KR890009906A - Paf 길항제로서의 2,5- 디아릴테트라하이드로푸란 및 이의 동족체 - Google Patents

Paf 길항제로서의 2,5- 디아릴테트라하이드로푸란 및 이의 동족체 Download PDF

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KR890009906A
KR890009906A KR1019880017017A KR880017017A KR890009906A KR 890009906 A KR890009906 A KR 890009906A KR 1019880017017 A KR1019880017017 A KR 1019880017017A KR 880017017 A KR880017017 A KR 880017017A KR 890009906 A KR890009906 A KR 890009906A
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비프투 테스파에
Dk 황 산-보
더블유.도에버 토마스
알.비티 토마스
센 청-잉
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제임스 에프, 노오튼
머크 앤드 캄파니 인코포레이티드
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Abstract

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Description

PAF 길항제로서의 2,5-디아릴테트라히다르로푸란 및 이의 동족체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(Ⅰ)의 화합물.
    상기식에서, R 및 R1은 독립적을 (a)수소; (b) 할로저급알킬; (c) 할로; (d)CONR2R3[여기서, R2및 R3는 독립적으로) 1) H; 2) 직쇄 또는 측쇄의 C1-20알킬; 3)C3-8사이클로알킬; 4) C2-20알케닐; 5) C2-20알키닐; 6) 탄소수 6 내지 14의 아릴; 또는 7)아르알킬이다]; (e) 저급 알케닐; (f) -COR2; (g) -CH2OR2; (h) 저급알키닐; (i)-CH2NR2R3; (j) -CH2SR2; (k) =O; (1) -OR2또는 (m) -R2이고 : Ar 및 Ar1은 서로 동일하거나 상이하며
    치환된 페닐[여기서, R4내지 R8은 독립적으로 1) R2; 2) YO- (여기서, Y는 -R2또는 Y1이고 여기서, Y1은 (1) -(CH2)1-6O(CO)R; (2) -(CH2)1-6 (3) -(CH2)1-6-C3-8사이클로알킬 (4) -(CH2)1-6COOR2; (5) -(CH2)1-6OR2; (6) -(CH2)1-6Ph; (7) -(CH2)1-6 [여기에서 n은 0,1 또는 2이다] (8) 할로저급 알킬; (9) -(CH2)1-7OSO2R2; 또는 (10) -(CH2)1-6NR2R3이다; 3)4) -S(O)n-(CH2)1-6OR2,[여기서, n은 0,1 또는 2이다]; 5) -OCOCF3; 6)7) -OCOR2, 8) Y1; 9) R2R3N-; 10)11) COOR2; 12) -CONR2R3; 13) -NR2COR3; 14) -OCONR2R3; 15) 0CR2R3R9[여기서, R9은 R2이고 R2와 동일하거나 상이할 수 있다]; 16) -(CH2)1-6OCOR2; 17) -(CH2)1-6NR2COR3; 18) -NHCH2COOR2; 19) -CONR2COR3; 20) -(CH2)1-6NR2R3; 21) 할로; 22) －ＮＲ2Ｒ3Ｒ9Ｘ[여기서 X-는 음이온이다]; 23) -(CH2)1-6NR2R3R9X-; 24) -NR2SO2R3; 25) -COR2; 26) -NO2; 27) CN; 28) -(CH2)1-6CN; 29) -N3; 30) -(CH2)1-6N3; 31)-CONR2(CH2)1-6NR3R9; 32) -PO3R2R3; 33) -(CH2)1-6PO3R2R3; 34) -PO3(R2)(CH2)1-6NR3R9; 35) 함께 결합하여 브릿지를 형성한 -R4-R3, R5-R6, R6-R7및 R7-R8; 36) SO2(CH2)1-6-CO-OR2;
    43) 하기에 정의한 바와 같은 헤테로아릴; 44) -SO(CH2)1-6CONH2; 45) -(CH2)1-6CONR2R3; 46) -(CH2)1-6NR2SO2R3; 47) -(CH2)1-6OSO2R2; 48) -O(CH2)1-6-NR2R3; 49) -CO-NOR2-CO-R3; 50) -S-CO-NR2R3; 51) -PO3(CH2CH2N(CH3)2)(C2H5); 52) -S(O)n(CH2)0-5CH2CH(OR2)R3; 53) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)R3; 54) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)NHR3; 55) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)OR3이다]; (b) 모노헤테로아릴, 디-또는 폴리헤테로아릴, 또는 하나 또는 그 이상의 헤테로원자, N,S 또는 01 내지 3개를 함유하는 융합된 헤테로아릴; (c) 헤테로아릴아킬; (d) 헤테로사이클로알킬; 또는 (e) 헤테로사이클로알케닐이다.
  2. 제1항에 있어서, a) 트란스-2,3-디메톡시-5-(테트라하이드로-5-(3-메톡시-4-프로폭시-5-(2-하이드록시에틸술포닐)-2-푸라닐)피리딘; b) 트란스-2-(3,4,5-트리메톡시페닐)-5-(3-메톡시-4-프로폭시-5-(2-하이드록시에틸술포닐) 테트라하이드로푸란; c) 트란스-2,3-디메톡시-5-(테트라하이드로-5-(4-에톡시-3-메톡시-5-프로필술포닐)-2-푸라닐)피리딘; d) 트란스-2-(3,4,5-트리메톡시페닐)-5-(4-에톡시-3-메톡시-5-프로필술포닐) 테트라하이드로푸란; e) 트란스-2-(3,4,5-트리메톡시페닐)-5-(3-메톡시-4-프로폭시-5-N-프로필카복시아미도페닐)테트라하이드로푸란; 또는 f) 트란스-2-(3,4,5-트리메톡시페닐)-5-(메톡시-4-프로폭시-5-(2-하이드록시프포필술포닐)페닐)-테트라하이드로푸란의 화합물
  3. 제1항에 있어서, 하기 일반식(A)의 화합물.
    상기식에서
    (a) R5가 OCH3인 경우, R4및 Y는 다음과 같고,
  4. 제1항에 있어서, 하기 일반식(B)의 화합물
    상기식에서, R4은 (a) SO2CH3; (b) SO2CH2CH2OH; 또는 SO2CH2CH(OH)CH3이고, Y는 C1-6알킬이다.
  5. 약제학적 담체 및 치료학적 유효량의 하기 일반식(Ⅰ)의 화합물을 함유함을 특징으로 하는, PAF에 의해 유발된 질병 또는 질환을 치료하기 위한 약제학적 조성물.
    상기식에서, R 및 R1은 독립적으로 (a) 수소; (b) 할로저급알킬; (c) 할로; (d) CONR2R3[여기서, R2및 R3은 독립적으로 1) H; 2) 직쇄 또는 측쇄의 C1-20알킬; 3) C3-8사이클로알킬; 4) C2-20알케닐; 5) C2-20알키닐; 6) 탄소수 6 내지 14의 아릴; 또는 7) 아르알킬이다]; e) 저급알케닐; (f) -COR2; (g) -CH2OR2; (h) 저급알키닐; (i) -CH2NR2R3; (j) -CH2SR2; (k) =O (1) -OR2; 또는 (m) -R2이고; Ar 및 Ar'은 서로 동일하거나 상이하며
    치환된 페닐[여기서, R4내지 R8은 독립적으로 1) R2; 2) YO- (여기서, Y는 -R2또는 Y1이고 여기서, Y1은 (1) -(CH2)1-6O(CO)R2; (2)(3) -(CH2)1-6-C3-8사이클로알킬; (4) -(CH2)1-6-COOR2; (5) -(CH2)1-6OR2; (6) -(CH2)1-6Ph; (7)[여기서, n은 0,1 또는 2이다]; (8) 할로저급알킬 (9) -(CH2)1-7OSO2R3; 또는 (10) -(CH2)1-6NR2R3이다]; 3)4) -S(O)n-(CH2)1-6OR22, [여기서, n은 0,1 또는 2이다]; 5) -OCOCF3; 6)7) -OCOR2; 8) Y1; 9) R2R3N-; 10)11) COOR2; 12) -CONR2R3; 13) -NR3COR3; 14) -CONR2R3; 15) CR2R3R9[여기서, R9는 R2이고, R2와 동일하거나 상이할 수 있다]; 16) -(CH2)1-6OCOR2; 17) -(CH2)1-6NR2COR3; 18) -NHCH2COOR3: 19) -CONR2COR3; 20) -(CH2)1-6NR2R3; 21) 할로; 22)[여기서 X-는 음이온이다]; 23)24) -NR2SO2R3; 25) COR2; 26) -NO2; 27) -CN; 28) -(CH2)1-6CN; 29) -N3; 30) -(CH2)1-6N3; 31) -CONR2(CH2)1-6NR3R9; 32)PO3R2R3; 33) -((CH2)1-6PO3R2R3;34) -PO3(R2)(CH2)1-6NR3R9; 35) 함께 결합하여 브릿지를 형성한 -R4-R5, R5-R6,R6-R7및 R7-R8, 36) SO-(CH2)1-6-CO-OR2;
    43) 하기에 정의한 바와 같은 헤테로아릴; 44) -SO2(CH2)1-6CONH245) -(CH2)1-6CONR2R3; 46) -(CH2)1-6NR2SO2R3; 47) -(CH2)1-6OSO2R2; 48) -O(CH2)1-6NR22R3; 49) -CO-NR2-CO-R3; 50) -S-CO-NR2R3; 51) -PO3(CH2CH2N(CH3)2)(C2H5); 52) -S(O)n(CH2)0-5CH2CH(OR2)R3; 53) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)R3; 54) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)NHR3; 55) -S(O)n(CH2)0-5CH2CH(OR2)-(CO)OR3이다]; (b) 모노헤테로아릴, 디- 또는 폴리헤테로아릴, 또는 하나 또는 그 이상의 헤테로원자 N,S 또는 01 내지 3개를 함유하는 융합된 헤테로아릴; (c) 헤테로아릴알킬; (d) 헤테로사이클로알킬; 또는 (e) 헤테로사이클로알케닐이다.
  6. 제5항에 있어서, 활성 화합물이 a) 트란스-2,3-디메톡시-5-(테트라하이드로-5-(3-메톡시-4-프로폭시-5-(2-하이드록시에틸술포닐)-2-푸라닐)피리딘; b) 트란스-2-(3,4,5-트리메톡시페닐)-5-(3-메톡시-4-프로폭시-5-(2-하이드록시에틸술포닐)테트라하이드로푸란; c) 트란스-2,3-디메톡시-5-(테트라하이드로-5-(4-에톡시-3-프로필술포닐)-2-푸라닐)피리딘; d) 트란스-2-(3,4,5-트리메톡시페닐)-5-(4-에톡시-3-프로필술포닐) 테트라하이드로푸란; e) 트란스-2-(3,4,5-트리메톡시페닐)-5-(3-메톡시-4-프로폭시-5-N-프로필카복시아미도페닐)테트라하이드로푸란; 또는 f) 트란스-2-(3,4,5-트리메톡시페닐)-3-(메톡시-4-프로폭시-5-(2-하이드록시프로필술포닐)페닐)-테트라하이드로푸란의 조성물.
  7. 제5항에 있어서, 활성 화합물의 하기 일반식(C)의 화합물의 조성물.
    (a) 상기식에서, R5이 OCH3인 경우, R4및 Y는 다음과 같고,
    TMP는 3,4,5-트리메톡시페닐이다.
  8. 제7항에 있어서, 화합물이 하기 일반식(B)의 화합물인 약제학적 조성물.
    상기식에서, R4은 (a)SO2CH3; (b) SO2CH2CH2OH; 또는 (c) SO2CH2CH(OH)CH3이고; Y는 C1-6알킬이다.
  9. (a) 하기 일반식(I-a)의 화합물을 환원제로 처리하거나; 또는 (b) 하기 일반식(I-b)의 화합물을 산화시키거나; 또는 (c) 하기 일반식(I-c)의 화합물을 수성산으로 처리함을 특징으로 하여, 제 1항에 따르는 하기 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서 R, R1, Ar 및 Ar1은 제 1항에서 정의한 바와 같고 A 및 B는 독립적으로 수소, 하이드록시-C1-6알킬, C1-6알콕시카보닐이다.
  10. 제9항에 있어서, 하기 일반식(B)의 화합물이 제조되는 방법.
    상기식에서, R4는 (a) SO2CH3; (b) SO2CH2OH; 또는 (c) SO2CH2CH(OH)CH3이고, Y는 C1-6알킬이다.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880017017A 1987-12-21 1988-12-20 Paf 길항제로서의 2,5- 디아릴테트라하이드로푸란 및 이의 동족체 KR890009906A (ko)

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US4977146A (en) * 1989-06-08 1990-12-11 Merck & Co., Inc. 2,5-diaryl tetrahydrofurans and analogs thereof as PAF antagonists
CA2045863A1 (en) * 1990-06-29 1991-12-30 Ichiro Shinkai Process of making 2,5-diaryl tetrahydrofurans and analogs thereof useful as paf antagonists
US5099033A (en) * 1990-06-29 1992-03-24 Merck & Co., Inc. Process of making 2,5-diaryl tetrahydrofurans and analogs thereof useful as PAF antagonists
US5639782A (en) * 1992-03-04 1997-06-17 Center For Innovative Technology Neolignan derivatives as platelet activating factor receptor antagonists and 5-lipoxygenase inhibitors
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AU666578B2 (en) * 1992-07-13 1996-02-15 Cytomed, Inc 2,5-diaryl tetrahydro-thiophenes, -furans and analogs for the treatment of inflammatory and immune disorders
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US5750565A (en) * 1995-05-25 1998-05-12 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
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