CA2625974A1 - Imidazole derivatives for the treatment of anxiety and related diseases - Google Patents
Imidazole derivatives for the treatment of anxiety and related diseases Download PDFInfo
- Publication number
- CA2625974A1 CA2625974A1 CA002625974A CA2625974A CA2625974A1 CA 2625974 A1 CA2625974 A1 CA 2625974A1 CA 002625974 A CA002625974 A CA 002625974A CA 2625974 A CA2625974 A CA 2625974A CA 2625974 A1 CA2625974 A1 CA 2625974A1
- Authority
- CA
- Canada
- Prior art keywords
- imidazol
- methanone
- phenyl
- biphenyl
- methoxy
- 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.)
- Abandoned
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 33
- 201000010099 disease Diseases 0.000 title claims abstract description 18
- 238000011282 treatment Methods 0.000 title claims abstract description 18
- 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 10
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 5
- 230000036506 anxiety Effects 0.000 title abstract description 4
- 150000002460 imidazoles Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 369
- 238000000034 method Methods 0.000 claims abstract description 207
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- -1 cycloalkylakyl Chemical group 0.000 claims description 206
- 239000000203 mixture Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- BTWJNRIUHQOEET-UHFFFAOYSA-N 1-[3-(2-fluoropyridin-4-yl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C=C(F)N=CC=2)=C1 BTWJNRIUHQOEET-UHFFFAOYSA-N 0.000 claims description 17
- ULPRGOXMKNYLEX-UHFFFAOYSA-N 1-[3-(3-fluoro-2-methoxyphenyl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=C(F)C=CC=2)OC)=C1 ULPRGOXMKNYLEX-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 206010047700 Vomiting Diseases 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- PHERIMRWNZMOEP-UHFFFAOYSA-N 1-(3-nitrophenyl)imidazole-4-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN1C1=CC=CC([N+]([O-])=O)=C1 PHERIMRWNZMOEP-UHFFFAOYSA-N 0.000 claims description 6
- 208000008811 Agoraphobia Diseases 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 208000019906 panic disease Diseases 0.000 claims description 6
- IMPUAGMIJOGFFD-UHFFFAOYSA-N [1-[3-(5-fluoro-2-methoxyphenyl)phenyl]imidazol-4-yl]-(3-methylpyridin-2-yl)methanone Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2C(=CC=CN=2)C)=C1 IMPUAGMIJOGFFD-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- KUHNQHXGKUVNPR-UHFFFAOYSA-N (5-methyl-1,3-thiazol-2-yl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 KUHNQHXGKUVNPR-UHFFFAOYSA-N 0.000 claims description 4
- FRTHZENWFZGPAU-UHFFFAOYSA-N 1-[1-(3-bromophenyl)imidazol-4-yl]-2-pyridin-3-yloxyethanone Chemical compound BrC1=CC=CC(N2C=C(N=C2)C(=O)COC=2C=NC=CC=2)=C1 FRTHZENWFZGPAU-UHFFFAOYSA-N 0.000 claims description 4
- QCIWNYZZHDYXKU-UHFFFAOYSA-N 1-[3-(2,4-difluoropyridin-3-yl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=NC=CC=2F)F)=C1 QCIWNYZZHDYXKU-UHFFFAOYSA-N 0.000 claims description 4
- VLXYZAOYQXNAHA-UHFFFAOYSA-N 1-[3-(2-chlorophenyl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=CC=CC=2)Cl)=C1 VLXYZAOYQXNAHA-UHFFFAOYSA-N 0.000 claims description 4
- UFSUWJUYWKASGN-UHFFFAOYSA-N 1-[3-(2-cyanophenyl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=CC=CC=2)C#N)=C1 UFSUWJUYWKASGN-UHFFFAOYSA-N 0.000 claims description 4
- LGMSAXQXQZWKCP-UHFFFAOYSA-N 1-[3-(5-fluoro-2-methoxyphenyl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=CC=C(F)C=2)OC)=C1 LGMSAXQXQZWKCP-UHFFFAOYSA-N 0.000 claims description 4
- CQOMURSCEMGNNV-UHFFFAOYSA-N 2-[3-[4-(1,3-thiazole-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound N=1C=CSC=1C(=O)C(N=C1)=CN1C(C=1)=CC=CC=1C1=CC=CC=C1C#N CQOMURSCEMGNNV-UHFFFAOYSA-N 0.000 claims description 4
- ZPLWDIMXUSWQAI-UHFFFAOYSA-N 2-[3-[4-(2-methoxybenzoyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound COC1=CC=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 ZPLWDIMXUSWQAI-UHFFFAOYSA-N 0.000 claims description 4
- HQRHTWPWDBPJFV-UHFFFAOYSA-N 2-[3-[4-(3-fluorobenzoyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound FC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)=C1 HQRHTWPWDBPJFV-UHFFFAOYSA-N 0.000 claims description 4
- KZPFIKYSUIHKKT-UHFFFAOYSA-N 2-[3-[4-(3-methoxybenzoyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound COC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)=C1 KZPFIKYSUIHKKT-UHFFFAOYSA-N 0.000 claims description 4
- WFULIPNQKDTXKW-UHFFFAOYSA-N 2-[3-[4-(3-methylpyridine-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound CC1=CC=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 WFULIPNQKDTXKW-UHFFFAOYSA-N 0.000 claims description 4
- WJMYSOWQRYHYNZ-UHFFFAOYSA-N 2-[3-[4-(4-fluorobenzoyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 WJMYSOWQRYHYNZ-UHFFFAOYSA-N 0.000 claims description 4
- HGGJXJIUCWIXOR-UHFFFAOYSA-N 2-[3-[4-(4-methoxybenzoyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 HGGJXJIUCWIXOR-UHFFFAOYSA-N 0.000 claims description 4
- NPZLOXHXWGWLIT-UHFFFAOYSA-N 2-[3-[4-(4-methylpyridine-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound CC1=CC=NC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)=C1 NPZLOXHXWGWLIT-UHFFFAOYSA-N 0.000 claims description 4
- FIFDAGHZBFAZSB-UHFFFAOYSA-N 2-[3-[4-(5-methyl-1,3-thiazole-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 FIFDAGHZBFAZSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- PMOAHPJUMBKXMA-UHFFFAOYSA-N [1-(3-bromophenyl)imidazol-4-yl]-phenylmethanone Chemical compound BrC1=CC=CC(N2C=C(N=C2)C(=O)C=2C=CC=CC=2)=C1 PMOAHPJUMBKXMA-UHFFFAOYSA-N 0.000 claims description 4
- RKQZGZNUGPYHOP-UHFFFAOYSA-N [1-[3-(2,4-difluoropyridin-3-yl)phenyl]imidazol-4-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC=CC=2F)F)C=N1 RKQZGZNUGPYHOP-UHFFFAOYSA-N 0.000 claims description 4
- XUTUULQJWLLWIV-UHFFFAOYSA-N [1-[3-(2,4-difluoropyridin-3-yl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC=CC=2F)F)C=N1 XUTUULQJWLLWIV-UHFFFAOYSA-N 0.000 claims description 4
- APZLLAOTHKULRU-UHFFFAOYSA-N [1-[3-(2,4-dimethoxypyrimidin-5-yl)phenyl]imidazol-4-yl]-(3-fluorophenyl)methanone Chemical compound COC1=NC(OC)=NC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2C=C(F)C=CC=2)=C1 APZLLAOTHKULRU-UHFFFAOYSA-N 0.000 claims description 4
- BEQJTHCJZLIMKH-UHFFFAOYSA-N [1-[3-(2,4-dimethoxypyrimidin-5-yl)phenyl]imidazol-4-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC(OC)=NC=2)OC)C=N1 BEQJTHCJZLIMKH-UHFFFAOYSA-N 0.000 claims description 4
- VCAWANMKWKJANQ-UHFFFAOYSA-N [1-[3-(2-chlorophenyl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)Cl)C=N1 VCAWANMKWKJANQ-UHFFFAOYSA-N 0.000 claims description 4
- NDKBPNDAEOSILK-UHFFFAOYSA-N [1-[3-(2-chloropyridin-3-yl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC=CC=2)Cl)C=N1 NDKBPNDAEOSILK-UHFFFAOYSA-N 0.000 claims description 4
- PZHMGMIWRDCPBJ-UHFFFAOYSA-N [1-[3-(2-fluoro-6-methoxyphenyl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2SC(C)=CN=2)=C1 PZHMGMIWRDCPBJ-UHFFFAOYSA-N 0.000 claims description 4
- RDMUKRVLCTYVOI-UHFFFAOYSA-N [1-[3-(2-fluoro-6-methoxyphenyl)phenyl]imidazol-4-yl]-(furan-2-yl)methanone Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2OC=CC=2)=C1 RDMUKRVLCTYVOI-UHFFFAOYSA-N 0.000 claims description 4
- ZYAOAWRPQFQHCO-UHFFFAOYSA-N [1-[3-(2-fluoropyridin-3-yl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C=N1 ZYAOAWRPQFQHCO-UHFFFAOYSA-N 0.000 claims description 4
- JKULIOIBNMJXRQ-UHFFFAOYSA-N [1-[3-(2-fluoropyridin-3-yl)phenyl]imidazol-4-yl]-(furan-2-yl)methanone Chemical compound FC1=NC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2OC=CC=2)=C1 JKULIOIBNMJXRQ-UHFFFAOYSA-N 0.000 claims description 4
- HSHQBPGMCHLYEN-UHFFFAOYSA-N [1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2SC(C)=CN=2)=C1 HSHQBPGMCHLYEN-UHFFFAOYSA-N 0.000 claims description 4
- AKMZIGLHEPTJRZ-UHFFFAOYSA-N [1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]-pyridin-2-ylmethanone Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2N=CC=CC=2)=C1 AKMZIGLHEPTJRZ-UHFFFAOYSA-N 0.000 claims description 4
- YKYNLQBYHQWURM-UHFFFAOYSA-N [1-[3-(3-fluoro-2-methoxyphenyl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound COC1=C(F)C=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2SC(C)=CN=2)=C1 YKYNLQBYHQWURM-UHFFFAOYSA-N 0.000 claims description 4
- WDXKEZMTLTVQRX-UHFFFAOYSA-N [1-[3-(3-fluoropyridin-4-yl)phenyl]imidazol-4-yl]-(5-methyl-1,3-thiazol-2-yl)methanone Chemical compound S1C(C)=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CN=CC=2)F)C=N1 WDXKEZMTLTVQRX-UHFFFAOYSA-N 0.000 claims description 4
- QLWCSJPANQFEAH-UHFFFAOYSA-N [1-[3-(5-fluoro-2-methoxyphenyl)phenyl]imidazol-4-yl]-(1,3-thiazol-2-yl)methanone Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2SC=CN=2)=C1 QLWCSJPANQFEAH-UHFFFAOYSA-N 0.000 claims description 4
- JPRXTJINYJBOST-UHFFFAOYSA-N [1-[3-(5-fluoro-2-methoxyphenyl)phenyl]imidazol-4-yl]-(1-methylimidazol-2-yl)methanone Chemical compound COC1=CC=C(F)C=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2N(C=CN=2)C)=C1 JPRXTJINYJBOST-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- DSZUXKHRHGJWEP-UHFFFAOYSA-N 1-(3-nitrophenyl)-n-propylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)NCCC)=CN1C1=CC=CC([N+]([O-])=O)=C1 DSZUXKHRHGJWEP-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Nutrition Science (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200501445 | 2005-10-14 | ||
| DKPA200501445 | 2005-10-14 | ||
| US72667705P | 2005-10-17 | 2005-10-17 | |
| US60/726,677 | 2005-10-17 | ||
| PCT/EP2006/067315 WO2007042546A1 (en) | 2005-10-14 | 2006-10-12 | Imidazole derivatives for the treatment of anxiety and related diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2625974A1 true CA2625974A1 (en) | 2007-04-19 |
Family
ID=37441005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002625974A Abandoned CA2625974A1 (en) | 2005-10-14 | 2006-10-12 | Imidazole derivatives for the treatment of anxiety and related diseases |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8030339B2 (https=) |
| EP (1) | EP1937649A1 (https=) |
| JP (1) | JP2009511547A (https=) |
| AU (1) | AU2006301222A1 (https=) |
| CA (1) | CA2625974A1 (https=) |
| WO (1) | WO2007042546A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8937184B2 (en) * | 2005-02-16 | 2015-01-20 | Abbvie B.V. | 1H-imidazole derivatives as cannabinoid CB2 receptor modulators |
| WO2009131957A2 (en) | 2008-04-21 | 2009-10-29 | Institute For Oneworld Health | Compounds, compositions and methods comprising oxadiazole derivatives |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| MX2010014066A (es) * | 2008-06-16 | 2011-06-01 | Univ Tennessee Res Foundation | Compuestos para el tratamiento del cancer. |
| JP2012503005A (ja) * | 2008-09-19 | 2012-02-02 | インスティテュート フォア ワンワールド ヘルス | イミダゾール誘導体およびトリアゾール誘導体を含む、化合物、組成物ならびに方法。 |
| WO2010034927A1 (fr) * | 2008-09-24 | 2010-04-01 | Zach System | Procede de preparation de nebivolol |
| US8343976B2 (en) | 2009-04-20 | 2013-01-01 | Institute For Oneworld Health | Compounds, compositions and methods comprising pyrazole derivatives |
| JP5879273B2 (ja) | 2010-03-01 | 2016-03-08 | ジーティーエックス・インコーポレイテッド | 癌を処置するための化合物 |
| WO2013120771A1 (en) * | 2012-02-13 | 2013-08-22 | F. Hoffmann-La Roche Ag | Imidazolylketone derivatives asd aldosterone synthase inhibitors |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| PE20230413A1 (es) * | 2020-04-03 | 2023-03-07 | Veru Inc | Metodos de tratamiento del coronavirus |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3627155A1 (de) * | 1986-08-11 | 1988-02-18 | Schering Ag | Imidazol-derivate |
| AU2003245259A1 (en) * | 2002-05-02 | 2003-11-17 | Neurogen Corporation | Substituted imidazole derivatives: gabaa receptor ligands |
| WO2004041809A2 (en) * | 2002-05-08 | 2004-05-21 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives and their use as gabaa receptor ligands |
-
2006
- 2006-10-12 WO PCT/EP2006/067315 patent/WO2007042546A1/en not_active Ceased
- 2006-10-12 EP EP06807183A patent/EP1937649A1/en not_active Withdrawn
- 2006-10-12 CA CA002625974A patent/CA2625974A1/en not_active Abandoned
- 2006-10-12 US US12/083,375 patent/US8030339B2/en not_active Expired - Fee Related
- 2006-10-12 JP JP2008535026A patent/JP2009511547A/ja not_active Abandoned
- 2006-10-12 AU AU2006301222A patent/AU2006301222A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090233929A1 (en) | 2009-09-17 |
| AU2006301222A1 (en) | 2007-04-19 |
| US8030339B2 (en) | 2011-10-04 |
| EP1937649A1 (en) | 2008-07-02 |
| WO2007042546A1 (en) | 2007-04-19 |
| JP2009511547A (ja) | 2009-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20121012 |