NO329107B1 - C-arylglukosider, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom - Google Patents
C-arylglukosider, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom Download PDFInfo
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- NO329107B1 NO329107B1 NO20044915A NO20044915A NO329107B1 NO 329107 B1 NO329107 B1 NO 329107B1 NO 20044915 A NO20044915 A NO 20044915A NO 20044915 A NO20044915 A NO 20044915A NO 329107 B1 NO329107 B1 NO 329107B1
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07—ORGANIC CHEMISTRY
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- C07H15/20—Carbocyclic rings
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/151,436 US6515117B2 (en) | 1999-10-12 | 2002-05-20 | C-aryl glucoside SGLT2 inhibitors and method |
PCT/US2003/015591 WO2003099836A1 (en) | 2002-05-20 | 2003-05-15 | C-aryl glucoside sglt2 inhibitors and method |
Publications (2)
Publication Number | Publication Date |
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NO20044915L NO20044915L (no) | 2004-12-16 |
NO329107B1 true NO329107B1 (no) | 2010-08-23 |
Family
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Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
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NO20044915A NO329107B1 (no) | 2002-05-20 | 2004-11-11 | C-arylglukosider, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom |
NO2013007C NO2013007I1 (no) | 2002-05-20 | 2013-04-12 | Dapagliflozin og farmasøytisk akseptable salter derav |
NO2014017C NO2014017I1 (no) | 2002-05-20 | 2014-07-09 | En kombinasjon av dapagliflozin eller et farmasøytisk akseptabelt salt derav og metformin eller et farmasøytisk akseptabelt salt derav |
NO2022041C NO2022041I1 (no) | 2002-05-20 | 2022-10-03 | Dapagliflozin og farmasøytisk akseptable salter derav - forlenget SPC |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
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NO2013007C NO2013007I1 (no) | 2002-05-20 | 2013-04-12 | Dapagliflozin og farmasøytisk akseptable salter derav |
NO2014017C NO2014017I1 (no) | 2002-05-20 | 2014-07-09 | En kombinasjon av dapagliflozin eller et farmasøytisk akseptabelt salt derav og metformin eller et farmasøytisk akseptabelt salt derav |
NO2022041C NO2022041I1 (no) | 2002-05-20 | 2022-10-03 | Dapagliflozin og farmasøytisk akseptable salter derav - forlenget SPC |
Country Status (39)
Country | Link |
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US (1) | US6515117B2 (nl) |
EP (1) | EP1506211B1 (nl) |
JP (4) | JP5090621B2 (nl) |
KR (1) | KR101021752B1 (nl) |
CN (5) | CN101092409A (nl) |
AR (1) | AR040032A1 (nl) |
AT (1) | ATE353334T1 (nl) |
AU (1) | AU2003237886B2 (nl) |
BE (2) | BE2013C025I2 (nl) |
BR (2) | BR122017015091B8 (nl) |
CA (1) | CA2486539C (nl) |
CY (3) | CY1106465T1 (nl) |
DE (1) | DE60311649T2 (nl) |
DK (1) | DK1506211T3 (nl) |
ES (1) | ES2280759T3 (nl) |
FR (2) | FR13C0022I2 (nl) |
GE (1) | GEP20084403B (nl) |
HK (2) | HK1068214A1 (nl) |
HR (1) | HRP20041084B1 (nl) |
IL (1) | IL165119A0 (nl) |
IN (1) | IN2004DE03573A (nl) |
IS (1) | IS7529A (nl) |
LT (1) | LTC1506211I2 (nl) |
LU (2) | LU92182I2 (nl) |
ME (2) | ME00091B (nl) |
MX (1) | MX249731B (nl) |
MY (1) | MY142499A (nl) |
NO (4) | NO329107B1 (nl) |
NZ (1) | NZ536605A (nl) |
PE (1) | PE20040760A1 (nl) |
PL (1) | PL210304B1 (nl) |
PT (1) | PT1506211E (nl) |
RS (1) | RS51469B (nl) |
RU (4) | RU2337916C2 (nl) |
SI (1) | SI1506211T1 (nl) |
TW (1) | TWI310770B (nl) |
UA (1) | UA77306C2 (nl) |
WO (1) | WO2003099836A1 (nl) |
ZA (1) | ZA200409295B (nl) |
Families Citing this family (330)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US6515117B2 (en) * | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
FR2809310B1 (fr) * | 2000-05-26 | 2004-02-13 | Centre Nat Rech Scient | Utilisation de derives de biguanide pour fabriquer un medicament ayant un effet cicatrisant |
US20020082222A1 (en) | 2000-11-30 | 2002-06-27 | Shapira Nathan Andrew | Treatments for neurogenetic disorders, impulse control disorder, and wound healing |
RS50955B (sr) * | 2001-02-24 | 2010-08-31 | Boehringer Ingelheim Pharma Gmbh. & Co.Kg. | Derivati ksantina, njihovo dobijanje i njihova primena kao lekova |
US6936590B2 (en) * | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
EP2065044A1 (en) * | 2001-04-04 | 2009-06-03 | Ortho-McNeil-Janssen Pharmaceuticals, Inc. | Combination therapy comprising glucose reabsorption inhibitors and PPAR modulators |
US6774112B2 (en) * | 2001-04-11 | 2004-08-10 | Bristol-Myers Squibb Company | Amino acid complexes of C-aryl glucosides for treatment of diabetes and method |
US20030087843A1 (en) * | 2001-09-05 | 2003-05-08 | Washburn William N. | O-pyrazole glucoside SGLT2 inhibitors and method of use |
TWI254635B (en) * | 2002-08-05 | 2006-05-11 | Yamanouchi Pharma Co Ltd | Azulene derivative and salt thereof |
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 |
WO2004031203A1 (ja) | 2002-10-04 | 2004-04-15 | Kissei Pharmaceutical Co., Ltd. | ピラゾール誘導体、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 |
DE10258007B4 (de) * | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
KR20050090437A (ko) * | 2003-01-03 | 2005-09-13 | 브리스톨-마이어스 스큅 컴퍼니 | C-아릴 글루코시드 sglt2 억제제의 제조 방법 |
EP1457206A1 (en) * | 2003-03-13 | 2004-09-15 | Fournier Laboratories Ireland Limited | Combined use of a fibrate and orlistat for the treatment of obesity |
ES2567571T3 (es) | 2003-03-14 | 2016-04-25 | Astellas Pharma Inc. | Derivados de C-glucósido y sales de los mismos |
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 |
WO2005012242A2 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica Nv | Substituted benzimidazole-, benztriazole-, and benzimidazolone-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 |
SI1651658T2 (sl) | 2003-08-01 | 2020-12-31 | Mitsubishi Tanabe Pharma Corporation | Nove spojine, ki imajo inhibitorno aktivnost proti transporterju, ki je odvisen od natrija |
EP1679965A4 (en) * | 2003-08-01 | 2009-05-27 | Janssen Pharmaceutica Nv | SUBSTITUTED FUSED HETEROCYCLIC C-GLYCOSIDES |
CA2549025A1 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indole-o-glucosides |
US7371759B2 (en) * | 2003-09-25 | 2008-05-13 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
US7420059B2 (en) * | 2003-11-20 | 2008-09-02 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
RU2387663C2 (ru) * | 2004-03-04 | 2010-04-27 | Киссеи Фармасьютикал Ко., Лтд. | Конденсированные гетероциклические производные, содержащие их медицинские композиции и их медицинское применение |
CN103467423B (zh) * | 2004-03-16 | 2016-03-16 | 贝林格尔.英格海姆国际有限公司 | 吡喃葡萄糖基取代的苯基衍生物、含该化合物的药物、其用途及其制造方法 |
EP1750862B1 (en) | 2004-06-04 | 2011-01-05 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
US7393836B2 (en) | 2004-07-06 | 2008-07-01 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
US7572805B2 (en) | 2004-07-14 | 2009-08-11 | Bristol-Myers Squibb Company | Pyrrolo(oxo)isoquinolines as 5HT ligands |
DE102004034690A1 (de) * | 2004-07-17 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Methyliden-D-xylopyranosyl-und Oxo-D-xylopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
TW200606129A (en) * | 2004-07-26 | 2006-02-16 | Chugai Pharmaceutical Co Ltd | Novel cyclohexane derivative, its prodrug, its salt and diabetic therapeutic agent containing the same |
CA2574451A1 (en) * | 2004-07-27 | 2006-02-02 | Boehringer Ingelheim International Gmbh | D-glucopyranosyl phenyl-substituted cyclene, medicaments containing these compounds, their use, and method for the production thereof |
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 |
DE102004048388A1 (de) | 2004-10-01 | 2006-04-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
US20090036355A1 (en) * | 2004-10-13 | 2009-02-05 | Sanjay Bhanot | Antisense Modulation of PTP1B Expression |
DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
TW200635599A (en) * | 2004-12-16 | 2006-10-16 | Boehringer Ingelheim Int | Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
TWI365186B (en) * | 2005-01-31 | 2012-06-01 | Mitsubishi Tanabe Pharma Corp | Indole derivatives |
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) |
WO2006086464A2 (en) * | 2005-02-10 | 2006-08-17 | Bristol-Myers Squibb Company | Dihydroquinazolinones as 5ht modulators |
EP1856082B1 (en) * | 2005-02-23 | 2009-10-14 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted ((hetero)arylethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter 2 (sglt2) inhibitors |
CA2605245A1 (en) * | 2005-04-15 | 2006-10-19 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives as sglt inhibitors |
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 |
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 |
US7772191B2 (en) * | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
WO2007000445A1 (en) * | 2005-06-29 | 2007-01-04 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
TW200726755A (en) * | 2005-07-07 | 2007-07-16 | Astellas Pharma Inc | A crystalline choline salt of an azulene derivative |
TW200733966A (en) * | 2005-07-27 | 2007-09-16 | Boehringer Ingelheim Int | Glucopyranosyl-substituted ((hetero)cycloalkylethynyl-benzyl)-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
MX2008000811A (es) * | 2005-07-28 | 2008-03-18 | Squibb Bristol Myers Co | Tetrahidro-1h-pitido[4,3-b]indoles substituidos como agonistas y antagonistas del receptor de serotonina. |
DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
US7795436B2 (en) * | 2005-08-24 | 2010-09-14 | Bristol-Myers Squibb Company | Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists |
JP5175191B2 (ja) * | 2005-08-30 | 2013-04-03 | 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 | グリコピラノシル置換ベンジルベンゼン誘導体、該化合物を含有する医薬品及びその使用と製造方法 |
CA2621314A1 (en) * | 2005-09-08 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(.beta.-d-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
AR056195A1 (es) * | 2005-09-15 | 2007-09-26 | Boehringer Ingelheim Int | Procedimientos para preparar derivados de (etinil-bencil)-benceno sustituidos de glucopiranosilo y compuestos intermedios de los mismos |
RU2438671C2 (ru) * | 2005-12-28 | 2012-01-10 | Такеда Фармасьютикал Компани Лимитед | Терапевтическое средство против диабета |
JP2009531291A (ja) * | 2006-02-15 | 2009-09-03 | 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 | グルコピラノシル置換ベンゾニトリル誘導体、それらの化合物を含有する医薬組成物、それらの使用及び製造方法 |
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 |
PE20110235A1 (es) * | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
NZ619413A (en) | 2006-05-04 | 2015-08-28 | Boehringer Ingelheim Int | Polymorphs of a dpp-iv enzyme inhibitor |
EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
US20090176717A1 (en) * | 2006-06-01 | 2009-07-09 | Glycomimetics, Inc. | Galactosides and thiodigalactosides as inhibitors of pa-il lectin from pseudomonas |
DE102006028862A1 (de) | 2006-06-23 | 2007-12-27 | Merck Patent Gmbh | 3-Amino-imidazo[1,2-a]pyridinderivate |
US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
US7795291B2 (en) | 2006-07-07 | 2010-09-14 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as anti-atherosclerotic, anti-dyslipidemic, anti-diabetic and anti-obesity agents and method |
TWI432446B (zh) | 2006-07-27 | 2014-04-01 | Chugai Pharmaceutical Co Ltd | 稠環螺酮縮醇衍生物、及其做為糖尿病治療藥之使用 |
TWI403516B (zh) | 2006-07-27 | 2013-08-01 | Chugai Pharmaceutical Co Ltd | To replace spirocyclic alcohol derivatives, and its use as a therapeutic agent for diabetes |
TWI418556B (zh) * | 2006-07-27 | 2013-12-11 | Mitsubishi Tanabe Pharma Corp | 吲哚衍生物 |
US8039441B2 (en) | 2006-08-15 | 2011-10-18 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted cyclopropylbenzene derivatives, pharmaceutical compositions containing such compounds, their use as SGLT inhibitors and process for their manufacture |
BRPI0716519A2 (pt) * | 2006-09-07 | 2013-10-08 | Glaxosmithkline Biolog Sa | Método para fabricar uma vacina |
TWI499414B (zh) * | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第2型共同運輸體(co-transporter 2)的抑制物與其應用方法 |
US20080194575A1 (en) * | 2006-10-04 | 2008-08-14 | Naiara Beraza | Treatment for non-alcoholic-steatohepatitis |
CN101522699A (zh) | 2006-10-13 | 2009-09-02 | 中外制药株式会社 | 硫葡萄糖螺缩酮衍生物、及其作为糖尿病治疗药的应用 |
US8283326B2 (en) | 2006-10-27 | 2012-10-09 | Boehringer Ingelheim International Gmbh | Crystalline form of 4-(beta-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments |
UY30730A1 (es) * | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
JP5298025B2 (ja) * | 2006-12-04 | 2013-09-25 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗糖尿病薬としてのチエニル含有グリコピラノシル誘導体 |
US8101634B2 (en) | 2006-12-06 | 2012-01-24 | Glaxosmithkline Llc | Bicyclic compounds and use as antidiabetics |
CN101568537A (zh) * | 2006-12-21 | 2009-10-28 | 安斯泰来制药有限公司 | C-糖苷衍生物的制造方法及其合成中间体 |
DE102007008420A1 (de) | 2007-02-21 | 2008-08-28 | Merck Patent Gmbh | Benzimidazolderivate |
WO2008109591A1 (en) * | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
AU2014201239B2 (en) * | 2007-03-22 | 2016-03-10 | Astrazeneca Ab | Pharmaceutical formulations containing dapagliflozin propylene glycol hydrate |
PE20090185A1 (es) * | 2007-03-22 | 2009-02-28 | Bristol Myers Squibb Co | Formulaciones farmaceuticas que contienen un inhibidor sglt2 |
TW200904454A (en) * | 2007-03-22 | 2009-02-01 | Bristol Myers Squibb Co | Methods for treating obesity employing an SGLT2 inhibitor and compositions thereof |
PE20090696A1 (es) | 2007-04-20 | 2009-06-20 | Bristol Myers Squibb Co | Formas cristalinas de saxagliptina y procesos para preparar las mismas |
MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
NZ582536A (en) * | 2007-07-26 | 2012-01-12 | Lexicon Pharmaceuticals Inc | Methods and compounds useful for the preparation of sodium glucose co-transporter 2 inhibitors |
CL2008002425A1 (es) * | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composición farmacéutica que comprende un inhibidor de sglt2 y 1-(4-metil-quinazolin-2-il)metil-3metil-7-(-2-butin-1-il)-8-(3-(r)-amino-piperidin-1il)-xantina, un inhibidor de dpp iv y su uso para el tratamiento de la obesidad y de la diabetes tipo 1 y 2 y complicaciones de esta. |
PE20090938A1 (es) * | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
KR101610005B1 (ko) * | 2007-08-17 | 2016-04-08 | 베링거 인겔하임 인터내셔날 게엠베하 | Fab 관련 질환의 치료에 사용하기 위한 푸린 유도체 |
HUE035947T2 (hu) * | 2007-08-23 | 2018-06-28 | Theracos Sub Llc | A (2S,3R,4R,5S,6R)-2-(4-klór-3-benzilfenil)-6-(hidroximetil)tetrahidro-2H-pirán-3,4,5-triol származékainak felhasználása a diabétesz kezelésében |
SI2200606T1 (sl) * | 2007-09-10 | 2017-12-29 | Janssen Pharmaceutica N.V. | Postopek za pripravo spojin, uporabnih kot inhibitorjev SGLT |
DE102007048716A1 (de) | 2007-10-11 | 2009-04-23 | Merck Patent Gmbh | Imidazo[1,2-a]pyrimidinderivate |
CA2706018C (en) * | 2007-11-30 | 2015-11-24 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo [3,4-d]pyrimidin-4-one derivatives and their use as pde9a modulators for the treatment of cns disorders |
UA101004C2 (en) | 2007-12-13 | 2013-02-25 | Теракос, Инк. | Derivatives of benzylphenylcyclohexane and use thereof |
CN104387354A (zh) * | 2007-12-27 | 2015-03-04 | 阿斯利康公司 | Sglt2 抑制剂的晶体结构及其制备方法 |
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. |
US20110003757A1 (en) * | 2008-01-31 | 2011-01-06 | Astellas Pharma Inc. | Pharmaceutical compositions for treating fatty liver disease |
CN101503399B (zh) * | 2008-02-04 | 2012-06-27 | 白鹭医药技术(上海)有限公司 | C-芳基葡萄糖苷sglt2抑制剂 |
UA105362C2 (en) * | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
AR071175A1 (es) * | 2008-04-03 | 2010-06-02 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante |
DE102008017590A1 (de) | 2008-04-07 | 2009-10-08 | Merck Patent Gmbh | Glucopyranosidderivate |
WO2009143021A1 (en) * | 2008-05-22 | 2009-11-26 | Bristol-Myers Squibb Company | Method for treating and preventing kidney stones employing an sglt2 inhibitor and composition containing same |
US8791077B2 (en) * | 2008-05-22 | 2014-07-29 | Astrazeneca Ab | Method for treating hyperuricemia employing an SGLT2 inhibitor and composition containing same |
WO2009143010A1 (en) * | 2008-05-22 | 2009-11-26 | Bristol-Myers Squibb Company | Method for treating hyponatremia employing an sglt2 inhibitor and composition containing same |
PE20100156A1 (es) * | 2008-06-03 | 2010-02-23 | Boehringer Ingelheim Int | Tratamiento de nafld |
JP2011522828A (ja) | 2008-06-04 | 2011-08-04 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
MX2011000637A (es) * | 2008-07-15 | 2011-05-02 | Theracos Inc | Derivados deuretados de bencilbenceno y metodos de uso. |
EP3241839B1 (en) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
EP3626238A1 (en) * | 2008-08-15 | 2020-03-25 | Boehringer Ingelheim International GmbH | Dpp-4 inhibitors for use for the treatment of wound healing in diabetic patients |
PT2324002T (pt) * | 2008-08-22 | 2016-11-09 | Theracos Sub Llc | Processos para a preparação de inibidores de sglt2 |
CA2733795C (en) * | 2008-08-28 | 2013-12-31 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
PE20110383A1 (es) | 2008-09-08 | 2011-07-15 | Boehringer Ingelheim Int | Pirazolopirimidinonas como inhibidores de la fosfodiesterasa 9a (pde9a) |
BRPI0919288A2 (pt) | 2008-09-10 | 2015-12-15 | Boehring Ingelheim Internat Gmbh | teriapia de combinação para tratamento de diabetes e condições relacionadas. |
CA2737830A1 (en) * | 2008-09-19 | 2010-03-25 | Novartis Ag | Glycoside derivatives and uses thereof |
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 |
WO2010045656A2 (en) * | 2008-10-17 | 2010-04-22 | Nectid, Inc. | Novel sglt2 inhibitor dosage forms |
CN102256976A (zh) | 2008-12-23 | 2011-11-23 | 贝林格尔.英格海姆国际有限公司 | 有机化合物的盐形式 |
AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
SG173587A1 (en) | 2009-02-13 | 2011-09-29 | Boehringer Ingelheim Int | Sglt-2 inhibitor for treating type 1 diabetes mellitus, type 2 diabetes mellitus, impaired glucose tolerance or hyperglycemia |
NZ594024A (en) | 2009-02-13 | 2013-08-30 | Boehringer Ingelheim Int | Pharmaceutical composition comprising glucopyranosyl diphenylmethane derivatives, pharmaceutical dosage form thereof, process for their preparation and uses thereof for improved glycemic control in a patient |
UY32441A (es) * | 2009-02-13 | 2010-09-30 | Boehringer Ingelheim Int | Composicion farmaceutica, metodos de tratamiento 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 |
CA2752212C (en) * | 2009-02-23 | 2016-08-16 | Taisho Pharmaceutical Co., Ltd. | 4-isopropylphenyl glucitol compounds as sglt1 inhibitors |
EP2226076A1 (de) | 2009-02-25 | 2010-09-08 | Henning Vollert | Pflanzlicher Extrakt zur Prophylaxe und Behandlung von hyperglykämischen Erkrankungen |
EP2414363B1 (en) * | 2009-03-31 | 2014-01-08 | Boehringer Ingelheim International GmbH | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives and their use as pde9a modulators |
JP2012528170A (ja) * | 2009-05-27 | 2012-11-12 | ブリストル−マイヤーズ スクイブ カンパニー | 別の抗糖尿病薬を用いた先の治療に抵抗性を有する2型糖尿病患者をsglt2阻害剤およびその組成物を用いて治療する方法 |
US20110009347A1 (en) * | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
JP5658751B2 (ja) | 2009-07-10 | 2015-01-28 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプJanssen Pharmaceutica Naamloze Vennootschap | 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼンのための結晶化方法 |
TW201118099A (en) * | 2009-08-12 | 2011-06-01 | Boehringer Ingelheim Int | New compounds for the treatment of CNS disorders |
WO2011039108A2 (en) * | 2009-09-30 | 2011-04-07 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
CA2775961C (en) * | 2009-09-30 | 2017-11-07 | 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 |
US10610489B2 (en) * | 2009-10-02 | 2020-04-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, pharmaceutical dosage form, process for their preparation, methods for treating and uses thereof |
RS55909B1 (sr) * | 2009-10-14 | 2017-09-29 | Janssen Pharmaceutica Nv | Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2 |
US8163704B2 (en) * | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
DK2496583T3 (en) | 2009-11-02 | 2015-02-02 | Pfizer | Dioxa-bicyclo [3.2.1] octane-2,3,4-triol DERIVATIVES |
DK2498758T3 (en) * | 2009-11-13 | 2018-10-15 | Astrazeneca Ab | TWO-LAYER TABLET FORMULATIONS |
AU2010319377B2 (en) | 2009-11-13 | 2014-10-23 | Astrazeneca Ab | Immediate release tablet formulations |
WO2011058193A1 (en) | 2009-11-16 | 2011-05-19 | Mellitech | [1,5]-diazocin derivatives |
KR20210033559A (ko) | 2009-11-27 | 2021-03-26 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 dpp-iv 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
WO2011070592A2 (en) | 2009-12-09 | 2011-06-16 | Panacea Biotec Ltd. | Novel sugar derivatives |
CN102134226B (zh) * | 2010-01-26 | 2013-06-12 | 天津药物研究院 | 一类苯基c-葡萄糖苷衍生物、其制备方法和用途 |
WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
JP2013523681A (ja) * | 2010-03-30 | 2013-06-17 | 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 | Sglt2インヒビター及びppar−ガンマアゴニストを含む医薬組成物並びにその使用 |
CN102946875A (zh) | 2010-05-05 | 2013-02-27 | 贝林格尔.英格海姆国际有限公司 | 组合疗法 |
SI2568988T1 (sl) | 2010-05-11 | 2016-10-28 | Janssen Pharmaceutica N.V. | Farmacevtske formulacije, obsegajoče 1-(beta-D-glukopiranozil)-2-tienilmetilbenzenske derivate kot inhibitorje SGLT |
CN102985075A (zh) | 2010-05-11 | 2013-03-20 | 田边三菱制药株式会社 | 含卡纳格列净的片剂 |
WO2011153712A1 (en) | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
EP3124041A1 (en) | 2010-06-24 | 2017-02-01 | Boehringer Ingelheim International GmbH | Diabetes therapy |
DK2603511T3 (en) | 2010-08-12 | 2017-05-08 | Boehringer Ingelheim Int | 6-CYCLOALKYL-1, 5-DIHYDRO-PYRAZOLO- [3,4-D] PYRIMIDIN-4-ON DERIVATIVES AND THEIR USES AS PDE9A INHIBITORS |
WO2012025857A1 (en) | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
US20130224296A1 (en) | 2010-09-03 | 2013-08-29 | Bristol-Myers Squibb Company | Drug Formulations Using Water Soluble Antioxidants |
WO2012037034A1 (en) | 2010-09-14 | 2012-03-22 | Glycomimetics, Inc. | E-selectin antagonists |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
WO2012041898A1 (en) | 2010-09-29 | 2012-04-05 | Celon Pharma Sp. Z O.O. | Combination of sglt2 inhibitor and a sugar compound for the treatment of diabetes |
CN102453026A (zh) | 2010-10-27 | 2012-05-16 | 上海艾力斯医药科技有限公司 | C-芳基葡糖苷衍生物、制备方法及其应用 |
US20120283169A1 (en) | 2010-11-08 | 2012-11-08 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
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 |
RU2607480C2 (ru) | 2011-02-01 | 2017-01-10 | Бристол-Майерс Сквибб Компани | Фармацевтические композиции, содержащие аминосоединение |
US20130035281A1 (en) | 2011-02-09 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
US8980829B2 (en) | 2011-02-18 | 2015-03-17 | Shanghai Yingli Science And Technology Co., Ltd | Aryl glycoside compound, preparation method and use thereof |
CN102167715B (zh) * | 2011-03-07 | 2013-04-24 | 上海惠斯生物科技有限公司 | 一种钠-葡萄糖协同运转蛋白-2原料药的共晶制备方法 |
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 |
RS55056B1 (sr) | 2011-04-13 | 2016-12-30 | Janssen Pharmaceutica Nv | Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2 |
AU2012248061C1 (en) * | 2011-04-25 | 2016-07-14 | Beijing Prelude Pharm. Sci. & Tech. Co., Ltd. | Inhibitor of sodium-dependent glucose transport protein and preparation method therefor and use thereof |
US9035044B2 (en) | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
BR112013030163A2 (pt) * | 2011-05-26 | 2017-03-01 | Tfchem | composto, uso cosmético de pelo menos um composto, composição farmacêutica ou cosmética e processo para preparar um composto. |
AU2012264736A1 (en) | 2011-06-03 | 2013-11-28 | Boehringer Ingelheim International Gmbh | SGLT-2 inhibitors for treating metabolic disorders in patients treated with neuroleptic agents |
ES2448398T3 (es) | 2011-06-03 | 2014-03-13 | Ratiopharm Gmbh | Composición farmacéutica que comprende dapagliflozina y ciclodextrina |
WO2012163546A1 (en) | 2011-06-03 | 2012-12-06 | Ratiopharm Gmbh | Pharmaceutical composition comprising dapagliflozin and cyclodextrin |
EP2725031B1 (en) | 2011-06-25 | 2016-08-03 | Xuanzhu Pharma Co., Ltd. | C-glycoside derivatives |
US20130035298A1 (en) | 2011-07-08 | 2013-02-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
AU2012285904C1 (en) | 2011-07-15 | 2017-08-31 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
WO2013038429A2 (en) | 2011-09-13 | 2013-03-21 | Panacea Biotec Ltd. | Novel sglt inhibitors |
KR20140097258A (ko) * | 2011-10-31 | 2014-08-06 | 시노팜 타이완 리미티드 | Sglt2 억제제의 결정성 및 비-결정성 형태 |
EP2597090A1 (en) | 2011-11-28 | 2013-05-29 | Sandoz AG | Crystalline dapagliflozin hydrate |
KR102055958B1 (ko) | 2011-12-22 | 2019-12-13 | 글리코미메틱스, 인크. | E-셀렉틴 길항제 화합물, 조성물, 및 이용 방법 |
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 |
US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
EP2849755A1 (en) | 2012-05-14 | 2015-03-25 | Boehringer Ingelheim International GmbH | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
WO2013178064A1 (zh) * | 2012-05-29 | 2013-12-05 | 广东东阳光药业有限公司 | 吡喃葡萄糖基衍生物、其制备方法及其在医药上的应用 |
EP2679229B1 (de) | 2012-06-30 | 2019-02-27 | BioActive Food GmbH | Zusammensetzung zur Behandlung von hyperglykämischen Erkrankungen |
EP2891499A4 (en) * | 2012-08-30 | 2016-02-24 | Taisho Pharmaceutical Co Ltd | ASSOCIATION OF A SGLT2 INHIBITOR AND AN ANTIHYPERTENSEUR |
AU2013355238B2 (en) | 2012-12-07 | 2017-12-14 | Glycomimetics, Inc. | Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells |
CN103910769B (zh) | 2012-12-31 | 2018-10-02 | 上海璎黎药业有限公司 | 葡萄糖衍生物和脯氨酸的复合物、晶体、制备方法及应用 |
EP2774619B1 (de) | 2013-03-04 | 2016-05-18 | BioActive Food GmbH | Zusammensetzung zur Behandlung von hyperglykämischen Erkrankungen |
US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
ES2969245T3 (es) | 2013-03-14 | 2024-05-17 | Msd Int Gmbh | Formas cristalinas y métodos para preparar inhibidores de SGLT2 |
US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
PT2981269T (pt) | 2013-04-04 | 2023-10-10 | Boehringer Ingelheim Vetmedica Gmbh | Tratamento de distúrbios metabólicos em animais equinos |
PT2981271T (pt) | 2013-04-05 | 2019-02-19 | Boehringer Ingelheim Int | Utilizações terapêuticas de empagliflozina |
US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
DK2986304T3 (da) | 2013-04-18 | 2022-04-04 | Boehringer Ingelheim Int | Farmaceutisk sammensætning, fremgangsmåder til behandling og anvendelser deraf. |
WO2014178040A1 (en) | 2013-04-29 | 2014-11-06 | Mapi Pharma Ltd. | Co-crystals of dapagliflozin |
EA201592263A1 (ru) | 2013-06-05 | 2016-05-31 | Синерджи Фармасьютикалз, Инк. | Ультрачистые агонисты гуанилатциклазы c, способ их получения и использования |
WO2015040571A1 (en) | 2013-09-23 | 2015-03-26 | Ranbaxy Laboratories Limited | Process for the preparation of dapagliflozin |
EP3049397A1 (en) * | 2013-09-27 | 2016-08-03 | Sun Pharmaceutical Industries Ltd | Process for the purification of dapagliflozin |
CN104513283B (zh) | 2013-09-27 | 2018-01-16 | 广东东阳光药业有限公司 | 吡喃葡萄糖基衍生物及其在医药上的应用 |
CN105611920B (zh) | 2013-10-12 | 2021-07-16 | 泰拉科斯萨普有限责任公司 | 羟基-二苯甲烷衍生物的制备 |
WO2015063726A1 (en) | 2013-10-31 | 2015-05-07 | Ranbaxy Laboratories Limited | Process for the preparation of 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene |
FI3862003T3 (fi) | 2013-12-17 | 2023-12-28 | Boehringer Ingelheim Vetmedica Gmbh | SGLT-2-ihibiittori käytettäväksi aineenvaihdutahäiriön hoidossa kissaeläimillä |
WO2015101916A1 (en) | 2013-12-30 | 2015-07-09 | Mylan Laboratories Ltd. | Process for the preparation of empagliflozin |
CN104761522B (zh) * | 2014-01-03 | 2017-02-15 | 山东轩竹医药科技有限公司 | 光学纯的苄基‑4‑氯苯基的c‑糖苷衍生物 |
US9315438B2 (en) | 2014-01-03 | 2016-04-19 | Xuanzhu Pharma Co., Ltd | Optically pure benzyl-4-chlorophenyl-C-glucoside derivative |
CN103739581B (zh) * | 2014-01-23 | 2016-11-23 | 中国药科大学 | C-芳基葡萄糖苷sglt2抑制剂 |
MX2016009421A (es) | 2014-01-23 | 2016-09-16 | Boehringer Ingelheim Vetmedica Gmbh | Tratamiento de trastornos metabolicos en animales caninos. |
CN104829572B (zh) * | 2014-02-10 | 2019-01-04 | 江苏豪森药业集团有限公司 | 达格列净新晶型及其制备方法 |
IN2014MU00626A (nl) * | 2014-02-21 | 2015-09-25 | Cadila Healthcare Ltd | |
US20170056365A1 (en) | 2014-02-28 | 2017-03-02 | Sun Pharmaceutical Industries Limited | Dapagliflozin compositions |
US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
EP3114115A4 (en) * | 2014-03-06 | 2017-08-23 | MSN Laboratories Private Limited | Process for the preparation of (1s)-1,5-anhydro-1-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-d-glucitol and its solvate thereof |
NZ723781A (en) | 2014-04-01 | 2022-09-30 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in equine animals |
CN105001213B (zh) * | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
JP2017515908A (ja) * | 2014-05-16 | 2017-06-15 | アストラゼネカ・アクチエボラーグAstrazeneca Aktiebolag | Sglt2インヒビター誘発性グルカゴン分泌の抑制方法 |
EP2944311A1 (de) | 2014-05-16 | 2015-11-18 | BioActive Food GmbH | Kombination von biologisch aktiven Substanzen zur Behandlung von hyperglykämischen Erkrankungen |
WO2015198227A1 (en) | 2014-06-23 | 2015-12-30 | Sun Pharmaceutical Industries Limited | Co-crystal of dapagliflozin with citric acid |
MX2017003716A (es) | 2014-09-25 | 2017-06-30 | Boehringer Ingelheim Vetmedica Gmbh | Tratamiento de combinacion y/o prevencion de transtorno metabolicos en animales equinos. |
KR20170049606A (ko) | 2014-09-25 | 2017-05-10 | 아스트라제네카 아베 | 간 질환을 치료하기 위한 오메가-3 지방산과 sglt-2 억제제의 조합 |
CN104327027B (zh) * | 2014-10-14 | 2017-04-05 | 中国药科大学 | 一类新型c‑芳基葡萄糖苷sglt2抑制剂 |
CN104478839A (zh) * | 2014-11-24 | 2015-04-01 | 苏州乔纳森新材料科技有限公司 | 一种达格列净的合成方法 |
CN104496952B (zh) * | 2014-11-28 | 2017-04-19 | 深圳翰宇药业股份有限公司 | 一种达格列净的合成方法 |
EP3569609A1 (en) | 2014-12-03 | 2019-11-20 | GlycoMimetics, Inc. | Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors |
CN105753910A (zh) * | 2014-12-16 | 2016-07-13 | 康普药业股份有限公司 | 一种卡格列净中间体的制备方法 |
CN104529970A (zh) * | 2015-01-08 | 2015-04-22 | 江苏联环药业股份有限公司 | 制备达格列净的方法 |
CN104478968A (zh) * | 2015-01-14 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 含噻唑基的o-半乳糖苷衍生物、其制备方法和用途 |
CN104478957A (zh) * | 2015-01-14 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 一种含腈基苯和双o-葡萄糖苷衍生物、其制备方法和用途 |
CN104530149A (zh) * | 2015-01-14 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | 卤代苯基双o-葡萄糖苷衍生物、其制备方法和用途 |
CN104478966A (zh) * | 2015-01-14 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 含苯胺噻唑基的o-半乳糖苷衍生物、其制备方法和用途 |
CN104478959A (zh) * | 2015-01-14 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 含腈基联苯双葡萄糖苷结构化合物、其制备方法和用途 |
CN104478965A (zh) * | 2015-01-15 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 一类烷氧基苯基s-葡萄糖苷衍生物、其制备方法和用途 |
CN104478963A (zh) * | 2015-01-15 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 一种含腈基苯s-葡萄糖苷结构的化合物及其用途 |
CN104497070A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 一种含三氟甲基苯s-葡萄糖苷结构的化合物和用途 |
WO2016128995A1 (en) | 2015-02-09 | 2016-08-18 | Indoco Remedies Limited | Process for the preparation of sglt inhibitor compounds |
WO2016144862A1 (en) | 2015-03-09 | 2016-09-15 | Intekrin Therapeutics, Inc. | Methods for the treatment of nonalcoholic fatty liver disease and/or lipodystrophy |
WO2016161995A1 (en) | 2015-04-08 | 2016-10-13 | Zentiva, K.S. | Solid forms of amorphous dapagliflozin |
US10556877B2 (en) | 2015-05-05 | 2020-02-11 | Glenmark Life Sciences Limited | Process for preparation of dapagliflozin |
CN106317068A (zh) * | 2015-06-23 | 2017-01-11 | 中国科学院上海药物研究所 | 一种c,o-螺环芳基糖苷类化合物及其制备和应用 |
CN104961715B (zh) * | 2015-07-10 | 2017-08-22 | 浙江美诺华药物化学有限公司 | 一种达格列净的制备方法 |
EP3349762B1 (en) | 2015-09-15 | 2021-08-25 | Laurus Labs Limited | Co-crystals of sglt2 inhibitors, process for their preparation and pharmaceutical compositions thereof |
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 |
CZ2015729A3 (cs) | 2015-10-13 | 2017-04-26 | Zentiva, K.S. | Příprava intermediátů pro syntézu Canagliflozinu a Dapagliflozinu |
CN105218329B (zh) * | 2015-10-15 | 2017-05-03 | 上海应用技术学院 | 一种列净类似物中间体及其制备方法 |
WO2017064193A1 (en) | 2015-10-15 | 2017-04-20 | Boehringer Ingelheim International Gmbh | Sglt-2 inhibitor for use in the treatment of a metabolic myopathy |
US9845303B2 (en) | 2015-10-19 | 2017-12-19 | Cadila Healthcare Limited | Process for the preparation of dapagliflozin |
CN106892929B (zh) * | 2015-12-17 | 2020-01-14 | 上海艾力斯医药科技有限公司 | 螺缩酮衍生物及其制备方法和应用 |
CN105693669A (zh) * | 2015-12-28 | 2016-06-22 | 南昌大学 | 一种抗糖尿病化合物及其制备方法和用途 |
EP3404033B1 (en) * | 2016-01-04 | 2020-08-05 | Jeil Pharmaceutical Co., Ltd. | C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same |
WO2017118945A1 (en) | 2016-01-08 | 2017-07-13 | Lupin Limited | Premix of dapagliflozin and process for the preparation thereof |
JP2019502727A (ja) | 2016-01-22 | 2019-01-31 | グリコミメティクス, インコーポレイテッド | Pa−ilおよび/またはpa−iilレクチンの糖模倣体阻害剤 |
US9834533B2 (en) * | 2016-02-19 | 2017-12-05 | Scinopharm Taiwan, Ltd. | Process for preparing SGLT2 inhibitors and intermediates thereof |
WO2017151708A1 (en) | 2016-03-02 | 2017-09-08 | Glycomimetics, Inc. | Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin |
US20190110994A1 (en) | 2016-03-31 | 2019-04-18 | Lupin Limited | Pharmaceutical composition of dapagliflozin |
CN107304194A (zh) * | 2016-04-20 | 2017-10-31 | 扬子江药业集团上海海尼药业有限公司 | 制备达格列净的方法 |
JP7007300B2 (ja) * | 2016-05-24 | 2022-01-24 | 江▲蘇▼豪森▲薬▼▲業▼集▲団▼有限公司 | ダパグリフロジンの新規な結晶形並びにその製造方法および用途 |
WO2017203229A1 (en) | 2016-05-27 | 2017-11-30 | Cipla Limited | Dapagliflozin premixes |
WO2017211979A1 (en) | 2016-06-10 | 2017-12-14 | Boehringer Ingelheim International Gmbh | Combinations of linagliptin and metformin |
WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
EP3497131B1 (en) | 2016-08-08 | 2022-03-09 | GlycoMimetics, Inc. | Combination of t-cell checkpoint inhibitors with inhibitors of e-selectin or cxcr4, or with heterobifunctional inhibitors of both e-selectin and cxcr4. |
ES2926403T3 (es) * | 2016-08-09 | 2022-10-25 | Laurus Labs Ltd | Nuevos procedimientos para la preparación de dapagliflozina o sus solvatos o co-cristales de la misma |
WO2018029264A1 (en) | 2016-08-10 | 2018-02-15 | Amneal Pharmaceuticals Company Gmbh | Process for preparation of dapagliflozin and intermediates thereof |
KR102653723B1 (ko) | 2016-10-07 | 2024-04-01 | 글리코미메틱스, 인크. | 매우 강력한 다량체성 e-셀렉틴 길항물질 |
CN109843279A (zh) | 2016-10-19 | 2019-06-04 | 勃林格殷格翰国际有限公司 | 包含ssao/vap-1抑制剂和sglt2抑制剂的药物组合、其用途 |
KR20180058510A (ko) | 2016-11-24 | 2018-06-01 | 한미약품 주식회사 | 다파글리플로진 l-프롤린을 포함하는 약제학적 제제 |
CN108218928B (zh) * | 2016-12-13 | 2020-06-30 | 华润双鹤药业股份有限公司 | 葡萄糖苷的二环衍生物及其制备方法和用途 |
WO2018142422A1 (en) * | 2017-02-02 | 2018-08-09 | Indoco Remedies Limited | Process for the preparation of dapagliflozin |
CA3054605A1 (en) | 2017-03-15 | 2018-09-20 | Glycomimetics, Inc. | Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists |
US11020412B2 (en) | 2017-03-16 | 2021-06-01 | Inventia Healthcare Limited | Pharmaceutical composition comprising dapagliflozin |
CA3058806A1 (en) | 2017-04-03 | 2018-10-11 | Coherus Biosciences Inc. | Ppar.gamma. agonist for treatment of progressive supranuclear palsy |
WO2018207113A1 (en) | 2017-05-09 | 2018-11-15 | Piramal Enterprises Limited | A process for the preparation of sglt2 inhibitor and intermediates thereof |
AR112015A1 (es) | 2017-06-09 | 2019-09-11 | Novo Nordisk As | Composiciones sólidas para administración oral |
KR101943382B1 (ko) | 2017-09-19 | 2019-01-29 | 오토텔릭바이오 주식회사 | Sglt-2 저해제 및 안지오텐신 수용체 차단제를 포함하는 의약 조성물 |
EP3717013A1 (en) | 2017-11-30 | 2020-10-07 | GlycoMimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
CN111566117A (zh) | 2017-12-29 | 2020-08-21 | 糖模拟物有限公司 | E-选择蛋白和半乳凝素-3的异双功能抑制剂 |
KR20200128025A (ko) | 2018-03-05 | 2020-11-11 | 글리코미메틱스, 인크. | 급성 골수성 백혈병 및 관련 병태의 치료 방법 |
JP2021520394A (ja) | 2018-04-17 | 2021-08-19 | 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 | 医薬組成物、処置方法及びその使用 |
KR102204439B1 (ko) | 2018-05-14 | 2021-01-18 | 에이치케이이노엔 주식회사 | Sglt-2 억제제 및 dpp-iv 억제제를 포함하는 약제학적 조성물 |
EP3810623A1 (en) | 2018-06-25 | 2021-04-28 | Pharmathen S.A. | A novel process for the preparation of sglt-2 inhibitors |
MX2021000601A (es) * | 2018-07-19 | 2021-04-13 | Astrazeneca Ab | Metodos de tratamiento de hfpef empleando dapagliflozina y composiciones que comprenden la misma. |
WO2020039394A1 (en) | 2018-08-24 | 2020-02-27 | Novartis Ag | New drug combinations |
KR102131359B1 (ko) | 2018-09-07 | 2020-07-07 | 오토텔릭바이오 주식회사 | 안정성이 향상된 의약 조성물 |
CN109705075B (zh) * | 2018-12-13 | 2022-12-23 | 苏中药业集团股份有限公司 | 一种达格列净的纯化方法 |
WO2020139962A1 (en) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
SG11202003971RA (en) | 2019-08-30 | 2021-04-29 | Astrazeneca Ab | Methods of treating heart failure with reduced ejection fraction with dapagliflozin |
KR20220109431A (ko) | 2019-11-28 | 2022-08-04 | 베링거잉겔하임베트메디카게엠베하 | 인간이 아닌 포유동물의 건유에서 sglt-2 억제제의 용도 |
WO2021165177A1 (en) | 2020-02-17 | 2021-08-26 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of cardiac diseases in felines |
EP4106732A1 (en) | 2020-02-21 | 2022-12-28 | Zaklady Farmaceutyczne Polpharma S.A. | Pharmaceutical composition comprising dapagliflozin |
EP4114365A1 (en) | 2020-03-05 | 2023-01-11 | KRKA, d.d., Novo mesto | Pharmaceutical composition comprising sglt2 inhibitor |
EP4114385A1 (en) | 2020-03-06 | 2023-01-11 | Vertex Pharmaceuticals Incorporated | Methods of treating apol-1 dependent focal segmental glomerulosclerosis |
CA3180674A1 (en) | 2020-04-22 | 2021-10-28 | Bayer Aktiengesellschaft | Combination of finerenone and a sglt2 inhibitor for the treatment and/or prevention of cardiovascular and/or renal diseases |
WO2021219691A1 (en) | 2020-04-29 | 2021-11-04 | Astrazeneca Ab | Dapagliflozin and ambrisentan for the prevention and treatment of covid-19 |
CN115867538A (zh) | 2020-06-05 | 2023-03-28 | 新梅斯托克公司 | 高纯的无定形达格列净的制备 |
WO2021260617A1 (en) * | 2020-06-25 | 2021-12-30 | Hikal Limited | An improved process for preparation of dapagliflozin propanediol monohydrate |
MX2023000276A (es) | 2020-07-10 | 2023-02-09 | Astrazeneca Ab | Combinacion de zibotentan y dapagliflozina para el tratamiento de la enfermedad renal cronica. |
TW202220672A (zh) | 2020-07-27 | 2022-06-01 | 瑞典商阿斯特捷利康公司 | 用達格列淨治療慢性腎臟病之方法 |
WO2022051316A1 (en) | 2020-09-03 | 2022-03-10 | Coherus Biosciences, Inc. | Fixed dose combinations of chs-131 and a sglt-2 inhibitor |
WO2022067724A1 (zh) | 2020-09-30 | 2022-04-07 | 北京睿创康泰医药研究院有限公司 | 一种sglt-2抑制剂·肌氨酸共晶体及其制备方法和应用 |
TR202019589A2 (tr) | 2020-12-03 | 2022-06-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dapagli̇flozi̇n ve metformi̇n hi̇droklorür i̇çeren fi̇lm kapli tablet formülasyonu |
TR202019590A2 (tr) | 2020-12-03 | 2022-06-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dapagli̇flozi̇n ve metformi̇n hi̇droklorür formülasyonlarina yöneli̇k bi̇r proses |
WO2022119543A1 (en) | 2020-12-03 | 2022-06-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | A process for tablet formulations comprising amorphous dapagliflozin and metformin hydrochloride |
TR202019592A2 (tr) | 2020-12-03 | 2022-06-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Amorf dapagliflozinin katı farmasötik formülasyonları |
EP4315350A1 (en) | 2021-04-01 | 2024-02-07 | AstraZeneca UK Limited | Systems and methods for managing prediabetes with a gliflozin sodium-glucose cotransport 2 inhibitor pharmaceutical composition |
EP4079296A1 (en) | 2021-04-21 | 2022-10-26 | Sanovel Ilac Sanayi Ve Ticaret A.S. | A bilayer tablet formulation comprising amorphous dapagliflozin and metformin |
KR20240040106A (ko) | 2021-07-28 | 2024-03-27 | 베링거잉겔하임베트메디카게엠베하 | 비-사람 포유류에서 신장 질환의 예방 및/또는 치료를 위한 sglt-2 억제제의 용도 |
CN117715640A (zh) | 2021-07-28 | 2024-03-15 | 勃林格殷格翰动物保健有限公司 | Sglt-2抑制剂用于在不包括猫科动物的非人哺乳动物,特别是犬科动物中预防和/或治疗心脏疾病的用途 |
US20240269105A1 (en) | 2021-07-28 | 2024-08-15 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of hypertension in non-human mammals |
CN113773194B (zh) | 2021-08-16 | 2023-05-02 | 浙江奥翔药业股份有限公司 | 作为降糖药合成原料的5-溴-2-氯-苯甲酸的制备方法 |
WO2023129595A1 (en) | 2021-12-30 | 2023-07-06 | Newamsterdam Pharma B.V. | Obicetrapib and sglt2 inhibitor combination |
EP4212150A1 (en) | 2022-01-13 | 2023-07-19 | Sanovel Ilac Sanayi Ve Ticaret A.S. | A bilayer tablet composition comprising amorphous dapagliflozin and metformin |
WO2023144722A1 (en) | 2022-01-26 | 2023-08-03 | Astrazeneca Ab | Dapagliflozin for use in the treatment of prediabetes or reducing the risk of developing type 2 diabetes |
WO2023227492A1 (en) | 2022-05-25 | 2023-11-30 | Boehringer Ingelheim Vetmedica Gmbh | Aqueous pharmaceutical compositions comprising sglt-2 inhibitors |
TW202415364A (zh) | 2022-06-07 | 2024-04-16 | 瑞典商阿斯特捷利康公司 | Rxfp1調節劑和sglt2抑制劑之組合 |
KR102490653B1 (ko) * | 2022-08-03 | 2023-01-20 | 진양제약주식회사 | 다파글리플로진 및 글리메피리드를 포함하는 약제학적 조성물 |
KR20240028315A (ko) | 2022-08-24 | 2024-03-05 | 주식회사 제뉴원사이언스 | 다파글리플로진, 시타글립틴, 및 메트포르민을 함유하는 복합 제제 |
US20240307383A1 (en) | 2023-02-08 | 2024-09-19 | Astrazeneca Ab | Combination of zibotentan and dapagliflozin for the treatment of proteinuria chronic kidney disease |
EP4427742A1 (en) | 2023-03-06 | 2024-09-11 | Galenicum Health S.L.U. | Pharmaceutical compositions comprising dapagliflozin and metformin |
US20240307628A1 (en) | 2023-03-06 | 2024-09-19 | Boehringer Ingelheim Vetmedica Gmbh | Systems and methods for delivery of liquid pharmaceutical compositions in particular comprising one or more sglt-2 inhibitor(s) |
EP4431088A1 (en) | 2023-03-06 | 2024-09-18 | Galenicum Health S.L.U. | Pharmaceutical compositions comprising dapagliflozin and metformin |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1088346A1 (ru) * | 1982-09-28 | 1986-12-30 | Тихоокеанский институт биоорганической химии Дальневосточного научного центра АН СССР | Ацетилированные гликозиды 2,5- и 2,8 -дигидрокси-1,4-нафтохинонов,обладающие антигрибковой активностью |
JPH03133746A (ja) * | 1989-10-19 | 1991-06-06 | Taiyo Kagaku Kogyo Kk | 自立袋およびその製造方法 |
CA2102591C (en) | 1992-11-12 | 2000-12-26 | Kenji Tsujihara | Hypoglycemic agent |
WO1994011030A1 (en) * | 1992-11-13 | 1994-05-26 | The Ohio State University Research Foundation | C-glycoside analogues of n-(4-hydroxyphenyl)retinamide-o-glucuronide |
US5444050A (en) * | 1994-04-29 | 1995-08-22 | Texas Biotechnology Corporation | Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa |
US5830873A (en) | 1994-05-11 | 1998-11-03 | Tanabe Seiyaku Co., Ltd. | Propiophenone derivative and a process for preparing the same |
JP2814950B2 (ja) | 1994-05-11 | 1998-10-27 | 田辺製薬株式会社 | 血糖降下剤 |
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 |
JP3034192B2 (ja) | 1995-11-07 | 2000-04-17 | 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 |
JP3006513B2 (ja) | 1995-11-07 | 2000-02-07 | 田辺製薬株式会社 | 医薬組成物 |
TW406086B (en) | 1996-12-26 | 2000-09-21 | Tanabe Seiyaku Co | Propiophenone derivatives and process for preparing the same |
WO1998031697A1 (en) | 1997-01-15 | 1998-07-23 | Sankyo Company, Limited | Aryl c-glycoside compounds and sulfated esters thereof |
JPH10245391A (ja) | 1997-03-03 | 1998-09-14 | Dainippon Ink & Chem Inc | 7−グリコシロキシベンゾピラン誘導体を有効成分とする糖尿病治療剤 |
AU735853B2 (en) * | 1997-04-04 | 2001-07-19 | Mitsubishi Pharma Corporation | 2-aminopropane-1,3-diol compound, Pharmaceutical use thereof and synthetic intermediates therefor |
JP3451000B2 (ja) | 1997-10-20 | 2003-09-29 | 新日本製鐵株式会社 | 方向性珪素鋼板の絶縁皮膜形成方法 |
DE19806803A1 (de) * | 1998-02-18 | 1999-11-25 | Hermann Koepsell | Transporter für Saccharid-gekoppelte Zytostatika in Tumorzellen |
GB9811427D0 (en) * | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
US6486299B1 (en) | 1998-09-28 | 2002-11-26 | Curagen Corporation | Genes and proteins predictive and therapeutic for stroke, hypertension, diabetes and obesity |
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 |
US6683056B2 (en) * | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
US6555519B2 (en) * | 2000-03-30 | 2003-04-29 | Bristol-Myers Squibb Company | O-glucosylated benzamide SGLT2 inhibitors and method |
US6774112B2 (en) * | 2001-04-11 | 2004-08-10 | Bristol-Myers Squibb Company | Amino acid complexes of C-aryl glucosides for treatment of diabetes and method |
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