CN1159300C - 1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用作抗癫痫药的用途 - Google Patents
1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用作抗癫痫药的用途 Download PDFInfo
- Publication number
- CN1159300C CN1159300C CNB988056755A CN98805675A CN1159300C CN 1159300 C CN1159300 C CN 1159300C CN B988056755 A CNB988056755 A CN B988056755A CN 98805675 A CN98805675 A CN 98805675A CN 1159300 C CN1159300 C CN 1159300C
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- China
- Prior art keywords
- weak
- modification
- medium
- difluorobenzyl
- triazole
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- 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
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- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 title abstract 2
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- 230000003556 anti-epileptic effect Effects 0.000 title 1
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- 239000000654 additive Substances 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001237 Raman spectrum Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 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
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- 235000019253 formic acid Nutrition 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
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
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- 101150064233 Pan2 gene Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- -1 Polyoxyethylene Polymers 0.000 description 1
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- 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
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Images
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
Description
改良体A: | 改良体B: | 改良体C: | |||
d[] | 强度 | d[] | 强度 | d[] | 强度 |
10.9 | 弱 | 11.0 | 中等 | 9.0 | 中等 |
10.5 | 中等 | 8.3 | 中等 | 7.0 | 弱 |
6.6 | 弱 | 8.1 | 很弱 | 5.49 | 弱 |
5.63 | 弱 | 5.68 | 很弱 | 5.11 | 很弱 |
5.25 | 弱 | 5.18 | 很强 | 4.80 | 弱 |
5.14 | 中等 | 5.11 | 弱 | 4.73 | 强 |
4.94 | 弱 | 4.88 | 中等 | 4.65 | 很强 |
4.84 | 很强 | 4.80 | 强 | 4.47 | 很弱 |
4.55 | 强 | 4.71 | 很弱 | 4.19 | 很弱 |
4.42 | 很弱 | 4.61 | 弱 | 4.11 | 很弱 |
4.34 | 中等 | 4.45 | 弱 | 3.98 | 很弱 |
4.23 | 很弱 | 4.42 | 强 | 3.83 | 很弱 |
4.16 | 弱 | 4.33 | 很强 | 3.75 | 强 |
4.07 | 中等 | 4.19 | 中等 | 3.73 | 弱 |
4.01 | 弱 | 4.12 | 强 | 3.54 | 中等 |
3.68 | 很弱 | 4.09 | 弱 | 3.50 | 弱 |
3.64 | 很弱 | 3.99 | 很弱 | 3.42 | 强 |
3.60 | 弱 | 3.95 | 很弱 | 3.25 | 中等 |
3.56 | 弱 | 3.84 | 弱 | 2.88 | 很弱 |
3.51 | 中等 | 3.81 | 中等 | 2.80 | 很弱 |
3.48 | 中等 | 3.65 | 弱 | 2.74 | 很弱 |
3.38 | 很弱 | 3.61 | 很弱 | 2.67 | 很弱 |
3.25 | 强 | 3.58 | 很弱 | 2.64 | 弱 |
3.19 | 中等 | 3.54 | 弱 |
3.15 | 中等 | 3.50 | 中等 | ||
3.11 | 弱 | 3.47 | 很弱 | ||
3.07 | 中等 | 3.41 | 中等 | ||
2.93 | 很弱 | 3.36 | 很强 | ||
2.87 | 很弱 | 3.32 | 强 | ||
2.81 | 中等 | 3.28 | 中等 | ||
2.76 | 弱 | 3.24 | 中等 | ||
2.73 | 很弱 | 3.10 | 弱 | ||
2.68 | 弱 | 3.07 | 弱 | ||
2.62 | 很弱 | 3.05 | 中等 | ||
2.53 | 弱 | 2.93 | 弱 | ||
2.43 | 弱 | 2.88 | 弱 | ||
2.40 | 很弱 | 2.87 | 很弱 | ||
2.83 | 中等 | ||||
2.66 | 弱 | ||||
2.63 | 很弱 | ||||
2.55 | 弱 | ||||
2.50 | 弱 | ||||
2.46 | 弱 | ||||
2.44 | 弱 | ||||
2.37 | 弱 | ||||
2.35 | 弱 |
Claims (5)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH140497 | 1997-06-10 | ||
CH1404/1997 | 1997-06-10 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004100473675A Division CN1298708C (zh) | 1997-06-10 | 1998-06-08 | 1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1259127A CN1259127A (zh) | 2000-07-05 |
CN1159300C true CN1159300C (zh) | 2004-07-28 |
Family
ID=4209650
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB988056755A Expired - Lifetime CN1159300C (zh) | 1997-06-10 | 1998-06-08 | 1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用作抗癫痫药的用途 |
CN988000113A Expired - Lifetime CN1132820C (zh) | 1997-06-10 | 1998-06-08 | 药物的结晶改良体 |
CNB2004100473675A Expired - Lifetime CN1298708C (zh) | 1997-06-10 | 1998-06-08 | 1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用途 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN988000113A Expired - Lifetime CN1132820C (zh) | 1997-06-10 | 1998-06-08 | 药物的结晶改良体 |
CNB2004100473675A Expired - Lifetime CN1298708C (zh) | 1997-06-10 | 1998-06-08 | 1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的结晶改良体及其用途 |
Country Status (37)
Country | Link |
---|---|
US (6) | US6740669B1 (zh) |
EP (2) | EP0994864B1 (zh) |
JP (2) | JP3672574B2 (zh) |
KR (2) | KR100425656B1 (zh) |
CN (3) | CN1159300C (zh) |
AR (4) | AR012945A1 (zh) |
AT (2) | ATE237599T1 (zh) |
AU (2) | AU725528B2 (zh) |
BR (2) | BR9804946A (zh) |
CA (3) | CA2256013C (zh) |
CO (2) | CO4940452A1 (zh) |
CY (1) | CY2007014I2 (zh) |
CZ (2) | CZ292260B6 (zh) |
DE (3) | DE69811500T2 (zh) |
DK (2) | DK0994864T3 (zh) |
ES (2) | ES2192779T3 (zh) |
FR (1) | FR07C0037I2 (zh) |
HK (3) | HK1028241A1 (zh) |
HU (2) | HU225153B1 (zh) |
ID (2) | ID21014A (zh) |
IL (2) | IL125732A (zh) |
LU (1) | LU91345I2 (zh) |
MY (2) | MY125854A (zh) |
NL (1) | NL300284I2 (zh) |
NO (2) | NO329315B1 (zh) |
NZ (2) | NZ331371A (zh) |
PE (2) | PE80999A1 (zh) |
PL (2) | PL192114B1 (zh) |
PT (1) | PT994864E (zh) |
RU (2) | RU2194041C2 (zh) |
SI (2) | SI0994863T1 (zh) |
SK (2) | SK283685B6 (zh) |
TR (2) | TR199801631T1 (zh) |
TW (2) | TW526195B (zh) |
UY (1) | UY25844A1 (zh) |
WO (2) | WO1998056772A1 (zh) |
ZA (2) | ZA984967B (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
ATE390425T1 (de) * | 2002-05-31 | 2008-04-15 | Schering Corp | Xanthin-phosphodiesterase-v-hemmer polymorphe |
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 (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 |
WO2011028288A1 (en) * | 2009-09-04 | 2011-03-10 | 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 |
WO2011135105A1 (en) * | 2010-04-30 | 2011-11-03 | 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 |
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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 (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 |
PH22568A (en) * | 1985-04-18 | 1988-10-17 | Ciba Geigy Ag | Fluorinated benzyl triazoles and pharmaceutical compositions containing the same |
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 |
DE69132340T2 (de) | 1990-11-06 | 2001-02-08 | 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 |
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GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
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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 PL PL330798A patent/PL192114B1/pl unknown
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 PT PT98934930T patent/PT994864E/pt unknown
- 1998-06-08 AT AT98934930T patent/ATE237599T1/de active
- 1998-06-08 HU HU0002113A patent/HU225153B1/hu unknown
- 1998-06-08 CA CA002256013A patent/CA2256013C/en not_active Expired - Lifetime
- 1998-06-08 CZ CZ19982534A patent/CZ292260B6/cs not_active IP Right Cessation
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 CA CA2614926A patent/CA2614926C/en not_active Expired - Lifetime
- 1998-06-08 PE PE1998000479A patent/PE80999A1/es not_active IP Right Cessation
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