KR970704675A - 치환된 벤즈아미딘, 이의 제조방법 및 약제로서의 이의 용도(Substituted benzamidines, their production and their use as medicaments) - Google Patents
치환된 벤즈아미딘, 이의 제조방법 및 약제로서의 이의 용도(Substituted benzamidines, their production and their use as medicaments) Download PDFInfo
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Abstract
화학식(Ⅰ)의 신규한 화합물(여기서, A 및 R1내지 R4는 명세서에 정의한 바와 같다)은 통상적인 방법으로 제조할 수 있고, 예를 들면, LTB4길항제로서 치료적으로 사용할 수 있다.
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Claims (13)
- 하기 화학식(Ⅰ)의 치환된 벤즈아미딘.상기 화학식(Ⅰ)에서, A는 하기 화학식(Ⅱ)의 그룹 또는 하기 화학식(Ⅲ)의 그룹이고, R1은 OH, CN, COR12〔여기서, R12는 C1-C6-알킬, C5-C7-사이클로알킬, 아릴, 헤테로아릴, 아르알킬 또는 헤테로아릴-(C1-C6-알킬)(여기서, 아릴 또는 헤테로아릴 그룹은 Cl, F, CF3, C1-C4-알킬, OH 또는 C1-C4-알콕시에 의해 일치환되거나 다치환될 수 있다)이다〕. COOR12(여기서, R12는 위에서 정의한 바와 같다) 또는 CHO이며, R2는 Br, Cl, F, CF3, OH, C1-C6-알킬, C5-C7-사이크로알킬, 아릴, O-아릴, CH2-아릴, CR5R6-아릴〔여기서, R5는 C5-C4-알킬, CH3,CH2OH, COOH 또는 COO(C1-C4-알킬)이고, R6은 H, C1-C4-알킬 또는 CF3이며, R5와 R6은 함께 C4-C6-알킬렌을 형성할 수 있다〕. C(CH3)2-R7〔여기서, R7은 CH2OH, COOH, COO(C1-C4-알킬), CONR10R11{여기서, R10은 H, C1-C6-알킬, 페닐, 페닐-(C1-C6-알킬), COR12(여기서, R12는 위에서 정의한 바와 같다), COOR12(여기서, R12는 위헤서 정의한 바와 같다), CHO, CONH2, CONHR12(여기서, R12는 위에서 정의한 바와 같다), SO2-(C1-C6-알킬) 또는 SO2-페닐(여기서, 페닐 그룹은 Cl, F, CF3, C1-C4-알킬, OH 및/또는 C1-C4-알콕시에 의해 일치환되거나 다치환될 수 있다)이고, R11은 H 또는 C1-C6-알킬이며, R10과 R11은 함께 C4-C5-알킬렌 그룹을 형성할 수 있다} 또는 CH2NR10R11(여기서, R10및 R11은 위에서 정의한 바와 같다)이다〕이고 A가 하기 화학식(Ⅲ)의 그룹이거나, X2가 하기 화학식(Ⅳ)의 그룹인 경우에는 R2는 또한 H이며, A가 하기 화학식(Ⅳ)의 그룹이다)인 경우나 A가 하기 화학식(Ⅲ)의 그룹이거나 X2가 하기 화학식(Ⅳ)의 그룹인 경우에는 R2는 또한 H이며, A가 하기 화학식(Ⅱ)의 그룹(여기서, X1은 이하 정의하는 바와 같고, X2는 NH, NCH3또는 하기 화학식(Ⅳ)의 그룹이다)인 경우에는 R2는 또한 C1-C6-알콕시이고, R3은 H, C1-C6-알킬, OH, Cl 또는 F이며, R2가 아릴, O-아릴, CH2-아릴, CR5R6-아릴(여기서, R5및 R6은 위에서 정의한 바와 같다) 또는 C(CH3)2-R7(여기서, R7은 위에서 정의한 바와 같다)인 경우나 X2가 하기 화학식(Ⅳ)의 그룹인 경우에는 R3은 또한 C1-C6-알콕시이고, R2와 R3은 함께 융합된 방향족 또는 헤테로방향족환을 형성할 수 있으며, R4는 H 또는 C1-C6-알킬이다.상기 화학식(Ⅱ) 및 (Ⅲ)에서, X1은 O, NH 또는 NCH3이고, X2는 O, NH, NCH3또는 하기 화학식(Ⅳ)의 그룹이며, m은 2내지 4이고, X3및X4는 각각 -X-CnH2n-(여기서, X는 0,NH 또는 NCH3이고, n은 1 또는 2이다)이며, R8및 R9는 각각H, Br, Cl, F,OH, C1-C6-알콕시이다.상기 화학식(Ⅳ)에서, X1은 위에서 정의한 바와 같다.
- 제1항에 있어서, 아릴이 페닐 또는 일치환되거나 다치환된 페닐을 나타내고 헤테로아릴이 피리딜, 피리다지닐, 피리미딜, 피라지닐, 티에닐 또는 푸릴을 나타내는 화합물.
- 제1항 또는 제2항에 있어서, A, m, n, X3, X4및 R1이 제1항에서 정의한 바와 같고 X1이 0이며 X2가 0 또는 화학식(Ⅳ)의 그룹(여기서, X1은 0이다)이고 R2가 Cl, F, CF3, OH, C1-C6-알킬, 아릴, 0-아릴, CH2-아릴 또는 CR5R5-아릴(여기서, R5는 C1-C3-알킬, CF3또는 CH2OH이고, R6은 H,C1-C3-알킬 또는 CF3이며, R5와 R6은 함께 C4-C5-알킬렌을 형성할 수 있다)이며 R2가 화학식(Ⅳ)의 그룹인 경우에는 R2는 또한 C1-C6-알콕시일 수 있고, R3이 H, C1-C6-알킬 또는 OH이며 R2가 CR5R6-아릴(여기서, R5및 R6은 위에서 정의한 바와 같다)인 경우에는 R3은 또한 C1-C6-알콕시이고 R4가 H이며 R8및R9가 H, F 또는 OH인 화합물.
- 제1항 또는 제2항에 있어서, X1이 0이고 X2가 화학식(Ⅳ)의 그룹(여기서, X1은 0이다)이며 X가 0이고 R1이 COOR12(여기서, R12는 C1-C6-알킬, 아르알킬 또는 C5-C7-사이클로알킬이다)이며 R2가 C1-C6-알킬, 아릴, 0-아릴, CH2-아릴 또는 CR5R5-아릴(여기서, R5및 R6은 C1-C3-알킬, CF3이다)이고 R3이 H, OH 또는 C1-C6-알킬 이며 R2가 CR5R5-아릴(여기서, R5와 R6은 위에서 정의한 바와 같다)인 경우엔 R3은 또한 C1-C6-알콕시이고 R8및 R9가 H인 화합물.
- (메톡시카보닐-이미노-{4'-〔2-(2-프로페녹시)에톡시〕비페닐-4-일}메틸)아민 및 이의 산 부가염.
- (벤질옥시카보닐-이미노-{4'-〔2-(2-프로페녹시)에톡시〕비페닐-4-일}메틸)아민 및 이의 산 부가염.
- 〔하이드록시-이미노-(4-{3-〔4-(1-메틸-1-페닐에틸)페녹시메틸〕벤조일옥시}페닐)메틸〕아민 및 이의 산 부가염.
- 〔에톡시카보닐-이미노-(4-{3-〔4-(1-메틸-1-페닐에틸)페녹시메틸〕벤조일옥시}페닐)메틸〕아민 및 이의 산 부가염.
- 〔3'-피리카보닐-이미노-(4-{3-〔4-(1-메틸-1-페닐에틸)페녹시메틸〕벤질옥시}페닐)메틸〕아민 및 이의 산 부가염.
- 제1항 내지 제9항 중 어느 한 항에 따르는 화합물을 약리학적으로 허용되는 희석제, 부형제 및/또는 담체와 함께 포함하는 약제학적 제제.
- LBT4- 길항제가 치료적으로 사용될 수 있는 질환 치료용 약제학적 조성물의 제조에 있어서의 제1항 내지 제9항 중의 어느 한 항에 따르는 화합물의 용도.
- 감염 및/또는 알러지성 진행이 관련된 질환, 특히 관절염, 천식, 만성 폐색성 폐질환, 건선, 궤양성 대장염, 알쯔하이머병, 쇼크, 아테롬성 동맥경화증, 복합경화증, 비스테로이드성 소염제로 인한 위병, 전이 및 만성 골수병 백혈병의 치료에 있어서의 제1항 내지 제9항 중의 어느 한 항에 따르는 화합물의 용도.
- (a) 하기 화학식(Ⅴ)의 아미딘을 하기 화학식(Ⅵ)의 화합물과 반응시키거나, (b) 하기 화학식(Ⅶ)의 화합물을 하기 화학식(Ⅷ) 또는 (Ⅸ)의 벤즈아미딘과 반응시키거나, (c) 하기 화학식(Ⅹ)의 화합물을 하기 화학식(XI) 또는 (XⅡ)의 화합물가 반응시키거나, (d) 하기 화학식(XⅢ)의 니트릴을 하이드록실아민과 반응시켜, R1이 OH인 화학식(Ⅰ)의 화합물을 제조하고, 생성된 생성물로부터 광학 이성체 또는 이성체의 부분입체 이성체쌍 또는 이들의 혼합물을 이들의 특성에 따라 제조할 수 있거나, 염기가 수득되는 경우, 산 부가염을 제조할 수 있고, 산 부가염이 초기에 수득되는 경우, 유리 염기를 수득할 수 있거나, 토오토머 형태를 제조할 수 있고/있거나 분리할 수 있음을 특징으로 하여, 제1항 내지 제9항 중의 어느 한 항에 따르는 화합물을 제조하는 방법.상기 화학식(Ⅴ) 내지 (XⅢ)에서, A, R1, R2, R3, R4, R8, R9, X1, X2, X3, X4, m 및 n은 제1항에서 정의한 바와 같고, R'1은 R1과 동일한 의미(단, OH는 제외된다)이며, L은 할로겐 원자(예:Cl 또는 Br) 또는 아실옥시와 같은 친핵 교환성 그룹이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4424713.3 | 1994-07-13 | ||
DE4424713A DE4424713A1 (de) | 1994-07-13 | 1994-07-13 | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
Publications (2)
Publication Number | Publication Date |
---|---|
KR970704675A true KR970704675A (ko) | 1997-09-06 |
KR100421580B1 KR100421580B1 (ko) | 2004-07-31 |
Family
ID=6523047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970700124A KR100421580B1 (ko) | 1994-07-13 | 1995-06-03 | 치환된벤즈아미딘및이의제조방법 |
Country Status (37)
Country | Link |
---|---|
US (1) | US5731332A (ko) |
EP (1) | EP0770059B1 (ko) |
JP (1) | JP2931410B2 (ko) |
KR (1) | KR100421580B1 (ko) |
CN (1) | CN1083830C (ko) |
AT (1) | ATE178590T1 (ko) |
AU (1) | AU700585B2 (ko) |
BG (1) | BG62090B1 (ko) |
BR (1) | BR9508374A (ko) |
CA (1) | CA2194885C (ko) |
CO (1) | CO4410184A1 (ko) |
CZ (1) | CZ289376B6 (ko) |
DE (2) | DE4424713A1 (ko) |
DK (1) | DK0770059T3 (ko) |
EE (1) | EE03311B1 (ko) |
ES (1) | ES2131830T3 (ko) |
FI (1) | FI970094A0 (ko) |
GR (1) | GR3030043T3 (ko) |
HK (1) | HK1011966A1 (ko) |
HR (1) | HRP950365B1 (ko) |
HU (1) | HU224823B1 (ko) |
IL (1) | IL114571A (ko) |
MX (1) | MX9700273A (ko) |
MY (1) | MY117090A (ko) |
NO (1) | NO307373B1 (ko) |
NZ (1) | NZ287883A (ko) |
PE (1) | PE32496A1 (ko) |
PL (1) | PL179595B1 (ko) |
RO (1) | RO118653B1 (ko) |
RU (1) | RU2159228C2 (ko) |
SA (1) | SA95160355B1 (ko) |
SK (1) | SK281744B6 (ko) |
TW (1) | TW555738B (ko) |
UA (1) | UA45351C2 (ko) |
WO (1) | WO1996002497A1 (ko) |
YU (1) | YU48934B (ko) |
ZA (1) | ZA955780B (ko) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6486181B1 (en) | 1992-08-28 | 2002-11-26 | City Of Hope | Human leukocutye 12-lipoxygenase and its role in the pathogenesis of disease states |
US6191169B1 (en) | 1992-08-28 | 2001-02-20 | City Of Hope | Human leukocyte 12-lipoxygenase and its role in the pathogenesis of disease states |
WO1996028427A1 (en) * | 1995-03-10 | 1996-09-19 | Berlex Laboratories, Inc. | Benzamidine derivatives their preparation and their use as anti-coagulants |
EP0743064A1 (en) * | 1995-05-17 | 1996-11-20 | Eli Lilly And Company | Leukotriene antagonists for use in the treatment or prevention of alzheimer's disease |
DE19636689A1 (de) | 1996-09-10 | 1998-03-12 | Boehringer Ingelheim Kg | Neue Benzamidinderivate |
DE19718334A1 (de) | 1997-04-30 | 1998-11-05 | Boehringer Ingelheim Pharma | Neue Benzylaminderivate und Phenylethylaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
TW513402B (en) * | 1997-05-30 | 2002-12-11 | Daiichi Seiyaku Co | Process for preparing 3-(7-amidino-2-naphthyl)-2-phenylpropionic acid derivatives |
AU1081399A (en) * | 1997-10-15 | 1999-05-03 | City Of Hope | 12(s)-hete receptor blockers |
ID24720A (id) | 1997-12-12 | 2000-08-03 | Novartis Ag | Senyawa amidino tersubstitusi dalam perawatan penyakit gangguan paru-paru kronis |
DE19834713A1 (de) * | 1998-07-31 | 2000-02-03 | Boehringer Ingelheim Pharma | Neue Phenylethylaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US6291531B1 (en) * | 1999-10-07 | 2001-09-18 | Boehringer Ingelheim Pharma Kg | LTB4 antagonist, processes for the preparation thereof and its use as a pharmaceutical composition |
DE10000907A1 (de) * | 2000-01-12 | 2001-07-19 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Aryl-iminomethyl-carbaminsäureestern |
US6417382B2 (en) | 2000-01-12 | 2002-07-09 | Boehringer Ingelheim Pharma Kg | Process for preparing aryl-iminomethyl-carbamino acid esters |
US6528491B2 (en) * | 2000-10-24 | 2003-03-04 | Boehringer Ingelheim Pharma Kg | Pyranoside derivatives |
CA2433451A1 (en) * | 2001-01-16 | 2002-07-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of an ltb4 antagonist for the treatment and/or prevention of diseases caused by increased expression of mucin genes |
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 |
CN1658852A (zh) * | 2001-08-31 | 2005-08-24 | 神经化学(国际)有限公司 | 用于治疗淀粉样变性的脒衍生物 |
RS20050390A (en) * | 2002-11-26 | 2008-04-04 | Boehringer Ingelheim Pharma Gmbh. & Co.Kg., | Pharmaceutical composition comprising a ltb4 antagonist and a cox-2 inhibitor or a combined cox 1/2 inhibitor |
DE10350528A1 (de) * | 2003-10-29 | 2005-06-09 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Arzneimittelformulierung, enthaltend einen LTB4-Antagonisten, sowie Verfahren zu deren Herstellung und deren Verwendung |
US7262223B2 (en) * | 2004-01-23 | 2007-08-28 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
CN103012200B (zh) * | 2011-09-20 | 2014-12-17 | 北京大学 | 具有β-分泌酶抑制功能的化合物及其制备方法与应用 |
CN110869362A (zh) | 2017-05-12 | 2020-03-06 | 国立研究开发法人理化学研究所 | A类gpcr结合性化合物改性体 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0518818A3 (en) * | 1991-06-11 | 1993-04-28 | Ciba-Geigy Ag | Arylethers, their manufacture and use as medicament |
ES2075672T3 (es) * | 1991-06-11 | 1995-10-01 | Ciba Geigy Ag | Amidinocompuestos, su fabricacion y uso como medicamento. |
US5451700A (en) * | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
SK281016B6 (sk) * | 1992-02-05 | 2000-10-09 | Boehringer Ingelheim Kg | Amidínové deriváty, spôsob ich výroby, použitie a farmaceutické prostriedky s ich obsahom |
US5455274A (en) * | 1992-12-09 | 1995-10-03 | Ciba-Geigy Corporation | Hydroxyamidine derivatives |
-
1994
- 1994-07-13 DE DE4424713A patent/DE4424713A1/de not_active Withdrawn
-
1995
- 1995-06-03 US US08/765,692 patent/US5731332A/en not_active Expired - Lifetime
- 1995-06-03 RU RU97102043/04A patent/RU2159228C2/ru not_active IP Right Cessation
- 1995-06-03 UA UA97020598A patent/UA45351C2/uk unknown
- 1995-06-03 AT AT95921824T patent/ATE178590T1/de active
- 1995-06-03 SK SK19-97A patent/SK281744B6/sk not_active IP Right Cessation
- 1995-06-03 ES ES95921824T patent/ES2131830T3/es not_active Expired - Lifetime
- 1995-06-03 RO RO97-00018A patent/RO118653B1/ro unknown
- 1995-06-03 DE DE59505600T patent/DE59505600D1/de not_active Expired - Lifetime
- 1995-06-03 CN CN95194048A patent/CN1083830C/zh not_active Expired - Fee Related
- 1995-06-03 WO PCT/EP1995/002112 patent/WO1996002497A1/de active IP Right Grant
- 1995-06-03 NZ NZ287883A patent/NZ287883A/xx not_active IP Right Cessation
- 1995-06-03 AU AU26742/95A patent/AU700585B2/en not_active Ceased
- 1995-06-03 CA CA002194885A patent/CA2194885C/en not_active Expired - Fee Related
- 1995-06-03 KR KR1019970700124A patent/KR100421580B1/ko not_active IP Right Cessation
- 1995-06-03 MX MX9700273A patent/MX9700273A/es not_active IP Right Cessation
- 1995-06-03 CZ CZ199766A patent/CZ289376B6/cs not_active IP Right Cessation
- 1995-06-03 HU HU9700059A patent/HU224823B1/hu not_active IP Right Cessation
- 1995-06-03 BR BR9508374A patent/BR9508374A/pt not_active IP Right Cessation
- 1995-06-03 PL PL95318115A patent/PL179595B1/pl not_active IP Right Cessation
- 1995-06-03 EP EP95921824A patent/EP0770059B1/de not_active Expired - Lifetime
- 1995-06-03 JP JP8504618A patent/JP2931410B2/ja not_active Expired - Lifetime
- 1995-06-03 EE EE9700066A patent/EE03311B1/xx not_active IP Right Cessation
- 1995-06-03 DK DK95921824T patent/DK0770059T3/da active
- 1995-06-28 HR HRP4424713.3A patent/HRP950365B1/xx not_active IP Right Cessation
- 1995-07-04 TW TW084106873A patent/TW555738B/zh active
- 1995-07-06 YU YU45295A patent/YU48934B/sh unknown
- 1995-07-11 PE PE1995273519A patent/PE32496A1/es not_active Application Discontinuation
- 1995-07-12 ZA ZA955780A patent/ZA955780B/xx unknown
- 1995-07-12 IL IL11457195A patent/IL114571A/xx not_active IP Right Cessation
- 1995-07-12 CO CO95030618A patent/CO4410184A1/es unknown
- 1995-07-13 MY MYPI95001982A patent/MY117090A/en unknown
- 1995-11-01 SA SA95160355A patent/SA95160355B1/ar unknown
-
1997
- 1997-01-04 BG BG101105A patent/BG62090B1/bg unknown
- 1997-01-10 NO NO970122A patent/NO307373B1/no unknown
- 1997-01-10 FI FI970094A patent/FI970094A0/fi not_active Application Discontinuation
-
1998
- 1998-12-14 HK HK98113328A patent/HK1011966A1/xx not_active IP Right Cessation
-
1999
- 1999-04-23 GR GR990401120T patent/GR3030043T3/el unknown
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