UA78566C2 - Substituted sulfamate derivatives as anticonvulsive agents - Google Patents

Substituted sulfamate derivatives as anticonvulsive agents Download PDF

Info

Publication number: UA78566C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; aryl; groups; independently selected
Prior art date: 2002-05-13

Application number

UA20041210256A

Other languages

English (en)

Ukrainian (uk)

Inventor

Patrick Rene Angibaud

Sherrill P Codrick

Allen B Reits

Original Assignee

Ortho Mcneil Pharm Inc

Priority date (The priority date 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 date listed.)

2002-05-13

Filing date

2003-09-05

Publication date

2007-04-10

2003-09-05 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2007-04-10 Publication of UA78566C2 publication Critical patent/UA78566C2/uk

Links

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
229910002027 silica gel Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
239000003814 drug Substances 0.000 description 7
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
239000012267 brine Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
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
239000004480 active ingredient Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000005191 phase separation Methods 0.000 description 5
239000006187 pill Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
230000001256 tonic effect Effects 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012261 resinous substance Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
244000215068 Acacia senegal Species 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
241000416162 Astragalus gummifer Species 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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230000036461 convulsion Effects 0.000 description 3
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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239000002244 precipitate Substances 0.000 description 3
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239000000651 prodrug Substances 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
235000015424 sodium Nutrition 0.000 description 3
239000008247 solid mixture Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
235000010487 tragacanth Nutrition 0.000 description 3
239000000196 tragacanth Substances 0.000 description 3
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KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
210000001747 pupil Anatomy 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
239000000565 sealant Substances 0.000 description 1
150000003865 secondary ammonium salts Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000005477 standard model Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical class BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003866 tertiary ammonium salts Chemical class 0.000 description 1
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Substances [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
229960002372 tetracaine Drugs 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1

Classifications

- 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
- 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)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Saccharide Compounds (AREA)

UA20041210256A 2002-05-13 2003-09-05 Substituted sulfamate derivatives as anticonvulsive agents UA78566C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
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

Family

ID=29549890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20041210256A UA78566C2 (en)	2002-05-13	2003-09-05	Substituted sulfamate derivatives as anticonvulsive agents

Country Status (19)

Country	Link
US (2)	US7060725B2 (fr)
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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JP2015522531A (ja)	2012-05-07	2015-08-06	セリックスビオプライヴェートリミテッド	神経筋疾患及び神経変性疾患の治療のための組成物及び方法
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US9242939B2 (en)	2012-05-10	2016-01-26	Cellix Bio Private Limited	Compositions and methods for the treatment of respiratory disorders
WO2013167997A2 (fr)	2012-05-10	2013-11-14	Mahesh Kandula	Compositions et méthodes de traitement du syndrome métabolique
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US9339484B2 (en)	2012-05-10	2016-05-17	Cellix Bio Private Limited	Compositions and methods for the treatment of restless leg syndrome and fibromyalgia
US9499527B2 (en)	2012-05-10	2016-11-22	Cellix Bio Private Limited	Compositions and methods for the treatment of familial amyloid polyneuropathy
SG11201407318UA (en)	2012-05-10	2014-12-30	Cellix Bio Private Ltd	Compositions and methods for the treatment of metabolic syndrome
WO2013168000A1 (fr)	2012-05-10	2013-11-14	Mahesh Kandula	Compositions et méthodes de traitement de la douleur sévère
WO2013168011A1 (fr)	2012-05-10	2013-11-14	Mahesh Kandula	Compositions et méthodes de traitement de la douleur chronique
WO2013168004A2 (fr)	2012-05-10	2013-11-14	Mahesh Kandula	Compositions et méthodes de traitement de la douleur fibromyalgique
US9315461B2 (en)	2012-05-10	2016-04-19	Cellix Bio Private Limited	Compositions and methods for the treatment of neurologic diseases
US9499526B2 (en)	2012-05-10	2016-11-22	Cellix Bio Private Limited	Compositions and methods for the treatment of neurologic diseases
AU2013264896A1 (en)	2012-05-23	2014-11-27	Cellixbio Private Limited	Compositions and methods for the treatment of multiple sclerosis
US9498461B2 (en)	2012-05-23	2016-11-22	Cellix Bio Private Limited	Compositions and methods for the treatment of inflammatory bowel disease
WO2013175347A2 (fr)	2012-05-23	2013-11-28	Mahesh Kandula	Compositions et méthodes pour le traitement de troubles respiratoires
WO2013175344A2 (fr)	2012-05-23	2013-11-28	Mahesh Kandula	Compositions et méthodes pour le traitement de la parodontite et de la polyarthrite rhumatoïde
AU2013264820A1 (en)	2012-05-23	2014-11-27	Cellixbio Private Limited	Compositions and methods for treatment of mucositis
WO2013175376A2 (fr)	2012-05-23	2013-11-28	Mahesh Kandula	Compositions et méthodes de traitement de la douleur locale
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
US9624168B2 (en)	2012-09-06	2017-04-18	Cellix Bio Private Limited	Compositions and methods for the treatment inflammation and lipid disorders
CA2873029A1 (fr)	2012-09-08	2014-03-13	Cellixbio Private Limited	Compositions et methodes de traitement d'une inflammation et de troubles lipidiques
HUE038423T2 (hu)	2012-12-07	2018-10-29	Glycomimetics Inc	E-szelektin antagonistákat felhasználó vegyületek, készítmények és eljárások vérképzõ sejtek mobilizációjára
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
EP3240779B1 (fr)	2014-09-26	2020-10-28	Cellixbio Private Limited	Compositions et méthodes de traitement de l'épilepsie et de troubles neurologiques
ES2799309T3 (es)	2014-09-29	2020-12-16	Cellix Bio Private Ltd	Compuestos y composiciones para el tratamiento de esclerosis múltiple
CA2965449C (fr)	2014-10-27	2020-11-10	Cellix Bio Private Limited	Sels ternaires d'ester monomethylique d'acide fumarique associes a la piperazine ou a l'ethylenediamine pour le traitement de la sclerose en plaques
US9284287B1 (en)	2014-11-05	2016-03-15	Cellix Bio Private Limited	Compositions and methods for the suppression of carbonic anhydrase activity
US9321716B1 (en)	2014-11-05	2016-04-26	Cellix Bio Private Limited	Compositions and methods for the treatment of metabolic syndrome
US9290486B1 (en)	2014-11-05	2016-03-22	Cellix Bio Private Limited	Compositions and methods for the treatment of epilepsy
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
US9175008B1 (en)	2014-11-05	2015-11-03	Cellix Bio Private Limited	Prodrugs of anti-platelet agents
US9150557B1 (en)	2014-11-05	2015-10-06	Cellix Bio Private Limited	Compositions and methods for the treatment of hyperglycemia
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2003
- 2003-05-08 US US10/434,387 patent/US7060725B2/en not_active Expired - Lifetime
- 2003-05-09 AU AU2003232112A patent/AU2003232112B2/en not_active Ceased
- 2003-05-09 MX MXPA04011232A patent/MXPA04011232A/es active IP Right Grant
- 2003-05-09 EP EP03753013A patent/EP1506212A2/fr not_active Withdrawn
- 2003-05-09 CN CN038159910A patent/CN1665828B/zh not_active Expired - Fee Related
- 2003-05-09 RU RU2004133334/04A patent/RU2328502C2/ru active
- 2003-05-09 BR BR0309964-4A patent/BR0309964A/pt not_active IP Right Cessation
- 2003-05-09 NZ NZ537139A patent/NZ537139A/en unknown
- 2003-05-09 PL PL03373910A patent/PL373910A1/xx not_active Application Discontinuation
- 2003-05-09 JP JP2004505387A patent/JP2005526852A/ja active Pending
- 2003-05-09 CA CA002485966A patent/CA2485966A1/fr not_active Abandoned
- 2003-05-09 WO PCT/US2003/014796 patent/WO2003097656A2/fr not_active Ceased
- 2003-05-09 HR HR20041042A patent/HRP20041042A2/xx not_active Application Discontinuation
- 2003-05-13 TW TW092112867A patent/TWI281472B/zh not_active IP Right Cessation
- 2003-05-13 AR AR20030101652A patent/AR040412A1/es unknown
- 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
TWI281472B (en)	2007-05-21
RU2004133334A (ru)	2005-06-10
RU2328502C2 (ru)	2008-07-10
TW200404078A (en)	2004-03-16
MXPA04011232A (es)	2005-08-16
BR0309964A (pt)	2005-03-01
CN1665828A (zh)	2005-09-07
PL373910A1 (en)	2005-09-19
WO2003097656A2 (fr)	2003-11-27
US7060725B2 (en)	2006-06-13
EP1506212A2 (fr)	2005-02-16
JP2005526852A (ja)	2005-09-08
US20060058373A1 (en)	2006-03-16
WO2003097656A3 (fr)	2004-06-10
US7560459B2 (en)	2009-07-14
HRP20041042A2 (hr)	2009-04-30
AU2003232112B2 (en)	2008-12-18
AU2003232112A1 (en)	2003-12-02
CN1665828B (zh)	2012-06-27
AR040412A1 (es)	2005-04-06
ZA200409989B (en)	2006-02-22
IL165108A0 (en)	2005-12-18
NO20045369L (no)	2004-12-08
US20040038911A1 (en)	2004-02-26
CA2485966A1 (fr)	2003-11-27
NZ537139A (en)	2008-05-30

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