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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- 229960001603 tamoxifen Drugs 0.000 claims 1
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- 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
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| 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 |
| WO2004003179A1 (en) * | 2002-06-27 | 2004-01-08 | The University Of Queensland | Differentiation modulating agents and uses therefor |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| EP2186811A1 (en) * | 2002-08-23 | 2010-05-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| EP1653951B1 (en) | 2003-07-11 | 2011-12-28 | Merck Patent GmbH | 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 |
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| US7432373B2 (en) | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
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| US8999289B2 (en) | 2005-03-22 | 2015-04-07 | President And Fellows Of Harvard College | Treatment of protein degradation disorders |
| WO2006106437A2 (en) * | 2005-04-04 | 2006-10-12 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
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| WO2007067257A2 (en) | 2005-12-02 | 2007-06-14 | Vanderbilt University | Broad-emission nanocrystals and methods of making and using same |
| US20090226444A1 (en) | 2005-12-21 | 2009-09-10 | Micromet Ag | Pharmaceutical antibody compositions with resistance to soluble cea |
| BRPI0620362A2 (pt) * | 2005-12-22 | 2012-07-03 | Astrazeneca Ab | composto ou um sal farmaceuticamente aceitável do mesmo, uso do mesmo, métodos para produzir um efeito inibidor de csf-1r quinase em um animal de sangue quente, para produzir um efeito anti-cáncer em um animal de sangue quente e para tratar doença, e, composição farmacêutica |
| US8222423B2 (en) | 2006-02-14 | 2012-07-17 | Dana-Farber Cancer Institute, Inc. | Bifunctional histone deacetylase inhibitors |
| WO2007095584A2 (en) | 2006-02-14 | 2007-08-23 | The President And Fellows Of Harvard College | 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 |
| US8304451B2 (en) | 2006-05-03 | 2012-11-06 | President And Fellows Of Harvard College | Histone deacetylase and tubulin deacetylase inhibitors |
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| US7851500B2 (en) * | 2007-01-05 | 2010-12-14 | Bristol-Myers Squibb Company | Aminopyrazole kinase inhibitors |
| ES2606505T3 (es) * | 2007-01-12 | 2017-03-24 | Ab Science | Tratamiento de combinación de cánceres sólidos con antimetabolitos e inhibidores de tirosina quinasa |
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| EP2620432A3 (en) | 2007-10-26 | 2013-12-18 | The Regents Of the University of California | Diarylhydantoin compounds |
| AU2009274549B2 (en) | 2008-07-23 | 2014-05-01 | Dana-Farber Cancer Institute, Inc. | Deacetylase inhibitors and uses thereof |
| 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 |
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| WO2010099363A1 (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 |
| WO2011019393A2 (en) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Class- and isoform-specific hdac inhibitors and uses thereof |
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| JP6043347B2 (ja) | 2011-06-16 | 2016-12-14 | アイオーニス ファーマシューティカルズ， インコーポレーテッドＩｏｎｉｓ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． | 線維芽細胞増殖因子受容体４の発現のアンチセンス調節 |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| US20170349540A1 (en) * | 2014-07-28 | 2017-12-07 | The General Hospital Corporation | Histone deacetylase inhibitors |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 |
| USRE50776E1 (en) | 2015-03-27 | 2026-02-03 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| AU2016319125B2 (en) * | 2015-09-09 | 2021-04-08 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| 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 |
| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| US6262096B1 (en) * | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| EP1087951B9 (en) * | 1998-06-18 | 2006-09-13 | 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 |
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| 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 |
| US6867300B2 (en) * | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| TW200300350A (en) * | 2001-11-14 | 2003-06-01 | Bristol Myers Squibb Co | C-5 modified indazolylpyrrolotriazines |
| TW200306841A (en) * | 2002-04-23 | 2003-12-01 | Bristol Myers Squibb Co | Aryl ketone pyrrolo-triazine compounds useful as kinase inhibitors |
| PT1497019E (pt) * | 2002-04-23 | 2015-09-10 | Bristol Myers Squibb Co | Compostos de pirrolotriazina anilina úteis como inibidores de quinase |
| 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 |
| AU2003265349A1 (en) * | 2002-08-02 | 2004-02-23 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
-
2003
- 2003-06-16 TW TW092116280A patent/TW200401638A/zh unknown
- 2003-06-18 JP JP2004515895A patent/JP4477492B2/ja not_active Expired - Fee Related
- 2003-06-18 DE DE60331061T patent/DE60331061D1/de not_active Expired - Lifetime
- 2003-06-18 US US10/464,139 patent/US7084160B2/en not_active Expired - Lifetime
- 2003-06-18 WO PCT/US2003/019243 patent/WO2004001059A2/en not_active Ceased
- 2003-06-18 AT AT03761106T patent/ATE455767T1/de not_active IP Right Cessation
- 2003-06-18 EP EP03761106A patent/EP1513818B1/en not_active Expired - Lifetime
- 2003-06-18 ES ES03761106T patent/ES2337246T3/es not_active Expired - Lifetime
- 2003-06-18 PL PL03374272A patent/PL374272A1/xx not_active Application Discontinuation
- 2003-06-18 AU AU2003251559A patent/AU2003251559A1/en not_active Abandoned
- 2003-06-19 AR ARP030102171A patent/AR040272A1/es not_active Application Discontinuation
- 2003-06-20 PE PE2003000622A patent/PE20040581A1/es not_active Application Discontinuation
-
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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