AU2006212179A1

AU2006212179A1 - Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer

Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer Download PDF

Info

Publication number: AU2006212179A1
Authority: AU; Australia
Prior art keywords: phenyl; cyano; thieno; dihydro; pyridine
Prior art date: 2005-02-11
Legal status : Abandoned

Application number

AU2006212179A

Other languages

English (en)

Inventor

Thomas Baer

Bjoern Bartels

Thomas Beckers

Klaus Pekari

Mathias Schmidt

Current Assignee

4SC AG

Original Assignee

4SC AG

Priority date

2005-02-11

Filing date

2006-02-10

Publication date

2006-08-17

2006-02-10 Application filed by 4SC AG filed Critical 4SC AG

2006-08-17 Publication of AU2006212179A1 publication Critical patent/AU2006212179A1/en

2008-10-02 Assigned to 4SC AG reassignment 4SC AG Request for Assignment Assignors: NYCOMED GMBH

Status Abandoned legal-status Critical Current

Links

206010028980 Neoplasm Diseases 0.000 title claims description 91
201000011510 cancer Diseases 0.000 title claims description 47
238000011282 treatment Methods 0.000 title claims description 22
WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical class N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 533
-1 cyano, hydroxyl Chemical group 0.000 claims description 423
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 129
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 83
239000001257 hydrogen Substances 0.000 claims description 77
229910052739 hydrogen Inorganic materials 0.000 claims description 77
125000000229 (C1-C4)alkoxy group Chemical class 0.000 claims description 71
150000003839 salts Chemical class 0.000 claims description 70
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 69
238000000034 method Methods 0.000 claims description 65
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
150000002431 hydrogen Chemical class 0.000 claims description 43
201000010099 disease Diseases 0.000 claims description 40
239000002246 antineoplastic agent Substances 0.000 claims description 36
125000004076 pyridyl group Chemical group 0.000 claims description 36
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 35
229910052757 nitrogen Inorganic materials 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 33
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
229910052736 halogen Inorganic materials 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 31
229910052799 carbon Inorganic materials 0.000 claims description 29
239000003814 drug Substances 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 27
230000003211 malignant effect Effects 0.000 claims description 27
239000008194 pharmaceutical composition Substances 0.000 claims description 27
230000009826 neoplastic cell growth Effects 0.000 claims description 26
230000006882 induction of apoptosis Effects 0.000 claims description 25
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 23
230000002062 proliferating effect Effects 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 21
125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
125000002950 monocyclic group Chemical group 0.000 claims description 16
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000002883 imidazolyl group Chemical group 0.000 claims description 14
239000005864 Sulphur Chemical group 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
150000001721 carbon Chemical group 0.000 claims description 13
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Chemical group 0.000 claims description 13
238000002560 therapeutic procedure Methods 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
SYAGAOUSVJBXTH-UHFFFAOYSA-N 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(O)=O)=C2S1 SYAGAOUSVJBXTH-UHFFFAOYSA-N 0.000 claims description 11
AMSSJLMJTRPWOA-UHFFFAOYSA-N 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(O)=O)=C2S1 AMSSJLMJTRPWOA-UHFFFAOYSA-N 0.000 claims description 11
UWSRUSYETIJRFM-UHFFFAOYSA-N 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(O)=O)C#N)=C1 UWSRUSYETIJRFM-UHFFFAOYSA-N 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 11
125000003226 pyrazolyl group Chemical group 0.000 claims description 11
DDQJELXIYYFGNC-UHFFFAOYSA-N 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(O)=O)=C2S1 DDQJELXIYYFGNC-UHFFFAOYSA-N 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
230000000973 chemotherapeutic effect Effects 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000003373 pyrazinyl group Chemical group 0.000 claims description 9
229930012538 Paclitaxel Natural products 0.000 claims description 8
238000009472 formulation Methods 0.000 claims description 8
229960001592 paclitaxel Drugs 0.000 claims description 8
229960004316 cisplatin Drugs 0.000 claims description 7
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
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 6
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 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
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 6
229960000435 oblimersen Drugs 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
WYIYANBMIOSQKM-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC3OC(C)(C)OC3)=C2S1 WYIYANBMIOSQKM-UHFFFAOYSA-N 0.000 claims description 5
GTALHEYWPAWLQW-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOC(C)=O)=C2S1 GTALHEYWPAWLQW-UHFFFAOYSA-N 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 5
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
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 description 5
229960004397 cyclophosphamide Drugs 0.000 claims description 5
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 5
229960001433 erlotinib Drugs 0.000 claims description 5
229960002584 gefitinib Drugs 0.000 claims description 5
MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 claims description 5
GLVAUDGFNGKCSF-UHFFFAOYSA-N purine-6-thione Natural products S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 5
DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 claims description 5
229960004641 rituximab Drugs 0.000 claims description 5
229960003787 sorafenib Drugs 0.000 claims description 5
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 5
230000001225 therapeutic effect Effects 0.000 claims description 5
QMTQJTZJWOFXGV-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)CO)=C2S1 QMTQJTZJWOFXGV-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
208000017604 Hodgkin disease Diseases 0.000 claims description 4
208000010747 Hodgkins lymphoma Diseases 0.000 claims description 4
102000014150 Interferons Human genes 0.000 claims description 4
108010050904 Interferons Proteins 0.000 claims description 4
239000005517 L01XE01 - Imatinib Substances 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
229940124613 TLR 7/8 agonist Drugs 0.000 claims description 4
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 4
229960000397 bevacizumab Drugs 0.000 claims description 4
125000002619 bicyclic group Chemical group 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
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 4
229960003668 docetaxel Drugs 0.000 claims description 4
HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 claims description 4
QXRSDHAAWVKZLJ-PVYNADRNSA-N epothilone B 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)O1)O)C)=C\C1=CSC(C)=N1 QXRSDHAAWVKZLJ-PVYNADRNSA-N 0.000 claims description 4
229960002949 fluorouracil Drugs 0.000 claims description 4
229960003297 gemtuzumab ozogamicin Drugs 0.000 claims description 4
229960001101 ifosfamide Drugs 0.000 claims description 4
IXWNTLSTOZFSCM-YVACAVLKSA-N ombrabulin Chemical compound C1=C(NC(=O)[C@@H](N)CO)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 IXWNTLSTOZFSCM-YVACAVLKSA-N 0.000 claims description 4
229950003600 ombrabulin Drugs 0.000 claims description 4
229930002330 retinoic acid Natural products 0.000 claims description 4
OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims description 4
229960001196 thiotepa Drugs 0.000 claims description 4
WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 4
229940044655 toll-like receptor 9 agonist Drugs 0.000 claims description 4
239000003744 tubulin modulator Substances 0.000 claims description 4
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims description 4
229960000604 valproic acid Drugs 0.000 claims description 4
239000004066 vascular targeting agent Substances 0.000 claims description 4
AHUXKFICWDIMHZ-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC3OC(C)(C)OC3)=C2S1 AHUXKFICWDIMHZ-UHFFFAOYSA-N 0.000 claims description 3
QEDMZBZDJSVFND-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOC(C)=O)=C2S1 QEDMZBZDJSVFND-UHFFFAOYSA-N 0.000 claims description 3
XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 claims description 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 3
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
108010006654 Bleomycin Proteins 0.000 claims description 3
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 description 3
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 description 3
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
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 3
108010069236 Goserelin Proteins 0.000 claims description 3
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 3
239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 3
239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 3
239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 3
239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 3
108010050144 Triptorelin Pamoate Proteins 0.000 claims description 3
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 3
229940122803 Vinca alkaloid Drugs 0.000 claims description 3
AUYLVPGDOVEOML-UHFFFAOYSA-N [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(piperidin-1-ylmethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 AUYLVPGDOVEOML-UHFFFAOYSA-N 0.000 claims description 3
229960000548 alemtuzumab Drugs 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 3
239000005557 antagonist Substances 0.000 claims description 3
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 3
229960001561 bleomycin Drugs 0.000 claims description 3
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 description 3
229960001467 bortezomib Drugs 0.000 claims description 3
229960004117 capecitabine Drugs 0.000 claims description 3
229960004562 carboplatin Drugs 0.000 claims description 3
210000001072 colon Anatomy 0.000 claims description 3
229960003603 decitabine Drugs 0.000 claims description 3
239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 3
229960004679 doxorubicin Drugs 0.000 claims description 3
229960005420 etoposide Drugs 0.000 claims description 3
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
229960000390 fludarabine Drugs 0.000 claims description 3
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 description 3
229960002074 flutamide Drugs 0.000 claims description 3
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 description 3
239000004052 folic acid antagonist Substances 0.000 claims description 3
229960005277 gemcitabine Drugs 0.000 claims description 3
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 3
229960002913 goserelin Drugs 0.000 claims description 3
230000003463 hyperproliferative effect Effects 0.000 claims description 3
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
229960002411 imatinib Drugs 0.000 claims description 3
KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 3
229960004768 irinotecan Drugs 0.000 claims description 3
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 description 3
229960001924 melphalan Drugs 0.000 claims description 3
229960001428 mercaptopurine Drugs 0.000 claims description 3
229960000485 methotrexate Drugs 0.000 claims description 3
210000002307 prostate Anatomy 0.000 claims description 3
239000003790 pyrimidine antagonist Substances 0.000 claims description 3
229960001796 sunitinib Drugs 0.000 claims description 3
WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 3
229960001603 tamoxifen Drugs 0.000 claims description 3
AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims description 3
XSAXBXMCCRYTPX-UHFFFAOYSA-N tert-butyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OC(C)(C)C)=C2S1 XSAXBXMCCRYTPX-UHFFFAOYSA-N 0.000 claims description 3
229940044693 topoisomerase inhibitor Drugs 0.000 claims description 3
229960000303 topotecan Drugs 0.000 claims description 3
229960000575 trastuzumab Drugs 0.000 claims description 3
229960004824 triptorelin Drugs 0.000 claims description 3
VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)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)C1=CC=C(O)C=C1 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 claims description 3
229950000578 vatalanib Drugs 0.000 claims description 3
YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 claims description 3
229960003048 vinblastine Drugs 0.000 claims description 3
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 3
229960004528 vincristine Drugs 0.000 claims description 3
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 3
229960002066 vinorelbine Drugs 0.000 claims description 3
SKPHRKAFMRDPQT-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC3OC(C)(C)OC3)=C2S1 SKPHRKAFMRDPQT-UHFFFAOYSA-N 0.000 claims description 2
UPLBBMBHIPAXKY-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC2OC(C)(C)OC2)C#N)=C1 UPLBBMBHIPAXKY-UHFFFAOYSA-N 0.000 claims description 2
ZIJSDTYUMYGITK-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(=O)OC)=C2S1 ZIJSDTYUMYGITK-UHFFFAOYSA-N 0.000 claims description 2
VOKSPSNUZGXZDC-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(=O)OC)=C2S1 VOKSPSNUZGXZDC-UHFFFAOYSA-N 0.000 claims description 2
RARPUJRJHBRMHH-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1OC RARPUJRJHBRMHH-UHFFFAOYSA-N 0.000 claims description 2
QBIGGRATLOKEMK-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(=O)OC)C#N)=C1 QBIGGRATLOKEMK-UHFFFAOYSA-N 0.000 claims description 2
JWKWBUINXJLDLW-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(=O)OC)C#N)=C1 JWKWBUINXJLDLW-UHFFFAOYSA-N 0.000 claims description 2
FHZVCPLXTYNSHO-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=NC=3)C)=C2S1 FHZVCPLXTYNSHO-UHFFFAOYSA-N 0.000 claims description 2
DJWQGKFVCZMCIM-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=NC=3)C)=C2S1 DJWQGKFVCZMCIM-UHFFFAOYSA-N 0.000 claims description 2
CDKZLFSSAHUMTA-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=NC=3)C)=C2S1 CDKZLFSSAHUMTA-UHFFFAOYSA-N 0.000 claims description 2
IMAOEOWQGAEXNY-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=NC=2)C)C#N)=C1 IMAOEOWQGAEXNY-UHFFFAOYSA-N 0.000 claims description 2
FCSIGPSPGNIQFY-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=NC=2)C)C#N)=C1 FCSIGPSPGNIQFY-UHFFFAOYSA-N 0.000 claims description 2
ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 claims description 2
BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 claims description 2
NVKGVBZZSJFQLM-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitrosourea Chemical compound NC(=O)N(N=O)CCCl NVKGVBZZSJFQLM-UHFFFAOYSA-N 0.000 claims description 2
CKTSBUTUHBMZGZ-SHYZEUOFSA-N 2'‐deoxycytidine Chemical class O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKTSBUTUHBMZGZ-SHYZEUOFSA-N 0.000 claims description 2
OCYQOWZMICUMMP-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)CO)=C2S1 OCYQOWZMICUMMP-UHFFFAOYSA-N 0.000 claims description 2
SBSJAKFYCHMUOT-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)CO)=C2S1 SBSJAKFYCHMUOT-UHFFFAOYSA-N 0.000 claims description 2
ROVDLIJTYCEJMA-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)CO)C#N)=C1 ROVDLIJTYCEJMA-UHFFFAOYSA-N 0.000 claims description 2
CELVEARRTYIWIE-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)CO)C#N)=C1 CELVEARRTYIWIE-UHFFFAOYSA-N 0.000 claims description 2
YJHZMUOJVRTDAB-UHFFFAOYSA-N 2-[3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)=O)=C2S1 YJHZMUOJVRTDAB-UHFFFAOYSA-N 0.000 claims description 2
IPDFVNSFJFSMAK-UHFFFAOYSA-N 2-[3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)=O)=C2S1 IPDFVNSFJFSMAK-UHFFFAOYSA-N 0.000 claims description 2
PPWARDSKMLZSDL-UHFFFAOYSA-N 2-[3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)=O)=C2S1 PPWARDSKMLZSDL-UHFFFAOYSA-N 0.000 claims description 2
CIEWPFXTLNENGJ-UHFFFAOYSA-N 2-[3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)=O)C#N)=C1 CIEWPFXTLNENGJ-UHFFFAOYSA-N 0.000 claims description 2
PDLKDTDZJMGWHO-UHFFFAOYSA-N 2-[3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)=O)C#N)=C1 PDLKDTDZJMGWHO-UHFFFAOYSA-N 0.000 claims description 2
ANJBCVVJKSMUKF-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOC(C)=O)=C2S1 ANJBCVVJKSMUKF-UHFFFAOYSA-N 0.000 claims description 2
MWMMVVWXEQUKPA-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCOC(C)=O)C#N)=C1 MWMMVVWXEQUKPA-UHFFFAOYSA-N 0.000 claims description 2
QQCDILQEJDCMGV-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCO)=C2S1 QQCDILQEJDCMGV-UHFFFAOYSA-N 0.000 claims description 2
PYODLLNFYGSZIP-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCO)=C2S1 PYODLLNFYGSZIP-UHFFFAOYSA-N 0.000 claims description 2
YOTDFNHAMNTIDD-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCO)=C2S1 YOTDFNHAMNTIDD-UHFFFAOYSA-N 0.000 claims description 2
VANCUKBXLDIRDA-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCO)C#N)=C1 VANCUKBXLDIRDA-UHFFFAOYSA-N 0.000 claims description 2
CQKBBPCOKXTRNS-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCO)C#N)=C1 CQKBBPCOKXTRNS-UHFFFAOYSA-N 0.000 claims description 2
TWPKAFYCQHPVCV-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C=NC=C3)=C2S1 TWPKAFYCQHPVCV-UHFFFAOYSA-N 0.000 claims description 2
MALUZLYISMPCJN-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C=NC=C2)C#N)=C1 MALUZLYISMPCJN-UHFFFAOYSA-N 0.000 claims description 2
YOZWOCYFKHLMGP-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOC)=C2S1 YOZWOCYFKHLMGP-UHFFFAOYSA-N 0.000 claims description 2
HUWJIKUHICFZLU-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1OC HUWJIKUHICFZLU-UHFFFAOYSA-N 0.000 claims description 2
JCNIZLAWCJEIFD-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(OC)=C1 JCNIZLAWCJEIFD-UHFFFAOYSA-N 0.000 claims description 2
HUXVIOZBSCFQME-UHFFFAOYSA-N 2-phenylmethoxyethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOCC=3C=CC=CC=3)=C2S1 HUXVIOZBSCFQME-UHFFFAOYSA-N 0.000 claims description 2
FCCVPSKOAANCBM-UHFFFAOYSA-N 2-phenylmethoxyethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOCC=3C=CC=CC=3)=C2S1 FCCVPSKOAANCBM-UHFFFAOYSA-N 0.000 claims description 2
NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 claims description 2
NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims description 2
208000030507 AIDS Diseases 0.000 claims description 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
108090000695 Cytokines Proteins 0.000 claims description 2
102000004127 Cytokines Human genes 0.000 claims description 2
102000009058 Death Domain Receptors Human genes 0.000 claims description 2
108010049207 Death Domain Receptors Proteins 0.000 claims description 2
108010002156 Depsipeptides Proteins 0.000 claims description 2
QXRSDHAAWVKZLJ-OXZHEXMSSA-N Epothilone B Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C QXRSDHAAWVKZLJ-OXZHEXMSSA-N 0.000 claims description 2
108010039471 Fas Ligand Protein Proteins 0.000 claims description 2
101000801228 Homo sapiens Tumor necrosis factor receptor superfamily member 1A Proteins 0.000 claims description 2
102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 2
108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 2
102000000588 Interleukin-2 Human genes 0.000 claims description 2
108010002350 Interleukin-2 Proteins 0.000 claims description 2
MLFKVJCWGUZWNV-UHFFFAOYSA-N L-alanosine Natural products OC(=O)C(N)CN(O)N=O MLFKVJCWGUZWNV-UHFFFAOYSA-N 0.000 claims description 2
206010025323 Lymphomas Diseases 0.000 claims description 2
206010027406 Mesothelioma Diseases 0.000 claims description 2
208000034578 Multiple myelomas Diseases 0.000 claims description 2
201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 2
108091034117 Oligonucleotide Proteins 0.000 claims description 2
206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
229940079156 Proteasome inhibitor Drugs 0.000 claims description 2
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 description 2
206010039491 Sarcoma Diseases 0.000 claims description 2
206010042971 T-cell lymphoma Diseases 0.000 claims description 2
208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 2
229940123237 Taxane Drugs 0.000 claims description 2
102000002689 Toll-like receptor Human genes 0.000 claims description 2
108020000411 Toll-like receptor Proteins 0.000 claims description 2
102100033732 Tumor necrosis factor receptor superfamily member 1A Human genes 0.000 claims description 2
108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 2
102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims description 2
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 2
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 2
208000008383 Wilms tumor Diseases 0.000 claims description 2
239000000556 agonist Substances 0.000 claims description 2
230000001270 agonistic effect Effects 0.000 claims description 2
229950005033 alanosine Drugs 0.000 claims description 2
239000004037 angiogenesis inhibitor Substances 0.000 claims description 2
229940045799 anthracyclines and related substance Drugs 0.000 claims description 2
230000002280 anti-androgenic effect Effects 0.000 claims description 2
229940046836 anti-estrogen Drugs 0.000 claims description 2
230000001833 anti-estrogenic effect Effects 0.000 claims description 2
239000000051 antiandrogen Substances 0.000 claims description 2
229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 2
239000003080 antimitotic agent Substances 0.000 claims description 2
239000003886 aromatase inhibitor Substances 0.000 claims description 2
229940046844 aromatase inhibitors Drugs 0.000 claims description 2
229960002756 azacitidine Drugs 0.000 claims description 2
229960003094 belinostat Drugs 0.000 claims description 2
NCNRHFGMJRPRSK-MDZDMXLPSA-N belinostat Chemical compound ONC(=O)\C=C\C1=CC=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 NCNRHFGMJRPRSK-MDZDMXLPSA-N 0.000 claims description 2
210000000988 bone and bone Anatomy 0.000 claims description 2
150000004648 butanoic acid derivatives Chemical class 0.000 claims description 2
229940127093 camptothecin Drugs 0.000 claims description 2
229940097647 casodex Drugs 0.000 claims description 2
229960005395 cetuximab Drugs 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
229960000684 cytarabine Drugs 0.000 claims description 2
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 2
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 2
239000003968 dna methyltransferase inhibitor Substances 0.000 claims description 2
210000003372 endocrine gland Anatomy 0.000 claims description 2
210000004696 endometrium Anatomy 0.000 claims description 2
INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 claims description 2
229930013356 epothilone Natural products 0.000 claims description 2
HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims description 2
210000003238 esophagus Anatomy 0.000 claims description 2
239000000328 estrogen antagonist Substances 0.000 claims description 2
PBDNPCGKQIZLEL-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,3-diethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(OCC)=C1OCC PBDNPCGKQIZLEL-UHFFFAOYSA-N 0.000 claims description 2
ISRSFKVZGIRDJK-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=C1OCC ISRSFKVZGIRDJK-UHFFFAOYSA-N 0.000 claims description 2
PQBVCKHZWRHHNA-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1OCC PQBVCKHZWRHHNA-UHFFFAOYSA-N 0.000 claims description 2
BYTBQDBIBCHAHA-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1OC BYTBQDBIBCHAHA-UHFFFAOYSA-N 0.000 claims description 2
VMSMEXMHKULCBA-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC(OCC)=C1 VMSMEXMHKULCBA-UHFFFAOYSA-N 0.000 claims description 2
SFVCDJZWPOFUJW-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(OCC)=C1 SFVCDJZWPOFUJW-UHFFFAOYSA-N 0.000 claims description 2
NGERUROSQUMZBY-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(OC)=C1 NGERUROSQUMZBY-UHFFFAOYSA-N 0.000 claims description 2
JZDVQHZRINOTQX-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-nitrophenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC([N+]([O-])=O)=C1 JZDVQHZRINOTQX-UHFFFAOYSA-N 0.000 claims description 2
FJNCVNPTVMYKKH-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=C(OCC)C=C1 FJNCVNPTVMYKKH-UHFFFAOYSA-N 0.000 claims description 2
GBOHFMPZLZBQBT-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=C(OC)C=C1 GBOHFMPZLZBQBT-UHFFFAOYSA-N 0.000 claims description 2
210000004602 germ cell Anatomy 0.000 claims description 2
XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical class C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 claims description 2
210000003128 head Anatomy 0.000 claims description 2
239000003481 heat shock protein 90 inhibitor Substances 0.000 claims description 2
229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 2
239000003276 histone deacetylase inhibitor Substances 0.000 claims description 2
230000003054 hormonal effect Effects 0.000 claims description 2
210000003026 hypopharynx Anatomy 0.000 claims description 2
DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 2
229960002751 imiquimod Drugs 0.000 claims description 2
230000003308 immunostimulating effect Effects 0.000 claims description 2
229940079322 interferon Drugs 0.000 claims description 2
229940047124 interferons Drugs 0.000 claims description 2
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 2
229950003954 isatoribine Drugs 0.000 claims description 2
210000003734 kidney Anatomy 0.000 claims description 2
229940043355 kinase inhibitor Drugs 0.000 claims description 2
210000000867 larynx Anatomy 0.000 claims description 2
208000032839 leukemia Diseases 0.000 claims description 2
210000004185 liver Anatomy 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
230000036210 malignancy Effects 0.000 claims description 2
210000003739 neck Anatomy 0.000 claims description 2
201000008026 nephroblastoma Diseases 0.000 claims description 2
210000001672 ovary Anatomy 0.000 claims description 2
229960001756 oxaliplatin Drugs 0.000 claims description 2
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 2
210000000496 pancreas Anatomy 0.000 claims description 2
FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims description 2
208000012111 paraneoplastic syndrome Diseases 0.000 claims description 2
229960005079 pemetrexed Drugs 0.000 claims description 2
239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 2
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
210000004180 plasmocyte Anatomy 0.000 claims description 2
150000003057 platinum Chemical class 0.000 claims description 2
239000003207 proteasome inhibitor Substances 0.000 claims description 2
IGJSSCIATPBAOJ-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N=CC=CC=3)=C2S1 IGJSSCIATPBAOJ-UHFFFAOYSA-N 0.000 claims description 2
DCUNPBVIMRPKDQ-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N=CC=CC=3)=C2S1 DCUNPBVIMRPKDQ-UHFFFAOYSA-N 0.000 claims description 2
BLYFHUBZQSPONZ-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N=CC=CC=3)=C2S1 BLYFHUBZQSPONZ-UHFFFAOYSA-N 0.000 claims description 2
ODTBADRRNRQTHL-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N=CC=CC=2)C#N)=C1 ODTBADRRNRQTHL-UHFFFAOYSA-N 0.000 claims description 2
UQYGKYMDGYUPCE-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N=CC=CC=2)C#N)=C1 UQYGKYMDGYUPCE-UHFFFAOYSA-N 0.000 claims description 2
CWUYYKAOSAHBNF-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N=CC=CC=2)C#N)=C1 CWUYYKAOSAHBNF-UHFFFAOYSA-N 0.000 claims description 2
VCGJHSAMVXAYPV-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=NC=CC=3)=C2S1 VCGJHSAMVXAYPV-UHFFFAOYSA-N 0.000 claims description 2
VYXCTKPVCDLARF-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=NC=CC=3)=C2S1 VYXCTKPVCDLARF-UHFFFAOYSA-N 0.000 claims description 2
VBWHOYYFGFCMDQ-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=NC=CC=3)=C2S1 VBWHOYYFGFCMDQ-UHFFFAOYSA-N 0.000 claims description 2
QUNKVLTUCXKBKN-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=NC=CC=2)C#N)=C1 QUNKVLTUCXKBKN-UHFFFAOYSA-N 0.000 claims description 2
UNFMLVTUCBFTMF-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=NC=CC=2)C#N)=C1 UNFMLVTUCBFTMF-UHFFFAOYSA-N 0.000 claims description 2
WFJWSIPLQGKYOB-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=NC=CC=2)C#N)=C1 WFJWSIPLQGKYOB-UHFFFAOYSA-N 0.000 claims description 2
NYLAEIKXBAYPDS-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=CN=CC=3)=C2S1 NYLAEIKXBAYPDS-UHFFFAOYSA-N 0.000 claims description 2
XZXOOZBLARYPGI-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=CN=CC=3)=C2S1 XZXOOZBLARYPGI-UHFFFAOYSA-N 0.000 claims description 2
LSCHHKKYEGUKPH-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=CN=CC=3)=C2S1 LSCHHKKYEGUKPH-UHFFFAOYSA-N 0.000 claims description 2
ZWWFSWOXEWTHGN-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=CN=CC=2)C#N)=C1 ZWWFSWOXEWTHGN-UHFFFAOYSA-N 0.000 claims description 2
LVPBRQHSUUPGOT-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=CN=CC=2)C#N)=C1 LVPBRQHSUUPGOT-UHFFFAOYSA-N 0.000 claims description 2
ATUKBOWJOALDGM-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=CN=CC=2)C#N)=C1 ATUKBOWJOALDGM-UHFFFAOYSA-N 0.000 claims description 2
229940044601 receptor agonist Drugs 0.000 claims description 2
239000000018 receptor agonist Substances 0.000 claims description 2
210000000664 rectum Anatomy 0.000 claims description 2
BXNMTOQRYBFHNZ-UHFFFAOYSA-N resiquimod Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 BXNMTOQRYBFHNZ-UHFFFAOYSA-N 0.000 claims description 2
229950010550 resiquimod Drugs 0.000 claims description 2
210000003491 skin Anatomy 0.000 claims description 2
210000000813 small intestine Anatomy 0.000 claims description 2
210000004872 soft tissue Anatomy 0.000 claims description 2
210000002784 stomach Anatomy 0.000 claims description 2
FPXRNBYJLCZXTM-UHFFFAOYSA-N tert-butyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OC(C)(C)C)=C2S1 FPXRNBYJLCZXTM-UHFFFAOYSA-N 0.000 claims description 2
HRBWJAOTXXZLQV-UHFFFAOYSA-N tert-butyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OC(C)(C)C)C#N)=C1 HRBWJAOTXXZLQV-UHFFFAOYSA-N 0.000 claims description 2
210000001550 testis Anatomy 0.000 claims description 2
229960003087 tioguanine Drugs 0.000 claims description 2
229940044616 toll-like receptor 7 agonist Drugs 0.000 claims description 2
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 description 2
229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 2
239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 2
210000000626 ureter Anatomy 0.000 claims description 2
210000003932 urinary bladder Anatomy 0.000 claims description 2
210000001215 vagina Anatomy 0.000 claims description 2
LLDWLPRYLVPDTG-UHFFFAOYSA-N vatalanib succinate Chemical compound OC(=O)CCC(O)=O.C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 LLDWLPRYLVPDTG-UHFFFAOYSA-N 0.000 claims description 2
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 2
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound 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 GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims description 2
210000003905 vulva Anatomy 0.000 claims description 2
RQXLYRSUIJCCAN-UHFFFAOYSA-N 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(O)=O)=C2S1 RQXLYRSUIJCCAN-UHFFFAOYSA-N 0.000 claims 4
RJXMOYCINHSYTL-UHFFFAOYSA-N 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(O)=O)C#N)=C1 RJXMOYCINHSYTL-UHFFFAOYSA-N 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
VSTDWZNJQANEBO-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=CN=3)C)=C2S1 VSTDWZNJQANEBO-UHFFFAOYSA-N 0.000 claims 1
CHXGNVHHUROWES-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=CN=3)C)=C2S1 CHXGNVHHUROWES-UHFFFAOYSA-N 0.000 claims 1
UPIAIJAJDRNQNO-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=CN=3)C)=C2S1 UPIAIJAJDRNQNO-UHFFFAOYSA-N 0.000 claims 1
CVZAWTAKUYLECJ-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=CN=2)C)C#N)=C1 CVZAWTAKUYLECJ-UHFFFAOYSA-N 0.000 claims 1
DGKUXLDGIJNFRD-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=CN=2)C)C#N)=C1 DGKUXLDGIJNFRD-UHFFFAOYSA-N 0.000 claims 1
NVCDCHNJHGGRSF-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=CN=2)C)C#N)=C1 NVCDCHNJHGGRSF-UHFFFAOYSA-N 0.000 claims 1
OCZSUYZZMWHIOQ-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC3OC(C)(C)OC3)=C2S1 OCZSUYZZMWHIOQ-UHFFFAOYSA-N 0.000 claims 1
TUECZFZXIDXERC-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC2OC(C)(C)OC2)C#N)=C1 TUECZFZXIDXERC-UHFFFAOYSA-N 0.000 claims 1
IVZDDWGECFNCEU-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=C1OC IVZDDWGECFNCEU-UHFFFAOYSA-N 0.000 claims 1
NXFBDJZJIPABCQ-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC(OC)=C1 NXFBDJZJIPABCQ-UHFFFAOYSA-N 0.000 claims 1
ZUKCEJAKZXABGA-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N(C=NC=3)C)=C2S1 ZUKCEJAKZXABGA-UHFFFAOYSA-N 0.000 claims 1
IPALXVNLHHFINO-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N(C=NC=2)C)C#N)=C1 IPALXVNLHHFINO-UHFFFAOYSA-N 0.000 claims 1
AFMKRFIYXCKTPH-UHFFFAOYSA-N (4-methoxypyridin-3-yl)methyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=NC=C1COC(=O)N1CC(SC(NC(=O)CCC=2C(=CC=C(C)C=2)OC)=C2C#N)=C2CC1 AFMKRFIYXCKTPH-UHFFFAOYSA-N 0.000 claims 1
VULUFOZFVXMSOO-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(C)C=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)CO)=C2S1 VULUFOZFVXMSOO-UHFFFAOYSA-N 0.000 claims 1
JENGSCKFGVPXRW-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)CO)=C2S1 JENGSCKFGVPXRW-UHFFFAOYSA-N 0.000 claims 1
LAFWGJACWPBLHN-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)CO)C#N)=C1 LAFWGJACWPBLHN-UHFFFAOYSA-N 0.000 claims 1
RBKOUPRHKZDMPS-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C(=NC(C)=C3)C)=C2S1 RBKOUPRHKZDMPS-UHFFFAOYSA-N 0.000 claims 1
JCMPCXLQEBNCQH-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C(=NC=C3)C)=C2S1 JCMPCXLQEBNCQH-UHFFFAOYSA-N 0.000 claims 1
SZQVWVSEUWHRHP-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C(=NC=C2)C)C#N)=C1 SZQVWVSEUWHRHP-UHFFFAOYSA-N 0.000 claims 1
SUFHHZNIZUCIAC-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C(=NC=C2)C)C#N)=C1 SUFHHZNIZUCIAC-UHFFFAOYSA-N 0.000 claims 1
QGBMERFETMYXFP-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C(=NC=C2)C)C#N)=C1 QGBMERFETMYXFP-UHFFFAOYSA-N 0.000 claims 1
GSMXWXYRAKTBEO-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C=C(C)N=C3)=C2S1 GSMXWXYRAKTBEO-UHFFFAOYSA-N 0.000 claims 1
BJYLDXZKYZVJPR-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)ethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C=C(C)N=C3)=C2S1 BJYLDXZKYZVJPR-UHFFFAOYSA-N 0.000 claims 1
NZBDLLJRXMTLNJ-UHFFFAOYSA-N 2-[3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC(O)=O)=C2S1 NZBDLLJRXMTLNJ-UHFFFAOYSA-N 0.000 claims 1
VXDFONYMNNONOS-UHFFFAOYSA-N 2-[3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC(O)=O)C#N)=C1 VXDFONYMNNONOS-UHFFFAOYSA-N 0.000 claims 1
SZJYZOPKRPFQLO-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCOC(C)=O)=C2S1 SZJYZOPKRPFQLO-UHFFFAOYSA-N 0.000 claims 1
CJXHGQQTVNWFAG-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCOC(C)=O)C#N)=C1 CJXHGQQTVNWFAG-UHFFFAOYSA-N 0.000 claims 1
BHKSJWUQDFCKRK-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(2,5-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(OC)C(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCO)C#N)=C1 BHKSJWUQDFCKRK-UHFFFAOYSA-N 0.000 claims 1
QHJVIRDFCKWRCX-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCO)=C2S1 QHJVIRDFCKWRCX-UHFFFAOYSA-N 0.000 claims 1
HOLPCQLWKIDQAH-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCO)C#N)=C1 HOLPCQLWKIDQAH-UHFFFAOYSA-N 0.000 claims 1
RFWJDQUYPALQRP-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(5-methoxy-2-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(C)C(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCO)C#N)=C1 RFWJDQUYPALQRP-UHFFFAOYSA-N 0.000 claims 1
UJAQYKAHKYSABU-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C=NC=C3)=C2S1 UJAQYKAHKYSABU-UHFFFAOYSA-N 0.000 claims 1
NYRZQYQOCFVILO-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3C=NC=C3)=C2S1 NYRZQYQOCFVILO-UHFFFAOYSA-N 0.000 claims 1
OMQYMGWCHPFBNJ-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C=NC=C2)C#N)=C1 OMQYMGWCHPFBNJ-UHFFFAOYSA-N 0.000 claims 1
SOXFNPRRMNCZQW-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C=NC=C2)C#N)=C1 SOXFNPRRMNCZQW-UHFFFAOYSA-N 0.000 claims 1
QYVJPVROQGJNQX-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCN2C=NC=C2)C#N)=C1 QYVJPVROQGJNQX-UHFFFAOYSA-N 0.000 claims 1
WBQMNEIKWSVEIC-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(C)C=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCN3CCOCC3)=C2S1 WBQMNEIKWSVEIC-UHFFFAOYSA-N 0.000 claims 1
DZHDUFJBRZSYGU-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2,5-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(OC)C(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2N=CC=CC=2)C#N)=C1 DZHDUFJBRZSYGU-UHFFFAOYSA-N 0.000 claims 1
AEMWJTPJUWAYBR-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3N=CC=CC=3)=C2S1 AEMWJTPJUWAYBR-UHFFFAOYSA-N 0.000 claims 1
DOMJJDHUKWBXFO-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3N=CC=CC=3)=C2S1 DOMJJDHUKWBXFO-UHFFFAOYSA-N 0.000 claims 1
MRAVFDXPWWRBCT-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(C)C=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3N=CC=CC=3)=C2S1 MRAVFDXPWWRBCT-UHFFFAOYSA-N 0.000 claims 1
CBXYMEWTZXSKDU-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3N=CC=CC=3)=C2S1 CBXYMEWTZXSKDU-UHFFFAOYSA-N 0.000 claims 1
QIHVYSCZJSQDAQ-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3N=CC=CC=3)=C2S1 QIHVYSCZJSQDAQ-UHFFFAOYSA-N 0.000 claims 1
DIRVKDGMXDCTAY-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2N=CC=CC=2)C#N)=C1 DIRVKDGMXDCTAY-UHFFFAOYSA-N 0.000 claims 1
GLPONYAXPUVEQP-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2N=CC=CC=2)C#N)=C1 GLPONYAXPUVEQP-UHFFFAOYSA-N 0.000 claims 1
LTEBHCNOQJUPEB-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2N=CC=CC=2)C#N)=C1 LTEBHCNOQJUPEB-UHFFFAOYSA-N 0.000 claims 1
IENUGCUUPHDZDC-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=NC=CC=3)=C2S1 IENUGCUUPHDZDC-UHFFFAOYSA-N 0.000 claims 1
LMTVPXGSGVNVRM-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=NC=CC=3)=C2S1 LMTVPXGSGVNVRM-UHFFFAOYSA-N 0.000 claims 1
OJAREJAZFWIYCT-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=NC=CC=2)C#N)=C1 OJAREJAZFWIYCT-UHFFFAOYSA-N 0.000 claims 1
NHYVMQYYSDGXRO-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=NC=CC=2)C#N)=C1 NHYVMQYYSDGXRO-UHFFFAOYSA-N 0.000 claims 1
CYDNTFTUPPYCHF-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=NC=CC=2)C#N)=C1 CYDNTFTUPPYCHF-UHFFFAOYSA-N 0.000 claims 1
MISJMGHJINRMJG-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=NC=CC=2)C#N)=C1 MISJMGHJINRMJG-UHFFFAOYSA-N 0.000 claims 1
IWDPRLPUQCHAGM-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=CN=CC=3)=C2S1 IWDPRLPUQCHAGM-UHFFFAOYSA-N 0.000 claims 1
YRSQLWCTTAWZCQ-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(2-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=CN=CC=3)=C2S1 YRSQLWCTTAWZCQ-UHFFFAOYSA-N 0.000 claims 1
XYYKHMNKAHDVQU-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=CN=CC=3)=C2S1 XYYKHMNKAHDVQU-UHFFFAOYSA-N 0.000 claims 1
HLHFYBFVNVDNAY-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(2-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCCC=3C=CN=CC=3)=C2S1 HLHFYBFVNVDNAY-UHFFFAOYSA-N 0.000 claims 1
BNNGCCQRTSZNAI-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=CN=CC=2)C#N)=C1 BNNGCCQRTSZNAI-UHFFFAOYSA-N 0.000 claims 1
YJUUQJWCMDDBEC-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=CN=CC=2)C#N)=C1 YJUUQJWCMDDBEC-UHFFFAOYSA-N 0.000 claims 1
RTJXTICZONZPRI-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=CN=CC=2)C#N)=C1 RTJXTICZONZPRI-UHFFFAOYSA-N 0.000 claims 1
KIVJEGLCSJOIOC-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCCC=2C=CN=CC=2)C#N)=C1 KIVJEGLCSJOIOC-UHFFFAOYSA-N 0.000 claims 1
TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
208000026310 Breast neoplasm Diseases 0.000 claims 1
102000015212 Fas Ligand Protein Human genes 0.000 claims 1
HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 claims 1
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
210000000133 brain stem Anatomy 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 claims 1
WDOGQTQEKVLZIJ-WAYWQWQTSA-N combretastatin a-4 phosphate Chemical compound C1=C(OP(O)(O)=O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 WDOGQTQEKVLZIJ-WAYWQWQTSA-N 0.000 claims 1
POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 claims 1
UVMPSXGPOGBLEC-UHFFFAOYSA-N ethyl 2-[3-(5-bromo-2-methoxyphenyl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC(Br)=CC=C1OC UVMPSXGPOGBLEC-UHFFFAOYSA-N 0.000 claims 1
SJXZEQNQFRCMPO-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,2,3,3-tetrafluoro-6-methoxy-1,4-benzodioxin-5-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(F)(F)C(F)(F)OC2=C1C=CC(OC)=C2CCC(=O)NC(S1)=C(C#N)C2=C1CN(C(=O)OCC)CC2 SJXZEQNQFRCMPO-UHFFFAOYSA-N 0.000 claims 1
SWRDIQQENIHVKF-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,3-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(OC)=C1OC SWRDIQQENIHVKF-UHFFFAOYSA-N 0.000 claims 1
PBFAKNBOESCMML-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,5-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC(OC)=CC=C1OC PBFAKNBOESCMML-UHFFFAOYSA-N 0.000 claims 1
RNNHSMSTXJTKEV-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC(C)=CC=C1OC RNNHSMSTXJTKEV-UHFFFAOYSA-N 0.000 claims 1
VHGIBAGXDSSTLH-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=C1OC VHGIBAGXDSSTLH-UHFFFAOYSA-N 0.000 claims 1
DZDBNSCQATWLIZ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3,5-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC(OC)=CC(OC)=C1 DZDBNSCQATWLIZ-UHFFFAOYSA-N 0.000 claims 1
ZSRKEBITYORZAA-UHFFFAOYSA-N ethyl 3-cyano-2-[3-[2-(trifluoromethoxy)phenyl]propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1OC(F)(F)F ZSRKEBITYORZAA-UHFFFAOYSA-N 0.000 claims 1
BCHADFMXECVBJM-UHFFFAOYSA-N ethyl 3-cyano-2-[[2-(2-methoxy-5-methylphenyl)cyclopropanecarbonyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)C1CC1C1=CC(C)=CC=C1OC BCHADFMXECVBJM-UHFFFAOYSA-N 0.000 claims 1
JABGXPCRNXUENL-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1N=CNC2=NC=N[C]12 JABGXPCRNXUENL-UHFFFAOYSA-N 0.000 claims 1
QOFFJEBXNKRSPX-ZDUSSCGKSA-N pemetrexed Chemical compound C1=N[C]2NC(N)=NC(=O)C2=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QOFFJEBXNKRSPX-ZDUSSCGKSA-N 0.000 claims 1
210000001428 peripheral nervous system Anatomy 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
229940124531 pharmaceutical excipient Drugs 0.000 claims 1
QOKDYUICIHRJSR-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3N=CC=CC=3)=C2S1 QOKDYUICIHRJSR-UHFFFAOYSA-N 0.000 claims 1
NBKLJINMRSIDPD-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2N=CC=CC=2)C#N)=C1 NBKLJINMRSIDPD-UHFFFAOYSA-N 0.000 claims 1
UTPTUQUKBGOFJS-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2,5-dimethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(OC)C(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=NC=CC=2)C#N)=C1 UTPTUQUKBGOFJS-UHFFFAOYSA-N 0.000 claims 1
JLHZOQVEWRVOTJ-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2-methoxy-5-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=C(C)C=C1CCC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=NC=CC=3)=C2S1 JLHZOQVEWRVOTJ-UHFFFAOYSA-N 0.000 claims 1
WYVAAWDFQYJPQT-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=NC=CC=3)=C2S1 WYVAAWDFQYJPQT-UHFFFAOYSA-N 0.000 claims 1
ANLCKNSKNXBCDS-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=NC=CC=2)C#N)=C1 ANLCKNSKNXBCDS-UHFFFAOYSA-N 0.000 claims 1
VWKJPIYZKKRERB-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(2-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCN(C2)C(=O)OCC=3C=CN=CC=3)=C2S1 VWKJPIYZKKRERB-UHFFFAOYSA-N 0.000 claims 1
LYDFCYOKQVGVNS-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(3-methoxyphenyl)butanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC=2C=CN=CC=2)C#N)=C1 LYDFCYOKQVGVNS-UHFFFAOYSA-N 0.000 claims 1
210000004027 cell Anatomy 0.000 description 69
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
238000002360 preparation method Methods 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 23
150000003254 radicals Chemical class 0.000 description 22
239000000243 solution Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
230000006907 apoptotic process Effects 0.000 description 18
208000035475 disorder Diseases 0.000 description 17
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 16
230000022131 cell cycle Effects 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 14
229940080818 propionamide Drugs 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 13
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 13
238000003786 synthesis reaction Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000003085 diluting agent Substances 0.000 description 12
238000000746 purification Methods 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
230000035899 viability Effects 0.000 description 11
230000001413 cellular effect Effects 0.000 description 10
238000010790 dilution Methods 0.000 description 10
239000012895 dilution Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000001028 anti-proliverative effect Effects 0.000 description 9
238000002648 combination therapy Methods 0.000 description 9
239000002609 medium Substances 0.000 description 9
210000000056 organ Anatomy 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
230000008569 process Effects 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
230000001594 aberrant effect Effects 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
230000014509 gene expression Effects 0.000 description 8
230000001939 inductive effect Effects 0.000 description 8
230000035755 proliferation Effects 0.000 description 8
239000000725 suspension Substances 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000005755 formation reaction Methods 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
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 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
206010027476 Metastases Diseases 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
102400001093 PAK-2p27 Human genes 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000010261 cell growth Effects 0.000 description 5
230000004663 cell proliferation Effects 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000001472 cytotoxic effect Effects 0.000 description 5
229940079593 drug Drugs 0.000 description 5
125000002541 furyl group Chemical group 0.000 description 5
239000000411 inducer Substances 0.000 description 5
125000001786 isothiazolyl group Chemical group 0.000 description 5
125000000842 isoxazolyl group Chemical group 0.000 description 5
210000005170 neoplastic cell Anatomy 0.000 description 5
125000001715 oxadiazolyl group Chemical group 0.000 description 5
125000002971 oxazolyl group Chemical group 0.000 description 5
239000005022 packaging material Substances 0.000 description 5
125000002098 pyridazinyl group Chemical group 0.000 description 5
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 5
125000000168 pyrrolyl group Chemical group 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
238000000926 separation method Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
125000001113 thiadiazolyl group Chemical group 0.000 description 5
125000000335 thiazolyl group Chemical group 0.000 description 5
125000001544 thienyl group Chemical group 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 description 4
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
HBJYIPIVHUNXLW-UHFFFAOYSA-N 3-cyano-2-[3-(3-ethoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(O)=O)C#N)=C1 HBJYIPIVHUNXLW-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000005396 acrylic acid ester group Chemical class 0.000 description 4
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 description 4
230000009471 action Effects 0.000 description 4
150000004657 carbamic acid derivatives Chemical class 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
150000003997 cyclic ketones Chemical class 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000002650 habitual effect Effects 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
230000011278 mitosis Effects 0.000 description 4
230000035407 negative regulation of cell proliferation Effects 0.000 description 4
238000010899 nucleation Methods 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000008177 pharmaceutical agent Substances 0.000 description 4
230000002265 prevention Effects 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
229940124597 therapeutic agent Drugs 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
PJYYBCXMCWDUAZ-JJJZTNILSA-N 2,3,14,20,22-pentahydroxy-(2β,3β,5β,22R)-Cholest-7-en-6-one Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 PJYYBCXMCWDUAZ-JJJZTNILSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
PJYYBCXMCWDUAZ-YKDQUOQBSA-N Ponasterone A Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@@](O)([C@@H](O)CCC(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 PJYYBCXMCWDUAZ-YKDQUOQBSA-N 0.000 description 3
230000005856 abnormality Effects 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000010976 amide bond formation reaction Methods 0.000 description 3
230000006909 anti-apoptosis Effects 0.000 description 3
238000003782 apoptosis assay Methods 0.000 description 3
230000008033 biological extinction Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000004364 calculation method Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
230000003833 cell viability Effects 0.000 description 3
230000033077 cellular process Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
239000003480 eluent Substances 0.000 description 3
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 3
IUOVJOCPOBNISH-UHFFFAOYSA-N ethyl 2-amino-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC2=C1SC(N)=C2C#N IUOVJOCPOBNISH-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000006870 function Effects 0.000 description 3
239000000499 gel Substances 0.000 description 3
230000012010 growth Effects 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000009401 metastasis Effects 0.000 description 3
ZJFIVCQTGOPXBG-UHFFFAOYSA-N methyl 2-(2-methylimidazol-1-yl)acetate Chemical compound COC(=O)CN1C=CN=C1C ZJFIVCQTGOPXBG-UHFFFAOYSA-N 0.000 description 3
LSHYODDMCVOPSZ-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-methoxyphenyl)propanamide Chemical compound COC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 LSHYODDMCVOPSZ-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
125000004816 2,2-dimethylethylene group Chemical group [H]C([H])([H])C([*:2])(C([H])([H])[H])C([H])([H])[*:1] 0.000 description 2
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
UKDWWUNLNDAURT-UHFFFAOYSA-N 3-(2-methoxyphenyl)butanoic acid Chemical compound COC1=CC=CC=C1C(C)CC(O)=O UKDWWUNLNDAURT-UHFFFAOYSA-N 0.000 description 2
SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
108010092160 Dactinomycin Proteins 0.000 description 2
206010059866 Drug resistance Diseases 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000006000 Knoevenagel condensation reaction Methods 0.000 description 2
108010000817 Leuprolide Proteins 0.000 description 2
238000005684 Liebig rearrangement reaction Methods 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
206010029113 Neovascularisation Diseases 0.000 description 2
108700020796 Oncogene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
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 description 2
230000010933 acylation Effects 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
230000004075 alteration Effects 0.000 description 2
229940041181 antineoplastic drug Drugs 0.000 description 2
229940120638 avastin Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229940112129 campath Drugs 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
230000030833 cell death Effects 0.000 description 2
229940044683 chemotherapy drug Drugs 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
201000010897 colon adenocarcinoma Diseases 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
238000005888 cyclopropanation reaction Methods 0.000 description 2
125000004980 cyclopropylene group Chemical group 0.000 description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
229960000640 dactinomycin Drugs 0.000 description 2
238000006705 deacetalization reaction Methods 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
125000005805 dimethoxy phenyl group Chemical group 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000003885 epothilone B derivatives Chemical class 0.000 description 2
229940082789 erbitux Drugs 0.000 description 2
239000012894 fetal calf serum Substances 0.000 description 2
OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
201000005787 hematologic cancer Diseases 0.000 description 2
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
229940022353 herceptin Drugs 0.000 description 2
150000002390 heteroarenes Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229960001001 ibritumomab tiuxetan Drugs 0.000 description 2
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000010661 induction of programmed cell death Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229960002014 ixabepilone Drugs 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
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 description 2
229960004338 leuprorelin Drugs 0.000 description 2
239000006166 lysate Substances 0.000 description 2
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
UOCUXOJCFGJJSR-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-ethoxyphenyl)propanamide Chemical compound CCOC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 UOCUXOJCFGJJSR-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
238000011275 oncology therapy Methods 0.000 description 2
230000002018 overexpression Effects 0.000 description 2
229950007460 patupilone Drugs 0.000 description 2
WBXPDJSOTKVWSJ-ZDUSSCGKSA-N pemetrexed Chemical compound C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 WBXPDJSOTKVWSJ-ZDUSSCGKSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000005522 programmed cell death Effects 0.000 description 2
239000012264 purified product Substances 0.000 description 2
230000003362 replicative effect Effects 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000012453 solvate Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000009121 systemic therapy Methods 0.000 description 2
230000008685 targeting Effects 0.000 description 2
229940063683 taxotere Drugs 0.000 description 2
HFWVFBQVIXKINU-UHFFFAOYSA-N tert-butyl 2-amino-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1SC(N)=C2C#N HFWVFBQVIXKINU-UHFFFAOYSA-N 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 2
229960005267 tositumomab Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 2
125000005500 uronium group Chemical group 0.000 description 2
BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 1
YXBQLONCIPUQKO-UJPOAAIJSA-N (1r)-1-[(3ar,5r,6s,6ar)-6-[3-(dimethylamino)propoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol Chemical compound O1C(C)(C)O[C@@H]2[C@@H](OCCCN(C)C)[C@@H]([C@H](O)CO)O[C@@H]21 YXBQLONCIPUQKO-UJPOAAIJSA-N 0.000 description 1
JZYQZJIQUVBWAR-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-[3-(3-methoxyphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCN(CC=3S2)C(=O)OCC2OC(C)(C)OC2)C#N)=C1 JZYQZJIQUVBWAR-UHFFFAOYSA-N 0.000 description 1
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
PUDHBTGHUJUUFI-SCTWWAJVSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2r)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-p Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](N)CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(N)=O)=O)C(C)C)C1=CC=C(O)C=C1 PUDHBTGHUJUUFI-SCTWWAJVSA-N 0.000 description 1
OMJKFYKNWZZKTK-POHAHGRESA-N (5z)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide Chemical compound CN(C)N\N=C1/N=CN=C1C(N)=O OMJKFYKNWZZKTK-POHAHGRESA-N 0.000 description 1
WTSKMKRYHATLLL-UHFFFAOYSA-N (6-benzoyloxy-3-cyanopyridin-2-yl) 3-[3-(ethoxymethyl)-5-fluoro-2,6-dioxopyrimidine-1-carbonyl]benzoate Chemical compound O=C1N(COCC)C=C(F)C(=O)N1C(=O)C1=CC=CC(C(=O)OC=2C(=CC=C(OC(=O)C=3C=CC=CC=3)N=2)C#N)=C1 WTSKMKRYHATLLL-UHFFFAOYSA-N 0.000 description 1
KMSKQZKKOZQFFG-YXRRJAAWSA-N (7S,9S)-7-[[(2R,4S,5S,6S)-4-amino-6-methyl-5-[[(2R)-2-oxanyl]oxy]-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)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]1CCCCO1 KMSKQZKKOZQFFG-YXRRJAAWSA-N 0.000 description 1
FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
MHFRGQHAERHWKZ-MHZLTWQESA-N (S)-edelfosine Chemical compound CCCCCCCCCCCCCCCCCCOC[C@H](OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-MHZLTWQESA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
CVQCUWHQOBRPPH-RUDMXATFSA-N (e)-2-(2-methoxy-5-methylphenyl)but-2-enoic acid Chemical compound COC1=CC=C(C)C=C1\C(=C/C)C(O)=O CVQCUWHQOBRPPH-RUDMXATFSA-N 0.000 description 1
USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical class OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 1
125000004815 1,2-dimethylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([*:2])C([H])([H])[H] 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 1
TVGMOUGXQYQZOL-UHFFFAOYSA-N 1-(2-ethoxyphenyl)ethanone Chemical compound CCOC1=CC=CC=C1C(C)=O TVGMOUGXQYQZOL-UHFFFAOYSA-N 0.000 description 1
RUWWFEHTGUJEDT-UHFFFAOYSA-N 1-(3-ethoxyphenyl)ethanone Chemical compound CCOC1=CC=CC(C(C)=O)=C1 RUWWFEHTGUJEDT-UHFFFAOYSA-N 0.000 description 1
125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
VBTCFNBQFGRGKD-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(C)C=C1C(=C)C(O)=O VBTCFNBQFGRGKD-UHFFFAOYSA-N 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
QXLQZLBNPTZMRK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2,4-dimethylphenyl)prop-2-en-1-one Chemical compound CN(C)CC(=C)C(=O)C1=CC=C(C)C=C1C QXLQZLBNPTZMRK-UHFFFAOYSA-N 0.000 description 1
RRECQJYPJNWFNK-BCKSSGNJSA-N 2-[(e)-[(1e)-1-(diaminomethylidenehydrazinylidene)propan-2-ylidene]amino]guanidine;hydrochloride Chemical compound Cl.NC(=N)N\N=C(/C)\C=N\NC(N)=N RRECQJYPJNWFNK-BCKSSGNJSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CNLWNYCFDMAZCB-HUVROIHYSA-N 2-[2-[[2-[[(2r)-1-[[(4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-16-benzyl-4-[[(2r,3r)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl]amino]-1-oxo-3-phe Chemical compound C([C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)NC(=O)CN(CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)CC(O)=O)C1=CC=CC=C1 CNLWNYCFDMAZCB-HUVROIHYSA-N 0.000 description 1
RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 description 1
BYZJBHCTZJGJFV-AOOOYVTPSA-N 2-[[(2s,3r)-2,3-dihydroxy-4-(2-methylsulfonyloxyethylamino)butyl]amino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC[C@H](O)[C@H](O)CNCCOS(C)(=O)=O BYZJBHCTZJGJFV-AOOOYVTPSA-N 0.000 description 1
UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical class NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
GGOUKXJLOUNPFF-UHFFFAOYSA-N 2-methoxy-1-(2-methylphenyl)ethanone Chemical compound COCC(=O)C1=CC=CC=C1C GGOUKXJLOUNPFF-UHFFFAOYSA-N 0.000 description 1
CJVIGQCGJUDKOE-UHFFFAOYSA-N 2-methoxy-5-methylbenzaldehyde Chemical compound COC1=CC=C(C)C=C1C=O CJVIGQCGJUDKOE-UHFFFAOYSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical compound N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 1
NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
MMDQGELAMOGWKS-UHFFFAOYSA-N 3-(2-ethoxyphenyl)butanoic acid Chemical compound CCOC1=CC=CC=C1C(C)CC(O)=O MMDQGELAMOGWKS-UHFFFAOYSA-N 0.000 description 1
IBGXZMNEERGARC-UHFFFAOYSA-N 3-(2-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC=C1CCC(O)=O IBGXZMNEERGARC-UHFFFAOYSA-N 0.000 description 1
ITXXGASEFOCNOS-UHFFFAOYSA-N 3-(2-methoxy-5-methylphenyl)butanoic acid Chemical compound COC1=CC=C(C)C=C1C(C)CC(O)=O ITXXGASEFOCNOS-UHFFFAOYSA-N 0.000 description 1
KLVRTUOZJWPLSU-UHFFFAOYSA-N 3-(2-methoxy-5-methylphenyl)propanoic acid Chemical compound COC1=CC=C(C)C=C1CCC(O)=O KLVRTUOZJWPLSU-UHFFFAOYSA-N 0.000 description 1
XSZSNLOPIWWFHS-UHFFFAOYSA-N 3-(2-methoxyphenyl)propanoic acid Chemical compound COC1=CC=CC=C1CCC(O)=O XSZSNLOPIWWFHS-UHFFFAOYSA-N 0.000 description 1
RPYQHOHIUOJNSU-UHFFFAOYSA-N 3-(3-ethoxyphenyl)butanoic acid Chemical compound CCOC1=CC=CC(C(C)CC(O)=O)=C1 RPYQHOHIUOJNSU-UHFFFAOYSA-N 0.000 description 1
GAMHAASXRNFGCJ-UHFFFAOYSA-N 3-(3-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC(CCC(O)=O)=C1 GAMHAASXRNFGCJ-UHFFFAOYSA-N 0.000 description 1
XDMVUTYPFLYVOH-UHFFFAOYSA-N 3-(3-methoxyphenyl)butanoic acid Chemical compound COC1=CC=CC(C(C)CC(O)=O)=C1 XDMVUTYPFLYVOH-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
BJJQJLOZWBZEGA-UHFFFAOYSA-N 3-Methoxybenzenepropanoic acid Chemical compound COC1=CC=CC(CCC(O)=O)=C1 BJJQJLOZWBZEGA-UHFFFAOYSA-N 0.000 description 1
QNKJFXARIMSDBR-UHFFFAOYSA-N 3-[2-[bis(2-chloroethyl)amino]ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound O=C1N(CCN(CCCl)CCCl)C(=O)NC11CCCCC1 QNKJFXARIMSDBR-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 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 description 1
CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
UEVABMBUZNGYQI-UHFFFAOYSA-N 4-methoxypyridine-2-carbaldehyde Chemical compound COC1=CC=NC(C=O)=C1 UEVABMBUZNGYQI-UHFFFAOYSA-N 0.000 description 1
BZWQQOVSUSJJJO-QAGDRQIHSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione;hydrate Chemical compound O.O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BZWQQOVSUSJJJO-QAGDRQIHSA-N 0.000 description 1
WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 1
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 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 description 1
102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 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 description 1
WOVKYSAHUYNSMH-UHFFFAOYSA-N BROMODEOXYURIDINE Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
MXSKNGCQFBRXJK-UHFFFAOYSA-N C(C)(=O)N.C(#N)C1=CSC=C1 Chemical class C(C)(=O)N.C(#N)C1=CSC=C1 MXSKNGCQFBRXJK-UHFFFAOYSA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
IKSJCVFYCIKDTB-GZZWOGMVSA-N CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@@H](C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@@H](C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O IKSJCVFYCIKDTB-GZZWOGMVSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
102000011727 Caspases Human genes 0.000 description 1
108010076667 Caspases Proteins 0.000 description 1
108010077544 Chromatin Proteins 0.000 description 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 description 1
HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 1
238000006942 Corey-Chaykovsky ring formation reaction Methods 0.000 description 1
102000000577 Cyclin-Dependent Kinase Inhibitor p27 Human genes 0.000 description 1
108010016777 Cyclin-Dependent Kinase Inhibitor p27 Proteins 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
230000004543 DNA replication Effects 0.000 description 1
230000006820 DNA synthesis Effects 0.000 description 1
GJKXGJCSJWBJEZ-XRSSZCMZSA-N Deslorelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)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)CC1=CNC2=CC=CC=C12 GJKXGJCSJWBJEZ-XRSSZCMZSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 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 description 1
238000002965 ELISA Methods 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 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 description 1
OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 description 1
KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
230000010190 G1 phase Effects 0.000 description 1
230000010337 G2 phase Effects 0.000 description 1
238000006937 Gewald synthesis reaction Methods 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
229940122904 Glucagon receptor antagonist Drugs 0.000 description 1
102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
238000007341 Heck reaction Methods 0.000 description 1
108010033040 Histones Proteins 0.000 description 1
102000006947 Histones Human genes 0.000 description 1
241000282412 Homo Species 0.000 description 1
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 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 description 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 description 1
239000005639 Lauric acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
230000027311 M phase Effects 0.000 description 1
190000032366 MIBOPLATIN Chemical compound 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
229930192392 Mitomycin Natural products 0.000 description 1
HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 description 1
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
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 description 1
OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
LYPFDBRUNKHDGX-SOGSVHMOSA-N N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 Chemical compound N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 LYPFDBRUNKHDGX-SOGSVHMOSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
108010016076 Octreotide Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
208000020584 Polyploidy Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 1
AHHFEZNOXOZZQA-ZEBDFXRSSA-N Ranimustine Chemical compound CO[C@H]1O[C@H](CNC(=O)N(CCCl)N=O)[C@@H](O)[C@H](O)[C@H]1O AHHFEZNOXOZZQA-ZEBDFXRSSA-N 0.000 description 1
201000000582 Retinoblastoma Diseases 0.000 description 1
190014017285 SATRAPLATIN Chemical compound 0.000 description 1
238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 1
102000011990 Sirtuin Human genes 0.000 description 1
108050002485 Sirtuin Proteins 0.000 description 1
OCOKWVBYZHBHLU-UHFFFAOYSA-N Sobuzoxane Chemical compound C1C(=O)N(COC(=O)OCC(C)C)C(=O)CN1CCN1CC(=O)N(COC(=O)OCC(C)C)C(=O)C1 OCOKWVBYZHBHLU-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
108010078233 Thymalfasin Proteins 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 description 1
102100031988 Tumor necrosis factor ligand superfamily member 6 Human genes 0.000 description 1
RLXPIABKJFUYFG-DOYDWZMXSA-M [(1R,2R)-2-(aminomethyl)cyclobutyl]methanamine (2S)-2-oxidopropanoate platinum(2+) Chemical compound [Pt+2].C[C@H]([O-])C([O-])=O.NC[C@@H]1CC[C@H]1CN RLXPIABKJFUYFG-DOYDWZMXSA-M 0.000 description 1
XJXKGUZINMNEDK-GPJOBVNKSA-L [(4r,5r)-5-(aminomethyl)-2-propan-2-yl-1,3-dioxolan-4-yl]methanamine;platinum(2+);propanedioate Chemical compound [Pt+2].[O-]C(=O)CC([O-])=O.CC(C)C1O[C@H](CN)[C@@H](CN)O1 XJXKGUZINMNEDK-GPJOBVNKSA-L 0.000 description 1
JQXXHWHPUNPDRT-ZNQWNCHJSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)Nc2c(O)c3c(O)c4C)C)OC)c4c1c3c(O)c2C=NN1CCN(C)CC1 JQXXHWHPUNPDRT-ZNQWNCHJSA-N 0.000 description 1
AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
229960002184 abarelix Drugs 0.000 description 1
108010023617 abarelix Proteins 0.000 description 1
229960000446 abciximab Drugs 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 1
229960004176 aclarubicin Drugs 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 description 1
229960002916 adapalene Drugs 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
210000004404 adrenal cortex Anatomy 0.000 description 1
238000003349 alamar blue assay Methods 0.000 description 1
229940060265 aldara Drugs 0.000 description 1
229940110282 alimta Drugs 0.000 description 1
229940098174 alkeran Drugs 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229960000473 altretamine Drugs 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960003437 aminoglutethimide Drugs 0.000 description 1
ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
229950010999 amiprilose Drugs 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
229960002550 amrubicin Drugs 0.000 description 1
VJZITPJGSQKZMX-XDPRQOKASA-N amrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)(N)C(=O)C)[C@H]1C[C@H](O)[C@H](O)CO1 VJZITPJGSQKZMX-XDPRQOKASA-N 0.000 description 1
229960002932 anastrozole Drugs 0.000 description 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 description 1
229950000242 ancitabine Drugs 0.000 description 1
BBDAGFIXKZCXAH-CCXZUQQUSA-N ancitabine Chemical compound N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 BBDAGFIXKZCXAH-CCXZUQQUSA-N 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
230000002804 anti-anaphylactic effect Effects 0.000 description 1
230000002942 anti-growth Effects 0.000 description 1
230000003326 anti-histaminergic effect Effects 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
229960004191 artemisinin Drugs 0.000 description 1
BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 1
229930101531 artemisinin Natural products 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 description 1
229960002170 azathioprine Drugs 0.000 description 1
LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
229960004669 basiliximab Drugs 0.000 description 1
229960002707 bendamustine Drugs 0.000 description 1
YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
229960000997 bicalutamide Drugs 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
229950004398 broxuridine Drugs 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
229960002092 busulfan Drugs 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229940088954 camptosar Drugs 0.000 description 1
239000012830 cancer therapeutic Substances 0.000 description 1
239000007894 caplet Substances 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
229960002115 carboquone Drugs 0.000 description 1
229960005243 carmustine Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000013592 cell lysate Substances 0.000 description 1
238000003570 cell viability assay Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229960003230 cetrorelix Drugs 0.000 description 1
SBNPWPIBESPSIF-MHWMIDJBSA-N cetrorelix Chemical compound C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 SBNPWPIBESPSIF-MHWMIDJBSA-N 0.000 description 1
108700008462 cetrorelix Proteins 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000012069 chiral reagent Substances 0.000 description 1
229960004630 chlorambucil Drugs 0.000 description 1
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
210000003483 chromatin Anatomy 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229960002436 cladribine Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229960003608 clomifene Drugs 0.000 description 1
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013066 combination product Substances 0.000 description 1
229940127555 combination product Drugs 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004976 cyclobutylene group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004977 cycloheptylene group Chemical group 0.000 description 1
125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004979 cyclopentylene group Chemical group 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
229960003901 dacarbazine Drugs 0.000 description 1
229960002806 daclizumab Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 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 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000009795 derivation Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
229960005408 deslorelin Drugs 0.000 description 1
108700025485 deslorelin Proteins 0.000 description 1
230000000368 destabilizing effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229960000605 dexrazoxane Drugs 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
NLORYLAYLIXTID-ISLYRVAYSA-N diethylstilbestrol diphosphate Chemical compound C=1C=C(OP(O)(O)=O)C=CC=1C(/CC)=C(\CC)C1=CC=C(OP(O)(O)=O)C=C1 NLORYLAYLIXTID-ISLYRVAYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 1
229950005454 doxifluridine Drugs 0.000 description 1
229950004203 droloxifene Drugs 0.000 description 1
229950005101 drostanolone Drugs 0.000 description 1
229950011461 edelfosine Drugs 0.000 description 1
VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
229960002759 eflornithine Drugs 0.000 description 1
229950005450 emitefur Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
229960001904 epirubicin Drugs 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
229950002973 epitiostanol Drugs 0.000 description 1
229950006835 eptaplatin Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
229960001842 estramustine Drugs 0.000 description 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 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
229960000752 etoposide phosphate Drugs 0.000 description 1
229960000255 exemestane Drugs 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
229950011548 fadrozole Drugs 0.000 description 1
239000012065 filter cake Substances 0.000 description 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 description 1
229960004039 finasteride Drugs 0.000 description 1
229960000961 floxuridine Drugs 0.000 description 1
ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
229960004413 flucytosine Drugs 0.000 description 1
229960005304 fludarabine phosphate Drugs 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229960000304 folic acid Drugs 0.000 description 1
235000019152 folic acid Nutrition 0.000 description 1
229960004421 formestane Drugs 0.000 description 1
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
229960005102 foscarnet Drugs 0.000 description 1
229960000297 fosfestrol Drugs 0.000 description 1
229960004783 fotemustine Drugs 0.000 description 1
YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229960002258 fulvestrant Drugs 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
229940020967 gemzar Drugs 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
IDINUJSAMVOPCM-UHFFFAOYSA-N gusperimus Chemical compound NCCCNCCCCNC(=O)C(O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-UHFFFAOYSA-N 0.000 description 1
229960002706 gusperimus Drugs 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940088013 hycamtin Drugs 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
238000007031 hydroxymethylation reaction Methods 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
229960004716 idoxuridine Drugs 0.000 description 1
YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
229950008097 improsulfan Drugs 0.000 description 1
DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229960000598 infliximab Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
230000009545 invasion Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229940084651 iressa Drugs 0.000 description 1
GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 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 description 1
229960002437 lanreotide Drugs 0.000 description 1
108010021336 lanreotide Proteins 0.000 description 1
239000010410 layer Substances 0.000 description 1
229960003881 letrozole Drugs 0.000 description 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 description 1
XZEUAXYWNKYKPL-WDYNHAJCSA-N levormeloxifene Chemical compound C1([C@H]2[C@@H](C3=CC=C(C=C3OC2(C)C)OC)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 XZEUAXYWNKYKPL-WDYNHAJCSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229950008991 lobaplatin Drugs 0.000 description 1
229960002247 lomustine Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000012139 lysis buffer Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229960004961 mechlorethamine Drugs 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940087646 methanolamine Drugs 0.000 description 1
IKXILDNPCZPPRV-RFMGOVQKSA-N metholone Chemical compound C1C[C@@H]2[C@@]3(C)C[C@@H](C)C(=O)C[C@@H]3CC[C@H]2[C@@H]2CC[C@H](O)[C@]21C IKXILDNPCZPPRV-RFMGOVQKSA-N 0.000 description 1
JVOOIPKYFSIXKN-UHFFFAOYSA-N methyl 2-(2,4-dimethylimidazol-1-yl)acetate Chemical compound COC(=O)CN1C=C(C)N=C1C JVOOIPKYFSIXKN-UHFFFAOYSA-N 0.000 description 1
FGLBWAGHMWYXNX-UHFFFAOYSA-N methyl 2-(4-methylimidazol-1-yl)acetate Chemical compound COC(=O)CN1C=NC(C)=C1 FGLBWAGHMWYXNX-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
QTFKTBRIGWJQQL-UHFFFAOYSA-N meturedepa Chemical compound C1C(C)(C)N1P(=O)(NC(=O)OCC)N1CC1(C)C QTFKTBRIGWJQQL-UHFFFAOYSA-N 0.000 description 1
229950009847 meturedepa Drugs 0.000 description 1
229950002777 miboplatin Drugs 0.000 description 1
VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 1
229960003248 mifepristone Drugs 0.000 description 1
PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 description 1
229960003775 miltefosine Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229950008541 mirimostim Drugs 0.000 description 1
CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
229960003539 mitoguazone Drugs 0.000 description 1
229950010913 mitolactol Drugs 0.000 description 1
VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
230000036456 mitotic arrest Effects 0.000 description 1
230000000394 mitotic effect Effects 0.000 description 1
210000000479 mitotic spindle apparatus Anatomy 0.000 description 1
229960001156 mitoxantrone Drugs 0.000 description 1
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 description 1
238000002156 mixing Methods 0.000 description 1
229950000844 mizoribine Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
229950011637 motexafin Drugs 0.000 description 1
JFOHFDSMPQIOES-UHFFFAOYSA-N motexafin Chemical compound C1=NC2=CC(OCCOCCOCCOC)=C(OCCOCCOCCOC)C=C2N=CC(C(=C2CCCO)C)=NC2=CC(C(CC)=C2CC)=NC2=CC2=C(CCCO)C(C)=C1N2 JFOHFDSMPQIOES-UHFFFAOYSA-N 0.000 description 1
230000036457 multidrug resistance Effects 0.000 description 1
230000035772 mutation Effects 0.000 description 1
OWVQMAAWIHBNJX-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2,3-dimethoxyphenyl)propanamide Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1OC OWVQMAAWIHBNJX-UHFFFAOYSA-N 0.000 description 1
MPCCBRAFQKTIEC-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2,5-dimethoxyphenyl)propanamide Chemical compound COC1=CC=C(OC)C(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 MPCCBRAFQKTIEC-UHFFFAOYSA-N 0.000 description 1
WDASGPNNZZBCFL-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-ethoxyphenyl)butanamide Chemical compound CCOC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCNC2)=C2S1 WDASGPNNZZBCFL-UHFFFAOYSA-N 0.000 description 1
FNIOAPBXZDLJBX-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-methoxyphenyl)butanamide Chemical compound COC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCNC2)=C2S1 FNIOAPBXZDLJBX-UHFFFAOYSA-N 0.000 description 1
ACTFZHMVSDSKNU-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-ethoxyphenyl)butanamide Chemical compound CCOC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 ACTFZHMVSDSKNU-UHFFFAOYSA-N 0.000 description 1
SBPSJCASRFWASG-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-ethoxyphenyl)propanamide Chemical compound CCOC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 SBPSJCASRFWASG-UHFFFAOYSA-N 0.000 description 1
NJOJOVLTCMDVKE-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-methoxyphenyl)butanamide Chemical compound COC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 NJOJOVLTCMDVKE-UHFFFAOYSA-N 0.000 description 1
KSDPNQKMUSKXLG-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-methoxyphenyl)propanamide Chemical compound COC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 KSDPNQKMUSKXLG-UHFFFAOYSA-N 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
229950010676 nartograstim Drugs 0.000 description 1
108010032539 nartograstim Proteins 0.000 description 1
229950007221 nedaplatin Drugs 0.000 description 1
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
229960002653 nilutamide Drugs 0.000 description 1
229960001420 nimustine Drugs 0.000 description 1
VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229960002700 octreotide Drugs 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003327 ormeloxifene Drugs 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
229960000402 palivizumab Drugs 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
HQQSBEDKMRHYME-UHFFFAOYSA-N pefloxacin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 HQQSBEDKMRHYME-UHFFFAOYSA-N 0.000 description 1
229960001744 pegaspargase Drugs 0.000 description 1
108010001564 pegaspargase Proteins 0.000 description 1
229960001373 pegfilgrastim Drugs 0.000 description 1
108010044644 pegfilgrastim Proteins 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229960003465 pentetreotide Drugs 0.000 description 1
108700023050 pentetreotide Proteins 0.000 description 1
FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
229960002340 pentostatin Drugs 0.000 description 1
229950009351 perfosfamide Drugs 0.000 description 1
VPAWVRUHMJVRHU-VGDKGRGNSA-N perfosfamide Chemical compound OO[C@@H]1CCO[P@@](=O)(N(CCCl)CCCl)N1 VPAWVRUHMJVRHU-VGDKGRGNSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 1
229950001100 piposulfan Drugs 0.000 description 1
229960001221 pirarubicin Drugs 0.000 description 1
229960003171 plicamycin Drugs 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
HIGSLXSBYYMVKI-UHFFFAOYSA-N pralidoxime chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1\C=N\O HIGSLXSBYYMVKI-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
229960004694 prednimustine Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000861 pro-apoptotic effect Effects 0.000 description 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
229960000624 procarbazine Drugs 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 1
229950002828 propagermanium Drugs 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
QZJPEEOEZVHUAE-UHFFFAOYSA-L prospidium chloride Chemical compound [Cl-].[Cl-].C1CN(CC(CCl)O)CC[N+]21CC[N+]1(CCN(CC(O)CCl)CC1)CC2 QZJPEEOEZVHUAE-UHFFFAOYSA-L 0.000 description 1
229950010755 prospidium chloride Drugs 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
108020000494 protein-tyrosine phosphatase Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000000649 purine antagonist Substances 0.000 description 1
229940117820 purinethol Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
229960004432 raltitrexed Drugs 0.000 description 1
229960002185 ranimustine Drugs 0.000 description 1
229950007649 ranpirnase Drugs 0.000 description 1
108010061338 ranpirnase Proteins 0.000 description 1
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
229960000424 rasburicase Drugs 0.000 description 1
108010084837 rasburicase Proteins 0.000 description 1
229960000460 razoxane Drugs 0.000 description 1
BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
229950003651 ritrosulfan Drugs 0.000 description 1
229950003733 romurtide Drugs 0.000 description 1
108700033545 romurtide Proteins 0.000 description 1
229950000261 ruboxistaurin Drugs 0.000 description 1
ZCBUQCWBWNUWSU-SFHVURJKSA-N ruboxistaurin Chemical compound O=C1NC(=O)C2=C1C(C1=CC=CC=C11)=CN1CCO[C@H](CN(C)C)CCN1C3=CC=CC=C3C2=C1 ZCBUQCWBWNUWSU-SFHVURJKSA-N 0.000 description 1
229960002530 sargramostim Drugs 0.000 description 1
108010038379 sargramostim Proteins 0.000 description 1
229960005399 satraplatin Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
208000011581 secondary neoplasm Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229960002930 sirolimus Drugs 0.000 description 1
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229950010372 sobuzoxane Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229950006050 spiromustine Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
229940034785 sutent Drugs 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940120982 tarceva Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960003102 tasonermin Drugs 0.000 description 1
229960001674 tegafur Drugs 0.000 description 1
WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
229960002197 temoporfin Drugs 0.000 description 1
229960004964 temozolomide Drugs 0.000 description 1
229960001278 teniposide Drugs 0.000 description 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 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
229960005353 testolactone Drugs 0.000 description 1
BPEWUONYVDABNZ-DZBHQSCQSA-N testolactone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(OC(=O)CC4)[C@@H]4[C@@H]3CCC2=C1 BPEWUONYVDABNZ-DZBHQSCQSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
229960004231 thymalfasin Drugs 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 description 1
229950011457 tiamiprine Drugs 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229960005026 toremifene Drugs 0.000 description 1
XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
229960003181 treosulfan Drugs 0.000 description 1
PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
229960004560 triaziquone Drugs 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
229960001099 trimetrexate Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229960000875 trofosfamide Drugs 0.000 description 1
UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
229950006929 uredepa Drugs 0.000 description 1
ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
229960000653 valrubicin Drugs 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
229940099039 velcade Drugs 0.000 description 1
ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N verteporfin Chemical compound C=1C([C@@]2([C@H](C(=O)OC)C(=CC=C22)C(=O)OC)C)=NC2=CC(C(=C2C=C)C)=NC2=CC(C(=C2CCC(O)=O)C)=NC2=CC2=NC=1C(C)=C2CCC(=O)OC ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N 0.000 description 1
229960003895 verteporfin Drugs 0.000 description 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine 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-CFWMRBGOSA-N 0.000 description 1
UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
229960004355 vindesine Drugs 0.000 description 1
GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound 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 GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
229960001771 vorozole Drugs 0.000 description 1
XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940053867 xeloda Drugs 0.000 description 1