AU2005204369B2 - Azabenzofuran substituted thioureas as inhibitors of viral replication - Google Patents
Azabenzofuran substituted thioureas as inhibitors of viral replication Download PDFInfo
- Publication number
- AU2005204369B2 AU2005204369B2 AU2005204369A AU2005204369A AU2005204369B2 AU 2005204369 B2 AU2005204369 B2 AU 2005204369B2 AU 2005204369 A AU2005204369 A AU 2005204369A AU 2005204369 A AU2005204369 A AU 2005204369A AU 2005204369 B2 AU2005204369 B2 AU 2005204369B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- phenyl
- carbonyl
- compound
- furo
- 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.)
- Ceased
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- 230000029812 viral genome replication Effects 0.000 title description 11
- 150000003585 thioureas Chemical class 0.000 title description 9
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 218
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 107
- 150000003839 salts Chemical class 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- -1 and (iv) CI-Csalkyl Chemical group 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- 125000001188 haloalkyl group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 36
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 230000010076 replication Effects 0.000 claims description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 238000003556 assay Methods 0.000 claims description 17
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229940079322 interferon Drugs 0.000 claims description 13
- 102000014150 Interferons Human genes 0.000 claims description 12
- 108010050904 Interferons Proteins 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 208000005176 Hepatitis C Diseases 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound 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 description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 229960000329 ribavirin Drugs 0.000 claims description 7
- 239000006188 syrup Substances 0.000 claims description 7
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- 210000004369 blood Anatomy 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
- 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 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
- 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
- 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
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 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
- 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
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
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- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
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- 230000036962 time dependent Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 238000012384 transportation and delivery Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 108010087967 type I signal peptidase Proteins 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53483904P | 2004-01-06 | 2004-01-06 | |
| US60/534,839 | 2004-01-06 | ||
| PCT/US2005/000339 WO2005067900A2 (en) | 2004-01-06 | 2005-01-05 | Azabenzofuran substituted thioureas as inhibitors of viral replication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005204369A1 AU2005204369A1 (en) | 2005-07-28 |
| AU2005204369B2 true AU2005204369B2 (en) | 2010-06-10 |
Family
ID=34794326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005204369A Ceased AU2005204369B2 (en) | 2004-01-06 | 2005-01-05 | Azabenzofuran substituted thioureas as inhibitors of viral replication |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7439374B2 (https=) |
| EP (1) | EP1709047B1 (https=) |
| JP (1) | JP2007517887A (https=) |
| KR (1) | KR20060121289A (https=) |
| CN (1) | CN1946720A (https=) |
| AP (1) | AP2006003659A0 (https=) |
| AR (1) | AR047367A1 (https=) |
| AT (1) | ATE479684T1 (https=) |
| AU (1) | AU2005204369B2 (https=) |
| BR (1) | BRPI0506705A (https=) |
| CA (1) | CA2552002A1 (https=) |
| DE (1) | DE602005023266D1 (https=) |
| EA (1) | EA200601281A1 (https=) |
| IL (1) | IL176486A0 (https=) |
| NO (1) | NO20062928L (https=) |
| NZ (1) | NZ548375A (https=) |
| OA (1) | OA13357A (https=) |
| TW (1) | TW200528459A (https=) |
| WO (1) | WO2005067900A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| AU2007286754A1 (en) * | 2006-08-25 | 2008-02-28 | Viropharma Incorporated | Identification and characterization of HCV replicon variants with reduced susceptibility to HCV-796, and methods related thereto |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US7985763B2 (en) * | 2007-04-10 | 2011-07-26 | National Health Research Institutes | Hepatitis C virus inhibitors |
| US7897764B2 (en) * | 2007-06-08 | 2011-03-01 | National Health Research Institutes | Thiourea derivatives |
| 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 |
| PA8855601A1 (es) | 2008-12-23 | 2010-07-27 | Forformidatos de nucleósidos | |
| NZ593649A (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Nucleoside analogs |
| AU2009329872B2 (en) | 2008-12-23 | 2016-07-07 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| TWI583692B (zh) | 2009-05-20 | 2017-05-21 | 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 |
| US8563530B2 (en) | 2010-03-31 | 2013-10-22 | Gilead Pharmassel LLC | Purine nucleoside phosphoramidate |
| UY33310A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Sintesis estereoselectiva de activos que contienen fosforo |
| SG184324A1 (en) | 2010-03-31 | 2012-11-29 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| AR082453A1 (es) | 2010-04-21 | 2012-12-12 | Novartis Ag | Compuestos de furopiridina, composiciones farmaceuticas que los contienen y usos de los mismos |
| CA2818853A1 (en) | 2010-11-30 | 2012-06-07 | Gilead Pharmasset Llc | 2'-spirocyclo-nucleosides for use in therapy of hcv or dengue virus |
| EP2709613B2 (en) | 2011-09-16 | 2020-08-12 | Gilead Pharmasset LLC | Methods for treating hcv |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| US9499561B2 (en) * | 2012-04-10 | 2016-11-22 | Shanghai Yingli Pharmaceutical Co., Ltd. | Fused pyrimidine compound, and preparation method, intermediate, composition, and uses thereof |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| PT3038601T (pt) | 2013-08-27 | 2020-06-30 | Gilead Pharmasset Llc | Formulação combinada de dois compostos antivirais |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| ES2990061T3 (es) | 2016-05-10 | 2024-11-28 | C4 Therapeutics Inc | Degronímeros espirocíclicos para la degradación de proteínas diana |
| 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 |
| 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 |
| MX388576B (es) | 2016-06-07 | 2025-03-20 | Jacobio Pharmaceuticals Co Ltd | Derivados heterociclicos novedosos utiles como inhibidores de shp2. |
| EA202190196A1 (ru) | 2017-03-23 | 2021-08-31 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| CN110769822A (zh) | 2017-06-20 | 2020-02-07 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| US20210393623A1 (en) | 2018-09-26 | 2021-12-23 | Jacobio Pharmaceuticals Co., Ltd. | Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004041201A2 (en) * | 2002-11-01 | 2004-05-21 | Viropharma Incorporated | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| WO2004046095A1 (en) * | 2002-11-19 | 2004-06-03 | Achillion Pharmaceuticals, Inc. | Substituted aryl thioureas and related compounds; inhibitors of viral replication |
| WO2005007601A2 (en) * | 2003-07-10 | 2005-01-27 | Achillion Pharmaceuticals, Inc. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
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| 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 |
-
2004
- 2004-12-30 TW TW093141409A patent/TW200528459A/zh unknown
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2005
- 2005-01-05 KR KR1020067013660A patent/KR20060121289A/ko not_active Withdrawn
- 2005-01-05 CA CA002552002A patent/CA2552002A1/en not_active Abandoned
- 2005-01-05 AT AT05705124T patent/ATE479684T1/de not_active IP Right Cessation
- 2005-01-05 AU AU2005204369A patent/AU2005204369B2/en not_active Ceased
- 2005-01-05 DE DE602005023266T patent/DE602005023266D1/de not_active Expired - Lifetime
- 2005-01-05 AP AP2006003659A patent/AP2006003659A0/xx unknown
- 2005-01-05 JP JP2006549390A patent/JP2007517887A/ja active Pending
- 2005-01-05 EP EP05705124A patent/EP1709047B1/en not_active Expired - Lifetime
- 2005-01-05 US US11/029,910 patent/US7439374B2/en not_active Expired - Fee Related
- 2005-01-05 WO PCT/US2005/000339 patent/WO2005067900A2/en not_active Ceased
- 2005-01-05 EA EA200601281A patent/EA200601281A1/ru unknown
- 2005-01-05 NZ NZ548375A patent/NZ548375A/en unknown
- 2005-01-05 OA OA1200600222A patent/OA13357A/en unknown
- 2005-01-05 CN CNA200580007223XA patent/CN1946720A/zh active Pending
- 2005-01-05 AR ARP050100026A patent/AR047367A1/es not_active Application Discontinuation
- 2005-01-05 BR BRPI0506705-7A patent/BRPI0506705A/pt not_active IP Right Cessation
-
2006
- 2006-06-21 IL IL176486A patent/IL176486A0/en unknown
- 2006-06-22 NO NO20062928A patent/NO20062928L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004041201A2 (en) * | 2002-11-01 | 2004-05-21 | Viropharma Incorporated | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| WO2004046095A1 (en) * | 2002-11-19 | 2004-06-03 | Achillion Pharmaceuticals, Inc. | Substituted aryl thioureas and related compounds; inhibitors of viral replication |
| WO2005007601A2 (en) * | 2003-07-10 | 2005-01-27 | Achillion Pharmaceuticals, Inc. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200528459A (en) | 2005-09-01 |
| AU2005204369A1 (en) | 2005-07-28 |
| AP2006003659A0 (en) | 2006-06-30 |
| ATE479684T1 (de) | 2010-09-15 |
| BRPI0506705A (pt) | 2007-05-02 |
| WO2005067900A2 (en) | 2005-07-28 |
| NO20062928L (no) | 2006-08-03 |
| CA2552002A1 (en) | 2005-07-28 |
| OA13357A (en) | 2007-04-13 |
| AR047367A1 (es) | 2006-01-18 |
| EA200601281A1 (ru) | 2006-12-29 |
| IL176486A0 (en) | 2006-10-05 |
| KR20060121289A (ko) | 2006-11-28 |
| WO2005067900A3 (en) | 2005-09-29 |
| NZ548375A (en) | 2010-07-30 |
| JP2007517887A (ja) | 2007-07-05 |
| US20050228013A1 (en) | 2005-10-13 |
| EP1709047A2 (en) | 2006-10-11 |
| EP1709047B1 (en) | 2010-09-01 |
| CN1946720A (zh) | 2007-04-11 |
| US7439374B2 (en) | 2008-10-21 |
| DE602005023266D1 (de) | 2010-10-14 |
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