JP2007502821A5 - - Google Patents
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- Publication number
- JP2007502821A5 JP2007502821A5 JP2006523955A JP2006523955A JP2007502821A5 JP 2007502821 A5 JP2007502821 A5 JP 2007502821A5 JP 2006523955 A JP2006523955 A JP 2006523955A JP 2006523955 A JP2006523955 A JP 2006523955A JP 2007502821 A5 JP2007502821 A5 JP 2007502821A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- benzimidazole
- carboxamide
- pyridin
- ylmethyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 18
- 239000011780 sodium chloride Substances 0.000 claims 18
- 150000001204 N-oxides Chemical class 0.000 claims 14
- -1 3- (3- {5-[(pyridin-3-ylmethylamino) carbonyl] -1H-benzimidazol-1-yl} phenoxy) pentyl Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 230000003463 hyperproliferative Effects 0.000 claims 7
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229940095102 methyl benzoate Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- ZWFXWHBENNJQOZ-UHFFFAOYSA-N 1-[4-(2-phenoxyethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=CC(OCCOC=4C=CC=CC=4)=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 ZWFXWHBENNJQOZ-UHFFFAOYSA-N 0.000 claims 2
- 206010000880 Acute myeloid leukaemia Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000007046 Leukemia, Myeloid, Acute Diseases 0.000 claims 2
- AHNSGCVISFJIFT-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]-1-[4-[2-(4-fluorophenoxy)ethoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCCCN(C)C)=CC=C2N1C(C=C1)=CC=C1OCCOC1=CC=C(F)C=C1 AHNSGCVISFJIFT-UHFFFAOYSA-N 0.000 claims 2
- SJAGKMVWNDQDRW-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]-1-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCCCN(C)C)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 SJAGKMVWNDQDRW-UHFFFAOYSA-N 0.000 claims 2
- VKIFNQRQAQESSP-UHFFFAOYSA-N N-ethyl-1-[4-[2-(4-fluorophenoxy)ethoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCC)=CC=C2N1C(C=C1)=CC=C1OCCOC1=CC=C(F)C=C1 VKIFNQRQAQESSP-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atoms Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RLGYAOWVMXAHKE-UHFFFAOYSA-N 1-[3-(1H-indol-3-ylmethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C5=CC=CC=C5NC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 RLGYAOWVMXAHKE-UHFFFAOYSA-N 0.000 claims 1
- IQLGMKHPGNYTGA-UHFFFAOYSA-N 1-[3-(2-ethoxyethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound CCOCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 IQLGMKHPGNYTGA-UHFFFAOYSA-N 0.000 claims 1
- ACMAFILGHQASAP-UHFFFAOYSA-N 1-[3-(2-methoxyethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound COCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 ACMAFILGHQASAP-UHFFFAOYSA-N 0.000 claims 1
- CHERBHFNOOKZDB-UHFFFAOYSA-N 1-[3-(2-morpholin-4-ylethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCN4CCOCC4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 CHERBHFNOOKZDB-UHFFFAOYSA-N 0.000 claims 1
- IUXXKMPXMFDIKF-UHFFFAOYSA-N 1-[3-(2-phenoxyethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCOC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 IUXXKMPXMFDIKF-UHFFFAOYSA-N 0.000 claims 1
- SNGZARYVVCXVAH-UHFFFAOYSA-N 1-[3-(2-phenylsulfanylethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCSC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 SNGZARYVVCXVAH-UHFFFAOYSA-N 0.000 claims 1
- LJMVRWVNPKZRCZ-UHFFFAOYSA-N 1-[3-(3-imidazol-1-ylpropylamino)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(NCCCN4C=NC=C4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 LJMVRWVNPKZRCZ-UHFFFAOYSA-N 0.000 claims 1
- NEDXGMUDNMZAJQ-UHFFFAOYSA-N 1-[3-(3-phenoxypropoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCCOC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 NEDXGMUDNMZAJQ-UHFFFAOYSA-N 0.000 claims 1
- UOKOXPRQVUAXSM-UHFFFAOYSA-N 1-[3-(3-phenylpropoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCCC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 UOKOXPRQVUAXSM-UHFFFAOYSA-N 0.000 claims 1
- YLIKCCYJBFBSPG-UHFFFAOYSA-N 1-[3-(4-phenylbutan-2-yloxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=CC=1OC(C)CCC1=CC=CC=C1 YLIKCCYJBFBSPG-UHFFFAOYSA-N 0.000 claims 1
- VXBKABGIXRIRAY-UHFFFAOYSA-N 1-[3-(4-phenylbutoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCCCC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 VXBKABGIXRIRAY-UHFFFAOYSA-N 0.000 claims 1
- XEYGIVWGIDDILH-UHFFFAOYSA-N 1-[3-(cyclobutylmethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC4CCC4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 XEYGIVWGIDDILH-UHFFFAOYSA-N 0.000 claims 1
- LGIHJBIHAJYBFQ-UHFFFAOYSA-N 1-[3-(cyclohexylmethylamino)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(NCC4CCCCC4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 LGIHJBIHAJYBFQ-UHFFFAOYSA-N 0.000 claims 1
- HDFBXXNQENNXAN-UHFFFAOYSA-N 1-[3-(naphthalen-2-ylmethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C=C5C=CC=CC5=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 HDFBXXNQENNXAN-UHFFFAOYSA-N 0.000 claims 1
- PFNMVTNRNRFNLC-UHFFFAOYSA-N 1-[3-(pyridin-3-ylmethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C=NC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 PFNMVTNRNRFNLC-UHFFFAOYSA-N 0.000 claims 1
- IQLAVJONSFPEAW-UHFFFAOYSA-N 1-[3-(pyridin-4-ylmethoxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C=CN=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 IQLAVJONSFPEAW-UHFFFAOYSA-N 0.000 claims 1
- CPOHLIPCZDEJTB-UHFFFAOYSA-N 1-[3-[(2,4-difluorophenyl)sulfonylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 CPOHLIPCZDEJTB-UHFFFAOYSA-N 0.000 claims 1
- YUTDNXQRBOAECW-UHFFFAOYSA-N 1-[3-[(2-methoxyphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound COC1=CC=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 YUTDNXQRBOAECW-UHFFFAOYSA-N 0.000 claims 1
- GFBXPSWVFMCODK-UHFFFAOYSA-N 1-[3-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound S1C(C)=NC(COC=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 GFBXPSWVFMCODK-UHFFFAOYSA-N 0.000 claims 1
- KGQDAYXMCACTOL-UHFFFAOYSA-N 1-[3-[(2-phenylphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C(=CC=CC=4)C=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 KGQDAYXMCACTOL-UHFFFAOYSA-N 0.000 claims 1
- AHOWBYRPSGEGEF-UHFFFAOYSA-N 1-[3-[(3,4-dichlorophenyl)sulfonylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 AHOWBYRPSGEGEF-UHFFFAOYSA-N 0.000 claims 1
- ZZVQEMWKALQWOZ-UHFFFAOYSA-N 1-[3-[(3,4-dimethoxyphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 ZZVQEMWKALQWOZ-UHFFFAOYSA-N 0.000 claims 1
- CGMIBULXRRAUIW-UHFFFAOYSA-N 1-[3-[(3-methoxy-4-phenylmethoxyphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1COC(C=1)=CC=CC=1N(C1=CC=2)C=NC1=CC=2C(=O)NCC1=CC=CN=C1 CGMIBULXRRAUIW-UHFFFAOYSA-N 0.000 claims 1
- JOFYZJVMBAYGGP-UHFFFAOYSA-N 1-[3-[(3-methoxyphenyl)methylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound COC1=CC=CC(CNC=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 JOFYZJVMBAYGGP-UHFFFAOYSA-N 0.000 claims 1
- OCRAKFXJIUBIRC-UHFFFAOYSA-N 1-[3-[(4-bromophenyl)methylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Br)=CC=C1CNC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 OCRAKFXJIUBIRC-UHFFFAOYSA-N 0.000 claims 1
- CPWHAJVERNJNRY-UHFFFAOYSA-N 1-[3-[(4-chlorophenyl)sulfonylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 CPWHAJVERNJNRY-UHFFFAOYSA-N 0.000 claims 1
- KJMZZSWTEIYXJW-UHFFFAOYSA-N 1-[3-[(4-cyanophenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCC=4C=CC(=CC=4)C#N)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 KJMZZSWTEIYXJW-UHFFFAOYSA-N 0.000 claims 1
- AAGKUZYTYRLBBB-UHFFFAOYSA-N 1-[3-[(4-methoxyphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 AAGKUZYTYRLBBB-UHFFFAOYSA-N 0.000 claims 1
- QDYKBBYZWNGRCV-UHFFFAOYSA-N 1-[3-[(4-methylphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 QDYKBBYZWNGRCV-UHFFFAOYSA-N 0.000 claims 1
- DLLHRZDSAULNNH-UHFFFAOYSA-N 1-[3-[(4-methylphenyl)sulfonylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 DLLHRZDSAULNNH-UHFFFAOYSA-N 0.000 claims 1
- BQFODSCTFSDMJO-UHFFFAOYSA-N 1-[3-[(4-nitrophenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 BQFODSCTFSDMJO-UHFFFAOYSA-N 0.000 claims 1
- IJOLZFRCADMGKC-UHFFFAOYSA-N 1-[3-[(4-tert-butylphenyl)methoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 IJOLZFRCADMGKC-UHFFFAOYSA-N 0.000 claims 1
- IBJDAZGGQIDREP-UHFFFAOYSA-N 1-[3-[1-(4-chlorophenyl)ethylamino]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(C=1)=CC=CC=1N(C1=CC=2)C=NC1=CC=2C(=O)NCC1=CC=CN=C1 IBJDAZGGQIDREP-UHFFFAOYSA-N 0.000 claims 1
- DFCYELUCZPWKEE-UHFFFAOYSA-N 1-[3-[2-(2-methoxyethoxy)ethoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound COCCOCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 DFCYELUCZPWKEE-UHFFFAOYSA-N 0.000 claims 1
- JBPGZRVPFLUOEX-UHFFFAOYSA-N 1-[3-[2-(3-chlorophenoxy)ethoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(OCCOC=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 JBPGZRVPFLUOEX-UHFFFAOYSA-N 0.000 claims 1
- KXQIJLQYFAXAQE-UHFFFAOYSA-N 1-[3-[2-(4-bromophenoxy)ethoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Br)=CC=C1OCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 KXQIJLQYFAXAQE-UHFFFAOYSA-N 0.000 claims 1
- UAKVQIWSIJKNAZ-UHFFFAOYSA-N 1-[3-[2-(4-chlorophenoxy)ethoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1OCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 UAKVQIWSIJKNAZ-UHFFFAOYSA-N 0.000 claims 1
- RYFILEKQJMPTHC-UHFFFAOYSA-N 1-[3-[2-(4-fluorophenoxy)ethoxy]phenyl]-N-(2-methoxyethyl)benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCCOC)=CC=C2N1C(C=1)=CC=CC=1OCCOC1=CC=C(F)C=C1 RYFILEKQJMPTHC-UHFFFAOYSA-N 0.000 claims 1
- PYWRIBMCKUCNMM-UHFFFAOYSA-N 1-[3-[2-(4-fluorophenoxy)ethoxy]phenyl]-N-(oxan-4-yl)benzimidazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1OCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NC2CCOCC2)=C1 PYWRIBMCKUCNMM-UHFFFAOYSA-N 0.000 claims 1
- HHELMSVTELDIOD-UHFFFAOYSA-N 1-[3-[2-(4-fluorophenoxy)ethoxy]phenyl]-N-(oxan-4-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1OCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC2CCOCC2)=C1 HHELMSVTELDIOD-UHFFFAOYSA-N 0.000 claims 1
- VKAJKJXVRLELDW-UHFFFAOYSA-N 1-[3-[2-(4-methylphenoxy)ethoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1OCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 VKAJKJXVRLELDW-UHFFFAOYSA-N 0.000 claims 1
- JHAOQWXKQNJECP-UHFFFAOYSA-N 1-[3-[3-(3,4-dichlorophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 JHAOQWXKQNJECP-UHFFFAOYSA-N 0.000 claims 1
- DRTXKNRRSWVZQI-UHFFFAOYSA-N 1-[3-[3-(3-chlorophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(OCCCOC=2C=C(C=CC=2)N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 DRTXKNRRSWVZQI-UHFFFAOYSA-N 0.000 claims 1
- CDIUBXDIBBTVBD-UHFFFAOYSA-N 1-[3-[3-(4-bromophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Br)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 CDIUBXDIBBTVBD-UHFFFAOYSA-N 0.000 claims 1
- BLFQUBXFZKAAPE-UHFFFAOYSA-N 1-[3-[3-(4-chlorophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 BLFQUBXFZKAAPE-UHFFFAOYSA-N 0.000 claims 1
- HPTBEMAVDMXLAL-UHFFFAOYSA-N 1-[3-[3-(4-cyanophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCCOC=4C=CC(=CC=4)C#N)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 HPTBEMAVDMXLAL-UHFFFAOYSA-N 0.000 claims 1
- HIUOFOZKFNEGFX-UHFFFAOYSA-N 1-[3-[3-(4-fluorophenoxy)propoxy]phenyl]-N-(3-morpholin-4-ylpropyl)benzimidazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCCCN2CCOCC2)=C1 HIUOFOZKFNEGFX-UHFFFAOYSA-N 0.000 claims 1
- VWGSLVWWABETMJ-UHFFFAOYSA-N 1-[3-[3-(4-fluorophenoxy)propoxy]phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 VWGSLVWWABETMJ-UHFFFAOYSA-N 0.000 claims 1
- NCILRMPNEMKULF-UHFFFAOYSA-N 1-[3-[3-(4-fluorophenoxy)propoxy]phenyl]-N-[3-(4-methylpiperazin-1-yl)propyl]benzimidazole-5-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)C1=CC=C(N(C=N2)C=3C=C(OCCCOC=4C=CC(F)=CC=4)C=CC=3)C2=C1 NCILRMPNEMKULF-UHFFFAOYSA-N 0.000 claims 1
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- YSAMCHGHOKVKFV-UHFFFAOYSA-N N-methyl-1-[4-(2-pyridin-2-yloxypropoxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1C(C=C1)=CC=C1OCC(C)OC1=CC=CC=N1 YSAMCHGHOKVKFV-UHFFFAOYSA-N 0.000 claims 1
- FEGOKLBKPMMLQO-UHFFFAOYSA-N N-methyl-1-[4-(3-pyridin-2-yloxybutan-2-yloxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1C(C=C1)=CC=C1OC(C)C(C)OC1=CC=CC=N1 FEGOKLBKPMMLQO-UHFFFAOYSA-N 0.000 claims 1
- ZOIPRIUBOKPQNW-UHFFFAOYSA-N N-methyl-1-[4-[[4-(trifluoromethoxy)phenyl]methylamino]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1C(C=C1)=CC=C1NCC1=CC=C(OC(F)(F)F)C=C1 ZOIPRIUBOKPQNW-UHFFFAOYSA-N 0.000 claims 1
- SEGPXRCUHLLFHB-UHFFFAOYSA-N N-methyl-1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 SEGPXRCUHLLFHB-UHFFFAOYSA-N 0.000 claims 1
- RCAVRZQHFZFMPK-UHFFFAOYSA-N N-methyl-1-[4-[[4-(trifluoromethylsulfanyl)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(SC(F)(F)F)C=C1 RCAVRZQHFZFMPK-UHFFFAOYSA-N 0.000 claims 1
- LIGIUNODHIDUKH-UHFFFAOYSA-N N-propan-2-yl-1-[4-(1-pyridin-2-yloxypropan-2-yloxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1OC(C)COC1=CC=CC=N1 LIGIUNODHIDUKH-UHFFFAOYSA-N 0.000 claims 1
- HDGKJUUIEYENDH-UHFFFAOYSA-N N-propan-2-yl-1-[4-(2-pyridin-2-yloxyethoxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1OCCOC1=CC=CC=N1 HDGKJUUIEYENDH-UHFFFAOYSA-N 0.000 claims 1
- CNEKCAXEVIXVET-UHFFFAOYSA-N N-propan-2-yl-1-[4-(2-pyridin-2-yloxypropoxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1OCC(C)OC1=CC=CC=N1 CNEKCAXEVIXVET-UHFFFAOYSA-N 0.000 claims 1
- QYJBDHAMSFUIJW-UHFFFAOYSA-N N-propan-2-yl-1-[4-(3-pyridin-2-yloxybutan-2-yloxy)phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1OC(C)C(C)OC1=CC=CC=N1 QYJBDHAMSFUIJW-UHFFFAOYSA-N 0.000 claims 1
- PJOIXUXVPFLNKW-UHFFFAOYSA-N N-propan-2-yl-1-[4-[[4-(trifluoromethoxy)phenyl]methylamino]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1NCC1=CC=C(OC(F)(F)F)C=C1 PJOIXUXVPFLNKW-UHFFFAOYSA-N 0.000 claims 1
- VBXXQYAMRZKUNX-UHFFFAOYSA-N N-propan-2-yl-1-[4-[[4-(trifluoromethylsulfanyl)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC(C)C)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(SC(F)(F)F)C=C1 VBXXQYAMRZKUNX-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000587 Small Cell Lung Carcinoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- MFEQPHZZMQEJTB-UHFFFAOYSA-N [1-[2-[2-(4-fluorophenoxy)ethoxy]phenyl]benzimidazol-5-yl]-[4-(1-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(C(O)C)CCN1C(=O)C1=CC=C(N(C=N2)C=3C(=CC=CC=3)OCCOC=3C=CC(F)=CC=3)C2=C1 MFEQPHZZMQEJTB-UHFFFAOYSA-N 0.000 claims 1
- WHGXFZRTULZWEQ-UHFFFAOYSA-N [1-[4-[2-(4-fluorophenoxy)ethoxy]phenyl]benzimidazol-5-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(CCO)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=CC(OCCOC=4C=CC(F)=CC=4)=CC=3)C2=C1 WHGXFZRTULZWEQ-UHFFFAOYSA-N 0.000 claims 1
- WKAHDJTZLUKUGX-UHFFFAOYSA-N [1-[4-[2-(4-fluorophenoxy)ethoxy]phenyl]benzimidazol-5-yl]-[4-(2-hydroxyethyl)piperidin-1-yl]methanone Chemical compound C1CC(CCO)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=CC(OCCOC=4C=CC(F)=CC=4)=CC=3)C2=C1 WKAHDJTZLUKUGX-UHFFFAOYSA-N 0.000 claims 1
- VNEUJYMWOQKZPV-UHFFFAOYSA-N [4-(1-hydroxyethyl)piperazin-1-yl]-[1-[3-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazol-5-yl]methanone Chemical compound C1CN(C(O)C)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=C(OCC=4C=CC(OC(F)(F)F)=CC=4)C=CC=3)C2=C1 VNEUJYMWOQKZPV-UHFFFAOYSA-N 0.000 claims 1
- RXRDWDMRVPMVFB-UHFFFAOYSA-N [4-(1-hydroxyethyl)piperidin-1-yl]-[1-[3-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazol-5-yl]methanone Chemical compound C1CC(C(O)C)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=C(OCC=4C=CC(OC(F)(F)F)=CC=4)C=CC=3)C2=C1 RXRDWDMRVPMVFB-UHFFFAOYSA-N 0.000 claims 1
- CETWUKKRQRXKQR-UHFFFAOYSA-N [4-(2-hydroxyethyl)piperazin-1-yl]-[1-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazol-5-yl]methanone Chemical compound C1CN(CCO)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=CC(OCC=4C=CC(OC(F)(F)F)=CC=4)=CC=3)C2=C1 CETWUKKRQRXKQR-UHFFFAOYSA-N 0.000 claims 1
- ZRKWNHMECZKQSM-UHFFFAOYSA-N [4-(2-methoxyethyl)piperazin-1-yl]-[1-[3-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazol-5-yl]methanone Chemical compound C1CN(CCOC)CCN1C(=O)C1=CC=C(N(C=N2)C=3C=C(OCC=4C=CC(OC(F)(F)F)=CC=4)C=CC=3)C2=C1 ZRKWNHMECZKQSM-UHFFFAOYSA-N 0.000 claims 1
- 201000011186 acute T cell leukemia Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 201000003076 angiosarcoma Diseases 0.000 claims 1
- 230000001772 anti-angiogenic Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 201000009030 carcinoma Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000001472 cytotoxic Effects 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000003914 endometrial carcinoma Diseases 0.000 claims 1
- 230000002496 gastric Effects 0.000 claims 1
- 230000002147 killing Effects 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- OMHDEIWLFJQWHA-UHFFFAOYSA-N morpholin-4-yl-[1-[3-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazol-5-yl]methanone Chemical compound C1=CC(OC(F)(F)F)=CC=C1COC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)N2CCOCC2)=C1 OMHDEIWLFJQWHA-UHFFFAOYSA-N 0.000 claims 1
- 201000001539 ovarian carcinoma Diseases 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 201000007416 salivary gland adenoid cystic carcinoma Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000005161 thyroid carcinoma Diseases 0.000 claims 1
Claims (26)
- 式(I):
R11、R12、R13およびR14のうちの1つは、−NR3COR31、−NR3CONR3R31、−NR3SO2R31、−CO2R3、−CO2H、−C0−8アルキルNR3R31または−CONR3R31であり、他は、各々独立して、F、Cl、C0−3アルキル、C0−8アルコキシ、または−N(C0−8アルキル)(C0−8アルキル)であり;
Xは、1から4個のハロゲン、−NR32R33、−NR32COR33、−NR32CO2R33、−NR32SO2R33、−OR32、−SR32、−SO2R32、−SO2NR32R33、−CO2R32、−CO2H、−CONR32R33、−C0−8アルキル、−C2−8アルケニル、−C2−8アルキニル、−CN、CF3、OCF3、NO2、オキソ、シクリルまたはヘテロシクリル置換基で場合により置換されている、シクリルまたはヘテロシクリル基であり;
Yは、不在であるか、
であり;
RaおよびRbは、各々独立して、C0−8アルキルまたはC3−8シクロアルキルであるか、
RaおよびRbは、これらが結合しているCと一緒になって、環の接続点に0から4個のN、O、S、SOまたはSO2を場合により有する飽和または不完全不飽和3から10員環を形成するが、但し、N、OまたはSは、環の接続点において互いに隣接した位置にないことを条件とし;
Rcは、C0−8アルキルであるか、
Rcは、RaまたはRbと一緒になって、3から7員飽和または不完全不飽和環を形成し;
mは、0、1、2、3、4または5であるが、但し、mが、0または1である場合には、N、OまたはS原子は、N−X−Y−Z架橋において互いに隣接しないことを条件とし;
nは、1、2、3、4または5であるが、但し、nが、1である場合には、N、OまたはS原子は、N−X−Y−Z架橋において互いに隣接しないことを条件とし;
Zは、1から5個の独立したハロゲン、−NR34R35、−NR34COR35、−NR34C(O)OR35、−NR34SO2R35、−OR34、−SR34、−SO2R34、−SO2NR34R35、−C(O)OR34、−CO2H、−CONR34R35、C0−8アルキル、C2−8アルケニル、C2−8アルキニル、−OC0−8アルキル、−SC0−8アルキル、−SO2C0−8アルキル、−SO2N(C0−8アルキル)(C0−8アルキル)、−C(O)OC0−8アルキル、CN、CF3、NO2、オキソ、シクリルもしくはヘテロシクリル置換基で場合により置換されている、シクリルもしくはヘテロシクリル基であり、またはYが存在する場合には、Zは、C0−8アルキル−O−C0−8アルキル、C0−8アルキル−O−C(O)−C0−8アルキル、またはC0−8アルキル−C(O)−O−C0−8アルキルであってもよく、
但し、
Yが、−OCH2−である場合には、Zは、1から5個の−NR34R35、−NR34COR35、−NR34C(O)OR35、−NR34SO2R35、−OR34、−SR34、−SO2R34、−SO2NR34R35、−CO2R34、−CO2H、−CONR34R35、C0−8アルキル、C2−8アルケニル、C2−8アルキニル、CF3、NO2、オキソ、シクリルまたはヘテロシクリル置換基で置換されていなければならないこと、
Yが、NHCH2である場合には、Zは、1から5個のハロゲン、−NR34R35、−NR34COR35、−NR34C(O)OR35、−NR34SO2R35、−OR34、−SR34、−SO2R34、−SO2NR34R35、−CO2R34、−CO2H、−CONR34R35、C0−8アルキル、C2−8アルケニル、C2−8アルキニル、CF3、NO2、オキソ、シクリルまたはヘテロシクリル置換基で置換されていなければならないこと、
Yが、不在である場合には、XおよびZは、Nを含有しなこと
を条件とし;
R3、R31、R32、R33、R34およびR35は、独立して、ヘテロシクリルもしくはOH置換基で置換されているC0−8アルキル、CF3、CHF2、−C0−8アルキル−O−C0−8アルキル、−C0−8アルキル−N(C0−8アルキル)(C0−8アルキル)、−C0−8アルキル−S(O)0−2−C0−8アルキルまたは−C0−8アルキル−S(O)2N(C0−8アルキル)(C0−8アルキル)であることを条件とする。)
によって表される化合物またはこの医薬適合性の塩もしくはN−オキシド。 - R12が、−NR3COR31、−NR3CONR3R31、−NR3SO2R31、−CO2R3、−CO2H、−C0−8アルキルNR3R31または−CONR3R31である、請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシド。
- R12が、−CONR3R31である、請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシド。
- Xが、シクリルである、請求項3に記載の化合物またはこの医薬適合性の塩もしくはN−オキシド。
- Yが、不在である、請求項4に記載の化合物またはこの医薬適合性の塩もしくはN−オキシド。
- 請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシドおよび医薬適合性担体を含む組成物。
- 請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシドおよび抗新生物薬、抗腫瘍薬、抗血管新生薬または化学療法薬を含む組成物。
- 請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシドおよび細胞障害性癌治療薬を含む組成物。
- 請求項1に記載の化合物またはこの医薬適合性の塩もしくはN−オキシドおよび血管新生阻害性癌治療薬を含む組成物。
- 1−{3−[2−(フェニルチオ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(フェニルチオ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド
から成る化合物またはこの医薬適合性の塩もしくはN−オキシド。 - 1−[3−(3−フェニルプロポキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−シアノベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
5−[(3−{5−[(ピリジン−3−イルメチルアミノ)カルボニル]−1H−ベンズイミダゾール−1−イル}フェノキシ)メチル]−2−フロン酸エチル;
酢酸3−(3−{5−[(ピリジン−3−イルメチルアミノ)カルボニル]−1H−ベンズイミダゾール−1−イル}フェノキシ)ペンチル;
1−[3−(2−ナフチルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(3−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
4−{3−[5−(ピリジン−3−イルメチルアミノカルボニル)−1H−ベンズイミダゾール−1−イル]フェノキシ}へキサン酸エチル;
1−[3−(2−モルホリン−4−イルエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(4−フルオロベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
4−[(4−{5−[(ピリジン−3−イルメチルアミノ)カルボニル]−1H−ベンズイミダゾール−1−イル}フェノキシ)メチル]安息香酸メチル;
5−[(4−{5−[(ピリジン−3−イルメチルアミノ)カルボニル]−1H−ベンズイミダゾール−1−イル}フェノキシ)メチル]−2−フロン酸エチル;
1−{3−[(4−メチルベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−ニトロベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(4−メチルベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
4−[(3−{5−[(ピリジン−3−イルメチルアミノ)カルボニル]−1H−ベンズイミダゾール−1−イル}フェノキシ)メチル]安息香酸メチル;
1−{4−[(4−トリフルオロメチルベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−ナフチルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(4−ニトロベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(シクロヘキシルメチルオキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(1−フェネチルエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(1−フェネチルエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(2−フェネチルエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−モルホリン−4−イルエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−フェノキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(2−フェノキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(1H−インドール−3−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(2−メトキシエトキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−メトキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(2−メトキシエトキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(2−メチルチアゾール−4−イルメチル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(キノリン−2−イルメチル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−クロロフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(ピリジン−3−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(1,1’−ビフェニル−2−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(3,4−ジメトキシベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(シクロブチルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−メトキシベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(2−メトキシベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−ベンジルオキシ−3−メトキシベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−{t−ブチル}ベンジル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(4−フェニルブチル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(ピリジン−4−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(3−ピリジン−4−イルプロポキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(ピリジン−3−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(ピリジン−4−イルメトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(3−ピリジン−4−イルプロポキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−(4−メチルチアゾール−5−イル)エトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(フラン−3−イルメチル)オキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{4−[(2−チオフェン−2−イルエチル)オキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[(2−チオフェン−2−イルエチル)オキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{4−[(2−チオフェン−3−イルエチル)オキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[1−(4−クロロフェニル)シクロプロピル]メトキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(4−{[1−(4−クロロフェニル)シクロプロピル]メトキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[(2−チオフェン−3−イルエチル)オキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−ジメチルアミノプロピル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ジメチルアミノエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−メトキシプロピル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−メトキシエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ピペリジン−1−イルエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
2−(4−{[1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−イル]カルボニル}ピペラジン−1−イル)エタノール;
N−[3−(4−メチルピペラジン−1−イル)プロピル]−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−モルホリン−4−イルプロピル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[(1−オキシドピリジン−3−イル)メチル]−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(2−オキソピリジン−1(2H)−イル)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−オキソピリジン−1(4H)−イル)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(4−{2−[2−オキソ−5−(トリフルオロメチル)ピリジン−1(2H)−イル]エトキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(5−クロロ−2−オキソピリジン−1(2H)−イル)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド
から成る化合物またはこの医薬適合性の塩もしくはN−オキシド。 - 1−[3−(3−フェノキシプロポキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−フェノキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(2−メトキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−(2−エトキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(2−エトキシエトキシ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−ブロモフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−ブロモフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−メチルチアゾール−4−イルメチル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(キノリン−2−イルメチル)オキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(4−{3−[3−(トリフルオロメトキシ)フェノキシ]プロポキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(3−メトキシフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(3−クロロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−シアノフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−メトキシフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(3−メチルフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(3−エチニルフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−メチルフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−シアノフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{3−[3−(トリフルオロメトキシ)フェノキシ]プロポキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(3−クロロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−クロロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−ブロモフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{3−[4−(トリフルオロメトキシ)フェノキシ]プロポキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(3,4−ジクロロフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−イミダゾール−1−イルフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{3−[4−(4H−1,2,4−トリアゾール−4−イル)フェノキシ]プロポキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{3−[4−(トリフルオロメチル)フェノキシ]プロポキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
4−(3−{3−[5−(N−ピリジン−3−イルメチル)アミノカルボニル]−1H−ベンズイミダゾール−1−イルフェノキシ}プロポキシ)安息香酸メチル;
1−{4−[3−(4−ブロモフェノキシ)プロポキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−メチルフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(3−クロロフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(3−エチニルフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(3−ブロモフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−シアノフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−クロロフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−メトキシフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(3−メチルフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(4−{2−[(3−トリフルオロメトキシ)フェノキシ]エトキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−メチルフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(3−メトキシフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(3−クロロフェノキシ)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−[3−(4−メチルピペラジン−1−イル)プロピル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(2−モルホリン−4−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−[2−(N,N−ジメチルアミノ)エチル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−[3−(N,N−ジメチルアミノ)プロピル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(3−メトキシプロピル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(2−メトキシエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
2−{1−[(1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−イル)カルボニル]ピペリジン−4−イル}エタノール;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(2−ピペリジン−1−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(3−モルホリン−4−イルプロピル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−エチル−1H−ベンズイミダゾール−5−カルボキサミド;
2−{1−[(1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−イル)カルボニル]ピペラジン−4−イル}エタノール;
N−ピリジン−3−イルメチル−1−{4−[3−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[3−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(2−オキソピリジン−1(2H)−イル)エトキシ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{4−[2−(ピリジン−3−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[3−(ピリジン−3−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{4−[2−(5−クロロピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
5−(2−{4−[5−(ピリジン−3−イルメチルアミノカルボニル)−1H−ベンズイミダゾール−1−イル]フェノキシ}エトキシ)ニコチン酸
から成る化合物またはこの医薬適合性の塩もしくはN−オキシド。 - 1−{3−[(4−ブロモベンジル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(3−メトキシベンジル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(ピリジン−4−イルメチル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[(ピリジン−3−イルメチル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド
から成る化合物またはこの医薬適合性の塩もしくはN−オキシド。 - N−[3−(ジメチルアミノ)プロピル]−1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
(4−{[1−([2−(4−フルオロフェノキシ)エトキシ]フェニル)−1H−ベンズイミダゾール−5−イル]カルボニル}ピペラジン−1−イル)エタノール;
N−エチル−1−{4−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−[3−(ジメチルアミノ)プロピル]−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(3−メトキシプロピル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(2−メトキシエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(3−モルホリン−4−イルプロピル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(2−モルホリン−4−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[2−(ジメチルアミノ)エチル]−1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−メトキシエチル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[2−(ジメチルアミノ)エチル]−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[3−(4−メチルピペラジン−1−イル)プロピル]−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[2−(1H−イミダゾール−2−イル)エチル]−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−ヒドロキシプロピル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(2−ヒドロキシエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(2−ピペリジン−1−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−モルホリン−4−イルプロピル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[3−(ジメチルアミノ)プロピル]−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(3−メトキシプロピル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
5−(モルホリン−4−イルカルボニル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール;
(4−{[1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−イル]カルボニル}ピペラジン−1−イル)エタノール;
(1−{[1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−イル]カルボニル}ピペリジン−4−イル)エタノール;
N−(2−ピペリジン−1−イルエチル)−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
5−[4−(2−メトキシエチル)ピペラジン−1−イルカルボニル]−1−[3−(4−トリフルオロメトキシ−ベンジルオキシ)−フェニル]−1H−ベンズイミダゾール;
N−エチル−1−(3−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−[3−(4−メチルピペラジン−1−イル)プロピル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[3−(4−フルオロフェノキシ)プロポキシ]フェニル}−N−(3−モルホリン−4−イルプロピル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−[2−(ジメチルアミノ)エチル]−1−{3−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−[3−(ジメチルアミノ)プロピル]−1−{3−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(2−メトキシエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−テトラヒドロ−2H−ピラン−4−イル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[2−(4−フルオロフェノキシ)エトキシ]フェニル}−N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−テトラヒドロ−2H−ピラン−4−イル−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ピロリジン−1−イルエチル)−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−メトキシエチル)−1−(4−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−(4−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−(4−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−(4−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1−(4−{[4−(トリフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−エチル−1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−[4−({4−[(トリフルオロメチル)チオ]ベンジル}オキシ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ピロリジン−1−イルエチル)−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−メトキシエチル)−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−(4−{[4−(ジフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ピロリジン−1−イルエチル)−1−(4−{[4−(ジフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−(4−{[4−(ジフルオロメチル)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1−(4−{[4−(ジフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ピロリジン−1−イルエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]オキシ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピラジン−2−イルオキシ)エトキシ]フェニル}−N−(ピリジン−3−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリミジン−2−イルオキシ)エトキシ]フェニル}−N−(ピリジン−3−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−エチル−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−メトキシエチル)−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−テトラヒドロ−2H−ピラン−4−イル−1H−ベンズイミダゾール−5−カルボキサミド;
N−シクロブチル−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−(ピロリジン−1−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
t−ブチル−4−{[(1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−イル)カルボニル]アミノ}エチル)ピペラジン−1−カルボキシレート;
N−イソプロピル−1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−(2−モルホリン−4−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシエチル)−1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−(2−ピロリジン−1−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−N−(2−ピロリジン−1−エチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−N−[3−(メチルチオ)プロピル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−[3−(メチルチオ)プロピル]−1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−ヒドロキシ)−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−N−(2−ピロリジン−1−イルエチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−N−(1−テトラヒドロ−2H−ピラン−4−イルメチル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−N−[3−(メチルチオ)プロピル]−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)エトキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−{4−[2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−{4−[1−メチル−2−(ピリジン−2−イルオキシ)プロポキシ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−(4−{[3−(2−ピリジルオキシメチル)シクロブチル]オキシ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(3−フェノキシプロピル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[4−(4−フルオロフェニル)ピペリジン−1−イル]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[4−(4−フルオロフェニル)ピペラジン−1−イル]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[4−(4−フルオロフェニル)ピペリジン−1−イル]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[(2−チエン−3−イルエチル)アミノ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
1−[3−(シクロヘキシルメチルアミノ)フェニル]−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{4−[(2−フェノキシエチル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[1−(4−クロロフェニル)エチル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[3−(1H−イミダゾール−1−イル)プロピル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−[3−(4−ピリミジン−2−イルピペラジン−1−イル)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−[1,4’]ビピペリジニル−1’−イル−フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[ベンジル(メチル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−イソプロピル−1−(4−{[4−(トリフルオロメトキシ)ベンジル]アミノ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−メチル−1−(4−{[4−(トリフルオロメトキシ)ベンジル]アミノ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−(2−モルホリン−4−イルエチル)−1−(4−{[4−(トリフルオロメトキシ)ベンジル]アミノ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−テトラヒドロ−2H−ピラン−4−イル−1−(4−{[4−(トリフルオロメトキシ)ベンジル]アミノ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−(3−{[4−(トリフルオロメトキシ)ベンジル]アミノ}フェニル)−1H−ベンズイミダゾール−5−カルボキサミド;
1−{3−[4−(トリフルオロメチルフェニル)アミノ]フェニル}−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[(4−メチルフェニル)スルホニル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[(4−クロロフェニル)スルホニル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−{3−[(チエン−2−イルスルホニル)アミノ]フェニル}−1H−ベンズイミダゾール−5−カルボキサミド;
N−ピリジン−3−イルメチル−1−[3−({[4−(トリフルオロメトキシ)フェニル]スルホニル}アミノ)フェニル]−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[(2,4−ジフルオロフェニル)スルホニル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド;
1−(3−{[(3,4−ジクロロフェニル)スルホニル]アミノ}フェニル)−N−ピリジン−3−イルメチル−1H−ベンズイミダゾール−5−カルボキサミド
から成る化合物またはこの医薬適合性の塩もしくはN−オキシド。 - 請求項1に記載の化合物の有効量を投与する段階を含む、高増殖性疾患の治療方法。
- 抗新生物薬、抗腫瘍薬、抗血管新生薬または化学療法薬を投与する段階をさらに含む、請求項19に記載の方法。
- 前記高増殖性疾患が、乳癌、頭部癌または頚部癌である、請求項19に記載の方法。
- 前記高増殖性疾患が、胃腸癌である、請求項19に記載の方法。
- 前記高増殖性疾患が、白血病である、請求項19に記載の方法。
- 前記高増殖性疾患が、卵巣癌、気管支癌、肺癌または膵臓癌である、請求項19に記載の方法。
- 前記高増殖性疾患が、小細胞肺癌または大腸癌である、請求項19に記載の方法。
- 前記高増殖性疾患が、副鼻腔(sinonasal)天然キラー/T細胞リンパ腫、精巣癌(精上皮腫)、甲状腺癌腫、悪性黒色腫、卵巣癌腫、腺様嚢胞癌腫、急性骨髄性白血病(AML)、乳癌腫、小児T細胞急性リンパ芽球性白血病、血管肉腫、未分化大細胞リンパ腫、子宮内膜癌腫、または前立腺癌腫である、請求項19に記載の方法。
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-
2004
- 2004-08-16 UA UAA200602942A patent/UA82395C2/uk unknown
- 2004-08-16 RU RU2006108803/04A patent/RU2006108803A/ru not_active Application Discontinuation
- 2004-08-16 CN CNA2004800240461A patent/CN1852905A/zh active Pending
- 2004-08-16 KR KR1020067003585A patent/KR20060121818A/ko not_active Application Discontinuation
- 2004-08-16 JP JP2006523955A patent/JP4769720B2/ja not_active Expired - Fee Related
- 2004-08-16 MX MXPA06002018A patent/MXPA06002018A/es unknown
- 2004-08-16 AU AU2004268949A patent/AU2004268949A1/en not_active Abandoned
- 2004-08-16 AP AP2006003549A patent/AP2006003549A0/xx unknown
- 2004-08-16 WO PCT/US2004/026482 patent/WO2005021531A1/en active Application Filing
- 2004-08-16 US US10/921,414 patent/US7521448B2/en not_active Expired - Fee Related
- 2004-08-16 BR BRPI0413746-9A patent/BRPI0413746A/pt not_active IP Right Cessation
- 2004-08-16 EP EP04781204A patent/EP1664021A1/en not_active Withdrawn
- 2004-08-16 CA CA002535896A patent/CA2535896A1/en not_active Abandoned
- 2004-08-20 TW TW093125230A patent/TW200524905A/zh unknown
- 2004-08-20 AR ARP040103008A patent/AR045387A1/es not_active Application Discontinuation
-
2006
- 2006-02-08 IL IL173614A patent/IL173614A0/en unknown
- 2006-02-10 NO NO20060664A patent/NO20060664L/no not_active Application Discontinuation
- 2006-02-21 IS IS8319A patent/IS8319A/is unknown
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