WO2003011880A1 - Glucopyrano syloxybenzyl benzene derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof - Google Patents

Glucopyrano syloxybenzyl benzene derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof 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
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
medicinal
syloxybenzyl
glucopyrano
intermediate
Prior art date
Application number
PCT/JP2002/007536
Other languages
French (fr)
Inventor
Nobuhiko Fushimi
Fumiaki Ito
Masayuki Isaji
Original Assignee
Kissei Pharmaceutical Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to JP2001231804 priority Critical
Priority to JP2001-231804 priority
Application filed by Kissei Pharmaceutical Co., Ltd. filed Critical Kissei Pharmaceutical Co., Ltd.
Publication of WO2003011880A1 publication Critical patent/WO2003011880A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin

Abstract

A glucopyranosyloxybenzylbenzene derivative represented by the general formula (I) (wherein R1 represents hydrogen, hydroxy, optionally substituted amino, cyano, carbamoyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, or optionally substituted cyclic amino; R2 represents hydrogen or lower alkyl; and R3 represents optionally substituted aryl, optionally substituted cycloalkyl, an optionally substituted aliphatic heterocyclic group, or an optionally substituted aromatic heterocyclic group), a pharmacologically acceptable salt of the derivative, or a prodrug of either. They have excellent human SGLT2 inhibitory activity and are useful as a preventive or remedy for diseases attributable to hyperglycemia, such as diabetes, complications of diabetes, and obesity.
PCT/JP2002/007536 2001-07-31 2002-07-25 Glucopyrano syloxybenzyl benzene derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof WO2003011880A1 (en)

Priority Applications (2)

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

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2003517071A JPWO2003011880A1 (en) 2001-07-31 2002-07-25 Glucopyranosyloxy benzyl benzene derivatives, pharmaceutical compositions containing them, their pharmaceutical use and its production intermediate

Publications (1)

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

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PCT/JP2002/007536 WO2003011880A1 (en) 2001-07-31 2002-07-25 Glucopyrano syloxybenzyl benzene derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof

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JP (1) JPWO2003011880A1 (en)
WO (1) WO2003011880A1 (en)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2004087727A1 (en) * 2003-03-31 2006-06-29 キッセイ薬品工業株式会社 Fused heterocyclic derivatives, pharmaceutical compositions containing them and their pharmaceutical use
US7084124B2 (en) 2003-08-01 2006-08-01 Janssen Pharmaceutica, N.V. Substituted indazole-O-glucosides
US7094763B2 (en) 2003-08-01 2006-08-22 Janssen Pharaceutica, N.V. Substituted fused heterocyclic C-glycosides
US7094764B2 (en) 2003-08-01 2006-08-22 Janssen Pharmaceutica N.V. Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides
US7129220B2 (en) 2003-08-01 2006-10-31 Janssen Pharmaceutica N.V Substituted indole-O-glucosides
JP2007515441A (en) * 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 Glucopyranosyl Noshiro carboxy-substituted aromatic compounds, medicaments containing said compounds, their use and processes for their preparation
WO2007128761A2 (en) 2006-05-04 2007-11-15 Boehringer Ingelheim International Gmbh Uses of dpp-iv inhibitors
WO2008016132A1 (en) 2006-08-04 2008-02-07 Daiichi Sankyo Company, Limited Benzyl phenyl glucopyranoside derivative
JPWO2005095429A1 (en) * 2004-03-31 2008-02-21 キッセイ薬品工業株式会社 Phenol derivatives, pharmaceutical compositions and pharmaceutical uses comprising the same
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
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
US7943788B2 (en) 2003-08-01 2011-05-17 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
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
WO2011107494A1 (en) 2010-03-03 2011-09-09 Sanofi Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof
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 (en) 2013-03-04 2014-09-10 BioActive Food GmbH Composition for the treatment of hyperglycaemic diseases
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 (en) 2014-05-16 2015-11-18 BioActive Food GmbH Combination of biologically active substances for treating hyperglycemic diseases
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

Citations (6)

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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 (en) * 1996-03-26 1997-09-30 Meiwa Kasei Kk Bis(hidroxybenzyl)biphenyl and its production
WO2001016147A1 (en) * 1999-08-31 2001-03-08 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
WO2001027128A1 (en) * 1999-10-12 2001-04-19 Bristol-Myers Squibb Company C-aryl glucoside sglt2 inhibitors
WO2001068660A1 (en) * 2000-03-17 2001-09-20 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxy benzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives
WO2001074834A1 (en) * 2000-03-30 2001-10-11 Bristol-Myers Squibb Company O-aryl glucoside sglt2 inhibitors and method

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 (en) * 1996-03-26 1997-09-30 Meiwa Kasei Kk Bis(hidroxybenzyl)biphenyl and its production
WO2001016147A1 (en) * 1999-08-31 2001-03-08 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
WO2001027128A1 (en) * 1999-10-12 2001-04-19 Bristol-Myers Squibb Company C-aryl glucoside sglt2 inhibitors
WO2001068660A1 (en) * 2000-03-17 2001-09-20 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxy benzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives
WO2001074834A1 (en) * 2000-03-30 2001-10-11 Bristol-Myers Squibb Company O-aryl glucoside sglt2 inhibitors and method

Cited By (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2004087727A1 (en) * 2003-03-31 2006-06-29 キッセイ薬品工業株式会社 Fused heterocyclic derivatives, pharmaceutical compositions containing them and their pharmaceutical use
JP4753716B2 (en) * 2003-03-31 2011-08-24 キッセイ薬品工業株式会社 Fused heterocyclic derivative, pharmaceutical composition containing the same, and pharmaceutical use thereof
US7816330B2 (en) 2003-08-01 2010-10-19 Janssen Pharmaceutica Nv Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides
US7094764B2 (en) 2003-08-01 2006-08-22 Janssen Pharmaceutica N.V. Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides
US7129220B2 (en) 2003-08-01 2006-10-31 Janssen Pharmaceutica N.V Substituted indole-O-glucosides
US8785403B2 (en) 2003-08-01 2014-07-22 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
US7094763B2 (en) 2003-08-01 2006-08-22 Janssen Pharaceutica, N.V. Substituted fused heterocyclic C-glycosides
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
US7482330B2 (en) 2003-08-01 2009-01-27 Janssen Pharmaceutica N.V. Substituted fused heterocyclic C-glycosides
US7511021B2 (en) 2003-08-01 2009-03-31 Janssen Pharmaceutica N.V. Substituted indazole-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
US7943788B2 (en) 2003-08-01 2011-05-17 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
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
US7816328B2 (en) 2003-08-01 2010-10-19 Janssen Pharmaceutica Nv Substituted fused heterocyclic C-glycosides
US7511020B2 (en) 2003-08-01 2009-03-31 Janssen Pharmaceutica N.V. Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides
JP2007515441A (en) * 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 Glucopyranosyl Noshiro carboxy-substituted aromatic compounds, medicaments containing said compounds, their use and processes for their preparation
JPWO2005095429A1 (en) * 2004-03-31 2008-02-21 キッセイ薬品工業株式会社 Phenol derivatives, pharmaceutical compositions and pharmaceutical uses comprising the same
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 (en) 2006-05-04 2011-08-03 Boehringer Ingelheim International GmbH Uses of dpp-iv inhibitors
WO2007128761A2 (en) 2006-05-04 2007-11-15 Boehringer Ingelheim International Gmbh Uses of dpp-iv inhibitors
US7851617B2 (en) 2006-07-27 2010-12-14 Mitsubishi Tanabe Pharma Corporation Indole derivatives
WO2008016132A1 (en) 2006-08-04 2008-02-07 Daiichi Sankyo Company, Limited Benzyl phenyl glucopyranoside derivative
US8476413B2 (en) 2006-09-29 2013-07-02 Lexicon Pharmaceuticals, Inc. Sulfanyl-tetrahydropyran-based compounds 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
US9365602B2 (en) 2006-09-29 2016-06-14 Lexicon Pharmaceuticals, Inc. Sodium glucose co-transporter inhibitors and methods of their use
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
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
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
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
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
US9439902B2 (en) 2009-11-02 2016-09-13 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
WO2011107494A1 (en) 2010-03-03 2011-09-09 Sanofi Novel aromatic glycoside derivatives, medicaments containing said compounds, and the 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
EP2774619A1 (en) 2013-03-04 2014-09-10 BioActive Food GmbH Composition for the treatment of hyperglycaemic diseases
US10414787B2 (en) 2013-03-14 2019-09-17 Mars, Incorporated Flavor composition containing HMG glucosides
WO2015173383A1 (en) 2014-05-16 2015-11-19 Bioactive Food Gmbh Combination of biologically active substances for treatment of hyperglycaemic disorders
EP2944311A1 (en) 2014-05-16 2015-11-18 BioActive Food GmbH Combination of biologically active substances for treating hyperglycemic diseases

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