JP2007517887A5 - - Google Patents
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- JP2007517887A5 JP2007517887A5 JP2006549390A JP2006549390A JP2007517887A5 JP 2007517887 A5 JP2007517887 A5 JP 2007517887A5 JP 2006549390 A JP2006549390 A JP 2006549390A JP 2006549390 A JP2006549390 A JP 2006549390A JP 2007517887 A5 JP2007517887 A5 JP 2007517887A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- carbonyl
- compound
- thiourea
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 60
- -1 hydroxy, cyano, nitro, amino, acetyl Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 75
- 150000003839 salts Chemical class 0.000 claims 58
- 229910052739 hydrogen Inorganic materials 0.000 claims 43
- 239000001257 hydrogen Substances 0.000 claims 43
- 229910052757 nitrogen Inorganic materials 0.000 claims 43
- 229910052736 halogen Inorganic materials 0.000 claims 37
- 150000002367 halogens Chemical class 0.000 claims 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 125000001424 substituent group Chemical group 0.000 claims 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 30
- 125000004438 haloalkoxy group Chemical group 0.000 claims 28
- 125000001188 haloalkyl group Chemical group 0.000 claims 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 16
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 13
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 150000003857 carboxamides Chemical class 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 208000005176 Hepatitis C Diseases 0.000 claims 3
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 3
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- RXDNIFCKLVMUIL-UHFFFAOYSA-N 4-(dimethylamino)-n-[(3-fluoro-4-pentoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=C(F)C(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(N(C)C)N=CC=C2O1 RXDNIFCKLVMUIL-UHFFFAOYSA-N 0.000 claims 1
- HBAJFUOZQUFDCB-UHFFFAOYSA-N 4-(dimethylamino)-n-[(3-phenylmethoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C=2C(N(C)C)=NC=CC=2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OCC1=CC=CC=C1 HBAJFUOZQUFDCB-UHFFFAOYSA-N 0.000 claims 1
- YRGKITFSTJREGS-UHFFFAOYSA-N 4-(dimethylamino)-n-[(4-pentoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(N(C)C)N=CC=C2O1 YRGKITFSTJREGS-UHFFFAOYSA-N 0.000 claims 1
- OBENDQDCMDFZAC-UHFFFAOYSA-N 4-(dimethylamino)-n-[(4-pentylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(N(C)C)N=CC=C2O1 OBENDQDCMDFZAC-UHFFFAOYSA-N 0.000 claims 1
- TXJUDQLTBKDQEM-UHFFFAOYSA-N 4-chloro-n-[(2-pentan-2-yloxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCCC(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=C(Cl)N=CC=C2O1 TXJUDQLTBKDQEM-UHFFFAOYSA-N 0.000 claims 1
- PXUBCZOQTLJLKU-UHFFFAOYSA-N 4-chloro-n-[(2-pentan-2-ylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCCC(C)C1=CC=CC=C1NC(=S)NC(=O)C1=CC2=C(Cl)N=CC=C2O1 PXUBCZOQTLJLKU-UHFFFAOYSA-N 0.000 claims 1
- CSJVBHSHXXTAOL-UHFFFAOYSA-N 4-chloro-n-[(3-phenoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C=2C(Cl)=NC=CC=2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 CSJVBHSHXXTAOL-UHFFFAOYSA-N 0.000 claims 1
- TWJWCYGLXGOXQN-UHFFFAOYSA-N 4-chloro-n-[(3-phenylmethoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C=2C(Cl)=NC=CC=2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OCC1=CC=CC=C1 TWJWCYGLXGOXQN-UHFFFAOYSA-N 0.000 claims 1
- LJXCRLVOKXQAJE-UHFFFAOYSA-N 4-chloro-n-[[2-(3-fluoropentan-2-yloxy)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCC(F)C(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=C(Cl)N=CC=C2O1 LJXCRLVOKXQAJE-UHFFFAOYSA-N 0.000 claims 1
- UVXGUDKTDZSDIN-UHFFFAOYSA-N 4-methoxy-n-[(3-phenoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C=2C(OC)=NC=CC=2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 UVXGUDKTDZSDIN-UHFFFAOYSA-N 0.000 claims 1
- HESQIYGICGSJNC-UHFFFAOYSA-N 4-methoxy-n-[(3-phenylmethoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C=2C(OC)=NC=CC=2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OCC1=CC=CC=C1 HESQIYGICGSJNC-UHFFFAOYSA-N 0.000 claims 1
- KIYJNKOHFHWPJI-UHFFFAOYSA-N 4-methoxy-n-[(4-pentoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(OC)N=CC=C2O1 KIYJNKOHFHWPJI-UHFFFAOYSA-N 0.000 claims 1
- RHTYRSVKZAWJHB-UHFFFAOYSA-N 4-methoxy-n-[(4-pentylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(OC)N=CC=C2O1 RHTYRSVKZAWJHB-UHFFFAOYSA-N 0.000 claims 1
- NGOJVNPVBUYNSO-UHFFFAOYSA-N 4-oxo-n-[(4-pentoxyphenyl)carbamothioyl]-5h-furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=C(O)N=CC=C2O1 NGOJVNPVBUYNSO-UHFFFAOYSA-N 0.000 claims 1
- AYTBXJOBLFDDEC-UHFFFAOYSA-N 7-chloro-n-[(3-phenoxyphenyl)carbamothioyl]furo[2,3-c]pyridine-2-carboxamide Chemical compound O1C=2C(Cl)=NC=CC=2C=C1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 AYTBXJOBLFDDEC-UHFFFAOYSA-N 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- WKDVUMBOPDPUNT-UHFFFAOYSA-N [2-(3-methoxyfuro[3,2-b]pyridine-2-carbonyl)-3-pentan-2-ylphenyl]thiourea Chemical compound CCCC(C)C1=CC=CC(NC(N)=S)=C1C(=O)C1=C(OC)C2=NC=CC=C2O1 WKDVUMBOPDPUNT-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- YKMNUIRLMZMTQU-UHFFFAOYSA-N butyl 4-(furo[3,2-c]pyridine-2-carbonylcarbamothioylamino)benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 YKMNUIRLMZMTQU-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- HHHPRFXBYIIPLR-UHFFFAOYSA-N n-[(2-pentan-2-yloxyphenyl)carbamothioyl]furo[2,3-c]pyridine-2-carboxamide Chemical compound CCCC(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CC=NC=C2O1 HHHPRFXBYIIPLR-UHFFFAOYSA-N 0.000 claims 1
- BAUFCFXQUAARKC-UHFFFAOYSA-N n-[(2-pentan-2-yloxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCCC(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 BAUFCFXQUAARKC-UHFFFAOYSA-N 0.000 claims 1
- JKMAPGGFQCOCFC-UHFFFAOYSA-N n-[(2-pentan-2-yloxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide;hydrochloride Chemical compound Cl.CCCC(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 JKMAPGGFQCOCFC-UHFFFAOYSA-N 0.000 claims 1
- LCKVCPZMBMSNJL-UHFFFAOYSA-N n-[(2-pentan-2-ylphenyl)carbamothioyl]furo[2,3-c]pyridine-2-carboxamide Chemical compound CCCC(C)C1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CC=NC=C2O1 LCKVCPZMBMSNJL-UHFFFAOYSA-N 0.000 claims 1
- ICBGVMXXUXGRPY-UHFFFAOYSA-N n-[(2-pentan-2-ylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCCC(C)C1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 ICBGVMXXUXGRPY-UHFFFAOYSA-N 0.000 claims 1
- SEYPOJAVOCOAAW-UHFFFAOYSA-N n-[(3-benzylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1CC1=CC=CC=C1 SEYPOJAVOCOAAW-UHFFFAOYSA-N 0.000 claims 1
- WXILXIORKVLWMF-UHFFFAOYSA-N n-[(3-methoxy-4-phenylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound COC1=CC(NC(=S)NC(=O)C=2OC3=CC=NC=C3C=2)=CC=C1C1=CC=CC=C1 WXILXIORKVLWMF-UHFFFAOYSA-N 0.000 claims 1
- AASPBOFGRVAYTH-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 AASPBOFGRVAYTH-UHFFFAOYSA-N 0.000 claims 1
- NCFWFWXCNIOVKT-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide;hydrochloride Chemical compound Cl.C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 NCFWFWXCNIOVKT-UHFFFAOYSA-N 0.000 claims 1
- ZTONRCBVYOQOSM-UHFFFAOYSA-N n-[(3-phenylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1C1=CC=CC=C1 ZTONRCBVYOQOSM-UHFFFAOYSA-N 0.000 claims 1
- OMPQYDSINDFCFV-UHFFFAOYSA-N n-[(4-benzylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=C1)=CC=C1CC1=CC=CC=C1 OMPQYDSINDFCFV-UHFFFAOYSA-N 0.000 claims 1
- ULJXODSETMQZJF-UHFFFAOYSA-N n-[(4-butoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 ULJXODSETMQZJF-UHFFFAOYSA-N 0.000 claims 1
- BTDYOEIBUFSOBJ-UHFFFAOYSA-N n-[(4-cyclohexylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=C1)=CC=C1C1CCCCC1 BTDYOEIBUFSOBJ-UHFFFAOYSA-N 0.000 claims 1
- DVRQLXNTBIPEDV-UHFFFAOYSA-N n-[(4-hexoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 DVRQLXNTBIPEDV-UHFFFAOYSA-N 0.000 claims 1
- KYZKEGFKSIKZGT-UHFFFAOYSA-N n-[(4-hexylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(CCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 KYZKEGFKSIKZGT-UHFFFAOYSA-N 0.000 claims 1
- OEUFOGVGIJVCAB-UHFFFAOYSA-N n-[(4-octoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(OCCCCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 OEUFOGVGIJVCAB-UHFFFAOYSA-N 0.000 claims 1
- DPUOENWBTXCZAZ-UHFFFAOYSA-N n-[(4-octylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=CC(CCCCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 DPUOENWBTXCZAZ-UHFFFAOYSA-N 0.000 claims 1
- YMZYGEAFILMBFK-UHFFFAOYSA-N n-[(4-phenoxyphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=C1)=CC=C1OC1=CC=CC=C1 YMZYGEAFILMBFK-UHFFFAOYSA-N 0.000 claims 1
- DFFKCTCEDXFPEI-UHFFFAOYSA-N n-[(4-phenylphenyl)carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=C1)=CC=C1C1=CC=CC=C1 DFFKCTCEDXFPEI-UHFFFAOYSA-N 0.000 claims 1
- JYVXQJUVUPBBIV-UHFFFAOYSA-N n-[(4-phenylphenyl)methylcarbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NCC(C=C1)=CC=C1C1=CC=CC=C1 JYVXQJUVUPBBIV-UHFFFAOYSA-N 0.000 claims 1
- FIVXJGQEIOHLHX-UHFFFAOYSA-N n-[2-(3-phenoxyphenyl)ethylcarbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NCCC(C=1)=CC=CC=1OC1=CC=CC=C1 FIVXJGQEIOHLHX-UHFFFAOYSA-N 0.000 claims 1
- CQWGUYIBIMARDL-UHFFFAOYSA-N n-[[2-(3-fluoropentan-2-yloxy)phenyl]carbamothioyl]-4-methoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CCC(F)C(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=C(OC)N=CC=C2O1 CQWGUYIBIMARDL-UHFFFAOYSA-N 0.000 claims 1
- PHPVCNFNKFBHPA-UHFFFAOYSA-N n-[[2-(3-fluoropentan-2-yloxy)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CCC(F)C(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 PHPVCNFNKFBHPA-UHFFFAOYSA-N 0.000 claims 1
- QIPZKLMZHLHBQI-UHFFFAOYSA-N n-[[2-(3-fluoropentan-2-yloxy)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide;hydrochloride Chemical compound Cl.CCC(F)C(C)OC1=CC=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 QIPZKLMZHLHBQI-UHFFFAOYSA-N 0.000 claims 1
- IOAIBIQJEOWTJO-UHFFFAOYSA-N n-[[3-(2,3-dihydro-1h-inden-2-yloxy)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(NC(=S)NC=3C=C(OC4CC5=CC=CC=C5C4)C=CC=3)=O)=CC2=C1 IOAIBIQJEOWTJO-UHFFFAOYSA-N 0.000 claims 1
- CDTSXQNDZSYDCD-UHFFFAOYSA-N n-[[3-(isoquinolin-3-ylmethoxy)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(NC(=S)NC=3C=C(OCC=4N=CC5=CC=CC=C5C=4)C=CC=3)=O)=CC2=C1 CDTSXQNDZSYDCD-UHFFFAOYSA-N 0.000 claims 1
- YDCNWDJUOZWCSB-UHFFFAOYSA-N n-[[3-[(2-methylpropan-2-yl)oxy]phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)(C)OC1=CC=CC(NC(=S)NC(=O)C=2OC3=CC=NC=C3C=2)=C1 YDCNWDJUOZWCSB-UHFFFAOYSA-N 0.000 claims 1
- BSBFNOOVSZSLNI-UHFFFAOYSA-N n-[[3-[(3,4-difluorophenyl)methoxy]phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=C(F)C(F)=CC=C1COC1=CC=CC(NC(=S)NC(=O)C=2OC3=CC=NC=C3C=2)=C1 BSBFNOOVSZSLNI-UHFFFAOYSA-N 0.000 claims 1
- BFJOVBAPNFHVSK-UHFFFAOYSA-N n-[[3-[(4-phenylphenyl)methoxy]phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C=1C2=CN=CC=C2OC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1 BFJOVBAPNFHVSK-UHFFFAOYSA-N 0.000 claims 1
- FZQZQXPTBPWDFA-UHFFFAOYSA-N n-[[4-(3,4-dihydro-1h-isoquinolin-2-yl)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(NC(=S)NC=3C=CC(=CC=3)N3CC4=CC=CC=C4CC3)=O)=CC2=C1 FZQZQXPTBPWDFA-UHFFFAOYSA-N 0.000 claims 1
- HSGJBPIQAPWIKZ-UHFFFAOYSA-N n-[[4-(cyclohexylmethoxy)-3-fluorophenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(NC(=S)NC(=O)C=2OC3=CC=NC=C3C=2)=CC=C1OCC1CCCCC1 HSGJBPIQAPWIKZ-UHFFFAOYSA-N 0.000 claims 1
- MYCFBZHUDPLGQF-UHFFFAOYSA-N n-[[4-heptoxy-3-(trifluoromethyl)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(OCCCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 MYCFBZHUDPLGQF-UHFFFAOYSA-N 0.000 claims 1
- IKKSPGCFBUJIGO-UHFFFAOYSA-N n-[[4-pentoxy-3-(trifluoromethyl)phenyl]carbamothioyl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CN=CC=C2O1 IKKSPGCFBUJIGO-UHFFFAOYSA-N 0.000 claims 1
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
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- 235000020357 syrup Nutrition 0.000 claims 1
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- 238000000034 method Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NNVMQMPFXMSLDX-UHFFFAOYSA-N 3-fluoro-4-pentoxyaniline Chemical compound CCCCCOC1=CC=C(N)C=C1F NNVMQMPFXMSLDX-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- NFIMWUKWQUEPCL-UHFFFAOYSA-N [3-(3-fluoropentan-2-yloxy)-2-(2-methyl-3h-furo[3,2-c]pyridine-2-carbonyl)phenyl]thiourea Chemical compound CCC(F)C(C)OC1=CC=CC(NC(N)=S)=C1C(=O)C1(C)OC2=CC=NC=C2C1 NFIMWUKWQUEPCL-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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| OA (1) | OA13357A (https=) |
| TW (1) | TW200528459A (https=) |
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| TW200600492A (en) * | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| TWI329102B (en) * | 2006-08-15 | 2010-08-21 | Nat Health Research Institutes | Thiourea compounds and method for inhibiting hepatitis c virus infection |
| BRPI0715714A2 (pt) * | 2006-08-25 | 2014-03-11 | Wyeth Corp | Métodos para diminuir a frequência de emergência de uma infecção viral de hepatite c resistente ao tratamento, para atrasar a emergência de uma infecção viral de hepatite c resistente ao tratamento, para diminuir o nível de resistência de uma infecção viral de hepatite c resistente ao tratamento, para diminuir a emergência de uma infecção viral de hepatite c resistente a hcv-796, para identificar um indivíduo com uma probabilidade diminuída de responder a uma terapia viral anti-hepatite c, para monitorar, diagnosticar ou prognosticar a infecção viral de hepatite c resistente ao tratamento em um paciente, para monitorar o curso de tratamento de uma infecção viral de hepatite c em um paciente, para prognosticar o desenvolvimento de um ainfecção viral de hepatite c resistente ao tratamento em um paciente, para monitorar a infecção viral de hepatite c em um paciente e para diagnosticar o desenvolvimento de uma infecção viral de hepatite ao tratamento em um paciente |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| WO2008124300A1 (en) * | 2007-04-10 | 2008-10-16 | National Health Research Institutes | Hepatitis c virus inhibitors |
| TW200848016A (en) * | 2007-06-08 | 2008-12-16 | Nat Health Research Institutes | Thiourea compound and composition of treating hepatitis C virus infection |
| TWI361808B (en) * | 2008-01-08 | 2012-04-11 | Nat Health Research Institutes | Imidazolidinone and imidazolidinethione derivatives |
| US8198284B2 (en) * | 2008-04-30 | 2012-06-12 | National Health Research Institutes | Treatment of neurodegenerative disorders with thiourea compounds |
| US8198449B2 (en) * | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| SG194404A1 (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| KR20110098849A (ko) | 2008-12-23 | 2011-09-01 | 파마셋 인코포레이티드 | 뉴클레오시드 유사체 |
| PT2376088T (pt) | 2008-12-23 | 2017-05-02 | Gilead Pharmasset Llc | Fosforamidatos de nucleósidos de 2-amino-purina 6-osubstituída |
| TWI598358B (zh) | 2009-05-20 | 2017-09-11 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| UY33312A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Fosforamidato de nucleosido de purina |
| PL3290428T3 (pl) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu |
| PT2609923T (pt) | 2010-03-31 | 2017-08-30 | Gilead Pharmasset Llc | Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo |
| AR082453A1 (es) | 2010-04-21 | 2012-12-12 | Novartis Ag | Compuestos de furopiridina, composiciones farmaceuticas que los contienen y usos de los mismos |
| AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
| PL2709613T5 (pl) | 2011-09-16 | 2020-12-14 | Gilead Pharmasset Llc | Metody leczenia hcv |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| CN103467482B (zh) * | 2012-04-10 | 2017-05-10 | 上海璎黎药业有限公司 | 稠合嘧啶类化合物，其制备方法，中间体，组合物和应用 |
| PT2950786T (pt) | 2013-01-31 | 2020-03-03 | Gilead Pharmasset Llc | Formulação de combinação de dois compostos antivirais |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| CN109790143A (zh) | 2016-05-10 | 2019-05-21 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3454862B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EA202092441A1 (ru) | 2016-06-07 | 2021-05-21 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| KR20240026521A (ko) | 2017-03-23 | 2024-02-28 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| EP4717317A2 (en) | 2017-06-20 | 2026-04-01 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1408198A (en) * | 1971-08-23 | 1975-10-01 | Medizinska Akad | Antiviral compositions |
| CN1071930A (zh) * | 1991-07-10 | 1993-05-12 | 伊莱利利公司 | 用作治疗艾滋病的人免疫缺陷病毒蛋白酶的抑制剂 |
| GB9504460D0 (en) | 1995-03-06 | 1995-04-26 | Bayer Ag | N-(3-Benzofuranyl)urea-derivatives |
| CA2253502A1 (en) * | 1996-05-06 | 1997-11-13 | Stephen Warren Kaldor | Anti-viral compounds |
| US6174905B1 (en) | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| CN1731993A (zh) | 2002-11-01 | 2006-02-08 | 维洛药品公司 | 苯并呋喃化合物、组合物以及治疗和预防丙型肝炎病毒感染及相关疾病的方法 |
| CN1738797A (zh) * | 2002-11-19 | 2006-02-22 | 阿基里昂药品公司 | 取代的芳基硫脲和相关的化合物,病毒复制的抑制剂 |
| CA2531068A1 (en) * | 2003-07-10 | 2005-01-27 | Achillion Pharmaceuticals, Inc. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
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2004
- 2004-12-30 TW TW093141409A patent/TW200528459A/zh unknown
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2005
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- 2005-01-05 EA EA200601281A patent/EA200601281A1/ru unknown
- 2005-01-05 CA CA002552002A patent/CA2552002A1/en not_active Abandoned
- 2005-01-05 KR KR1020067013660A patent/KR20060121289A/ko not_active Withdrawn
- 2005-01-05 AU AU2005204369A patent/AU2005204369B2/en not_active Ceased
- 2005-01-05 AR ARP050100026A patent/AR047367A1/es not_active Application Discontinuation
- 2005-01-05 WO PCT/US2005/000339 patent/WO2005067900A2/en not_active Ceased
- 2005-01-05 OA OA1200600222A patent/OA13357A/en unknown
- 2005-01-05 NZ NZ548375A patent/NZ548375A/en unknown
- 2005-01-05 BR BRPI0506705-7A patent/BRPI0506705A/pt not_active IP Right Cessation
- 2005-01-05 CN CNA200580007223XA patent/CN1946720A/zh active Pending
- 2005-01-05 JP JP2006549390A patent/JP2007517887A/ja active Pending
- 2005-01-05 AP AP2006003659A patent/AP2006003659A0/xx unknown
- 2005-01-05 US US11/029,910 patent/US7439374B2/en not_active Expired - Fee Related
- 2005-01-05 AT AT05705124T patent/ATE479684T1/de not_active IP Right Cessation
- 2005-01-05 EP EP05705124A patent/EP1709047B1/en not_active Expired - Lifetime
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2006
- 2006-06-21 IL IL176486A patent/IL176486A0/en unknown
- 2006-06-22 NO NO20062928A patent/NO20062928L/no not_active Application Discontinuation
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