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WO2003011880A1 - Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition - Google Patents

Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition Download PDF

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Publication number
WO2003011880A1
WO2003011880A1 PCT/JP2002/007536 JP0207536W WO03011880A1 WO 2003011880 A1 WO2003011880 A1 WO 2003011880A1 JP 0207536 W JP0207536 W JP 0207536W WO 03011880 A1 WO03011880 A1 WO 03011880A1
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Prior art keywords
optionally substituted
medicinal
syloxybenzyl
glucopyrano
production
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PCT/JP2002/007536
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English (en)
Japanese (ja)
Inventor
Nobuhiko Fushimi
Fumiaki Ito
Masayuki Isaji
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Kissei Pharmaceutical Co., Ltd.
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Priority to JP2003517071A priority Critical patent/JPWO2003011880A1/ja
Publication of WO2003011880A1 publication Critical patent/WO2003011880A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Molecular Biology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne un dérivé de glucopyranosyloxybenzylbenzène, représenté par la formule générale (I), un sel pharmacologiquement acceptable de ce dérivé ou un promédicament de ceux-ci. Dans la formule (I), R1 est un atome d'hydrogène, un groupe hydroxy, un groupe amino éventuellement substitué, un groupe cyano, un groupe carbamoyle, un groupe alkyle inférieur éventuellement substitué, un groupe alkoxy inférieur éventuellement substitué ou un groupe amino cyclique éventuellement substitué, R2 est un atome d'hydrogène ou un groupe alkyle inférieur et R3 est un groupe aryle éventuellement substitué, un groupe cycloalkyle éventuellement substitué, un groupe hétérocyclique aliphatique éventuellement substitué ou un groupe hétérocyclique aromatique éventuellement substitué. Ces substances présentent une excellente activité inhibitrice de la SGLT2 humaine et sont utiles pour prévenir ou traiter des maladies liées à l'hyperglycémie, telles que le diabète, des complications du diabète et l'obésité.
PCT/JP2002/007536 2001-07-31 2002-07-25 Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition WO2003011880A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2003517071A JPWO2003011880A1 (ja) 2001-07-31 2002-07-25 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

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001231804 2001-07-31
JP2001-231804 2001-07-31

Publications (1)

Publication Number Publication Date
WO2003011880A1 true WO2003011880A1 (fr) 2003-02-13

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PCT/JP2002/007536 WO2003011880A1 (fr) 2001-07-31 2002-07-25 Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition

Country Status (2)

Country Link
JP (1) JPWO2003011880A1 (fr)
WO (1) WO2003011880A1 (fr)

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005154418A (ja) * 2003-10-31 2005-06-16 Takeda Chem Ind Ltd 固形製剤
JPWO2004087727A1 (ja) * 2003-03-31 2006-06-29 キッセイ薬品工業株式会社 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
US7084124B2 (en) 2003-08-01 2006-08-01 Janssen Pharmaceutica, N.V. Substituted indazole-O-glucosides
US7094764B2 (en) 2003-08-01 2006-08-22 Janssen Pharmaceutica N.V. Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides
US7094763B2 (en) 2003-08-01 2006-08-22 Janssen Pharaceutica, N.V. Substituted fused heterocyclic C-glycosides
US7129220B2 (en) 2003-08-01 2006-10-31 Janssen Pharmaceutica N.V Substituted indole-O-glucosides
JP2007515441A (ja) * 2003-12-22 2007-06-14 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 グルコピラノシロキシ置換芳香族化合物、前記化合物を含む医薬、それらの使用及びそれらの製造方法
WO2007128761A2 (fr) 2006-05-04 2007-11-15 Boehringer Ingelheim International Gmbh Utilisations d'inhibiteurs de l'enzyme dpp iv
WO2008016132A1 (fr) 2006-08-04 2008-02-07 Daiichi Sankyo Company, Limited Dérivé du benzyl phényl glucopyranoside
JPWO2005095429A1 (ja) * 2004-03-31 2008-02-21 キッセイ薬品工業株式会社 フェノール誘導体、それを含有する医薬組成物及びその医薬用途
US7666845B2 (en) 2006-12-04 2010-02-23 Janssen Pharmaceutica N.V. Compounds having inhibitory activity against sodium-dependent glucose transporter
US7767651B2 (en) 2005-01-28 2010-08-03 Chugai Seiyaku Kabushiki Kaisha Spiroketal derivatives and use thereof as diabetic medicine
US7781577B2 (en) 2006-09-29 2010-08-24 Lexicon Pharmaceuticals, Inc. Inhibitors of sodium glucose co-transporter 2 and methods of their use
US7846945B2 (en) 2007-03-08 2010-12-07 Lexicon Pharmaceuticals, Inc. Piperdine-based inhibitors of sodium glucose co-transporter 2 and methods of their use
US7851617B2 (en) 2006-07-27 2010-12-14 Mitsubishi Tanabe Pharma Corporation Indole derivatives
US7888365B2 (en) * 2007-03-02 2011-02-15 The University Of Tennessee Research Foundation Tri-aryl/heteroaromatic cannabinoids and use thereof
US7935674B2 (en) 2005-01-31 2011-05-03 Mitsubishi Tanabe Pharma Corporation Indole derivatives
US7943748B2 (en) 2004-07-27 2011-05-17 Chugai Seiyaku Kabushiki Kaisha Glucitol derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes
US7943788B2 (en) 2003-08-01 2011-05-17 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US7943582B2 (en) 2006-12-04 2011-05-17 Mitsubishi Tanabe Pharma Corporation Crystalline form of 1-(β-D-glucopyransoyl)-4-methyl-3-[5-(4-fluorophenyl)-2- thienylmethyl]benzene hemihydrate
WO2011107494A1 (fr) 2010-03-03 2011-09-09 Sanofi Nouveaux dérivés aromatiques de glycoside, médicaments contenants ces composés, et leur utilisation
US8048897B2 (en) 2004-07-26 2011-11-01 Chugai Seiyaku Kabushiki Kaisha Cyclohexane derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes
US8785403B2 (en) 2003-08-01 2014-07-22 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
EP2774619A1 (fr) 2013-03-04 2014-09-10 BioActive Food GmbH Composition pour le traitement de pathologies hyperglycémiques
US8853385B2 (en) 2008-01-17 2014-10-07 Mitsubishi Tanabe Pharma Corporation Combination therapy comprising SGLT inhibitors and DPP4 inhibitors
US9024009B2 (en) 2007-09-10 2015-05-05 Janssen Pharmaceutica N.V. Process for the preparation of compounds useful as inhibitors of SGLT
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
US9056850B2 (en) 2008-10-17 2015-06-16 Janssen Pharmaceutica N.V. Process for the preparation of compounds useful as inhibitors of SGLT
US9061060B2 (en) 2008-07-15 2015-06-23 Theracos Inc. Deuterated benzylbenzene derivatives and methods of use
US9174971B2 (en) 2009-10-14 2015-11-03 Janssen Pharmaceutica Nv Process for the preparation of compounds useful as inhibitors of SGLT2
EP2944311A1 (fr) 2014-05-16 2015-11-18 BioActive Food GmbH Combinaison de substances biologiques actives destinée au traitement de pathologies hypoglycémiques
US9308204B2 (en) 2009-11-02 2016-04-12 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
US10414787B2 (en) 2013-03-14 2019-09-17 Mars, Incorporated Flavor composition containing HMG glucosides
US10544135B2 (en) 2011-04-13 2020-01-28 Janssen Pharmaceutica Nv Process for the preparation of compounds useful as inhibitors of SGLT2
US10617668B2 (en) 2010-05-11 2020-04-14 Janssen Pharmaceutica Nv Pharmaceutical formulations
US11207337B2 (en) 2015-09-15 2021-12-28 Janssen Pharmaceutica Nv Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders
US11576894B2 (en) 2009-07-08 2023-02-14 Janssen Pharmaceutica Nv Combination therapy for the treatment of diabetes
CN116768756A (zh) * 2023-05-30 2023-09-19 湖南大学 一种新型2-羟基二芳基甲烷类化合物及其高效合成方法
WO2023222144A1 (fr) * 2022-05-18 2023-11-23 上海科利生物医药有限公司 Analogue de thioglycoside gliflozine, son procédé de préparation et son utilisation

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JPH09255603A (ja) * 1996-03-26 1997-09-30 Meiwa Kasei Kk ビス（ヒドロキシベンジル）ビフェニル及びその製法
WO2001016147A1 (fr) * 1999-08-31 2001-03-08 Kissei Pharmaceutical Co., Ltd. Derives de glucopyranosyloxypyrazole, compositions medicinales renfermant lesdits derives et produits intermediaires obtenus au cours de leur production
WO2001027128A1 (fr) * 1999-10-12 2001-04-19 Bristol-Myers Squibb Company Inhibiteurs de sglt2 a base de glucoside c-aryle
WO2001068660A1 (fr) * 2000-03-17 2001-09-20 Kissei Pharmaceutical Co., Ltd. Derives glucopyranosyloxybenzylbenzene, preparations medicinales les contenant et intermediaires pour la preparation desdits derives
WO2001074834A1 (fr) * 2000-03-30 2001-10-11 Bristol-Myers Squibb Company Inhibiteurs de sglt2 a o-aryl glucoside et procede correspondant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4874763A (en) * 1987-11-28 1989-10-17 Roehm Gmbh Chemische Fabrik Pharmaceutically efficacious pteridine derivatives
JPH09255603A (ja) * 1996-03-26 1997-09-30 Meiwa Kasei Kk ビス（ヒドロキシベンジル）ビフェニル及びその製法
WO2001016147A1 (fr) * 1999-08-31 2001-03-08 Kissei Pharmaceutical Co., Ltd. Derives de glucopyranosyloxypyrazole, compositions medicinales renfermant lesdits derives et produits intermediaires obtenus au cours de leur production
WO2001027128A1 (fr) * 1999-10-12 2001-04-19 Bristol-Myers Squibb Company Inhibiteurs de sglt2 a base de glucoside c-aryle
WO2001068660A1 (fr) * 2000-03-17 2001-09-20 Kissei Pharmaceutical Co., Ltd. Derives glucopyranosyloxybenzylbenzene, preparations medicinales les contenant et intermediaires pour la preparation desdits derives
WO2001074834A1 (fr) * 2000-03-30 2001-10-11 Bristol-Myers Squibb Company Inhibiteurs de sglt2 a o-aryl glucoside et procede correspondant

Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4753716B2 (ja) * 2003-03-31 2011-08-24 キッセイ薬品工業株式会社 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
JPWO2004087727A1 (ja) * 2003-03-31 2006-06-29 キッセイ薬品工業株式会社 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
US7816328B2 (en) 2003-08-01 2010-10-19 Janssen Pharmaceutica Nv Substituted fused heterocyclic C-glycosides
US7482330B2 (en) 2003-08-01 2009-01-27 Janssen Pharmaceutica N.V. Substituted fused heterocyclic C-glycosides
US7094763B2 (en) 2003-08-01 2006-08-22 Janssen Pharaceutica, N.V. Substituted fused heterocyclic C-glycosides
US7129220B2 (en) 2003-08-01 2006-10-31 Janssen Pharmaceutica N.V Substituted indole-O-glucosides
US7943788B2 (en) 2003-08-01 2011-05-17 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US8785403B2 (en) 2003-08-01 2014-07-22 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US8222219B2 (en) 2003-08-01 2012-07-17 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US8202984B2 (en) 2003-08-01 2012-06-19 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US7511020B2 (en) 2003-08-01 2009-03-31 Janssen Pharmaceutica N.V. Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides
US7511021B2 (en) 2003-08-01 2009-03-31 Janssen Pharmaceutica N.V. Substituted indazole-O-glucosides
US7094764B2 (en) 2003-08-01 2006-08-22 Janssen Pharmaceutica N.V. Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides
US7511022B2 (en) 2003-08-01 2009-03-31 Janssen Pharmaceutica N.V. Substituted indole-O-glucosides
US7084124B2 (en) 2003-08-01 2006-08-01 Janssen Pharmaceutica, N.V. Substituted indazole-O-glucosides
US7820630B2 (en) 2003-08-01 2010-10-26 Janssen Pharmaceutica Nv Substituted indole-O-glucosides
US7816331B2 (en) 2003-08-01 2010-10-19 Janssen Pharmaceutica Nv Substituted indazole-O-glucosides
US7816330B2 (en) 2003-08-01 2010-10-19 Janssen Pharmaceutica Nv Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides
JP2005154418A (ja) * 2003-10-31 2005-06-16 Takeda Chem Ind Ltd 固形製剤
JP2007515441A (ja) * 2003-12-22 2007-06-14 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 グルコピラノシロキシ置換芳香族化合物、前記化合物を含む医薬、それらの使用及びそれらの製造方法
JPWO2005095429A1 (ja) * 2004-03-31 2008-02-21 キッセイ薬品工業株式会社 フェノール誘導体、それを含有する医薬組成物及びその医薬用途
US8048897B2 (en) 2004-07-26 2011-11-01 Chugai Seiyaku Kabushiki Kaisha Cyclohexane derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes
US7943748B2 (en) 2004-07-27 2011-05-17 Chugai Seiyaku Kabushiki Kaisha Glucitol derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes
US7767651B2 (en) 2005-01-28 2010-08-03 Chugai Seiyaku Kabushiki Kaisha Spiroketal derivatives and use thereof as diabetic medicine
US7935674B2 (en) 2005-01-31 2011-05-03 Mitsubishi Tanabe Pharma Corporation Indole derivatives
EP2351568A2 (fr) 2006-05-04 2011-08-03 Boehringer Ingelheim International GmbH Utilisations d'inhibiteurs de l'enzyme dpp iv
EP2397142A2 (fr) 2006-05-04 2011-12-21 Boehringer Ingelheim International GmbH Utilisations d'inhibiteurs de l'enzyme dpp iv
WO2007128761A2 (fr) 2006-05-04 2007-11-15 Boehringer Ingelheim International Gmbh Utilisations d'inhibiteurs de l'enzyme dpp iv
US7851617B2 (en) 2006-07-27 2010-12-14 Mitsubishi Tanabe Pharma Corporation Indole derivatives
WO2008016132A1 (fr) 2006-08-04 2008-02-07 Daiichi Sankyo Company, Limited Dérivé du benzyl phényl glucopyranoside
US9365602B2 (en) 2006-09-29 2016-06-14 Lexicon Pharmaceuticals, Inc. Sodium glucose co-transporter inhibitors and methods of their use
US7781577B2 (en) 2006-09-29 2010-08-24 Lexicon Pharmaceuticals, Inc. Inhibitors of sodium glucose co-transporter 2 and methods of their use
US8476413B2 (en) 2006-09-29 2013-07-02 Lexicon Pharmaceuticals, Inc. Sulfanyl-tetrahydropyran-based compounds and methods of their use
US7666845B2 (en) 2006-12-04 2010-02-23 Janssen Pharmaceutica N.V. Compounds having inhibitory activity against sodium-dependent glucose transporter
US8513202B2 (en) 2006-12-04 2013-08-20 Mitsubishi Tanabe Pharma Corporation Crystalline form of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate
US7943582B2 (en) 2006-12-04 2011-05-17 Mitsubishi Tanabe Pharma Corporation Crystalline form of 1-(β-D-glucopyransoyl)-4-methyl-3-[5-(4-fluorophenyl)-2- thienylmethyl]benzene hemihydrate
US7888365B2 (en) * 2007-03-02 2011-02-15 The University Of Tennessee Research Foundation Tri-aryl/heteroaromatic cannabinoids and use thereof
US9139546B2 (en) 2007-03-02 2015-09-22 The University Of Tennessee Research Foundation Tri-aryl/heteroaromatic cannabinoids and use thereof
US7846945B2 (en) 2007-03-08 2010-12-07 Lexicon Pharmaceuticals, Inc. Piperdine-based inhibitors of sodium glucose co-transporter 2 and methods of their use
US9024009B2 (en) 2007-09-10 2015-05-05 Janssen Pharmaceutica N.V. Process for the preparation of compounds useful as inhibitors of SGLT
US8853385B2 (en) 2008-01-17 2014-10-07 Mitsubishi Tanabe Pharma Corporation Combination therapy comprising SGLT inhibitors and DPP4 inhibitors
US9061060B2 (en) 2008-07-15 2015-06-23 Theracos Inc. Deuterated benzylbenzene derivatives and methods of use
US9056850B2 (en) 2008-10-17 2015-06-16 Janssen Pharmaceutica N.V. Process for the preparation of compounds useful as inhibitors of SGLT
US11576894B2 (en) 2009-07-08 2023-02-14 Janssen Pharmaceutica Nv Combination therapy for the treatment of diabetes
US9174971B2 (en) 2009-10-14 2015-11-03 Janssen Pharmaceutica Nv Process for the preparation of compounds useful as inhibitors of SGLT2
US9308204B2 (en) 2009-11-02 2016-04-12 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
US9439901B2 (en) 2009-11-02 2016-09-13 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
US9439902B2 (en) 2009-11-02 2016-09-13 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
WO2011107494A1 (fr) 2010-03-03 2011-09-09 Sanofi Nouveaux dérivés aromatiques de glycoside, médicaments contenants ces composés, et leur utilisation
US10617668B2 (en) 2010-05-11 2020-04-14 Janssen Pharmaceutica Nv Pharmaceutical formulations
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EP2774619A1 (fr) 2013-03-04 2014-09-10 BioActive Food GmbH Composition pour le traitement de pathologies hyperglycémiques
US10414787B2 (en) 2013-03-14 2019-09-17 Mars, Incorporated Flavor composition containing HMG glucosides
WO2015173383A1 (fr) 2014-05-16 2015-11-19 Bioactive Food Gmbh Association de substances bioactives pour le traitement de maladies liées à une hyperglycémie
EP2944311A1 (fr) 2014-05-16 2015-11-18 BioActive Food GmbH Combinaison de substances biologiques actives destinée au traitement de pathologies hypoglycémiques
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