JP2009511547A5 - - Google Patents
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- Publication number
- JP2009511547A5 JP2009511547A5 JP2008535026A JP2008535026A JP2009511547A5 JP 2009511547 A5 JP2009511547 A5 JP 2009511547A5 JP 2008535026 A JP2008535026 A JP 2008535026A JP 2008535026 A JP2008535026 A JP 2008535026A JP 2009511547 A5 JP2009511547 A5 JP 2009511547A5
- Authority
- JP
- Japan
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- -1 5′-fluoro-2′-methoxy-biphenyl-3-yl Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 206010010904 Convulsion Diseases 0.000 claims 3
- 206010047700 Vomiting Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000008673 vomiting Effects 0.000 claims 3
- 208000008811 Agoraphobia Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- IKKVHAQXACIJIX-UHFFFAOYSA-N [1-(3-phenylphenyl)imidazol-4-yl]-pyrazol-1-ylmethanone Chemical compound C1=CC=NN1C(=O)C(N=C1)=CN1C(C=1)=CC=CC=1C1=CC=CC=C1 IKKVHAQXACIJIX-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- ROXBHERZWSHUSY-UHFFFAOYSA-N (1-ethylimidazol-2-yl)-[1-[3-(5-fluoro-2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound CCN1C=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=C(F)C=2)OC)C=N1 ROXBHERZWSHUSY-UHFFFAOYSA-N 0.000 claims 1
- HOQMVJRYQSUDJC-UHFFFAOYSA-N (1-methylimidazol-2-yl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound CN1C=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 HOQMVJRYQSUDJC-UHFFFAOYSA-N 0.000 claims 1
- QTQQCMFOLIRUNJ-UHFFFAOYSA-N (2-methoxyphenyl)-[1-(3-phenylphenyl)imidazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C=CC=CC=2)C=N1 QTQQCMFOLIRUNJ-UHFFFAOYSA-N 0.000 claims 1
- HCKXKBFRDKPJNS-UHFFFAOYSA-N (2-methoxyphenyl)-[1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC)C=N1 HCKXKBFRDKPJNS-UHFFFAOYSA-N 0.000 claims 1
- SIGMNVCIIPOVPO-UHFFFAOYSA-N (2-methoxyphenyl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 SIGMNVCIIPOVPO-UHFFFAOYSA-N 0.000 claims 1
- MULSOQOHGYQXPZ-UHFFFAOYSA-N (3-fluorophenyl)-[1-(3-phenylphenyl)imidazol-4-yl]methanone Chemical compound FC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 MULSOQOHGYQXPZ-UHFFFAOYSA-N 0.000 claims 1
- OSZRZGSSPXUQMQ-UHFFFAOYSA-N (3-fluorophenyl)-[1-[3-(2-fluoropyridin-3-yl)phenyl]imidazol-4-yl]methanone Chemical compound FC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)=C1 OSZRZGSSPXUQMQ-UHFFFAOYSA-N 0.000 claims 1
- JKZMDJHEPLTCQD-UHFFFAOYSA-N (3-fluorophenyl)-[1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2C=C(F)C=CC=2)=C1 JKZMDJHEPLTCQD-UHFFFAOYSA-N 0.000 claims 1
- HBSHWTRGTXBDRE-UHFFFAOYSA-N (3-fluorophenyl)-[1-[3-(3-fluoropyridin-4-yl)phenyl]imidazol-4-yl]methanone Chemical compound FC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CN=CC=2)F)=C1 HBSHWTRGTXBDRE-UHFFFAOYSA-N 0.000 claims 1
- ITFDUDHIHRBTHO-UHFFFAOYSA-N (3-fluorophenyl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound FC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)=C1 ITFDUDHIHRBTHO-UHFFFAOYSA-N 0.000 claims 1
- QLRBXYHGLVYFKC-UHFFFAOYSA-N (3-methoxyphenyl)-[1-(3-phenylphenyl)imidazol-4-yl]methanone Chemical compound COC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 QLRBXYHGLVYFKC-UHFFFAOYSA-N 0.000 claims 1
- OFQKBEKTCHOPNA-UHFFFAOYSA-N (3-methoxyphenyl)-[1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC)=C1 OFQKBEKTCHOPNA-UHFFFAOYSA-N 0.000 claims 1
- YQLWHEIPHOPVNW-UHFFFAOYSA-N (3-methoxyphenyl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)=C1 YQLWHEIPHOPVNW-UHFFFAOYSA-N 0.000 claims 1
- RGOYBDSEBXKTRQ-UHFFFAOYSA-N (3-methylpyridin-2-yl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound CC1=CC=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 RGOYBDSEBXKTRQ-UHFFFAOYSA-N 0.000 claims 1
- KLDZLPGURPXBHH-UHFFFAOYSA-N (4-fluorophenyl)-[1-(3-phenylphenyl)imidazol-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C=CC=CC=2)C=N1 KLDZLPGURPXBHH-UHFFFAOYSA-N 0.000 claims 1
- OXLINOQICORNDN-UHFFFAOYSA-N (4-fluorophenyl)-[1-[3-(2-fluoropyridin-3-yl)phenyl]imidazol-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C=N1 OXLINOQICORNDN-UHFFFAOYSA-N 0.000 claims 1
- BHPLPLVXXGOYEU-UHFFFAOYSA-N (4-fluorophenyl)-[1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2C=CC(F)=CC=2)=C1 BHPLPLVXXGOYEU-UHFFFAOYSA-N 0.000 claims 1
- NQVLYZFTQPIEGC-UHFFFAOYSA-N (4-fluorophenyl)-[1-[3-(3-fluoropyridin-4-yl)phenyl]imidazol-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CN=CC=2)F)C=N1 NQVLYZFTQPIEGC-UHFFFAOYSA-N 0.000 claims 1
- MLEJGARVMXHQJN-UHFFFAOYSA-N (4-fluorophenyl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 MLEJGARVMXHQJN-UHFFFAOYSA-N 0.000 claims 1
- UPWSBSAFFQZEME-UHFFFAOYSA-N (4-methoxyphenyl)-[1-(3-phenylphenyl)imidazol-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C=CC=CC=2)C=N1 UPWSBSAFFQZEME-UHFFFAOYSA-N 0.000 claims 1
- GYVMLXMIZCOZRK-UHFFFAOYSA-N (4-methoxyphenyl)-[1-[3-(2-methoxyphenyl)phenyl]imidazol-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC)C=N1 GYVMLXMIZCOZRK-UHFFFAOYSA-N 0.000 claims 1
- SGDPXLYRUWMOEN-UHFFFAOYSA-N (4-methoxyphenyl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)C=N1 SGDPXLYRUWMOEN-UHFFFAOYSA-N 0.000 claims 1
- CGBABTLWWNKPIM-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[1-(3-nitrophenyl)imidazol-4-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN(C=2C=C(C=CC=2)[N+]([O-])=O)C=N1 CGBABTLWWNKPIM-UHFFFAOYSA-N 0.000 claims 1
- KWIOOFJIZZYKPN-UHFFFAOYSA-N (4-methylpyridin-2-yl)-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound CC1=CC=NC(C(=O)C=2N=CN(C=2)C=2C=C(C=CC=2)C=2C(=CC=CC=2)OC(F)(F)F)=C1 KWIOOFJIZZYKPN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AKFHDVUXBYMFGP-UHFFFAOYSA-N 1,3-thiazol-2-yl-[1-[3-[2-(trifluoromethoxy)phenyl]phenyl]imidazol-4-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=CC=CC(N2C=C(N=C2)C(=O)C=2SC=CN=2)=C1 AKFHDVUXBYMFGP-UHFFFAOYSA-N 0.000 claims 1
- AZWHGOCIOJHCMW-UHFFFAOYSA-N 1-(3-nitrophenyl)-n-propan-2-ylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CN1C1=CC=CC([N+]([O-])=O)=C1 AZWHGOCIOJHCMW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- RYKFSWXVHXTSEJ-UHFFFAOYSA-N 1-[1-(3-phenylphenyl)imidazol-4-yl]pentan-1-one Chemical compound C1=NC(C(=O)CCCC)=CN1C1=CC=CC(C=2C=CC=CC=2)=C1 RYKFSWXVHXTSEJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GTBNPDXSFUKJMV-UHFFFAOYSA-N 1-[3-(2,4-dimethoxypyrimidin-5-yl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=NC(OC)=NC=2)OC)=C1 GTBNPDXSFUKJMV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RSINVOMGLSZTMK-UHFFFAOYSA-N 1-[3-(2-chloropyridin-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=2)Cl)=C1 RSINVOMGLSZTMK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FINMKKPGDWFNBG-UHFFFAOYSA-N 1-[3-(2-fluoro-6-methoxyphenyl)phenyl]-n-methoxy-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)N(C)OC)=CN1C1=CC=CC(C=2C(=CC=CC=2F)OC)=C1 FINMKKPGDWFNBG-UHFFFAOYSA-N 0.000 claims 1
- DLEPTPHTKDXTEZ-UHFFFAOYSA-N 1-[3-(2-fluoropyridin-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=2)F)=C1 DLEPTPHTKDXTEZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- OUONURCBDJTSFW-UHFFFAOYSA-N 2-[3-[4-(1-methylimidazole-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound CN1C=CN=C1C(=O)C1=CN(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C#N)C=N1 OUONURCBDJTSFW-UHFFFAOYSA-N 0.000 claims 1
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- RUKYNEATRREJEF-UHFFFAOYSA-N 2-[3-[4-(pyridine-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound C=1C=CC=NC=1C(=O)C(N=C1)=CN1C(C=1)=CC=CC=1C1=CC=CC=C1C#N RUKYNEATRREJEF-UHFFFAOYSA-N 0.000 claims 1
- ZCGKWDLVJYMMQU-UHFFFAOYSA-N 2-[3-[4-(pyrimidine-2-carbonyl)imidazol-1-yl]phenyl]benzonitrile Chemical compound N=1C=CC=NC=1C(=O)C(N=C1)=CN1C(C=1)=CC=CC=1C1=CC=CC=C1C#N ZCGKWDLVJYMMQU-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000032755 Anticipatory Vomiting Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000017164 Chronobiology disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000002091 Febrile Seizures Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 206010028813 Nausea Diseases 0.000 claims 1
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| DKPA200501445 | 2005-10-14 | ||
| US72667705P | 2005-10-17 | 2005-10-17 | |
| PCT/EP2006/067315 WO2007042546A1 (en) | 2005-10-14 | 2006-10-12 | Imidazole derivatives for the treatment of anxiety and related diseases |
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| JP2009511547A JP2009511547A (ja) | 2009-03-19 |
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| 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 |
| EP2278879B1 (en) | 2008-04-21 | 2016-06-15 | PATH Drug Solutions | Compounds, compositions and methods comprising oxadiazole derivatives |
| UA105005C2 (uk) * | 2008-06-16 | 2014-04-10 | Юніверсіті Оф Теннессі Рісерч Фаундейшн | Сполуки для лікування раку |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of 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。 |
| BRPI0919257B8 (pt) * | 2008-09-24 | 2021-05-25 | Zach System | processo de preparação de nebivolol |
| US8343976B2 (en) | 2009-04-20 | 2013-01-01 | Institute For Oneworld Health | Compounds, compositions and methods comprising pyrazole derivatives |
| CA2791738C (en) | 2010-03-01 | 2020-06-09 | Gtx, Inc. | Aryl imidazolyl compounds for the treatment of cancer |
| CA2860099A1 (en) * | 2012-02-13 | 2013-08-22 | Johannes Aebi | 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 |
| IL293661B2 (en) | 2020-04-03 | 2025-11-01 | Veru Inc | Sabizabulin for treating coronavirus infection |
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| DE3627155A1 (de) | 1986-08-11 | 1988-02-18 | Schering Ag | Imidazol-derivate |
| US7030144B2 (en) | 2002-05-02 | 2006-04-18 | Neurogen Corporation | Substituted imidazole derivatives: GABAA receptor ligands |
| CA2484936A1 (en) | 2002-05-08 | 2004-05-21 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives and their use as gabaa receptor ligands |
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2006
- 2006-10-12 CA CA002625974A patent/CA2625974A1/en not_active Abandoned
- 2006-10-12 JP JP2008535026A patent/JP2009511547A/ja not_active Abandoned
- 2006-10-12 WO PCT/EP2006/067315 patent/WO2007042546A1/en not_active Ceased
- 2006-10-12 US US12/083,375 patent/US8030339B2/en not_active Expired - Fee Related
- 2006-10-12 AU AU2006301222A patent/AU2006301222A1/en not_active Abandoned
- 2006-10-12 EP EP06807183A patent/EP1937649A1/en not_active Withdrawn
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