ZA200605587B - Novel phenylalanine derivative - Google Patents
Novel phenylalanine derivative Download PDFInfo
- Publication number
- ZA200605587B ZA200605587B ZA200605587A ZA200605587A ZA200605587B ZA 200605587 B ZA200605587 B ZA 200605587B ZA 200605587 A ZA200605587 A ZA 200605587A ZA 200605587 A ZA200605587 A ZA 200605587A ZA 200605587 B ZA200605587 B ZA 200605587B
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- ZA
- South Africa
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- pharmaceutically acceptable
- acceptable salts
- carbon atoms
- hydrogen atom
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Classifications
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Landscapes
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| JP2003425347 | 2003-12-22 | ||
| JP2004074943 | 2004-03-16 | ||
| JP2004159919 | 2004-05-28 | ||
| JP2004260319 | 2004-09-07 |
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| ZA200605587B true ZA200605587B (en) | 2008-02-27 |
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| ZA200605587A ZA200605587B (en) | 2003-12-22 | 2004-12-22 | Novel phenylalanine derivative |
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| EP (3) | EP1700850B1 (pt) |
| JP (1) | JP4743659B2 (pt) |
| KR (2) | KR20110098980A (pt) |
| CN (2) | CN1917881B (pt) |
| AU (1) | AU2004303696B2 (pt) |
| BR (1) | BRPI0418026A (pt) |
| CA (1) | CA2550843C (pt) |
| ES (1) | ES2548853T3 (pt) |
| IL (1) | IL176469A (pt) |
| NO (1) | NO337628B1 (pt) |
| NZ (1) | NZ548420A (pt) |
| RU (1) | RU2390520C2 (pt) |
| WO (1) | WO2005061466A1 (pt) |
| ZA (1) | ZA200605587B (pt) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
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| YU12203A (sh) | 2000-08-18 | 2006-03-03 | Ajinomoto Co.Inc. | Novi derivati fenilalanina |
| JP4895067B2 (ja) * | 2000-09-29 | 2012-03-14 | 味の素株式会社 | 新規フェニルアラニン誘導体 |
| DE60332093D1 (de) * | 2002-02-20 | 2010-05-27 | Ajinomoto Kk | Neues phenylalaninderivat |
| WO2004074264A1 (ja) * | 2003-02-20 | 2004-09-02 | Ajinomoto Co., Inc. | キナゾリンジオン骨格を有するフェニルアラニン誘導体の製造方法及び製造中間体 |
| CN100563658C (zh) * | 2003-11-14 | 2009-12-02 | 味之素株式会社 | 苯丙氨酸衍生物的固体分散体或固体分散体医药制剂 |
| EP1683525B1 (en) * | 2003-11-14 | 2017-05-17 | EA Pharma Co., Ltd. | Sustained-release phenylalanine derivative preparation for oral administration |
| WO2005051925A1 (ja) * | 2003-11-27 | 2005-06-09 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の結晶及びその製造方法 |
| EP1700850B1 (en) * | 2003-12-22 | 2015-07-15 | Ajinomoto Co., Inc. | Phenylalanine derivative |
| CA2613249A1 (en) * | 2005-06-21 | 2006-12-28 | Ajinomoto Co., Inc. | Crystals of phenylalanine derivatives, production method thereof and use thereof |
| WO2007028789A1 (en) * | 2005-09-07 | 2007-03-15 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Quinazoline derivatives as antiviral agents |
| CN101360736A (zh) * | 2005-11-23 | 2009-02-04 | 阿斯利康(瑞典)有限公司 | L-丙氨酸衍生物 |
| WO2007089335A2 (en) * | 2005-12-29 | 2007-08-09 | Lexicon Pharmaceutical Inc. | Multicyclic amino acid derivatives and methods of their use |
| US7834050B2 (en) | 2006-03-29 | 2010-11-16 | Duke University | Small molecule insulin mimetics absent quinones |
| US20080045521A1 (en) * | 2006-06-09 | 2008-02-21 | Astrazeneca Ab | Phenylalanine derivatives |
| MX297306B (es) * | 2006-11-22 | 2012-03-22 | Ajinomoto Kk | Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. |
| WO2008093065A1 (en) * | 2007-01-29 | 2008-08-07 | Astrazeneca Ab | L-ALANINE DERIVATIVES AS α5βL ANTAGONISTS |
| WO2008125811A1 (en) * | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
| US20100113391A1 (en) * | 2007-04-19 | 2010-05-06 | Astellas Pharma Inc. | Bicyclic heterocyclic compound |
| WO2011094890A1 (en) | 2010-02-02 | 2011-08-11 | Argusina Inc. | Phenylalanine derivatives and their use as non-peptide glp-1 receptor modulators |
| WO2011122619A1 (ja) | 2010-03-29 | 2011-10-06 | 味の素株式会社 | フェニルアラニン誘導体の塩の結晶 |
| JP2013530963A (ja) | 2010-06-09 | 2013-08-01 | レセプトス インコーポレイテッド | 新規のｇｌｐ−１受容体安定化薬および調節薬 |
| JP6007417B2 (ja) | 2011-05-31 | 2016-10-12 | レセプトス エルエルシー | 新規ｇｌｐ−１受容体安定剤および調節剤 |
| AU2012352349B2 (en) * | 2011-12-12 | 2017-08-17 | Receptos Llc | Carboxylic acid derivatives comprising four cycles acting as GLP-1 receptor modulators for therapy of diseases such as diabetes |
| WO2013161904A1 (ja) | 2012-04-24 | 2013-10-31 | 味の素株式会社 | スルホンアミド誘導体及びその医薬用途 |
| CN102993105B (zh) * | 2012-12-19 | 2014-06-11 | 西南大学 | 1-甲基-2,4-喹唑啉二酮衍生物及其制备方法和应用 |
| US9260427B2 (en) * | 2013-06-11 | 2016-02-16 | Receptos, Inc. | GLP-1 receptor modulators |
| RU2667520C9 (ru) | 2013-10-29 | 2019-03-05 | ЕА Фарма Ко., Лтд. | Производное сульфонамида и его применение в медицине |
| US9474755B2 (en) | 2014-07-25 | 2016-10-25 | Celgene International Ii Sarl | GLP-1 receptor modulators |
| ES2844573T3 (es) | 2014-12-10 | 2021-07-22 | Receptos Llc | Moduladores del receptor de GLP-1 |
| RU2018117503A (ru) | 2015-10-27 | 2019-11-28 | Мерк Шарп И Доум Корп. | ЗАМЕЩЕННЫЕ ИНДАЗОЛЬНЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ RORγТ И ИХ ПРИМЕНЕНИЕ |
| ES2856125T3 (es) | 2016-02-05 | 2021-09-27 | Ea Pharma Co Ltd | Derivado de sulfonamida y composición farmacéutica que contiene la misma |
| CA3114240C (en) | 2018-10-30 | 2023-09-05 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
| JP7189368B2 (ja) | 2018-10-30 | 2022-12-13 | ギリアード サイエンシーズ， インコーポレイテッド | アルファ４ベータ７インテグリンの阻害のための化合物 |
| CA3115830C (en) | 2018-10-30 | 2023-09-12 | Gilead Sciences, Inc. | Compounds for inhibition of .alpha.4.beta.7 integrin |
| US20220119383A1 (en) | 2018-10-30 | 2022-04-21 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| EP4013499A1 (en) | 2019-08-14 | 2022-06-22 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4111394A1 (de) * | 1991-04-09 | 1992-10-15 | Behringwerke Ag | Amidinophenylalaninderivate, verfahren zu deren herstellung, deren verwendung und diese enthaltende mittel |
| ES2102009T5 (es) | 1992-01-13 | 2004-12-16 | Biogen Inc | Tratamiento para el asma. |
| EP0625912B1 (en) | 1992-02-12 | 1997-04-16 | Biogen, Inc. | Treatment for inflammatory bowel disease |
| EP0677060A1 (en) | 1993-01-08 | 1995-10-18 | Tanabe Seiyaku Co., Ltd. | Peptide inhibitors of cell adhesion |
| SG44845A1 (en) | 1993-01-12 | 1997-12-19 | Biogen Inc | Recombitant anti-vla4 antibody molecules |
| WO1995015973A1 (en) | 1993-12-06 | 1995-06-15 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
| DE122006000043I1 (de) | 1994-01-25 | 2007-02-15 | Elan Pharm Inc | Humanisierte Antik¦rper gegen das Leukozytenadh{sionsmolek}l vla-4 |
| 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 |
| DE19650975A1 (de) * | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| AU744028B2 (en) | 1997-02-28 | 2002-02-14 | Pfizer Products Inc. | Atropisomers of 3-aryl-4(3H)-quinazolinones and their use as ampa-receptor antagonists |
| EP1001972A1 (en) | 1997-07-31 | 2000-05-24 | Elan Pharmaceuticals, Inc. | Substituted phenylalanine type compounds which inhibit leukocyte adhesion mediated by vla-4 |
| HU229362B1 (en) | 1997-08-22 | 2013-11-28 | Hoffmann La Roche | N-alkanoylphenylalanine derivatives |
| JP3727536B2 (ja) | 1997-08-22 | 2005-12-14 | エフ．ホフマン−ラ ロシュ アーゲー | Ｎ−アルカノイルフェニルアラニン誘導体 |
| US6197794B1 (en) | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| JP2002504534A (ja) | 1998-02-26 | 2002-02-12 | セルテック・セラピューティクス・リミテッド | α４インテグリンの阻害剤としてのフェニルアラニン誘導体 |
| DE19817461A1 (de) * | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Benzamide, deren Herstellung und Anwendung |
| DE19818614A1 (de) * | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
| US6171578B1 (en) * | 1999-04-14 | 2001-01-09 | Diatide, Inc. | Benzodiazepine derivatives for imaging thrombi |
| JP3795305B2 (ja) | 1999-07-19 | 2006-07-12 | 田辺製薬株式会社 | 医薬組成物 |
| GB2354440A (en) | 1999-07-20 | 2001-03-28 | Merck & Co Inc | Aryl amides as cell adhesion inhibitors |
| DE60033684T2 (de) * | 1999-11-18 | 2007-12-06 | Ajinomoto Co., Inc. | Phenylalaninderivate |
| PT1244625E (pt) | 1999-12-06 | 2005-09-30 | Hoffmann La Roche | 4-piridinil-n-acil-l-fenilalaninas |
| WO2001042225A2 (en) | 1999-12-06 | 2001-06-14 | F. Hoffmann-La Roche Ag | 4-pyrimidinyl-n-acyl-l-phenylalanines |
| JP4784803B2 (ja) * | 1999-12-28 | 2011-10-05 | 味の素株式会社 | 新規フェニルアラニン誘導体 |
| EP1270547A4 (en) | 2000-03-23 | 2005-07-13 | Ajinomoto Kk | NEW PHENYL ALANIDE DERIVATIVES |
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| YU12203A (sh) * | 2000-08-18 | 2006-03-03 | Ajinomoto Co.Inc. | Novi derivati fenilalanina |
| MY129000A (en) | 2000-08-31 | 2007-03-30 | Tanabe Seiyaku Co | INHIBITORS OF a4 MEDIATED CELL ADHESION |
| JP4895067B2 (ja) * | 2000-09-29 | 2012-03-14 | 味の素株式会社 | 新規フェニルアラニン誘導体 |
| WO2003010135A1 (fr) * | 2001-07-26 | 2003-02-06 | Ajinomoto Co., Inc. | Nouveaux derives de l'acide phenylpropionique |
| EP1454898A4 (en) * | 2001-12-13 | 2006-12-13 | Ajinomoto Kk | NEW PHENYL ALANIDE DERIVATIVES |
| DE60332093D1 (de) * | 2002-02-20 | 2010-05-27 | Ajinomoto Kk | Neues phenylalaninderivat |
| WO2004074264A1 (ja) * | 2003-02-20 | 2004-09-02 | Ajinomoto Co., Inc. | キナゾリンジオン骨格を有するフェニルアラニン誘導体の製造方法及び製造中間体 |
| WO2005032488A2 (en) * | 2003-10-03 | 2005-04-14 | Portola Pharmaceuticals, Inc. | 2,4-dioxo-3-quinazolinylaryl sulfonylureas |
| WO2005051925A1 (ja) * | 2003-11-27 | 2005-06-09 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の結晶及びその製造方法 |
| EP1700850B1 (en) * | 2003-12-22 | 2015-07-15 | Ajinomoto Co., Inc. | Phenylalanine derivative |
| MX297306B (es) * | 2006-11-22 | 2012-03-22 | Ajinomoto Kk | Procedimiento para la produccion de derivados de fenilalanina que tienen estructuras de base de quinazolinodiona e intermediarios para la produccion. |
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- 2004-12-22 AU AU2004303696A patent/AU2004303696B2/en not_active Ceased
- 2004-12-22 US US11/018,226 patent/US7345049B2/en not_active Expired - Fee Related
- 2004-12-22 CN CN200480041967.9A patent/CN1917881B/zh not_active Expired - Fee Related
- 2004-12-22 KR KR1020117019338A patent/KR20110098980A/ko not_active Application Discontinuation
- 2004-12-22 RU RU2006126651/04A patent/RU2390520C2/ru not_active IP Right Cessation
- 2004-12-22 JP JP2005516537A patent/JP4743659B2/ja not_active Expired - Fee Related
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- 2004-12-22 KR KR1020067014754A patent/KR101194176B1/ko active IP Right Grant
- 2004-12-22 ZA ZA200605587A patent/ZA200605587B/en unknown
- 2004-12-22 CA CA2550843A patent/CA2550843C/en not_active Expired - Fee Related
- 2004-12-22 WO PCT/JP2004/019704 patent/WO2005061466A1/ja active Application Filing
- 2004-12-22 CN CN201410016206.3A patent/CN103784458B/zh not_active Expired - Fee Related
- 2004-12-22 NZ NZ548420A patent/NZ548420A/en not_active IP Right Cessation
- 2004-12-22 EP EP13152904.2A patent/EP2615087A3/en not_active Withdrawn
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