RU2006108803A - N-замещенные бензимидазолильные ингибиторы с-kit - Google Patents
N-замещенные бензимидазолильные ингибиторы с-kit Download PDFInfo
- Publication number
- RU2006108803A RU2006108803A RU2006108803/04A RU2006108803A RU2006108803A RU 2006108803 A RU2006108803 A RU 2006108803A RU 2006108803/04 A RU2006108803/04 A RU 2006108803/04A RU 2006108803 A RU2006108803 A RU 2006108803A RU 2006108803 A RU2006108803 A RU 2006108803A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- benzimidazole
- carboxamide
- pyridin
- ylmethyl
- Prior art date
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- -1 BENZIMIDAZOLYL Chemical class 0.000 title claims 22
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000001204 N-oxides Chemical class 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 230000003463 hyperproliferative effect Effects 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 230000001772 anti-angiogenic effect Effects 0.000 claims 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims 2
- 230000000259 anti-tumor effect Effects 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 239000012830 cancer therapeutic Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- ZFSLEFLFJNPIHI-UHFFFAOYSA-N n-(2-methoxyethyl)-1-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NCCOC)=CC=C2N1C(C=C1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 ZFSLEFLFJNPIHI-UHFFFAOYSA-N 0.000 claims 2
- DZNQBSSFDVUIGZ-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-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)NCCN2CCOCC2)C=C1 DZNQBSSFDVUIGZ-UHFFFAOYSA-N 0.000 claims 2
- FCIQIHYFADRZTO-UHFFFAOYSA-N n-(oxan-4-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)NCC2CCOCC2)C=C1 FCIQIHYFADRZTO-UHFFFAOYSA-N 0.000 claims 2
- MVLRPCZFEJIGPI-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[3-[3-[4-(trifluoromethoxy)phenoxy]propoxy]phenyl]benzimidazole-5-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1OCCCOC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C=NC=CC=2)=C1 MVLRPCZFEJIGPI-UHFFFAOYSA-N 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[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
- YIHVZTRDKGZLDQ-UHFFFAOYSA-N 1-[3-(2-phenylethoxy)phenyl]-n-(pyridin-3-ylmethyl)benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C=3C=C(OCCC=4C=CC=CC=4)C=CC=3)C=NC2=CC=1C(=O)NCC1=CC=CN=C1 YIHVZTRDKGZLDQ-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
- 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
- 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
- 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
- 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
- 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
- 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
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 208000000587 small cell lung 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
- 125000003944 tolyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Ceramic Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49680603P | 2003-08-21 | 2003-08-21 | |
| US60/496,806 | 2003-08-21 |
Publications (1)
| Publication Number | Publication Date |
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| RU2006108803A true RU2006108803A (ru) | 2007-09-27 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| RU2006108803/04A RU2006108803A (ru) | 2003-08-21 | 2004-08-16 | N-замещенные бензимидазолильные ингибиторы с-kit |
Country Status (18)
| Country | Link |
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| US (1) | US7521448B2 (https=) |
| EP (1) | EP1664021A1 (https=) |
| JP (1) | JP4769720B2 (https=) |
| KR (1) | KR20060121818A (https=) |
| CN (1) | CN1852905A (https=) |
| AP (1) | AP2006003549A0 (https=) |
| AR (1) | AR045387A1 (https=) |
| AU (1) | AU2004268949A1 (https=) |
| BR (1) | BRPI0413746A (https=) |
| CA (1) | CA2535896A1 (https=) |
| IL (1) | IL173614A0 (https=) |
| IS (1) | IS8319A (https=) |
| MX (1) | MXPA06002018A (https=) |
| NO (1) | NO20060664L (https=) |
| RU (1) | RU2006108803A (https=) |
| TW (1) | TW200524905A (https=) |
| UA (1) | UA82395C2 (https=) |
| WO (1) | WO2005021531A1 (https=) |
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| DE60137273D1 (de) | 2000-10-20 | 2009-02-12 | Eisai R&D Man Co Ltd | Verfahren zur Herstellung von 4-Phenoxy chinolin Derivaten |
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| AU2005283422C1 (en) * | 2004-09-17 | 2017-02-02 | Eisai R & D Management Co., Ltd. | Medicinal composition |
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-
2004
- 2004-08-16 AU AU2004268949A patent/AU2004268949A1/en not_active Abandoned
- 2004-08-16 EP EP04781204A patent/EP1664021A1/en not_active Withdrawn
- 2004-08-16 KR KR1020067003585A patent/KR20060121818A/ko not_active Withdrawn
- 2004-08-16 JP JP2006523955A patent/JP4769720B2/ja not_active Expired - Fee Related
- 2004-08-16 BR BRPI0413746-9A patent/BRPI0413746A/pt not_active IP Right Cessation
- 2004-08-16 AP AP2006003549A patent/AP2006003549A0/xx unknown
- 2004-08-16 US US10/921,414 patent/US7521448B2/en not_active Expired - Fee Related
- 2004-08-16 UA UAA200602942A patent/UA82395C2/uk unknown
- 2004-08-16 CA CA002535896A patent/CA2535896A1/en not_active Abandoned
- 2004-08-16 WO PCT/US2004/026482 patent/WO2005021531A1/en not_active Ceased
- 2004-08-16 MX MXPA06002018A patent/MXPA06002018A/es unknown
- 2004-08-16 RU RU2006108803/04A patent/RU2006108803A/ru not_active Application Discontinuation
- 2004-08-16 CN CNA2004800240461A patent/CN1852905A/zh active Pending
- 2004-08-20 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
Also Published As
| Publication number | Publication date |
|---|---|
| NO20060664L (no) | 2006-05-16 |
| CA2535896A1 (en) | 2005-03-10 |
| AR045387A1 (es) | 2005-10-26 |
| UA82395C2 (en) | 2008-04-10 |
| EP1664021A1 (en) | 2006-06-07 |
| IS8319A (is) | 2006-02-21 |
| TW200524905A (en) | 2005-08-01 |
| JP2007502821A (ja) | 2007-02-15 |
| US20060189629A1 (en) | 2006-08-24 |
| KR20060121818A (ko) | 2006-11-29 |
| CN1852905A (zh) | 2006-10-25 |
| AP2006003549A0 (en) | 2006-04-30 |
| JP4769720B2 (ja) | 2011-09-07 |
| MXPA06002018A (es) | 2006-05-31 |
| BRPI0413746A (pt) | 2006-10-24 |
| WO2005021531A1 (en) | 2005-03-10 |
| US7521448B2 (en) | 2009-04-21 |
| AU2004268949A1 (en) | 2005-03-10 |
| IL173614A0 (en) | 2006-07-05 |
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