KR870700063A - 메발로노락톤의 인덴유도체 및 이들의 유도체 - Google Patents

메발로노락톤의 인덴유도체 및 이들의 유도체

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KR870700063A
KR870700063A KR1019860700524A KR860700524A KR870700063A KR 870700063 A KR870700063 A KR 870700063A KR 1019860700524 A KR1019860700524 A KR 1019860700524A KR 860700524 A KR860700524 A KR 860700524A KR 870700063 A KR870700063 A KR 870700063A
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alkyl
hydrogen
compound
benzyloxy
phenoxy
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지. 카타왈라 페이줄라
와타나신 솜풍
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예안 크래머·한즈 루돌프 하우즈
산도즈 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids

Abstract

내용 없음.

Description

메발로노락톤의 인덴유도체 및 이들의 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 유리산 형태 또는 그의 에스테르 또는 δ-락톤형태 또는 염형태의 일반식(I)의 화합물.
    상기 식에서, R은 수소, 또는 1급 또는 2급 C1-6알킬이고, R1는 1급 또는 2급 C1-6알킬이거나, R 및 R1은 함께 -(CH2)m(여기에서 m은 2,3,4,5 또는 6 이다) 또는 (Z)-CH2-CH=CH-CH2-이며, R0은 C1-6알킬, C3-7사이클로알킬 또는 환
    R2및 R4는 각각 독립적으로 수소, C1-4알킬, C1-4알콕시(t-부톡시 제외), 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이며, R3및 R5는 각각 독립적으로 수소, C1-3알킬, C1-3알콕시, 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이고, R6는 수소, C1-2알킬, C1-2알콕시, 플루오로 또는 클로로이며, 단, 페닐 및 인덴환의 각각에 트리플루오로메틸, 페녹시 또는 벤질옥시가 각각 하나만 위치할 수 있어야 하고, X는 -(CH2)n- 또는 -(CH2)qCH=CH(CH2)q- (여기에서 n은 1,2, 또는 3이고, q는 모두 0이거나, 하나는 0이고 다른 하나는 1이다)이며, Z는 다음 일반식(II)의 그룹이고,
    상기식에서, Q는또는이며, R7은 각각 동일한 1급 또는 2급 C1-6알킬이거나
    함께 -(CH2)2-, -(CH2)3-이고, R10은 수소 또는 C1-3알킬이며, 단, X가 -CH=CH- 또는 -CH2-CH=CH-이고/이거나 R10인 C1-3알킬일 경우에만은 Q는가 아닐수 있다.
  2. 제1항에 있어서, R0가 환(A)을 나타내며, R이 수소, 또는 비대칭 탄소원자 함유하지 않는 1급 또는 2급 C1-6알킬이고, R1이 비대칭 탄소원자를 함유하지 않는 1급 또는 2급 C1-6알킬이거나, R 및 R1이 함께 (CH2)m- 또는 (Z)-CH2-CH=CH-CH2-이며, R2가 수소, C1-3알킬, n-부틸, I-부틸, t-부틸, C1-3알콕시, n-부톡시, I-부톡시, 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이고, R3가 수소, C1-3알킬, C1-3알콕시, 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이며, 단 R2및 R3중 하나 이하가 트리플루오로메틸이고, R2및 R3중 하나 이하가 페녹시이며, R2및 R3중 하나 이하가 벤질옥시이어야 하고, R4가 수소, C1-3알킬, n-부틸, I-부틸, t-틸부, C1-3알콕시, n-부톡시, I-부톡시, 틀리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이며, R5가 수소, C1-3알킬, C1-3알콕시, 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이고, R6가 수소, C1-2알킬, C1-2알콕시, 플루오로 또는 클로로이며, 단, R4및 R5중 하나 이하가 틀리플루오로 메틸이고, R4및 R5중 하나 이하가 페녹시이며, R4및 R5중 하나 이하가 벤질옥시이어야 하고, X가 -(CH2)n-(여기에서 n은 1,2, 또는 3이다) 또는 (E)-CH=CH-이며, Z가(a) 또는(b)이고, R10이 수소 또는 C1-3알킬이며, R11이 수소, R12또는 M이고, R12가 생리학적으로 허용되며 가수분해 가능한 에스테르 그룹이며, M이 약제학적으로 허용되는 양이온인 화합물.
  3. 제1항에 있어서 R,R1,R0,R2내지 R6,X 및 Z가 그룹(i) 내지 (1vi)에서 정의한 의미중에서 선택된 의미를 갖는 화합물.
  4. 유리산 형태의 에리트로-(E)-3,5-디하이드록시-7-[3′-(4″-플루오로 페닐)-스피로[사이클로펜탄-1,1′(1H)-인덴]-2′-일]헵트-6-에노산 및 에리트로-(E)-3,5-디하이드록시-7-[3′-(3″,5″-디메틸페닐)-스피로[사이클로펜탄-1,1′(1H)-인덴]-2′-일]헵트-6-에노산 또는 이들이 염중에서 선택되는 화합물.
  5. 제4항에 있어서, 나트륨염 형태의 화합물.
  6. 제1항에 따르는, 화합물을 필요한 경우 유리산 형태로 또는 생리학적으로 가수분해될 수 있고 생리학적으로 허용되는 에스테르 또는 락톤의 형태로 또는 약제학적으로 허용되는 염 형태로, 약제학적으로 허용되는 희석제 또는 담체와 함께 함유하는 약제학적 조성물.
  7. 제1항에 있어서, 필요한 경우, 약제로서 사용하기 위한, 유리산 형태 또는 생리학적으로 가수분해 될 수 있고 생리학적으로 허용되는 에스테르 또는 락톤의 형태 또는 약제학적으로 허용되는 염형태의 화합물.
  8. 제1항에 있어서, 필요한 경우, 콜레스테롤 생합성을 억제하거나 아테롬성 동맥경화증을 치료하는데 사용하기 위한, 유리산 형태, 생리학적으로 가수분해 가능하며 허용되는 에스테르 또는 락톤형태 또는 약제학적으로 허용되는 염형태의 화합물.
  9. 에스테르 또는 락톤 형태의 일반식(I)의 화합물을 가수분해시키거나, 유리산 형태의 일반식(I) 화합물을 에스테르화 또는 락톤화 시키고, 유리카복실 그룹이 존재할 경우 수득 화합물을 유리산 형태 또는 염의 형태로 회수함을 특징으로 하여, 제1항에 따르는 화합물을 제조하는 방법.
  10. a) X가 -(CH2)n- 또는 (E)-CH=CH-이고 R10이 수소일 경우, 일반식(IV)의 화합물을 환원시키거나, b) X가 -(CH2)n- 또는 -(E)-CH=CH-이며 R10이 C1-3알킬일 경우 일반식(XII)의 화합물을 가수분해 시키거나, c) X가 -CH=CH- 또는 -CH2-CH=CH-이고, (IIb)가 4R,6S 배열이거나, X가 -CH2CH2또는 -CH2CH2CH2이며 (IIb)가 4R,6R 배열일 경우, 일반식(XXXIX)의 화합물을 탈보호시키거나, d) X가 -(CH2)2-, -(CH2)3-, -(CH2)qCH=CH(CH2)q-일 경우 일반식(XXXII)의 화합물을 탈보호시키거나, e) Q가일 경우 Q가인 상응하는 일반식(I)의 화합물을 산화시키거나, f) Q가이고 (II)가 에스테르 형태일 경우 Q가인 상응하는 일반식(I)의 화합물을 케탈화시키거나, g) 에스테르 또는 락톤 형태의 일반식(I)의 화합물을 가수분해 시키거나, h) 유리산 형태의 일반식(I)의 화합물을 에스테르화 또는 락톤화 시키고, 유리카복실 그룹이 존재할 경우 수득화합물을 유리산 형태 또는 염의 형태로 회수시킴을 특징으로 하여, 제1항에 따르는 화합물을 제조하는 방법.
    상기식에서, R13는 에스테르 형성기이며, X1은 -(CH2)n- 또는 (E)-CH=CH-이고 R10a는 C1-3알킬이며, R14는 에스테르 형성 그룹의 부분이고, X″는 -CH2CH2, -CH2CH2CH2, -CH=CH- 또는 -CH2CH=CH 이며, Pro는 보호 그룹이고, X″′는 -(CH2)2-, -(CH2)3- 또는 -(CH2)q=CH=CH-(CH2)q-이다,
  11. 일반식(XXXIII), (XXXIV), (XXXVII), (XXXIX), (XLVI), (XLVI), (XLVIII), (L-LII), (LV), (LVII-LIX), (LX), (LXI) 및 (LXIV) 중에서 선택되는 화합물.
  12. 제1항에 따른 화합물 또는 실시예 1 내지 7 및/또는 화합물 1 내지 30에 관하여 전술한 바와 거의 같은 제1항에 따른 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019860700524A 1984-12-04 1985-11-29 메발로노락톤의 인덴동족체 및 이들의 유도체의 제법 KR910003427B1 (ko)

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US67791784A 1984-12-04 1984-12-04
US677917 1984-12-04
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NZ214402A (en) 1989-01-27
PH24502A (en) 1990-07-18
FI863121A0 (fi) 1986-07-30
EP0216785A1 (en) 1987-04-08
PT81603B (pt) 1988-04-21
ZA859303B (en) 1987-07-29
DK369086A (da) 1986-08-01
HUT40398A (en) 1986-12-28
PL256608A1 (en) 1988-01-07
GR852895B (ko) 1986-04-01
PT81603A (en) 1986-01-01
AU599580B2 (en) 1990-07-26
HU198005B (en) 1989-07-28
AU5230686A (en) 1986-07-01
WO1986003488A1 (en) 1986-06-19
DE3581638D1 (de) 1991-03-07
MY100972A (en) 1991-06-15
PL147645B1 (en) 1989-07-31
ES8800888A1 (es) 1987-12-01
ES549546A0 (es) 1987-12-01
EP0216785B1 (en) 1991-01-30
IL77199A (en) 1990-02-09
ATE60571T1 (de) 1991-02-15
FI863121A (fi) 1986-07-30
JPS62501009A (ja) 1987-04-23
DK369086D0 (da) 1986-08-01

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