JP2005533808A5 - - Google Patents
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- Publication number
- JP2005533808A5 JP2005533808A5 JP2004515895A JP2004515895A JP2005533808A5 JP 2005533808 A5 JP2005533808 A5 JP 2005533808A5 JP 2004515895 A JP2004515895 A JP 2004515895A JP 2004515895 A JP2004515895 A JP 2004515895A JP 2005533808 A5 JP2005533808 A5 JP 2005533808A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- ylamino
- thiazol
- pyridin
- group
- 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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- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 102000009465 Growth Factor Receptors Human genes 0.000 claims 4
- 108010009202 Growth Factor Receptors Proteins 0.000 claims 4
- 229910005965 SO 2 Inorganic materials 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- 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 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
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 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
- BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical group CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims 1
- JIMHRVUJVAYWAR-UHFFFAOYSA-N 2,4-difluoro-n-methyl-5-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]benzamide Chemical compound C1=C(F)C(C(=O)NC)=CC(NCC=2SC(NC=3N=CC=CC=3)=NC=2)=C1F JIMHRVUJVAYWAR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DYLWWKFXSFUWIY-UHFFFAOYSA-N 4-fluoro-3-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]-n-(pyridin-2-ylmethyl)benzamide Chemical compound FC1=CC=C(C(=O)NCC=2N=CC=CC=2)C=C1NCC(S1)=CN=C1NC1=CC=CC=N1 DYLWWKFXSFUWIY-UHFFFAOYSA-N 0.000 claims 1
- SVHJGWNFQAITHR-UHFFFAOYSA-N 4-fluoro-3-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]-n-(thiophen-2-ylmethyl)benzamide Chemical compound FC1=CC=C(C(=O)NCC=2SC=CC=2)C=C1NCC(S1)=CN=C1NC1=CC=CC=N1 SVHJGWNFQAITHR-UHFFFAOYSA-N 0.000 claims 1
- MSDMKXQMYQOPJU-UHFFFAOYSA-N 4-fluoro-n-(3-morpholin-4-ylpropyl)-3-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]benzamide Chemical compound FC1=CC=C(C(=O)NCCCN2CCOCC2)C=C1NCC(S1)=CN=C1NC1=CC=CC=N1 MSDMKXQMYQOPJU-UHFFFAOYSA-N 0.000 claims 1
- UCMYSEIPKICNET-UHFFFAOYSA-N 4-fluoro-n-methyl-3-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]benzamide Chemical compound CNC(=O)C1=CC=C(F)C(NCC=2SC(NC=3N=CC=CC=3)=NC=2)=C1 UCMYSEIPKICNET-UHFFFAOYSA-N 0.000 claims 1
- NMLKITREXVWJDE-UHFFFAOYSA-N 4-fluoro-n-prop-2-ynyl-3-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]benzamide Chemical compound FC1=CC=C(C(=O)NCC#C)C=C1NCC(S1)=CN=C1NC1=CC=CC=N1 NMLKITREXVWJDE-UHFFFAOYSA-N 0.000 claims 1
- SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical group OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 claims 1
- HCQFHIDURTWNJM-UHFFFAOYSA-N 6-[[5-[2-[5-(cyclopropylcarbamoyl)-2-fluorophenyl]ethyl]-1,3-thiazol-2-yl]amino]-n-[2-(ethylamino)ethyl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCCNCC)=CC=C1NC(S1)=NC=C1CCC1=CC(C(=O)NC2CC2)=CC=C1F HCQFHIDURTWNJM-UHFFFAOYSA-N 0.000 claims 1
- IKZWCHTUHNPSBS-UHFFFAOYSA-N 6-[[5-[[5-(cyclopropylcarbamoyl)-2,4-difluoroanilino]methyl]-1,3-thiazol-2-yl]amino]-n-[2-(dimethylamino)ethyl]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)N(C)CCN(C)C)=CC=C1NC(S1)=NC=C1CNC1=CC(C(=O)NC2CC2)=C(F)C=C1F IKZWCHTUHNPSBS-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
- 102000012936 Angiostatins Human genes 0.000 claims 1
- 108010079709 Angiostatins Proteins 0.000 claims 1
- 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 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 1
- 108010092160 Dactinomycin Proteins 0.000 claims 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 claims 1
- AADVCYNFEREWOS-OBRABYBLSA-N Discodermolide Chemical class C=C\C=C/[C@H](C)[C@H](OC(N)=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C/[C@H](C)[C@@H](O)[C@@H](C)\C=C/[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C AADVCYNFEREWOS-OBRABYBLSA-N 0.000 claims 1
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims 1
- 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 1
- BHWACYLXMMINQC-UHFFFAOYSA-N Fc1ccc(cc1NCc1cnc(Nc2ccccn2)s1)C(=O)Nc1ccon1.Cc1cc(NC(=O)c2ccc(F)c(NCc3cnc(Nc4ccccn4)s3)c2)no1 Chemical compound Fc1ccc(cc1NCc1cnc(Nc2ccccn2)s1)C(=O)Nc1ccon1.Cc1cc(NC(=O)c2ccc(F)c(NCc3cnc(Nc4ccccn4)s3)c2)no1 BHWACYLXMMINQC-UHFFFAOYSA-N 0.000 claims 1
- 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 claims 1
- 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 108010069236 Goserelin Proteins 0.000 claims 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 claims 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims 1
- JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 claims 1
- 108010047852 Integrin alphaVbeta3 Proteins 0.000 claims 1
- 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 1
- 108010000817 Leuprolide Proteins 0.000 claims 1
- 101710170181 Metalloproteinase inhibitor Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 claims 1
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 claims 1
- 102000004504 Urokinase Plasminogen Activator Receptors Human genes 0.000 claims 1
- 108010042352 Urokinase Plasminogen Activator Receptors Proteins 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
- 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 1
- 150000003838 adenosines Chemical class 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 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 1
- 229960001220 amsacrine Drugs 0.000 claims 1
- 229960002932 anastrozole Drugs 0.000 claims 1
- 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 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000003936 benzamides Chemical class 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 229960000997 bicalutamide Drugs 0.000 claims 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 claims 1
- 229960001467 bortezomib Drugs 0.000 claims 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 229960004630 chlorambucil Drugs 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 229960000978 cyproterone acetate Drugs 0.000 claims 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims 1
- 229960000640 dactinomycin Drugs 0.000 claims 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
- 229950004203 droloxifene Drugs 0.000 claims 1
- 229960001904 epirubicin Drugs 0.000 claims 1
- 229930013356 epothilone Natural products 0.000 claims 1
- 150000003883 epothilone derivatives Chemical class 0.000 claims 1
- 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 1
- 229960005420 etoposide Drugs 0.000 claims 1
- 229960000255 exemestane Drugs 0.000 claims 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims 1
- 229960004039 finasteride Drugs 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 229960002074 flutamide Drugs 0.000 claims 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims 1
- 229960003690 goserelin acetate Drugs 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229960000908 idarubicin Drugs 0.000 claims 1
- 239000000367 immunologic factor Substances 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 229960003881 letrozole Drugs 0.000 claims 1
- 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 1
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 claims 1
- 229960004338 leuprorelin Drugs 0.000 claims 1
- 229960004961 mechlorethamine Drugs 0.000 claims 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims 1
- 229960004296 megestrol acetate Drugs 0.000 claims 1
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- 229940126170 metalloproteinase inhibitor Drugs 0.000 claims 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
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- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229960004622 raloxifene Drugs 0.000 claims 1
- 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 1
- BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 claims 1
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- 229960001603 tamoxifen Drugs 0.000 claims 1
- 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 1
- 229960001278 teniposide Drugs 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- 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 1
- 229960005026 toremifene Drugs 0.000 claims 1
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| JP2005533808A JP2005533808A (ja) | 2005-11-10 |
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| JP (1) | JP4477492B2 (https=) |
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| PL (1) | PL374272A1 (https=) |
| TW (1) | TW200401638A (https=) |
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| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| WO1999001124A1 (en) * | 1996-12-03 | 1999-01-14 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| TW200401638A (en) * | 2002-06-20 | 2004-02-01 | Bristol Myers Squibb Co | Heterocyclic inhibitors of kinases |
| CA2490261A1 (en) * | 2002-06-27 | 2004-01-08 | The University Of Queensland | Differentiation modulating agents and uses therefor |
| DE60330407D1 (de) * | 2002-08-23 | 2010-01-14 | Sloan Kettering Inst Cancer | Synthese von Epothilonen, Zwischenprodukte davon, Analoga und ihre Verwendung |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| CA2531859C (en) | 2003-07-11 | 2013-08-06 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Benzimidazole derivatives as raf kinase inhibitors |
| EP1684750B1 (en) | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
| GB0326601D0 (en) * | 2003-11-14 | 2003-12-17 | Novartis Ag | Organic compounds |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| US7432373B2 (en) | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| US7449167B2 (en) * | 2004-07-08 | 2008-11-11 | Air Products And Chemicals, Inc. | Catalyst and process for improving the adiabatic steam-reforming of natural gas |
| CN101495116A (zh) | 2005-03-22 | 2009-07-29 | 哈佛大学校长及研究员协会 | 蛋白降解病症的治疗 |
| AU2006231929B2 (en) * | 2005-04-04 | 2012-09-06 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
| WO2006134989A1 (ja) * | 2005-06-15 | 2006-12-21 | Kyowa Hakko Kogyo Co., Ltd. | 含窒素複素環化合物 |
| WO2007067257A2 (en) | 2005-12-02 | 2007-06-14 | Vanderbilt University | Broad-emission nanocrystals and methods of making and using same |
| CA2633756C (en) | 2005-12-21 | 2015-11-24 | Micromet Ag | Pharmaceutical antibody compositions with resistance to soluble cea |
| AU2006328186A1 (en) * | 2005-12-22 | 2007-06-28 | Astrazeneca Ab | Chemical compounds |
| AU2007345292B2 (en) | 2006-02-14 | 2013-10-31 | Dana-Farber Cancer Institute, Inc. | Bifunctional histone deacetylase inhibitors |
| AU2007214458C1 (en) | 2006-02-14 | 2012-12-06 | Dana-Farber Cancer Institute, Inc. | Histone deacetylase inhibitors |
| WO2007120669A1 (en) * | 2006-04-13 | 2007-10-25 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Tetrahalogenated compounds useful as inhibitors of angiogenesis |
| CA2654540C (en) | 2006-05-03 | 2017-01-17 | President And Fellows Of Harvard College | Histone deacetylase and tubulin deacetylase inhibitors |
| US20080112888A1 (en) | 2006-06-30 | 2008-05-15 | Schering Corporation | Igfbp2 biomarker |
| WO2008060907A2 (en) | 2006-11-10 | 2008-05-22 | Bristol-Myers Squibb Company | Pyrrolo-pyridine kinase inhibitors |
| ATE548364T1 (de) * | 2007-01-05 | 2012-03-15 | Bristol Myers Squibb Co | Aminopyrazolkinasehemmer |
| ES2606505T3 (es) * | 2007-01-12 | 2017-03-24 | Ab Science | Tratamiento de combinación de cánceres sólidos con antimetabolitos e inhibidores de tirosina quinasa |
| WO2009046141A2 (en) | 2007-10-01 | 2009-04-09 | Isis Pharmaceuticals, Inc. | Antisense modulation of fibroblast growth factor receptor 4 expression |
| TWI469971B (zh) | 2007-10-26 | 2015-01-21 | Univ California | 二芳基乙內醯脲類化合物 |
| RU2515611C2 (ru) | 2008-07-23 | 2014-05-20 | Президент Энд Феллоуз Оф Гарвард Колледж | Ингибиторы деацетилазы и их применение |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| WO2010099139A2 (en) | 2009-02-25 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Combination anti-cancer therapy |
| WO2010099138A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| JP2012519282A (ja) | 2009-02-27 | 2012-08-23 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 間葉様腫瘍細胞またはその生成を阻害する薬剤を同定するための方法 |
| EP2401614A1 (en) | 2009-02-27 | 2012-01-04 | OSI Pharmaceuticals, LLC | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| WO2011019393A2 (en) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Class- and isoform-specific hdac inhibitors and uses thereof |
| US9180127B2 (en) | 2009-12-29 | 2015-11-10 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| EP2702173A1 (en) | 2011-04-25 | 2014-03-05 | OSI Pharmaceuticals, LLC | Use of emt gene signatures in cancer drug discovery, diagnostics, and treatment |
| WO2012174476A2 (en) | 2011-06-16 | 2012-12-20 | Isis Pharmaceuticals, Inc. | Antisense modulation of fibroblast growth factor receptor 4 expression |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| WO2016018795A1 (en) * | 2014-07-28 | 2016-02-04 | The General Hospital Corporation | Histone deacetylase inhibitors |
| AU2015371251B2 (en) | 2014-12-23 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
| HK1246645A1 (zh) | 2015-03-27 | 2018-09-14 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| EP3347018B1 (en) | 2015-09-09 | 2021-09-01 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| US12187701B2 (en) | 2018-06-25 | 2025-01-07 | Dana-Farber Cancer Institute, Inc. | Taire family kinase inhibitors and uses thereof |
| CN116751195B (zh) * | 2023-06-21 | 2025-03-07 | 杭州科兴生物化工有限公司 | 联吡啶类化合物、其可药用的盐以及制备方法和应用 |
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| JPH0841008A (ja) * | 1994-07-29 | 1996-02-13 | Ono Pharmaceut Co Ltd | 一酸化窒素合成酵素阻害剤 |
| US6262096B1 (en) * | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| CA2332325A1 (en) * | 1998-06-18 | 1999-12-23 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
| US6214852B1 (en) * | 1998-10-21 | 2001-04-10 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| AUPP873799A0 (en) * | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| US6982265B1 (en) * | 1999-05-21 | 2006-01-03 | Bristol Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| US6515004B1 (en) * | 1999-12-15 | 2003-02-04 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| US6867300B2 (en) * | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| US6670357B2 (en) * | 2000-11-17 | 2003-12-30 | Bristol-Myers Squibb Company | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
| TW200300350A (en) * | 2001-11-14 | 2003-06-01 | Bristol Myers Squibb Co | C-5 modified indazolylpyrrolotriazines |
| JP2005529890A (ja) * | 2002-04-23 | 2005-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なアリールケトンピロロトリアジン化合物 |
| KR101025675B1 (ko) * | 2002-04-23 | 2011-03-30 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 억제제로서 유용한 피롤로-트리아진 아닐린 화합물 |
| TW200400034A (en) * | 2002-05-20 | 2004-01-01 | Bristol Myers Squibb Co | Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors |
| TW200401638A (en) * | 2002-06-20 | 2004-02-01 | Bristol Myers Squibb Co | Heterocyclic inhibitors of kinases |
| TWI329112B (en) * | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| WO2004013145A1 (en) * | 2002-08-02 | 2004-02-12 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
-
2003
- 2003-06-16 TW TW092116280A patent/TW200401638A/zh unknown
- 2003-06-18 AT AT03761106T patent/ATE455767T1/de not_active IP Right Cessation
- 2003-06-18 DE DE60331061T patent/DE60331061D1/de not_active Expired - Lifetime
- 2003-06-18 ES ES03761106T patent/ES2337246T3/es not_active Expired - Lifetime
- 2003-06-18 JP JP2004515895A patent/JP4477492B2/ja not_active Expired - Fee Related
- 2003-06-18 US US10/464,139 patent/US7084160B2/en not_active Expired - Lifetime
- 2003-06-18 EP EP03761106A patent/EP1513818B1/en not_active Expired - Lifetime
- 2003-06-18 AU AU2003251559A patent/AU2003251559A1/en not_active Abandoned
- 2003-06-18 PL PL03374272A patent/PL374272A1/xx not_active Application Discontinuation
- 2003-06-18 WO PCT/US2003/019243 patent/WO2004001059A2/en not_active Ceased
- 2003-06-19 AR ARP030102171A patent/AR040272A1/es not_active Application Discontinuation
- 2003-06-20 PE PE2003000622A patent/PE20040581A1/es not_active Application Discontinuation
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2004
- 2004-11-29 NO NO20045220A patent/NO330043B1/no not_active IP Right Cessation
- 2004-12-15 IS IS7599A patent/IS7599A/is unknown
-
2006
- 2006-02-08 US US11/349,767 patent/US7547711B2/en not_active Expired - Lifetime
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