KR960704842A - 저콜레스테롤혈증제로서 유용한 하이드록시-치환된 아제티디논 화합물 (Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents) - Google Patents
저콜레스테롤혈증제로서 유용한 하이드록시-치환된 아제티디논 화합물 (Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents)Info
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Abstract
Description
Claims (22)
- 하기 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염.상기 식에서, Ar1및 Ar2는 독립적으로 아릴 및 R4- 치환된 아릴로 이루어진 그룹중에서 선택되고; Ar3은 아릴 또는 R5- 치환된 아릴이며; X,Y 및 Z는 독립적으로 -CH2-, CH(저급 알킬)- 및 -C(디저급 알킬)-로 이루어진 그룹중에서 선택되고;R 및 R2는 독립적으로 -OR6, -O(CO)R6-O(CO)OR9및 -O(CO)NR6R7으로 이루어진 그룹중에서 선택되며; R1및 R3은 독립적으로 수소, 저급 알킬 및 아릴로 이루어진 그룹중에서 선택되고; -q는 0 또는 1이며; r은 0 또는 1이고; m,n 및 p는 독립적으로 0,1,2,3, 또는 4이며; 단, q 및 r 중의 하나 이상은 1이고 m,n,p,q 및 r의 합은 1,2,3,4,5 또는 6이며; p가 0이고 r이 1일때 m,q 및 n의 합은 1,2,3,4 또는 5이며; R4는 독립적으로 저급 알킬, -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7,-NR6(CO)R7, -NR6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, CONR6R7, - COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10-CONR6R7, -(저급 알킬렌)COOR6-CH=CH=COOR6-CF3,-CN, -NO2및 할로겐으로 이루어진 그룹중에서 선택된 1 내지 5개의 치환체이고; R5는 독립적으로 -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7,-NR6(CO)R7, -NR|6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, CONR6R7, - COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10-CONR6R7, -(저급 알킬렌)COOR6및 -CH=CH=COOR6으로 이루어진 그룹중에서 선택된 1 내지 5개의 치환체이며; R6, R7및 R8은 독립적으로 수소, 저급 알킬, 아릴 및 아릴-치환된 저급 알킬로 이루어진 그룹중에서 선택되고; R9는 저급 알킬, 아릴 또는 아릴-치환된 저급 알킬이다.
- 제1항에 있어서 Ar1이 페닐 또는 R4-치환된 페닐이고,Ar2가 페닐 또는 R4-치환된 페닐이며, Ar3이 R5-치환된 페닐인 화합물.
- 제2항에 있어서 Ar1이 R4-치환된 페닐(여기서,R6는 할로겐이다)이고, Ar2가 R4-치환된 페닐[여기서,R4는 할로겐 또는 -OR5(여기서, R6는 저급 알킬 또는 수소이다)이다]이며, Ar3이 R5-치환된 페닐[여기서,R5는 -OR6(여기서, R5는 저급 알킬 또는 수소이다)이다]인 화합물.
- 제1항 내지 제3항 중 어느 한 항에 있어서, X,Y 및 Z가 각각 -CH2-이고,R1및 R3가 각각 수소이며, R 및 R2가 각각 -OR5(여기서, R5는 수소이다)이고, m,n,p,q, 및 r의 합이 2,3,또는 4인 화합물.
- 제1항 내지 제4항 중 어느 한 항에 있어서, m,n 및 r이 각각 0이고, q가 1이며, p가 2인 화합물.
- 제1항 내지 제4항 중 어느 한 항에 있어서, p,q 및 n이 각각 0이고, r이 1이며, m이 2 또는 3인 화합물.
- 제1항에 있어서 rel 3(R)-(2-(R)-하이드록시-2-페닐에틸)-4(R)-(4 메톡시페닐)-1-페닐-2-아제티디논; rel 3(R)-(2-(R)-하이드록시-2-페닐에틸)-4(S)-(4-메톡시페닐)-1-페닐-2-아제티디논; 3(S)-(1-(S)-하이드록시-3-페닐프로필)-4(S)-(4 메톡시페닐)-1-페닐-2-아제티디논;3(S)-(1-(R)-하이드록시-3-페닐프로필)-4(S)-(4 메톡시페닐)-1-페닐-2-아제티디논;3(R)-(1(R)-하이드록시-3-페닐프로필)-4(S)-(4-메톡시페닐)-1-페닐_2-아제티디본;rel-3(R)-[(S)-하이드록시-2-나프탈레닐)메틸]-4(S)-(4-메톡시페닐)-1-페닐-2-아제티디논; rel-3(R)-[(R)-하이드록시-2-나프탈레닐)메틸]4(S)-(4 메톡시페닐)-1-페닐-2-아제티디논; 3(R)-(3(R)-하이드록시-3-페닐프로필)-1,4(S)-비스-(4-메톡시페닐)-1-페닐-2-아제티디논; 3(R)-(3(S)-하이드록시-3-페닐프로필)-1,4(S)-비스-(4-메톡시페닐)-2-아제티디논;4(S)-(4-하이드록시페닐)-3(R)-(3(R)하이드록시-3-페닐프로필)-1-(4-메톡시페닐)-2-아제티디논;4(S)-(4-하이드록시페닐)-3(R)-(3(S)하이드록시-3-페닐프로필)-1-(4-메톡시페닐)-2-아제티디논; rel-3(R)-[3(RS)-하이드록시-3-[4-메톡시메톡시)-페닐]프로필]-1,4(S)-비스-(4-메톡시페닐)-2-아제티디논; 1-(4-플루오로페닐)-3(R)-[3(S)-(4-플루오로페닐)-3-하이드록시프로필)]-4(S)-(4-하이드록시페닐)-2-아제티디논;1-(4-플루오로페닐)-3(R)[3(R)-(4-플루오로페닐)-3-하이드록시프로필)]-4(S)-(4-하이드록시페닐)-2-아제티디논;4(S)-[4-(아세틸옥시)페닐]-3(R)-(3(R)-하이드록시-3-페닐프로필)-1-(4-메톡시페닐)-2-아제티디논;4(S)-[4-(아세틸옥시)페닐]-3(R)-(3(S)-하이드록시-3-페닐프로필)-1-(4-메톡시페닐)-2-아제티디논;1-(4-플루오로페닐)-3(R)-[3(S)-(4-플루오로페닐)-3-하이드록시프로필)]-4(S)-(4-페닐메톡시)페닐]-2-아제티디논;3(R)-[3(R)-(아세틸옥시)-3-페닐프로필]-1,4(S)-비스-(4-메톡시페닐)-2-아제티디논;3(R)-[3(S)-(아세틸옥시)-3-페닐프로필]-1,4(S)-비스-(4-메톡시페닐)-2-아제티디논;3(R)-[3(R)-(아세틸옥시)-3-(4-플루오로페닐)프로필]-4(S)-[4-(아세틸옥시)-페닐]-1-(4-플루오로페닐)-2-아제티디논;3(R)-[3(S)-(아세틸옥시)-3-(4-플루오로페닐)프로필]-4(S)-[4-(아세틸옥시)-페닐]-1-(4-플루오로페닐)-2-아제티디논;3(R)-[3(R)-(아세틸옥시)-3-(4-클로로페닐)프로필]-4(S)-[4-(아세틸옥시)-페닐]-1-(4-클로로페닐)-2-아제티디논;3(R)-[3(S)-(아세틸옥시)-3-(4-클로로페닐)프로필]-4(S)-[4-(아세틸옥시)-페닐]-1-(4-클로로페닐)-2-아제티디논 및 rel 1-(4-플루오로페닐)-4(S)-(하이드록시페닐)-3(R)-(1(R)-하이드록시-3-페닐프로필)-2-아제티디논으로 이루어진 그룹중에서 선택된 화합물.
- 약제학적으로 허용되는 담체중에 유효량의 제1항 내지 제7항 중 어느 한 항의 화합물을 단독으로 또는 클레스테롤 생합성 억제제와 배합하여 포함하는, 아테롬성 동맥경화증을 치료 또는 예방하거나 혈장 콜레스테롤 수준을 감소시키기 위한 약제학적 조성물.
- 아테롬성 동매경화증을 치료 또는 예방하거나 혈장 콜레스테롤 수준을 감소시키기 위한 약제의 제조에 있어서 제1항 내지 제7항 중 어느 한 항에 따른 화합물의 용도.
- 제1항 내지 제7항 중 어느 한 항에 정의된 화합물을 약제학적으로 허용되는 담체와 혼합함을 특징으로 하여, 제8항의 약제학적 조성물을 제조하는 방법.
- 제1항 내지 제7항 중 어느 한 항에 정의된 화합물 및 콜레스테롤 생합성 억제제를 약제학적으로 허용되는 담체와 혼합함을 특징으로 하여, 제8항의 약제학적 조성물을 제조하는 방법.
- 아테롬성 동매경화증의 치료 또는 예방에서 또는 혈장 클레스테롤 수준 감소를 위한 콜레스테롤 생합성 억제제와의 배합 사용용 약제 제조시 제1항 내지 제7항 중 어느 한 항에 따른 화합물의 용도.
- 아테롬성 동매경화증의 치료 또는 예방에서 또는 혈장 클레스테롤 수준 감소를 위한 제1항 내지 제7항 중 어느 한 항에 따른 화합물과의 배합 사용용 약제 제조시 콜레스테롤 생합성 억제제의 용도.
- 약제학적으로 허용되는 담체중의 유효량의 콜레스테롤 생합성 억제제를 함유하는 약제학적 조성물을 제1용기에 포함하고 약제학적으로 허용되는 담체중의 유효량의 제1항 내지 제7항 중 어느 한항에 정의된 화합물을 함유하는 약제학적 조성물을 제2용기에 포함하는, 아테롬성 동맥경화증을 치료 또는 예방하거나 혈장 콜레스테롤 수준을 감소시키기 위한 배합 사용용 약제학적 조성물을 단일 팩키지중의 분리 용기에 포함하는 키트.
- 제1항 내지 제7항 중 어느 한 항에 정의된 유효량의 화합물을 단독으로 또는 유효량의 콜레스테롤 생합성 억제제와 배합하여 아테롬성 동맥경화증의 치료를 필요로 하는 포유동물에게 투여함을 특징으로 하여, 아테롬성 동맥경화증을 치료 또는 에방하거나 혈장 코레스테롤 수준을 감소시키는 방법.
- 제8항, 제11항 또는 제14항에 있어서, 콜레스테롤 생합성 억제제가 HMG CoA환원효소 억제제, 스쿠알렌 합성 억제제 및 스쿠알렌 에폭시다제 억제제로 이루어진 그룹중에서 선택되는 약제학적 조성물.
- 제16항에 있어서, 콜레스테롤 생합성 억제제가 로바스타틴, 프라바스타틴, 플루바스타틴, 심바스타틴,CI-981,DMP-565,L-659,699, 스쿠알렌스타틴 1 및 NB-598로 이루어진 그룹중에서 선택되는 약제학적 조성물.
- 제12항 또는 제13항에 있어서, 콜레스테롤 생합성 억제제가 제16항 또는 제17항에 정의된 바와 같은 억제제인 용도.
- 제15항에 있어서, 콜레스테롤 생합성 억제제가 제16항 또는 제17항에 정의된 바와 같은 억제제인 방법.
- (a)일반식(A)의 락톤을 강 염기로 처리하고, (b)단계(a)의 생성물을 일반식의 이민(여기서, Ar20은 Ar2,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이고;Ar30은 Ar3,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이다)과 반응시키며,(c)반응물을 산으로 켄칭시키고,(d) R′,Ar10, Ar20및 Ar30으로부터 존재하는 보호그룹을 임의로 제거하며, (e)R3치환체가 부착되어 있는 탄소 및 R에서의 치환기, 및 Ar1, Ar2및 Ar3에서의 하이드록시 또는 아미노 치환기를 임의로 작용화시킴을 특징으로 하여, 일반식(ⅠA)의 화합물을 제조하는 방법.상기 식에서,Ar1, Ar2, Ar3,X,Y,Z,R,R1,R3,m,n,p및 q는 제1항에 정의한 바와 같고, 단, m,n,p및 q이 합은 1내지 6이며; R′는 보호된 하이드록시 그룹이고; Ar10은 상기 정의된 바와 같은 Ar1,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이다.
- (a)일반식(B)의 락톤을 강 염기로 처리하고, (b)단계(a)의 생성물을 일반식의 이민(여기서, Ar20은 Ar2,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이고;Ar30은 Ar3,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이다)과 반응시키며,(c)반응물을 산으로 켄칭시키고,(d) R2′,Ar10, Ar20및 Ar30으로부터 존재하는 보호그룹을 임의로 제거하며, (e)R1치환체가 부착되어 있는 탄소에서의 치환기 및 Ar1, Ar2및 Ar3에서의 하이드록시 또는 아미노 치환기를 작용화시킴을 특징으로 하여, 일반식(ⅠB)의 화합물을 제조하는 방법.상기 식에서,Ar1, Ar2, Ar3,X,Y,Z,R,R1,R2,R3,m,n,p및 r은 제1항에 정의한 바와 같고, 단, m,n,p및 r의 합은 1내지 6이며;r 및 n이 각각 0이면, p는 1 내지 4이고; Ar10은 상기 정의된 Ar1,적절히 보호된 하이드록시-치환된 아릴 또는 적절히 보호된 아미노-치환된 아릴이고;R2′는 보호된 하이드록시 그룹이다.
- 공정 A:일반식(Ⅲ)의 에스테르(여기서,R1,R3,X,Y,Z,m,n,p,q및 r은 제1항에 정의한 바와 같고, R1및 Ar10은 제20항에 정의한 바와 같으며;R2′는 제21항에 정의한 바와 같고; R10은 저급 알킬, 메틸 또는 10-(디이소프로필설폰아미도)이소보르닐이다)를 강 염기로 처리하고, 이어서 일반식(Ⅱ)의 이민(여기서, Ar20및 Ar30은 제20항에 정의한 바와 같다)으로 처리하여 제1항에 정의된 바와 같은 일반식(Ⅰ)의 화합물을 수득하거나;공정 B:일반식(Ⅴ)의 아제티디논(여기서,Ar20및 Ar30은 제20항에 정의한 바와 같다)을 강 염기로 처리하고, 이어서 일반식(Ⅵ)의 알데하이드 또는 케톤(여기서,R1,R3,X,Y,m,n 및 q는 제1항에 정의한 바와 같고, R′ 및 Ar10은 제20항에 정의한 바와 같다)으로 처리하여 r이 1이고 p가 0이며 R2가 OH인 일반식(I)의 화합물인 일반식 (Ie)의 화합물을 수득하거나;공정 C:일반식(X)의 화합물(여기서, 변수는 상기 공정 A 및 공정 B에 정의한 바와 같다)을 트리알킬포스핀 및 디알킬아조디카복실레이트로 폐환시켜 일반식(I)의 상대적인 3,4-트란스 화합물인 일반식(Ia)의 화합물을 수득하거나;공정 D:일반식(Ⅱ)의 이민(여기서,Ar20및 Ar30은 공정 A에 정의한 바와 같다)을 일반식(Ⅶ)의 활성화된 카복실산(여기서, L은 Cl,OP(O)(Cl)OPh,2-옥시-N메틸피리디늄 요오다이드 또는 2-티오피리딜 에스테르이고, 나머지 변수는 공정 A 및 공정 B에 정의한 바와 같다)으로 3급 아민 염기의 존재하에 처리하거나;공정 E:일반식(ⅩⅢ) 의 화합물(여기서, 변수는 상기 공정 A 및 공정 B에 정의한 바와 같다)을 강 비-친핵성 염기로 처리하여 일반식(I)의 상대적인 3,4-트란스 화합물인 일반식(Ia)의 화합물을 수득하거나;공정 F:일반식 (ⅩⅥ)의 알데하이드 또는 케톤(여기서, 변수는 상기 공정 A및 공정 B에 정의한 바와 같다)을 Ar10-유기금속성 시약(여기서, Ar10은 상기 공정 A에 정의한 바와 같다)으로 처리하여 R이 OH인 일반식(I)의 화합물인 일반식(Ig)의 화합물을 수득하고, 이어서 보호 그룹을 임의로 제거하거나;공정 G:일반식(ⅩⅧ)의 화합물(여기서, Hal은 Cl,Br 또는 I이고, Ar1, Ar2, Ar3,R1,R2,R3,Y,Z,q,n,r및 p는 제1항에 정의한 바와 같다)을 테트라알킬-암모늄 염 또는 테트라 n-부틸암모늄 트리플루오로아세테이트로 처리하고, 이어서 온화한 염기로 처리하여 m이 0이고, R이 OH인 일반식(I)의 화합물인 일반식(Ii)의 화합물을 수득하거나;공정 H:일반식(ⅩⅩ)의 케톤(여기서,Ar10, Ar20, Ar30,R2′,R3,X,Y,Z,m,n,r및 p는 공정 A항에 정의한 바와 같다)을 환원시켜 q가 1이고 R이 OH이며 R1이 H이고 나머지 변수가 일반식(ⅩⅩ)에 정의한 바와 같은 일반식(I)의 화합물인 일반식(Ij)의 화합물을 수득하고, 이어서 보호 그룹을 임의로 제거하거나;공정 I:일반식(ⅩⅩⅥ) 의 알릴 알콜(여기서,Ar1, Ar2, Ar3및 R1는 제1항에 정의한 바와 같고, X′Y′중 및 하나는 -CH=CH-이고 다른 하나는 -CH=CH-,-CH2-,CH2CH2-,-CH(저급 알킬)-,-CH(디저급 알킬)또는 결합이다)을 수소화하여 Ar1, Ar2, Ar3및 R1이 상기 정의한 바와 같고 X″ 및 Y″중 하나가 -CH2=CH2-이고 다른 하나가 -CH2=CH2-,-CH2-,-CH(저급 알킬)-,-CH(디저급 알킬)또는 결합으로 이루어진 그룹중에서 선택되는 일반식(I)의 화합물인 일반식(Ik)의 화합물을 수득하거나;공정 I:일반식(ⅩⅩⅨ)의 알콜 (여기서, 변수는 공정 A에 정의한 바와 같다)을 트리스(트리메틸실릴)실란으로 라디칼개시제의 존재하에 탈할로겐화시켜 일반식(Im)및 (In) 의 이성체의 혼합물(여기서, 변수는 상기 정의한 바와 같다)을 수득하고, 이어서 임의로 이성체를 분리하고 보호 그룹을 제거함을 특징으로 하여, 일반식(I)의 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100820983B1 (ko) * | 2001-01-26 | 2008-04-10 | 쉐링 코포레이션 | 치환된 아제티딘온 화합물을 포함하는 약제학적 조성물 |
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