JP2004538247A5 - - Google Patents
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- Publication number
- JP2004538247A5 JP2004538247A5 JP2002547920A JP2002547920A JP2004538247A5 JP 2004538247 A5 JP2004538247 A5 JP 2004538247A5 JP 2002547920 A JP2002547920 A JP 2002547920A JP 2002547920 A JP2002547920 A JP 2002547920A JP 2004538247 A5 JP2004538247 A5 JP 2004538247A5
- Authority
- JP
- Japan
- Prior art keywords
- carbamoylamino
- indeno
- methyl
- phenyl
- amino
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- -1 1,2-dihydropyridyl Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000000694 effects Effects 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 4
- 229960000485 methotrexate Drugs 0.000 claims 4
- OYODOQNYJLSLJE-UHFFFAOYSA-N pyrazol-4-one Chemical compound O=C1C=NN=C1 OYODOQNYJLSLJE-UHFFFAOYSA-N 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- GHFDYLOGYDGRHI-UHFFFAOYSA-N 1h-indeno[1,2-c]pyrazol-4-one Chemical compound C12=CC=CC=C2C(=O)C2=C1NN=C2 GHFDYLOGYDGRHI-UHFFFAOYSA-N 0.000 claims 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 3
- 229960004316 cisplatin Drugs 0.000 claims 3
- 239000000824 cytostatic agent Substances 0.000 claims 3
- 230000001085 cytostatic effect Effects 0.000 claims 3
- 229960003668 docetaxel Drugs 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229930013356 epothilone Natural products 0.000 claims 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 3
- 229960005420 etoposide Drugs 0.000 claims 3
- 229960002949 fluorouracil Drugs 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- 229960001603 tamoxifen Drugs 0.000 claims 3
- 229960000303 topotecan Drugs 0.000 claims 3
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims 2
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 2
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 2
- GYOZYWVXFNDGLU-XLPZGREQSA-N dTMP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 GYOZYWVXFNDGLU-XLPZGREQSA-N 0.000 claims 2
- 229960004679 doxorubicin Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 2
- 229960005277 gemcitabine Drugs 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 229940125697 hormonal agent Drugs 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 claims 1
- YFMGMLYLTWKYMF-UHFFFAOYSA-N 1-[3-(2,4-dimethyl-1,3-thiazol-5-yl)-4-oxo-2h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(oxan-4-yl)amino]urea Chemical compound C1COCCC1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C=1SC(C)=NC=1C YFMGMLYLTWKYMF-UHFFFAOYSA-N 0.000 claims 1
- UMLHPJQKVJJUFG-UHFFFAOYSA-N 1-[3-[4-(4-ethylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(oxan-4-yl)amino]urea Chemical compound C1CN(CC)CCN1C1=CC=C(C2=C3C(=O)C4=C(NC(=O)NN(C)C5CCOCC5)C=CC=C4C3=NN2)C=C1 UMLHPJQKVJJUFG-UHFFFAOYSA-N 0.000 claims 1
- ZOOWQWMJUNKICE-UHFFFAOYSA-N 1-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(1,3-thiazol-2-yl)amino]urea Chemical compound N=1C=CSC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 ZOOWQWMJUNKICE-UHFFFAOYSA-N 0.000 claims 1
- APIGPHDSZSFWTR-UHFFFAOYSA-N 1-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(pyrazin-2-yl)amino]urea Chemical compound C=1N=CC=NC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 APIGPHDSZSFWTR-UHFFFAOYSA-N 0.000 claims 1
- IMCIZNQWGZICKL-UHFFFAOYSA-N 1-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(pyridin-2-yl)amino]urea Chemical compound C=1C=CC=NC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 IMCIZNQWGZICKL-UHFFFAOYSA-N 0.000 claims 1
- MZCTYFCSJNIYTA-UHFFFAOYSA-N 1-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(pyridin-3-yl)amino]urea Chemical compound C=1C=CN=CC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 MZCTYFCSJNIYTA-UHFFFAOYSA-N 0.000 claims 1
- KXKMMQNYFZWYTP-UHFFFAOYSA-N 1-[3-[4-[4-(dimethylamino)piperidin-1-yl]phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]-3-[methyl(oxan-4-yl)amino]urea Chemical compound C1CC(N(C)C)CCN1C1=CC=C(C2=C3C(=O)C4=C(NC(=O)NN(C)C5CCOCC5)C=CC=C4C3=NN2)C=C1 KXKMMQNYFZWYTP-UHFFFAOYSA-N 0.000 claims 1
- IHCIBEUAPFOGMQ-UHFFFAOYSA-N 1-[cyclohexyl(methyl)amino]-3-[3-[4-(4-ethylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(C2=C3C(=O)C4=C(NC(=O)NN(C)C5CCCCC5)C=CC=C4C3=NN2)C=C1 IHCIBEUAPFOGMQ-UHFFFAOYSA-N 0.000 claims 1
- PWHOSMWTLZIJBV-UHFFFAOYSA-N 1-[cyclohexyl(methyl)amino]-3-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1CCCCC1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 PWHOSMWTLZIJBV-UHFFFAOYSA-N 0.000 claims 1
- ZWEZGNFTHWWSGI-UHFFFAOYSA-N 1-[cyclohexyl(methyl)amino]-3-[4-oxo-3-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1CN(C(C)C)CCN1C1=CC=C(C2=C3C(=O)C4=C(NC(=O)NN(C)C5CCCCC5)C=CC=C4C3=NN2)C=C1 ZWEZGNFTHWWSGI-UHFFFAOYSA-N 0.000 claims 1
- UVCWRUZNUNUVTR-UHFFFAOYSA-N 1-[methyl(1,3-thiazol-2-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound N=1C=CSC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 UVCWRUZNUNUVTR-UHFFFAOYSA-N 0.000 claims 1
- PDVQFIUVCVLMHG-UHFFFAOYSA-N 1-[methyl(oxan-4-yl)amino]-3-[3-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxo-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1COCCC1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCN(C)CC1 PDVQFIUVCVLMHG-UHFFFAOYSA-N 0.000 claims 1
- IZKOSUJSODTJGO-UHFFFAOYSA-N 1-[methyl(oxan-4-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1COCCC1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 IZKOSUJSODTJGO-UHFFFAOYSA-N 0.000 claims 1
- XWTPMRYJAWYNQK-UHFFFAOYSA-N 1-[methyl(oxan-4-yl)amino]-3-[4-oxo-3-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1CN(C(C)C)CCN1C1=CC=C(C2=C3C(=O)C4=C(NC(=O)NN(C)C5CCOCC5)C=CC=C4C3=NN2)C=C1 XWTPMRYJAWYNQK-UHFFFAOYSA-N 0.000 claims 1
- JOOCWOAUSDJSQF-UHFFFAOYSA-N 1-[methyl(oxan-4-yl)amino]-3-[4-oxo-3-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1COCCC1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N(CC1)CCC1N1CCCC1 JOOCWOAUSDJSQF-UHFFFAOYSA-N 0.000 claims 1
- IDCOZGMVPAZOAM-UHFFFAOYSA-N 1-[methyl(pyrazin-2-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C=1N=CC=NC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 IDCOZGMVPAZOAM-UHFFFAOYSA-N 0.000 claims 1
- KAWFIYJMZVLRRF-UHFFFAOYSA-N 1-[methyl(pyridin-2-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C=1C=CC=NC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 KAWFIYJMZVLRRF-UHFFFAOYSA-N 0.000 claims 1
- DJMXFKPCBLSZRS-UHFFFAOYSA-N 1-[methyl(pyridin-3-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C=1C=CN=CC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 DJMXFKPCBLSZRS-UHFFFAOYSA-N 0.000 claims 1
- NRXVIVKRRIZCSQ-UHFFFAOYSA-N 1-[methyl(pyridin-4-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C=1C=NC=CC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 NRXVIVKRRIZCSQ-UHFFFAOYSA-N 0.000 claims 1
- QXDUGHAHZDXFQK-UHFFFAOYSA-N 1-[methyl(pyrimidin-2-yl)amino]-3-[4-oxo-3-(4-piperazin-1-ylphenyl)-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound N=1C=CC=NC=1N(C)NC(=O)NC(C=1C(=O)C2=3)=CC=CC=1C2=NNC=3C(C=C1)=CC=C1N1CCNCC1 QXDUGHAHZDXFQK-UHFFFAOYSA-N 0.000 claims 1
- QXLQZLBNPTZMRK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2,4-dimethylphenyl)prop-2-en-1-one Chemical compound CN(C)CC(=C)C(=O)C1=CC=C(C)C=C1C QXLQZLBNPTZMRK-UHFFFAOYSA-N 0.000 claims 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 108010024976 Asparaginase Proteins 0.000 claims 1
- 102000015790 Asparaginase Human genes 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
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| US25411600P | 2000-12-08 | 2000-12-08 | |
| PCT/US2001/046904 WO2002046182A1 (en) | 2000-12-08 | 2001-12-07 | Semicarbazides and their uses as cyclin dependent kinase inhibitors |
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| EP (1) | EP1351956A1 (enExample) |
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| AU (1) | AU2002228849A1 (enExample) |
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| US6706718B2 (en) | 2000-12-01 | 2004-03-16 | Bristol-Myers Squibb Company | 3-(2,4-dimethylthiazol-5-yl)indeno[1,2-c]pyrazol-4-one derivatives and their uses |
| WO2003082337A1 (en) * | 2002-03-27 | 2003-10-09 | Cyclacel Limited | Combination comprising a cdk inhibitor and doxorubicin |
| US20050222054A1 (en) * | 2002-03-27 | 2005-10-06 | Cyclacel Limited | Combination comprising a CDK inhibitor and doxorubicin |
| MXPA05004919A (es) * | 2002-11-06 | 2005-08-18 | Cyclacel Ltd | Composicion farmaceutica que comprende un inhibidor cdk y gemcitabina. |
| AU2003276467A1 (en) * | 2002-11-06 | 2004-06-07 | Cyclacel Limited | Combination comprising docetaxel and a cdk inhibitor |
| MXPA05004920A (es) * | 2002-11-06 | 2005-08-18 | Cyclacel Ltd | Combinacion que comprende un inhibidor cdk y cisplatin. |
| GB0225873D0 (en) * | 2002-11-06 | 2002-12-11 | Cyclacel Ltd | Combination |
| US7456169B2 (en) | 2003-02-27 | 2008-11-25 | Abbott Laboratories Inc. | Heterocyclic kinase inhibitors |
| US7320986B2 (en) | 2003-03-07 | 2008-01-22 | Abbott Labortories | Fused tri and tetra-cyclic pyrazole kinase inhibitors |
| WO2004092139A2 (en) * | 2003-04-07 | 2004-10-28 | Gpc Biotech, Inc. | Inhibitors of cyclin-dependent kinases, compositions and uses related thereto |
| US20050043233A1 (en) * | 2003-04-29 | 2005-02-24 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation, migration or apoptosis of myeloma cells or angiogenesis |
| GB0313511D0 (en) * | 2003-06-11 | 2003-07-16 | Cyclacel Ltd | Combination |
| WO2005039506A2 (en) * | 2003-10-24 | 2005-05-06 | Exelixis, Inc. | P70s6 kinase modulators and method of use |
| GB0328180D0 (en) | 2003-12-04 | 2004-01-07 | Cyclacel Ltd | Combination |
| ES2551293T3 (es) | 2004-03-24 | 2015-11-17 | Abbvie Inc. | Inhibidores de quinasas de pirazol tricíclicos |
| EP1884512A4 (en) * | 2005-05-23 | 2011-09-28 | Sagami Chem Res | PYRAZOLE-1-CARBOXYL ESTER DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND PROCESS FOR PRODUCING PYRAZOLE DERIVATIVE |
| GB0625283D0 (en) | 2006-12-19 | 2007-01-24 | Cyclacel Ltd | Combination |
| WO2009014642A1 (en) * | 2007-07-19 | 2009-01-29 | Amgen Inc. | Combination of a de novo purine biosynthesis inhibitor and a cyclin dependent kinase inhibitor for the treatment of cancer |
| US8530445B2 (en) | 2008-06-09 | 2013-09-10 | Cyclacel Limited | Combinations of sapacitabine or CNDAC with DNA methyltransferase inhibitors such as decitabine and procaine |
| CN102395557A (zh) * | 2008-12-09 | 2012-03-28 | 佛罗里达大学研究基金会公司 | 激酶抑制剂化合物 |
| EP2696878B1 (en) | 2011-04-14 | 2019-07-10 | Cyclacel Limited | Dosage regimen for sapacitabine and decitabine in combination for treating acute myeloid leukemia |
| MX2017013383A (es) | 2015-04-20 | 2017-12-07 | Tolero Pharmaceuticals Inc | Prediccion de respuesta a alvocidib mediante perfilado mitocondrial. |
| PL3298021T3 (pl) | 2015-05-18 | 2019-11-29 | Tolero Pharmaceuticals Inc | Proleki alvocidibu o zwiększonej biodostępności |
| MX2018001289A (es) | 2015-08-03 | 2018-04-30 | Tolero Pharmaceuticals Inc | Terapias de combinacion para el tratamiento del cancer. |
| WO2018094275A1 (en) | 2016-11-18 | 2018-05-24 | Tolero Pharmaceuticals, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
| WO2018119000A1 (en) | 2016-12-19 | 2018-06-28 | Tolero Pharmaceuticals, Inc. | Profiling peptides and methods for sensitivity profiling |
| WO2019055579A1 (en) | 2017-09-12 | 2019-03-21 | Tolero Pharmaceuticals, Inc. | TREATMENT REGIME FOR CANCERS THAT ARE INSENSITIVE TO BCL-2 INHIBITORS USING THE MCL-1 ALVOCIDIB INHIBITOR |
| AU2019391097B2 (en) | 2018-12-04 | 2025-07-03 | Sumitomo Pharma America, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
| WO2020191326A1 (en) | 2019-03-20 | 2020-09-24 | Sumitomo Dainippon Pharma Oncology, Inc. | Treatment of acute myeloid leukemia (aml) with venetoclax failure |
| US11242430B2 (en) | 2019-10-17 | 2022-02-08 | Ppg Industries Ohio, Inc. | Crosslinking compositions and coatings formed therefrom |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2223946A (en) | 1988-10-24 | 1990-04-25 | Shell Int Research | Herbicidal compositions and their use |
| PT1023063E (pt) * | 1997-10-06 | 2004-02-27 | Abbott Gmbh & Co Kg | Derivados de indeno¬1,2-c|- nafto¬1,2-c|- e benzo¬6,7|ciclo-hepta¬1,2-c|pirazole |
| ES2281941T3 (es) | 1997-12-13 | 2007-10-01 | Bristol-Myers Squibb Company | Uso de pirazolo(3,4-b)piridina como inhibidores de quinasa dependiente de ciclina. |
| DE69940951D1 (de) * | 1998-04-21 | 2009-07-16 | Bristol Myers Squibb Pharma Co | Nd wachstumshemmende mittel |
| CZ20011563A3 (cs) * | 1998-11-06 | 2003-02-12 | Basf Aktiengesellschaft | Tricyklické pyrazolové deriváty |
| US6114365A (en) | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
-
2001
- 2001-12-07 US US10/010,979 patent/US6849631B2/en not_active Expired - Lifetime
- 2001-12-07 AU AU2002228849A patent/AU2002228849A1/en not_active Abandoned
- 2001-12-07 WO PCT/US2001/046904 patent/WO2002046182A1/en not_active Ceased
- 2001-12-07 JP JP2002547920A patent/JP2004538247A/ja not_active Abandoned
- 2001-12-07 EP EP01989969A patent/EP1351956A1/en not_active Withdrawn
- 2001-12-07 CA CA002430376A patent/CA2430376A1/en not_active Abandoned
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