KR960704874A - 에스트로겐 작용물질로서의 벤조티오펜 및 관련 화합물 (benzothiophenes and related compounds as estrogen agonists) - Google Patents

에스트로겐 작용물질로서의 벤조티오펜 및 관련 화합물 (benzothiophenes and related compounds as estrogen agonists)

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KR960704874A
KR960704874A KR1019960701899A KR19960701899A KR960704874A KR 960704874 A KR960704874 A KR 960704874A KR 1019960701899 A KR1019960701899 A KR 1019960701899A KR 19960701899 A KR19960701899 A KR 19960701899A KR 960704874 A KR960704874 A KR 960704874A
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킴벌리 오. 카메론
실바-자르딘 폴 다
에릭 알. 라슨
제임스 알. 하우스케
로버트 엘. 로사티
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알렌 제이. 스피겔
화이자 인코포레이티드
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Abstract

본 발명은 A, B 및 Z가 독립적으로 -CH=, -CR4=, 또는 =N-이고; X가 -S-, -O-, -NH-, -NR2, -CH2CH2-, -CH2CH2CH2-, CH2O-, -OCH2-, -CH2S-, -CO-, -SCH2-, -N=CR2-, 또는 -R2C=N-이고; Y가 임으로 치환된 페닐, 알킬, 사이클로알킬, 사이클로알케닐, 헤테로사이클 또는 비사이클 고리 시스템 D는 -CO-, CR2R3-, -CONH-, NHCO-, -CR2(OH)-, -CONR2-, NOR2, CH-NO2, N-CO-, NR2CO-, -C-, -C-, -C-이고; E는 단일 결합, 임의로 치환된 페닐, 헤테로사이클이고; Z1은 -(CH2)pW(CH2)q-, -O(CH2)pCR5R6-, 또는 -O(CH2)pW(CH2)q-이고; G는 -NR7R8, 하기 (a), (b), (c), 브릿지되거나 융합되거나 임의로 치환되며, 5개 내지 12개의 탄소 원자를 함유하는 5원 또는 6원 포화, 불포화 또는 부분 불포화 및 임의로 치환된 헤테로사이클 또는 비사이클 아민이고; R은 할로겐, -NR2R3-, -NHCOR2-, -NHSO2R2, -CR2R3OH, -CONR2R3, -SO2NR2R3, OH, OR1, -O-COR1-인 하기 일반식(1)의 벤조티오펜 및 관련 화합물에 관한 것으로, 상기 화합물에 관한 것으로, 상기 화합물은 에스트로겐 결핍으로 인한 증상 및 질병을 치료하는데 유용하다:

Description

에스트로겐 작용물질로서의 벤조티오펜 및 관련 화합물(BENZOTHIOPHENES AND RELATED COMPOUNDS AS ESTROGEN AGONISTS)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (22)

  1. 하기 일반식 (1)의 화합물 및 그의 기하이성체 및 광학이성체, 그의 약학적으로 허용되는 에스테르, 에테르 및 염:
    상기 식에서 A, B 및 Z는 독립적으로 (a) -CH-, (b) -CR4=, 또는 (c) =N-이고; (a) -S-, (b) -O-, (c) -NH-, (d) -NR2-, (e) -CH2CH2-, (f) -CH2CH2CH2-, (g) -CH2O-, (h) -OCH2-, (i) -CH2S-, (j), (k) -SCH2-, (l) -N=CR2-, 또는 (m) -R2C=N-이고 ; Y는 (a) 할로, 하이드록시, C1-C4알킬, C1-C4알콕시,및 R1SO2NH-로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환된 페닐; (b) -OH, -OR2, 및 R1SO2NH-로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환된 C1-C8알킬; (c) -OH, -OR2, -NH2,및 R1SO2NH-로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환된 C3-C8사이클로알킬; (d) -OH, -OR1, 및 R1SO2NH-로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환된 C3-C8사이클로알케닐; (e) 수소, 하이드록실, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시|,C1-C4아실옥시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, 하이드록시(C|1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되는, -O-, -NR2, -N= 및 -S(O)n- 로 이루어진 그룹으로부터 선택된 2개 이하의 헤테로 원자를 함유하는 5원 포화, 불포화 또는 부분 불포화 헤테로 사이클; (f) 수소, 하이드록실, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시,C1-C4아실옥시, C1-C|4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, 하이드록시(C1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO|2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되는, -O-, -NR2, -N= 및 -S(O)n- 로 이루어진 그룹으로부터 선택된 2개 이하의 헤테로 원자를 함유하는 5원 또는 6원 포화, 불포화 또는 부분 불포화 헤테로 사이클; (g) 수소, 하이드록실, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시|,C1-C4아실옥시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, 하이드록시(C1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR|1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되는, -O-, -NR2, -N= 및 -S(O)n-로 이루어진 그룹으로부터 선택된 2개 이하의 헤테로 원자를 함유하는 , 페닐 고리에 융합된 5원 또는 6원 포화, 불포화 또는 부분 불포화 헤테로 사이클고리를 포함하는 비사이클 고리 시스템이고; D는 (a) -CO-, (b) -CR2R3-, (c) -CONH-, (d) -NHCO-, (e) -CR2(OH), (f) -CONR2-, (g) -NR2CO-, (h)(i)(j)이고; e는 (a) 단일결합; 수소, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시,C1-C4아실옥시, C1-C4알킬티오, C1-C4알킬설피닐, C|1-C4알킬설포닐, 하이드록시(C1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR|1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 3개의 이하의 치환체로 임의로 치환되는 페닐; 또는 (c) 수소, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시,C1-C|4아실옥시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, 하이드록시(C1-C|4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되는, -O-, -NR2, -N= 및 -S(O)n-로 이루어진 그룹으로부터 선택된 2개 이하의 헤테로 원자를 함유하는 , 페닐 고리에 융합된 5원 또는 6원 포화, 불포화 또는 부분 불포화 헤테로 사이클이고; Z1은 (a) -(CH2)pW(CH|2)q-, (b) -O(CH2)pCR5R6-, (c) -O(CH2)pW(CH2)q-, 이고; G는 (a) -NR7R8, (b) 하기 일반식을 갖고, 인접한 탄소 원자상에 1개 내지 2개의 페닐 고리와 임의로 융합되거나, 임의로 1대 내지 3개의 치환체로 탄소상에 독립적으로 치환되거나, 임의로 하기 (1) 내지 (22)에서 선택된 1개의 화학적으로 적합한 치환체로 질소상에 독립적으로 치환된 화합물:
    (여기서, n은 0,1 또는 2이고; m은 1,2 또는 3이고, Z2는 -NH, -O-, -S(O)n또는 -CH2이다)
    (e) 수소, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시|,C1-C4아실옥시, C1-C4알킬티오, C1-C4알킬설피닐, C|1-C4알킬설포닐, 하이드록시(C1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR|1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되는, -O-, -NR2, -N= 및 -S(O)n-로 이루어진 그룹으로부터 선택된 2개 이하의 헤테로 원자를 함유하고 Z1그룹이 탄소-탄소 결합 도는 탄소-질소 결합된 5원 또는 6원 포화, 불포화 또는 부분 불포화 헤테로 사이클; 또는 (f) 수소, 할로, C1-C4알킬, 트리할로메틸, C1-C4알콕시, 트리할로메톡시,C1-C4아실옥시, C1-C4알킬티오, C1-C|4알킬설피닐, C1-C4알킬설포닐, 하이드록시(C1-C4)알킬, 아릴(C1-C4)알킬, -CO2H, -CN, -CONHR1, -SO2NHR1, -NH2, C1-C4알킬아미노, C1-C4디알킬아미노, -NHSO2R1, -NHCOR1, -NO2및 -아릴로 이루어진 그룹으로부터 독립적으로 선택된 1 내지 3개의 치환체로 임의로 치환되고, 분지되거나 융합되며, 5개 내지 12개의 탄소원자를 함유하는 비사이클 아민이고; Ar은 R4로부터 독립적으로 선택된 3개 이하의 치환체로 임의로 치환된 페닐 또는 나프틸이고; W는 (a) -CH2-, (b) -CH=CH-, (c) -O-, (d) -NR2-, (e) -S(O)n-, (f)(g) -CR2(OH)-, (h) -CONR2-, (i) -NR2CO-, (j)또는 (k)-C≡C-이고; R은 (a) 할로겐, (b) -NR2R3-, (c) -NHCOR2, (d) -NHSO2R2, (e) -CR2R3OH, (f) -CONR2R3, (g) -SO2NR2R3, (h) 하이드록실, (i) R1O-, 또는 (j)이고; R1은 C1-C6알킬, 할로겐, 알콕시, 하이드록시 및 카복시에서 독립적으로 선택되는 3개 이하의 치환체로 임의로 치환되는 C1-C6알킬 또는 페닐이고; R2및 R3은 독립적으로 (a)수소, 또는 (b) C1-C|4알킬이고; R4는 (a) 수소, (b) 할로겐, (c) C1-C4알킬, (d) C1-C4알콕시, (e)C|1-C4아실옥시, (f) C1-C4알킬티오, (g) C1-C4알킬설피닐, (h) C1-C4알킬설포닐, (i)하이드록(C1-C4)알킬, (j) 아릴(C1-C4)알킬, (k) -CO2H-, (l) -CN, (m) -CONHOR, (n) -SO2NHR, (o) -NH2, (p) C1-C4알킬아미노, (q) C1-C4디알킬아미노, (r) -NHSO2R, (s) -NO2, 또는 (t)-아릴이고; R5및 R6은 독립적으로 C1-C8알킬이거나 C3-C|10카보사이클 고리를 형성하고; R7및 R8은 독립적으로 (a) 페닐, (b) 포화 또는 불포화 C3-C10카보사이클 고리, (c) -O-, -N- 및 -S-로부터 선택되는 2개 이하의 헤테로 원자를 함유하는 C3-C10헤테로사이클 고리, (d) H, 또는 (e) C1-C6알킬이거나, (f) R5및 R6와 함께 3 내지 8원 질소 함유 고리를 형성하고; 선형 또는 고리형태의 R7및 R9은 C1-C6알킬, 할로겐 알콕시, 하이드록시 및 카복시에서 독립적으로 선택되는 3개 이하의 치환체로 임의로 치환될 수 있고; R7및 R9에 의해 형성된 고리는 페닐 고리에 임의로 융합될 수 있고; m은 1,2 또는 3이고; n은 0,1 또는 2이고; p는 0,1,2 또는 3이고; q는 0,1,2 또는 3이나; 단 A, B 및 Z가 각각 -CH=이고, Y가 4-하이드록시 페닐이고, X가 황이고, D가 -CO-이고, E가 1,4-이치환된 페닐이고, R이 -OH이고, Z1이 -OCH2CH2인 경우 G는 반드시또는 -N-(C1-C4알킬)2이 아니어야 하고; R이인 경우, G는 반드시이 아니어야 하고; A, B 및 Z가 각각 -CH=이고, X가 S이고, Y가 사이클로알킬 또는 사이클로알케닐이고, D가이고, E가 1,4-이치환된 페닐이고, Z'이 메틸렌, O(CH2)m-, 에틸렌 또는 프로필렌인 경우, G는 반드시또는이 아니어야 하고; D가 -CR2R3이고, W가 -CO- 또는 -S(O)n-인 경우, G는 반드시 a) -NR|11R12(여기서 R11및 R12는 독립적으로 수소, 알킬, 알케닐, 사이클로알킬, 할로알킬, 아릴 또는 아릴알킬이다) 또는 (b)(여기서, n은 0,1 또는 2이고, m은 1,2 또는 3이고, Z2는 -NH-, -O-, -S- 또는 -CH2이다)가 아니어야 하고; A, B 및 Z가 각각 -CH=이고, Y가 4-하이드록시페닐이고, X가 -CH2-CH2- 또는 -CH=CH-이고, D가 CO이고 , E가 1,4-이치환된 페닐이고, Z1이 -OCH2CH2인 경우, G는 반드시또는가 아니어야 한다.
  2. 제 1항에 있어서, R이 -OH인 화합물.
  3. 제 1항에 있어서, A, B 및 Z가 독립적으로 -CH= 및 -CF=로부터 선택되는 화합물.
  4. 제 1항에 있어서, X가 -S-인 화합물.
  5. 제 1항에 있어서, D가 -CO- 또는 -CH2인 화합물.
  6. 제 1항에 있어서, E가 1,4-결합된 페닐, 피리딜, 피리미딘,또는인 화합물.
  7. 제 1항에 있어서, Z1이 -OCH2CH2-, -CH2CH2-, -CH|2-, , -C≡C-CH2-이거나, 또는 Z가 G와 함께인 화합물.
  8. 제 1항에 있어서, G가
    또는인 화합물.
  9. 제 1항에 있어서, R이 -OH이고; A, B 및 Z가 -CH=이고; X가 S이고; Y가또는이고; D가또는 -CH2-이고; E가또는이고; Z1이 -CH2-CH2-CH2- 또는 인 화합물.
  10. 제 1항에 있어서, A, B 및 Z가 -CH=이고; X가 -S-이고; Y가 페닐, 4-하이드록시페닐, 4-클로로페닐, 4-플루오로페닐,또는이고; R이 -OH이고; D가 -CO- 또는 -CH2-이고; E가 페닐 또는 피리딜이고; Z1이 -OCH2CH|2-, -C≡C-CH2-, -OCH2- 또는 -NHCH2CH2-인 화합물.
  11. 제 10항에 있어서, G가(여기서 n은 0,1 또는 2이고, m은 1,2 또는 3이고 Z2는 -NH, -O-, -S- 또는 -CH2이다)인 화합물.
  12. 제 10항에 있어서, G가
    또는 인 화합물.
  13. 제 10항에 있어서, G가
    인 화합물.
  14. 제 1항에 있어서, Z가 =N- 또는 -CF=이고; X가 -S-이고; Y가 4-하이드록시페닐이고; R이 -OH-이고; D가 -CO- 또는 -CH2-이고; E가 페닐 또는 피리딜이고; Z1이 -OCH2CH2-인 화합물.
  15. 제 1항에 있어서, {4-[2-(2-아자-비사이클로[2,2,1]헵트-2-일)-에톡시]-페닐}-[6-하이드록시-2-(4-하이드로시-페닐)-벤조[b]티오펜-3-일]-메탄온인 화합물.
  16. 제 1항에 있어서, [6-하이드록시-2-(4-하이드록시-페닐)-벤조[b]티오펜-3-일]-[4-(1-메틸-피페리딘-2-일-메톡시)-페닐]-메탄온인 화합물.
  17. 제 1항에 있어서, [2-(4-플루오로-페닐)-6-하이드록시-벤조[b]티오펜-3-일]-[4-(2-피페리딘-1-일)에톡시]-페닐]-메탄온인 화합물.
  18. 제 1항에 있어서, [6-하이드록시-2-(4-하이드록시-페닐)벤조[b]티오펜-3-일][4-(3-피페리딘-1-일-프로프-1-이닐)-페닐]-메탄온인 화합물.
  19. 제 1항에 있어서, 2-(4-하이드록시-페닐)-3-[4-(2-피페리딘-1-일-에톡시)-벤질]벤조[b]티오펜-6-올인 화합물.
  20. 에스트로겐 결핍과 관련된 뼈손실 치료를 필요로 하는 포유동물에게 제 1항의 화합물을 뼈손실을 치료하기에 효과적인 양으로 투여함을 포함하는, 포유동물의 에스트로겐 결핍과 관련된 뼈손실 치료 방법.
  21. 심혈관 질환의 치료를 필요로 하는 포유동물에게 제 1항의 화합물을 심혈관 질환을 치료 또는 예방하기에 효과적인 양으로 투여함을 포함하는, 포유동물의 심혈관 질환의 치료 또는 예방 방법.
  22. 에스트로겐 결핍상태에 의해 유발된 질병 또는 증상의 치료 또는 예방이 필요한 포유동물에게 제 1항의 화합물을 에스트로겐 결핍 상태에 의해 유발된 질병 또는 증상의 치료에 효과적인 양으로 투여함을 포함하는, 포유동물의 에스트로겐 결핍상태에 의해 유발된 질병 또는 증상의 치료 또는 예방 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960701899A 1993-10-12 1994-09-19 에스트로겐 작용물질로서의 벤조티오펜 및 관련 화합물 (benzothiophenes and related compounds as estrogen agonists) KR960704874A (ko)

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CA2173243A1 (en) 1995-04-20
US6756388B1 (en) 2004-06-29
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FI944771A (fi) 1995-04-13
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PL313905A1 (en) 1996-08-05
NO961432D0 (no) 1996-04-11
AU7545394A (en) 1995-05-04
BR9407790A (pt) 1997-03-18
EP0723537A1 (en) 1996-07-31
WO1995010513A1 (en) 1995-04-20
CN1133040A (zh) 1996-10-09
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JPH08511273A (ja) 1996-11-26
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HUT75231A (en) 1997-04-28

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