JP2005539022A - 悪性腫瘍の治療のためのシクロオキシゲナーゼ−2選択的阻害剤及びカルボニックアンヒドラーゼ阻害剤の組成物 - Google Patents
悪性腫瘍の治療のためのシクロオキシゲナーゼ−2選択的阻害剤及びカルボニックアンヒドラーゼ阻害剤の組成物 Download PDFInfo
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- JP2005539022A JP2005539022A JP2004527530A JP2004527530A JP2005539022A JP 2005539022 A JP2005539022 A JP 2005539022A JP 2004527530 A JP2004527530 A JP 2004527530A JP 2004527530 A JP2004527530 A JP 2004527530A JP 2005539022 A JP2005539022 A JP 2005539022A
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| US8673341B2 (en) | 2004-04-30 | 2014-03-18 | Allergan, Inc. | Intraocular pressure reduction with intracameral bimatoprost implants |
| US9498457B2 (en) | 2004-04-30 | 2016-11-22 | Allergan, Inc. | Hypotensive prostamide-containing biodegradable intraocular implants and related implants |
| US8722097B2 (en) | 2004-04-30 | 2014-05-13 | Allergan, Inc. | Oil-in-water method for making polymeric implants containing a hypotensive lipid |
| US7799336B2 (en) * | 2004-04-30 | 2010-09-21 | Allergan, Inc. | Hypotensive lipid-containing biodegradable intraocular implants and related methods |
| MY147767A (en) | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| WO2006127184A1 (en) | 2005-05-20 | 2006-11-30 | Janssen Pharmaceutica N.V. | Process for preparation of sulfamide derivatives |
| JP4872076B2 (ja) * | 2005-09-15 | 2012-02-08 | 国立大学法人 長崎大学 | 硝子体可視化剤 |
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| US8937096B2 (en) | 2005-12-19 | 2015-01-20 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder |
| US20070155823A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
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| EP2026790A2 (en) | 2006-05-19 | 2009-02-25 | Janssen Pharmaceutica, N.V. | Co-therapy for the treatment of epilepsy and related disorders |
| US8969415B2 (en) | 2006-12-01 | 2015-03-03 | Allergan, Inc. | Intraocular drug delivery systems |
| WO2008075148A2 (en) * | 2006-12-15 | 2008-06-26 | Pfizer Products Inc. | Tricyclic inhibitors of carbonic anhydrase |
| EP2240171B1 (en) * | 2008-01-09 | 2014-08-13 | Molecular Insight Pharmaceuticals, Inc. | Inhibitors of carbonic anhydrase IX |
| US8562945B2 (en) | 2008-01-09 | 2013-10-22 | Molecular Insight Pharmaceuticals, Inc. | Technetium- and rhenium-bis(heteroaryl) complexes and methods of use thereof |
| WO2010008776A2 (en) | 2008-06-23 | 2010-01-21 | Janssen Pharmaceutica Nv | Disposable patch and reusable sensor assembly for use in medical device localization and mapping systems |
| US8815939B2 (en) | 2008-07-22 | 2014-08-26 | Janssen Pharmaceutica Nv | Substituted sulfamide derivatives |
| AU2009322171A1 (en) | 2008-12-05 | 2011-06-30 | Molecular Insight Pharmaceuticals, Inc. | CA-IX specific radiopharmaceuticals for the treatment and imaging of cancer |
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| WO2010125004A1 (en) * | 2009-04-29 | 2010-11-04 | Nerviano Medical Sciences S.R.L. | Cdk inhibitor salts |
| AU2010260195B2 (en) | 2009-06-15 | 2014-11-20 | Molecular Insight Pharmaceuticals, Inc. | Process for production of heterodimers of glutamic acid |
| JP2013508320A (ja) * | 2009-10-21 | 2013-03-07 | バイエル・ファルマ・アクチェンゲゼルシャフト | 置換されたハロフェノキシベンズアミド誘導体 |
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| WO2012021963A1 (en) * | 2010-07-09 | 2012-02-23 | Metasignal Therapeutics Inc. | Novel sulfonamide compounds for inhibition of metastatic tumor growth |
| CN103298816A (zh) * | 2010-12-17 | 2013-09-11 | 内尔维阿诺医学科学有限公司 | 作为激酶抑制剂的取代的吡唑并-喹唑啉衍生物 |
| CN102351793B (zh) * | 2011-08-30 | 2013-11-06 | 江苏正大清江制药有限公司 | 4-[3-(4-甲基苯基)-5-(三氟甲基)-1-氢-吡唑-1-基]苯磺酰胺的直接合成方法 |
| CN103929964A (zh) | 2011-09-23 | 2014-07-16 | 拜耳知识产权有限责任公司 | 4-取代的1-苯基吡唑-3-甲酸衍生物作为对抗非生物植物胁迫的活性物质的用途 |
| AU2013207486A1 (en) | 2012-01-06 | 2014-08-21 | Molecular Insight Pharmaceuticals | Metal complexes of poly(carboxyl)amine-containing ligands having an affinity for carbonic anhydrase IX |
| PL2943227T3 (pl) | 2013-01-14 | 2018-02-28 | Molecular Insight Pharmaceuticals, Inc. | Triazynowe radiofarmaceutyki i środki do obrazowania radiologicznego |
| WO2017110874A1 (ja) * | 2015-12-22 | 2017-06-29 | 日油株式会社 | 涙液油層安定化剤およびこれを含有する点眼剤 |
| EP3624885A4 (en) | 2017-05-19 | 2021-03-10 | Trudell Medical International | EXPIRATORY OVERPRESSURE DEVICE |
| USD874064S1 (en) | 2018-05-18 | 2020-01-28 | Trudell Medical International | Mask |
| USD903097S1 (en) | 2018-05-18 | 2020-11-24 | Trudell Medical International | Mask |
| USD893806S1 (en) | 2018-11-09 | 2020-08-18 | Trudell Medical Internationl | Mask and shroud |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN109557309B (zh) * | 2018-12-04 | 2021-09-10 | 九江学院附属医院 | 碳酸酐酶-2作为检测标记物在肾结石诊断方面的应用 |
| CN111233786B (zh) * | 2020-02-04 | 2021-11-26 | 中国人民解放军军事科学院军事医学研究院 | 含五元杂环的苯磺酰胺类化合物及其制备方法和用途 |
| CN115607567A (zh) * | 2022-09-28 | 2023-01-17 | 长春工业大学 | 一种环保型改善心肌缺血的血液透析液 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53142536A (en) * | 1977-05-14 | 1978-12-12 | Centrala Ind Medicamente | Pharmaceutical composition for treating gastric and duodenum ulser |
| US5157044A (en) * | 1983-02-04 | 1992-10-20 | University Of Iowa Research Foundation | Analogs of carbonic anhydrase inhibitors and their use as topical IOP inhibitors |
| US5095026A (en) * | 1983-02-04 | 1992-03-10 | University Of Iowa Research Foundation | Prodrugs of carbonic anhydrase inhibitors |
| US4911920A (en) * | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| AU665341B2 (en) * | 1990-12-18 | 1996-01-04 | Wellcome Foundation Limited, The | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| AU653279B2 (en) * | 1991-12-30 | 1994-09-22 | Sanofi | Novel 2-saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| US6090834A (en) * | 1993-05-21 | 2000-07-18 | G.D. Searle & Co. | Substituted oxazoles for the treatment of inflammation |
| US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| KR100263817B1 (ko) * | 1993-11-30 | 2000-08-16 | 윌리암스 로저 에이 | 염증치료용 치환 피라졸일벤젠술폰아미드 |
| US6369103B1 (en) * | 1994-01-18 | 2002-04-09 | Bristol-Myers Squibb Company | Method for preventing or reducing risk of onset of cardiovascular events employing an HMG CoA reductase inhibitor |
| US5547975A (en) * | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| JP3181190B2 (ja) * | 1994-12-20 | 2001-07-03 | 日本たばこ産業株式会社 | オキサゾール誘導体 |
| US5633272A (en) * | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
| EP0809636B1 (en) * | 1995-02-13 | 2002-09-04 | G.D. Searle & Co. | Substituted isoxazoles for the treatment of inflammation |
| US5944021A (en) * | 1995-06-07 | 1999-08-31 | Rodriguez; Victorio C. | Therapeutic use of a carbonic anhydrase enzyme inhibitor for the treatment of brain edema |
| DE19600721A1 (de) * | 1996-01-12 | 1997-07-17 | Hoechst Ag | Verwendung von Inhibitoren des Carboanhydratase (CAH) zum Herstellen eines Medikaments zur Behandlung von Krebs |
| SK284371B6 (sk) * | 1996-02-26 | 2005-02-04 | Advanced Research And Technology Institute | Použitie oftalmologickej kompozície obsahujúcej účinné množstvo lokálneho inhibítora anhydrázy kyseliny uhličitej na prípravu liečiva |
| US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| CA2372912C (en) * | 1997-10-14 | 2008-12-02 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
| US5972986A (en) * | 1997-10-14 | 1999-10-26 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
| US6025353A (en) * | 1997-11-19 | 2000-02-15 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents |
| US5972684A (en) * | 1997-11-25 | 1999-10-26 | Incyte Pharmaceuticals, Inc. | Carbonic anhydrase VIII |
| ES2140354B1 (es) * | 1998-08-03 | 2000-11-01 | S A L V A T Lab Sa | Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2. |
| WO2000018741A2 (en) * | 1998-09-30 | 2000-04-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole compounds as cox-2 inhibitors |
| SE9803761D0 (sv) * | 1998-11-04 | 1998-11-04 | Synphora Ab | Method to avoid increased iridial pigmentation during prostaglandin treatment |
| ES2273688T3 (es) * | 1999-04-14 | 2007-05-16 | Dana-Farber Cancer Institute, Inc. | Procedimiento y composicion para el tratamiento de cancer. |
| US6465448B1 (en) * | 1999-08-13 | 2002-10-15 | Case Western Reserve University | Methoxyamine potentiation of temozolomide anti-cancer activity |
| US6323226B1 (en) * | 1999-10-19 | 2001-11-27 | Texas Heart Institute | Treatment of heart disease with cox-2 inhibitors |
| US6822102B2 (en) * | 2000-01-03 | 2004-11-23 | Pharmacia Corporation | Dihydrobenzopyrans, dihydrobenzothiopyrans, and tetrahydroquinolines for the treatment of COX-2 mediated disorders |
| AU2001233286B2 (en) * | 2000-02-01 | 2006-04-06 | Cayman Chemical Company, Incorporated | Internal 1,15-lactones of fluprostenol and related prostaglandin F2alpha analogs and their use in the treatment of glaucoma and intraocular hypertension |
| US6448030B1 (en) * | 2000-02-18 | 2002-09-10 | University Of Nevada-Las Vegas | Method for predicting the efficacy of anti-cancer drugs |
| JP2002179657A (ja) * | 2000-05-26 | 2002-06-26 | Japan Tobacco Inc | 5−(4−アミノスルホニル−3−フルオロフェニル)−4−シクロヘキシル−2−メチルオキサゾールの結晶多形 |
| AU2001275004A1 (en) * | 2000-06-01 | 2001-12-11 | Pharmacia Corporation | Use of cox2 inhibitors for treating skin injury from exposure to ultraviolet radiation |
| US20020128267A1 (en) * | 2000-07-13 | 2002-09-12 | Rebanta Bandyopadhyay | Method of using COX-2 inhibitors in the treatment and prevention of ocular COX-2 mediated disorders |
| PE20020146A1 (es) * | 2000-07-13 | 2002-03-31 | Upjohn Co | Formulacion oftalmica que comprende un inhibidor de ciclooxigenasa-2 (cox-2) |
| US20020035148A1 (en) * | 2000-07-20 | 2002-03-21 | Ryuji Ueno | Treatment of ocular hypertension |
| CA2419158A1 (en) * | 2000-08-11 | 2002-02-21 | Einar Stefansson | Method for the prevention and treatment of retinopathy |
| SE0004229D0 (sv) * | 2000-11-17 | 2000-11-17 | Aga Ab | Inhalation of nitric oxide |
| EP1414522A2 (en) * | 2001-08-10 | 2004-05-06 | Pharmacia Corporation | Carbonic anhydrase inhibitors |
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- 2003-02-14 JP JP2004527531A patent/JP2005539023A/ja not_active Withdrawn
- 2003-02-14 BR BR0313282-0A patent/BR0313282A/pt not_active IP Right Cessation
- 2003-02-14 PL PL03374994A patent/PL374994A1/xx unknown
- 2003-02-14 CA CA002495502A patent/CA2495502A1/en not_active Abandoned
- 2003-02-14 WO PCT/US2003/004469 patent/WO2004014430A1/en not_active Ceased
- 2003-02-14 JP JP2004527530A patent/JP2005539022A/ja not_active Withdrawn
- 2003-02-14 BR BR0313299-4A patent/BR0313299A/pt not_active IP Right Cessation
- 2003-02-14 CA CA002495516A patent/CA2495516A1/en not_active Abandoned
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| KR20050056189A (ko) | 2005-06-14 |
| CA2495516A1 (en) | 2004-02-19 |
| EP1526895A2 (en) | 2005-05-04 |
| AU2003213062A1 (en) | 2004-02-25 |
| US20040198781A1 (en) | 2004-10-07 |
| CN1681557A (zh) | 2005-10-12 |
| BR0313299A (pt) | 2005-06-14 |
| JP2005539023A (ja) | 2005-12-22 |
| EP1526869A1 (en) | 2005-05-04 |
| IL166685A0 (en) | 2006-01-15 |
| WO2004014430A1 (en) | 2004-02-19 |
| BR0313282A (pt) | 2005-10-18 |
| WO2004014352A2 (en) | 2004-02-19 |
| PL374994A1 (en) | 2005-11-14 |
| MXPA05001496A (es) | 2005-05-16 |
| CA2495502A1 (en) | 2004-02-19 |
| MXPA05001497A (es) | 2005-05-27 |
| US20030100594A1 (en) | 2003-05-29 |
| AU2003225571A1 (en) | 2004-02-25 |
| WO2004014352A3 (en) | 2004-09-10 |
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