JP2009529059A5 - - Google Patents
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- JP2009529059A5 JP2009529059A5 JP2008558416A JP2008558416A JP2009529059A5 JP 2009529059 A5 JP2009529059 A5 JP 2009529059A5 JP 2008558416 A JP2008558416 A JP 2008558416A JP 2008558416 A JP2008558416 A JP 2008558416A JP 2009529059 A5 JP2009529059 A5 JP 2009529059A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- thiazol
- trifluoromethyl
- pyridin
- amino
- 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.)
- Withdrawn
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- -1 alkyl carbamate Chemical compound 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000003282 alkyl amino group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- 235000021317 phosphate Nutrition 0.000 claims 4
- COYUWWHXFFZSAH-UHFFFAOYSA-N 1-[4-[methyl(pentyl)amino]-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 COYUWWHXFFZSAH-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- BQLUUHGCSLGJCN-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 BQLUUHGCSLGJCN-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- SRDHVNLUJWGSQV-UHFFFAOYSA-N 1-(3-fluoro-4-pentoxyphenyl)-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 SRDHVNLUJWGSQV-UHFFFAOYSA-N 0.000 claims 1
- KGLWABYMDPSEFP-UHFFFAOYSA-N 1-(3-fluoro-4-pentoxyphenyl)-1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 KGLWABYMDPSEFP-UHFFFAOYSA-N 0.000 claims 1
- JWTZHVDNWFHULT-UHFFFAOYSA-N 1-(4-hexoxyphenyl)-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 JWTZHVDNWFHULT-UHFFFAOYSA-N 0.000 claims 1
- LSQGZKVSOGEIHG-UHFFFAOYSA-N 1-(4-hexoxyphenyl)-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 LSQGZKVSOGEIHG-UHFFFAOYSA-N 0.000 claims 1
- BPBNHYGURVGCOK-UHFFFAOYSA-N 1-(4-octoxyphenyl)-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 BPBNHYGURVGCOK-UHFFFAOYSA-N 0.000 claims 1
- ABIZFELEDDDVTB-UHFFFAOYSA-N 1-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-1-[4-hexyl-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(CCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 ABIZFELEDDDVTB-UHFFFAOYSA-N 0.000 claims 1
- IYMMAKXGGQXSGL-UHFFFAOYSA-N 1-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-1-[4-octoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 IYMMAKXGGQXSGL-UHFFFAOYSA-N 0.000 claims 1
- PQKQQYANIZNQNV-UHFFFAOYSA-N 1-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-1-[4-octyl-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(CCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 PQKQQYANIZNQNV-UHFFFAOYSA-N 0.000 claims 1
- DVUXHKUCLWZNII-UHFFFAOYSA-N 1-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-1-[4-pentoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 DVUXHKUCLWZNII-UHFFFAOYSA-N 0.000 claims 1
- ONVIXLQJRPOJON-UHFFFAOYSA-N 1-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-1-[4-pentoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C(=CC(F)=CC=2)F)=CS1 ONVIXLQJRPOJON-UHFFFAOYSA-N 0.000 claims 1
- ZEHPMRGPAJPVOZ-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 ZEHPMRGPAJPVOZ-UHFFFAOYSA-N 0.000 claims 1
- OFLWYLCWNONOIJ-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 OFLWYLCWNONOIJ-UHFFFAOYSA-N 0.000 claims 1
- DGYTYRIPKFAFAO-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-[4-(3-oxo-4h-1,4-benzoxazin-6-yl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=C3NC(=O)COC3=CC=2)=CS1 DGYTYRIPKFAFAO-UHFFFAOYSA-N 0.000 claims 1
- LDHSVIOWFASFMS-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 LDHSVIOWFASFMS-UHFFFAOYSA-N 0.000 claims 1
- XNPZBGSSIYIMMD-UHFFFAOYSA-N 1-[4-(2-methylpyridin-3-yl)-1,3-thiazol-2-yl]-1-[4-pentoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C(=NC=CC=2)C)=CS1 XNPZBGSSIYIMMD-UHFFFAOYSA-N 0.000 claims 1
- ZGTWRYRRURKLRW-UHFFFAOYSA-N 1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-1-(4-hexoxyphenyl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 ZGTWRYRRURKLRW-UHFFFAOYSA-N 0.000 claims 1
- PDNPOROPMBQFNT-UHFFFAOYSA-N 1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 PDNPOROPMBQFNT-UHFFFAOYSA-N 0.000 claims 1
- SMNSKSZBALHCSI-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-(4-heptoxyphenyl)urea Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 SMNSKSZBALHCSI-UHFFFAOYSA-N 0.000 claims 1
- UMYXYGUUDPNHMA-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-(4-hexoxyphenyl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 UMYXYGUUDPNHMA-UHFFFAOYSA-N 0.000 claims 1
- QQNQGKPZXMBLOW-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 QQNQGKPZXMBLOW-UHFFFAOYSA-N 0.000 claims 1
- VBNKFZYIXUOARE-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-[4-[methyl(pentyl)amino]-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 VBNKFZYIXUOARE-UHFFFAOYSA-N 0.000 claims 1
- VMRDMLIWJUSYFM-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-[4-methoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 VMRDMLIWJUSYFM-UHFFFAOYSA-N 0.000 claims 1
- UJQVYRRSPAUHSQ-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-[4-pentoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 UJQVYRRSPAUHSQ-UHFFFAOYSA-N 0.000 claims 1
- PYFAJRXXUOTBIB-UHFFFAOYSA-N 1-[4-(cyclohexylmethoxy)-3-fluorophenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(OCC2CCCCC2)C(F)=CC=1N(C(=O)N)C(SC=1)=NC=1C1=CC=CN=C1 PYFAJRXXUOTBIB-UHFFFAOYSA-N 0.000 claims 1
- HMXSYFXAAABFPL-UHFFFAOYSA-N 1-[4-(cyclohexylmethoxy)-3-fluorophenyl]-1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]urea Chemical compound C=1C=C(OCC2CCCCC2)C(F)=CC=1N(C(=O)N)C(SC=1)=NC=1C1=CC=C(F)C(F)=C1 HMXSYFXAAABFPL-UHFFFAOYSA-N 0.000 claims 1
- BQCSGHQZABRFMZ-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 BQCSGHQZABRFMZ-UHFFFAOYSA-N 0.000 claims 1
- ALNSJKPRDKPHGD-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-4-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CN=CC=2)=CS1 ALNSJKPRDKPHGD-UHFFFAOYSA-N 0.000 claims 1
- ZFOTZQYIMPPYNA-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]urea;1-[4-[methyl(pentyl)amino]-3-(trifluoromethyl)phenyl]-1-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1.C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 ZFOTZQYIMPPYNA-UHFFFAOYSA-N 0.000 claims 1
- PJUVXSJNODTDMA-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 PJUVXSJNODTDMA-UHFFFAOYSA-N 0.000 claims 1
- XVOUMRQSDWQERK-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 XVOUMRQSDWQERK-UHFFFAOYSA-N 0.000 claims 1
- JBSIOXNVUHMPJS-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(F)C(C(F)(F)F)=CC=1N(C(=O)N)C(SC=1)=NC=1C1=CC=CN=C1 JBSIOXNVUHMPJS-UHFFFAOYSA-N 0.000 claims 1
- YZZMVGKBKZIRPR-UHFFFAOYSA-N 1-[4-methoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 YZZMVGKBKZIRPR-UHFFFAOYSA-N 0.000 claims 1
- XTNDGPMOYHENMO-UHFFFAOYSA-N 1-[4-octoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 XTNDGPMOYHENMO-UHFFFAOYSA-N 0.000 claims 1
- NDWXDDSCFMMNAH-UHFFFAOYSA-N 1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 NDWXDDSCFMMNAH-UHFFFAOYSA-N 0.000 claims 1
- DOBZOQOOGVSLPK-UHFFFAOYSA-N 1-[4-pentoxy-3-(trifluoromethyl)phenyl]-3-phenyl-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C=1SC=C(N=1)C=1C=NC=CC=1)C(=O)NC1=CC=CC=C1 DOBZOQOOGVSLPK-UHFFFAOYSA-N 0.000 claims 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 claims 1
- GZQCERHCRZKVBU-UHFFFAOYSA-N 2-[[(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-[4-octoxy-3-(trifluoromethyl)phenyl]carbamoyl]amino]acetic acid Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)NCC(O)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 GZQCERHCRZKVBU-UHFFFAOYSA-N 0.000 claims 1
- BAMQFDSKUZJXHV-UHFFFAOYSA-N 2-[[[4-octoxy-3-(trifluoromethyl)phenyl]-(4-pyridin-3-yl-1,3-thiazol-2-yl)carbamoyl]amino]acetic acid Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)NCC(O)=O)C1=NC(C=2C=NC=CC=2)=CS1 BAMQFDSKUZJXHV-UHFFFAOYSA-N 0.000 claims 1
- ZMCNRRNKEMQNMD-UHFFFAOYSA-N 3-ethyl-1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)NCC)C1=NC(C=2C=NC=CC=2)=CS1 ZMCNRRNKEMQNMD-UHFFFAOYSA-N 0.000 claims 1
- ZIMUFHZVVIRLPQ-UHFFFAOYSA-N 3-tert-butyl-1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)NC(C)(C)C)C1=NC(C=2C=NC=CC=2)=CS1 ZIMUFHZVVIRLPQ-UHFFFAOYSA-N 0.000 claims 1
- DYODLMDOLJHUJB-UHFFFAOYSA-N 4-[4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)CCC(O)=O)C1=NC(C=2C=NC=CC=2)=CS1 DYODLMDOLJHUJB-UHFFFAOYSA-N 0.000 claims 1
- HFDITUDABQZIRP-UHFFFAOYSA-N 4-[n-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-4-(4-thiophen-2-ylbutoxy)-3-(trifluoromethyl)anilino]-4-oxobutanoic acid Chemical compound C=1C=C(OCCCCC=2SC=CC=2)C(C(F)(F)F)=CC=1N(C(=O)CCC(=O)O)C(SC=1F)=NC=1C1=CC=CN=C1 HFDITUDABQZIRP-UHFFFAOYSA-N 0.000 claims 1
- INSQVYKNZQRRJL-UHFFFAOYSA-N 4-[n-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-4-octoxy-3-(trifluoromethyl)anilino]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)CCC(O)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 INSQVYKNZQRRJL-UHFFFAOYSA-N 0.000 claims 1
- IYLQDBSUKVOFSC-UHFFFAOYSA-N 5-[2-[4-butoxy-n-carbamoyl-3-(trifluoromethyl)anilino]-1,3-thiazol-4-yl]-2-hydroxybenzamide Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=C(C(O)=CC=2)C(N)=O)=CS1 IYLQDBSUKVOFSC-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 1
- GYPUOUQFOYKIRN-UHFFFAOYSA-N [1-(n-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]-4-octoxyanilino)-1-oxopropan-2-yl] acetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(C)OC(C)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 GYPUOUQFOYKIRN-UHFFFAOYSA-N 0.000 claims 1
- VTPDOWKIIZISAU-UHFFFAOYSA-N [2-(4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoethyl] acetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=NC=CC=2)=CS1 VTPDOWKIIZISAU-UHFFFAOYSA-N 0.000 claims 1
- RMHIQDZAZHQKKW-UHFFFAOYSA-N [2-(n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-4-octoxyanilino)-2-oxoethyl] acetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 RMHIQDZAZHQKKW-UHFFFAOYSA-N 0.000 claims 1
- OTASFOFPHPJXLW-UHFFFAOYSA-N [2-(n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-octoxyanilino)-2-oxoethyl] acetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 OTASFOFPHPJXLW-UHFFFAOYSA-N 0.000 claims 1
- HRYNPPWEEMPJCG-UHFFFAOYSA-N [2-[4-[methyl(pentyl)amino]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-2-oxoethyl] acetate Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=NC=CC=2)=CS1 HRYNPPWEEMPJCG-UHFFFAOYSA-N 0.000 claims 1
- MAMKNGNJRINEHG-UHFFFAOYSA-N [2-[4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-2-oxoethyl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=NC=CC=2)=CS1 MAMKNGNJRINEHG-UHFFFAOYSA-N 0.000 claims 1
- XJSDXDRGKAFWPT-UHFFFAOYSA-N [2-[n-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-4-octoxy-3-(trifluoromethyl)anilino]-2-oxoethyl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 XJSDXDRGKAFWPT-UHFFFAOYSA-N 0.000 claims 1
- BVIIZTVVVWKVTB-UHFFFAOYSA-N [2-[n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-4-pentoxy-3-(trifluoromethyl)anilino]-2-oxoethyl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)COC(C)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 BVIIZTVVVWKVTB-UHFFFAOYSA-N 0.000 claims 1
- FLPKMSLEFQUPAA-UHFFFAOYSA-N [2-oxo-2-[4-pentoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-1-phenylethyl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C=1SC=C(N=1)C=1C=NC=CC=1)C(=O)C(OC(C)=O)C1=CC=CC=C1 FLPKMSLEFQUPAA-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- FGWPGLBHOOXQNV-UHFFFAOYSA-N ethyl 2-(4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(=O)OCC)C1=NC(C=2C=NC=CC=2)=CS1 FGWPGLBHOOXQNV-UHFFFAOYSA-N 0.000 claims 1
- 239000003889 eye drop Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- AJWPRRKSRHHWEF-UHFFFAOYSA-N methyl 2-(3-fluoro-4-pentoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 AJWPRRKSRHHWEF-UHFFFAOYSA-N 0.000 claims 1
- WYWGTENDABLBKZ-UHFFFAOYSA-N methyl 2-(3-fluoro-n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-pentoxyanilino)-2-oxoacetate Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 WYWGTENDABLBKZ-UHFFFAOYSA-N 0.000 claims 1
- ZELXVXHSONGIOI-UHFFFAOYSA-N methyl 2-(4-heptoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 ZELXVXHSONGIOI-UHFFFAOYSA-N 0.000 claims 1
- UVESKLHONKPZRP-UHFFFAOYSA-N methyl 2-(4-octyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 UVESKLHONKPZRP-UHFFFAOYSA-N 0.000 claims 1
- NSUVGYQHAWCHFW-UHFFFAOYSA-N methyl 2-(n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-4-octoxyanilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 NSUVGYQHAWCHFW-UHFFFAOYSA-N 0.000 claims 1
- MJGVWVXLBNGYHL-UHFFFAOYSA-N methyl 2-(n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-heptoxyanilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2SC(Cl)=CC=2)=CS1 MJGVWVXLBNGYHL-UHFFFAOYSA-N 0.000 claims 1
- WOBUBTJOQDBDSA-UHFFFAOYSA-N methyl 2-(n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-octoxyanilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2SC(Cl)=CC=2)=CS1 WOBUBTJOQDBDSA-UHFFFAOYSA-N 0.000 claims 1
- LWJYKQGCEJMOML-UHFFFAOYSA-N methyl 2-[4-[methyl(pentyl)amino]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 LWJYKQGCEJMOML-UHFFFAOYSA-N 0.000 claims 1
- OJTHMXSHEYXBLN-UHFFFAOYSA-N methyl 2-[n-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-4-pentoxy-3-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C(=CC(F)=CC=2)F)=CS1 OJTHMXSHEYXBLN-UHFFFAOYSA-N 0.000 claims 1
- BGNDIBDLXANVMP-UHFFFAOYSA-N methyl 2-[n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-pentoxy-3-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 BGNDIBDLXANVMP-UHFFFAOYSA-N 0.000 claims 1
- BZFJUZHNQISWSR-UHFFFAOYSA-N methyl 2-[n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-pentoxy-3-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2SC(Cl)=CC=2)=CS1 BZFJUZHNQISWSR-UHFFFAOYSA-N 0.000 claims 1
- CEMZBWPSKYISTN-UHFFFAOYSA-N methyl 2-amino-3-methylbutanoate Chemical compound COC(=O)C(N)C(C)C CEMZBWPSKYISTN-UHFFFAOYSA-N 0.000 claims 1
- IIDHBBQBRLLOAK-UHFFFAOYSA-N methyl 3-(3-fluoro-n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-pentoxyanilino)-3-oxopropanoate Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(=O)CC(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 IIDHBBQBRLLOAK-UHFFFAOYSA-N 0.000 claims 1
- ZNEJJCFXEPQUQE-UHFFFAOYSA-N methyl 3-(n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-octoxyanilino)-3-oxopropanoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)CC(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 ZNEJJCFXEPQUQE-UHFFFAOYSA-N 0.000 claims 1
- HGWUXGUEUDRDSR-UHFFFAOYSA-N methyl 3-[n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-pentoxy-3-(trifluoromethyl)anilino]-3-oxopropanoate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)CC(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 HGWUXGUEUDRDSR-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QMHOOHDBIPAOCW-UHFFFAOYSA-N n-[4-(1,3-benzothiazol-2-yl)-1,3-thiazol-2-yl]-n-(4-heptoxyphenyl)-5-methyl-1,2-oxazole-3-carboxamide Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C=1SC=C(N=1)C=1SC2=CC=CC=C2N=1)C(=O)C1=NOC(C)=C1 QMHOOHDBIPAOCW-UHFFFAOYSA-N 0.000 claims 1
- UOCWPJUZVFPODC-UHFFFAOYSA-N n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-n-(4-heptoxyphenyl)-5-methyl-1,2-oxazole-3-carboxamide Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C=1SC=C(N=1)C=1SC(Cl)=CC=1)C(=O)C1=NOC(C)=C1 UOCWPJUZVFPODC-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- PJTXAVLKGKLBCK-UHFFFAOYSA-M sodium;4-[4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-4-oxobutanoate Chemical compound [Na+].C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(=O)CCC([O-])=O)C1=NC(C=2C=NC=CC=2)=CS1 PJTXAVLKGKLBCK-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 229960002935 telaprevir Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78060906P | 2006-03-08 | 2006-03-08 | |
| PCT/US2007/006023 WO2007103550A2 (en) | 2006-03-08 | 2007-03-08 | Substituted aminothiazole derivatives with anti-hcv activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009529059A JP2009529059A (ja) | 2009-08-13 |
| JP2009529059A5 true JP2009529059A5 (enExample) | 2010-03-11 |
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Family Applications (1)
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| US (1) | US20070213301A1 (enExample) |
| EP (2) | EP2460800A1 (enExample) |
| JP (1) | JP2009529059A (enExample) |
| AU (1) | AU2007223797A1 (enExample) |
| CA (1) | CA2645072A1 (enExample) |
| NZ (1) | NZ570835A (enExample) |
| WO (1) | WO2007103550A2 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| BRPI0608910A2 (pt) * | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| CN101426774B (zh) | 2006-04-19 | 2012-04-25 | 安斯泰来制药有限公司 | 唑类甲酰胺衍生物 |
| BRPI0811939A2 (pt) * | 2007-05-22 | 2014-11-25 | Achillion Pharmaceuticals Inc | Tiazóis substituídos por heteroarila |
| WO2008154601A1 (en) * | 2007-06-12 | 2008-12-18 | Genelabs Technologies, Inc. | Anti-viral inhibitors and methods of use |
| ES2331220B1 (es) * | 2007-10-02 | 2010-09-23 | Palobiofarma, S.L. | Nuevos compuestos como antagonistas de los receptores a1 de adenosina. |
| WO2009054468A1 (ja) | 2007-10-24 | 2009-04-30 | Astellas Pharma Inc. | アゾールカルボキサミド化合物又はその塩 |
| US9029376B2 (en) | 2008-06-03 | 2015-05-12 | Siga Technologies, Inc. | Small molecule inhibitors for the treatment or prevention of dengue virus infection |
| US8106209B2 (en) * | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| EA201170349A1 (ru) * | 2008-08-18 | 2011-08-30 | Йейл Юниверсити | Модуляторы mif |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| EP2320738A4 (en) * | 2008-08-29 | 2011-08-24 | Transtech Pharma Inc | SUBSTITUTED AMINOTHIAZOL DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF AND USE THEREOF |
| CA2751210C (en) * | 2009-01-30 | 2015-04-21 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis c infection |
| US8481483B2 (en) * | 2009-02-19 | 2013-07-09 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| US8349312B2 (en) * | 2009-07-09 | 2013-01-08 | Enanta Pharmaceuticals, Inc. | Proline substituted cyclosporin analogues |
| US8685917B2 (en) * | 2009-07-09 | 2014-04-01 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| US8367053B2 (en) * | 2009-07-09 | 2013-02-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| US8623814B2 (en) * | 2010-02-23 | 2014-01-07 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| CN103957908A (zh) * | 2011-10-04 | 2014-07-30 | 肝炎和病毒研究所 | 作为包括肝细胞癌在内的癌症的抑制剂和作为肝炎病毒复制抑制剂的取代的氨基噻唑 |
| US8906853B2 (en) | 2012-11-28 | 2014-12-09 | Enanta Pharmaceuticals, Inc. | [N-Me-4-hydroxyleucine]-9-cyclosporin analogues for treatment and prevention of hepatitis C infection |
| EP3038626A4 (en) | 2013-08-26 | 2017-04-19 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis c |
| WO2016073480A1 (en) | 2014-11-03 | 2016-05-12 | Enanta Pharmaceuticals, Inc. | Novel cyclosporin analogues for preventing or treating hepatitis c infection |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467666A (en) * | 1966-11-07 | 1969-09-16 | Geigy Chem Corp | 2-substituted aminothiazoles |
| BE795907A (fr) * | 1972-02-25 | 1973-06-18 | Luso Farmaco Inst | 2-amino-4-arylthiazoles 5-substitues et leur preparation |
| DE3406329A1 (de) * | 1984-02-22 | 1985-08-22 | Merck Patent Gmbh, 6100 Darmstadt | Pyridone |
| DE674513T1 (de) | 1992-12-29 | 1996-01-18 | Abbott Lab | Inhibitoren der retroviralen protease. |
| DE69526958T2 (de) * | 1994-11-29 | 2003-01-16 | Hisamitsu Pharmaceutical Co., Inc. | Antibakterielle oder bakterizide mittel, die 2-aminothiazolderivate und deren salze enthalten |
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| AU762245B2 (en) * | 1998-09-18 | 2003-06-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| US7169931B2 (en) * | 2001-01-26 | 2007-01-30 | Shionogi & Co., Ltd. | Cyclic compounds exhibiting thrombopoietin receptor agonism |
| US7232838B2 (en) * | 2001-08-13 | 2007-06-19 | Janssen Pharmaceutica N.V. | 2-amino-4,5-trisubstituted thiazolyl derivatives |
| US7163952B2 (en) * | 2001-12-03 | 2007-01-16 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
| DE60221627D1 (de) * | 2001-12-21 | 2007-09-20 | Virochem Pharma Inc | Thiazolderivate und ihre Verwendung zur Behandlung oder Vorbeugung von Infektionen durch Flaviviren |
| JP4675318B2 (ja) * | 2003-02-10 | 2011-04-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｎ−アリールカルバミン酸エステルとハロ−ヘテロアリールとを反応させることによるｎ−ヘテロアリール−ｎ−アリール−アミンの調製のためのプロセスおよび類似のプロセス |
| TW200505902A (en) * | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| AU2004299198A1 (en) * | 2003-12-08 | 2005-06-30 | F. Hoffmann-La Roche Ag | Novel thiazole derivates |
| BRPI0608910A2 (pt) * | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| GB0513702D0 (en) * | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| BRPI0811939A2 (pt) * | 2007-05-22 | 2014-11-25 | Achillion Pharmaceuticals Inc | Tiazóis substituídos por heteroarila |
| US20090208550A1 (en) * | 2007-10-26 | 2009-08-20 | Cronstein Bruce N | Methods and compositions for treating hepatic diseases |
| US8106209B2 (en) * | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
-
2007
- 2007-03-08 AU AU2007223797A patent/AU2007223797A1/en not_active Abandoned
- 2007-03-08 JP JP2008558416A patent/JP2009529059A/ja not_active Withdrawn
- 2007-03-08 EP EP11187750A patent/EP2460800A1/en not_active Withdrawn
- 2007-03-08 US US11/683,749 patent/US20070213301A1/en not_active Abandoned
- 2007-03-08 CA CA002645072A patent/CA2645072A1/en not_active Abandoned
- 2007-03-08 EP EP07752705A patent/EP1996565A2/en not_active Withdrawn
- 2007-03-08 WO PCT/US2007/006023 patent/WO2007103550A2/en not_active Ceased
- 2007-03-08 NZ NZ570835A patent/NZ570835A/en not_active IP Right Cessation
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