ZA200507995B - Process for the preparation of anticonvulsant derivatives of topiramate - Google Patents
Process for the preparation of anticonvulsant derivatives of topiramate Download PDFInfo
- Publication number
- ZA200507995B ZA200507995B ZA200507995A ZA200507995A ZA200507995B ZA 200507995 B ZA200507995 B ZA 200507995B ZA 200507995 A ZA200507995 A ZA 200507995A ZA 200507995 A ZA200507995 A ZA 200507995A ZA 200507995 B ZA200507995 B ZA 200507995B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- aqueous organic
- base
- sulfuryl diamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 71
- 230000008569 process Effects 0.000 title claims description 69
- 238000002360 preparation method Methods 0.000 title claims description 16
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical class C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 title description 7
- 230000001773 anti-convulsant effect Effects 0.000 title description 3
- 239000001961 anticonvulsive agent Substances 0.000 title description 3
- 229960003965 antiepileptics Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 79
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
- 150000007530 organic bases Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000007529 inorganic bases Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- PSSHGMIAIUYOJF-XBWDGYHZSA-N [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methanol Chemical compound C1O[C@@]2(CO)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 PSSHGMIAIUYOJF-XBWDGYHZSA-N 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- -1 methylenedioxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002009 alkene group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000008096 xylene Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 150000003738 xylenes Chemical class 0.000 description 11
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 10
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 10
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229960004394 topiramate Drugs 0.000 description 5
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 4
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJXREUZUPGMAII-UHFFFAOYSA-N sulfurazidic acid Chemical compound OS(=O)(=O)N=[N+]=[N-] WJXREUZUPGMAII-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- YUMNNMSNSLHINV-UHFFFAOYSA-N chloro sulfamate Chemical compound NS(=O)(=O)OCl YUMNNMSNSLHINV-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
-
- 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
-
- 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
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- 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
- A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45186303P | 2003-03-04 | 2003-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507995B true ZA200507995B (en) | 2007-01-31 |
Family
ID=32962650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507995A ZA200507995B (en) | 2003-03-04 | 2005-10-03 | Process for the preparation of anticonvulsant derivatives of topiramate |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7157589B2 (es) |
| EP (1) | EP1599490B8 (es) |
| JP (1) | JP4725976B2 (es) |
| KR (1) | KR20050119111A (es) |
| CN (1) | CN100376591C (es) |
| AR (1) | AR043466A1 (es) |
| AT (1) | ATE421521T1 (es) |
| AU (1) | AU2004217974A1 (es) |
| BR (1) | BRPI0407967A (es) |
| CA (1) | CA2517964A1 (es) |
| CL (1) | CL2004000438A1 (es) |
| DE (1) | DE602004019191D1 (es) |
| DK (1) | DK1599490T3 (es) |
| ES (1) | ES2254047T3 (es) |
| HK (1) | HK1088336A1 (es) |
| HR (1) | HRP20050756A2 (es) |
| MX (1) | MXPA05009384A (es) |
| MY (1) | MY139235A (es) |
| NO (1) | NO20054538L (es) |
| NZ (1) | NZ541811A (es) |
| PT (1) | PT1599490E (es) |
| RU (1) | RU2333216C2 (es) |
| SI (1) | SI1599490T1 (es) |
| TW (1) | TW200504089A (es) |
| UA (1) | UA81657C2 (es) |
| WO (1) | WO2004078769A1 (es) |
| ZA (1) | ZA200507995B (es) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7638291B2 (en) * | 2004-10-25 | 2009-12-29 | Seradyn, Inc. | Immunoassays for topiramate |
| US20060088886A1 (en) * | 2004-10-25 | 2006-04-27 | Anlong Ouyang | Topiramate analogs |
| WO2007099388A1 (en) * | 2006-03-01 | 2007-09-07 | Glade Organics Private Limited | An improved process for the manufacture of topiramate |
| WO2008010231A2 (en) * | 2006-05-26 | 2008-01-24 | Alembic Limited | A process for the purification of topiramate |
| US20090076128A1 (en) * | 2007-09-15 | 2009-03-19 | Protia Llc | Deuterium-enriched topiramate |
| US9303038B2 (en) | 2011-09-06 | 2016-04-05 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy and neurological diseases |
| AU2013257742A1 (en) | 2012-05-07 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for treatment of neuromuscular disorders and neurodegenerative disorders |
| WO2013167985A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological disorders |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| WO2013168025A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of blood clotting disorders |
| US9403826B2 (en) | 2012-05-08 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory disorders |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| US9266823B2 (en) | 2012-05-08 | 2016-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of parkinson's disease |
| WO2013167991A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic disorders |
| WO2013168000A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of severe pain |
| US9499527B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| US9315461B2 (en) | 2012-05-10 | 2016-04-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| US9403857B2 (en) | 2012-05-10 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168015A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of asthma and allergy |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168005A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| US9233161B2 (en) | 2012-05-10 | 2016-01-12 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological conditions |
| US9346742B2 (en) | 2012-05-10 | 2016-05-24 | Cellix Bio Private Limited | Compositions and methods for the treatment of fibromyalgia pain |
| WO2013168012A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| US9499526B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| US9492409B2 (en) | 2012-05-23 | 2016-11-15 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| WO2013175377A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| CN104603097A (zh) | 2012-05-23 | 2015-05-06 | 塞利克斯比奥私人有限公司 | 用于治疗多发性硬化症的组合物和方法 |
| US9227974B2 (en) | 2012-05-23 | 2016-01-05 | Cellex Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| SG11201407319YA (en) | 2012-05-23 | 2014-12-30 | Cellix Bio Private Ltd | Compositions and methods for treatment of inflammatory bowel disease |
| WO2013175344A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9187427B2 (en) | 2012-08-03 | 2015-11-17 | Cellix Bio Private Limited | N-substituted nicotinamide compounds and compositions for the treatment migraine and neurologic diseases |
| WO2014037833A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment inflammation and lipid disorders |
| CN104364231A (zh) | 2012-09-08 | 2015-02-18 | 塞利克斯比奥私人有限公司 | 用于治疗炎症和脂质异常的组合物和方法 |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| AU2014276346A1 (en) | 2013-06-04 | 2015-12-24 | Cellixbio Private Limited | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| WO2016110865A1 (en) | 2015-01-06 | 2016-07-14 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammation and pain |
| CA2976314C (en) | 2014-09-26 | 2021-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| EP3201168B1 (en) | 2014-09-29 | 2020-03-18 | Cellix Bio Private Limited | Compounds and compositions for the treatment of multiple sclerosis |
| EP3212626B1 (en) | 2014-10-27 | 2018-11-07 | Cellix Bio Private Limited | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| CN106632530A (zh) * | 2016-12-08 | 2017-05-10 | 陕西大生制药科技有限公司 | 高纯度托吡酯的制备方法 |
| CN108341844A (zh) * | 2018-04-25 | 2018-07-31 | 广州小桔生物科技有限公司 | 一种高纯度托吡酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513006A (en) * | 1983-09-26 | 1985-04-23 | Mcneil Lab., Inc. | Anticonvulsant sulfamate derivatives |
| US4582916A (en) * | 1983-09-26 | 1986-04-15 | Mcneilab, Inc. | Chlorosulfate and azidosulfate esters of tetrahydro-2H-pyran-2-yl-methanol |
| AU651244B2 (en) * | 1991-09-19 | 1994-07-14 | Mcneilab, Inc. | Process for the preparation of chlorosulfate and sulfamate derivatives of 2,3:4,5-bis-0-(1-methylethylidene)-beta-D- fructopyranose and (1-methylcyclohexyl)methanol |
-
2004
- 2004-02-03 UA UAA200508358A patent/UA81657C2/ru unknown
- 2004-03-01 US US10/790,274 patent/US7157589B2/en not_active Expired - Lifetime
- 2004-03-02 RU RU2005127626/04A patent/RU2333216C2/ru active
- 2004-03-02 JP JP2006508970A patent/JP4725976B2/ja not_active Expired - Fee Related
- 2004-03-02 AU AU2004217974A patent/AU2004217974A1/en not_active Abandoned
- 2004-03-02 EP EP04716438A patent/EP1599490B8/en not_active Expired - Lifetime
- 2004-03-02 MX MXPA05009384A patent/MXPA05009384A/es active IP Right Grant
- 2004-03-02 DK DK04716438T patent/DK1599490T3/da active
- 2004-03-02 PT PT04716438T patent/PT1599490E/pt unknown
- 2004-03-02 CA CA002517964A patent/CA2517964A1/en not_active Abandoned
- 2004-03-02 SI SI200431098T patent/SI1599490T1/sl unknown
- 2004-03-02 DE DE602004019191T patent/DE602004019191D1/de not_active Expired - Lifetime
- 2004-03-02 AT AT04716438T patent/ATE421521T1/de not_active IP Right Cessation
- 2004-03-02 NZ NZ541811A patent/NZ541811A/en unknown
- 2004-03-02 WO PCT/US2004/006263 patent/WO2004078769A1/en active Application Filing
- 2004-03-02 KR KR1020057016420A patent/KR20050119111A/ko not_active Application Discontinuation
- 2004-03-02 ES ES04716438T patent/ES2254047T3/es not_active Expired - Lifetime
- 2004-03-02 BR BRPI0407967-1A patent/BRPI0407967A/pt not_active IP Right Cessation
- 2004-03-02 CN CNB2004800057108A patent/CN100376591C/zh not_active Expired - Fee Related
- 2004-03-03 TW TW093105458A patent/TW200504089A/zh unknown
- 2004-03-03 MY MYPI20040728A patent/MY139235A/en unknown
- 2004-03-04 AR ARP040100680A patent/AR043466A1/es not_active Application Discontinuation
- 2004-03-04 CL CL200400438A patent/CL2004000438A1/es unknown
-
2005
- 2005-08-31 HR HR20050756A patent/HRP20050756A2/xx not_active Application Discontinuation
- 2005-10-03 ZA ZA200507995A patent/ZA200507995B/en unknown
- 2005-10-03 NO NO20054538A patent/NO20054538L/no not_active Application Discontinuation
-
2006
- 2006-08-04 HK HK06108677A patent/HK1088336A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20050756A2 (en) | 2006-07-31 |
| DE602004019191D1 (de) | 2009-03-12 |
| EP1599490A1 (en) | 2005-11-30 |
| NO20054538L (no) | 2005-10-03 |
| NZ541811A (en) | 2008-07-31 |
| CL2004000438A1 (es) | 2005-01-21 |
| TW200504089A (en) | 2005-02-01 |
| JP2006519860A (ja) | 2006-08-31 |
| ES2254047T1 (es) | 2006-06-16 |
| AU2004217974A1 (en) | 2004-09-16 |
| ATE421521T1 (de) | 2009-02-15 |
| RU2005127626A (ru) | 2006-01-27 |
| DK1599490T3 (da) | 2009-04-27 |
| KR20050119111A (ko) | 2005-12-20 |
| JP4725976B2 (ja) | 2011-07-13 |
| CN1756760A (zh) | 2006-04-05 |
| BRPI0407967A (pt) | 2006-03-07 |
| HK1088336A1 (en) | 2006-11-03 |
| MXPA05009384A (es) | 2006-02-28 |
| AR043466A1 (es) | 2005-07-27 |
| CN100376591C (zh) | 2008-03-26 |
| US7157589B2 (en) | 2007-01-02 |
| US20040215004A1 (en) | 2004-10-28 |
| EP1599490B8 (en) | 2009-04-08 |
| PT1599490E (pt) | 2009-04-03 |
| RU2333216C2 (ru) | 2008-09-10 |
| CA2517964A1 (en) | 2004-09-16 |
| EP1599490B1 (en) | 2009-01-21 |
| WO2004078769A1 (en) | 2004-09-16 |
| SI1599490T1 (sl) | 2009-06-30 |
| ES2254047T3 (es) | 2009-05-14 |
| UA81657C2 (ru) | 2008-01-25 |
| MY139235A (en) | 2009-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200507995B (en) | Process for the preparation of anticonvulsant derivatives of topiramate | |
| AU2021314375A1 (en) | Method for large-scale synthesis of tetrodotoxin | |
| KR102689384B1 (ko) | 엔잘루타미드를 제조하는 방법 | |
| AU2007287386B2 (en) | Process for the manufacture of HI-6 dimethanesulfonate | |
| Rajappa et al. | Quinone-imides: regiospecificity of nucleophilic attack on n-alkanesulphonyl-n'-alkanoyl 14-benzoquinone-imines. | |
| KR20240056726A (ko) | 니로가세스타트의 합성 | |
| Grehn et al. | Synthesis and use of benzyl tert-butyl iminodicarbonate, a versatile reagent for the preparation of amines | |
| WO2004108732A1 (en) | PROCESS FOR THE PREPARATION OF 2,3:4,5-BIS-O(1-METHYLETHYLIDENE)-ß-D-FRUCTOPYRANOSE SULFAMATE | |
| EP1558624B1 (en) | Continuous process for the preparation of fructopyranose sulfamate derivatives | |
| ZA200504408B (en) | Continuous process for the preparation of fructopyranose sulfamate derivatives | |
| PT1802635E (pt) | Compostos tricíclicos contendo heteroátomos | |
| Tafesse et al. | An efficient parallel synthesis of capsazepine and capsazepine analogs | |
| Kakuta et al. | Solid-phase synthesis of oligodeoxynucleotides using nucleobase N-unprotected oxazaphospholidine derivatives bearing a long alkyl chain | |
| EP1051402A1 (de) | Verfahren zur herstellung von s-alkyl(aryl)-substituierten imidazol-derivaten | |
| DE3534774A1 (de) | Nucleosid-analoge verbindungen mit antiviraler aktivitaet, verfahren zu deren herstellung sowie arzneimittel mit antiviraler wirkung | |
| JPH07291942A (ja) | カルボアサイクリックヌクレオシド誘導体およびその合成用中間体 | |
| PL97877B2 (es) | ||
| WO1993025518A1 (en) | NOVEL PROCESS FOR THE PREPARATION OF α-AMINOACYLANILIDES | |
| CZ319599A3 (cs) | Způsob přípravy derivátů esterů kyseliny máselné | |
| KR20010019370A (ko) | Ｎ-(4-메틸벤젠술포닐)-ｎ'-(3-아자바이시클로[3,3,0]옥탄)우레아의 제조방법 |