ZA200302519B - Pyrazole derivatives for treatment of viral diseases. - Google Patents
Pyrazole derivatives for treatment of viral diseases. Download PDFInfo
- Publication number
- ZA200302519B ZA200302519B ZA200302519A ZA200302519A ZA200302519B ZA 200302519 B ZA200302519 B ZA 200302519B ZA 200302519 A ZA200302519 A ZA 200302519A ZA 200302519 A ZA200302519 A ZA 200302519A ZA 200302519 B ZA200302519 B ZA 200302519B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- substituted
- substituents
- methyl
- alkoxy
- Prior art date
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- 201000010099 disease Diseases 0.000 title claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 26
- 150000003217 pyrazoles Chemical class 0.000 title description 14
- 230000003612 virological effect Effects 0.000 title description 6
- -1 3,5-dichlorophenyl Chemical group 0.000 claims description 499
- 125000001424 substituent group Chemical group 0.000 claims description 233
- 239000000460 chlorine Substances 0.000 claims description 133
- 229910052801 chlorine Inorganic materials 0.000 claims description 133
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 132
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 117
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 117
- 229910052794 bromium Inorganic materials 0.000 claims description 117
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 125000003107 substituted aryl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 230000001404 mediated effect Effects 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 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 12
- 150000002170 ethers Chemical class 0.000 claims description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
- 229960004217 benzyl alcohol Drugs 0.000 claims description 4
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- UCQXGBRCZAAKQA-UHFFFAOYSA-N 4-benzyl-1-butan-2-yl-5-(3,5-dichlorophenyl)sulfanyl-3-methylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)CC)N=C(C)C=1CC1=CC=CC=C1 UCQXGBRCZAAKQA-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
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 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
- 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
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-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
- 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
- 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
- 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
- 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
- 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
- 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 1
- BKODVIQULRWQCC-UHFFFAOYSA-N 4-[[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-3,5-dimethyl-1,2-oxazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC=1C(C)=NOC=1C BKODVIQULRWQCC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- HPXJAFUCKPOGAL-UHFFFAOYSA-N 4-[[5-(3-chloro-5-methoxyphenyl)sulfanyl-3-methyl-1-propan-2-ylpyrazol-4-yl]methyl]-2-methoxypyridine Chemical compound COC1=CC(Cl)=CC(SC=2N(N=C(C)C=2CC=2C=C(OC)N=CC=2)C(C)C)=C1 HPXJAFUCKPOGAL-UHFFFAOYSA-N 0.000 claims 1
- LGJHDDLFPIHPES-UHFFFAOYSA-N 4-benzyl-1-cyclohexyl-5-(3,5-dichlorophenyl)sulfanyl-3-methylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(CC=2C=CC=CC=2)C(C)=NN1C1CCCCC1 LGJHDDLFPIHPES-UHFFFAOYSA-N 0.000 claims 1
- SDHAKPVEGVKHBF-UHFFFAOYSA-N 4-benzyl-1-cyclopentyl-5-(3,5-dichlorophenyl)sulfanyl-3-methylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(CC=2C=CC=CC=2)C(C)=NN1C1CCCC1 SDHAKPVEGVKHBF-UHFFFAOYSA-N 0.000 claims 1
- ADGAITDHGZTICM-UHFFFAOYSA-N 4-benzyl-3-methyl-5-(3-nitrophenoxy)-1-phenylpyrazole Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(C=2C=CC=CC=2)C=1OC1=CC=CC([N+]([O-])=O)=C1 ADGAITDHGZTICM-UHFFFAOYSA-N 0.000 claims 1
- NRDDVXVNLZJGGZ-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-(methoxymethyl)pyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(COC)C=1CC1=CC=CC=C1 NRDDVXVNLZJGGZ-UHFFFAOYSA-N 0.000 claims 1
- FRXKMTUYHPDRBS-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CC1=CC=CC=C1 FRXKMTUYHPDRBS-UHFFFAOYSA-N 0.000 claims 1
- IIOYYHRCLJFDDI-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-(methoxymethyl)-1-methylpyrazole Chemical compound C=1C=CC=CC=1CC=1C(COC)=NN(C)C=1SC1=CC(Cl)=CC(Cl)=C1 IIOYYHRCLJFDDI-UHFFFAOYSA-N 0.000 claims 1
- MUWAVSUCAADCFE-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-(2,2,2-trifluoroethyl)pyrazole Chemical compound C=1C=CC=CC=1CC=1C(C)=NN(CC(F)(F)F)C=1SC1=CC(Cl)=CC(Cl)=C1 MUWAVSUCAADCFE-UHFFFAOYSA-N 0.000 claims 1
- DHPKIWKGJWSJGG-UHFFFAOYSA-N 4-benzyl-5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-(2-methylpropyl)pyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC(C)C)N=C(C)C=1CC1=CC=CC=C1 DHPKIWKGJWSJGG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- SGMXMBTXAHPIPQ-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methyl-4-(2-phenylethyl)pyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1CCC1=CC=CC=C1 SGMXMBTXAHPIPQ-UHFFFAOYSA-N 0.000 claims 1
- QMPQNKAGOKXPBO-OUKQBFOZSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-(methoxymethyl)-1-phenyl-4-[(e)-2-phenylethenyl]pyrazole Chemical compound C=1C=CC=CC=1/C=C/C=1C(COC)=NN(C=2C=CC=CC=2)C=1SC1=CC(Cl)=CC(Cl)=C1 QMPQNKAGOKXPBO-OUKQBFOZSA-N 0.000 claims 1
- 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 1
- 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 1
- GSSWVAZGAOYXPZ-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-yl-4-(thiophen-3-ylmethyl)pyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1CC=1C=CSC=1 GSSWVAZGAOYXPZ-UHFFFAOYSA-N 0.000 claims 1
- GOUPGFWUJXZNJB-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-methyl-4-(phenylmethoxymethyl)-1-propan-2-ylpyrazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(C)C=1COCC1=CC=CC=C1 GOUPGFWUJXZNJB-UHFFFAOYSA-N 0.000 claims 1
- XBYTXCGZSDPHIV-UHFFFAOYSA-N 5-(3-chlorophenyl)sulfanyl-3-(methoxymethyl)-1-methyl-4-(2-phenylethenyl)pyrazole Chemical compound C=1C=CC=CC=1C=CC=1C(COC)=NN(C)C=1SC1=CC=CC(Cl)=C1 XBYTXCGZSDPHIV-UHFFFAOYSA-N 0.000 claims 1
- FOUAEZVKMRMHGK-UHFFFAOYSA-N 5-[[5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-3-methylpyrazol-4-yl]methoxy]-2-methylpyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(C)C=1COC1=CC=C(C)N=C1 FOUAEZVKMRMHGK-UHFFFAOYSA-N 0.000 claims 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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- A61K31/41—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
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- 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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- A61K31/495—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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- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302519B true ZA200302519B (en) | 2004-06-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| ZA200302519A ZA200302519B (en) | 2000-10-10 | 2003-03-31 | Pyrazole derivatives for treatment of viral diseases. |
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| EP (1) | EP1326843A1 (enExample) |
| JP (1) | JP4015548B2 (enExample) |
| KR (1) | KR100534158B1 (enExample) |
| CN (2) | CN1680333A (enExample) |
| AR (1) | AR030858A1 (enExample) |
| AU (2) | AU2002221651B2 (enExample) |
| BR (1) | BR0114483A (enExample) |
| CA (1) | CA2423515A1 (enExample) |
| CZ (1) | CZ20031297A3 (enExample) |
| EC (1) | ECSP034547A (enExample) |
| GB (1) | GB0024795D0 (enExample) |
| GT (1) | GT200100201A (enExample) |
| HR (1) | HRP20030251A2 (enExample) |
| HU (1) | HUP0302722A2 (enExample) |
| IL (1) | IL154875A0 (enExample) |
| MA (1) | MA26951A1 (enExample) |
| MX (1) | MXPA03003070A (enExample) |
| NO (1) | NO20031615L (enExample) |
| NZ (1) | NZ524740A (enExample) |
| PA (1) | PA8530301A1 (enExample) |
| PE (1) | PE20020750A1 (enExample) |
| PL (1) | PL362918A1 (enExample) |
| RU (1) | RU2270832C2 (enExample) |
| UY (1) | UY26956A1 (enExample) |
| WO (1) | WO2002030907A1 (enExample) |
| YU (1) | YU27203A (enExample) |
| ZA (1) | ZA200302519B (enExample) |
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 |
| 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 |
| DE60319254T2 (de) | 2002-09-26 | 2009-02-12 | Pfizer Inc. | Pyrazolamide zur behandlung von hiv-infektionen |
| US6933312B2 (en) | 2002-10-07 | 2005-08-23 | Agouron Pharmaceuticals, Inc. | Pyrazole derivatives |
| GB0223234D0 (en) * | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
| GB0223232D0 (en) * | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| CA2518823A1 (en) * | 2003-03-24 | 2004-10-07 | F.Hoffmann-La Roche Ag | Benzyl-pyridazinons as reverse transcriptase inhibitors |
| US7220772B2 (en) | 2003-09-05 | 2007-05-22 | Pfizer, Inc. | Pyrazole derivatives |
| CA2569530C (en) * | 2004-07-01 | 2013-07-30 | Daiichi Asubio Pharma Co.,Ltd. | Thienopyrazole derivative having pde 7 inhibitory activity |
| US20070005049A1 (en) * | 2005-06-30 | 2007-01-04 | Comben Richard H | Apparatus and Method of Treating Urinary Incontinence by Heating Urethra |
| AU2007270814B2 (en) * | 2006-07-05 | 2011-07-14 | Pfizer Products Inc. | Pyrazole derivatives as cytochrome P450 inhibitors |
| PL2057125T3 (pl) * | 2006-08-16 | 2011-09-30 | Hoffmann La Roche | Nienukleozydowe inhibitory odwrotnej transkryptazy |
| GB0713479D0 (en) * | 2007-07-11 | 2007-08-22 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| RU2495878C2 (ru) | 2007-12-21 | 2013-10-20 | Ф.Хоффманн-Ля Рош Аг | Гетероциклические антивирусные соединения |
| GB0823000D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isothiazole and pyrazole derivatives with plant growth regulating properties |
| NZ595233A (en) | 2009-02-25 | 2013-01-25 | Daiichi Sankyo Co Ltd | Tricyclic pyrazolopyrimidine derivatives |
| FR2951549B1 (fr) | 2009-10-15 | 2013-08-23 | Olivier Schussler | Procede d'obtention de bioprotheses medicales implantables |
| EP2610260A4 (en) | 2010-08-23 | 2014-01-15 | Daiichi Sankyo Co Ltd | CRYSTAL OF TRICYCLIC PYRAZOLPYRIMIDINE DERIVATIVE |
| 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 |
| WO2014074628A1 (en) * | 2012-11-08 | 2014-05-15 | 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 |
| EP3778583B1 (en) | 2018-03-30 | 2025-06-18 | Sumitomo Chemical Company, Limited | Heterocyclic compound and arthropod pest control composition containing same |
| WO2020081856A1 (en) * | 2018-10-18 | 2020-04-23 | 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 |
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| EP0627423A4 (en) | 1992-01-22 | 1995-02-15 | Nissan Chemical Ind Ltd | SUBSTITUTED PYRAZOLE DERIVATIVES AND BACTERICIDES FOR AGRICULTURE AND GARDENING. |
| BR9307664A (pt) * | 1992-12-17 | 1999-06-29 | Pfizer | Pirazóis substituídos como antagonistas |
| US6005109A (en) | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| WO1994013643A1 (en) * | 1992-12-17 | 1994-06-23 | Pfizer Inc. | Pyrazoles and pyrazolopyrimidines having crf antagonist activity |
| TW336932B (en) * | 1992-12-17 | 1998-07-21 | Pfizer | Amino-substituted pyrazoles |
| WO2006027423A1 (fr) * | 2004-08-09 | 2006-03-16 | Simag Developpement | Dispositif de saisie comportant un capteur optique suivi d’un moyen de filtrage |
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2000
- 2000-10-10 GB GBGB0024795.7A patent/GB0024795D0/en not_active Ceased
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2001
- 2001-09-20 US US09/956,656 patent/US6699887B2/en not_active Expired - Fee Related
- 2001-10-04 CN CNA2005100088329A patent/CN1680333A/zh active Pending
- 2001-10-04 AU AU2002221651A patent/AU2002221651B2/en not_active Ceased
- 2001-10-04 KR KR10-2003-7004984A patent/KR100534158B1/ko not_active Expired - Fee Related
- 2001-10-04 AU AU2165102A patent/AU2165102A/xx active Pending
- 2001-10-04 NZ NZ524740A patent/NZ524740A/en unknown
- 2001-10-04 PL PL01362918A patent/PL362918A1/xx not_active Application Discontinuation
- 2001-10-04 MX MXPA03003070A patent/MXPA03003070A/es active IP Right Grant
- 2001-10-04 HR HR20030251A patent/HRP20030251A2/hr not_active Application Discontinuation
- 2001-10-04 EP EP01986680A patent/EP1326843A1/en not_active Withdrawn
- 2001-10-04 JP JP2002534293A patent/JP4015548B2/ja not_active Expired - Fee Related
- 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 CZ CZ20031297A patent/CZ20031297A3/cs unknown
- 2001-10-04 CN CNB018171710A patent/CN1191239C/zh not_active Expired - Fee Related
- 2001-10-04 CA CA002423515A patent/CA2423515A1/en not_active Abandoned
- 2001-10-04 HU HU0302722A patent/HUP0302722A2/hu unknown
- 2001-10-04 IL IL15487501A patent/IL154875A0/xx unknown
- 2001-10-04 BR BR0114483-9A patent/BR0114483A/pt not_active Application Discontinuation
- 2001-10-04 WO PCT/EP2001/011474 patent/WO2002030907A1/en not_active Ceased
- 2001-10-05 AR ARP010104697A patent/AR030858A1/es not_active Application Discontinuation
- 2001-10-05 PE PE2001000993A patent/PE20020750A1/es not_active Application Discontinuation
- 2001-10-09 UY UY26956A patent/UY26956A1/es not_active Application Discontinuation
- 2001-10-09 PA PA20018530301A patent/PA8530301A1/es unknown
- 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
-
2004
- 2004-01-27 US US10/766,712 patent/US7183296B2/en not_active Expired - Fee Related
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