JP4015548B2 - ウイルス性疾患の処置のためのピラゾール誘導体 - Google Patents
ウイルス性疾患の処置のためのピラゾール誘導体 Download PDFInfo
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- JP4015548B2 JP4015548B2 JP2002534293A JP2002534293A JP4015548B2 JP 4015548 B2 JP4015548 B2 JP 4015548B2 JP 2002534293 A JP2002534293 A JP 2002534293A JP 2002534293 A JP2002534293 A JP 2002534293A JP 4015548 B2 JP4015548 B2 JP 4015548B2
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- alkyl
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- methyl
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- alkoxy
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- 201000010099 disease Diseases 0.000 title claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 32
- 150000003217 pyrazoles Chemical class 0.000 title description 22
- 230000003612 virological effect Effects 0.000 title description 8
- -1 nitro, substituted Phenyl Chemical group 0.000 claims description 535
- 125000001424 substituent group Chemical group 0.000 claims description 236
- 239000000460 chlorine Substances 0.000 claims description 139
- 229910052801 chlorine Inorganic materials 0.000 claims description 139
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 138
- 125000000623 heterocyclic group Chemical group 0.000 claims description 123
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 122
- 229910052794 bromium Inorganic materials 0.000 claims description 122
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 239000011737 fluorine Substances 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 229910052760 oxygen Inorganic materials 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 45
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 38
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 29
- 125000003107 substituted aryl group Chemical group 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 230000001404 mediated effect Effects 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 12
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- UKHRNAGNSSSBMC-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]-pyridin-4-ylmethanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1C(O)C1=CC=NC=C1 UKHRNAGNSSSBMC-UHFFFAOYSA-N 0.000 claims description 4
- OSJKUHXHFYDTML-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenyl-4-(2-phenylethenyl)pyrazole Chemical compound C=1C=CC=CC=1C=CC=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 OSJKUHXHFYDTML-UHFFFAOYSA-N 0.000 claims description 3
- PXJZTWQGYYERLN-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenylpyrazol-4-yl]-phenylmethanol Chemical compound C=1C=CC=CC=1C(O)C=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 PXJZTWQGYYERLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- FIAXOWSLAQCROP-UHFFFAOYSA-N 1-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridin-2-one Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CN1C=CC=CC1=O FIAXOWSLAQCROP-UHFFFAOYSA-N 0.000 claims description 2
- KBPZFCJPKNTSPL-UHFFFAOYSA-N 2-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methoxy]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1COC1=CC=CC=N1 KBPZFCJPKNTSPL-UHFFFAOYSA-N 0.000 claims description 2
- VXJZQHIRXNSXSN-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]-fluoromethyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1C(F)C1=CC=NC=C1 VXJZQHIRXNSXSN-UHFFFAOYSA-N 0.000 claims description 2
- MZEWYAGMQKPAPE-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methoxymethyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1COCC1=CC=NC=C1 MZEWYAGMQKPAPE-UHFFFAOYSA-N 0.000 claims description 2
- UTAAZPLXPDPKSP-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-3-fluoropyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1F UTAAZPLXPDPKSP-UHFFFAOYSA-N 0.000 claims description 2
- OPLKUWLCOHVKMH-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1 OPLKUWLCOHVKMH-UHFFFAOYSA-N 0.000 claims description 2
- QKLZOOFFVIMLOV-UHFFFAOYSA-N 4-benzyl-1-ethyl-5-(4-methoxyphenoxy)-3-methylpyrazole Chemical compound C=1C=C(OC)C=CC=1OC=1N(CC)N=C(C)C=1CC1=CC=CC=C1 QKLZOOFFVIMLOV-UHFFFAOYSA-N 0.000 claims description 2
- BELDDQVPIKPQKG-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenylpyrazole Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 BELDDQVPIKPQKG-UHFFFAOYSA-N 0.000 claims description 2
- UDNFNXMKTZIXSA-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CC=C1 UDNFNXMKTZIXSA-UHFFFAOYSA-N 0.000 claims description 2
- TZFNTMLGNKIZGC-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenyl-4-(2-phenylethyl)pyrazole Chemical compound C=1C=CC=CC=1CCC=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 TZFNTMLGNKIZGC-UHFFFAOYSA-N 0.000 claims description 2
- JAAADHXPOZHZQH-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenyl-4-(phenylmethoxymethyl)pyrazole Chemical compound C=1C=CC=CC=1COCC=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 JAAADHXPOZHZQH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- PPFREGQIWFNILB-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methyl]pyridin-3-amine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CNC1=CC=CN=C1 PPFREGQIWFNILB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- GBBYUGXMSGDMCC-UHFFFAOYSA-N 1,4-dibenzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(CC=2C=CC=CC=2)C(C)=NN1CC1=CC=CC=C1 GBBYUGXMSGDMCC-UHFFFAOYSA-N 0.000 claims 1
- ZECUEMIZXXOONH-UHFFFAOYSA-N 2-[4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methylpyrazol-1-yl]pyridine Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(C=2N=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 ZECUEMIZXXOONH-UHFFFAOYSA-N 0.000 claims 1
- WBQXODHQJHNXFA-UHFFFAOYSA-N 2-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyrazine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CN=CC=N1 WBQXODHQJHNXFA-UHFFFAOYSA-N 0.000 claims 1
- CJSUPRFAHXVIAW-UHFFFAOYSA-N 2-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CC=N1 CJSUPRFAHXVIAW-UHFFFAOYSA-N 0.000 claims 1
- BXPONJWMNKTFSB-UHFFFAOYSA-N 2-[[5-(3,5-dimethylphenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(C)=CC(C)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CC=N1 BXPONJWMNKTFSB-UHFFFAOYSA-N 0.000 claims 1
- DGZURKPHVUGBDU-UHFFFAOYSA-N 2-[[5-(3-chlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CC=N1 DGZURKPHVUGBDU-UHFFFAOYSA-N 0.000 claims 1
- MWSYVKYDNOBLRJ-UHFFFAOYSA-N 2-chloro-4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-6-methylpyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC(C)=NC(Cl)=C1 MWSYVKYDNOBLRJ-UHFFFAOYSA-N 0.000 claims 1
- JJMVIAVHVDAOQL-UHFFFAOYSA-N 2-chloro-4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC(Cl)=C1 JJMVIAVHVDAOQL-UHFFFAOYSA-N 0.000 claims 1
- DTFBMXODKHDNGD-UHFFFAOYSA-N 3-(4-benzyl-5-methyl-2-phenylpyrazol-3-yl)oxybenzonitrile Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(C=2C=CC=CC=2)C=1OC1=CC=CC(C#N)=C1 DTFBMXODKHDNGD-UHFFFAOYSA-N 0.000 claims 1
- KBXUADRPWKKREM-UHFFFAOYSA-N 3-(4-benzyl-5-methyl-2-phenylpyrazol-3-yl)sulfanylbenzonitrile Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(C=2C=CC=CC=2)C=1SC1=CC=CC(C#N)=C1 KBXUADRPWKKREM-UHFFFAOYSA-N 0.000 claims 1
- PAGOZPBZCPPXGB-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methoxy]-2-nitropyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1COC1=CC=CN=C1[N+]([O-])=O PAGOZPBZCPPXGB-UHFFFAOYSA-N 0.000 claims 1
- KIIGFIZNMOAOIU-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methoxy]pyridin-2-amine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1COC1=CC=CN=C1N KIIGFIZNMOAOIU-UHFFFAOYSA-N 0.000 claims 1
- SOWSJMQBQBJPQE-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CC1=CC=CN=C1 SOWSJMQBQBJPQE-UHFFFAOYSA-N 0.000 claims 1
- HVMDHYHORZFSPN-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-phenylpyrazol-4-yl]methyl]-2-methylsulfanylpyridine Chemical compound CSC1=NC=CC=C1CC1=C(SC=2C=C(Cl)C=C(Cl)C=2)N(C=2C=CC=CC=2)N=C1C HVMDHYHORZFSPN-UHFFFAOYSA-N 0.000 claims 1
- QALYOWILIKVWDB-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-n,n-dimethylaniline Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CC(N(C)C)=C1 QALYOWILIKVWDB-UHFFFAOYSA-N 0.000 claims 1
- AGUSHARPIQFZFJ-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=CN=C1 AGUSHARPIQFZFJ-UHFFFAOYSA-N 0.000 claims 1
- XIYKXPGYVLXAFH-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyrimidin-4-one Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CN1C=NC=CC1=O XIYKXPGYVLXAFH-UHFFFAOYSA-N 0.000 claims 1
- STXOGQHTZZZEOJ-UHFFFAOYSA-N 3-bromo-5-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CC1=CN=CC(Br)=C1 STXOGQHTZZZEOJ-UHFFFAOYSA-N 0.000 claims 1
- JPVDHVQXTLFVFZ-UHFFFAOYSA-N 3-chloro-4-[[3-methyl-5-(3-methylphenyl)sulfanyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C=CC(C)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1Cl JPVDHVQXTLFVFZ-UHFFFAOYSA-N 0.000 claims 1
- YKSQVZIMDMEPHF-UHFFFAOYSA-N 3-chloro-4-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CC1=CC=NC=C1Cl YKSQVZIMDMEPHF-UHFFFAOYSA-N 0.000 claims 1
- JCJHQZQQRRVNKE-UHFFFAOYSA-N 3-chloro-4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1Cl JCJHQZQQRRVNKE-UHFFFAOYSA-N 0.000 claims 1
- HQBXJVUFAGWDFF-UHFFFAOYSA-N 3-chloro-4-[[5-(3,5-dimethylphenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C(C)=CC(C)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1Cl HQBXJVUFAGWDFF-UHFFFAOYSA-N 0.000 claims 1
- SMVRHZQOYFTTEJ-UHFFFAOYSA-N 3-chloro-5-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methoxy]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1COC1=CN=CC(Cl)=C1 SMVRHZQOYFTTEJ-UHFFFAOYSA-N 0.000 claims 1
- RFPKTPQOUWUSNE-UHFFFAOYSA-N 3-fluoro-4-[[3-methyl-5-(3-methylphenyl)sulfanyl-1-propan-2-ylpyrazol-4-yl]methyl]pyridine Chemical compound C=1C=CC(C)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1F RFPKTPQOUWUSNE-UHFFFAOYSA-N 0.000 claims 1
- RJCKJSBFDURLME-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methoxy]-6-methylpyrimidin-2-amine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1COC1=CC(C)=NC(N)=N1 RJCKJSBFDURLME-UHFFFAOYSA-N 0.000 claims 1
- PAKNDVVTUZQMMJ-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methoxy]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1COC1=CC=NC=C1 PAKNDVVTUZQMMJ-UHFFFAOYSA-N 0.000 claims 1
- LZKHRNBLWZMRKJ-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methyl]-3-fluoropyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CC1=CC=NC=C1F LZKHRNBLWZMRKJ-UHFFFAOYSA-N 0.000 claims 1
- BYLVKNZCHCZQJJ-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methylsulfanyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CSC1=CC=NC=C1 BYLVKNZCHCZQJJ-UHFFFAOYSA-N 0.000 claims 1
- RXHCDGHYECLYSU-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methoxy]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1COC1=CC=NC=C1 RXHCDGHYECLYSU-UHFFFAOYSA-N 0.000 claims 1
- DCQKJVDZKJRVGC-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]benzonitrile Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=C(C#N)C=C1 DCQKJVDZKJRVGC-UHFFFAOYSA-N 0.000 claims 1
- QHDWDRCKDFVYRZ-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]pyrimidine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=N1 QHDWDRCKDFVYRZ-UHFFFAOYSA-N 0.000 claims 1
- QKBTVDWERRHCQF-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methylsulfanyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CSC1=CC=NC=C1 QKBTVDWERRHCQF-UHFFFAOYSA-N 0.000 claims 1
- UYVYBZPOAAITRW-UHFFFAOYSA-N 4-[[5-(3,5-dimethylphenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-3-fluoropyridine Chemical compound C=1C(C)=CC(C)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1F UYVYBZPOAAITRW-UHFFFAOYSA-N 0.000 claims 1
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- ZUNNGUKWUYNWKA-UHFFFAOYSA-N 4-[[5-(3-bromophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-3-fluoropyridine Chemical compound C=1C=CC(Br)=CC=1SC=1N(C(C)C)N=C(C)C=1CC1=CC=NC=C1F ZUNNGUKWUYNWKA-UHFFFAOYSA-N 0.000 claims 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/18—Antivirals for RNA viruses for HIV
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0024795.7A GB0024795D0 (en) | 2000-10-10 | 2000-10-10 | Pyrazole derivatives for the treatment of viral diseases |
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Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2083005A1 (en) * | 2000-09-29 | 2009-07-29 | TopoTarget UK Limited | Carbamic acid compounds comprising an amide linkage as HDAC inhibitors |
| GB0113524D0 (en) | 2001-06-04 | 2001-07-25 | Hoffmann La Roche | Pyrazole derivatives |
| CA2495338A1 (en) | 2002-09-26 | 2004-04-08 | Pfizer Inc. | Pyrazole amides for treating hiv infections |
| US7230025B2 (en) | 2002-09-26 | 2007-06-12 | Pfizer, Inc. | Pyrazole derivatives |
| EP1546132A1 (en) * | 2002-09-26 | 2005-06-29 | Pfizer Limited | Pyrazole derivatives as reverse transcriptase inhibitors |
| GB0223234D0 (en) * | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
| GB0223232D0 (en) * | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
| US6933312B2 (en) | 2002-10-07 | 2005-08-23 | Agouron Pharmaceuticals, Inc. | Pyrazole derivatives |
| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| MXPA05010081A (es) | 2003-03-24 | 2005-11-23 | Hoffmann La Roche | Bencil-piridazinonas como inhibidores de transcriptasa inversa. |
| US7220772B2 (en) | 2003-09-05 | 2007-05-22 | Pfizer, Inc. | Pyrazole derivatives |
| DK1775298T3 (da) * | 2004-07-01 | 2013-05-21 | Daiichi Sankyo Co Ltd | Thienopyrazolderivat med PDE7-inhibitorisk aktivitet |
| US20070005049A1 (en) * | 2005-06-30 | 2007-01-04 | Comben Richard H | Apparatus and Method of Treating Urinary Incontinence by Heating Urethra |
| NZ574207A (en) * | 2006-07-05 | 2010-10-29 | Pfizer Prod Inc | Pyrazole derivatives as cytochrome p450 inhibitors |
| AU2007286345B2 (en) | 2006-08-16 | 2012-03-08 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| GB0713479D0 (en) * | 2007-07-11 | 2007-08-22 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| JP5411160B2 (ja) | 2007-12-21 | 2014-02-12 | エフ.ホフマン−ラ ロシュ アーゲー | 複素環式抗ウイルス性化合物 |
| GB0823000D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isothiazole and pyrazole derivatives with plant growth regulating properties |
| CN102333781B (zh) | 2009-02-25 | 2014-06-11 | 第一三共株式会社 | 三环吡唑并嘧啶衍生物 |
| FR2951549B1 (fr) | 2009-10-15 | 2013-08-23 | Olivier Schussler | Procede d'obtention de bioprotheses medicales implantables |
| WO2012026433A1 (ja) | 2010-08-23 | 2012-03-01 | 第一三共株式会社 | 三環性ピラゾロピリミジン誘導体のフリー体結晶 |
| WO2012026434A1 (ja) | 2010-08-23 | 2012-03-01 | 第一三共株式会社 | 三環性ピラゾロピリミジン誘導体の結晶 |
| US9695127B2 (en) | 2012-11-08 | 2017-07-04 | University of Pittsburgh—of the Commonwealth System of Higher Education | Compounds for treating HIV and methods for using the compounds |
| US9925190B2 (en) | 2015-02-16 | 2018-03-27 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecules targeting HIV-1 Nef |
| JP7301042B2 (ja) | 2018-03-30 | 2023-06-30 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除組成物 |
| US20220380341A1 (en) * | 2018-10-18 | 2022-12-01 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Inhibitors of hiv-1 nef for the treatment of hiv disease |
| FR3121927B1 (fr) | 2021-04-19 | 2023-03-31 | Eiffage Genie Civil Terrassement | Procédé d’inertage des boues d’excavation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993015060A1 (fr) | 1992-01-22 | 1993-08-05 | Nissan Chemical Industries, Ltd. | Derive de pyrazole substitue et bactericide agrohorticole |
| RU2130453C1 (ru) * | 1992-12-17 | 1999-05-20 | Пфайзер Инк. | Замещенные пиразолы, фармацевтическая композиция на их основе, способ лечения, промежуточный продукт |
| TW336932B (en) * | 1992-12-17 | 1998-07-21 | Pfizer | Amino-substituted pyrazoles |
| JP2862374B2 (ja) * | 1992-12-17 | 1999-03-03 | フアイザー・インコーポレイテツド | Crfアンタゴニスト活性を有するピラゾール及びピラゾロピリミジン |
| US6005109A (en) | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| WO2006027423A1 (fr) * | 2004-08-09 | 2006-03-16 | Simag Developpement | Dispositif de saisie comportant un capteur optique suivi d’un moyen de filtrage |
-
2000
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2001
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- 2001-10-04 RU RU2003112610/04A patent/RU2270832C2/ru not_active IP Right Cessation
- 2001-10-04 YU YU27203A patent/YU27203A/sh unknown
- 2001-10-04 JP JP2002534293A patent/JP4015548B2/ja not_active Expired - Fee Related
- 2001-10-04 IL IL15487501A patent/IL154875A0/xx unknown
- 2001-10-04 MX MXPA03003070A patent/MXPA03003070A/es active IP Right Grant
- 2001-10-04 PL PL01362918A patent/PL362918A1/xx not_active Application Discontinuation
- 2001-10-04 KR KR10-2003-7004984A patent/KR100534158B1/ko not_active Expired - Fee Related
- 2001-10-04 AU AU2002221651A patent/AU2002221651B2/en not_active Ceased
- 2001-10-04 BR BR0114483-9A patent/BR0114483A/pt not_active Application Discontinuation
- 2001-10-04 EP EP01986680A patent/EP1326843A1/en not_active Withdrawn
- 2001-10-04 CA CA002423515A patent/CA2423515A1/en not_active Abandoned
- 2001-10-04 AU AU2165102A patent/AU2165102A/xx active Pending
- 2001-10-04 HU HU0302722A patent/HUP0302722A2/hu unknown
- 2001-10-04 CN CNA2005100088329A patent/CN1680333A/zh active Pending
- 2001-10-04 WO PCT/EP2001/011474 patent/WO2002030907A1/en not_active Ceased
- 2001-10-04 NZ NZ524740A patent/NZ524740A/en unknown
- 2001-10-04 CN CNB018171710A patent/CN1191239C/zh not_active Expired - Fee Related
- 2001-10-04 CZ CZ20031297A patent/CZ20031297A3/cs unknown
- 2001-10-05 PE PE2001000993A patent/PE20020750A1/es not_active Application Discontinuation
- 2001-10-05 AR ARP010104697A patent/AR030858A1/es not_active Application Discontinuation
- 2001-10-09 PA PA20018530301A patent/PA8530301A1/es unknown
- 2001-10-09 UY UY26956A patent/UY26956A1/es not_active Application Discontinuation
- 2001-10-09 GT GT200100201A patent/GT200100201A/es unknown
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2003
- 2003-03-31 ZA ZA200302519A patent/ZA200302519B/en unknown
- 2003-04-07 MA MA27096A patent/MA26951A1/fr unknown
- 2003-04-08 EC EC2003004547A patent/ECSP034547A/es unknown
- 2003-04-09 NO NO20031615A patent/NO20031615L/no unknown
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2004
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