KR970706250A - 5-membered heterocyclic compounds (FIVE MEMBERED HETEROCYCLIC COMPOUNDS) - Google Patents

5-membered heterocyclic compounds (FIVE MEMBERED HETEROCYCLIC COMPOUNDS)

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Publication number
KR970706250A
KR970706250A KR1019970701970A KR19970701970A KR970706250A KR 970706250 A KR970706250 A KR 970706250A KR 1019970701970 A KR1019970701970 A KR 1019970701970A KR 19970701970 A KR19970701970 A KR 19970701970A KR 970706250 A KR970706250 A KR 970706250A
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South Korea
Prior art keywords
acetic acid
methylpyrrol
benzoyl
alkyl
bond
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KR1019970701970A
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Korean (ko)
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리 성재
다쿠야 세코
라저 프라이어슨 맨턴
챈드라 서카 재거디시
시안 카오 찰스
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우에노 도시오
오노 야쿠힝 고교 가부시키가이샤
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Publication of KR970706250A publication Critical patent/KR970706250A/en

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Abstract

본 발명은 (1)활성 성분으로서 하기 화학식(Ia)의 5원 헤테로시클릭 화합물 및 이의 비독성 염을 포함하는 5α-환원효소상의 억제제, (2)하기 화학식(Ib)의 5원 헤테로시클릭 화합물 및 이의 비독성 염, (3)하기 화학식(Ib)의 5원 헤테로시클릭 화합물 이의 비독성 염의 제조방법에 관한 것이다. 화학식(Ia)의 화합물은 포유동물의 다하이드로테스토스테론의 과잉 생성으로 인해서 야기되는 탈모증(나드로젠성 탈모증), 여드름, 전립선 비대중 및 전립선 암의 예방 치료에 유용하다:(1) an inhibitor of a 5-membered heterocyclic compound of formula (Ia) and a non-toxic salt thereof as an active ingredient, (2) a 5-membered heterocyclic compound of formula (Ib) (3) a 5-membered heterocyclic compound of the formula (Ib): < EMI ID = 4.1 > The compounds of formula (Ia) are useful for the prophylactic treatment of alopecia (neurogenic alopecia), acne, prostatic hypertrophy and prostate cancer caused by the overproduction of polyhydrotestosterone in mammals:

Description

5원 헤테로시클릭 화합물(FIVE MEMBERED HETEROCYCLIC COMPLUNDS)5-membered heterocyclic compounds (FIVE MEMBERED HETEROCYCLIC COMPLUNDS)

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (22)

활성 성분으로서 유효량의 하기 화학식(Ia)의 화합물 또는 이의 비독성 염 및 약학적 담체 또는 코팅물을 포함하는 포유동물의 디하이드로테스토스테론의 과잉 생성으로 인해서 야기되는 탈모증(안드로젠성 탈모증). 여드름, 전립선 비대증 및 전립선 암의 예방 및 치료를 위한 약학적 조성물:Alopecia (androgenic alopecia) caused by the overproduction of dihydrootestosterone in a mammal comprising an effective amount of a compound of the formula (Ia) as an active ingredient or a non-toxic salt thereof and a pharmaceutical carrier or coating. Pharmaceutical composition for the prevention and treatment of acne, hypertrophy of prostate and prostate cancer: 상기 식에서, ⓩ은 R4로 치환된 질소를 포함하는 피롤, 티오펜, 푸란, R4로 치환된 질소를 포함하는 이미다졸, 티아졸, 옥사졸, R4로 치환된 질소를 포함하는 트리아졸이며, 이때, R4는 수소, C1-C4알킬, 페닐 또는 페닐(C1-C4)알킬이며; A는 결합, C1-C6알킬렌 또는 C2-C6알케닐렌이며; E는 결합 또는 C1-C6알킬렌이며;는 벤젠, C4-C7시클로알칸, 나트탈렌, 벤조(C4-C7)시클로알칸, 인덴, 시클로펜타(C4-C7)시클로알칸,(이때, m은 0 또는 1임) 또는 하나의 질소, 하나의 황 또는 하나의 산소 원자를 포함하는 벤젠 융합된 4 내지 7원 헤테로시클릭 고리이며; R1은 수소 또는 C1-C4알킬이며; R2은 수소 또는 C1-C4알킬이며; n은 1 내지 3이며; R3각각은 독립적으로 (1)수소, C1-C6알킬, C1-C6알콕시, 할로겐, 니트로, 메틸티오, 트리플루오로메틸 또는 사아노, (2)-Q-T-U-R5이며; 이때, Q는 결합 또는 C1-C6알킬렌이며; T 는 결합, -O-,-S-, -SO2-, -NR7- 또는 -NR7CO-이며, 이때, R7은 수소, C1-C4알킬, 페닐 또는 페닐(C1-C4) 아킬이며, -NR7CO-에서의 N은 -Q-또는 -U-에 결합될 수 있으며; U는 결합, C1-C6알킬렌, C2-C6알케닐렌, C2-C6알키닐렌 또는 C1-C6알킬렌 -O-이며, 이때, 산소 원자는 R5만으로 결합될 수 있으며; R는 (i) C4-C7시클로알킬, (ii)페닐, (iii)디페닐메킬 또는 (iv)하나의 질소, 하나의 황 또는 하나의 산소를 포함하는 4 내지 7원 헤테로시클릭 고리이거나 또는 하나의 질소, 하나의 황 또는 하나의 산소를 포함하는 벤젠 융합된 4 내지 7원 헤테로시클릭 고리이거나 또는 R5의(i),(ii),(iii),(iv)에서의 고리는 1 내지 3개의 C1-C10알킬, C1-C10알콕시, 히드록시, 할로겐, 트리플루오로메틸, 니트로 또는 COR6로 치환될 수 있으며, 이때, R6는 C1-C4알킬, NR8R9이며, 이때, R8및 R9은 각각 독립적으로 수소 또는 C1-C4알킬이며; 또는 -Q-T-U-R5는 C7-C10알킬, C7-C10알콕시이며; 단, (i)ⓩ가 티오펜이며, E가 결합이며,가 벤젠 또는 나프탈렌인 경우, T는 -O-또는 -NR7-이며, U는 결합이며, R로 나타낸 -Q-T-U-R5에서의 R5는 디페닐메틸이며; (ii) ⓩ가 티오펜이며, E가 결합이며,가 벤젠 또는 나프탈렌인 경우, T는 -O-또는 -NR7-이며, U는 C1-C6알킬렌이며, R3로 나타낸 -Q-T-U-R5에서의 R5는 페닐 또는 디페닐메틸이며; (iii) ⓩ은 R4로 치환된 질소를 포함하는 피롤이며, R4는 수소, C1-C3알킬 또는 페닐이며, A는 결합또는 메틸렌이며, E는 결합이며,는 벤진이며, R3는 수소 또는 메틸이며, R는 각각 독립적으로 수소 또는 할로겐인 화합물은 제외한다.Wherein X is a pyrrole containing nitrogen substituted by R 4 , thiophene, furan, imidazole containing nitrogen substituted by R 4 , thiazole, oxazole, triazole containing nitrogen substituted by R 4 , Wherein R 4 is hydrogen, C 1 -C 4 alkyl, phenyl or phenyl (C 1 -C 4 ) alkyl; A is a bond, C 1 -C 6 alkylene or C 2 -C 6 alkenylene; E is a bond or C 1 -C 6 alkylene; Is selected from the group consisting of benzene, C 4 -C 7 cycloalkane, naphthalene, benzo (C 4 -C 7 ) cycloalkane, indene, cyclopenta (C 4 -C 7 ) (Wherein m is 0 or 1) or a benzene fused 4- to 7-membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen atom; R 1 is hydrogen or C 1 -C 4 alkyl; R 2 is hydrogen or C 1 -C 4 alkyl; n is 1 to 3; Each R 3 is independently selected from the group consisting of (1) hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, nitro, methylthio, trifluoromethyl or cyano, (2) -QTUR 5 ; Wherein Q is a bond or C 1 -C 6 alkylene; T is a bond, -O-, -S-, -SO 2 -, -NR 7 - or -NR 7 CO-, wherein R 7 is hydrogen, C 1 -C 4 alkyl, phenyl or phenyl (C 1 -C 4 ) 7 in CO- can be bonded to -Q- or -U-; U is a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene or C 1 -C 6 alkylene-O-, wherein the oxygen atom is bonded only to R 5 ; R is selected from the group consisting of (i) C 4 -C 7 cycloalkyl, (ii) phenyl, (iii) diphenylmecyl or (iv) a 4-7 membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen Or a benzene fused 4 to 7 membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen, or is a ring of fused 4 to 7 membered heterocyclic rings of R 5 , or of rings (i), (ii), (iii) May be substituted with one to three C 1 -C 10 alkyl, C 1 -C 10 alkoxy, hydroxy, halogen, trifluoromethyl, nitro or COR 6 , wherein R 6 is C 1 -C 4 alkyl , NR 8 R 9 , wherein R 8 and R 9 are each independently hydrogen or C 1 -C 4 alkyl; Or -QTUR 5 is C 7 -C 10 alkyl, C 7 -C 10 alkoxy; Provided that (i) is a thiophene, E is a bond, The case of benzene or naphthalene, T is -O- or -NR 7 -, and U is a bond, R 5 in -QTUR 5 represented by R is a diphenyl methyl; (ii) E is thiophene, E is a bond, When the benzene or naphthalene, T is -O- or -NR 7 - and, U is an alkylene C 1 -C 6 alkyl, R 5 in -QTUR 5 represented by R 3 are phenyl or diphenyl-methyl; (iii) ⓩ is a pyrrole comprising a nitrogen substituted with R 4, R 4 is hydrogen, C 1 -C 3 alkyl or phenyl, A is a bond or methylene, and E is a bond, Is benzene, R < 3 > is hydrogen or methyl, and R is independently hydrogen or halogen. 유효량이 제1항에 도시된 화학식(Ia)의 화합물 또는 이의 비독성 염을 투여하는 것을 포함하는, 포유동물의 디하이드로테스토테론의 과잉 생성으로 인해서 야기되는 탈모증(안드로젠성 탈모증), 여드름, 전립선 비대증 및 전립선 암을 예방 및 치료하는 방법.(Androgenic alopecia) caused by the overproduction of dihydrotestosterone in a mammal, comprising administering an effective amount of a compound of formula (Ia) as set forth in claim 1 or a non-toxic salt thereof, acne, prostatitis A method of preventing and treating hyperplasia and prostate cancer. 하기 화학식 (Ib)의 화합물 또는 이의 비독성 염;A compound of the formula (Ib) or a non-toxic salt thereof; 상기 식에서, ⓩ은 R4로 치환된 질소를 포함하는 피롤, 티오펜, 푸란, R4로 치환된 질소를 포함하는 이미다졸, 티아졸, 옥사졸, R4로 치환된 질소를 포함하는 트리아졸이며, 이때, R4는 수소, C1-C4알킬, 페닐 또는 페닐(C1-C4)알킬이며; A는 결합, C1-C6알킬렌 또는 C2-C6알케닐렌이며; E는 결합 또는 C1-C6알킬렌이며;는 벤젠, C4-C7시클로알칸, 나트탈렌, 벤조(C4-C7)시클로알칸, 인덴, 시클로펜타(C4-C7)시클로알칸,(이때, m은 0 또는 1임) 또는 하나의 질소, 하나의 황 또는 하나의 산소 원자를 포함하는 벤젠 융합된 4 내지 7원 헤테로시클릭 고리이며; R1은 수소 또는 C1-C4알킬이며; R2은 수소 또는 C1-C4알킬이며; n은 1 내지 3이며; R3각각은 독립적으로 (1)수소, C1-C6알킬, C1-C6알콕시, 할로겐, 니트로, 메틸티오, 트리플루오로메틸 또는 사아노, (2)-Q-T-U-R5이며; 이때, Q는 결합 또는 C1-C6알킬렌이며; T 는 결합, -O-,-S-, -SO2-, -NR7- 또는 -NR7CO-이며, 이때, R7은 수소, C1-C4알킬, 페닐 또는 페닐(C1-C4) 아킬이며, -NR7CO-에서의 N은 -Q-또는 -U-에 결합될 수 있으며; U는 결합, C1-C6알킬렌, C2-C6알케닐렌, C2-C6알키닐렌 또는 C1-C6알킬렌 -O-이며, 이때, 산소 원자는 R5만으로 결합될 수 있으며; R5는 (i)C4-C7시클로알킬, (ii)페닐, (iii)디페닐메킬 또는 (iv)하나의 질소, 하나의 황 또는 하나의 산소를 포함하는 4 내지 7원 헤테로시클릭 고리이거나 또는 하나의 질소, 하나의 황 또는 하나의 산소를 포함하는 벤젠 융합된 4 내지 7원 헤테로시클릭 고리이거나 또는 R5의(i),(ii),(iii),(iv)에서의 고리는 1 내지 3개의 C1-C10알킬, C1-C10알콕시, 히드록시, 할로겐, 트리플루오로메틸, 니트로 또는 COR6로 치환될 수 있으며, 이때, R6는 C1-C4알킬, NR8R9이며, 이때, R8및 R9은 각각 독립적으로 수소 또는 C1-C4알킬이며; 또는 -Q-T-U-R5는 C7-C10알킬, C7-C10알콕시이며; 단,(a)(i)ⓩ가 티오펜이며, E가 결합이며,가 벤젠 또는 나프탈렌인 경우, T는 -O-또는 -NR7-이며, U는 결합이며, R3로 나타낸 -Q-T-U-R5에서의 R5는 디페닐메틸이며; (ii) ⓩ가 티오펜이며, E가 결합이며,가 벤젠 또는 나프탈렌인 경우, T는 -O-또는 -NR7-이며, U는 C1-C6알킬렌이며, R3로 나타낸 -Q-T-U-R5에서의 R5는 페닐 또는 디페닐메틸인 화합물은 제외하며, (b)E가 결합이며,가 벤젠인 경우, (R3)n의 하나 이상의 R3은 -Q-T-U-R5인 군(2)에서 선택된 치환제이며;(c) E가 결합이며,가 C4-C7시클로알칸이거나 또는 E는 메틸렌이며,가 벤젠인 경우, (R3)n의 모든 R3은 동시에 수소가 아니며; (d) 2-[5-[2-클로로-4-(1H-피롤-1일)벤조일]티오펜-2-일]아세트산 및 이의 메틸 에스테르 및 2-[5-[2-클로로-4-(2,5-디메틸-1H-피롤-1일)벤조일]티오펜-2-일]아세트산 및 이의 메틸 에스테르인 화합물은 제외한다.Wherein X is a pyrrole containing nitrogen substituted by R 4 , thiophene, furan, imidazole containing nitrogen substituted by R 4 , thiazole, oxazole, triazole containing nitrogen substituted by R 4 , Wherein R 4 is hydrogen, C 1 -C 4 alkyl, phenyl or phenyl (C 1 -C 4 ) alkyl; A is a bond, C 1 -C 6 alkylene or C 2 -C 6 alkenylene; E is a bond or C 1 -C 6 alkylene; Is selected from the group consisting of benzene, C 4 -C 7 cycloalkane, naphthalene, benzo (C 4 -C 7 ) cycloalkane, indene, cyclopenta (C 4 -C 7 ) (Wherein m is 0 or 1) or a benzene fused 4- to 7-membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen atom; R 1 is hydrogen or C 1 -C 4 alkyl; R 2 is hydrogen or C 1 -C 4 alkyl; n is 1 to 3; Each R 3 is independently selected from the group consisting of (1) hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, nitro, methylthio, trifluoromethyl or cyano, (2) -QTUR 5 ; Wherein Q is a bond or C 1 -C 6 alkylene; T is a bond, -O-, -S-, -SO 2 -, -NR 7 - or -NR 7 CO-, wherein R 7 is hydrogen, C 1 -C 4 alkyl, phenyl or phenyl (C 1 -C 4 ) 7 in CO- can be bonded to -Q- or -U-; U is a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene or C 1 -C 6 alkylene-O-, wherein the oxygen atom is bonded only to R 5 ; R 5 is selected from the group consisting of (i) C 4 -C 7 cycloalkyl, (ii) phenyl, (iii) diphenylmecyl or (iv) 4- to 7-membered heterocycles comprising one nitrogen, one sulfur or one oxygen Or a benzene fused 4- to 7-membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen, or R < 5 > The ring may be substituted with one to three C 1 -C 10 alkyl, C 1 -C 10 alkoxy, hydroxy, halogen, trifluoromethyl, nitro or COR 6 , wherein R 6 is C 1 -C 4 Alkyl, NR 8 R 9 , wherein R 8 and R 9 are each independently hydrogen or C 1 -C 4 alkyl; Or -QTUR 5 is C 7 -C 10 alkyl, C 7 -C 10 alkoxy; Provided that (a) (i) is a thiophene, E is a bond, The case of benzene or naphthalene, T is -O- or -NR 7 -, and U is a bond, R 5 in -QTUR 5 represented by R 3 is a diphenyl methyl; (ii) E is thiophene, E is a bond, When the benzene or naphthalene, T is -O- or -NR 7 - and, U is C 1 -C 6 alkylene, R 5 is phenyl or diphenyl-methyl compound in -QTUR 5 represented by R 3 is (B) E is a bond, (R 3 ) n is a substituent selected from the group (2) wherein R 3 is -QTUR 5 , (c) when E is a bond, Is C 4 -C 7 cycloalkane, or E is methylene, If the benzene is, (R 3) R 3 of all n are not simultaneously hydrogen; (d) 2- [5- [2-chloro-4- (1H-pyrrol-1-yl) benzoyl] thiophen-2-yl] acetic acid and its methyl ester and 2- [ (2,5-dimethyl-1H-pyrrol-1-yl) benzoyl] thiophen-2-yl] acetic acid and its methyl ester. 제3항에 있어서, ⓩ은 R4로 치환된 질소를 포함하는 피롤이며, 이때, R4는 제3항에서 정의된 것과 동일한 화합물.4. The compound of claim 3 wherein X is pyrrole containing nitrogen substituted with R < 4 & gt ;, wherein R < 4 > is the same as defined in claim 3. 제3항에 있어서, ⓩ가 티오펜인 화합물.The compound according to claim 3, wherein X is thiophene. 제3항에 있어서, ⓩ가 푸란인 화합물.The compound according to claim 3, wherein X is furan. 제3항에 있어서, ⓩ가 R4로 치환된 질소를 포함하는 이미다졸이며, 이때, R4는 제3항에서 정의된 것과 동일한 화합물.4. The compound of claim 3, wherein X is imidazole containing nitrogen substituted by R < 4 & gt ;, wherein R < 4 > is the same as defined in claim 3. 제3항에 있어서, ⓩ가 티아졸인 화합물.4. The compound according to claim 3, wherein X is thiazole. 제3항에 있어서, ⓩ가 옥사졸인 화합물.The compound according to claim 3, wherein X is oxazole. 제3항에 있어서, ⓩ가 R4로 치환된 질소를 포함하는 트리아졸이며, 이때, R4는 제3항에서 정의된 것과 동일한 화합물.4. A compound according to claim 3, wherein X is a triazole comprising nitrogen substituted by R < 4 & gt ;, wherein R < 4 > is the same as defined in claim 3. 제3항에 있어서,가 벤젠인 화합물.The method of claim 3, Lt; / RTI > is benzene. 제3항에 있어서,가 C4-C7시클로알칸일 화합물.The method of claim 3, Is a C 4 -C 7 cycloalkane. 제3항에 있어서,가 나프탈렌, 벤조(C4-C7) 시클로알칸, 인덴, 시클로펜타(C4-C7) 시클로알칸 또는(이때, m은 0또는 1임)인 화합물.The method of claim 3, Benzo (C 4 -C 7 ) cycloalkane, indene, cyclopenta (C 4 -C 7 ) cycloalkane or (Wherein m is 0 or 1). 제3항에 있어서,가 하나의 질소, 하나의 황 또는 하나의 산소원자를 포함하는 벤젠 융합된 4 내지 7원헤테로시클릭 고리인 화합물.The method of claim 3, Is a benzene fused 4- to 7-membered heterocyclic ring containing one nitrogen, one sulfur or one oxygen atom. 제3항에 있어서, 2-[5-[4-(4-에틸페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-(4-시클로 헥실벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-벤젤벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-벤조일벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-벤젤벤조일)-1-메틸피롤-2-일]아세트산,2-[5-(3-펜옥시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-벤질옥시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-벤질옥시벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-에틸벤질옥시)벤조일-1-메틸피롤-2-일])아세트산벤질옥시벤조일, 2-[5-[4-(4-이소프로필벤질옥시)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-부틸벤질옥시)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-t-부틸벤질옥시)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-페닐벤질)카르보닐-1메틸피롤-2-일]아세트산, 2-[5-(3-벤질옥시-4-메톡시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-[4-벤질옥시-2메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-벤질옥시-2,3-디메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-페닐프로필)카르보닐-1-메틸피롤-2-일]아세트산, 2-[5-(4-피닐부틸)카르보닐-1-메틸피롤-2-일]아세트산, 2-[5-(4-헵틸페닐)벤조일-1-메틸피롤-2-일]아세트산, 2-[4-(4-페닐벤조일)-1-메틸피롤-2-일]아세트산, 3-[5-(4-페닐벤조일)-1-메틸피롤-2-일]-2-프로펜산, 3-[5-(4-페닐벤조일)-1-메틸피롤-2-일]프로피온산, 4-[5-(4-페닐벤조일)-1-메틸피롤-2-일]부탄산, 2-[5-(4-페닐벤조일)-1-벤질피롤-2-일]아세트산, 5-[5-(4-페닐벤조일)-1-메틸피롤-2-일]펜탄산, 5-[5-[4-(4-이소프로필벤질옥시)벤조일]-1-메틸피롤-2-일]부탄산, 5-[5-[4-(4-이소프로필벤질옥시)벤조일]-1-메틸피롤-2-일]펜단산, 5-[5-(2-펜옥시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-시클로헥시옥시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5[4-(4-니트로페닐옥시)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-(3-디페닐메틸아미노벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-디벤질아미노벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-디벤질아미노메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-페닐카르보닐아미노벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐카르보닐아미노벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐티오메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-페닐티오메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐설포닐메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3-페닐설포닐메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-페닐에틸)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-페닐에티닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-페닐에테닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[5-(4,4′-비페닐)펜틸카르보닐]-1메틸피롤-2-일]아세트산, 2-[5-(3-피롤벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-피롤벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-이소인렐벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2,5-디메틸피롤)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[3-(2-티에닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-티에닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[3-(5-브로모-2-티에닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-(4-헵틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-프로필시클로헥실)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-메틸페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-메틸페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-프로필페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-플루오로페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-클로로페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(3-클로로-4-플루오로페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(3-트리플루오로메틸페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-트리플루오로메틸페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(3-니트로페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-메틸카르보닐페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(4-디메틸아미노카르보닐페닐)벤조일]-1-메틸피롤-2-일]아세트산, 5-(4-페닐벤조일)-1-메틸피롤-2-일 카르복실산, 4-(4-페닐벤조일)-1-메틸피롤-2-일 카르복실산, 5-(4-페닐벤조일)-1H-피롤-2-일 카르복실산, 4-(4-페닐벤조일)-1H-피롤-2-일 카르복실산, 2-[5-[4-(4-보로모페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐벤조일)-1H-피롤-2-일]아세트산, 2-[5-[4-(2,4-디클로로페닐)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(3,5-디클로로페닐)벤조일]-1-메틸피롤-2-일]아세트산, -[5-(3-메틸-4-페닐벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-[4-[(N-메틸-N-페닐)카르바모일]벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-[(N-페닐카르바모일]벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-[N-(디페닐메틸)카르바모일]벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-[N-(N-메틸-N-벤질)카르바모일]벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(N-벤질카르바모일)벤조일]-1-메틸피롤-2-일]아세트산, 2-[5-[4-(2-펜옥시에톡시)벤조일]-1-메틸피롤-2-일]아세트산 및 5-(3-페닐프로파노일)-1-메틸-2-피롤아세트산으로 구성된 군에서 선택된 화합물.4. The compound according to claim 3, which is 2- [5- (4- (4-ethylphenyl) benzoyl] -1-methylpyrrol- Pyrrol-2-yl] acetic acid, 2- [5- (4-phenylbenzoyl) Acetic acid, 2- [5- (4-benzylbenzoyl) -1-methylpyrrol-2-yl] acetic acid, 2- [ Yl] acetic acid, 2- [5- (4-benzyloxybenzoyl) -1-methylpyrrol-2- 1-methylpyrrol-2-yl] acetic acid, 2- [5- [4- (4-ethylbenzyloxy) benzoyl- Benzyloxybenzoyl] -1-methylpyrrol-2-yl] acetic acid, 2- [5- [4- (4-butylbenzyloxy) benzoyl] Yl] acetic acid, 2- [5- [4- (4-t-butylbenzyloxy) benzoyl] 4- (4-phenylbenzyl) carbonyl-1-methylpyrrol-2-yl] 2-yl] acetic acid, 2- [5- [4-benzyloxy-2-methylbenzoyl) -1-methyl Yl] acetic acid, 2- [5- (3-phenylpropyl) -carbamic acid ethyl ester, 2- [ 2-yl] acetic acid, 2- [5- (4-phenylbutyl) carbonyl-1-methylpyrrol- Yl] acetic acid, 2- [4- (4-phenylbenzoyl) -1-methylpyrrol- Yl] propionic acid, 4- [5- (4-phenylbenzoyl) -1-methylpyrrole- Yl] butanoic acid, 2- [5- (4-phenylbenzoyl) -1-benzylpyrrol-2-yl] acetic acid, 5- [ 5- [5- [4- (4-isopropylbenzyloxy) benzoyl] -1-methylpyrrol-2-yl] butanoic acid, 5- [ Benzoyl] -1-methylpyrrol-2-yl] pentanoic acid, 5- [5- (2-phenoxybenzoyl) Yl] acetic acid, 2- [5 [4- (4-nitrophenyloxy) benzoyl] ] -1-methylpyrrol-2-yl] acetic acid, 2- [5- (3-dibenzylamino Yl] acetic acid, 2- [5- (3-phenylcarbamoyl) -1-methylpyrrol- 2-yl] acetic acid, 2- [5- (4-phenylpiperidin-4-ylmethoxybenzoyl) Yl] acetic acid, 2- [5- (4-fluorophenyl) thiomethylbenzoyl) -1- Yl] acetic acid, 2- [5- (3-phenylsulfonylmethylbenzoyl) -1-methylpyrrol-2- Yl] acetic acid, 2- [5- [4- (2-phenylethynyl) benzoyl] -1-methylpyrrol- 2-yl] acetic acid, 2- [5- [5- (4,4'-biphenyl) pentyl 2-yl] acetic acid, 2- [5- (4-pyrrolbenzoyl) -1-methylpyrrol- 2-yl] acetic acid, 2- [5- [4- (2,5-dimethylpyrrole-1-methylpyrrolidin- ) Benzoyl] -1- methylpyrrol-2-yl] acetic acid, 2- [5- [3- (2-thienyl) Yl] acetic acid, 2- [5- [3- (5-bromo-2-thienyl) benzoyl] -1-methylpyrrole- Yl] acetic acid, 2- [5- [4- (4-propylcyclohexyl) benzoyl] -1-methylpyrrole- Yl] acetic acid, 2- [5- [4- (2-methylphenyl) benzoyl] -1- Yl] acetic acid, 2- [5- [4- (4-propylphenyl) benzoyl] Yl] acetic acid, 2- [5- [4- (4-chlorophenyl) benzoyl] -1-methylpyrrol- , 2- [5- [4- (3-trifluoromethylphenyl) benzoyl] -1-methylpyrrol-2-yl] 2- [5- [4- (4-trifluoromethylphenyl) benzoyl] -1-methylpyrrol-2-yl] acetic acid, 2- [ Yl] acetic acid, 2- [5- [4- (4-methylcarbonylphenyl) benzoyl] -1-methylpyrrol-2-yl] Yl) acetic acid, 5- (4-phenylbenzoyl) -1-methylpyrrol-2-yl (4-phenylbenzoyl) -lH-pyrrole-2-ylcarboxylic acid, 4- (4-phenylbenzoyl) 2-yl] acetic acid, 2- [5- (4-fluorophenyl) benzoyl] 4-phenylbenzoyl) -1H-pyrrol-2-yl] Acetic acid, 2- [5- [4- (3,5-dichlorophenyl) benzoyl] -1- Yl] acetic acid, 2- [5- [4 - [(N- (1-methylpyrrolidin- Yl] acetic acid, 2- [5- [4 - [(N-phenylcarbamoyl) benzoyl] -1-methylpyrrol- Yl] acetic acid, 2- [5- [4- [N- (diphenylmethyl) carbamoyl] benzoyl] Yl] acetic acid, 2- [5- [4- (N-benzylcarbamoyl) benzoyl] -1-methylpyrrole Yl] acetic acid and 5- (3-phenylpropanoyl) -1- (4-methylpiperazin-1- Methyl-2-pyrrole acetic acid. 제3항에 있어서, 2-[5-(4-t-부틸시클로헥실카르보닐)-1-메틸피롤-2-일]아세트산, 2-[5-(4-페닐시클로헥실카르보닐)-1-메틸피롤-2-일]아세트산 및 2-[5-[3-(1,2,3,4-테트라히드로-2-나프틸)프로필카르보닐]-1-메틸피롤-2-일]아세트산으로 구성된 군에서 선택된 화합물.4. The compound according to claim 3, wherein the compound is 2- [5- (4-t-butylcyclohexylcarbonyl) -1-methylpyrrol- Yl] acetic acid and 2- [5- [3- (1,2,3,4-tetrahydro-2-naphthyl) propylcarbonyl] -1-methylpyrrol- ≪ / RTI > 제3항에 있어서, 5-(2-나프틸)카르보닐-1-메틸-2-피롤아세트산 또는 5-(9-옥소플루오렌-2-일)카르보닐-1-메틸-2-피롤아세트산인 화합물.4. The method according to claim 3, wherein the compound is 5- (2-naphthyl) carbonyl-1-methyl-2-pyrrole acetic acid or 5- (9-oxofluoren- / RTI > 제3항에 있어서, 5-(2-벤조티에닐)카르보닐-1-메틸-2-피롤아세트산 또는 5-(2-벤조푸라닐)카르보닐-1-메틸-2-피롤아세트산인 화합물.The compound according to claim 3, which is 5- (2-benzothienyl) carbonyl-1-methyl-2-pyrrole acetic acid or 5- (2-benzofuranyl) carbonyl-1-methyl-2-pyrrole acetic acid. 제3항에 있어서, 2-[5-(4-페닐벤조일)-2-티에닐]아세트산 또는 2-[5-(4-펜옥시벤조일)-2-티에닐]아세트산인 화합물.4. The compound according to claim 3, which is 2- [5- (4-phenylbenzoyl) -2-thienyl] acetic acid or 2- [5- (4-phenoxybenzoyl) -2-thienyl] acetic acid. 제3항에 있어서, 2-[5-(4-페닐벤조일)-2-푸라닐]아세트산인 화합물.4. A compound according to claim 3 which is 2- [5- (4-phenylbenzoyl) -2-furanyl] acetic acid. 제3항에 있어서, 2-[2-(4-페닐벤조일)-1-메틸이미다졸-5-일]아세트산 또는 2-(4-페닐벤조일)-1-메틸이미다졸-5-일 카르복실산인 화합물.4. The compound of claim 3 which is 2- [2- (4-phenylbenzoyl) -1-methylimidazol-5-yl] acetic acid or 2- (4-phenylbenzoyl) Carboxylic acid. 제1항에 있어서, 2-[5-(4-페닐벤조일)-1-메틸이미다졸-5-일]아세트산, 2-[5-(4-t-부틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(3,5-디-t-부틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-헥실옥시벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-트리플루오로메틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-이소부틸벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-니트로벤조일)-1-메틸피롤-2-일]아세트산, 2-[5-(4-이소프로필옥시벤조일)-1-메틸피롤-2-일]아세트산 및 5-벤질카르보닐-1-메틸-2-피롤아세트산으로 구성된 군에서 선택된 약학적 조성물.2. The compound of claim 1 which is 2- [5- (4-phenylbenzoyl) -1-methylimidazol-5-yl] acetic acid, 2- [5- Yl] acetic acid, 2- [5- (4-hexyloxybenzoyl) -1- Yl] acetic acid, 2- [5- (4-trifluoromethylbenzoyl) -1-methylpyrrol- 2-yl] acetic acid, 2- [5- (4-isopropyloxybenzoyl) -1-methylpyrrole -2-yl] acetic acid and 5-benzylcarbonyl-1-methyl-2-pyrroleacetic acid. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019970701970A 1994-09-27 1995-09-27 5-membered heterocyclic compounds (FIVE MEMBERED HETEROCYCLIC COMPOUNDS) KR970706250A (en)

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