CN107602546A - 化合物的晶型及其制备方法、组合物和应用 - Google Patents
化合物的晶型及其制备方法、组合物和应用 Download PDFInfo
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- CN107602546A CN107602546A CN201710558261.9A CN201710558261A CN107602546A CN 107602546 A CN107602546 A CN 107602546A CN 201710558261 A CN201710558261 A CN 201710558261A CN 107602546 A CN107602546 A CN 107602546A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2016105396146 | 2016-07-11 | ||
CN201610539614 | 2016-07-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107602546A true CN107602546A (zh) | 2018-01-19 |
CN107602546B CN107602546B (zh) | 2022-04-22 |
Family
ID=60952813
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710558261.9A Active CN107602546B (zh) | 2016-07-11 | 2017-07-10 | 化合物的晶型及其制备方法、组合物和应用 |
Country Status (4)
Country | Link |
---|---|
US (1) | US10611757B2 (zh) |
EP (1) | EP3461822B1 (zh) |
CN (1) | CN107602546B (zh) |
WO (1) | WO2018010622A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107661302A (zh) * | 2016-07-29 | 2018-02-06 | 武汉朗来科技发展有限公司 | 一种口服固体制剂及其应用 |
CN115463133A (zh) * | 2021-06-10 | 2022-12-13 | 武汉朗来科技发展有限公司 | 一种药物组合物、制剂及其制备方法和应用 |
Families Citing this family (2)
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CN112110909A (zh) * | 2016-05-20 | 2020-12-22 | 武汉朗来科技发展有限公司 | 化合物及其制备方法、组合物和应用 |
WO2018064945A1 (zh) * | 2016-10-08 | 2018-04-12 | 武汉朗来科技发展有限公司 | 药物组合物 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1946717A (zh) * | 2004-02-25 | 2007-04-11 | 武田药品工业株式会社 | 苯并咪唑衍生物及其作为aⅱ受体拮抗剂的用途 |
WO2013114305A1 (en) * | 2012-02-02 | 2013-08-08 | Ranbaxy Laboratories Limited | Process for the preparation of azilsartan medoxomil or pharmaceutically acceptable salts thereof |
CN103709154A (zh) * | 2012-09-28 | 2014-04-09 | 武汉启瑞药业有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
CN104039779A (zh) * | 2012-01-14 | 2014-09-10 | 广东东阳光药业有限公司 | 阿齐沙坦酯钾的晶型及其制备方法及其用途 |
CN104774196A (zh) * | 2014-01-09 | 2015-07-15 | 武汉朗来科技发展有限公司 | 一种苯并咪唑衍生物的制备方法 |
CN105153141A (zh) * | 2013-02-04 | 2015-12-16 | 武汉朗来科技发展有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014530805A (ja) * | 2011-09-30 | 2014-11-20 | スンシネ ルアケ プハルマ カンパニー リミテッド | アジルサルタンの結晶形並びにその製造及び使用 |
WO2016145622A1 (zh) * | 2015-03-18 | 2016-09-22 | 武汉朗来科技发展有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
CN112110909A (zh) * | 2016-05-20 | 2020-12-22 | 武汉朗来科技发展有限公司 | 化合物及其制备方法、组合物和应用 |
EA039493B1 (ru) * | 2016-06-29 | 2022-02-02 | Университе Де Монреаль | Биарилметильные гетероциклы |
EP3492466B1 (en) * | 2016-07-29 | 2022-06-01 | Wuhan LL Science And Technology Development Co., Ltd. | Oral solid preparation and use thereof |
-
2017
- 2017-07-10 US US16/301,027 patent/US10611757B2/en active Active
- 2017-07-10 EP EP17826958.5A patent/EP3461822B1/en active Active
- 2017-07-10 CN CN201710558261.9A patent/CN107602546B/zh active Active
- 2017-07-10 WO PCT/CN2017/092416 patent/WO2018010622A1/zh unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1946717A (zh) * | 2004-02-25 | 2007-04-11 | 武田药品工业株式会社 | 苯并咪唑衍生物及其作为aⅱ受体拮抗剂的用途 |
CN104039779A (zh) * | 2012-01-14 | 2014-09-10 | 广东东阳光药业有限公司 | 阿齐沙坦酯钾的晶型及其制备方法及其用途 |
WO2013114305A1 (en) * | 2012-02-02 | 2013-08-08 | Ranbaxy Laboratories Limited | Process for the preparation of azilsartan medoxomil or pharmaceutically acceptable salts thereof |
CN103709154A (zh) * | 2012-09-28 | 2014-04-09 | 武汉启瑞药业有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
CN105237527A (zh) * | 2012-09-28 | 2016-01-13 | 武汉朗来科技发展有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
CN105153141A (zh) * | 2013-02-04 | 2015-12-16 | 武汉朗来科技发展有限公司 | 苯并咪唑衍生物及其制备方法和医药用途 |
CN104774196A (zh) * | 2014-01-09 | 2015-07-15 | 武汉朗来科技发展有限公司 | 一种苯并咪唑衍生物的制备方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107661302A (zh) * | 2016-07-29 | 2018-02-06 | 武汉朗来科技发展有限公司 | 一种口服固体制剂及其应用 |
CN107661302B (zh) * | 2016-07-29 | 2021-08-27 | 武汉朗来科技发展有限公司 | 一种口服固体制剂及其应用 |
CN115463133A (zh) * | 2021-06-10 | 2022-12-13 | 武汉朗来科技发展有限公司 | 一种药物组合物、制剂及其制备方法和应用 |
CN115463133B (zh) * | 2021-06-10 | 2024-03-01 | 武汉朗来科技发展有限公司 | 一种药物组合物、制剂及其制备方法和应用 |
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EP3461822A1 (en) | 2019-04-03 |
EP3461822A4 (en) | 2019-10-30 |
CN107602546B (zh) | 2022-04-22 |
WO2018010622A1 (zh) | 2018-01-18 |
US20190177312A1 (en) | 2019-06-13 |
US10611757B2 (en) | 2020-04-07 |
EP3461822B1 (en) | 2022-11-02 |
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