ZA200306107B - Imidazolidine derivatives, their preparation, and their use as anti-inflamatory agent. - Google Patents
Imidazolidine derivatives, their preparation, and their use as anti-inflamatory agent. Download PDFInfo
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- ZA200306107B ZA200306107B ZA200306107A ZA200306107A ZA200306107B ZA 200306107 B ZA200306107 B ZA 200306107B ZA 200306107 A ZA200306107 A ZA 200306107A ZA 200306107 A ZA200306107 A ZA 200306107A ZA 200306107 B ZA200306107 B ZA 200306107B
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- South Africa
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- formula
- methyl
- compound
- phenyl
- physiologically tolerable
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Diabetes (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
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- Emergency Medicine (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10111877A DE10111877A1 (de) | 2001-03-10 | 2001-03-10 | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306107B true ZA200306107B (en) | 2004-09-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306107A ZA200306107B (en) | 2001-03-10 | 2003-08-07 | Imidazolidine derivatives, their preparation, and their use as anti-inflamatory agent. |
Country Status (35)
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| US (1) | US6680333B2 (es) |
| EP (1) | EP1373249B1 (es) |
| JP (1) | JP4482277B2 (es) |
| KR (1) | KR100991678B1 (es) |
| CN (1) | CN1227248C (es) |
| AR (1) | AR035692A1 (es) |
| AT (1) | ATE293621T1 (es) |
| AU (1) | AU2002233358B2 (es) |
| BG (1) | BG108134A (es) |
| BR (1) | BR0207981A (es) |
| CA (1) | CA2440648C (es) |
| CZ (1) | CZ301893B6 (es) |
| DE (2) | DE10111877A1 (es) |
| DK (1) | DK1373249T3 (es) |
| EE (1) | EE05401B1 (es) |
| ES (1) | ES2240687T3 (es) |
| HK (1) | HK1062173A1 (es) |
| HR (1) | HRP20030713B1 (es) |
| HU (1) | HU228304B1 (es) |
| IL (2) | IL157830A0 (es) |
| ME (1) | MEP61108A (es) |
| MX (1) | MXPA03007634A (es) |
| MY (1) | MY129029A (es) |
| NO (1) | NO326001B1 (es) |
| NZ (1) | NZ528075A (es) |
| PE (1) | PE20020904A1 (es) |
| PL (1) | PL204622B1 (es) |
| PT (1) | PT1373249E (es) |
| RS (1) | RS51140B (es) |
| RU (1) | RU2303592C2 (es) |
| SI (1) | SI1373249T1 (es) |
| SK (1) | SK286652B6 (es) |
| TW (1) | TWI328587B (es) |
| WO (1) | WO2002072573A1 (es) |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19647380A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-Ring-Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| BR0009277A (pt) * | 1999-03-22 | 2002-02-05 | Ortho Mcneil Pharm Inc | Processo de preparação de ácido propiÈnico de 3s-3-amino-3-arila e derivados deste |
| WO2005034953A1 (ja) * | 2003-10-10 | 2005-04-21 | Kowa Co., Ltd. | 血管新生抑制薬 |
| US20090275529A1 (en) * | 2008-05-05 | 2009-11-05 | Reiss Allison B | Method for improving cardiovascular risk profile of cox inhibitors |
| EP2632492B1 (en) | 2010-10-25 | 2017-10-04 | Biogen MA Inc. | METHODS FOR DETERMINING DIFFERENCES IN ALPHA-4 INTEGRIN ACTIVITY BY CORRELATING DIFFERENCES IN sVCAM AND/OR sMAdCAM LEVELS |
| CN112707874A (zh) * | 2020-12-29 | 2021-04-27 | 广东中科药物研究有限公司 | 一种抗病毒化合物及其制备方法 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4009506A1 (de) | 1990-03-24 | 1991-09-26 | Hoechst Ag | Hydantoinderivate |
| DE4126277A1 (de) | 1991-08-08 | 1993-02-11 | Cassella Ag | Hydantoinderivate |
| JPH07506091A (ja) | 1992-01-13 | 1995-07-06 | バイオゲン インコーポレイテッド | 喘息の処置 |
| JPH07506566A (ja) | 1992-02-12 | 1995-07-20 | バイオゲン インコーポレイテッド | 炎症性胃腸病の処置 |
| DE4207254A1 (de) | 1992-03-07 | 1993-09-09 | Cassella Ag | 4-oxo-2-thioxoimidazolidin-derivate |
| DE4213634A1 (de) | 1992-04-24 | 1993-10-28 | Cassella Ag | 2,4-Dioxo-imidazolidin-Derivate |
| DE4224414A1 (de) | 1992-07-24 | 1994-01-27 | Cassella Ag | Phenylimidazolidin-derivate, ihre Herstellung und ihre Verwendung |
| DE4228717A1 (de) | 1992-08-28 | 1994-03-03 | Cassella Ag | Imidazolidin-Derivate |
| EP0677060A1 (en) | 1993-01-08 | 1995-10-18 | Tanabe Seiyaku Co., Ltd. | Peptide inhibitors of cell adhesion |
| DE69419721T2 (de) | 1993-01-12 | 2000-04-27 | Biogen Inc | Rekombinante anti-vla4 antikörpermoleküle |
| ATE161730T1 (de) | 1993-02-09 | 1998-01-15 | Biogen Inc | Antikörper zur behandlung von insulinabhängigen diabetes |
| DE4308034A1 (de) | 1993-03-13 | 1994-09-15 | Cassella Ag | Neue Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4427979A1 (de) | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| AU693143B2 (en) | 1993-12-06 | 1998-06-25 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
| CN1211123C (zh) | 1994-01-25 | 2005-07-20 | 雅典娜神经科学公司 | 抗白细胞粘附分子vla－4的人源化抗体 |
| WO1996000581A1 (en) | 1994-06-29 | 1996-01-11 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin alpha 4 beta 1 to vcam-1 or fibronectin |
| US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
| GB9524630D0 (en) | 1994-12-24 | 1996-01-31 | Zeneca Ltd | Chemical compounds |
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| DE19515177A1 (de) | 1995-04-28 | 1996-10-31 | Cassella Ag | Hydantoinderivate als Zwischenprodukte für pharmazeutische Wirkstoffe |
| US6248713B1 (en) | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
| ES2171768T3 (es) | 1996-03-20 | 2002-09-16 | Hoechst Ag | Inhibidores de la resorcion osea y antagonistas de receptores de vitronectina. |
| SG124234A1 (en) | 1996-07-25 | 2006-08-30 | Biogen Idec Inc | Cell adhesion inhibitors |
| DE19647381A1 (de) | 1996-11-15 | 1998-05-20 | Hoechst Ag | Neue Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| PL323130A1 (en) | 1996-11-15 | 1998-05-25 | Hoechst Ag | Application of heterocyclic compounds in production of a pharmaceutic agent, novel heterocyclic compounds and pharmaceutic agent as such |
| DE19647380A1 (de) | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-Ring-Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| WO1998042656A1 (en) | 1997-03-21 | 1998-10-01 | Cytel Corporation | Novel compounds |
| DE19741235A1 (de) | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19741873A1 (de) | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| AU748041B2 (en) | 1997-10-31 | 2002-05-30 | Aventis Pharma Limited | Substituted anilides |
| GB9723789D0 (en) * | 1997-11-12 | 1998-01-07 | Zeneca Ltd | Chemical compounds |
| DE19751251A1 (de) * | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate |
| AU3716499A (en) | 1998-04-21 | 1999-11-08 | Aventis Pharma Limited | Substituted diamines and their use as cell adhesion inhibitors |
| DE19821483A1 (de) * | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| BR9911701A (pt) * | 1998-06-30 | 2001-03-20 | Pfizer Prod Inc | Inibidores não peptidila da ligação à célula dependente de vla-4 úteis no tratamento de doenças inflamatórias, auto-imunes e respiratórias |
| WO2000002903A1 (en) | 1998-07-10 | 2000-01-20 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
| DE19922462A1 (de) * | 1999-05-17 | 2000-11-23 | Aventis Pharma Gmbh | Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate |
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