JP2009526072A5 - - Google Patents
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- Publication number
- JP2009526072A5 JP2009526072A5 JP2008554398A JP2008554398A JP2009526072A5 JP 2009526072 A5 JP2009526072 A5 JP 2009526072A5 JP 2008554398 A JP2008554398 A JP 2008554398A JP 2008554398 A JP2008554398 A JP 2008554398A JP 2009526072 A5 JP2009526072 A5 JP 2009526072A5
- Authority
- JP
- Japan
- Prior art keywords
- indazol
- amide
- carboxylic acid
- benzimidazol
- ylamino
- 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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- 150000001875 compounds Chemical class 0.000 claims 19
- -1 1H-indazol-5-yl Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 102000003989 Aurora Kinases Human genes 0.000 claims 3
- 108090000433 Aurora Kinases Proteins 0.000 claims 3
- AISDZXDUJKGHKF-UHFFFAOYSA-N N-(1H-indazol-6-yl)-6-piperazin-1-yl-2-[2-(trifluoromethyl)anilino]-3H-benzimidazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1=NC2=CC(C(=O)NC=3C=C4NN=CC4=CC=3)=C(N3CCNCC3)C=C2N1 AISDZXDUJKGHKF-UHFFFAOYSA-N 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 2
- 201000011231 colorectal cancer Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 230000001404 mediated Effects 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XNBMZVUUWHZORT-UHFFFAOYSA-N 2-[(1-cyclopentylimidazol-2-yl)amino]-N-(1H-indazol-5-yl)-6-(4-methylpiperazin-1-yl)-3H-benzimidazole-5-carboxamide Chemical compound C1CN(C)CCN1C(C(=C1)C(=O)NC=2C=C3C=NNC3=CC=2)=CC2=C1N=C(NC=1N(C=CN=1)C1CCCC1)N2 XNBMZVUUWHZORT-UHFFFAOYSA-N 0.000 claims 1
- MHMXIVBSMSQWOH-UHFFFAOYSA-N 2-[(1-cyclopentylimidazol-2-yl)amino]-N-(1H-indazol-6-yl)-6-(4-propan-2-ylpiperazin-1-yl)-3H-benzimidazole-5-carboxamide Chemical compound C1CN(C(C)C)CCN1C(C(=C1)C(=O)NC=2C=C3NN=CC3=CC=2)=CC2=C1N=C(NC=1N(C=CN=1)C1CCCC1)N2 MHMXIVBSMSQWOH-UHFFFAOYSA-N 0.000 claims 1
- FWXDOFFJAJEPOE-UHFFFAOYSA-N 2-[(1-cyclopentylimidazol-2-yl)amino]-N-(1H-indazol-6-yl)-6-piperazin-1-yl-3H-benzimidazole-5-carboxamide Chemical compound C=1C=C2C=NNC2=CC=1NC(=O)C(C(=CC=1N2)N3CCNCC3)=CC=1N=C2NC1=NC=CN1C1CCCC1 FWXDOFFJAJEPOE-UHFFFAOYSA-N 0.000 claims 1
- YEJWSBSLTSIZIY-UHFFFAOYSA-N 2-[(3-chloropyridin-2-yl)amino]-6-(diethylamino)-N-(1H-indazol-6-yl)-3H-benzimidazole-5-carboxamide Chemical compound N=1C=2C=C(C(=O)NC=3C=C4NN=CC4=CC=3)C(N(CC)CC)=CC=2NC=1NC1=NC=CC=C1Cl YEJWSBSLTSIZIY-UHFFFAOYSA-N 0.000 claims 1
- GNDHBBKCIJNNJX-UHFFFAOYSA-N 2-[[1-(cyclohexylmethyl)imidazol-2-yl]amino]-6-(4-methylpiperazin-1-yl)-3H-benzimidazole-5-carboxylic acid Chemical compound C1CN(C)CCN1C(C(=C1)C(O)=O)=CC2=C1NC(NC=1N(C=CN=1)CC1CCCCC1)=N2 GNDHBBKCIJNNJX-UHFFFAOYSA-N 0.000 claims 1
- VZVZWGALLRTOJR-UHFFFAOYSA-N 6-(diethylamino)-N-(1H-indazol-6-yl)-2-[(3-methylpyridin-2-yl)amino]-3H-benzimidazole-5-carboxamide Chemical compound N=1C=2C=C(C(=O)NC=3C=C4NN=CC4=CC=3)C(N(CC)CC)=CC=2NC=1NC1=NC=CC=C1C VZVZWGALLRTOJR-UHFFFAOYSA-N 0.000 claims 1
- WFKBDVICDXSCBN-UHFFFAOYSA-N 6-(dimethylamino)-N-(1H-indazol-6-yl)-2-[(3-methylpyridin-2-yl)amino]-3H-benzimidazole-5-carboxamide Chemical compound N=1C=2C=C(C(=O)NC=3C=C4NN=CC4=CC=3)C(N(C)C)=CC=2NC=1NC1=NC=CC=C1C WFKBDVICDXSCBN-UHFFFAOYSA-N 0.000 claims 1
- JJSYIPLPEMLERA-UHFFFAOYSA-N 6-(dimethylamino)-N-(1H-indazol-6-yl)-2-[2-(trifluoromethyl)anilino]-3H-benzimidazole-5-carboxamide Chemical compound N=1C=2C=C(C(=O)NC=3C=C4NN=CC4=CC=3)C(N(C)C)=CC=2NC=1NC1=CC=CC=C1C(F)(F)F JJSYIPLPEMLERA-UHFFFAOYSA-N 0.000 claims 1
- AZYKAQIJICDKJX-UHFFFAOYSA-N 6-[bis(2-methylpropyl)amino]-N-(1H-indazol-6-yl)-2-[2-(trifluoromethyl)anilino]-3H-benzimidazole-5-carboxamide Chemical compound N1C=2C=C(C(=O)NC=3C=C4NN=CC4=CC=3)C(N(CC(C)C)CC(C)C)=CC=2N=C1NC1=CC=CC=C1C(F)(F)F AZYKAQIJICDKJX-UHFFFAOYSA-N 0.000 claims 1
- 102000004000 Aurora Kinase A Human genes 0.000 claims 1
- 108090000461 Aurora Kinase A Proteins 0.000 claims 1
- 102000004228 Aurora Kinase B Human genes 0.000 claims 1
- 108090000749 Aurora Kinase B Proteins 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- OWXBQGSFKUUCAG-UHFFFAOYSA-N CC(C)Cn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound CC(C)Cn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 OWXBQGSFKUUCAG-UHFFFAOYSA-N 0.000 claims 1
- BGZNNNSDCWMGML-UHFFFAOYSA-N CC(C)N1CCN(CC1)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CC(C)N1CCN(CC1)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 BGZNNNSDCWMGML-UHFFFAOYSA-N 0.000 claims 1
- KCVDJGFWSFUZGV-UHFFFAOYSA-N CC(C)N1CCN(CC1)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CC(C)N1CCN(CC1)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 KCVDJGFWSFUZGV-UHFFFAOYSA-N 0.000 claims 1
- CJRZGNRFLQUGNM-UHFFFAOYSA-N CC(C)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound CC(C)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 CJRZGNRFLQUGNM-UHFFFAOYSA-N 0.000 claims 1
- OSAJIBRKWBPHOU-UHFFFAOYSA-N CC(C)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCOCC1 Chemical compound CC(C)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCOCC1 OSAJIBRKWBPHOU-UHFFFAOYSA-N 0.000 claims 1
- VSLORNBGAYLGEF-UHFFFAOYSA-N CC1CN(CC(C)O1)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CC1CN(CC(C)O1)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 VSLORNBGAYLGEF-UHFFFAOYSA-N 0.000 claims 1
- WHFYBXJIWPFYDR-UHFFFAOYSA-N CCC(CC)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound CCC(CC)n1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 WHFYBXJIWPFYDR-UHFFFAOYSA-N 0.000 claims 1
- VEWNTHCXMCUYJH-UHFFFAOYSA-N CCCCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound CCCCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 VEWNTHCXMCUYJH-UHFFFAOYSA-N 0.000 claims 1
- HKKPGPCUDCXJNH-UHFFFAOYSA-N CCCN(CC)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCCN(CC)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 HKKPGPCUDCXJNH-UHFFFAOYSA-N 0.000 claims 1
- UPUZFYDYADSBFR-UHFFFAOYSA-N CCCN(CC)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCCN(CC)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 UPUZFYDYADSBFR-UHFFFAOYSA-N 0.000 claims 1
- IYHUJCAONMPBNA-UHFFFAOYSA-N CCCN(CCC)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCCN(CCC)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 IYHUJCAONMPBNA-UHFFFAOYSA-N 0.000 claims 1
- CWMLARGLZYFTJP-UHFFFAOYSA-N CCCN(CCC)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCCN(CCC)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 CWMLARGLZYFTJP-UHFFFAOYSA-N 0.000 claims 1
- YIGDOBRALYFCJQ-UHFFFAOYSA-N CCN(C)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(C)c1cc2[nH]c(Nc3ccccc3C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 YIGDOBRALYFCJQ-UHFFFAOYSA-N 0.000 claims 1
- IFLWXALNGKDTGU-UHFFFAOYSA-N CCN(C)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(C)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 IFLWXALNGKDTGU-UHFFFAOYSA-N 0.000 claims 1
- MHVOYYLQTMGVEX-UHFFFAOYSA-N CCN(CC)c1cc2[nH]c(Nc3cc(F)cc(F)c3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2[nH]c(Nc3cc(F)cc(F)c3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 MHVOYYLQTMGVEX-UHFFFAOYSA-N 0.000 claims 1
- OGQBIIGEBPWICU-UHFFFAOYSA-N CCN(CC)c1cc2[nH]c(Nc3cc(F)ccc3F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2[nH]c(Nc3cc(F)ccc3F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 OGQBIIGEBPWICU-UHFFFAOYSA-N 0.000 claims 1
- GASNFYRDSZSJDU-UHFFFAOYSA-N CCN(CC)c1cc2[nH]c(Nc3cc(ccc3Cl)C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2[nH]c(Nc3cc(ccc3Cl)C(F)(F)F)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 GASNFYRDSZSJDU-UHFFFAOYSA-N 0.000 claims 1
- MMWGJBJWRXZBOZ-UHFFFAOYSA-N CCN(CC)c1cc2[nH]c(Nc3ccc(Cl)cc3Cl)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2[nH]c(Nc3ccc(Cl)cc3Cl)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 MMWGJBJWRXZBOZ-UHFFFAOYSA-N 0.000 claims 1
- IMNQPXYVRRLLSN-UHFFFAOYSA-N CCN(CC)c1cc2[nH]c(Nc3ccccc3C(C)C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2[nH]c(Nc3ccccc3C(C)C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 IMNQPXYVRRLLSN-UHFFFAOYSA-N 0.000 claims 1
- KFYMPXUJZIUONK-UHFFFAOYSA-N CCN(CC)c1cc2nc(Nc3nc(C)ccc3CC)[nH]c2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN(CC)c1cc2nc(Nc3nc(C)ccc3CC)[nH]c2cc1C(=O)Nc1ccc2cn[nH]c2c1 KFYMPXUJZIUONK-UHFFFAOYSA-N 0.000 claims 1
- BANFFPBKLPICNV-UHFFFAOYSA-N CCN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CCN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 BANFFPBKLPICNV-UHFFFAOYSA-N 0.000 claims 1
- BFFQMYCYFLMCTR-UHFFFAOYSA-N CCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound CCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 BFFQMYCYFLMCTR-UHFFFAOYSA-N 0.000 claims 1
- OWTJCECDYIEATM-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3cc(F)cc(F)c3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3cc(F)cc(F)c3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 OWTJCECDYIEATM-UHFFFAOYSA-N 0.000 claims 1
- FVVCFLZKMPPLDQ-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3ccc(Cl)cc3Cl)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3ccc(Cl)cc3Cl)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 FVVCFLZKMPPLDQ-UHFFFAOYSA-N 0.000 claims 1
- VRUMRPCYMJXMED-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3ncccc3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 VRUMRPCYMJXMED-UHFFFAOYSA-N 0.000 claims 1
- DRJKSGDFAAPDEI-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 DRJKSGDFAAPDEI-UHFFFAOYSA-N 0.000 claims 1
- WBARYMQGZWFQNY-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 WBARYMQGZWFQNY-UHFFFAOYSA-N 0.000 claims 1
- YQETTXJSGLCTML-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 YQETTXJSGLCTML-UHFFFAOYSA-N 0.000 claims 1
- YHQVKJDVDWVMAG-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3nccn3C3CCCCC3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 YHQVKJDVDWVMAG-UHFFFAOYSA-N 0.000 claims 1
- CEJIKJXISWFZPL-UHFFFAOYSA-N CN1CCN(CC1)c1cc2[nH]c(Nc3nccs3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 Chemical compound CN1CCN(CC1)c1cc2[nH]c(Nc3nccs3)nc2cc1C(=O)Nc1ccc2cn[nH]c2c1 CEJIKJXISWFZPL-UHFFFAOYSA-N 0.000 claims 1
- ZJGUPCSKJFJOCP-UHFFFAOYSA-N COCCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 Chemical compound COCCn1ccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCN(C)CC1 ZJGUPCSKJFJOCP-UHFFFAOYSA-N 0.000 claims 1
- LUURBAICLUVVGT-UHFFFAOYSA-N Cc1cccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCOCC1 Chemical compound Cc1cccnc1Nc1nc2cc(C(=O)Nc3ccc4cn[nH]c4c3)c(cc2[nH]1)N1CCOCC1 LUURBAICLUVVGT-UHFFFAOYSA-N 0.000 claims 1
- KEFTXIIEXNSQFP-UHFFFAOYSA-N Clc1ccc(Nc2nc3cc(C(=O)Nc4ccc5cn[nH]c5c4)c(cc3[nH]2)N2CCOCC2)c(Cl)c1 Chemical compound Clc1ccc(Nc2nc3cc(C(=O)Nc4ccc5cn[nH]c5c4)c(cc3[nH]2)N2CCOCC2)c(Cl)c1 KEFTXIIEXNSQFP-UHFFFAOYSA-N 0.000 claims 1
- AAKJLRGGTJKAMG-UHFFFAOYSA-N Erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims 1
- 229960001433 Erlotinib Drugs 0.000 claims 1
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2007
- 2007-02-09 EP EP10194622A patent/EP2295432A1/en not_active Withdrawn
- 2007-02-09 CN CN2012101215887A patent/CN102633783A/zh active Pending
- 2007-02-09 WO PCT/US2007/003579 patent/WO2007095124A2/en active Application Filing
- 2007-02-09 JP JP2008554398A patent/JP5188988B2/ja not_active Expired - Fee Related
- 2007-02-09 CA CA2641744A patent/CA2641744C/en not_active Expired - Fee Related
- 2007-02-09 EP EP07750418A patent/EP1987028A2/en not_active Withdrawn
- 2007-02-09 CN CN2007800047858A patent/CN101379060B/zh not_active Expired - Fee Related
- 2007-02-09 US US11/704,431 patent/US7820821B2/en not_active Expired - Fee Related
- 2007-02-09 BR BRPI0708034-4A patent/BRPI0708034A2/pt not_active IP Right Cessation
- 2007-02-09 AU AU2007215247A patent/AU2007215247B2/en not_active Ceased
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2008
- 2008-07-02 IL IL192580A patent/IL192580A0/en unknown
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2009
- 2009-04-30 HK HK09104027.0A patent/HK1125631A1/xx not_active IP Right Cessation
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2010
- 2010-02-10 US US12/703,604 patent/US8377983B2/en not_active Expired - Fee Related
