ZA200603234B - Novel crystalline forms of {2-[1-(3,5-bis-trifluoromethyul-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-[2-chlorophenyl)-methanone - Google Patents
Novel crystalline forms of {2-[1-(3,5-bis-trifluoromethyul-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-[2-chlorophenyl)-methanone Download PDFInfo
- Publication number
- ZA200603234B ZA200603234B ZA200603234A ZA200603234A ZA200603234B ZA 200603234 B ZA200603234 B ZA 200603234B ZA 200603234 A ZA200603234 A ZA 200603234A ZA 200603234 A ZA200603234 A ZA 200603234A ZA 200603234 B ZA200603234 B ZA 200603234B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridin
- chlorophenyl
- methanone
- triazol
- compound
- Prior art date
Links
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 title 1
- 238000000034 method Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 17
- 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 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims 8
- 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
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- GMNRLJOAZMNQMK-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone Chemical group C=1C=NC=CC=1C(O)=CC1=NC=CC=C1C(=O)C1=CC=CC=C1Cl GMNRLJOAZMNQMK-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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 229910019142 PO4 Inorganic materials 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
- 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
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims 1
- 229960001681 croscarmellose sodium Drugs 0.000 claims 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 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
- 230000001404 mediated effect Effects 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
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate 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
- 229960004274 stearic acid Drugs 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 8
- 206010041250 Social phobia Diseases 0.000 description 6
- 102000003141 Tachykinin Human genes 0.000 description 6
- 108060008037 tachykinin Proteins 0.000 description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 description 4
- 208000011688 Generalised anxiety disease Diseases 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- 208000029364 generalized anxiety disease Diseases 0.000 description 3
- 208000024714 major depressive disease Diseases 0.000 description 3
- 208000019906 panic disease Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 208000030090 Acute Disease Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 201000004813 Bronchopneumonia Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- -1 CHLOROPHENYL Chemical class 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- 206010021639 Incontinence Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000020114 Schizophrenia and other psychotic disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 102000007124 Tachykinin Receptors Human genes 0.000 description 1
- 108010072901 Tachykinin Receptors Proteins 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000005388 cross polarization Methods 0.000 description 1
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000010996 solid-state NMR spectroscopy Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000002455 vasospastic effect Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51430003P | 2003-10-24 | 2003-10-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200603234B true ZA200603234B (en) | 2007-07-25 |
Family
ID=34549327
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200603234A ZA200603234B (en) | 2003-10-24 | 2006-04-21 | Novel crystalline forms of {2-[1-(3,5-bis-trifluoromethyul-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-[2-chlorophenyl)-methanone |
Country Status (28)
Country | Link |
---|---|
US (1) | US7381826B2 (da) |
JP (1) | JP4959336B2 (da) |
KR (1) | KR100848407B1 (da) |
CN (1) | CN1863791B (da) |
AR (1) | AR046131A1 (da) |
AT (1) | ATE462700T1 (da) |
AU (1) | AU2004285855B8 (da) |
BR (1) | BRPI0415010B8 (da) |
CA (1) | CA2542140C (da) |
CL (2) | CL2009001310A1 (da) |
CR (1) | CR8353A (da) |
DE (1) | DE602004026333D1 (da) |
DK (1) | DK1675846T3 (da) |
EA (1) | EA008881B1 (da) |
EC (1) | ECSP066517A (da) |
ES (1) | ES2340772T3 (da) |
HR (1) | HRP20100207T1 (da) |
IL (1) | IL174926A0 (da) |
MA (1) | MA28329A1 (da) |
MY (1) | MY157375A (da) |
NO (1) | NO335090B1 (da) |
NZ (2) | NZ545917A (da) |
PE (1) | PE20050481A1 (da) |
PT (1) | PT1675846E (da) |
TW (1) | TW200524906A (da) |
UA (1) | UA82901C2 (da) |
WO (1) | WO2005042515A1 (da) |
ZA (1) | ZA200603234B (da) |
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 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
2004
- 2004-10-12 DE DE602004026333T patent/DE602004026333D1/de active Active
- 2004-10-12 EA EA200600829A patent/EA008881B1/ru not_active IP Right Cessation
- 2004-10-12 AU AU2004285855A patent/AU2004285855B8/en active Active
- 2004-10-12 WO PCT/US2004/030914 patent/WO2005042515A1/en active Application Filing
- 2004-10-12 BR BRPI0415010A patent/BRPI0415010B8/pt active IP Right Grant
- 2004-10-12 NZ NZ545917A patent/NZ545917A/en unknown
- 2004-10-12 CA CA2542140A patent/CA2542140C/en active Active
- 2004-10-12 US US10/574,712 patent/US7381826B2/en active Active
- 2004-10-12 KR KR1020067007751A patent/KR100848407B1/ko active IP Right Grant
- 2004-10-12 ES ES04793893T patent/ES2340772T3/es active Active
- 2004-10-12 JP JP2006536635A patent/JP4959336B2/ja active Active
- 2004-10-12 PT PT04793893T patent/PT1675846E/pt unknown
- 2004-10-12 DK DK04793893.1T patent/DK1675846T3/da active
- 2004-10-12 CN CN2004800291393A patent/CN1863791B/zh active Active
- 2004-10-12 NZ NZ580480A patent/NZ580480A/en unknown
- 2004-10-12 AT AT04793893T patent/ATE462700T1/de active
- 2004-10-20 AR ARP040103801A patent/AR046131A1/es not_active Application Discontinuation
- 2004-10-20 PE PE2004001008A patent/PE20050481A1/es not_active Application Discontinuation
- 2004-10-21 MY MYPI20044338A patent/MY157375A/en unknown
- 2004-10-22 TW TW093132097A patent/TW200524906A/zh unknown
- 2004-12-10 UA UAA200604473A patent/UA82901C2/uk unknown
-
2006
- 2006-04-11 IL IL174926A patent/IL174926A0/en unknown
- 2006-04-21 CR CR8353A patent/CR8353A/es not_active Application Discontinuation
- 2006-04-21 EC EC2006006517A patent/ECSP066517A/es unknown
- 2006-04-21 ZA ZA200603234A patent/ZA200603234B/en unknown
- 2006-05-22 MA MA29043A patent/MA28329A1/fr unknown
- 2006-05-24 NO NO20062371A patent/NO335090B1/no unknown
-
2009
- 2009-05-29 CL CL2009001310A patent/CL2009001310A1/es unknown
- 2009-05-29 CL CL2009001311A patent/CL2009001311A1/es unknown
-
2010
- 2010-04-13 HR HR20100207T patent/HRP20100207T1/hr unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200603234B (en) | Novel crystalline forms of {2-[1-(3,5-bis-trifluoromethyul-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-[2-chlorophenyl)-methanone | |
JP7042175B2 (ja) | 3-(イミダゾ[1,2-b]ピリダジン-3-イルエチニル)-4-メチル-N-{4-[(4-メチルピペラジン-1-イル)メチル]-3-(トリフルオロメチル)フェニル}ベンズアミドおよびその一塩酸塩の結晶形 | |
EP3243819A1 (en) | New crystal form of neratinib maleate and preparation method therefor | |
WO1994010167A1 (en) | Tachykinin antagonists | |
EP0707006A1 (de) | Aroyl-piperidin-Derivate | |
TWI445697B (zh) | 塔適那偉(atazanavir)硫酸氫鹽之製法及其新穎的形式 | |
SK6112003A3 (en) | Amidoalkyl-piperidine and amidoalkyl-piperazine derivatives for the treatment of nervous system disorders | |
WO2016131431A1 (en) | Solid forms of empagliflozin | |
WO2023087611A1 (zh) | 一类依巴斯汀的盐及其制备方法和应用 | |
CZ180898A3 (cs) | Způsob a meziprodukty pro výrobu 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidinu | |
JP2019517494A (ja) | 腎髄質外層カリウムチャネル阻害剤としての医薬的に許容される塩 | |
AU2017331930A1 (en) | Crystalline forms | |
EP3724176B1 (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 | |
NO171362B (no) | Analogifremgangsmaate for fremstilling av nye aralkylaminforbindelser og deres salter | |
WO2018103663A1 (zh) | 一种取代的吡嗪甲酰胺类化合物及包含该化合物的组合物及其用途 | |
WO2002076447A1 (en) | Hallogenated aminobenzophenones and aminobenzoylpyridines as inhibitors of il-1 and tnf | |
CN114456150A (zh) | Nr2b受体拮抗剂或其可药用的盐、制备方法及用途 | |
SK5282002A3 (en) | Phenyl- and pyridyl-tetrahydro-pyridines having tnf inhibiting activity | |
US20220235030A1 (en) | Selective histamine h3 antagonist acid addition salts and process for the preparation thereof | |
EP1675846B1 (en) | 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 | |
JP2018526365A (ja) | 1−(4−(2−((1−(3,4−ジフルオロフェニル)−1h−ピラゾール−3−イル)メトキシ)エチル)ピペラジン−1−イル)エタノン塩 | |
EP3256477A1 (en) | Solid forms of dolutegravir salts and a method of their preparation | |
WO2005080385A1 (ja) | インダノール誘導体 | |
CN113631554A (zh) | 苯并噻唑化合物的药用盐、多晶型物及其制备方法 | |
CN113382633A (zh) | (4-(2-氟-4-(1-甲基-1H-苯并[d]咪唑-5-基)苯甲酰基)哌嗪-1-基)(1-羟基环丙基)甲酮的固体形式 |