CA2807034C - C-aryl glucoside derivatives, preparation process and pharmaceutical use thereof - Google Patents

C-aryl glucoside derivatives, preparation process and pharmaceutical use thereof Download PDF

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Publication number
CA2807034C
CA2807034C CA2807034A CA2807034A CA2807034C CA 2807034 C CA2807034 C CA 2807034C CA 2807034 A CA2807034 A CA 2807034A CA 2807034 A CA2807034 A CA 2807034A CA 2807034 C CA2807034 C CA 2807034C
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Prior art keywords
phenyl
chloro
mmol
methoxy
reaction mixture
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CA2807034A
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English (en)
French (fr)
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CA2807034A1 (en
Inventor
Fanglong Yang
Peng Cho Tang
Qing Dong
Wangyang Tu
Jiang Fan
Dongliang Guan
Guangyuan Shen
Yang Wang
Jijun Yuan
Limin Zhang
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Jiangsu Hengrui Medicine Co Ltd
Shanghai Hengrui Pharmaceutical Co Ltd
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Jiangsu Hengrui Medicine Co Ltd
Shanghai Hengrui Pharmaceutical Co Ltd
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • 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
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed 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
    • 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
    • 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
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07H7/04—Carbocyclic radicals

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
CA2807034A 2010-08-10 2011-06-30 C-aryl glucoside derivatives, preparation process and pharmaceutical use thereof Active CA2807034C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CN201010249618.3 2010-08-10
CN201010249618 2010-08-10
CN201010589606.5 2010-12-06
CN2010105896065A CN102372722A (zh) 2010-08-10 2010-12-06 C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用
PCT/CN2011/076680 WO2012019496A1 (zh) 2010-08-10 2011-06-30 C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用

Publications (2)

Publication Number Publication Date
CA2807034A1 CA2807034A1 (en) 2012-02-16
CA2807034C true CA2807034C (en) 2019-05-07

Family

ID=45567352

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2807034A Active CA2807034C (en) 2010-08-10 2011-06-30 C-aryl glucoside derivatives, preparation process and pharmaceutical use thereof

Country Status (11)

Country Link
US (1) US8609622B2 (enExample)
EP (1) EP2604612B1 (enExample)
JP (1) JP5984808B2 (enExample)
KR (1) KR101862891B1 (enExample)
CN (2) CN102372722A (enExample)
BR (1) BR112013002125A2 (enExample)
CA (1) CA2807034C (enExample)
ES (1) ES2581728T3 (enExample)
MX (1) MX2013001098A (enExample)
RU (1) RU2606501C2 (enExample)
WO (1) WO2012019496A1 (enExample)

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US9018249B2 (en) 2011-09-13 2015-04-28 Panacea Biotec Limited SGLT inhibitors
CN102627535A (zh) * 2012-03-31 2012-08-08 天津药物研究院 含1,1-二苯基环丙基结构的化合物的制备方法
CN103450214B (zh) * 2012-05-29 2016-04-06 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
EP3466431B1 (en) 2013-03-14 2023-11-15 MSD International GmbH Crystalline forms and methods for preparing sglt2 inhibitors
CN104151306A (zh) * 2013-05-13 2014-11-19 北京新天宇科技开发有限公司 一种坎格列净的新的制备方法
WO2014187365A1 (zh) * 2013-05-24 2014-11-27 四川海思科制药有限公司 氧杂双环衍生物、制备方法及其应用
WO2014206349A1 (zh) * 2013-06-28 2014-12-31 四川海思科制药有限公司 氧杂-硫杂-双环[3.2.1]辛烷衍生物、制备方法及其用途
EP3056507B1 (en) * 2013-09-09 2020-09-23 Youngene Therapeutics Co., Ltd. C-aryl glucoside derivative, preparation method for same, and medical applications thereof
CN104447893B (zh) * 2013-09-25 2018-01-23 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
US9394329B2 (en) 2013-09-27 2016-07-19 Sunshine Lake Pharma Co., Ltd. Glucopyranosyl derivatives and their uses in medicine
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RU2696490C2 (ru) 2014-05-19 2019-08-02 Пфайзер Инк. Замещенные-6,8-диоксабицикло[3.2.1.]октан-2,3-диольные соединения в качестве агентов, нацеленных на ASGPR
CN104031098A (zh) * 2014-06-21 2014-09-10 李友香 降糖药物
CN104017031A (zh) * 2014-06-21 2014-09-03 李友香 降血糖药物和组合物
CN105294785A (zh) * 2014-07-02 2016-02-03 上海阳帆医药科技有限公司 C-苯并五元杂芳环类芳基葡萄糖苷衍生物及其制备方法与用途
US20160002275A1 (en) * 2014-07-03 2016-01-07 Cadila Healthcare Limited Process for preparation and purification of canagliflozin
CN104119324B (zh) * 2014-07-23 2016-03-30 齐鲁天和惠世制药有限公司 一种卡格列净的制备方法
CN105461762B (zh) * 2014-09-27 2018-12-04 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
KR20170060035A (ko) * 2014-09-30 2017-05-31 지앙수 헨그루이 메디슨 컴퍼니 리미티드 나트륨 글루코스 공동운반체 2 억제제의 ｌ- 프롤린 화합물, 및 ｌ- 프롤린 화합물의 모노하이드레이트 및 결정
WO2016088081A1 (en) * 2014-12-03 2016-06-09 Sun Pharmaceutical Industries Limited Processes for the preparation of ertugliflozin
US10294239B2 (en) 2015-05-25 2019-05-21 Sun Pharmaceutical Industries Limited Ertugliflozin co-crystals and process for their preparation
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
CN106955273B (zh) * 2016-01-11 2020-10-20 江苏恒瑞医药股份有限公司 一种含有钠-葡萄糖协同转运蛋白2抑制剂的药物组合物
CN107686496B (zh) * 2016-08-05 2021-01-19 江苏恒瑞医药股份有限公司 一种钠-葡萄糖协同转运蛋白2抑制剂的制备方法
CN106674245B (zh) * 2017-01-10 2019-07-26 北京中海康医药科技发展有限公司 吡喃葡萄糖基衍生物的制备及医药上的应用
CN109549939A (zh) * 2017-09-26 2019-04-02 江苏恒瑞医药股份有限公司 Sglt2抑制剂和dpp-4抑制剂联合在制备治疗糖尿病的药物中的用途
CN109806397A (zh) * 2017-11-20 2019-05-28 江苏恒瑞医药股份有限公司 Sglt2抑制剂与arb联合在制备治疗高血压等疾病的药物中的用途
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CN113004349A (zh) * 2019-12-19 2021-06-22 上海研健新药研发有限公司 一种SGLTs抑制剂的制备方法及其关键中间体
CN113330017B (zh) * 2019-12-19 2023-01-31 上海研健新药研发有限公司 一种SGLTs抑制剂的纯化方法及其应用
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Also Published As

Publication number Publication date
RU2606501C2 (ru) 2017-01-10
EP2604612B1 (en) 2016-04-20
HK1167395A1 (en) 2012-11-30
ES2581728T3 (es) 2016-09-07
CN102372722A (zh) 2012-03-14
KR101862891B1 (ko) 2018-05-30
JP2013533291A (ja) 2013-08-22
JP5984808B2 (ja) 2016-09-06
CN102482290B (zh) 2014-01-15
CN102482290A (zh) 2012-05-30
CA2807034A1 (en) 2012-02-16
EP2604612A4 (en) 2013-07-24
RU2013107748A (ru) 2014-09-20
MX2013001098A (es) 2013-06-05
WO2012019496A1 (zh) 2012-02-16
BR112013002125A2 (pt) 2016-05-24
US20130130997A1 (en) 2013-05-23
KR20130095741A (ko) 2013-08-28
EP2604612A1 (en) 2013-06-19
US8609622B2 (en) 2013-12-17

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