CN1259127A - 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
- CN1259127A CN1259127A CN98805675A CN98805675A CN1259127A CN 1259127 A CN1259127 A CN 1259127A CN 98805675 A CN98805675 A CN 98805675A CN 98805675 A CN98805675 A CN 98805675A CN 1259127 A CN1259127 A CN 1259127A
- Authority
- CN
- China
- Prior art keywords
- weak
- modification
- medium
- difluorobenzyl
- triazole
- 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
- 238000012986 modification Methods 0.000 title claims abstract description 102
- 230000004048 modification Effects 0.000 title claims abstract description 102
- 239000013078 crystal Substances 0.000 title abstract description 12
- 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
- 239000001961 anticonvulsive agent Substances 0.000 title description 3
- 230000003556 anti-epileptic effect Effects 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000001228 spectrum Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- 230000003595 spectral effect Effects 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000005079 FT-Raman Methods 0.000 claims description 6
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 6
- 238000001028 reflection method Methods 0.000 claims description 5
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 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
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000001138 tear Anatomy 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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 101150064233 Pan2 gene Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000020245 homoiothermy Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- -1 polyoxyethylene Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000005477 standard model Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000012982 x-ray structure analysis Methods 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
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 (16)
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 true CN1259127A (zh) | 2000-07-05 |
CN1159300C 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 |
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 |
CN988000113A Expired - Lifetime CN1132820C (zh) | 1997-06-10 | 1998-06-08 | 药物的结晶改良体 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
CN988000113A Expired - Lifetime CN1132820C (zh) | 1997-06-10 | 1998-06-08 | 药物的结晶改良体 |
Country Status (37)
Country | Link |
---|---|
US (6) | US6740669B1 (zh) |
EP (2) | EP0994864B1 (zh) |
JP (2) | JP3672575B2 (zh) |
KR (2) | KR100425656B1 (zh) |
CN (3) | CN1159300C (zh) |
AR (4) | AR012945A1 (zh) |
AT (2) | ATE237599T1 (zh) |
AU (2) | AU725528B2 (zh) |
BR (2) | BR9804947A (zh) |
CA (3) | CA2256015C (zh) |
CO (2) | CO4940452A1 (zh) |
CY (1) | CY2007014I2 (zh) |
CZ (2) | CZ292260B6 (zh) |
DE (3) | DE69813560T2 (zh) |
DK (2) | DK0994863T3 (zh) |
ES (2) | ES2192779T3 (zh) |
FR (1) | FR07C0037I2 (zh) |
HK (3) | HK1028242A1 (zh) |
HU (2) | HU225153B1 (zh) |
ID (2) | ID27660A (zh) |
IL (2) | IL125733A (zh) |
LU (1) | LU91345I2 (zh) |
MY (2) | MY120156A (zh) |
NL (1) | NL300284I2 (zh) |
NO (2) | NO329315B1 (zh) |
NZ (2) | NZ331370A (zh) |
PE (2) | PE79799A1 (zh) |
PL (2) | PL192114B1 (zh) |
PT (1) | PT994864E (zh) |
RU (2) | RU2198167C2 (zh) |
SI (2) | SI0994864T1 (zh) |
SK (2) | SK283685B6 (zh) |
TR (2) | TR199801631T1 (zh) |
TW (2) | TW403740B (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 |
---|---|---|---|---|
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 (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 |
KR101597338B1 (ko) * | 2009-09-04 | 2016-02-24 | 탁티칼 떼라페우틱스 인크. | 5-아미노 또는 치환된 아미노 1,2,3-트리아졸 화합물 및 이의 오로트산염 제형들의 신규한 조성물들 및 이의 제조방법 |
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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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 (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 |
CA2095444C (en) | 1990-11-06 | 2001-06-19 | Shuichi Sakamoto | Fused pyrazine derivatives |
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 |
US6096779A (en) | 1995-02-22 | 2000-08-01 | Hoechst Pharmaceuticals & Chemicals K.K. | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
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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/zh not_active IP Right Cessation
- 1998-06-04 TW TW087108858A patent/TW526195B/zh 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
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