HRP20240713T1 - Polimorfi od (r)-n-(5-(5-etil-1,2,4-oksadiazol-3-il)-2,3-dihidro-1h-inden- 1-il)-1-metil-1h-pirazol-4-karboksamida - Google Patents
Polimorfi od (r)-n-(5-(5-etil-1,2,4-oksadiazol-3-il)-2,3-dihidro-1h-inden- 1-il)-1-metil-1h-pirazol-4-karboksamida Download PDFInfo
- Publication number
- HRP20240713T1 HRP20240713T1 HRP20240713TT HRP20240713T HRP20240713T1 HR P20240713 T1 HRP20240713 T1 HR P20240713T1 HR P20240713T T HRP20240713T T HR P20240713TT HR P20240713 T HRP20240713 T HR P20240713T HR P20240713 T1 HRP20240713 T1 HR P20240713T1
- Authority
- HR
- Croatia
- Prior art keywords
- polymorph
- polymorphic form
- maxima
- degrees
- ethyl
- Prior art date
Links
- IOVAZWDIRCRMTM-OAHLLOKOSA-N N-[(1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl]-1-methylpyrazole-4-carboxamide Chemical compound C(C)C1=NC(=NO1)C=1C=C2CC[C@H](C2=CC=1)NC(=O)C=1C=NN(C=1)C IOVAZWDIRCRMTM-OAHLLOKOSA-N 0.000 title claims 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 18
- 238000000034 method Methods 0.000 claims 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims 15
- 239000002904 solvent Substances 0.000 claims 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 238000002360 preparation method Methods 0.000 claims 10
- 238000001816 cooling Methods 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims 6
- 208000019622 heart disease Diseases 0.000 claims 6
- 238000002411 thermogravimetry Methods 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 230000000747 cardiac effect Effects 0.000 claims 3
- 206010020871 hypertrophic cardiomyopathy Diseases 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 206010052337 Diastolic dysfunction Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 208000038003 heart failure with preserved ejection fraction Diseases 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 210000002235 sarcomere Anatomy 0.000 claims 2
- 230000002861 ventricular Effects 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000004990 Cardiorenal syndrome Diseases 0.000 claims 1
- 208000002330 Congenital Heart Defects Diseases 0.000 claims 1
- 229920002785 Croscarmellose sodium Polymers 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 206010061876 Obstruction Diseases 0.000 claims 1
- 206010038748 Restrictive cardiomyopathy Diseases 0.000 claims 1
- 206010039163 Right ventricular failure Diseases 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 210000005242 cardiac chamber Anatomy 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 208000028831 congenital heart disease Diseases 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 229960001681 croscarmellose sodium Drugs 0.000 claims 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000015210 hypertensive heart disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000005240 left ventricle Anatomy 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 238000003801 milling Methods 0.000 claims 1
- 230000035772 mutation Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 238000007634 remodeling Methods 0.000 claims 1
- 230000009758 senescence Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
Classifications
-
- 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
- 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
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962875350P | 2019-07-17 | 2019-07-17 | |
| EP20753562.6A EP3999180B1 (en) | 2019-07-17 | 2020-07-16 | Polymorphs of (r)-n-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1h-inden-1-yl)-1-methyl-1h-pyrazole-4-carboxamide |
| PCT/US2020/042387 WO2021011807A1 (en) | 2019-07-17 | 2020-07-16 | Polymorphs of (r)-n-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1h-inden-1-yl)-1-methyl-1h-pyrazole-4-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20240713T1 true HRP20240713T1 (hr) | 2024-09-13 |
Family
ID=71995103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20240713TT HRP20240713T1 (hr) | 2019-07-17 | 2020-07-16 | Polimorfi od (r)-n-(5-(5-etil-1,2,4-oksadiazol-3-il)-2,3-dihidro-1h-inden- 1-il)-1-metil-1h-pirazol-4-karboksamida |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20220315571A1 (https=) |
| EP (2) | EP3999180B1 (https=) |
| JP (2) | JP7624431B2 (https=) |
| KR (1) | KR20220084008A (https=) |
| CN (3) | CN114555590B (https=) |
| AU (1) | AU2020313965A1 (https=) |
| BR (1) | BR112022000494A2 (https=) |
| CA (1) | CA3144975A1 (https=) |
| CL (1) | CL2022000054A1 (https=) |
| DK (1) | DK3999180T3 (https=) |
| ES (1) | ES2980885T3 (https=) |
| FI (1) | FI3999180T3 (https=) |
| HR (1) | HRP20240713T1 (https=) |
| HU (1) | HUE066891T2 (https=) |
| IL (1) | IL289875A (https=) |
| LT (1) | LT3999180T (https=) |
| MX (1) | MX2022000504A (https=) |
| PH (1) | PH12022550123A1 (https=) |
| PL (1) | PL3999180T3 (https=) |
| PT (1) | PT3999180T (https=) |
| RS (1) | RS65611B1 (https=) |
| SI (1) | SI3999180T1 (https=) |
| SM (1) | SMT202400224T1 (https=) |
| TW (1) | TWI865562B (https=) |
| WO (1) | WO2021011807A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019144041A1 (en) | 2018-01-19 | 2019-07-25 | Cytokinetics, Inc. | Dihydrobenzofuran and inden analogs as cardiac sarcomere inhibitors |
| JP7610985B2 (ja) | 2018-06-26 | 2025-01-09 | サイトキネティックス， インコーポレイテッド | 心臓サルコメア阻害剤 |
| JP7438148B2 (ja) | 2018-06-26 | 2024-02-26 | サイトキネティックス， インコーポレイテッド | 心臓サルコメア阻害剤 |
| MA53491A (fr) | 2018-08-31 | 2021-09-15 | Cytokinetics Inc | Inhibiteurs de sarcomes cardiaques |
| CN117083275A (zh) | 2021-03-04 | 2023-11-17 | 赛特凯恩蒂克公司 | 心脏肌节抑制剂 |
| PT4370116T (pt) | 2021-07-16 | 2025-03-14 | Cytokinetics Inc | Regimes de administração de aficamten para o tratamento da cardiomiopatia hipertrófica obstrutiva |
| MX2024001294A (es) | 2021-08-03 | 2024-02-13 | Cytokinetics Inc | Proceso para la preparacion de aficamten. |
| WO2024020468A1 (en) | 2022-07-20 | 2024-01-25 | Cytokinetics, Incorporated | Methods for treating non-obstructive hypertrophic cardiomyopathy |
| EP4565230A1 (en) | 2022-08-04 | 2025-06-11 | Cytokinetics, Inc. | Methods for treating obstructive hypertrophic cardiomyopathy |
| WO2024134498A1 (en) | 2022-12-22 | 2024-06-27 | Assia Chemical Industries Ltd. | Solid state forms of aficamten and process for preparation thereof |
| WO2024179422A1 (zh) * | 2023-03-02 | 2024-09-06 | 苏州科睿思制药有限公司 | Aficamten的共晶及其制备方法和用途 |
| US20250295639A1 (en) | 2024-03-20 | 2025-09-25 | Cytokinetics, Incorporated | Methods for treating heart diseases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019144041A1 (en) | 2018-01-19 | 2019-07-25 | Cytokinetics, Inc. | Dihydrobenzofuran and inden analogs as cardiac sarcomere inhibitors |
| MX2024001294A (es) * | 2021-08-03 | 2024-02-13 | Cytokinetics Inc | Proceso para la preparacion de aficamten. |
-
2020
- 2020-07-16 EP EP20753562.6A patent/EP3999180B1/en active Active
- 2020-07-16 CN CN202080059660.0A patent/CN114555590B/zh active Active
- 2020-07-16 DK DK20753562.6T patent/DK3999180T3/da active
- 2020-07-16 CN CN202411172321.XA patent/CN119119018A/zh active Pending
- 2020-07-16 ES ES20753562T patent/ES2980885T3/es active Active
- 2020-07-16 PT PT207535626T patent/PT3999180T/pt unknown
- 2020-07-16 RS RS20240598A patent/RS65611B1/sr unknown
- 2020-07-16 MX MX2022000504A patent/MX2022000504A/es unknown
- 2020-07-16 SM SM20240224T patent/SMT202400224T1/it unknown
- 2020-07-16 PL PL20753562.6T patent/PL3999180T3/pl unknown
- 2020-07-16 LT LTEPPCT/US2020/042387T patent/LT3999180T/lt unknown
- 2020-07-16 SI SI202030443T patent/SI3999180T1/sl unknown
- 2020-07-16 PH PH1/2022/550123A patent/PH12022550123A1/en unknown
- 2020-07-16 WO PCT/US2020/042387 patent/WO2021011807A1/en not_active Ceased
- 2020-07-16 CA CA3144975A patent/CA3144975A1/en active Pending
- 2020-07-16 HR HRP20240713TT patent/HRP20240713T1/hr unknown
- 2020-07-16 US US17/627,599 patent/US20220315571A1/en active Pending
- 2020-07-16 EP EP24174636.1A patent/EP4487911A1/en active Pending
- 2020-07-16 KR KR1020227004639A patent/KR20220084008A/ko active Pending
- 2020-07-16 HU HUE20753562A patent/HUE066891T2/hu unknown
- 2020-07-16 BR BR112022000494A patent/BR112022000494A2/pt unknown
- 2020-07-16 JP JP2022502215A patent/JP7624431B2/ja active Active
- 2020-07-16 AU AU2020313965A patent/AU2020313965A1/en active Pending
- 2020-07-16 TW TW109124093A patent/TWI865562B/zh active
- 2020-07-16 CN CN202411172308.4A patent/CN118908951A/zh active Pending
- 2020-07-16 FI FIEP20753562.6T patent/FI3999180T3/fi active
-
2022
- 2022-01-10 CL CL2022000054A patent/CL2022000054A1/es unknown
- 2022-01-16 IL IL289875A patent/IL289875A/en unknown
-
2025
- 2025-01-20 JP JP2025007662A patent/JP7755090B2/ja active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20240713T1 (hr) | Polimorfi od (r)-n-(5-(5-etil-1,2,4-oksadiazol-3-il)-2,3-dihidro-1h-inden- 1-il)-1-metil-1h-pirazol-4-karboksamida | |
| JP2022540668A5 (https=) | ||
| CN103221047B (zh) | 化合物和方法 | |
| WO2005058848A1 (en) | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists | |
| EP1625123A2 (en) | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as s1p receptor agonists | |
| CN100509789C (zh) | 替米沙坦的晶体钠盐及其作为血管紧张素的拮抗药的用途 | |
| WO1997046556A1 (en) | OXADIAZOLE BENZENESULFONAMIDES AS SELECTIVE β3 AGONISTS FOR THE TREATMENT OF DIABETES AND OBESITY | |
| WO2011144338A1 (en) | Pyrazole derivatives as s1p1 agonists | |
| EP1670463A2 (en) | 3,5-aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as s1p receptor agonists | |
| CN116547270A (zh) | 4-(2-氟-4-甲氧基-5-3-(((1-甲基环丁基)甲基)氨基甲酰基)双环[2.2.1]庚-2-基)氨基甲酰基)苯氧基)-1-甲基环己烷-1-甲酸衍生物以及类似化合物作为rxfp1调节剂用于治疗心力衰竭 | |
| JP5483880B2 (ja) | イミノピリジン誘導体およびその用途 | |
| WO2012012477A1 (en) | Substituted 3-phenyl-1,2,4-oxadiazole compounds | |
| JP2011518766A (ja) | イミノピリジン誘導体およびその用途 | |
| JP2022542803A5 (https=) | ||
| TWI895453B (zh) | 雜環類化合物的晶型及其製備方法和應用 | |
| JP2022540678A5 (https=) | ||
| WO2004046107A1 (en) | Indole derivatives as somatostatin agonists or antagonists | |
| DK2207776T3 (en) | Drug active in neuropathic pain | |
| JP2018521001A (ja) | 化合物 （ｓ）−３−｛４−［５−（２−シクロペンチル−６−メトキシ−ピリジン−４−イル）−［１，２，４］オキサジアゾール−３−イル］−２−エチル−６−メチル−フェノキシ｝−プロパン−１，２−ジオールの結晶形 | |
| JPS61257983A (ja) | １，４−ジヒドロピリジン及びこれを有効成分とする医薬組成物 | |
| JPH08507299A (ja) | ヒドロキシメチルフラザンカルボン酸誘導体及びこれを心臓血管系疾患の治療に使用する方法 | |
| JP2009040702A (ja) | 新規アミドプロピオン酸誘導体を含有する医薬組成物 | |
| AU2018385438B2 (en) | Fumarate salt of (R)-3-(1-(2,3-dichloro-4-(pyrazin-2-yl)phenyl)-2,2,2-trifluoroethyl)-1-methyl-1-(1-methylpiperidin-4-yl) urea, methods of preparation, and uses thereof | |
| RU2018135072A (ru) | Кристаллическая (2s,4r)-5-(5'-хлор-2'-фтор-[1,1'-бифенил]-4-ил)-2-(этоксиметил)-4-(3-гидроксиизоксазол-5-карбоксамидо)-2-метилпентановая кислота и ее применения | |
| NZ784930B2 (en) | Polymorphs of (r)-n-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1h-inden-1-yl)-1-methyl-1h-pyrazole-4-carboxamide |