CN100390158C - 二苯基乙烯化合物的新的杂环类似物 - Google Patents
二苯基乙烯化合物的新的杂环类似物 Download PDFInfo
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- CN100390158C CN100390158C CNB018204457A CN01820445A CN100390158C CN 100390158 C CN100390158 C CN 100390158C CN B018204457 A CNB018204457 A CN B018204457A CN 01820445 A CN01820445 A CN 01820445A CN 100390158 C CN100390158 C CN 100390158C
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Abstract
Description
类别 | 批准的药物 | 机理 | 限制 |
磺酰脲 | 4(第一代)2(第二代) | 作用于胰腺,使其释放更多胰岛素 | 产生抗性 |
双缩胍 | 甲福明 | 减少肝脏的葡萄糖产生量;改进胰岛素敏感性 | 肝脏问题,乳酸中毒症 |
α-葡萄糖苷酶抑制剂 | 阿卡波糖 | 干扰消化过程;减少葡萄糖吸收 | 仅在食后有用 |
噻唑烷二酮 | Troglitazone(已撤回)rosiglitazonepioglitazone | 减少胰岛素抗性 | 胰岛素的附件;对患有心脏和肝脏疾病的人无效 |
Claims (32)
Applications Claiming Priority (6)
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US59110500A | 2000-06-09 | 2000-06-09 | |
US09/591,105 | 2000-06-09 | ||
US09/785,554 | 2001-02-20 | ||
US09/785,554 US20020025975A1 (en) | 1998-05-08 | 2001-02-20 | Novel Heterocyclic analogs of diphenylethylene compounds |
US09/843,167 US7105552B2 (en) | 1998-05-08 | 2001-04-27 | Heterocyclic analogs of diphenylethylene compounds |
US09/843,167 | 2001-04-27 |
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CN1537002A CN1537002A (zh) | 2004-10-13 |
CN100390158C true CN100390158C (zh) | 2008-05-28 |
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US (2) | US7105552B2 (zh) |
EP (1) | EP1360178B1 (zh) |
JP (1) | JP5048199B2 (zh) |
KR (2) | KR100844098B1 (zh) |
CN (1) | CN100390158C (zh) |
AT (1) | ATE422886T1 (zh) |
AU (2) | AU2001266670B9 (zh) |
CA (1) | CA2410171A1 (zh) |
DE (1) | DE60137718D1 (zh) |
DK (1) | DK1360178T3 (zh) |
ES (1) | ES2317911T3 (zh) |
HK (1) | HK1058190A1 (zh) |
MX (1) | MXPA02012038A (zh) |
NZ (1) | NZ522660A (zh) |
WO (1) | WO2001095859A2 (zh) |
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US7105552B2 (en) * | 1998-05-08 | 2006-09-12 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
US7407978B2 (en) * | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
CN1384825A (zh) * | 1999-08-31 | 2002-12-11 | 马克西亚药品公司 | 亚苄基-噻唑烷二酮及其类似物以及它们在治疗糖尿病中的应用 |
US7323496B2 (en) * | 1999-11-08 | 2008-01-29 | Theracos, Inc. | Compounds for treatment of inflammation, diabetes and related disorders |
US20080108825A1 (en) * | 1999-11-08 | 2008-05-08 | Theracos, Inc. | Compounds for treatment of inflammation, diabetes and related disorders |
US7321050B2 (en) | 1999-12-06 | 2008-01-22 | Welichem Biotech Inc. | Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxy stilbenes and novel stilbene derivatives and analogues |
EP1251738B1 (en) * | 2000-02-04 | 2008-12-17 | Theracos, Inc. | Novel diphenylethylene compounds |
US20080103302A1 (en) * | 2000-02-04 | 2008-05-01 | Theracos, Inc. | Compounds for treatment of inflammation, diabetes and related disorders |
CN100462354C (zh) | 2001-01-18 | 2009-02-18 | 天济药业(深圳)有限公司 | 治疗免疫疾病的新的1,2-二苯基乙烯衍生物 |
AU2002319677B8 (en) * | 2001-07-23 | 2009-04-30 | Atwater Management Llc | Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods |
WO2004033632A2 (en) | 2002-10-04 | 2004-04-22 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or tnf-alpha converting enzyme (tace) |
US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
US8969291B2 (en) | 2004-10-08 | 2015-03-03 | Enzo Therapeutics, Inc. | Methods for decreasing leptin levels or activity for treating inflammation |
US20100305174A1 (en) * | 2005-04-13 | 2010-12-02 | Orchid Research Laboratories Limited | Novel Heterocyclic Derivatives |
ES2675588T3 (es) | 2012-05-29 | 2018-07-11 | Parion Sciences, Inc. | Dendrímero como aminoamidas que posee actividad de bloqueador de canal de sodio para el tratamiento del ojo seco y otras enfermedades mucosas |
CN112209896B (zh) * | 2019-07-10 | 2023-05-16 | 苏州泽璟生物制药股份有限公司 | 噻唑烷二酮衍生物以及包含其的药物组合物 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4297429A (en) * | 1979-06-18 | 1981-10-27 | Mitsubishi Paper Mills, Ltd. | Photographic material and diffusion transfer processing solution for making printing plates and method for making printing plates |
Family Cites Families (63)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3683009A (en) | 1968-10-10 | 1972-08-08 | Du Pont | {60 , {62 -bis(trifluoromethyl) stilbenes |
US3609183A (en) | 1969-01-08 | 1971-09-28 | Parke Davis & Co | {60 -{8 {11 -(dimethylaminoalkyl)phenyl{9 -4-methoxy-{60 {40 -nitrostilbene compounds |
US3846398A (en) | 1969-04-17 | 1974-11-05 | Merck & Co Inc | Method for controlled stepwise synthesis of polypeptides utilizing n-thiocarboxy anhydrides of amino acids as reagents |
US4312855A (en) | 1970-11-16 | 1982-01-26 | Colgate-Palmolive Company | Compositions containing aminopolyureylene resin |
US4092335A (en) | 1973-07-26 | 1978-05-30 | Politechnika Gdanska | Desalanyltetaine derivatives and the method for their preparation |
US4326055A (en) | 1977-12-22 | 1982-04-20 | Hoffmann-La Roche Inc. | Stilbene derivatives |
JPS6045632B2 (ja) | 1978-03-09 | 1985-10-11 | 三菱化学株式会社 | ω−アミノアルコキシスチルベン類及びその酸付加塩 |
US4284637A (en) | 1978-03-09 | 1981-08-18 | Mitsubishi Chemical Ind., Limited | Pharmaceutically active 2-(4-aminobutoxy)stilbenes |
DE2832213A1 (de) | 1978-07-21 | 1980-01-31 | Bayer Ag | Stilbenderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
JPS5629548A (en) | 1979-08-16 | 1981-03-24 | Mitsubishi Chem Ind Ltd | Omega-aminoalkoxystilbenes and their acid addition salts |
JPS5697277A (en) | 1980-01-07 | 1981-08-05 | Takeda Chem Ind Ltd | Thiazolidine derivative |
FR2562539B1 (fr) | 1984-04-06 | 1987-04-17 | Chauvin Blache Lab | Nouveaux derives de l'acide vinyl-4 benzoique, leur procede de preparation et leurs applications en therapeutique et comme ligands |
US4716905A (en) | 1985-09-25 | 1988-01-05 | Fluorochrome, Inc. | Method of retrograde fluorescent labeling of neurons |
CA1338645C (en) | 1987-01-06 | 1996-10-15 | George R. Pettit | Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins" |
GB8716650D0 (en) | 1987-07-15 | 1987-08-19 | Ici Plc | Use of olefinic compounds |
CA1340955C (en) | 1988-02-24 | 2000-04-11 | Michael Klaus | Stilbene derivatives |
US5250562A (en) | 1988-02-24 | 1993-10-05 | Hoffmann-La Roche Inc. | Stilbene derivatives |
US5208250A (en) * | 1988-05-25 | 1993-05-04 | Warner-Lambert Company | Known and selected novel arylmethylenyl derivatives of thiazolidinones, imidazolidinones and oxazolidinones useful as antiallergy agents and anti-inflammatory agents |
DE3926148A1 (de) | 1989-08-08 | 1991-02-28 | Basf Ag | Diarylacetylene, ihre herstellung und verwendung |
US5053420A (en) | 1989-10-13 | 1991-10-01 | Pershadsingh Harrihar A | Thiazolidine derivatives for the treatment of hypertension |
US5189056A (en) | 1989-12-19 | 1993-02-23 | University Of North Carolina At Chapel Hill | Protection of moist stratified squamous epithelia against damage from noxious luminal agents |
US5162337A (en) | 1990-10-05 | 1992-11-10 | Merck & Co., Inc. | Animal growth promotion |
DK0498095T3 (da) | 1991-02-05 | 1995-06-19 | Merrell Dow Pharma | Sulfoniske stilbenderivater til behandling af virussygdomme |
US5158966A (en) * | 1991-02-22 | 1992-10-27 | The University Of Colorado Foundation, Inc. | Method of treating type i diabetes |
CH683151A5 (de) | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
US5171753A (en) | 1991-05-15 | 1992-12-15 | A. H. Robins Company, Incorporated | Derivatives of 2-amino-1-phenylethanol having antiulcer activity |
JP3509859B2 (ja) | 1991-11-07 | 2004-03-22 | ナノトロニクス,インコーポレイテッド | 供与体−供与体エネルギー転移系を創製するための発色団および蛍光団でコンジュゲート化されたポリヌクレオチドのハイブリダイゼーション |
AU3231093A (en) * | 1991-12-20 | 1993-07-28 | Upjohn Company, The | A reduction method for substituted 5-methylene-thiazolidinediones |
US5246936A (en) | 1991-12-20 | 1993-09-21 | American Cyanamid Company | Methods and compositions containing pesticides and stilbene compounds for enhanced pesticidal activity |
US5314693A (en) | 1992-02-07 | 1994-05-24 | Kioritz Corporation | Pest control chemicals against pine wood nematodes |
US5430062A (en) | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
WO1994020456A1 (en) | 1993-03-10 | 1994-09-15 | Morinaga Milk Industry Co., Ltd. | Stilbene derivative and stilbene analog derivative, and use thereof |
US5731353A (en) | 1993-09-08 | 1998-03-24 | Ajinomoto Co., Inc. | Stilbene derivatives and pharmaceutical compositions containing them |
TW325458B (en) | 1993-09-08 | 1998-01-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer |
US6046222A (en) | 1993-09-15 | 2000-04-04 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus |
US6046202A (en) | 1993-09-15 | 2000-04-04 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of insulin resistance |
JPH07138258A (ja) | 1993-11-16 | 1995-05-30 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
IT1264988B1 (it) | 1993-12-14 | 1996-10-17 | Sigma Prod Chim | Composizioni cosmetiche e dermatologiche per la protezione da radiazioni uv contenenti derivati dallo stilbene |
TW308598B (zh) | 1994-01-14 | 1997-06-21 | Hoffmann La Roche | |
CZ289317B6 (cs) | 1994-04-11 | 2002-01-16 | Sankyo Company Limited | Heterocyklická sloučenina, farmaceutický prostředek ji obsahující a její pouľití |
US5559151A (en) | 1994-11-30 | 1996-09-24 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of chloride channel blockers |
TW334418B (en) | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
CA2174582A1 (en) | 1995-05-05 | 1996-11-06 | Alexander Chucholowski | Sulphuric acid esters of amino-sugars |
US5716928A (en) | 1995-06-07 | 1998-02-10 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
US5770620A (en) | 1995-06-19 | 1998-06-23 | Ontogen Corporation | Aryl acrylic acid derivatives useful as protein tyrosine phosphatase inhibitors |
TW438587B (en) | 1995-06-20 | 2001-06-07 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
US5733909A (en) | 1996-02-01 | 1998-03-31 | Merck Frosst Canada, Inc. | Diphenyl stilbenes as prodrugs to COX-2 inhibitors |
JPH09323930A (ja) | 1996-04-04 | 1997-12-16 | Takeda Chem Ind Ltd | 悪液質の予防・治療剤 |
EP2253327A1 (en) | 1996-04-05 | 2010-11-24 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition containing a compound having angiotensin II antagonistic activity in combination with another compound |
KR100579765B1 (ko) | 1996-07-01 | 2006-12-28 | 닥터 레디스 레보러터리즈 리미티드 | 신규헤테로고리형화합물의제조방법,이를함유하는약제조성물및당뇨병및이와관련된질병의치료에있어서그의용도 |
US6114526A (en) | 1996-07-01 | 2000-09-05 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
US5827898A (en) | 1996-10-07 | 1998-10-27 | Shaman Pharmaceuticals, Inc. | Use of bisphenolic compounds to treat type II diabetes |
US5859037A (en) | 1997-02-19 | 1999-01-12 | Warner-Lambert Company | Sulfonylurea-glitazone combinations for diabetes |
US6011036A (en) | 1997-04-15 | 2000-01-04 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic hypolipidemic antihypertensive properties process for their preparation and pharmaceutical compositions containing them |
US6011031A (en) | 1997-05-30 | 2000-01-04 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them |
US6008237A (en) | 1997-12-19 | 1999-12-28 | Merck & Co., Inc. | Arylthiazolidinedione derivatives |
US6034110A (en) | 1998-01-12 | 2000-03-07 | Allergan Sales, Inc. | Method for preventing onset of restenosis after angioplasty employing an RXR-specific retinoid and a PPARγ ligand |
US6245814B1 (en) * | 1998-05-08 | 2001-06-12 | Calyx Therapeutics, Inc. | Diphenylethylene compounds |
US20020025975A1 (en) | 1998-05-08 | 2002-02-28 | Bishwajit Nag | Novel Heterocyclic analogs of diphenylethylene compounds |
US6624197B1 (en) * | 1998-05-08 | 2003-09-23 | Calyx Therapeutics, Inc. | Diphenylethylene compounds |
US6331633B1 (en) * | 1998-05-08 | 2001-12-18 | Calyx Therapeutics Inc. | Heterocyclic analogs of diphenylethylene compounds |
US7105552B2 (en) * | 1998-05-08 | 2006-09-12 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
US7407978B2 (en) | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
-
2001
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- 2001-06-05 ES ES01944241T patent/ES2317911T3/es not_active Expired - Lifetime
- 2001-06-05 AU AU2001266670A patent/AU2001266670B9/en not_active Ceased
- 2001-06-05 CA CA002410171A patent/CA2410171A1/en not_active Abandoned
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- 2001-06-05 MX MXPA02012038A patent/MXPA02012038A/es active IP Right Grant
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- 2001-06-05 DK DK01944241T patent/DK1360178T3/da active
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- 2001-06-05 DE DE60137718T patent/DE60137718D1/de not_active Expired - Lifetime
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4297429A (en) * | 1979-06-18 | 1981-10-27 | Mitsubishi Paper Mills, Ltd. | Photographic material and diffusion transfer processing solution for making printing plates and method for making printing plates |
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MXPA02012038A (es) | 2003-10-15 |
CA2410171A1 (en) | 2001-12-20 |
US20040186299A1 (en) | 2004-09-23 |
JP2004527455A (ja) | 2004-09-09 |
KR100844098B1 (ko) | 2008-07-04 |
KR20080009244A (ko) | 2008-01-25 |
KR100826991B1 (ko) | 2008-05-02 |
AU6667001A (en) | 2001-12-24 |
US20020032225A1 (en) | 2002-03-14 |
CN1537002A (zh) | 2004-10-13 |
ES2317911T3 (es) | 2009-05-01 |
US7105552B2 (en) | 2006-09-12 |
JP5048199B2 (ja) | 2012-10-17 |
DK1360178T3 (da) | 2009-03-30 |
AU2001266670B2 (en) | 2006-10-05 |
EP1360178A4 (en) | 2004-05-26 |
KR20030068398A (ko) | 2003-08-21 |
ATE422886T1 (de) | 2009-03-15 |
DE60137718D1 (de) | 2009-04-02 |
NZ522660A (en) | 2005-05-27 |
US7202366B2 (en) | 2007-04-10 |
EP1360178A2 (en) | 2003-11-12 |
WO2001095859A3 (en) | 2003-08-28 |
AU2001266670B9 (en) | 2006-11-30 |
WO2001095859A2 (en) | 2001-12-20 |
HK1058190A1 (en) | 2004-05-07 |
EP1360178B1 (en) | 2009-02-18 |
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