CN114787153A - 一种Resmetirom晶型及其制备方法和用途 - Google Patents
一种Resmetirom晶型及其制备方法和用途 Download PDFInfo
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- CN114787153A CN114787153A CN202080082971.9A CN202080082971A CN114787153A CN 114787153 A CN114787153 A CN 114787153A CN 202080082971 A CN202080082971 A CN 202080082971A CN 114787153 A CN114787153 A CN 114787153A
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- 239000013078 crystal Substances 0.000 title claims abstract description 126
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 229940121486 resmetirom Drugs 0.000 title claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 76
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 8
- 229940123876 Thyroid hormone receptor beta agonist Drugs 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 230000005855 radiation Effects 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 41
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 238000005457 optimization Methods 0.000 abstract 1
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- 238000000113 differential scanning calorimetry Methods 0.000 description 7
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- 239000002994 raw material Substances 0.000 description 6
- 231100000331 toxic Toxicity 0.000 description 6
- 230000002588 toxic effect Effects 0.000 description 6
- 229910017488 Cu K Inorganic materials 0.000 description 5
- 229910017541 Cu-K Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
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- 230000004584 weight gain Effects 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000003908 quality control method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000009509 drug development Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
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- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229910002483 Cu Ka Inorganic materials 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- -1 hydrogen Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 108010030696 low density lipoprotein triglyceride Proteins 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
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- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009521 phase II clinical trial Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000001195 ultra high performance liquid chromatography Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Resmetirom(称为“化合物I”)的新晶型及其制备方法，含有该晶型的药物组合物，以及该晶型在制备THR‑β选择性激动剂药物和治疗NASH和HeFH药物中的用途。该化合物I的晶型比现有技术具有一种或多种改进的性质，对未来该药物的优化和开发具有重要价值。
Description
PCT国内申请，说明书已公开。
Claims (15)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911369416 | 2019-12-26 | ||
| CN201911366681 | 2019-12-26 | ||
| CN201911369416X | 2019-12-26 | ||
| CN2019113666812 | 2019-12-26 | ||
| CN2020103004368 | 2020-04-16 | ||
| CN202010300436 | 2020-04-16 | ||
| PCT/CN2020/136551 WO2021129465A1 (zh) | 2019-12-26 | 2020-12-15 | 一种Resmetirom晶型及其制备方法和用途 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114787153A true CN114787153A (zh) | 2022-07-22 |
Family
ID=76573663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080082971.9A Pending CN114787153A (zh) | 2019-12-26 | 2020-12-15 | 一种Resmetirom晶型及其制备方法和用途 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US20220372021A1 (zh) |
| CN (1) | CN114787153A (zh) |
| WO (1) | WO2021129465A1 (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230364099A1 (en) | 2020-10-19 | 2023-11-16 | Teva Pharmaceuticals International Gmbh | Solid state forms of resmetirom |
| CN114907327A (zh) * | 2021-02-10 | 2022-08-16 | 杭州领业医药科技有限公司 | Resmetirom的晶型及其制备方法和用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101228135A (zh) * | 2005-07-21 | 2008-07-23 | 霍夫曼-拉罗奇有限公司 | 作为甲状腺激素受体激动剂的哒嗪酮衍生物 |
| WO2020010068A1 (en) * | 2018-07-02 | 2020-01-09 | Madrigal Pharmaceuticals, Inc. | Solid forms of 2-(3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile |
| WO2020073974A1 (en) * | 2018-10-12 | 2020-04-16 | Inventisbio Shanghai Ltd. | Thyroid hormone receptor agonists |
| WO2020227549A1 (en) * | 2019-05-08 | 2020-11-12 | Aligos Therapeutics, Inc. | MODULATORS OF THR-β AND METHODS OF USE THEREOF |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101966490B1 (ko) * | 2012-09-17 | 2019-08-14 | 마드리갈 파마슈티칼스, 인크. | 갑상선 호르몬 유사체 및 이의 다형의 합성 방법 |
-
2020
- 2020-12-15 WO PCT/CN2020/136551 patent/WO2021129465A1/zh active Application Filing
- 2020-12-15 CN CN202080082971.9A patent/CN114787153A/zh active Pending
-
2022
- 2022-06-24 US US17/849,281 patent/US20220372021A1/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101228135A (zh) * | 2005-07-21 | 2008-07-23 | 霍夫曼-拉罗奇有限公司 | 作为甲状腺激素受体激动剂的哒嗪酮衍生物 |
| WO2020010068A1 (en) * | 2018-07-02 | 2020-01-09 | Madrigal Pharmaceuticals, Inc. | Solid forms of 2-(3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile |
| CN112638904A (zh) * | 2018-07-02 | 2021-04-09 | 马德里加尔制药公司 | 2-(3,5-二氯-4-((5-异丙基-6-氧代-1,6-二氢哒嗪-3-基)氧基)苯基)-3,5-二氧代-2,3,4,5-四氢-1,2,4-三嗪-6-腈的固体形式 |
| WO2020073974A1 (en) * | 2018-10-12 | 2020-04-16 | Inventisbio Shanghai Ltd. | Thyroid hormone receptor agonists |
| CN112739692A (zh) * | 2018-10-12 | 2021-04-30 | 益方生物科技(上海)股份有限公司 | 甲状腺激素受体激动剂 |
| WO2020227549A1 (en) * | 2019-05-08 | 2020-11-12 | Aligos Therapeutics, Inc. | MODULATORS OF THR-β AND METHODS OF USE THEREOF |
| CN114096531A (zh) * | 2019-05-08 | 2022-02-25 | 阿利戈斯治疗公司 | THR-β 调节剂和其使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2021129465A1 (zh) | 2021-07-01 |
| US20220372021A1 (en) | 2022-11-24 |
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