UA78566C2 - Substituted sulfamate derivatives as anticonvulsive agents - Google Patents
Substituted sulfamate derivatives as anticonvulsive agents Download PDFInfo
- Publication number
- UA78566C2 UA78566C2 UA20041210256A UA20041210256A UA78566C2 UA 78566 C2 UA78566 C2 UA 78566C2 UA 20041210256 A UA20041210256 A UA 20041210256A UA 20041210256 A UA20041210256 A UA 20041210256A UA 78566 C2 UA78566 C2 UA 78566C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- alkyl
- aryl
- groups
- independently selected
- Prior art date
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- 239000001961 anticonvulsive agent Substances 0.000 title description 4
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 304
- 238000000034 method Methods 0.000 claims abstract description 68
- 206010015037 epilepsy Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 574
- 125000003118 aryl group Chemical group 0.000 claims description 440
- 125000001424 substituent group Chemical group 0.000 claims description 350
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 298
- -1 - trifluoromethyl Chemical group 0.000 claims description 221
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 213
- 229910052736 halogen Inorganic materials 0.000 claims description 213
- 150000002367 halogens Chemical class 0.000 claims description 212
- 125000003545 alkoxy group Chemical group 0.000 claims description 210
- 125000003282 alkyl amino group Chemical group 0.000 claims description 199
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 197
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 192
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 187
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 184
- 125000003277 amino group Chemical group 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 138
- 125000001072 heteroaryl group Chemical group 0.000 claims description 125
- 229910052757 nitrogen Inorganic materials 0.000 claims description 101
- 150000002431 hydrogen Chemical class 0.000 claims description 100
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 99
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 92
- 229910052799 carbon Inorganic materials 0.000 claims description 79
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 74
- 125000003342 alkenyl group Chemical group 0.000 claims description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 32
- 125000006239 protecting group Chemical group 0.000 claims description 32
- 238000006467 substitution reaction Methods 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 30
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 27
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 27
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 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 19
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
- 125000002009 alkene group Chemical group 0.000 claims description 17
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 16
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 16
- 238000003776 cleavage reaction Methods 0.000 claims description 14
- 230000007017 scission Effects 0.000 claims description 14
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 5
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 5
- 229940067157 phenylhydrazine Drugs 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 241000989913 Gunnera petaloidea Species 0.000 claims 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- 150000001721 carbon Chemical group 0.000 description 42
- 239000007788 liquid Substances 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- 235000002639 sodium chloride Nutrition 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 206010010904 Convulsion Diseases 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- 229960004394 topiramate Drugs 0.000 description 14
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound 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 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
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- 230000000694 effects Effects 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
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- 229940079593 drug Drugs 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- 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
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- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
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- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US37801702P | 2002-05-13 | 2002-05-13 | |
| PCT/US2003/014796 WO2003097656A2 (fr) | 2002-05-13 | 2003-05-09 | Nouveaux derivés anticonvulsifs à substitution sulfamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78566C2 true UA78566C2 (en) | 2007-04-10 |
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Family Applications (1)
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|---|---|---|---|
| UA20041210256A UA78566C2 (en) | 2002-05-13 | 2003-09-05 | Substituted sulfamate derivatives as anticonvulsive agents |
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| EP (1) | EP1506212A2 (fr) |
| JP (1) | JP2005526852A (fr) |
| CN (1) | CN1665828B (fr) |
| AR (1) | AR040412A1 (fr) |
| AU (1) | AU2003232112B2 (fr) |
| BR (1) | BR0309964A (fr) |
| CA (1) | CA2485966A1 (fr) |
| HR (1) | HRP20041042A2 (fr) |
| IL (1) | IL165108A0 (fr) |
| MX (1) | MXPA04011232A (fr) |
| NO (1) | NO20045369L (fr) |
| NZ (1) | NZ537139A (fr) |
| PL (1) | PL373910A1 (fr) |
| RU (1) | RU2328502C2 (fr) |
| TW (1) | TWI281472B (fr) |
| UA (1) | UA78566C2 (fr) |
| WO (1) | WO2003097656A2 (fr) |
| ZA (1) | ZA200409989B (fr) |
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| US20060088886A1 (en) * | 2004-10-25 | 2006-04-27 | Anlong Ouyang | Topiramate analogs |
| US7638291B2 (en) * | 2004-10-25 | 2009-12-29 | Seradyn, Inc. | Immunoassays for topiramate |
| WO2007099388A1 (fr) * | 2006-03-01 | 2007-09-07 | Glade Organics Private Limited | Procédé amélioré de fabrication du topiramate |
| WO2014037832A2 (fr) * | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions et méthodes de traitement de l'épilepsie et de maladies neurologiques |
| WO2013168021A1 (fr) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes pour le traitement des troubles neuromusculaires et des troubles neurodégénératifs |
| US9399634B2 (en) | 2012-05-07 | 2016-07-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of depression |
| WO2013167985A1 (fr) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement de troubles neurologiques |
| WO2013168023A1 (fr) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes pour le traitement de la maladie de parkinson |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| WO2013168025A1 (fr) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement des maladies de coagulation du sang |
| WO2013167992A1 (fr) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement de troubles inflammatoires |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| WO2013168012A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement de troubles respiratoires |
| WO2013168015A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes pour le traitement de l'asthme et de l'allergie |
| WO2013168016A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement du syndrome métabolique |
| WO2013167997A2 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement du syndrome métabolique |
| WO2013168033A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et methodes pour le traitement de maladies neurologiques |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| WO2013168000A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement de la douleur sévère |
| WO2013168005A2 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement du syndrome des jambes sans repos et de la fibromyalgie |
| WO2013168002A1 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement d'affections neurologiques |
| WO2013168004A2 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement de la douleur fibromyalgique |
| US9499527B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
| WO2013167999A2 (fr) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions et méthodes de traitement d'affections neurologiques |
| NZ701832A (en) | 2012-05-23 | 2016-08-26 | Cellix Bio Private Ltd | Compositions and methods for treatment of inflammatory bowel disease |
| AU2013264820A1 (en) | 2012-05-23 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for treatment of mucositis |
| WO2013175344A2 (fr) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions et méthodes pour le traitement de la parodontite et de la polyarthrite rhumatoïde |
| JP2015518854A (ja) | 2012-05-23 | 2015-07-06 | セリックスビオ プライヴェート リミテッド | 多発性硬化症の治療のための組成物および方法 |
| WO2013175347A2 (fr) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions et méthodes pour le traitement de troubles respiratoires |
| US9492409B2 (en) | 2012-05-23 | 2016-11-15 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| WO2014020480A2 (fr) | 2012-08-03 | 2014-02-06 | Mahesh Kandula | Compositions et méthodes pour le traitement de la migraine et de maladies neurologiques |
| WO2014037833A2 (fr) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions et méthodes de traitement d'une inflammation et de troubles lipidiques |
| SG11201407325YA (en) | 2012-09-08 | 2014-12-30 | Cellix Bio Private Ltd | Compositions and methods for treatment of inflammation and lipid disorders |
| US9867841B2 (en) | 2012-12-07 | 2018-01-16 | Glycomimetics, Inc. | Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells |
| 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 |
| SG11201509782TA (en) | 2013-06-04 | 2015-12-30 | Cellix Bio Private Ltd | 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 |
| CN103910770B (zh) * | 2014-03-14 | 2017-01-04 | 天津南开允公医药科技有限公司 | 一种托吡酯的制备方法以及该方法中所涉及的中间体晶型及其制备方法 |
| NZ736131A (en) | 2014-09-26 | 2019-04-26 | Cellix Bio Private Ltd | Compositions and methods for the treatment of epilepsy and neurological disorders |
| ES2799309T3 (es) | 2014-09-29 | 2020-12-16 | Cellix Bio Private Ltd | Compuestos y composiciones para el tratamiento de esclerosis múltiple |
| JP6564868B2 (ja) | 2014-10-27 | 2019-08-21 | セリックス バイオ プライヴェート リミテッドＣｅｌｌｉｘ Ｂｉｏ Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 多発性硬化症の治療のための、フマル酸モノメチルエステルとピペラジン又はエチレンジアミンとの３つの成分の塩 |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| 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 |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| WO2016088132A1 (fr) | 2014-12-01 | 2016-06-09 | Cellix Bio Private Limited | Compositions et méthodes pour le traitement de la sclérose en plaques |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| SG11201705524SA (en) | 2015-01-06 | 2017-08-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of inflammation and pain |
| WO2019188200A1 (fr) * | 2018-03-27 | 2019-10-03 | ダイキン工業株式会社 | Procédé de production de sulfamate de lithium, et nouveau sulfamate de lithium |
| CN110655542A (zh) * | 2018-06-29 | 2020-01-07 | 鲁南制药集团股份有限公司 | 一种2,3:4,5-双-O-(1-甲基亚乙基)-β-D-吡喃果糖氯磺酸酯的晶型 |
| CN114685526A (zh) * | 2020-12-25 | 2022-07-01 | 长沙博源医疗科技有限公司 | 一种托吡酯衍生物、免疫原、抗托吡酯特异性抗体及其制备方法与应用 |
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| US4513006A (en) | 1983-09-26 | 1985-04-23 | Mcneil Lab., Inc. | Anticonvulsant sulfamate derivatives |
| US5273993A (en) | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| US5194446A (en) | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| PT94305B (pt) | 1989-06-12 | 1997-02-28 | Robins Co Inc A H | Processo para a preparacao de compostos tendo um ou mais radicais aminossulfoniloxi uteis como produtos farmaceuticos |
| US5192785A (en) | 1989-09-03 | 1993-03-09 | A. H. Robins Company, Incorporated | Sulfamates as antiglaucoma agents |
| US5025031A (en) | 1989-11-30 | 1991-06-18 | A. H. Robins Co., Inc. | Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants |
| IL103172A (en) * | 1991-09-19 | 1997-01-10 | Mcneilab Inc | Preparation of chlorosulfate and sulfamate derivatives of 2, 3:4, 5-bis-o-(1-methylethylidene)-beta-d-fructopyranose and (1-methylcyclohexyl) methanol |
| US5242942A (en) * | 1992-04-28 | 1993-09-07 | Mcneilab, Inc. | Anticonvulsant fructopyranose cyclic sulfites and sulfates |
| CA2179733C (fr) | 1993-12-23 | 2007-03-27 | Michael J. Costanzo | Sulfamates de pseudofructopyranose anticonvulsifs |
| US5998380A (en) | 1995-10-13 | 1999-12-07 | New England Medical Center Hospitals, Inc. | Treatment of migraine |
| US5952187A (en) | 1995-12-01 | 1999-09-14 | Oxis International, Inc. | Topiramate immunoassay |
| JP3602906B2 (ja) * | 1996-03-05 | 2004-12-15 | 富士写真フイルム株式会社 | 熱現像感光材料 |
-
2003
- 2003-05-08 US US10/434,387 patent/US7060725B2/en not_active Expired - Lifetime
- 2003-05-09 CN CN038159910A patent/CN1665828B/zh not_active Expired - Fee Related
- 2003-05-09 AU AU2003232112A patent/AU2003232112B2/en not_active Ceased
- 2003-05-09 RU RU2004133334/04A patent/RU2328502C2/ru active
- 2003-05-09 WO PCT/US2003/014796 patent/WO2003097656A2/fr not_active Ceased
- 2003-05-09 CA CA002485966A patent/CA2485966A1/fr not_active Abandoned
- 2003-05-09 HR HR20041042A patent/HRP20041042A2/xx not_active Application Discontinuation
- 2003-05-09 JP JP2004505387A patent/JP2005526852A/ja active Pending
- 2003-05-09 MX MXPA04011232A patent/MXPA04011232A/es active IP Right Grant
- 2003-05-09 NZ NZ537139A patent/NZ537139A/en unknown
- 2003-05-09 PL PL03373910A patent/PL373910A1/xx not_active Application Discontinuation
- 2003-05-09 EP EP03753013A patent/EP1506212A2/fr not_active Withdrawn
- 2003-05-09 BR BR0309964-4A patent/BR0309964A/pt not_active IP Right Cessation
- 2003-05-13 AR AR20030101652A patent/AR040412A1/es unknown
- 2003-05-13 TW TW092112867A patent/TWI281472B/zh not_active IP Right Cessation
- 2003-09-05 UA UA20041210256A patent/UA78566C2/uk unknown
-
2004
- 2004-11-09 IL IL16510804A patent/IL165108A0/xx unknown
- 2004-12-08 NO NO20045369A patent/NO20045369L/no not_active Application Discontinuation
- 2004-12-09 ZA ZA200409989A patent/ZA200409989B/xx unknown
-
2005
- 2005-11-02 US US11/265,670 patent/US7560459B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NZ537139A (en) | 2008-05-30 |
| CA2485966A1 (fr) | 2003-11-27 |
| AU2003232112B2 (en) | 2008-12-18 |
| US7560459B2 (en) | 2009-07-14 |
| WO2003097656A3 (fr) | 2004-06-10 |
| RU2328502C2 (ru) | 2008-07-10 |
| PL373910A1 (en) | 2005-09-19 |
| WO2003097656A2 (fr) | 2003-11-27 |
| TW200404078A (en) | 2004-03-16 |
| HRP20041042A2 (hr) | 2009-04-30 |
| AR040412A1 (es) | 2005-04-06 |
| IL165108A0 (en) | 2005-12-18 |
| ZA200409989B (en) | 2006-02-22 |
| MXPA04011232A (es) | 2005-08-16 |
| CN1665828B (zh) | 2012-06-27 |
| US20040038911A1 (en) | 2004-02-26 |
| US20060058373A1 (en) | 2006-03-16 |
| JP2005526852A (ja) | 2005-09-08 |
| TWI281472B (en) | 2007-05-21 |
| CN1665828A (zh) | 2005-09-07 |
| BR0309964A (pt) | 2005-03-01 |
| US7060725B2 (en) | 2006-06-13 |
| RU2004133334A (ru) | 2005-06-10 |
| EP1506212A2 (fr) | 2005-02-16 |
| NO20045369L (no) | 2004-12-08 |
| AU2003232112A1 (en) | 2003-12-02 |
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