OA13187A - Substituted arylthiourea derivatives useful as inhibitors of viral replication. - Google Patents
Substituted arylthiourea derivatives useful as inhibitors of viral replication. Download PDFInfo
- Publication number
- OA13187A OA13187A OA1200600003A OA1200600003A OA13187A OA 13187 A OA13187 A OA 13187A OA 1200600003 A OA1200600003 A OA 1200600003A OA 1200600003 A OA1200600003 A OA 1200600003A OA 13187 A OA13187 A OA 13187A
- Authority
- OA
- OAPI
- Prior art keywords
- phenyl
- thiourea
- halogen
- amino
- compound
- Prior art date
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- 230000029812 viral genome replication Effects 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 51
- 150000003839 salts Chemical class 0.000 claims abstract 48
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 208000005176 Hepatitis C Diseases 0.000 claims abstract 3
- 239000003085 diluting agent Substances 0.000 claims abstract 2
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims 68
- 150000002367 halogens Chemical group 0.000 claims 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 57
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 49
- 229910052739 hydrogen Inorganic materials 0.000 claims 46
- 239000001257 hydrogen Substances 0.000 claims 46
- -1 hydroxy, amino Chemical group 0.000 claims 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims 38
- 150000002431 hydrogen Chemical group 0.000 claims 38
- 125000004076 pyridyl group Chemical group 0.000 claims 34
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 27
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 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 19
- 125000003386 piperidinyl group Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 14
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 230000010076 replication Effects 0.000 claims 4
- LDXFKNPMJRMPKT-UHFFFAOYSA-N (3-benzylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(CC=2C=CC=CC=2)=C1 LDXFKNPMJRMPKT-UHFFFAOYSA-N 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- ZYUGKPCKYSSZRA-UHFFFAOYSA-N (3-phenylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(C=2C=CC=CC=2)=C1 ZYUGKPCKYSSZRA-UHFFFAOYSA-N 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- YOSSYFDRJQJTRS-UHFFFAOYSA-N [3-[(3-methoxyphenyl)methyl]phenyl]thiourea Chemical compound COC1=CC=CC(CC=2C=C(NC(N)=S)C=CC=2)=C1 YOSSYFDRJQJTRS-UHFFFAOYSA-N 0.000 claims 2
- XDLWTDDWPOSDFD-UHFFFAOYSA-N [4-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1N1CC2CCCCC2CC1 XDLWTDDWPOSDFD-UHFFFAOYSA-N 0.000 claims 2
- WOLIEOCUONISCT-UHFFFAOYSA-N [4-(3,4-dihydro-1h-isoquinolin-2-yl)phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1N1CC2=CC=CC=C2CC1 WOLIEOCUONISCT-UHFFFAOYSA-N 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- XDEYCMDTQXGWSJ-UHFFFAOYSA-N (3-fluoro-2-pentan-2-yloxyphenyl)thiourea Chemical compound CCCC(C)OC1=C(F)C=CC=C1NC(N)=S XDEYCMDTQXGWSJ-UHFFFAOYSA-N 0.000 claims 1
- NVYVWHZBRGWOSH-UHFFFAOYSA-N (3-methyl-4-piperidin-1-ylphenyl)thiourea Chemical compound CC1=CC(NC(N)=S)=CC=C1N1CCCCC1 NVYVWHZBRGWOSH-UHFFFAOYSA-N 0.000 claims 1
- NYAJJEYQQQLXHZ-UHFFFAOYSA-N (3-phenoxyphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(OC=2C=CC=CC=2)=C1 NYAJJEYQQQLXHZ-UHFFFAOYSA-N 0.000 claims 1
- ZJVBHZKCEMFREY-UHFFFAOYSA-N (3-phenylmethoxyphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(OCC=2C=CC=CC=2)=C1 ZJVBHZKCEMFREY-UHFFFAOYSA-N 0.000 claims 1
- FKDYIMBVGIWRAH-UHFFFAOYSA-N (3-phenylphenyl)methylthiourea Chemical compound NC(=S)NCC1=CC=CC(C=2C=CC=CC=2)=C1 FKDYIMBVGIWRAH-UHFFFAOYSA-N 0.000 claims 1
- PNSHMNNIDDOKIL-UHFFFAOYSA-N (4-butyl-2-methylphenyl)thiourea Chemical compound CCCCC1=CC=C(NC(N)=S)C(C)=C1 PNSHMNNIDDOKIL-UHFFFAOYSA-N 0.000 claims 1
- RQFIEYITEYTCNW-UHFFFAOYSA-N (4-butylphenyl)methylthiourea Chemical compound CCCCC1=CC=C(CNC(N)=S)C=C1 RQFIEYITEYTCNW-UHFFFAOYSA-N 0.000 claims 1
- CDHAWWZFIVSHCQ-UHFFFAOYSA-N (4-pentoxyphenyl)thiourea Chemical compound CCCCCOC1=CC=C(NC(N)=S)C=C1 CDHAWWZFIVSHCQ-UHFFFAOYSA-N 0.000 claims 1
- QRMAQPKLEOPEER-UHFFFAOYSA-N (4-pentylphenyl)thiourea Chemical compound CCCCCC1=CC=C(NC(N)=S)C=C1 QRMAQPKLEOPEER-UHFFFAOYSA-N 0.000 claims 1
- VTJGIHFDKNNRLZ-UHFFFAOYSA-N (4-phenoxyphenyl)methylthiourea Chemical compound C1=CC(CNC(=S)N)=CC=C1OC1=CC=CC=C1 VTJGIHFDKNNRLZ-UHFFFAOYSA-N 0.000 claims 1
- JDKGVSBSGLEWAM-UHFFFAOYSA-N (4-phenylphenyl)methylthiourea Chemical compound C1=CC(CNC(=S)N)=CC=C1C1=CC=CC=C1 JDKGVSBSGLEWAM-UHFFFAOYSA-N 0.000 claims 1
- HQBMVCGLMQPTFB-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethylthiourea Chemical compound C1=CC(C(NC(N)=S)C)=CC=C1OC1=CC=CC=C1 HQBMVCGLMQPTFB-UHFFFAOYSA-N 0.000 claims 1
- BMKOTUYNZNCGDG-UHFFFAOYSA-N 2-(4-phenoxyphenyl)ethylthiourea Chemical compound C1=CC(CCNC(=S)N)=CC=C1OC1=CC=CC=C1 BMKOTUYNZNCGDG-UHFFFAOYSA-N 0.000 claims 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 claims 1
- JVLMEYNQKMBKAD-UHFFFAOYSA-N [1-(4-phenoxyphenyl)cyclopentyl]thiourea Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C1(NC(=S)N)CCCC1 JVLMEYNQKMBKAD-UHFFFAOYSA-N 0.000 claims 1
- NSRWDUDSMPTHKQ-UHFFFAOYSA-N [3-(2-phenylethoxy)phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC(OCCC=2C=CC=CC=2)=C1 NSRWDUDSMPTHKQ-UHFFFAOYSA-N 0.000 claims 1
- HUIGXVYUJPJCJM-LLVKDONJSA-N [3-[(1r)-1-phenylethoxy]phenyl]thiourea Chemical compound O([C@H](C)C=1C=CC=CC=1)C1=CC=CC(NC(N)=S)=C1 HUIGXVYUJPJCJM-LLVKDONJSA-N 0.000 claims 1
- HUIGXVYUJPJCJM-NSHDSACASA-N [3-[(1s)-1-phenylethoxy]phenyl]thiourea Chemical compound O([C@@H](C)C=1C=CC=CC=1)C1=CC=CC(NC(N)=S)=C1 HUIGXVYUJPJCJM-NSHDSACASA-N 0.000 claims 1
- XIGSCFASUOGHMJ-UHFFFAOYSA-N [3-[(4-phenylphenyl)methoxy]phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC(OCC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 XIGSCFASUOGHMJ-UHFFFAOYSA-N 0.000 claims 1
- GKFKSIKWHGSIEX-UHFFFAOYSA-N [3-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC(OCC=2C=C(C=CC=2)C(F)(F)F)=C1 GKFKSIKWHGSIEX-UHFFFAOYSA-N 0.000 claims 1
- LXSWDBAGQAKOJV-UHFFFAOYSA-N [3-fluoro-4-(4-phenylpiperidin-1-yl)phenyl]thiourea Chemical compound FC1=CC(NC(=S)N)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 LXSWDBAGQAKOJV-UHFFFAOYSA-N 0.000 claims 1
- CJVLVRFEHWKSIC-UHFFFAOYSA-N [3-fluoro-4-[methyl(pentyl)amino]phenyl]thiourea Chemical compound CCCCCN(C)C1=CC=C(NC(N)=S)C=C1F CJVLVRFEHWKSIC-UHFFFAOYSA-N 0.000 claims 1
- WXKPCCNYVYGSNK-UHFFFAOYSA-N [4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1N1C2CCCCC2CCC1 WXKPCCNYVYGSNK-UHFFFAOYSA-N 0.000 claims 1
- YNJXVPMWZQAFSE-UHFFFAOYSA-N [4-(3,4-dihydro-1h-isoquinolin-2-yl)-3-fluorophenyl]thiourea Chemical compound FC1=CC(NC(=S)N)=CC=C1N1CC2=CC=CC=C2CC1 YNJXVPMWZQAFSE-UHFFFAOYSA-N 0.000 claims 1
- QNSJRYXZVQVXKP-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methylthiourea Chemical compound NC(=S)NCC1=CC=C(C(F)(F)F)C=C1 QNSJRYXZVQVXKP-UHFFFAOYSA-N 0.000 claims 1
- FTIPDESXWVLDOH-UHFFFAOYSA-N [4-[3-(dimethylamino)propoxy]phenyl]thiourea Chemical compound CN(C)CCCOC1=CC=C(NC(N)=S)C=C1 FTIPDESXWVLDOH-UHFFFAOYSA-N 0.000 claims 1
- IBQHVBKSWWWJHO-UHFFFAOYSA-N [4-piperidin-1-yl-3-(trifluoromethyl)phenyl]thiourea Chemical compound FC(F)(F)C1=CC(NC(=S)N)=CC=C1N1CCCCC1 IBQHVBKSWWWJHO-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- LTTJRSJHJDEASV-UHFFFAOYSA-N butyl 1-[3-(carbamothioylamino)phenyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCCCC)(C=2C=CC=CC=2)CCN1C1=CC=CC(NC(N)=S)=C1 LTTJRSJHJDEASV-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- CCONRQQOWWFUEU-UHFFFAOYSA-N ethyl 1-[3-(carbamothioylamino)phenyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1C1=CC=CC(NC(N)=S)=C1 CCONRQQOWWFUEU-UHFFFAOYSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229940054534 ophthalmic solution Drugs 0.000 claims 1
- 239000002997 ophthalmic solution Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- DOFNIDPLSQZBSU-UHFFFAOYSA-N tritylthiourea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NC(=S)N)C1=CC=CC=C1 DOFNIDPLSQZBSU-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract 2
- 241000711549 Hepacivirus C Species 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 229940124639 Selective inhibitor Drugs 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C335/12—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- C07C335/14—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- 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
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48669703P | 2003-07-10 | 2003-07-10 | |
| US49614603P | 2003-08-18 | 2003-08-18 | |
| US50669903P | 2003-09-26 | 2003-09-26 | |
| US50999503P | 2003-10-08 | 2003-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA13187A true OA13187A (en) | 2006-12-13 |
Family
ID=34084732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200600003A OA13187A (en) | 2003-07-10 | 2004-07-08 | Substituted arylthiourea derivatives useful as inhibitors of viral replication. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7718671B2 (fr) |
| EP (1) | EP1648862A2 (fr) |
| JP (1) | JP2007523868A (fr) |
| KR (1) | KR20070007759A (fr) |
| AU (1) | AU2004257277B2 (fr) |
| BR (1) | BRPI0412502A (fr) |
| CA (1) | CA2531068A1 (fr) |
| EA (1) | EA010017B1 (fr) |
| IL (1) | IL172876A0 (fr) |
| MX (1) | MXPA06000418A (fr) |
| NO (1) | NO20060126L (fr) |
| NZ (1) | NZ544674A (fr) |
| OA (1) | OA13187A (fr) |
| WO (1) | WO2005007601A2 (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200528459A (en) | 2004-01-06 | 2005-09-01 | Achillion Pharmaceuticals Inc | Azabenzofuran substituted thioureas; 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 |
| CL2008000812A1 (es) * | 2007-04-03 | 2008-10-10 | Bayer Cropscience Ag | Compuestos derivados de bencil-oxazolidin-2-iliden-amina; procedimiento de preparacion; composicion que comprende a dichos compuestos; procedimiento para controlar plagas; y uso de dichos compuestos para controlar plagas |
| EP1977644A1 (fr) * | 2007-04-03 | 2008-10-08 | Bayer CropScience Aktiengesellschaft | Dérivés insecticides de benzylamines substitués |
| EP1977645A1 (fr) * | 2007-04-03 | 2008-10-08 | Bayer CropScience Aktiengesellschaft | Dérivés insecticides de phenylalkylamines substitués |
| CL2008000773A1 (es) * | 2007-04-03 | 2008-10-10 | Bayer Cropscience Ag | Compuestos derivados de bencilaminas sustituidas; procedimiento para la preparacion de dichos compuestos; composicion; procedimiento para controlar plagas; y uso de dichos compuestos. |
| US7985763B2 (en) * | 2007-04-10 | 2011-07-26 | National Health Research Institutes | Hepatitis C virus inhibitors |
| WO2008141227A1 (fr) | 2007-05-10 | 2008-11-20 | Intermune, Inc. | Nouveaux inhibiteurs peptidiques de la réplication du virus de l'hépatite c |
| 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 |
| MX2013004906A (es) | 2010-11-01 | 2013-12-06 | Genoscience Pharma | Nuevos inhibidores especificos de la proteasa ns3 de hcv. |
| CN103073455B (zh) * | 2011-10-25 | 2015-08-19 | 中国科学院上海药物研究所 | 一类新型的kcnq钾通道激动剂、其制备方法和用途 |
| US9040479B2 (en) | 2012-01-12 | 2015-05-26 | Cocrystal Pharma, Inc. | HCV NS3 protease inhibitors |
| EP3214071B1 (fr) | 2013-03-05 | 2019-07-03 | Asahi Kasei Kabushiki Kaisha | Composition à base d'isothiocyanate |
| WO2017026830A1 (fr) * | 2015-08-12 | 2017-02-16 | 서울대학교 산학협력단 | Utilisation d'une composition pharmaceutique comprenant un dérivé de thio-urée pour la prévention ou le traitement de maladies auto-immunes |
| KR20180088412A (ko) * | 2015-12-11 | 2018-08-03 | 데이진 화-마 가부시키가이샤 | 아미노아졸 유도체 |
| 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 |
| EP3454856B1 (fr) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Dégronimères hétérocycliques pour la dégradation de protéines cibles |
| 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 |
| ES2990061T3 (es) | 2016-05-10 | 2024-11-28 | C4 Therapeutics Inc | Degronímeros espirocíclicos para la degradación de proteínas diana |
| 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 |
| US10702525B1 (en) * | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
| KR102727491B1 (ko) * | 2021-11-15 | 2024-11-11 | 서울대학교산학협력단 | RORα의 활성자로서의 신규한 티오우레아 유도체 및 이를 포함하는 약학적 조성물 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1408198A (en) | 1971-08-23 | 1975-10-01 | Medizinska Akad | Antiviral compositions |
| GB1465794A (en) * | 1974-05-17 | 1977-03-02 | Wyeth John & Brother Ltd | Thiourea derivatives |
| US4194008A (en) * | 1976-09-03 | 1980-03-18 | Bayer Aktiengesellschaft | N-aryl-N'-(cyclo)-alkyl-thioureas and their use as agents for combating animal pests and plant pests |
| DE2639738C2 (de) | 1976-09-03 | 1982-08-12 | Phoenix Ag, 2100 Hamburg | Zylinderförmiges Hubelement |
| NZ186237A (en) | 1977-01-20 | 1978-12-18 | Bayer Ag | N-aryl-n'-alkyl-thioureas and pesticidal compositions for both plant and animal use |
| US4307106A (en) * | 1978-06-02 | 1981-12-22 | Pfizer Inc. | Aminothiazoles |
| ZA801680B (en) * | 1979-04-03 | 1981-03-25 | Fujisawa Pharmaceutical Co | 2-imidazoline derivatives,process for the preparation thereof and the pharmaceutical composition of the same |
| JPS55167282A (en) * | 1979-06-12 | 1980-12-26 | Fujisawa Pharmaceut Co Ltd | Piperazine derivative or its salt and its preparation |
| WO1996018607A1 (fr) * | 1994-12-12 | 1996-06-20 | Chugai Seiyaku Kabushiki Kaisha | Derive d'aniline inhibant la synthase du monoxyde d'azote |
| ES2168121T7 (es) * | 1995-12-21 | 2013-09-24 | Syngenta Participations Ag | Derivados de ácido 3-amino-2-mercaptobenzoico y procedimientos para su preparación |
| CA2253502A1 (fr) | 1996-05-06 | 1997-11-13 | Stephen Warren Kaldor | Composes antiviraux |
| AU6421998A (en) | 1997-03-24 | 1998-10-20 | Chugai Seiyaku Kabushiki Kaisha | Hetero-tricyclic compouds exhibiting inhibitory activity against nos |
| JP2001519808A (ja) * | 1997-04-10 | 2001-10-23 | ファルマシア・アンド・アップジョン・カンパニー | ポリ芳香族抗菌組成物 |
| CN1294590A (zh) * | 1997-12-12 | 2001-05-09 | 欧罗赛铁克股份有限公司 | 通过2－硫代黄嘌呤制备3－取代腺嘌呤的方法 |
| WO1999040088A1 (fr) * | 1998-02-09 | 1999-08-12 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines et guanidines utiles en tant qu'inhibiteurs de protease et plus particulierement en tant qu'inhibiteurs d'urokinase |
| EP1083172A4 (fr) * | 1998-05-26 | 2001-10-10 | Rimma Iliinichna Ashkinazi | Derives n-substitues d'acide 5-oxyiminobarbiturique |
| BR9915993A (pt) * | 1998-12-09 | 2001-09-04 | American Home Prod | Composto, composição farmacêutica, processo para inibir a replicação de um vìrus herpes, e, processo para tratar um paciente sofrendo de uma infecção de vìrus herpes |
| EP1144399A3 (fr) * | 1998-12-09 | 2002-09-11 | Wyeth | Inhibiteurs heterocycliques de thio-uree des virus de l'herpes contenant du carboxamide et un groupe phenylenediamine substitue |
| US6677360B2 (en) * | 1998-12-16 | 2004-01-13 | Bayer Aktiengesellschaft | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US6492403B1 (en) * | 1999-02-09 | 2002-12-10 | 3-Dimensional Pharmaceuticals, Inc. | Methods of treating C1s-mediated diseases and conditions and compositions thereof |
| KR20010098982A (ko) * | 1999-02-09 | 2001-11-08 | 3-디멘져널 파마슈티칼즈 인코오포레이티드 | 프로테아제 억제제로서의 헤테로아릴 아미딘, 메틸아미딘및 구아니딘 |
| JP2002540086A (ja) * | 1999-03-19 | 2002-11-26 | パーカー ヒューズ インスティテュート | チオ尿素および尿素液相コンビナトリアルライブラリ、合成およびアポトーシス誘導 |
| WO2001083429A1 (fr) | 2000-04-28 | 2001-11-08 | Chugai Seiyaku Kabushiki Kaisha | Derives d'aniline |
| JP2001316314A (ja) * | 2000-05-09 | 2001-11-13 | Euro Celtique Sa | 増強されたホスホジエステラーゼｉｖ阻害活性を有する６，５−融合芳香環系 |
| AU2001281817B2 (en) * | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| FR2812633A1 (fr) * | 2000-08-04 | 2002-02-08 | Aventis Cropscience Sa | Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides |
| JP2002255964A (ja) * | 2000-10-24 | 2002-09-11 | Sankyo Co Ltd | イミダゾピリジン誘導体 |
| RU2302411C2 (ru) | 2001-05-09 | 2007-07-10 | Байер Кропсайенс Аг | Замещенные арилкетоны и гербицидное средство на их основе |
-
2004
- 2004-07-08 BR BRPI0412502-9A patent/BRPI0412502A/pt not_active IP Right Cessation
- 2004-07-08 US US10/887,227 patent/US7718671B2/en not_active Expired - Fee Related
- 2004-07-08 AU AU2004257277A patent/AU2004257277B2/en not_active Ceased
- 2004-07-08 MX MXPA06000418A patent/MXPA06000418A/es not_active Application Discontinuation
- 2004-07-08 EA EA200600227A patent/EA010017B1/ru not_active IP Right Cessation
- 2004-07-08 OA OA1200600003A patent/OA13187A/en unknown
- 2004-07-08 WO PCT/US2004/022599 patent/WO2005007601A2/fr not_active Ceased
- 2004-07-08 JP JP2006518982A patent/JP2007523868A/ja active Pending
- 2004-07-08 NZ NZ544674A patent/NZ544674A/en not_active IP Right Cessation
- 2004-07-08 CA CA002531068A patent/CA2531068A1/fr not_active Abandoned
- 2004-07-08 EP EP04756991A patent/EP1648862A2/fr not_active Withdrawn
- 2004-07-08 KR KR1020067000589A patent/KR20070007759A/ko not_active Withdrawn
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2005
- 2005-12-28 IL IL172876A patent/IL172876A0/en unknown
-
2006
- 2006-01-09 NO NO20060126A patent/NO20060126L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7718671B2 (en) | 2010-05-18 |
| NO20060126L (no) | 2006-02-08 |
| WO2005007601A2 (fr) | 2005-01-27 |
| NZ544674A (en) | 2009-03-31 |
| KR20070007759A (ko) | 2007-01-16 |
| WO2005007601A3 (fr) | 2005-06-23 |
| MXPA06000418A (es) | 2006-04-05 |
| AU2004257277A1 (en) | 2005-01-27 |
| CA2531068A1 (fr) | 2005-01-27 |
| EA200600227A1 (ru) | 2006-06-30 |
| AU2004257277B2 (en) | 2011-03-31 |
| JP2007523868A (ja) | 2007-08-23 |
| IL172876A0 (en) | 2006-06-11 |
| EA010017B1 (ru) | 2008-06-30 |
| BRPI0412502A (pt) | 2006-09-19 |
| US20050032849A1 (en) | 2005-02-10 |
| EP1648862A2 (fr) | 2006-04-26 |
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