HRP20241515T1 - Kokristali (1r,3s)-3-(5-cijano-4-fenil-1,3-tiazol-2-ilkarbamoil)ciklopentankarboksilne kiseline - Google Patents
Kokristali (1r,3s)-3-(5-cijano-4-fenil-1,3-tiazol-2-ilkarbamoil)ciklopentankarboksilne kiseline Download PDFInfo
- Publication number
- HRP20241515T1 HRP20241515T1 HRP20241515TT HRP20241515T HRP20241515T1 HR P20241515 T1 HRP20241515 T1 HR P20241515T1 HR P20241515T T HRP20241515T T HR P20241515TT HR P20241515 T HRP20241515 T HR P20241515T HR P20241515 T1 HRP20241515 T1 HR P20241515T1
- Authority
- HR
- Croatia
- Prior art keywords
- cocrystal
- crystal
- thiazol
- cyano
- phenyl
- Prior art date
Links
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 title 2
- 239000013078 crystal Substances 0.000 claims 14
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- MSZKZEFOAPULKG-NWDGAFQWSA-N (1r,3s)-3-[(5-cyano-4-phenyl-1,3-thiazol-2-yl)carbamoyl]cyclopentane-1-carboxylic acid Chemical compound C1[C@H](C(=O)O)CC[C@@H]1C(=O)NC1=NC(C=2C=CC=CC=2)=C(C#N)S1 MSZKZEFOAPULKG-NWDGAFQWSA-N 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 229960005219 gentisic acid Drugs 0.000 claims 4
- 229960003966 nicotinamide Drugs 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000002441 X-ray diffraction Methods 0.000 claims 3
- 239000013066 combination product Substances 0.000 claims 3
- 229940127555 combination product Drugs 0.000 claims 3
- 238000000113 differential scanning calorimetry Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- 238000001757 thermogravimetry curve Methods 0.000 claims 3
- 108010060263 Adenosine A1 Receptor Proteins 0.000 claims 2
- 102000030814 Adenosine A1 receptor Human genes 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- 230000008485 antagonism Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000001747 exhibiting effect Effects 0.000 claims 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 229940045136 urea Drugs 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 claims 1
- 208000033626 Renal failure acute Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 201000011040 acute kidney failure Diseases 0.000 claims 1
- 208000012998 acute renal failure Diseases 0.000 claims 1
- 229940127282 angiotensin receptor antagonist Drugs 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/02—Salts; Complexes; Addition compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20382194.7A EP3882240A1 (en) | 2020-03-16 | 2020-03-16 | Cocrystals of (1r,3s)-3-(5-cyano-4-phenyl-1,3-thiazol-2-ylcabamoyl)cyclopentane carboxylic acid |
| EP21710531.1A EP4121419B1 (en) | 2020-03-16 | 2021-03-15 | Cocrystals of (1r,3s)-3-(5-cyano-4-phenyl-1,3-thiazol-2-ylcarbamoyl)cyclopentane carboxylic acid |
| PCT/EP2021/056506 WO2021185748A1 (en) | 2020-03-16 | 2021-03-15 | Cocrystals of (1r,3s)-3-(5-cyano-4-phenyl-1,3-thiazol-2-ylcabamoyl)cyclopentane carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20241515T1 true HRP20241515T1 (hr) | 2025-01-03 |
Family
ID=69953938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20241515TT HRP20241515T1 (hr) | 2020-03-16 | 2021-03-15 | Kokristali (1r,3s)-3-(5-cijano-4-fenil-1,3-tiazol-2-ilkarbamoil)ciklopentankarboksilne kiseline |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US12384754B2 (https=) |
| EP (2) | EP3882240A1 (https=) |
| JP (1) | JP7779846B2 (https=) |
| KR (1) | KR20220154791A (https=) |
| CN (1) | CN115298169B (https=) |
| AU (1) | AU2021237686B2 (https=) |
| BR (1) | BR112022018449A2 (https=) |
| CA (1) | CA3171894C (https=) |
| DK (1) | DK4121419T3 (https=) |
| ES (1) | ES3002084T3 (https=) |
| FI (1) | FI4121419T3 (https=) |
| HR (1) | HRP20241515T1 (https=) |
| HU (1) | HUE068886T2 (https=) |
| LT (1) | LT4121419T (https=) |
| MX (1) | MX2022011530A (https=) |
| PL (1) | PL4121419T3 (https=) |
| PT (1) | PT4121419T (https=) |
| RS (1) | RS66214B1 (https=) |
| SI (1) | SI4121419T1 (https=) |
| WO (1) | WO2021185748A1 (https=) |
| ZA (1) | ZA202211247B (https=) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2331220B1 (es) | 2007-10-02 | 2010-09-23 | Palobiofarma, S.L. | Nuevos compuestos como antagonistas de los receptores a1 de adenosina. |
| US8779146B2 (en) | 2010-04-28 | 2014-07-15 | Nuformix Limited | Cilostazol cocrystals and compositions |
| LT3592734T (lt) | 2017-03-06 | 2021-07-26 | Palobiofarma, S.L. | (1r,3s)-3-(5-ciano-4-fenil-1,3-tiazol-2-ilkarbamoil)ciklopentankarboksirūgšties amino druska |
-
2020
- 2020-03-16 EP EP20382194.7A patent/EP3882240A1/en not_active Withdrawn
-
2021
- 2021-03-15 CN CN202180021708.3A patent/CN115298169B/zh active Active
- 2021-03-15 EP EP21710531.1A patent/EP4121419B1/en active Active
- 2021-03-15 PT PT217105311T patent/PT4121419T/pt unknown
- 2021-03-15 MX MX2022011530A patent/MX2022011530A/es unknown
- 2021-03-15 HR HRP20241515TT patent/HRP20241515T1/hr unknown
- 2021-03-15 ES ES21710531T patent/ES3002084T3/es active Active
- 2021-03-15 AU AU2021237686A patent/AU2021237686B2/en active Active
- 2021-03-15 BR BR112022018449A patent/BR112022018449A2/pt unknown
- 2021-03-15 RS RS20241203A patent/RS66214B1/sr unknown
- 2021-03-15 CA CA3171894A patent/CA3171894C/en active Active
- 2021-03-15 HU HUE21710531A patent/HUE068886T2/hu unknown
- 2021-03-15 WO PCT/EP2021/056506 patent/WO2021185748A1/en not_active Ceased
- 2021-03-15 DK DK21710531.1T patent/DK4121419T3/da active
- 2021-03-15 US US17/906,367 patent/US12384754B2/en active Active
- 2021-03-15 KR KR1020227035871A patent/KR20220154791A/ko active Pending
- 2021-03-15 LT LTEPPCT/EP2021/056506T patent/LT4121419T/lt unknown
- 2021-03-15 SI SI202130224T patent/SI4121419T1/sl unknown
- 2021-03-15 PL PL21710531.1T patent/PL4121419T3/pl unknown
- 2021-03-15 FI FIEP21710531.1T patent/FI4121419T3/fi active
- 2021-03-15 JP JP2022555805A patent/JP7779846B2/ja active Active
-
2022
- 2022-10-13 ZA ZA2022/11247A patent/ZA202211247B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES3002084T3 (en) | 2025-03-06 |
| JP7779846B2 (ja) | 2025-12-03 |
| KR20220154791A (ko) | 2022-11-22 |
| MX2022011530A (es) | 2022-10-13 |
| HUE068886T2 (hu) | 2025-02-28 |
| EP4121419A1 (en) | 2023-01-25 |
| CN115298169A (zh) | 2022-11-04 |
| FI4121419T3 (fi) | 2024-11-04 |
| US12384754B2 (en) | 2025-08-12 |
| LT4121419T (lt) | 2024-11-25 |
| CA3171894C (en) | 2025-03-11 |
| EP3882240A1 (en) | 2021-09-22 |
| WO2021185748A1 (en) | 2021-09-23 |
| CN115298169B (zh) | 2024-11-19 |
| US20230183195A1 (en) | 2023-06-15 |
| DK4121419T3 (da) | 2024-10-28 |
| ZA202211247B (en) | 2023-12-20 |
| AU2021237686A1 (en) | 2022-10-06 |
| BR112022018449A2 (pt) | 2022-11-01 |
| AU2021237686B2 (en) | 2026-04-09 |
| PL4121419T3 (pl) | 2025-02-17 |
| CA3171894A1 (en) | 2021-09-23 |
| EP4121419B1 (en) | 2024-08-14 |
| PT4121419T (pt) | 2024-11-18 |
| SI4121419T1 (sl) | 2025-02-28 |
| RS66214B1 (sr) | 2024-12-31 |
| JP2023517722A (ja) | 2023-04-26 |
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