1 ' -비페닐 ]ᅳ4-일메틸 )-5-니트로 -2-옥소 -N-펜에틸 -1，2-디하이드 로퀴놀린 -3-카복사마이드;  (10) 1— ([1,1'-biphenyl] ᅳ 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 -Nᅳ펜에틸 -1— (4-페녹시벤질) -1 , 2-디하이드로퀴놀린 -3- 카복사마이드;  (12) 5-nitro-2-oxo-N ᅳ phenethyl-1— (4-phenoxybenzyl) -1, 2-dihydroquinoline-3-carboxamide;
( 13) 1ᅳ(4ᅳ클로로펜에틸) -5-니트로 -2-옥소 -N-펜에틸ᅳ 1， 2-디하이드로퀴놀린- 3-카복사마이드;  (13) 1 '(4'chlorophenethyl) -5-nitro-2-oxo-N-phenethyl ᅳ 1,2-dihydroquinoline-3-carboxamide;
( 14) 1ᅳ (4-아미노펜에틸 )-5-니트로 -2-옥소 -N-펜에틸 -1 , 2-디하이드로퀴놀린一 3—카복사마이드; (15) l-(4-시아노펜에틸 )-5-니트로 -2-옥소 -N-펜에틸 -1， 2-디하이드로퀴놀린- 3-카복사마이드; (14) 1 ′ (4-aminophenethyl) -5-nitro-2-oxo-N-phenethyl-1, 2-dihydroquinoline Ⅰ 3—carboxamide; (15) l- (4-cyanophenethyl) -5-nitro-2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
(16) 5-니트로 -1-(4ᅳ니트로펜에틸 )-2-옥소 -Nᅳ펜에틸 -1,2-디하이드로퀴놀린- 3-카복사마이드;  (16) 5-nitro-1- (4 ᅳ nitropenethyl) -2-oxo-N ᅳ phenethyl-1,2-dihydroquinoline-3-carboxamide;
(17) 메틸 7-니트로 -2-옥소— 1,2-디하이드로퀴놀린ᅳ 3-카르복실레이트; (17) methyl 7-nitro-2-oxo— 1,2-dihydroquinoline® 3-carboxylate;
(18) 메틸 1-(2ᅳ (사이클로펜타 -1,3-디엔 -1-일)에틸) -그니트로 -2-옥소 -1,2- 디하이드로퀴놀린」 3-카르복실레이트；  (18) methyl 1- (2 ′ (cyclopenta-1,3-diene-1-yl) ethyl) -gnitro-2-oxo-1,2-dihydroquinoline ”3-carboxylate;
(19) 메틸 5-니트로 -2-옥소 -1,2ᅳ디하이드로퀴놀린 -3-카르복실레이트;  (19) methyl 5-nitro-2-oxo-1,2'dihydroquinoline-3-carboxylate;
(20) 메틸 1-에틸—5ᅳ니트로 -2-옥소 -1，2-디하이드로퀴놀린 -3-카르복실레이트; (21) 메틸 1-메틸 -5-니트로 -2-옥소 -1,2—디하이드로퀴놀린 -3-카르복실레이트; (20) methyl 1-ethyl-5phenylni-2--2-oxo-1,2-dihydroquinoline-3-carboxylate; (21) methyl 1-methyl-5-nitro-2-oxo-1,2—dihydroquinoline-3-carboxylate;
(22) 메틸 1-아세틸 -5-니트로—2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카르복실레이 트； (22) methyl 1-acetyl-5-nitro-2-oxo-1, 2'dihydroquinoline-3-carboxylate;
(23) 메틸 2-옥소ᅳ 1，2-디하이드로퀴놀린 -3-카르복실레이트;  (23) methyl 2-oxo ᅳ 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 -3ᅳ카르보닐 브로마이드; (25) 2-oxo-1,2-dihydroquinoline-3'carbonyl bromide;
(26) 2-옥소 -1,2-디하이드로퀴놀린 -3—카르보닐 플루오라이드;  (26) 2-oxo-1,2-dihydroquinoline-3-carbonyl fluoride;
(27) 2-옥소 -1，2-떠하이드로퀴놀린 -3-카르보닐 아이오다이드;  (27) 2-oxo-1,2-subhydroquinoline-3-carbonyl iodide;
(28) 2-옥소 -N-페닐 -1,2-디하이드로퀴놀린ᅳ 3-카복사마이드;  (28) 2-oxo-N-phenyl-1,2-dihydroquinoline® 3-carboxamide;
(29) 1-메틸— 2ᅳ옥소 -N-페닐 -1,2-디하이드로퀴놀린 -3-카복사마이드;  (29) 1-methyl—2oxo-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 페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (32) 5-benzamido-2-oxo phenyl-1, 2-dihydroquinoline-3-carboxamide;
(33) 1— ( (2H-피롤— 2-일)메틸) -5-벤즈아미도 -2-옥소ᅳ N—페닐 -1， 2-디하이드로 퀴놀린 -3-카복사마이드; (33) 1— ((2H-pyrrole— 2-yl) methyl) -5-benzamido-2-oxoze N-phenyl-1, 2-dihydro quinoline-3-carboxamide;
(34) 5-(4ᅳ메틸벤즈아미도) -2-옥소 -Nᅳ페닐 -1,2-디하이드로퀴놀린ᅳ 3-카복사 마이드; (34) 5- (4'methylbenzamido) -2-oxo-N'phenyl-l, 2-dihydroquinoline® 3-carboxamide;
(35) 1-(2-(2Η—피를 -2—일)에틸) -5— (4-메틸벤즈아미도 )-2-옥소 -N-페닐 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드;  (35) 1- (2- (2Η—blood -2—yl) ethyl) -5— (4-methylbenzamido) -2-oxo-N-phenyl-1, 2-dihydroquinoline-3- Carboxamide;
(36) 5-(4-브로모벤즈아미도) -2-옥소 -N-페닐— 1，2—디하이드로퀴놀린 -3-카복 사마이드;  (36) 5- (4-bromobenzamido) -2-oxo-N-phenyl— 1,2-dihydroquinoline-3-carboxamide;
(37) 2-옥소 -Nᅳ (P-를일) -1,2ᅳ디하이드로퀴놀린 -3-카복사마이드; (38) 1-메틸 -2-옥소 -N-(p-를일 )-1 , 2—디하이드로퀴놀린 -3-카복사마이드；(37) 2-oxo-N '(P-ylyl) -1,2'dihydroquinoline-3-carboxamide; (38) 1-methyl-2-oxo-N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(39) 1-에틸 -2-옥소 -Ν-(ρ-를일 )-1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드；(39) 1-ethyl-2-oxo-Ν- (ρ-ylyl) -1,2'dihydroquinoline-3-carboxamide;
(40) 5— (4-클로로벤즈아미도)ᅳ 2ᅳ옥소 -Ν-(ρ-를일) -1， 2-디하이드로퀴놀린 -3- 카복사마이드; (40) 5— (4-chlorobenzamido) ᅳ 2 ᅳ oxo-Ν- (ρ-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(41) Ν-(4-메톡시페닐) -2—옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드; (41) Ν- (4-methoxyphenyl) -2—oxo-1, 2-dihydroquinoline® 3-carboxamide;
(42) 5-(4-플루오로벧즈아미도) -Ν-(4-메톡시페닐 )-2-옥소ᅳ 1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (42) 5- (4-fluorobetasamido) -Ν- (4-methoxyphenyl) -2-oxoxol 1, 2-dihydro quinoline-3-carboxamide;
(43) 5-(4-에틸벤즈아미도) -Ν-(4ᅳ메록시페닐 )-2-옥소ᅳ 1 , 2ᅳ디하이드로퀴놀린 -3-카복사마이드;  (43) 5- (4-ethylbenzamido) -Ν- (4'methoxyphenyl) -2-oxo '1, 2'dihydroquinoline-3-carboxamide;
(44) Ν-(4-브로모페닐) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (44) Ν- (4-bromophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(45) Ν-(4-브로모페닐) -2-옥소ᅳ 5-(4-비닐벤즈아미도 )ᅳ1，2ᅳ디하이드로퀴놀린 -3-카복사마이드;  (45) Ν- (4-bromophenyl) -2-oxoze 5- (4-vinylbenzamido) # 1,2'dihydroquinoline-3-carboxamide;
(46) Ν-(4-브로모페닐) -2-옥소 -1-(2- (티오펜ᅳ 2ᅳ일)에틸) -5-(4-비닐벤즈 아미도 )-1， 2-디하이드로퀴놀린 -3-카복사마이드；  (46) Ν- (4-bromophenyl) -2-oxo-1- (2- (thiophenyl-2-hexyl) ethyl) -5- (4-vinylbenz amido) -1, 2-dihydroquinoline -3-carboxamide;
(47) Ν-(4-클로로페닐 )ᅳ2ᅳ옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드; (47) Ν- (4-chlorophenyl) ᅳ 2 ᅳ oxo-1,2-dihydroquinoline-3-carboxamide;
(48) Ν-(4-클로로페닐) -1-메틸— 2-옥소 -1， 2—디하이드로퀴놀린 -3-카복사 마이드； '·..  (48) Ν- (4-chlorophenyl) -1-methyl- 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(49) Ν-(4ᅳ클로로페닐) -1-에틸 -2—옥소 -1ᅳ 2-디하이드로퀴놀린 -3-카복사 마이드;  (49) Ν- (4′chlorophenyl) -1-ethyl-2—oxo-1′2-dihydroquinoline-3-carboxamide;
(50) Ν-(4-클로로페닐) -5_(4-니트로벤즈아미도) -2-옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드; (50) Ν- (4-chlorophenyl) -5_ (4-nitrobenzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(51 ) Ν-(4ᅳ클로로페닐 )-1-메틸 -5— (4-니트로벤즈아미도)— 2-옥소— 1， 2-디하이 드로퀴놀린 -3-카복사마이드;  (51) Ν- (4 ᅳ chlorophenyl) -1-methyl-5— (4-nitrobenzamido) —2-oxo—1,2-dihydrodroquinoline-3-carboxamide;
(52) Ν-(4ᅳ클로로페닐 )-1-에틸 -5ᅳ (4-니트로벤즈아미도) -2-옥소 -1， 2-디하이 드로퀴놀린 -3-카복사마이드;  (52) Ν- (4′chlorophenyl) -1-ethyl-5 ′ (4-nitrobenzamido) -2-oxo-1,2-dihydrodroquinoline-3-carboxamide;
(53) 5ᅳ(4-브로모벤즈아미도) -Νᅳ (4-클로로페닐 )-2—옥소— 1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (53) 5 ′ (4-bromobenzamido) -Ν ᅳ (4-chlorophenyl) -2—oxo—1,2-dihydro quinoline-3-carboxamide;
(54) 5-(4-브로모벤즈아미도) -Ν-(4-클로로페닐) -1-메틸 -2-옥소 -1，2-디하이 드로퀴놀린 -3-카복사마이드；  (54) 5- (4-bromobenzamido) -Ν- (4-chlorophenyl) -1-methyl-2-oxo-1,2-dihydrodroquinoline-3-carboxamide;
(55) 5— (4-브로모벤즈아미도)ᅳ Ν-(4-클로로페닐)—1-에틸 -2-옥소 -1 , 2-디하이 드로퀴놀린 -3-카복사마이드; (56) N-(4-클로로페닐) -5-(4- (하이드록시메틸)벤즈아미도) -2-옥소 -1，2- 디하이드로퀴놀린 -3-카복사마이드; (55) 5— (4-bromobenzamido) 'Ν- (4-chlorophenyl) —1-ethyl-2-oxo-1, 2-dihydrodroquinoline-3-carboxamide; (56) N- (4-chlorophenyl) -5 (4- (hydroxymethyl) benzamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(57) N- -클로로페닐) -5-(4- (하이드록시메틸)벤즈아미도) -1-메틸 -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (57) N-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) N- (4—chlorophenyl) — 1- (furan-2-ylmethyl) — 5— (4- (hydroxymethyl) benzamido) -2—oxo-1, 2-dihydroquinoline- 3-carboxamide;
(60) N-(4—클로로페닐) -5-(4ᅳ니트로벤즈아미도) -2-옥소 -1 , 2-디하이드로 퀴놀린 -3—카복사마이드; (60) N- ( 4 —chlorophenyl) -5 (4-nitrobenzamido) -2-oxo-1, 2-dihydro quinoline-3—carboxamide;
(61) N-(4-클로로페닐) -1-메틸— 5-(4—니트로벤즈아미도) -2ᅳ옥소 -1，2-디하이 드로퀴놀린 -3—카복사마이드;  (61) N- (4-chlorophenyl) -1-methyl- 5- (4-nitrobenzamido) -2ioxo-l, 2-dihydrodroquinoline-3-carboxamide;
' (62) N-(4-클로로페닐) -1-에틸 -5-(4-니트로벤즈아미도 )-2-옥소 -1 , 2-디하이 드로퀴놀린 -3-카복사마이드; '(62) N- (4-chlorophenyl) -1-ethyl-5- (4-nitro-benz amido) -2-oxo-1,2-di-high draw-3-carboxamide;
(63) N— (4-클로로페닐 )ᅳ1-(2- (퓨란 -2-일)에틸 )-5ᅳ(4-니트로벤즈아미도) -2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (63) N— (4-chlorophenyl) ᅳ 1- (2- (furan-2-yl) ethyl) -5 ᅳ (4-nitrobenzamido) -2-oxo-1, 2-dihydroquinoline- 3-carboxamide;
(64) N-(4-클로로페닐 )-2-옥소 -5_(2-페닐아세트아미도) -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (64) N- (4-chlorophenyl) -2-oxo-5_ (2-phenylacetamido) -1, 2-dihydro quinoline-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—디하이드로 퀴놀린 -3-카복사마이드;  (67) N- (4-chlorophenyl) -5 (4—ethylbenzamido) —2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(68) N-(4-클로로페닐) -5-(4ᅳ에틸벤즈아미도) -1-메틸 -2-옥소 -1，2-디하이드 로퀴놀린 -3-카복사마이드;  (68) N- (4-chlorophenyl) -5- (4 ᅳ ethylbenzamido) -1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(69) N-(4—클로 έ페닐) -1-에틸 -5-(4-에틸벤즈아미도) -2-옥소ᅳ 1 , 2-디하이드 로퀴놀린 -3-카복사마이드;  (69) N- (4—chlorophenyl) -1-ethyl-5- (4-ethylbenzamido) -2-oxoxin 1, 2-dihydroquinoline-3-carboxamide;
(70) Ν-(4-플루오로페닐) -2-옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드； (71) Ν— (4-플루오로페닐 )-1ᅳ메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3ᅳ카복사 마이드; (72) 1ᅳ에틸 -N-(4-플루오로페닐 )-2-옥소— 1 , 2-디하이드로퀴놀린 -3-카복사 마이드; (70) Ν- (4-fluorophenyl) -2-oxo-1, 2-dihydroquinoline— 3-carboxamide; (71) Ν— (4-fluorophenyl) -1 ᅳ methyl-2- Oxo-1,2-dihydroquinoline-3′carboxamide; (72) 1 ᅳ ethyl-N- (4-fluorophenyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(73) 1-( (2H-피를 -3-일)메틸) -N-(4—플루오로페닐 )-2—옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (73) 1- ((2H-pyr-3-yl) methyl) -N- (4—fluorophenyl) -2—oxo-1, 2-dihydro quinoline-3-carboxamide;
(74) N-(4-플루오로페닐 )-2-옥소 -5-(2-(p-를일)아세트아미도 )-1 , 2-디하이드 로퀴놀린 -3-카복사마이드; (74) N- (4-fluorophenyl) -2-oxo-5- (2- (p-ylyl) acetamido) -1, 2-dihydroquinoline-3-carboxamide;
(75) N-(4-플루오로페닐 )ᅳ1-메틸 -2-옥소 -5-(2-(p-를일)아세트아미도 )ᅳ1，2- 디하이드로퀴놀린 -3-카복사마이드;  (75) N- (4-fluorophenyl) ᅳ 1-methyl-2-oxo-5- (2- (p-ylyl) acetamido) ᅳ 1,2-dihydroquinoline-3-carboxamide;
(76) 1-에틸 -N-(4-플루오로페닐 )-2ᅳ옥소 -5-(2-(p-틀일)아세트아미도 )-1， 2- 디하이드로퀴놀린 -3-카복사마이드;  (76) 1-ethyl-N- (4-fluorophenyl) -2 ᅳ oxo-5- (2- (p-tyl) acetamido) -1,2-dihydroquinoline-3-carboxamide;
(77) N-(4-에틸페닐 )-2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드；  (77) N- (4-ethylphenyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide;
(78) N-(4-에틸페닐 )-1-메틸 -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3-카복사마이드； (78) N- (4-ethylphenyl) -1-methyl-2-oxo-1,2'dihydroquinoline-3-carboxamide;
(79) 1-에틸 -N-(4—에틸페닐 )-2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복사마이드；(79) 1-ethyl-N- (4—ethylphenyl) -2-oxoxo 1, 2-dihydroquinoline-3-carboxamide;
(80) 1-(2-(2Η-피를 -3-일)에틸 )-N— (4-에틸페닐 )-2-옥소 -1 ,2-디하이드로 퀴놀린 ᅳ3-카복사마이드; (80) 1- (2- (2Η-pyr-3-yl) ethyl) -N— (4-ethylphenyl) -2-oxo-1,2-dihydro quinoline X3-carboxamide;
(81) 5-(2-(4-브루모페닐 )아세트아미도) -N-(4-에틸페닐 )-2-옥소 -1， 2-디하이 드로퀴놀린 -3-카복사마이드;  (81) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(82) 5-(2-(4-브로모페닐)아세트아미도) -N-(4-에틸페닐) -2—옥소ᅳ 1- (티오펜- 2-일메틸 )-1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (82) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -2—oxoze 1- (thiophene-2-ylmethyl) -1, 2-di Hydroquinoline-3-carboxamide;
(83) 5-(2-(4-브로모페닐)아세트아미도) -N-(4-에틸페닐) -1-메틸— 2-옥소- 1， 2-디하이드로퀴놀린 -3-카복사마이드； (83) 5- (2- (4-bromophenyl) acetamido) -N- (4-ethylphenyl) -1-methyl- 2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(84) 5-(2-(4-브로모페닐)아세트아미도 )-1ᅳ에틸 -N-(4-에틸페닐 )-2-옥소- 1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (84) 5- (2- (4-bromophenyl) acetamido) -1 ᅳ ethyl-N- (4-ethylphenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(85) N-(4-하이드록시페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드; (86) N-(4-하이드록시페닐) -1-메틸 -2-옥소ᅳ 1 , 2-디하이드로퀴놀린 -3ᅳ 카복사마이드;  (85) N- (4-hydroxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (86) N- (4-hydroxyphenyl) -1-methyl-2-oxoxin 1, 2-dihydroquinoline-3 ′ carboxamide;
(87) 1-에틸 -N-(4ᅳ하이드록시페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (87) 1-ethyl-N- (4′hydroxyphenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(88) N-(4-하이드록시페닐 )-2-옥소 -1ᅳ(2- (티오펜 -2—일)에틸 )-1 , 2-디하이드 로퀴놀린 -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-하이드톡시페닐 )-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-(4ᅳ하이드록시페닐) -1-메틸ᅳ 2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (90) 5- (2- (4-chlorophenyl) acetamido) — N- (4 ᅳ hydroxyphenyl) -1-methyl ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide ;
(91) 5-(2-(4-클로로페닐 )아세트아미도 )-1-에틸 -N-(4-하이드록시페닐 )ᅳ2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (91) 5- (2- (4-chlorophenyl) acetamido) -1-ethyl-N- (4-hydroxyphenyl) ᅳ 2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(92) N-(4-니트로페닐 )ᅳ2-옥소— 1 , 2ᅳ디하이드로퀴놀린 -3—카복사마이드； (92) N- (4-nitrophenyl) ᅳ 2-oxo— 1, 2'dihydroquinoline-3—carboxamide;
(93) 5-(2-(4-플루오로페닐)아세트아미도)— N-(4-니트로페닐 )-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-디하이 드로퀴놀린— 3-카복사마이드;  (94) 5- (2- (4-ethylphenyl) acetamido) -N- (4-nitrophenyl) -2-oxo-1, 2-dihydrodroquinoline—3-carboxamide;
(95) Ν-(4-(Ν , N-디메틸설파모일 )페닐 )-2-옥소 -1， 2—디하이드로퀴놀린 -3- 카복사마이드;  (95) Ν- (4- (Ν, N-dimethylsulfamoyl) phenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(96) Ν-(4-(Ν ,Ν-디메틸설파모일)페닐 )-1-메틸 -2-옥소 -1， 2-디하이드로퀴놀린 一 3-카복사마이드;  (96) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -1-methyl-2-oxo-1,2-dihydroquinoline one 3-carboxamide;
(97) Ν-(4-(Ν , Ν-디메틸설파모일)페닐) -1-에틸ᅳ 2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (97) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -1-ethyl ᅳ 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(98) 1- (사이클로핵실메틸 )-Ν-(4-(Ν,Ν-디메틸설파모일)페닐 )— 2-옥소— 1 , 2- 디하이드로퀴놀린 -3-카복사마이드;  (98) 1- (cyclonucleosilmethyl) -Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) — 2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(99) 1-(2ᅳ사이클로핵실에틸) -Ν-(4-(Ν ,Ν-디메틸설파모일)페닐) -2-옥소 -1，2- 디하이드로퀴놀린 -3-카복사마이드;  (99) 1- (2′cyclonucleosilethyl) -Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
( 100) Ν-(4- (하이드록시메틸)페닐) -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (100) Ν- (4- (hydroxymethyl) phenyl) -2oxoo-1, 2-dihydroquinoline-3-carboxamide;
( 101) Ν— (4- (하이드록시메틸)페닐 )ᅳ1-메틸 -2—옥소 -1， 2—디하이드로퀴놀린 -3- 카복사마이드;  (101) Ν-(4- (hydroxymethyl) phenyl) ᅳ 1 -methyl -2-oxo-1, 2 -dihydroquinoline-3-carboxamide;
( 102) 1-에틸 -Ν-(4- (하이드톡시메틸)페닐) -2-옥소 -1，2—디하이드로퀴놀린 -3- 카복사마이드; (102) 1-ethyl-Ν- (4- (hydroxymethyl) phenyl) -2-oxo-1,2—dihydroquinoline-3-carboxamide;
( 103) 1- (사이클로펜틸메틸)— Ν-(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) 2ᅳ옥소 -Ν-(4-비닐페닐 )—1， 2-디하이드로퀴놀린 -3-카복사마이드；  (104) 2oxo-N- (4-vinylphenyl) —1, 2-dihydroquinoline-3-carboxamide;
( 105) 1-메틸 -2-옥소— Ν-(4-비닐페닐) -1 , 2-디하이드로퀴놀린 -3-카복사마이드; ( 106) 1-에틸 -2-옥소ᅳ Ν—( 4-비닐페닐 )-1， 2—디하이드로퀴놀린 -3-카복사마이드； (107) 1_(2-사이클로펜틸에틸) -2-옥소 -N-(4-비닐페닐 )-1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (105) 1-methyl-2-oxo- Ν- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide; (106) 1-ethyl-2-oxo ᅳ N— (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide; (107) 1_ (2-cyclopentylethyl) -2-oxo-N- (4-vinylphenyl) -1, 2-dihydro quinoline-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 -Nᅳ (4-비닐페닐 ) -1， 2-디하이드로퀴놀린ᅳ 3—카복사마이드; (109) 5- (2- (4-hydroxyphenyl) acetamido) -1-methyl-_ 2-oxo-eu -N (4-vinylphenyl) -1, 2-dihydro-quinoline-3-carboxamide eu ;
( Π0) 1-에틸 -5-(2-(4ᅳ하이드록시페닐)아세트아미도 )-2-옥소 -N-(4-비닐페닐 ) -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (Π0) 1-ethyl-5- (2- (4'hydroxyphenyl) acetamido) -2-oxo-N- (4-vinylphenyl) -1,2-dihydroquinoline® 3-carboxamide ;
( 111) 1-( (2，3ᅳ디하이드로 1H-인덴 -2-일)메틸) -5-(2ᅳ(4-하이드록시페닐) 아세트아미도 )-2-옥소 -N- (4-비닐페닐) -1 , 2-디하이드로퀴놀린 -3-카복사마이  (111) 1-((2,3'dihydro 1H-inden-2-yl) methyl) -5- (2 '(4-hydroxyphenyl) acetamido) -2-oxo-N- (4-vinyl Phenyl) -1, 2-dihydroquinoline-3-carboxamide
( 112) 5-(2— (4-니트로페닐)아세트아미도)ᅳ 2-옥소 -N-(4-비닐페닐) -1 , 2- 디하이드로퀴놀린 -3-카복사마이드; (112) 5- (2— (4-nitrophenyl) acetamido) ᅳ 2-oxo-N- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide;
( 113) 1ᅳ메틸 -5-(2-(4-니트로페닐)아세트아미도 )ᅳ2-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 -^ -^-니트로페닐)아세트아미도 )ᅳ2-옥소 -N-(4-비닐페닐) - 1 , 2—디하이드로퀴놀린 -3-카복사마이드;  (114) 1-ethyl-^-^-nitrophenyl) acetamido) ᅳ 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-니트로 페닐)아세트아미도 ) -2-옥소ᅳ N- ( 4—비닐페닐) - 1， 2-디하이드로퀴놀린 -3ᅳ카복사 마이드；  (115) 1-((4-methoxy-2,3-dihydro-1H—inden-2-yl) methyl) -5— (2- (4-nitrophenyl) acetamido) -2-oxoxo N- (4—vinylphenyl) -1, 2-dihydroquinoline-3′carboxamide;
( 116) 1-( (5-메록시 -2ᅳ 3-디하이드로 -1H-인덴 -2-일 )메틸 )-5-(2-(4-니트로 페닐 )아세트아미도) -2-옥소 -N—( 4—비닐페닐 )-1 , 2ᅳ디하이드로퀴놀린 -3-카복사 마이드;  (116) 1-((5-Methoxy-2 ′ 3-dihydro-1H-inden-2-yl) methyl) -5- (2- (4-nitrophenyl) acetamido) -2-oxo- 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 -1ᅳ메틸—2-옥소 -1 , 2—디하이드로퀴놀린 -3-카복사마이드; (118) N-benzyl-1 -methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(119) N-벤질 -1ᅳ에'틸 -2-옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드; (119) N- benzyl-1 to eu 'butyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
( 120) 5_(2ᅳ(4—메록시페닐)아세트아미도 )-2-옥소 -N-페닐 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (120) 5_ (2 ′ (4—methoxyphenyl) acetamido) -2-oxo-N-phenyl-1,2-dihydro quinoline-3-carboxamide;
( 121) 1-( (5-에틸 -2 , 3-디하이드로 -1H-인덴— 2-일)메틸) -5-(2-(4—메록시페닐) 아세트아미도 )-2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (121) 1-((5-ethyl-2, 3-dihydro-1H-indene- 2-yl) methyl) -5 (2- (4- methoxyphenyl) acetamido) -2-oxo- N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
( 122) 1-( (5-플루오로 -2 , 3-디하이드로 -1H-인덴 -2-일)메틸 )ᅳ5-(2-(4-메특시 페닐)아세트아미도 )-2-옥소 -N-페닐ᅳ 1 , 2ᅳ디하이드로퀴놀린 -3-카복사마이드；(122) 1-((5-fluoro-2,3-dihydro-1H-inden-2-yl) methyl) ᅳ 5- (2- (4-method Phenyl) acetamido) -2-oxo-N-phenyl ᅳ 1, 2'dihydroquinoline-3-carboxamide;
( 123) 1-( (5-클로로 -2， 3-디하이드로ᅳ 1H-인덴 -2ᅳ일 )메틸 )-5_(2-(4-메특시페닐 ) 아세트아미도 )-2-옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드；(123) 1-((5-Chloro-2,3-dihydro ᅳ 1H-inden-2 ylyl) methyl) -5_ (2- (4-methoxyphenyl) acetamido) -2-oxo-N- Phenyl-1, 2-dihydroquinoline-3-carboxamide;
( 124) 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )ᅳ2ᅳ옥소 -N—페닐 -1， 2- 디하이드로퀴놀린 -,3-카복사마이드; (124) 5- (2- (4- (hydroxymethyl) phenyl) acetamido) ᅳ 2ioxo-N-phenyl-1,2-dihydroquinoline- , 3-carboxamide;
( 125 ) 5-(2-( 4- (하이드록시메틸)페닐)아세트아미도) - 1- ( ( 5—아이오도 -2， 3- 디하이드로 -1Hᅳ인덴 -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-1H ᅳ inden-2-yl) methyl) 2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
( 126) . 5-(2-(4- (하이드록시메틸)페닐)아세트아미도 )-1ᅳ( (5-니트로 -2，3- 디하이드로 -1H-인덴 -2-일)메틸)ᅳ 2-옥소 페닐 -1， 2-디하이드로퀴놀린 -3- 카복사마이드; (126) . 5- (2- (4- (hydroxymethyl) phenyl) acetamido) -1 ᅳ ((5-nitro-2,3-dihydro-1H-inden-2-yl) methyl) ᅳ 2-oxo phenyl -1, 2-dihydroquinoline-3-carboxamide;
( 127) 2-옥소 -N-페닐 -5- (3-페닐프로판아미도) -1 , 2-디하이드로퀴놀린 -3- 카복사마이드;  (127) 2-oxo-N-phenyl-5- (3-phenylpropaneamido) -1, 2-dihydroquinoline-3-carboxamide;
( 128) 1-( (5-에틸 -2， 3-디하이드로 -1H-인덴 -2-일 )메틸) -2—옥소 -N-페닐ᅳ5-(3- 페닐프로판아미도) ,-1，2-디하이드로퀴놀린 -3-카복사마이드;  (128) 1-((5-ethyl-2, 3-dihydro-1H-inden-2-yl) methyl) -2—oxo-N-phenyl ᅳ 5- (3-phenylpropaneamido),-1 , 2-dihydroquinoline-3-carboxamide;
( 129) 5- (2- (4-에틸페닐)아세트아미도 )-2-옥소ᅳ N-페닐 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (129) 5- (2- (4-ethylphenyl) acetamido) -2-oxoze N-phenyl-1, 2-dihydro quinoline-3-carboxamide;
( 130) 1- ( 2- ( 2 , 3-디하이드로 - 1H—인덴 -2-일)에틸) -5- ( 2- ( 4-에틸페닐)아세트 아미도 )-2-옥소— N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드；  (130) 1- (2- (2, 3-dihydro-1H—inden-2-yl) ethyl) -5- (2- (4-ethylphenyl) acet amido) -2-oxo- N-phenyl -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-카복사 마이드;  (132) 1- (4-methoxybenzyl) -2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
( 133) 2-옥소 -N-펜에틸 -1-(4- (트리플루오로메톡시)벤질) -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (133) 2-oxo-N-phenethyl-1- (4- (trifluoromethoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide;
( 134) 1-(2-(4-메록시 -2，3-디하이드로 -1H-인덴 -2ᅳ일)에틸) 2-옥소 -N-펜에틸 -1ᅳ 2-디하이드로퀴놀린 -3-카복사마이드; (134) 1- (2- (4-Methoxy-2,3-dihydro-1H-inden-2 ylyl) ethyl) 2-oxo-N-phenethyl-1 '2-dihydroquinoline-3-car Copyamide;
( 135) 2-옥소 -N-펜에틸 -1-(2— (4— (트리플루오로메톡시) -2 , 3-디하이드로-lH- 인덴 -2-일)에틸 )-1 , 2-디하이드로퀴놀린— 3-카복사마이드；  (135) 2-oxo-N-phenethyl-1- (2— (4— (trifluoromethoxy) -2, 3-dihydro-lH-inden-2-yl) ethyl) -1, 2-di Hydroquinoline—3-carboxamide;
( 136) 5— (2— (4-메록시페닐 )아세트아미도 )-2-옥소 -N-펜에틸 -1 , 2-디하이드로 퀴놀린—3-카복사마이드;  (136) 5— (2— (4-methoxyphenyl) acetamido) -2-oxo-N-phenethyl-1, 2-dihydro quinoline—3-carboxamide;
( 137) 1-(4—메록시벤질) -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-3-carboxamide;
(138) 1-((4-하이드록시 -2,3-디하이드로 -1Η-인덴 -2-일)메틸) -5-(2-(4- 메톡시페닐)아세트아미도 )-2-옥소 -Ν-펜에틸 -1 ,2-디하이드로퀴놀린 -3—카복 사마이드;  (138) 1-((4-hydroxy-2,3-dihydro-1Η-inden-2-yl) methyl) -5 (2- (4-methoxyphenyl) acetamido) -2-oxo -N-phenethyl-l, 2-dihydroquinoline-3-carboxamide;
(139) 1-((4- 르밀 -2，3ᅳ디하이드로 -1Η-인덴— 2-일)메틸) -5-(2-(4ᅳ메록시 페닐)아세트아미도 )-2-옥소 펜에틸 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；(139) 1-((4-Rethyl-2,3 ᅳ dihydro-1Η-indene- 2-yl) methyl) -5 (2- (4 ᅳ methoxyphenyl) acetamido) -2-oxophenethyl- 1, 2-dihydroquinoline ᅳ 3-carboxamide;
(140) 1- ( ( 4-시아노 -2 , 3-디하이드로 - 1H-인덴 -2-일)메틸) -5- ( 2- ( 4-메톡시 페닐)아세트아미도 )-2-옥소 -Ν-펜에틸 -1,2-디하이드로퀴놀린ᅳ 3-카복사마이드;(140) 1-((4-cyano-2,3-dihydro-1H-inden-2-yl) methyl) -5 (2- (4-methoxyphenyl) acetamido) -2-oxo -N-phenethyl-1,2-dihydroquinoline® 3-carboxamide;
( 141) 5-(2-(4-브로모페닐 )아세트아미도 )—2-옥소 -Νᅳ펜에틸ᅳ 1， 2-디하이드로 퀴놀린 -3-카복사마이드; (141) 5- (2- (4-bromophenyl) acetamido) —2-oxo-N-phenphenethyl ᅳ 1, 2-dihydro quinoline-3-carboxamide;
(142) 5-(2-(4-브로모페닐)아세트아미도 )— 1-(4—메록시벤질) -2-옥소 -Ν- 펜에틸 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (142) 5- (2- (4-bromophenyl) acetamido) — 1- (4—methoxybenzyl) -2-oxo-Ν-phenethyl-1,2-dihydroquinoline-3-car Radiation amide;
(143) 2-옥소 -Ν-(3—페닐프로필) -1,2-디하이드로퀴놀린 -3-카복사마이드;  (143) 2-oxo-Ν- (3—phenylpropyl) -1,2-dihydroquinoline-3-carboxamide;
(144) 1-(4-메톡시벤질) -2-옥소 -Ν-(3-페닐프로필) -1,2-디하이드로퀴놀린 -3- 카복사마이드;  (144) 1- (4-methoxybenzyl) -2-oxo-Ν- (3-phenylpropyl) -1,2-dihydroquinoline-3-carboxamide;
( 145) 1-(2-(5-포르밀 2 , 3-디하이드로 -1Hᅳ인덴 -2-일)에틸 )ᅳ2ᅳ옥소 -Νᅳ (3- 페닐프로필) -1,2-디하이드로퀴놀린 -3-카복사마이드;  (145) 1- (2- (5-formyl 2,3-dihydro-1H ᅳ inden-2-yl) ethyl) ᅳ 2 ᅳ oxo-Ν ᅳ (3-phenylpropyl) -1,2-di Hydroquinoline-3-carboxamide;
(146) 1ᅳ(2-(5- (메틸티오) -2， 3-디하이드로 -1Η-인덴 -2-일)에틸 )-2-옥소 -Ν- (3-페닐프로필 )-1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (146) 1 '(2- (5- (methylthio) -2, 3-dihydro-1 Η-inden-2-yl) ethyl) -2-oxo-Ν- (3-phenylpropyl) -1, 2 -Dihydroquinoline® 3-carboxamide;
(147) Ν-(4-메틸벤질) -2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드; (147) Ν- (4-methylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(148) 1-(4-메톡시벤질) -Ν-(4-메틸벤질 )ᅳ2-옥소— 1，2-디하이드로퀴놀린 -3- 카복사마이드;  (148) 1- (4-methoxybenzyl) -Ν- (4-methylbenzyl) ᅳ 2-oxo— 1,2-dihydroquinoline-3-carboxamide;
(149) Ν-(4-메틸벤질) -2-옥소 -1-(3_ (트리플루오로메특시)펜에틸 )-1,2- 디하이드로퀴놀린 -3—카복사마이드;  (149) Ν- (4-methylbenzyl) -2-oxo-1- (3_ (trifluoromepoxy) phenethyl) -1,2-dihydroquinoline-3—carboxamide;
(150) 1-(3-시아노펜에틸) -Ν-(4-메틸벤질) -2-옥소ᅳ 1,2-디하이드로퀴놀린 -3- 카복사마이드; (150) 1- (3-cyanophenethyl) -Ν- (4-methylbenzyl) -2-oxoze 1,2-dihydroquinoline-3-carboxamide;
(151) Ν-(4ᅳ메틸펜에틸 )-2-옥소 -1 , 2—디하이드로퀴놀린 -3-카복사마이드； (151) Ν- (4 ᅳ methylphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 152) 1ᅳ(4- (하이드록시메틸 )벤질) -Ν-(4-메틸펜에틸) -2-옥소 -1 , 2ᅳ 디하이드로퀴놀린 -3-카복사마이드; (152) 1 ′ (4- (hydroxymethyl) benzyl) -Ν- (4-methylphenethyl) -2-oxo-1,2 ′ dihydroquinoline-3-carboxamide;
(153) 1-(4-에틸벤질) -N- -메틸펜에틸 )ᅳ2ᅳ옥소 -1,2-디하이드로퀴놀린 -3- 카복사마이드; ( 154) l-(4-메톡시벤질 )-N-(4-메틸펜에틸 )-2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드; (153) 1- (4-ethylbenzyl) -N-methylphenethyl) x2ioxo-l, 2-dihydroquinoline-3-carboxamide; (154) 1- (4-methoxybenzyl) -N- (4-methylphenethyl) -2ioxo-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 )ᅳ1-(4-메록시벤질) -N-(4-메틸펜 에틸 )-2-옥소— 1， 2ᅳ디하이드로퀴놀린 -3ᅳ카복사마이드； 156 5- (2- (4 '- chlorophenyl) acetamido) eu 1- (4-hydroxy-benzyl) -N- (4-methyl-phenethyl) -2-oxo-1,2 dihydro-quinoline eudi -3 ᅳ carboxamide;
( 157) N-(4-메록시벤질) -2—옥소ᅳ 1 , 2—디하이드로퀴놀린 -3-카복사마이드; (157) N- (4-methoxybenzyl) -2—oxoxin 1, 2—dihydroquinoline-3-carboxamide;
( 158) 1-(2-(5-아미노 -2，3ᅳ디하이드로 -1H-인덴 -2—일)에틸) -N-(4-메특시 벤질 )-2-옥소 -1， 2ᅳ디하이드로퀴놀린ᅳ 3ᅳ카복사마이드； (158) 1- (2- (5-amino-2,3'dihydro-1H-inden-2-2-yl) ethyl) -N- (4-methoxybenzyl) -2-oxo-1,2'dihydroquinoline '3'carboxamide;
( 159) 1-(2-(5_에틸 -2 , 3-디하이드로 -1H-인덴— 2-일)에틸 )— N-(4-메톡시벤질) -(159) 1- (2- (5_ethyl-2, 3-dihydro-1H-indene- 2-yl) ethyl)-N- (4-methoxybenzyl)-
2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 160) N-(4-메톡시펜에틸 )-2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (160) N- (4-methoxyphenethyl) -2 ᅳ oxo-1, 2-dihydroquinoline-3-carboxamide;
( 161) 1-(4-메록시벤질) -N-(4—메록시펜에틸 )-2-옥소ᅳ 1，2-디하이드로퀴놀린-(161) 1- (4-Methoxybenzyl) -N- (4—methoxyphenethyl) -2-oxo ᅳ 1,2-dihydroquinoline-
3-카복사마이드; 3-carboxamide;
( 162) 1-(2-(5-하이드록시 -2， 3-디하이드로 -1H-인덴 -2-일)에틸 )-N_(4-메톡시 펜에틸 )-2-옥소— 1ᅳ 2-디하이드로퀴놀린 -3-카복사마이드; (162) 1- (2- (5-hydroxy-2, 3-dihydro-1H-inden-2-yl) ethyl) -N_ (4-methoxy phenethyl) -2-oxo— 1- 2- Dihydroquinoline-3-carboxamide;
( 163) 1-( (2，3—디하이드로 -1H-인덴 -5-일)메틸) N-(4ᅳ메톡시펜에틸) -2-옥소- 1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (163) 1-((2,3—dihydro-1H-indene-5-yl) methyl) N- (4 ᅳ methoxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carbox Amide;
( 164) 1- ( 2— ( 2， 3-디하이드로 - 1Hᅳ인덴 -5-일)에틸) -N— ( 4-메톡시펜에틸 ) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (164) 1- (2— (2, 3-dihydro-1H ᅳ inden-5-yl) ethyl) -N— (4-methoxyphenethyl) -2-oxo-1, 2-dihydroquinoline -3-carboxamide;
( 165) 5— (2— (4-플루오로페닐)아세트아미도) -N-(4-메톡시펜에틸 )—2ᅳ옥소 -1 , 2 -디하이드로퀴놀린 -3-카복사마이드;  (165) 5— (2— (4-fluorophenyl) acetamido) -N- (4-methoxyphenethyl) —2oxoo-1,2-dihydroquinoline-3-carboxamide;
( 166) 5- ( 2- ( 4-에틸페닐)아세트아미도 ) -N- ( 4-메특시펜에틸)ᅳ 2-옥소 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드;  (166) 5- (2- (4-ethylphenyl) acetamido) -N- (4-mesoxifenethyl) ᅳ 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) -2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드; (168) 1-benzoyl -N- (4-bromobenzyl) -2oxoo-1, 2-dihydroquinoline-3-carboxamide;
( 169) N-(4-브로모벤질) -1-(4—메록시벤조일 )-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- -브로모펜에틸 )-1-(4ᅳ메록시벤질 )-2-옥소 -1，2-디하이드로퀴놀린- 3-카복사마이드; (171) N-bromophenethyl) -1- (4 ᅳ methoxybenzyl) -2-oxo-1,2-dihydroquinoline- 3-carboxamide;
(172) N-(4-브로모펜에틸 )-2-옥소 -1-(4- (트리플루오로메특시)벤조일 )-1，2- 디하이드로퀴놀린ᅳ 3-카복사마이드;  (172) N- (4-bromophenethyl) -2-oxo-1- (4- (trifluoromepoxy) benzoyl) -1,2-dihydroquinoline® 3-carboxamide;
( 173) N-(4-브로모펜에틸) -5-(2-(4-하이드록시페닐)아세트아미도) -2ᅳ옥소- 1， 2ᅳ디하이드로퀴놀린 -3-카복사마이드;  (173) N- (4-bromophenethyl) -5 (2- (4-hydroxyphenyl) acetamido) -2 ioxo-1,2 ᅳ dihydroquinoline-3-carboxamide;
( 174) N-(4-클로로벤질 )-2-옥소 -1 , 2—디하이드로퀴놀린— 3ᅳ카복사마이드； (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 )ᅳ2-옥소 -1,2-디하이드로 퀴놀린 -3-카복사마이드;  (176) N- (4-chlorobenzyl) -1- (4—hydroxybenzoyl) ᅳ 2-oxo-1,2-dihydro quinoline-3-carboxamide;
(177) N-(4-클로로펜에틸 )-2ᅳ옥소—1,2-디하이드로퀴놀린— 3-카복사마이드; (177) N- (4-chlorophenethyl) -2oxo-—1,2-dihydroquinoline—3-carboxamide;
(178) N-(4-클로로펜에틸 )-1-(4-메록시벤질) -2-옥소 -1，2-디하이드로퀴놀린- 3-카복사마이드; (178) N- (4-chlorophenethyl) -1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(179) 1ᅳ(4-클로로벤조일) -N-(4-클로로펜에틸 )-2-옥소 -1,2-디하이드로 퀴놀린 -3-카복사마이드;  (179) 1 ′ (4-chlorobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
(180) N-(4-클로로펜에틸 )-1— (4-아이오도벤조일) -2-옥소 -1,2-디하이드로 퀴놀린 -3-카복사마이드;  (180) N- (4-chlorophenethyl) -1— (4-iodobenzoyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
(181) N-(4-클로로펜에틸 )-1-(4-니트로벤조일 )-2-옥소— 1，2-디하이드로 퀴놀린 -3-카복사마이드;  (181) N- (4-chlorophenethyl) -1- (4-nitrobenzoyl) -2-oxo— 1,2-dihydro quinoline-3-carboxamide;
(182) 1-(4-아미노벤조일) -N-(4-클로로펜에틸 )-2-옥소 -1,2-디하이드로 퀴놀린 -3—카복사마이드; (182) 1- (4-aminobenzoyl) -N- (4-chlorophenethyl) -2-oxo-1,2-dihydro quinoline-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-(4ᅳ플루오로벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (185) N-(4- 루오로벤질) -1-(4-포르밀벤조일 )-2-옥소 -1,2-디하이드로 퀴놀린 -3-카복사마이드;  (184) N- (4'fluorobenzyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (185) N- (4- roobenzyl) -1- (4-form Milbenzoyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
( 186) 1-(4-시아노벤조일) -Ν-(4-플루오로벤질 )-2-옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (186) 1- (4-cyanobenzoyl) -N- (4-fluorobenzyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(187) Ν— (4-플루오로벤질 )-1-(4— (메틸티오)벤조일 )-2—옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드;  (187) Ν— (4-fluorobenzyl) -1- (4— (methylthio) benzoyl) -2—oxo-1,2-dihydro quinoline-3-carboxamide;
( 188) Ν-(4-플루오로펜에틸) -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3-카복사마이드； ( 189) N-(4-플루오로펜에틸 )ᅳ1-(4-메톡시벤질 )-2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드; (188) Ν- (4-fluorophenethyl) -2-oxoxol 1,2-dihydroquinoline-3-carboxamide; (189) N- (4-fluorophenethyl) ᅳ 1- (4-methoxybenzyl) -2-oxo-1, 2-dihydro quinoline-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-dihydro quinoline, -3-carboxamide;
( 191) N-(4ᅳ플루오로펜에틸) -1-(2-(4-메특시페닐)아세틸 )-2-옥소 -1，2- 디하이드로퀴놀린ᅳ 3ᅳ카복사마이드； (191) N- (4'fluorophenethyl) -1- (2- (4-methoxyphenyl) acetyl) -2-oxo-1,2-dihydroquinoline 3'carboxamide;
( 192) N-(4ᅳ플루오로펜에틸) -2ᅳ옥소 1ᅳ (2-(4- (트리플루오로메특시)페닐) 아세틸 )-1， 2-디하이드로퀴놀린 -3-카복사마이드;  (192) N- (4 ᅳ fluorophenethyl) -2 ᅳ oxo 1 ᅳ (2- (4- (trifluoromepoxy) phenyl) acetyl) -1,2-dihydroquinoline-3-carboxamide ;
( 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 )ᅳ2-옥소 -1， 2-디하이 드로퀴놀린 -3-카복사마이드； (194) N- (4-ethylbenzyl) -1- (2- (4-hydroxyphenyl) acetyl) ᅳ 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 195) N-(4ᅳ에틸벤질) -1-(2ᅳ(4-에틸페닐)아세틸 )-2-옥소 -1 , 2ᅳ디하이드로 퀴놀린 -3-카복사마이드;  (195) N- (4'ethylbenzyl) -1- (2 '(4-ethylphenyl) acetyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide;
( 196) N- ( 4ᅳ에 ,틸벤질 ) - 1- ( 2- ( 4-플루오로페닐)아세틸 )ᅳ2ᅳ옥소 - 1， 2-디하이 드로퀴놀린 -3-카복사마이드; (196) N- (4 eu on, butyl-benzyl) - 1- (2- (4-fluorophenyl) acetyl) eu 2, eu-oxo-1, 2-D high-draw-3-carboxamide;
( 197) 1-(2-(4-클로로페닐 )아세틸) -N-(4-에틸벤질 )-2-옥소—1， 2-디하이드로 퀴놀린—3-카복사마이드;  (197) 1- (2- (4-chlorophenyl) acetyl) -N- (4-ethylbenzyl) -2-oxo—1, 2-dihydro quinoline—3-carboxamide;
( 198) N-(4-에틸벤질 )-1-(2-(4-아이오도페닐 )아세틸 )-2-옥소 -1 , 2—디하이 드로퀴놀린 -3ᅳ카복사마이드;  (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-디하이드로 퀴놀린—3-카복사마이드; (199) N- (4-ethylbenzyl) -1- (2- (4-nitrophenyl) acetyl) -2-oxo-1, 2-dihydro quinoline—3-carboxamide;
(200) 1-(2-(4-아미노페닐)아세틸 )-N-(4-에틸벤질 )-2ᅳ옥소 -1， 2ᅳ디하이드로 퀴놀린 -3-카복사마이드;  (200) 1- (2- (4-aminophenyl) acetyl) -N- (4-ethylbenzyl) -2ioxo-1,2'dihydroquinoline-3-carboxamide;
(201) N— (4-에틸펜에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (202) N-(4-에틸펜에틸) -1-(2-(4—포르밀페닐)아세틸 )-2-옥소ᅳ 1，2-디하이드 로퀴놀린 -3-카복사마이드；  (201) N— (4-ethylphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (202) N- (4-ethylphenethyl) -1- (2- ( 4—formylphenyl) acetyl) -2-oxo ᅳ 1,2-dihydroquinoline-3-carboxamide;
(203) 1-(2-(4-시아노페닐)아세틸) -N-(4-에틸펜에틸)ᅳ 2-옥소ᅳ 1， 2-디하이드 로퀴놀린 -3-카복사마이드;  (203) 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) '2-oxo' 1, 2-dihydroquinoline-3-carboxamide;
(204) N-(4-에틸펜에틸 )ᅳ1-(2-(4ᅳ(메틸티오)페닐)아세틸 )-2-옥소 -1， 2- 디하이드로퀴놀린 -3-카복사마이드;  (204) N- (4-ethylphenethyl) ᅳ 1- (2- (4 ᅳ (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—디하이드로 퀴놀린 -3-카복사마이드; (207) N- (4—hydroxybenzyl) -1- (4- (methylthio) benzyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
(208) N-(4-하이드록시벤질) -1-(4- (메틸티오)펜에틸 )-2-옥소 -1 , 2-디하이드 로퀴놀린 -3-카복사마이드; (208) N- (4-hydroxybenzyl) -1- (4- (methylthio) phenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(209) N-(4-하이드록시벤질)— 2ᅳ옥소 -1-(4ᅳ (트리플루오로메특시)펜에틸 )-1，2 ᅳ디하이드로퀴놀린 -3-카복사마이드;  (209) N- (4-hydroxybenzyl) —2ioxo--1- (4 '(trifluoromepoxy) phenethyl) -1,2 ᅳ dihydroquinoline-3-carboxamide;
(210) N- -하이드록시펜에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이 드;  (210) N-hydroxyphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(211) N-(4-하이드톡시펜에틸) -1-(4-메특시펜에틸 )ᅳ2-옥소 -1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (211) N- (4-hydroxyphenethyl) -1- (4-mesoxifenethyl) ᅳ 2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(212) N-(4-니트로벤질) -2-옥소ᅳ 1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드； (212) N- (4-nitrobenzyl) -2-oxo ᅳ 1, 2-dihydroquinoline-3'carboxamide;
(213) 1-(4-아이오도벤질 )-N-(4-니트로벤질 )-2-옥소 -1， 2-다하이드로퀴놀린- 3-카복사마이드; (213) 1- (4-iodobenzyl) -N- (4-nitrobenzyl) -2-oxo-1, 2-polyhydroquinoline-3-carboxamide;
(214) 1-(4-아이오도펜에틸 )-N-(4-니트로벤질) -2-옥소 -1ᅳ 2-디하이드로 퀴놀린 -3-카복사마이드;  (214) 1- (4-iodophenethyl) -N- (4-nitrobenzyl) -2-oxo-1'2-dihydro quinoline-3-carboxamide;
(215) N-(4ᅳ니트로펜에틸 )-2ᅳ옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드； (215) N- (4′nitrophenethyl) -2 ᅳ oxo-1, 2-dihydroquinoline ᅳ 3-carboxamide;
(216) 1-(4-포르밀벤질) -N-(4-니트로펜에틸 )-2-옥소ᅳ 1，2-디하이드로퀴놀린- 3-카복사마이드; (216) 1- (4-formylbenzyl) -N- (4-nitrophenethyl) -2-oxo ᅳ 1,2-dihydroquinoline-3-carboxamide;
(217) 1-(4-포르밀펜에틸) -N-(4-니트로펜에틸 )-2-옥소 -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (217) 1- (4-formylphenethyl) -N- (4-nitrophenethyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(218) 1-(4- (디플루오로메틸)펜에틸)ᅳ N-(4-니트로펜에틸 )-2-옥소ᅳ 1，2-디하 이드로퀴놀린 -3-카복사마이드；  (218) 1- (4- (difluoromethyl) phenethyl) ᅳ N- (4-nitrophenethyl) -2-oxo ᅳ 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 -3ᅳ카복사마이드；  (220) 1- (4- (difluoromethyl) benzyl) -N- (4- (N, N-dimethylsulfamoyl) benzyl) -2-oxo-1,2-dihydroquinoline-3′carboxamide ;
(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 )-2ᅳ옥소 -1， 2—디하이드로퀴놀린 -3-카복사 마이드; (222) N- (4- (hydroxymethyl) benzyl) -2 ioxo-1, 2—dihydroquinoline-3-carbox Amide;
(223) N-(4- (하이드록시메틸)펜에틸 )— 2—옥소 -1， 2-디하이드로퀴놀린 -3-카복 사마이드;  (223) N- (4- (hydroxymethyl) phenethyl) -2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(224) 2-옥소 -N-(4-비닐벤질)ᅳ 1， 2-디하이드로퀴놀린 -3—카복사마이드； (225) 2-옥소 -N-(4-비닐펜에틸)ᅳ 1， 2—디하이드로퀴놀린 -3-카복사마이드; (224) 2-oxo-N- (4-vinylbenzyl) ᅳ 1, 2-dihydroquinoline-3—carboxamide; (225) 2-oxo-N- (4-vinylphenethyl) ᅳ 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- 디하이드로퀴놀린ᅳ 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 -2ᅳ일)아세틸) -N-메틸 -2-옥소 -N-페닐 - 1， 2-디하이드로퀴놀린 -3-카복사마이드;  (228) 1— (2- (2, 3-dihydro-1H-inden-2 ylyl) acetyl) -N-methyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carbox Amide;
(229) 1-(3ᅳ(2， 3-디하이드로ᅳ 1H-인덴 -2ᅳ일 )프로파노일 )-N-메틸 -2—옥소 -N- 페닐— 1， 2-디하이드로퀴놀린 -3-카복사마이드；  (229) 1- (3 ′ (2, 3-dihydro ᅳ 1H-inden-2 ylyl) propanoyl) -N-methyl-2—oxo-N-phenyl— 1, 2-dihydroquinoline-3- Carboxamide;
(230) N-에틸 - 1- ( 2- ( 5—메록시 -2， 3-디하이드로- 1H-인덴 -2-일)아세틸 )—2-옥소 -N-페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (230) N-ethyl-1-(2- (5—methoxy-2, 3-dihydro-1H-inden-2-yl) acetyl)-2-oxo-N-phenyl-1, 2-dihydro Quinoline-3-carboxamide;
(231) N-에틸 -1-(2-(5- (메틸티오) -2 , 3-디하이드로-lH-인덴-2-일)아세틸)-2- 옥소-N—페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드； (231) N-ethyl-1- (2- (5- (methylthio) -2, 3-dihydro-lH-inden-2-yl) acetyl) -2-oxo-N—phenyl-1, 2- Dihydroquinoline-3-carboxamide;
(232) N-에틸ᅳ 2-옥소 -N-페닐 -1— (2-(5- (트리플루오로메록시 )-2 , 3-디하이드로 -1H-인덴 -2-일)아세틸 )-1， 2-디하이드로퀴놀린 -3-카복사마이드；  (232) N-ethyl ᅳ 2-oxo-N-phenyl-1— (2- (5- (trifluoromethoxy) -2, 3-dihydro-1H-inden-2-yl) acetyl) -1, 2-dihydroquinoline-3-carboxamide;
(233) N-에틸ᅳ 1-(2-(5-하이드록시 -2 , 3-디하이드로 -1H-인덴 -2-일)아세틸 )-2- 옥소 -N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (233) N-ethyl ᅳ 1- (2- (5-hydroxy-2, 3-dihydro-1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1, 2-dihydro Quinoline-3-carboxamide;
(234) N-에틸— 1-(2-(5-에틸 -2，3-디하이드로— 1H-인덴 -2ᅳ일)아세틸) -2-옥소- N-페닐 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (234) N-ethyl— 1- (2- (5-ethyl-2,3-dihydro— 1H-indened-2-hexyl) acetyl) -2-oxo-N-phenyl-1, 2-dihydroquinoline- 3-carboxamide;
(235) N-에틸 -1ᅳ(2-(5-플루오로 -2，3ᅳ디하이드로-lH-인덴-2ᅳ일)아세틸)-2- 옥소-N-페닐-l , 2-디하이드로퀴놀린 -3—카복사마이드；  (235) N-ethyl -1 '(2- (5-fluoro-2,3'dihydro-lH-inden-2xyl) acetyl) -2-oxo-N-phenyl-l, 2-dihydroquinoline- 3—carboxamide;
(236) 1-(2-(5_클로로 -2 , 3-디하이드로 -1H-인덴 -2-일)아세틸) -N-에틸 -2-옥소 ᅳ N-페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (236) 1- (2- (5_Chloro-2, 3-dihydro-1H-inden-2-yl) acetyl) -N-ethyl-2-oxo ᅳ N-phenyl-1, 2-dihydroquinoline -3-carboxamide;
(237) Nᅳ에틸 -1-(2-(5-아이오도 -2， 3ᅳ디하이드로 -1H-인덴 -2-일)아세틸 )-2- 옥소 -N-페닐 -1， 2-디하이드로퀴놀린— 3-카복사마이드;  (237) N ᅳ ethyl-1- (2- (5-iodo-2,3 ᅳ dihydro-1H-inden-2-yl) acetyl) -2-oxo-N-phenyl-1,2-dihydroquinoline — 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) 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—디하이드로ᅳ 1Hᅳ인덴 -2-일)아세틸 )-Nᅳ에틸 -2-옥소 —N-페닐 -1， 2-디하이드로퀴놀린 -3-카복사마이드; (239) 1- (2- (5-amino-2,3—dihydro ᅳ 1H ᅳ inden-2-yl) acetyl) -N ᅳ ethyl-2-oxo —N-phenyl-1, 2-dihydroquinoline-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-디하이드 '로퀴놀린 -3—카복사마이드； (241) 1- (3- (2,3-dihydro-1H—inden-2-yl) propanoyl) -N-ethyl-2-oxo-N-phenyl-1,2-dihydro ' roquinoline -3—carboxamide;
(242) N-에틸— 2-옥소 -N-페닐 -5-프로피온아미도 -1 , 2-디하이드로퀴놀린 -3-카 복사마 ol드 ;  (242) N-ethyl- 2-oxo-N-phenyl-5-propionamido-1, 2-dihydroquinoline-3-carboxoma old;
(243) 5-부티라미도ᅳ N-에틸 -2-옥소 -N—페닐 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (243) 5-butyramimid® N-ethyl-2-oxo-N-phenyl-1, 2-dihydroquinoline-3-carboxamide;
(244) N-메틸 -2-옥소ᅳ N-(p-를일 )-1， 2-디하이드로퀴놀린 -3-카복사마이드； (245) N-에틸 -2-옥소 -5-펜탄아미도 -N-(p-를일) -1， 2-디하이드로퀴놀린 -3-카 복사마이드;  (244) N-methyl-2-oxoxo N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide; (245) N-ethyl-2-oxo-5-pentaneamido- N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(246) N-에틸 -5-(2-메톡시아세트아미도 )-2-옥소 -N-(p-를일 )-1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (246) N-ethyl-5 (2-methoxyacetamido) -2-oxo-N- (p-ylyl) -1, 2-dihydro quinoline-3-carboxamide;
(247) N-에틸 -2-옥소 -N— (P-를일) -1， 2-디하이드로퀴놀린 -3-카복사마이드； (248) N-에틸 -2-옥소 -1-(4- (페닐티오)벤질) -N-(p-를일) -1 , 2-디하이드로 퀴놀린 -3-카복사마이드;  (247) N-ethyl-2-oxo-N— (P-ylyl) -1, 2-dihydroquinoline-3-carboxamide; (248) N-ethyl-2-oxo-1- (4- ( Phenylthio) benzyl) -N- (p-ylyl) -1,2-dihydroquinoline-3-carboxamide;
(249) N—에틸 -2-옥소ᅳ 1-(4-페녹시벤조일 )-N-(p-를일 )-1， 2-디하이드로퀴놀린 -3-카복사마이드;  (249) N—ethyl-2-oxoxo 1- (4-phenoxybenzoyl) -N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(250) N-에틸— 2-옥소 -1-(4- (페닐티오)벤조일) -N-(p-를일) -1 , 2-디하이드로 퀴놀린 -3-카복사마이드; ' (250) N-ethyl- 2-oxo-1- (4- (phenylthio) benzoyl) -N- (p-ylyl) -1, 2-dihydro quinoline-3-carboxamide; '
(251) N-에틸 -2-옥소ᅳ1-(2-(4- (페닐티오)페닐)아세틸) -N-(p-를일) 1，2-디하 이드로퀴놀린 -3-카복사마이드; (251) N-ethyl-2-oxoxo1- (2- (4- (phenylthio) phenyl) acetyl) -N- (p-ylyl) 1,2-dihydroquinoline-3-carboxamide;
(252) N-에틸— 2—옥소ᅳ 1-(2— (4—페녹시페닐)아세틸) -N_(p-를일 )-1，2-디하이드 로퀴놀린 -3-카복사마이드;  (252) N-ethyl— 2—oxoze 1- (2— (4—phenoxyphenyl) acetyl) -N_ (p-ylyl) -1,2-dihydroquinoline-3-carboxamide;
(253) 1-(2-(4-벤질페닐)아세틸 )-N-에틸 -2-옥소 -N-(p-를일) -1 , 2-디하이드로 퀴놀린 -3—카복사마이드;  (253) 1- (2- (4-benzylphenyl) acetyl) -N-ethyl-2-oxo-N- (p-ylyl) -1, 2-dihydro quinoline-3—carboxamide;
• (254) 1-(4-벤질벤조일) -N-에틸 -2—옥소 -N-(p-를일) -1 , 2-디하이드로퀴놀린- 3-카복사마이드; (254) 1- (4-benzylbenzoyl) -N-ethyl-2—oxo-N- (p-ylyl) -1, 2-dihydroquinoline-3-carboxamide;
(255) N-(4-메특시페닐) -N-메틸— 2-옥소 -1 , 2—디하이드로퀴놀린 -3-카복사마이 드;  (255) N- (4-methoxyphenyl) -N-methyl- 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(256) N-에틸 -N-(4-메특시페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이 (257) 5-(2-브로모아세트아미도) -N—에틸— N-(4-메록시페닐 )-2-옥소 -1， 2-디하 이드로퀴놀린 -3-카복사마이드； (256) N-ethyl-N- (4-methoxyphenyl) -2-oxo-1, 2-dihydroquinoline-3 ᅳ carboxamide (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-카복사마 이드;  (258) N- (4-bromophenyl) —N-methyl-2-oxo-1, 2-dihydroquinoline—3-carboxamide;
(259) N-(4-브로모페닐) -1ᅳ (사이클로펜티ᅳ1，3-디엔카르보닐 ) -N-메틸 -2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (259) N- (4-bromophenyl) -1 '(cyclopenti ᅳ 1,3-dienecarbonyl) -N-methyl-2-oxo-1,2-dihydroquinoline® 3-carboxamide;
(260) N-(4-브로모페닐) -Nᅳ메틸 -2-옥소 -1-(2H-피를ᅳ 3-카르보닐 )-1， 2-디하이 드로퀴놀린ᅳ 3-카복사마이드;  (260) N- (4-bromophenyl) -N ᅳ methyl-2-oxo-1- (2H-pyrrjan 3-carbonyl) -1, 2-dihydrodroquinolin ᅳ 3-carboxamide;
(261) N-(4-브로모페닐) -N-메틸 -2-옥소 -1- (티오펜 -2-카르보닐) -1 , 2-디하이 드로퀴놀린ᅳ 3-카복사마이드; (261) N- (4-bromophenyl) -N-methyl-2-oxo-1- (thiophene-2-carbonyl) -1, 2-dihydrodroquinolin ᅳ 3-carboxamide;
(262) N-(4—브로모페닐 )-1- (퓨란ᅳ2-카르보닐) -N-메틸 -2-옥소 -1， 2- 디하이드로퀴놀린 -3—카복사마이드;  (262) N- (4—bromophenyl) -1- (furan-2-2-carbonyl) -N-methyl-2-oxo-1, 2-dihydroquinoline-3—carboxamide;
(263) N-(4-브로 '보페닐) -N-메틸 -2-옥소— 1-(2— (티오펜 -2-일)아세틸 )— 1 , 2-디 하이드로퀴놀린 -3-카복사마이드; (263) N- (4- bromo "beam-phenyl) -N- methyl-2-oxo-1- (2- (thiophen-2-yl) acetyl) - 1, 2-dihydro-quinoline-3-carboxamide Amide;
(264) N-(4-브로모페닐) -1— (2- (퓨란 -2-일)아세틸 )-N-메틸 -2-옥소 -1， 2-디하 이드로퀴놀린 -3ᅳ카복사마이드;  (264) N- (4-bromophenyl) -1— (2- (furan-2-yl) acetyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3′carboxamide;
(265) 1-(2-(2Η-피를 -2-일 )아세틸) -N-(4-브로모페닐) 메틸 -2-옥소 -1， 2- 디하이드로퀴놀린 -3-카복사마이드；  (265) 1- (2- (2Η-pyr-2-yl) acetyl) -N- (4-bromophenyl) methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(266) N-(4-브로모페닐) -N-에틸 -2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이 (266) N- (4-bromophenyl) -N-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
(267) N-(4-브로모페닐) -1- (사이클로핵산카르보닐) -N-에틸 -2-옥소 -1， 2-디하 이드로퀴놀린 -3-카복사마이드; (267) N- (4-bromophenyl) -1- (cyclonucleic acid carbonyl) -N-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(268) N-(4ᅳ브로 £페닐 )— 1-(3ᅳ사이클로핵실프로파노일 )-N-에틸 -2—옥소 -1 , 2- 디하이드로퀴놀린 -3-카복사마이드;  (268) N- (4vibro £ phenyl) — 1- (3′cyclonucleosilpropanoyl) -N-ethyl-2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(269) N-(4-브로모페닐 )-5-(2-클로로아세트아미도) -N-에틸 -2-옥소 -1， 2-디하 이드로퀴놀린 -3ᅳ카복사마이드;  (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-카복사마이 (271) N- -클로로페닐) -1- (사이클로펜탄카르보닐) -N-메틸 -2—옥소— 1，2-디하 이드로퀴놀린 -3-카복사마이드; (272) N-(4-클로로페닐 )-1ᅳ (퓨란 -2-카르보닐) -N-메틸 -2-옥소 -1 , 2-디하이드 로퀴놀린 -3ᅳ카복사마이드; (270). N- (4-Chlorophenyl) -N-methyl-2-oxo-1, 2-dihydroquinoline— 3-carboxymai (271) N-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-클로^페닐 )-N-메틸 -2—옥소 -1- (티오펜 -2-카르보닐 )-1 , 2-디하이 드로퀴놀린ᅳ 3-카복사마이드;  (273) N- (4-chloro ^ phenyl) -N-methyl-2—oxo-1- (thiophene-2-carbonyl) -1, 2-dihydrodroquinolin ᅳ 3-carboxamide;
(274) N-(4-클로로페닐)ᅳ N-메틸— 2-옥소 -1-(2H-피를 -2-카르보닐) -1，2-디하이 드로퀴놀린ᅳ 3-카복사마이드; (274) N- (4-chlorophenyl) ᅳ N-methyl- 2-oxo-1- (2H-pyrid-2-carbonyl) -1,2-dihydrodroquinoline ᅳ 3-carboxamide;
(275) N-(4-클로로페닐)ᅳ Nᅳ에틸—2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이 드 ·  (275) N- (4-chlorophenyl) ᅳ N ᅳ ethyl—2-oxo-1, 2-dihydroquinoline-3-carboxamide
(276) N— (4-클로로페닐) -1-(2-사이클로펜틸아세틸) -N-에틸 -2-옥소ᅳ 1 , 2-디하 이드로퀴놀린 -3—카복사마이드;  (276) N— (4-chlorophenyl) -1- (2-cyclopentylacetyl) -N-ethyl-2-oxoxol 1, 2-dihydroquinoline-3—carboxamide;
(277) N-(4-클로로페닐 )-N-에틸 -1ᅳ(2- (퓨란 -2-일)아세틸 )-2_옥소ᅳ1 , 2-디하 이드로퀴놀린 -3-카복사마이드;  (277) N- (4-chlorophenyl) -N-ethyl-1 '(2- (furan-2-yl) acetyl) -2_oxox1, 2-dihydroquinoline-3-carboxamide;
(278) N-(4ᅳ클로로페닐) -N-에틸 -2ᅳ옥소 -1-(2ᅳ (티오펜 -2-일)아세틸 )-1，2-디 하이드로퀴놀린 -3-카복사마이드；  (278) N- (4′chlorophenyl) -N-ethyl-2-2-oxo-1- (2 ′ (thiophen-2-yl) acetyl) -1,2-di hydroquinoline-3-carboxamide;
(279) 1-(2-(2Η-피를ᅳ 2-일)아세틸) -N-(4-클로로페닐) -N-에틸 -2ᅳ옥소 -1，2-디 하이드로퀴놀린 -3-카복사마이드; (279) 1- (2- (2Η-Pyryl 2-yl) acetyl) -N- (4-chlorophenyl) -N-ethyl-2-2-oxo-1,2-dihydroquinoline-3-carbox Amide;
(280) N-(4-플루오로페닐 )— N-메틸 -2-옥소 -1 , 2ᅳ디하이드로퀴놀린 -3-카복사마 이드;  (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-디하 이드로퀴놀린 -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-메특시페닐) -2-옥소-에틸 )-N-메틸 -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (282) N- (4-fluorophenyl) -1- (2- (4-methoxyphenyl) -2-oxo-ethyl) -N-methyl-2-oxo-1,2-dihydroquinoline-3 -Carboxamide;
(283) N-(4-플루오로페닐) -N-메틸 -2-옥소 -1-(2-옥소 -2-(4- (트리플루오로 메특시 )페닐)에틸) -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (283) N- (4-fluorophenyl) -N-methyl-2-oxo-1- (2-oxo-2- (4- (trifluoro meso) phenyl) ethyl) -1,2-di Hydroquinoline-3-carboxamide;
(284) N-(4-플루오로페닐) -Nᅳ메틸 -1-(2-(4ᅳ니트로페닐 )-2-옥소-에틸) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드; (284) N- (4-fluorophenyl) -N ᅳ methyl-1- (2- (4 ᅳ nitrophenyl) -2-oxo-ethyl) -2-oxo-1, 2-dihydroquinoline-3- 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) -N-methyl-oxo-1, 2-dihydroquinoline-3 —Carboxamide;
(286) N-(4-플루오로페닐 )-1-(2-(4-플루오로페닐 )-2ᅳ옥소-에틸 )_N—메틸 -2- 옥소ᅳ1， 2-디하이드로퀴놀린 -3-카복사마이드；  (286) N- (4-fluorophenyl) -1- (2- (4-fluorophenyl) -2 ᅳ oxo-ethyl) _N—methyl-2-oxo ᅳ 1, 2-dihydroquinoline-3- Carboxamide;
(287) 1-(2-(4-에틸페닐) -2-옥소-에틸) -N-(4-플루오로페닐 )-N_메틸ᅳ2—옥소- 1， 2-디하이드로퀴놀린 -3-카복사마이드; (287) 1- (2- (4-ethylphenyl) -2-oxo-ethyl) -N- (4-fluorophenyl) -N_methyl'2—oxo- 1, 2-dihydroquinoline-3-carboxamide;
(288) 1-(2-(4-시아노페닐)아세틸 )-N-(4-에틸펜에틸) -2-옥소 -1， 2-디하이드 로퀴놀린 -3ᅳ카복사마이드；  (288) 1- (2- (4-cyanophenyl) acetyl) -N- (4-ethylphenethyl) -2-oxo-1,2-dihydroquinoline-3′carboxamide;
(289) Nᅳ에틸 -N-(4-플루오로페닐)— 2ᅳ옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사 마이드;  (289) N ᅳ ethyl —N- (4-fluorophenyl) —2oxoo-1, 2-dihydroquinoline ᅳ 3-carboxamide;
(290) 1ᅳ(2-(4-아미노페닐 )-2-옥소ᅳ에틸 )-N-에틸ᅳ N'-(4-플루오로페닐 )-2- 옥소 -1 , 2-디하이드로퀴놀린 -3ᅳ카복사마이드;  (290) 1 '(2- (4-aminophenyl) -2-oxo ᅳ ethyl) -N-ethyl'N'-(4-fluorophenyl) -2-oxo-1, 2-dihydroquinoline-3 Yolkcaramide;
(291) 1-(2-(4-시아노페닐 )-2ᅳ옥소-에틸) -Nᅳ에틸 -N-(4-플루오로페닐 )-2- 옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드；  (291) 1- (2- (4-cyanophenyl) -2 ᅳ oxo-ethyl) -N ᅳ ethyl-N- (4-fluorophenyl) -2-oxo-1,2-dihydroquinoline ᅳ 3 -Carboxamide;
(292) N-에틸 -N-(4-플루오로페닐 )-1-(2ᅳ(4- (메틸티오)페닐) -2ᅳ옥소-에틸) - 2-옥소 -1， 2-디하이드로퀴놀린ᅳ 3-카복사마이드； (292) N-ethyl-N- (4-fluorophenyl) -1- (2 '(4- (methylthio) phenyl) -2ioxo-ethyl) -2-oxo-1,2-dihydroquinoline Iii 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 HH4-에틸페닐) -N-메틸 -2-옥소ᅳ 1， 2-디하이드로 퀴놀린 -3-카복사마이드; (294) 1- (2, 4-dimethylbenzyl HH4-ethylphenyl) -N-methyl-2-oxoxol 1, 2-dihydro quinoline-3-carboxamide;
(295) 1-(2ᅳ4-디메틸펜에틸) -N-(4—에틸페닐) -Nᅳ메틸 -2-옥소ᅳ 1，2-디하이드로 퀴놀린 -3-카복사마이드; (295) 1- (2'4-Dimethylphenethyl) -N- (4-ethylphenyl) -N'methyl-2-oxo '1,2-dihydro quinoline-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-디하이 드로퀴놀린 -3-카복사마이드;  (297) N- (4-ethylphenyl) -N-methyl-1- (2-methyl-4-nitrobenzyl) -2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(298) 1-(4—에틸 -2-메틸펜에틸) -N-(4-에틸페닐) -N-메틸 -2-옥소— 1， 2-디하이 드로퀴놀린— 3-카복사마이드;  (298) 1- (4—ethyl-2-methylphenethyl) -N- (4-ethylphenyl) -N-methyl-2-oxo—1, 2-dihydrodroquinoline—3-carboxamide;
(299) N-(4-에틸페닐) -1-(4ᅳ하이드록시 2ᅳ메틸펜에틸) -N-메틸 -2-옥소ᅳ 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-디하 이드로퀴놀린—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-디하이 드로퀴놀린 -3-카복사마이드;  (301) 1- (4-ethyl-2-methylbenzyl) -N— (4-ethylphenyl) -N-methyl-2-oxo-1,2-dihydrodroquinoline-3-carboxamide;
(302) 1- ( 2， 3-디메틸벤질) -N- ( 4-에틸페닐) -Nᅳ메틸 -2-옥소 - 1， 2-디하이드로 퀴놀린 -3-카복사마이드;  (302) 1- (2, 3-dimethylbenzyl) -N- (4-ethylphenyl) -N ᅳ methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide;
(303) N-(4—에틸페닐) -5-(2-플루오로아세트아미도)— Nᅳ메틸 -2-옥소 -1 , 2-디하 이드로퀴놀린 -3-카복사마이드； (303) N- (4—ethylphenyl) -5 (2-fluoroacetamido) —N ᅳ methyl-2-oxo-1, 2-diha Idroquinoline-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-디하이드로 퀴놀린 -3-카복사마이드; (305) 1- (2, 5-dimethylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-1, 2-dihydro quinoline-3-carboxamide;
(306) 1-(3 , 4-디메틸벤질) -N-에틸ᅳ N-(4-에틸페닐) -2-옥소 -1，2-디하이드로 퀴놀린 -3-카복사마이드; (306) 1- (3, 4-dimethylbenzyl) -N-ethyl ᅳ N- (4-ethylphenyl) -2-oxo-1,2-dihydro quinoline-3-carboxamide;
(307) 1-(2， 6-디메틸벤질) -N-에틸 -N-(4—에틸페닐 )-2-옥소— 1， 2-디하이드로 퀴놀린—3-카복사마이드;  (307) 1- (2, 6-dimethylbenzyl) -N-ethyl-N- (4—ethylphenyl) -2-oxo—1, 2-dihydro quinoline—3-carboxamide;
(308) N-에틸 -N— (4-에틸페닐)— 2-옥소 -1-(2，4，6-트리메틸벤질 )-1，2-디하이 드로퀴놀린 -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) 1- (4- (difluoromethyl) —2-methylbenzyl) -N-ethyl-N- (4-ethylphenyl) -2-oxo-l, 2-dihydroquinoline-3-carbox Amide;
(310) (E)-l (2-(4- (디플루오로메틸) -2—메틸사이클로핵사 -2 , 4-디엔 -1- 일리딘)에틸 )-N-에틸 -N-(4-에틸페닐) -2ᅳ옥소 -1， 2-디하이드로퀴놀린 -3-카복 사마이드;  (310) (E) -l (2- (4- (difluoromethyl) -2—methylcyclonucleus-2, 4-diene-1-ylidine) ethyl) -N-ethyl-N- (4- Ethylphenyl) -2-hexoxo-1, 2-dihydroquinoline-3-carboxamide;
(311) N-(4-하이드록시페닐) -N-메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드;  (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) ^(4-하이드록시페닐) —메틸-2-옥소-1-(2，3，4，5，6-펜타메틸벤질)- 1， 2-디하이드로퀴놀린 -3-카복사마이드; (313) ^ (4-hydroxyphenyl) —methyl-2-oxo-1- (2,3,4,5,6-pentamethylbenzyl) -1,2-dihydroquinoline-3-carboxamide;
(314) (E)-5- (부트 -2-엔아미도)— N-(4-하이드톡시페닐 )-Nᅳ메틸 -2-옥소 -1， 2- 디하이드로퀴놀린， 3-카복사마이드;  (314) (E) -5- (but-2-enamido) — N- (4-hydroxyphenyl) -N ᅳ methyl-2-oxo-1, 2-dihydroquinoline, 3-carboxamide ;
(315) N-에틸ᅳ N-(4-하이드록시페닐 )— 2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (315) N-ethyl ᅳ 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， 3ᅳ디메틸펜에틸) -N-에틸 -Nᅳ (4-하이드록시페닐) -2-옥소 -1 , 2-디하 이드로퀴놀린—3-카복사마이드;  (317) 1— (2, 3′dimethylphenethyl) -N-ethyl-N ′ (4-hydroxyphenyl) -2-oxo-1, 2-dihydroquinoline—3-carboxamide;
(318) 1-(2 , 5ᅳ디메틸펜에틸) -N-에틸— N-(4-하이드록시페닐)— 2-옥소 -1 , 2-디하 이드로퀴놀린 -3-카복사마이드; (319) l-(2 , 6—디메틸펜에틸) -N—에틸 -N-(4-하이드록시페닐 )-2-옥소 -1， 2-디하 이드로퀴놀린ᅳ 3-카복사마이드; (318) 1- (2,5'dimethylphenethyl) -N-ethyl—N- (4-hydroxyphenyl) —2-oxo-1, 2-dihydroquinoline-3-carboxamide; (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-카복사마이 (321) N-methyl-N- (4-nitrophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxami
(322) Ν-메틸 -Ν-(4-니트로페닐) 2-옥소 -1-(2，3 , 4，5，6-펜타메틸펜에틸) _1，2- 디하이드로퀴놀린 -3-카복사마이드; (322) Ν-methyl-Ν- (4-nitrophenyl) 2-oxo-1- (2,3,4,5,6-pentamethylphenethyl) _1,2-dihydroquinoline-3-carboxamide ;
(323) Ν-에틸 -Ν-(4-니트로페닐) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이 드;  (323) Ν-ethyl -Ν- (4-nitrophenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(324) Ν-(4-(Ν， Ν-디메틸설파모일)페닐 )-Ν_메틸 -2-옥소ᅳ 1， 2—디하이드로퀴놀 린 -3-카복사마이드;  (324) Ν- (4- (Ν, Ν-dimethylsulfamoyl) phenyl) -Ν_methyl-2-oxo ᅳ 1,2-dihydroquinoline-3-carboxamide;
(325) Ν-(4-(Ν , Ν! -디메틸설파모일)페닐) -Ν-에틸 -2-옥소 -1， 2-디하이드로퀴놀 린 -3-카복사마이드; (325) Ν- (4- (Ν, Ν ! -Dimethylsulfamoyl) phenyl) -Ν-ethyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(326) Ν-(4- (하이드록시메틸)페닐)—Ν-메틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3- 카복사마이드; (326) Ν- (4- (hydroxymethyl) phenyl) —Ν-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(327) 1-(4-( 1Η-피라졸 -1-일)벤질) -Ν-(4- (하이드록시메틸)페닐) -Ν—메틸 -2- 옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (327) 1- (4- (1Η-pyrazol-1-yl) benzyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-2-oxo-1, 2-dihydroquinoline- 3-carboxamide;
(328) 1-(4-( 1Η-피라졸 -1-일)벤조일 )-Ν-(4- (하이드록시메틸)페닐 )-Ν_메틸- 2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;  (328) 1- (4- (1Η-pyrazol-1-yl) benzoyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν_methyl- 2-oxo-1, 2-dihydroquinoline- 3-carboxamide;
(329) 1-(2 , 2-디페닐아세틸) -Ν-(4- (하이드록시메틸)페닐 )-Ν—메틸 -2-옥소 -1， 2-디하이드로퀴놀린 -3ᅳ카복사마이드;  (329) 1- (2, 2-diphenylacetyl) -Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-2-oxo-1, 2-dihydroquinoline-3′carboxamide;
(330) 1-(2 , 2-디페닐에틸 )-Ν— (4— (하이드록시메틸)페닐 )-Ν-메틸 -2-옥소 -1， 2- 디하이드로퀴놀린 -3ᅳ카복사마이드;  (330) 1- (2, 2-diphenylethyl) -Ν— (4— (hydroxymethyl) phenyl) -Ν-methyl-2-oxo-1, 2-dihydroquinoline-3′carboxamide;
(331) Ν-(4- (하이드톡시메틸)페닐) -5-(3-하이드록시프로판아미도) -Ν-메틸- 2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (331) Ν- (4- (hydroxymethyl) phenyl) -5 (3-hydroxypropaneamido) -Ν-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(332) Ν- (4- (하이드록시메틸)페닐 )-Ν-메틸 -5- (2-니트로아세트아미도) -2- 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (332) Ν- (4- (hydroxymethyl) phenyl) -Ν-methyl-5- (2-nitroacetamido) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(333) Ν-에틸 -Ν-(4- (하이드록시메틸)페닐 )-2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드;  (333) Ν-ethyl -Ν- (4- (hydroxymethyl) phenyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(334) Ν-메틸 -2-옥소 -Ν-(4-비닐페닐) -1， 2-디하이드로퀴놀린 -3-카복사마이드； (335) (E)-5- (부트 -2-엔아미도) -N-메틸ᅳ 2-옥소 -Nᅳ (4-비닐페닐) -1 , 2-디하이 드로퀴놀린 -3-카복사마이드； (334) Ν-methyl-2-oxo-Ν- (4-vinylphenyl) -1, 2-dihydroquinoline-3-carboxamide; (335) (E) -5- (but-2-enamido) -N-methyl ᅳ 2-oxo-N ᅳ (4-vinylphenyl) -1, 2-dihydrodroquinoline-3-carboxamide ;
(336) N-에틸ᅳ 2-옥소— N-(4-비닐페닐) -1 , 2—디하이드로퀴놀린 -3-카복사마이드； (336) N-ethyl ᅳ 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-디하이드로 퀴놀린 -3-카복사마이드; (339) 5- (3, 4-dihydroxybenzamido) -N—ethyl— 2-oxo-1, 2-dihydro quinoline-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- (메록시메틸 )-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 -3ᅳ카복사마이드；  (342) N— (bromomethyl) -2-oxo— 1, 2-dihydroquinoline-3′carboxamide;
(343) N- (클로로메,틸) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드； (343) N- (chlorometh , til) -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； (346) N- (니트로메틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (345) N- (hydroxymethyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide; (346) N- (nitromethyl) -2-oxo-1, 2-dihydroquinoline -3-carboxamide;
(347) 5-(2- (벤조 [d] [ l , 3]디옥솔 -5—일)아세트아미도) -N- (니트로메틸 )-2ᅳ 옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；  (347) 5- (2- (benzo [d] [l, 3] dioxol-5-yl) acetamido) -N- (nitromethyl) -2′oxo-1,2-dihydroquinoline-3 -Carboxamide;
(348) N-(2-하이드록시에틸 )-2-옥소-1 , 2-디하이드로퀴놀린 -3-카복사마이드； (348) N- (2-hydroxyethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(349) 2ᅳ옥소 -N—프로필 1， 2-디하이드로퀴놀린— 3-카복사마이드； (349) 2oxo-N—propyl 1, 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-1,2-dihydroquinoline-3-carbox Amide;
(351) (E)-2-옥소 (프로프 -1-엔 -1-일) -1，2-디하이드로퀴놀린 -3-카복사 마이드;  (351) (E) -2-oxo (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- (naphthalene— 2-yl) propaneamido) -2-oxo-N- (prop-1-en-1-yl) -1,2-dihydroquinoline -3—carboxamide;
(353) (E)-5-(2— (나프탈렌 -2-일)아세트아.미도) -2-옥소 -N- (프로프— 1-엔 -1- 일) -1 , 2—디하이드로퀴놀린 -3-카복사마이드;  (353) (E) -5- (2— (naphthalen-2-yl) acet.mido) -2-oxo-N- (prop— 1-en-1-yl) -1, 2-dihydro Quinoline-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； (356) 5-(2-( [ 1， 1 ' -비페닐] -4-일)아세트아미도) -N—( 2-브로모에틸) -2-옥소- 1， 2-디하이드로퀴놀린ᅳ 3—카복사마이드; (357) N-(2-클로로에틸 )ᅳ2-옥소— 1 , 2-디하이드로퀴놀린— 3-카복사마이드；(355) N- (2—bromoethyl) -2-oxo— 1, 2-dihydroquinoline-3—carboxamide; (356) 5- (2-([1,1′-biphenyl]- 4-yl) acetamido) -N— (2-bromoethyl) -2-oxo-1,2-dihydroquinoline® 3—carboxamide; (357) N- (2-chloroethyl) ᅳ 2-oxo— 1, 2-dihydroquinoline— 3-carboxamide;
(358) Ν-(2-플루오로에틸) -2—옥소— 1 , 2-디하이드로퀴놀린 -3-카복사마이드；(358) Ν- (2-fluoroethyl) -2—oxo— 1, 2-dihydroquinoline-3-carboxamide;
(359) Ν-(2-하이드록시에틸 )-2ᅳ옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드；(359) Ν- (2-hydroxyethyl) -2 ᅳ oxo-1, 2-dihydroquinoline-3-carboxamide;
(360) Ν-(2—니트로에틸 )-2-옥소ᅳ1 , 2-디하이드로퀴놀린 -3-카복사마이드； (361) Ν-(3-하이드록시프로필) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이 드 ' (360) Ν- (2—nitroethyl) -2-oxox1, 2-dihydroquinoline-3-carboxamide; (361) Ν- (3-hydroxypropyl) -2-oxo-1, 2 -Dihydroquinoline-3-carboxamide '
(362) (Ε)-2-옥소 -Νᅳ (펜트 -3ᅳ엔 -1ᅳ일) -1 , 2-디하이드로퀴놀린 -3ᅳ카복사마이  (362) (Ε) -2-oxo-Ν ᅳ (pent-3yen-1syl) -1, 2-dihydroquinoline-3 Carboxy mai
(363) Ν-부틸 -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (363) N-butyl-2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(364) Ν-(3-메특시프로필 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드;(364) Ν- (3-methoxypropyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(365) Ν-(3-브로모프로필 )-2—옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；(365) Ν- (3-bromopropyl) -2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(366) Ν-(3-클로로프로필 )-2-옥소— 1， 2-디하이드로퀴놀린 -3-카복사마이드；(366) Ν- (3-chloropropyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(367) Ν-(3-플루오로프로필)— 2-옥소 -1 , 2-디하이드로퀴놀린— 3-카복사마이드;(367) Ν- (3-fluoropropyl) — 2-oxo-1, 2-dihydroquinoline— 3-carboxamide;
(368) (Ε)-Ν- (핵스 -4-엔 -1-일) -2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드; (368) (Ε) -Ν- (nux-4-en-1-yl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(369) Ν-(3-하이드록시프로필 )-2-옥소 -1， 2ᅳ디하이드로퀴놀린 -3-카복사 마이드;  (369) Ν- (3-hydroxypropyl) -2-oxo-1, 2'dihydroquinoline-3-carboxamide;
(370) Ν-(3—니트로프로필 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드; (370) Ν- (3—nitropropyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(371) Ν— (4-하이드록시부틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3—카복사마이드; (372) Ν-(3 ,4-디하이드록시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -3-카복사 마이드； (371) Ν— (4-hydroxybutyl) -2-oxo-1, 2-dihydroquinoline-3—carboxamide; (372) Ν- (3,4-dihydroxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(373) Ν-(3 , 4-디에,틸벤질 )-2-옥소 -1，2-디하이드로퀴놀린 -3-카복사마이드;(373) Ν- (3, 4- di-on, butyl-benzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(374) Ν-(3 ,4-디메틸벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；(374) Ν- (3,4-dimethylbenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(375) Ν-(3 , 4-디하이드톡시펜에틸 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사 마이드; (375) Ν- (3, 4-dihydroxyphenethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(376) 5— (2-(4-벤질페닐)아세트아미도) -Ν-(3 , 4—디하이드록시펜에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드;  (376) 5— (2- (4-benzylphenyl) acetamido) -Ν- (3, 4-dihydroxyphenethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide ;
(377) Ν-(3， 4-디하이드록시펜에틸) -2-옥소 -5-프로피온아미도 -1， 2-디하이드 로퀴놀린 -3-카복사마이드;  (377) Ν- (3, 4-dihydroxyphenethyl) -2-oxo-5-propionamido-1, 2-dihydroquinoline-3-carboxamide;
(378) 5-부티라미도 -Ν-(3 , 4-디하이드록시펜에틸 )-2-옥소 -1， 2ᅳ디하이드로 퀴놀린 -3-카복사마이드; (379) N-(3，4-디하이드록시펜에틸 )-2-옥소 -5-펜탄아미도 -1， 2-디하이드로 퀴놀린 -3-카복사마이드; (378) 5-butyramido-N- (3,4-dihydroxyphenethyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide; (379) N- (3,4-dihydroxyphenethyl) -2-oxo-5-pentaneamido-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， 2ᅳ디하이드로퀴놀린 -3-카복사마이드； (382) N- (벤조 [d][l, 3]디옥솔 -5ᅳ일메틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3- 카복사마이드; (381) N- (3,4-dimethylphenethyl) -2-oxo-1,2'dihydroquinoline-3-carboxamide; (382) N- (benzo [d] [l, 3] dioxol- 5 boylmethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(383) N-(2- (벤조 [d][l, 3]디옥솔 -5-일)에틸) -2-옥소 -1,2-디하이드로퀴놀린ᅳ 3-카복사마이드;  (383) N- (2- (benzo [d] [l, 3] dioxol-5-yl) ethyl) -2-oxo-1,2-dihydroquinoline® 3-carboxamide;
(384) N- (나프탈렌 -2-일메틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드； (385) N-(2- (나프탈렌 -2-일)에틸) -2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사 마이드;  (384) N- (naphthalen-2-ylmethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide; (385) N- (2- (naphthalen-2-yl) ethyl)- 2-oxo-1, 2-dihydroquinoline-3-carboxamide;
( 386 ) 5- ( 2- (에.틸티오)아세트아미도) -N- ( 2- (나프탈렌 -2ᅳ일 )에틸) -2-옥소- 1,2—디하이드로퀴놀린 -3-카복사마이드;  (386) 5- (2- (Ethylthio) acetamido) -N- (2- (naphthalene-2xyl) ethyl) -2-oxo- 1,2-dihydroquinoline-3-carboxamide ;
(387) 5-(2- (에틸아미노)아세트아미도)ᅳ 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-에록시아세트아미도) -N-(2- (나프탈렌 -2-일)에틸) -2-옥소 -1，2ᅳ 디하이드로퀴놀린 -3-카복사마이드;  (388) 5- (2-ethoxyacetamido) -N- (2- (naphthalen-2-yl) ethyl) -2-oxo-1,2 ′ dihydroquinoline-3-carboxamide;
(389) ([1，1'-비페닐]-4-일메틸)-2-옥소—1,2-디하이드로퀴놀린-3- 카복사마이드;  (389) ([1,1'-biphenyl] -4-ylmethyl) -2-oxo—1,2-dihydroquinoline-3-carboxamide;
(390) Ν-(2-([1,1'-비페닐 ]-4-일)에틸) -2-옥소 -1,2-디하이드로퀴놀린 -3- 카복사마이드; (390) Ν- (2-([1,1'-biphenyl] -4-yl) ethyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(391) Ν-(4-벤질벤,질 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복사마이드； (391) Ν- (4- benzyl Ben, quality) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(392) Ν-(4-벤질펜에틸) -2-옥소 -1ᅳ 2-디하이드로퀴놀린 -3-카복사마이드;  (392) Ν- (4-benzylphenethyl) -2-oxo-1'2-dihydroquinoline-3-carboxamide;
(393) Ν- (에록시메틸 )-2-옥소ᅳ 1,2-디하이드로퀴놀린 -3-카복사마이드;  (393) Ν- (ethoxymethyl) -2-oxoze 1,2-dihydroquinoline-3-carboxamide;
(394) Ν- ((에틸티오)메틸) -2-옥소 -1,2-디하이드로퀴놀린 -3-카복사마이드;(394) Ν-((ethylthio) methyl) -2-oxo-1,2-dihydroquinoline-3-carboxamide;
(395) Ν-(2-메록시에틸 )-2-옥소 -1， 2-디하이드로퀴놀린 -3-카복사마이드；(395) Ν- (2-methoxyethyl) -2-oxo-1, 2-dihydroquinoline-3-carboxamide;
(396) Ν- ((에틸아미노)메틸) -2-옥소 -1,2-디하이드로퀴놀린ᅳ 3-카복사마이드;(396) Ν- ((ethylamino) methyl) -2-oxo-1,2-dihydroquinoline® 3-carboxamide;
(397) Ν-(2- (메틸티오)에틸) -2-옥소 -1， 2ᅳ디하이드로퀴놀린ᅳ 3-카복사마이드；(397) Ν- (2- (methylthio) ethyl) -2-oxo-1,2 "dihydroquinoline" 3-carboxamide;
(398) Ν-(2- (메틸아미노)에틸)—2-옥소 -1,2-디하이드로퀴놀린— 3-카복사마이 드; (398) Ν- (2- (methylamino) ethyl) —2-oxo-1,2-dihydroquinoline—3-carboxamide;
(399) 3- (페닐아미노)퀴놀린 2(1Η)—은; (400) 3-(p-를일아미노)퀴놀린 -2(1H)-은; (399) 3- (phenylamino) quinoline 2 (1Η) —silver; (400) 3- (p-ylylamino) quinoline-2 (1H) -silver;
(401) 3-((4-메록시페닐)아미노)퀴놀린 -2(1H)-은;  (401) 3-((4-methoxyphenyl) amino) quinoline-2 (1H) -silver;
(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)-은; (404) 3-((4-fluorophenyl) amino) quinoline-2 (1H) -silver;
(405) 3-((4-에틸페닐)아미노)퀴놀린 -2(1H)-은;  (405) 3-((4-ethylphenyl) amino) quinoline-2 (1H) -silver;
(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) Ν,Ν -디메틸 -4-((2-옥소 -1，2-디하이드로퀴놀린 -3-일)아미노)벤젠 설폰아미드;  (410) Ν, Ν-dimethyl-4-((2-oxo-1,2-dihydroquinolin-3-yl) amino) benzene sulfonamide;
(411) 3- (벤질아미노)퀴놀린 -2(1Η)-온;  (411) 3- (benzylamino) quinolin-2 (1Η) -one;
(412) 3_((4-메틸벤질)아미노)퀴놀린 -2(1Η)-온;  (412) 3 _ ((4-methylbenzyl) amino) quinolin-2 (1Η) -one;
(413) 3_((4-메특시벤질)아미노)퀴놀린 -2(1Η)-온; (413) 3 _ ((4-mesoxybenzyl) amino) quinolin-2 (1Η) -one;
(414) 3— ((4-브로모벤질)아미노)퀴놀린 -2(1Η)_온;  (414) 3— ((4-bromobenzyl) amino) quinolin-2 (1Η) _one;
(415) 3_((4-클로로벤질)아미노)퀴놀린 -2(1Η)_온;  (415) 3 _ ((4-chlorobenzyl) amino) quinolin-2 (1Η) _one;
(416) 3-((4-클로로벤질)아미노)퀴놀린 -2(1Η)-온;  (416) 3-((4-chlorobenzyl) amino) quinolin-2 (1Η) -one;
(417) 3-((4-에틸벤질)아미노)퀴놀린 -2(1Η)-온;  (417) 3-((4-ethylbenzyl) amino) quinolin-2 (1Η) -one;
(418) 3-((4-하이드록시벤질)아미노)퀴놀린 -2(1Η)-온; (418) 3-((4-hydroxybenzyl) amino) quinolin-2 (1Η) -one;
(419) 3-((4-니트로벤질)아미노)퀴놀린 -2(1Η)-온;  (419) 3-((4-nitrobenzyl) amino) quinolin-2 (1Η) -one;
(420) Ν， Ν-디메틸 -4-( ( (2-옥소 -1 , 2-디하이드로퀴놀린 -3-일 )아미노)메틸) 벤젠설폰아미드;  (420) Ν, Ν-dimethyl-4- (((2-oxo-1, 2-dihydroquinolin-3-yl) amino) methyl) benzenesulfonamide;
(421) 3-((4- (하이드록시메틸)벤질)아미노)퀴놀린 -2(1Η)-온;  (421) 3-((4- (hydroxymethyl) benzyl) amino) quinolin-2 (1Η) -one;
(422) 3-((4-비닐벤질)아미노)퀴놀린 -2(1Η)-온； (422) 3-((4-vinylbenzyl) amino) quinolin-2 (1Η) -one;
(423) 3- (메틸 (페닐)아미노)퀴놀린 -2(1Η)—온;  (423) 3- (methyl (phenyl) amino) quinolin-2 (1Η) —one;
(424) 3- (에틸 (페닐)아미노)퀴놀린 -2(1Η)—온;  (424) 3- (ethyl (phenyl) amino) quinolin-2 (1Η) —one;
(425) 3- (에틸 (Ρ-를일)아미노)퀴놀린 -2(1Η)_온;  (425) 3- (ethyl (Ρ-ylyl) amino) quinolin-2 (1Η) _one;
(426) 3- (메틸 (Ρ-를일)아미노)퀴놀린 2(1Η)—온;  (426) 3- (methyl (Ρ-ylyl) amino) quinolin 2 (1Η) —one;
(427) 3-((4-메특시페닐) (메틸)아미노)퀴놀린 -2(1Η)-온; (427) 3-((4-methoxyphenyl) (methyl) amino) quinolin-2 (1Η) -one;
(428) 3- (에틸 (4-메록시페닐)아미노)퀴놀린 -2(1Η)-온; (429) 3-〔(4-브로모페닐) (에틸)아미노)퀴놀린 -2(1H)_온; (428) 3- (ethyl (4-methoxyphenyl) amino) quinolin-2 (1Η) -one; (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 )아미노)퀴놀린 -2( 1L1 )-온；  (434) 3-: ethyl (4-fluorophenyl) amino) quinolin-2 (1L1) -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 트로페닐)아미노)퀴놀린 -2(1H)_온; (440) 3-: ethyl trophenyl) 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)-은; (443) 3-: methyl (4-vinylphenyl) amino) quinoline-2 (1H) -silver;
(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(110-온；  (445) 3-: (3,4-dimethylphenyl) amino) quinolin-2 (110-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)-은;  (448) 3-: (3,4-dihydroxybenzyl) amino) quinoline 2 (1H) -silver;
(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][l,3]디옥솔 -5-일)에틸)아미노)퀴놀린 -2(1H)—온;(450) 3- ( : (2- (benzo ' [d] [l, 3] dioxol-5-yl) ethyl) amino) quinolin-2 (1H) —one;
(451) 3-1 ： (나프탈렌 -2—일메틸)아미노)퀴놀린 -2(1H)-온; (451) 3-1: (naphthalene-2—ylmethyl) amino) quinolin-2 (1H) -one;
(452) 3- :(2- (나프탈렌 -2-일)에틸)아미노)퀴놀린 -2(1H)_은  (452) 3-:( 2- (naphthalen-2-yl) ethyl) amino) quinoline-2 (1H)
(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)퀴놀린ᅳ 2(1H)-온;  (457) 3-: ethylamino) quinolin ᅳ 2 (1H) -one;
(458) 3-( ：프로필아미노)퀴놀린 -2(1H)_온; (458) 3- ( : propylamino) quinolin-2 (1H) _one;
(459) 3-( ：부틸아미노)퀴놀린 -2(1H)_온; (460) 3ᅳ ( (에톡시맹틸)아미노)퀴놀린 -2( 1H)—은; (459) 3- ( ： butylamino) quinolin-2 (1H) _one; (460) 3 ᅳ ((ethoxymantyl) amino) quinoline-2 (1H) —silver;
(461) 3-( ( (에틸티오)메틸)아미노)퀴놀린 -2( 1H)-은; 및  (461) 3- (((ethylthio) methyl) amino) quinoline-2 (1H) -silver; 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- (트라이플루오로메록시)벤질) -1，2- 디하이드로퀴놀린 -3-카르복스아미드;  (463) 5-chloro-2-oxo-N-phenethyl-1- (4- (trifluoromethoxyoxy) benzyl) -1,2-dihydroquinoline-3-carboxamide;
(464) 5-클로로 -1-(4-에틸벤질 )-2-옥소ᅳ N-페네틸 -1， 2—디하이드로퀴놀린 -3- 카프복스아미드;  (464) 5-chloro-1- (4-ethylbenzyl) -2-oxoze N-phenethyl-1,2—dihydroquinoline-3-capboxamide;
(465) 5ᅳ클로로 -1-(4-아이소프로필벤질 )-2-옥소 -Nᅳ페네틸 -1， 2-디하이드로 퀴놀린 -3-카르복스아미드;  (465) 5'chloro-1- (4-isopropylbenzyl) -2-oxo-N ᅳ phenethyl-1,2-dihydroquinoline-3-carboxamide;
(466) 5-클로로 -1-(4-나이트로벤질 )-2ᅳ옥소 -N-페네틸 1ᅳ 2-디하이드로퀴놀린 -3-카르복스아미드; (466) 5-chloro-1- (4-nitrobenzyl) -2) oxo-N-phenethyl 1'2-dihydroquinoline-3-carboxamide;
(467) 5-클로로 -1-(4-메록시벤질 )ᅳ2-옥소 -N-페네틸 -1， 2-디하이드로퀴놀린- 3-카르복스아미드;  (467) 5-chloro-1- (4-methoxybenzyl) 질 2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
(468) 5ᅳ클로로 -1-(4-에틸벤질 )-N-(4-플루오로페네틸) -2-옥소 -1， 2-디하이 드로퀴놀린 -3—카프복스아미드;  (468) 5'chloro-1- (4-ethylbenzyl) -N- (4-fluorophenethyl) -2-oxo-1, 2-dihydrodroquinoline-3—capboxamide;
(469) 5-클로로 -N-(4-플루오로페네틸 )ᅳ1-(4-아이소프로필벤질 )-2-옥소— 1， 2- 디하이드로퀴놀린 -3-카르복스아미드;  (469) 5-chloro-N- (4-fluorophenethyl) ᅳ 1- (4-isopropylbenzyl) -2-oxo— 1, 2-dihydroquinoline-3-carboxamide;
(470) 5-클로로 -N-(4-플루오로페네틸) -1-(4-나이트로벤질 )-2—옥소 -1 , 2-디하 이드로퀴놀린 -3-카르복스아미드;  (470) 5-chloro-N- (4-fluorophenethyl) -1- (4-nitrobenzyl) -2—oxo-1, 2-dihydroquinoline-3-carboxamide;
(471) 5-클로로 -N-(4ᅳ플루오로페네틸) -1— (4-메록시벤질) -2-옥소 -1 , 2-디하이 드로퀴놀린 -3-카르복스아미드; (471) 5-chloro-N- (4 ᅳ fluorophenethyl) -1— (4-methoxybenzyl) -2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(472) 5-클로로 -N-(4-플루오로페네틸 )-2-옥소ᅳ1-(4- (트라이플루오로메록시 ) 벤질) -1， 2-디하이드로퀴놀린 -3-카르복스아미드；  (472) 5-chloro-N- (4-fluorophenethyl) -2-oxox1- (4- (trifluoromethoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide;
(473) 1-(4-에틸벤질 )-N-(4-플루오로펜에틸)— 5-니트로 -2-옥소 -1 , 2-디하이드 로퀴놀린 -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-니트로 -2-옥소 -1， 2- 디하이드로퀴놀린 -3-카르복사마이드) ;  (474) N- (4-fluorophenethyl) -1- (4-isopropylbenzyl) -5-nitro-2-oxo-1,2-dihydroquinoline-3-carboxamide);
(475) N-(4-플루오로펜에틸 )ᅳ5-니트로 -1— (4-니트로벤질)— 2-옥소 -1， 2-디하이 드로퀴놀린 -3-카르복사마이드;  (475) N- (4-fluorophenethyl) ᅳ 5-nitro-1— (4-nitrobenzyl) — 2-oxo-1, 2-dihydrodroquinoline-3-carboxamide;
(476) 5-아미노 -N-(4-브로모펜에틸 )-1ᅳ(4-메특시벤질) -2-옥소 -1 , 2-디하이드 로퀴놀린— 3-카르복사마이드) ; (477) l-(4-메록서벤질) -5ᅳ니트로 -2-옥소 -N-펜에틸 -1 , 2-디하이드로퀴놀린 -3 -카르복사마이드; (476) 5-amino-N- (4-bromophenethyl) -1 '(4-mesoxybenzyl) -2-oxo-1, 2-dihydroquinoline—3-carboxamide); (477) 1- (4-meroxabenzyl) -5mnitro-2-oxo-N-phenethyl-1, 2-dihydroquinoline-3-carboxamide;
(478) N-(4-플루오로펜에틸 )-1ᅳ (4-메특시벤질 )-5-니트로 -2-옥소 -1 , 2-디하이 드로퀴놀린ᅳ 3-카르복사마이드;  (478) N- (4-fluorophenethyl) -1 '(4-mesoxybenzyl) -5-nitro-2-oxo-1, 2-dihydrodroquinoline 3-carboxamide;
(479) 5-니트로 -2-옥소 -N—펜에틸 -1ᅳ(4— (트리플루오로메록시)벤질) -1，2-디하 이드로퀴놀린 -3ᅳ카르복사마이드; (479) 5-nitro-2-oxo-N—phenethyl-1 ′ (4— (trifluoromethoxy) benzyl) -1,2-dihydroquinoline-3′carboxamide;
(480) N-(4-플루오로펜에틸)ᅳ 5-니트로 -2-옥소 -1-(4- (트리플루오로메톡시 ) 벤질) -1 , 2-디하이드로퀴놀린 -3-카르복사마이드;  (480) N- (4-fluorophenethyl) ᅳ 5-nitro-2-oxo-1- (4- (trifluoromethoxy) benzyl) -1, 2-dihydroquinoline-3-carboxamide;
(481) 1-(4-이소프로필벤질 )-5ᅳ니트로— 2-옥소 -Nᅳ펜에틸 -1 , 2-디하이드로퀴놀 린 -3-카르복사마이드;  (481) 1- (4-isopropylbenzyl) -5mnitro—2-oxo-Nkphenethyl-1, 2-dihydroquinoline-3-carboxamide;
(482) 메틸 1-(4—쩨톡시벤질) -2-옥소 -5-(3-페닐프로파나미노) -1 , 2-디하이드 로퀴놀린 -3-카복실레이트;  (482) methyl 1- (4—ethoxybenzyl) -2-oxo-5- (3-phenylpropanamino) -1, 2-dihydroquinoline-3-carboxylate;
(483) 메틸 5ᅳ (3-사이클로펜틸프로파나미도 )-1— (4-메록시벤질) -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-메록시벤질) -2-옥소 -5-(2-페닐아세타미도)ᅳ 1 , 2-디하이드로 퀴놀린 -3-카복실레이트; (484) methyl 1- (4-methoxybenzyl) -2-oxo-5- (2-phenylacetamido) '1, 2-dihydro quinoline-3-carboxylate;
(485) 메틸 5-벤즈아미도 -1-(4-메록시벤질) -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 )-1ᅳ(4-메특시벤질) -2-옥소- 1， 2-디하이드로퀴놀린 -3-카복실레이트;  (486) methyl 5- (2- (4-chlorophenyl) acetamido) -1 ′ (4-mesoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(487) 메틸 5- (아다만테인 -1—카복시아미도 )-1— (4-메특시벤질) -2-옥소 -1，2- 디하이드로퀴놀린 -3-카복실레이트;  (487) methyl 5- (adamantane-1—carboxyxamido) -1— (4-methoxybenzyl) -2-oxo-1,2-dihydroquinoline-3-carboxylate;
(488) 메틸 5-(3 , 5-디메틸아다만테인 -1-카복시아미도 )-1_(4-메특시벤질) -2- 옥소 -1ᅳ 2-디하이드로퀴놀린 -3-카복실레이트；  (488) methyl 5- (3,5-dimethyladamantane-1-carboxyxamido) -1_ (4-methoxybenzyl) -2-oxo-1'2-dihydroquinoline-3-carboxylate;
(489) 메틸 5-(3ᅳ브로모아다만테인 -1ᅳ카복시아미도)— 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-메록시벤질) 5-(3ᅳ메틸아다만테인 -1-카복시아미도 )-2-옥소 -1 , 2-디하이드로퀴놀린 -3-카복실레이트;  (490) methyl 1- (4-methoxybenzyl) 5- (3'methyladamantane-1-carboxyxamido) -2-oxo-1, 2-dihydroquinoline-3-carboxylate;
(491) 메틸 5-(2- (아다만테인 -1-일)아미도 )-1-(4-메록시벤질) -2-옥소 -1ᅳ 2- 디하이드로퀴놀린 -3ᅳ카복실레이트;  (491) methyl 5- (2- (adamantane-1-yl) amido) -1- (4-methoxybenzyl) -2-oxo-1'2-dihydroquinoline-3'carboxylate;
(492) 메틸 ^(^ᅳ -다메틸아다만테인 -일ᅵ아세트아미도^；卜^-메특시 벤질 )-2-옥소 -1， 2」다이하이드톡시퀴놀린 -3—카복실레이트； (492) methyl ^ (^^-dimethyl adamantane -yl) acetamido ^; Benzyl) -2-oxo-1,2 "dihydroxyquinoline-3-carboxylate;
(493) 메틸 5— (2ᅳ(3—브로모메테인 -1-일)아세트아미도 )-1-(4-메특시벤질) -2- 옥소 -1 , 2-디클로로퀴놀린 -3-카복실레이트;  (493) Methyl 5— (2 ′ (3—bromomethane-1-yl) acetamido) -1- (4-mesoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxyl Rate;
( 494 ) 메틸 1- ( 4ᅳ메록시벤질) -5- ( 2- ( 3-메틸아다만테인 - 1-일)아세트아미도) - 2-옥소 -1 , 2—디클로로퀴놀린 -3-카복실레이트;  (494) Methyl 1- (4 ᅳ methoxybenzyl) -5 (2- (3-methyladamantane-1-yl) acetamido) -2-oxo-1,2—dichloroquinoline-3-carboxylate ;
(495) 메틸 5-(2-사이크로핵실아세트아미도 )-1-(4—메록시벤질) -2—옥소 -1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (495) methyl 5- (2-cyclonucleosilacetamido) -1- (4—methoxybenzyl) -2—oxo-1,2-dichloroquinoline-3-carboxylate;
(496) 메틸 5- (사이클로핵센카복시아미도) -1-(4-메특시벤질) -2-옥소 -1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (496) methyl 5- (cyclonucleosencarboxamido) -1- (4-mesoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate;
(497) 메틸 5ᅳ (아다만테인 -1ᅳ카복시아미도 )-1-(4-에틸벤질) -2-옥소 -1，2- 디클로로퀴놀린 -3 카복실레이트； (497) methyl 5 ′ (adamantane-1′carboxyaxido) -1- (4-ethylbenzyl) -2-oxo-1,2-dichloroquinoline-3 carboxylate;
(498) 메틸 5- (아다만테인 -1-카복시아미도 )-1-(3-메록시벤질) -2-옥소 -1 , 2- 디클로로퀴놀린 -3-카복실레이트;  (498) methyl 5- (adamantane-1-carboxyxamido) -1- (3-methoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylate;
(499) 메틸 5— (아다만테인 -1-카복시아미도 )-1-(4ᅳ나이트로벤질 )-2-옥소 -1 , 2 -디클로로퀴놀린 -3-카복실레이트;  (499) methyl 5— (adamantane-1-carboxyxamido) -1- (4 ᅳ nitrobenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(500) 메틸 5- (아다만테인 -1-카복시아미도 )-2-옥소 -1-(4- (트라이플루오로 메특시 )벤질) -1， 2ᅳ디클로로퀴놀린 -3-카복실레이트;  (500) methyl 5- (adamantane-1-carboxyxamido) -2-oxo-1- (4- (trifluoro meso) benzyl) -1,2'dichloroquinoline-3-carboxylate;
(501) 메틸 5ᅳ (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-디클로로퀴놀 ¾-3-카복실레이트; (502) methyl 5- (adamantane-1-carboxyxamido) _1- (4-fluorobenzyl) -2-oxo-1, 2-dichloroquinol ¾-3-carboxylate;
(503) 5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤질 )-2-옥소 -1， 2-다이클 로로퀴놀린 -3-카복실릭액시드;  (503) 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1, 2-dichloroquinoline-3-carboxylic acid;
(504) 에틸 5- (아다만테인ᅳ 1ᅳ카복시아미도 )-1-(4—메록시벤질) -2-옥소 -1，2- 디클로로퀴놀린 -3-카복실레이트;  (504) ethyl 5- (adamantane ᅳ 1 ᅳ carboxyxamido) -1- (4—methoxybenzyl) -2-oxo-1,2-dichloroquinoline-3-carboxylate;
(505) 5- (아다만테인 -1-카복시아미도 )-1-(4-메톡시벤질) -N-메틸 -2-옥소ᅳ 1 , 2 -디클로로퀴놀린ᅳ 3-카복시아미도;  (505) 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -N-methyl-2-oxoze 1, 2-dichloroquinoline 3-carboxyboxido;
(506) 5- (아다만테인 -1-카복시아미도 )-1-(4-메록시벤질) -Ν, Ν-디메틸 -2- 옥소— 1， 2-디하이드로퀴놀린ᅳ 3-카복시아마이드;  (506) 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -N, N-dimethyl-2-oxo—1,2-dihydroquinoline® 3-carboxyxamide;
(507) 프로필 5- (아다만테인 -1-카복시아미도 )-1-(4-메톡시벤질) -2-옥소- 1 , 2-디클로로퀴놀 ¾-3—카복실레이트； (508) 아이소프로필 5- (아다만테인 -1—카복시아미도 )-1-(4-메특시벤질) -2- 옥소 -1 , 2—디클로로퀴놀린 -3-카복실레이트; (507) propyl 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2-oxo-1,2-dichloroquinol ¾-3—carboxylate; (508) isopropyl 5- (adamantane-1—carboxyxamido) -1- (4-mesoxybenzyl) -2-oxo-1, 2—dichloroquinoline-3-carboxylate;
(509) N-( l-(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-carboxamide;
(510) N-(3- (에록시메틸 )-1-(4-메톡시벤질) 2-옥소 -1 , 2ᅳ디하이드로퀴놀린 - 5-일)아다만테인 -1-카복시아마이드； (510) N- (3- (ethoxymethyl) -1- (4-methoxybenzyl) 2-oxo-1,2'dihydroquinolin-5-yl) adamantane-1-carboxamide;
(511) S-메틸 5- (아다만테인 -1-카복시아미도 )-1-(4-메톡시벤질) -2—옥소ᅳ1，2 -디하이드로퀴놀린 -3-카보싸이오에이트;  (511) S-methyl 5- (adamantane-1-carboxyxamido) -1- (4-methoxybenzyl) -2—oxo ᅳ 1,2-dihydroquinoline-3-carbothioate;
(512) S-에틸 5- (아다만테인 -1-카복시아미도 )-1ᅳ(4-메톡시벤질) -2-옥소ᅳ 1 , 2 -디하이드로퀴놀린 -3-카보싸이오에이트;  (512) S-ethyl 5- (adamantane-1-carboxyxamido) -1 ′ (4-methoxybenzyl) -2-oxoze 1, 2-dihydroquinoline-3-carbothioate;
(513) 1-(4-메톡시 '변 1질) -5-나이트로퀴놀린 -2( 1H)-온; (513) 1- (4-methoxy ' mod 1) -5-nitroquinolin-2 (1H) -one;
(514) 5-아미노 -1-(4-메특시벤질)퀴놀린 -2( 1H)_온;  (514) 5-amino-1- (4-mesoxybenzyl) quinolin-2 (1H) _one;
(515) 5-하이드라지닐 -1-(4-메톡시벤질)퀴놀린 -2( 1H)-온；  (515) 5-hydrazinyl-1- (4-methoxybenzyl) quinolin-2 (1H) -one;
(516) N-( l-(4-메록시벤질) -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-( l-(4-메톡시벤질) -2-옥소 -1 , 2-디하이드로퀴놀린 -5-일) -3-메틸아다 만테인 -1—카복사마이드;  (517) N- (1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinolin-5-yl) -3-methyladamantane-1—carboxamide;
(518) N-( l-(4-메록시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -5-일) -3 , 5-디메틸 아다만테인 -1-카복사마이드；  (518) N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3, 5-dimethyl adamantane-1-carboxamide;
(519) 3-브로모 -N-( l-(4-메특시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -5-일) 아다만테인 -1-카복사마이드； (519) 3-bromo-N- (l- (4-mesoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carboxamide;
(520) 3-클로로 -N-( 1-(4—메톡시벤질) -2-옥소ᅳ1ᅳ 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-( l-(4-메톡시벤질) -2-옥소 -1 , 2-디하이드로 퀴놀 린 -5-일)아세트아마이드;  (521) 2- (adamantane-l-yl) -N- (l- (4-methoxybenzyl) -2-oxo-l, 2-dihydroquinolin-5-yl) acetamide;
(522) N-( 1-(4-메록시벤질 )-2-옥소 -1， 2-디하이드로퀴놀린 -5-일 )-2-(3ᅳ메틸 아다만탄 -1-일)아세트아마이드;  (522) N- (1- (4-methoxybenzyl) -2-oxo-1, 2-dihydroquinolin-5-yl) -2- (3′methyl adamantan-1-yl) acetamide;
(523) 2-(3， 5-디메틸아다만탄 -1ᅳ일 )-N-( 1-(4-메톡시벤질 )-2-옥소 -1， 2- 디하이드로퀴놀린 -5-일)아세트아마이드；  (523) 2- (3,5-dimethyladamantane-1 boilyl) -N- (1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) acetamide ;
(524) 2-(3-브로모아다만탄 -1-일) -N-( l-(4-메톡시벤질) -2-옥소 -1 , 2-디하이 드로퀴놀린 -5-일)아세트아마이드; (525) 2-(3-클로로아다만탄 -1-일) -N-(l-(4—메록시벤질) -2-옥소 -1,2-디하이 드로퀴놀린— 5-일)아세트아마이드; (524) 2- (3-bromoadamantane-1-yl) -N- (l- (4-methoxybenzyl) -2-oxo-1,2-dihedroquinolin-5-yl) acetamide ; (525) 2- (3-chloroadamantane-1-yl) -N- (l- (4—methoxybenzyl) -2-oxo-1,2-dihydrodroquinolin—5-yl) acetamide ;
(526) N'-(l-(4-메톡시벤질) -2-옥소 -1，2-디하이드로퀴놀린 -5-일)아다만테인 -1-카르보하이드라자이드;  (526) N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) adamantane-1-carbohydrazide;
(527) N'-(l-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -5-일) -3- 메틸아다만테인 -1-카르보하이드라자이드； (527) N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) -3-methyladamantane-1-carbohydrazide;
(528) N'-(l— (4ᅳ메톡시밴질 )— 2—옥소 -1，2—디하이드로퀴놀린 -5-일) -3,5- 디메틸아다만테인 -1—카르보하이드라자이드；  (528) N '-(l— (4'methoxybenzyl) — 2—oxo-1,2—dihydroquinolin-5-yl) -3,5-dimethyladamantane-1—carbohydrazide;
(529) 3-브로모 -N'-(l-(4-메록시벤질) -2-옥소 -1,2-디하이드로퀴놀린 -5ᅳ일) 아다만테인 -1—카르보하이드라자이드;  (529) 3-bromo-N '-(l- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5xyl) adamantane-1—carbohydrazide;
(530) 3-클로로 -N ' - ( 1-(4-메록시벤질 )-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-디하이드로 퀴놀린 -5-일)아세토하이드라자이드;  (531) 2- (adamantane-1-yl) -N '-(1- (4—methoxybenzyl) -2-oxo-1, 2-dihydro quinolin-5-yl) acetohydrazide;
(532) N'-(l— (4-메록시벤질) -2-옥소— 1，2-디하이드로퀴놀린 -5-일) -2-(3_메틸 아다만탄—1-일)아세토하이드라자이드; (532) N '-(l— (4-methoxybenzyl) -2-oxo— 1,2-dihydroquinolin-5-yl) -2- (3_methyl adamantane-1-yl) acetohai Dragazide;
(533) 2-(3,5-디메틸아다만탄-1-일)ᅦ'-(1-(4-메록시벤질)-2-옥소-1，2- 디하이드로퀴놀린 -5-일)아세토하이드라자이드；  (533) 2- (3,5-dimethyladamantan-1-yl) ''-(1- (4-methoxybenzyl) -2-oxo-1,2-dihydroquinolin-5-yl) aceto Hydrazide;
(534) 2-(3—브로모아다만탄 -1-일) -N'-(l-(4-메특시벤질)— 2-옥소 -1，2-디하이 드로퀴놀린 -5-일)아세토하이드라자이드; 및  (534) 2- (3—bromoadamantane-1-yl) -N '-(l- (4-methoxybenzyl) — 2-oxo-1,2-dihedroquinolin-5-yl) aceto Hydrazide; And
(535) 2— (3-클로로아다만탄 -1-일) -N'-(l— (4-메톡시벤질) -2-옥소 -1,2-디하이 드로퀴놀린 -5-일)아세토하이드라자이드  (535) 2— (3-Chloroadamantane-1-yl) -N '-(l— (4-methoxybenzyl) -2-oxo-1,2-dihydrodroquinolin-5-yl) aceto Hydrazide
로 구성된 군으로부터 선택되는 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염. Quinolinone derivative or a pharmaceutically acceptable salt thereof, characterized in that selected from the group consisting of.
- 【청구항 6】  -Claim 6
제 5 항에 있어서， 상기 퀴놀리논 유도체는  The method of claim 5, wherein the quinolinone derivative 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; (3) l-(4-플루오로벤질 )-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) l- (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-아미 ί·벤질 )-5-니트로 -2-옥소— Ν-펜에틸 -1， 2-디하이드로퀴놀린 -3- 카복사마이드; ：.  (7) 1- (4-amilo benzyl) -5-nitro-2-oxo—N-phenethyl-1, 2-dihydroquinoline-3-carboxamide; ：.
(8) 1-(4-시아노벤질) -5-니트로 -2-옥소 -Ν-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 -Ν-펜에틸 -1， 2-디하이드로퀴놀린- 3—카복사마이드; 및  (14) 1- (4-aminophenethyl) -5-nitro-2-oxo-Ν-phenethyl-1, 2-dihydroquinoline-3—carboxamide; And
( 16) 5-니트로 -1-(4-니트로펜에틸 )-2-옥소 -Ν-펜에틸 -1，2-디하이드로퀴놀린- 3-카복사마이드 (16) 5-nitro-1- (4-nitrophenethyl) -2-oxo-Ν-phenethyl-1,2-dihydroquinoline-3-carboxamide
로 구성된 군으로부터 선택되는 것을 특징으로 하는 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염. 【청구항 7】 Quinolinone derivative or a pharmaceutically acceptable salt thereof, characterized in that selected from the group consisting of. [Claim 7]
제 1 항 내지 제 6 항 중 어느 한 항의 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 IL— 2( Inter l eukin-2 )의 활성 억제용 조성물. [청구항 8】  A composition for inhibiting activity of IL-2 (Inter l eukin-2) comprising a quinolinone derivative of any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof as an active ingredient. [Claim 8]
제 1 항 내지 제 6 항 중 어느 한 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 an autoimmune disease comprising the quinolinone derivative of any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof as an active ingredient.
【청구항 9】 [Claim 9]
제 8 항에 있어서， 상기 염증성 질환은 만성폐쇄성 폐질환 (chroni c obstructive pulmonary disease) , 기도 과민성 질환 (airways hyper- responsiveness ), 폐혈성 쇼크 (septic shock) , 사구체 신염， 염증성 장질환， 크론병 (Crohn's disease), 궤양잘록창자염 (ulcerat ive colitis), 아테롬성 동맥경화증， 골수아구 세포성 백혈병 (myoblast ic leukaemia), 당뇨, 화상， 허혈성 심장질환， 뇌졸중， 수막염 및 정맥류로 구성된 군으로부터 선택되는 질환인 것을 특징으로 하는 조성물. The method of claim 8, wherein the inflammatory disease is chronic obstructive pulmonary disease (chroni c obstructive pulmonary disease, airways hyper- responsiveness, septic shock, glomerulonephritis, inflammatory bowel disease, Crohn's disease, ulcerat ive colitis, atherosclerosis And myoblast ic leukaemia, diabetes, burns, ischemic heart disease, stroke, meningitis and varicose veins.
【청구항 10】 [Claim 10]
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 of 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.
[청구항 11】 [Claim 11]
제 1 항 내지 제 6 항 중 어느 한 항의 퀴놀리논 유도체 또는 이의 약제학적으로 허용되는 염을 유효성분으로 포함하는 조성물을 대상체에 투여하는 단계를 포함하는 염증성 질환 또는 자가면역 질환의 예방 또는 치료방법.  A method for preventing or treating an inflammatory disease or an autoimmune disease comprising administering to a subject a composition comprising a quinolinone derivative of any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof as an active ingredient. .
PCT/KR2014/009272 2013-10-01 2014-10-01 Novel quinolinone derivative and use thereof WO2015050379A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020167008791A KR101731102B1 (en) 2013-10-01 2014-10-01 Novel Quinolinone Derivatives and Uses Thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20130117515 2013-10-01
KR10-2013-0117515 2013-10-01

Publications (1)

Publication Number Publication Date
WO2015050379A1 true WO2015050379A1 (en) 2015-04-09

Family

ID=52778922

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/009272 WO2015050379A1 (en) 2013-10-01 2014-10-01 Novel quinolinone derivative and use thereof

Country Status (2)

Country Link
KR (1) KR101731102B1 (en)
WO (1) WO2015050379A1 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106146464A (en) * 2015-04-10 2016-11-23 复旦大学 Quinolinones compound and its production and use
WO2018033455A1 (en) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2018174288A1 (en) 2017-03-24 2018-09-27 大正製薬株式会社 2(1h)-quinolinone derivative
CN109535305A (en) * 2018-11-26 2019-03-29 贵州省化工研究院 A kind of preparation method of Rhein adsorbent material
CN111187169A (en) * 2019-08-27 2020-05-22 福建永晶科技股份有限公司 Process for producing fluorobenzene derivative and hypofluorite benzoate derivative
RU2732297C2 (en) * 2018-11-14 2020-09-15 Общество с ограниченной ответственностью "Гурус БиоФарм" Derivatives of non-steroid anti-inflammatory agents
AU2016317968B2 (en) * 2015-09-04 2021-03-25 Shin Poong Pharmaceutical Co., Ltd. Compound having effect of inhibiting platelet aggregation and salt thereof, and composition for preventing or treating thrombotic diseases, containing same
US20230159493A1 (en) * 2021-09-13 2023-05-25 Eli Lilly And Company Ahr agonists
CN117186001A (en) * 2023-09-07 2023-12-08 南京中医药大学 AHA1 inhibitor with multiple myeloma-resisting activity and preparation method and application thereof

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 (2)

* Cited by examiner, † Cited by third party
Title
IWAMURA, H. ET AL.: "In Vitro and in Vivo Pharmacological Characterization of JTE-907, a Novel Selective Ligand for Cannabinoid CB2 Receptor", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 296, no. 2, 2001, pages 420 - 425 *
MEHTA, M. ET AL.: "Influence of Novel KGFR Tyrosine Kinase Inhibitors on KGF-mediated Proliferation of Breast Cancer.", ANTICANCER RESEARCH., vol. 30, 2010, pages 4883 - 4890 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106146464A (en) * 2015-04-10 2016-11-23 复旦大学 Quinolinones compound and its production and use
AU2016317968B2 (en) * 2015-09-04 2021-03-25 Shin Poong Pharmaceutical Co., Ltd. Compound having effect of inhibiting platelet aggregation and salt thereof, and composition for preventing or treating thrombotic diseases, containing same
WO2018033455A1 (en) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2018174288A1 (en) 2017-03-24 2018-09-27 大正製薬株式会社 2(1h)-quinolinone derivative
KR20190133667A (en) 2017-03-24 2019-12-03 다이쇼 세이야꾸 가부시끼가이샤 2 (1H) -quinolinone derivative
RU2732297C2 (en) * 2018-11-14 2020-09-15 Общество с ограниченной ответственностью "Гурус БиоФарм" Derivatives of non-steroid anti-inflammatory agents
CN109535305A (en) * 2018-11-26 2019-03-29 贵州省化工研究院 A kind of preparation method of Rhein adsorbent material
CN109535305B (en) * 2018-11-26 2021-12-03 贵州省化工研究院 Preparation method of rhein adsorbing material
CN111187169A (en) * 2019-08-27 2020-05-22 福建永晶科技股份有限公司 Process for producing fluorobenzene derivative and hypofluorite benzoate derivative
CN111187169B (en) * 2019-08-27 2023-05-09 福建永晶科技股份有限公司 Preparation process of fluorobenzene derivative and benzoic acid hypofluorite derivative
US20230159493A1 (en) * 2021-09-13 2023-05-25 Eli Lilly And Company Ahr agonists
CN117186001A (en) * 2023-09-07 2023-12-08 南京中医药大学 AHA1 inhibitor with multiple myeloma-resisting activity and preparation method and application thereof

Also Published As

Publication number Publication date
KR20160055181A (en) 2016-05-17
KR101731102B1 (en) 2017-04-27

Similar Documents

Publication Publication Date Title
WO2015050379A1 (en) Novel quinolinone derivative and use thereof
US20060247439A1 (en) Mchir antagonists
US6506747B1 (en) Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents
US9540360B2 (en) Sulfonamide compounds having TRPM8 antagonistic activity
CZ20033368A3 (en) Thiophene derivatives as antiviral agents for flavivirus infection
WO2011055270A1 (en) Indole based receptor crth2 antagonists
SK10102003A3 (en) Acylated indanyl amines, pharmaceutical composition containing same, method of the synthesis and their use as pharmaceuticals
JP2009529496A (en) Quinolones useful as inducible nitric oxide synthase inhibitors
KR20060121818A (en) N-substituted benzimidazolyl c-kit inhibitors
JPH0625134B2 (en) New heterocyclic compound
KR20070086865A (en) N-substituted benzimidazolyl c-kit inhibitors and combinatorial benzimidazole library
KR20000010905A (en) Tetrahydroisoquinoline derivative as regulator of dopamine d3 receptor
JP2010507664A (en) Benzimidazole compounds
KR100745307B1 (en) Aminoquinoline derivatives and their use as adenosine a3 ligands
JP2004525184A (en) 3-Substituted quinoline-4-carboxamide derivatives as NK-3 and NK-2 receptor antagonists
AU2002304358A1 (en) Aminoquinoline and aminopyridine derivatives and their use as adenosine A3 ligands
AU2011295408B2 (en) Substituted 2-oxo- and 2-thioxo-dihydroquinoline-3-carboxamides as KCNQ2/3 modulators
JP2000026430A (en) 2,5,6-substituted benzimidazole compound derivative
WO2014042238A1 (en) Sulfonamide compound
US20090048295A1 (en) Substituted 5,6,7,8-tetrahydroquinoline derivatives, compositions, and methods of use thereof
KR20070034136A (en) Imidazoquinoline derivatives
JP5323059B2 (en) ((Phenyl) imidazolyl) methyl heteroaryl compounds
JP2000226373A (en) Amine derivative, its production and agent therefor
JP2001508402A (en) Substituted benzamide derivatives and their use as anticonvulsants
WO2011161615A1 (en) 5-lipoxygenase inhibitors

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14850339

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20167008791

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205N DATED 07.06.2016)

122 Ep: pct application non-entry in european phase

Ref document number: 14850339

Country of ref document: EP

Kind code of ref document: A1