TWI558703B - 三唑并吡啶 - Google Patents

Info

Publication number

TWI558703B

TWI558703B TW101114259A TW101114259A TWI558703B TW I558703 B TWI558703 B TW I558703B TW 101114259 A TW101114259 A TW 101114259A TW 101114259 A TW101114259 A TW 101114259A TW I558703 B TWI558703 B TW I558703B

Authority

TW

Taiwan

Prior art keywords

amino

phenyl

triazolo

pyridin

alkyl

Prior art date

2011-04-21

Links

• Espacenet
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• OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 title 1
• -1 hydroxy- Chemical class 0.000 claims description 373
• 239000000203 mixture Substances 0.000 claims description 353
• 150000001875 compounds Chemical class 0.000 claims description 335
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 271
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 180
• 125000005843 halogen group Chemical group 0.000 claims description 116
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 112
• 125000001424 substituent group Chemical group 0.000 claims description 88
• 238000000034 method Methods 0.000 claims description 82
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 81
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 72
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
• 238000002360 preparation method Methods 0.000 claims description 56
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 31
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 31
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 150000001412 amines Chemical class 0.000 claims description 21
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
• 238000006243 chemical reaction Methods 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 238000005859 coupling reaction Methods 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 17
• 150000001204 N-oxides Chemical class 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 125000000524 functional group Chemical group 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 230000024932 T cell mediated immunity Effects 0.000 claims description 6
• 150000001502 aryl halides Chemical class 0.000 claims description 6
• 230000010261 cell growth Effects 0.000 claims description 6
• 230000001413 cellular effect Effects 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000001475 halogen functional group Chemical group 0.000 claims description 6
• 230000028709 inflammatory response Effects 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 230000004083 survival effect Effects 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
• 150000004677 hydrates Chemical class 0.000 claims description 5
• 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 4
• DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
• 206010027476 Metastases Diseases 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• UCFBXUOGFYVMQX-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[2-[4-(hydroxymethyl)-2-methoxyanilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound COC1=CC(CO)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 UCFBXUOGFYVMQX-UHFFFAOYSA-N 0.000 claims description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
• 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 2
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 2
• 208000009849 Female Genital Neoplasms Diseases 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
• 206010029098 Neoplasm skin Diseases 0.000 claims description 2
• 241000232901 Nephroma Species 0.000 claims description 2
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 210000000481 breast Anatomy 0.000 claims description 2
• 201000011523 endocrine gland cancer Diseases 0.000 claims description 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
• 201000005787 hematologic cancer Diseases 0.000 claims description 2
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• JREFLQVSJHVDBB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-methoxy-4-[2-(2-methoxy-4-methylsulfonylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1NC1=NN2C=C(C=3C=C(OC)C(C(=O)NCC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 JREFLQVSJHVDBB-UHFFFAOYSA-N 0.000 claims description 2
• KJTGLXIKIHJFGM-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[2-(2-methoxy-4-methylsulfonylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 KJTGLXIKIHJFGM-UHFFFAOYSA-N 0.000 claims description 2
• MMBNWTKRVCOPSO-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[2-[4-methylsulfonyl-2-(2,2,2-trifluoroethoxy)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound FC(F)(F)COC1=CC(S(=O)(=O)C)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 MMBNWTKRVCOPSO-UHFFFAOYSA-N 0.000 claims description 2
• 208000025351 nephroma Diseases 0.000 claims description 2
• 208000023958 prostate neoplasm Diseases 0.000 claims description 2
• 201000004477 skin sarcoma Diseases 0.000 claims description 2
• 238000012546 transfer Methods 0.000 claims description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
• 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
• 150000001408 amides Chemical class 0.000 claims 3
• 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 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
• 229960004316 cisplatin Drugs 0.000 claims 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 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
• 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
• JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 claims 1
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 1
• FWNWOXNNGAKBKY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[2-(2-methoxy-4-methylsulfinylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound COC1=CC(S(C)=O)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 FWNWOXNNGAKBKY-UHFFFAOYSA-N 0.000 claims 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
• QZGQAOOKHGOLRY-UHFFFAOYSA-N 4-[2-(2-methyl-4-methylsulfonylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-[(4-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1CNC(=O)C1=CC=C(C2=CN3N=C(NC=4C(=CC(=CC=4)S(C)(=O)=O)C)N=C3C=C2)C=C1 QZGQAOOKHGOLRY-UHFFFAOYSA-N 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
• 108010006654 Bleomycin Proteins 0.000 claims 1
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 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
• 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
• 206010059282 Metastases to central nervous system Diseases 0.000 claims 1
• XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 claims 1
• 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 1
• 229930012538 Paclitaxel Natural products 0.000 claims 1
• BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 0.000 claims 1
• 229940123237 Taxane Drugs 0.000 claims 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
• 229940009456 adriamycin Drugs 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
• 230000002280 anti-androgenic effect Effects 0.000 claims 1
• 239000000051 antiandrogen Substances 0.000 claims 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 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
• 229960000997 bicalutamide Drugs 0.000 claims 1
• 229960001561 bleomycin Drugs 0.000 claims 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 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
• 229960001467 bortezomib Drugs 0.000 claims 1
• 229960004117 capecitabine Drugs 0.000 claims 1
• 229960004562 carboplatin Drugs 0.000 claims 1
• 210000000038 chest Anatomy 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
• 229960004397 cyclophosphamide 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
• 229960000684 cytarabine Drugs 0.000 claims 1
• 229960000975 daunorubicin 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
• 229960003957 dexamethasone Drugs 0.000 claims 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
• 229960003668 docetaxel Drugs 0.000 claims 1
• 229960004679 doxorubicin Drugs 0.000 claims 1
• 229930013356 epothilone Natural products 0.000 claims 1
• 150000003883 epothilone derivatives Chemical class 0.000 claims 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
• 229960000390 fludarabine Drugs 0.000 claims 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 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
• 229960000908 idarubicin Drugs 0.000 claims 1
• 229960001101 ifosfamide Drugs 0.000 claims 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
• FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 claims 1
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