JP2010536876A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010536876A5 JP2010536876A5 JP2010522030A JP2010522030A JP2010536876A5 JP 2010536876 A5 JP2010536876 A5 JP 2010536876A5 JP 2010522030 A JP2010522030 A JP 2010522030A JP 2010522030 A JP2010522030 A JP 2010522030A JP 2010536876 A5 JP2010536876 A5 JP 2010536876A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- pyrrolo
- compound
- composition
- cancer
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 —CH 2 -aryl Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 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 description 8
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 8
- 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 description 8
- 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 description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 210000004027 cell Anatomy 0.000 claims description 8
- 229940127089 cytotoxic agent Drugs 0.000 claims description 8
- 229960001433 erlotinib Drugs 0.000 claims description 8
- 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 description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 230000002062 proliferating effect Effects 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 239000002207 metabolite Substances 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 claims description 4
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 4
- 101100002068 Bacillus subtilis (strain 168) araR gene Proteins 0.000 claims description 4
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 4
- 108010092160 Dactinomycin Proteins 0.000 claims description 4
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims description 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 claims description 4
- 108010069236 Goserelin Proteins 0.000 claims description 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 description 4
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 4
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- KYRVNWMVYQXFEU-UHFFFAOYSA-N Nocodazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CS1 KYRVNWMVYQXFEU-UHFFFAOYSA-N 0.000 claims description 4
- 229930012538 Paclitaxel Natural products 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 4
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims description 4
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims description 4
- 229960001220 amsacrine Drugs 0.000 claims description 4
- 229960002932 anastrozole Drugs 0.000 claims description 4
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims description 4
- 101150044616 araC gene Proteins 0.000 claims description 4
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229960000397 bevacizumab Drugs 0.000 claims description 4
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 4
- 229940127093 camptothecin Drugs 0.000 claims description 4
- 229960004562 carboplatin Drugs 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 229960005395 cetuximab Drugs 0.000 claims description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
- 229960004316 cisplatin Drugs 0.000 claims description 4
- 229960004397 cyclophosphamide Drugs 0.000 claims description 4
- 229960000640 dactinomycin Drugs 0.000 claims description 4
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 4
- 229960003668 docetaxel Drugs 0.000 claims description 4
- 229960004679 doxorubicin Drugs 0.000 claims description 4
- 229960001904 epirubicin Drugs 0.000 claims description 4
- 229930013356 epothilone Natural products 0.000 claims description 4
- 150000003883 epothilone derivatives Chemical class 0.000 claims description 4
- 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 description 4
- 229960005420 etoposide Drugs 0.000 claims description 4
- 229960000255 exemestane Drugs 0.000 claims description 4
- 229960002949 fluorouracil Drugs 0.000 claims description 4
- 229960002584 gefitinib Drugs 0.000 claims description 4
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229960005277 gemcitabine Drugs 0.000 claims description 4
- 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 description 4
- 229960002913 goserelin Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 4
- 229960003881 letrozole Drugs 0.000 claims description 4
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims description 4
- 229960004844 lovastatin Drugs 0.000 claims description 4
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 4
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 4
- 229960000485 methotrexate Drugs 0.000 claims description 4
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 4
- 229960001156 mitoxantrone Drugs 0.000 claims description 4
- 229940086322 navelbine Drugs 0.000 claims description 4
- 229950006344 nocodazole Drugs 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229960001592 paclitaxel Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229960004622 raloxifene Drugs 0.000 claims description 4
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 4
- 208000002320 spinal muscular atrophy Diseases 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229960001603 tamoxifen Drugs 0.000 claims description 4
- 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 description 4
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide 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](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims description 4
- 229960001278 teniposide Drugs 0.000 claims description 4
- 229960003048 vinblastine Drugs 0.000 claims description 4
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 4
- 229960004528 vincristine Drugs 0.000 claims description 4
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 4
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 4
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- CYZDKOSGLHTOBO-UHFFFAOYSA-N 3-[1-(5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carbonyl)-piperidin-4-yl]-n-hydroxy-propionamide Chemical compound C1CC(CCC(=O)NO)CCN1C(=O)C1=CN2C3=C1C=CC=C3CCC2 CYZDKOSGLHTOBO-UHFFFAOYSA-N 0.000 claims description 2
- JKIZKMYMKFMYEN-UHFFFAOYSA-N 4-[1-(5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-1-ylcarbonyl)piperidin-4-yl]butan-2-one Chemical compound C1CC(CCC(=O)C)CCN1C(=O)C1=CN2C3=C1C=CC=C3CCC2 JKIZKMYMKFMYEN-UHFFFAOYSA-N 0.000 claims description 2
- WAFYQXMJDRSPSG-UHFFFAOYSA-N 4-[[2-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)-2-oxoacetyl]amino]-N-hydroxybutanamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)C(=O)NCCCC(=O)NO WAFYQXMJDRSPSG-UHFFFAOYSA-N 0.000 claims description 2
- CYMDMEIWWITWNA-UHFFFAOYSA-N 4-[[2-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)-2-oxoacetyl]amino]-N-hydroxypentanamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)C(=O)NC(CCC(=O)NO)C CYMDMEIWWITWNA-UHFFFAOYSA-N 0.000 claims description 2
- ONEUCCISOJRBMM-UHFFFAOYSA-N 5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (5-hydroxy carbamoyl-pentyl)-amide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)NCCCCCC(=O)NO ONEUCCISOJRBMM-UHFFFAOYSA-N 0.000 claims description 2
- MVVPTNAUYQYMKV-UHFFFAOYSA-N 6-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-ylcarbamoylamino)-N-hydroxyhexanamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3NC(=O)NCCCCCC(=O)NO MVVPTNAUYQYMKV-UHFFFAOYSA-N 0.000 claims description 2
- YNHWIAIXSNSJRH-UHFFFAOYSA-N 6-[[2-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)-2-oxoacetyl]amino]-N-hydroxyhexanamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)C(=O)NCCCCCC(=O)NO YNHWIAIXSNSJRH-UHFFFAOYSA-N 0.000 claims description 2
- FTQMHSQPUYFMNX-UHFFFAOYSA-N 7-{[5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-1-yl(oxo)acetyl]amino}-n-hydroxyheptanamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)C(=O)NCCCCCCC(=O)NO FTQMHSQPUYFMNX-UHFFFAOYSA-N 0.000 claims description 2
- 206010000830 Acute leukaemia Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000018142 Leiomyosarcoma Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000036626 Mental retardation Diseases 0.000 claims description 2
- 208000026072 Motor neurone disease Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- LZZMIITWPJDCBZ-UHFFFAOYSA-N N-[5-(hydroxyamino)-5-oxopentyl]-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene-3-carboxamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)NCCCCC(=O)NO LZZMIITWPJDCBZ-UHFFFAOYSA-N 0.000 claims description 2
- GCRJCJYORXVXKU-UHFFFAOYSA-N N-[7-(2-amino-4,5-dichloroanilino)-7-oxoheptyl]-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene-3-carboxamide Chemical compound NC1=CC(Cl)=C(Cl)C=C1NC(=O)CCCCCCNC(=O)C1=CN2C3=C1C=CC=C3CCC2 GCRJCJYORXVXKU-UHFFFAOYSA-N 0.000 claims description 2
- YXVYWXJQRXAWQI-UHFFFAOYSA-N N-[8-(hydroxyamino)-8-oxooctyl]-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene-3-carboxamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)NCCCCCCCC(=O)NO YXVYWXJQRXAWQI-UHFFFAOYSA-N 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 208000006994 Precancerous Conditions Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000006289 Rett Syndrome Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 208000024207 chronic leukemia Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- 208000029824 high grade glioma Diseases 0.000 claims description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 201000011614 malignant glioma Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 208000037819 metastatic cancer Diseases 0.000 claims description 2
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 208000005264 motor neuron disease Diseases 0.000 claims description 2
- WQFNMMAWEXUDIB-UHFFFAOYSA-N n-(6-oxoheptyl)-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)NCCCCCC(=O)C WQFNMMAWEXUDIB-UHFFFAOYSA-N 0.000 claims description 2
- XFHLLPYFEXLXMN-UHFFFAOYSA-N n-[7-(hydroxyamino)-7-oxoheptyl]-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxamide Chemical compound C1CCC2=CC=CC3=C2N1C=C3C(=O)NCCCCCCC(=O)NO XFHLLPYFEXLXMN-UHFFFAOYSA-N 0.000 claims description 2
- MWNIBCCCJVALQB-UHFFFAOYSA-N n-[7-(hydroxyamino)-7-oxoheptyl]-6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazole-2-carboxamide Chemical compound COC1=CC=CC(C=2N=C3SC(=CN3C=2)C(=O)NCCCCCCC(=O)NO)=C1 MWNIBCCCJVALQB-UHFFFAOYSA-N 0.000 claims description 2
- SESSWCGDZHNKHR-UHFFFAOYSA-N n-benzyl-n-[7-(hydroxyamino)-7-oxoheptyl]-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxamide Chemical compound C=1N(C=23)CCCC3=CC=CC=2C=1C(=O)N(CCCCCCC(=O)NO)CC1=CC=CC=C1 SESSWCGDZHNKHR-UHFFFAOYSA-N 0.000 claims description 2
- HQHOVGRLHAUNON-UHFFFAOYSA-N n-{4-[2-(hydroxyamino)-2-oxoethyl]phenyl}-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxamide Chemical compound C1=CC(CC(=O)NO)=CC=C1NC(=O)C1=CN2C3=C1C=CC=C3CCC2 HQHOVGRLHAUNON-UHFFFAOYSA-N 0.000 claims description 2
- CTBONNKEEAZCOP-UHFFFAOYSA-N n-{7-[(2-aminophenyl)amino]-7-oxoheptyl}-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline-1-carboxamide Chemical compound NC1=CC=CC=C1NC(=O)CCCCCCNC(=O)C1=CN2C3=C1C=CC=C3CCC2 CTBONNKEEAZCOP-UHFFFAOYSA-N 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 230000004083 survival effect Effects 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 16
- 238000000034 method Methods 0.000 description 13
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96558407P | 2007-08-21 | 2007-08-21 | |
| PCT/US2008/073873 WO2009026446A2 (en) | 2007-08-21 | 2008-08-21 | Hdac inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010536876A JP2010536876A (ja) | 2010-12-02 |
| JP2010536876A5 true JP2010536876A5 (OSRAM) | 2012-09-13 |
Family
ID=39828970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010522030A Withdrawn JP2010536876A (ja) | 2007-08-21 | 2008-08-21 | Ｈｄａｃインヒビター |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100261710A1 (OSRAM) |
| EP (1) | EP2190845A2 (OSRAM) |
| JP (1) | JP2010536876A (OSRAM) |
| CN (1) | CN101835778A (OSRAM) |
| CA (1) | CA2695452A1 (OSRAM) |
| WO (1) | WO2009026446A2 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102186822A (zh) | 2008-08-29 | 2011-09-14 | 顶标公司 | 新脲和硫脲衍生物 |
| WO2011082266A2 (en) | 2009-12-30 | 2011-07-07 | Arqule, Inc. | Substituted heterocyclic compounds |
| WO2011106627A1 (en) | 2010-02-26 | 2011-09-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US20110212969A1 (en) * | 2010-02-26 | 2011-09-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2013041407A1 (en) * | 2011-09-19 | 2013-03-28 | Cellzome Ag | Hydroxamic acids as hdac6 inhibitors |
| JP6272773B2 (ja) * | 2011-11-29 | 2018-01-31 | ナンジン アルゲン ファルマ カンパニー リミテッドＮａｎｊｉｎｇ Ａｌｌｇｅｎ Ｐｈａｒｍａ Ｃｏ． Ｌｔｄ． | Ｈｄａｃ６阻害剤・抗腫瘍剤用複素環アミド化合物 |
| US9387209B2 (en) | 2012-04-10 | 2016-07-12 | Annji Pharmaceutical Co., Ltd. | Histone deacetylases (HDACs) inhibitors |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| JP6117430B2 (ja) | 2013-04-29 | 2017-04-19 | チョン クン ダン ファーマシューティカル コーポレーション | 選択的ヒストン脱アセチル化酵素抑制剤としての新規化合物およびこれを含む薬剤学的組成物 |
| CN110621317B (zh) | 2017-05-16 | 2023-05-12 | 安基生技新药股份有限公司 | 组蛋白去乙酰化酶（hdacs）抑制剂 |
| CN113121527B (zh) * | 2019-12-31 | 2024-09-06 | 上海辉启生物医药科技有限公司 | 三环类化合物及其用途 |
| US20230212129A1 (en) | 2020-06-08 | 2023-07-06 | Annji Pharmaceutical Co., Ltd. | Quinazoline derivatives useful as selective hdac6 inhibitors |
| CN119143740B (zh) * | 2024-08-15 | 2025-11-14 | 杭州科兴生物化工有限公司 | 一种苯并噻吩类衍生物及其制备方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2083005A1 (en) * | 2000-09-29 | 2009-07-29 | TopoTarget UK Limited | Carbamic acid compounds comprising an amide linkage as HDAC inhibitors |
| AR035417A1 (es) * | 2001-01-27 | 2004-05-26 | Hoffmann La Roche | Derivados triciclicos de lactama y sultama, procesos para su elaboracion, medicamentos que los contienen, y el uso de dichos compuestos en la preparacion de medicamentos |
| CA2531661C (en) * | 2003-07-07 | 2013-03-12 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| ITFI20050041A1 (it) * | 2005-03-15 | 2006-09-16 | Menarini Internat Operations Luxembourg Sa | Idrossammati come inibitori dell'istone deacelitasi, loro preparazione e formulazioni farmaceutiche che li contengono |
-
2008
- 2008-08-21 US US12/671,351 patent/US20100261710A1/en not_active Abandoned
- 2008-08-21 CA CA2695452A patent/CA2695452A1/en not_active Abandoned
- 2008-08-21 CN CN200880112378A patent/CN101835778A/zh active Pending
- 2008-08-21 WO PCT/US2008/073873 patent/WO2009026446A2/en not_active Ceased
- 2008-08-21 JP JP2010522030A patent/JP2010536876A/ja not_active Withdrawn
- 2008-08-21 EP EP08827808A patent/EP2190845A2/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010536876A5 (OSRAM) | ||
| JP7169469B2 (ja) | Ｂｒａｆ関連疾患および障害を処置するために有用なキナゾリン－４－オン誘導体 | |
| CN114599361B (zh) | Prmt5抑制剂的药物组合物 | |
| JP2018534289A5 (OSRAM) | ||
| JP5537035B2 (ja) | Ｃｄｋ阻害剤、および成長因子抗体または抗有糸分裂剤を含む組合せ | |
| US20150141429A1 (en) | Parp inhibitor compounds, compositions and methods of use | |
| JP7394768B2 (ja) | キナーゼ阻害剤としての環状イミノピリミジン誘導体 | |
| TWI757722B (zh) | 以雜環化合物作為激酶抑制劑的治療用途 | |
| JP6862563B2 (ja) | ナフチリジン化合物、薬物組成物およびそれらの使用 | |
| JP7778745B2 (ja) | Ｒｈｏ関連コイルドコイル含有プロテインキナーゼの阻害剤 | |
| CN112204027A (zh) | Erk 抑制剂及其应用 | |
| KR20100024932A (ko) | 비사이클로아닐린 유도체 | |
| JP2015523390A5 (OSRAM) | ||
| JP2020536971A5 (OSRAM) | ||
| JP2008156336A5 (OSRAM) | ||
| JP2013056930A5 (OSRAM) | ||
| WO2015192981A1 (en) | Novel compounds as dual inhibitors of histone methyltransferases and dna methyltransferases | |
| RU2012120288A (ru) | Новые производные нафтиридина и их применение в качестве ингибиторов киназы | |
| JP2010533699A5 (OSRAM) | ||
| JP2015530975A5 (OSRAM) | ||
| RU2008102381A (ru) | Ингибиторы тирозинкиназы | |
| PT2004653E (pt) | N- (aril ou heteroaril)-pirazo [1,5-a] pirimidinas substituídas na posição 3 como inibidoras de quinases | |
| JP2017513893A5 (OSRAM) | ||
| JPWO2020032105A5 (OSRAM) | ||
| JP2010530885A5 (OSRAM) |