RU2017130849A - Дейтерированная производная хенодезоксихолевой кислоты и фармацевтическая композиция, содержащая данное соединение - Google Patents
Дейтерированная производная хенодезоксихолевой кислоты и фармацевтическая композиция, содержащая данное соединение Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims 8
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical class C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 title 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 102100038495 Bile acid receptor Human genes 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 229940121360 farnesoid X receptor (fxr) agonists Drugs 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 108070000005 Bile acid receptors Proteins 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 108091006027 G proteins Proteins 0.000 claims 1
- 102100025353 G-protein coupled bile acid receptor 1 Human genes 0.000 claims 1
- 102000030782 GTP binding Human genes 0.000 claims 1
- 108091000058 GTP-Binding Proteins 0.000 claims 1
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims 1
- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000001801 chenodeoxycholic acids Chemical class 0.000 claims 1
- 201000001883 cholelithiasis Diseases 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000001130 gallstones Diseases 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- ZXERDUOLZKYMJM-ZWECCWDJSA-N obeticholic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(O)=O)CC[C@H]21 ZXERDUOLZKYMJM-ZWECCWDJSA-N 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
-
- 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
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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
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- 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
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/007—Steroids
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (22)
1. Дейтерированная производная хенодезоксихолевой кислоты, представленная формулой (I) или ее кристаллической формой, фармацевтически приемлемой солью, гидратами или сольватами:
где R1, R2, R3, R4, R5 и R6 по отдельности представляют собой водород или дейтерий;
с оговоркой, что по меньшей мере один из R1, R2, R3, R4, R5 или R6 представляет собой дейтерий.
2. Соединение по п. 1, где R2 представляет собой дейтерий и/или R1 представляет собой дейтерий.
3. Соединение по п. 1, где соединение является соединением, выбранным из следующей группы соединений или их фармацевтически приемлемой соли:
4. Соединение по п. 1, где соединение не содержит какого-либо недейтерированного соединения.
5. Соединение по п. 4, где недейтерированным соединением является 3α,7α-дигидрокси-6α-этил-5β-холан-24-овая кислота.
6. Фармацевтическая композиция, содержащая фармацевтически приемлемый носитель и соединение по любому из пп. 1-5 или их кристаллическую форму, фармацевтически приемлемую соль, гидрат или сольват.
7. Фармацевтическая композиция по п. 6, дополнительно содержащая дополнительный терапевтический агент, и дополнительный терапевтический агент является представляет собой лекарство для лечения раковых заболеваний, сердечно-сосудистых заболеваний, воспалений, инфекций, иммунных заболеваний или нарушений обмена веществ.
8. Фармацевтическая композиция по п. 6, где фармацевтическая композиция представлена в форме инъекций, капсул, таблеток, пилюлей, порошков или гранул.
9. Применение соединения по п. 1 или его кристаллической формы, фармацевтически приемлемой соли, гидрата или сольвата, или фармацевтической композиции по п. 6 при приготовлении фармацевтических композиций, используемых в качестве агониста фарнезоидного X рецептора (FXR) и/или агониста рецептора желчной кислоты, сопряженного с G-белком (GPBAR или TGR5).
10. Применение по п. 9, отличающееся тем, что упомянутая фармацевтическая композиция используется при приготовлении лекарственных средств для лечения и профилактики заболеваний, выбранных из группы, состоящей из: неалкогольного стеатогепатита, неалкогольной жировой болезни печени, желчных камней, первичного билиарного цирроза, цирроза, фиброза печени, диабета, атеросклероза, ожирения.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510084738.5A CN105985396A (zh) | 2015-02-16 | 2015-02-16 | 氘代鹅去氧胆酸衍生物以及包含该化合物的药物组合物 |
| CN201510084738.5 | 2015-02-16 | ||
| PCT/CN2016/073891 WO2016131414A1 (zh) | 2015-02-16 | 2016-02-16 | 氘代鹅去氧胆酸衍生物以及包含该化合物的药物组合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017130849A3 RU2017130849A3 (ru) | 2019-03-18 |
| RU2017130849A true RU2017130849A (ru) | 2019-03-18 |
| RU2712033C2 RU2712033C2 (ru) | 2020-01-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017130849A RU2712033C2 (ru) | 2015-02-16 | 2016-02-16 | Дейтерированное производное хенодезоксихолевой кислоты и фармацевтическая композиция, содержащая данное соединение |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10544185B2 (ru) |
| EP (1) | EP3260463B1 (ru) |
| JP (1) | JP6947644B2 (ru) |
| KR (1) | KR102042112B1 (ru) |
| CN (2) | CN105985396A (ru) |
| AU (1) | AU2016222174B2 (ru) |
| BR (1) | BR112017017529A2 (ru) |
| CA (1) | CA2977109C (ru) |
| RU (1) | RU2712033C2 (ru) |
| WO (1) | WO2016131414A1 (ru) |
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| WO2014169832A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
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| EP3885352B1 (en) | 2014-10-16 | 2024-11-27 | Sage Therapeutics, Inc. | A compound, compositions thereof and this compound for use in methods of treating cns disorders |
| EP4275748A3 (en) | 2014-10-16 | 2024-01-03 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| RS60343B1 (sr) | 2014-11-27 | 2020-07-31 | Sage Therapeutics Inc | Kompozicije i postupci za lečenje poremećaja cns-a |
| SMT202100113T1 (it) | 2015-01-26 | 2021-05-07 | Sage Therapeutics Inc | Composizioni e metodi per trattare disturbi del snc |
| EP3258939B1 (en) | 2015-02-20 | 2022-09-07 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
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| MA45599A (fr) | 2016-07-11 | 2019-05-15 | Sage Therapeutics Inc | Stéroïdes neuroactifs substitués en c17, c20 et c21 et leurs procédés d'utilisation |
| AU2017296295B2 (en) | 2016-07-11 | 2022-02-24 | Sage Therapeutics, Inc. | C7, C12, and C16 substituted neuroactive steroids and their methods of use |
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| CN112142814B (zh) * | 2019-06-26 | 2021-09-28 | 江苏吉贝尔药业股份有限公司 | 牛磺熊去氧胆酸衍生物以及包含其的药物组合物和制剂 |
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| CN112409435B (zh) * | 2019-08-23 | 2023-07-18 | 深圳云合医药科技合伙企业(有限合伙) | 胆汁酸衍生物及其组合物和应用 |
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| WO2010054158A2 (en) * | 2008-11-07 | 2010-05-14 | Auspex Pharmaceuticals, Inc. | Steroid modulators of glucocorticoid receptor |
| AU2009316566B9 (en) * | 2008-11-19 | 2014-05-15 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and method of use thereof |
| ES2592452T3 (es) | 2008-11-19 | 2016-11-30 | Intercept Pharmaceuticals, Inc. | Moduladores de TGR5 y métodos de uso de los mismos |
| WO2013037482A1 (en) * | 2011-09-15 | 2013-03-21 | Phenex Pharmaceuticals Ag | Farnesoid x receptor agonists for cancer treatment and prevention |
| ES2822375T3 (es) * | 2012-06-19 | 2021-04-30 | Intercept Pharmaceuticals Inc | Preparación de la forma no cristalina del ácido obeticólico |
| US20150112089A1 (en) * | 2013-10-22 | 2015-04-23 | Metselex, Inc. | Deuterated bile acids |
-
2015
- 2015-02-16 CN CN201510084738.5A patent/CN105985396A/zh active Pending
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2016
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| KR20170110723A (ko) | 2017-10-11 |
| CN107250149B (zh) | 2020-11-24 |
| CN107250149A (zh) | 2017-10-13 |
| CA2977109A1 (en) | 2016-08-25 |
| JP6947644B2 (ja) | 2021-10-13 |
| BR112017017529A2 (pt) | 2018-04-17 |
| AU2016222174A1 (en) | 2017-09-14 |
| CA2977109C (en) | 2020-04-14 |
| JP2018505220A (ja) | 2018-02-22 |
| EP3260463A1 (en) | 2017-12-27 |
| RU2017130849A3 (ru) | 2019-03-18 |
| KR102042112B1 (ko) | 2019-11-08 |
| CN105985396A (zh) | 2016-10-05 |
| US20180030083A1 (en) | 2018-02-01 |
| HK1248712A1 (en) | 2018-10-19 |
| EP3260463A4 (en) | 2018-10-31 |
| WO2016131414A1 (zh) | 2016-08-25 |
| RU2712033C2 (ru) | 2020-01-24 |
| AU2016222174B2 (en) | 2019-04-11 |
| US10544185B2 (en) | 2020-01-28 |
| EP3260463B1 (en) | 2020-09-02 |
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