CA2256013C - 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 antiepileptic Download PDFInfo
- Publication number
- CA2256013C CA2256013C CA002256013A CA2256013A CA2256013C CA 2256013 C CA2256013 C CA 2256013C CA 002256013 A CA002256013 A CA 002256013A CA 2256013 A CA2256013 A CA 2256013A CA 2256013 C CA2256013 C CA 2256013C
- Authority
- CA
- Canada
- Prior art keywords
- ang
- weak
- modification
- medium
- 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.)
- Expired - Lifetime
Links
- 238000012986 modification Methods 0.000 title claims abstract description 109
- 230000004048 modification Effects 0.000 title claims abstract description 108
- 239000013078 crystal Substances 0.000 title claims abstract description 29
- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 230000003556 anti-epileptic effect Effects 0.000 title description 3
- 239000001961 anticonvulsive agent Substances 0.000 title description 3
- 206010015037 epilepsy Diseases 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000000843 powder Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 6
- 239000008188 pellet Substances 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims description 5
- 230000009102 absorption Effects 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000001028 reflection method Methods 0.000 claims description 4
- 238000005079 FT-Raman Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000001237 Raman spectrum Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- PVIAOIJYIQHKPL-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole-4-carbonitrile Chemical compound FC1=CC=CC(F)=C1CN1N=NC(C#N)=C1 PVIAOIJYIQHKPL-UHFFFAOYSA-N 0.000 description 1
- OPJHWTKDQYKYHL-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1=C(F)C=CC=C1F OPJHWTKDQYKYHL-UHFFFAOYSA-N 0.000 description 1
- JSZUBPHMRHROHZ-UHFFFAOYSA-N 2-(azidomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CN=[N+]=[N-] JSZUBPHMRHROHZ-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- 101710179738 6,7-dimethyl-8-ribityllumazine synthase 1 Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101710186608 Lipoyl synthase 1 Proteins 0.000 description 1
- 101710137584 Lipoyl synthase 1, chloroplastic Proteins 0.000 description 1
- 101710090391 Lipoyl synthase 1, mitochondrial Proteins 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 239000004353 Polyethylene glycol 8000 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 238000004279 X-ray Guinier Methods 0.000 description 1
- 238000005147 X-ray Weissenberg Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- XVEURJOWGBWEPY-UHFFFAOYSA-N methyl 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1CC1=C(F)C=CC=C1F XVEURJOWGBWEPY-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940085678 polyethylene glycol 8000 Drugs 0.000 description 1
- 235000019446 polyethylene glycol 8000 Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (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)
- Plural Heterocyclic Compounds (AREA)
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 CA2256013A1 (en) | 1998-12-17 |
| CA2256013C true CA2256013C (en) | 2007-10-16 |
Family
ID=4209650
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
Country Status (36)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW526195B (en) | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
| WO2003101991A1 (en) * | 2002-05-31 | 2003-12-11 | 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 |
| JP2012505191A (ja) * | 2008-10-13 | 2012-03-01 | シプラ・リミテッド | ルフィナマイドの製造方法 |
| CN101768124B (zh) * | 2008-12-30 | 2012-01-04 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
| IT1395736B1 (it) * | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | Forme cristalline di rufinamide |
| SG178413A1 (en) * | 2009-09-04 | 2012-03-29 | Tactical Therapeutics Inc | 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 |
| EP2563766B1 (en) * | 2010-04-30 | 2014-06-25 | Laboratorios Lesvi, S.L. | Improved process for preparing rufinamide intermediate |
| ITMI20110718A1 (it) * | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | Procedimento per la purificazione di 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 |
| FI834666A7 (fi) | 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 (fi) * | 1985-04-18 | 1995-04-25 | Ciba Geigy Ag | Menetelmä fluorattujen, antikonvulsiivisesti vaikuttavien 1-bentsyyli-1H-1,2,3-triatsoliyhdisteiden valmistamiseksi |
| CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
| JPH02214504A (ja) | 1989-02-15 | 1990-08-27 | Nissan Chem Ind Ltd | 光学活性キノキサリン化合物の晶析法 |
| JPH04506967A (ja) | 1989-07-27 | 1992-12-03 | ジー．ディー．サール アンド カンパニー | 高血圧症治療用腎選択性生成物 |
| IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| ATE194985T1 (de) | 1990-11-06 | 2000-08-15 | Yamanouchi Pharma Co Ltd | Kondensiertes pyrazinderivat |
| JP2753911B2 (ja) | 1991-12-06 | 1998-05-20 | キッセイ薬品工業株式会社 | Ｎ−ｔｅｒｔ−ブチル−１−メチル−３，３−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 |
| DE4217952A1 (de) | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
| 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 |
| DK0812320T3 (da) | 1995-02-22 | 2003-04-14 | Aventis Pharma Ltd | Amorft piretanid, polymorfe former deraf, fremgangsmåde til fremstilling deraf og deres anvendelse |
| JP3537147B2 (ja) * | 1996-07-11 | 2004-06-14 | ノバルティス アクチエンゲゼルシャフト | １―置換４―シアノ―１，２，３―トリアゾールの製造法 |
| TW526195B (en) | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
-
1998
- 1998-06-04 TW TW087108858A patent/TW526195B/zh not_active IP Right Cessation
- 1998-06-04 TW TW087108859A patent/TW403740B/zh not_active IP Right Cessation
- 1998-06-08 CN CNB2004100473675A patent/CN1298708C/zh not_active Expired - Lifetime
- 1998-06-08 JP JP53628998A patent/JP3672575B2/ja not_active Expired - Lifetime
- 1998-06-08 NZ NZ331371A patent/NZ331371A/xx not_active IP Right Cessation
- 1998-06-08 EP EP98934929A patent/EP0994863B1/en not_active Expired - Lifetime
- 1998-06-08 RU RU99104300/04A patent/RU2198167C2/ru active
- 1998-06-08 AT AT98934930T patent/ATE237599T1/de active
- 1998-06-08 AU AU84371/98A patent/AU725528B2/en not_active Expired
- 1998-06-08 CZ CZ19982533A patent/CZ292481B6/cs not_active IP Right Cessation
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 WO PCT/EP1998/003428 patent/WO1998056773A1/en active IP Right Grant
- 1998-06-08 DE DE122007000051C patent/DE122007000051I2/de active Active
- 1998-06-08 SI SI9830405T patent/SI0994863T1/xx unknown
- 1998-06-08 AT AT98934929T patent/ATE232852T1/de active
- 1998-06-08 IL IL12573298A patent/IL125732A/en not_active IP Right Cessation
- 1998-06-08 CA CA002256013A patent/CA2256013C/en not_active Expired - Lifetime
- 1998-06-08 ID IDW980066D patent/ID21014A/id unknown
- 1998-06-08 ES ES98934929T patent/ES2192779T3/es not_active Expired - Lifetime
- 1998-06-08 JP JP53628898A patent/JP3672574B2/ja not_active Expired - Lifetime
- 1998-06-08 BR BR9804946A patent/BR9804946A/pt not_active Application Discontinuation
- 1998-06-08 AU AU84372/98A patent/AU725517B2/en not_active Expired
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 ES ES98934930T patent/ES2197485T3/es not_active Expired - Lifetime
- 1998-06-08 CZ CZ19982534A patent/CZ292260B6/cs not_active IP Right Cessation
- 1998-06-08 KR KR10-1998-0708149A patent/KR100409168B1/ko not_active Expired - Lifetime
- 1998-06-08 NZ NZ331370A patent/NZ331370A/xx not_active IP Right Cessation
- 1998-06-08 KR KR10-1998-0708150A patent/KR100425656B1/ko not_active Expired - Lifetime
- 1998-06-08 SK SK1093-98A patent/SK283685B6/sk not_active IP Right Cessation
- 1998-06-08 DK DK98934929T patent/DK0994863T3/da active
- 1998-06-08 HU HU0000798A patent/HU226107B1/hu unknown
- 1998-06-08 RU RU99104299/04A patent/RU2194041C2/ru active
- 1998-06-08 SK SK1094-98A patent/SK283734B6/sk not_active IP Right Cessation
- 1998-06-08 DE DE69813560T patent/DE69813560T2/de not_active Expired - Lifetime
- 1998-06-08 PT PT98934930T patent/PT994864E/pt unknown
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