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 27
- 150000003839 salts Chemical class 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 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 230000003463 hyperproliferative effect Effects 0.000 claims 7
- 239000002246 antineoplastic agent Substances 0.000 claims 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 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
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 230000001772 anti-angiogenic effect Effects 0.000 claims 2
- 229940034982 antineoplastic agent Drugs 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 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
- NCTMLJGPAUDVJW-UHFFFAOYSA-N 1-[3-(3-phenylbutan-2-yloxy)phenyl]-N-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C1(=CC=CC=C1)C(C)C(C)OC=1C=C(C=CC=1)N1C=NC2=C1C=CC(=C2)C(=O)NCC=1C=NC=CC=1 NCTMLJGPAUDVJW-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
- 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
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- OIQFUQWNZAELLU-UHFFFAOYSA-N n-(3-methoxypropyl)-1-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCCCOC)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 OIQFUQWNZAELLU-UHFFFAOYSA-N 0.000 claims 1
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- FGQVWDGHBNXOIG-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1COC1=CC=C(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)C=C1 FGQVWDGHBNXOIG-UHFFFAOYSA-N 0.000 claims 1
- KHPQLCXANVBKBO-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1COC1=CC=C(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)C=C1 KHPQLCXANVBKBO-UHFFFAOYSA-N 0.000 claims 1
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-
2004
- 2004-08-16 WO PCT/US2004/026482 patent/WO2005021531A1/en not_active Ceased
- 2004-08-16 US US10/921,414 patent/US7521448B2/en not_active Expired - Fee Related
- 2004-08-16 JP JP2006523955A patent/JP4769720B2/ja not_active Expired - Fee Related
- 2004-08-16 CA CA002535896A patent/CA2535896A1/en not_active Abandoned
- 2004-08-16 RU RU2006108803/04A patent/RU2006108803A/ru not_active Application Discontinuation
- 2004-08-16 KR KR1020067003585A patent/KR20060121818A/ko not_active Withdrawn
- 2004-08-16 AU AU2004268949A patent/AU2004268949A1/en not_active Abandoned
- 2004-08-16 UA UAA200602942A patent/UA82395C2/uk unknown
- 2004-08-16 BR BRPI0413746-9A patent/BRPI0413746A/pt not_active IP Right Cessation
- 2004-08-16 MX MXPA06002018A patent/MXPA06002018A/es unknown
- 2004-08-16 AP AP2006003549A patent/AP2006003549A0/xx unknown
- 2004-08-16 CN CNA2004800240461A patent/CN1852905A/zh active Pending
- 2004-08-16 EP EP04781204A patent/EP1664021A1/en not_active Withdrawn
- 2004-08-20 AR ARP040103008A patent/AR045387A1/es not_active Application Discontinuation
- 2004-08-20 TW TW093125230A patent/TW200524905A/zh unknown
-
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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