BG108488A - Фармацевтични състави, съдържащи слаборазтворими и/или киселинно-сензитивни лекарства и неутрализирани кисели полимери - Google Patents
Фармацевтични състави, съдържащи слаборазтворими и/или киселинно-сензитивни лекарства и неутрализирани кисели полимери Download PDFInfo
- Publication number
- BG108488A BG108488A BG108488A BG10848803A BG108488A BG 108488 A BG108488 A BG 108488A BG 108488 A BG108488 A BG 108488A BG 10848803 A BG10848803 A BG 10848803A BG 108488 A BG108488 A BG 108488A
- Authority
- BG
- Bulgaria
- Prior art keywords
- phenyl
- amino
- methyl
- propanol
- trifluoro
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 193
- 239000003814 drug Substances 0.000 title claims abstract description 180
- 229940079593 drug Drugs 0.000 title claims abstract description 176
- 230000002378 acidificating effect Effects 0.000 title claims abstract description 143
- 239000002253 acid Substances 0.000 title claims abstract description 79
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- -1 carboxymethyl ethyl Chemical group 0.000 claims description 329
- 239000000203 mixture Substances 0.000 claims description 98
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- 230000000968 intestinal effect Effects 0.000 claims description 47
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- 238000000034 method Methods 0.000 claims description 23
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- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 15
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 claims description 15
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 15
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 14
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 14
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 239000004815 dispersion polymer Substances 0.000 claims description 12
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 9
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 9
- 239000001856 Ethyl cellulose Substances 0.000 claims description 8
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 8
- 229920001249 ethyl cellulose Polymers 0.000 claims description 8
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 230000003472 neutralizing effect Effects 0.000 claims description 7
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 claims description 6
- PLEULVPCZZDBNB-UHFFFAOYSA-N acetic acid;butanedioic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O PLEULVPCZZDBNB-UHFFFAOYSA-N 0.000 claims description 6
- 229920000609 methyl cellulose Polymers 0.000 claims description 6
- 235000010981 methylcellulose Nutrition 0.000 claims description 6
- 239000001923 methylcellulose Substances 0.000 claims description 6
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- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 claims description 5
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- 230000009477 glass transition Effects 0.000 claims description 5
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- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 4
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 4
- 125000005591 trimellitate group Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
- ZNPLZHBZUSCANM-UHFFFAOYSA-N acetic acid;benzene-1,3-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC(C(O)=O)=C1 ZNPLZHBZUSCANM-UHFFFAOYSA-N 0.000 claims description 3
- FMTQGBMMIVVKSN-UHFFFAOYSA-N acetic acid;terephthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 FMTQGBMMIVVKSN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- VYGAQHDGEYQIJU-UHFFFAOYSA-N butanedioic acid;phthalic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O VYGAQHDGEYQIJU-UHFFFAOYSA-N 0.000 claims description 3
- VHEMBTYWURNBQQ-UHFFFAOYSA-N butanoic acid;phthalic acid Chemical compound CCCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O VHEMBTYWURNBQQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001727 cellulose butyrate Polymers 0.000 claims description 3
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- CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 claims description 3
- ZNNQGSGPVUYWOS-UHFFFAOYSA-N 2-(3-hydroxypropoxy)benzoic acid Chemical compound OCCCOC1=CC=CC=C1C(O)=O ZNNQGSGPVUYWOS-UHFFFAOYSA-N 0.000 claims description 2
- OEXIDSNKGPWFGB-UHFFFAOYSA-N 2-ethyl-3-(3-hydroxypropyl)benzoic acid Chemical compound CCC1=C(CCCO)C=CC=C1C(O)=O OEXIDSNKGPWFGB-UHFFFAOYSA-N 0.000 claims description 2
- NMGBFVPQUCLJGM-UHFFFAOYSA-N 3-ethylphthalic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1C(O)=O NMGBFVPQUCLJGM-UHFFFAOYSA-N 0.000 claims description 2
- INTNEELQXPKMNM-UHFFFAOYSA-N 3-ethylpyridine-2-carboxylic acid Chemical compound CCC1=CC=CN=C1C(O)=O INTNEELQXPKMNM-UHFFFAOYSA-N 0.000 claims description 2
- GZRANGIRVYGSDJ-UHFFFAOYSA-N acetic acid;pyridine-2,3-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CN=C1C(O)=O GZRANGIRVYGSDJ-UHFFFAOYSA-N 0.000 claims description 2
- JZXYXNDNNNMXNG-CTNGQTDRSA-N propan-2-yl (2r,4s)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)CC)C(=O)OCCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JZXYXNDNNNMXNG-CTNGQTDRSA-N 0.000 claims description 2
- RESGCFMULOVHHB-UHFFFAOYSA-N 2-ethylpyridine-3-carboxylic acid Chemical compound CCC1=NC=CC=C1C(O)=O RESGCFMULOVHHB-UHFFFAOYSA-N 0.000 claims 1
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- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 332
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 253
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 244
- 125000000217 alkyl group Chemical group 0.000 description 225
- 125000004432 carbon atom Chemical group C* 0.000 description 206
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 155
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 151
- 229910052757 nitrogen Inorganic materials 0.000 description 134
- 150000001875 compounds Chemical class 0.000 description 128
- 229910052717 sulfur Inorganic materials 0.000 description 128
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 116
- 125000004043 oxo group Chemical group O=* 0.000 description 109
- 125000005843 halogen group Chemical group 0.000 description 105
- 229910052799 carbon Inorganic materials 0.000 description 103
- 229920006395 saturated elastomer Polymers 0.000 description 102
- 229910052739 hydrogen Inorganic materials 0.000 description 100
- 239000001257 hydrogen Substances 0.000 description 98
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 94
- 125000003545 alkoxy group Chemical group 0.000 description 90
- 125000003118 aryl group Chemical group 0.000 description 88
- 229910052760 oxygen Inorganic materials 0.000 description 86
- 125000001424 substituent group Chemical group 0.000 description 84
- 125000005842 heteroatom Chemical group 0.000 description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 76
- 239000001301 oxygen Substances 0.000 description 76
- 229910052736 halogen Inorganic materials 0.000 description 75
- 239000011593 sulfur Substances 0.000 description 74
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- 125000000623 heterocyclic group Chemical group 0.000 description 72
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 70
- 125000001072 heteroaryl group Chemical group 0.000 description 69
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 28
- 125000001153 fluoro group Chemical group F* 0.000 description 28
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- 125000001188 haloalkyl group Chemical group 0.000 description 26
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- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 24
- 125000004429 atom Chemical group 0.000 description 23
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- KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 description 21
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 20
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 19
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 15
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- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
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- 125000005164 aryl thioalkyl group Chemical group 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 12
- 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 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 10
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 10
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 9
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- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 9
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- 125000005368 heteroarylthio group Chemical group 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 8
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 8
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 8
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- 230000002209 hydrophobic effect Effects 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
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- 125000004391 aryl sulfonyl group Chemical group 0.000 description 7
- 125000002843 carboxylic acid group Chemical group 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
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- 238000010438 heat treatment Methods 0.000 description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
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- 230000002496 gastric effect Effects 0.000 description 6
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- 229960004592 isopropanol Drugs 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
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- 229960003212 sodium propionate Drugs 0.000 description 1
- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
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- XZSDLXJALXRMAW-UNMCSNQZSA-N tert-butyl (2S,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C2=CC(=CC=C12)C(F)(F)F)NCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1CC1 XZSDLXJALXRMAW-UNMCSNQZSA-N 0.000 description 1
- VWHKCKWNWNEPGK-QRWLVFNGSA-N tert-butyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@@H]1C2=CC(OC)=C(OC)C=C2N(C(=O)OC(C)(C)C)[C@H](C)C1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VWHKCKWNWNEPGK-QRWLVFNGSA-N 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
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- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
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Classifications
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polymerisation Methods In General (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30025601P | 2001-06-22 | 2001-06-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
BG108488A true BG108488A (bg) | 2005-01-31 |
Family
ID=23158332
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG108488A BG108488A (bg) | 2001-06-22 | 2003-12-22 | Фармацевтични състави, съдържащи слаборазтворими и/или киселинно-сензитивни лекарства и неутрализирани кисели полимери |
Country Status (28)
Country | Link |
---|---|
US (3) | US20030054038A1 (fr) |
EP (1) | EP1399190B1 (fr) |
JP (1) | JP2004534822A (fr) |
KR (1) | KR20040011549A (fr) |
CN (1) | CN1545421A (fr) |
AT (1) | ATE480226T1 (fr) |
BG (1) | BG108488A (fr) |
BR (1) | BR0210530A (fr) |
CA (1) | CA2450762A1 (fr) |
CO (1) | CO5540325A2 (fr) |
CR (1) | CR7171A (fr) |
CZ (1) | CZ20033457A3 (fr) |
DE (1) | DE60237602D1 (fr) |
EA (1) | EA200301250A1 (fr) |
EC (1) | ECSP034913A (fr) |
EE (1) | EE200400033A (fr) |
HU (1) | HUP0400264A2 (fr) |
IL (1) | IL158991A0 (fr) |
IS (1) | IS7047A (fr) |
MA (1) | MA27039A1 (fr) |
MX (1) | MXPA03011933A (fr) |
NO (1) | NO20035699D0 (fr) |
OA (1) | OA12624A (fr) |
PL (1) | PL368587A1 (fr) |
SK (1) | SK15732003A3 (fr) |
TN (1) | TNSN03137A1 (fr) |
WO (1) | WO2003000292A1 (fr) |
ZA (1) | ZA200308989B (fr) |
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-
2002
- 2002-05-08 OA OA1200300325A patent/OA12624A/en unknown
- 2002-05-08 PL PL02368587A patent/PL368587A1/xx not_active Application Discontinuation
- 2002-05-08 CN CNA028163338A patent/CN1545421A/zh active Pending
- 2002-05-08 HU HU0400264A patent/HUP0400264A2/hu unknown
- 2002-05-08 CZ CZ20033457A patent/CZ20033457A3/cs unknown
- 2002-05-08 KR KR10-2003-7016765A patent/KR20040011549A/ko not_active Application Discontinuation
- 2002-05-08 WO PCT/IB2002/001710 patent/WO2003000292A1/fr not_active Application Discontinuation
- 2002-05-08 EP EP02730571A patent/EP1399190B1/fr not_active Expired - Lifetime
- 2002-05-08 BR BR0210530-6A patent/BR0210530A/pt not_active IP Right Cessation
- 2002-05-08 CA CA002450762A patent/CA2450762A1/fr not_active Abandoned
- 2002-05-08 AT AT02730571T patent/ATE480226T1/de not_active IP Right Cessation
- 2002-05-08 MX MXPA03011933A patent/MXPA03011933A/es not_active Application Discontinuation
- 2002-05-08 EE EEP200400033A patent/EE200400033A/xx unknown
- 2002-05-08 DE DE60237602T patent/DE60237602D1/de not_active Expired - Lifetime
- 2002-05-08 TN TNPCT/IB2002/001710A patent/TNSN03137A1/fr unknown
- 2002-05-08 SK SK1573-2003A patent/SK15732003A3/sk unknown
- 2002-05-08 JP JP2003506934A patent/JP2004534822A/ja active Pending
- 2002-05-08 IL IL15899102A patent/IL158991A0/xx unknown
- 2002-05-08 EA EA200301250A patent/EA200301250A1/ru unknown
- 2002-06-17 US US10/175,566 patent/US20030054038A1/en not_active Abandoned
-
2003
- 2003-11-19 ZA ZA200308989A patent/ZA200308989B/en unknown
- 2003-11-20 IS IS7047A patent/IS7047A/is unknown
- 2003-11-27 CR CR7171A patent/CR7171A/es not_active Application Discontinuation
- 2003-12-11 MA MA27436A patent/MA27039A1/fr unknown
- 2003-12-15 CO CO03109223A patent/CO5540325A2/es not_active Application Discontinuation
- 2003-12-18 EC EC2003004913A patent/ECSP034913A/es unknown
- 2003-12-19 NO NO20035699A patent/NO20035699D0/no not_active Application Discontinuation
- 2003-12-22 BG BG108488A patent/BG108488A/bg unknown
-
2005
- 2005-08-26 US US11/213,118 patent/US8147872B2/en not_active Expired - Fee Related
-
2006
- 2006-06-05 US US11/422,133 patent/US8173142B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DE60237602D1 (de) | 2010-10-21 |
IS7047A (is) | 2003-11-20 |
MXPA03011933A (es) | 2004-03-26 |
CN1545421A (zh) | 2004-11-10 |
EP1399190A1 (fr) | 2004-03-24 |
ATE480226T1 (de) | 2010-09-15 |
ECSP034913A (es) | 2004-01-28 |
US8147872B2 (en) | 2012-04-03 |
MA27039A1 (fr) | 2004-12-20 |
US20060204577A1 (en) | 2006-09-14 |
EE200400033A (et) | 2004-06-15 |
CA2450762A1 (fr) | 2003-01-03 |
US8173142B2 (en) | 2012-05-08 |
KR20040011549A (ko) | 2004-02-05 |
HUP0400264A2 (hu) | 2004-08-30 |
JP2004534822A (ja) | 2004-11-18 |
TNSN03137A1 (fr) | 2005-12-23 |
BR0210530A (pt) | 2004-06-22 |
WO2003000292A1 (fr) | 2003-01-03 |
US20060003011A1 (en) | 2006-01-05 |
US20030054038A1 (en) | 2003-03-20 |
IL158991A0 (en) | 2004-05-12 |
CR7171A (es) | 2004-02-23 |
OA12624A (en) | 2006-06-12 |
NO20035699D0 (no) | 2003-12-19 |
CO5540325A2 (es) | 2005-07-29 |
PL368587A1 (en) | 2005-04-04 |
CZ20033457A3 (cs) | 2004-09-15 |
EP1399190B1 (fr) | 2010-09-08 |
ZA200308989B (en) | 2004-11-19 |
SK15732003A3 (sk) | 2005-01-03 |
EA200301250A1 (ru) | 2004-06-24 |
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