CA2256013A1 - Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic - Google Patents
Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepilepticInfo
- Publication number
- CA2256013A1 CA2256013A1 CA002256013A CA2256013A CA2256013A1 CA 2256013 A1 CA2256013 A1 CA 2256013A1 CA 002256013 A CA002256013 A CA 002256013A CA 2256013 A CA2256013 A CA 2256013A CA 2256013 A1 CA2256013 A1 CA 2256013A1
- Authority
- CA
- Canada
- Prior art keywords
- carboxamide
- triazole
- antiepileptic
- difluorobenzyl
- crystal modification
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
Abstract
The invention relates to the novel modification A or A' of the compound 1-(2, 6-difluoroben-zyl)-1H-1,2,3-triazole-4-carboxamide of formula (I), its use for the treatment of epilepsy, and pharmaceutical preparations comprising this crystal modification.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1404/97 | 1997-06-10 | ||
CH140497 | 1997-06-10 | ||
PCT/EP1998/003427 WO1998056772A1 (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3--triazole-4-carboxamide and its use as antiepileptic |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2256013A1 true CA2256013A1 (en) | 1998-12-17 |
CA2256013C CA2256013C (en) | 2007-10-16 |
Family
ID=4209650
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002256015A Expired - Lifetime CA2256015C (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
CA2614926A Expired - Lifetime CA2614926C (en) | 1997-06-10 | 1998-06-08 | Crystal modification c of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
CA002256013A Expired - Lifetime CA2256013C (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002256015A Expired - Lifetime CA2256015C (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
CA2614926A Expired - Lifetime CA2614926C (en) | 1997-06-10 | 1998-06-08 | Crystal modification c of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
Country Status (37)
Country | Link |
---|---|
US (6) | US6740669B1 (en) |
EP (2) | EP0994864B1 (en) |
JP (2) | JP3672575B2 (en) |
KR (2) | KR100425656B1 (en) |
CN (3) | CN1159300C (en) |
AR (4) | AR012945A1 (en) |
AT (2) | ATE237599T1 (en) |
AU (2) | AU725528B2 (en) |
BR (2) | BR9804947A (en) |
CA (3) | CA2256015C (en) |
CO (2) | CO4940452A1 (en) |
CY (1) | CY2007014I2 (en) |
CZ (2) | CZ292260B6 (en) |
DE (3) | DE69813560T2 (en) |
DK (2) | DK0994863T3 (en) |
ES (2) | ES2192779T3 (en) |
FR (1) | FR07C0037I2 (en) |
HK (3) | HK1028242A1 (en) |
HU (2) | HU225153B1 (en) |
ID (2) | ID27660A (en) |
IL (2) | IL125733A (en) |
LU (1) | LU91345I2 (en) |
MY (2) | MY120156A (en) |
NL (1) | NL300284I2 (en) |
NO (2) | NO329315B1 (en) |
NZ (2) | NZ331370A (en) |
PE (2) | PE79799A1 (en) |
PL (2) | PL192114B1 (en) |
PT (1) | PT994864E (en) |
RU (2) | RU2198167C2 (en) |
SI (2) | SI0994864T1 (en) |
SK (2) | SK283685B6 (en) |
TR (2) | TR199801631T1 (en) |
TW (2) | TW403740B (en) |
UY (1) | UY25844A1 (en) |
WO (2) | WO1998056772A1 (en) |
ZA (2) | ZA984967B (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW403740B (en) | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
EP1509524B1 (en) * | 2002-05-31 | 2008-03-26 | Schering Corporation | Xanthine phosphodiesterase v inhibitor polymorphs |
GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
US20090069390A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched rufinamide |
NZ591725A (en) | 2008-10-13 | 2012-09-28 | Cipla Ltd | PROCESS FOR THE PREPARATION OF RUFINAMIDE which is also known as 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
CN101768124B (en) * | 2008-12-30 | 2012-01-04 | 北京本草天源药物研究院 | Medicine crystal, preparation method and purpose thereof |
IT1395736B1 (en) * | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | CRYSTALLINE FORMS OF RUFINAMIDE |
KR101597338B1 (en) * | 2009-09-04 | 2016-02-24 | 탁티칼 떼라페우틱스 인크. | Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulations |
EP2465853A1 (en) * | 2010-12-14 | 2012-06-20 | Laboratorios Lesvi, S.L. | Polymorph of rufinamide and process for obtaining it |
WO2011135105A1 (en) | 2010-04-30 | 2011-11-03 | Laboratorios Lesvi, S.L. | Improved process for preparing rufinamide intermediate |
ITMI20110718A1 (en) | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | PROCEDURE FOR PURIFICATION OF RUFINAMIDE |
US10206874B2 (en) | 2012-07-20 | 2019-02-19 | Hetero Research Foundation | Rufinamide solid dispersion |
WO2021099481A1 (en) | 2019-11-20 | 2021-05-27 | Medichem, S.A. | Solid composition containing rufinamide |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3992378A (en) | 1973-12-26 | 1976-11-16 | Eli Lilly And Company | Fluoralkyl quinoxadinediones |
US4156734A (en) * | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
GB1511195A (en) | 1976-10-18 | 1978-05-17 | Ici America Inc | Triazole derivatives |
US4536518A (en) * | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
US4346097A (en) * | 1980-09-30 | 1982-08-24 | Warner-Lambert Company | Method for treating convulsions with pyrazole-4-carboxamide derivatives |
FI834666A (en) | 1982-12-23 | 1984-06-24 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV NYA ARALKYLTRIAZOLFOERENINGAR. |
US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
US4511572A (en) * | 1983-03-18 | 1985-04-16 | The University Of Kentucky Research Foundation | Triazoline anticonvulsant drugs |
FI93544C (en) * | 1985-04-18 | 1995-04-25 | Ciba Geigy Ag | Process for the preparation of fluorinated 1-benzyl-1H-1,2,3-triazole compounds with anticonvulsant action |
CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
JPH02214504A (en) | 1989-02-15 | 1990-08-27 | Nissan Chem Ind Ltd | Method for depositing crystal of compound having plural crystal forms |
JPH04506967A (en) | 1989-07-27 | 1992-12-03 | ジー.ディー.サール アンド カンパニー | Renal selective products for the treatment of hypertension |
IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
CA2095444C (en) | 1990-11-06 | 2001-06-19 | Shuichi Sakamoto | Fused pyrazine derivatives |
JP2753911B2 (en) | 1991-12-06 | 1998-05-20 | キッセイ薬品工業株式会社 | Crystal polymorph of N-tert-butyl-1-methyl-3,3-diphenylpropylamine hydrochloride and method for producing the same |
DE4217952A1 (en) | 1992-05-30 | 1993-12-02 | Basf Ag | Quinoxaline-2,3 (1H, 4H) diones |
US5248699A (en) * | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
US5631373A (en) | 1993-11-05 | 1997-05-20 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
GB9419318D0 (en) | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
US6096779A (en) | 1995-02-22 | 2000-08-01 | Hoechst Pharmaceuticals & Chemicals K.K. | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
CN1083436C (en) * | 1996-07-11 | 2002-04-24 | 诺瓦提斯公司 | Process for preparing 1-substituted 4-cyano-1,2,3-triazoles |
TW403740B (en) * | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
-
1998
- 1998-06-04 TW TW087108859A patent/TW403740B/en not_active IP Right Cessation
- 1998-06-04 TW TW087108858A patent/TW526195B/en not_active IP Right Cessation
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 CA CA002256015A patent/CA2256015C/en not_active Expired - Lifetime
- 1998-06-08 IL IL12573398A patent/IL125733A/en active Protection Beyond IP Right Term
- 1998-06-08 CA CA2614926A patent/CA2614926C/en not_active Expired - Lifetime
- 1998-06-08 DE DE69813560T patent/DE69813560T2/en not_active Expired - Lifetime
- 1998-06-08 ES ES98934929T patent/ES2192779T3/en not_active Expired - Lifetime
- 1998-06-08 US US09/125,329 patent/US6740669B1/en not_active Expired - Lifetime
- 1998-06-08 KR KR10-1998-0708150A patent/KR100425656B1/en not_active IP Right Cessation
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 PE PE1998000478A patent/PE79799A1/en not_active IP Right Cessation
- 1998-06-08 NZ NZ331370A patent/NZ331370A/en not_active IP Right Cessation
- 1998-06-08 CN CNB988056755A patent/CN1159300C/en not_active Expired - Lifetime
- 1998-06-08 SI SI9830450T patent/SI0994864T1/en unknown
- 1998-06-08 PL PL330798A patent/PL192114B1/en unknown
- 1998-06-08 TR TR1998/01631T patent/TR199801631T1/en unknown
- 1998-06-08 AT AT98934930T patent/ATE237599T1/en active
- 1998-06-08 EP EP98934929A patent/EP0994863B1/en not_active Expired - Lifetime
- 1998-06-08 RU RU99104300/04A patent/RU2198167C2/en active
- 1998-06-08 CZ CZ19982534A patent/CZ292260B6/en not_active IP Right Cessation
- 1998-06-08 ID IDW980065D patent/ID27660A/en unknown
- 1998-06-08 DE DE69811500T patent/DE69811500T2/en not_active Expired - Lifetime
- 1998-06-08 CA CA002256013A patent/CA2256013C/en not_active Expired - Lifetime
- 1998-06-08 CZ CZ19982533A patent/CZ292481B6/en not_active IP Right Cessation
- 1998-06-08 AT AT98934929T patent/ATE232852T1/en active
- 1998-06-08 SK SK1093-98A patent/SK283685B6/en not_active IP Right Cessation
- 1998-06-08 KR KR10-1998-0708149A patent/KR100409168B1/en not_active IP Right Cessation
- 1998-06-08 CN CNB2004100473675A patent/CN1298708C/en not_active Expired - Lifetime
- 1998-06-08 DK DK98934929T patent/DK0994863T3/en active
- 1998-06-08 HU HU0002113A patent/HU225153B1/en unknown
- 1998-06-08 ID IDW980066D patent/ID21014A/en unknown
- 1998-06-08 SK SK1094-98A patent/SK283734B6/en not_active IP Right Cessation
- 1998-06-08 AU AU84371/98A patent/AU725528B2/en not_active Expired
- 1998-06-08 PL PL330764A patent/PL191943B1/en unknown
- 1998-06-08 RU RU99104299/04A patent/RU2194041C2/en active
- 1998-06-08 IL IL12573298A patent/IL125732A/en not_active IP Right Cessation
- 1998-06-08 HU HU0000798A patent/HU226107B1/en unknown
- 1998-06-08 DE DE122007000051C patent/DE122007000051I2/en active Active
- 1998-06-08 NZ NZ331371A patent/NZ331371A/en not_active IP Right Cessation
- 1998-06-08 SI SI9830405T patent/SI0994863T1/en unknown
- 1998-06-08 AU AU84372/98A patent/AU725517B2/en not_active Expired
- 1998-06-08 PT PT98934930T patent/PT994864E/en unknown
- 1998-06-08 JP JP53628998A patent/JP3672575B2/en not_active Expired - Lifetime
- 1998-06-08 BR BR9804947A patent/BR9804947A/en not_active Application Discontinuation
- 1998-06-08 BR BR9804946A patent/BR9804946A/en not_active Application Discontinuation
- 1998-06-08 JP JP53628898A patent/JP3672574B2/en not_active Expired - Lifetime
- 1998-06-08 DK DK98934930T patent/DK0994864T3/en active
- 1998-06-08 TR TR1998/01630T patent/TR199801630T1/en unknown
- 1998-06-08 PE PE1998000479A patent/PE80999A1/en not_active IP Right Cessation
- 1998-06-08 ES ES98934930T patent/ES2197485T3/en not_active Expired - Lifetime
- 1998-06-08 CN CN988000113A patent/CN1132820C/en not_active Expired - Lifetime
- 1998-06-08 WO PCT/EP1998/003428 patent/WO1998056773A1/en active IP Right Grant
- 1998-06-09 CO CO98032879A patent/CO4940452A1/en unknown
- 1998-06-09 CO CO98032885A patent/CO4940448A1/en unknown
- 1998-06-09 ZA ZA984967A patent/ZA984967B/en unknown
- 1998-06-09 MY MYPI98002570A patent/MY120156A/en unknown
- 1998-06-09 AR ARP980102707A patent/AR012945A1/en not_active Application Discontinuation
- 1998-06-09 AR ARP980102708A patent/AR012946A1/en not_active Application Discontinuation
- 1998-06-09 MY MYPI98002572A patent/MY125854A/en unknown
- 1998-06-09 ZA ZA984966A patent/ZA984966B/en unknown
- 1998-08-11 NO NO19983667A patent/NO329315B1/en not_active IP Right Cessation
- 1998-08-11 NO NO19983666A patent/NO329314B1/en not_active IP Right Cessation
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1999
- 1999-12-10 UY UY25844A patent/UY25844A1/en not_active Application Discontinuation
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2000
- 2000-10-25 HK HK00106807A patent/HK1028242A1/en not_active IP Right Cessation
- 2000-10-25 HK HK00106804A patent/HK1028241A1/en not_active IP Right Cessation
- 2000-11-17 HK HK00107340A patent/HK1028031A1/en not_active IP Right Cessation
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2001
- 2001-05-31 US US09/871,366 patent/US6455556B2/en not_active Expired - Lifetime
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2002
- 2002-11-14 US US10/294,408 patent/US20030125568A1/en not_active Abandoned
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2004
- 2004-02-26 US US10/787,528 patent/US20040167186A1/en not_active Abandoned
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2006
- 2006-01-11 US US11/329,945 patent/US7750028B2/en not_active Expired - Fee Related
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2007
- 2007-05-17 AR ARP070102132A patent/AR061005A2/en not_active Application Discontinuation
- 2007-05-17 AR ARP070102131A patent/AR061004A2/en unknown
- 2007-07-03 NL NL300284C patent/NL300284I2/en unknown
- 2007-07-04 LU LU91345C patent/LU91345I2/en unknown
- 2007-07-06 FR FR07C0037C patent/FR07C0037I2/fr active Active
- 2007-07-13 CY CY200700014C patent/CY2007014I2/en unknown
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2010
- 2010-04-26 US US12/767,003 patent/US8076362B2/en not_active Expired - Fee Related
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20180608 |