OA12961A - Substituted aryl thioureas and related compounds, inhibitors of viral replication. - Google Patents
Substituted aryl thioureas and related compounds, inhibitors of viral replication. Download PDFInfo
- Publication number
- OA12961A OA12961A OA1200500150A OA1200500150A OA12961A OA 12961 A OA12961 A OA 12961A OA 1200500150 A OA1200500150 A OA 1200500150A OA 1200500150 A OA1200500150 A OA 1200500150A OA 12961 A OA12961 A OA 12961A
- Authority
- OA
- OAPI
- Prior art keywords
- phenyl
- thiourea
- carbonyl
- c4alkyl
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 294
- -1 Substituted aryl thioureas Chemical class 0.000 title claims description 319
- 230000029812 viral genome replication Effects 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 239000003937 drug carrier Substances 0.000 claims abstract description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 10
- 239000003085 diluting agent Substances 0.000 claims abstract description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 318
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 206
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 229910052736 halogen Inorganic materials 0.000 claims description 168
- 150000002367 halogens Chemical class 0.000 claims description 168
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 162
- 125000001424 substituent group Chemical group 0.000 claims description 157
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 239000001257 hydrogen Substances 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 229910052760 oxygen Inorganic materials 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 150000003857 carboxamides Chemical class 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 47
- 125000005842 heteroatom Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000004043 oxo group Chemical group O=* 0.000 claims description 42
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 39
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 36
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 32
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 31
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 25
- 229940124530 sulfonamide Drugs 0.000 claims description 25
- 150000003456 sulfonamides Chemical class 0.000 claims description 25
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
- 238000003556 assay Methods 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000005605 benzo group Chemical group 0.000 claims description 16
- 125000002971 oxazolyl group Chemical group 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 15
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000003003 spiro group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000005176 Hepatitis C Diseases 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000006071 cream Substances 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 239000006188 syrup Substances 0.000 claims description 6
- 235000020357 syrup Nutrition 0.000 claims description 6
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 6
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 4
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 3
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 102220595473 Major vault protein_R18A_mutation Human genes 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229940054534 ophthalmic solution Drugs 0.000 claims description 2
- 239000002997 ophthalmic solution Substances 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 3
- YBTMLDCZMDOLGJ-UHFFFAOYSA-N 4-methyl-n-[(4-pentoxyphenyl)carbamothioyl]thiadiazole-5-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=C(C)N=NS1 YBTMLDCZMDOLGJ-UHFFFAOYSA-N 0.000 claims 2
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- UFHVQJAWSVKQOB-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamothioyl]-1,2-oxazole-5-carboxamide Chemical compound C=1C=NOC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 UFHVQJAWSVKQOB-UHFFFAOYSA-N 0.000 claims 2
- WRAWEYIOCXAKMC-UHFFFAOYSA-N 1,5-dimethyl-n-[(3-phenoxyphenyl)carbamothioyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)NC(=S)NC=2C=C(OC=3C=CC=CC=3)C=CC=2)=N1 WRAWEYIOCXAKMC-UHFFFAOYSA-N 0.000 claims 1
- GRRLYFCWRDKBRV-UHFFFAOYSA-N 1-methyl-n-[(4-pentoxyphenyl)carbamothioyl]piperidine-3-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1CN(C)CCC1 GRRLYFCWRDKBRV-UHFFFAOYSA-N 0.000 claims 1
- OHXSSTLZBWLEIU-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-[(3-phenoxyphenyl)carbamothioyl]acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 OHXSSTLZBWLEIU-UHFFFAOYSA-N 0.000 claims 1
- ACWQHFJOMKSIKL-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-[(3-phenylmethoxyphenyl)carbamothioyl]acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(=O)NC(=S)NC(C=1)=CC=CC=1OCC1=CC=CC=C1 ACWQHFJOMKSIKL-UHFFFAOYSA-N 0.000 claims 1
- JFRYDTOHPPHFFB-UHFFFAOYSA-N 2-hydroxy-n-[(3-phenylmethoxyphenyl)carbamothioyl]acetamide Chemical compound OCC(=O)NC(=S)NC1=CC=CC(OCC=2C=CC=CC=2)=C1 JFRYDTOHPPHFFB-UHFFFAOYSA-N 0.000 claims 1
- OGSWCGCKKWIAMM-UHFFFAOYSA-N 2-methylpropyl 4-[(2-phenoxyacetyl)carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCC(C)C)=CC=C1NC(=S)NC(=O)COC1=CC=CC=C1 OGSWCGCKKWIAMM-UHFFFAOYSA-N 0.000 claims 1
- DNLVKBSTPCPYML-UHFFFAOYSA-N 2-morpholin-4-yl-n-[(3-phenoxyphenyl)carbamothioyl]acetamide Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1NC(=S)NC(=O)CN1CCOCC1 DNLVKBSTPCPYML-UHFFFAOYSA-N 0.000 claims 1
- NCIFTOYFADVUDP-UHFFFAOYSA-N 3,4-dichloro-n-[(3-phenylmethoxyphenyl)carbamothioyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(=S)NC1=CC=CC(OCC=2C=CC=CC=2)=C1 NCIFTOYFADVUDP-UHFFFAOYSA-N 0.000 claims 1
- HIFNLHFDJGSIGE-UHFFFAOYSA-N 3-(difluoromethyl)-n-[(3-phenoxyphenyl)carbamothioyl]benzamide Chemical compound FC(F)C1=CC=CC(C(=O)NC(=S)NC=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1 HIFNLHFDJGSIGE-UHFFFAOYSA-N 0.000 claims 1
- SDVOECOEPYYUIO-UHFFFAOYSA-N 3-methyl-n-[(4-pentoxyphenyl)carbamothioyl]-1,2-oxazole-4-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CON=C1C SDVOECOEPYYUIO-UHFFFAOYSA-N 0.000 claims 1
- CWFVBPDHNMSOIW-UHFFFAOYSA-N 3-methyl-n-[(4-pentylphenyl)carbamothioyl]-1,2-oxazole-4-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CON=C1C CWFVBPDHNMSOIW-UHFFFAOYSA-N 0.000 claims 1
- JWPMOTCWQWIFHV-UHFFFAOYSA-N 4-chloro-n-[(4-pentylphenyl)carbamothioyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 JWPMOTCWQWIFHV-UHFFFAOYSA-N 0.000 claims 1
- LDKJZIWMKGVWSC-UHFFFAOYSA-N 4-cyano-n-[(3-phenoxyphenyl)carbamothioyl]benzamide Chemical compound C=1C=C(C#N)C=CC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 LDKJZIWMKGVWSC-UHFFFAOYSA-N 0.000 claims 1
- WJLRCRMKGOCSPH-UHFFFAOYSA-N 4-methyl-n-[(4-pentylphenyl)carbamothioyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 WJLRCRMKGOCSPH-UHFFFAOYSA-N 0.000 claims 1
- OLWVJHALVIRPPY-UHFFFAOYSA-N 5-bromo-n-[(4-pentylphenyl)carbamothioyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CC(Br)=CC=C2O1 OLWVJHALVIRPPY-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- 101100379081 Emericella variicolor andC gene Proteins 0.000 claims 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 claims 1
- SAOLGSHCAMOQOU-UHFFFAOYSA-N butyl 4-(1-benzofuran-2-carbonylcarbamothioylamino)benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)C1=CC2=CC=CC=C2O1 SAOLGSHCAMOQOU-UHFFFAOYSA-N 0.000 claims 1
- HXSVWYXRQBJJTA-UHFFFAOYSA-N butyl 4-(3-phenoxypropanoylcarbamothioylamino)benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)CCOC1=CC=CC=C1 HXSVWYXRQBJJTA-UHFFFAOYSA-N 0.000 claims 1
- PJVSALAJPLXZDO-UHFFFAOYSA-N butyl 4-(acetylcarbamothioylamino)benzoate Chemical compound CCCCOC(=O)C1=CC=C(NC(=S)NC(C)=O)C=C1 PJVSALAJPLXZDO-UHFFFAOYSA-N 0.000 claims 1
- AGIXTDRWMBDZAR-UHFFFAOYSA-N butyl 4-[(2-methoxyacetyl)carbamothioylamino]benzoate Chemical compound CCCCOC(=O)C1=CC=C(NC(=S)NC(=O)COC)C=C1 AGIXTDRWMBDZAR-UHFFFAOYSA-N 0.000 claims 1
- PPWHKCHMKJIIPA-UHFFFAOYSA-N butyl 4-[(2-naphthalen-2-yloxyacetyl)carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=C(C=CC=C2)C2=C1 PPWHKCHMKJIIPA-UHFFFAOYSA-N 0.000 claims 1
- YGJLDOQZBHULJW-UHFFFAOYSA-N butyl 4-[[2-(2,4,6-trichlorophenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=C(Cl)C=C(Cl)C=C1Cl YGJLDOQZBHULJW-UHFFFAOYSA-N 0.000 claims 1
- YZANBRFAGPVRRY-UHFFFAOYSA-N butyl 4-[[2-(2,4-dichlorophenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=C(Cl)C=C1Cl YZANBRFAGPVRRY-UHFFFAOYSA-N 0.000 claims 1
- PPYBJURDDKSVLH-UHFFFAOYSA-N butyl 4-[[2-(2,6-dichlorophenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=C(Cl)C=CC=C1Cl PPYBJURDDKSVLH-UHFFFAOYSA-N 0.000 claims 1
- FLVZJSZNLDIGEQ-UHFFFAOYSA-N butyl 4-[[2-(2-methoxyethoxy)acetyl]carbamothioylamino]benzoate Chemical compound CCCCOC(=O)C1=CC=C(NC(=S)NC(=O)COCCOC)C=C1 FLVZJSZNLDIGEQ-UHFFFAOYSA-N 0.000 claims 1
- VXJJVJLMJAVOBE-UHFFFAOYSA-N butyl 4-[[2-(2-methoxyphenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=CC=C1OC VXJJVJLMJAVOBE-UHFFFAOYSA-N 0.000 claims 1
- YAZWPMWDGPGSBW-UHFFFAOYSA-N butyl 4-[[2-(2-methylphenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=CC=C1C YAZWPMWDGPGSBW-UHFFFAOYSA-N 0.000 claims 1
- LEGXZXOBYCESRD-UHFFFAOYSA-N butyl 4-[[2-(3,4-dichlorophenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=C(Cl)C(Cl)=C1 LEGXZXOBYCESRD-UHFFFAOYSA-N 0.000 claims 1
- XJHDGZUPPXIBOY-UHFFFAOYSA-N butyl 4-[[2-(3-chlorophenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=CC(Cl)=C1 XJHDGZUPPXIBOY-UHFFFAOYSA-N 0.000 claims 1
- NVXXKDQWIOWWMI-UHFFFAOYSA-N butyl 4-[[2-(3-methoxyphenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=CC(OC)=C1 NVXXKDQWIOWWMI-UHFFFAOYSA-N 0.000 claims 1
- YKQSUMJTRHIJNT-UHFFFAOYSA-N butyl 4-[[2-(4-phenylmethoxyphenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC(C=C1)=CC=C1OCC1=CC=CC=C1 YKQSUMJTRHIJNT-UHFFFAOYSA-N 0.000 claims 1
- MKIQRKLXYYYTJL-UHFFFAOYSA-N butyl 4-[[2-(4-tert-butylphenoxy)acetyl]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=S)NC(=O)COC1=CC=C(C(C)(C)C)C=C1 MKIQRKLXYYYTJL-UHFFFAOYSA-N 0.000 claims 1
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- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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| AU2005326813B2 (en) * | 2002-11-19 | 2011-08-04 | Achillion Pharmaceuticals, Inc. | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| KR20050111306A (ko) * | 2002-11-19 | 2005-11-24 | 아칠리온 파르마세우티칼스 인코포레이티드 | 바이러스 복제 억제제로서의 치환된 아릴 티오우레아 및관련 화합물 |
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- 2003-11-18 EP EP03786803A patent/EP1562895A1/en not_active Withdrawn
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- 2003-11-18 BR BR0316397-0A patent/BR0316397A/pt not_active IP Right Cessation
- 2003-11-18 NZ NZ540033A patent/NZ540033A/en not_active IP Right Cessation
- 2003-11-18 WO PCT/US2003/036809 patent/WO2004046095A1/en not_active Ceased
- 2003-11-18 AU AU2003295605A patent/AU2003295605A1/en not_active Abandoned
- 2003-11-18 CA CA002506415A patent/CA2506415A1/en not_active Abandoned
- 2003-11-18 EA EA200500846A patent/EA200500846A1/ru unknown
- 2003-11-18 JP JP2004553861A patent/JP4206382B2/ja not_active Expired - Fee Related
- 2003-11-18 MX MXPA05005379A patent/MXPA05005379A/es unknown
- 2003-11-18 OA OA1200500150A patent/OA12961A/en unknown
-
2004
- 2004-12-17 US US11/015,300 patent/US7476686B2/en not_active Expired - Fee Related
-
2005
- 2005-05-26 NO NO20052546A patent/NO20052546L/no not_active Application Discontinuation
-
2006
- 2006-10-03 JP JP2006272359A patent/JP2007084548A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004046095A1 (en) | 2004-06-03 |
| US20040138205A1 (en) | 2004-07-15 |
| EA200500846A1 (ru) | 2005-12-29 |
| NO20052546L (no) | 2005-07-18 |
| JP2006506439A (ja) | 2006-02-23 |
| KR20050111306A (ko) | 2005-11-24 |
| JP4206382B2 (ja) | 2009-01-07 |
| BR0316397A (pt) | 2005-09-27 |
| JP2007084548A (ja) | 2007-04-05 |
| US7094807B2 (en) | 2006-08-22 |
| US20060014836A1 (en) | 2006-01-19 |
| AP2005003319A0 (en) | 2005-06-30 |
| NO20052546D0 (no) | 2005-05-26 |
| AU2003295605A1 (en) | 2004-06-15 |
| CN1738797A (zh) | 2006-02-22 |
| CA2506415A1 (en) | 2004-06-03 |
| EP1562895A1 (en) | 2005-08-17 |
| NZ540033A (en) | 2007-05-31 |
| US7476686B2 (en) | 2009-01-13 |
| MXPA05005379A (es) | 2006-02-17 |
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