JP2007530582A - 代謝可能部分を含む複素環抗ウイルス化合物およびその使用 - Google Patents
代謝可能部分を含む複素環抗ウイルス化合物およびその使用 Download PDFInfo
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- JP2007530582A JP2007530582A JP2007505199A JP2007505199A JP2007530582A JP 2007530582 A JP2007530582 A JP 2007530582A JP 2007505199 A JP2007505199 A JP 2007505199A JP 2007505199 A JP2007505199 A JP 2007505199A JP 2007530582 A JP2007530582 A JP 2007530582A
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- substituted
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- aryl
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 331
- 125000000623 heterocyclic group Chemical group 0.000 title description 8
- 230000000840 anti-viral effect Effects 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 132
- 241000711549 Hepacivirus C Species 0.000 claims abstract description 91
- 208000015181 infectious disease Diseases 0.000 claims abstract description 36
- 230000010076 replication Effects 0.000 claims abstract description 23
- 230000035755 proliferation Effects 0.000 claims abstract description 13
- -1 -C (O) H Chemical group 0.000 claims description 371
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 291
- 238000000034 method Methods 0.000 claims description 220
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000003107 substituted aryl group Chemical group 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 230000002194 synthesizing effect Effects 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
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- 125000004397 aminosulfonyl group Chemical class NS(=O)(=O)* 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000006371 dihalo methyl group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 6
- 241000700605 Viruses Species 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000099 in vitro assay Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000006372 monohalo methyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004405 heteroalkoxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- PUDFKSZFWZMYLT-UHFFFAOYSA-N 4,4a,5,6,7,8a-hexahydropyrano[2,3-d][1,3]dioxine-5,7-diol Chemical compound C1OCOC2OC(O)CC(O)C21 PUDFKSZFWZMYLT-UHFFFAOYSA-N 0.000 claims description 3
- PXRCACAJKIBESG-UHFFFAOYSA-N 5,7-dihydroxy-4,4a,5,6,7,8a-hexahydropyrano[2,3-d][1,3]dioxin-2-one Chemical compound C1OC(=O)OC2OC(O)CC(O)C21 PXRCACAJKIBESG-UHFFFAOYSA-N 0.000 claims description 3
- PMMURAAUARKVCB-UHFFFAOYSA-N 6-(hydroxymethyl)oxane-2,4,5-triol Chemical compound OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 238000001727 in vivo Methods 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 150000003527 tetrahydropyrans Chemical class 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 2
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 claims description 2
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- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000651 prodrug Substances 0.000 abstract description 160
- 229940002612 prodrug Drugs 0.000 abstract description 160
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- 238000013459 approach Methods 0.000 abstract description 7
- 125000006267 biphenyl group Chemical group 0.000 abstract description 3
- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 242
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 147
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 139
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 122
- 239000000243 solution Substances 0.000 description 117
- 238000003786 synthesis reaction Methods 0.000 description 104
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
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- 239000011541 reaction mixture Substances 0.000 description 64
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
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- 238000006243 chemical reaction Methods 0.000 description 45
- 238000003818 flash chromatography Methods 0.000 description 45
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
- 238000003556 assay Methods 0.000 description 41
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 37
- 210000004027 cell Anatomy 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
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- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
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- 125000003342 alkenyl group Chemical group 0.000 description 10
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- MUSLLWVESNMNOT-UHFFFAOYSA-N 2,2-dichloro-n-[2-[3-(2,6-dichlorophenyl)-1,2-oxazol-5-yl]pyridin-4-yl]-n-(3-morpholin-4-yl-3-oxopropyl)acetamide Chemical compound C=1C=NC(C=2ON=C(C=2)C=2C(=CC=CC=2Cl)Cl)=CC=1N(C(=O)C(Cl)Cl)CCC(=O)N1CCOCC1 MUSLLWVESNMNOT-UHFFFAOYSA-N 0.000 description 7
- UAVZKRLWYOSHHP-UHFFFAOYSA-N 3,4-diphenyl-1,2-oxazole Chemical class C=1ON=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 UAVZKRLWYOSHHP-UHFFFAOYSA-N 0.000 description 7
- GYHTYFJZHBSJLA-UHFFFAOYSA-N 4-[3-[(2,2-dichloroacetyl)-[2-[3-(2,6-dichlorophenyl)-1,2-oxazol-5-yl]pyridin-4-yl]amino]propanoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)CCN(C(=O)C(Cl)Cl)C1=CC=NC(C=2ON=C(C=2)C=2C(=CC=CC=2Cl)Cl)=C1 GYHTYFJZHBSJLA-UHFFFAOYSA-N 0.000 description 7
- ADGSRHFYCLHHJZ-UHFFFAOYSA-N [4-[3-[(2,2-dichloroacetyl)-[2-[3-(2,6-dichlorophenyl)-1,2-oxazol-5-yl]pyridin-4-yl]amino]propyl]phenyl]methylphosphonic acid Chemical compound C1=CC(CP(O)(=O)O)=CC=C1CCCN(C(=O)C(Cl)Cl)C1=CC=NC(C=2ON=C(C=2)C=2C(=CC=CC=2Cl)Cl)=C1 ADGSRHFYCLHHJZ-UHFFFAOYSA-N 0.000 description 7
- 239000012190 activator Substances 0.000 description 7
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
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- Biochemistry (AREA)
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- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55662504P | 2004-03-26 | 2004-03-26 | |
| US58290304P | 2004-06-24 | 2004-06-24 | |
| PCT/US2005/009909 WO2005097760A1 (en) | 2004-03-26 | 2005-03-25 | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007530582A true JP2007530582A (ja) | 2007-11-01 |
| JP2007530582A5 JP2007530582A5 (https=) | 2008-05-01 |
Family
ID=34963905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007505199A Pending JP2007530582A (ja) | 2004-03-26 | 2005-03-25 | 代謝可能部分を含む複素環抗ウイルス化合物およびその使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20050239751A1 (https=) |
| EP (1) | EP1740556A1 (https=) |
| JP (1) | JP2007530582A (https=) |
| WO (1) | WO2005097760A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016034946A (ja) * | 2009-02-05 | 2016-03-17 | トーカイ ファーマシューティカルズ,インク. | ステロイド性cyp17阻害剤/抗アンドロゲン剤の新しいプロドラッグ |
| US9808472B2 (en) | 2013-08-12 | 2017-11-07 | Tokai Pharmaceuticals, Inc. | Biomarkers for treatment of neoplastic disorders using androgen-targeted therapies |
| US9884067B2 (en) | 2013-03-14 | 2018-02-06 | University Of Maryland, Baltimore | Androgen receptor down-regulating agents and uses thereof |
| JP2018536015A (ja) * | 2015-09-16 | 2018-12-06 | メタクリン,インク. | ファルネソイドx受容体アゴニストとその使用 |
| US10927082B2 (en) | 2017-03-15 | 2021-02-23 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US11084817B2 (en) | 2018-09-18 | 2021-08-10 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US11236071B1 (en) | 2017-03-15 | 2022-02-01 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US12491160B2 (en) | 2020-03-18 | 2025-12-09 | Eli Lilly And Company | Formulations of a farnesoid X receptor agonist |
| US12545660B2 (en) | 2020-03-18 | 2026-02-10 | Eli Lilly And Company | Crystalline forms of a farnesoid X receptor agonist |
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|---|---|---|---|---|
| US7410979B2 (en) | 2003-11-19 | 2008-08-12 | Rigel Pharmaceuticals, Inc. | Synergistically effective combinations of dihaloacetamide compounds and interferon or ribavirin against HCV infections |
| CA2606106A1 (en) * | 2005-05-02 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
| PT2178858E (pt) | 2007-08-02 | 2012-02-24 | Recordati Ireland Ltd | Novos compostos heterocíclicos como antagonistas de mglu5 |
| WO2011009484A1 (en) * | 2009-07-22 | 2011-01-27 | Novartis Ag | Arylpyrazoles and arylisoxazoles and their use as pkd modulators |
| US20130210836A1 (en) | 2010-07-19 | 2013-08-15 | Syngenta Crop Protection Llc | Microbicides |
| EP2595985A1 (en) | 2010-07-19 | 2013-05-29 | Syngenta Participations AG | Isoxazole, isothiazole, furane and thiophene compounds as microbicides |
| WO2013007550A1 (en) | 2011-07-08 | 2013-01-17 | Syngenta Participations Ag | Fungicide mixtures |
| WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
| WO2014027696A1 (ja) | 2012-08-17 | 2014-02-20 | 中外製薬株式会社 | 抗hcv作用を有する経口投与可能なビリジオファンジン誘導体 |
| CN103145688A (zh) * | 2013-04-02 | 2013-06-12 | 黄冈鲁班药业有限公司 | 4,5-二氯甲基-1,3-二氧杂环戊烯-2-酮的制备方法 |
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| WO2003040112A1 (en) * | 2001-11-02 | 2003-05-15 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl heterocycles useful for treating hcv infection |
| WO2004018463A2 (en) * | 2002-08-23 | 2004-03-04 | Rigel Pharmaceuticals, Inc. | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| WO2004099164A1 (en) * | 2003-05-02 | 2004-11-18 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating hcv infection |
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| DE3514182A1 (de) * | 1985-04-19 | 1986-10-23 | Basf Ag, 6700 Ludwigshafen | Elektrophotographisches aufzeichnungsmaterial |
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| DE4408084A1 (de) * | 1994-03-10 | 1995-09-14 | Hoechst Ag | 3,5-Disubstituierte und 3,4,5-trisubstituierte 2-Isoxazoline und Isoxazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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2005
- 2005-03-25 WO PCT/US2005/009909 patent/WO2005097760A1/en not_active Ceased
- 2005-03-25 JP JP2007505199A patent/JP2007530582A/ja active Pending
- 2005-03-25 US US11/090,823 patent/US20050239751A1/en not_active Abandoned
- 2005-03-25 EP EP05726121A patent/EP1740556A1/en not_active Withdrawn
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| WO2003040112A1 (en) * | 2001-11-02 | 2003-05-15 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl heterocycles useful for treating hcv infection |
| WO2004018463A2 (en) * | 2002-08-23 | 2004-03-04 | Rigel Pharmaceuticals, Inc. | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| WO2004099164A1 (en) * | 2003-05-02 | 2004-11-18 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating hcv infection |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016034946A (ja) * | 2009-02-05 | 2016-03-17 | トーカイ ファーマシューティカルズ,インク. | ステロイド性cyp17阻害剤/抗アンドロゲン剤の新しいプロドラッグ |
| US9884067B2 (en) | 2013-03-14 | 2018-02-06 | University Of Maryland, Baltimore | Androgen receptor down-regulating agents and uses thereof |
| US9808472B2 (en) | 2013-08-12 | 2017-11-07 | Tokai Pharmaceuticals, Inc. | Biomarkers for treatment of neoplastic disorders using androgen-targeted therapies |
| JP2018536015A (ja) * | 2015-09-16 | 2018-12-06 | メタクリン,インク. | ファルネソイドx受容体アゴニストとその使用 |
| US11214538B2 (en) | 2015-09-16 | 2022-01-04 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US10927082B2 (en) | 2017-03-15 | 2021-02-23 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US10961198B2 (en) | 2017-03-15 | 2021-03-30 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US11236071B1 (en) | 2017-03-15 | 2022-02-01 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US11084817B2 (en) | 2018-09-18 | 2021-08-10 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| US11773094B2 (en) | 2018-09-18 | 2023-10-03 | Organovo, Inc. | Farnesoid X receptor agonists and uses thereof |
| US12491160B2 (en) | 2020-03-18 | 2025-12-09 | Eli Lilly And Company | Formulations of a farnesoid X receptor agonist |
| US12545660B2 (en) | 2020-03-18 | 2026-02-10 | Eli Lilly And Company | Crystalline forms of a farnesoid X receptor agonist |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050239751A1 (en) | 2005-10-27 |
| WO2005097760A1 (en) | 2005-10-20 |
| EP1740556A1 (en) | 2007-01-10 |
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