KR890011859A - 3,5-디하이드록시 카복실산 및 이의 유도체, 이의 제조방법, 약물로서의 이의 용도, 약제학적 생성물 및 중간체 - Google Patents
3,5-디하이드록시 카복실산 및 이의 유도체, 이의 제조방법, 약물로서의 이의 용도, 약제학적 생성물 및 중간체 Download PDFInfo
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Abstract
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Claims (10)
- 일반식(Ⅰ)의 3,5-디하이드록시 카복실산 및 이의 유도체 및 일반식(Ⅱ)의 상응하는 락톤.상기식에서, X-Y는 구조식 -CH=CH- 또는 -CH2-CH2-의 라디탈을 나타내고, R1, R2및 R3는 서로 독립적으로 수소; 말단 탄소상에서 탄소수 3 내지 6의 포화 또는 불포화 사이클릭 탄화수소라디칼에 의해 임의로 치환될 수 있는 탄소수 6이하의 포화 또는 불포화, 직쇄 또는 측쇄 탄화수소라디칼을 나타내거나, 탄소수 3내지 7의 포화 또는 이중 불포화 사이클릭 탄화수소라디칼; 페닐, 푸릴, 티에닐 및 피리딜 중에서 선택된 방향족라디칼(이는 핵에 할로겐, 트리플루오로메틸, 각각의 경우에 탄소수 6이하의 알킬 또는 알케닐, 하이드록실, 탄소수 1 내지 6의 알콕시, 카복실 또는 알콕시 잔기의 탄소수가 1 내지 6인 카브알콕시그룹중에서 선택된 동일하거나 상이한 치환체 1 내지 3개를 임의로 함유할 수 있다)을 나타내고, R4는 수소, 탄소수 8이하의 직쇄 또는 측쇄, 포화 또는 불포화 탄화수소라디칼, 탄소수 1 내지 4의 모노- 또는 디하이드록시알킬, 페닐 또는 벤질라디칼 (이의 핵은 할로겐 또는 탄소수 1 내지 4의 알킬라디칼에 의해 1회 또는 2회 치환될 수 있다)이거나, 알칼리금속 또는 암모늄이온을 나타낸다.
- 제1항에 있어서, R1및 R2가 탄소수 1 내지 4의 직쇄 또는 측쇄 알칼라디칼 ; 탄소수 5 내지 6의 사이클로알킬라디칼 ; 탄소수 5 내지 6의 환크기를 갖는 사이클로알킬메틸 또는 사이클로알케닐메틸라디칼 ; 할로겐, 트리플루오로메틸 탄소수 1 내지 4의 알킬, 하이드록실, 탄소수 1 내지 4의 알콕시 또는 알콕시잔기의 탄소수가 1 내지 4인 카브알콕시 중에서 선택된 동일하거나 상이한 치환체 1 내지 3개를 임의로 함유할 수 있는 페닐라디칼을 나타내고, R3가 수소, 탄소수 6이하의 직쇄 또는 측쇄알킬 또는 알케닐라디칼, 각각의 탄소수가 5 내지 6인 사이클로알킬 또는 사이클로알케닐라디칼, 페닐 또는 피리딜라디칼을 나타내고, 방향족라디칼이 할로겐, 탄소수 1 내지 4의 알킬, 하이드록실, 탄소수 1 내지 4의 알콕시 또는 알킬잔기의 탄소수가 1내지 4인 카브알콕시 중에서 선택된 동일하거나 상이한 치환체 1 내지 3개를 임의로 함유할 수 있으며, R4가 수소, 메틸, 에틸, 이소프로필, 이소부틸, 벤질, 나트륨, 칼륨, 암모늄(NH4) 또는 메틸트리스 (하이드록시메틸) 암모늄을 나타내는 일반식(Ⅰ) 및 (Ⅱ)의 화합물.
- 제1항에 있어서, R1이 메틸, 이소프로필, 2급-부틸, 3급-부틸, 사이클로헥실, 페닐, 4-클로로-페닐, 4-플루오로페닐, 4-메톡시페닐, 4-플루오로-3-메틸-페닐, 3,5-디메틸페닐, 사이클로헥실메틸 또는 트리플루오로메틸페닐을 나타내고, R2가 메틸, 이소프로필, 2급-부틸, 3급-부틸, 사이클로헥실, 페닐, 4-클로로페닐, 4-플루오로페닐, 4-에톡시페닐, 4-플루오로-3-메틸페닐, 3,5-디메틸페닐, 사이클로헥실메틸 또는 4-트리플루오로메틸페닐을 나타내며, R3가 수소, 메틸, 이소프로필, 2급-부틸, 3급-부틸, 사이클로헥실, 페닐, 4-플루오로페닐, 2,5-디메틸페닐, 3,5-디메틸페닐 또는 4-트리플루오로메틸페닐을 나타내고, R4가 수소, 메틸, 에틸 나트륨 또는 칼륨인 일반식(I) 및 (II)의 화합물.
- 제1항에 있어서, 일반식(Ⅰ)의 화합물.
- a) 일반식(Ⅲ)의 적당히 치환된 알데하이드를 일반식(Ⅳ)의 상응한는 하이드록시 케토 에스테르로 전환시키고,b) 일반식(Ⅳ)의 하이드록시 케토 에스테르를 일반식(Ⅰ)의 상응하는 3,5-디하이드록시 화합물로 전환시키며, 경우에 따라 생성된 화합물을 가수분해시켜 R4가 알칼리금속 양이온을 나타내는 일반식(Ⅰ)의 화합물을 수득하고, 경우에 따라 이로부터 유리산(여기에서 R4는 수소이다)을 유리시킨 다음, 경우에 따라 유리산을 R4가 수소를 제외하고는 일반식(Ⅰ)에서 정의한 바와 같은 일반식(Ⅰ)의 화합물로 전환시키고,c) 경우에 따라 생성된 일반식(Ⅰ)의 화합물을 일반식(Ⅱ)의 락톤으로 전환시킨 다음,d) 경우에 따라 X-Y가 CH=CH그룹을 나타내는 생성된 화합물을 가수분해하여 X-Y가 CH2-CH2-그룹인 화합물을 수득함을 특징으로하여, 일반식(Ⅰ) 및 (Ⅱ)의 화합물을 제조하는 방법.상기식에서 X-Y, R1, R2및 R3는 제1항에서 정의한 바와 같고, R4는 탄소수 1내지 8의 알킬이다.
- 제1항에 따른 화합물을 함유하는 약제학적 생성물.
- 과콜레스테린 혈증의 예방 및 치료를 위한 제1항에 따른 화합물의 용도.
- 일반식(Ⅲ)의 화합물상기식에서 X-Y, R1, R2및 R3는 제1항에서 정의한 바와같다.
- 일반식(Ⅴ)의 화합물.상기식에서 X-Y, R1, R2및 R3는 제1항에서 정의한 바와같고, R4는 탄소수 1 내지 8의 알킬이다.
- 일반식(Ⅵ)의 화합물, 일반식(Ⅶ)의 화합물, 일반식(Ⅷ)의 화합물, 및 일반식 (Ⅸ)의 화합물.상기식에서 R1, R2, R3및 X-Y는 제1항에서 정의한 바와같고, R6는 산보호 그룹이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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DE3800785A DE3800785A1 (de) | 1988-01-09 | 1988-01-14 | Substituierte 7-(pyridazin-5-yl)-3,5-dihydroxyheptan(en)- saeuren, ihre entsprechenden (delta)-lactone bzw. derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
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DE3826814A1 (de) * | 1988-08-06 | 1990-02-08 | Hoechst Ag | Neue 6-fluor-3,5-dihydroxycarbonsaeuren und deren derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
DE3832570A1 (de) * | 1988-09-24 | 1990-03-29 | Hoechst Ag | 7-substituierte derivate der 3,5-dihydroxyhept-6-insaeure, verfahren zur ihrer herstellung, ihre verwendung als arzneimittel, sowie zwischenprodukte |
DK483689A (da) * | 1988-10-03 | 1990-04-04 | Glaxo Group Ltd | Imidazolderivater |
IE903606A1 (en) * | 1989-10-10 | 1991-04-24 | Glaxo Group Ltd | Chemical compounds |
IT1237792B (it) * | 1989-12-21 | 1993-06-17 | Zambon Spa | Composti attivi come inibitori dell'enzima hmg-coa reduttasi |
JPH054943A (ja) * | 1990-08-30 | 1993-01-14 | Sagami Chem Res Center | 光学活性β,δ−ジケト酸エステル及びその還元体 |
DE4208051A1 (de) * | 1992-03-13 | 1993-09-16 | Bayer Ag | Substituierte phenylessigsaeureamide |
DE4208052A1 (de) * | 1992-03-13 | 1993-09-16 | Bayer Ag | Imidazolyl substituierte phenylessigsaeureamide |
DE4212796A1 (de) * | 1992-04-16 | 1993-10-21 | Bayer Ag | Propenoyl-imidazolderivate |
DE4215588A1 (de) * | 1992-05-12 | 1993-11-18 | Bayer Ag | Biphenylmethyl-substituierte Pyridone |
DE4215587A1 (de) * | 1992-05-12 | 1993-11-18 | Bayer Ag | Sulfonylbenzyl-substituierte Benzo- und Pyridopyridone |
DE4220983A1 (de) * | 1992-06-26 | 1994-01-05 | Bayer Ag | Imidazolyl-substituierte Phenylpropion- und -zimtsäurederivate |
DE4319041A1 (de) * | 1992-10-23 | 1994-04-28 | Bayer Ag | Trisubstituierte Biphenyle |
EP1628665A2 (en) * | 2003-04-16 | 2006-03-01 | Amgen Inc. | 3-phenyl-4-(pyrimidin-2-yl)-6-(piperidin-4-yl) derivatives and related compounds as tnf-alpha and il-1 inhibitors for the treatment of inflammations |
US8372877B2 (en) | 2010-04-16 | 2013-02-12 | Cumberland Pharmaceuticals | Stabilized statin formulations |
US20130210860A1 (en) | 2010-10-06 | 2013-08-15 | Kowa Co., Ltd. | Prophylactic and/or therapeutic agent against lymphedema |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2752820A1 (de) * | 1977-11-26 | 1979-05-31 | Bayer Ag | Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
US4375475A (en) * | 1979-08-17 | 1983-03-01 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
US4540796A (en) * | 1982-05-03 | 1985-09-10 | Merck & Co., Inc. | Process for preparing inhibitors of 3-hydroxy-3-methylglutaryl coenzyme a reductase via a chiral synthon |
US4613610A (en) * | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
HU198711B (en) * | 1984-06-22 | 1989-11-28 | Sandoz Ag | Process for producing mevalolacton, derivatives and pyrazol analogues and pharmaceutical composition containing them |
US4647576A (en) * | 1984-09-24 | 1987-03-03 | Warner-Lambert Company | Trans-6-[2-(substitutedpyrrol-1-yl)alkyl]-pyran-2-one inhibitors of cholesterol synthesis |
US4681893A (en) * | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
US4735958A (en) * | 1986-12-22 | 1988-04-05 | Warner-Lambert Company | Trans-6-[2-[2-(substituted-phenyl)-3- (or 4-) heteroaryl-5-substituted-1H-pyrrol-1-yl]-ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one inhibitors of cholesterol biosynthesis |
US4761419A (en) * | 1987-12-07 | 1988-08-02 | Warner-Lambert Company | 6-(((substituted)quinolinyl)ethyl)-and ethenyl)tetrahydro-4-hydroxypyran-2-one inhibitors of cholesterol biosynthesis |
DE3826814A1 (de) * | 1988-08-06 | 1990-02-08 | Hoechst Ag | Neue 6-fluor-3,5-dihydroxycarbonsaeuren und deren derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
-
1988
- 1988-01-14 DE DE3800785A patent/DE3800785A1/de not_active Withdrawn
-
1989
- 1989-01-03 EP EP19890100031 patent/EP0324347A3/de not_active Withdrawn
- 1989-01-05 FI FI890050A patent/FI890050A/fi not_active IP Right Cessation
- 1989-01-06 DK DK005289A patent/DK5289A/da not_active Application Discontinuation
- 1989-01-06 PT PT89409A patent/PT89409B/pt not_active IP Right Cessation
- 1989-01-06 US US07/294,096 patent/US4946841A/en not_active Expired - Fee Related
- 1989-01-06 JP JP64000586A patent/JPH01213270A/ja active Pending
- 1989-01-06 HU HU8945A patent/HU202502B/hu unknown
- 1989-01-06 PH PH38012A patent/PH26148A/en unknown
- 1989-01-06 NO NO89890062A patent/NO890062L/no unknown
- 1989-01-06 AU AU27780/89A patent/AU612449B2/en not_active Ceased
- 1989-01-06 ZA ZA89121A patent/ZA89121B/xx unknown
- 1989-01-06 NZ NZ227551A patent/NZ227551A/en unknown
- 1989-01-07 KR KR1019890000100A patent/KR890011859A/ko unknown
- 1989-01-09 IL IL88908A patent/IL88908A0/xx unknown
Also Published As
Publication number | Publication date |
---|---|
US4946841A (en) | 1990-08-07 |
JPH01213270A (ja) | 1989-08-28 |
DE3800785A1 (de) | 1989-07-20 |
FI890050A (fi) | 1989-07-10 |
EP0324347A3 (de) | 1990-12-05 |
ZA89121B (en) | 1989-09-27 |
DK5289D0 (da) | 1989-01-06 |
PT89409A (pt) | 1990-02-08 |
FI890050A0 (fi) | 1989-01-05 |
EP0324347A2 (de) | 1989-07-19 |
NO890062D0 (no) | 1989-01-06 |
NO890062L (no) | 1989-07-10 |
HUT50790A (en) | 1990-03-28 |
IL88908A0 (en) | 1989-08-15 |
PT89409B (pt) | 1993-12-31 |
AU612449B2 (en) | 1991-07-11 |
HU202502B (en) | 1991-03-28 |
NZ227551A (en) | 1990-11-27 |
AU2778089A (en) | 1989-07-13 |
PH26148A (en) | 1992-03-18 |
DK5289A (da) | 1989-07-10 |
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