KR950700241A - 신규한 아미딘 유도체, 이의 제조방법 및 LTB_4 길항작용을 하는 약제로서의 이의 용도(Novel amidine derivatives, their preparation and their use as medicaments with LTB_4 antagonistic effect) - Google Patents
신규한 아미딘 유도체, 이의 제조방법 및 LTB_4 길항작용을 하는 약제로서의 이의 용도(Novel amidine derivatives, their preparation and their use as medicaments with LTB_4 antagonistic effect)Info
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Abstract
본 발명은 통상적인 방법으로 제조될 수 있고 통상적인 생약 제조로서 치료용으로 사용되는 다음 일반식(Ⅰ)의 화합물에 관한 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 라세미체로서, 순수하거나 집중적인 형태를 이룬 거울상 이성체, 가능하게는 부분입체이성체의 쌍으로서, 시스- 또는 트랜스 형태로서, 및 유리 염기 또는 염, 바람직하게는 약리학적으로 허용되는 산과의 염으로서의 다음 일반식(Ⅰ)의 화합물.상기식에서, R1및 R2는 동일하거나 상이하며, CF3, 할로겐, R5, OR5, COR6, SR6, SOR6, S02R6, S02NR5R7또는 C(OH)R5R7이거나, 벤젠 환의 인접한 탄소 원자와 결합하여, 각각 C1-4알킬에 의해 치환될 수 있는 -CR8=CR9-CH=CH-, -CH=CR8-CR9=CH-, -CR8=CH-CR9=CH-, -0-CHR10-CH12-, 0-CH2-0-, -0-CH|2-CH2-0-, -(CH2)3-4, -NH-CO-0-, -NH-CO-CH2-0-, -CO-CH2-0- 또는 -CO-CH2CH2-0의 이중결합된 그룹을 나타낼 수 있고, R3은 할로겐, OH, CF3, R5, OR6, COR6, CONH5R7, CH2OH, CH2-0(C1-4-알킬), SR6, SOR6, SO2R6, S02NR5R7, NH-CO-(C1-4-알킬), NH-S02-(C1-4-알킬), NR5R7또는 C(OH)R5R7[여기서, R3이 R5와 동일한 경우, 치환체 R1및 R2중의 적어도 하나가 H가 아니라면 R5는 반드시 H이다]이거나, 1 내지 3개의 헤테로 원자를 갖는 일반식헤테로사이클릭 5원환[여기서, D, E 및 G는 동일하거나 상이하며, CH, N, C-(C1-4-알킬) 또는 C-페닐이고, L은 0 또는 S이다]이며, R4는 할로겐, NH2, NH-(C1-4-알킬); N(C1-4-알킬)2, OH 또는 C1-4-알콕시이고, R5는 H, C1-12-알킬 또는 페닐이거나, 할로겐, C1-4-알킬, C1-4-알콕시 또는 C2-5-아실에 의해 임의로 치환된 페닐이거나, 또는 페닐-(C1-4-알킬)이며, R6은 C1-12-알킬 또는 페닐이거나, 할로겐, C1-4-알킬, C1-4-알콕시 또는 C2-C5-아실에 의해 임의로 치환된 페닐이고, R7은 H 또는 C1-12-알킬이며, R8및 R9는 동일하거나 상이하고, H, OH, C1-4-알킬, C1-4-알콕시 또는 C2-5-아실이며, R10은 H 또는 C1-4-알킬이고, R11및 R12는 동일하거나 상이하며, H, OH, 할로겐, CF3, C1-4-알킬 또는 C1-4-알콕시이고, A는 그룹X1-A1-X2(Ⅱ)X2-A2-X3(Ⅲ)X4-A2-X2(Ⅳ)(CH2)1-2-NH-CO-(CH2)1-3-X2(Ⅴ)-CH=CH-A2-X2(Ⅵ)중의 하나이며, B는 CH=CH, CH=N, S 또는이고, A1은 C2-4-알킬렌, 시스- 또는 트랜스 -CH2-CH=CH-CH2,CH2-CC-CH2,또는이며, A는 C1-5-알킬렌이고, X1은 O, NH, S, SO, SO2, CO, CH2또는이며, X2는 O, NH, S 또는이고, X3은 NH-CO, CO-NH, SO2-NH 또는이며, X4는 NH-CO, CO-NH, NH-S02, S02-NH 또는 NH-CO-NH이다.
- 다음 일반식(Ⅰ')의 화합물.상기식에서, R1및 R2는 동일하거나 상이하며, R7, OR7, COR6또는 할로겐이거나, 벤젠 환의 인접한 탄소원자와 결합하여, -CR8=R9-CH=CH-, -CH=CR8-CR9=CH-, -0-CHR10-CH2- 또는 -CO-CH2-CH2-0-의 이중결합된 그룹을 나타낼 수 있고, R3은 할로겐, CF3, R7, OR7, C0-(C1-4-알킬), NH-CO-(C1-4-알킬), NHS02-(C1-4-알킬) 또는 N(R10)2[여기서, 치환체 R1및 R2중의 적어도 하나가 H가 아닌 경우, R7은 반드시 H이다]이거나, 일반식헤테로사이클릭 5원 환이며, R6및 R7은 위에서 정의한 바와 같고, A는 그룹(Ⅱ)이다.
- 제1항 또는 제2항에 있어서, R1/R2/R3이 C2-5-아실/H/H, C6H5CO/H/H, C1-4-알킬/OH/H, C2-5-아실/C1-4-알킬/H, C2-5-아실/OH/C1-4-알킬 또는 OH/C2-5-아실/C1-4-알킬인 화합물.
- 제1항 내지 제3항 중의 어느 한 항에 있어서, A가 0-(CH2)2-0, 0-(CH2)4-0 또는인 화합물.
- 제1항 내지 제4항 중의 어느 한 항에 있어서, 그룹(Ⅱ)가 아세틸페닐렌 화합물.
- 제1항 내지 제5항 중의 어느 한 항에 있어서, 그룹이인 화합물.
- 유리 염기 또는 산 부가염 형태인 다음 일반식의 화합물.상기식에서, a는 0 또는 1이고, b는 1 또는 2이며, R은 C1-4-알킬이고, 단 a가 0 또는 1이고 b가 1인 경우와 a가 1이고, b가 2인 경우에는, R이 수소일 수도 있다.
- 제7항에 있어서, 유리 염기로서 또는 산 부가염으로서, a가 0 또는 1이고 b가 1이거나 a가 0이고 b가 2인 화합물.
- 제8항에 있어서, 유리 염기로서 또는 산 부가염으로서, R이 H, CH3또는 C2H5이고 a가 0 또는 1이며, b가 1인 화합물.
- 제8항에 있어서, 유리 염기로서 또는 산 부가염으로서, a가 0이고 b가 2이며 R이 CH3인 화합물.
- 제1항 내지 제10항 중의 어느 한 항에 따른 화합물을 함유함을 특징으로 하는 약제학적 조성물.
- 염증성 및/또는 알레르기성 증상이 관련된 질환, 특히 천식, 궤양성 대장염 및 건선의 치료와 비스테로이드성 소염제에 의해 유도된 위장질환의 치료를 목적으로 하는 약제학적 조성물을 제조하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 화합물의 용도.
- LTB4길항성 화합물이 사용될 수 있는 질환을 치료하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 유효 복용량의 화합물의 용도.
- 염증성 및/또는 알레르기성 증상이 관련된 질환, 특히 천식, 궤양성 대장염 및 건선을 치료하고 비스테로이드성 소염제에 의해 유도된 위장 질환을 치료하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 유효 복용량의 화합물의 용도.
- (a) 일반식(X)의 이미도에스테르를 암모니아와 반응시키거나, (b1) 일반식(XI)의 페놀 또는 티오페놀을 일반식(XII) 또는 (XIII)의 화합물과 반응시키거나, (b2) 일반식(XIV)의 페놀 또는 티오페놀을 일반식(XV), (XVI), (XVII) 또는 (XVIII)의 화합물과 반응시키거나, (c) 일반식(XIX)의 아미드옥심을 상응하는 아미딘이 형성되도록 환원시킴을 특징으로 하는, 제1항 내지 제10항 중의 어느 한 항에 따른 화합물의 제조방법.상기식에서, R1내지 R4, A, B, A1, A2, X2및 X3은 제1항에서 정의한 바와 같고, R은 바람직하게는 C1-6알킬 그룹 또는 벤질이며, Z는 OH 또는 SH이고, L은 이핵성 이탈 그룹이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4203201.6 | 1992-02-05 | ||
DE4203201A DE4203201A1 (de) | 1992-02-05 | 1992-02-05 | Neue amidinderivate, ihre herstellung und verwendung |
DE4224289A DE4224289A1 (de) | 1992-07-23 | 1992-07-23 | Neue Amidinderivate, ihre Herstellung und Verwendung |
DEP4224289.4 | 1992-07-23 | ||
DEP4244241.9 | 1992-12-24 | ||
DE4244241A DE4244241A1 (de) | 1992-12-24 | 1992-12-24 | Neue Verbindungen, ihre Herstellung und ihre Verwendung |
PCT/EP1993/000070 WO1993016036A1 (de) | 1992-02-05 | 1993-01-14 | Neue amidinderivate, ihre herstellung und verwendung als arzneimittel mit ltb4-antagonischer wirkung |
Publications (2)
Publication Number | Publication Date |
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KR950700241A true KR950700241A (ko) | 1995-01-16 |
KR0163222B1 KR0163222B1 (ko) | 1999-01-15 |
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Application Number | Title | Priority Date | Filing Date |
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KR1019940702669A KR0163222B1 (ko) | 1992-02-05 | 1993-01-14 | 아미딘 유도체, 이의 제조방법 및 이를 함유하는 ltd4 길항작용을 갖는 약제 |
Country Status (29)
Country | Link |
---|---|
US (3) | US6037377A (ko) |
EP (2) | EP0902013B1 (ko) |
JP (2) | JP3487851B2 (ko) |
KR (1) | KR0163222B1 (ko) |
AT (2) | ATE180770T1 (ko) |
AU (1) | AU673343B2 (ko) |
CA (2) | CA2129526A1 (ko) |
CZ (2) | CZ287209B6 (ko) |
DE (2) | DE59309630D1 (ko) |
DK (2) | DK0902013T3 (ko) |
ES (2) | ES2132216T3 (ko) |
FI (1) | FI943618A (ko) |
GR (1) | GR3030468T3 (ko) |
HR (1) | HRP930102B1 (ko) |
HU (1) | HU216191B (ko) |
IL (1) | IL104589A0 (ko) |
MX (1) | MX9300630A (ko) |
NO (1) | NO301540B1 (ko) |
NZ (1) | NZ246593A (ko) |
PL (2) | PL173789B1 (ko) |
PT (1) | PT902013E (ko) |
RU (1) | RU2124002C1 (ko) |
SG (1) | SG44837A1 (ko) |
SI (1) | SI9300066B (ko) |
SK (1) | SK281016B6 (ko) |
TW (1) | TW232005B (ko) |
UA (1) | UA43318C2 (ko) |
WO (1) | WO1993016036A1 (ko) |
YU (1) | YU49038B (ko) |
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US5451700A (en) * | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
US5488160A (en) * | 1991-06-11 | 1996-01-30 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and method of treatment |
US5455274A (en) * | 1992-12-09 | 1995-10-03 | Ciba-Geigy Corporation | Hydroxyamidine derivatives |
DE4309285A1 (de) * | 1993-03-23 | 1994-09-29 | Boehringer Ingelheim Kg | Heterocyclen enthaltende Amidinderivate, ihre Herstellung und Verwendung |
DE4424713A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
DE4424714A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Neue chemische Verbindung, ihre Herstellung und ihre Verwendung als Arnzneistoff |
DE19546452A1 (de) * | 1995-12-13 | 1997-06-19 | Boehringer Ingelheim Kg | Neue Phenylamidinderivate, Verfahren zu ihrer Herstelung und ihre Verwendung als Arzneimittel |
CA2256309C (en) | 1995-12-29 | 2006-08-15 | 3-Dimensional Pharmaceuticals, Inc. | Amidino protease inhibitors |
US5942544A (en) * | 1996-02-22 | 1999-08-24 | Dupont Pharmaceuticals Company | α-branched anilines, toluenes, and analogs thereof as factor Xa inhibitors |
DE19636689A1 (de) * | 1996-09-10 | 1998-03-12 | Boehringer Ingelheim Kg | Neue Benzamidinderivate |
DE19637123A1 (de) * | 1996-09-12 | 1998-03-19 | Boehringer Ingelheim Kg | Neue Pyranosidderivate |
WO1998013347A1 (en) * | 1996-09-26 | 1998-04-02 | Novartis Ag | Aryl-substituted acrylamides with leukotriene b4 (ltb-4) receptor antagonist activity |
US6670398B2 (en) * | 1997-05-14 | 2003-12-30 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
NZ528906A (en) | 1997-05-14 | 2005-06-24 | Atherogenics Inc | Compounds and methods for the inhibition of the expression of VCAM-1 |
US5872122A (en) * | 1997-10-16 | 1999-02-16 | Monsanto Company | Pyrimidinylamidino β-amino acid derivatives useful as inhibitors of platelet aggregation |
ID24720A (id) | 1997-12-12 | 2000-08-03 | Novartis Ag | Senyawa amidino tersubstitusi dalam perawatan penyakit gangguan paru-paru kronis |
WO1999032125A1 (en) * | 1997-12-23 | 1999-07-01 | Schering Corporation | Composition for treating respiratory and skin diseases, comprising at least one leukotriene antagonist and at least one antihistamine |
US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
DE19948428A1 (de) * | 1999-10-07 | 2001-04-12 | Boehringer Ingelheim Pharma | Neuer LTB¶4¶-Antagonist, Verfahren zu dessen Herstellung und dessen Verwendung als Arzneimittel |
FR2801053B1 (fr) * | 1999-11-16 | 2004-06-25 | Sod Conseils Rech Applic | Nouveaux derives d'amidines, leur preparation et leur application a titre de medicaments |
DE10052333A1 (de) * | 2000-10-24 | 2002-05-02 | Boehringer Ingelheim Pharma | Neue Sulfooxybenzamide |
US6528491B2 (en) * | 2000-10-24 | 2003-03-04 | Boehringer Ingelheim Pharma Kg | Pyranoside derivatives |
JP4334233B2 (ja) * | 2001-04-11 | 2009-09-30 | アセロジエニクス・インコーポレイテツド | プロブコールモノエステルによって血漿hdlコレステロールレベルを上昇させ、hdlの機能性を改善するための方法 |
US20030119901A1 (en) * | 2001-07-14 | 2003-06-26 | Boehringer Ingelheim Pharma Kg | Pharmaceutical formulation containing an LTB4 antagonist |
IL159493A0 (en) * | 2001-07-14 | 2004-06-01 | Boehringer Ingeiheim Pharma Gm | Pharmaceutical formulation containing an ltb4 antagonist |
WO2003017994A1 (en) * | 2001-08-31 | 2003-03-06 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
WO2004058722A1 (en) * | 2002-12-24 | 2004-07-15 | Arena Pharmaceuticals, Inc. | Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a |
EP1493739A1 (fr) * | 2003-07-03 | 2005-01-05 | Warner-Lambert Company LLC | Dérivés thiophényliques d'aminoacides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
US7262223B2 (en) | 2004-01-23 | 2007-08-28 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
GB2445920A (en) * | 2007-01-25 | 2008-07-30 | Mucokinetica Ltd | Amidino compounds for treatment of respiratory disease |
BRPI0809423A2 (pt) * | 2007-03-26 | 2014-09-09 | Salutria Pharmaceuticals Llc | Usos e composições de derivados de probucol para o tratamento de diabetes |
US20080280985A1 (en) * | 2007-03-27 | 2008-11-13 | Scott Robert A D | Methods and Compositions Using Certain Phenolic Derivatives for the Treatment of Diabetes |
US8691866B2 (en) | 2008-12-10 | 2014-04-08 | The General Hospital Corporation | HIF inhibitors and use thereof |
WO2014134391A1 (en) | 2013-02-28 | 2014-09-04 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效rock1及rock2抑制劑之苯基吡唑衍生物 |
WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4889871A (en) * | 1987-05-29 | 1989-12-26 | G. D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives |
AU626033B2 (en) * | 1988-10-25 | 1992-07-23 | Government Of The United States Of America, As Represented By The Secretary Of The Army, The | Methods for the treatment and prophylaxis of pneumocystis carinii pneumonia and other diseases and compounds and formulations for use in said methods |
EP0518818A3 (en) * | 1991-06-11 | 1993-04-28 | Ciba-Geigy Ag | Arylethers, their manufacture and use as medicament |
US5246965A (en) * | 1991-06-11 | 1993-09-21 | Ciba-Geigy | Arylethers, their manufacture and methods of treatment |
ATE125791T1 (de) * | 1991-06-11 | 1995-08-15 | Ciba Geigy Ag | Amidino-verbindungen, ihre herstellung und verwendung als arzneimittel. |
US5424334A (en) * | 1991-12-19 | 1995-06-13 | G. D. Searle & Co. | Peptide mimetic compounds useful as platelet aggregation inhibitors |
-
1993
- 1993-01-14 DE DE59309630T patent/DE59309630D1/de not_active Expired - Fee Related
- 1993-01-14 AU AU33497/93A patent/AU673343B2/en not_active Ceased
- 1993-01-14 PT PT98121305T patent/PT902013E/pt unknown
- 1993-01-14 CZ CZ19941886A patent/CZ287209B6/cs unknown
- 1993-01-14 DE DE59310252T patent/DE59310252D1/de not_active Expired - Fee Related
- 1993-01-14 KR KR1019940702669A patent/KR0163222B1/ko not_active IP Right Cessation
- 1993-01-14 RU RU94041836A patent/RU2124002C1/ru not_active IP Right Cessation
- 1993-01-14 AT AT93902195T patent/ATE180770T1/de not_active IP Right Cessation
- 1993-01-14 PL PL93304713A patent/PL173789B1/pl unknown
- 1993-01-14 ES ES93902195T patent/ES2132216T3/es not_active Expired - Lifetime
- 1993-01-14 EP EP98121305A patent/EP0902013B1/de not_active Expired - Lifetime
- 1993-01-14 JP JP51370193A patent/JP3487851B2/ja not_active Expired - Fee Related
- 1993-01-14 SK SK914-94A patent/SK281016B6/sk unknown
- 1993-01-14 WO PCT/EP1993/000070 patent/WO1993016036A1/de active Application Filing
- 1993-01-14 CA CA002129526A patent/CA2129526A1/en not_active Abandoned
- 1993-01-14 CA CA002427890A patent/CA2427890A1/en not_active Abandoned
- 1993-01-14 EP EP93902195A patent/EP0625138B1/de not_active Expired - Lifetime
- 1993-01-14 NZ NZ246593A patent/NZ246593A/en unknown
- 1993-01-14 SG SG1996008431A patent/SG44837A1/en unknown
- 1993-01-14 AT AT98121305T patent/ATE210634T1/de not_active IP Right Cessation
- 1993-01-14 ES ES98121305T patent/ES2165122T3/es not_active Expired - Lifetime
- 1993-01-14 PL PL93316750A patent/PL173781B1/pl unknown
- 1993-01-14 UA UA94095773A patent/UA43318C2/uk unknown
- 1993-01-14 DK DK98121305T patent/DK0902013T3/da active
- 1993-01-14 DK DK93902195T patent/DK0625138T3/da active
- 1993-01-14 HU HU9402291A patent/HU216191B/hu not_active IP Right Cessation
- 1993-01-29 TW TW082100562A patent/TW232005B/zh active
- 1993-02-03 YU YU6393A patent/YU49038B/sh unknown
- 1993-02-03 IL IL104589A patent/IL104589A0/xx not_active IP Right Cessation
- 1993-02-03 HR HRP4244241.9A patent/HRP930102B1/xx not_active IP Right Cessation
- 1993-02-04 MX MX9300630A patent/MX9300630A/es not_active IP Right Cessation
- 1993-02-05 SI SI9300066A patent/SI9300066B/sl not_active IP Right Cessation
-
1994
- 1994-08-04 NO NO942903A patent/NO301540B1/no not_active IP Right Cessation
- 1994-08-04 FI FI943618A patent/FI943618A/fi unknown
-
1995
- 1995-06-05 US US08/460,961 patent/US6037377A/en not_active Expired - Lifetime
-
1997
- 1997-04-18 CZ CZ19971203A patent/CZ287173B6/cs unknown
-
1999
- 1999-06-09 GR GR990401541T patent/GR3030468T3/el unknown
-
2000
- 2000-01-18 US US09/484,073 patent/US6489365B1/en not_active Expired - Lifetime
-
2002
- 2002-03-18 JP JP2002073593A patent/JP2002322143A/ja active Pending
- 2002-09-23 US US10/252,976 patent/US20030130232A1/en not_active Abandoned
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