CN108864077B - 小檗碱有机酸盐的固体形式及其制备方法 - Google Patents

小檗碱有机酸盐的固体形式及其制备方法 Download PDF

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Publication number
CN108864077B
CN108864077B CN201710335467.5A CN201710335467A CN108864077B CN 108864077 B CN108864077 B CN 108864077B CN 201710335467 A CN201710335467 A CN 201710335467A CN 108864077 B CN108864077 B CN 108864077B
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solid form
ether
crystal
berberine
berberine ursodeoxycholate
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Chinese (zh)
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CN108864077A (zh
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于萌
刘利平
付鑫祥
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Shenzhen Hightide Biopharmaceutical Ltd
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Shenzhen Hightide Biopharmaceutical Ltd
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Priority to CN201710335467.5A priority Critical patent/CN108864077B/zh
Application filed by Shenzhen Hightide Biopharmaceutical Ltd filed Critical Shenzhen Hightide Biopharmaceutical Ltd
Priority to NZ759154A priority patent/NZ759154B2/en
Priority to EP18798004.0A priority patent/EP3625229B9/en
Priority to CA3062833A priority patent/CA3062833A1/en
Priority to AU2018264384A priority patent/AU2018264384B2/en
Priority to EP23167629.7A priority patent/EP4234568A3/en
Priority to JP2019562655A priority patent/JP7685314B2/ja
Priority to KR1020197036227A priority patent/KR102761338B1/ko
Priority to EA201992607A priority patent/EA201992607A1/ru
Priority to KR1020257002617A priority patent/KR20250017765A/ko
Priority to ES18798004T priority patent/ES2988672T3/es
Priority to US16/608,457 priority patent/US10959999B2/en
Priority to PCT/CN2018/086461 priority patent/WO2018205987A1/en
Publication of CN108864077A publication Critical patent/CN108864077A/zh
Application granted granted Critical
Publication of CN108864077B publication Critical patent/CN108864077B/zh
Priority to US17/182,715 priority patent/US12138258B2/en
Priority to AU2022206685A priority patent/AU2022206685B2/en
Priority to JP2023020228A priority patent/JP7728295B2/ja
Priority to US18/904,564 priority patent/US20250099456A1/en
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    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN201710335467.5A 2017-05-12 2017-05-12 小檗碱有机酸盐的固体形式及其制备方法 Active CN108864077B (zh)

Priority Applications (17)

Application Number Priority Date Filing Date Title
CN201710335467.5A CN108864077B (zh) 2017-05-12 2017-05-12 小檗碱有机酸盐的固体形式及其制备方法
PCT/CN2018/086461 WO2018205987A1 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
CA3062833A CA3062833A1 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
AU2018264384A AU2018264384B2 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
EP23167629.7A EP4234568A3 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
JP2019562655A JP7685314B2 (ja) 2017-05-12 2018-05-11 ベルベリンウルソデオキシコール酸の固体形態ならびにその組成物および方法
KR1020197036227A KR102761338B1 (ko) 2017-05-12 2018-05-11 베르베린 우르소데옥시콜레이트의 고체 형태 및 그 조성물 및 방법
EA201992607A EA201992607A1 (ru) 2017-05-12 2018-05-11 Твердые формы берберина урсодезоксихолата, их композиции и способы
NZ759154A NZ759154B2 (en) 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
ES18798004T ES2988672T3 (es) 2017-05-12 2018-05-11 Formas sólidas de ursodesoxicolato de berberina y composiciones y métodos de las mismas
US16/608,457 US10959999B2 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
EP18798004.0A EP3625229B9 (en) 2017-05-12 2018-05-11 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
KR1020257002617A KR20250017765A (ko) 2017-05-12 2018-05-11 베르베린 우르소데옥시콜레이트의 고체 형태 및 그 조성물 및 방법
US17/182,715 US12138258B2 (en) 2017-05-12 2021-02-23 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
AU2022206685A AU2022206685B2 (en) 2017-05-12 2022-07-18 Solid forms of berberine ursodeoxycholate and compositions and methods thereof
JP2023020228A JP7728295B2 (ja) 2017-05-12 2023-02-13 ベルベリンウルソデオキシコール酸の固体形態ならびにその組成物および方法
US18/904,564 US20250099456A1 (en) 2017-05-12 2024-10-02 Solid forms of berberine ursodeoxycholate and compositions and methods thereof

Applications Claiming Priority (1)

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CN201710335467.5A CN108864077B (zh) 2017-05-12 2017-05-12 小檗碱有机酸盐的固体形式及其制备方法

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CN108864077A CN108864077A (zh) 2018-11-23
CN108864077B true CN108864077B (zh) 2020-05-22

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US (3) US10959999B2 (enExample)
EP (2) EP4234568A3 (enExample)
JP (2) JP7685314B2 (enExample)
KR (2) KR20250017765A (enExample)
CN (1) CN108864077B (enExample)
AU (2) AU2018264384B2 (enExample)
CA (1) CA3062833A1 (enExample)
EA (1) EA201992607A1 (enExample)
ES (1) ES2988672T3 (enExample)
WO (1) WO2018205987A1 (enExample)

Families Citing this family (16)

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CN108864077B (zh) * 2017-05-12 2020-05-22 深圳君圣泰生物技术有限公司 小檗碱有机酸盐的固体形式及其制备方法
CN110954645B (zh) * 2019-09-09 2020-09-29 山东琪康生物技术有限公司 一种高质量四黄止痢颗粒的检测方法
CN112851660B (zh) * 2019-11-12 2022-03-18 广东药科大学 含有小檗碱的酸-碱加成盐、其制备方法及其作为药物的用途
CN111920777A (zh) * 2020-09-18 2020-11-13 四川迪菲特药业有限公司 一种盐酸小檗碱片及其制备方法
KR102636847B1 (ko) * 2020-09-18 2024-02-19 경북대학교 산학협력단 티아민 유도체를 포함하는 이식편대숙주질환 예방 또는 치료용 약학적 조성물
US20230112845A1 (en) * 2020-10-23 2023-04-13 Shenzhen Hightide Biopharmaceutical Ltd. Compositions of berberine ursodeoxycholate and methods thereof for treating fatty liver disease, diabetes and hyperlipidemia
WO2022083713A1 (en) * 2020-10-23 2022-04-28 Shenzhen Hightide Biopharmaceutical Ltd. Compositions of berberine ursodeoxycholate and methods thereof for treating fatty liver disease, diabetes and hyperlipidemia
WO2022161468A1 (en) * 2021-01-28 2022-08-04 Shenzhen Hightide Biopharmaceutical Ltd. Compositions of berberine ursodeoxycholate and methods thereof for treating primary sclerosing cholangitis
US20230346803A1 (en) * 2021-01-28 2023-11-02 Shenzhen Hightide Biopharmaceutical Ltd. Compositions of berberine ursodeoxycholate and methods thereof for treating primary sclerosing cholangitis
WO2023088463A1 (en) * 2021-11-22 2023-05-25 Shenzhen Hightide Biopharmaceutical Ltd. Compositions and methods of berberine ursodeoxycholate for modulating gut microbiome compositions
CN114716498B (zh) * 2022-01-20 2024-01-23 成都贝诺科成生物科技有限公司 一种高稳定性的失碳熊去氧胆酸小檗碱盐晶型及其制备方法
CN115477647A (zh) * 2022-10-26 2022-12-16 山西医科大学 小檗碱富马酸盐晶型及其制备方法和其组合物与应用
WO2024120452A1 (en) * 2022-12-07 2024-06-13 Shenzhen Hightide Biopharmaceutical Ltd. Compositions and methods for prophylaxis and treatment of covid-19
EP4642454A1 (en) * 2022-12-30 2025-11-05 Shenzhen Hightide Biopharmaceutical Ltd. Pharmaceutical combinations and compositions, and methods of use thereof
KR20250166895A (ko) * 2023-02-15 2025-11-28 센젠 하이타이드 바이오파마슈티컬 리미티드 베르베린 타우로우르소데옥시콜레이트 조성물 및 이의 방법
WO2024179570A1 (en) * 2023-03-01 2024-09-06 Shenzhen Hightide Biopharmaceutical Ltd. Compositions and methods for treating severe hypertriglyceridemia

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CN105693805A (zh) * 2016-03-15 2016-06-22 合肥华方医药科技有限公司 一种胆酸类小檗碱偶合物的制备及医药用途

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EP3625229B9 (en) 2024-10-09
US12138258B2 (en) 2024-11-12
WO2018205987A1 (en) 2018-11-15
EP4234568A2 (en) 2023-08-30
US20250099456A1 (en) 2025-03-27
CN108864077A (zh) 2018-11-23
EA201992607A1 (ru) 2020-06-29
AU2022206685A1 (en) 2022-08-11
US20210251981A1 (en) 2021-08-19
EP4234568A3 (en) 2024-01-03
KR102761338B1 (ko) 2025-02-04
US10959999B2 (en) 2021-03-30
NZ759154A (en) 2024-07-26
JP2020519654A (ja) 2020-07-02
EP3625229B1 (en) 2024-07-31
JP7685314B2 (ja) 2025-05-29
JP2023104925A (ja) 2023-07-28
AU2018264384A1 (en) 2019-12-12
AU2022206685B2 (en) 2024-05-02
KR20230017930A (ko) 2023-02-07
JP7728295B2 (ja) 2025-08-22
EP3625229A1 (en) 2020-03-25
EP3625229A4 (en) 2021-03-03
CA3062833A1 (en) 2018-11-15
EP3625229C0 (en) 2024-07-31
ES2988672T3 (es) 2024-11-21
AU2018264384B2 (en) 2022-05-19
KR20250017765A (ko) 2025-02-04
US20200188387A1 (en) 2020-06-18

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