CA2534022C - Di-aryl glycoside derivatives and their use as sglt inhibitors - Google Patents

Di-aryl glycoside derivatives and their use as sglt inhibitors Download PDF

Info

Publication number
CA2534022C
CA2534022C CA2534022A CA2534022A CA2534022C CA 2534022 C CA2534022 C CA 2534022C CA 2534022 A CA2534022 A CA 2534022A CA 2534022 A CA2534022 A CA 2534022A CA 2534022 C CA2534022 C CA 2534022C
Authority
CA
Canada
Prior art keywords
group
compound
ring
lower alkyl
halogen atom
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA2534022A
Other languages
English (en)
French (fr)
Other versions
CA2534022A1 (en
Inventor
Sumihiro Nomura
Toshiaki Sakamoto
Kiichiro Ueta
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tanabe Pharma Corp
Original Assignee
Mitsubishi Tanabe Pharma Corp
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
Application filed by Mitsubishi Tanabe Pharma Corp filed Critical Mitsubishi Tanabe Pharma Corp
Publication of CA2534022A1 publication Critical patent/CA2534022A1/en
Application granted granted Critical
Publication of CA2534022C publication Critical patent/CA2534022C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic 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
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Diabetes (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Neurosurgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2534022A 2003-08-01 2004-07-30 Di-aryl glycoside derivatives and their use as sglt inhibitors Expired - Fee Related CA2534022C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US49152303P 2003-08-01 2003-08-01
US60/491,523 2003-08-01
PCT/JP2004/011311 WO2005012321A1 (en) 2003-08-01 2004-07-30 Novel compounds

Publications (2)

Publication Number Publication Date
CA2534022A1 CA2534022A1 (en) 2005-02-10
CA2534022C true CA2534022C (en) 2012-10-02

Family

ID=34115512

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2534022A Expired - Fee Related CA2534022C (en) 2003-08-01 2004-07-30 Di-aryl glycoside derivatives and their use as sglt inhibitors

Country Status (18)

Country Link
US (1) US7521430B2 (enExample)
EP (1) EP1654269B1 (enExample)
JP (1) JP4717811B2 (enExample)
KR (1) KR101101500B1 (enExample)
CN (2) CN102060888A (enExample)
AU (1) AU2004260760B2 (enExample)
BR (1) BRPI0413233A (enExample)
CA (1) CA2534022C (enExample)
EA (1) EA011025B1 (enExample)
ES (1) ES2527053T3 (enExample)
IL (1) IL173051A (enExample)
MX (1) MXPA06001273A (enExample)
NO (1) NO333679B1 (enExample)
NZ (1) NZ545305A (enExample)
TW (1) TWI377209B (enExample)
UA (5) UA86042C2 (enExample)
WO (1) WO2005012321A1 (enExample)
ZA (2) ZA200601686B (enExample)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104109155A (zh) 2003-08-01 2014-10-22 田边三菱制药株式会社 新颖化合物
US8785403B2 (en) 2003-08-01 2014-07-22 Mitsubishi Tanabe Pharma Corporation Glucopyranoside compound
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)
JP5073948B2 (ja) * 2005-01-31 2012-11-14 田辺三菱製薬株式会社 医薬組成物
TWI418556B (zh) * 2006-07-27 2013-12-11 Mitsubishi Tanabe Pharma Corp 吲哚衍生物
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
NZ577391A (en) * 2006-12-04 2011-11-25 Janssen Pharmaceutica Nv Thienyl-containing glycopyranosyl derivatives as antidiabetics
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
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
MX2010002695A (es) 2007-09-10 2010-04-01 Janssen Pharmaceutica Nv Proceso para la preparacion de compuestos utiles como inhibidores de transportador de glucosa dependiente de sodio (sglt).
CL2008003653A1 (es) 2008-01-17 2010-03-05 Mitsubishi Tanabe Pharma Corp Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica.
EP2291189B1 (en) 2008-05-22 2014-10-01 AstraZeneca AB Method for treating hyperuricemia employing an sglt2 inhibitor and composition containing same
ES2380408T3 (es) 2008-08-28 2012-05-11 Pfizer Inc. Derivados de dioxa-biciclo[3.2.1]octano-2,3,4-triol
AU2009294606A1 (en) * 2008-09-19 2010-03-25 Novartis Ag Glycoside derivatives and uses thereof
US9056850B2 (en) * 2008-10-17 2015-06-16 Janssen Pharmaceutica N.V. Process for the preparation of compounds useful as inhibitors of SGLT
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
WO2011047113A1 (en) * 2009-10-14 2011-04-21 Janssen Pharmaceutica Nv Process for the preparation of compounds useful as inhibitors of sglt2
US8669380B2 (en) 2009-11-02 2014-03-11 Pfizer Inc. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
NZ703128A (en) 2010-05-11 2016-04-29 Janssen Pharmaceutica Nv Pharmaceutical formulations comprising 1 - (beta-d-glucopyranosyl) - 2 -thienylmethylbenzene derivatives as inhibitors of sglt
WO2012140120A1 (en) 2011-04-13 2012-10-18 Janssen Pharmaceutica Nv Process for the preparation of compounds useful as inhibitors of sglt2
TWI542596B (zh) * 2011-05-09 2016-07-21 健生藥品公司 （２ｓ,３ｒ,４ｒ,５ｓ,６ｒ）－２－（３－（（５－（４－氟苯基）噻吩－２－基）甲基）－４－甲基苯基）－６－（羥甲基）四氫－２ｈ－哌喃－３,４,５－三醇之ｌ－脯胺酸及檸檬酸共晶體
WO2014132940A1 (ja) * 2013-02-26 2014-09-04 田辺三菱製薬株式会社 α－ハロテトラアシルグルコースの製造方法
CN103896930B (zh) * 2014-04-02 2016-08-17 安徽联创生物医药股份有限公司 卡格列净半水合物药用晶型的制备方法
ES2711804T3 (es) 2014-05-27 2019-05-07 Glenmark Pharmaceuticals Ltd Proceso para preparación de canagliflozina
CN104045673B (zh) * 2014-06-06 2017-01-18 安徽省食品药品检验研究院 双‑三氮唑缀合的假二糖衍生物及其制备方法
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
CN106188022A (zh) * 2015-04-30 2016-12-07 上海医药工业研究院 伊格列净的制备方法
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
LT3716979T (lt) 2017-11-30 2025-07-10 Idorsia Pharmaceuticals Ltd 4-pirimidinsulfamido darinio derinys su sglt-2 inhibitoriumi, skirtas su endotelinu susijusių ligų gydymui
JOP20210009A1 (ar) 2018-07-19 2021-01-12 Astrazeneca Ab طرق لعلاج HFpEF باستعمال داباجليفلوزين وتركيبات تشمله
JP2023536009A (ja) 2020-07-27 2023-08-23 アストラゼネカ・アクチエボラーグ ダパグリフロジンによる慢性腎疾患の処置方法
WO2022208172A1 (en) 2021-04-01 2022-10-06 Astrazeneca Uk Limited Systems and methods for managing prediabetes with a gliflozin sodium-glucose cotransport 2 inhibitor pharmaceutical composition
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
IL329013A (en) 2023-12-15 2026-08-01 Astrazeneca Ireland Ltd SGLT2 inhibitors and baxadrostat for the treatment of chronic kidney disease and hypertension

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1075626B (de) * 1960-02-18 Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brunmg, Frankfurt/M Verfahren zur Herstellung von wasserlöslichen chemotherapeutisch wirksamen Glykosiden
PH12000002657B1 (en) 1999-10-12 2006-02-21 Bristol Myers Squibb Co C-aryl glucoside SGLT2 inhibitors
ES2254376T3 (es) * 2000-03-17 2006-06-16 Kissei Pharmaceutical Co., Ltd. Derivados glucopiranosiloxibencilbenceno, preparaciones medicinales que los contienen e intermediarios para la preparacion de los indicados derivados.
US6683056B2 (en) * 2000-03-30 2004-01-27 Bristol-Myers Squibb Company O-aryl glucoside SGLT2 inhibitors and method
JP3798375B2 (ja) * 2000-09-29 2006-07-19 キッセイ薬品工業株式会社 グルコピラノシルオキシベンジルベンゼン誘導体およびそれを含有する医薬組成物
WO2002044192A1 (en) * 2000-11-30 2002-06-06 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxybenzyl benzene derivatives, medicinal compositions containing the same and intermediates in the production thereof
SK287786B6 (sk) 2000-12-28 2011-09-05 Kissei Pharmaceutical Co., Ltd. Glukopyranosyloxypyrazolový derivát, farmaceutická kompozícia alebo kombinácia s jeho obsahom a ich použitie
TWI255817B (en) * 2001-02-14 2006-06-01 Kissei Pharmaceutical Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof
US20030087843A1 (en) 2001-09-05 2003-05-08 Washburn William N. O-pyrazole glucoside SGLT2 inhibitors and method of use
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

Also Published As

Publication number Publication date
ES2527053T3 (es) 2015-01-20
EA011025B1 (ru) 2008-12-30
BRPI0413233A (pt) 2006-10-03
UA85569C2 (ru) 2009-02-10
NO20060219L (no) 2006-04-28
JP2007518682A (ja) 2007-07-12
UA86042C2 (en) 2009-03-25
ZA200601686B (en) 2007-05-30
US7521430B2 (en) 2009-04-21
TW200510440A (en) 2005-03-16
CN1829728A (zh) 2006-09-06
KR20060132539A (ko) 2006-12-21
WO2005012321A1 (en) 2005-02-10
AU2004260760A1 (en) 2005-02-10
EP1654269B1 (en) 2014-10-15
KR101101500B1 (ko) 2012-01-03
US20070060545A1 (en) 2007-03-15
EP1654269A1 (en) 2006-05-10
ZA200603880B (en) 2010-01-27
UA86599C2 (en) 2009-05-12
CN102060888A (zh) 2011-05-18
IL173051A (en) 2012-06-28
UA87991C2 (en) 2009-09-10
MXPA06001273A (es) 2006-04-11
NO333679B1 (no) 2013-08-05
UA83377C2 (uk) 2008-07-10
TWI377209B (en) 2012-11-21
CA2534022A1 (en) 2005-02-10
EA200600348A1 (ru) 2006-08-25
AU2004260760B2 (en) 2009-08-13
JP4717811B2 (ja) 2011-07-06
NZ545305A (en) 2008-11-28
IL173051A0 (en) 2006-06-11

Similar Documents

Publication Publication Date Title
EP1654269B1 (en) Novel compounds
JP5905926B2 (ja) Ｓｇｌｔの阻害物質として有用な化合物の調製方法
JP5973551B2 (ja) Ｓｇｌｔ２の阻害物質として有用な化合物の調製プロセス
MX2007009178A (es) Derivados de indol.
JP5073948B2 (ja) 医薬組成物
EP2712360B1 (en) Process for the preparation of compounds useful as inhibittors of sglt-2
EP2712359A2 (en) Process for the preparation of compounds useful as inhibitors of sglt-2
HK1192753A (en) Process for the preparation of compounds useful as inhibitors of sglt

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20160801