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
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.)
Jiangsu Hengrui Medicine Co Ltd
Shanghai Hengrui Pharmaceutical Co Ltd
Original Assignee
Jiangsu Hengrui Medicine Co Ltd
Shanghai Hengrui Pharmaceutical Co Ltd
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Publication of CA2807034A1 publication Critical patent/CA2807034A1/en
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Publication of CA2807034C publication Critical patent/CA2807034C/en
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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)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Ophthalmology & Optometry (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 2010-08-10
CN201010249618.3 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)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012146075A1 (zh) * 2011-04-25 2012-11-01 北京普禄德医药科技有限公司 一种钠依赖性葡萄糖转运蛋白抑制剂及其制备方法和用途
WO2013038429A2 (en) 2011-09-13 2013-03-21 Panacea Biotec Ltd. Novel 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
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
ES2740299T3 (es) * 2013-03-14 2020-02-05 Msd Int Gmbh Métodos para preparar inhibidores de SGLT2
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
JP6353054B2 (ja) * 2013-09-09 2018-07-04 ヤンジェン セラピューティクス カンパニー リミテッド Ｃ−アリールグルコシド誘導体、その製造方法およびその医薬適用
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
EP2895490B1 (en) * 2013-09-27 2016-10-19 Sunshine Lake Pharma Co., Ltd. Glucopyranosyl derivatives and their uses in medicine
BR112016015578A2 (pt) * 2014-01-03 2017-08-08 Elexopharm Gmbh Inibidores de 17beta-hidroxiesteroide desidrogenases tipo 1 e tipo 2
JP6193513B2 (ja) 2014-05-19 2017-09-06 ファイザー・インク Ａｓｇｐｒ標的化剤としての置換６，８−ジオキサビシクロ［３．２．１］オクタン−２，３−ジオール化合物
CN104017031A (zh) * 2014-06-21 2014-09-03 李友香 降血糖药物和组合物
CN104031098A (zh) * 2014-06-21 2014-09-10 李友香 降糖药物
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
HUE051212T2 (hu) 2016-01-04 2021-03-01 Jeil Pharmaceutical Co Ltd Kondenzált fenilgyûrût tartalmazó C-glükozid származék vagy annak gyógyászatilag elfogadható sója, eljárás annak elõállítására és azt tartalmazó gyógyászati kompozíció
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
WO2020039394A1 (en) 2018-08-24 2020-02-27 Novartis Ag New drug combinations
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
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
WO2021176096A1 (en) 2020-03-05 2021-09-10 Krka, D.D., Novo Mesto Pharmaceutical composition comprising sglt2 inhibitor
EP4161912A1 (en) 2020-06-05 2023-04-12 KRKA, d.d., Novo mesto Preparation of highly pure amorphous dapagliflozin
CN114195748B (zh) * 2020-09-17 2023-11-14 上海森辉医药有限公司 一种钠-葡萄糖协同转运蛋白2抑制剂的制备方法
CN112375087A (zh) * 2020-11-27 2021-02-19 浙江天宇药业股份有限公司 一种脯氨酸恒格列净的合成方法
CN113880701A (zh) * 2021-10-10 2022-01-04 浙江司太立制药股份有限公司 一种抗糖尿病药物中间体及其制备方法
CN116785268A (zh) * 2022-03-14 2023-09-22 江苏万邦生化医药集团有限责任公司 一种sglt-2抑制剂的药物组合物

Family Cites Families (14)

* Cited by examiner, † Cited by third party
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
WO2002083066A2 (en) * 2001-04-11 2002-10-24 Bristol-Myers Squibb Company Amino acid complexes of c-aryl glucosides for treatment of diabetes and method
TWI254635B (en) 2002-08-05 2006-05-11 Yamanouchi Pharma Co Ltd Azulene derivative and salt thereof
BRPI0408140B8 (pt) * 2003-03-14 2018-12-11 Astellas Pharma Inc derivado de c-glicosídeo ou seu sal, composição farmacêutica e uso do derivado de c-glicosídeo ou seu sal
LT2896397T (lt) 2003-08-01 2017-11-27 Mitsubishi Tanabe Pharma Corporation Nauji junginiai, turintys inhibitorinį aktyvumą prieš nuo natrio priklausomą gliukozės transporterį
EP2074130A1 (en) * 2006-09-21 2009-07-01 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted difluorobenzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
EP3318562A3 (en) 2007-08-23 2018-09-12 Theracos Sub, LLC Benzylbenzene derivatives and methods of use
US9061060B2 (en) * 2008-07-15 2015-06-23 Theracos Inc. Deuterated benzylbenzene derivatives and methods of use
HRP20161648T1 (hr) 2008-08-22 2017-02-10 Theracos Sub, Llc Postupak za pripravu sglt2 inhibitora
ATE540040T1 (de) 2008-08-28 2012-01-15 Pfizer Dioxabicycloä3.2.1üoctan-2,3,4-triolderivate
WO2010048358A2 (en) 2008-10-22 2010-04-29 Auspex Pharmaceutical, Inc. Ethoxyphenylmethyl inhibitors of sglt2
WO2010074219A1 (ja) * 2008-12-26 2010-07-01 アステラス製薬株式会社 ベンゾチオフェン化合物
ME02016B (me) 2009-11-02 2015-05-20 Pfizer Derivati dioksabiciklo[3.2.1]oktan-2,3,4-triola
US20140228303A1 (en) * 2011-06-13 2014-08-14 Panacea Biotec Ltd Novel sglt inhibitors

Also Published As

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

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