KR900004686A - 류코트리엔 길항질 에스테르 전약제 - Google Patents
류코트리엔 길항질 에스테르 전약제 Download PDFInfo
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- KR900004686A KR900004686A KR1019890013778A KR890013778A KR900004686A KR 900004686 A KR900004686 A KR 900004686A KR 1019890013778 A KR1019890013778 A KR 1019890013778A KR 890013778 A KR890013778 A KR 890013778A KR 900004686 A KR900004686 A KR 900004686A
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- hydrogen
- methyl
- phenyl
- alkyl
- compound
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
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- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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Abstract
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Description
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Claims (20)
- 다음 일반식(I)의 화합물, 또는 이의 약제학적으로 허용되는 염.상기식에서, (a) R1은 C8내지 C13알킬, C7내지 C12알콕시, C7내지 C12알키티오, C10내지 C12I-알키닐, 10-운데시닉옥시, 11-도데시닐, 페닐 -C4내지 C10알킬, 페닐-C3내지 C9알콕시, 페닐티오-C3내지 C9알킬(여기에서 페닐은 브로모, 클로로, 트리플루오로메틸, C1내지 C4알콕시, 메틸티오 또는 트리플루오로 메틸티오에 의해 임의로 1치환된다.), 티에닐-C4,내지 C10알킬, 푸릴-C4내지 C10알킬, 트리플루오로메틸, -C7내지C12알킬 또는 사이클로헥실 -C4내지 C10알킬이며; R2수소,브로모,클로로,메틸,트리플루오로메틸,하이드록시, C1내지 C4알콕시 또는 니트로이거나; (b) R1은 수소이고; R2는 C8내지 C13알킬, C7내지C12알콕시, C7내지C12알킬티오, C10내지 C12I-알키닐, 10-운데시닐옥시, 11-도데시닐, 페닐 -C4내지 C10알킬, 페닐-C3내지 C9알콕시, 페닐티오-C3내지 C9알킬(여기에서 페닐은 브로모, 클로로, 트리플루오로메틸, C1내지 C4알콕시, 메틸티오 또는 트리플루오로 메틸티오에 의해 임의로 1치환된다.)푸릴-C4내지 C10알킬, 트리플루오로메틸, -C7내지C12알킬 또는 사이클로헥실 -C4내지 C10알킬이며; q는 0,1 또는 2이고 ; Y는 COR3,(CH2)m COR3또는(CH2)m 테트라졸 -5-일이며 ; 여기에서 테르라졸-5-일은 비치환되거나 A에 의해 치환되며 ; A는이고 ; 여기에서 R16및 R17은 독립적으로 수소 또는 C1-4알킬이며; j는 0 내지 6이고; R18은 수소, C1-4알킬,COR3,SO3H,SO2H,NH2,COCH2OH 또는 CHOHCH2OH이며; R3는 아미노, (CH2)n CO2CH2CONR16R17또는 OR14이고; R14는 수소, C1내지 C6알킬, 사이클로알킬, 아릴,아릴알킬,알킬아릴,알킬아릴알킬,알킬 치환된 아미노 또는 알킬아미노, -OCH2CONR7R8,인다닐,피발로일 옥시메틸, 아세톡시메틸, 프로피오닐 옥시메틸, 글리실옥시 메틸, 페닐 글리실 옥시메틸 또는 티에닐 글리실 옥시 메틸이며; R4는 수소, 메틸, C1내지 C4알콕시, 플루오로 또는 하이드록시이고; m은 0 또는 1이며; R(CH2)nCH(C O2H) CH2CO2R6, (CH2)n CO2CH2CONR16R17또는 다음 일반식의 이미다졸이고 ;n은 0 내지 6이며; R5는 수소, 아미노 또는 NHCOCH2CH2CH(NH2)CO2H이고; R6는 아니노, NH(CH2)n CO2H,SO3H,SO2NH2CN, 비치환되거나 상기 정의한 A로 치환된 테트라졸-5-일, 또는 OR15이며; R7는 수소, C1내지 C4알킬 또는 C3내지 C4알케닐 이고; R8은 수소, C1내지 C4알킬, 카복실 또는 카복스아미도이거나, R7및 R9이 수소 또는 C1내지 C4알킬일 경우 (CH2)m COOR15이며; R9은 수소, C1내지 C4알킬 또는 (CH2)m COOR15이고; R15는 수소, C1내지 C6알킬, 사이클로알킬, 아릴,아릴알킬,알킬아릴,알킬아릴알킬,알킬치환된 아미노 또는 알킬아미노, -OCH2CONR7R8,인다닐,피발로일 옥시메틸, 아세톡시메틸, 프로피오닐 옥시메틸, 글리실옥시 메틸, 페닐글리실 옥시메틸 또는 티에닐 글리실 옥시메틸이며; 단, 1) n이 0일때, R5는 수소이어야 하고, 2) R7,R8및 R9은 모두 수소이어서는 안되며; 3) q가 1 또는 2일때, R1및 R2중 어느 것도 알킬티오 또는 페닐 티오알킬이어서는 안되며; 4) R3및 R6는 모두 수소이어서는 안되며; 5) OR14및 OR15은 동시에 하이드록시 이어서는 안되고; 6) R4가 하이드록시이고 m이 0일 경우, R14는 수소이어야 한다.
- 제1항에 있어서, 일반식(IIA)의 화합물.상기식에서 R4는 하이들고시이고; m이 0이며; R3는 아니노 또는 OH이고; R15는 수소가 아니다.
- 제2항에 있어서, 2-하이드록시-3-[(2-카보이소프로폭시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산; 2-하이드록시-3-[(2-카보사이클로펜톡시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산; 하이드록시-3-[(2-카보이소프로폭시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산; 2-(S)-하이드록시-3(R)-[(2-카보이소프로폭시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산; 2-(S)-하이드록시-3(R)-[(2-카보에톡시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산; 2-하이드록시-3-[(2-에톡시에틸)티오]-3-2-(8-페닐옥틸)페닐]프로파노산; 2-하이드록시-3[(디에틸아미노카보닐)메톡시(2-카보닐 에틸티오)]-3-[2-(8-페닐옥틸)페닐]프로파노산; 또는 3-[2-(2-디메틸아미노에톡시 카보닐에틸)티오]-2-하이드록시-3-[2-(8-페닐옥틸)페닐]프로파노산인 화합물 또는 이의 약제학적으로 허용되는 염.
- 제1항에 있어서, 다음 일반식(Ⅲ)의 화합물.상기식에서 R4는 하이드록시가 아니고; R14는 수소이며; R15는 수소가 아니다.
- 제4항에 있어서, 메틸 4-티아-5-(2-도데실페닐)-5-(테트라졸-5-일)펜타노에이트; 메틸 4-티아-5-(2-도데실 페닐)-5-카복스 아미도 펜타노에이트; 메틸 4-티아-5-(2-도데실페닐)-6-(테트라졸-5-일)헥사노에이트; 또는 3-[(2-카보메톡시 에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노산인 화합물 또는 이의 약제학적으로 허용되는 염.
- 제1항에 있어서, 일반식(IVA)의 화합물.상기식에서 R15는 수소이고, R14는 수소가 아니다.
- 제6항에 있어서, 메틸 2-(3-카복시프로필티오)-2-(2-도데실페닐)아세테이트; 메틸 2-(2-카복스아미도 에틸티도)-2-(2-도데실페닐)아세테이트; 메틸 2-(2-도데실페닐)-5-설포-3-티아-펜타노에이트; 5-카보메톡시-5-(2-도데실페닐)-3-카복시-4-티아펜타노산; 메틸 2-(2-설폰아미도 에틸티오)-2-(2-도데실 페닐)아세테이트; 또는 메틸 2-(2-시아노에틸티오)-2-(2-도데실페닐)아세테이트인 화합물.
- 제1항에 있어서, 일반식(IVB)의 화합물.상기식에서 R4는 m이 0일때 하이드록시가 아니고, R15는 수소이며, R14는 수소가 아니다.
- 제8항에 있어서, t-부틸 3-(2-카복시에틸티오)-3-(2-도데실페닐)프로피오네이트; 메틸 2-메틸-3-(2-카복시에틸티오)-3-(2-도데실페닐)프로파노에이트; 또는 t-부틸 3-(2-카복시에틸티오)-3-[2-(8-페닐옥틸)-5-트리플루오로메틸페닐]프로파노에이트인 화합물.
- 제1항에 있어서, 일반식(VA)의 화합물.상기식에서 R14및 R15는 수소가 아니다.
- 제10항에 있어서, 메틸 2-(카보메톡시메틸티오)-2-2-(도데실페닐)아세테이트; 메틸 2-(2-카보메톡시 에틸티오)-2-(2-도데실 페닐)아세테이트; 3-아자-4-옥소-7-티아-8-(2-도데실페닐)-노난디오산 디메틸 에스테로; 메틸 2-(2-카보메톡시 에틸티오)-2-[2-(8-페닐옥틸)페닐]아세테이트; 또는 디-(5-부틸)-3-아자-4-옥소-7-티아-8-(2-도데실페닐)-데칸디오에이트인 화합물.
- 제1항에 있어서, 일반식(VB)의 화합물.상기식에서 R4는 m이 0일때 하이드록시가 아니고, R14및 R15는 수소가 아니다.
- 제12항에 있어서, 메틸 3(S)-[(2-카보메톡시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노에이트; 디-(t-부틸)-3-아자-4-옥소-7-티아-8-(2-도데실페닐)-데간디오에이트; 또는 메틸 3-[(2-카보메톡시에틸)티오]-3-[2-(8-페닐옥틸)페닐]프로파노에이트인 화합물.
- 제1항에 있어서, 다음 일반식의 이미다졸 치환된 화합물.상기식에서 R8및 R9중 하나는 (CH2)m COOR15이고, R15는 수소가 아니다.
- 제14항에 있어서, 메틸 2-(2-도데실페닐)-2-(1,4-디메틸-5-카보에톡시-2-이미다졸릴티오)아세테이트; 또는 메틸 2-(2-도데실페닐)-2-(1-메틸-4-프로필-5-카보에톡시-2-이미다졸릴티오)아세테이트인 화합물.
- 약제학적 담체 또는 희석제 및 뉴코트리엔의 효과를 억제하기에 충분한 무독량의 제1항 내지 제15항중 어느 한 항의 화합물을 함유하는 약제학적 조성물.
- 제16항에 있어서, 약제학적 담체 또는 희석제 및 뉴코트리엔의 효과를 억제하는데 충분한 무독량을 함유하는, 류코트리엔의 효과를 억제하기 위한 약제학적 조성물.
- 제17항에 있어서, 활성성분이 2-하이드록시-3-(카보메톡시 에틸티오)-3-[2-(8-페닐옥틸)-페닐]프로파노산 또는 이의 약제학적으로 허용되는 염인 약제학적 조성물.
- 제18항에 있어서, 활성성분이 2-하이드록시-3-(2-카보메톡시 에틸티오)-3-[2-(8-페닐옥틸)-페닐]프로파노산 또는 이의 약제학적으로 허용되는 염 및 2-[4-(5-브로모-3-메틸피리드-2-일)부틸아니노]-5-[(6-메틸피리드-3-일)메틸]4-피리미돈인 약제학적 조성물.
- 류코트리엔 길항질 활성을 갖는 약제를 제조하는데 있어서 제1항 내지 제15항중 어는 한 항의 화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US248770 | 1988-09-23 | ||
US07/248,770 US4937253A (en) | 1985-04-19 | 1988-09-23 | Ester prodrugs |
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KR900004686A true KR900004686A (ko) | 1990-04-12 |
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US (1) | US4937253A (ko) |
EP (1) | EP0365149A3 (ko) |
JP (1) | JPH02124869A (ko) |
KR (1) | KR900004686A (ko) |
CN (1) | CN1041359A (ko) |
AU (1) | AU4156989A (ko) |
DK (1) | DK466689A (ko) |
FI (1) | FI894498A (ko) |
HU (1) | HUT53353A (ko) |
IL (1) | IL91714A0 (ko) |
NO (1) | NO893772L (ko) |
PT (1) | PT91788A (ko) |
ZA (1) | ZA897232B (ko) |
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US5034537A (en) * | 1988-09-23 | 1991-07-23 | Smithkline Beecham Corporation | Leukotriene antagonists |
DE69113048T2 (de) * | 1990-08-01 | 1996-02-22 | Smithkline Beecham Corp | Verfahren und zwischenprodukte für die herstellung von 2-hydroxy-3-sulfido-3-phenylpropansäuren. |
CZ45193A3 (en) * | 1990-09-21 | 1994-02-16 | Smithkline Beecham Corp | Salts of (r)-4-nitro-alphamethyl benzene methaneamine |
US5262433A (en) * | 1991-08-06 | 1993-11-16 | Wakamoto Pharmaceutical Co., Ltd. | Tetrazoleacetic acid derivatives and method of aldose reductase inhibition therewith |
CZ299375B6 (cs) | 1998-11-30 | 2008-07-09 | Nihon Nohyaku Co., Ltd. | Ftalamidové deriváty nebo jejich soli, zemedelsko-zahradnický insekticid je obsahující a jeho použití |
US6765019B1 (en) | 1999-05-06 | 2004-07-20 | University Of Kentucky Research Foundation | Permeable, water soluble, non-irritating prodrugs of chemotherapeutic agents with oxaalkanoic acids |
EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
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US4069744A (en) * | 1975-01-30 | 1978-01-24 | Texas Instruments Incorporated | Gas metering orifice for decreasing gas consumption of pneumatic actuator |
GB1577550A (en) * | 1976-10-18 | 1980-10-22 | Sagami Chem Res | -thio-alkanoic acid derivatives |
US4513005A (en) * | 1981-06-18 | 1985-04-23 | Lilly Industries Limited | SRS-A antagonists |
IL69691A (en) * | 1982-09-23 | 1988-01-31 | Merck Frosst Canada Inc | Leukotriene antagonists,their preparation and pharmaceutical compositions containing them |
US4661505A (en) * | 1982-11-03 | 1987-04-28 | Eli Lilly And Company | Leukotriene antagonists |
EP0123543B1 (en) * | 1983-04-21 | 1988-02-03 | Merck Frosst Canada Inc. | Leukotriene antagonists, their production and use and compositions containing them |
CA1242195A (en) * | 1983-07-18 | 1988-09-20 | David K. Herron | Leukotriene antagonists |
US5105017A (en) * | 1983-07-18 | 1992-04-14 | Eli Lilly And Company | Leukotriene antagonist intermediates |
GB8320943D0 (en) * | 1983-08-03 | 1983-09-07 | Lilly Industries Ltd | Organic compounds |
EP0202759B1 (en) * | 1985-04-19 | 1990-06-20 | Smithkline Beecham Corporation | Leukotriene antagonists |
CA1334200C (en) * | 1987-06-24 | 1995-01-31 | James Simpson Frazee | Leukotriene antagonists |
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1988
- 1988-09-23 US US07/248,770 patent/US4937253A/en not_active Expired - Fee Related
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1989
- 1989-09-20 AU AU41569/89A patent/AU4156989A/en not_active Abandoned
- 1989-09-21 IL IL91714A patent/IL91714A0/xx unknown
- 1989-09-21 EP EP89309643A patent/EP0365149A3/en not_active Withdrawn
- 1989-09-21 DK DK466689A patent/DK466689A/da not_active Application Discontinuation
- 1989-09-22 CN CN89107500A patent/CN1041359A/zh active Pending
- 1989-09-22 NO NO89893772A patent/NO893772L/no unknown
- 1989-09-22 KR KR1019890013778A patent/KR900004686A/ko not_active Application Discontinuation
- 1989-09-22 PT PT91788A patent/PT91788A/pt not_active Application Discontinuation
- 1989-09-22 HU HU894973A patent/HUT53353A/hu unknown
- 1989-09-22 JP JP1247854A patent/JPH02124869A/ja active Pending
- 1989-09-22 FI FI894498A patent/FI894498A/fi not_active Application Discontinuation
- 1989-09-22 ZA ZA897232A patent/ZA897232B/xx unknown
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JPH02124869A (ja) | 1990-05-14 |
AU4156989A (en) | 1990-03-29 |
PT91788A (pt) | 1990-03-30 |
NO893772L (no) | 1990-03-26 |
US4937253A (en) | 1990-06-26 |
FI894498A (fi) | 1990-03-24 |
HUT53353A (en) | 1990-10-28 |
NO893772D0 (no) | 1989-09-22 |
ZA897232B (en) | 1990-09-26 |
IL91714A0 (en) | 1990-06-10 |
CN1041359A (zh) | 1990-04-18 |
DK466689D0 (da) | 1989-09-21 |
DK466689A (da) | 1990-03-24 |
EP0365149A2 (en) | 1990-04-25 |
EP0365149A3 (en) | 1990-07-25 |
FI894498A0 (fi) | 1989-09-22 |
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