CN102471260B - 苯磺酰胺化合物、其合成方法及其在药品以及美容用品中的用途 - Google Patents

苯磺酰胺化合物、其合成方法及其在药品以及美容用品中的用途 Download PDF

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CN102471260B
CN102471260B CN201080029354.9A CN201080029354A CN102471260B CN 102471260 B CN102471260 B CN 102471260B CN 201080029354 A CN201080029354 A CN 201080029354A CN 102471260 B CN102471260 B CN 102471260B
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hydroxyl
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CN102471260A (zh
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L.克拉里
S.尚邦
L.尚塔拉
C.罗西格诺利
O.鲁瓦耶
J-C.帕斯卡尔
M.舒普利
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Galderma Research and Development SNC
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FR2947268B1 (fr) 2009-06-30 2011-08-26 Galderma Res & Dev Nouveaux composes benzene-sulfonamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique
FR2950057B1 (fr) * 2009-09-17 2011-08-26 Galderma Res & Dev Nouveaux composes benzene-carboxylamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique
US20140275108A1 (en) * 2013-03-15 2014-09-18 Galderma Research & Development Novel benzenesulfonamide compounds, method for synthesizing same, and use thereof in medicine as well as in cosmetics
US9586832B2 (en) * 2013-03-15 2017-03-07 Dru L. DeLaet Method for destruction of halons
CN103224476A (zh) * 2013-05-25 2013-07-31 上高县瑞雅精细化工有限公司 二乙醇胺法制备1-[2-(2-羟基乙氧基)乙基]哌嗪新工艺
FR3030521B1 (fr) * 2014-12-23 2019-07-26 Galderma Research & Development Nouveaux composes heterocycliques et leur utilisation en medecine ainsi qu'en cosmetique
EP3199534B1 (en) 2016-02-01 2018-09-05 Galderma Research & Development Benzenesulfonamide compounds, method for synthesizing same, and use thereof in medicine and cosmetics
US12023310B2 (en) * 2022-08-30 2024-07-02 Gongwin Biopharm Co., Ltd Method for treating peripheral nerve sheath tumor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1337944A (zh) * 1999-01-27 2002-02-27 美国氰胺公司 作为TACE抑制剂的炔β-氨磺酰和次膦酸酰胺异羟肟酸
CN1610661A (zh) * 2001-11-01 2005-04-27 惠氏控股公司 用作基质金属蛋白酶和tace的抑制剂的丙二烯芳基磺酰胺异羟肟酸
WO2008045671A1 (en) * 2006-10-06 2008-04-17 Janssen Pharmaceutica, N.V. Matrix metalloprotease inhibitors

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5506242A (en) 1993-01-06 1996-04-09 Ciba-Geigy Corporation Arylsufonamido-substituted hydroxamic acids
TR199800849T2 (xx) 1995-11-13 1998-07-21 Hoechst Aktiengesellschaft Siklikle heterosiklik N-ikame edilmi� alfa-iminohidroksamla karbon asitleri
TW453995B (en) 1995-12-15 2001-09-11 Novartis Ag Certain alpha-substituted arylsulfonamido acetohydroxamic acids
TW448172B (en) * 1996-03-08 2001-08-01 Pharmacia & Upjohn Co Llc Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation
DE69709160T2 (de) 1996-10-16 2002-08-14 American Cyanamid Co., Madison Herstellung und anwendung von ortho-sulfonamido-aryl-hydroxamsäuren als matrix-metalloproteinase- und tace-inhibitoren
KR20000049197A (ko) 1996-10-16 2000-07-25 윌리암 에이취 캘넌, 에곤 이 버그 매트릭스 메탈로프로테이나제 및 종양 괴사 인자-α 전환 효소억제제로서의 오르토-설폰아미도 헤테로아릴 하이드록삼산의 제조 및 용도
AU743901B2 (en) 1996-10-16 2002-02-07 Wyeth Holdings Corporation Ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloprote inase and tace inhibitors
NZ335053A (en) 1996-10-16 2000-10-27 American Cyanamid Co Beta-sulfonamido hydroxamic acids or ortho-sulfonamido aryl hydroxamic acids as matrix metalloproteinase MMP and TACE (tumour necrosis factor, TNF, alpha converting enzyme) inhibitors
JP3563411B2 (ja) 1997-01-23 2004-09-08 エフ・ホフマン−ラ ロシュ アーゲー スルファミド−メタロプロテアーゼ阻害剤
CN1213021C (zh) 1998-02-19 2005-08-03 惠氏控股公司 作为基质金属蛋白酶抑制剂的 n -羟基- 2 - (烷基、芳基或杂芳基硫烷基、亚磺酰基或磺酰基 ) - 3 -取代的烷
JP3092798B2 (ja) * 1998-06-30 2000-09-25 日本電気株式会社 適応送受信装置
CZ20012294A3 (cs) 1998-12-22 2001-12-12 F. Hoffmann-La Roche Ag Sulfonamidové hydroxamáty
AR035313A1 (es) 1999-01-27 2004-05-12 Wyeth Corp Inhibidores de tace acetilenicos de acido hidroxamico de sulfonamida a base de alfa-aminoacidos, composiciones farmaceuticas y el uso de los mismos para la manufactura de medicamentos.
US6326516B1 (en) * 1999-01-27 2001-12-04 American Cyanamid Company Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors
EP1431285B1 (en) 2001-09-07 2009-01-07 Kaken Pharmaceutical Co., Ltd. Reverse hydroxamic acid derivatives
TW200616612A (en) 2004-10-08 2006-06-01 Wyeth Corp Method for the teatment of polycystic kidney disease field of invention
FR2947268B1 (fr) * 2009-06-30 2011-08-26 Galderma Res & Dev Nouveaux composes benzene-sulfonamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1337944A (zh) * 1999-01-27 2002-02-27 美国氰胺公司 作为TACE抑制剂的炔β-氨磺酰和次膦酸酰胺异羟肟酸
CN1610661A (zh) * 2001-11-01 2005-04-27 惠氏控股公司 用作基质金属蛋白酶和tace的抑制剂的丙二烯芳基磺酰胺异羟肟酸
WO2008045671A1 (en) * 2006-10-06 2008-04-17 Janssen Pharmaceutica, N.V. Matrix metalloprotease inhibitors

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