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- Withdrawn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 (OSRAM) | 2010-03-11 |
Family
ID=38328551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008558416A Withdrawn JP2009529059A (ja) | 2006-03-08 | 2007-03-08 | 抗ｃ型肝炎ウイルス活性を有する置換アミノチアゾール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070213301A1 (OSRAM) |
| EP (2) | EP2460800A1 (OSRAM) |
| JP (1) | JP2009529059A (OSRAM) |
| AU (1) | AU2007223797A1 (OSRAM) |
| CA (1) | CA2645072A1 (OSRAM) |
| NZ (1) | NZ570835A (OSRAM) |
| WO (1) | WO2007103550A2 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2607617A1 (en) * | 2005-05-09 | 2006-11-16 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
| KR20090004976A (ko) | 2006-04-19 | 2009-01-12 | 아스테라스 세이야쿠 가부시키가이샤 | 아졸카르복사미드 유도체 |
| MX2009012613A (es) | 2007-05-22 | 2010-04-21 | Achillion Pharmaceuticals Inc | Tiazoles substituidos por heteroarilo y su uso como agentes antivirales. |
| TW200906826A (en) * | 2007-06-12 | 2009-02-16 | Genelabs Tech 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. |
| EP2206707B1 (en) | 2007-10-24 | 2014-07-23 | Astellas Pharma Inc. | Azolecarboxamide compound or salt thereof |
| MX338530B (es) * | 2008-06-03 | 2016-04-21 | Siga Technologies Inc | Inhibidores de molecula pequeña para el tratamiento o prevencion de infeccion de virus del dengue. |
| US8106209B2 (en) * | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| EP2326631A4 (en) * | 2008-08-18 | 2012-03-21 | Univ Yale | MIF MODULATORS |
| JP2012501334A (ja) * | 2008-08-29 | 2012-01-19 | トランス テック ファーマ，インコーポレイテッド | 置換アミノチアゾール誘導体、医薬組成物、および使用の方法 |
| AU2010208071C1 (en) | 2009-01-30 | 2013-06-20 | 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 |
| 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 |
| US8349312B2 (en) * | 2009-07-09 | 2013-01-08 | Enanta Pharmaceuticals, Inc. | Proline substituted cyclosporin analogues |
| US8623814B2 (en) * | 2010-02-23 | 2014-01-07 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| WO2013052613A1 (en) * | 2011-10-04 | 2013-04-11 | Institute For Hepatitis And Virus Research | Substituted aminothiazoles as inhibitors of cancers, including hepatocellular carcinoma, and as inhibitors of hepatitis virus replication |
| WO2014085623A1 (en) | 2012-11-28 | 2014-06-05 | Enanta Pharmaceuticals, Inc. | Novel [n-me-4-hydroxyleucine]-9-cyclosporin analogues |
| SG11201601274QA (en) | 2013-08-26 | 2016-03-30 | Enanta Pharm 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 |
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| 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 |
| KR100187613B1 (ko) | 1992-12-29 | 1999-06-01 | 스티븐 에프. 웨인스톡 | 레트로바이러스성 프로테이제 억제 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
| US5856347A (en) * | 1994-11-29 | 1999-01-05 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
| 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 |
| WO2002059099A1 (en) * | 2001-01-26 | 2002-08-01 | Shionogi & Co., Ltd. | Cyclic compounds having thrombopoietin receptor agonism |
| NZ530950A (en) * | 2001-08-13 | 2006-03-31 | Janssen Pharmaceutica Nv | 2-amino-4,5-trisubstituted thiazolyl derivatives and their use against autoimmune diseases |
| EP1452530A4 (en) * | 2001-12-03 | 2005-11-30 | Japan Tobacco Inc | AZOL CONNECTION AND THEIR MEDICAL USE |
| DE60221627D1 (de) * | 2001-12-21 | 2007-09-20 | Virochem Pharma Inc | Thiazolderivate und ihre Verwendung zur Behandlung oder Vorbeugung von Infektionen durch Flaviviren |
| KR20050101200A (ko) * | 2003-02-10 | 2005-10-20 | 버텍스 파마슈티칼스 인코포레이티드 | Ｎ-아릴 카밤산 에스테르를 할로-헤테로아릴과반응시킴으로써 ｎ-헤테로아릴-ｎ-아릴-아민을 제조하는방법 및 유사 방법 |
| AR043633A1 (es) * | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
| ES2298840T3 (es) * | 2003-12-08 | 2008-05-16 | F. Hoffmann-La Roche Ag | Derivados de tiazol. |
| CA2607617A1 (en) * | 2005-05-09 | 2006-11-16 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
| GB0513702D0 (en) * | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| MX2009012613A (es) * | 2007-05-22 | 2010-04-21 | Achillion Pharmaceuticals Inc | Tiazoles substituidos por heteroarilo y su uso como agentes antivirales. |
| 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 US US11/683,749 patent/US20070213301A1/en not_active Abandoned
- 2007-03-08 WO PCT/US2007/006023 patent/WO2007103550A2/en not_active Ceased
- 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 CA CA002645072A patent/CA2645072A1/en not_active Abandoned
- 2007-03-08 AU AU2007223797A patent/AU2007223797A1/en not_active Abandoned
- 2007-03-08 NZ NZ570835A patent/NZ570835A/en not_active IP Right Cessation
- 2007-03-08 EP EP07752705A patent/EP1996565A2/en not_active Withdrawn
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