HRP20100207T1 - Novi kristalni oblici {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1h-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona - Google Patents
Novi kristalni oblici {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1h-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona Download PDFInfo
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- HRP20100207T1 HRP20100207T1 HR20100207T HRP20100207T HRP20100207T1 HR P20100207 T1 HRP20100207 T1 HR P20100207T1 HR 20100207 T HR20100207 T HR 20100207T HR P20100207 T HRP20100207 T HR P20100207T HR P20100207 T1 HRP20100207 T1 HR P20100207T1
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- Prior art keywords
- pyridin
- chlorophenyl
- methanone
- triazol
- bistrifluoromethylbenzyl
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- CAVRKWRKTNINFF-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridin-3-yl]-(2-chlorophenyl)methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(=C(N=N2)C=2C(=CC=CN=2)C(=O)C=2C(=CC=CC=2)Cl)C=2C=CN=CC=2)=C1 CAVRKWRKTNINFF-UHFFFAOYSA-N 0.000 title claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 6
- 238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 238000002360 preparation method Methods 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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 group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000008025 crystallization Effects 0.000 claims 3
- GMNRLJOAZMNQMK-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone Chemical compound C=1C=NC=CC=1C(O)=CC1=NC=CC=C1C(=O)C1=CC=CC=C1Cl GMNRLJOAZMNQMK-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003945 anionic surfactant Substances 0.000 claims 2
- 239000012296 anti-solvent Substances 0.000 claims 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- KFPMDNNVMQLXCF-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone phosphoric acid Chemical group P(=O)(O)(O)O.ClC1=C(C=CC=C1)C(=O)C=1C(=NC=CC1)C=C(C1=CC=NC=C1)O KFPMDNNVMQLXCF-UHFFFAOYSA-N 0.000 claims 1
- JKGHUBCPWOLOFQ-UHFFFAOYSA-N 1-(azidomethyl)-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CN=[N+]=[N-])=CC(C(F)(F)F)=C1 JKGHUBCPWOLOFQ-UHFFFAOYSA-N 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
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 claims 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 229960001855 mannitol Drugs 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 abstract 1
- -1 {2- [1- (3,5-bistrifluoromethylbenzyl) -5-pyridin-4-yl-1H- [1,2,3] triazol-4-yl] pyridin-3-yl} (2-chlorophenyl) Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero 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
-
- 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
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- 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
- A61P25/22—Anxiolytics
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- 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
- A61P25/24—Antidepressants
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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Abstract
Kristalni Oblik IV {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona, naznačen time što ga karakterizira najmanje jedno od sljedećeg: a) 13C spektar nuklearne magnetske rezonancije čvrstog stanja, kojeg čine signali na sljedećim kemijskim pomacima: 52,3 ± 0,2 i 195,4 ± 0,2 ppm; b) uzorak difrakcije rendgenskih zraka na prahu, kojeg čine najmanje dva signala, gdje jedan signal je 12,1 ± 0,1°, a drugi signal se bira iz skupine koju čine 8,3 ± 0,1°, 14,3 ± 0,1°, 16,6 ± 0,1°, 16,9 ± 0,1°, te 18,5 ± 0,1° u 2θ; ic) uzorak difrakcije rendgenskih zraka na prahu, kojeg u najmanju ruku čine sljedeći signali: 8,3 ± 0,1°, 12,1 ± 0,1°, 16,6 ± 0,1°, 16,9 ± 0,1°, te 18,5 ± 0,1° u 2θ. Patent sadrži još 19 patentnih zahtjeva.
Claims (20)
1. Kristalni Oblik IV {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona, naznačen time što ga karakterizira najmanje jedno od sljedećeg:
a) 13C spektar nuklearne magnetske rezonancije čvrstog stanja, kojeg čine signali na sljedećim kemijskim pomacima: 52,3 ± 0,2 i 195,4 ± 0,2 ppm;
b) uzorak difrakcije rendgenskih zraka na prahu, kojeg čine najmanje dva signala, gdje jedan signal je 12,1 ± 0,1°, a drugi signal se bira iz skupine koju čine 8,3 ± 0,1°, 14,3 ± 0,1°, 16,6 ± 0,1°, 16,9 ± 0,1°, te 18,5 ± 0,1° u 2θ; i
c) uzorak difrakcije rendgenskih zraka na prahu, kojeg u najmanju ruku čine sljedeći signali: 8,3 ± 0,1°, 12,1 ± 0,1°, 16,6 ± 0,1°, 16,9 ± 0,1°, te 18,5 ± 0,1° u 2θ.
2. Kristalni Oblik V {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona, naznačen time što ga karakterizira najmanje jedno od sljedećeg:
a) 13C spektar nuklearne magnetske rezonancije čvrstog stanja, kojeg čine signali na sljedećim kemijskim pomacima: 54,3 ± 0,2 i 196,6 ± 0,2 ppm;
b) uzorak difrakcije rendgenskih zraka na prahu, kojeg čine najmanje dva signala, gdje jedan signal je 12,5 ± 0,1°, a drugi signal se bira iz skupine koju čine 15,8 ± 0,1°, 16,5 ± 0,1°, 19,1 ± 0,1°, 19,7 ± 0,1°, 21,5 ± 0,1, 25,3 ± 0,1, 27,7 ± 0,1, te 28,6 ± 0,1° u 2θ; i
c) uzorak difrakcije rendgenskih zraka na prahu, kojeg u najmanju ruku čine sljedeći signali: 12,5 ± 0,1°, 25,3 ± 0,1°, 27,7 ± 0,1°, te 28,6 ± 0,1° u 2θ.
3. Spoj, naznačen time što je (2-klorfenil)[2-(2-hidroksi-2-piridin-4-ilvinil)piridin-3-il]metanon, ili njegova sol.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je (2-klorfenil)[2-(2-hidroksi-2-piridin-4-ilvinil)piridin-3-il]metanon-fosfat.
5. Postupak dobivanja spoja koji je {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanon, naznačen time što se sastoji u reakciji (2-klorfenil)[2-(2-hidroksi-2-piridin-4-ilvinil)piridin-3-il]metanona, ili njegove fosfatne soli, s 1-azidometil-3,5-bistrifluormetilbenzenom, u prisutnosti pogodne baze i otapala.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time što baza je kalijev karbonat.
7. Postupak u skladu s patentnim zahtjevom 5 ili 6, naznačen time što otapalo se bira iz skupine koju čine dimetil-sulfokid, izopropanol, etanol, tetrahidrofuran i toluen.
8. Postupak dobivanja spoja u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u kristalizaciji {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona iz otapala.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što otapalo se bira iz skupine koju čine izopropanol, aceton, acetonitril, propanol, butanol, etil-acetat, metil-tert-butil-eter i diklormetan.
10. Postupak dobivanja spoja u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u kristalizaciji {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona transformacijom faze iz otopine.
11. Postupak dobivanja spoja u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u kristalizaciji {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona iz smjese otapala i protuotapala.
12. Postupak u skladu s patentnim zahtjevom 11, naznačen time što otapalo je metanol ili etanol.
13. Postupak u skladu s bilo kojim od patentnih zahtjeva 11 ili 12, naznačen time što protuotapalo je voda.
14. Farmaceutski pripravak, naznačen time što sadrži kristalni spoj u skladu s bilo kojim od patentnih zahtjeva 1 ili 2, u kombinaciji s jednim ili više farmaceutski prihvatljivih podloga, pomoćnih tvari ili razrjeđivača.
15. Pripravak u skladu s patentnim zahtjevom 14, naznačen time što sadrži najmanje jedno od sljedećeg: manitol, mikrokristalnu celulozu, hidroksipropilcelulozu, koloidni silicijev dioksid, umreženu natrij-karboksimetilcelulozu i stearinsku kiselinu.
16. Pripravak u skladu s bilo kojim od patentnih zahtjeva 14 ili 15, naznačen time što sadrži anionski surfaktant.
17. Pripravak u skladu s patentnim zahtjevom 16, naznačen time što anionski surfaktant je natrijev lauril-sulfat.
18. Pripravak u skladu s bilo kojim od patentnih zahtjeva 14 do 17, naznačen time što sadrži kiselinu.
19. Pripravak u skladu s patentnim zahtjevom 18, naznačen time što kiselina je limunska kiselina.
20. Pripravak u skladu s bilo kojim od patentnih zahtjeva 14 do 19, naznačen time što sadrži Kristalni Oblik IV {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1H-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51430003P | 2003-10-24 | 2003-10-24 | |
| PCT/US2004/030914 WO2005042515A1 (en) | 2003-10-24 | 2004-10-12 | Novel crystalline forms of {2-[1-(3,5-bis-trifluoromethylbenzyl)-5-pyridin-4-yl-1h-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100207T1 true HRP20100207T1 (hr) | 2010-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100207T HRP20100207T1 (hr) | 2003-10-24 | 2010-04-13 | Novi kristalni oblici {2-[1-(3,5-bistrifluormetilbenzil)-5-piridin-4-il-1h-[1,2,3]triazol-4-il]piridin-3-il}(2-klorfenil)metanona |
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| US (1) | US7381826B2 (hr) |
| JP (1) | JP4959336B2 (hr) |
| KR (1) | KR100848407B1 (hr) |
| CN (1) | CN1863791B (hr) |
| AR (1) | AR046131A1 (hr) |
| AT (1) | ATE462700T1 (hr) |
| AU (1) | AU2004285855B8 (hr) |
| BR (1) | BRPI0415010B8 (hr) |
| CA (1) | CA2542140C (hr) |
| CL (2) | CL2009001310A1 (hr) |
| CR (1) | CR8353A (hr) |
| DE (1) | DE602004026333D1 (hr) |
| DK (1) | DK1675846T3 (hr) |
| EA (1) | EA008881B1 (hr) |
| EC (1) | ECSP066517A (hr) |
| ES (1) | ES2340772T3 (hr) |
| HR (1) | HRP20100207T1 (hr) |
| IL (1) | IL174926A0 (hr) |
| MA (1) | MA28329A1 (hr) |
| MY (1) | MY157375A (hr) |
| NO (1) | NO335090B1 (hr) |
| NZ (2) | NZ545917A (hr) |
| PE (1) | PE20050481A1 (hr) |
| PT (1) | PT1675846E (hr) |
| TW (1) | TW200524906A (hr) |
| UA (1) | UA82901C2 (hr) |
| WO (1) | WO2005042515A1 (hr) |
| ZA (1) | ZA200603234B (hr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA200970604A1 (ru) | 2006-12-20 | 2009-10-30 | Эли Лилли Энд Компани | Новое промежуточное соединение и способ, используемый для получения {2-[1-(3,5-бис-трифторметилбензил)-5-пиридин-4-ил-1н-[1,2,3]триазол-4-ил]пиридин-3-ил}-(2-хлорфенил)метанона |
| WO2009075778A2 (en) * | 2007-12-06 | 2009-06-18 | The Regents Of The University Of California | Nonpeptidic inhibitors of cruzain |
| US8080568B1 (en) * | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| RU2770050C2 (ru) | 2015-03-04 | 2022-04-14 | Ванда Фармасьютиклз Инк. | Способ лечения с применением традипитанта |
| US10287287B2 (en) | 2015-08-17 | 2019-05-14 | Eli Lilly And Company | Process development of a pyridine-containing NK-1 receptor antagonist |
| US11549147B2 (en) | 2017-09-13 | 2023-01-10 | Vanda Pharmaceuticals Inc. | Treatment of atopic dermatitis with tradipitant |
| CN111343981A (zh) | 2017-11-17 | 2020-06-26 | 万达制药公司 | 使用川地匹坦治疗胃肠疾病的方法 |
| EP3801514A1 (en) | 2018-06-08 | 2021-04-14 | Vanda Pharmaceuticals Inc. | Method of treatment with tradipitant |
| US10821099B2 (en) | 2018-09-28 | 2020-11-03 | Vanda Pharmaceuticals Inc. | Use of tradipitant in motion sickness |
| JP7468964B2 (ja) | 2018-09-28 | 2024-04-16 | バンダ・ファーマシューティカルズ・インコーポレイテッド | 動揺病におけるトラジピタントの使用 |
| WO2020117811A1 (en) | 2018-12-03 | 2020-06-11 | Vanda Pharmaceuticals Inc. | Method of treatment with tradipitant |
| CA3169449A1 (en) | 2020-02-25 | 2021-09-02 | Vanda Pharmaceuticals Inc. | Improved treatment of atopic dermatitis with tradipitant |
| US20230145932A1 (en) | 2020-03-26 | 2023-05-11 | Vanda Pharmaceuticals Inc. | Treatment of lower respiratory tract infection with tradipitant |
| WO2023019084A1 (en) | 2021-08-12 | 2023-02-16 | Vanda Pharmaceuticals Inc. | Treatment of gastric accommodation with tradipitant |
| EP4395778A1 (en) | 2021-08-31 | 2024-07-10 | Vanda Pharmaceuticals Inc. | Treatment of lower respiratory tract infection with tradipitant |
| WO2024138040A1 (en) | 2022-12-21 | 2024-06-27 | Vanda Pharmaceuticals Inc. | Methods of treatment with tradipitant |
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| US20020099067A1 (en) * | 1993-07-08 | 2002-07-25 | Ulrich Posanski | Pharmaceutical compositions for sparingly soluble therapeutic agents |
| GB9505492D0 (en) * | 1995-03-18 | 1995-05-03 | Merck Sharp & Dohme | Therapeutic agents |
| GB9525296D0 (en) * | 1995-12-11 | 1996-02-07 | Merck Sharp & Dohme | Therapeutic agents |
| ATE333879T1 (de) * | 1996-10-07 | 2006-08-15 | Merck Sharp & Dohme | Zns-penetrierende nk-1 rezeptorantagonisten als antidepressivum und / oder anxiolytikum |
| CZ2002534A3 (cs) * | 1999-08-13 | 2002-07-17 | Vertex Pharmaceuticals Incorporated | Inhibitory protein-kináz, farmaceutické prostředky, které je obsahují, a jejich pouľití |
| CA2388202A1 (en) | 1999-10-29 | 2001-05-10 | Merck & Co., Inc. | Polymorphic form of a tachykinin receptor antagonist |
| US20020044971A1 (en) * | 2000-07-07 | 2002-04-18 | Amidon Gordon L. | Dissolution rate of poorly soluble drugs |
| PE20040600A1 (es) * | 2002-04-26 | 2004-09-15 | Lilly Co Eli | Derivados de triazol como antagonistas del receptor de taquicinina |
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