AU2006212224A1 - Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer - Google Patents

Info

Publication number

AU2006212224A1

AU2006212224A1 AU2006212224A AU2006212224A AU2006212224A1 AU 2006212224 A1 AU2006212224 A1 AU 2006212224A1 AU 2006212224 A AU2006212224 A AU 2006212224A AU 2006212224 A AU2006212224 A AU 2006212224A AU 2006212224 A1 AU2006212224 A1 AU 2006212224A1

Authority

AU

Australia

Prior art keywords

cyano

dihydro

thieno

pyridine

carboxylic acid

Prior art date

2005-02-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 206010028980 Neoplasm Diseases 0.000 title claims description 91
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 71
• 201000011510 cancer Diseases 0.000 title claims description 47
• 201000010099 disease Diseases 0.000 title claims description 42
• 230000002062 proliferating effect Effects 0.000 title claims description 24
• 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 8
• 150000001875 compounds Chemical class 0.000 claims description 477
• -1 1-4C-alkoxycarbonyl Chemical group 0.000 claims description 384
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 174
• 229910052801 chlorine Inorganic materials 0.000 claims description 111
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 110
• 239000000460 chlorine Substances 0.000 claims description 110
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 97
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
• 229910052731 fluorine Inorganic materials 0.000 claims description 80
• 239000011737 fluorine Substances 0.000 claims description 80
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 79
• 125000004076 pyridyl group Chemical group 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 69
• 238000000034 method Methods 0.000 claims description 62
• 229910052799 carbon Inorganic materials 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 52
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 50
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 50
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 49
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 48
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
• 125000002541 furyl group Chemical group 0.000 claims description 47
• 125000001544 thienyl group Chemical group 0.000 claims description 47
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 150000003254 radicals Chemical class 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 37
• 239000002246 antineoplastic agent Substances 0.000 claims description 36
• 150000001721 carbon Chemical group 0.000 claims description 34
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
• 239000000470 constituent Substances 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 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
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
• 230000009826 neoplastic cell growth Effects 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 230000006882 induction of apoptosis Effects 0.000 claims description 25
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
• 239000001301 oxygen Chemical group 0.000 claims description 23
• 125000002883 imidazolyl group Chemical group 0.000 claims description 21
• 125000004122 cyclic group Chemical group 0.000 claims description 20
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 18
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 18
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
• 125000002950 monocyclic group Chemical group 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 15
• 229910052717 sulfur Chemical group 0.000 claims description 15
• 125000000229 (C1-C4)alkoxy group Chemical class 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 239000005864 Sulphur Chemical group 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 238000002560 therapeutic procedure Methods 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 11
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 10
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 10
• 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000001425 triazolyl 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
• HJUKZVDEKGIRHY-UHFFFAOYSA-N 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound S1C=2CN(C(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 HJUKZVDEKGIRHY-UHFFFAOYSA-N 0.000 claims description 7
• 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
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 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
• 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
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
• 229960000435 oblimersen Drugs 0.000 claims description 6
• 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
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
• 239000003795 chemical substances by application Substances 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
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 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
• 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
• 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
• 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
• SJGPTRDNBRAKDG-UHFFFAOYSA-N ethyl 3-cyano-2-[(2-morpholin-4-ylacetyl)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)CN1CCOCC1 SJGPTRDNBRAKDG-UHFFFAOYSA-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
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 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
• IDXDMHGZQWHGAV-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 IDXDMHGZQWHGAV-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
• HKJONPXSQFRXIK-UHFFFAOYSA-N ethyl 3-cyano-2-[[2-(2,3-dihydroindol-1-yl)acetyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1CC2=CC=CC=C2N1CC(=O)NC(S1)=C(C#N)C2=C1CN(C(=O)OCC)CC2 HKJONPXSQFRXIK-UHFFFAOYSA-N 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
• OCRUFYDNBJQRAL-UHFFFAOYSA-N tert-butyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 OCRUFYDNBJQRAL-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
• SHUYVCSHMBOIAR-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CN=CN1C SHUYVCSHMBOIAR-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
• JJCSZDOAJMEADZ-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 JJCSZDOAJMEADZ-UHFFFAOYSA-N 0.000 claims description 2
• UMAVFHLBRFORJA-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC(O)CO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 UMAVFHLBRFORJA-UHFFFAOYSA-N 0.000 claims description 2
• BQUXDRQDUMDGRV-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 BQUXDRQDUMDGRV-UHFFFAOYSA-N 0.000 claims description 2
• DNHZZPLVTHWYJP-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=CN=C1 DNHZZPLVTHWYJP-UHFFFAOYSA-N 0.000 claims description 2
• AIXSBPCKFQRKHP-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-(3-phenylpropanoylamino)-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=C1 AIXSBPCKFQRKHP-UHFFFAOYSA-N 0.000 claims description 2
• LPAXGZFTPQZCEW-UHFFFAOYSA-N 2-phenylmethoxyethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCOCC=3C=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 LPAXGZFTPQZCEW-UHFFFAOYSA-N 0.000 claims description 2
• CTIQKCBYKPKJJI-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 CTIQKCBYKPKJJI-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
• 229940060265 aldara 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
• 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 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
• 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
• LFDUVKNXFWYBKC-UHFFFAOYSA-N ethyl 2-[3-(2-bromophenyl)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=CC=C1Br LFDUVKNXFWYBKC-UHFFFAOYSA-N 0.000 claims description 2
• UGESIBIPQUWSIR-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenyl)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=CC=C1Cl UGESIBIPQUWSIR-UHFFFAOYSA-N 0.000 claims description 2
• IBVRGOGPGFVSPF-UHFFFAOYSA-N ethyl 2-[3-(3-chlorophenyl)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=CC(Cl)=C1 IBVRGOGPGFVSPF-UHFFFAOYSA-N 0.000 claims description 2
• LJTHHKCFHVZWQL-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)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=C(Cl)C=C1 LJTHHKCFHVZWQL-UHFFFAOYSA-N 0.000 claims description 2
• LQEYHCYNUJJGOG-UHFFFAOYSA-N ethyl 3-cyano-2-(3-cyclohexylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1CCCCC1 LQEYHCYNUJJGOG-UHFFFAOYSA-N 0.000 claims description 2
• VMYIOABIKYDVDU-UHFFFAOYSA-N ethyl 3-cyano-2-(3-phenylbutanoylamino)-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=C1 VMYIOABIKYDVDU-UHFFFAOYSA-N 0.000 claims description 2
• XHYULAYWWRGZBB-UHFFFAOYSA-N ethyl 3-cyano-2-(3-thiophen-2-ylpropanoylamino)-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=CS1 XHYULAYWWRGZBB-UHFFFAOYSA-N 0.000 claims description 2
• OZOLJVHMRJMLIT-UHFFFAOYSA-N ethyl 3-cyano-2-[(2-methyl-3-phenylpropanoyl)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)C(C)CC1=CC=CC=C1 OZOLJVHMRJMLIT-UHFFFAOYSA-N 0.000 claims description 2
• YVQANBWUHBRXPI-UHFFFAOYSA-N ethyl 3-cyano-2-[(3-methyl-3-phenylbutanoyl)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)CC(C)(C)C1=CC=CC=C1 YVQANBWUHBRXPI-UHFFFAOYSA-N 0.000 claims description 2
• MISQHTMFDQFFHU-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-fluorophenyl)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=C1F MISQHTMFDQFFHU-UHFFFAOYSA-N 0.000 claims description 2
• KTXNLXRVQDSQHD-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-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=CC=C1C KTXNLXRVQDSQHD-UHFFFAOYSA-N 0.000 claims description 2
• DRQSCSBZVFDSFV-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-fluorophenyl)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(F)=C1 DRQSCSBZVFDSFV-UHFFFAOYSA-N 0.000 claims description 2
• JHVZMRAARHOQEQ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-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=CC(C)=C1 JHVZMRAARHOQEQ-UHFFFAOYSA-N 0.000 claims description 2
• CDHRNLISPUMGKK-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-fluorophenyl)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(F)C=C1 CDHRNLISPUMGKK-UHFFFAOYSA-N 0.000 claims description 2
• WMKSYONSCKXRPJ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-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(C)C=C1 WMKSYONSCKXRPJ-UHFFFAOYSA-N 0.000 claims description 2
• VLUFMGNROYTKQS-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(5-methylpyrazol-1-yl)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)CCN1N=CC=C1C VLUFMGNROYTKQS-UHFFFAOYSA-N 0.000 claims description 2
• XEQHDALQOYILDN-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(oxolan-2-yl)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)CCC1CCCO1 XEQHDALQOYILDN-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
• JPCFSXKVQLDSQF-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CC=N1 JPCFSXKVQLDSQF-UHFFFAOYSA-N 0.000 claims description 2
• CBNOOOGNFHFAFV-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 CBNOOOGNFHFAFV-UHFFFAOYSA-N 0.000 claims description 2
• HVRYPCDTMGFNLL-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CN=C1 HVRYPCDTMGFNLL-UHFFFAOYSA-N 0.000 claims description 2
• XFSIYWBNCKCDJV-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 XFSIYWBNCKCDJV-UHFFFAOYSA-N 0.000 claims description 2
• OOCHYCXBMDBIBT-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=NC=C1 OOCHYCXBMDBIBT-UHFFFAOYSA-N 0.000 claims description 2
• PCASJTPNQGJRSA-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 PCASJTPNQGJRSA-UHFFFAOYSA-N 0.000 claims description 2
• ZLGYFIIXVZIVCW-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=NC=C1 ZLGYFIIXVZIVCW-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
• 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 2
• ARVPUUPXULZPEU-UHFFFAOYSA-N tert-butyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 ARVPUUPXULZPEU-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
• FHGNBCOZVYLRND-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=CN=C1COC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 FHGNBCOZVYLRND-UHFFFAOYSA-N 0.000 claims 2
• LLKVZVINYADQJG-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-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=N1 LLKVZVINYADQJG-UHFFFAOYSA-N 0.000 claims 2
• NRIRQMHKBWLBJA-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=NC=C1COC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 NRIRQMHKBWLBJA-UHFFFAOYSA-N 0.000 claims 2
• QAZBYKUZGBGZTD-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 QAZBYKUZGBGZTD-UHFFFAOYSA-N 0.000 claims 2
• BSWYAPKJOGFSSP-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CC1=NC(C)=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 BSWYAPKJOGFSSP-UHFFFAOYSA-N 0.000 claims 2
• HVTWCXBGHCKQCO-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CC1=NC=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 HVTWCXBGHCKQCO-UHFFFAOYSA-N 0.000 claims 2
• ZXFHOKZMOOWTBP-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1=NC(C)=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 ZXFHOKZMOOWTBP-UHFFFAOYSA-N 0.000 claims 2
• KXGRJVLZEWQYEL-UHFFFAOYSA-N 2-[3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound C1N(C(=O)OCC(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 KXGRJVLZEWQYEL-UHFFFAOYSA-N 0.000 claims 2
• DEFLRAIQDAMFIB-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 DEFLRAIQDAMFIB-UHFFFAOYSA-N 0.000 claims 2
• WSHYFIVKQNBLOX-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 WSHYFIVKQNBLOX-UHFFFAOYSA-N 0.000 claims 2
• IJSBTLYHVZFAQV-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 IJSBTLYHVZFAQV-UHFFFAOYSA-N 0.000 claims 2
• SXTYQHGVUDWKMX-UHFFFAOYSA-N 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 SXTYQHGVUDWKMX-UHFFFAOYSA-N 0.000 claims 2
• BGSQSPCZKPLNDK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=CN=C1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 BGSQSPCZKPLNDK-UHFFFAOYSA-N 0.000 claims 1
• LMVJCUHXYQLVMK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=NC=CN1C LMVJCUHXYQLVMK-UHFFFAOYSA-N 0.000 claims 1
• ZUGDTMRHFVDJEN-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 ZUGDTMRHFVDJEN-UHFFFAOYSA-N 0.000 claims 1
• YVPMOHUBFAAEPH-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 YVPMOHUBFAAEPH-UHFFFAOYSA-N 0.000 claims 1
• XSYPHRKLEHRGCA-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 XSYPHRKLEHRGCA-UHFFFAOYSA-N 0.000 claims 1
• RLUUHGOPGDBVAS-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2C=NC=CC=2)=C2C#N)=C2CC1 RLUUHGOPGDBVAS-UHFFFAOYSA-N 0.000 claims 1
• SSSMCUBUVRFCNO-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-phenylbutanoylamino)-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=C1 SSSMCUBUVRFCNO-UHFFFAOYSA-N 0.000 claims 1
• IIXWTFCZHKOFOG-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-phenylpropanoylamino)-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=C1 IIXWTFCZHKOFOG-UHFFFAOYSA-N 0.000 claims 1
• ZMVCFGQLEXNRBC-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-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=N1 ZMVCFGQLEXNRBC-UHFFFAOYSA-N 0.000 claims 1
• JKJCSLZNLUYLFW-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-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=CN=C1 JKJCSLZNLUYLFW-UHFFFAOYSA-N 0.000 claims 1
• QELNEDNOUOZLRT-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=NC=C1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 QELNEDNOUOZLRT-UHFFFAOYSA-N 0.000 claims 1
• YHDCPDBYBUFGER-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CN=CN1C YHDCPDBYBUFGER-UHFFFAOYSA-N 0.000 claims 1
• LFTNBIMSPUTPTK-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC(O)CO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 LFTNBIMSPUTPTK-UHFFFAOYSA-N 0.000 claims 1
• LUHNFRINOIKMHI-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=C(C)N=C1C LUHNFRINOIKMHI-UHFFFAOYSA-N 0.000 claims 1
• PWCFTEXMOCDTTP-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CC1=NC(C)=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 PWCFTEXMOCDTTP-UHFFFAOYSA-N 0.000 claims 1
• RNJFEZXETMRPEB-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=C(C)N=C1C RNJFEZXETMRPEB-UHFFFAOYSA-N 0.000 claims 1
• ATMOQTHXJPXBAS-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=CN=C1C ATMOQTHXJPXBAS-UHFFFAOYSA-N 0.000 claims 1
• TUFCKEJBYKBYJR-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CC1=NC=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 TUFCKEJBYKBYJR-UHFFFAOYSA-N 0.000 claims 1
• QJUBBFLKXBHEDD-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=CN=C1C QJUBBFLKXBHEDD-UHFFFAOYSA-N 0.000 claims 1
• ZMUCUUWHGNUMQS-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1=NC(C)=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 ZMUCUUWHGNUMQS-UHFFFAOYSA-N 0.000 claims 1
• HLNUNVVCUVOLMN-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)ethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=NC(C)=C1 HLNUNVVCUVOLMN-UHFFFAOYSA-N 0.000 claims 1
• MDZSCSKZEOGQJF-UHFFFAOYSA-N 2-[3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound S1C=2CN(C(=O)OCC(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 MDZSCSKZEOGQJF-UHFFFAOYSA-N 0.000 claims 1
• HUYACICMAUONCQ-UHFFFAOYSA-N 2-[3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound C1N(C(=O)OCC(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 HUYACICMAUONCQ-UHFFFAOYSA-N 0.000 claims 1
• BJIMGNKTRVBQFL-UHFFFAOYSA-N 2-[3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound S1C=2CN(C(=O)OCC(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 BJIMGNKTRVBQFL-UHFFFAOYSA-N 0.000 claims 1
• OYJLBWHIZKNMGR-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCOC(C)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 OYJLBWHIZKNMGR-UHFFFAOYSA-N 0.000 claims 1
• OPWSFZUYWUCXGX-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 OPWSFZUYWUCXGX-UHFFFAOYSA-N 0.000 claims 1
• JBEGARJICCXINZ-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCOC(C)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 JBEGARJICCXINZ-UHFFFAOYSA-N 0.000 claims 1
• KWJCVYFDEOOKCO-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 KWJCVYFDEOOKCO-UHFFFAOYSA-N 0.000 claims 1
• JLIQCWVJAAXJMG-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCOC(C)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CN=C1 JLIQCWVJAAXJMG-UHFFFAOYSA-N 0.000 claims 1
• RVCGYUXTFHNVJV-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 RVCGYUXTFHNVJV-UHFFFAOYSA-N 0.000 claims 1
• RKZPBFNPQVHZEY-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 RKZPBFNPQVHZEY-UHFFFAOYSA-N 0.000 claims 1
• OGGZYEXIZCKZHX-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 OGGZYEXIZCKZHX-UHFFFAOYSA-N 0.000 claims 1
• QYGQVENYNIFJKI-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 QYGQVENYNIFJKI-UHFFFAOYSA-N 0.000 claims 1
• KZIHIAIWVPIBJL-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 KZIHIAIWVPIBJL-UHFFFAOYSA-N 0.000 claims 1
• MIDZZDPBPRQYSN-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=CN=C1 MIDZZDPBPRQYSN-UHFFFAOYSA-N 0.000 claims 1
• FIMLESRTZLZFED-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-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=CN=C1 FIMLESRTZLZFED-UHFFFAOYSA-N 0.000 claims 1
• QURAJZKIGSIKKP-UHFFFAOYSA-N 2-methoxyethyl 3-cyano-2-[3-(furan-2-yl)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=CO1 QURAJZKIGSIKKP-UHFFFAOYSA-N 0.000 claims 1
• KDLPCTLFJYZLPN-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3CCOCC3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 KDLPCTLFJYZLPN-UHFFFAOYSA-N 0.000 claims 1
• ZGYRZYIOYGNSON-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3CCOCC3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 ZGYRZYIOYGNSON-UHFFFAOYSA-N 0.000 claims 1
• ZQCUJPIHLAFZIO-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3CCOCC3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 ZQCUJPIHLAFZIO-UHFFFAOYSA-N 0.000 claims 1
• YPYJNUQKDGBPTF-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=CC=N1 YPYJNUQKDGBPTF-UHFFFAOYSA-N 0.000 claims 1
• OGEJCNXOJKFOTQ-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 OGEJCNXOJKFOTQ-UHFFFAOYSA-N 0.000 claims 1
• LKDJCACMXMUAEK-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 LKDJCACMXMUAEK-UHFFFAOYSA-N 0.000 claims 1
• GIXGDIVVBKCZSE-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 GIXGDIVVBKCZSE-UHFFFAOYSA-N 0.000 claims 1
• SYXVXDSTKQOCOH-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 SYXVXDSTKQOCOH-UHFFFAOYSA-N 0.000 claims 1
• MKTIKGLSTYBNAK-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=CN=C1 MKTIKGLSTYBNAK-UHFFFAOYSA-N 0.000 claims 1
• ZXRXHVQTMYUWHN-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 ZXRXHVQTMYUWHN-UHFFFAOYSA-N 0.000 claims 1
• GMCDKZGGJKHVLG-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=NC=C1 GMCDKZGGJKHVLG-UHFFFAOYSA-N 0.000 claims 1
• CNTGWMYLFSPNOY-UHFFFAOYSA-N 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 CNTGWMYLFSPNOY-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
• 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
• QERKELASDRXTRX-UHFFFAOYSA-N ethyl 2-[3-(1,3-benzodioxol-4-yl)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=CC2=C1OCO2 QERKELASDRXTRX-UHFFFAOYSA-N 0.000 claims 1
• KAFBQXUGJXDZMM-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-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=N1 KAFBQXUGJXDZMM-UHFFFAOYSA-N 0.000 claims 1
• QPMZVQCJGXEQTE-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-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=N1 QPMZVQCJGXEQTE-UHFFFAOYSA-N 0.000 claims 1
• SPJLEEAKQDTWNM-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-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=CN=C1 SPJLEEAKQDTWNM-UHFFFAOYSA-N 0.000 claims 1
• HWMUOKKDTWNHBO-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-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=CN=C1 HWMUOKKDTWNHBO-UHFFFAOYSA-N 0.000 claims 1
• QADDFRXDJAEOBT-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyrimidin-5-ylpropanoylamino)-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=CN=CN=C1 QADDFRXDJAEOBT-UHFFFAOYSA-N 0.000 claims 1
• LKZLMVZBJQVMRP-UHFFFAOYSA-N ethyl 3-cyano-2-[(2-phenylcyclopropanecarbonyl)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=CC=C1 LKZLMVZBJQVMRP-UHFFFAOYSA-N 0.000 claims 1
• KFKNSWMQLDEFMI-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,3-dihydro-1,4-benzodioxin-5-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1CCOC2=C1C=CC=C2CCC(=O)NC(S1)=C(C#N)C2=C1CN(C(=O)OCC)CC2 KFKNSWMQLDEFMI-UHFFFAOYSA-N 0.000 claims 1
• BJQPCQHGXPETDQ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4,5-dimethylfuran-2-yl)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)=C(C)O1 BJQPCQHGXPETDQ-UHFFFAOYSA-N 0.000 claims 1
• SYRFWYKFRLMPJG-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(furan-2-yl)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=CO1 SYRFWYKFRLMPJG-UHFFFAOYSA-N 0.000 claims 1
• QWMCCJNSESILSJ-UHFFFAOYSA-N ethyl 3-cyano-2-[[2-(furan-2-yl)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=CO1 QWMCCJNSESILSJ-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
• 125000000325 methylidene group Chemical group [H]C([H])=* 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
• ZLNBTEKAONFXEE-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CC=N1 ZLNBTEKAONFXEE-UHFFFAOYSA-N 0.000 claims 1
• PMVUJBIGLXVLLR-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 PMVUJBIGLXVLLR-UHFFFAOYSA-N 0.000 claims 1
• WIXIKSKCEZHZLY-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 WIXIKSKCEZHZLY-UHFFFAOYSA-N 0.000 claims 1
• PAFSUSZTQWDKQU-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 PAFSUSZTQWDKQU-UHFFFAOYSA-N 0.000 claims 1
• RAOJEKDSRNNIEO-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CN=C1 RAOJEKDSRNNIEO-UHFFFAOYSA-N 0.000 claims 1
• FIUNWHOUCVQLLC-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 FIUNWHOUCVQLLC-UHFFFAOYSA-N 0.000 claims 1
• UIXSAJZPFJYUII-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 UIXSAJZPFJYUII-UHFFFAOYSA-N 0.000 claims 1
• OLQCBXOJYKFSCG-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 OLQCBXOJYKFSCG-UHFFFAOYSA-N 0.000 claims 1
• QOXFVNSZRSHZBM-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=NC=C1 QOXFVNSZRSHZBM-UHFFFAOYSA-N 0.000 claims 1
• WPTOXDXTEJMNHS-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 WPTOXDXTEJMNHS-UHFFFAOYSA-N 0.000 claims 1
• JAVUDBZOJRVZMC-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 JAVUDBZOJRVZMC-UHFFFAOYSA-N 0.000 claims 1
• RFLLJIRRBAJMGX-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 RFLLJIRRBAJMGX-UHFFFAOYSA-N 0.000 claims 1
• ZLFTTYVNDGLFQL-UHFFFAOYSA-N tert-butyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 ZLFTTYVNDGLFQL-UHFFFAOYSA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
• 210000004027 cell Anatomy 0.000 description 69
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000002904 solvent Substances 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 23
• 239000000243 solution Substances 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 230000006907 apoptotic process Effects 0.000 description 18
• 208000035475 disorder Diseases 0.000 description 17
• 230000022131 cell cycle Effects 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 13
• 239000002585 base Substances 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 13
• 238000000746 purification Methods 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
• 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
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 230000001028 anti-proliverative effect Effects 0.000 description 9
• 238000002648 combination therapy Methods 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• 239000002609 medium Substances 0.000 description 9
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
• 239000000047 product Substances 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• 239000007858 starting material Substances 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
• 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 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
• 238000001914 filtration Methods 0.000 description 8
• 230000001939 inductive effect Effects 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• 230000035755 proliferation Effects 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 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
• 238000005755 formation reaction Methods 0.000 description 7
• 230000014509 gene expression Effects 0.000 description 7
• 125000001786 isothiazolyl group Chemical group 0.000 description 7
• 125000000842 isoxazolyl group Chemical group 0.000 description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 description 7
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 7
• 125000002098 pyridazinyl group Chemical group 0.000 description 7
• 238000007127 saponification reaction Methods 0.000 description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 description 7
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 6
• 125000002393 azetidinyl group Chemical group 0.000 description 6
• 125000004069 aziridinyl group Chemical group 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 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 6
• 239000002552 dosage form Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 125000002632 imidazolidinyl group Chemical group 0.000 description 6
• 125000002757 morpholinyl group Chemical group 0.000 description 6
• 125000004193 piperazinyl group Chemical group 0.000 description 6
• 125000003386 piperidinyl group Chemical group 0.000 description 6
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 125000004568 thiomorpholinyl group Chemical group 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
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 230000010261 cell growth Effects 0.000 description 5
• 230000004663 cell proliferation Effects 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
• 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 5
• 238000001704 evaporation Methods 0.000 description 5
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
• 239000000411 inducer Substances 0.000 description 5
• 210000005170 neoplastic cell Anatomy 0.000 description 5
• 239000005022 packaging material Substances 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 229940086542 triethylamine Drugs 0.000 description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
• 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
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• 102400001093 PAK-2p27 Human genes 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 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
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
• 150000003997 cyclic ketones Chemical class 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• 238000005516 engineering process Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 230000002650 habitual effect Effects 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
• 239000008177 pharmaceutical agent Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
• 238000011321 prophylaxis Methods 0.000 description 4
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([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
• 238000003756 stirring Methods 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 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 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
• ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 description 3
• 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
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
• 125000004457 alkyl amino carbonyl group Chemical group 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
• 238000004364 calculation method Methods 0.000 description 3
• 239000002775 capsule Substances 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
• 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
• 238000006705 deacetalization reaction Methods 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
• 230000006870 function Effects 0.000 description 3
• 239000007789 gas Substances 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
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
• 239000002674 ointment Substances 0.000 description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
• 239000000825 pharmaceutical preparation Substances 0.000 description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
• JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 2
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 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
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
• 229940112129 campath Drugs 0.000 description 2
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 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
• 238000004587 chromatography analysis Methods 0.000 description 2
• 201000010897 colon adenocarcinoma Diseases 0.000 description 2
• 208000029742 colonic neoplasm Diseases 0.000 description 2
• 238000005859 coupling reaction Methods 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
• 229960000640 dactinomycin Drugs 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
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
• 239000000839 emulsion Substances 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
• 125000001153 fluoro group Chemical group F* 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
• 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
• 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
• 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
• 150000004702 methyl esters Chemical class 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
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 230000020477 pH reduction 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
• 230000005522 programmed cell death Effects 0.000 description 2
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
• 229940080818 propionamide Drugs 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
• 125000004434 sulfur atom Chemical group 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
• 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
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([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
• 238000005406 washing Methods 0.000 description 2
• VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
• 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
• BRIQSCDTIRHDSP-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=NC=CN1C BRIQSCDTIRHDSP-UHFFFAOYSA-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
• QDDOCCCGTFEHPG-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 QDDOCCCGTFEHPG-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
• 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
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 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
• 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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
• 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
• XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical class NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 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
• DHNATINBDYSRKZ-UHFFFAOYSA-N 2-pyridin-2-ylethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=CC=N1 DHNATINBDYSRKZ-UHFFFAOYSA-N 0.000 description 1
• XKUDEUFAQONCQQ-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=CN=C1 XKUDEUFAQONCQQ-UHFFFAOYSA-N 0.000 description 1
• DTLLWHFPVUNKIT-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCC1=CC=NC=C1 DTLLWHFPVUNKIT-UHFFFAOYSA-N 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
• FHJPXFFTECMWCZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1Cl FHJPXFFTECMWCZ-UHFFFAOYSA-N 0.000 description 1
• JKXFUBSLDHLHEG-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)propanamide Chemical compound ClC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 JKXFUBSLDHLHEG-UHFFFAOYSA-N 0.000 description 1
• DXJYTCPQPGIIDR-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC(Cl)=C1 DXJYTCPQPGIIDR-UHFFFAOYSA-N 0.000 description 1
• HQYORGGHUBIWHO-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)propanamide Chemical compound ClC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 HQYORGGHUBIWHO-UHFFFAOYSA-N 0.000 description 1
• XLTJXJJMUFDQEZ-UHFFFAOYSA-N 3-(furan-2-yl)propanoic acid Chemical compound OC(=O)CCC1=CC=CO1 XLTJXJJMUFDQEZ-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
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 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
• 229940110282 alimta Drugs 0.000 description 1
• 229940098174 alkeran Drugs 0.000 description 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000000217 alkyl 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
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
• 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 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
• 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
• 125000001309 chloro group Chemical group Cl* 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
• 239000013078 crystal Substances 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
• 125000004956 cyclohexylene group Chemical group 0.000 description 1
• 125000004979 cyclopentylene group Chemical group 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
• FIKYVUYVAGBVGL-UHFFFAOYSA-N ethyl 3-cyano-2-(3-phenylpropanoylamino)-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=C1 FIKYVUYVAGBVGL-UHFFFAOYSA-N 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
• 125000004494 ethyl ester group Chemical group 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
• 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
• 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
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 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
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 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
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 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
• 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
• URTABAGGJUANIO-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2,3-dimethylphenyl)propanamide Chemical compound CC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1C URTABAGGJUANIO-UHFFFAOYSA-N 0.000 description 1
• VXTQFVVGWOVPPZ-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2,5-dimethylphenyl)propanamide Chemical compound CC1=CC=C(C)C(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 VXTQFVVGWOVPPZ-UHFFFAOYSA-N 0.000 description 1
• VTLWFOIVBYTEIY-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-ethylphenyl)butanamide Chemical compound CCC1=CC=CC=C1C(C)CC(=O)NC1=C(C#N)C(CCNC2)=C2S1 VTLWFOIVBYTEIY-UHFFFAOYSA-N 0.000 description 1
• KGLIYQOIVLDDNG-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-ethylphenyl)propanamide Chemical compound CCC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 KGLIYQOIVLDDNG-UHFFFAOYSA-N 0.000 description 1
• NMTRECFXIWZWBK-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-fluorophenyl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1F NMTRECFXIWZWBK-UHFFFAOYSA-N 0.000 description 1
• PSOXACUKAKJGMJ-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-fluorophenyl)propanamide Chemical compound FC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 PSOXACUKAKJGMJ-UHFFFAOYSA-N 0.000 description 1
• VOHCQRUJJDIWGI-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-methylphenyl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1C VOHCQRUJJDIWGI-UHFFFAOYSA-N 0.000 description 1
• HJEVNJDCSLETGD-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(2-methylphenyl)propanamide Chemical compound CC1=CC=CC=C1CCC(=O)NC1=C(C#N)C(CCNC2)=C2S1 HJEVNJDCSLETGD-UHFFFAOYSA-N 0.000 description 1
• ZFAJTPJBOYFQDV-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-ethylphenyl)butanamide Chemical compound CCC1=CC=CC(C(C)CC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 ZFAJTPJBOYFQDV-UHFFFAOYSA-N 0.000 description 1
• LRIKXRWWFWEHFE-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-ethylphenyl)propanamide Chemical compound CCC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 LRIKXRWWFWEHFE-UHFFFAOYSA-N 0.000 description 1
• BEZFLNAIOZBPFS-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-fluorophenyl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC(F)=C1 BEZFLNAIOZBPFS-UHFFFAOYSA-N 0.000 description 1
• MFLWJGHVVOQHKO-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-fluorophenyl)propanamide Chemical compound FC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 MFLWJGHVVOQHKO-UHFFFAOYSA-N 0.000 description 1
• YDPZDGTYISRHJR-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-methylphenyl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC(C)=C1 YDPZDGTYISRHJR-UHFFFAOYSA-N 0.000 description 1
• JPWAWPWWODCQCJ-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(3-methylphenyl)propanamide Chemical compound CC1=CC=CC(CCC(=O)NC2=C(C=3CCNCC=3S2)C#N)=C1 JPWAWPWWODCQCJ-UHFFFAOYSA-N 0.000 description 1
• COFRHRKVFSZXNR-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(furan-2-yl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CO1 COFRHRKVFSZXNR-UHFFFAOYSA-N 0.000 description 1
• OHRHUYFOLBKYHK-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(furan-2-yl)propanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 OHRHUYFOLBKYHK-UHFFFAOYSA-N 0.000 description 1
• VSIGSSMZRQAICP-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(furan-3-yl)butanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C=1C=COC=1 VSIGSSMZRQAICP-UHFFFAOYSA-N 0.000 description 1
• XTTORHUVHFCTKN-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-(furan-3-yl)propanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC=1C=COC=1 XTTORHUVHFCTKN-UHFFFAOYSA-N 0.000 description 1
• KQWUTTGOUQOLTL-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-phenylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 KQWUTTGOUQOLTL-UHFFFAOYSA-N 0.000 description 1
• TUJUPQPYZNRLQU-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-phenylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 TUJUPQPYZNRLQU-UHFFFAOYSA-N 0.000 description 1
• RTGJSUUQUSMFTE-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-2-ylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 RTGJSUUQUSMFTE-UHFFFAOYSA-N 0.000 description 1
• MGWBGBQMQFDXAI-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-2-ylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 MGWBGBQMQFDXAI-UHFFFAOYSA-N 0.000 description 1
• IGJSIORCPIJGNW-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-3-ylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CN=C1 IGJSIORCPIJGNW-UHFFFAOYSA-N 0.000 description 1
• OAWHLTKVRKLETG-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-3-ylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 OAWHLTKVRKLETG-UHFFFAOYSA-N 0.000 description 1
• JHMLLWDIVUDYIW-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-4-ylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=NC=C1 JHMLLWDIVUDYIW-UHFFFAOYSA-N 0.000 description 1
• XTXRTQFAVYSNLI-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-pyridin-4-ylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=NC=C1 XTXRTQFAVYSNLI-UHFFFAOYSA-N 0.000 description 1
• UEYNAJKCCVHABD-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-thiophen-2-ylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CS1 UEYNAJKCCVHABD-UHFFFAOYSA-N 0.000 description 1
• YNGDQGGKWOESCM-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-thiophen-2-ylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC1=CC=CS1 YNGDQGGKWOESCM-UHFFFAOYSA-N 0.000 description 1
• LWNZTAVMFWGXMQ-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-thiophen-3-ylbutanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CC(C)C=1C=CSC=1 LWNZTAVMFWGXMQ-UHFFFAOYSA-N 0.000 description 1
• GYFMWIKLLDFSSX-UHFFFAOYSA-N n-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-3-thiophen-3-ylpropanamide Chemical compound S1C=2CNCCC=2C(C#N)=C1NC(=O)CCC=1C=CSC=1 GYFMWIKLLDFSSX-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
• 125000005476 oxopyrrolidinyl group Chemical group 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
• 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
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 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
• 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
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• QKUJMKZCTCJKKE-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CC=N1 QKUJMKZCTCJKKE-UHFFFAOYSA-N 0.000 description 1
• KVOSTBOTXZNEQY-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CN=C1 KVOSTBOTXZNEQY-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 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
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 150000003462 sulfoxides Chemical group 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
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 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
• 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
• 229940053867 xeloda Drugs 0.000 description 1