JP2005524668A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005524668A5 JP2005524668A5 JP2003572983A JP2003572983A JP2005524668A5 JP 2005524668 A5 JP2005524668 A5 JP 2005524668A5 JP 2003572983 A JP2003572983 A JP 2003572983A JP 2003572983 A JP2003572983 A JP 2003572983A JP 2005524668 A5 JP2005524668 A5 JP 2005524668A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrimidin
- amino
- phenylamino
- benzimidazol
- 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.)
- Pending
Links
- -1 —NR 8 R 9 Chemical group 0.000 claims 75
- 229910052739 hydrogen Inorganic materials 0.000 claims 46
- 239000001257 hydrogen Substances 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 32
- 150000002431 hydrogen Chemical group 0.000 claims 32
- 150000001408 amides Chemical class 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- XZWYLPKSDKATEV-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1 XZWYLPKSDKATEV-UHFFFAOYSA-N 0.000 claims 2
- SVEPWTZXIDDIJQ-UHFFFAOYSA-N 3-[[4-[[2-[(3-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC(Cl)=C1 SVEPWTZXIDDIJQ-UHFFFAOYSA-N 0.000 claims 2
- BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-UHFFFAOYSA-N 0.000 claims 2
- IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 2
- TYDWDJHIOGMALG-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound C1CC1(C=1C(=CC=C(F)C=1)F)C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 TYDWDJHIOGMALG-UHFFFAOYSA-N 0.000 claims 1
- ITAPLFRHLLOCEL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 ITAPLFRHLLOCEL-UHFFFAOYSA-N 0.000 claims 1
- LYISPJAHVAQSTK-UHFFFAOYSA-N 1-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-3-phenylurea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)NC1=CC=CC=C1 LYISPJAHVAQSTK-UHFFFAOYSA-N 0.000 claims 1
- BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims 1
- PGGQBCCZVDGRAS-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1OC PGGQBCCZVDGRAS-UHFFFAOYSA-N 0.000 claims 1
- MZWNAJJDJXOZLV-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-n-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]-1-methylbenzimidazol-2-yl]acetamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)CC=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 MZWNAJJDJXOZLV-UHFFFAOYSA-N 0.000 claims 1
- KYFRVPBBRPZBSZ-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C=1C(F)=CC=C(F)C=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 KYFRVPBBRPZBSZ-UHFFFAOYSA-N 0.000 claims 1
- QATMPMUKHIHJLS-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=C(OC)C(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1 QATMPMUKHIHJLS-UHFFFAOYSA-N 0.000 claims 1
- NHMJPJQHCQVSLN-UHFFFAOYSA-N 2-(2-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC=C1CC(=O)NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C NHMJPJQHCQVSLN-UHFFFAOYSA-N 0.000 claims 1
- IOYCCLXBNASNOV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]-1-methylbenzimidazol-2-yl]acetamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)CC=4C=C(Cl)C(Cl)=CC=4)N(C)C=3C=CC=2)=C1 IOYCCLXBNASNOV-UHFFFAOYSA-N 0.000 claims 1
- QDCKWOPBRJZWNI-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 QDCKWOPBRJZWNI-UHFFFAOYSA-N 0.000 claims 1
- GZLRFAKVIBWDAK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C GZLRFAKVIBWDAK-UHFFFAOYSA-N 0.000 claims 1
- XBLMGJGVFXRKFD-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC(OC)=CC(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1 XBLMGJGVFXRKFD-UHFFFAOYSA-N 0.000 claims 1
- QORPXAVIKCCCAO-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-N,1-dimethyl-5-N-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-3H-benzimidazole-2,5-diamine Chemical compound FC=1C=C(C=CC=1)C1(NC2=C(N1C)C=CC(=C2)N(C)C1=NC(=NC=C1)NC1=CC=C(C=C1)CS(=O)(=O)C)N QORPXAVIKCCCAO-UHFFFAOYSA-N 0.000 claims 1
- TVVHQKVXGSTWOE-UHFFFAOYSA-N 2-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-5-N-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-3H-benzimidazole-2,5-diamine Chemical compound C(C)(C)(C)C1=CC(=NO1)C1(NC2=C(N1C)C=CC(=C2)NC1=NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)N TVVHQKVXGSTWOE-UHFFFAOYSA-N 0.000 claims 1
- DDDCWHGPCPPUQF-UHFFFAOYSA-N 2-[4-[[4-[[2-(benzylamino)-1-ethylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound N=1C2=CC(N(C)C=3N=C(NC=4C=CC(CCS(=O)(=O)NC)=CC=4)N=CC=3)=CC=C2N(CC)C=1NCC1=CC=CC=C1 DDDCWHGPCPPUQF-UHFFFAOYSA-N 0.000 claims 1
- RQMVPNXYNWUDJM-UHFFFAOYSA-N 2-[4-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC=CC=4)N(C)C3=CC=2)=N1 RQMVPNXYNWUDJM-UHFFFAOYSA-N 0.000 claims 1
- PVMDISLAIYKXGY-UHFFFAOYSA-N 2-[4-[[4-[[2-[(4-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC(Cl)=CC=4)N(C)C3=CC=2)=N1 PVMDISLAIYKXGY-UHFFFAOYSA-N 0.000 claims 1
- PJPVFWAHEFAFPJ-UHFFFAOYSA-N 2-[4-[[4-[[2-[(4-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC(F)=CC=4)N(C)C3=CC=2)=N1 PJPVFWAHEFAFPJ-UHFFFAOYSA-N 0.000 claims 1
- NMZWIFIUVBUUBO-UHFFFAOYSA-N 2-[4-[[4-[[2-[(4-methoxyphenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC(OC)=CC=4)N(C)C3=CC=2)=N1 NMZWIFIUVBUUBO-UHFFFAOYSA-N 0.000 claims 1
- BRMLQKPXGGJKOH-UHFFFAOYSA-N 2-benzyl-1-ethyl-5-N-methyl-5-N-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-3H-benzimidazole-2,5-diamine Chemical compound C(C1=CC=CC=C1)C1(NC2=C(N1CC)C=CC(=C2)N(C)C1=NC(=NC=C1)NC1=CC=C(C=C1)CS(=O)(=O)C)N BRMLQKPXGGJKOH-UHFFFAOYSA-N 0.000 claims 1
- LLJGESJIVOHITE-UHFFFAOYSA-N 2-chloro-5-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(Cl)C(S(N)(=O)=O)=C1 LLJGESJIVOHITE-UHFFFAOYSA-N 0.000 claims 1
- MIBFTLBYFXKULA-UHFFFAOYSA-N 2-cyclohexyl-5-N,1-dimethyl-5-N-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-3H-benzimidazole-2,5-diamine Chemical compound C1(CCCCC1)C1(NC2=C(N1C)C=CC(=C2)N(C)C1=NC(=NC=C1)NC1=CC=C(C=C1)CS(=O)(=O)C)N MIBFTLBYFXKULA-UHFFFAOYSA-N 0.000 claims 1
- QGOKQMFAMJWRJS-UHFFFAOYSA-N 2-methyl-5-[[4-[methyl-[1-(1-phenylpropan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CC1=C(C=C(C=C1)NC1=NC=CC(=N1)N(C1=CC2=C(N(C=N2)NC(CC2=CC=CC=C2)C)C=C1)C)S(=O)(=O)N QGOKQMFAMJWRJS-UHFFFAOYSA-N 0.000 claims 1
- RXVPGXBALZQUSP-UHFFFAOYSA-N 2-methyl-5-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 RXVPGXBALZQUSP-UHFFFAOYSA-N 0.000 claims 1
- DCLCJVCWWUSCQB-UHFFFAOYSA-N 2-methyl-5-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 DCLCJVCWWUSCQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- GFIZMLKLJWDKGY-UHFFFAOYSA-N 3-[[4-[(2-anilino-1-methylbenzimidazol-5-yl)-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1 GFIZMLKLJWDKGY-UHFFFAOYSA-N 0.000 claims 1
- TVGRXDVZDNNSTE-UHFFFAOYSA-N 3-[[4-[3H-benzimidazol-5-yl-(1-phenylpropan-2-ylamino)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound CC(CC1=CC=CC=C1)NN(C1=CC=C2NC=NC2=C1)C1=CC=NC(NC2=CC=CC(=C2)S(N)(=O)=O)=N1 TVGRXDVZDNNSTE-UHFFFAOYSA-N 0.000 claims 1
- CNWPZQLWWQQCDH-UHFFFAOYSA-N 3-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 CNWPZQLWWQQCDH-UHFFFAOYSA-N 0.000 claims 1
- GDYWDCSTSZQTFL-UHFFFAOYSA-N 3-[[4-[[2-(4-tert-butylanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(C)(C)C)C=C1 GDYWDCSTSZQTFL-UHFFFAOYSA-N 0.000 claims 1
- YQIONXKHSYVTQK-UHFFFAOYSA-N 3-[[4-[[2-(benzylamino)-1-ethylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N=1C2=CC(N(C)C=3N=C(NC=4C=C(C=CC=4)S(N)(=O)=O)N=CC=3)=CC=C2N(CC)C=1NCC1=CC=CC=C1 YQIONXKHSYVTQK-UHFFFAOYSA-N 0.000 claims 1
- PVLQQOOFOKCMAJ-UHFFFAOYSA-N 3-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC=C1 PVLQQOOFOKCMAJ-UHFFFAOYSA-N 0.000 claims 1
- KHGVFVLEOIFLQW-UHFFFAOYSA-N 3-[[4-[[2-[(2-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]methyl]benzenesulfonamide Chemical compound C=1C=NC(CC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC=C1F KHGVFVLEOIFLQW-UHFFFAOYSA-N 0.000 claims 1
- SACFUILRGOIIDS-UHFFFAOYSA-N 3-[[4-[[2-[(3-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC(F)=C1 SACFUILRGOIIDS-UHFFFAOYSA-N 0.000 claims 1
- HSWOIKBIQNJRFP-UHFFFAOYSA-N 3-[[4-[[2-[(4-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(Cl)C=C1 HSWOIKBIQNJRFP-UHFFFAOYSA-N 0.000 claims 1
- BLLVZORDYPOSTK-UHFFFAOYSA-N 3-[[4-[[2-[(4-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(F)C=C1 BLLVZORDYPOSTK-UHFFFAOYSA-N 0.000 claims 1
- LYZKNWGHYAXECF-UHFFFAOYSA-N 3-[[4-[[2-[(4-methoxyphenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=C(C=CC=4)S(N)(=O)=O)N=CC=3)=CC=C2N1C LYZKNWGHYAXECF-UHFFFAOYSA-N 0.000 claims 1
- CVWHWBPEQRSDFN-UHFFFAOYSA-N 3-[[4-[methyl-[1-methyl-2-(1-phenylethylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=CC=CC=1C(C)NC(N(C1=CC=2)C)=NC1=CC=2N(C)C(N=1)=CC=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 CVWHWBPEQRSDFN-UHFFFAOYSA-N 0.000 claims 1
- CKKNJWOTUSTMLF-UHFFFAOYSA-N 3-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 CKKNJWOTUSTMLF-UHFFFAOYSA-N 0.000 claims 1
- GGRRCYZACOPBRI-UHFFFAOYSA-N 3-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 GGRRCYZACOPBRI-UHFFFAOYSA-N 0.000 claims 1
- AQWYJZJPVSMTLU-UHFFFAOYSA-N 4-[[4-[methyl-(1-methyl-2-methylsulfanylbenzimidazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(SC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 AQWYJZJPVSMTLU-UHFFFAOYSA-N 0.000 claims 1
- BTQNREUEBQJRML-UHFFFAOYSA-N 4-[[4-[methyl-(1-methyl-2-methylsulfinylbenzimidazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(S(C)=O)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 BTQNREUEBQJRML-UHFFFAOYSA-N 0.000 claims 1
- URBGGDNKOFNDAH-UHFFFAOYSA-N 4-[[4-[methyl-[1-methyl-2-[4-(trifluoromethyl)anilino]benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(F)(F)F)C=C1 URBGGDNKOFNDAH-UHFFFAOYSA-N 0.000 claims 1
- PXZKSVXXOAPOFX-UHFFFAOYSA-N 4-methoxy-n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C1=CC=NC(NC=2C=C(C=CC=2)S(=O)(=O)N2CCOCC2)=N1 PXZKSVXXOAPOFX-UHFFFAOYSA-N 0.000 claims 1
- OWTZECZTNWLOEI-UHFFFAOYSA-N 4-methoxy-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C1=CC=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=N1 OWTZECZTNWLOEI-UHFFFAOYSA-N 0.000 claims 1
- RRUUVHUXEZBQLY-UHFFFAOYSA-N 4-methyl-1-nitro-n-[3-(trifluoromethyl)phenyl]benzimidazol-2-amine Chemical compound N=1C=2C(C)=CC=CC=2N([N+]([O-])=O)C=1NC1=CC=CC(C(F)(F)F)=C1 RRUUVHUXEZBQLY-UHFFFAOYSA-N 0.000 claims 1
- ORRYGPADFIKKGD-UHFFFAOYSA-N 5-N,1-dimethylbenzimidazole-2,5-diamine Chemical compound CNc1ccc2n(C)c(N)nc2c1 ORRYGPADFIKKGD-UHFFFAOYSA-N 0.000 claims 1
- VSTOOIFVFYFJLY-UHFFFAOYSA-N 5-[[4-[[2-(4-tert-butylanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(C)(C)C)C=C1 VSTOOIFVFYFJLY-UHFFFAOYSA-N 0.000 claims 1
- XJTKJYFNTGIYNZ-UHFFFAOYSA-N 5-[[4-[[2-(benzylamino)-1-ethylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound N=1C2=CC(N(C)C=3N=C(NC=4C=C(C(C)=CC=4)S(N)(=O)=O)N=CC=3)=CC=C2N(CC)C=1NCC1=CC=CC=C1 XJTKJYFNTGIYNZ-UHFFFAOYSA-N 0.000 claims 1
- LXKCUVWKFCRSBB-UHFFFAOYSA-N 5-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC=C1 LXKCUVWKFCRSBB-UHFFFAOYSA-N 0.000 claims 1
- SEMACTOEPIEMPC-UHFFFAOYSA-N 5-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-n-methoxy-2-methylbenzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)NOC)=CC(NC=2N=C(C=CN=2)N(C)C=2C=C3N=C(NCC=4C=CC=CC=4)N(C)C3=CC=2)=C1 SEMACTOEPIEMPC-UHFFFAOYSA-N 0.000 claims 1
- VDLNATFLPHYPDV-UHFFFAOYSA-N 5-[[4-[[2-(cyclohexylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1CCCCC1 VDLNATFLPHYPDV-UHFFFAOYSA-N 0.000 claims 1
- IAIHLMOTGKGUCP-UHFFFAOYSA-N 5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-2-n-[4-(trifluoromethyl)phenyl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(F)(F)F)C=C1 IAIHLMOTGKGUCP-UHFFFAOYSA-N 0.000 claims 1
- 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims 1
- ATDWYWUORBWAHL-UHFFFAOYSA-N C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(N(C)C=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)C=CC=C2N1C Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(N(C)C=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)C=CC=C2N1C ATDWYWUORBWAHL-UHFFFAOYSA-N 0.000 claims 1
- DHNAZQZPGYWWSJ-UHFFFAOYSA-N C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)C=CC=C2N1C Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)C=CC=C2N1C DHNAZQZPGYWWSJ-UHFFFAOYSA-N 0.000 claims 1
- LTWHWELMGUCLHT-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)C(C)(C)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)C(C)(C)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 LTWHWELMGUCLHT-UHFFFAOYSA-N 0.000 claims 1
- UUNDBJFNDOXJBH-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)C(C)(C)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)C(C)(C)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 UUNDBJFNDOXJBH-UHFFFAOYSA-N 0.000 claims 1
- MQSRFXJHXOWZJG-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)C(C)C)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)C(C)C)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 MQSRFXJHXOWZJG-UHFFFAOYSA-N 0.000 claims 1
- ZUGGTNJWCOSSCQ-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)C(CCC)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)C(CCC)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 ZUGGTNJWCOSSCQ-UHFFFAOYSA-N 0.000 claims 1
- KQASEDQMLLAAMH-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 KQASEDQMLLAAMH-UHFFFAOYSA-N 0.000 claims 1
- BOTYLTMPWWCREI-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 BOTYLTMPWWCREI-UHFFFAOYSA-N 0.000 claims 1
- IKXCETOSIYIBCC-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)CCCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)CCCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 IKXCETOSIYIBCC-UHFFFAOYSA-N 0.000 claims 1
- FMYQFSUHDXTEGY-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C(C)(C)C=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C(C)(C)C=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 FMYQFSUHDXTEGY-UHFFFAOYSA-N 0.000 claims 1
- ULCXXJWEINVZPU-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 ULCXXJWEINVZPU-UHFFFAOYSA-N 0.000 claims 1
- HDQNOIZKHMJIBB-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 HDQNOIZKHMJIBB-UHFFFAOYSA-N 0.000 claims 1
- ZRRLLCMQWJAWSS-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 ZRRLLCMQWJAWSS-UHFFFAOYSA-N 0.000 claims 1
- UESDUQLUSIMOHX-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 UESDUQLUSIMOHX-UHFFFAOYSA-N 0.000 claims 1
- QMKXDFCALCUGGV-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3(CC3)C=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 QMKXDFCALCUGGV-UHFFFAOYSA-N 0.000 claims 1
- LIWYWPUZMVAHLO-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3=COC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3=COC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 LIWYWPUZMVAHLO-UHFFFAOYSA-N 0.000 claims 1
- PMGKBKPAIRJVFV-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3=CSC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3=CSC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 PMGKBKPAIRJVFV-UHFFFAOYSA-N 0.000 claims 1
- AUZWQSGVLAXSCR-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3CC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3CC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 AUZWQSGVLAXSCR-UHFFFAOYSA-N 0.000 claims 1
- QXSRRPJLUVDXHL-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3CCCCC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3CCCCC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 QXSRRPJLUVDXHL-UHFFFAOYSA-N 0.000 claims 1
- ZJVSKZNEBYMBKI-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 ZJVSKZNEBYMBKI-UHFFFAOYSA-N 0.000 claims 1
- BCPJAJXFEBOWNM-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3C(=CC=CC=3)C)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3C(=CC=CC=3)C)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 BCPJAJXFEBOWNM-UHFFFAOYSA-N 0.000 claims 1
- RCKNAENLAPRPBW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3C=C4NC=NC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3C=C4NC=NC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 RCKNAENLAPRPBW-UHFFFAOYSA-N 0.000 claims 1
- VVYBCVNENPZMAN-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3C=C4NN=NC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3C=C4NN=NC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 VVYBCVNENPZMAN-UHFFFAOYSA-N 0.000 claims 1
- GRVOSPUTAGMVDF-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 GRVOSPUTAGMVDF-UHFFFAOYSA-N 0.000 claims 1
- JYOMTSQYKVXLHD-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 JYOMTSQYKVXLHD-UHFFFAOYSA-N 0.000 claims 1
- ZQFHRHQSZXBWSP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3SC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3SC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 ZQFHRHQSZXBWSP-UHFFFAOYSA-N 0.000 claims 1
- OOCAVVWYHYOVRM-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 OOCAVVWYHYOVRM-UHFFFAOYSA-N 0.000 claims 1
- UQENFDSCDUKTQN-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC(=CC=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC(=CC=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 UQENFDSCDUKTQN-UHFFFAOYSA-N 0.000 claims 1
- JCFBAPUDWPIHNK-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(C=3)C(F)(F)F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(C=3)C(F)(F)F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 JCFBAPUDWPIHNK-UHFFFAOYSA-N 0.000 claims 1
- DPVULGFRLBJLMU-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(Cl)C=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(Cl)C=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 DPVULGFRLBJLMU-UHFFFAOYSA-N 0.000 claims 1
- BBVHFASUUWPMDJ-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 BBVHFASUUWPMDJ-UHFFFAOYSA-N 0.000 claims 1
- VYUFMERFYJPIGH-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=C(F)C=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 VYUFMERFYJPIGH-UHFFFAOYSA-N 0.000 claims 1
- GSZZYNNCGSLSDW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 GSZZYNNCGSLSDW-UHFFFAOYSA-N 0.000 claims 1
- YITTWJOZVKVLAP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 YITTWJOZVKVLAP-UHFFFAOYSA-N 0.000 claims 1
- SJTRQOXWZMITFL-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 SJTRQOXWZMITFL-UHFFFAOYSA-N 0.000 claims 1
- FCCQAUIIMZYCIM-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 FCCQAUIIMZYCIM-UHFFFAOYSA-N 0.000 claims 1
- LBIISYCCVMUXBX-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 LBIISYCCVMUXBX-UHFFFAOYSA-N 0.000 claims 1
- PSXUEADVMQGUBJ-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 PSXUEADVMQGUBJ-UHFFFAOYSA-N 0.000 claims 1
- IGOBGZXAPLDYSP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 IGOBGZXAPLDYSP-UHFFFAOYSA-N 0.000 claims 1
- YWXAICOAYLVFGO-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(F)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(F)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 YWXAICOAYLVFGO-UHFFFAOYSA-N 0.000 claims 1
- QWNWYKIAYZXPEL-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C4OCOC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C4OCOC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 QWNWYKIAYZXPEL-UHFFFAOYSA-N 0.000 claims 1
- XUISJVYOUZLVAC-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 XUISJVYOUZLVAC-UHFFFAOYSA-N 0.000 claims 1
- YHCLYBNNQKLUAW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(F)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(F)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 YHCLYBNNQKLUAW-UHFFFAOYSA-N 0.000 claims 1
- WLOGMAZQQXESSN-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=CC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 WLOGMAZQQXESSN-UHFFFAOYSA-N 0.000 claims 1
- FEQLOGDQKQGSOD-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 FEQLOGDQKQGSOD-UHFFFAOYSA-N 0.000 claims 1
- KIPQFNBAOKBBNP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 KIPQFNBAOKBBNP-UHFFFAOYSA-N 0.000 claims 1
- QSZCXGRRFODHOK-UHFFFAOYSA-N CC(C)(C)OC(N(C1(CC(=CC=C1)C(F)(F)F)C=1NC2=C(N=1)C=CC=C2)CN)=O Chemical compound CC(C)(C)OC(N(C1(CC(=CC=C1)C(F)(F)F)C=1NC2=C(N=1)C=CC=C2)CN)=O QSZCXGRRFODHOK-UHFFFAOYSA-N 0.000 claims 1
- VJNWXBYIVXQIOR-UHFFFAOYSA-N CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)C4(CC4)C=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)C4(CC4)C=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 VJNWXBYIVXQIOR-UHFFFAOYSA-N 0.000 claims 1
- 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims 1
- MXKIEMGHMAQAFR-UHFFFAOYSA-N N-[4-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound CNc1nc2cc(ccc2n1C)N(C)c1ccnc(Nc2ccc(NS(C)(=O)=O)cc2)n1 MXKIEMGHMAQAFR-UHFFFAOYSA-N 0.000 claims 1
- DWQZBGVJOATFCG-UHFFFAOYSA-N N-methyl-2-[4-[[4-[methyl-[1-(1-phenylpropan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]ethanesulfonamide Chemical compound CNS(=O)(=O)CCC1=CC=C(C=C1)NC1=NC=CC(=N1)N(C1=CC2=C(N(C=N2)NC(CC2=CC=CC=C2)C)C=C1)C DWQZBGVJOATFCG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 1
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 1
- IBYAJZJDSNWXMS-UHFFFAOYSA-N [3-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=C(OS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 IBYAJZJDSNWXMS-UHFFFAOYSA-N 0.000 claims 1
- YATVAEFMOPQUTG-UHFFFAOYSA-N [3-[[4-[[2-[(4-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=C(OS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(Cl)C=C1 YATVAEFMOPQUTG-UHFFFAOYSA-N 0.000 claims 1
- QOKGLZLMAPYOHE-UHFFFAOYSA-N [3-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(OS(C)(=O)=O)=C1 QOKGLZLMAPYOHE-UHFFFAOYSA-N 0.000 claims 1
- QRPLYICUVXYRFX-UHFFFAOYSA-N [4-[[4-[(2-anilino-1-methylbenzimidazol-5-yl)-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=CC(OS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1 QRPLYICUVXYRFX-UHFFFAOYSA-N 0.000 claims 1
- SIJHPUOOPUXJFA-UHFFFAOYSA-N [4-[[4-[(2-anilino-1-methylbenzimidazol-5-yl)-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1 SIJHPUOOPUXJFA-UHFFFAOYSA-N 0.000 claims 1
- GZUMRJWAIIJQJO-UHFFFAOYSA-N [4-[[4-[[1-ethyl-2-(methylamino)benzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2N(CC)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(N)(=O)=O)C=C1 GZUMRJWAIIJQJO-UHFFFAOYSA-N 0.000 claims 1
- DEALAAPCCVAXRV-UHFFFAOYSA-N [4-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=CC(OS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 DEALAAPCCVAXRV-UHFFFAOYSA-N 0.000 claims 1
- FEDMPXBUDSJLCB-UHFFFAOYSA-N [4-[[4-[[2-(benzylamino)-1-ethylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound N=1C2=CC(N(C)C=3N=C(NC=4C=CC(CS(N)(=O)=O)=CC=4)N=CC=3)=CC=C2N(CC)C=1NCC1=CC=CC=C1 FEDMPXBUDSJLCB-UHFFFAOYSA-N 0.000 claims 1
- DGJXNWGMGFPVKX-UHFFFAOYSA-N [4-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC=C1 DGJXNWGMGFPVKX-UHFFFAOYSA-N 0.000 claims 1
- JQLPATKOJYIBON-UHFFFAOYSA-N [4-[[4-[methyl-[1-(1-phenylpropan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound CN(C1=NC(=NC=C1)NC1=CC=C(C=C1)CS(=O)(=O)N)C1=CC2=C(N(C=N2)NC(CC2=CC=CC=C2)C)C=C1 JQLPATKOJYIBON-UHFFFAOYSA-N 0.000 claims 1
- AMEUJNYVEPYGHA-UHFFFAOYSA-N [4-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(N)(=O)=O)C=C1 AMEUJNYVEPYGHA-UHFFFAOYSA-N 0.000 claims 1
- HMKCXHYVJGWKKM-UHFFFAOYSA-N [4-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(OS(C)(=O)=O)C=C1 HMKCXHYVJGWKKM-UHFFFAOYSA-N 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- OVQFEQAEBMNKDM-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-[3-(trifluoromethylsulfanyl)phenyl]acetamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC(SC(F)(F)F)=C1 OVQFEQAEBMNKDM-UHFFFAOYSA-N 0.000 claims 1
- DPKJPBGMAMNRBP-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-1-phenylcyclopropane-1-carboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1(C=2C=CC=CC=2)CC1 DPKJPBGMAMNRBP-UHFFFAOYSA-N 0.000 claims 1
- FLKXTTFHQGBXMJ-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2,3-dihydroindole-1-carboxamide Chemical compound C=1C=C2N(C)C(NC(=O)N3C4=CC=CC=C4CC3)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 FLKXTTFHQGBXMJ-UHFFFAOYSA-N 0.000 claims 1
- NBGGDSPMHASSKR-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-[3-(trifluoromethylsulfanyl)phenyl]acetamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC(SC(F)(F)F)=C1 NBGGDSPMHASSKR-UHFFFAOYSA-N 0.000 claims 1
- BVMVACISWKDUEU-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-phenylacetamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC=C1 BVMVACISWKDUEU-UHFFFAOYSA-N 0.000 claims 1
- KCFDLEQPPPVHBJ-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1=CC=CC=C1 KCFDLEQPPPVHBJ-UHFFFAOYSA-N 0.000 claims 1
- JGGSDHJGWNVSNT-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclohexanecarboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1CCCCC1 JGGSDHJGWNVSNT-UHFFFAOYSA-N 0.000 claims 1
- KDLLRDZCSRHSMF-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1=CC=NC=C1 KDLLRDZCSRHSMF-UHFFFAOYSA-N 0.000 claims 1
- UJESAISRIUHHOS-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C=1C(C)=NOC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 UJESAISRIUHHOS-UHFFFAOYSA-N 0.000 claims 1
- YKHSOJKKGGKLDB-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-[3-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C=1C(C)=NOC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCN(C)CC1 YKHSOJKKGGKLDB-UHFFFAOYSA-N 0.000 claims 1
- ATAALTKEYPLXQN-UHFFFAOYSA-N n-methyl-2-[4-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]ethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NC(C)C)N(C)C3=CC=2)=N1 ATAALTKEYPLXQN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- IQIKQNNUWRSHOX-UHFFFAOYSA-N tert-butyl n-(4-methyl-1-nitrobenzimidazol-2-yl)-n-[3-(trifluoromethyl)phenyl]carbamate Chemical compound N=1C=2C(C)=CC=CC=2N([N+]([O-])=O)C=1N(C(=O)OC(C)(C)C)C1=CC=CC(C(F)(F)F)=C1 IQIKQNNUWRSHOX-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36074102P | 2002-03-01 | 2002-03-01 | |
| PCT/US2003/006022 WO2003074515A1 (en) | 2002-03-01 | 2003-02-28 | Diamino-pyrimidines and their use as angiogenesis inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005524668A JP2005524668A (ja) | 2005-08-18 |
| JP2005524668A5 true JP2005524668A5 (https=) | 2006-03-09 |
Family
ID=27789011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003572983A Pending JP2005524668A (ja) | 2002-03-01 | 2003-02-28 | ジアミノピリミジン類及びそれらの血管新生阻害薬としての使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7338959B2 (https=) |
| EP (1) | EP1487824B1 (https=) |
| JP (1) | JP2005524668A (https=) |
| AT (1) | ATE365165T1 (https=) |
| AU (1) | AU2003220970A1 (https=) |
| CA (1) | CA2477505A1 (https=) |
| DE (1) | DE60314500T2 (https=) |
| ES (1) | ES2290479T3 (https=) |
| MX (1) | MXPA04008458A (https=) |
| WO (1) | WO2003074515A1 (https=) |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| WO2003082272A1 (en) * | 2002-03-29 | 2003-10-09 | Chiron Corporation | Substituted benzazoles and use thereof as raf kinase inhibitors |
| HRP20050089B1 (hr) | 2002-07-29 | 2015-06-19 | Rigel Pharmaceuticals | Upotreba 2,4 pirimidindiaminskog spoja za proizvodnju lijeka za lijeäśenje ili sprjeäśavanje autoimunosne bolesti |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| US7531553B2 (en) * | 2003-03-21 | 2009-05-12 | Amgen Inc. | Heterocyclic compounds and methods of use |
| WO2004087153A2 (en) * | 2003-03-28 | 2004-10-14 | Chiron Corporation | Use of organic compounds for immunopotentiation |
| WO2005012294A1 (en) | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| DE10337942A1 (de) * | 2003-08-18 | 2005-03-17 | Merck Patent Gmbh | Aminobenzimidazolderivate |
| DE10342503A1 (de) * | 2003-09-12 | 2005-04-14 | Merck Patent Gmbh | Benzyl-Benzimidazolylderivate |
| US20070105839A1 (en) * | 2003-09-18 | 2007-05-10 | Patricia Imbach | 2, 4-Di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| DE10349587A1 (de) * | 2003-10-24 | 2005-05-25 | Merck Patent Gmbh | Benzimidazolylderivate |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| MXPA06008606A (es) | 2004-01-30 | 2007-04-13 | Vertex Pharma | Moduladores de transportadores con casete de union a atp. |
| WO2005079791A1 (en) * | 2004-02-12 | 2005-09-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Thiophene -2- carboxylic acid - (1h - benzimidazol - 2 yl) - amide derivatives and related compounds as inhibitors of the tec kinase itk (interleukin -2- inducible t cell kinase) for the treatment of inflammation, immunological and allergic disorders |
| EP2543376A1 (en) * | 2004-04-08 | 2013-01-09 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
| US7652051B2 (en) | 2004-08-25 | 2010-01-26 | Targegen, Inc. | Heterocyclic compounds and methods of use |
| JP2008515986A (ja) * | 2004-10-13 | 2008-05-15 | ワイス | Ｎ−ベンゼンスルホニル置換アニリノ−ピリミジン類似物 |
| SI1814878T1 (sl) | 2004-11-24 | 2012-06-29 | Rigel Pharmaceuticals Inc | Spojine spiro-2,4-pirimidindiamina in njihova uporaba |
| EP1674469A1 (en) * | 2004-12-22 | 2006-06-28 | Schering Aktiengesellschaft | Sulfonamido-macrocycles as Tie2 inhibitors |
| EP1674470A1 (en) * | 2004-12-22 | 2006-06-28 | Schering Aktiengesellschaft | Sulfonamido-macrocycles as Tie2 inhibitors |
| EP1674466A1 (en) * | 2004-12-27 | 2006-06-28 | 4Sc Ag | 2,5- and 2,6-disubstituted benzazole analogues useful as protein kinase inhibitors |
| US7576090B2 (en) | 2004-12-27 | 2009-08-18 | 4Sc Ag | Benzazole analogues and uses thereof |
| AU2006206458B2 (en) | 2005-01-19 | 2012-10-25 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US20060247263A1 (en) * | 2005-04-19 | 2006-11-02 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| AU2006254825A1 (en) * | 2005-06-08 | 2006-12-14 | Targegen, Inc. | Methods and compositions for the treatment of ocular disorders |
| BRPI0610876B8 (pt) | 2005-06-08 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, formulação farmacêutica, e métodos de inibir uma atividade de uma jak cinase, e de inibir uma cascata de transdução de sinal em que jak3 cinase desempenha um papel |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| JP5191391B2 (ja) | 2005-11-01 | 2013-05-08 | ターゲジェン インコーポレーティッド | キナーゼのビ−アリールメタ−ピリミジン阻害剤 |
| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8133900B2 (en) * | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2007056075A2 (en) * | 2005-11-02 | 2007-05-18 | Targegen, Inc. | Six membered heteroaromatic inhibitors targeting resistant kinase mutations |
| ES2622493T3 (es) | 2006-02-24 | 2017-07-06 | Rigel Pharmaceuticals, Inc. | Composiciones y métodos para la inhibición de la ruta de JAK |
| EP2258700A1 (en) | 2006-05-09 | 2010-12-08 | Pfizer Products Inc. | Cycloalkylamino acid derivatives and pharmaceutical compositions thereof |
| WO2008008234A1 (en) | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| AU2007296743B2 (en) | 2006-09-11 | 2012-02-16 | Curis, Inc. | Tyrosine kinase inhibitors containing a zinc binding moiety |
| WO2008128231A1 (en) | 2007-04-16 | 2008-10-23 | Hutchison Medipharma Enterprises Limited | Pyrimidine derivatives |
| CL2008001626A1 (es) | 2007-06-05 | 2009-06-05 | Takeda Pharmaceuticals Co | Compuestos derivados de heterociclos fusionados, agente farmaceutico que los comprende y su uso en la profilaxis y tratamiento del cancer. |
| EP2181987B9 (en) | 2007-08-23 | 2014-09-03 | Takeda Pharmaceutical Company Limited | 2-Carbonylaminobenzothiazoles and their use for the prophylaxis and treatment of cancer |
| WO2009036066A1 (en) * | 2007-09-10 | 2009-03-19 | Curis, Inc. | Vegfr inhibitors containing a zinc binding moiety |
| US8063058B2 (en) | 2008-04-16 | 2011-11-22 | Portola Pharmaceuticals, Inc. | Inhibitors of syk and JAK protein kinases |
| US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| SG165655A1 (en) | 2008-04-16 | 2010-11-29 | Portola Pharm Inc | 2, 6-diamino- pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors |
| AU2009238590A1 (en) | 2008-04-22 | 2009-10-29 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| EP2307456B1 (en) | 2008-06-27 | 2014-10-15 | Amgen Inc. | Ang-2 inhibition to treat multiple sclerosis |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| CZ302548B6 (cs) * | 2008-10-22 | 2011-07-07 | Zentiva, A.S. | Zpusob výroby 5-amino-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-1H-benzimidazolu a 5-(1H-pyrrol-1-yl)-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-1H-benzimidazolu |
| US8697874B2 (en) | 2008-12-01 | 2014-04-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| JO3101B1 (ar) | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
| UY32470A (es) | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| CA2763633A1 (en) * | 2009-05-27 | 2010-12-02 | Gary T. Wang | Pyrimidine inhibitors of kinase activity |
| CA2799579A1 (en) | 2010-05-21 | 2011-11-24 | Intellikine, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| US8927547B2 (en) | 2010-05-21 | 2015-01-06 | Noviga Research Ab | Pyrimidine derivatives |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US20130317029A1 (en) | 2010-11-01 | 2013-11-28 | Portola Pharmaceuticals, Inc. | Oxypyrimidines as syk modulators |
| EP2975027A1 (en) | 2010-11-01 | 2016-01-20 | Portola Pharmaceuticals, Inc. | Nicotinamides as jak kinase modulators |
| CA2816219C (en) | 2010-11-01 | 2019-10-29 | Portola Pharmaceuticals, Inc. | Nicotinamides as syk modulators |
| AU2010363329A1 (en) | 2010-11-07 | 2013-05-09 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
| UY33779A (es) | 2010-12-10 | 2012-07-31 | Boehringer Ingelheim Int | ?2-(fenilamino)-1H-bencimidazol-5-carboxamidas novedosas? |
| US9962361B2 (en) | 2011-01-03 | 2018-05-08 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
| US9532969B2 (en) | 2011-02-08 | 2017-01-03 | The William M. Yarbrough Foundation | Method for treating psoriasis |
| DK2688883T3 (en) | 2011-03-24 | 2016-09-05 | Noviga Res Ab | pyrimidine |
| WO2013054351A1 (en) * | 2011-08-08 | 2013-04-18 | Cadila Healthcare Limited | Heterocyclic compounds |
| WO2013024427A1 (en) * | 2011-08-16 | 2013-02-21 | Glenmark Pharmaceuticals S.A. | Novel urea derivatives as tec kinase inhibitors and uses thereof |
| MX2014002542A (es) | 2011-08-29 | 2014-07-09 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos. |
| MX363551B (es) | 2011-11-23 | 2019-03-27 | Portola Pharmaceuticals Inc Star | Compuestos derivados de pirazina como inhibidores de cinasa. |
| US10434081B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Inhibitors of macrophage migration inhibitory factor |
| US10335387B2 (en) | 2012-07-26 | 2019-07-02 | The William M. Yarbrough Foundation | Method for treating infectious diseases with isothiocyanate functional compounds |
| US10434082B2 (en) | 2012-07-26 | 2019-10-08 | The William M. Yarbrough Foundation | Isothiocyanate functional compounds augmented with secondary antineoplastic medicaments and associated methods for treating neoplasms |
| US10441561B2 (en) | 2012-07-26 | 2019-10-15 | The William M. Yanbrough Foundation | Method for treating benign prostatic hyperplasia (BPH), prostatitis, and prostate cancer |
| WO2014058921A2 (en) | 2012-10-08 | 2014-04-17 | Portola Pharmaceuticals, Inc. | Substituted pyrimidinyl kinase inhibitors |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| US9951027B2 (en) | 2014-02-11 | 2018-04-24 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as MIDH1 inhibitors |
| EA031655B1 (ru) | 2014-02-11 | 2019-02-28 | Байер Фарма Акциенгезельшафт | Бензимидазол-2-амины в качестве ингибиторов midhi |
| KR102494596B1 (ko) * | 2014-07-31 | 2023-01-31 | 재단법인 한국파스퇴르연구소 | 2-아미노-벤즈이미다졸 유도체 및 5-리폭시게나아제 및/또는 프로스타글란딘 e 합성효소 억제제로서의 이들의 용도 |
| JP6672288B2 (ja) | 2014-10-23 | 2020-03-25 | バイエル・ファルマ・アクティエンゲゼルシャフト | 腫瘍の治療のためのｍｉｄｈ１阻害剤としての１−シクロヘキシル−２−フェニルアミノベンゾイミダゾール |
| WO2016062677A1 (en) | 2014-10-23 | 2016-04-28 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as midh1 inhibitors |
| US9957241B2 (en) | 2015-03-31 | 2018-05-01 | Seika Corporation | Aromatic diamine, an intermediate therefor, a method for producing the aromatic diamine, and a method for producing the intermediate therefor |
| WO2016176473A1 (en) | 2015-04-28 | 2016-11-03 | Sanford-Burnham Medical Researc Institute | Apelin receptor agonists and methods of use thereof |
| EP3303302B1 (en) | 2015-06-08 | 2019-03-20 | Bayer Pharma Aktiengesellschaft | N-menthylbenzimidazoles as midh1 inhibitors |
| JP6824954B2 (ja) | 2015-07-16 | 2021-02-03 | ドイチェス クレープスフォルシュングスツェントルム シュティフトゥング デス エッフェントリッヒェン レヒツ | ｍＩＤＨ１阻害剤としての５−ヒドロキシアルキルベンズイミダゾール |
| US12293809B2 (en) | 2019-08-23 | 2025-05-06 | Insilico Medicine Ip Limited | Workflow for generating compounds with biological activity against a specific biological target |
| WO2021038419A1 (en) * | 2019-08-23 | 2021-03-04 | Insilico Medicine Ip Limited | Kinase inhibitors and methods of synthesis and treatment |
| US12064421B2 (en) | 2020-11-02 | 2024-08-20 | Boehringer Ingelheim International Gmbh | Substituted 1H-pyrazolo[4,3-c]pyridines and derivatives as EGFR inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| CA2341409A1 (en) * | 1998-08-31 | 2000-03-09 | Merck And Co., Inc. | Novel angiogenesis inhibitors |
| BR0116452A (pt) | 2000-12-21 | 2003-09-30 | Glaxo Group Ltd | Composto, composição farmacêutica, uso de um composto |
-
2003
- 2003-02-28 AU AU2003220970A patent/AU2003220970A1/en not_active Abandoned
- 2003-02-28 US US10/506,447 patent/US7338959B2/en not_active Expired - Fee Related
- 2003-02-28 EP EP03743709A patent/EP1487824B1/en not_active Expired - Lifetime
- 2003-02-28 JP JP2003572983A patent/JP2005524668A/ja active Pending
- 2003-02-28 WO PCT/US2003/006022 patent/WO2003074515A1/en not_active Ceased
- 2003-02-28 CA CA002477505A patent/CA2477505A1/en not_active Abandoned
- 2003-02-28 AT AT03743709T patent/ATE365165T1/de not_active IP Right Cessation
- 2003-02-28 ES ES03743709T patent/ES2290479T3/es not_active Expired - Lifetime
- 2003-02-28 DE DE60314500T patent/DE60314500T2/de not_active Expired - Fee Related
- 2003-02-28 MX MXPA04008458A patent/MXPA04008458A/es active IP Right Grant
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005524668A5 (https=) | ||
| JP2007514003A5 (https=) | ||
| JP2004517925A5 (https=) | ||
| RU2006138022A (ru) | Пиримидиновые производные и способы лечения, связанные с их применением | |
| RU2312860C2 (ru) | Циклические ингибиторы протеинтирозинкиназ | |
| CA2432000A1 (en) | Pyrimidineamines as angiogenesis modulators | |
| CA2583742A1 (en) | 2,6-substituted-4-monosubstituted amino-pyrimidine as prostaglandin d2 receptor antagonists | |
| JP2004525951A5 (https=) | ||
| JP2004527503A5 (https=) | ||
| HRP20130128T1 (hr) | Supstituirani aromatski derivati karboksamida i ureje kao ligandi vaniloidnog receptora | |
| RU2006105639A (ru) | Новые производные аминобензофенона | |
| ZA200508722B (en) | Pyrimidine derivatives useful for the treatment of diseases mediated by CRTH2 | |
| HRP20130220T1 (hr) | Modulatori indolamin 2,3-dioksigenaze i postupci upotrebe istih | |
| ZA200606880B (en) | Diaminopyrimidines as P2X3 and P2X2/3 antagonists | |
| JP2010502716A5 (https=) | ||
| RU2017139727A (ru) | Гетероциклические ингибиторы erk1 и erk2 и их применение для лечения злокачественного новообразования | |
| JP2014508128A5 (https=) | ||
| JP2007519754A5 (https=) | ||
| ME02642B (me) | Sulfonamid derivati i kao BCL- 2 selektivni agensi za induciranje apoptoze namijenjeni liječenju raka i imunih bolesti | |
| JP2008516974A5 (https=) | ||
| JP2005511543A5 (https=) | ||
| JP2009537543A5 (https=) | ||
| CA2494695A1 (en) | 2-(3-aminoaryl)amino-4-aryl-thiazoles and their use as c-kit inhibitors | |
| JP2013517273A5 (https=) | ||
| RU2019136279A (ru) | C5 -Анилинохиназолиновые соединения и их использование в лечении рака |