KR840007555A - 메발로노락톤 및 그 유도체의 제조방법과 이를 함유한 약학적 조성물 - Google Patents
메발로노락톤 및 그 유도체의 제조방법과 이를 함유한 약학적 조성물 Download PDFInfo
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- KR840007555A KR840007555A KR1019840000290A KR840000290A KR840007555A KR 840007555 A KR840007555 A KR 840007555A KR 1019840000290 A KR1019840000290 A KR 1019840000290A KR 840000290 A KR840000290 A KR 840000290A KR 840007555 A KR840007555 A KR 840007555A
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- compound
- alkyl
- hydrogen
- benzyloxy
- phenoxy
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- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- JYVXNLLUYHCIIH-UHFFFAOYSA-N (+/-)-mevalonolactone Natural products CC1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-UHFFFAOYSA-N 0.000 title 1
- JYVXNLLUYHCIIH-ZCFIWIBFSA-N R-mevalonolactone, (-)- Chemical compound C[C@@]1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-ZCFIWIBFSA-N 0.000 title 1
- 229940057061 mevalonolactone Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- -1 t-butoxy Chemical group 0.000 claims 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 150000002596 lactones Chemical class 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- RWNJOXUVHRXHSD-UHFFFAOYSA-N hept-6-enoic acid Chemical compound OC(=O)CCCCC=C RWNJOXUVHRXHSD-UHFFFAOYSA-N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
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- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/202—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a naphthalene
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
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- 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
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- C07C59/40—Unsaturated compounds
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- 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
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
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- 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
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Confectionery (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 하기식(I)의 화합물 또는 에리트로-(E)-3,5 디히드록시-7-(2′-[4″-플루오로페닐]나프트-1′-일)헵트-6-에노에이트 또는 에리트로-(E)-3,5-디히드록시-7-(1′-[4″-플루오로페닐]-3′-[1′-메틸에틸)나프트-2′-일)헵트-6-에노에이트 또는 (E)- 트란스 -6-(2′-[3″-에틸-1″-(4″-플루오로페닐)나프트-2″-일]에테닐)-4-히드록시-3,4,5,6-테트라히드로피란-2-온 및 각각의 염형의 유리산형 또는 생리학적-가수분해성과 허용 가능한 에스테르형 또는 락톤형 또는 약학적 허용가능한 염형의 화합물과 약학적으로 허용가능한 희석제 또는 담체로 구성된 약학적 조성물.상기식에서 두 R0기는또는 -(CH2)4-의 라디칼을 형성하며, 이중 R2는 수소, C1-4알킬, C14-4알콕시(t-부톡시제외), 트리플루오로메틸, 플루오로, 클로로, 페녹시, 벤질옥시이며, R3는 수소, C1-3알킬, C1-3알콕시, 트리플루오로메틸, 플루오로, 클로로, 페녹시, 벤질옥시이며, R2및 R3중 적어도 어느 하나가 트리플루오로 메틸이며 R3및 R2중 적어도 어느 하나가 페녹시이며 R2및 R3중 적어도 어느 하나가 벤질옥시임을 조건으로하며, R1는 수소, C1-4알킬, 플루오로, 클로로 또는 벤질옥시이며, R4는 수소, C1-4알킬, C1-4알콕시(t-부톡시제외), 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이며, R5는 수소, C1-3알킬, C1-3알콕시, 트리플루오로메틸, 플루오로, 클로로, 페녹시 또는 벤질옥시이며, R5a는 수소, C1-2알킬, C1-2알콕시, 플루오로 또는 클로로이며; R4및 R5중 적어도 하나는 트리플루오로메틸이며 R4및 R5중 적어도 하나는 페녹시이며 R4및 R5중 적어도 하나는 벤질옥시이며, X는 -(CH2)n,이며, 이중 n은 0, 1, 2 또는 3이며 두 q 모두가 0이거나, 하나가 0이고 다른 하나가 1이며, Z는이며, 이중 R6는 수소 또는 C1-3알킬이며, 페닐기에서-X-Z와 R4는 서로 오르토 위치.
- R6가 수소일 때 하기식(VI)의 화합물을 환원하고 R6가 C1-3알킬일 때 식(XVII)의 화합물을 가수분해하고 X가일 때 식(LIX)의 화합물을 탈보호화하고 생리학적-가수분해성 에스테르 또는 락톤형의 화합물을 가수분해하고 유리산형의 화합물을 에스테르화 또는 락톤화하고이 기본적 고리구조일 때 유리산행 또는 염형의 화합물을 회수하는 것으로 구성된 식(I) 화합물의 제조방법.상기식에서 R14는 생리학적으로 가수분해성과 허용가능한 에스테르를 형성하는 라디칼, R60는 C1-3알킬, R15는 에스테르 형성기의 일부 Pro는 보호기, R0, Rl, R4, R5, X와 Z는 제1항에서 정의된 것과 같다.
- 에스테르 또는 락톤형의 화합물을 가수분해하고 유리산형의 화합물을 락톤화 또는 에스테르화하여 유리 카복실기가 존재할 때 유리산형 또는 염형의 화합물을 회수하는 것으로 구성된 식(I) 화합물의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US46060083A | 1983-01-24 | 1983-01-24 | |
US460600 | 1983-01-24 |
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KR840007555A true KR840007555A (ko) | 1984-12-08 |
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KR1019840000290A KR840007555A (ko) | 1983-01-24 | 1984-01-24 | 메발로노락톤 및 그 유도체의 제조방법과 이를 함유한 약학적 조성물 |
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EP (1) | EP0117228B1 (ko) |
JP (1) | JPS60500499A (ko) |
KR (1) | KR840007555A (ko) |
AT (1) | ATE23326T1 (ko) |
AU (1) | AU570942B2 (ko) |
CA (1) | CA1268473A (ko) |
DE (1) | DE3461180D1 (ko) |
DK (1) | DK454184D0 (ko) |
ES (1) | ES8609193A1 (ko) |
FI (1) | FI843560L (ko) |
GR (1) | GR81711B (ko) |
HU (1) | HU199769B (ko) |
IE (1) | IE840153L (ko) |
IL (1) | IL70767A (ko) |
NZ (1) | NZ206919A (ko) |
PL (1) | PL144594B1 (ko) |
PT (1) | PT77996B (ko) |
WO (1) | WO1984002903A1 (ko) |
ZA (1) | ZA84547B (ko) |
Families Citing this family (17)
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US4613610A (en) * | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
WO1986003488A1 (en) * | 1984-12-04 | 1986-06-19 | Sandoz Ag | Indene analogs of mevalonolactone and derivatives thereof |
US5001255A (en) * | 1984-12-04 | 1991-03-19 | Sandoz Pharm. Corp. | Idene analogs of mevalonolactone and derivatives thereof |
US4668794A (en) * | 1985-05-22 | 1987-05-26 | Sandoz Pharm. Corp. | Intermediate imidazole acrolein analogs |
WO1987002662A2 (en) * | 1985-10-25 | 1987-05-07 | Sandoz Ag | Heterocyclic analogs of mevalonolactone and derivatives thereof, processes for their production and their use as pharmaceuticals |
US4851427A (en) * | 1985-10-25 | 1989-07-25 | Sandoz Pharm. Corp. | Pyrrole analogs of mevalonolactone, derivatives thereof and pharmaceutical use |
ZW10287A1 (en) * | 1986-07-15 | 1988-01-13 | Hoffmann La Roche | Tetrahydronaphthaline and indane derivatives |
US4751235A (en) * | 1986-12-23 | 1988-06-14 | Sandoz Pharm. Corp. | Anti-atherosclerotic indolizine derivatives |
NZ221717A (en) * | 1986-09-10 | 1990-08-28 | Sandoz Ltd | Azaindole and indolizine derivatives and pharmaceutical compositions |
US4898949A (en) * | 1987-02-25 | 1990-02-06 | Bristol-Myers Company | Intermediates for the preparation of antihypercholesterolemic tetrazole compounds |
US4897490A (en) * | 1987-02-25 | 1990-01-30 | Bristol-Meyers Company | Antihypercholesterolemic tetrazole compounds |
US4904646A (en) * | 1987-05-22 | 1990-02-27 | E. R. Squibb & Sons, Inc. | Phosphorus-containing HMG-COA reductase inhibitors |
US5091378A (en) * | 1987-05-22 | 1992-02-25 | E. R. Squibb & Sons, Inc. | Phosphorus-containing HMG-CoA reductase inhibitors, new intermediates and method |
US5010205A (en) * | 1988-08-23 | 1991-04-23 | Bristol-Myers Company | Antihypercholesterolemic tetrazol-1-yl intermediates |
US5506219A (en) * | 1988-08-29 | 1996-04-09 | E. R. Squibb & Sons, Inc. | Pyridine anchors for HMG-CoA reductase inhibitors |
WO2006123355A2 (en) * | 2004-11-03 | 2006-11-23 | Sun Pharmaceutical Industries Limited | Novel statin derivatives |
JP6024259B2 (ja) * | 2011-07-25 | 2016-11-16 | 東ソー株式会社 | 新規なナフタルアルデヒド化合物、その製造法、および該化合物からトリアリールアミン化合物を製造する方法 |
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JPS5559140A (en) * | 1978-10-30 | 1980-05-02 | Sankyo Co Ltd | 3,5-dihydroxypentanoic alkyl ester derivative, its preparation and remedy for hyperlipemia containing the same as the effective component |
AU548996B2 (en) * | 1980-02-04 | 1986-01-09 | Merck & Co., Inc. | Tetrahydro-2h-pyran-2-one derivatives |
-
1984
- 1984-01-23 CA CA000445903A patent/CA1268473A/en not_active Expired - Lifetime
- 1984-01-23 GR GR73574A patent/GR81711B/el unknown
- 1984-01-23 AT AT84810039T patent/ATE23326T1/de not_active IP Right Cessation
- 1984-01-23 EP EP84810039A patent/EP0117228B1/en not_active Expired
- 1984-01-23 DE DE8484810039T patent/DE3461180D1/de not_active Expired
- 1984-01-23 IE IE840153A patent/IE840153L/xx unknown
- 1984-01-23 ES ES529090A patent/ES8609193A1/es not_active Expired
- 1984-01-23 PT PT77996A patent/PT77996B/pt not_active IP Right Cessation
- 1984-01-24 IL IL70767A patent/IL70767A/xx unknown
- 1984-01-24 KR KR1019840000290A patent/KR840007555A/ko not_active Application Discontinuation
- 1984-01-24 JP JP59500672A patent/JPS60500499A/ja active Pending
- 1984-01-24 ZA ZA84547A patent/ZA84547B/xx unknown
- 1984-01-24 NZ NZ206919A patent/NZ206919A/en unknown
- 1984-01-24 PL PL1984245886A patent/PL144594B1/pl unknown
- 1984-01-24 WO PCT/EP1984/000018 patent/WO1984002903A1/de active Application Filing
- 1984-01-24 AU AU24331/84A patent/AU570942B2/en not_active Ceased
- 1984-01-24 HU HU84660A patent/HU199769B/hu not_active IP Right Cessation
- 1984-09-11 FI FI843560A patent/FI843560L/fi not_active Application Discontinuation
- 1984-09-21 DK DK454184A patent/DK454184D0/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
GR81711B (ko) | 1984-12-12 |
WO1984002903A1 (en) | 1984-08-02 |
ZA84547B (en) | 1985-09-25 |
HUT37380A (en) | 1985-12-28 |
DK454184A (da) | 1984-09-21 |
CA1268473A (en) | 1990-05-01 |
PT77996A (en) | 1984-02-01 |
AU2433184A (en) | 1984-08-15 |
JPS60500499A (ja) | 1985-04-11 |
PT77996B (en) | 1986-05-30 |
NZ206919A (en) | 1987-08-31 |
PL245886A1 (en) | 1985-12-03 |
FI843560A0 (fi) | 1984-09-11 |
ES8609193A1 (es) | 1986-07-16 |
PL144594B1 (en) | 1988-06-30 |
IE840153L (en) | 1984-07-24 |
EP0117228A1 (en) | 1984-08-29 |
FI843560L (fi) | 1984-09-11 |
AU570942B2 (en) | 1988-03-31 |
DE3461180D1 (en) | 1986-12-11 |
IL70767A0 (en) | 1984-04-30 |
HU199769B (en) | 1990-03-28 |
IL70767A (en) | 1988-06-30 |
ATE23326T1 (de) | 1986-11-15 |
ES529090A0 (es) | 1986-07-16 |
DK454184D0 (da) | 1984-09-21 |
EP0117228B1 (en) | 1986-11-05 |
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