KR101984121B1 - 피리미디논 유도체 화합물 및 이의 용도 - Google Patents

피리미디논 유도체 화합물 및 이의 용도 Download PDF

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KR101984121B1
KR101984121B1 KR1020170105707A KR20170105707A KR101984121B1 KR 101984121 B1 KR101984121 B1 KR 101984121B1 KR 1020170105707 A KR1020170105707 A KR 1020170105707A KR 20170105707 A KR20170105707 A KR 20170105707A KR 101984121 B1 KR101984121 B1 KR 101984121B1
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methyl
phenyl
oxo
butyl
oxadiazol
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정원근
이준광
정희진
유병욱
박용
남은혜
김경희
진정욱
정경진
양덕모
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보령제약 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • Y10S514/866—

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Abstract

본 발명은 피리미디논 유도체, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염을 제공한다. 본 발명의 화합물은 고혈압 및/또는 당뇨병의 치료, 예방 또는 개선 활성을 나타낸다.

Description

피리미디논 유도체 화합물 및 이의 용도 {Pyrimininone derivative compounds and use thereof}
본 발명은 피리미디논 유도체 화합물 및 이의 용도에 관한 것이다.
고혈압은 만성 질환으로 아직까지 원인이 밝혀지지 않은 본태성 고혈압(1차성 고혈압)이 전체 환자의 90%를 차지하며, 고혈압 상태가 지속될 경우 심장마비, 뇌졸중 등의 치명적인 질환이 발생할 가능성이 증가한다. 특히, 대사성 질환의 하나인 당뇨가 동반되는 경우 그 치명성은 수배가 증가하게 된다.
안지오텐신 I으로부터 안지오텐신 전환 효소에 의해 생성되는 안지오텐신 II는 세포막 단백질로서 혈관 세포벽에 존재하는 안지오텐신 II 수용체를 통해 혈압을 증가시킨다는 사실이 알려져 있다. 따라서, 안지오텐신 II 길항제는 안지오텐신에 의해 발생되는 고혈압을 치료하는데 사용되었다. 지금까지, 경구 투여 안지오텐신 II 길항제로서 개발된 약물로, 로사르탄(losartan), 칸데사르탄 실레세틸(candesartan cilexetil), 올메사르탄 메독소밀(olmesartan medoxomil), 텔미사르탄(telmisartan), 피마사르탄(fimasartan) 등이 알려져 있다.
한편, 당뇨병은 혈중 혈당 조절에 문제가 발생하며, 이로 인해 신장 질환, 혈관 질환 등이 발생하고 욕창, 실명, 신부전 등으로 진행하여 심한 경우 생명을 위협하는 질환이다.
TZD(티아졸리딘디온)로 알려진 약물군은 PPARγ를 타겟으로 하며, 혈당 조절 이상 환자에 대해 인슐린에 대한 저항성을 완화시킴으로서 혈당 조절 능력을 회복시켜 주는 약물이다. 이러한 TZD 계열의 약물은 핵 수용체인 PPARγ를 활성화시키는데, 이로 인해 지방대사, 당대사 등 다양한 유전자의 발현이 증가하게 된다고 알려져 있다. 이로 인해 의도하지 않게 부종이나 비만 등이 부작용으로 나타나며, 이러한 부작용을 줄이고 인슐린 내성 극복이라는 약리 효과만을 얻기 위해 부분 활성화제, 선택적 조절제 등의 개발이 시도되어 왔다.
고혈압과 당뇨가 동반되는 환자군을 치료하기 위하여, 고혈압과 당뇨를 동시에 치료할 수 있는 치료제의 개발이 진행된 적이 있으나, 실제 약물 개발까지 이루어지지는 못하였다. 이에 본 발명자들은 고혈압 치료와 함께 인슐린 저항성을 조절하는 약물을 개발하고자 하였다.
한국등록특허 제10-0300566호 한국등록특허 제10-0617953호 한국등록특허 제10-0521980호
본 발명은 고혈압 및/또는 당뇨병의 치료 활성을 나타내는 피리미디논 유도체 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염을 제공하고자 한다.
또한, 본 발명은 본 발명의 피리미디논 유도체 화합물의 제조방법을 제공하고자 한다.
또한, 본 발명은 본 발명의 피리미디논 유도체 화합물의 용도를 제공하고자 한다.
본 발명자들은 고혈압 및/또는 당뇨병의 치료 활성을 나타내는 피리미디논 유도체 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염을 발견하고 본 발명을 완성하였다.
화학식 I의 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염
상기 목적에 따라 본 발명에서는, 하기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염을 제공한다:
[화학식 I]
Figure 112017080786708-pat00001
상기 화학식 I 에서,
Ra1 및 Ra2 는 각각 독립적으로 C1-C6 알킬, C3-C7 시클로알킬, C2-C6 헤테로시클로알킬, C2-C5 1차 또는 2차 아민, C2-C5 알콕시, 또는 C2-C5 설파이드이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H, 할로, C1-C4 알킬 또는 C1-C4 할로알킬이고,
Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
X1 및 X2 는 각각 독립적으로 O 또는 S 이고,
Y 는 C1-C4 알킬, C2-C4 알케닐, C2-C4 알키닐 또는 아무것도 아니고 (null) {여기서, 상기 C1-C4 알킬, C2-C4 알케닐 또는 C2-C4 알키닐의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
Z 는 OR1 또는 NR2R3 이고,
R1 은 H, C1-C6 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 카르복실산 또는 설포닐로 치환될 수 있음},
R2 및 R3 는 각각 독립적으로 H, C1-C6 알킬, C3-C7 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C6 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시, 아릴 또는 헤테로아릴로 치환될 수 있음}, 또는
R2 및 R3 는 연결된 질소 원자와 함께 5원-7원의 단일 고리 또는 7원-12원의 이중 고리를 형성한다 {여기서, 상기 단일 고리 또는 이중 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 할로알킬, C1-C4 알콕시, 히드록시, 카르복실산, 니트로, 설폰닐, C3-C7 시클로알킬, C2-C6 헤테로시클로알킬, 아릴 또는 헤테로아릴로 치환될 수 있음}.
또한, 본 발명의 일 구체예에 따르면, 상기 화학식 I 로 표시되는 화합물은,
상기 화학식 I 에서,
Ra1 및 Ra2 는 각각 독립적으로 C1-C6 알킬 또는 C3-C7 시클로알킬이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H 또는 할로이고,
Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
X1 및 X2 는 각각 독립적으로 O 또는 S 이고,
Y 는 C1-C4 알킬 또는 아무것도 아니고 (null) {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
Z 는 OR1 또는 NR2R3 이고,
R1 은 H, C1-C4 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 카르복실산 또는 설포닐로 치환될 수 있음},
R2 및 R3 는 각각 독립적으로 H, C1-C4 알킬, C3-C6 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시 또는 헤테로아릴로 치환될 수 있음}, 또는
R2 및 R3 는 연결된 질소 원자와 함께 5원-7원의 단일 고리, 6원-8원의 브릿지 이중 고리, 8원-10원의 융합 이중 고리 또는 9원-11원의 스파이로 이중 고리를 형성한다 {여기서, 상기 단일 고리, 브릿지 이중 고리, 융합 이중 고리 또는 스파이로 이중 고리의 하나 이상의 H는 할로, C1-C4 알킬 또는 C1-C4 할로알킬, 아릴 또는 헤테로아릴로 치환될 수 있음}.
또한, 본 발명의 일 구체예에 따르면, 상기 화학식 I 로 표시되는 화합물은,
상기 화학식 I 에서,
Ra1 및 Ra2 는 각각 독립적으로 C1-C4 알킬 또는 C3-C6 시클로알킬이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H 또는 할로이고,
Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
X1 및 X2 는 각각 독립적으로 O 또는 S 이고,
Y 는 C1-C4 알킬 또는 아무것도 아니고 (null) {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
Z 는 OR1 또는 NR2R3 이고,
R1 은 H, C1-C4 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시 또는 히드록시로 치환될 수 있음},
R2 및 R3 는 각각 독립적으로 H, C1-C4 알킬, C3-C7 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C6 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시 또는 헤테로아릴로 치환될 수 있음}, 또는
R2 및 R3 는 연결된 질소 원자와 함께 하기 고리 중 어느 하나를 형성하는 것이고 {여기서, 상기 고리의 하나 이상의 H는 할로, C1-C4 알킬 또는 C1-C4 할로알킬로 치환될 수 있음},
Figure 112017080786708-pat00002
R4 는 H, C1-C4 알킬, 아릴 또는 헤테로아릴이다 {여기서, 상기 아릴 또는 헤테로아릴은 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}.
또한, 본 발명의 구체예에 따르면, 상기 화학식 I 로 표시되는 화합물은, 하기 화합물들로 이루어진 군으로부터 선택된 어느 하나인 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염일 수 있다:
1) 에틸 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
2) 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세트산;
3) 메틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
4) 프로필 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
5) 부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
6) 펜틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
7) 아이소프로필 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
8) 아이소부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
9) 2-메틸부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
10) 벤질 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
11) 2-메톡시페네틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
12) 사이클로헥실 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
13) (1r,4r)-4-메틸사이클로헥실 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
14) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세트산;
15) 2-메틸부틸 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
16) 펜탄-3-일 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
17) 아이소프로필 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
18) 1-메톡시프로판2-일 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
19) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
20) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)프로파노에이트;
21) 에틸 2-(2-부틸-4-메틸-1-((2'-(4-메틸-5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트;
22) 에틸 2-(2-(1-브로모부틸)-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트 트리플루오로아세트산염;
23) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-2-하이드록시아세테이트 트리플루오로아세트산염;
24) 3-[2-[4-[[5-[2-[(1R)-2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일]-2-옥소-에틸]-2-부틸-4-사이클로프로필-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
25) 에틸 2-(4-터트-부틸-2-부틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
26) 페닐 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
27) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
28) {2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
29) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필아세트아마이드;
30) N-부틸-2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]아세트아마이드;
31) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이에틸아세트아마이드;
32) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일아세트아마이드;
33) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-아이소프로필-N-메틸아세트아마이드;
34) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)아세트아마이드;
35) {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
36) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
37) 3-[2-[4-[[2-부틸-4-메틸-5-(2-몰폴린-4-일에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
38) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
39) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(1-하이드록시프로판-2-일)아세트아마이드;
40) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
41) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드;
42) 2-부틸-N,N,4-트리메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카복스아마이드;
43) 2-부틸-N,4-다이메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-N-프로판-2-일피리미딘-5-카복스아마이드;
44) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(피페리딘-1-카보닐)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
45) 3-[2-[4-[[2-부틸-4-메틸-5-(몰폴린-4-카보닐)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
46) 3-[2-[4-[[5-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-카보닐)-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
47) 2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-N-프로판-2-일피리미딘-5-카복스아마이드;
48) 2-부틸-N-사이클로헥실-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카복스아마이드;
49) 2-부틸-N,4-다이메틸-N-(2-메틸프로필)-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카복스아마이드;
50) 3-[2-[4-[[2-부틸-5-(3,5-다이메틸피페리딘-1-카보닐)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
51) 2-부틸-4-메틸-N-(2-메틸프로필)-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카복스아마이드;
52) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
53) N-메톡시-N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]아세트아마이드;
54) N,N-다이메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]아세트아마이드;
55) 3-[2-[4-[[4-메틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
56) 3-[2-[4-[[4-메틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
57) 3-[2-[4-[[5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
58) 3-[2-[4-[[5-[2-(3,5-다이메틸몰폴린-4-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
59) N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]-N-프로판-2-일아세트아마이드;
60) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸프로판아마이드;
61) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일프로판아마이드;
62) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-사이클로프로필프로판아마이드;
63) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(3-옥소-3-피페리딘-1-일프로필)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
64) 3-[2-[4-[[2-부틸-4-메틸-5-(3-몰폴린-4-일-3-옥소프로필)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
65) 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일l)-3-옥소프로필]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
66) 3-[2-[4-[[2-부틸-4-메틸-5-[3-(4-메틸피페리딘-1-일)-3-옥소프로필]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
67) 3-[2-[4-[[2-부틸-5-[3-(3,3-다이메틸피페리딘-1-일)-3-옥소프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
68) 3-[2-[4-[[2-부틸-5-[3-(3,5-다이메틸몰폴린-4-일)-3-옥소프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
69) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부탄-2-일-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
70) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드;
71) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
72) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
73) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
74) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸몰폴린-4-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
75) 3-[2-[4-[[2-부틸-5-[2-(3,4-다이하이드로-1H-아이소퀴놀린-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
76) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-1H-아이소퀴놀린-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
77) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸피롤리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
78) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-2H-퀴놀린-1-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
79) 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2-옥소에틸)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
80) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸-1,3,3a,4,6,6a-헥사하이드로피롤로[3,4-c]피롤-5-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
81) 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-헥사하이드로-1H-사이클로펜타[c]피롤-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
82) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
83) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-옥소-2-(4-프로판-2-일피페리딘-1-일)에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
84) 3-[2-[4-[[2-부틸-5-[2-(2,3-다이하이드로인돌-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
85) 3-[2-[4-[[2-부틸-5-[2-(4-플루오로-1,3-다이하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
86) 2-[2-사이클로프로필-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
87) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-사이클로프로필-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
88) 3-(4'-((2-부틸-4-메틸-5-(2-(옥타하이드로-1H-인돌-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
89) 3-(4'-((2-부틸-5-(2-(다이하이드로-1H-피리도[1,2-a]피라진-2(6H,7H,8H,9H,9aH)-일)-2-옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
90) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
91) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
92) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-옥소-2-[4-(트리풀루오로메틸)피페리딘-1-일]에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
93) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
94) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
95) 3-[2-[4-[[2-부틸-5-[2-(4,4-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
96) 3-[2-[4-[[5-[2-(4,4-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
97) 3-[2-[4-[[2-부틸-5-[2-(2,5-다이메틸피롤리딘-1-일)-2-옥소-에틸]-4-메틸-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
98) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2S)-2-메틸피롤리딘-1-일]-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
99) 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6-다이메틸피페리딘-1-일]-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
100) 3-[2-[4-[[5-[2-[(4aS,8aR)-3,4,4a,5,6,7,8,8a-옥타하이드로-2H-퀴놀린-1-일]-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
101) 3-(4'-((2-부틸-4-메틸-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
102) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
103) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-사이클로프로필-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
104) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
105) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)아세트아마이드;
106) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-아이소프로필-N-메틸아세트아마이드;
107) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
108) 3-[2-[4-[[2-부틸-4-사이클로프로필-5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
109) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
110) 3-[2-[4-[[2-부틸-4-사이클로프로필-5-(2-몰폴린-4-일-2-옥소에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
111) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(1-하이드록시프로판-2-일)아세트아마이드;
112) N-부틸-2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]아세트아마이드;
113) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필아세트아마이드;
114) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일아세트아마이드;
115) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드
116) 3-(4'-((2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-(피롤리딘-1-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
117) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2,6-다이메틸피페라진-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
118) (S)-3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피롤리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
119) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
120) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-사이클로프로필아세트아마이드;
121) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이에틸아세트아마이드;
122) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸몰폴리노)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
123) 3-(4'-((2-부틸-4-사이클로프로필l-5-(2-((2S,6R)-2,6-다이메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
124) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-몰폴리노-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
125) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
126) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(4-하이드록시피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
127) 3-[2-[4-[[2-부틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
128) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸피페라진-1-일)-2-옥소에틸]-6-옥소-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
129) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이메틸아세트아마이드;
130) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이에틸아세트아마이드;
131) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
132) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-사이클로프로필아세트아마이드;
133) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
134) 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6-다이메틸피페리딘-1-일)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
135) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
136) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(3-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
137) 3-(4'-((2-부틸-4-아이소프로필-5-(2-몰폴리노-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
138) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
139) (S)-3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피롤리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
140) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
141) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
142) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
143) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
144) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
145) 3-[2-[4-[[2-부틸-4-에틸-5-(2-몰폴린-4-일-2-옥소에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
146) 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4-메틸피페리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
147) 3-[2-[4-[[2-부틸-5-[2-(3,3-다이메틸피페리딘-1-일)-2-옥소에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
148) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-옥소에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
149) 3-(4'-((2-부틸-4-메틸-6-옥소-5-(2-옥소-2-(싸이아졸리딘-3-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
150) 3-(4'-((2-부틸-4-메틸-5-(2-(4-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
151) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
152) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-(2-메톡시에틸)아세트아마이드;
153) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-(2-(싸이오펜-2-일)에틸)아세트아마이드;
154) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이아이소프로필아세트아마이드;
155) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
156) 3-(4'-((5-(2-(1H-아이소인돌-2(3H,3aH,4H,5H,6H,7H,7aH)-일)-2-싸이옥소에틸)-2-부틸-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
157) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
158) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
159) 3-[2-[4-[[2-부틸-4-메틸-5-(2-몰폴린-4-일-2-설파닐리덴에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
160) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일에탄싸이오아마이드;
161) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
162) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
163) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
164) 2-부틸-N,4-다이메틸-N-(2-메틸프로필)-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카보싸이오아마이드;
165) 2-부틸-N,N,4-트리메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카보싸이오아마이드;
166) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(피페리딘-1-카보싸이오일)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
167) 3-[2-[4-[[2-부틸-4-메틸-5-(몰폴린-4-카보싸이오일)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
168) 2-부틸-N,4-다이메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-N-프로판-2-일피리미딘-5-카보싸이오아마이드;
169) 3-[2-[4-[[5-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-카보싸이오일)-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
170) 2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-N-프로판-2-일피리미딘-5-카보싸이오아마이드;
171) 2-부틸-N-사이클로헥실-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카보싸이오아마이드;
172) 3-[2-[4-[[2-부틸-5-(3,5-다이메틸피페리딘-1-카보싸이오일)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
173) 2-부틸-4-메틸-N-(2-메틸프로필)-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카보싸이오아마이드;
174) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이에틸에탄싸이오아마이드;
175) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필에탄싸이오아마이드;
176) N-부틸-2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]에탄싸이오아마이드;
177) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
178) N-메톡시-N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]에탄싸이오아마이드;
179) N,N-다이메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]에탄싸이오아마이드;
180) 3-[2-[4-[[4-메틸-6-옥소-2-프로필-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
181) 3-[2-[4-[[4-메틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
182) 3-[2-[4-[[5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
183) 3-[2-[4-[[5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
184) N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일l)페닐]페닐]메틸]-2-프로필피리미딘-5-일]-N-프로판-2-일에탄싸이오아마이드;
185) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸프로판싸이오아마이드;
186) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일프로판싸이오아마이드;
187) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-사이클로프로필프로판싸이오아마이드;
188) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(3-피페리딘-1-일-3-설파닐리덴프로필)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
189) 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-3-설파닐리덴프로필]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
190) 3-[2-[4-[[2-부틸-4-메틸-5-[3-(4-메틸피페리딘-1-일)-3-설파닐리덴프로필]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
191) 3-[2-[4-[[2-부틸-5-[3-(3,3-다이메틸피페리딘-1-일)-3-설파닐리덴프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
192) 3-[2-[4-[[2-부틸-5-[3-(3,5-다이메틸몰폴린-4-일)-3-설파닐리덴프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
193) 3-[2-[4-[[2-부틸-4-메틸-5-(3-몰폴린-4-일-3-설파닐리덴프로필)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
194) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부탄-2-일-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
195) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
196) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
197) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
198) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
199) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
200) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
201) 3-[2-[4-[[2-부틸-5-[2-(3,4-다이하이드로-1H-아이소퀴놀린-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
202) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-1H-아이소퀴놀린-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
203) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-설파닐리덴-2-(1,3-싸이아졸리딘-3-일)에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
204) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
205) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
206) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
207) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(2-메톡시에틸)-N-메틸에탄싸이오아마이드;
208) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(2-싸이오펜-2-일에틸)에탄싸이오아마이드;
208) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이아이소프로필아세트아마이드;
209) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이(프로판-2-일)에탄싸이오아마이드;
210) 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2-설파닐리덴에틸)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
211) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸피롤리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
212) 2-[2-사이클로프로필-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
213) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-사이클로프로필-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
214) 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
215) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
216) 3-[2-[4-[[2-부틸-5-[2-(2,3-다이하이드로인돌-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
217) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-(4-프로판-2-일피페리딘-1-일)-2-설파닐리덴에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
218) 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-헥사하이드로-1H-사이클로펜타[c]피롤-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
219) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
220) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[4-(4-나이트로페닐)피페라진-1-일]-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
221) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
222) 2-[2-부틸-1-[[4-[5-플루오로-2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-메틸-6-옥소피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
223) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
224) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
225) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
226) 2-[2-부틸-1-[[4-[5-플루오로-2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-메틸-6-옥소피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
227) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸-1,3,3a,4,6,6a-헥사하이드로피롤로[3,4-c]피롤-5-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
228) 3-(4'-((2-부틸-5-(2-(헥사하이드로사이클로펜타[c]피롤-2(1H)-일)-2-싸이옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
229) 3-[2-[4-[[5-[2-(1,3,4,6,7,8,9,9a-옥타하이드로피리도[1,2-a]피라진-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
230) 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일)-2-싸이옥소-에틸]-2-부틸-4-메틸-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
231) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
232) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-설파닐리덴-2-[4-(트리플루오로메틸)피페리딘-1-일]에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
233) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
234) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
235) 3-[2-[4-[[2-부틸-5-[2-(4,4-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
236) 3-[2-[4-[[5-[2-(4,4-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
237) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
238) 5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-6-메틸-3-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-4-온;
239) 2-부틸-6-메틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-3-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-4-온;
240) 3-[2-[4-[[2-부틸-5-[2-(2,5-다이메틸피롤리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
241) 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6-다이메틸피페리딘-1-일]-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H6-1,2,4-옥사다이아졸-5-온;
242) 3-[2-[4-[[5-[2-[(4aS,7aR)-1,3,4,4a,5,6,7,7a-옥타하이드로사이클로펜타[c]피리딘-2-일]-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
243) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2S)-2-메틸피롤리딘-1-일]-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
244) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2R)-2-메틸피롤리딘-1-일]-2-싸이옥소-에틸]-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
245) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
246) 3-(4'-((2-부틸-4-메틸-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
247) 3-(4'-((2-부틸-4-메틸-6-옥소-5-(2-싸이옥소-2-(3-(트리플루오로메틸)-5,6-다이하이드로-[1,2,4]트리아졸로[4,3-a]피라진-7(8H)-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
248) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
249) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
250) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-사이클로프로필-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
251) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
252) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
253) 3-(4'-((2-부틸-4-사이클로프로필-6-옥소-5-(2-(피롤리딘-1-일)-2-싸이옥소에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
254) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2,6-다이메틸피페라진-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
255) (S)-3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피롤리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
256) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
257) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-사이클로프로필에탄싸이오아마이드;
258) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이에틸에탄싸이오아마이드;
259) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸몰폴리노)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
260) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-((2S,6R)-2,6-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
261) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-몰폴리노-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
262) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
263) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(4-하이드록시피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
264) 3-[2-[4-[[2-부틸-6-옥소-4-프로판-2-일-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
265) 3-[2-[4-[[2-부틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
266) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸피페라진-1-일)-2-설파닐리덴에틸]-6-옥소-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
267) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
268) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이에틸에탄싸이오아마이드;
269) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
270) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-사이클로프로필에탄싸이오아마이드;
271) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-싸이옥소에틸)-6-옥소-5,6-다이하이드로피리미딘-1(4H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
272) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일l)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
273) 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
274) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
275) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(3-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
276) 3-(4'-((2-부틸-4-아이소프로필-5-(2-몰폴리노-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
277) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
278) (S)-3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피롤리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
279) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
280) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
281) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
282) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
283) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
284) 3-[2-[4-[[2-부틸-4-에틸-5-(2-몰폴린-4-일-2-설파닐리덴에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
285) 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
286) 3-[2-[4-[[2-부틸-5-[2-(3,3-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온; 및
287) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온.
본 발명에서, 약제학적으로 허용가능한 염은 의약업계에서 통상적으로 사용되는 염을 의미하며, 예를 들어 칼슘, 포타슘, 소듐 및 마그네슘 등으로 제조된 무기이온염, 염산, 질산, 인산, 브롬산, 요오드산, 과염소산 및 황산 등으로 제조된 무기산염; 아세트산, 트라이플루오로아세트산, 시트르산, 말레인산, 숙신산, 옥살산, 벤조산, 타르타르산, 푸마르산, 만데르산, 프로피온산, 젖산, 글리콜산, 글루콘산, 갈락투론산, 글루탐산, 글루타르산, 글루쿠론산, 아스파르트산, 아스코르브산, 카본산, 바닐릭산, 하이드로 아이오딕산 등으로 제조된 유기산염; 메탄설폰산, 에탄설폰산, 벤젠설폰산, p-톨루엔설폰산 및 나프탈렌설폰산 등으로 제조된 설폰산염; 글리신, 아르기닌, 라이신 등으로 제조된 아미노산염; 및 트리메틸아민, 트라이에틸아민, 암모니아, 피리딘, 피콜린 등으로 제조된 아민염 등이 있으나, 열거된 이들 염에 의해 본 발명에서 의미하는 염의 종류가 한정되는 것은 아니다.
본 발명의 화학식 I 로 표시되는 화합물은 1 개 이상의 비대칭 탄소를 함유할 수 있으며, 이에 따라 라세미체, 라세믹 혼합물, 단일의 에난티오머, 부분입체이성체 혼합물 및 각각의 부분입체이성체로서 존재할 수 있다. 이러한 이성질체는 종래기술, 예를 들어 화학식 I 로 표시된 화합물은 관 크로마토그래피 또는 HPLC 등의 분할에 의해 분리가 가능하다. 또는, 화학식 I 로 표시되는 화합물 각각의 입체 이성질체는 공지된 배열의 광학적으로 순수한 출발 물질 및/또는 시약을 사용하여 입체 특이적으로 합성할 수 있다.
화학식 I 화합물의 제조방법
본 발명은 화학식 I 로 표시되는 화합물, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염의 제조방법을 제공한다.
Figure 112017080786708-pat00003
상업적으로 구입가능한 화합물 1 및 화합물 2 로부터 염기(base)를 이용한 중합반응을 통해 화합물 3을 얻고, 이와 아미딘 4의 고리형성 반응을 통해 화합물 5를 얻는다. 화합물 6과 염기(base)를 이용한 중합반응을 통해 화합물 7을 얻고 이후 시아노 기를 공지된 방법을 통해 옥사다이졸론으로 변형하여 화합물 11을 얻는다.
화합물 11을 가수분해 후 여러가지 알코올과 반응시켜 다양한 종류의 에스터를 얻거나, 아민과 트란스 에스터반응으로 아미드화합물을 얻은 후 로손시약을 이용하여 티오아미드화합물을 얻었다.
화학식 I 화합물을 포함하는 조성물, 이의 용도 및 이를 이용한 치료방법
본 발명은 하기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 고혈압 또는 당뇨병의 치료 또는 예방용 약학적 조성물을 제공한다.
[화학식 I]
Figure 112017080786708-pat00004
상기 화학식 I 은 위에서 정의한 바와 같다.
본 발명에 있어서, 상기 고혈압은 본태성 고혈압일 수 있고, 상기 당뇨병은 제2형 당뇨병일 수 있다.
본 발명의 일 구체예에 따르면, 본 발명의 화합물은 고혈압 및 당뇨병 모두에 대하여 약리활성을 나타낸다. 따라서, 본 발명의 약학적 조성물은 고혈압 및 당뇨병을 동시에 치료 또는 예방하기 위하여 유용하게 사용될 수 있다.
본 발명의 약학적 조성물은 투여를 위해서 상기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염 외에 추가로 약제학적으로 허용가능한 담체를 1 종 이상 더 포함할 수 있다. 약제학적으로 허용 가능한 담체는 식염수, 멸균수, 링거액, 완충 식염수, 덱스트로즈 용액, 말토 덱스트린 용액, 글리세롤, 에탄올 및 이들 성분 중 1 성분 이상을 혼합하여 사용할 수 있으며, 필요에 따라 항산화제, 완충액, 정균제 등 다른 통상의 첨가제를 첨가할 수 있다. 또한 희석제, 분산제, 계면활성제, 결합제 및 윤활제를 부가적으로 첨가하여 수용액, 현탁액, 유탁액 등과 같은 주사용 제형, 환약, 캡슐, 과립 또는 정제로 제제화할 수 있다. 따라서, 본 발명의 조성물은 패치제, 액제, 환약, 캡슐, 과립, 정제, 좌제 등일 수 있다. 이들 제제는 당 분야에서 제제화에 사용되는 통상의 방법 또는 Remington's Pharmaceutical Science(최근판), Mack Publishing Company, Easton PA 에 개시되어 있는 방법으로 제조될 수 있으며 각 질환에 따라 또는 성분에 따라 다양한 제제로 제제화될 수 있다.
본 발명의 조성물은 목적하는 방법에 따라 경구 투여하거나 비경구 투여(예를 들어, 정맥 내, 피하, 복강 내 또는 국소에 적용)할 수 있으며, 투여량은 환자의 체중, 연령, 성별, 건강상태, 식이, 투여시간, 투여방법, 배설율 및 질환의 중증도 등에 따라 그 범위가 다양하다. 본 발명의 화학식 I 로 표시되는 화합물의 일일 투여량은 약 1 내지 1000 ㎎/㎏ 이고, 바람직하게는 5 내지 100 ㎎/㎏ 이며, 하루 일회 내지 수회에 나누어 투여할 수 있다.
본 발명의 상기 약학적 조성물은 상기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염 외에 동일 또는 유사한 약효를 나타내는 유효성분을 1 종 이상 더 포함할 수 있다.
본 발명은 상기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염의 치료학적으로 유효한 양을 인간을 포함하는 포유류에 투여하는 단계를 포함하는, 고혈압 또는 당뇨병을 치료하는 방법을 제공한다.
본 발명에서 사용되는 “치료학적으로 유효한 양”이라는 용어는 고혈압 또는 당뇨병의 치료에 유효한 상기 화학식 I 로 표시되는 화합물의 양을 나타낸다.
본 발명의 치료방법은 상기 화학식 I 로 표시되는 화합물을 투여함으로써, 징후의 발현 전에 질병 그 자체를 다룰 뿐만 아니라, 이의 징후를 저해하거나 피하는 것을 또한 포함한다. 질환의 관리에 있어서, 특정 활성 성분의 예방적 또는 치료학적 용량은 질병 또는 상태의 본성(nature)과 심각도, 그리고 활성 성분이 투여되는 경로에 따라 다양할 것이다. 용량 및 용량의 빈도는 개별 환자의 연령, 체중 및 반응에 따라 다양할 것이다. 적합한 용량 용법은 이러한 인자를 당연히 고려하는 이 분야의 통상의 지식을 가진 자에 의해 쉽게 선택될 수 있다. 또한, 본 발명의 치료방법은 상기 화학식 I 로 표시되는 화합물과 함께 질환 치료에 도움이 되는 추가적인 활성 제제의 치료학적으로 유효한 양의 투여를 더 포함할 수 있으며, 추가적인 활성제제는 상기 화학식 I 의 화합물과 함께 시너지 효과 또는 보조적 효과를 나타낼 수 있다.
본 발명은 또한 고혈압 또는 당뇨병의 치료용 약제의 제조를 위한 상기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체 또는 이의 약제학적으로 허용가능한 염의 용도를 제공하고자 한다. 약제의 제조를 위한 상기 화학식 I 로 표시되는 화합물은 허용되는 보조제, 희석제, 담체 등을 혼합할 수 있으며, 기타 활성제제와 함께 복합 제제로 제조되어 활성 성분들의 상승 작용을 가질 수 있다.
본 발명의 조성물, 용도, 치료방법에서 언급된 사항은 서로 모순되지 않는 한 동일하게 적용된다.
본 발명의 피리미디논 유도체 화합물은 고혈압 및/또는 당뇨병의 치료 활성을 나타낸다.
이하, 하기 실시예 및 실험예를 들어 본 발명을 더욱 구체적으로 설명한다. 그러나 이들 실시예 및 실험예는 본 발명에 대한 이해를 돕기 위해 예시의 목적으로만 제공된 것일 뿐 본 발명의 범위가 하기 실시예 및 실험예에 의해 제한되는 것은 아니다.
< 실시예 1> 에틸 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Ethyl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
[단계 1] 에틸 2-(2-부틸-1-((2'-시아노바이페닐-4-일)메틸)-4-아이소프로필-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트 {Ethyl 2-(2-butyl-1-((2'-cyanobiphenyl-4-yl)methyl)-4-isopropyl-6-oxo-1,6-dihydropyrimidin-5-yl)acetate}의 제조
Figure 112017080786708-pat00005
플라스크에 에틸 2-(2-부틸-4-아이소프로필-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트 (28.0 g, 0.1 mol)과 4'-(브로모메틸)바이페닐-2-카보니트릴 (29.9 g, 0.11 mol)을 투입한 후, 9:1의 에틸아세테이트/다이메틸포름아마이드 혼합비로 섞은 혼합 용액 132 mL를 주입하였다. 30 분 동안 실온에서 교반한 후, 리튬 하이드라이드 (950 mg, 0.12mol)을 분가하여 투입하였다. 혼합 용액을 65 ℃에서 15 시간 동안 가온 교반한 후, 감압 농축하여 용매를 제거하고 에틸아세테이트 150 mL와 정제수 150 mL를 가하여 유기층을 분리하였다. 분리한 유기층을 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 2:1 에틸아세테이트/n-헥산을 사용하여 크로마토그래피로 정제하여 미황백색 고체의 표제 화합물 22 g (수율: 47.3 %)을 얻었다.
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.29 (t, 3H), 1.42 (m, 2H), 1.71 (m, 2H), 2.33 (s, 3H), 2.69 (t, 2H), 3.64 (s, 2H), 4.21 (q, 2H), 5.38 (s, 2H), 7.27 (d, 2H), 7.49 (m, 2H), 7.53 (d, 2H), 7.73 (t, 1H), 7.80 (t, 1H)
[단계 2] (Z)-에틸 2-(2-부틸-1-((2'-(N'-하이드록시카밤이미도일)바이페닐-4-일)메틸)-4-아이소프로필-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트 {(Z)-ethyl 2-(2-butyl-1-((2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-4-isopropyl-6-oxo-1,6-dihydropyrimidin-5-yl)acetate} 의 제조
Figure 112017080786708-pat00006
플라스크에 단계 1에서 제조된 화합물 (13.2g, 28 mmole)을 투입하고 다이메틸설파이드 72 mL를 주입한 후, 50 % 암모늄 하이드록사이드 수용액 (7.2 mL, 118 mmole)를 적가하고 95 ℃ 로 15 시간 동안 가온 교반하였다. 가온 교반을 완료한 후, 감압농축하고 에틸아세테이트 300 mL와 정제수 150 mL을 가하여 유기층을 분리하였다. 분리한 유기층을 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 1:2 에틸아세테이트/n-헥산을 사용하여 크로마토그래피로 정제하여 미황색 액체의 표제 화합물 11.7 g (수율: 86.0 %)을 얻었다.
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.28 (t, 3H), 1.41 (m, 2H), 1.68 (m, 2H), 2.32 (s, 3H), 2.67 (t, 2H), 3.64 (s, 2H), 4.21 (q, 2H), 4.42 (b, 2H), 5.35 (s, 2H), 7.25 (d, 2H), 7.49 (m, 2H), 7.53 (m, 3H), 7.80 (d, 1H)
[단계 3] 에틸 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트 {Ethyl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate} 의 제조
Figure 112017080786708-pat00007
플라스크에 단계 2에서 제조된 화합물 (12.3 g, 24.8 mmole)을 투입하고 다이메틸설파이드 용액 62 mL를 주입하였다. 온도를 10 ℃ 이하로 유지하며 다이메틸카보네이트 6.28 mL를 주입하고, 28 % 소듐 메톡사이드 (9.4 mL, 73.8 mmole)를 15 분 동안 서서히 적가하였다. 적가가 완료되면 10 분 동안 실온 교반하고, 차가운 정제수 150 mL와 클로로포름 200 mL를 주입한 후, 2N-염산 수용액을 적가하여 pH를 3~3.5로 조절하고 클로로포름층을 분리하였다. 분리한 클로로포름층을 정제수 150 mL, 소금물 150 mL로 세척하고 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 1:1 에틸아세테이트/n-헥산 100 mL를 사용하여 미황색 고체의 표제 화합물 6.65 g (수율: 50.6 %)을 얻었다.
1H-NMR (400MHz): δ 0.94 (t, 3H), 1.28 (t, 3H), 1.43 (m, 2H), 1.72 (m, 2H), 2.32 (s, 3H), 2.69 (t, 2H), 3.59 (s, 2H), 4.15 (q, 2H), 5.31 (s, 2H), 7.26 (d, 2H), 7.33 (d, 2H), 7.43 (m, 1H), 7.53 (t, 1H), 7.63 (d, 1H), 7.82 (d, 1H), 8.19 (b, 1H)
< 실시예 2> 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세트산 {2-(2- butyl -4- isopropyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetic acid } 의 제조
Figure 112017080786708-pat00008
플라스크에 실시예 1에서 제조된 화합물 (6.2 g, 11.7 mmole)을 투입하고 메틸알콜 50 mL를 주입하였다. 온도를 15 ℃ 이하로 유지하며 2.5N 수산화나트륨 수용액 10 mL를 적가하고 15 시간 동안 실온 교반하였다. 실온 교반을 완료한 후, 감압농축하고 클로로포름 150 mL와 정제수 150 mL을 주입하고, 2N 염산 수용액을 적가하여 pH를 3~4로 조절하고 클로로포름층을 분리하였다. 분리한 클로로포름층을 정제수 150 mL로 세척하고 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 1:2 에틸아세테이트/n-헥산 60 mL를 사용하여 미황색 고체의 표제 화합물 4.4 g (수율: 75.7 %)을 얻었다.
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.42 (m, 2H), 1.72 (m, 2H), 2.33 (s, 3H), 2.65 (t, 2H), 3.49 (s, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 3> 메틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Methyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
[단계 1] 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세트산 {2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetic acid}의 제조
Figure 112017080786708-pat00009
출발물질을 에틸 2-(2-부틸-4-메틸-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트을 사용하여 위 합성 스킴과 같이 실시예 1 및 2와 동일한 합성 방법을 사용하여 백색 분말의 표제 화합물(수율: 50%)을 얻었다.
[단계 2] 메틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트 {Methyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
Figure 112017080786708-pat00010
플라스크에 단계 1에서 제조된 화합물 (5.0 mmole)을 투입하고 메틸알콜 50 mL를 주입하였다. 1 mL 황산을 첨가한 후 16 시간 동안 환류 교반하였다. 실온으로 냉각 후 감압농축한 후 클로로포름 150 mL와 정제수 150 mL을 주입하고 클로로포름층을 분리하였다. 분리한 클로로포름층을 정제수 150 mL로 세척하고 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 1:2 에틸아세테이트/n-헥산을 60 mL를 사용하여 백색 고체의 표제 화합물 (수율: 90%, 4.5 mmole)을 얻었다.
1H-NMR (400MHz, CDCl3): δ 0.86-0.92 (3H, t), 1.31-1.40 (2H, m), 1.57-1.68 (2H, m), 2.24 (3H, s), 2.60-2.65 (2H, t), 3.56 (3H, s), 3.99-4.04 (2H, t), 5.23 (2H, s), 7.12-7.71 (8H, m)
< 실시예 4 내지 실시예 26>
실시예 4 내지 실시예 26 는 실시예 3과 다른 종류의 알코올을 용매로 사용하거나, 알코올 2 당량과 THF 용매에서 동일 방법으로 합성하였다.
< 실시예 4> 프로필 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Propyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.86-0.92 (6H, m), 1.31-1.40 (2H, m), 1.57-1.68 (4H, m), 2.24 (3H, s), 2.60-2.64 (2H, t), 3.50 (2H, s), 3.99-4.03 (2H, t), 5.23 (2H, s), 7.11-7.71 (8H, m)
< 실시예 5> 부틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Butyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.86-0.92 (6H, m), 1.29-1.40 (4H, m), 1.54-1.68 (4H, m), 2.24 (3H, s), 2.60-2.64 (2H, t), 3.49 (2H, s), 4.04-4.07 (2H, t), 5.23 (2H, s), 7.12-7.72 (8H, m)
< 실시예 6> 펜틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Pentyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.86-0.90 (6H, m), 1.26-1.40 (6H, m), 1.56-1.68 (4H, m), 2.23 (3H, s), 2.59-2.63 (2H, t), 3.49 (2H, s), 4.02-4.06 (2H, t), 5.23 (2H, s), 7.11-7.71 (8H, m)
< 실시예 7> 아이소프로필 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트; Isopropyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (3H, t), 1.20-1.21 (6H, d), 1.31-1.41 (2H, m), 1.61-1.69 (2H, m), 2.24 (3H, s), 2.60-2.64 (2H, t), 3.47 (2H, s), 4.93-5.02 (1H, m), 5.23 (2H, s), 7.12-7.73 (8H, m)
< 실시예 8> 아이소부틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Isobutyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (9H, m), 1.32-1.41 (2H, m), 1.62-1.70 (2H, m), 1.85-1.95 (1H, m), 2.26 (3H, s), 2.62-2.66 (2H, t), 3.52 (2H, s), 3.84-3.85 (2H, d), 5.24 (2H, s), 7.14-7.76 (8H, m)
< 실시예 9> 2- 메틸부틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하 이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트 {2- methylbutyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.85-0.90 (9H, m), 1.09-1.20 (1H, m), 1.31-1.41 (3H, m), 1.61-1.72 (3H, m), 2.25 (3H, s), 2.60-2.64 (2H, t), 3.51 (2H, s), 3.83-3.97 (2H, m), 5.23 (2H, s), 7.13-7.73 (8H, m)
< 실시예 10> 벤질 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Benzyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (3H, t), 1.31-1.41 (2H, m), 1.61-1.69 (2H, m), 2.23 (3H, s), 2.61-2.65 (2H, t), 3.56 (2H, s), 5.10 (2H, s), 5.23 (2H, s), 7.12-7.73 (13H, m)
< 실시예 11> 2- 메톡시페네틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리 미딘-5-일)아세테이트 {2- methoxyphenethyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz, CDCl3): δ 0.87-0.90 (3H), 1.30-1.42 (2H), 1.62-1.70 (2H), 2.23 (3H), 2.60-2.65 (2H), 3.56 (2H), 3.89 (3H), 5.11 (2H, s), 5.23 (2H, s), 7.12-7.73 (12H, m)
< 실시예 12> 사이클로헥실 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미 딘-5-일)아세테이트 { Cyclohexyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.89-0.93 (3H, t), 1.32-1.84 (14H, m), 2.28 (3H, s), 2.65-2.69 (2H, t), 3.53 (2H, s), 4.73-4.79 (1H, m), 5.28 (2H, s), 7.18-7.82 (8H, m)
< 실시예 13> (1r,4r)-4- 메틸사이클로헥실 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이 하이드로피리미딘-5-일)아세테이트 {( 1r,4r )-4- methylcyclohexyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.89-0.93 (3H, t), 1.34-1.43 (2H, m), 1.64-1.72 (2H, m), 2.21 (3H, s), 2.64-2.68 (2H, t), 2.91-2.95 (2H, t), 3.51 (3H, s), 3.80 (3H, s), 4.25-4.288 (2H, t), 5.25 (2H, s), 6.83-6.87 (2H, m), 7.08-7.79 (8H, m)
< 실시예 14> 2-(2-부틸-4- 사이클로프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세트산 {2-(2- butyl -4- cyclopropyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetic acid }의 제조
Figure 112017080786708-pat00011
위 합성 스킴과 같이 출발물질을 에틸 2-(2-부틸-4-사이클로프로필-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트를 사용하여 실시예 1 및 2와 동일한 합성 방법을 사용하여 백색 분말의 표제 화합물(수율: 35%)을 얻었다.
1H-NMR (400MHz): δ 0.95 (m, 5H), 1.20 (m, 2H), 1.38 (m, 2H), 1.71 (m, 2H), 2.05 (m, 1H), 2.61 (t, 2H), 3.76 (s, 3H), 4.18 (q, 2H), 5.25 (s, 2H), 7.22 (d, 2H), 7.31 (m, 2H), 7.41 (d, 1H), 7.54 (t, 1H), 7.66 (t, 1H), 7.89 (d, 1H)
< 실시예 15> 2- 메틸부틸 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5-다 이하이 드로-1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로 피리미딘-5-일)아세테이트 {2- methylbutyl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (9H, m), 1.15-1.16 (6H, d), 1.31-1.39 (2H, m), 1.60-1.70 (2H, m), 1.85-1.94 (1H, m), 2.88-2.97 (1H, m), 2.61-2.66 (2H, t), 3.52 (2H, s), 3.83-3.85 (2H, d), 5.24 (2H, s), 7.13-7.76 (8H, m)
< 실시예 16> 펜탄-3-일 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5-다 이하이 드로-1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로 피리미딘-5-일)아세테이트 { Pentan -3- yl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-1.10 (9H, m), 1.15-1.16 (6H, d), 1.31-1.39 (2H, m), 1.60-1.70 (4H, m), 1.85-1.94 (1H, m), 2.88-2.97 (1H, m), 2.61-2.66 (2H, t), 3.52 (2H, s), 3.83-3.85 (2H, d), 5.24 (2H, s), 7.13-7.76 (8H, m)
< 실시예 17> 아이소프로필 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5-다 이하이 드로-1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드 로피리미딘-5-일)아세테이트 { Isopropyl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (9H, m), 1.15-1.16 (6H, d), 1.31-1.39 (2H, m), 1.85-1.94 (1H, m), 2.88-2.97 (1H, m), 2.61-2.66 (2H, t), 3.52 (2H, s), 3.83-3.85 (2H, d), 5.24 (2H, s), 7.13-7.76 (8H, m)
< 실시예 18> 1- 메톡시프로판2 -일 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이 하이드로피리미딘-5-일)아세테이트 {1- methoxypropan -2- yl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.87-0.91 (6H, m), 1.15-1.16 (6H, d), 1.31-1.39 (2H, m), 1.86-1.95 (1H, m), 2.88-2.97 (1H, m), 2.61-2.66 (2H, t), 3.52 (2H, s), 3.83-3.85 (5H, m), 5.23 (2H, s), 7.13-7.77 (8H, m)
< 실시예 19> 에틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Ethyl 2-(2- butyl -4- methyl -6- oxo -1-((2'-(5- oxo -4,5- dihydro -1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 7.69-7.63 (m, 2H), 7.56-7.51 (m, 2H), 7.34 (d, 2H), 7.22 (d, 2H), 5.42 (s, 2H), 4.16 (q, 2H), 3.63 (s, 2H), 2.69 (t, 2H), 2.31 (s, 3H), 1.62 (quint, 2H), 1.35 (sx, 2H), 1.25 (t, 3H), 0.88 (t, 3H)
< 실시예 20> 에틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)프로파노에이트 { Ethyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)propanoate}의 제조
1H-NMR (400MHz): δ 7.70-7.63 (m, 2H), 7.56-7.51 (m, 2H), 7.34 (d, 2H), 7.20 (d, 2H), 5.55 (s, 2H), 5.54-5.24 (m, 3H), 4.12 (q, 2H), 3.85-3.51 (m, 1H), 2.72-2.66 (m, 2H), 2.31 (s, 2H), 1.60 (quint, 3H), 1.41-1.32 (m, 2H), 1.18 (t, 3H), 0.88 (t, , 3H)
< 실시예 21> 에틸 2-(2-부틸-4- 메틸 -1-((2'-(4- 메틸 -5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-6-옥소-1,6- 다이하이드로피리미 딘-5-일)아세테이트 { Ethyl 2-(2-butyl-4-methyl-1-((2'-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-6-oxo-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 7.77-7.73 (m, 1H), 7.64-7.57 (m, 3H), 7.39 (d, 2H), 7.24 (d, 2H), 5.45 (s, 2H), 4.16 (q, 2H), 3.65 (s, 2H), 2.81 (t, 2H), 2.55 (s, 3H), 2.36 (s, 3H), 1.59 (quint, 2H), 1.39 (sx, 2H), 1.25 (t, 3H), 0.88 (t, 3H)
< 실시예 22> 에틸 2-(2-(1- 브로모부틸 )-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리 미딘-5-일)아세테이트 트리플루오로아세트산염 { Ethyl 2-(2-(1-bromobutyl)-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate trifluoroacetic acid salt }의 제조
1H-NMR (400MHz): δ 7.71-7.65 (m, 2H), 7.58-7.50 (m, 2H), 7.38 (d, 2H), 7.25 (d, 2H), 5.97 (d, 1H), 5.13 (d, 1H), 4.84 (t, 1H), 4.21 (q, 2H), 3.68 (s, 2H), 2.37 (s, 3H), 2.34-2.25 (m, 1H), 2.21-2.10 (m, 1H), 1.28-1.26 (m, 3H), 1.25-1.18 (m, 2H), 0.80 (t, 3H)
< 실시예 23> 에틸 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-2-하이드록시아세테이트 트리플루오로아세트산염 { Ethyl 2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-2-hydroxyacetate trifluoroacetic acid salt }의 제조
1H-NMR (400MHz): δ 7.71-7.65 (m, 2H), 7.58-7.53 (m, 2H), 7.37 (d, 2H), 7.26 (d, 2H), 5.51 (m, 1H), 5.40 (s, 2H), 5.36 (m, 1H), 4.24-4.17 (m, 2H), 2.74-2.70 (m, 2H), 2.42 (s, 3H), 1.25 (t, 3H), 0.92 (m, 5H)
< 실시예 24> 3-[2-[4-[[5-[2-[(1R)-2,3,3a,4,5,6,7,7a- 옥타하이드로인돌 -1-일]-2-옥소-에틸]-2-부틸-4- 사이클로프로필 -6-옥소-피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-[(1R)-2,3, 3a,4 ,5,6,7,7a- octahydroindol -1- yl ]-2- oxo - ethyl ]-2- butyl -4-cyclopropyl-6-oxo-pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR(400MHz, CDCl3): δ 0.95 (m, 5H), 1.15-1.17 (m, 4H), 1.35 (m, 4H), 1.63-1.67 (m, 4H), 1.7-1.9(m, 2H), 2.2-2.4 (m, 2H), 2.64 (dd, 2H), 3.65-3.69 (m, 4H), 4.03-4.06 (m, 1H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 25> 에틸 2-(4- 터트 -부틸-2-부틸-6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)아세테이트 { Ethyl 2-(4-tert-butyl-2-butyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 1.20 (t, 9H), 1.26 (t, 3H), 1.43 (m, 2H), 1.77 (m, 2H), 2.69 (t, 2H), 2.71 (t, 2H), 2.98 (q, 1H), 3.61 (s, 2H), 4.17 (q, 2H), 5.30 (s, 2H), 7.26 (m, 2H), 7.33 (d, 2H), 7.43 (d, 1H), 7.51 (t, 1H), 7.62 (d, 1H), 7.85 (d, 1H)
< 실시예 26> 페닐 2-(2-부틸-4- 아이소프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미 딘-5-일)아세테이트 { Phenyl 2-(2-butyl-4-isopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)acetate}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.23 (d, 6H), 1.41 (m, 2H), 1.78 (m, 2H), 2.71 (t, 2H), 3.41 (q, 1H), 3.98 (s, 2H), 5.25 (s, 2H), 6.91 (m, 4H), 7.01 (m, 2H), 7.31 (d, 2H), 7.34 (d, 2H), 7.75 (m, 2H), 7.78 (d, 1H)
< 실시예 27> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(2-옥소-2- 피롤리딘 -1- 일에틸 )피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(2-oxo-2-pyrrolidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
Figure 112017080786708-pat00012
플라스크에 실시예 3의 단계 1에서 제조된 화합물 (150 mg, 0.32 mmole)을 투입하고 메틸렌클로라이드 10 mL를 주입하였다. 온도를 15 ℃ 이하로 유지하며 다이메틸아미노프로필 에틸카보디이미드 염산염 (81.1 mg, 0.41 mmole), 하이드록시벤조트리아졸 (55.4 mg, 0.41 mmole), 피롤리딘 (0.35 mmole)을 투입한 후, 트리에틸아민 (97.1 mg, 0.96 mmole)를 적가하고 15 시간 동안 실온 교반하였다. 실온 교반 후, 메틸렌클로라이드 50 mL와 정제수 50 mL를 가하여 유기층을 분리하였다. 분리한 유기층을 마그네슘설페이트 1 g으로 건조한 후 여과하여 농축하였다. 잔사를 97:3 클로로포름/메틸알콜을 사용하여 크로마토그래피로 정제하여 미황색 액체의 표제 화합물 (수율 81.3 %)을 얻었다.
1H-NMR (400MHz): δ 0.91 (3H, t), 1.359-2.00 (8H, m), 2.29 (3H, s), 2.66 (2H, t,), 3.38-3.61 (6H, m), 5.23 (2H, s), 7.14-7.76 (8H, m)
<실시예 28 내지 154>
아래 실시예 28 내지 154는 각각의 아민을 사용하여 실시예 27과 동일 방법으로 합성하였다.
< 실시예 28> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 1.08 (d, 3H), 1.19 (d, 3H), 1.43 (m, 2H), 1.74 (m, 2H), 2.28 (d, 3H), 2.67 (t, 2H), 2.79 (s, 1.3H), 2.95 (s, 1.7H), 3.59 (d, 2H), 4.22 (m, 0.44H), 4.85 (m, 0.56H), 5.24 (s, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 29> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 프로필아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propylacetamide}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 0.92 (t, 3H), 1.41 (m, 4H), 1.71 (m, 2H), 2.41 (s, 3H), 2.67 (t, 2H), 3.12 (q, 2H), 3.47 (s, 2H), 5.31 (s, 2H), 6.69 (s, 1H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 30> N-부틸-2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일] 아세트아마이드 {N-butyl-2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]acetamide}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 0.92 (t, 3H), 1.28 (m, 2H), 1.41 (m, 4H), 1.71 (m, 2H), 2.38 (s, 3H), 2.67 (t, 2H), 3.15 (q, 2H), 3.47 (s, 2H), 5.29 (s, 2H), 6.69 (s, 1H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 31> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이에틸아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-diethylacetamide}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.12 (t, 3H), 1.21 (t, 3H), 1.39 (m, 2H), 1.71 (m, 2H), 2.31 (s, 3H), 2.64 (t, 2H), 3.35 (q, 3H), 3.46 (q, 3H), 3.58 (s, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 32> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-프로판- 2일아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 1.08 (d, 6H), 1.41 (m, 2H), 1.74 (m, 2H), 2.48 (s, 3H), 2.67 (t, 2H), 3.41 (s, 2H), 3.94 (m, 1H), 5.33 (s, 2H), 6.69 (s, 1H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 33> 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N-아이소프로필-N-메틸아세트아마이드 {2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N-isopropyl-N-methylacetamide}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.04-1.06 (d, 6H), 1.37-1.75 (m, 4H), 2.45 (s, 2H), 3.90-3.99 (m, 4H), 5.32 (s, 2H), 6.54 (m, 1H), 7.1-7.8 (m, 8H)
< 실시예 34> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-(2- 메틸프로필 ) 아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-(2-methylpropyl)acetamide}의 제조
1H-NMR (400MHz): δ 0.86 (d, 3H), 0.92 (t, 3H), 0.98 (d, 3H), 1.45 (m, 2H), 1.70 (m, 2H), 1.89-2.14 (mm, 1H), 2.29 (d, 3H), 2.67 (t, 2H), 2.91 (s, 1.5H), 3.12 (s, 1.5H), 3.19-3.24 (dd, 2H), 3.59 (d, 2H), 5.26 (d, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 35> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.89 (t, 3H), 1.37-1.69 (m, 14H), 2.19 (m, 1H), 2.28 (s, 3H), 2.29 (m, 1H), 2.64 (t, 2H), 3.34 (m, 2H), 3.36 (m, 1H), 3.52 (d, 2H), 3.61 (m, 1H), 5.22 (s, 2H), 7.13 (d, 2H), 7.22 (d, 2H), 7.36 (d, 1H), 7.45 (t, 1H), 7.56 (t, 1H), 7.69 (d, 1H)
< 실시예 36> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(2-옥소-2-피페리딘-1- 일에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(2-oxo-2-piperidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.48-1.78 (m, 8H), 2.33 (s, 3H), 2.72 (t, 2H), 3.52 (t, 4H), 3.59 (s, 2H), 5.28 (s, 2H), 7.19 (d, 2H), 7.27 (d, 2H), 7.43 (m, 1H), 7.52 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 37> 3-[2-[4-[[2-부틸-4- 메틸 -5-(2- 몰폴린 -4- 일에틸 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.41 (m, 2H), 1.72 (m, 2H), 2.32 (s, 3H), 2.68 (t, 2H), 3.52-3.70 (m, 10H), 5.25 (s, 2H), 7.19 (d, 2H), 7.27 (d, 2H), 7.43 (m, 1H), 7.52 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 38> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (3H, t), 1.36-1.76 (14H, m), 2.31 (3H, s), 2.70 (2H, t), 3.51-3.57 (6H, m), 5.27 (2H, s), 7.20-7.84 (8H, m)
< 실시예 39> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-(1- 하이드록시프로판 -2-일) 아세트아마 이드 {2-[2- butyl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-(1-hydroxypropan-2-yl)acetamide}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.05 (d, 3H), 1.39 (m, 2H), 1.78 (m, 2H), 2.31 (s, 3H), 2.71 (t, 2H), 3.21-3.35 (tt, 2H), 3.38 (s, 2H), 3.46 (b, 1H), 5.20 (dd, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 40> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.62 (t, 2H), 2.94 (s, 3H), 3.19 (s, 3H), 3.63 (s, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 41> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메톡시 -N- 메틸아세트아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methoxy-N-methylacetamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.92 (t, 3H), 1.36-1.45 (m, 2H), 1.67-1.74 (m, 2H), 2.18 (s, 4H), 2.30 (s, 3H), 2.68 (t, 2H), 3.20 (s, 3H), 3.71 (s, 2H), 3.78 (s, 3H), 5.28 (s, 2H), 7.20-7.84 (m, 8H)
< 실시예 42> 2-부틸-N,N,4- 트리메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카복스아마이드 {2-butyl-N,N,4-trimethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.88-0.92 (t, 3H), 1.32-1.42 (m, 2H), 1.60-1.70 (m, 2H), 2.21 (s, 3H), 2.67-2.70 (t, 2H), 2.90 (s, 3H), 3.00 (s, 3H), 5.18-5.28 (m, 2H), 7.15-7.71 (m, 8H)
< 실시예 43> 2-부틸-N,4- 다이메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-N-프로판-2- 일피리미딘 -5- 카복스아마이드 {2-Butyl-N,4-dimethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-N-propan-2-ylpyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.88-0.92 (t, 3H), 1.14-1.18 (m, 6H), 1.33-1.43 (m, 2H), 1.63-1.71 (m, 2H), 2.19-2.22 (d, 3H), 2.66-2.71 (m, 2H), 2.74-2.87 (d, 3H), 3.77-3.83 (m, 0.5H), 4.84-4.95 (m, 0.5H), 5.17-5.31 (m, 2H), 7.16-7.73 (m, 8H)
< 실시예 44> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(피페리딘-1- 카보닐 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(piperidine-1-carbonyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.35-1.45 (m, 4H, m), 1.65-1.73 (m, 6H), 2.26 (s, 3H), 2.68-2.72 (t, 2H), 3.26-3.27 (m, 2H), 3.46-3.51 (m, 1H), 3.82-3.85 (m, 1H), 5.19-5.33 (m, 2H), 7.22-7.80 (m, 8H)
< 실시예 45> 3-[2-[4-[[2-부틸-4- 메틸 -5-( 몰폴린 -4- 카보닐 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(morpholine-4-carbonyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.34-1.45 (m, 2H), 1.61-1.73 (m, 2H), 2.30 (s, 3H), 2.69-2.73 (t, 2H), 3.29-3.83 (m, 8H), 5.18-5.37 (m, 2H), 7.19-7.75 (m, 8H)
< 실시예 46> 3-[2-[4-[[5-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2- 카보닐 )-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-(1,3, 3a,4 ,5,6,7,7a- octahydroisoindole -2- carbonyl )-2- butyl -4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.35-1.46 (m, 4H), 1.65-1.74 (m, 8H), 2.26 (s, 3H), 2.68-2.72 (t, 2H), 3.26-3.28 (m, 2H), 3.46-3.51 (m, 1H), 3.82-3.85 (m, 1H), 5.18-5.33 (m, 2H), 7.21-7.79 (m, 8H)
< 실시예 47> 2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-N-프로판-2- 일피리미딘 -5- 카복스아마이드 {2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-N-propan-2-ylpyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.20-1.21 (d, 6H), 1.35-1.450 (m, 2H), 1.69-1.76 (m, 3H), 2.70-2.74 (m, 5H), 4.12-4.20 (m, 1H), 5.34 (s, 2H), 7.21-7.85 (m, 8H)
< 실시예 48> 2-부틸-N- 사이클로헥실 -4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카복스아마이드 {2-butyl-N-cyclohexyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.18-1.95 (m, 14H), 2.70-2.74 (m, 5H), 3.85-3.92 (m, 1H), 5.34 (s, 2H), 7.20-7.83 (m, 8H)
< 실시예 49> 2-부틸-N,4- 다이메틸 -N-(2- 메틸프로필 )-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카복스아마이드 {2-butyl-N,4-dimethyl-N-(2-methylpropyl)-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.79-0.98 (m, 10H), 1.36-1.45 (m, 2H), 1.66-1.74 (m, 2H), 2.01-2.10 (m, 2H), 2.27-2.28 (m, 3H), 2.69-2.73 (m, 2H), 2.90-3.01 (d, 3H), 5.29 (s, 2H), 7.21-7.81 (m, 8H)
< 실시예 50> 3-[2-[4-[[2-부틸-5-(3,5- 다이메틸피페리딘 -1- 카보닐 )-4- 메틸 -6-옥 소피리미 딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-(3,5-dimethylpiperidine-1-carbonyl)-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.77-1.04 (m, 9H), 1.39-1.76 (m, 8H), 2.25-2.31 (m, 3H), 2.69-2.75 (m, 2H), 3.34-3.43 (m, 1.5H), 4.65-4.73 (m, 0.5H), 5.22-5.38 (m, 2H), 7.24-7.85 (m, 8H)
< 실시예 51> 2-부틸-4- 메틸 -N-(2- 메틸프로필 )-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카복스아마이드 {2-butyl-4-methyl-N-(2-methylpropyl)-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carboxamide}의 제조
1H-NMR (400MHz): δ 0.90-0.95 (m, 9H), 1.36-1.45 (m, 2H), 1.69-1.76 (m, 2H), 1.80-1.90 (m, 1H), 2.68-2.74 (m, 5H), 3.11-3.14 (t, 2H), 5.35 (s, 2H), 7.20-7.84 (m, 8H)
< 실시예 52> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.35-1.49 (m, 8H), 1.70 (m, 2H), 2.17 (s, 2H), 2.27 (s, 3H), 2.61 (t, 3H), 3.31-3.37 (m, 3H), 3.44 (d, 2H), 3.50-3.59 (m, 1H), 5.22 (s, 2H), 7.06 (d, 2H), 7.17 (d, 2H), 7.29 (d, 1H), 7.35 (t, 1H), 7.48 (t, 1H), 7.59 (dd, 1H)
< 실시예 53> N- 메톡시 -N- 메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일] 아세트아마이드 {N-methoxy-N-methyl-2-[4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]acetamide}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.68-1.74 (m, 2H), 2.28 (s, 3H), 2.61 (t, 2H), 3.17 (s, 3H), 3.69 (s, 2H), 3.73 (s, 3H), 5.22 (s, 2H), 7.02 (d, 2H), 7.12 (d, 2H), 7.25 (d, 1H), 7.30 (d, 1H), 7.42 (t, 1H), 7.55 (d, 1H)
< 실시예 54> N,N- 다이메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일] 아세트아마이드 {N,N-dimethyl-2-[4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]acetamide}의 제조
1H-NMR (400MHz): δ 1.02 (t, 3H), 1.74-1.80 (m, 2H), 1.84-1.87 (m, 1.7H), 2.40 (s, 3H), 2.91 (s. 3H), 3.13 (s, 3H), 3.57 (s, 2H), 3.72-3.76 (m, 1.3H), 5.28 (s, 2H), 7.20 (d, 2H), 7.29 (d, 2H), 7.38 (d, 1H), 7.50 (t, 1H), 7.60 (t, 1H), 7.77 (d, 1H)
< 실시예 55> 3-[2-[4-[[4- 메틸 -6-옥소-5-(2-옥소-2- 피롤리딘 -1- 일에틸 )-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[4-methyl-6-oxo-5-(2-oxo-2-pyrrolidin-1-ylethyl)-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.97 (t, 3H), 1.69-1.74 (m, 2H), 1.82-1.87 (m, 2H), 1.93-1.98 (m, 2H), 2.28 (s, 3H), 2.67 (t, 2H), 3.36 (t, 2H), 3.50 (s, 2H), 3.58 (t, 2H), 5.22 (s, 2H), 7.12 (d, 2H), 7.23 (d, 2H), 7.35 (d, 1H), 7.45 (t, 1H), 7.56 (t, 1H), 7.69 (d, 1H)
< 실시예 56> 3-[2-[4-[[4- 메틸 -6-옥소-5-(2-옥소-2-피페리딘-1- 일에틸 )-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[4-methyl-6-oxo-5-(2-oxo-2-piperidin-1-ylethyl)-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.98 (t, 3H), 1.49-1.63 (m, 6H), 1.67-1.77 (m, 2H), 2.30 (s, 3H), 2.72 (t, 2H), 3.44-3.51 (m, 4H), 3.56 (s, 2H), 5.24 (s, 2H), 7.14 (d, 2H), 7.26 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.70 (d, 1H)
< 실시예 57> 3-[2-[4-[[5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.83-0.96 (m, 9H), 1.42-1.61 (m, 2H), 1.66-1.72 (m, 2H), 1.80 (d, 1H), 1.95 (t, 1H), 2.27 (s, 3H), 2.52 (t, 1H), 2.70 (t, 2H), 2.91-2.98 (m, 0.3H), 3.20-3.27 (m, 0.3H), 3.47-3.66 (m, 3H), 3.89 (d, 0.7H), 4.39 (d, 0.7H), 5.23 (s, 2H), 7.12 (d, 2H), 7.25 (d, 2H), 7.37 (d, 1H), 7.44 (t, 1H), 7.56 (t, 1H), 7.65 (d, 1H)
< 실시예 58> 3-[2-[4-[[5-[2-(3,5- 다이메틸몰폴린 -4-일)-2- 옥소에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(3,5-dimethylmorpholin-4-yl)-2-oxoethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.96 (t, 3H), 1.11-1.21 (m, 6H), 1.68-1.74 (m, 2H), 2.31 (s, 3H), 2.71 (t, 2H), 2.82 (dd, 1H), 3.13-3.35 (m, 1H), 3.50-3.65 (m, 4H), 3.87 (d, 0.7H), 3.92-4.05 (m, 0.6H), 4.30 (d, 0.7H), 5.23 (s, 2H), 7.13 (d, 2H), 7.26 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.67 (d, 1H)
< 실시예 59> N- 메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일]-N-프로판-2- 일아세트아마이드 {N-methyl-2-[4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.98 (t, 3H), 1.04 (d, 3H), 1.21 (d, 3H), 1.66-1.76 (m, 2H), 2.34 (s, 3H), 2.67 (s, 3H), 2.83 (br, 2H), 2.91 (s, 1.7H), 3.54 (s, 1.1H), 3.61 (s, 0.9H), 4.22-4.26 (m, 0.5H), 4.65-4.69 (m, 0.5H), 5.26 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.37 (d, 1H), 7.45 (t, 1H), 7.57 (t, 1H), 7.67 (d, 1H)
< 실시예 60> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸프로판아마이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylpropanamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.85 (m,2H), 2.43 (s, 3H), 2.52 (t, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (s, 3H), 3.21 (s, 3H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 61> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일프로판아마이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylpropanamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.28 (t,3H), 1.40 (m, 2H), 1.60 (m, 2H), 1.85 (m, 2H), 2.52 (t, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (s, 4H), 5.26 (s, 2H), 6.87 (d, 1H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 62> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 사이클로프로필프로판아마이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-cyclopropylpropanamide}의 제조
1H-NMR (400MHz): δ 0.80 (m, 5H), 0.91 (t, 3H), 1.40 (m, 2H), 1.85 (m, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (m, 4H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 63> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(3-옥소-3-피페리딘-1- 일프로필 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(3-oxo-3-piperidin-1-ylpropyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.10 (t, 2H), 2.36 (t, 2H), 2.60-2.90 (m, 4H), 3.84 (s, 2H), 3.95 (m, 3H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 64> 3-[2-[4-[[2-부틸-4- 메틸 -5-(3- 몰폴린 -4-일-3- 옥소프로필 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(3-morpholin-4-yl-3-oxopropyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 4H), 3.84 (m, 5H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 65> 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일l)-3- 옥소프로필 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-3-oxopropyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.86 (t, 2H), 2.90 (m, 2H), 3.84 (s, 2H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 66> 3-[2-[4-[[2-부틸-4- 메틸 -5-[3-(4- 메틸피페리딘 -1-일)-3- 옥소프로필 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[3-(4-methylpiperidin-1-yl)-3-oxopropyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.41 (m, 5H), 1.71 (m, 8H), 2.31 (s, 3H), 2.68 (t, 2H), 3.52 (m, 4H), 4.28 (m, 4H), 5.27 (s, 2H), 7.20 (d, 2H), 7.25 (d, 2H), 7.42 (m, 1H), 7.48 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 67> 3-[2-[4-[[2-부틸-5-[3-(3,3- 다이메틸피페리딘 -1-일)-3- 옥소프로필 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[3-(3,3-dimethylpiperidin-1-yl)-3-oxopropyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.43 (m, 6H), 1.52 (m, 5H), 1.85 (m, 3H), 2.64 (t, 2H), 2.86 (t, 2H), 3.20 (d, 2H), 3.50 (d, 2H), 3.85 (m, 4H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 68> 3-[2-[4-[[2-부틸-5-[3-(3,5- 다이메틸몰폴린 -4-일)-3- 옥소프로필 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[3-(3,5-dimethylmorpholin-4-yl)-3-oxopropyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 6H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 3H), 3.84 (m, 4H), 3.95 (m, 3H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 69> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-2-부탄-2-일-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-2-butan-2-yl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.72-0.76 (m, 3H), 1.16 (d, 3H), 1.36-1.87 (m, 12H), 2.31 (s, 2H), 2.73-2.79 (m, 1H), 3.29-3.38 (m, 2H), 3.45-3.61 (m, 4H), 5.38 (q, 2H), 7.13 (d, 2H), 7.25 (d, 2H), 7.36 (d, 1H), 7.46 (t, 1H), 7.71 (d, 1H)
< 실시예 70> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메톡시 -N- 메틸아세트아마이드 {2-[2-butan-2-yl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methoxy-N-methylacetamide}의 제조
1H-NMR (400MHz): δ 0.76 (t, 3H), 1.16 (d, 3H), 1.46-1.55 (m, 1H), 1.78-1.85 (m, 1H), 2.29 (s, 3H), 2.73-2.78 (m, 1H), 3.18 (s, 3H), 3.70 (d, 2H), 3.77 (s, 3H), 5.31 (q, 2H), 7.13 (d, 2H), 7.27 (d, 2H), 7.39 (d, 1H), 7.47 (t, 1H), 7.59 (t, 1H), 7.71 (d, 1H)
< 실시예 71> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸아세트아마이드 {2-[2-butan-2-yl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz): δ 0.75 (t 3H), 1.16 (d, 3H), 1.47-1.55 (m, 1H), 1.77-1.85 (m, 1H), 2.23 (s, 3H), 2.73-2.79 (m, 1H), 2.92 (s, 3H), 3.13 (s, 3H), 3.57 (q, 2H), 5.27 (q, 2H), 7.09 (d, 2H), 7.22 (d, 2H), 7.35 (d, 1H), 7.40 (t, 1H), 7.54 (t, 1H), 7.65 (d, 1H)
< 실시예 72> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일아세트아마이 드 {2-[2- butan -2- yl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.74 (t, 3H), 1.07 (d, 3H), 1.17 (d, 3H), 1.20 (d, 2H), 1.46-1.53 (m, 1H), 2.29 (s, 3H), 2.37-2.76 (m, 2.6H), 2.93 (s, 1.4H), 3.50-3.69 (m, 2H), 4.26-4.32 (m, 0.4H), 4.78-4.85 (m. 0.6H), 5.27 (q, 2H), 6.79 (d, 2H), 7.13 (d, 2H), 7.35 (d, 1H), 7.47 (t 1H), 7.58 (t, 1H), 7.75 (d, 1H)
< 실시예 73> 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butan-2-yl-5-[2-(2,6-dimethylpiperidin-1-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.73 (t, 3H), 0.84-0.90 (m, 6H), 0.96 (d, 1H), 1.16 (d, 3H), 1.42-1.58 (m, 3H), 1.80 (d, 2H), 1.99 (t, 1H), 2.39 (s, 3H), 2.52 (t, 1H), 2.72-2.79 (m, 1H), 2.97-3.06 (m, 0.4H), 3.23-3.31 (m, 0.4H), 3.48-3.71 (m, 3H), 3.93 (d, 0.6H), 4.51 (d, 0.6H), 5.17-5.46 (m, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.37 (d, 1H), 7.49 (d, 1H), 7.59 (t, 1H), 7.77 (d 1H)
< 실시예 74> 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6- 다이메틸몰폴린 -4-일)-2- 옥소에틸 ]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butan-2-yl-5-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.76 (t, 3H), 1.15-1.22 (m, 9H), 1.48-1.55 (m, 1H), 1.66 (br, 1H), 1.78-1.84 (m, 1H), 2.33 (s, 3H), 2.74-2.86 (m, 1.4H), 3.20-3.37 (m, 0.6H), 3.48-3.75 (m, 4H), 3.92-4.03 (m, 1.4H), 4.39 (d, 0.6H), 5.20-5.42 (m, 2H), 7.17 (d, 2H), 7.28 (d, 2H), 7.37 (d, 2H), 7.49 (t, 1H), 7.60 (t, 2H), 7.80 (d, 1H)
< 실시예 75> 3-[2-[4-[[2-부틸-5-[2-(3,4- 다이하이드로 -1H- 아이소퀴놀린 -2-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 1.38 (m, 2H), 1.66 (m, 3H), 1.96 (m, 3H), 2.66 (m, 2H), 3.21 (t, 2H), 3.68 (s, 2H), 4.21 (t, 2H), 5.21 (s, 2H), 7.02 (t, 1H), 7.14 (m, 4H), 7.25 (m, 4H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H), 8.14 (d, 1H)
< 실시예 76> 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a- 옥타하이드로 -1H- 아이소퀴놀린 -2-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl)-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H NMR (300 MHz, d6-CDCl3): δ 0.90 (t, 3H), 0.98-1.39 (m, 8H), 1.50-1.82 (m, 7H), 2.30 (d, 3H), 2.66 (m, 2H), 3.60 (s, 2H), 3.82-4.06 (dd, 1H), 4.39-4.55 (dd, 1H), 5.11 (s, 2H), 7.22 (m, 1H), 7.53 (m, 1H), 7.60 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 77> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-(2- 메틸피롤리딘 -1-일)-2- 옥소에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-2H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-(2-methylpyrrolidin-1-yl)-2-oxoethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-2H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 1.12 (d, 2H), 1.27 (d, 1H), 1.38 (m, 2H), 1.66 (m, 3H), 1.96 (m, 3H), 2.27 (s, 3H), 2.65 (dd, 2H), 3.51 (m, 4H), 3.49 (m, 1H), 3.64 (m, 1H), 5.11 (s, 2H), 7.11 (m, 2H), 7.22 (m, 2H), 7.25 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 78> 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a- 옥타하이드로 -2H-퀴놀린-1-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-2H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-yl)-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-2H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 6H), 1.66 (m, 6H), 1.96 (m, 3H), 2.27 (s, 3H), 2.65 (dd, 2H), 3.51 (m, 4H), 3.69 (m, 2H), 3.97 (m, 1H), 5.11 (s, 2H), 7.11 (m, 2H), 7.22 (m, 2H), 7.25 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 79> 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2- 옥소에틸 )-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-2H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-(2-indol-1-yl-2-oxoethyl)-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-2H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 2H), 1.66 (m, 2H), 2.37 (s, 3H), 2.67 (dd, 2H), 3.80 (s, 2H), 5.30 (s, 2H), 7.08 (m, 2H), 7.11 (m, 3H), 7.22 (m, 3H), 7.38 (m, 3H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 80> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-(2- 메틸 -1,3,3a,4,6,6a- 헥사하이드로피롤로[3,4-c]피롤 -5-일)-2- 옥소에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)-2-oxoethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 6H), 1.66 (m, 2H), 2.41 (s, 3H), 2.67 (dd, 2H), 3.80 (m, 4H), 3.93 (d, 1H), 4.13 (d, 1H), 5.30 (dd, 2H), 7.08 (m, 2H), 7.11 (m, 4H), 7.53 (m, 1H), 7.62 (m, 1H)
< 실시예 81> 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a- 헥사하이드로 -1H- 사이클로펜타[c]피롤 -2-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 2H), 1.46 (m, 2H), 1.66 (m, 3H), 1.82 (m, 3H), 2.27 (s, 3H), 2.67 (dd, 3H), 2.65 (m, 1H), 3.16 (dd, 1H), 3.21 (dd, 1H), 3.35 (d, 2H), 3.62 (m, 1H), 3.83 (m, 1H), 5.20 (dd, 2H), 7.12 (d, 2H), 7.24 (m, 2H), 7.38 (d, 1H), 7.53 (m, 1H), 7.62 (m, 1H), 7.71 (d, 1H)
< 실시예 82> 3-[2-[4-[[2-부틸-5-[2-(1,3- 다이하이드로아이소인돌 -2-일)-2-옥소에틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(1,3- dihydroisoindol -2- yl )-2- oxoethyl ]-4- methyl -6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 2H), 1.66 (m, 2H), 2.37 (s, 3H), 2.67 (dd, 2H), 3.61 (s, 2H), 4.76 (s, 2H), 5.01 (s, 2H), 5.20 (s, 2H), 7.19 (m, 2H), 7.29 (m, 5H), 7.38 (m, 31H), 7.48 (m, 1H), 7.56 (m, 1H), 7.76 (d, 1H)
< 실시예 83> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-[2-옥소-2-(4-프로판-2- 일피페리딘 -1-일)에틸]피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-[2-oxo-2-(4-propan-2-ylpiperidin-1-yl)ethyl]pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (m, 9H), 1.22 (m, 3H), 1.38 (m, 3H), 1.66 (m, 4H), 2.37 (s, 3H), 2.48 (t, 1H), 2.63 (dd, 2H), 2.97 (t, 1H), 3.59 (s, 2H), 4.09 (t, 1H), 4.57 (t, 1H), 5.24 (s, 2H), 7.17 (m, 2H), 7.22 (m, 2H), 7.38 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 84> 3-[2-[4-[[2-부틸-5-[2-(2,3- 다이하이드로인돌 -1-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(2,3-dihydroindol-1-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 2H), 1.66 (m, 2H), 2.37 (s, 3H), 2.67 (dd, 2H), 3.61 (s, 2H), 4.76 (s, 2H), 5.01 (s, 2H), 5.20 (s, 2H), 7.19 (m, 2H), 7.29 (m, 5H), 7.38 (m, 3H), 7.48 (m, 1H), 7.56 (m, 1H), 7.76 (d, 1H)
< 실시예 85> 3-[2-[4-[[2-부틸-5-[2-(4- 플루오로 -1,3- 다이하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(4-fluoro-1,3-dihydroisoindol-2-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 2H), 1.66 (m, 2H), 2.37 (d, 3H), 2.67 (dd, 2H), 3.61 (s, 2H), 4.76 (s, 2H), 5.01 (s, 2H), 5.20 (s, 2H), 7.05 (m, 4H), 7.09 (m, 3H), 7.24 (m, 3H), 7.38 (m, 1H), 7.48 (m, 1H), 7.56 (m, 1H), 7.76 (d, 1H)
< 실시예 86> 2-[2- 사이클로프로필 -4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸아세트아마 이드 {2-[2- cyclopropyl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz): δ 0.96 (m, 2H), 1.17 (m, 2H), 1.81 (m, 1H), 2.21 (s, 3H), 2.91 (s, 3H), 3.55 (s, 2H), 5.41 (s, 2H), 7.11 (m, 4H), 7.22 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.74 (d, 1H)
< 실시예 87> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-2- 사이클로프로필 -4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-2-cyclopropyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.97 (m, 2H), 1.17 (m, 2H), 1.44-1.51 (m, 8H), 1.83 (m, 1H), 2.08 (m, 1H), 2.21 (s, 3H), 2.32 (m, 1H), 3.32 (m, 2H), 3.45 (m, 3H), 3.62 (m, 1H), 5.41 (s, 2H), 7.11 (m, 4H), 7.22 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.74 (d, 1H)
< 실시예 88> 3-(4'-((2-부틸-4- 메틸 -5-(2-( 옥타하이드로 -1H-인돌-1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2- butyl -4- methyl -5-(2-( octahydro -1H- indol -1- yl )-2- oxoethyl )-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.38 (m, 6H), 1.66 (m, 6H), 1.96 (m, 3H), 2.27 (s, 3H), 2.65 (dd, 2H), 3.51 (m, 4H), 3.69 (m, 2H), 3.97 (m, 1H), 5.11 (s, 2H), 7.11 (m, 2H), 7.22 (m, 2H), 7.25 (m, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 89> 3-(4'-((2-부틸-5-(2-( 다이하이드로 -1H- 피리도[1,2-a]피라진 -2(6H,7H,8H,9H,9aH)-일)-2- 옥소에틸 )-4- 메틸 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페 닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-(dihydro-1H-pyrido[1,2-a]pyrazin-2(6H,7H,8H,9H,9aH)-yl)-2-oxoethyl)-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.42 (m, 4H), 1.67 (m, 6H), 1.96 (m, 3H), 2.27 (s, 3H), 2.40 (s, 2H), 2.73-3.20 (m, 5H), 3.51-4.05 (m, 3H), 4.47 (d, 1H), 5.20 (dd, 2H), 7.17 (m, 2H), 7.33 (m, 3H), 7.41 (m, 1H), 7.47 (m, 1H), 7.62 (d, 1H)
< 실시예 90> 3-[2-[4-[[5-[2-(7- 아자바이사이클로[2.2.1]헵탄 -7-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(7- azabicyclo[2.2.1]heptan -7- yl )-2- oxoethyl ]-2- butyl -4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.88 (t, 3H), 1.33-1.52 (m, 6H), 1.61-1.82 (m, 6H), 2.33 (s, 3H), 2.67 (t, 2H), 3.54 (s, 2H), 4.41 (t, 1H), 4.52 (t, 1H), 5.25 (s, 2H), 7.12 (d, 2H), 7.25 (d, 2H), 7.36 (d, 1H), 7.43 (t, 1H), 7.55 (t, 1H), 7.66 (d, 1H)
< 실시예 91> 3-[2-[4-[[5-[2-(7- 아자바이사이클로[2.2.1]헵탄 -7-일)-2- 옥소에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아 졸-5-온 {3-[2-[4-[[5-[2-(7- azabicyclo[2.2.1]heptan -7- yl )-2- oxoethyl ]-4- methyl -6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.37-1.53 (m, 4H), 1.65-1.85 (m, 6H), 2.33 (s, 3H), 2.74 (t, 2H), 3.53 (s, 2H), 4.39 (t, 1H), 4.48 (t, 1H), 5.25 (s, 2H), 7.13 (d, 2H), 7.26 (d, 2H), 7.36 (d, 1H), 7.44 (t, 1H), 7.56 (t, 1H), 7.66 (d, 1H)
< 실시예 92> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-[2-옥소-2-[4-( 트리풀루오로메틸 )피페리딘-1-일]에틸]피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-[2-oxo-2-[4-(trifluoromethyl)piperidin-1-yl]ethyl]pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.93 (t, 3H), 1.35-1.95 (m, 8H), 2.23-2.29 (m, 1H), 2.33 (s, 3H), 2.53-2.59 (m, 1H), 2.66-2.70 (t, 2H), 3.05-3.11 (m, 1H), 3.61 (s, 2H), 4.23-4.71 (m, 2H), 5.28 (s, 2H), 7.21-7.84 (m, 8H)
< 실시예 93> 3-[2-[4-[[5-[2-(8- 아자스파이로[4.5]데칸 -8-일)-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.87 (t, 3H), 1.32-1.48 (m, 10H), 1.58-1.66 (m, 6H), 2.26 (s, 3H), 2.63 (t, 2H), 3.46-3.51 (m, 4H), 3.58 (s, 2H), 7.12 (d, 2H), 7.22 (d, 2H), 7.35 (d, 1H), 7.43 (t, 1H), 7.55 (t, 1H), 7.65 (d, 1H)
< 실시예 94> 3-[2-[4-[[5-[2-(8- 아자스파이로[4.5]데칸 -8-일)-2- 옥소에틸 ]-4-메틸-6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(8- azaspiro[4.5]decan -8- yl )-2- oxoethyl ]-4- methyl -6- oxo -2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.37 (t, 2H), 1.43-1.46 (m, 6H), 1.60-1.71 (m, 6H), 2.22 (s, 3H), 2.58 (t, 2H), 3.44-3.50 (m, 4H), 3.56 (s, 2H), 5.20 (s, 2H), 7.09 (d, 2H), 7.22 (d, 2H), 7.36 (d, 1H), 7.43 (t, 1H), 7.56 (t, 1H), 7.64 (d, 1H)
< 실시예 95> 3-[2-[4-[[2-부틸-5-[2-(4,4- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(4,4-dimethylpiperidin-1-yl)-2-oxoethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.97 (s, 6H), 1.32-1.44 (m, 6H), 1.65-1.73 (m, 2H), 2.32 (s, 3H), 2.70 (t, 2H), 3.51-3.55 (m, 4H), 3.59 (s, 2H), 5.26 (s, 2H), 7.20 (d, 2H), 7.26 (d, 2H), 7.38 (d, 1H), 7.60 (t, 1H), 7.78 (d, 1H)
< 실시예 96> 3-[2-[4-[[5-[2-(4,4- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(4,4-dimethylpiperidin-1-yl)-2-oxoethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.95-1.00 (m, 9H), 1.29-1.39 (m, 4H), 1.69-1.77 (m, 2H), 2.29 (s, 3H), 2.65 (t, 2H), 3.48-3.53 (m, 4H), 3.58 (s, 2H), 5.24 (s, 2H), 7.16 (d, 2H), 7.26 (d, 2H), 7.38 (d, 1H), 7.49 (t, 1H), 7.60 (t, 1H), 7.78 (d, 1H)
< 실시예 97> 3-[2-[4-[[2-부틸-5-[2-(2,5- 다이메틸피롤리딘 -1-일)-2-옥소-에틸]-4- 메틸 -6-옥소-피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-2H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(2,5-dimethylpyrrolidin-1-yl)-2-oxo-ethyl]-4-methyl-6-oxo-pyrimidin-1-yl]methyl]phenyl]phenyl]-2H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.26 (m, 4H), 1.33 (m, 6H), 1.71 (m, 4H), 2.05 (m, 2H), 2.29 (s, 3H), 2.67 (m, 2H), 4.00 (m, 1H), 4.26 (m, 1H), 5.14 (s, 2H), 7.03 (m, 4H), 7.38 (d, 1H), 7.50 (m, 2H), 7.88 (d, 1H)
< 실시예 98> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-[(2S)-2- 메틸피롤리딘 -1-일]-2-옥소에틸]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-[(2S)-2-methylpyrrolidin-1-yl]-2-oxoethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.26 (m, 4H), 1.33 (m, 3H), 1.71 (m, 4H), 2.05 (m, 2H), 2.29 (s, 3H), 2.67 (m, 2H), 3.42 (m, 2H), 4.00 (m, 1H), 5.14 (s, 2H), 7.03 (m, 4H), 7.38 (d, 1H), 7.50 (m, 2H), 7.88 (d, 1H)
< 실시예 99> 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6- 다이메틸피페리딘 -1-일]-2-옥 소에 틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-[( 2S,6R )-2,6- dimethylpiperidin -1- yl ]-2- oxoethyl ]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.93 (m, 5H), 1.15 (m, 3H), 1.40 (m, 7H), 1.48-1.88 (m, 9H), 2.26 (s, 3H), 2.69 (t, 2H), 3.60 (dd, 2H), 4.29 (m, 1H), 4.67 (s, 1H), 5.16 (m, 2H), 7.03 (m, 2H), 7.11 (m, 2H), 7.39 (d, 1H), 7.50 (m, 2H), 7.92 (d, 1H)
< 실시예 100> 3-[2-[4-[[5-[2-[(4 aS ,8aR)-3,4,4a,5,6,7,8,8a- 옥타하이드로 -2H-퀴놀린-1-일]-2- 옥소에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-[(4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-yl]-2-oxoethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 1.37 (m, 8H), 1.50-1.92 (m, 9H), 2.22 (s, 3H), 2.63 (m, 2H), 3.57 (m, 2H), 3.93 (dd, 1H), 4.33-4.54 (dd, 1H), 5.11 (s, 2H), 6.96 (m, 4H), 7.38 (d, 2H), 7.47-7.79 (m, 2H), 7.81 (d, 1H)
< 실시예 101> 3-(4'-((2-부틸-4-메틸-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-methyl-5-(2-(2-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.87-0.96 (m, 3H), 1.19-1.44 (m, 8H), 1.71-1.81 (m, 3H), 1.94-2.05 (d, 3H), 2.43-3.01 (m, 4H), 4.28-4.62 (m, 3H), 5.26-5.37 (m, 3H), 6.88-7.80 (m, 8H)
< 실시예 102> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸아세트아마 이드 {2-[2- butyl -4- cyclopropyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz): δ 0.89 (t, 3H), 0.92 (m, 2H), 1.19 (m, 2H), 1.39 (m, 2H), 1.70 (m, 2H), 1.92 (m, 1H), 2.66 (t, 2H), 2.94 (s, 3H), 3.14 (s, 3H), 3.74 (s, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 103> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-2-부틸-4- 사이클로프로필 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-2-butyl-4-cyclopropyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.89 (m, 7H), 1.37-1.69 (m, 15H), 2.64 (t, 2H), 3.41 (m, 2H), 3.62 (6, 2H), 3.65 (m, 1H), 5.25 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.39 (d, 1H), 7.45 (t, 1H), 7.56 (t, 1H), 7.69 (d, 1H)
< 실시예 104> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2-일아세트아마이드 {2-[2- butyl -4- cyclopropyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.89 (m, 7H), 1.08 (d, 3H), 1.19 (d, 3H), 1.42 (m, 2H), 1.71 (m, 2H), 1.94 (m, 1H), 2.67 (t, 2H), 2.79, 2.95 (s(d), 3H), 3.82, 3.89 ((s)d, 2H), 4.28, 4.86 (m(m), 1H), 5.24 (s, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 105> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-(2- 메틸프로필 )아세트아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-(2-methylpropyl)acetamide}의 제조
1H-NMR (400MHz): δ 0.89 (t, 3H), 1.07 (d, 3H), 1.15-1.18 (m, 5H), 1.31-1.37 (m, 3H), 1.62-1.72 (m, 2H), 1.91-2.05 (m, 1H), 2.61 (t, 2H), 2.84 (d, 3H), 3.72 (d, 2H), 4.27-4.88 (m, 2H), 5.21 (s, 2H), 7.16-7.80 (m, 8H)
< 실시예 106> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 아이소프로필 -N- 메틸아 세트아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-isopropyl-N-methyl-acetamide}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 0.96 (m, 2H), 1.10 (d, 6H), 1.25 (d, 2H), 1.31 (m, 2H), 1.64 (m, 2H), 1.94 (mm, 1H), 2.01 (m, 1H), 2.62 (t, 2H), 3.17 (s, 1.5H), 3.30 (s, 1.5H), 3.98 (s, 1H), 4.10 (s, 1H), 4.30 (m, 1H), 4.76 (m, 0.5H), 5.19 (d, 2H), 5.90 (m, 0.5H), 7.13 (d, 2H), 7.25 (m, 2H), 7.46 (d, 1H), 7.58 (t, 1H), 7.62 (t, 1H), 7.75 (d, 1H)
< 실시예 107> 3-[2-[4-[[2-부틸-4- 사이클로프로필 -6-옥소-5-(2-옥소-2- 피롤리딘 -1- 일에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-cyclopropyl-6-oxo-5-(2-oxo-2-pyrrolidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one)의 제조
1H-NMR (400MHz): δ 0.89 (t, 3H), 0.92 (m, 2H), 1.19 (m, 2H), 1.41 (m, 2H), 1.70 (m, 4H), 1.89 (t, 2H), 1.93 (t, 1H), 2.08 (m, 2H), 2.71 (t, 2H), 3.34 (t, 2H), 3.64 (t, 2H), 3.69 (s, 2H), 5.21 (s, 2H), 7.18 (d, 2H), 7.28 (d, 2H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 108> 3-[2-[4-[[2-부틸-4- 사이클로프로필 -5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아 졸-5-온 {3-[2-[4-[[2-butyl-4-cyclopropyl-5-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.86-0.97 (m, 10H), 0.92 (m, 2H), 1.19 (m, 2H), 1.39 (m, 2H), 1.48-2.05 (m, 5H), 2.69 (t, 2H), 3.13-4.65 (m, 4H), 5.28 (dd, 2H), 7.19 (d, 2H), 7.27 (d, 2H), 7.43 (m, 1H), 7.52 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 109> 3-[2-[4-[[2-부틸-4- 사이클로프로필 -6-옥소-5-(2-옥소-2-피페리딘-1- 일에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-cyclopropyl-6-oxo-5-(2-oxo-2-piperidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.88-0.96 (m, 5H), 1.17-1.39 (m, 4H), 1.63-1.72 (m, 4H), 2.09-2.10 (m, 1H), 2.60-2.64 (t, 2H), 3.59-3.72 (m, 10H), 5.22 (s, 2H), 7.15-7.78 (m, 8H)
< 실시예 110> 3-[2-[4-[[2-부틸-4- 사이클로프로필 -5-(2- 몰폴린 -4-일-2- 옥소에틸 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-cyclopropyl-5-(2-morpholin-4-yl-2-oxoethyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.89 (t, 3H), 0.92 (m, 2H), 1.19 (m, 2H), 1.41 (m, 2H), 1.58 (m, 2H), 1.75 (m, 4H), 2.04 (m, 1H), 2.68 (t, 2H), 3.52 (m, 4H), 3.73 (s, 2H), 5.24 (s, 2H), 7.19 (d, 2H), 7.27 (d, 2H), 7.43 (m, 1H), 7.52 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 111> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-(1- 하이드록시프로판 -2-일)아세트아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-(1-hydroxypropan-2-yl)acetamide}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 0.96 (m, 2H), 1.10 (d, 6H), 1.25 (d, 2H), 1.31 (m, 2H), 1.64 (m, 2H), 1.94-2.01 (m, 3H), 2.62 (t, 2H), 3.98 (m, 4H), 4.10 (s, 1H), 4.30 (m, 1H), 4.76 (m, 0.5H), 5.19 (d, 2H), 5.90 (m, 0.5H), 7.13 (d, 2H), 7.25 (m, 2H), 7.46 (d, 1H), 7.58 (t, 1H), 7.62 (t, 1H), 7.75 (d, 1H)
< 실시예 112> N-부틸-2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일] 아세트아마이드 {N-butyl-2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]acetamide}의 제조
1H-NMR (400MHz): δ 0.87-0.97 (6H, m), 1.13-1.17 (4H, m), 1.29-1.39 (4H, m), 1.43-1.70 (4H, m), 1.96-2.05 (5H, m), 3.50-3.55 (4H, m), 3.73 (2H, s), 5.23 (2H, s), 7.19-7.82 (8H, m)
< 실시예 113> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 프로필아세트아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propylacetamide}의 제조
1H-NMR (400MHz): δ 0.89-0.97 (6H, m), 1.13-1.17 (4H, m), 1.28-1.39 (2H, m), 1.43-1.69 (4H, m), 1.96-2.04 (5H, m), 3.50-3.45 (4H, m), 3.71 (2H, s), 5.23 (2H, s), 7.19-7.85 (8H, m)
< 실시예 114> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-프로판-2- 일아세트아마 이드 {2-[2- butyl -4- cyclopropyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 0.96 (m, 2H), 1.10 (d, 6H), 1.25 (d, 2H), 1.31 (m, 2H), 1.64 (m, 2H), 1.94-2.01 (m, 3H), 2.62 (t, 2H), 4.10 (s, 1H), 4.30 (m, 1H), 5.19 (d, 2H), 7.13 (d, 2H), 7.25 (m, 2H), 7.46 (d, 1H), 7.58 (t, 1H), 7.62 (t, 1H), 7.75 (d, 1H)
< 실시예 115> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메톡시 -N- 메틸아세트아 마이드 {2-[2- butyl -4- cyclopropyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methoxy-N-methylacetamide}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.00-1.21 (m, 4H), 1.36-1.45 (m, 2H), 1.67-1.74 (m, 2H), 2.18 (s, 4H), 2.30 (m, 1H), 2.68 (t, 2H), 3.20 (s, 3H), 3.71 (s, 2H), 3.78 (s, 3H), 5.28 (s, 2H), 7.20-7.84 (m, 8H)
< 실시예 116> 3-(4'-((2-부틸-4- 사이클로프로필 -6-옥소-5-(2-옥소-2-( 피롤리딘 -1-일)에틸)피리미딘-1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2- butyl -4- cyclopropyl -6- oxo -5-(2- oxo -2-( pyrrolidin -1-yl)ethyl)pyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (t, 3H), 1.18 (d, 2H), 1.20 (m, 2H), 1.69 (m, 2H), 2.01 (t, 1H), 2.63 (t, 2H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 117> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2,6- 다이메틸피페라진 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2,6-dimethylpiperazin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (m, 4H), 1.18 (t,1H), 1.20 (m, 4H), 1.67 (dd, 2H), 1.86 (m, 8H), 2.01 (m, 4H), 3.45 (d, 2H), 3.62 (t, 2H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 118> (S)-3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2- 메틸피롤리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {(S)-3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2-methylpyrrolidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 5H), 0.96 (m, 4H), 1.18 (m, 3H), 1.20 (m, 1H), 1.67 (dd, 2H), 1.86 (m, 8H), 2.62 (m, 2H), 3.45 (d, 2H), 3.62 (t, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 119> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(3,5- 다이메틸피페리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.22 (m, 4H), 1.36 (m, 2H), 1.67 (dd, 3H), 2.01 (m, 3H), 2.66 (dd, 2H), 3.37 (dd, 2H), 3.40 (dd, 2H), 3.56-3.73 (m, 4H), 4.45 (m, 1H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 120> 2-(2-부틸-4- 사이클로프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N-사이클로프로필아세트아마이드 {2-(2-butyl-4-cyclopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N-cyclopropylacetamide}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (m, 2H), 1.17 (s, 2H), 1.20 (m, 2H), 1.37 (dd, 2H), 2.01 (m, 5H), 2.66 (m, 4H), 3.62 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 121> 2-(2-부틸-4- 사이클로프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N,N-다이에틸아세트아마이드 {2-(2-butyl-4-cyclopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N,N-diethylacetamide}의 제조
1H-NMR (400MHz): δ 0.95 (m, 5H), 1.22 (m, 7H), 1.36 (m, 2H), 1.67 (dd, 2H), 2.01 (m, 1H), 2.66 (dd, 2H), 3.37 (dd, 2H), 3.40 (dd, 2H), 3.62 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 122> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(3,5- 다이메틸몰폴리노 )-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아 졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(3,5-dimethylmorpholino)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.22 (m, 4H), 1.36 (m, 2H), 1.67 (dd, 3H), 2.01 (m, 3H), 2.66 (dd, 2H), 3.37 (dd, 2H), 3.40 (dd, 2H), 3.56-3.73 (m, 4H), 4.45 (m, 1H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 123> 3-(4'-((2-부틸-4- 사이클로프로필 l-5-(2-((2S,6R)-2,6- 다이메틸피페리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-((2S,6R)-2,6-dimethylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 5H), 1.22 (m, 4H), 1.36 (m, 5H), 1.67 (dd, 4H), 2.01 (m, 5H), 2.66 (dd, 2H), 3.80 (dd, 2H), 4.30-4.70 (m, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 124> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2- 몰폴리노 -2- 옥소에틸 )-6-옥 소피리미 딘-1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-morpholino-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92-0.95 (m, 5H), 1.22 (m, 2H), 1.36 (m, 2H), 1.67 (dd, 2H), 2.19 (m, 1H), 2.68 (t, 2H), 3.70 (d, 2H), 3.79 (d, 2H), 4.00 (s, 2H), 4.09 (s, 2H), 4.45 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 125> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2- 메틸피페리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아 졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2-methylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 4H), 1.15-1.17 (m, 4H), 1.35-1.37 (m, 4H), 1.64-1.68 (m, 8H), 2.01 (m, 3H), 2.64 (dd, 2H), 3.16 (t, 1H), 3.80 (dd, 2H), 4.30-4.70 (m, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 126> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(4- 하이드록시피페리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(4-hydroxypiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 7H), 1.15-1.17 (m, 2H), 1.35-1.37 (m, 8H), 2.64 (dd, 2H), 3.71-3.73 (m, 4H), 3.80 (dd, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 127> 3-[2-[4-[[2-부틸-6-옥소-5-(2-옥소-2-피페리딘-1- 일에틸 )-4-프로판-2- 일피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-6-oxo-5-(2-oxo-2-piperidin-1-ylethyl)-4-propan-2-ylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz, CDCl3): δ 0.9 (m, 3H), 1.0 (m, 6H), 1.4 (m, 3H), 1.6 (m, 8H), 1.8 (m, 2H), 2.7 (m, 2H), 3.0 (m, 1H), 3.4 (m, 1H), 3.8 (m, 5H), 4.0 (m, 4H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 128> 3-[2-[4-[[2-부틸-5-[2-(2,6- 다이메틸피페라진 -1-일)-2- 옥소에틸 ]-6-옥소-4-프로판-2- 일피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(2,6- dimethylpiperazin -1- yl )-2- oxoethyl ]-6- oxo -4-propan-2-ylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz, CDCl3): δ 0.9 (m, 4H), 1.0 (m, 5H), 1.4 (m, 10H), 1.6 (m, 2H), 1.8 (m, 2H), 2.7 (m, 4H), 3.0 (m, 2H), 3.4 (m, 2H), 3.8 (m, 2H), 4.3 (m, 3H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 129> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N,N- 다이메틸아세트아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz, CDCl3): δ 0.9 (m, 3H), 1.0 (m, 6H), 1.4 (m, 2H), 1.6 (m, 2H), 1.8 (m, 2H), 2.7 (m, 2H), 3.0 (m, 4H), 3.4 (m, 6H), 3.6 (m, 3H), 3.8 (m, 2H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 130> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N,N- 다이에틸아세트아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N,N-diethylacetamide}의 제조
1H-NMR (400MHz, CDCl3): δ 0.9 (m, 3H), 1.0 (m, 4H), 1.4 (m, 9H), 1.6 (m, 2H), 1.8 (m, 5H), 2.7 (m, 2H), 3.0 (m, 1H), 3.4 (m, 5H), 3.8 (m, 2H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 131> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N- 메틸 -N-프로판-2- 일아세트아마 이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N-methyl-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.86 (d, 3H), 0.92 (t, 3H), 0.98 (d, 3H), 1.45 (m, 2H), 1.70 (m, 2H), 1.89-2.14 (mm, 7H), 2.67 (t, 2H), 2.91 (s, 1.5H), 3.12 (s, 1.5H), 3.19-3.24 (dd, 2H), 3.59 (d, 2H), 5.26 (d, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 132> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N- 사이클로프로필아세트아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N-cyclopropylacetamide}의 제조
1H-NMR (400MHz): δ 0.86 (d, 3H), 0.92 (t, 3H), 0.98 (d, 3H), 1.45 (m, 2H), 1.70 (m, 2H), 1.89-2.14 (m, 2H), 2.67 (m, 4H), 2.91 (m, 1H), 3.12 (m, 2H), 3.59 (d, 2H), 5.26 (d, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 133> 3-(4'-((2-부틸-5-(2-(3,5- 다이메틸피페리딘 -1-일)-2- 옥소에틸 )-4- 아이소프로필 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 9H), 1.17 (m, 6H), 1.29 (dd, 6H), 1.68 (m, 2H), 1.70 (m, 2H), 1.93 (t, 1H), 2.45 (m, 2H), 2.95 (m, 1H), 3.60 (m, 3H), 3.95 (d, 0.5H), 4.42 (d, 0.5H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 134> 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6- 다이메틸피페리딘 -1-일)-2-옥소에틸)-4- 아이소프로필 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-((2R,6S)-2,6-dimethylpiperidin-1-yl)-2-oxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.93 (m, 5H), 1.15 (m, 3H), 1.21 (m, 6H), 1.40 (m, 7H), 1.48-1.88 (m, 9H), 2.95 (m, 1H), 2.69 (t, 2H), 3.60 (dd, 2H), 4.29 (m, 1H), 4.67 (s, 1H), 5.16 (m, 2H), 7.03 (m, 2H), 7.11 (m, 2H), 7.39 (d, 1H), 7.50 (m, 2H), 7.92 (d, 1H)
< 실시예 135> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(2- 메틸피페리딘 -1-일)-2-옥 소에 틸)-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-(2-methylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.92 (m, 2H), 1.17 (m, 6H), 1.29 (dd, 6H), 1.68 (m, 2H), 1.70 (m, 6H), 1.93 (t, 1H), 2.45 (m, 2H), 2.95 (m, 1H), 3.60 (m, 3H), 3.95 (d, 0.5H), 4.42 (d, 0.5H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 136> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(3- 메틸피페리딘 -1-일)-2-옥 소에 틸)-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-(3-methylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 6H), 1.17 (m, 6H), 1.35 (m, 5H), 1.70 (m, 5H), 2.52 (m, 2H), 2.95 (m, 1H), 3.60 (m, 2H), 3.95 (m, 1H), 4.31 (m, 1H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 137> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2- 몰폴리노 -2- 옥소에틸 )-6-옥소피리미딘-1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-morpholino-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.91 (m, 6H), 1.36 (m, 2H), 1.74 (m, 2H), 2.66 (m, 2H), 3.01 (m, 1H), 3.50 (m, 2H), 3.59 (m, 8H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 138> 3-(4'-((2-부틸-5-(2-(2,6- 다이메틸몰폴리노 )-2- 옥소에틸 )-4-아이소프로필-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-5-(2-(2,6-dimethylmorpholino)-2-oxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.91 (m, 12H), 1.36 (m, 2H), 1.74 (m, 2H), 2.28 (m, 1H), 2.66 (m, 2H), 2.80 (m, 1H), 3.01 (m, 1H), 3.50 (m, 2H), 3.59 (m, 6H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 139> (S)-3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(2- 메틸피롤리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아 졸-5(4H)-온 {(S)-3-(4'-((2-butyl-4-isopropyl-5-(2-(2-methylpyrrolidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.11 (d, 2H), 1.19 (m, 6H), 1.21 (d, 1H), 1.37 (m, 2H), 1.74 (m, 2H), 1.92 (m, 3H), 2.66 (m, 2H), 3.01 (m, 1H), 3.41 (m, 1H), 3.65 (m, 3H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 140> 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드 {2-[2-butyl-4-ethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylacetamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.84 (m, 3H), 3.95 (m, 4H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 141> 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일아세트아마이드 {2-[2-butyl-4-ethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylacetamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.84 (m, 6H), 3.95 (m, 4H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 142> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 옥소에틸 ]-2-부틸-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-oxoethyl]-2-butyl-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.20-1.70 (m, 19H), 2.34 (s, 2H), 2.66 (t, 2H), 3.84 (m, 5H), 3.95 (m, 2H), 4.34 (m, 4H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 143> 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2- 피롤리딘 -1- 일에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-6-oxo-5-(2-oxo-2-pyrrolidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.9 (m, 3H), 1.0 (m, 8H), 1.4 (m, 5H), 1.6 (m, 4H), 1.8 (m, 2H), 2.7 (m, 2H), 4.0 (m, 4H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 144> 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2-피페리딘-1- 일에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-6-oxo-5-(2-oxo-2-piperidin-1-ylethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 5H), 1.40 (m, 2H), 1.70 (m, 4H), 2.34 (s, 3H), 2.66 (t, 2H), 3.72 (m, 4H), 3.84 (s, 2H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 145> 3-[2-[4-[[2-부틸-4-에틸-5-(2- 몰폴린 -4-일-2- 옥소에틸 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-5-(2-morpholin-4-yl-2-oxoethyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (t, 3H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 4H), 3.84 (s, 2H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 146> 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4- 메틸피페리딘 -1-일)-2- 옥소에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-5-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.41 (m, 8H), 1.71 (m, 8H), 2.31 (s, 3H), 2.68 (t, 2H), 3.52 (m, 4H), 4.28 (s, 2H), 5.27 (s, 2H), 7.20 (d, 2H), 7.25 (d, 2H), 7.42 (m, 1H), 7.48 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 147> 3-[2-[4-[[2-부틸-5-[2-(3,3- 다이메틸피페리딘 -1-일)-2- 옥소에틸 ]-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(3,3-dimethylpiperidin-1-yl)-2-oxoethyl]-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.43 (m, 9H), 1.52 (m, 5H), 1.85 (m, 3H), 2.64 (t, 2H), 2.86 (t, 2H), 3.20 (d, 2H), 3.50 (d, 2H), 3.85 (s, 2H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 148> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸몰폴린 -4-일)-2- 옥소에틸 ]-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(3,5-dimethylmorpholin-4-yl)-2-oxoethyl]-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 9H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 3H), 3.84 (s, 2H), 3.95 (m, 3H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 149> 3-(4'-((2-부틸-4- 메틸 -6-옥소-5-(2-옥소-2-( 싸이아졸리딘 -3-일)에틸)피리미딘-1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-methyl-6-oxo-5-(2-oxo-2-(thiazolidin-3-yl)ethyl)pyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H), 1.34-1.44 (m, 2H), 1.65-1.73 (m, 2H), 2.33 (d, 3H), 2.66 (t, 2H), 2.97-3.13 (m, 2H), 3.60 (d, 2H), 3.81-3.95 (m, 2H), 4.55 (s, 1H), 4.67 (s, 1H), 5.26 (s, 2H), 7.17-7.78 (m, 8H)
< 실시예 150> 3-(4'-((2-부틸-4- 메틸 -5-(2-(4- 메틸피페리딘 -1-일)-2- 옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-methyl-5-(2-(4-methylpiperidin-1-yl)-2-oxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.89-0.95 (m, 6H), 1.06-1.15 (m, 2H), 1.34-1.44 (m, 2H), 1.58-1.73 (m, 5H), 2.30 (s, 3H), 2.52-2.68 (m, 3H), 3.01-3.07 (m, 1H), 3.59 (s, 2H), 3.99-4.52 (m, 2H), 5.27 (s, 2H), 7.19-7.81 (m, 8H)
< 실시예 151> 3-(4'-((2-부틸-5-(2-(2,6- 다이메틸몰폴리노 )-2- 옥소에틸 )-4-메틸-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-5-(2-(2,6-dimethylmorpholino)-2-oxoethyl)-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H), 1.14-1.22 (m, 6H), 1.35-1.44 (m, 2H), 1.65-1.73 (m, 2H), 2.32 (s, 3H), 2.23-2.35 (m, 4H), 2.67 (t, 2H), 2.79-2.85 (m, 1H), 3.19-4.40 (m, 6H), 7.18-7.80 (m, 8H)
< 실시예 152> 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N-(2-메톡시에틸)아세트아마이드 {2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N-(2-methoxyethyl)acetamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.93 (t, 3H), 1.37-1.46 (m, 2H), 1.67-1.75 (m, 4H), 2.43 (s, 3H), 2.71 (t, 2H), 3.25 (s, 3H), 3.33-3.39 (m, 4H), 3.45 (s, 2H), 5.29 (s, 2H), 6.84 (s, 1H), 7.20-7.83 (m, 8H), 8.43 (s, 1H)
< 실시예 153> 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N-(2-(싸이오펜-2-일)에틸)아세트아마이드 {2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N-(2-(thiophen-2-yl)ethyl)acetamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.93 (t, 3H), 1.37-1.46 (m, 2H), 1.68-1.76 (m, 2H), 2.18 (s, 3H), 2.43 (s, 3H), 2.70 (t, 2H), 2.95 (t, 2H), 3.41-3.46 (m, 4H), 5.27 (s, 2H), 6.74-6.79 (m, 2H), 6.86-6.89 (m, 1H), 7.08-7.10 (m, 1H), 7.18-7.84 (m, 8H)
< 실시예 154> 2-(2-부틸-4- 메틸 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4-옥 사다 이아졸-3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N,N-다이아이소프로필아세트아마이드 {2-(2-butyl-4-methyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N,N-diisopropylacetamide 의 제조
1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H), 1.22-1.44 (m, 14H), 1.65-1.73 (m, 2H), 2.28 (s, 3H), 2.65 (t, 2H), 3.47 (s, 1H), 3.59 (s, 1H), 4.13-4.20 (m, 1H), 5.29 (s, 2H), 7.23-7.84 (m, 8H)
< 실시예 155> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
Figure 112017080786708-pat00013
플라스크에 실시예 39에서 제조된 화합물 (70 mg, 0.14 mmole)을 투입하고 톨루엔 7 mL를 주입한 후, 로신 시약 (44.4 mg, 0.11 mmole)을 투입하였다. 85 ℃에서 4 시간 가온 교반 후, 감압 농축하여 용매를 제거하고, 클로로포름 150 mL와 정제수 150 mL를 가하여 유기층을 분리하였다. 분리한 유기층을 정제수 150 mL로 세척하고 마그네슘설페이트 0.3 g으로 건조한 후 여과하여 농축하였다. 잔사를 99:1 클로로포름/메틸알콜로 크로마토그래피로 정제하여 미황색 고체의 표제 화합물 32 mg(수율: 44.2 %)을 얻었다.
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 2H), 1.71 (m, 2H), 2.38 (s, 3H), 2.63 (t, 2H), 3.45 (s, 3H), 3.51 (s, 3H), 3.81 (s, 2H), 5.26 (s, 2H), 7.19 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 156 내지 실시예 287>
아래 실시예 156 내지 287은 각 실시예에 대응되는 출발물질로부터 실시예 155와 동일한 방법으로 합성하였다.
< 실시예 156> 3-(4'-((5-(2-(1H- 아이소인돌 -2(3H,3 aH ,4H,5H,6H,7H,7 aH )-일)-2-싸 이옥소에 틸)-2-부틸-4- 메틸 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((5-(2-(1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)-2-thioxoethyl)-2-butyl-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 14H), 2.28 (s, 3H), 2.36 (m, 1H), 2.38 (m, 1H), 2.63 (t, 2H), 3.58-3.87 (m, 6H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 157> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-(2- 메틸프로필 ) 에탄싸이오아마 이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-(2-methylpropyl)ethanethioamide}의 제조
1H-NMR (400MHz): δ 0.94 (m, 6H), 1.02 (d, 3H), 1.41 (m, 2H), 1.72 (m, 2H), 2.17 (m, 1H), 2.34 (d, 3H), 2.67 (t, 2H), 3.44 (d, 3H), 3.61 (d, 1H), 3.84 (d, 2H), 3.92 (d, 1H), 5.27 (d, 2H), 7.20 (d, 2H), 7.27 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 158> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(2-피페리딘-1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(2-piperidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.41 (m, 2H), 1.71 (m, 8H), 2.31 (s, 3H), 2.68 (t, 2H), 3.52 (m, 4H), 4.28 (s, 2H), 5.27 (s, 2H), 7.20 (d, 2H), 7.25 (d, 2H), 7.42 (m, 1H), 7.48 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 159> 3-[2-[4-[[2-부틸-4- 메틸 -5-(2- 몰폴린 -4-일-2- 설파닐리덴에틸 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(2-morpholin-4-yl-2-sulfanylideneethyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.72 (m, 4H), 3.84 (s, 2H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 160> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-프로판-2- 일에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.11 (d, 6H), 1.37 (m, 2H), 1.68 (m, 2H), 2.58 (s, 3H), 2.67 (t, 2H), 3.94 (s, 2H), 4.46 (m, 1H), 5.30 (s, 2H), 7.16 (d, 2H), 7.28 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 161> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일에탄싸이오아마이 드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 1.17 (d, 3H), 1.29 (d, 3H), 1.43 (m, 2H), 1.74 (m, 2H), 2.31 (d, 3H), 2.69 (t, 2H), 3.20-3.28 (d, 3H), 3.79-3.92 (d, 2H), 4.85-5.05 (m, 1H), 5.28 (s, 2H), 7.19 (d, 2H), 7.26 (m, 2H), 7.41 (d, 1H), 7.50 (t, 1H), 7.61 (t, 1H), 7.78 (d, 1H)
< 실시예 162> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(2- 피롤리딘 -1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(2-pyrrolidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 2H), 1.70 (m, 2H), 1.95 (m, 2H), 2.13 (m, 2H), 2.38 (s, 3H), 2.68 (t, 2H), 3.78 (s, 2H), 3.89 (m, 4H), 5.28 (s, 2H), 7.19 (d, 2H), 7.27 (d, 2H), 7.45 (m, 1H), 7.56 (t, 1H), 7.64 (d, 1H), 7.79 (d, 1H)
< 실시예 163> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(3,5- dimethylpiperidin -1- yl )-2- sulfanylideneethyl ]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.90-0.96 (m, 9H), 1.02 (d, 1H), 1.36-1.76 (m, 6H), 1.88 (d, 1H), 2.31 (s, 3H), 2.41 (t, 1H), 2.67-2.75 (m, 3H), 3.72-3.92 (m, 2H), 4.40 (d, 1H), 5.29 (s, 2H), 5.60-5.64 (m, 1H), 7.21-7.83 (m, 8H)
< 실시예 164> 2-부틸-N,4- 다이메틸 -N-(2- 메틸프로필 )-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카보싸이오아마이드 {2-butyl-N,4-dimethyl-N-(2-methylpropyl)-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.80-1.02 (m, 9H), 1.36-1.45 (m, 2H), 1.66-1.74 (m, 4H), 1.94-2.05 (m, 1H), 2.30-2.43 (m, 4H), 2.67-2.73 (m, 2H), 3.11-3.45 (m, 4H), 3.78-3.98 (m, 1H), 5.15-5.40 (m, 2H), 7.16-7.80 (m, 8H)
< 실시예 165> 2-부틸-N,N,4- 트리메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카보싸이오아마이드 ; 2-butyl-N,N,4-trimethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.36-1.45 (m, 2H), 1.66-1.73 (m, 2H), 2.28 (s, 3H), 2.69-2.74 (m, 2H), 3.14 (s, 3H), 3.49 (s, 3H), 5.14-5.34 (m, 2H), 7.17-7.79 (m, 8H)
< 실시예 166> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(피페리딘-1- 카보싸이오일 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(piperidine-1-carbothioyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.93 (t, 3H), 1.35-1.73 (m, 10H), 2.25 (s, 3H), 2.68-2.72 (t, 2H), 3.26-3.34 (m, 2H), 3.45-3.50 (m, 1H), 3.80-3.84 (m, 1H), 5.18-5.32 (m, 2H), 7.19-7.76 (m, 8H)
< 실시예 167> 3-[2-[4-[[2-부틸-4- 메틸 -5-( 몰폴린 -4- 카보싸이오일 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(morpholine-4-carbothioyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90-0.94 (t, 3H), 1.35-1.44 (m, 2H), 1.65-1.73 (m, 2H), 2.28 (s, 3H), 2.69-2.73 (t, 2H), 3.27-3.79 (m, 8H), 5.18-5.35 (m, 2H), 7.22-7.79 (m, 8H)
< 실시예 168> 2-부틸-N,4- 다이메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-N-프로판-2- 일피리미딘 -5- 카보싸이오아마이드 {2-butyl-N,4-dimethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-N-propan-2-ylpyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.88-0.92 (t, 3H), 1.14-1.18 (m, 6H), 1.33-1.43 (m, 2H), 1.63-1.71 (m, 2H), 2.19-2.22 (d, 3H), 2.65-2.71 (m, 2H), 2.74-2.87 (d, 3H), 3.77-3.83 (m, 0.5H), 4.84-4.95 (m, 0.5H), 5.17-5.31 (m, 2H), 7.16-7.73 (m, 8H)
< 실시예 169> 3-[2-[4-[[5-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2- 카보싸이오일 )-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-(1,3,3a,4,5,6,7,7a-octahydroisoindole-2-carbothioyl)-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.89-0.92 (t, 3H), 1.28-1.70 (m, 12H), 2.23-2.24 (m, 5H), 2.65-2.70 (m, 2H), 2.99-3.49 (m, 4H), 5.18-5.40 (m, 2H), 7.18-7.75 (m, 8H)
< 실시예 170> 2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-N-프로판-2- 일피리미딘 -5- 카보싸이오아마이드 {2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-N-propan-2-ylpyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.88-0.92 (t, 3H), 1.14-1.18 (m, 6H), 1.33-1.43 (m, 2H), 1.63-1.71 (m, 2H), 2.65-2.71 (m, 2H), 2.74-2.87 (d, 3H), 3.77-3.83 (m, 0.5H), 4.84-4.95 (m, 0.5H), 5.17-5.31 (m, 2H), 7.16-7.73 (m, 8H)
< 실시예 171> 2-부틸-N- 사이클로헥실 -4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카보싸이오아마이드 {2-butyl-N-cyclohexyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.88-0.96 (t, 3H), 1.12-1.76 (m, 10H), 1.96-1.98 (m, 2H), 2.31 (s, 3H), 2.64-2.72 (m, 2H), 2.79-2.83 (t, 2H), 4.30-4.40 (m, 1H), 5.15-5.33 (m, 2H), 7.12-7.73 (m, 8H)
< 실시예 172> 3-[2-[4-[[2-부틸-5-(3,5- 다이메틸피페리딘 -1- 카보싸이오일 )-4-메틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-(3,5-dimethylpiperidine-1-carbothioyl)-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.76-1.07 (m, 9H), 1.33-1.80 (m, 8H), 2.16-2.29 (m, 3H, m), 2.57-2.73 (m, 2H), 3.51-4.12 (m, 2H), 4.98-5.58 (m, 3H), 7.12-7.75 (m, 8H)
< 실시예 173> 2-부틸-4- 메틸 -N-(2- 메틸프로필 )-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5- 카보싸이오아마이드 {2-butyl-4-methyl-N-(2-methylpropyl)-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidine-5-carbothioamide}의 제조
1H-NMR (400MHz): δ 0.87-0.97 (m, 9H), 1.35-1.49 (m, 2H), 1.69-1.80 (m, 2H), 2.02-2.08 (m, 1H), 2.37 (s, 3H), 2.81-2.85 (t, 2H), 3.45-3.48 (t, 2Ht), 5.18 (s, 2H), 7.16-7.79 (m, 8H)
< 실시예 174> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이에틸에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-diethylethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.88 (t, 3H), 1.25-1.40 (m, 8H), 1.62-1.70 (m, 2H), 2.28 (s, 3H), 2.60 (t, 2H), 3.76 (q, 2H), 3.99 (q, 2H), 5.23 (s, 2H), 7.14-7.73 (m, 8H), 9.56 (s, 1H)
< 실시예 175> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 프로필에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-propylethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.84-0.91 (m, 6H), 1.31-1.41 (m, 2H), 1.49-1.59 (m, 2H), 1.63-1.70 (m, 2H), 2.56 (s, 3H), 2.65 (t, 2H), 3.46 (q, 2H), 3.95 (s, 2H), 5.29 (s, 2H), 7.13-7.74 (m, 8H), 9.20 (t, 1H), 9.54 (s, 1H)
< 실시예 176> N-부틸-2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일] 에탄싸이오아마이드 {N-butyl-2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]ethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.84-0.90 (m, 6H), 1.25-1.70 (m, 8H), 2.55 (s, 3H), 2.64 (t, 2H), 3.47-3.52 (m, 2H), 3.94 (s, 2H), 5.29 (s, 2H), 7.13-7.74 (m, 8H), 9.19 (t, 2H), 9.62 (s, 1H)
< 실시예 177> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.39-1.72 (m, 10H), 2.30 (s, 3H), 2.33-2.39 (m, 2H), 2.63 (t, 2H), 3.65-3.83 (m, 6H), 5.22 (s, 2H), 7.14 (d, 2H), 7.26 (d, 2H), 7.37 (d, 1H), 7.45 (t, 1H), 7.57 (t, 1H), 7.69 (d, 1H)
< 실시예 178> N- 메톡시 -N- 메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일] 에탄싸이오아마 이드 {N- methoxy -N- methyl -2-[4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]ethanethioamide}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.68-1.74 (m, 2H), 2.28 (s, 3H), 2.64 (t, 2H), 3.66 (s, 3H), 3.84 (s, 3H), 3.94 (s, 2H), 5.24 (s, 2H), 7.15 (d, 2H), 7.28 (d, 2H), 7.39 (d, 1H), 7.46 (t, 1H), 7.59 (t, 1H), 7.72 (d, 1H)
< 실시예 179> N,N- 다이메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일] 에탄싸이오아마이드 {N,N-dimethyl-2-[4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]ethanethioamide}의 제조
1H-NMR (400MHz): δ 0.96 (t, 3H), 1.67-1.77 (m, 2H), 2.29 (s, 3H), 2.62 (dd, 2H), 3.43 (s, 2H), 3.49 (s, 3H), 3.80 (s, 2H), 5.24 (s, 2H), 7.16 (d, 2H), 7.28 (d, 2H), 7.39 (d, 1H), 7.47 (t, 1H), 7.59 (t, 1H), 7.75 (d, 1H)
< 실시예 180> 3-[2-[4-[[4- 메틸 -6-옥소-2-프로필-5-(2- 피롤리딘 -1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[4-methyl-6-oxo-2-propyl-5-(2-pyrrolidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.97 (t, 3H), 1.68-1.75 (m, 2H), 1.92-2.00 (m, 2H), 2.05-2.15 (m, 2H), 2.33 (s, 3H), 2.68 (t, 2H), 3.75 (s, 2H), 3,78-3.85 (m, 4H), 5.24 (s, 2H), 7.16 (d, 2H), 7.28 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.73 (d, 1H)
< 실시예 181> 3-[2-[4-[[4- 메틸 -6-옥소-5-(2-피페리딘-1-일-2- 설파닐리덴에틸 )-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[4-methyl-6-oxo-5-(2-piperidin-1-yl-2-sulfanylideneethyl)-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 1.64-1.76 (m, 8H), 2.27 (s, 3H), 2.60 (t, 2H), 3.82 (s, 4H), 4.26 (s, 2H), 5.23 (s, 2H), 7.14 (d, 2H), 7.27 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.72 (d, 2H)
< 실시예 182> 3-[2-[4-[[5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(3,5-dimethylpiperidin-1-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.86-1.00 (m, 9H), 1.45-1.57 (m, 1H), 1.67-1.75 (m, 3.4H), 2.02-2.08 (m, 1H), 2.25 (s, 3H), 2.39 (t, 0.6H), 2.60 (t, 2H), 2.69 (t, 0.6H), 3.56-3.62 (m, 0.4H), 3.69-3.87 (m, 3.4H), 4.34 (d, 0.6H), 4.62 (d, 0.4H), 5.23 (s, 2H), 5.60 (d, 0.6H), 7.15 (d, 2H), 7.27 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.72 (d, 1H)
< 실시예 183> 3-[2-[4-[[5-[2-(3,5- 다이메틸몰폴린 -4-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(3,5-dimethylmorpholin-4-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.98 (t, 3H), 1.19-1.25 (m, 6H), 1.71-1.78 (m, 2H), 2.32 (s, 3H), 2.62-2.66 (m, 3H), 2.93-3.01 (m, 1H), 3.62-3.28 (m, 2H), 3.78-3.91 (m, 3.6H), 4.39 (d, 0.7H), 5.27 (s, 2H), 5.55 (d, 0.7H), 7.19 (d, 2H), 7.29 (d, 2H), 7.39 (d, 1H), 7.48 (t, 1H), 7.60 (t, 1H), 7.77 (d, 1H)
< 실시예 184> N- 메틸 -2-[4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일l) 페닐 ] 페닐 ] 메틸 ]-2- 프로필피리미딘 -5-일]-N-프로판-2- 일에탄싸이오아마 이드 {N-methyl-2-[4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-2-propylpyrimidin-5-yl]-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.97 (t, 3H), 1.18 (d, 3H), 1.29 (d, 3H), 1.70-1.78 (m, 2H), 2.33 (s, 3H), 2.74 (t, 2H), 3.19 (s, 1.7H), 3.28 (s, 1.3H), 3.89 (d, 2H), 4.73-4.80 (m, 0.4H), 5.27 (s, 2H), 5.87-5.93 (m, 0.6H), 7.19 (d, 2H), 7.29 (d, 2H), 7.38 (d, 1H), 7.47 (t, 1H), 7.59 (t, 1H), 7.74 (d, 1H)
< 실시예 185> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸프로판싸이오아마이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylpropanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.85 (m, 2H), 2.43 (s, 3H), 2.52 (t, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (s, 3H), 3.21 (s, 3H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 186> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일프로판싸이오아마 이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylpropanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.28 (t, 3H), 1.40 (m, 2H), 1.60 (m, 2H), 1.85 (m, 2H), 2.52 (t, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (s, 4H), 5.26 (s, 2H), 6.87 (d, 1H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 187> 3-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 사이클로프로필프로판싸이오아마이드 {3-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-cyclopropylpropanethioamide}의 제조
1H-NMR (400MHz): δ 0.80 (m, 5H), 0.91 (t, 3H), 1.40 (m, 2H), 1.85 (m, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 2.95 (m, 4H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 188> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(3-피페리딘-1-일-3- 설파닐리덴프로필 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(3-piperidin-1-yl-3-sulfanylidenepropyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.10 (t, 2H), 2.36 (t, 2H), 2.60-2.90 (m, 4H), 3.84 (s, 2H), 3.95 (m, 3H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 189> 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-3- 설파닐리덴프로필 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-3-sulfanylidenepropyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.86 (t, 2H), 2.90 (m, 2H), 3.84 (s, 2H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 190> 3-[2-[4-[[2-부틸-4- 메틸 -5-[3-(4- 메틸피페리딘 -1-일)-3- 설파닐리덴프로필 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[3-(4-methylpiperidin-1-yl)-3-sulfanylidenepropyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.41 (m, 5H), 1.71 (m, 8H), 2.31 (s, 3H), 2.68 (t, 2H), 3.52 (m, 4H), 4.28 (m, 4H), 5.27 (s, 2H), 7.20 (d, 2H), 7.25 (d, 2H), 7.42 (m, 1H), 7.48 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 191> 3-[2-[4-[[2-부틸-5-[3-(3,3- 다이메틸피페리딘 -1-일)-3- 설파닐리덴프로필 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[3-(3,3-dimethylpiperidin-1-yl)-3-sulfanylidenepropyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.43 (m, 6H), 1.52 (m, 5H), 1.85 (m, 3H), 2.64 (t, 2H), 2.86 (t, 2H), 3.20 (d, 2H), 3.50 (d, 2H), 3.85 (m, 4H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 192> 3-[2-[4-[[2-부틸-5-[3-(3,5- 다이메틸몰폴린 -4-일)-3- 설파닐리덴프로필 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[3-(3,5-dimethylmorpholin-4-yl)-3-sulfanylidenepropyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 6H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 3H), 3.84 (m, 4H), 3.95 (m, 3H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 193> 3-[2-[4-[[2-부틸-4- 메틸 -5-(3- 몰폴린 -4-일-3- 설파닐리덴프로필 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-(3-morpholin-4-yl-3-sulfanylidenepropyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 4H), 3.84 (m, 5H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 194> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2-부탄-2-일-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-butan-2-yl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.75 (t, 3H), 1.17 (d, 3H), 1.38-1.62 (m, 11H), 1.77-1.88 (m, 1H), 2.38 (s, 3H), 2.73-2.78 (m, 1H), 3.70-3.87 (m, 6H), 5.30 (br, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.37 (d, 1H), 7.47 (t, 1H), 7.59 (t, 1H), 7.76 (d, 1H)
< 실시예 195> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메톡시 -N- 메틸에탄싸이오아마이 드 {2-[2- butan -2- yl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methoxy-N-methylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.73 (t, 3H), 1.15 (d, 3H), 1.46-1.53 (m, 1H), 1.77-1.82 (m, 1H), 2.31 (s, 3H), 2.70-2.76 (m, 1H), 3.67 (s, 3H), 3.87 (s, 3H), 3.93 (s, 2H), 5.29 (br, 2H), 7.12 (d, 2H), 7.26 (d, 2H), 7.37 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.70 (d, 1H)
< 실시예 196> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오아마이드 {2-[2-butan-2-yl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.76 (t, 3H), 1.18 (d, 3H), 1.48-1.56 (m, 1H), 1.79-1.87 (m, 1H), 2.34 (s, 3H), 2.73-2.79 (m, 1H), 3.45 (s, 3H), 3.50 (s, 3H), 3.82 (s, 2H), 5.30 (br, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.37 (d, 1H), 7.48 (t, 1H), 7.59 (t, 1H), 7.78 (d, 1H)
< 실시예 197> 2-[2-부탄-2-일-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일에탄싸이오 아마이드 {2-[2-butan-2-yl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.74 (s, 3H), 1.18 (d, 6H), 1.26-1.29 (m, 3H), 1.49-1.56 (m, 1H), 1.78-1.86 (m, 1H), 2.34 (s, 3H), 2.75-2.80 (m, 1H), 3.19 (s, 1.6H), 3.29 (s, 1.4H), 3.79 (s, 2H), 4.75-4.82 (m, 0.5H), 5.33 (s, 2H), 5.88-5.96 (m, 0.5H), 7.17 (d, 2H), 7.26 (d, 2H), 7.36 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.74 (d, 1H)
< 실시예 198> 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6- 다이메틸피페리딘 -1-일)-2-설파닐리덴에틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butan-2-yl-5-[2-(2,6-dimethylpiperidin-1-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.71 (t, 3H), 0.86-1.00 (m, 7H), 1.18 (d, 3H), 1.49-1.89 (m, 5H), 2.08 (br, 1H), 2.35 (s, 3H), 2.70 (t, 1H), 2.79-2.84 (m, 1H), 3.70-3.89 (m, 3.4H), 4.34 (d, 0.6H), 4.60 (t, 0.4H), 5.32 (s, 2H), 5.59 (d, 0.6H), 7.14 (d, 2H), 7.24 (d, 2H), 7.35 (d, 1H), 7.43 (t, 1H), 7.56 (t, 1H), 7.67 (d, 1H)
< 실시예 199> 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butan-2-yl-5-[2-(2,6-dimethylmorpholin-4-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.77 (t, 3H), 1.19-1.28 (m, 9H), 1.51-1.58 (m, 1H), 1.81-1.88 (m, 1H), 2.34 (s, 2H), 2.64-2.79 (m, 2H), 2.98 (t, 1H), 3.62-3.69 (m, 2H), 3.84-4.00 (m, 2H), 4.41 (d, 1H), 5.28 (s, 2H), 5.57 (d, 1H), 7.13 (d, 2H), 7.22 (d, 2H), 7.40 (d, 1H), 7.50 (t, 1H), 7.62 (t, 1H), 7.77 (d, 1H)
< 실시예 200> 3-(4'-((2-부틸-5-(2-(3,5- 다이메틸피페리딘 -1-일)-2- 싸이옥소에틸 )-4- 메틸 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-5-(2-(3,5-dimethylpiperidin-1-yl)-2-thioxoethyl)-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.90-0.96 (m, 9H, m), 1.02 (d, 1H), 1.36-1.76 (m, 6H), 1.88 (d, 1H), 2.31 (s, 3H), 2.41 (t, 1H), 2.67-2.75 (m, 3H), 3.72-3.92 (m, 2H), 4.40 (d, 1H), 5.29 (s, 2H), 5.60-5.64 (m, 1H), 7.21-7.83 (m, 8H)
< 실시예 201> 3-[2-[4-[[2-부틸-5-[2-(3,4- 다이하이드로 -1H- 아이소퀴놀린 -2-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20-1.30 (m, 2H), 1.40-1.80 (m, 2H), 2.64 (s, 3H), 2.66 (m, 2H), 2.90 (m, 2H), 3.95 (m, 2H), 4.30-4.60 (dd, 1H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 2H), 7.49 (t, 2H), 7.62-7.80 (m, 3H), 8.10 (d, 1H)
< 실시예 202> 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a- 옥타하이드로 -1H- 아이소퀴놀린 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]페닐]-4H-1,2,4-옥사다이아졸-5-온; 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91(t, 3H), 1.20-1.30 (m, 8H), 1.40-1.80 (m, 9H), 2.64 (s, 3H), 2.67 (m, 2H), 2.90 (m, 1H), 3.95 (m, 4H), 4.30-4.60 (dd, 1H), 5.26 (s, 2H), 5.50-5.70 (dd, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 203> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-[2- 설파닐리덴 -2-(1,3- 싸이아졸리딘 -3-일)에틸]피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-[2-sulfanylidene-2-(1,3-thiazolidin-3-yl)ethyl]pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H), 1.34-1.74 (m, 4H), 2.34 (d, 3H), 2.68 (t, 2H), 3.07-3.23 (m, 2H), 3.81 (s, 2H), 4.13-4.23 (m, 2H), 4.90 (d, 2H), 5.25 (s, 2H), 7.16-7.79 (m, 8H), 8.77 (s, 1H)
< 실시예 204> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-(4- 메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-(4-methylpiperidin-1-yl)-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.89 (t, 3H), 0.96 (d, 3H), 1.17-1.41 (m, 4H), 1.63-1.78 (m, 5H), 2.27 (s, 3H), 2.62 (t, 2H), 2.97-3.24 (m, 2H), 3.82 (q, 2H), 4.43 (d, 1H), 5.23 (s, 2H), 5.52 (d, 1H), 7.14-7.74 (m, 8H), 9.49 (s, 1H)
< 실시예 205> 3-[2-[4-[[2-부틸-5-[2-(2,6- 다이메틸몰폴린 -4-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(2,6-dimethylmorpholin-4-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H NMR (400 MHz, CDCl3): δ 0.90 (t, 3H), 1.20-1.73 (m, 10H), 2.31 (s, 3H), 2.62-2.66 (m, 3H), 2.95 (t, 1H), 3.62-3.91 (m, 4H), 4.38 (d, 1H), 5.25 (s, 2H), 5.54 (d, 1H), 7.16-7.77 (m, 8H), 9.00 (s, 1H)
< 실시예 206> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메톡시 -N- 메틸에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methoxy-N-methylethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.88 (t, 3H), 1.31-1.40 (m, 2H), 1.62-1.70 (m, 2H), 2.25 (s, 3H), 2.60 (t, 2H), 3.66 (s, 3H), 3.84 (s, 3H), 3.90 (s, 2H), 5.23 (s, 2H), 7.14-7.74 (m, 8H), 9.46 (s, 1H)
< 실시예 207> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N-(2- 메톡시에틸 )-N- 메틸에탄싸이오아마 이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-(2-methoxyethyl)-N-methylethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.93 (t, 3H), 1.37-1.46 (m, 2H), 1.68-1.76 (m, 2H), 2.59 (s, 3H), 2.72 (t, 2H), 3.25 (s, 3H), 3.45-3.49 (m, 2H), 3.72-3.76 (m, 2H), 5.32 (s, 2H), 7.23-7.84 (m, 8H), 7.89 (s, 1H), 9.35 (s, 1H)
< 실시예 208> 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(2-싸이오펜-2-일에틸)에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-(2-thiophen-2-ylethyl)ethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.93 (t, 3H), 1.37-1.76 (m, 4H), 2.17 (s, 2H), 2.59 (s, 3H), 2.70 (t, 2H), 3.09 (t, 2H), 3.81-3.86 (m, 2H), 3.98 (s, 2H), 5.26 (s, 2H), 6.77-7.85 (m, 11H), 9.29 (s, 1H)
< 실시예 209> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이(프로판-2-일)에탄싸이오아마이 드 {2-[2- butyl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-di(propan-2-yl)ethanethioamide}의 제조
1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H), 1.25-1.74 (m, 18H), 2.31 (s, 3H), 2.65 (t, 2H), 3.87 (s, 2H), 5.31 (s, 2H), 7.22-7.83 (m, 8H), 8.32 (s, 1H)
< 실시예 210> 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2- 설파닐리덴에틸 )-4- 메틸 -6-옥 소피리미 딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-(2-indol-1-yl-2-sulfanylideneethyl)-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.62 (t, 2H), 3.63 (m, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 7H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 211> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-(2- 메틸피롤리딘 -1-일)-2- 설파닐리덴에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-(2-methylpyrrolidin-1-yl)-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 5H), 1.70 (m, 4H), 1.80-2.10 (m,5H), 2.34 (s, 3H), 2.62 (t, 2H), 3.63 (m, 2H), 5.25 (s, 2H), 7.18 (d, 2H), 7.28 (d, 7H), 7.41 (m, 1H), 7.51 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 212> 2-[2- 사이클로프로필 -4- 메틸 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오 아마이드 {2-[2- cyclopropyl -4- methyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 2.40-2.63 (m, 8H), 3.45 (s, 3H), 3.51 (s, 3H), 5.26 (s, 2H), 7.19 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 213> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2- 사이클로프로필 -4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-cyclopropyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 1.39-1.74 (m, 14H), 2.28 (m, 4H), 2.36 (m, 1H), 2.38 (m, 1H), 2.63 (t, 2H), 3.58 (m, 2H), 3.65 (s, 2H), 5.25 (s, 2H), 7.19 (d, 2H), 7.31 (m, 2H), 7.43 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.72 (d, 1H)
< 실시예 214> 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a- 옥타하이드로인돌 -1-일)-2-설 파닐리덴에 틸]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.86 (t, 2H), 2.90 (m, 2H), 3.84 (s, 2H), 3.95 (m, 2H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 215> 3-[2-[4-[[2-부틸-5-[2-(1,3- 다이하이드로아이소인돌 -2-일)-2-설파닐리덴에틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(1,3-dihydroisoindol-2-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20-1.30 (m, 2H), 1.40-1.80 (m, 2H), 2.64 (s, 3H), 2.90 (m, 2H), 3.95 (m, 2H), 4.30-4.60 (dd, 1H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 2H), 7.49 (t, 2H), 7.62-7.80 (m, 3H), 8.10 (d, 1H)
< 실시예 216> 3-[2-[4-[[2-부틸-5-[2-(2,3- 다이하이드로인돌 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(2,3- dihydroindol -1- yl )-2- sulfanylideneethyl ]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.20-1.40 (m, 2H), 1.50-1.80 (m, 2H), 2.63 (s, 3H), 2.90 (m, 2H), 3.80 (m, 2H), 4.46-4.53 (m, 1H), 5.28 (s, 2H), 7.28 (m, 4H), 7.42 (m, 2H), 7.49 (t, 2H), 7.62-7.80 (m, 3H), 8.10 (d, 1H)
< 실시예 217> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-[2-(4-프로판-2- 일피페리딘 -1-일)-2- 설파닐리덴에틸 ]피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-[2-(4-propan-2-ylpiperidin-1-yl)-2-sulfanylideneethyl]pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20-1.30 (m, 9H), 1.40-1.80 (m, 4H), 2.64 (m, 4H), 2.90 (m, 4H), 3.95 (m, 4H), 4.30-4.60 (dd, 2H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (d, 1H), 7.49 (d, 1H), 7.62 (d, 1H), 8.10 (d, 1H)
< 실시예 218> 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a- 헥사하이드로 -1H- 사이클로펜타[c]피롤 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20-1.30 (m, 2H), 1.40-1.60 (m, 6H), 1.80 (m, 3H), 2.30 (s, 3H), 2.64 (m, 4H), 2.90 (m, 4H), 3.95 (m, 4H), 4.30-4.60 (dd, 2H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (d, 1H), 7.49 (d, 1H), 7.62 (d, 1H), 8.10 (d, 1H)
< 실시예 219> 3-[2-[4-[[2-부틸-5-[2-(1,3- 다이하이드로아이소인돌 -2-일)-2-설파닐리덴에틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(1,3-dihydroisoindol-2-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.40-1.60 (t, 2H), 1.80 (t, 2H), 2.80 (d, 2H), 3.95 (m, 4H), 4.30-4.60 (dd, 2H), 5.26 (s, 2H), 7.27 (m, 9H), 7.42 (d, 1H), 7.49 (d, 1H), 7.62 (d, 1H), 8.10 (d, 1H)
< 실시예 220> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-[4-(4- 나이트로페닐 )피페라진-1-일]-2- 설파닐리덴에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-[4-(4-nitrophenyl)piperazin-1-yl]-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 1.34-1.40 (m, 2H), 1.65-1.71 (m, 2H), 2.36 (s, 3H), 2.65 (t, 2H), 3.58-3.64 (m, 4H), 3.90 (s, 2H), 4.22 (t, 2H), 4.45 (t, 2H), 5.24 (s, 2H), 6.73 (d, 2H), 7.15 (d, 2H), 7.27 (d, 2H), 7.36 (d, 1H), 7.47 (t, 1H), 7.58 (t, 1H), 7.74 (d, 1H)
< 실시예 221> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]-4- 플루오 로페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]-4-fluorophenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.88 (t, 3H), 1.34-1.68 (m, 12H), 2.32 (s, 2H), 2.35-2.39 (m, 1H), 2.68 (br, 2H), 3.64-3.85 (m, 7H), 5.30 (s, 2H), 7.07 (d, 1H), 7.13-7.25 (m, 5H), 7.62-7.67 (m, 1H)
< 실시예 222> 2-[2-부틸-1-[[4-[5- 플루오로 -2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4- 메틸 -6- 옥소피리미딘 -5-일]-N- 메톡시 -N- 메틸에탄싸이오 아마이드 {2-[2-butyl-1-[[4-[5-fluoro-2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-methyl-6-oxopyrimidin-5-yl]-N-methoxy-N-methylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.88 (t, 3H), 1.32-1.39 (m, 2H), 1.64-1.70 (m, 2H), 2.28 (s, 2H), 2.65 (t, 2H), 3.66 (s, 3H), 3.85 (s, 3H), 3.89 (s, 2H), 5.24 (s, 2H), 7.09 (d, 1H), 7.13-7.27 (m, 5H), 7.69-7.72 (m, 1H)
< 실시예 223> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-(2- 피롤리딘 -1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ]-4- 플루오로페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-(2-pyrrolidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]-4-fluorophenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.85 (t, 3H), 1.32-1.39 (m, 2H), 1.63-1.68 (m, 2H), 1.93-2.18 (m, 4H), 2.36 (s, 3H), 2.85 (t, 2H), 3.74-3.86 (m, 6H), 5.28 (s, 2H), 7.07 (d, 1H), 7.11-7.24 (m, 5H), 7.66-7.82 (m, 1H)
< 실시예 224> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]-4- 플루오로페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(3,5-dimethylpiperidin-1-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]-4-fluorophenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.87-0.95 (m, 9H), 1.33-1.42 (m, 2H), 1.65-1.90 (m, 4H), 2.27 (s, 3H), 2.40 (t, 1H), 2.64 (t, 2H), 2.70 (t, 1H), 3.20-3.88 (m, 2H), 4.36 (d, 1H), 5.24 (s, 2H), 5.60 (d, 1H), 7.09 (d, 1H), 7.14-7.19 (m, 3H), 7.25-7.28 (m, 2H), 7.75 (dd, 1H)
< 실시예 225> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸몰폴린 -4-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]-4- 플루오로페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(3,5-dimethylmorpholin-4-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]-4-fluorophenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.85 (t, 3H), 1.13-1.25 (m, 6H), 1.32-1.41 (m, 2H), 1.64-1.72 (m, 2H), 2.36 (s, 3H), 2.91 (t, 2H), 3.64 (s, 2H), 3.75-3.87 (m, 4H), 4.28 (br, 1H), 5.30 (s, 2H), 5.48 (d, 1H), 7.04-7.24 (m, 6H), 7.65 (d, 1H)
< 실시예 226> 2-[2-부틸-1-[[4-[5- 플루오로 -2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4- 메틸 -6- 옥소피리미딘 -5-일]-N- 메틸 -N-(2- 메틸프로필 )에탄싸이오아마이드 {2-[2-butyl-1-[[4-[5-fluoro-2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-methyl-6-oxopyrimidin-5-yl]-N-methyl-N-(2-methylpropyl)ethanethioamide}의 제조
1H-NMR (400MHz): δ 0.83 (t, 3H), 0.92 (d, 3H), 0.99 (d, 3H), 1.32-1.39 (m, 2H), 1.64-1.70 (m, 2H), 2.42 (s, 3H), 3.06 (t, 2H), 3.38 (d, 2H), 3.55 (d, 1H), 3.74-3.83 (m, 5H), 5.32 (s, 2H), 7.06-7.25 (m, 6H), 7.67 (d, 1H)
< 실시예 227> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-(2- 메틸 -1,3,3a,4,6,6a- 헥사하이드로피롤로[3,4-c]피롤 -5-일)-2- 설파닐리덴에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 13H), 2.28 (s, 3H), 2.36 (m, 1H), 2.38 (m, 1H), 2.63 (t, 2H), 3.58-3.87 (d, 2H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 228> 3-(4'-((2-부틸-5-(2-( 헥사하이드로사이클로펜타[c]피롤 -2(1H)-일)-2- 싸이옥소에틸 )-4- 메틸 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-2-thioxoethyl)-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.30-1.74 (m, 12H), 2.03 (m, 2H), 2.63 (t, 2H), 2.91 (s, 3H), 3.58-3.86 (d, 4H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 229> 3-[2-[4-[[5-[2-(1,3,4,6,7,8,9,9a- 옥타하이드로피리도[1,2-a]피라진 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 14H), 2.28 (s, 3H), 2.36 (m, 1H), 2.40 (m, 4H), 2.63 (t, 2H), 3.58-3.87 (m, 4H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 230> 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a- 옥타하이드로인돌 -1-일)-2-싸 이옥 소-에틸]-2-부틸-4- 메틸 -6-옥소-피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-2H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)-2-thioxo-ethyl]-2-butyl-4-methyl-6-oxo-pyrimidin-1-yl]methyl]phenyl]phenyl]-2H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.29-1.75 (m, 14H), 2.05 (m, 2H), 2.64 (t, 2H), 2.91 (s, 3H), 3.68-3.86 (d, 4H), 5.25 (s, 2H), 7.17-7.28 (m, 4H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 231> 3-[2-[4-[[5-[2-(7- 아자바이사이클로[2.2.1]헵탄 -7-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(7-azabicyclo[2.2.1]heptan-7-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.99 (t, 3H), 1.58-1.65 (m, 2H), 1.71-2.05 (m, 8H), 2.61 (s, 3H), 2.68 (t, 2H), 3.97 (s, 2H), 5.30 (s, 2H), 5.52-5.64 (m, 2H), 7.20 (d, 2H), 7.31 (d, 2H), 7.38 (d, 1H), 7.53 (t, 1H), 7.63 (t, 1H), 7.82 (d, 1H)
< 실시예 232> 3-[2-[4-[[2-부틸-4- 메틸 -6-옥소-5-[2- 설파닐리덴 -2-[4-( 트리플루오로메틸 )피페리딘-1-일]에틸]피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-4-methyl-6-oxo-5-[2-sulfanylidene-2-[4-(trifluoromethyl)piperidin-1-yl]ethyl]pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.89-0.93 (t, 3H), 1.34-1.43 (m, 2H), 1.63-1.74 (m, 4H), 1.98-2.01 (m, 2H), 2.33 (s, 3H), 2.38-2.46 (m, 1H), 2.64-2.68 (t, 2H), 2.98-3.31 (m, 2H), 3.79-3.92 (m, 2H), 4.62-4.65 (m, 1H), 5.26 (s, 2H), 5.68-5.71 (m, 1H), 7.17-7.79 (m, 8H)
< 실시예 233> 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(8-azaspiro[4.5]decan-8-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.85 (t, 3H), 1.33-1.39 (m, 2H), 1.48-1.69 (m, 14H), 2.39 (s, 3H), 2.97 (t, 2H), 3.73-3.84 (m, 6H), 5.32 (s, 2H), 7.22 (d, 2H), 7.28 (d, 2H), 7.38 (d, 1H), 7.46 (t, 1H), 7.58 (t, 1H), 7.72 (d, 1H)
< 실시예 234> 3-[2-[4-[[5-[2-(8- 아자스파이로[4.5]데칸 -8-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아 졸-5-온 {3-[2-[4-[[5-[2-(8-azaspiro[4.5]decan-8-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.97 (t, 3H), 1.47-1.76 (m, 14H), 2.38 (s, 3H), 2.87-2.92 (m, 2H), 3.75-3.86 (m, 6H), 5.31 (s, 2H), 7.22 (d, 2H), 7.27 (d, 2H), 7.38 (d, 1H), 7.45 (t, 1H), 7.58 (t, 1H), 7.70 (d, 1H)
< 실시예 235> 3-[2-[4-[[2-부틸-5-[2-(4,4- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(4,4- dimethylpiperidin -1- yl )-2- sulfanylideneethyl ]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.81 (t, 3H), 1.03 (s, 6H), 1.32-1.36 (m, 2H), 1.46-1.50 (m, 4H), 1.64-1.68 (m, 2H), 2.42 (s, 3H), 3.07 (t, 2H), 3.74-3.84 (m, 6H), 5.32 (s, 2H), 7.21 (d, 2H), 7.26 (d, 2H), 7.36 (d, 1H), 7.44 (t, 1H), 7.57 (t, 1H), 7.68 (d, 1H)
< 실시예 236> 3-[2-[4-[[5-[2-(4,4- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6-옥소-2- 프로필피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[5-[2-(4,4-dimethylpiperidin-1-yl)-2-sulfanylideneethyl]-4-methyl-6-oxo-2-propylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 1.02 (s, 6H), 1.45-1.50 (m, 4H), 1.68-1.78 (m, 2H), 2.42 (s, 3H), 3.05 (t, 2H), 3.70-3.82 (m, 6H), 5.32 (s, 2H), 7.20-7.27 (m, 4H), 7.36 (d, 1H), 7.43 (t, 1H), 7.56 (t, 1H), 7.67 (d, 1H)
< 실시예 237> 2-[2-부틸-4- 메틸 -6-옥소-1-[[4-[2-(5- 설파닐리덴 -4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오아마이드 {2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(5-sulfanylidene-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.92-0.95 (t, 3H), 1.38-1.47 (m, 2H), 1.71-1.79 (m, 2H), 2.34 (s, 3H), 2.68-2.72 (t, 2H), 3.48 (s, 3H), 3.53 (s, 3H), 3.83 (s, 2H), 5.30 (s, 2H), 7.22-7.85 (m, 8H)
< 실시예 238> 5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-6- 메틸 -3-[[4-[2-(5- 설파닐리덴 -4H-1,2,4- 옥사다이아졸 -3-일)페닐]페닐]메틸]피리미딘-4-온 {5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-butyl-6-methyl-3-[[4-[2-(5-sulfanylidene-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-4-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.28-1.75 (m, 14H), 2.05 (m, 2H), 2.65 (t, 2H), 2.90 (s, 3H), 3.68-3.86 (d, 4H), 5.25 (s, 2H), 7.17-7.29 (m, 4H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 239> 2-부틸-6- 메틸 -5-[2-(4- 메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-3-[[4-[2-(5- 설파닐리덴 -4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-4-온 {2-butyl-6-methyl-5-[2-(4-methylpiperidin-1-yl)-2-sulfanylideneethyl]-3-[[4-[2-(5-sulfanylidene-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-4-one}의 제조
1H-NMR (400MHz): δ 0.93 (t, 3H), 1.28-1.73 (m, 12H), 2.05 (m, 2H), 2.65 (t, 2H), 2.90 (s, 3H), 3.70-3.86 (m, 4H), 5.28 (s, 2H), 7.17-7.30 (m, 4H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 240> 3-[2-[4-[[2-부틸-5-[2-(2,5- 다이메틸피롤리딘 -1-일)-2- 설파닐리덴에틸 ]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(2,5-dimethylpyrrolidin-1-yl)-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 10H), 1.71 (m, 6H), 2.38 (s, 3H), 2.45 (m, 5H), 2.63 (t, 2H), 3.81 (s, 2H), 5.26 (s, 2H), 7.19 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 241> 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6- 다이메틸피페리딘 -1-일]-2-설 파닐리덴에 틸]-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-[(2S,6R)-2,6-dimethylpiperidin-1-yl]-2-sulfanylideneethyl]-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39 (m, 10H), 1.71 (m, 6H), 1.90 (m, 3H), 2.38 (s, 3H), 2.45 (m, 5H), 2.63 (t, 2H), 3.81 (s, 2H), 5.26 (s, 2H), 7.19 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 242> 3-[2-[4-[[5-[2-[(4 aS ,7aR)-1,3,4,4a,5,6,7,7a- 옥타하이드로사이클로펜타[c]피리딘 -2-일]-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-[(4aS,7aR)-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyridin-2-yl]-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 14H), 2.28 (s, 3H), 2.36 (m, 1H), 2.40 (m, 3H), 2.63 (t, 2H), 3.58-3.87 (m, 4H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 243> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-[(2S)-2- 메틸피롤리딘 -1-일]-2-설파닐리덴에틸]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-[(2S)-2-methylpyrrolidin-1-yl]-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 5H), 2.28 (s, 3H), 2.36 (m, 4H), 2.40 (m, 5H), 2.63 (t, 2H), 3.58-3.87 (t, 2H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 244> 3-[2-[4-[[2-부틸-4- 메틸 -5-[2-[(2R)-2- 메틸피롤리딘 -1-일]-2-싸이옥소-에틸]-6-옥소-피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-methyl-5-[2-[(2R)-2-methylpyrrolidin-1-yl]-2-thioxo-ethyl]-6-oxo-pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 5H), 2.28 (s, 3H), 2.36 (m, 4H), 2.40 (m, 5H), 2.63 (t, 2H), 3.58-3.87 (t,2H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 245> 3-[2-[4-[[5-[2-(7- 아자바이사이클로[2.2.1]헵탄 -7-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 메틸 -6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(7-azabicyclo[2.2.1]heptan-7-yl)-2-sulfanylideneethyl]-2-butyl-4-methyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.34-1.44 (m, 2H), 1.50-1.75 (m, 6H), 1.95-1.99 (m, 4H), 2.42 (s, 3H), 2.70 (t, 2H), 3.74-3.86 (m, 4H), 5.29 (s, 2H), 7.20 (d, 2H), 7.27 (d, 2H), 7.39 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.80 (d, 1H)
< 실시예 246> 3-(4'-((2-부틸-4- 메틸 -5-(2-(2- 메틸 -7,8- 다이하이드로피리도[4,3-d]피리미딘 -6(5H)-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이 페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-methyl-5-(2-(2-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.86-0.91 (m, 3H), 1.30-1.41 (m, 2H), 1.66-1.67 (m, 2H), 2.44-2.64 (m, 5H), 3.01-3.04 (m, 1H), 4.20-4.59 (m, 3H), 5.30-5.34 (m, 3H), 6.92-7.79 (m, 8H)
< 실시예 247> 3-(4'-((2-부틸-4- 메틸 -6-옥소-5-(2- 싸이옥소 -2-(3-( 트리플루오로메틸 )-5,6- 다이하이드로 -[1,2,4] 트리아졸로 [4,3-a]피라진-7(8H)-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-methyl-6-oxo-5-(2-thioxo-2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)pyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 2H), 2.28 (s, 3H), 2.36 (m, 4H), 2.40 (m, 4H), 2.63 (t, 2H), 3.58-3.87 (t, 2H), 5.23 (s, 2H), 7.18 (d, 2H), 7.28 (m, 2H), 7.42 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.70 (d, 1H)
< 실시예 248> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오 아마이드 {2-[2- butyl -4- cyclopropyl -6- oxo -1-[[4-[2-(5- oxo -4H-1,2,4- oxadiazol -3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.95 (d, 2H), 0.96 (t, 3H), 1.18 (d, 2H), 1.20 (m, 2H), 1.69 (m, 2H), 2.01 (t, 1H), 2.63 (t, 2H), 3.43 (s, 3H), 3.51 (s, 3H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 249> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2-일에탄싸이오아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.94 (t, 3H), 0.96 (m, 2H), 1.10 (d, 6H), 1.25 (d, 2H), 1.31 (m, 2H), 1.64 (m, 2H), 1.94 (mm, 1H), 2.01 (m, 1H), 2.62 (t, 2H), 3.17 (s, 1.5H), 3.30 (s, 1.5H), 3.98 (s, 1H), 4.10 (s, 1H), 4.30 (m, 1H), 4.76 (m, 0.5H), 5.19 (d, 2H), 5.90 (m, 0.5H), 7.13 (d, 2H), 7.25 (m, 2H), 7.46 (d, 1H), 7.58 (t, 1H), 7.62 (t, 1H), 7.75 (d, 1H)
< 실시예 250> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4- 사이클로프로필 -6- 옥소피리미딘 -1-일] 메틸 ]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-butyl-4-cyclopropyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.39-1.74 (m, 16H), 2.28 (s, 3H), 2.36 (m, 1H), 2.38 (m, 1H), 2.63 (t, 2H), 3.58 (m, 2H), 3.65 (s, 2H), 3.87 (m, 2H), 5.25 (s, 2H), 7.19 (d, 2H), 7.31 (m, 2H), 7.43 (d, 1H), 7.49 (t, 1H), 7.61 (t, 1H), 7.72 (d, 1H)
< 실시예 251> 2-[2-부틸-4- 사이클로프로필 -6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥 사다 이아졸-3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 l-N-(2- 메틸프로 필)에탄싸이오아마이드 {2-[2-butyl-4-cyclopropyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-(2-methylpropyl)ethanethioamide}의 제조
1H-NMR (400MHz): δ 0.88 (d, 2H), 0.94 (t, 3H), 1.06 (d, 3H), 1.19 (dd, 5H), 1.37 (m, 2H), 1.70 (m, 2H), 1.94 (mm, 1H), 2.61 (t, 2H), 2.72-2.91 (d, 3H), 3.68-3.76 (d, 2H), 4.30 (m, 0.5H), 4.84 (m, 0.5H), 5.19 (d, 2H), 7.12 (d, 2H), 7.25 (m, 2H), 7.44 (d, 1H), 7.55 (t, 1H), 7.61 (t, 1H), 7.73 (d, 1H)
< 실시예 252> 3-[2-[4-[[2-부틸-4- 사이클로프로필 -6-옥소-5-(2-피페리딘-1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온; 3-[2-[4-[[2-butyl-4-cyclopropyl-6-oxo-5-(2-piperidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.99-1.02 (m, 5H), 1.22-1.31 (m, 4H), 1.63-1.85 (m, 8H), 2.10 (t, 1H), 2.68 (t, 2H), 3.84 (t, 2H), 4.05 (s, 2H), 4.29 (t, 2H), 5.25 (s, 2H), 7.16 (t, 4H), 7.44 (d, 1H), 7.54-7.61 (m, 2H), 8.10 (d, 1H)
< 실시예 253> 3-(4'-((2-부틸-4- 사이클로프로필 -6-옥소-5-(2-( 피롤리딘 -1-일)-2- 싸이옥소에틸 )피리미딘-1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-6-oxo-5-(2-(pyrrolidin-1-yl)-2-thioxoethyl)pyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (s, 2H), 1.18 (t, 1H), 1.20 (dd, 2H), 1.67 (dd, 2H), 1.86 (m, 4H), 2.01 (m, 6H), 2.63 (t, 2H), 3.45 (d, 2H), 3.62 (t, 2H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 254> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2,6- 다이메틸피페라진 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2,6-dimethylpiperazin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (m, 4H), 1.18 (t, 1H), 1.20 (m, 4H), 1.67 (dd, 2H), 1.86 (m, 8H), 2.01 (m, 4H), 3.45 (d, 2H), 3.62 (t, 2H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 255> (S)-3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2- 메틸피롤리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {(S)-3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2-methylpyrrolidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 5H), 0.96 (m, 4H), 1.18 (m, 3H), 1.20 (m, 1H), 1.67 (dd, 2H), 1.86 (m, 8H), 2.62 (m, 2H), 3.45 (d, 2H), 3.62 (t, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 256> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(3,5- 다이메틸피페리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(3,5-dimethylpiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (m, 4H), 1.18 (t, 1H), 1.20 (m, 6H), 1.67 (dd, 2H), 1.86 (m, 8H), 2.01 (m, 4H), 3.45 (d, 2H), 3.62 (t, 2H), 3.98 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 257> 2-(2-부틸-4- 사이클로프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N-사이클로프로필에탄싸이오아마이드 {2-(2-butyl-4-cyclopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N-cyclopropylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 0.96 (m, 2H), 1.17 (s, 2H), 1.20 (m, 2H), 1.37 (dd, 2H), 2.01 (m, 5H), 2.66 (m, 4H), 3.62 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 258> 2-(2-부틸-4- 사이클로프로필 -6-옥소-1-((2'-(5-옥소-4,5- 다이하이드로 -1,2,4- 옥사다이아졸 -3-일) 바이페닐 -4-일) 메틸 )-1,6- 다이하이드로피리미딘 -5-일)-N,N-다이에틸에탄싸이오아마이드 {2-(2-butyl-4-cyclopropyl-6-oxo-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N,N-diethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.95 (m, 5H), 1.22 (m, 7H), 1.36 (m, 2H), 1.67 (dd, 2H), 2.01 (m, 1H), 2.66 (dd, 2H), 3.37 (dd, 2H), 3.40 (dd, 2H), 3.62 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 259> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(3,5- 다이메틸몰폴리노 )-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(3,5-dimethylmorpholino)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92-0.94 (m, 5H), 1.20-1.22 (m, 8H), 1.39 (dd, 2H), 1.71 (t, 2H), 2.68 (dd, 2H), 2.95 (t, 1H), 3.60-3.70 (m, 2H), 4.05-4.09 (dd, 2H), 4.47 (d, 1H), 5.25 (t, 2H), 5.60 (d, 1H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 260> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-((2S,6R)-2,6- 다이메틸피페리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-((2S,6R)-2,6-dimethylpiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 3H), 1.22 (m, 4H), 1.36 (m, 2H), 1.67 (dd, 3H), 2.01 (m, 3H), 2.66 (dd, 2H), 3.37 (dd, 2H), 3.40 (dd, 2H), 3.56-3.73 (m, 4H), 4.45 (m, 1H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 261> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2- 몰폴리노 -2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아졸 -5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-morpholino-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92-0.95 (m, 5H), 1.22 (m, 2H), 1.36 (m, 2H), 1.67 (dd, 2H), 2.19 (m, 1H), 2.68 (t, 2H), 3.70 (d, 2H), 3.79 (d, 2H), 4.00 (s, 2H), 4.09 (s, 2H), 4.45 (s, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 262> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(2- 메틸피페리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(2-methylpiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.95 (t, 4H), 1.15-1.17 (m, 4H), 1.35-1.37 (m, 4H), 1.64- 1.68 (m, 8H), 2.01 (m, 3H), 2.64 (dd, 2H), 3.16 (t, 1H), 3.80 (dd, 2H), 4.30-4.70 (m, 2H), 5.18 (s, 2H), 7.15 (d, 2H), 7.26 (d, 2H), 7.41 (d, 1H), 7.48 (t, 1H), 7.61 (t, 1H), 7.75 (d, 1H)
< 실시예 263> 3-(4'-((2-부틸-4- 사이클로프로필 -5-(2-(4- 하이드록시피페리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-cyclopropyl-5-(2-(4-hydroxypiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.21 (m, 6H), 1.36 (m, 2H), 1.74 (m, 2H), 1.82 (m, 2H), 2,24 (m, 2H), 2.80 (m, 2H), 3.01 (m, 1H), 3.91 (m, 4H), 4.14 (m, 1H), 5.01 (m, 1H), 5.18 (dd, 2H), 5.18 (m, 2H), 7.15 (m, 2H), 7.28 (m, 2H), 7.42 (m, 1H), 7.50 (d, 1H), 7.62 (m, 1H)
< 실시예 264> 3-[2-[4-[[2-부틸-6-옥소-4-프로판-2-일-5-(2- 피롤리딘 -1-일-2-설 파닐리덴에 틸)피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-6-oxo-4-propan-2-yl-5-(2-pyrrolidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz, CDCl3): δ 0.9 (m, 3H), 1.0 (m, 8H), 1.4 (m, 2H), 1.6 (m, 2H), 1.8 (m, 2H), 2.7 (m, 2H), 4.0 (m, 4H), 5.3 (d, 2H), 7.0-7.2 (m, 4H), 7.4-7.6 (m, 4H)
< 실시예 265> 3-[2-[4-[[2-부틸-6-옥소-5-(2-피페리딘-1-일-2- 설파닐리덴에틸 )-4-프로판-2- 일피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-6-oxo-5-(2-piperidin-1-yl-2-sulfanylideneethyl)-4-propan-2-ylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.72 (m, 4H), 3.84 (s, 2H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 266> 3-[2-[4-[[2-부틸-5-[2-(2,6- 다이메틸피페라진 -1-일)-2- 설파닐리덴에틸 ]-6-옥소-4-프로판-2- 일피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이 아졸-5-온 {3-[2-[4-[[2-butyl-5-[2-(2,6-dimethylpiperazin-1-yl)-2-sulfanylideneethyl]-6-oxo-4-propan-2-ylpyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 10H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.72 (m, 4H), 3.84 (s, 2H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 267> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N,N- 다이메틸에탄싸이오아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 5H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 2.80 (m, 6H), 3.84 (s, 2H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 268> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N,N- 다이에틸에탄싸이오아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N,N-diethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 2H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 2H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 2.80 (m, 6H), 3.84 (m, 4H), 3.95 (t, 4H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 269> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N- 메틸 -N-프로판-2- 일에탄싸이오 아마이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N-methyl-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 6H), 1.20-1.40 (m, 12H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.84 (s, 3H), 3.95 (t, 2H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 270> 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]-4-프로판-2- 일피리미딘 -5-일]-N- 사이클로프로필에탄싸이오아마 이드 {2-[2-butyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]-4-propan-2-ylpyrimidin-5-yl]-N-cyclopropylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 0.92-0.98 (m, 3H), 1.20-1.40 (m, 6H), 1.70 (m, 2H), 2.34 (s, 3H), 2.66 (t, 3H), 3.84 (s, 3H), 3.95 (m, 4H), 4.34 (t, 2H), 5.26 (s, 2H), 7.16 (d, 2H), 7.27 (d, 2H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 271> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(2- 메틸 -7,8- 다이하이드로피리도[4,3-d]피리미딘 -6(5H)-일)-2- 싸이옥소에틸 )-6-옥소-5,6- 다이하이드로피리 미딘-1(4H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-(2-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-2-thioxoethyl)-6-oxo-5,6-dihydropyrimidin-1(4H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.87-0.96 (m, 3H), 1.19-1.44 (m, 8H), 1.71-1.81 (m, 3H), 1.94-2.05 (d, 3H), 2.43-3.01 (m, 4H), 4.28-4.62 (m, 3H), 5.26-5.37 (m, 3H), 6.88-7.80 (m, 8H)
< 실시예 272> 3-(4'-((2-부틸-5-(2-(3,5- 다이메틸피페리딘 -1-일l)-2- 싸이옥소에틸 )-4- 아이소프로필 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-(3,5-dimethylpiperidin-1-yl)-2-thioxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.86 (t, 3H), 0.88 (m, 2H), 0.91 (m, 6H), 1.36 (m, 4H), 1.67 (m, 4H), 1.73 (m, 1H), 2.66 (m, 2H), 3.01 (m, 1H), 3.50 (m, 2H), 4.27 (m, 1H), 4.57 (m, 1H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 273> 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6- 다이메틸피페리딘 -1-일)-2-싸이옥소에틸)-4- 아이소프로필 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-((2R,6S)-2,6-dimethylpiperidin-1-yl)-2-thioxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.92 (m, 2H), 1.17 (m, 6H), 1.29 (dd, 6H), 1.68 (m, 2H), 1.70 (m, 6H), 1.93 (t, 1H), 2.45 (m, 2H), 2.95 (m, 1H), 3.60 (m, 3H), 3.95 (d, 0.5H), 4.42 (d, 0.5H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 274> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(2- 메틸피페리딘 -1-일)-2-싸 이옥소에 틸)-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아 졸-5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-(2-methylpiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.93 (m, 7H), 1.25 (m, 8H), 1.41 (m, 2H), 1.80 (m, 4H), 2.69 (m, 4H), 3.06 (m, 3H), 3.88 (s, 2H), 4.28 (dd, 1H), 5.28 (s, 2H), 5.42 (dd, 1H), 7.17 (m, 2H), 7.31 (m, 2H), 7.42 (d, 1H), 7.48 (d, 1H), 7.60 (d, 1H), 7.79 (d, 1H)
< 실시예 275> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(3- 메틸피페리딘 -1-일)-2-싸 이옥소에 틸)-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이아 졸-5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-(3-methylpiperidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.21 (m, 8H), 1.33 (m, 3H), 1.66 (m, 2H), 1.78 (m, 5H), 2.69 (m, 2H), 3.08 (m, 2H), 3.27 (t, 1H), 3.88 (m, 2H), 4.28 (d, 0.5H) 4.87 (m, 0.5H), 5.24 (s, 2H), 5.62(d, 0.5H), 6.01 (t, 0.5H), 7.17 (m, 2H), 7.31 (m, 2H), 7.42 (d, 1H), 7.60 (d, 1H), 7.76 (d, 1H), 7.83 (d, 1H)
< 실시예 276> 3-(4'-((2-부틸-4- 아이소프로필 -5-(2- 몰폴리노 -2- 싸이옥소에틸 )-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온 {3-(4'-((2-butyl-4-isopropyl-5-(2-morpholino-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.91 (m, 6H), 1.36 (m, 2H), 1.74 (m, 2H), 2.66 (m, 2H), 3.01 (m, 1H), 3.50 (m, 2H), 3.59 (m, 8H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 277> 3-(4'-((2-부틸-5-(2-(2,6- 다이메틸몰폴리노 )-2- 싸이옥소에틸 )-4- 아이소프로필 -6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4- 옥사다이 아졸-5(4H)-온 {3-(4'-((2-butyl-5-(2-(2,6-dimethylmorpholino)-2-thioxoethyl)-4-isopropyl-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.90 (t, 3H), 0.91 (m, 12H), 1.36 (m, 2H), 1.74 (m, 2H), 2.28 (m, 1H), 2.66 (m, 2H), 2.80 (m, 1H), 3.01 (m, 1H), 3.50 (m, 2H), 3.59 (m, 6H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 278> (S)-3-(4'-((2-부틸-4- 아이소프로필 -5-(2-(2- 메틸피롤리딘 -1-일)-2- 싸이옥소에틸 )-6- 옥소피리미딘 -1(6H)-일) 메틸 ) 바이페닐 -2-일)-1,2,4-옥사다이아졸-5(4H)-온 {(S)-3-(4'-((2-butyl-4-isopropyl-5-(2-(2-methylpyrrolidin-1-yl)-2-thioxoethyl)-6-oxopyrimidin-1(6H)-yl)methyl)biphenyl-2-yl)-1,2,4-oxadiazol-5(4H)-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.11 (d, 2H), 1.19 (m, 6H), 1.21 (d, 1H), 1.37 (m, 2H), 1.74 (m, 2H), 1.92 (m, 3H), 2.66 (m, 2H), 3.01 (m, 1H), 3.41 (m, 1H), 3.65 (m, 3H), 5.18 (m, 2H), 7.09 (m, 2H), 7.11 (m, 2H), 7.25 (m, 1H), 7.33 (d, 1H), 7.48 (m, 1H), 7.62 (m, 1H), 7.83 (d, 1H)
< 실시예 279> 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N,N- 다이메틸에탄싸이오아마이드 {2-[2-butyl-4-ethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (t, 3H), 1.40 (m, 2H), 1.85 (m, 2H), 2.64 (t, 2H), 2.86 (t, 2H), 3.50 (d, 6H), 3.85 (s, 2H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 280> 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4- 옥사다이아졸 -3-일) 페닐 ] 페닐 ] 메틸 ]피리미딘-5-일]-N- 메틸 -N-프로판-2- 일에탄싸이오아마이 드 {2-[2-butyl-4-ethyl-6-oxo-1-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N-methyl-N-propan-2-ylethanethioamide}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 9H), 1.40 (m, 2H), 1.85 (m, 3H), 2.64 (t, 2H), 2.86 (t, 2H), 3.50 (d, 3H) 3.85 (s, 2H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 281> 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a- 옥타하이드로아이소인돌 -2-일)-2- 설파닐리덴에틸 ]-2-부틸-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4-옥사다이아졸-5-온 {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-2-sulfanylideneethyl]-2-butyl-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.86 (t, 2H), 2.90 (m, 2H), 3.84 (s, 2H), 3.95 (m, 2H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 282> 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2- 피롤리딘 -1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-6-oxo-5-(2-pyrrolidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 3H), 1.40 (m, 2H), 1.70 (m, 3H), 1.96 (m, 2H), 2.10 (t, 2H), 2.36 (t, 2H), 2.60-2.90 (m, 4H), 3.84 (s, 2H), 3.95 (m, 3H), 5.26 (s, 2H), 7.27 (m, 5H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 283> 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-피페리딘-1-일-2- 설파닐리덴에틸 )피리미딘-1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-6-oxo-5-(2-piperidin-1-yl-2-sulfanylideneethyl)pyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 3H), 1.40 (m, 2H), 1.70-1.85 (m, 8H), 2.60-2.90 (m, 3H), 3.95 (m, 4H), 4.30 (m, 2H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 284> 3-[2-[4-[[2-부틸-4-에틸-5-(2- 몰폴린 -4-일-2- 설파닐리덴에틸 )-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-5-(2-morpholin-4-yl-2-sulfanylideneethyl)-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (t, 3H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 4H), 3.84 (s, 2H), 3.95 (m, 4H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 285> 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4- 메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-4-ethyl-5-[2-(4-methylpiperidin-1-yl)-2-sulfanylideneethyl]-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.92 (t, 3H), 1.41 (m, 8H), 1.71 (m, 8H), 2.31 (s, 3H), 2.68 (t, 2H), 3.52 (m, 4H), 4.28 (s, 2H), 5.27 (s, 2H), 7.20 (d, 2H), 7.25 (d, 2H), 7.42 (m, 1H), 7.48 (t, 1H), 7.61 (d, 1H), 7.77 (d, 1H)
< 실시예 286> 3-[2-[4-[[2-부틸-5-[2-(3,3- 다이메틸피페리딘 -1-일)-2- 설파닐리덴에틸 ]-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2- butyl -5-[2-(3,3- dimethylpiperidin -1- yl )-2- sulfanylideneethyl ]-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.43 (m, 9H), 1.52 (m, 5H), 1.85 (m, 3H), 2.64 (t, 2H), 2.86 (t, 2H), 3.20 (d, 2H), 3.50 (d, 2H), 3.85 (s, 2H), 5.26 (s, 2H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
< 실시예 287> 3-[2-[4-[[2-부틸-5-[2-(3,5- 다이메틸몰폴린 -4-일)-2- 설파닐리덴에틸 ]-4-에틸-6- 옥소피리미딘 -1-일] 메틸 ] 페닐 ] 페닐 ]-4H-1,2,4- 옥사다이아졸 -5-온 {3-[2-[4-[[2-butyl-5-[2-(3,5-dimethylmorpholin-4-yl)-2-sulfanylideneethyl]-4-ethyl-6-oxopyrimidin-1-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one}의 제조
1H-NMR (400MHz): δ 0.91 (t, 3H), 1.20 (m, 9H), 1.40 (m, 2H), 1.70 (m, 2H), 2.64 (dd, 2H), 2.86 (t, 2H), 2.90 (m, 3H), 3.84 (s, 2H), 3.95 (m, 3H), 5.26 (s, 2H), 7.16 (d, 1H), 7.27 (m, 4H), 7.42 (m, 1H), 7.49 (t, 1H), 7.62 (d, 1H), 7.76 (d, 1H)
실시예 1 내지 287에서 제조한 본 발명의 화합물들의 구조는 다음 표 1에 정리된 바와 같다.
[표 1]
Figure 112017080786708-pat00014
Figure 112017080786708-pat00015
Figure 112017080786708-pat00016
Figure 112017080786708-pat00017
Figure 112017080786708-pat00018
Figure 112017080786708-pat00019
Figure 112017080786708-pat00020
Figure 112017080786708-pat00021
Figure 112017080786708-pat00022
Figure 112017080786708-pat00023
Figure 112017080786708-pat00024
Figure 112017080786708-pat00025
Figure 112017080786708-pat00026
Figure 112017080786708-pat00027
Figure 112017080786708-pat00028
Figure 112017080786708-pat00029
Figure 112017080786708-pat00030
Figure 112017080786708-pat00031
Figure 112017080786708-pat00032
Figure 112017080786708-pat00033
Figure 112017080786708-pat00034
Figure 112019004510925-pat00058
Figure 112017080786708-pat00036
Figure 112017080786708-pat00037
Figure 112017080786708-pat00038
Figure 112019004510925-pat00059
Figure 112019004510925-pat00060
Figure 112019004510925-pat00061
Figure 112019004510925-pat00062
Figure 112019004510925-pat00063
Figure 112019004510925-pat00064
Figure 112017080786708-pat00045
< 실험예 1> 칼슘 동원 실험 (Calcium mobilization 분석)
1. 실험 방법
- 사용세포: PathHunter® CHO-K1 AGTR1 β-Arrestin Cell Line (DiscoverX, 93-0312C2)
- 사용배지: Assay Complete Cell Plating 2 Reagent
- 사용 kit: Calcium NoWash plus (Ca NW plus) Assay kit (DiscoverX, 90-0091)
[Day-1]
96 well plate에 세포를 2 X 104 / well로 seeding 하고, CO2 5 %, 37 ℃ incubator에서 1 일 동안 배양하였다.
[Day-2]
1) 상기 plate의 배지를 제거하고, 9 mL의 Dye loading buffer (20 mM HEPES in HBSS, pH 7.4), 1 mL의 시험 kit에서 제공하는 Additive A, 10 μL의 CaNW dye 및 100 μL의 Probenicid solution을 잘 섞어 100 μL/well로 넣은 뒤, 5 % CO2, 37 ℃에서 1 시간 동안 incubation 하였다.
2) 각 실시예의 화합물 용액(농도: 20 nM, 200 nM) 25 μL 를 더 넣어준 후, 상온에서 30분 동안 정치시켰다.
3) Flexstation3 (Molecular Devices) 로 옮긴 후, 다음과 같은 조건으로 측정하여 Ca mobilization 저해력을 구하였다.
- Excitation at 494 nm, emission at 516 nm
- 2 minutes at 2 second intervals
- Agonist (angiotensin) 처리농도 : 0.1nM
- Agonist (angiotensin) 처리량 : 25 μL
2. 실험 결과
[표 2]
Figure 112017080786708-pat00046
Figure 112017080786708-pat00047
Figure 112017080786708-pat00048
Figure 112017080786708-pat00049
< 실험예 2> PPAR γ Transactivation Assay Protocol
1. 실험 방법
- 사용 세포: Cos-7 (Fibroblast-like cell line derived from monkey kidney tissue)
- 사용 배지: Cos-7 cell_DMEM 10% FBS (DMEM : Invitrogen, #11995-065 or 073)
각 실시예의 화합물을 DMSO에 녹여 1mM 농도의 용액을 제조한 후, 10 % FBS 배지로 희석하여 10 μM 농도의 용액으로 실험하였다.
[Day-1]
48 well plate에 세포를 3 X 104 cells / 250 μL / well 로 seeding 하고, 37 ℃, 5 % CO2 에서 24 시간 동안 incubation 하였다.
[Day-2]
1) 상기 plate의 각 well을 PBS 0.5 mL로 2회 세척한 후, serum free media (DMEM) 250 μL씩 넣고 37 ℃, 5 % CO2 incubator에 넣어두었다.
2) 다음의 Mix 1과 Mix 2를 각각 제조한 뒤, Mix 1과 Mix 2를 잘 섞고 5분간 실온에 두었다.
- Mix 1
Figure 112017080786708-pat00050
- Mix 2
Figure 112017080786708-pat00051
- Lipofectamine 3000 (Invitrogen, #L3000008)
- Opti-MEM media (Invitrogen, #L31985-070)
3) incubator에 넣어둔 plate에 잘 섞인 Mix 1과 Mix 2 를 well당 25 μL씩 넣고, 37 ℃, 5 % CO2 incubator에서 6 시간 동안 배양하였다.
4) 상기 plate의 배양액을 제거한 후 각 well당 각 실시예의 화합물 용액을 250 μL씩 넣고, 37 ℃, 5 % CO2 incubator에서 20 시간 동안 배양하였다.
[Day-3]
1) 48 well plate를 PBS로 1회 세척한 후 각 well에 65 μL씩 passive Lysis Buffer(PLB)를 넣고, 15 분 동안 80 rpm으로 shaking 한 뒤, e-tube로 옮겨 4 ℃, 13000 rpm에서 1 분 동안 원심분리하였다.
2) 상층액 20 μL를 white well plate로 옮기고, Luciferase buffer 100 μL를 각 well에 넣고 Luminometer 기기로 Firefly activity를 측정하였다.
3) Renilla로 보정하여 Firefly activity를 산정한 후, DMSO를 기준으로 PPARγ 활성도를 측정하였다.
2. 실험 결과
[표 3]
Figure 112017080786708-pat00052
Figure 112017080786708-pat00053
Figure 112017080786708-pat00054
Figure 112017080786708-pat00055

Claims (8)

  1. 하기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염:
    [화학식 I]
    Figure 112019004510925-pat00056

    상기 화학식 I 에서,
    Ra1 및 Ra2 는 각각 독립적으로 C1-C6 알킬 또는 C3-C7 시클로알킬이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
    Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H, 할로, C1-C4 알킬 또는 C1-C4 할로알킬이고,
    Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
    X1 및 X2 는 각각 독립적으로 O 또는 S이고,
    Y 는 C1-C4 알킬이고 {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
    Z 는 OR1 또는 NR2R3 이고,
    R1 은 H, C1-C6 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 카르복실산 또는 설포닐로 치환될 수 있음},
    R2 및 R3 는 각각 독립적으로 H, C1-C6 알킬, C3-C7 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C6 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시, 아릴 또는 헤테로아릴로 치환될 수 있음}, 또는
    R2 및 R3 는 연결된 질소 원자와 함께 5원-7원의 단일 고리 또는 7원-12원의 이중 고리를 형성한다 {여기서, 상기 단일 고리 또는 이중 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 할로알킬, C1-C4 알콕시, 히드록시, 카르복실산, 니트로, 설폰닐, C3-C7 시클로알킬, C2-C6 헤테로시클로알킬, 아릴, 니트로 치환된 페닐 또는 헤테로아릴로 치환될 수 있음}.
  2. 제 1 항에 있어서,
    Ra1 및 Ra2 는 각각 독립적으로 C1-C6 알킬 또는 C3-C7 시클로알킬이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
    Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H 또는 할로이고,
    Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
    X1 및 X2 는 각각 독립적으로 O 또는 S이고,
    Y 는 C1-C4 알킬이고 {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
    Z 는 OR1 또는 NR2R3 이고,
    R1 은 H, C1-C4 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 카르복실산 또는 설포닐로 치환될 수 있음},
    R2 및 R3 는 각각 독립적으로 H, C1-C4 알킬, C3-C6 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시 또는 헤테로아릴로 치환될 수 있음}, 또는
    R2 및 R3 는 연결된 질소 원자와 함께 5원-7원의 단일 고리, 6원-8원의 브릿지 이중 고리, 8원-10원의 융합 이중 고리 또는 9원-11원의 스파이로 이중 고리를 형성하는 것인 {여기서, 상기 단일 고리, 브릿지 이중 고리, 융합 이중 고리 또는 스파이로 이중 고리의 하나 이상의 H는 할로, C1-C4 알킬 또는 C1-C4 할로알킬, 아릴, 니트로 치환된 페닐 또는 헤테로아릴로 치환될 수 있음},
    화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염.
  3. 하기 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염:
    [화학식 I]
    Figure 112019026203489-pat00065

    상기 화학식 I 에서,
    Ra1 및 Ra2 는 각각 독립적으로 C1-C6 알킬 또는 C3-C7 시클로알킬이고 {여기서, 상기 C1-C6 알킬 또는 C3-C7 시클로알킬의 하나 이상의 H는 할로로 치환될 수 있음},
    Rb1, Rb2, Rc1 및 Rc2 는 각각 독립적으로 H 또는 할로이고,
    Rd1 및 Rd2 는 각각 독립적으로 H 또는 C1-C4 알킬이고,
    X1 및 X2 는 각각 독립적으로 O 또는 S이고,
    Y 는 C1-C4 알킬이고 {여기서, 상기 C1-C4 알킬의 하나 이상의 H는 할로, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}
    Z 는 OR1 또는 NR2R3 이고,
    R1 은 H, C1-C4 알킬, C1-C4 알킬-O(C1-C4 알킬), C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐이고 {여기서, 상기 C3-C7 시클로알킬, 페닐 또는 C1-C4 알킬-페닐 고리의 하나 이상의 H는 할로, C1-C4 알킬, C1-C4 알콕시 또는 히드록시로 치환될 수 있음},
    R2 및 R3 는 각각 독립적으로 H, C1-C6 알킬, C3-C7 시클로알킬 또는 C1-C6 알콕시이고 {여기서, 상기 C1-C6 알킬의 하나 이상의 H는 C1-C4 알콕시, 히드록시 또는 헤테로아릴로 치환될 수 있음}, 또는
    R2 및 R3 는 연결된 질소 원자와 함께 하기 고리 중 어느 하나를 형성하는 것이고 {여기서, 상기 고리의 하나 이상의 H는 할로, C1-C4 알킬 또는 C1-C4 할로알킬로 치환될 수 있음},
    Figure 112019026203489-pat00057

    R4 는 H, C1-C4 알킬, 아릴 또는 헤테로아릴임 {여기서, 상기 아릴 또는 헤테로아릴은 할로, C1-C4 알킬, C1-C4 알콕시, 히드록시, 니트로, 시아노 또는 설포닐로 치환될 수 있음}.
  4. 제 1 항에 있어서, 하기 화합물들로 이루어진 군으로부터 선택된 어느 하나인 화학식 I 로 표시되는 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염:
    1) 에틸 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    2) 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세트산;
    3) 메틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    4) 프로필 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    5) 부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    6) 펜틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    7) 아이소프로필 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    8) 아이소부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    9) 2-메틸부틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    10) 벤질 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    11) 2-메톡시페네틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    12) 사이클로헥실 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    13) (1r,4r)-4-메틸사이클로헥실 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    14) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세트산;
    15) 2-메틸부틸 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    16) 펜탄-3-일 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    17) 아이소프로필 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    18) 1-메톡시프로판2-일 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    19) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    20) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)프로파노에이트;
    21) 에틸 2-(2-부틸-4-메틸-1-((2'-(4-메틸-5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-6-옥소-1,6-다이하이드로피리미딘-5-일)아세테이트;
    22) 에틸 2-(2-(1-브로모부틸)-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트 트리플루오로아세트산염;
    23) 에틸 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-2-하이드록시아세테이트 트리플루오로아세트산염;
    24) 3-[2-[4-[[5-[2-[(1R)-2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일]-2-옥소-에틸]-2-부틸-4-사이클로프로필-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    25) 에틸 2-(4-터트-부틸-2-부틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    26) 페닐 2-(2-부틸-4-아이소프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)아세테이트;
    27) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    28) {2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
    29) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필아세트아마이드;
    30) N-부틸-2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]아세트아마이드;
    31) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이에틸아세트아마이드;
    32) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일아세트아마이드;
    33) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-아이소프로필-N-메틸아세트아마이드;
    34) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)아세트아마이드;
    35) {3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    36) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    37) 3-[2-[4-[[2-부틸-4-메틸-5-(2-몰폴린-4-일에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    38) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    39) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(1-하이드록시프로판-2-일)아세트아마이드;
    40) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    41) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드;
    52) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    53) N-메톡시-N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]아세트아마이드;
    54) N,N-다이메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]아세트아마이드;
    55) 3-[2-[4-[[4-메틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    56) 3-[2-[4-[[4-메틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    57) 3-[2-[4-[[5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    58) 3-[2-[4-[[5-[2-(3,5-다이메틸몰폴린-4-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    59) N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]-N-프로판-2-일아세트아마이드;
    60) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸프로판아마이드;
    61) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일프로판아마이드;
    62) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-사이클로프로필프로판아마이드;
    63) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(3-옥소-3-피페리딘-1-일프로필)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    64) 3-[2-[4-[[2-부틸-4-메틸-5-(3-몰폴린-4-일-3-옥소프로필)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    65) 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일l)-3-옥소프로필]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    66) 3-[2-[4-[[2-부틸-4-메틸-5-[3-(4-메틸피페리딘-1-일)-3-옥소프로필]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    67) 3-[2-[4-[[2-부틸-5-[3-(3,3-다이메틸피페리딘-1-일)-3-옥소프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    68) 3-[2-[4-[[2-부틸-5-[3-(3,5-다이메틸몰폴린-4-일)-3-옥소프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    69) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부탄-2-일-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    70) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드;
    71) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    72) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
    73) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    74) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸몰폴린-4-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    75) 3-[2-[4-[[2-부틸-5-[2-(3,4-다이하이드로-1H-아이소퀴놀린-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    76) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-1H-아이소퀴놀린-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    77) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸피롤리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
    78) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-2H-퀴놀린-1-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
    79) 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2-옥소에틸)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
    80) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸-1,3,3a,4,6,6a-헥사하이드로피롤로[3,4-c]피롤-5-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    81) 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-헥사하이드로-1H-사이클로펜타[c]피롤-2-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    82) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    83) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-옥소-2-(4-프로판-2-일피페리딘-1-일)에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    84) 3-[2-[4-[[2-부틸-5-[2-(2,3-다이하이드로인돌-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    85) 3-[2-[4-[[2-부틸-5-[2-(4-플루오로-1,3-다이하이드로아이소인돌-2-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    86) 2-[2-사이클로프로필-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    87) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-사이클로프로필-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    88) 3-(4'-((2-부틸-4-메틸-5-(2-(옥타하이드로-1H-인돌-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    89) 3-(4'-((2-부틸-5-(2-(다이하이드로-1H-피리도[1,2-a]피라진-2(6H,7H,8H,9H,9aH)-일)-2-옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    90) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    91) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    92) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-옥소-2-[4-(트리풀루오로메틸)피페리딘-1-일]에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    93) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    94) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    95) 3-[2-[4-[[2-부틸-5-[2-(4,4-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    96) 3-[2-[4-[[5-[2-(4,4-다이메틸피페리딘-1-일)-2-옥소에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    97) 3-[2-[4-[[2-부틸-5-[2-(2,5-다이메틸피롤리딘-1-일)-2-옥소-에틸]-4-메틸-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
    98) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2S)-2-메틸피롤리딘-1-일]-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    99) 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6-다이메틸피페리딘-1-일]-2-옥소에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    100) 3-[2-[4-[[5-[2-[(4aS,8aR)-3,4,4a,5,6,7,8,8a-옥타하이드로-2H-퀴놀린-1-일]-2-옥소에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    101) 3-(4'-((2-부틸-4-메틸-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    102) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    103) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-사이클로프로필-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    104) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
    105) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)아세트아마이드;
    106) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-아이소프로필-N-메틸아세트아마이드;
    107) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    108) 3-[2-[4-[[2-부틸-4-사이클로프로필-5-[2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    109) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    110) 3-[2-[4-[[2-부틸-4-사이클로프로필-5-(2-몰폴린-4-일-2-옥소에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    111) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(1-하이드록시프로판-2-일)아세트아마이드;
    112) N-부틸-2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]아세트아마이드;
    113) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필아세트아마이드;
    114) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일아세트아마이드;
    115) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸아세트아마이드
    116) 3-(4'-((2-부틸-4-사이클로프로필-6-옥소-5-(2-옥소-2-(피롤리딘-1-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    117) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2,6-다이메틸피페라진-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    118) (S)-3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피롤리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    119) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    120) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-사이클로프로필아세트아마이드;
    121) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이에틸아세트아마이드;
    122) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸몰폴리노)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    123) 3-(4'-((2-부틸-4-사이클로프로필l-5-(2-((2S,6R)-2,6-다이메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    124) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-몰폴리노-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    125) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    126) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(4-하이드록시피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    127) 3-[2-[4-[[2-부틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    128) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸피페라진-1-일)-2-옥소에틸]-6-옥소-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    129) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    130) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이에틸아세트아마이드;
    131) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
    132) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-사이클로프로필아세트아마이드;
    133) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    134) 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6-다이메틸피페리딘-1-일)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    135) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    136) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(3-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    137) 3-(4'-((2-부틸-4-아이소프로필-5-(2-몰폴리노-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    138) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    139) (S)-3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피롤리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    140) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸아세트아마이드;
    141) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일아세트아마이드;
    142) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-옥소에틸]-2-부틸-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    143) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2-피롤리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    144) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-옥소-2-피페리딘-1-일에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    145) 3-[2-[4-[[2-부틸-4-에틸-5-(2-몰폴린-4-일-2-옥소에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    146) 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4-메틸피페리딘-1-일)-2-옥소에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    147) 3-[2-[4-[[2-부틸-5-[2-(3,3-다이메틸피페리딘-1-일)-2-옥소에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    148) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-옥소에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    149) 3-(4'-((2-부틸-4-메틸-6-옥소-5-(2-옥소-2-(싸이아졸리딘-3-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    150) 3-(4'-((2-부틸-4-메틸-5-(2-(4-메틸피페리딘-1-일)-2-옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    151) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    152) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-(2-메톡시에틸)아세트아마이드;
    153) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-(2-(싸이오펜-2-일)에틸)아세트아마이드;
    154) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이아이소프로필아세트아마이드;
    155) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    156) 3-(4'-((5-(2-(1H-아이소인돌-2(3H,3aH,4H,5H,6H,7H,7aH)-일)-2-싸이옥소에틸)-2-부틸-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    157) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
    158) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    159) 3-[2-[4-[[2-부틸-4-메틸-5-(2-몰폴린-4-일-2-설파닐리덴에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    160) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로판-2-일에탄싸이오아마이드;
    161) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
    162) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    163) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    164) 2-부틸-N,4-다이메틸-N-(2-메틸프로필)-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-카보싸이오아마이드;
    174) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이에틸에탄싸이오아마이드;
    175) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-프로필에탄싸이오아마이드;
    176) N-부틸-2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]에탄싸이오아마이드;
    177) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    178) N-메톡시-N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]에탄싸이오아마이드;
    179) N,N-다이메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-2-프로필피리미딘-5-일]에탄싸이오아마이드;
    180) 3-[2-[4-[[4-메틸-6-옥소-2-프로필-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    181) 3-[2-[4-[[4-메틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    182) 3-[2-[4-[[5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    183) 3-[2-[4-[[5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    184) N-메틸-2-[4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일l)페닐]페닐]메틸]-2-프로필피리미딘-5-일]-N-프로판-2-일에탄싸이오아마이드;
    185) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸프로판싸이오아마이드;
    186) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일프로판싸이오아마이드;
    187) 3-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-사이클로프로필프로판싸이오아마이드;
    188) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(3-피페리딘-1-일-3-설파닐리덴프로필)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    189) 3-[2-[4-[[5-[3-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-3-설파닐리덴프로필]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    190) 3-[2-[4-[[2-부틸-4-메틸-5-[3-(4-메틸피페리딘-1-일)-3-설파닐리덴프로필]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    191) 3-[2-[4-[[2-부틸-5-[3-(3,3-다이메틸피페리딘-1-일)-3-설파닐리덴프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    192) 3-[2-[4-[[2-부틸-5-[3-(3,5-다이메틸몰폴린-4-일)-3-설파닐리덴프로필]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    193) 3-[2-[4-[[2-부틸-4-메틸-5-(3-몰폴린-4-일-3-설파닐리덴프로필)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    194) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부탄-2-일-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    195) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
    196) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    197) 2-[2-부탄-2-일-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
    198) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    199) 3-[2-[4-[[2-부탄-2-일-5-[2-(2,6-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    200) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    201) 3-[2-[4-[[2-부틸-5-[2-(3,4-다이하이드로-1H-아이소퀴놀린-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    202) 3-[2-[4-[[5-[2-(3,4,4a,5,6,7,8,8a-옥타하이드로-1H-아이소퀴놀린-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    203) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-설파닐리덴-2-(1,3-싸이아졸리딘-3-일)에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    204) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    205) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    206) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
    207) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(2-메톡시에틸)-N-메틸에탄싸이오아마이드;
    208) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-(2-싸이오펜-2-일에틸)에탄싸이오아마이드;
    208) 2-(2-부틸-4-메틸-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이아이소프로필아세트아마이드;
    209) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이(프로판-2-일)에탄싸이오아마이드;
    210) 3-[2-[4-[[2-부틸-5-(2-인돌-1-일-2-설파닐리덴에틸)-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    211) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸피롤리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    212) 2-[2-사이클로프로필-4-메틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    213) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-사이클로프로필-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    214) 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    215) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    216) 3-[2-[4-[[2-부틸-5-[2-(2,3-다이하이드로인돌-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    217) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-(4-프로판-2-일피페리딘-1-일)-2-설파닐리덴에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    218) 3-[2-[4-[[5-[2-(3,3a,4,5,6,6a-헥사하이드로-1H-사이클로펜타[c]피롤-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    219) 3-[2-[4-[[2-부틸-5-[2-(1,3-다이하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    220) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[4-(4-나이트로페닐)피페라진-1-일]-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    221) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
    222) 2-[2-부틸-1-[[4-[5-플루오로-2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-메틸-6-옥소피리미딘-5-일]-N-메톡시-N-메틸에탄싸이오아마이드;
    223) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
    224) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
    225) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]-4-플루오로페닐]-4H-1,2,4-옥사다이아졸-5-온;
    226) 2-[2-부틸-1-[[4-[5-플루오로-2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-메틸-6-옥소피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
    227) 3-[2-[4-[[2-부틸-4-메틸-5-[2-(2-메틸-1,3,3a,4,6,6a-헥사하이드로피롤로[3,4-c]피롤-5-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    228) 3-(4'-((2-부틸-5-(2-(헥사하이드로사이클로펜타[c]피롤-2(1H)-일)-2-싸이옥소에틸)-4-메틸-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    229) 3-[2-[4-[[5-[2-(1,3,4,6,7,8,9,9a-옥타하이드로피리도[1,2-a]피라진-2-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    230) 3-[2-[4-[[5-[2-(2,3,3a,4,5,6,7,7a-옥타하이드로인돌-1-일)-2-싸이옥소-에틸]-2-부틸-4-메틸-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-2H-1,2,4-옥사다이아졸-5-온;
    231) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    232) 3-[2-[4-[[2-부틸-4-메틸-6-옥소-5-[2-설파닐리덴-2-[4-(트리플루오로메틸)피페리딘-1-일]에틸]피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    233) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    234) 3-[2-[4-[[5-[2-(8-아자스파이로[4.5]데칸-8-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    235) 3-[2-[4-[[2-부틸-5-[2-(4,4-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    236) 3-[2-[4-[[5-[2-(4,4-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소-2-프로필피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    237) 2-[2-부틸-4-메틸-6-옥소-1-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    238) 5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-6-메틸-3-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-4-온;
    239) 2-부틸-6-메틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-3-[[4-[2-(5-설파닐리덴-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-4-온;
    240) 3-[2-[4-[[2-부틸-5-[2-(2,5-다이메틸피롤리딘-1-일)-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    241) 3-[2-[4-[[2-부틸-5-[2-[(2S,6R)-2,6-다이메틸피페리딘-1-일]-2-설파닐리덴에틸]-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H6-1,2,4-옥사다이아졸-5-온;
    242) 3-[2-[4-[[5-[2-[(4aS,7aR)-1,3,4,4a,5,6,7,7a-옥타하이드로사이클로펜타[c]피리딘-2-일]-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    243) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2S)-2-메틸피롤리딘-1-일]-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    244) 3-[2-[4-[[2-부틸-4-메틸-5-[2-[(2R)-2-메틸피롤리딘-1-일]-2-싸이옥소-에틸]-6-옥소-피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    245) 3-[2-[4-[[5-[2-(7-아자바이사이클로[2.2.1]헵탄-7-일)-2-설파닐리덴에틸]-2-부틸-4-메틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    246) 3-(4'-((2-부틸-4-메틸-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    247) 3-(4'-((2-부틸-4-메틸-6-옥소-5-(2-싸이옥소-2-(3-(트리플루오로메틸)-5,6-다이하이드로-[1,2,4]트리아졸로[4,3-a]피라진-7(8H)-일)에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    248) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    249) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
    250) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-사이클로프로필-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    251) 2-[2-부틸-4-사이클로프로필-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-(2-메틸프로필)에탄싸이오아마이드;
    252) 3-[2-[4-[[2-부틸-4-사이클로프로필-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    253) 3-(4'-((2-부틸-4-사이클로프로필-6-옥소-5-(2-(피롤리딘-1-일)-2-싸이옥소에틸)피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    254) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2,6-다이메틸피페라진-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    255) (S)-3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피롤리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    256) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    257) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N-사이클로프로필에탄싸이오아마이드;
    258) 2-(2-부틸-4-사이클로프로필-6-옥소-1-((2'-(5-옥소-4,5-다이하이드로-1,2,4-옥사다이아졸-3-일)바이페닐-4-일)메틸)-1,6-다이하이드로피리미딘-5-일)-N,N-다이에틸에탄싸이오아마이드;
    259) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(3,5-다이메틸몰폴리노)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    260) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-((2S,6R)-2,6-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    261) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-몰폴리노-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    262) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(2-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    263) 3-(4'-((2-부틸-4-사이클로프로필-5-(2-(4-하이드록시피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    264) 3-[2-[4-[[2-부틸-6-옥소-4-프로판-2-일-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    265) 3-[2-[4-[[2-부틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    266) 3-[2-[4-[[2-부틸-5-[2-(2,6-다이메틸피페라진-1-일)-2-설파닐리덴에틸]-6-옥소-4-프로판-2-일피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    267) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    268) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N,N-다이에틸에탄싸이오아마이드;
    269) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
    270) 2-[2-부틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]-4-프로판-2-일피리미딘-5-일]-N-사이클로프로필에탄싸이오아마이드;
    271) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸-7,8-다이하이드로피리도[4,3-d]피리미딘-6(5H)-일)-2-싸이옥소에틸)-6-옥소-5,6-다이하이드로피리미딘-1(4H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    272) 3-(4'-((2-부틸-5-(2-(3,5-다이메틸피페리딘-1-일l)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    273) 3-(4'-((2-부틸-5-(2-((2R,6S)-2,6-다이메틸피페리딘-1-일)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    274) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    275) 3-(4'-((2-부틸-4-아이소프로필-5-(2-(3-메틸피페리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    276) 3-(4'-((2-부틸-4-아이소프로필-5-(2-몰폴리노-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    277) 3-(4'-((2-부틸-5-(2-(2,6-다이메틸몰폴리노)-2-싸이옥소에틸)-4-아이소프로필-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    278) (S)-3-(4'-((2-부틸-4-아이소프로필-5-(2-(2-메틸피롤리딘-1-일)-2-싸이옥소에틸)-6-옥소피리미딘-1(6H)-일)메틸)바이페닐-2-일)-1,2,4-옥사다이아졸-5(4H)-온;
    279) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N,N-다이메틸에탄싸이오아마이드;
    280) 2-[2-부틸-4-에틸-6-옥소-1-[[4-[2-(5-옥소-4H-1,2,4-옥사다이아졸-3-일)페닐]페닐]메틸]피리미딘-5-일]-N-메틸-N-프로판-2-일에탄싸이오아마이드;
    281) 3-[2-[4-[[5-[2-(1,3,3a,4,5,6,7,7a-옥타하이드로아이소인돌-2-일)-2-설파닐리덴에틸]-2-부틸-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    282) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-피롤리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    283) 3-[2-[4-[[2-부틸-4-에틸-6-옥소-5-(2-피페리딘-1-일-2-설파닐리덴에틸)피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    284) 3-[2-[4-[[2-부틸-4-에틸-5-(2-몰폴린-4-일-2-설파닐리덴에틸)-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    285) 3-[2-[4-[[2-부틸-4-에틸-5-[2-(4-메틸피페리딘-1-일)-2-설파닐리덴에틸]-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온;
    286) 3-[2-[4-[[2-부틸-5-[2-(3,3-다이메틸피페리딘-1-일)-2-설파닐리덴에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온; 및
    287) 3-[2-[4-[[2-부틸-5-[2-(3,5-다이메틸몰폴린-4-일)-2-설파닐리덴에틸]-4-에틸-6-옥소피리미딘-1-일]메틸]페닐]페닐]-4H-1,2,4-옥사다이아졸-5-온.
  5. 제 1 항 내지 제 4 항 중 어느 하나의 항의 화합물, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 고혈압 또는 당뇨병의 치료 또는 예방용 약학적 조성물.
  6. 제 5 항에 있어서, 상기 고혈압은 본태성 고혈압인 약학적 조성물.
  7. 제 5 항에 있어서, 상기 당뇨병은 제2형 당뇨병인 약학적 조성물.
  8. 제 5 항에 있어서, 고혈압 및 당뇨병을 동시에 치료 또는 예방하기 위한 약학적 조성물.
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US5472967A (en) * 1991-02-20 1995-12-05 Synthelabo 4-pyrimidinone derivatives their preparation and their application in therapy
US20010020100A1 (en) * 1994-06-14 2001-09-06 G.D. Searle & Co. N-substituted-1, 2, 4-triazolone compounds for treatment of cardiovascular disorders
KR100300566B1 (ko) 1994-09-17 2001-11-22 조생현 피리미디논유도체와그의제조방법및용도
KR19990081093A (ko) * 1998-04-25 1999-11-15 조생현 피리미디논 화합물, 이를 함유하는 약제학적 조성물 및 이의제조방법
KR100617953B1 (ko) 2000-03-23 2006-08-30 보령제약 주식회사 피리미디논 화합물 및 이의 염의 제조방법
KR100521980B1 (ko) 2002-10-10 2005-10-17 보령제약 주식회사 피리미디논 화합물 및 이의 염의 삼수화물의 제조 방법

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EP0520423B1 (en) * 1991-06-27 2003-05-14 Takeda Chemical Industries, Ltd. Heterocyclic compounds, their production and use as angiotensin II antagonists
WO2008062905A2 (en) * 2006-11-24 2008-05-29 Takeda Pharmaceutical Company Limited Heteromonocyclic compound and use thereof

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