JP2004531535A5 - - Google Patents
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- Publication number
- JP2004531535A5 JP2004531535A5 JP2002583387A JP2002583387A JP2004531535A5 JP 2004531535 A5 JP2004531535 A5 JP 2004531535A5 JP 2002583387 A JP2002583387 A JP 2002583387A JP 2002583387 A JP2002583387 A JP 2002583387A JP 2004531535 A5 JP2004531535 A5 JP 2004531535A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- methyl
- oxy
- diethyl
- dichlorophenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 38
- 125000001424 substituent group Chemical group 0.000 claims 37
- -1 homopiperidinyl Chemical group 0.000 claims 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 22
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- JGOLOOOFWVLWTN-UHFFFAOYSA-N 3-[1-(2-aminoethyl)-3,5-diethylpyrazol-4-yl]oxy-5-methylbenzonitrile Chemical compound CCC1=NN(CCN)C(CC)=C1OC1=CC(C)=CC(C#N)=C1 JGOLOOOFWVLWTN-UHFFFAOYSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- MCPUZZJBAHRIPO-UHFFFAOYSA-N Lersivirine Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(C#N)=CC(C#N)=C1 MCPUZZJBAHRIPO-UHFFFAOYSA-N 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- NWCGPEVEQLFEQE-UHFFFAOYSA-N 2-[4-(2,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(Cl)=CC=C1Cl NWCGPEVEQLFEQE-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- NMFHKIRUHWFKKA-UHFFFAOYSA-N 3-[(3,5-diethyl-1h-pyrazol-4-yl)oxy]-5-methylbenzonitrile Chemical compound CCC1=NNC(CC)=C1OC1=CC(C)=CC(C#N)=C1 NMFHKIRUHWFKKA-UHFFFAOYSA-N 0.000 claims 2
- QIWSCZSULIZKIY-UHFFFAOYSA-N 3-[1-(2-aminoethyl)-3,5-diethylpyrazol-4-yl]oxy-5-chlorobenzonitrile Chemical compound CCC1=NN(CCN)C(CC)=C1OC1=CC(Cl)=CC(C#N)=C1 QIWSCZSULIZKIY-UHFFFAOYSA-N 0.000 claims 2
- SVTFKLREEGKUHR-UHFFFAOYSA-N 3-[3,5-diethyl-1-(2-hydroxyethyl)pyrazol-4-yl]oxy-5-fluorobenzonitrile Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(F)=CC(C#N)=C1 SVTFKLREEGKUHR-UHFFFAOYSA-N 0.000 claims 2
- CVJGKKWYCMRWBA-UHFFFAOYSA-N 3-[3,5-diethyl-1-(2-hydroxyethyl)pyrazol-4-yl]oxy-5-methylbenzonitrile Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(C)=CC(C#N)=C1 CVJGKKWYCMRWBA-UHFFFAOYSA-N 0.000 claims 2
- WCWBYFXDBZAXMC-UHFFFAOYSA-N 3-[[3-[(benzylamino)methyl]-5-methyl-1h-pyrazol-4-yl]oxy]-5-chlorobenzonitrile Chemical compound C=1C(Cl)=CC(C#N)=CC=1OC=1C(C)=NNC=1CNCC1=CC=CC=C1 WCWBYFXDBZAXMC-UHFFFAOYSA-N 0.000 claims 2
- SDECLXAHXDUCCV-UHFFFAOYSA-N 3-chloro-5-[(3,5-diethyl-1h-pyrazol-4-yl)oxy]benzonitrile Chemical compound CCC1=NNC(CC)=C1OC1=CC(Cl)=CC(C#N)=C1 SDECLXAHXDUCCV-UHFFFAOYSA-N 0.000 claims 2
- AWTYEVJZOYXDMK-UHFFFAOYSA-N 3-chloro-5-[3,5-diethyl-1-(2-hydroxyethyl)pyrazol-4-yl]oxybenzonitrile Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(Cl)=CC(C#N)=C1 AWTYEVJZOYXDMK-UHFFFAOYSA-N 0.000 claims 2
- WYKYIZNMDJQGBI-UHFFFAOYSA-N 3-chloro-5-[[3-[[(4-cyanophenyl)methylamino]methyl]-5-methyl-1h-pyrazol-4-yl]oxy]benzonitrile Chemical compound C=1C(Cl)=CC(C#N)=CC=1OC=1C(C)=NNC=1CNCC1=CC=C(C#N)C=C1 WYKYIZNMDJQGBI-UHFFFAOYSA-N 0.000 claims 2
- LTSBRJXQVVZDJZ-UHFFFAOYSA-N 5-[(3,5-diethyl-1h-pyrazol-4-yl)oxy]benzene-1,3-dicarbonitrile Chemical compound CCC1=NNC(CC)=C1OC1=CC(C#N)=CC(C#N)=C1 LTSBRJXQVVZDJZ-UHFFFAOYSA-N 0.000 claims 2
- KLZJUQBUULSKHW-UHFFFAOYSA-N 5-[1-(2-aminoethyl)-3,5-diethylpyrazol-4-yl]oxybenzene-1,3-dicarbonitrile Chemical compound CCC1=NN(CCN)C(CC)=C1OC1=CC(C#N)=CC(C#N)=C1 KLZJUQBUULSKHW-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- NYBBRMVVCBSWRG-UHFFFAOYSA-N 1-(azetidin-3-yl)-4-(3,5-dichlorophenoxy)-3,5-diethylpyrazole Chemical compound CCC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(CC)=NN1C1CNC1 NYBBRMVVCBSWRG-UHFFFAOYSA-N 0.000 claims 1
- DUZFAQQKLXQTSC-UHFFFAOYSA-N 1-[1-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethyl]piperidin-4-yl]ethanone Chemical compound CCC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(CC)=NN1CCN1CCC(C(C)=O)CC1 DUZFAQQKLXQTSC-UHFFFAOYSA-N 0.000 claims 1
- GXZSRCLTCYULLM-UHFFFAOYSA-N 1-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]propan-2-ol Chemical compound CCC1=NN(CC(C)O)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 GXZSRCLTCYULLM-UHFFFAOYSA-N 0.000 claims 1
- DCSGVEWLFVIKGQ-UHFFFAOYSA-N 1-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]-n,n-dimethylmethanamine Chemical compound N1N=C(C)C(OC=2C=C(Cl)C=C(Cl)C=2)=C1CN(C)C DCSGVEWLFVIKGQ-UHFFFAOYSA-N 0.000 claims 1
- SPKKRWFYZLEGEL-UHFFFAOYSA-N 1-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]-n-methylmethanamine Chemical compound N1N=C(C)C(OC=2C=C(Cl)C=C(Cl)C=2)=C1CNC SPKKRWFYZLEGEL-UHFFFAOYSA-N 0.000 claims 1
- BEFFQGDEDVCFBM-UHFFFAOYSA-N 1-[4-[[2-(2-aminoethyl)-4-(3,5-dichlorophenoxy)-5-ethylpyrazol-3-yl]methyl]piperazin-1-yl]ethanone Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(CC)=NN(CCN)C=1CN1CCN(C(C)=O)CC1 BEFFQGDEDVCFBM-UHFFFAOYSA-N 0.000 claims 1
- KHDLQAWMKKSSOQ-UHFFFAOYSA-N 1-[4-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(C)=NN1 KHDLQAWMKKSSOQ-UHFFFAOYSA-N 0.000 claims 1
- HSGPFODMGRUDDU-UHFFFAOYSA-N 1-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]-1,2,4-triazole Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CN1C=NC=N1 HSGPFODMGRUDDU-UHFFFAOYSA-N 0.000 claims 1
- XXDQXYIYZSMCTQ-UHFFFAOYSA-N 1-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]-4-methoxypiperidine Chemical compound C1CC(OC)CCN1CC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(C)=NN1 XXDQXYIYZSMCTQ-UHFFFAOYSA-N 0.000 claims 1
- OTHXHMUYSZKLJB-UHFFFAOYSA-N 1-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(C)=NN1 OTHXHMUYSZKLJB-UHFFFAOYSA-N 0.000 claims 1
- RRYQOVHSSBBPOA-UHFFFAOYSA-N 1-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]piperidine-4-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CN1CCC(C(N)=O)CC1 RRYQOVHSSBBPOA-UHFFFAOYSA-N 0.000 claims 1
- DHTIAWMRGUUHGB-UHFFFAOYSA-N 1-cyclopropyl-n-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]methanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CNCC1CC1 DHTIAWMRGUUHGB-UHFFFAOYSA-N 0.000 claims 1
- YIVHNLCDRURFJJ-UHFFFAOYSA-N 2-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethoxy]ethanamine Chemical compound CCC1=NN(CCOCCN)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 YIVHNLCDRURFJJ-UHFFFAOYSA-N 0.000 claims 1
- XSQURKUBVDDYAN-UHFFFAOYSA-N 2-[3,5-diethyl-4-(2-fluorophenoxy)pyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=CC=C1F XSQURKUBVDDYAN-UHFFFAOYSA-N 0.000 claims 1
- JEFJCIIUQZLQRX-UHFFFAOYSA-N 2-[3,5-diethyl-4-(3-fluorophenoxy)pyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=CC(F)=C1 JEFJCIIUQZLQRX-UHFFFAOYSA-N 0.000 claims 1
- WAHRCWYJYQHTPZ-UHFFFAOYSA-N 2-[3,5-diethyl-4-(4-fluoro-3-methylphenoxy)pyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=C(F)C(C)=C1 WAHRCWYJYQHTPZ-UHFFFAOYSA-N 0.000 claims 1
- BIKRHHKVIRIPEL-UHFFFAOYSA-N 2-[4-(2,3-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=CC(Cl)=C1Cl BIKRHHKVIRIPEL-UHFFFAOYSA-N 0.000 claims 1
- RAXLWUCSQWGNPP-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=C(Cl)C=C1Cl RAXLWUCSQWGNPP-UHFFFAOYSA-N 0.000 claims 1
- SMUZAERATLKDCJ-UHFFFAOYSA-N 2-[4-(2,5-difluorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(F)=CC=C1F SMUZAERATLKDCJ-UHFFFAOYSA-N 0.000 claims 1
- AXFOKGBZAPBYOS-UHFFFAOYSA-N 2-[4-(2,6-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=C(Cl)C=CC=C1Cl AXFOKGBZAPBYOS-UHFFFAOYSA-N 0.000 claims 1
- IARZIPPMTKPNEJ-UHFFFAOYSA-N 2-[4-(2,6-difluorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=C(F)C=CC=C1F IARZIPPMTKPNEJ-UHFFFAOYSA-N 0.000 claims 1
- JUMRJIOEHDJHHX-UHFFFAOYSA-N 2-[4-(2-chlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=CC=C1Cl JUMRJIOEHDJHHX-UHFFFAOYSA-N 0.000 claims 1
- YEVODJYHJDIACX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=C(Cl)C(Cl)=C1 YEVODJYHJDIACX-UHFFFAOYSA-N 0.000 claims 1
- LGZJKMCHDMGPGW-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]-n'-hydroxyethanimidamide Chemical compound CCC1=NN(CC(=N)NO)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 LGZJKMCHDMGPGW-UHFFFAOYSA-N 0.000 claims 1
- SDPUYEBCBLQALO-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]-n,n-dimethylethanamine Chemical compound CCC1=NN(CCN(C)C)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 SDPUYEBCBLQALO-UHFFFAOYSA-N 0.000 claims 1
- GIPXCSHRAOHOKB-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]-n-methylethanamine Chemical compound CCC1=NN(CCNC)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 GIPXCSHRAOHOKB-UHFFFAOYSA-N 0.000 claims 1
- IMDWKWMSCFEAFH-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]acetohydrazide Chemical compound CCC1=NN(CC(=O)NN)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 IMDWKWMSCFEAFH-UHFFFAOYSA-N 0.000 claims 1
- LQYBWWAKXOIVBY-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]acetonitrile Chemical compound CCC1=NN(CC#N)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 LQYBWWAKXOIVBY-UHFFFAOYSA-N 0.000 claims 1
- WHIHJIHBDBTVEQ-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanamine Chemical compound CCC1=NN(CCN)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 WHIHJIHBDBTVEQ-UHFFFAOYSA-N 0.000 claims 1
- PFFCLZRYUXYYMI-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 PFFCLZRYUXYYMI-UHFFFAOYSA-N 0.000 claims 1
- UOLIKVWUFHHUHI-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3,5-dimethylpyrazol-1-yl]ethanol Chemical compound CC1=NN(CCO)C(C)=C1OC1=CC(Cl)=CC(Cl)=C1 UOLIKVWUFHHUHI-UHFFFAOYSA-N 0.000 claims 1
- LOPSNSATWNGZMH-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3-ethyl-5-(pyrazol-1-ylmethyl)pyrazol-1-yl]ethanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(CC)=NN(CCN)C=1CN1C=CC=N1 LOPSNSATWNGZMH-UHFFFAOYSA-N 0.000 claims 1
- FBFPCQPPGUKQAK-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3-ethyl-5-methoxypyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(OC)=C1OC1=CC(Cl)=CC(Cl)=C1 FBFPCQPPGUKQAK-UHFFFAOYSA-N 0.000 claims 1
- FQQPXUVJYJBXQP-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3-ethylpyrazol-1-yl]ethanamine Chemical compound CCC1=NN(CCN)C=C1OC1=CC(Cl)=CC(Cl)=C1 FQQPXUVJYJBXQP-UHFFFAOYSA-N 0.000 claims 1
- PGRNGUQELZJDEH-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-3-methyl-5-[(pyridin-3-ylmethylamino)methyl]pyrazol-1-yl]ethanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NN(CCO)C=1CNCC1=CC=CN=C1 PGRNGUQELZJDEH-UHFFFAOYSA-N 0.000 claims 1
- PIWKXOXFTGYFHS-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-5-(ethoxymethyl)-3-ethylpyrazol-1-yl]ethanamine Chemical compound CCC1=NN(CCN)C(COCC)=C1OC1=CC(Cl)=CC(Cl)=C1 PIWKXOXFTGYFHS-UHFFFAOYSA-N 0.000 claims 1
- HHOAPRCZIDSCSS-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-5-ethylpyrazol-1-yl]ethanamine Chemical compound C1=NN(CCN)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 HHOAPRCZIDSCSS-UHFFFAOYSA-N 0.000 claims 1
- CXSYHEDXHVMPSC-CYBMUJFWSA-N 2-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]-1-[(3r)-3-hydroxypiperidin-1-yl]ethanone Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CC(=O)N1CCC[C@@H](O)C1 CXSYHEDXHVMPSC-CYBMUJFWSA-N 0.000 claims 1
- PWQLVXLMSDXMJR-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]-1-piperidin-1-ylethanone Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CC(=O)N1CCCCC1 PWQLVXLMSDXMJR-UHFFFAOYSA-N 0.000 claims 1
- HFVIUKIZYBUYQK-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]acetonitrile Chemical compound CC1=NNC(CC#N)=C1OC1=CC(Cl)=CC(Cl)=C1 HFVIUKIZYBUYQK-UHFFFAOYSA-N 0.000 claims 1
- VSKHALLTUYRNDT-UHFFFAOYSA-N 2-[4-(3,5-difluorophenoxy)-3,5-diethylpyrazol-1-yl]ethanamine Chemical compound CCC1=NN(CCN)C(CC)=C1OC1=CC(F)=CC(F)=C1 VSKHALLTUYRNDT-UHFFFAOYSA-N 0.000 claims 1
- GOEPJNXINNCOPB-UHFFFAOYSA-N 2-[4-(3,5-difluorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(F)=CC(F)=C1 GOEPJNXINNCOPB-UHFFFAOYSA-N 0.000 claims 1
- JCADGWQNNIKRMS-UHFFFAOYSA-N 2-[4-(3,5-dimethylphenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC(C)=CC(C)=C1 JCADGWQNNIKRMS-UHFFFAOYSA-N 0.000 claims 1
- MIRJXXTZRISRIE-UHFFFAOYSA-N 2-[4-(3-chlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=CC(Cl)=C1 MIRJXXTZRISRIE-UHFFFAOYSA-N 0.000 claims 1
- PXLBQTAADMELSY-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)-3,5-diethylpyrazol-1-yl]ethanol Chemical compound CCC1=NN(CCO)C(CC)=C1OC1=CC=C(Cl)C=C1 PXLBQTAADMELSY-UHFFFAOYSA-N 0.000 claims 1
- JQQDVFDNPADCPD-UHFFFAOYSA-N 2-amino-6-[[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]methyl]-1h-pyrimidin-4-one Chemical compound CCC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(CC)=NN1CC1=CC(=O)NC(N)=N1 JQQDVFDNPADCPD-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
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- ORLPZPFFVGBJNE-UHFFFAOYSA-N n-[1-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1CC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(C)=NN1 ORLPZPFFVGBJNE-UHFFFAOYSA-N 0.000 claims 1
- XSUWKBCIEIRDSE-UHFFFAOYSA-N n-[2-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethylamino]ethyl]acetamide Chemical compound CCC1=NN(CCNCCNC(C)=O)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 XSUWKBCIEIRDSE-UHFFFAOYSA-N 0.000 claims 1
- SSYXBCHFNDKJEE-UHFFFAOYSA-N n-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethyl]-2-methoxyacetamide Chemical compound CCC1=NN(CCNC(=O)COC)C(CC)=C1OC1=CC(Cl)=CC(Cl)=C1 SSYXBCHFNDKJEE-UHFFFAOYSA-N 0.000 claims 1
- OVOKTFGRMMQQAG-UHFFFAOYSA-N n-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethyl]pyrazine-2-carboxamide Chemical compound CCC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(CC)=NN1CCNC(=O)C1=CN=CC=N1 OVOKTFGRMMQQAG-UHFFFAOYSA-N 0.000 claims 1
- UFXPCCFXVGOZGS-UHFFFAOYSA-N n-[2-[4-(3,5-dichlorophenoxy)-3,5-diethylpyrazol-1-yl]ethyl]pyridine-2-carboxamide Chemical compound CCC1=C(OC=2C=C(Cl)C=C(Cl)C=2)C(CC)=NN1CCNC(=O)C1=CC=CC=N1 UFXPCCFXVGOZGS-UHFFFAOYSA-N 0.000 claims 1
- CWIZWBWPKLWYFB-UHFFFAOYSA-N n-[2-[4-(3,5-dicyanophenoxy)-3,5-diethylpyrazol-1-yl]ethyl]-2-methoxyacetamide Chemical compound CCC1=NN(CCNC(=O)COC)C(CC)=C1OC1=CC(C#N)=CC(C#N)=C1 CWIZWBWPKLWYFB-UHFFFAOYSA-N 0.000 claims 1
- FZGBIAUPWMHGBY-UHFFFAOYSA-N n-[2-[[2-(2-aminoethyl)-4-(3,5-dichlorophenoxy)-5-ethylpyrazol-3-yl]methylamino]ethyl]acetamide Chemical compound CCC1=NN(CCN)C(CNCCNC(C)=O)=C1OC1=CC(Cl)=CC(Cl)=C1 FZGBIAUPWMHGBY-UHFFFAOYSA-N 0.000 claims 1
- BDSOEEKUKVCTLS-UHFFFAOYSA-N n-[2-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methylamino]ethyl]acetamide Chemical compound N1N=C(C)C(OC=2C=C(Cl)C=C(Cl)C=2)=C1CNCCNC(=O)C BDSOEEKUKVCTLS-UHFFFAOYSA-N 0.000 claims 1
- ZIFCJHSNDKBOIS-UHFFFAOYSA-N n-[2-[[4-(3-chloro-5-cyanophenoxy)-5-methyl-1h-pyrazol-3-yl]methylamino]ethyl]acetamide Chemical compound N1N=C(C)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1CNCCNC(=O)C ZIFCJHSNDKBOIS-UHFFFAOYSA-N 0.000 claims 1
- WCIDEPTVPAEOCP-UHFFFAOYSA-N n-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]-1-(4-fluorophenyl)methanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(C)=NNC=1CNCC1=CC=C(F)C=C1 WCIDEPTVPAEOCP-UHFFFAOYSA-N 0.000 claims 1
- KOMLNYOJIYEVIO-UHFFFAOYSA-N n-[[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]methyl]-2-methoxyethanamine Chemical compound N1N=C(C)C(OC=2C=C(Cl)C=C(Cl)C=2)=C1CNCCOC KOMLNYOJIYEVIO-UHFFFAOYSA-N 0.000 claims 1
- ZJIDSAHBJOWBOU-UHFFFAOYSA-N n-benzyl-2-[4-(3,5-dichlorophenoxy)-5-methyl-1h-pyrazol-3-yl]-n-methylacetamide Chemical compound N1N=C(C)C(OC=2C=C(Cl)C=C(Cl)C=2)=C1CC(=O)N(C)CC1=CC=CC=C1 ZJIDSAHBJOWBOU-UHFFFAOYSA-N 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003585 oxepinyl group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- BPOBLVMISWOGJA-UHFFFAOYSA-N tert-butyl n-[2-[4-(3,5-dichlorophenoxy)-3-ethyl-5-(hydroxymethyl)pyrazol-1-yl]ethyl]carbamate Chemical compound CCC1=NN(CCNC(=O)OC(C)(C)C)C(CO)=C1OC1=CC(Cl)=CC(Cl)=C1 BPOBLVMISWOGJA-UHFFFAOYSA-N 0.000 claims 1
- LUZHUNALIVHPSZ-UHFFFAOYSA-N tert-butyl n-[2-[4-(3,5-dichlorophenoxy)-3-ethyl-5-(pyrazol-1-ylmethyl)pyrazol-1-yl]ethyl]carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(CC)=NN(CCNC(=O)OC(C)(C)C)C=1CN1C=CC=N1 LUZHUNALIVHPSZ-UHFFFAOYSA-N 0.000 claims 1
- UKDGKNUBWLRPCC-UHFFFAOYSA-N tert-butyl n-[2-[4-(3,5-dichlorophenoxy)-3-ethyl-5-[[(4-methoxyphenyl)methylamino]methyl]pyrazol-1-yl]ethyl]carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(CC)=NN(CCNC(=O)OC(C)(C)C)C=1CNCC1=CC=C(OC)C=C1 UKDGKNUBWLRPCC-UHFFFAOYSA-N 0.000 claims 1
- QBZQQSZMAUBXMI-UHFFFAOYSA-N tert-butyl n-[2-[4-(3,5-dichlorophenoxy)-5-(ethoxymethyl)-3-ethylpyrazol-1-yl]ethyl]carbamate Chemical compound CCC1=NN(CCNC(=O)OC(C)(C)C)C(COCC)=C1OC1=CC(Cl)=CC(Cl)=C1 QBZQQSZMAUBXMI-UHFFFAOYSA-N 0.000 claims 1
- LWDILVRYYTWWRF-UHFFFAOYSA-N tert-butyl n-[2-[5-(aminomethyl)-4-(3,5-dichlorophenoxy)-3-ethylpyrazol-1-yl]ethyl]carbamate Chemical compound CCC1=NN(CCNC(=O)OC(C)(C)C)C(CN)=C1OC1=CC(Cl)=CC(Cl)=C1 LWDILVRYYTWWRF-UHFFFAOYSA-N 0.000 claims 1
- XWVBCSAEYWTGAU-UHFFFAOYSA-N tert-butyl n-[2-[5-(bromomethyl)-4-(3,5-dichlorophenoxy)-3-ethylpyrazol-1-yl]ethyl]carbamate Chemical compound CCC1=NN(CCNC(=O)OC(C)(C)C)C(CBr)=C1OC1=CC(Cl)=CC(Cl)=C1 XWVBCSAEYWTGAU-UHFFFAOYSA-N 0.000 claims 1
- NCGRVQYYISBJFB-UHFFFAOYSA-N tert-butyl n-[2-[5-[(4-acetylpiperazin-1-yl)methyl]-4-(3,5-dichlorophenoxy)-3-ethylpyrazol-1-yl]ethyl]carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC=1C(CC)=NN(CCNC(=O)OC(C)(C)C)C=1CN1CCN(C(C)=O)CC1 NCGRVQYYISBJFB-UHFFFAOYSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 125000005490 tosylate group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
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| GB0108999A GB0108999D0 (en) | 2001-04-10 | 2001-04-10 | Pyrazole derivatives |
| GB0127426A GB0127426D0 (en) | 2001-11-15 | 2001-11-15 | Pyrazole derivatives |
| PCT/IB2002/001234 WO2002085860A1 (en) | 2001-04-10 | 2002-04-04 | Pyrazole derivatives for treating hiv |
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| JP2004531535A JP2004531535A (ja) | 2004-10-14 |
| JP2004531535A5 true JP2004531535A5 (https=) | 2005-12-22 |
| JP3806090B2 JP3806090B2 (ja) | 2006-08-09 |
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| 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 |
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| BRPI0408704A (pt) | 2003-03-24 | 2006-03-07 | Hoffmann La Roche | benzil-piridazinonas como inibidores de transcriptase reversa |
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| US7220772B2 (en) | 2003-09-05 | 2007-05-22 | Pfizer, Inc. | Pyrazole derivatives |
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| 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 |
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- 2002-04-04 EA EA200300943A patent/EA007184B1/ru not_active IP Right Cessation
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- 2002-04-04 EE EEP200300497A patent/EE05400B1/xx unknown
- 2002-04-04 AT AT02708600T patent/ATE358669T1/de active
- 2002-04-04 PT PT02708600T patent/PT1377556E/pt unknown
- 2002-04-04 AU AU2002242926A patent/AU2002242926B2/en not_active Expired
- 2002-04-04 MX MXPA03009380A patent/MXPA03009380A/es active IP Right Grant
- 2002-04-04 DE DE60219292T patent/DE60219292T2/de not_active Expired - Lifetime
- 2002-04-04 CA CA002443449A patent/CA2443449C/en not_active Expired - Lifetime
- 2002-04-04 WO PCT/IB2002/001234 patent/WO2002085860A1/en not_active Ceased
- 2002-04-04 SK SK1244-2003A patent/SK287858B6/sk unknown
- 2002-04-04 SI SI200230986T patent/SI1762567T1/sl unknown
- 2002-04-04 DK DK02708600T patent/DK1377556T3/da active
- 2002-04-04 IL IL15787502A patent/IL157875A0/xx unknown
- 2002-04-04 PL PL396946A patent/PL217224B1/pl unknown
- 2002-04-04 OA OA1200300258A patent/OA12501A/en unknown
- 2002-04-04 ES ES02708600T patent/ES2283532T3/es not_active Expired - Lifetime
- 2002-04-04 NZ NZ529403A patent/NZ529403A/en not_active IP Right Cessation
- 2002-04-04 EP EP02708600A patent/EP1377556B1/en not_active Expired - Lifetime
- 2002-04-04 HU HU0303735A patent/HU229025B1/hu unknown
- 2002-04-05 US US10/118,512 patent/US7109228B2/en not_active Expired - Lifetime
- 2002-04-08 MY MYPI20021264A patent/MY146669A/en unknown
- 2002-04-08 AR ARP020101281A patent/AR037319A1/es active IP Right Grant
- 2002-04-09 UY UY27248A patent/UY27248A1/es not_active IP Right Cessation
- 2002-04-09 TW TW091107115A patent/TWI333488B/zh not_active IP Right Cessation
- 2002-04-10 PA PA20028543601A patent/PA8543601A1/es unknown
- 2002-04-10 PE PE2002000297A patent/PE20021056A1/es active IP Right Grant
- 2002-04-10 DO DO2002000378A patent/DOP2002000378A/es unknown
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2003
- 2003-09-04 IS IS6939A patent/IS2734B/is unknown
- 2003-09-09 CR CR7069A patent/CR7069A/es unknown
- 2003-09-11 IL IL157875A patent/IL157875A/en active IP Right Grant
- 2003-10-06 MA MA27336A patent/MA27009A1/fr unknown
- 2003-10-08 BG BG108244A patent/BG66349B1/bg unknown
- 2003-10-09 NO NO20034523A patent/NO326518B1/no not_active IP Right Cessation
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2005
- 2005-06-20 US US11/157,340 patent/US7435728B2/en not_active Expired - Lifetime
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2007
- 2007-05-10 CY CY20071100627T patent/CY1107626T1/el unknown
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2008
- 2008-08-25 US US12/197,655 patent/US8063044B2/en not_active Expired - Fee Related
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2010
- 2010-03-19 AR ARP100100890A patent/AR076259A2/es active IP Right Grant
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2011
- 2011-10-07 US US13/269,278 patent/US20120029192A1/en not_active Abandoned
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2012
- 2012-06-27 CY CY20121100571T patent/CY1113515T1/el unknown
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