TWI437996B - 含有ｓｇｌｔ抑制劑及ｄｐｐ４抑制劑之醫藥組成物 - Google Patents
含有ｓｇｌｔ抑制劑及ｄｐｐ４抑制劑之醫藥組成物 Download PDFInfo
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- TWI437996B TWI437996B TW098101763A TW98101763A TWI437996B TW I437996 B TWI437996 B TW I437996B TW 098101763 A TW098101763 A TW 098101763A TW 98101763 A TW98101763 A TW 98101763A TW I437996 B TWI437996 B TW I437996B
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- 229940090124 dipeptidyl peptidase 4 (dpp-4) inhibitors for blood glucose lowering Drugs 0.000 title claims description 93
- 239000003112 inhibitor Substances 0.000 title claims description 11
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- WQWNUPFPUXHKAQ-OSKXVONFSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[5-(6-fluoropyridin-3-yl)thiophen-2-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2SC(=CC=2)C=2C=NC(F)=CC=2)=C1 WQWNUPFPUXHKAQ-OSKXVONFSA-N 0.000 claims description 5
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
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| US2177708P | 2008-01-17 | 2008-01-17 |
Publications (2)
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| TW200932249A TW200932249A (en) | 2009-08-01 |
| TWI437996B true TWI437996B (zh) | 2014-05-21 |
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Family Applications (1)
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| EP (1) | EP2252289B1 (enExample) |
| JP (3) | JP5204849B2 (enExample) |
| KR (1) | KR101257554B1 (enExample) |
| CN (2) | CN101932321B (enExample) |
| AR (1) | AR070193A1 (enExample) |
| AU (1) | AU2009205060C1 (enExample) |
| BR (1) | BRPI0906735A2 (enExample) |
| CA (1) | CA2712614C (enExample) |
| CL (1) | CL2008003653A1 (enExample) |
| ES (1) | ES2763239T3 (enExample) |
| MX (1) | MX2010007818A (enExample) |
| TW (1) | TWI437996B (enExample) |
| WO (1) | WO2009091082A1 (enExample) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| NZ619413A (en) | 2006-05-04 | 2015-08-28 | Boehringer Ingelheim Int | Polymorphs of a dpp-iv enzyme inhibitor |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20090938A1 (es) | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
| NZ600110A (en) | 2007-09-10 | 2013-03-28 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of sglt |
| CL2008003653A1 (es) * | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| JP2009196984A (ja) * | 2008-01-25 | 2009-09-03 | Mitsubishi Tanabe Pharma Corp | 医薬組成物 |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| KR20190016601A (ko) | 2008-08-06 | 2019-02-18 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| AU2009286380B2 (en) | 2008-08-28 | 2011-09-15 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| ES2797503T3 (es) | 2009-02-13 | 2020-12-02 | Boehringer Ingelheim Int | Composición farmacéutica que comprende un inhibidor de SGLT2, un inhibidor de DPP-IV y opcionalmente un agente antidiabético adicional y sus usos |
| UY32427A (es) * | 2009-02-13 | 2010-09-30 | Boheringer Ingelheim Internat Gmbh | Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| DK2451797T3 (da) | 2009-07-10 | 2013-06-24 | Janssen Pharmaceutica Nv | Fremgangsmåde til krystallisation for 1-(b-D-GLUCOPYRANOSYL)-4-METHYL-3-[5-(4-fluorphenyl)-2- thienylmethyl]benzen |
| DK2486029T3 (en) | 2009-09-30 | 2015-08-24 | Boehringer Ingelheim Int | Methods of making of glucopyranosyl-substituted benzyl-benzene derivatives. |
| AU2010303123B2 (en) | 2009-09-30 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (Beta-D-glucopyranos-1-yl)-2-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)benzene |
| UY32919A (es) | 2009-10-02 | 2011-04-29 | Boehringer Ingelheim Int | Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos |
| MX340214B (es) | 2009-10-14 | 2016-06-30 | Janssen Pharmaceutica Nv * | Procedimiento para la preparación de compuestos útiles como inhibidores del transportador de glucosa dependiente de sodio 2. |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| NZ599945A (en) | 2009-11-02 | 2014-05-30 | Pfizer | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| MX364651B (es) | 2009-11-27 | 2019-05-03 | Boehringer Ingelheim Int Gmbh Star | Inhibidores de dpp-iv, tales como la linagliptina, y composiciones farmacéuticas o combinaciones que comprenden los mismos, para usarse en el tratamiento de pacientes diabéticos tipificados genéticamente. |
| TWI562775B (en) * | 2010-03-02 | 2016-12-21 | Lexicon Pharmaceuticals Inc | Methods of using inhibitors of sodium-glucose cotransporters 1 and 2 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| MX339570B (es) * | 2010-05-11 | 2016-05-31 | Janssen Pharmaceutica Nv | Formulaciones farmaceuticas que comprenden derivados de 1-(beta-d-glucopiranosil)-2-tienil-metilbenceno como inhibidores de transportadores de glucosa dependientes de sodio. |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| TWI631963B (zh) * | 2011-01-05 | 2018-08-11 | 雷西肯製藥股份有限公司 | 包含鈉－葡萄糖共同輸送體１與２之抑制劑的組合物與應用方法 |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| PT2697218T (pt) | 2011-04-13 | 2016-07-13 | Janssen Pharmaceutica Nv | Processo para preparação de compostos úteis como inibidores da sglt2 |
| TWI542596B (zh) | 2011-05-09 | 2016-07-21 | 健生藥品公司 | （２ｓ,３ｒ,４ｒ,５ｓ,６ｒ）－２－（３－（（５－（４－氟苯基）噻吩－２－基）甲基）－４－甲基苯基）－６－（羥甲基）四氫－２ｈ－哌喃－３,４,５－三醇之ｌ－脯胺酸及檸檬酸共晶體 |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| EP3685839A1 (en) | 2012-05-14 | 2020-07-29 | Boehringer Ingelheim International GmbH | Linagliptin for use in the treatment of albuminuria and kidney related diseases |
| ES2929025T3 (es) | 2012-05-14 | 2022-11-24 | Boehringer Ingelheim Int | Linagliptina, un derivado de xantina como inhibidor de dpp-4, para su uso en el tratamiento del SRIS y/o de la septicemia |
| CA2812519A1 (en) | 2013-04-05 | 2014-10-05 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| HRP20190101T1 (hr) | 2013-04-05 | 2019-03-08 | Boehringer Ingelheim International Gmbh | Terapeutske uporabe empagliflozina |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CA3175715A1 (en) | 2013-04-18 | 2014-10-23 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| JP6507154B2 (ja) * | 2013-06-14 | 2019-04-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糖尿病及びその合併症を治療するためのｄｄｐ−４阻害薬 |
| CN104739835A (zh) * | 2013-12-30 | 2015-07-01 | 中美华世通生物医药科技（武汉）有限公司 | 一种治疗糖尿病的新型药物组合物 |
| EP3142661B1 (en) * | 2014-05-16 | 2021-10-06 | Astrazeneca AB | Method for suppressing glucagon secretion of an sglt2 inhibitor |
| WO2016104643A1 (ja) * | 2014-12-25 | 2016-06-30 | 田辺三菱製薬株式会社 | 糖尿病治療用固形製剤 |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
| CN109922813A (zh) | 2016-11-10 | 2019-06-21 | 勃林格殷格翰国际有限公司 | 药物组合物、治疗方法及其用途 |
| WO2018167589A1 (en) | 2017-03-16 | 2018-09-20 | Inventia Healthcare Private Limited | Pharmaceutical composition comprising dapagliflozin |
| KR101943382B1 (ko) | 2017-09-19 | 2019-01-29 | 오토텔릭바이오 주식회사 | Sglt-2 저해제 및 안지오텐신 수용체 차단제를 포함하는 의약 조성물 |
| KR102204439B1 (ko) * | 2018-05-14 | 2021-01-18 | 에이치케이이노엔 주식회사 | Sglt-2 억제제 및 dpp-iv 억제제를 포함하는 약제학적 조성물 |
| CN108976291B (zh) * | 2018-08-31 | 2021-06-08 | 华南理工大学 | 一种改善糖尿病和老年性痴呆的十六肽 |
| CN109021074B (zh) * | 2018-08-31 | 2021-08-10 | 华南理工大学 | 一种改善糖尿病和老年性痴呆症症状的七肽 |
| EP4114365A1 (en) | 2020-03-05 | 2023-01-11 | KRKA, d.d., Novo mesto | Pharmaceutical composition comprising sglt2 inhibitor |
| EP4161912A1 (en) | 2020-06-05 | 2023-04-12 | KRKA, d.d., Novo mesto | Preparation of highly pure amorphous dapagliflozin |
| CN111494358B (zh) * | 2020-06-22 | 2021-06-22 | 广州市力鑫药业有限公司 | 用于治疗和预防糖尿病肾病的药物 |
| AU2023355275A1 (en) * | 2022-10-05 | 2025-04-24 | Daewoong Pharmaceutical Co., Ltd. | Pharmaceutical composition for prevention or treatment of nephropathy and/or diabetes mellitus, comprising enavogliflozin |
Family Cites Families (155)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160861A (en) | 1977-10-03 | 1979-07-10 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
| US4584369A (en) | 1981-07-31 | 1986-04-22 | Sloan-Kettering Institute For Cancer Research | Anti-leukemic beta-glycosyl C-nucleosides |
| JP2544609B2 (ja) | 1986-10-07 | 1996-10-16 | 和光純薬工業株式会社 | Ｔｃｎｑ錯体 |
| EP0355750B1 (en) | 1988-08-19 | 1995-01-25 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
| CN1020944C (zh) | 1990-01-30 | 1993-05-26 | 阿图尔-费希尔股份公司费希尔厂 | 紧固件 |
| JPH04253974A (ja) | 1991-02-05 | 1992-09-09 | Ishihara Sangyo Kaisha Ltd | スルホニル尿素系化合物、それらの製造方法及びそれらを含有する除草剤 |
| US5149838A (en) | 1991-09-20 | 1992-09-22 | Merck & Co., Inc. | Intermediates for substituted azetidinones useful as anti-inflammatory and antidegenerative agents |
| GB9208161D0 (en) | 1992-04-14 | 1992-05-27 | Pfizer Ltd | Indoles |
| US5334225A (en) | 1992-07-15 | 1994-08-02 | Kao Corporation | Keratinous fiber dye composition containing a 2-substituted amino-5-alkylphenol derivative coupler |
| CA2102591C (en) | 1992-11-12 | 2000-12-26 | Kenji Tsujihara | Hypoglycemic agent |
| US5731292A (en) | 1992-11-12 | 1998-03-24 | Tanabe Seiyaku Co., Ltd. | Dihydrochalcone derivatives which are hypoglycemic agents |
| US6297363B1 (en) | 1993-02-12 | 2001-10-02 | Nomura Co., Ltd. | Glycoside indoles |
| IL111785A0 (en) | 1993-12-03 | 1995-01-24 | Ferring Bv | Dp-iv inhibitors and pharmaceutical compositions containing them |
| US5830873A (en) | 1994-05-11 | 1998-11-03 | Tanabe Seiyaku Co., Ltd. | Propiophenone derivative and a process for preparing the same |
| US5780483A (en) | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| WO1997025033A1 (en) | 1995-10-31 | 1997-07-17 | Eli Lilly And Company | Antithrombotic diamines |
| JP3059088B2 (ja) | 1995-11-07 | 2000-07-04 | 田辺製薬株式会社 | プロピオフェノン誘導体およびその製法 |
| JPH09263549A (ja) | 1996-01-25 | 1997-10-07 | Fujisawa Pharmaceut Co Ltd | ベンゼン誘導体の製造法 |
| US20020006899A1 (en) | 1998-10-06 | 2002-01-17 | Pospisilik Andrew J. | Use of dipeptidyl peptidase IV effectors for lowering blood pressure in mammals |
| DE19616486C5 (de) | 1996-04-25 | 2016-06-30 | Royalty Pharma Collection Trust | Verfahren zur Senkung des Blutglukosespiegels in Säugern |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| ATE216704T1 (de) | 1996-12-26 | 2002-05-15 | Tanabe Seiyaku Co | Propiophenonderivate und verfahren zu ihrer herstellung |
| WO1999051430A1 (en) | 1998-04-07 | 1999-10-14 | Seydel Research, Inc. | Water dispersible/redispersible hydrophobic polyester resins and their application in coatings |
| US6153632A (en) | 1997-02-24 | 2000-11-28 | Rieveley; Robert B. | Method and composition for the treatment of diabetes |
| JPH10324632A (ja) | 1997-03-25 | 1998-12-08 | Takeda Chem Ind Ltd | 医薬組成物 |
| DE19823831A1 (de) | 1998-05-28 | 1999-12-02 | Probiodrug Ges Fuer Arzneim | Neue pharmazeutische Verwendung von Isoleucyl Thiazolidid und seinen Salzen |
| US6274725B1 (en) * | 1998-06-02 | 2001-08-14 | Isis Pharmaceuticals, Inc. | Activators for oligonucleotide synthesis |
| JP2000034239A (ja) | 1998-07-16 | 2000-02-02 | Asahi Glass Co Ltd | トリフルオロメチル化芳香族化合物の製造方法 |
| JP3857429B2 (ja) | 1998-07-17 | 2006-12-13 | ポーラ化成工業株式会社 | 含硫黄抗真菌剤 |
| CO5150173A1 (es) | 1998-12-10 | 2002-04-29 | Novartis Ag | Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv |
| US20020032164A1 (en) | 1998-12-30 | 2002-03-14 | Dale Roderic M. K. | Antimicrobial compounds and methods for their use |
| GB9912961D0 (en) | 1999-06-03 | 1999-08-04 | Pfizer Ltd | Metalloprotease inhibitors |
| US6107317A (en) | 1999-06-24 | 2000-08-22 | Novartis Ag | N-(substituted glycyl)-thiazolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| US6172081B1 (en) | 1999-06-24 | 2001-01-09 | Novartis Ag | Tetrahydroisoquinoline 3-carboxamide derivatives |
| US6110949A (en) | 1999-06-24 | 2000-08-29 | Novartis Ag | N-(substituted glycyl)-4-cyanothiazolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| BRPI0013667B8 (pt) | 1999-08-31 | 2021-05-25 | Kissei Pharmaceutical | derivados de glucopiranosiloxipirazol, composições medicinais contendo os mesmos e seus intermediários na produção deles |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| GB9928330D0 (en) | 1999-11-30 | 2000-01-26 | Ferring Bv | Novel antidiabetic agents |
| EP1741445B1 (en) | 2000-01-21 | 2013-08-14 | Novartis AG | Combinations comprising dipeptidylpeptidase-IV inhibitors and antidiabetic agents |
| US6627611B2 (en) | 2000-02-02 | 2003-09-30 | Kotobuki Pharmaceutical Co Ltd | C-glycosides and preparation of thereof as antidiabetic agents |
| JP4456768B2 (ja) | 2000-02-02 | 2010-04-28 | 壽製薬株式会社 | Ｃ−配糖体を含有する薬剤 |
| AU3217501A (en) | 2000-03-03 | 2001-09-12 | Pfizer Prod Inc | Pyrazole ether derivatives as anti-inflammatory/analgesic agents |
| US6395767B2 (en) | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
| UA72586C2 (en) | 2000-03-17 | 2005-03-15 | Kissei Pharmaceutical | Glucopyranozyloxybenzylbenzene derivatives, a pharmaceutical composition containing these derivatives, and intermediary compounds for obtaining said derivatives |
| US6555519B2 (en) | 2000-03-30 | 2003-04-29 | Bristol-Myers Squibb Company | O-glucosylated benzamide SGLT2 inhibitors and method |
| US6683056B2 (en) | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| GB0010188D0 (en) | 2000-04-26 | 2000-06-14 | Ferring Bv | Inhibitors of dipeptidyl peptidase IV |
| GB0010183D0 (en) | 2000-04-26 | 2000-06-14 | Ferring Bv | Inhibitors of dipeptidyl peptidase IV |
| TW583185B (en) | 2000-06-13 | 2004-04-11 | Novartis Ag | N-(substituted glycyl)-2-cyanopyrrolidines and pharmaceutical composition for inhibiting dipeptidyl peptidase-IV (DPP-IV) or for the prevention or treatment of diseases or conditions associated with elevated levels of DPP-IV comprising the same |
| DE10029014A1 (de) * | 2000-06-15 | 2001-12-20 | Univ Schiller Jena | Urokinase-Hemmstoffe |
| US7078397B2 (en) * | 2000-06-19 | 2006-07-18 | Smithkline Beecham Corporation | Combinations of dipeptidyl peptidase IV inhibitors and other antidiabetic agents for the treatment of diabetes mellitus |
| GB0014969D0 (en) | 2000-06-19 | 2000-08-09 | Smithkline Beecham Plc | Novel method of treatment |
| AU7775401A (en) | 2000-08-10 | 2002-02-25 | Welfide Corp | Proline derivatives and use thereof as drugs |
| EP1329456B1 (en) | 2000-09-29 | 2006-08-09 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same |
| ATE407924T1 (de) | 2000-10-06 | 2008-09-15 | Mitsubishi Tanabe Pharma Corp | Stickstoffhaltige, fünfgliedrige ringverbindungen |
| EP1338603B1 (en) | 2000-11-02 | 2010-01-20 | Ajinomoto Co., Inc. | Novel pyrazole derivatives and diabetes remedies containing the same |
| US6476352B2 (en) | 2000-12-18 | 2002-11-05 | General Electric Company | Laser beam stop sensor and method for automatically detecting the presence of laser beam stop material using a laser beam stop sensor |
| WO2002051836A1 (en) | 2000-12-27 | 2002-07-04 | Kyowa Hakko Kogyo Co., Ltd. | Dipeptidyl peptidase iv inhibitor |
| DK1354888T3 (da) | 2000-12-28 | 2009-09-21 | Kissei Pharmaceutical | Glukopyranosyloxypyrazolderivater og anvendelse deraf i medikamenter |
| EP1364957B1 (en) | 2001-02-26 | 2008-12-31 | Kissei Pharmaceutical Co., Ltd. | Glycopyranosyloxypyrazole derivatives and medicinal use thereof |
| DE60237580D1 (de) | 2001-02-27 | 2010-10-21 | Kissei Pharmaceutical | Glykopyranosyloxypyrazolderivate und deren medizinische verwendung |
| US7018610B2 (en) | 2001-03-02 | 2006-03-28 | University Of Western Ontario | Polymer precursors of radiolabeled compounds, and methods of making and using the same |
| JP2002265439A (ja) | 2001-03-08 | 2002-09-18 | Mitsubishi Pharma Corp | シアノピロリジン誘導体およびその医薬用途 |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| MXPA03008614A (es) | 2001-03-28 | 2003-12-08 | Hercules Inc | Metodos para usar acidos de lupulo para controlar organismos. |
| ES2258141T3 (es) | 2001-04-11 | 2006-08-16 | Bristol-Myers Squibb Company | Complejos de aminoacidos de glucosidos c-arilo para el tratamiento de la diabetes y procedimiento. |
| US6573287B2 (en) | 2001-04-12 | 2003-06-03 | Bristo-Myers Squibb Company | 2,1-oxazoline and 1,2-pyrazoline-based inhibitors of dipeptidyl peptidase IV and method |
| JP4292570B2 (ja) | 2001-04-27 | 2009-07-08 | 味の素株式会社 | Ｎ−置換ピラゾール−ｏ−グリコシド誘導体及びそれらを含有する糖尿病治療薬 |
| GB0112122D0 (en) | 2001-05-18 | 2001-07-11 | Lilly Co Eli | Heteroaryloxy 3-substituted propanamines |
| US7271153B2 (en) | 2001-06-20 | 2007-09-18 | Kissei Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivatives, medicinal compositions containing the same, medicinal uses thereof, and intermediates therefor |
| GB0115517D0 (en) | 2001-06-25 | 2001-08-15 | Ferring Bv | Novel antidiabetic agents |
| ES2296962T3 (es) | 2001-06-27 | 2008-05-01 | Smithkline Beecham Corporation | Pirrolidinas como inhibidores de dipeptidil peptidasa. |
| JP4357293B2 (ja) | 2001-06-27 | 2009-11-04 | スミスクライン ビーチャム コーポレーション | ジペプチジルペプチダーゼ阻害剤としてのフルオロピロリジン類 |
| JP3909056B2 (ja) | 2001-06-27 | 2007-04-25 | スミスクライン ビーチャム コーポレーション | ジペプチジルペプチダーゼ阻害剤としてのフルオロピロリジン類 |
| JP4115105B2 (ja) | 2001-07-02 | 2008-07-09 | 協和醗酵工業株式会社 | ピラゾール誘導体 |
| UA74912C2 (en) | 2001-07-06 | 2006-02-15 | Merck & Co Inc | Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes |
| JPWO2003011880A1 (ja) | 2001-07-31 | 2004-11-18 | キッセイ薬品工業株式会社 | グルコピラノシルオキシベンジルベンゼン誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| US20030087843A1 (en) | 2001-09-05 | 2003-05-08 | Washburn William N. | O-pyrazole glucoside SGLT2 inhibitors and method of use |
| US20040259883A1 (en) | 2001-09-14 | 2004-12-23 | Hiroshi Sakashita | Thiazolidine derivative and medicinal use thereof |
| GB0125445D0 (en) | 2001-10-23 | 2001-12-12 | Ferring Bv | Protease Inhibitors |
| US7323488B2 (en) | 2001-10-24 | 2008-01-29 | Michael Burton | Chromogenic enzyme substrates |
| MXPA04004673A (es) | 2001-11-16 | 2005-05-17 | Cutanix Corp | Composiciones farmaceuticas y cosmeticas que contienen aldehidos aromaticos qeue portan un grupo oxi. |
| US6617313B1 (en) | 2002-03-13 | 2003-09-09 | Council Of Scientific And Industrial Research | Glucopyranoside and process of isolation thereof from pterocarpus marsupium pharmaceutical composition containing the same and use thereof |
| US6562791B1 (en) | 2002-03-29 | 2003-05-13 | Council Of Scientific And Industrial Research | Glucopyranoside, process for isolation thereof, pharmaceutical composition containing same and use thereof |
| NZ561993A (en) | 2002-04-18 | 2008-09-26 | Astrazeneca Ab | Spiroazabicyclic heterocyclic amines as potent ligands for nicotinic acetylcholine receptors |
| US6710040B1 (en) | 2002-06-04 | 2004-03-23 | Pfizer Inc. | Fluorinated cyclic amides as dipeptidyl peptidase IV inhibitors |
| DE10231370B4 (de) | 2002-07-11 | 2006-04-06 | Sanofi-Aventis Deutschland Gmbh | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| TW200401635A (en) | 2002-07-23 | 2004-02-01 | Yamanouchi Pharma Co Ltd | 2-Cyano-4-fluoropyrrolidine derivative or salt thereof |
| TWI254635B (en) | 2002-08-05 | 2006-05-11 | Yamanouchi Pharma Co Ltd | Azulene derivative and salt thereof |
| UA77300C2 (en) | 2002-08-09 | 2006-11-15 | Taisho Pharmaceutical Co Ltd | 5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes |
| US20040102477A1 (en) | 2002-08-23 | 2004-05-27 | Dr. Reddy's Laboratories Limited | Polymorphic forms of (S)-Repaglinide and the processes for preparation thereof |
| WO2004019958A1 (ja) | 2002-08-27 | 2004-03-11 | Kissei Pharmaceutical Co., Ltd. | ピラゾール誘導体、それを含有する医薬組成物及びその医薬用途 |
| US7304166B2 (en) | 2002-08-29 | 2007-12-04 | Taisho Pharmaceutical Co., Ltd. | Benzenesulfonate salt of 4-fluoro-2-cyanopyrrolidine derivatives |
| DE10258008B4 (de) | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| BR0317929A (pt) | 2003-01-03 | 2006-04-11 | Bristol Myers Squibb Co | métodos de produzir inibidores de sglt2 de glicosìdeo de c-arila |
| DE10303270A1 (de) | 2003-01-28 | 2004-08-05 | Technische Universität Darmstadt | Medizintechnische Vorrichtung mit einer langgestreckten Einrichtung |
| WO2004067509A1 (ja) | 2003-01-31 | 2004-08-12 | Sanwa Kagaku Kenkyusho Co., Ltd. | ジペプチジルペプチダーゼivを阻害する化合物 |
| EP1609785B1 (en) | 2003-03-14 | 2016-02-03 | Astellas Pharma Inc. | C-glycoside derivatives and salts thereof |
| JP2004300102A (ja) | 2003-03-31 | 2004-10-28 | Kissei Pharmaceut Co Ltd | 縮合複素環誘導体、それを含有する医薬組成物およびその医薬用途 |
| AU2003902263A0 (en) | 2003-05-12 | 2003-05-29 | Fujisawa Pharmaceutical Co., Ltd. | Monosaccharide compounds |
| JP2007511467A (ja) | 2003-05-14 | 2007-05-10 | タケダ サン ディエゴ インコーポレイテッド | ジペプチジルペプチダーゼインヒビター |
| WO2004113359A1 (ja) | 2003-06-20 | 2004-12-29 | Kissei Pharmaceutical Co., Ltd. | ピラゾール誘導体、それを含有する医薬組成物及びその製造中間体 |
| US6995183B2 (en) | 2003-08-01 | 2006-02-07 | Bristol Myers Squibb Company | Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods |
| UA86042C2 (en) | 2003-08-01 | 2009-03-25 | Янссен Фармацевтика Н.В. | Substituted indazole-o-glucosides |
| US8785403B2 (en) * | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
| EA010655B1 (ru) | 2003-08-01 | 2008-10-30 | Янссен Фармацевтика Н.В. | Замещенные индазол-о-глюкозиды |
| US7094764B2 (en) | 2003-08-01 | 2006-08-22 | Janssen Pharmaceutica N.V. | Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides |
| CA2549015A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted fused heterocyclic c-glycosides |
| EA015104B1 (ru) * | 2003-08-01 | 2011-06-30 | Мицубиси Танабе Фарма Корпорейшн | Новые соединения, обладающие ингибирующей активностью в отношении натрийзависимого транспортера |
| WO2005012243A2 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indole-o-glucosides |
| EP1697342A2 (en) | 2003-09-08 | 2006-09-06 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2005026148A1 (en) | 2003-09-08 | 2005-03-24 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| WO2005030127A2 (en) | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Novel crystalline form of a phosphoric acid salt of a dipeptidyl peptidase-iv inhibitor |
| TW200519105A (en) | 2003-10-20 | 2005-06-16 | Lg Life Science Ltd | Novel inhibitors of DPP-IV, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent |
| US7214735B2 (en) | 2004-02-02 | 2007-05-08 | 3M Innovative Properties Company | Microsphere-filled sealant materials |
| AU2005210285B2 (en) | 2004-02-05 | 2008-01-24 | Kyorin Pharmaceutical Co., Ltd. | Bicycloester derivative |
| EP1717225A4 (en) | 2004-02-18 | 2009-10-21 | Kyorin Seiyaku Kk | BICYCLIC AMIDE DERIVATIVES |
| EP1719757B1 (en) | 2004-02-27 | 2013-10-09 | Kyorin Pharmaceutical Co., Ltd. | Bicyclo derivative |
| WO2005085265A1 (ja) | 2004-03-04 | 2005-09-15 | Kissei Pharmaceutical Co., Ltd. | 縮合ヘテロ環誘導体、それを含有する医薬組成物およびその医薬用途 |
| CN1950389B (zh) | 2004-03-04 | 2011-01-19 | 橘生药品工业株式会社 | 含氮稠环衍生物，含该衍生物的药物组合物，和其作为药物的用途 |
| CN102134231B (zh) | 2004-03-15 | 2020-08-04 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| EA011158B1 (ru) | 2004-03-16 | 2009-02-27 | Бёрингер Ингельхайм Интернациональ Гмбх | Замещённые глюкопиранозилом бензольные производные, содержащие эти соединения лекарственные средства, их применение и способ их получения |
| WO2006018150A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| AR051446A1 (es) | 2004-09-23 | 2007-01-17 | Bristol Myers Squibb Co | Glucosidos de c-arilo como inhibidores selectivos de transportadores de glucosa (sglt2) |
| WO2006035796A1 (ja) | 2004-09-29 | 2006-04-06 | Kissei Pharmaceutical Co., Ltd. | １－（β－Ｄ－グリコピラノシル）－３－置換含窒素ヘテロ環化合物、それを含有する医薬組成物及びその医薬用途 |
| WO2006073167A1 (ja) * | 2005-01-07 | 2006-07-13 | Ono Pharmaceutical Co., Ltd. | ピロリジン誘導体 |
| AR053329A1 (es) | 2005-01-31 | 2007-05-02 | Tanabe Seiyaku Co | Derivados de indol utiles como inhibidores de los transportadores de glucosa dependientes del sodio (sglt) |
| KR20130076903A (ko) | 2005-02-18 | 2013-07-08 | 미쓰비시 타나베 파마 코퍼레이션 | 프롤린 유도체의 염 또는 그 용매화물 및 그 제조 방법 |
| WO2006090244A1 (en) | 2005-02-22 | 2006-08-31 | Glenmark Pharmaceuticals S.A. | New adamantane derivatives as dipeptidyl, peptidase iv inhibitors, processes for their preparation, and pharmaceutical compositions containing them |
| EP1741790A1 (en) | 2005-03-24 | 2007-01-10 | DIGILAB BioVisioN GmbH | Methods to identify and characterize prolyl oligopeptidases by using substrates and products thereof |
| TWI357902B (en) | 2005-04-01 | 2012-02-11 | Lg Life Science Ltd | Dipeptidyl peptidase-iv inhibiting compounds, meth |
| ES2338041T3 (es) | 2005-04-15 | 2010-05-03 | Boehringer Ingelheim International Gmbh | Derivados de (heteroariloxi-bencil)-benceno sustituidos con glucopiranosilo en calidad de inhibidores de sglt. |
| ES2477868T3 (es) * | 2005-04-22 | 2014-07-18 | Alantos Pharmaceuticals Holding, Inc. | Inhibidores de dipeptidil peptidasa-IV |
| US7723309B2 (en) | 2005-05-03 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| DK1894567T3 (da) | 2005-06-03 | 2012-11-19 | Mitsubishi Tanabe Pharma Corp | Ledsagende farmaceutiske midler og anvendelse deraf |
| US20090221592A1 (en) | 2005-07-25 | 2009-09-03 | Ellison Martha E | Dodecylsulfate Salt Of A Dipeptidyl Peptidase-Iv Inhibitor |
| WO2007054978A2 (en) | 2005-11-10 | 2007-05-18 | Jubilant Organosys Limited | Process for preparing paroxetine hydrochloride hemihydrate |
| WO2007063928A1 (ja) * | 2005-11-30 | 2007-06-07 | Toray Industries, Inc. | 新規な非環状アミンカルボキシアミド誘導体及びその塩 |
| EP1842850A1 (en) | 2006-03-23 | 2007-10-10 | Sandoz AG | Rosiglitazone hydrochloride hemihydrate |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| US8158617B2 (en) * | 2006-05-16 | 2012-04-17 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| EP2019679B1 (en) | 2006-05-23 | 2018-06-20 | Theracos, Inc. | Glucose transport inhibitors and methods of use |
| TWI418556B (zh) | 2006-07-27 | 2013-12-11 | Mitsubishi Tanabe Pharma Corp | 吲哚衍生物 |
| US20080027014A1 (en) * | 2006-07-28 | 2008-01-31 | Tanabe Seiyaku Co., Ltd. | Novel SGLT inhibitors |
| US20070172525A1 (en) * | 2007-03-15 | 2007-07-26 | Ramesh Sesha | Anti-diabetic combinations |
| PE20090696A1 (es) * | 2007-04-20 | 2009-06-20 | Bristol Myers Squibb Co | Formas cristalinas de saxagliptina y procesos para preparar las mismas |
| PE20090987A1 (es) | 2007-08-16 | 2009-08-14 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de pirazol-o-glucosido |
| PE20090603A1 (es) | 2007-08-16 | 2009-06-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de sglt2 y un inhibidor de dpp iv |
| CL2008003653A1 (es) * | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| ES2797503T3 (es) | 2009-02-13 | 2020-12-02 | Boehringer Ingelheim Int | Composición farmacéutica que comprende un inhibidor de SGLT2, un inhibidor de DPP-IV y opcionalmente un agente antidiabético adicional y sus usos |
| UY32427A (es) | 2009-02-13 | 2010-09-30 | Boheringer Ingelheim Internat Gmbh | Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma |
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- 2009-01-16 CN CN200980102300.8A patent/CN101932321B/zh active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2252289B1 (en) | 2019-10-23 |
| KR20100103874A (ko) | 2010-09-28 |
| EP2252289A1 (en) | 2010-11-24 |
| US20140371162A1 (en) | 2014-12-18 |
| ES2763239T3 (es) | 2020-05-27 |
| JP2015044845A (ja) | 2015-03-12 |
| MX2010007818A (es) | 2010-08-09 |
| KR101257554B1 (ko) | 2013-04-23 |
| BRPI0906735A2 (pt) | 2015-07-07 |
| CA2712614A1 (en) | 2009-07-23 |
| CN101932321B (zh) | 2016-05-18 |
| JP5646588B2 (ja) | 2014-12-24 |
| AU2009205060B2 (en) | 2013-06-27 |
| JP2013091654A (ja) | 2013-05-16 |
| AR070193A1 (es) | 2010-03-17 |
| AU2009205060A1 (en) | 2009-07-23 |
| JP2011509922A (ja) | 2011-03-31 |
| RU2010134362A (ru) | 2012-02-27 |
| CA2712614C (en) | 2014-05-27 |
| US8853385B2 (en) | 2014-10-07 |
| US20110059912A1 (en) | 2011-03-10 |
| WO2009091082A1 (en) | 2009-07-23 |
| JP5908563B2 (ja) | 2016-04-26 |
| TW200932249A (en) | 2009-08-01 |
| CN101932321A (zh) | 2010-12-29 |
| JP5204849B2 (ja) | 2013-06-05 |
| AU2009205060C1 (en) | 2013-12-19 |
| CN103599539A (zh) | 2014-02-26 |
| CL2008003653A1 (es) | 2010-03-05 |
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