ZA200507752B - Compositions and methods for treating cancer - Google Patents
Compositions and methods for treating cancer Download PDFInfo
- Publication number
- ZA200507752B ZA200507752B ZA200507752A ZA200507752A ZA200507752B ZA 200507752 B ZA200507752 B ZA 200507752B ZA 200507752 A ZA200507752 A ZA 200507752A ZA 200507752 A ZA200507752 A ZA 200507752A ZA 200507752 B ZA200507752 B ZA 200507752B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- alkyl
- amide
- neoplastic agent
- unsubstituted
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 80
- 201000011510 cancer Diseases 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 title claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 260
- 239000002246 antineoplastic agent Substances 0.000 claims description 232
- 229940034982 antineoplastic agent Drugs 0.000 claims description 224
- -1 keto, amino Chemical group 0.000 claims description 211
- 150000001408 amides Chemical class 0.000 claims description 173
- 229940124530 sulfonamide Drugs 0.000 claims description 130
- 150000003456 sulfonamides Chemical class 0.000 claims description 129
- 206010021143 Hypoxia Diseases 0.000 claims description 123
- 230000001146 hypoxic effect Effects 0.000 claims description 119
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 114
- 150000002148 esters Chemical class 0.000 claims description 110
- 239000012190 activator Substances 0.000 claims description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 87
- 125000005842 heteroatom Chemical group 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
- 229910052799 carbon Inorganic materials 0.000 claims description 61
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 57
- 150000003573 thiols Chemical class 0.000 claims description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 150000003568 thioethers Chemical class 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 45
- 150000001734 carboxylic acid salts Chemical class 0.000 claims description 41
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 34
- 125000005647 linker group Chemical group 0.000 claims description 34
- 150000003462 sulfoxides Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 150000003457 sulfones Chemical class 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 30
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 29
- 150000002431 hydrogen Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 210000004027 cell Anatomy 0.000 claims description 25
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical group [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 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 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 150000003857 carboxamides Chemical class 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 150000003536 tetrazoles Chemical class 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000000468 ketone group Chemical group 0.000 claims description 14
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 13
- 229930194542 Keto Natural products 0.000 claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 12
- 229940127089 cytotoxic agent Drugs 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 8
- 230000003111 delayed effect Effects 0.000 claims description 8
- 229960004679 doxorubicin Drugs 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1h-pyrrole Chemical group [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 claims description 7
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 7
- 229930012538 Paclitaxel Natural products 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 230000002950 deficient Effects 0.000 claims description 7
- 229960001592 paclitaxel Drugs 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000001959 radiotherapy Methods 0.000 claims description 7
- 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 7
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 6
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 6
- ILTUTLWVTBBXNS-UHFFFAOYSA-N Tedanolide Natural products C1OC(=O)C(O)C(OC)C(C)C(=O)C(C)C(O)C(C)=CC(C)C(=O)CC(O)C(C)C(=O)C1C(O)C1(C)C(C(C)C=CC)O1 ILTUTLWVTBBXNS-UHFFFAOYSA-N 0.000 claims description 6
- 229960004562 carboplatin Drugs 0.000 claims description 6
- 229960003901 dacarbazine Drugs 0.000 claims description 6
- 229960000975 daunorubicin Drugs 0.000 claims description 6
- VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 claims description 6
- 229960005501 duocarmycin Drugs 0.000 claims description 6
- 229930184221 duocarmycin Natural products 0.000 claims description 6
- 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 6
- 229960005420 etoposide Drugs 0.000 claims description 6
- 229960000390 fludarabine Drugs 0.000 claims description 6
- 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 6
- 229960002949 fluorouracil Drugs 0.000 claims description 6
- 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 claims description 6
- 229960001156 mitoxantrone Drugs 0.000 claims description 6
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 6
- 229960000624 procarbazine Drugs 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229960003087 tioguanine Drugs 0.000 claims description 6
- 210000001519 tissue Anatomy 0.000 claims description 6
- 229960004528 vincristine Drugs 0.000 claims description 6
- 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 6
- 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 6
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 5
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 5
- 108010006654 Bleomycin Proteins 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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 5
- 229940123237 Taxane Drugs 0.000 claims description 5
- 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 5
- 125000004036 acetal group Chemical group 0.000 claims description 5
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class 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 5
- 229930195731 calicheamicin Natural products 0.000 claims description 5
- 235000013877 carbamide Nutrition 0.000 claims description 5
- 229960000684 cytarabine Drugs 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 229960004961 mechlorethamine Drugs 0.000 claims description 5
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims description 5
- 229960001428 mercaptopurine Drugs 0.000 claims description 5
- 229960004857 mitomycin Drugs 0.000 claims description 5
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims description 5
- 229960001278 teniposide Drugs 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- 229960003048 vinblastine Drugs 0.000 claims description 5
- 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 5
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical group [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 claims description 4
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical group NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229960001561 bleomycin Drugs 0.000 claims description 4
- 229960005537 combretastatin A-4 Drugs 0.000 claims description 4
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 claims description 4
- 230000003211 malignant effect Effects 0.000 claims description 4
- HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 claims description 4
- 150000004957 nitroimidazoles Chemical class 0.000 claims description 4
- 229950004406 porfiromycin Drugs 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 229960000303 topotecan Drugs 0.000 claims description 4
- 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 4
- YZBAXVICWUUHGG-UHFFFAOYSA-N 2-[[4-[2-[dimethyl(oxido)azaniumyl]ethylamino]-5,8-dihydroxy-9,10-dioxoanthracen-1-yl]amino]-n,n-dimethylethanamine oxide Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCC[N+](C)(C)[O-])=CC=C2NCC[N+](C)([O-])C YZBAXVICWUUHGG-UHFFFAOYSA-N 0.000 claims description 3
- HUNDJKXYCIAYJT-UHFFFAOYSA-N 2-nitro-1,3-oxazole Chemical group [O-][N+](=O)C1=NC=CO1 HUNDJKXYCIAYJT-UHFFFAOYSA-N 0.000 claims description 3
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical group [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 claims description 3
- GONFBOIJNUKKST-UHFFFAOYSA-N 5-ethylsulfanyl-2h-tetrazole Chemical compound CCSC=1N=NNN=1 GONFBOIJNUKKST-UHFFFAOYSA-N 0.000 claims description 3
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 3
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims 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
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 229930192392 Mitomycin Natural products 0.000 claims description 3
- 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 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical class C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229940127093 camptothecin Drugs 0.000 claims description 3
- 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 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
- 229960004316 cisplatin Drugs 0.000 claims description 3
- 229960001338 colchicine Drugs 0.000 claims description 3
- 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 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 229960001904 epirubicin Drugs 0.000 claims description 3
- 229930013356 epothilone Natural products 0.000 claims description 3
- 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 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 201000010536 head and neck cancer Diseases 0.000 claims description 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 229960000485 methotrexate Drugs 0.000 claims description 3
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical class CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical group NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 claims description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 3
- 229960004618 prednisone Drugs 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 230000001780 adrenocortical effect Effects 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000000340 anti-metabolite Effects 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 37
- 201000006747 infectious mononucleosis Diseases 0.000 claims 30
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 8
- 108010092160 Dactinomycin Proteins 0.000 claims 7
- 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 6
- CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 claims 6
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 claims 6
- 206010039491 Sarcoma Diseases 0.000 claims 5
- DVQHYTBCTGYNNN-UHFFFAOYSA-N azane;cyclobutane-1,1-dicarboxylic acid;platinum Chemical compound N.N.[Pt].OC(=O)C1(C(O)=O)CCC1 DVQHYTBCTGYNNN-UHFFFAOYSA-N 0.000 claims 5
- 208000003174 Brain Neoplasms Diseases 0.000 claims 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 4
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims 4
- 229960000640 dactinomycin Drugs 0.000 claims 4
- 206010020718 hyperplasia Diseases 0.000 claims 4
- PVYJZLYGTZKPJE-UHFFFAOYSA-N streptonigrin Chemical compound C=1C=C2C(=O)C(OC)=C(N)C(=O)C2=NC=1C(C=1N)=NC(C(O)=O)=C(C)C=1C1=CC=C(OC)C(OC)=C1O PVYJZLYGTZKPJE-UHFFFAOYSA-N 0.000 claims 4
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 claims 3
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 claims 3
- FLWWDYNPWOSLEO-HQVZTVAUSA-N (2s)-2-[[4-[1-(2-amino-4-oxo-1h-pteridin-6-yl)ethyl-methylamino]benzoyl]amino]pentanedioic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1C(C)N(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FLWWDYNPWOSLEO-HQVZTVAUSA-N 0.000 claims 3
- VRYALKFFQXWPIH-RANCGNPWSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxy-2-tritiohexanal Chemical compound O=CC([3H])[C@@H](O)[C@H](O)[C@H](O)CO VRYALKFFQXWPIH-RANCGNPWSA-N 0.000 claims 3
- 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 claims 3
- BTOTXLJHDSNXMW-POYBYMJQSA-N 2,3-dideoxyuridine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(=O)NC(=O)C=C1 BTOTXLJHDSNXMW-POYBYMJQSA-N 0.000 claims 3
- BOMZMNZEXMAQQW-UHFFFAOYSA-N 2,5,11-trimethyl-6h-pyrido[4,3-b]carbazol-2-ium-9-ol;acetate Chemical compound CC([O-])=O.C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 BOMZMNZEXMAQQW-UHFFFAOYSA-N 0.000 claims 3
- QCXJFISCRQIYID-IAEPZHFASA-N 2-amino-1-n-[(3s,6s,7r,10s,16s)-3-[(2s)-butan-2-yl]-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-9-n-[(3s,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propa 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=C2C(C(=O)N[C@@H]3C(=O)N[C@H](C(N4CCC[C@H]4C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]3C)=O)[C@@H](C)CC)=C(N)C(=O)C(C)=C2O2)C2=C(C)C=C1 QCXJFISCRQIYID-IAEPZHFASA-N 0.000 claims 3
- VNBAOSVONFJBKP-UHFFFAOYSA-N 2-chloro-n,n-bis(2-chloroethyl)propan-1-amine;hydrochloride Chemical compound Cl.CC(Cl)CN(CCCl)CCCl VNBAOSVONFJBKP-UHFFFAOYSA-N 0.000 claims 3
- IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims 3
- VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 claims 3
- 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 claims 3
- MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 claims 3
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 claims 3
- NNJPGOLRFBJNIW-UHFFFAOYSA-N Demecolcine Natural products C1=C(OC)C(=O)C=C2C(NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-UHFFFAOYSA-N 0.000 claims 3
- SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 claims 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 3
- 102000006992 Interferon-alpha Human genes 0.000 claims 3
- 108010047761 Interferon-alpha Proteins 0.000 claims 3
- 102000003996 Interferon-beta Human genes 0.000 claims 3
- 108090000467 Interferon-beta Proteins 0.000 claims 3
- 102000008070 Interferon-gamma Human genes 0.000 claims 3
- 108010074328 Interferon-gamma Proteins 0.000 claims 3
- 102000000588 Interleukin-2 Human genes 0.000 claims 3
- 108010002350 Interleukin-2 Proteins 0.000 claims 3
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims 3
- 229920001491 Lentinan Polymers 0.000 claims 3
- VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 claims 3
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims 3
- 229930187135 Olivomycin Natural products 0.000 claims 3
- 108010057150 Peplomycin Proteins 0.000 claims 3
- 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 claims 3
- 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 claims 3
- 229920000519 Sizofiran Polymers 0.000 claims 3
- UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 claims 3
- FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 claims 3
- 229950002684 aceglatone Drugs 0.000 claims 3
- ZOZKYEHVNDEUCO-XUTVFYLZSA-N aceglatone Chemical compound O1C(=O)[C@H](OC(C)=O)[C@@H]2OC(=O)[C@@H](OC(=O)C)[C@@H]21 ZOZKYEHVNDEUCO-XUTVFYLZSA-N 0.000 claims 3
- 229930188522 aclacinomycin Natural products 0.000 claims 3
- LJZPVWKMAYDYAS-QKKPTTNWSA-N aclacinomycin T Chemical class 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)[C@H]1C[C@H](N(C)C)[C@H](O)[C@H](C)O1 LJZPVWKMAYDYAS-QKKPTTNWSA-N 0.000 claims 3
- 229930183665 actinomycin Natural products 0.000 claims 3
- 229960002749 aminolevulinic acid Drugs 0.000 claims 3
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims 3
- 229960001220 amsacrine Drugs 0.000 claims 3
- 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 claims 3
- 229950000242 ancitabine Drugs 0.000 claims 3
- 229960002756 azacitidine Drugs 0.000 claims 3
- 229950005567 benzodepa Drugs 0.000 claims 3
- VFIUCBTYGKMLCM-UHFFFAOYSA-N benzyl n-[bis(aziridin-1-yl)phosphoryl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NP(=O)(N1CC1)N1CC1 VFIUCBTYGKMLCM-UHFFFAOYSA-N 0.000 claims 3
- 108700002839 cactinomycin Proteins 0.000 claims 3
- 229950009908 cactinomycin Drugs 0.000 claims 3
- 229960002115 carboquone Drugs 0.000 claims 3
- 108010047060 carzinophilin Proteins 0.000 claims 3
- 229960004630 chlorambucil Drugs 0.000 claims 3
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 3
- 229960001480 chlorozotocin Drugs 0.000 claims 3
- 229960005052 demecolcine Drugs 0.000 claims 3
- 229950000549 elliptinium acetate Drugs 0.000 claims 3
- 229950011487 enocitabine Drugs 0.000 claims 3
- QSRLNKCNOLVZIR-KRWDZBQOSA-N ethyl (2s)-2-[[2-[4-[bis(2-chloroethyl)amino]phenyl]acetyl]amino]-4-methylsulfanylbutanoate Chemical compound CCOC(=O)[C@H](CCSC)NC(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 QSRLNKCNOLVZIR-KRWDZBQOSA-N 0.000 claims 3
- 229960005237 etoglucid Drugs 0.000 claims 3
- 229960000961 floxuridine Drugs 0.000 claims 3
- 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 claims 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 3
- 229960002074 flutamide Drugs 0.000 claims 3
- 229940044658 gallium nitrate Drugs 0.000 claims 3
- 229930182470 glycoside Natural products 0.000 claims 3
- 229960001101 ifosfamide Drugs 0.000 claims 3
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 3
- 229960002411 imatinib Drugs 0.000 claims 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 3
- 229960003130 interferon gamma Drugs 0.000 claims 3
- 229960001388 interferon-beta Drugs 0.000 claims 3
- 229940115286 lentinan Drugs 0.000 claims 3
- 229960003538 lonidamine Drugs 0.000 claims 3
- WDRYRZXSPDWGEB-UHFFFAOYSA-N lonidamine Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Cl)C=C1Cl WDRYRZXSPDWGEB-UHFFFAOYSA-N 0.000 claims 3
- 229960001924 melphalan Drugs 0.000 claims 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 3
- 229950009847 meturedepa Drugs 0.000 claims 3
- QTFKTBRIGWJQQL-UHFFFAOYSA-N meturedepa Chemical compound C1C(C)(C)N1P(=O)(NC(=O)OCC)N1CC1(C)C QTFKTBRIGWJQQL-UHFFFAOYSA-N 0.000 claims 3
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 229960005485 mitobronitol Drugs 0.000 claims 3
- 229950010913 mitolactol Drugs 0.000 claims 3
- 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 claims 3
- CPTIBDHUFVHUJK-NZYDNVMFSA-N mitopodozide Chemical compound C1([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(=O)NNCC)=CC(OC)=C(OC)C(OC)=C1 CPTIBDHUFVHUJK-NZYDNVMFSA-N 0.000 claims 3
- FOYWNSCCNCUEPU-UHFFFAOYSA-N mopidamol Chemical compound C12=NC(N(CCO)CCO)=NC=C2N=C(N(CCO)CCO)N=C1N1CCCCC1 FOYWNSCCNCUEPU-UHFFFAOYSA-N 0.000 claims 3
- 229950010718 mopidamol Drugs 0.000 claims 3
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims 3
- 229960000951 mycophenolic acid Drugs 0.000 claims 3
- QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 claims 3
- CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin 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=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 claims 3
- 229950005848 olivomycin Drugs 0.000 claims 3
- 229960002340 pentostatin Drugs 0.000 claims 3
- 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 claims 3
- 229950003180 peplomycin Drugs 0.000 claims 3
- QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin 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)NCCCN[C@@H](C)C=1C=CC=CC=1)[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=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 claims 3
- NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 claims 3
- 229960000952 pipobroman Drugs 0.000 claims 3
- 229960003171 plicamycin Drugs 0.000 claims 3
- 229960004694 prednimustine Drugs 0.000 claims 3
- WOLQREOUPKZMEX-UHFFFAOYSA-N pteroyltriglutamic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C=C1 WOLQREOUPKZMEX-UHFFFAOYSA-N 0.000 claims 3
- 229950010131 puromycin Drugs 0.000 claims 3
- 229960002185 ranimustine Drugs 0.000 claims 3
- 229950001403 sizofiran Drugs 0.000 claims 3
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 3
- 229960001603 tamoxifen Drugs 0.000 claims 3
- 229960001674 tegafur Drugs 0.000 claims 3
- YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 claims 3
- 229950011457 tiamiprine Drugs 0.000 claims 3
- 229950001353 tretamine Drugs 0.000 claims 3
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 claims 3
- 229960000875 trofosfamide Drugs 0.000 claims 3
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 claims 3
- 229950009811 ubenimex Drugs 0.000 claims 3
- 229960001055 uracil mustard Drugs 0.000 claims 3
- 229950009268 zinostatin Drugs 0.000 claims 3
- CGMTUJFWROPELF-YPAAEMCBSA-N (3E,5S)-5-[(2S)-butan-2-yl]-3-(1-hydroxyethylidene)pyrrolidine-2,4-dione Chemical compound CC[C@H](C)[C@@H]1NC(=O)\C(=C(/C)O)C1=O CGMTUJFWROPELF-YPAAEMCBSA-N 0.000 claims 2
- AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 claims 2
- PWMYMKOUNYTVQN-UHFFFAOYSA-N 3-(8,8-diethyl-2-aza-8-germaspiro[4.5]decan-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C[Ge](CC)(CC)CCC11CN(CCCN(C)C)CC1 PWMYMKOUNYTVQN-UHFFFAOYSA-N 0.000 claims 2
- WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 claims 2
- HDZZVAMISRMYHH-UHFFFAOYSA-N 9beta-Ribofuranosyl-7-deazaadenin Natural products C1=CC=2C(N)=NC=NC=2N1C1OC(CO)C(O)C1O HDZZVAMISRMYHH-UHFFFAOYSA-N 0.000 claims 2
- 208000003200 Adenoma Diseases 0.000 claims 2
- 206010001233 Adenoma benign Diseases 0.000 claims 2
- CEIZFXOZIQNICU-UHFFFAOYSA-N Alternaria alternata Crofton-weed toxin Natural products CCC(C)C1NC(=O)C(C(C)=O)=C1O CEIZFXOZIQNICU-UHFFFAOYSA-N 0.000 claims 2
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 2
- 206010005949 Bone cancer Diseases 0.000 claims 2
- 208000018084 Bone neoplasm Diseases 0.000 claims 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 claims 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims 2
- 206010008263 Cervical dysplasia Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 208000007569 Giant Cell Tumors Diseases 0.000 claims 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims 2
- 208000009164 Islet Cell Adenoma Diseases 0.000 claims 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 2
- 208000007054 Medullary Carcinoma Diseases 0.000 claims 2
- 206010029260 Neuroblastoma Diseases 0.000 claims 2
- KGTDRFCXGRULNK-UHFFFAOYSA-N Nogalamycin Natural products COC1C(OC)(C)C(OC)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=C4C5(C)OC(C(C(C5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C(C(=O)OC)C(C)(O)C1 KGTDRFCXGRULNK-UHFFFAOYSA-N 0.000 claims 2
- KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin 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-HSUXVGOQSA-N 0.000 claims 2
- 201000000582 Retinoblastoma Diseases 0.000 claims 2
- 201000010208 Seminoma Diseases 0.000 claims 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 2
- CGMTUJFWROPELF-UHFFFAOYSA-N Tenuazonic acid Natural products CCC(C)C1NC(=O)C(=C(C)/O)C1=O CGMTUJFWROPELF-UHFFFAOYSA-N 0.000 claims 2
- VGQOVCHZGQWAOI-UHFFFAOYSA-N UNPD55612 Natural products N1C(O)C2CC(C=CC(N)=O)=CN2C(=O)C2=CC=C(C)C(O)=C12 VGQOVCHZGQWAOI-UHFFFAOYSA-N 0.000 claims 2
- IFJUINDAXYAPTO-UUBSBJJBSA-N [(8r,9s,13s,14s,17s)-17-[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4OC(=O)COC(=O)CCCC=1C=CC(=CC=1)N(CCCl)CCCl)C)CC2=CC=3OC(=O)C1=CC=CC=C1 IFJUINDAXYAPTO-UUBSBJJBSA-N 0.000 claims 2
- 208000009956 adenocarcinoma Diseases 0.000 claims 2
- 230000001919 adrenal effect Effects 0.000 claims 2
- VGQOVCHZGQWAOI-HYUHUPJXSA-N anthramycin Chemical compound N1[C@@H](O)[C@@H]2CC(\C=C\C(N)=O)=CN2C(=O)C2=CC=C(C)C(O)=C12 VGQOVCHZGQWAOI-HYUHUPJXSA-N 0.000 claims 2
- 229950011321 azaserine Drugs 0.000 claims 2
- 229950008548 bisantrene Drugs 0.000 claims 2
- 229960002092 busulfan Drugs 0.000 claims 2
- 208000002458 carcinoid tumor Diseases 0.000 claims 2
- XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin 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=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 claims 2
- XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 claims 2
- 229960003261 carmofur Drugs 0.000 claims 2
- 229960005243 carmustine Drugs 0.000 claims 2
- 229950001725 carubicin Drugs 0.000 claims 2
- 201000001883 cholelithiasis Diseases 0.000 claims 2
- ZYVSOIYQKUDENJ-WKSBCEQHSA-N chromomycin A3 Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1OC(C)=O)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](OC(C)=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](OC)[C@@H](C)O1 ZYVSOIYQKUDENJ-WKSBCEQHSA-N 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- WVYXNIXAMZOZFK-UHFFFAOYSA-N diaziquone Chemical compound O=C1C(NC(=O)OCC)=C(N2CC2)C(=O)C(NC(=O)OCC)=C1N1CC1 WVYXNIXAMZOZFK-UHFFFAOYSA-N 0.000 claims 2
- 229950002389 diaziquone Drugs 0.000 claims 2
- 108010067396 dornase alfa Proteins 0.000 claims 2
- 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 claims 2
- 229950005454 doxifluridine Drugs 0.000 claims 2
- VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 claims 2
- 229960002759 eflornithine Drugs 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 claims 2
- 229960004783 fotemustine Drugs 0.000 claims 2
- 208000001130 gallstones Diseases 0.000 claims 2
- 210000003128 head Anatomy 0.000 claims 2
- 230000000148 hypercalcaemia Effects 0.000 claims 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims 2
- 230000002390 hyperplastic effect Effects 0.000 claims 2
- DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 claims 2
- 229950008097 improsulfan Drugs 0.000 claims 2
- 201000004933 in situ carcinoma Diseases 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 201000002529 islet cell tumor Diseases 0.000 claims 2
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 208000037841 lung tumor Diseases 0.000 claims 2
- 230000000527 lymphocytic effect Effects 0.000 claims 2
- MQXVYODZCMMZEM-ZYUZMQFOSA-N mannomustine Chemical compound ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl MQXVYODZCMMZEM-ZYUZMQFOSA-N 0.000 claims 2
- 229950008612 mannomustine Drugs 0.000 claims 2
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 230000001394 metastastic effect Effects 0.000 claims 2
- 206010061289 metastatic neoplasm Diseases 0.000 claims 2
- 229960003539 mitoguazone Drugs 0.000 claims 2
- MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 claims 2
- NJSMWLQOCQIOPE-OCHFTUDZSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 NJSMWLQOCQIOPE-OCHFTUDZSA-N 0.000 claims 2
- 210000003739 neck Anatomy 0.000 claims 2
- 210000005036 nerve Anatomy 0.000 claims 2
- 230000001537 neural effect Effects 0.000 claims 2
- 229960001420 nimustine Drugs 0.000 claims 2
- VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 claims 2
- YMVWGSQGCWCDGW-UHFFFAOYSA-N nitracrine Chemical compound C1=CC([N+]([O-])=O)=C2C(NCCCN(C)C)=C(C=CC=C3)C3=NC2=C1 YMVWGSQGCWCDGW-UHFFFAOYSA-N 0.000 claims 2
- 229950008607 nitracrine Drugs 0.000 claims 2
- 229950009266 nogalamycin Drugs 0.000 claims 2
- KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 210000000496 pancreas Anatomy 0.000 claims 2
- 208000022102 pancreatic neuroendocrine neoplasm Diseases 0.000 claims 2
- 230000000849 parathyroid Effects 0.000 claims 2
- 229960001221 pirarubicin Drugs 0.000 claims 2
- 208000030266 primary brain neoplasm Diseases 0.000 claims 2
- 229940107568 pulmozyme Drugs 0.000 claims 2
- BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 claims 2
- 229960000460 razoxane Drugs 0.000 claims 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 206010040882 skin lesion Diseases 0.000 claims 2
- 231100000444 skin lesion Toxicity 0.000 claims 2
- 229950006315 spirogermanium Drugs 0.000 claims 2
- 210000002784 stomach Anatomy 0.000 claims 2
- 229960001052 streptozocin Drugs 0.000 claims 2
- 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 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 claims 2
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 230000000699 topical effect Effects 0.000 claims 2
- PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 claims 2
- 229960004560 triaziquone Drugs 0.000 claims 2
- 229960001099 trimetrexate Drugs 0.000 claims 2
- 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 claims 2
- HDZZVAMISRMYHH-LITAXDCLSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O HDZZVAMISRMYHH-LITAXDCLSA-N 0.000 claims 2
- 229950006929 uredepa Drugs 0.000 claims 2
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 claims 2
- 229960000641 zorubicin Drugs 0.000 claims 2
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin 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)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 claims 2
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims 1
- 241000428352 Amma Species 0.000 claims 1
- 229930195573 Amycin Natural products 0.000 claims 1
- 108010024976 Asparaginase Proteins 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 229940122361 Bisphosphonate Drugs 0.000 claims 1
- 244000253759 Carya myristiciformis Species 0.000 claims 1
- XCDXSSFOJZZGQC-UHFFFAOYSA-N Chlornaphazine Chemical compound C1=CC=CC2=CC(N(CCCl)CCCl)=CC=C21 XCDXSSFOJZZGQC-UHFFFAOYSA-N 0.000 claims 1
- 229940123414 Folate antagonist Drugs 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 101001018097 Homo sapiens L-selectin Proteins 0.000 claims 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims 1
- 235000014072 Juglans neotropica Nutrition 0.000 claims 1
- 102100033467 L-selectin Human genes 0.000 claims 1
- 241000577218 Phenes Species 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims 1
- 101710183280 Topoisomerase Chemical class 0.000 claims 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims 1
- 208000008383 Wilms tumor Diseases 0.000 claims 1
- SPJCRMJCFSJKDE-ZWBUGVOYSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 SPJCRMJCFSJKDE-ZWBUGVOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229960000473 altretamine Drugs 0.000 claims 1
- 229940000806 amaryl Drugs 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 claims 1
- 239000003886 aromatase inhibitor Substances 0.000 claims 1
- 229940046844 aromatase inhibitors Drugs 0.000 claims 1
- 150000004663 bisphosphonates Chemical class 0.000 claims 1
- 210000000621 bronchi Anatomy 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229950008249 chlornaphazine Drugs 0.000 claims 1
- 229960001842 estramustine Drugs 0.000 claims 1
- FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 208000024386 fungal infectious disease Diseases 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical group O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 claims 1
- 229960001330 hydroxycarbamide Drugs 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 230000029115 microtubule polymerization Effects 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 201000005962 mycosis fungoides Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 210000002997 osteoclast Anatomy 0.000 claims 1
- 230000002188 osteogenic effect Effects 0.000 claims 1
- 208000028591 pheochromocytoma Diseases 0.000 claims 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 claims 1
- 229950001100 piposulfan Drugs 0.000 claims 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 1
- 201000008261 skin carcinoma Diseases 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 description 23
- 239000000651 prodrug Substances 0.000 description 23
- 229940079593 drug Drugs 0.000 description 21
- 125000001475 halogen functional group Chemical group 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 230000001472 cytotoxic effect Effects 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 6
- 231100000331 toxic Toxicity 0.000 description 6
- 230000002588 toxic effect Effects 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 238000001994 activation Methods 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 238000002512 chemotherapy Methods 0.000 description 4
- 231100000433 cytotoxic Toxicity 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000007954 hypoxia Effects 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 238000010913 antigen-directed enzyme pro-drug therapy Methods 0.000 description 3
- 208000035269 cancer or benign tumor Diseases 0.000 description 3
- 231100000599 cytotoxic agent Toxicity 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 108700012359 toxins Proteins 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000012661 PARP inhibitor Substances 0.000 description 2
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 239000002254 cytotoxic agent Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 238000010914 gene-directed enzyme pro-drug therapy Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000005181 nitrobenzenes Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000004222 uncontrolled growth Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 210000005166 vasculature Anatomy 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UKIWLFJYNMJPEG-UHFFFAOYSA-N 5-bromo-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(O)=NC=CC2=C1Br UKIWLFJYNMJPEG-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- 102000004328 Cytochrome P-450 CYP3A Human genes 0.000 description 1
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 1
- 101710112752 Cytotoxin Proteins 0.000 description 1
- 230000008265 DNA repair mechanism Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000756171 Hypoxis Species 0.000 description 1
- BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 description 1
- 108010045510 NADPH-Ferrihemoprotein Reductase Proteins 0.000 description 1
- 206010061309 Neoplasm progression Diseases 0.000 description 1
- 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 description 1
- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 description 1
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 101150049278 US20 gene Proteins 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- CGRNNEJYAQQCOQ-UHFFFAOYSA-N carbamic acid;2-nitro-1h-imidazole Chemical compound NC(O)=O.[O-][N+](=O)C1=NC=CN1 CGRNNEJYAQQCOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000011443 conventional therapy Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 239000002619 cytotoxin Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- QJIWQTQZVBIUTA-UHFFFAOYSA-N furan;1,3-thiazole Chemical compound C=1C=COC=1.C1=CSC=N1 QJIWQTQZVBIUTA-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002534 radiation-sensitizing agent Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- PFXVKGGZWQQTSE-UHFFFAOYSA-N sulfuryl dicyanide Chemical compound N#CS(=O)(=O)C#N PFXVKGGZWQQTSE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229950002376 tirapazamine Drugs 0.000 description 1
- ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/559—Redox delivery systems, e.g. dihydropyridine pyridinium salt redox systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6891—Pre-targeting systems involving an antibody for targeting specific cells
- A61K47/6899—Antibody-Directed Enzyme Prodrug Therapy [ADEPT]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45884503P | 2003-03-28 | 2003-03-28 | |
US46528103P | 2003-04-21 | 2003-04-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200507752B true ZA200507752B (en) | 2007-01-31 |
Family
ID=33135116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200507752A ZA200507752B (en) | 2003-03-28 | 2004-03-28 | Compositions and methods for treating cancer |
Country Status (14)
Country | Link |
---|---|
US (2) | US7550496B2 (ko) |
EP (2) | EP1622608A4 (ko) |
JP (2) | JP2006521409A (ko) |
KR (2) | KR101198526B1 (ko) |
CN (2) | CN1791403A (ko) |
AU (1) | AU2004226338C1 (ko) |
CA (1) | CA2520000C (ko) |
ES (1) | ES2759176T3 (ko) |
IL (1) | IL170970A (ko) |
MX (1) | MXPA05010407A (ko) |
NO (1) | NO336266B1 (ko) |
NZ (1) | NZ543223A (ko) |
WO (1) | WO2004087075A2 (ko) |
ZA (1) | ZA200507752B (ko) |
Families Citing this family (77)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA200507752B (en) * | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
US7691838B2 (en) | 2003-05-30 | 2010-04-06 | Kosan Biosciences Incorporated | Method for treating diseases using HSP90-inhibiting agents in combination with antimitotics |
DE50305909D1 (de) * | 2003-10-13 | 2007-01-18 | Salama Zoser B | Pharmazeutische Zusammensetzung umfassend Oxoplatin und dessen Salze |
US20080132458A1 (en) * | 2004-03-10 | 2008-06-05 | Threshold Pharmaceuticals, Inc. | Hypoxia-Activated Anti-Cancer Agents |
GB0421296D0 (en) * | 2004-09-24 | 2004-10-27 | Angiogene Pharm Ltd | Bioreductively-activated prodrugs |
US7208611B2 (en) | 2005-02-23 | 2007-04-24 | Xenoport, Inc. | Platinum-containing compounds exhibiting cytostatic activity, synthesis and methods of use |
JP2006282653A (ja) * | 2005-03-10 | 2006-10-19 | Kyoto Univ | 標的部位で選択的に活性化される新規化合物およびその利用 |
JP5180824B2 (ja) | 2005-06-29 | 2013-04-10 | スレッシュホールド ファーマシューティカルズ, インコーポレイテッド | ホスホルアミデートアルキル化剤プロドラッグ |
WO2008083101A1 (en) * | 2006-12-26 | 2008-07-10 | Threshold Pharmaceuticals, Inc. | Phosphoramidate alkylator prodrugs for the treatment of cancer |
CN101765369A (zh) | 2007-03-19 | 2010-06-30 | 俄勒冈州由俄勒冈州立大学代表州高等教育委员会行使 | 曼尼希碱n-氧化物药物 |
WO2008151253A1 (en) * | 2007-06-04 | 2008-12-11 | Threshold Pharmaceuticals, Inc. | Hypoxia activated prodrugs of antineoplastic agents |
WO2009018163A1 (en) * | 2007-07-27 | 2009-02-05 | Threshold Pharmaceuticals, Inc. | Hypoxia activated prodrugs of anthracyclines |
WO2009033165A1 (en) * | 2007-09-06 | 2009-03-12 | Threshold Pharmaceuticals, Inc. | Hypoxia activated prodrugs of bis-alkylating agents |
US20090118031A1 (en) * | 2007-11-01 | 2009-05-07 | Qualizza Gregory K | Shaft Structure with Configurable Bending Profile |
ES2884674T3 (es) | 2008-10-21 | 2021-12-10 | Immunogenesis Inc | Tratamiento del cáncer con el profármaco activado por hipoxia TH-302 en combinación con docetaxel o pemetrexed |
WO2010073126A2 (en) * | 2008-12-22 | 2010-07-01 | The Governors Of The University Of Alberta | Compounds useful in delivering anti-neoplastic therapy and diagnostic imaging to hypoxic cells and methods of use thereof |
CN101538256B (zh) * | 2009-04-28 | 2014-05-21 | 沈阳药科大学 | 3,4-二芳基呋喃-2,5-二酮类衍生物与3,4-二芳基-1h-吡咯-2,5-二酮类衍生物及其用途 |
GB0907551D0 (en) | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
EP3311835B1 (en) | 2010-07-12 | 2021-03-24 | Threshold Pharmaceuticals Inc. | Administration of hypoxia activated prodrugs and antiangiogenic agents for the treatment of cancer |
CN103327983A (zh) * | 2010-12-06 | 2013-09-25 | 梅里麦克制药股份有限公司 | 在使用包含蒽环类化疗剂的erbb2靶向免疫脂质体的治疗中防止心肌毒性的剂量和给药 |
WO2012145684A1 (en) | 2011-04-22 | 2012-10-26 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Transient hypoxia inducers and their use |
CN102260273B (zh) * | 2011-05-13 | 2015-04-22 | 兰州大学 | 脱氧鬼臼与5-氟尿嘧啶的拼合物及其制备与用途 |
EP2793882A4 (en) | 2011-12-22 | 2015-04-29 | Threshold Pharmaceuticals Inc | ADMINISTRATION OF HYPOXIA ACTIVATED DRUGS IN COMBINATION WITH CHK1 INHIBITORS FOR THE TREATMENT OF CANCER |
PT2797416T (pt) | 2011-12-28 | 2017-10-23 | Global Blood Therapeutics Inc | Compostos de benzaldeído substituído e métodos para a sua utilização no aumento da oxigenação de tecidos |
ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
CN104427984A (zh) | 2012-01-20 | 2015-03-18 | D·布朗 | 包括二脱水半乳糖醇和类似物的经取代的己糖醇类于治疗包括多形性胶质母细胞瘤和成神经管细胞瘤的肿瘤疾病和癌症干细胞的用途 |
JP5676020B2 (ja) | 2012-02-13 | 2015-02-25 | 国立大学法人 筑波大学 | ニトロイミダゾールを用いたプロドラッグ |
CN104204035B (zh) | 2012-03-30 | 2017-05-24 | 宇部兴产株式会社 | 具有封端基团的聚轮烷的制造方法 |
WO2014058974A1 (en) * | 2012-10-10 | 2014-04-17 | Emory University | Methods of managing inflammation using glycolysis pathway inhibitors |
US9278124B2 (en) | 2012-10-16 | 2016-03-08 | Halozyme, Inc. | Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods |
JP5922791B2 (ja) | 2012-10-29 | 2016-05-24 | 京セラ株式会社 | 弾性表面波センサ |
JP2016501234A (ja) | 2012-12-03 | 2016-01-18 | メリマック ファーマスーティカルズ, インコーポレイテッドMerrimack Pharmaceuticals, Inc. | Her2陽性癌を処置するための併用療法 |
EP2777694A1 (en) | 2013-03-14 | 2014-09-17 | Brij P. Giri | Hypoxia-Targeted Polymeric Micelles for Cancer Therapy and Imaging |
US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
AP2015008718A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
CN105073728A (zh) | 2013-03-15 | 2015-11-18 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
WO2014150261A1 (en) | 2013-03-15 | 2014-09-25 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulaton of hemoglobin |
US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
MY180206A (en) | 2013-03-15 | 2020-11-25 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
JP2016519684A (ja) | 2013-04-08 | 2016-07-07 | デニス エム ブラウン | 準最適に投与された薬物療法の有効性を改善するための及び/又は副作用を低減するための方法および組成物 |
WO2014181314A1 (en) | 2013-05-10 | 2014-11-13 | Department Of Biotechnology | Placental like alkaline phosphatase (plap) promoter mediated cell targeting |
CN112472699A (zh) | 2013-07-26 | 2021-03-12 | 种族肿瘤学公司 | 改善比生群及衍生物的治疗益处的组合方法 |
EP3024490A1 (en) | 2013-07-26 | 2016-06-01 | Threshold Pharmaceuticals, Inc. | Treatment of pancreatic cancer with a combination of a hypoxia-acti vated prodrug and a taxane |
CN104434876B (zh) * | 2013-09-13 | 2018-04-27 | 布里吉·P·吉里 | 用于癌症疗法及成像的缺氧-标靶聚合微胞 |
EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
DK3102208T3 (da) | 2014-02-07 | 2021-03-08 | Global Blood Therapeutics Inc | Krystallinsk polymorf af den frie base af 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyd |
CN106659765B (zh) | 2014-04-04 | 2021-08-13 | 德玛医药 | 二脱水半乳糖醇及其类似物或衍生物用于治疗非小细胞肺癌和卵巢癌的用途 |
US10131683B2 (en) | 2014-07-17 | 2018-11-20 | Molecular Templates, Inc. | TH-302 solid forms and methods related thereto |
AU2016229136B2 (en) | 2015-03-10 | 2018-08-09 | Obi Pharma, Inc. | DNA alkylating agents |
MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
BR112017021167A2 (pt) | 2015-04-02 | 2018-07-03 | Obi Pharma, Inc. | composto, método de tratamento de câncer, e processo para preparar o composto de fórmula i |
TWI772263B (zh) | 2015-06-24 | 2022-08-01 | 美商免疫原公司 | 含有dna烷化劑之氮丙啶 |
BR112018005200A2 (pt) | 2015-09-16 | 2018-10-09 | Dfb Soria Llc | liberação de nanopartículas de fármaco e métodos de uso dos mesmos |
CN105250325A (zh) * | 2015-10-28 | 2016-01-20 | 淄博齐鼎立专利信息咨询有限公司 | Demissine在制备治疗肾癌药物中的应用 |
MA43373A (fr) | 2015-12-04 | 2018-10-10 | Global Blood Therapeutics Inc | Régimes posologiques pour 2-hydroxy-6-((2- (1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)méthoxy)benzaldéhyde |
AR108435A1 (es) | 2016-05-12 | 2018-08-22 | Global Blood Therapeutics Inc | Proceso para sintetizar 2-hidroxi-6-((2-(1-isopropil-1h-pirazol-5-il)-piridin-3-il)metoxi)benzaldehído |
CN106554375B (zh) * | 2016-06-08 | 2019-10-18 | 浙江海正药业股份有限公司 | 一种蒽环类化合物、其制备方法及其用途 |
TWI778983B (zh) | 2016-10-12 | 2022-10-01 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
ES2955884T3 (es) | 2017-03-15 | 2023-12-07 | Dfb Soria Llc | Terapia tópica para el tratamiento de malignidades de la piel con nanoparticulas de taxanos |
CN106977501A (zh) * | 2017-03-20 | 2017-07-25 | 华东师范大学 | 一种基于2‑硝基咪唑‑1‑烷基醇的低氧激活前药 |
CN107417672A (zh) * | 2017-04-12 | 2017-12-01 | 华东师范大学 | 一种基于2,2‑二甲基‑3‑(2‑硝基咪唑基)丙酸的低氧激活前药 |
ES2935729T3 (es) * | 2017-09-14 | 2023-03-09 | Lankenau Inst Medical Res | Métodos y composiciones para el tratamiento del cáncer |
CA3091027A1 (en) | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
JP7372252B2 (ja) | 2018-03-16 | 2023-10-31 | ディーエフビー ソリア リミテッド ライアビリティ カンパニー | タキサンのナノ粒子を用いる子宮頸部上皮内腫瘍(cin)および子宮頸癌の処置のための局所療法 |
WO2020072377A1 (en) | 2018-10-01 | 2020-04-09 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin for the treatment of sickle cell disease |
KR20230023463A (ko) | 2021-08-10 | 2023-02-17 | 경북대학교 산학협력단 | 두경부암의 예후 예측을 위한 암 관련 섬유아세포의 바이오마커 |
KR20240047452A (ko) | 2021-08-27 | 2024-04-12 | 아센타위츠 파마슈티컬즈 리미티드 | 동결건조 제형 용액과 동결건조 제형, 및 이의 방법과 용도 |
WO2023025312A1 (zh) | 2021-08-27 | 2023-03-02 | 深圳艾欣达伟医药科技有限公司 | 使用th-302治疗parp抑制剂耐药的患者 |
CN113968867A (zh) * | 2021-11-10 | 2022-01-25 | 聊城大学 | 一种喜树碱类前药及其用途 |
CN114617876B (zh) * | 2022-01-28 | 2023-04-07 | 四川大学华西医院 | 一种抗肿瘤联合用药物 |
CN116675620A (zh) * | 2022-02-22 | 2023-09-01 | 东南大学 | No供体化合物及其制备方法、药物组合物和应用 |
Family Cites Families (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3652579A (en) | 1969-06-26 | 1972-03-28 | Hoffmann La Roche | 1-methyl-2-substituted 5-nitroimidazoles |
DE2229223C3 (de) | 1971-07-30 | 1975-12-18 | Gruppo Lepetit S.P.A., Mailand (Italien) | 2-Nitro-S-imidazol-Derivate und Verfahren zu deren Herstellung |
US4921963A (en) * | 1987-04-13 | 1990-05-01 | British Columbia Cancer Foundation | Platinum complexes with one radiosensitizing ligand |
JPH0819111B2 (ja) | 1987-10-22 | 1996-02-28 | ポーラ化成工業株式会社 | 2―ニトロイミダゾール誘導体及びこれを有効成分とする放射線増感剤 |
US5190929A (en) | 1988-05-25 | 1993-03-02 | Research Corporation Technologies, Inc. | Cyclophosphamide analogs useful as anti-tumor agents |
US4908356A (en) | 1988-05-25 | 1990-03-13 | Research Corporation Technologies, Inc. | Aldophosphamide derivatives useful as antitumor agents |
US5403932A (en) | 1988-05-25 | 1995-04-04 | Research Corporation Technologies, Inc. | Phosphoramidates useful as antitumor agents |
DE3835772A1 (de) | 1988-10-20 | 1990-04-26 | Deutsches Krebsforsch | Tumorhemmende saccharid-konjugate |
JP2626727B2 (ja) | 1990-01-26 | 1997-07-02 | ポーラ化成工業株式会社 | 2―ニトロイミダゾール誘導体、その製造法及びこれを有効成分とする放射線増感剤 |
US5233031A (en) * | 1991-09-23 | 1993-08-03 | University Of Rochester | Phosphoramidate analogs of 2'-deoxyuridine |
WO1993008288A1 (en) | 1991-10-23 | 1993-04-29 | Cancer Research Campaign Technology Limited | Bacterial nitroreductase for the reduction of cb 1954 and analogues thereof to a cytotoxic form |
US5750782A (en) | 1992-11-27 | 1998-05-12 | Cancer Research Campaign Technology Limited | Nitroaniline derivatives and their use as anti-tumour agents |
US5306727A (en) | 1993-04-30 | 1994-04-26 | Research Corporation Technologies, Inc. | Phosphoramidates useful as antitumor agents |
AU6859394A (en) | 1993-05-25 | 1994-12-20 | Auckland Uniservices Limited | Nitrobenzyl mustard quaternary salts and their use as hypoxia-selective cytotoxic agents |
EP0648503B1 (en) | 1993-09-22 | 2000-07-26 | Hoechst Aktiengesellschaft | Pro-prodrugs, their production and use |
JPH07309761A (ja) | 1994-05-20 | 1995-11-28 | Kyowa Hakko Kogyo Co Ltd | デュオカルマイシン誘導体の安定化法 |
US5659061A (en) | 1995-04-20 | 1997-08-19 | Drug Innovation & Design, Inc. | Tumor protease activated prodrugs of phosphoramide mustard analogs with toxification and detoxification functionalities |
GB9516943D0 (en) | 1995-08-18 | 1995-10-18 | Cancer Soc Auckland Div Nz Inc | Novel cyclopropylindoles and their secoprecursors,and their use as prodrugs |
GB9526391D0 (en) | 1995-12-22 | 1996-02-21 | Diversey Equipment Technologie | Dispenser |
US6218519B1 (en) | 1996-04-12 | 2001-04-17 | Pro-Neuron, Inc. | Compounds and methods for the selective treatment of cancer and bacterial infections |
US6130237A (en) | 1996-09-12 | 2000-10-10 | Cancer Research Campaign Technology Limited | Condensed N-aclyindoles as antitumor agents |
US6251933B1 (en) | 1996-12-13 | 2001-06-26 | The Cancer Research Campaign Technology Limited | Seco precursors of cyclopropylindolines and their use as prodrugs |
DE19720312A1 (de) | 1997-05-15 | 1998-11-19 | Hoechst Ag | Zubereitung mit erhöhter in vivo Verträglichkeit |
GB9818730D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
US6240925B1 (en) | 1999-03-23 | 2001-06-05 | Cynosure, Inc. | Photothermal vascular targeting with bioreductive agents |
GB9909612D0 (en) | 1999-04-26 | 1999-06-23 | Cancer Res Campaign Tech | N-protected amines and their use as prodrugs |
JP4629238B2 (ja) * | 1999-05-24 | 2011-02-09 | サザン・リサーチ・インスティテュート | イソホスホアミドマスタード・アナログ及びその使用 |
AU5935600A (en) | 1999-07-14 | 2001-01-30 | Richard F. Borch | Phosphoramide compounds |
DE60117247D1 (de) * | 2000-03-31 | 2006-04-20 | Purdue Research Foundation West Lafayette | Phosphoramidat-prodrugs |
JP2002046334A (ja) | 2000-08-04 | 2002-02-12 | Riso Kagaku Corp | 孔版印刷装置及び該装置の印刷ドラム |
EP1243276A1 (en) | 2001-03-23 | 2002-09-25 | Franciscus Marinus Hendrikus De Groot | Elongated and multiple spacers containing activatible prodrugs |
US6506739B1 (en) | 2001-05-01 | 2003-01-14 | Telik, Inc. | Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents |
KR20030033007A (ko) | 2001-05-31 | 2003-04-26 | 코울터 파머수티컬, 인코포레이티드 | 세포독소, 약물전구체, 링커 및 이에 유용한 안정화제 |
FR2825926A1 (fr) * | 2001-06-14 | 2002-12-20 | Sod Conseils Rech Applic | Derives d'imidazoles modulant les canaux sodiques |
US7091186B2 (en) | 2001-09-24 | 2006-08-15 | Seattle Genetics, Inc. | p-Amidobenzylethers in drug delivery agents |
KR20030067275A (ko) | 2002-02-07 | 2003-08-14 | 주식회사 하이폭시 | 니트로이미다졸 및 위상 이성질화 효소 저해제를유효성분으로 포함하는 항암제 |
JP4187096B2 (ja) | 2003-01-15 | 2008-11-26 | 独立行政法人科学技術振興機構 | 3次元フォトニック結晶製造方法 |
GB0306907D0 (en) | 2003-03-26 | 2003-04-30 | Angiogene Pharm Ltd | Boireductively-activated prodrugs |
GB0306908D0 (en) | 2003-03-26 | 2003-04-30 | Angiogene Pharm Ltd | Bioreductively activated stilbene prodrugs |
ZA200507752B (en) * | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
US6855695B2 (en) | 2003-06-13 | 2005-02-15 | Vion Pharmaceuticals, Inc. | Water-soluble SHPs as novel alkylating agents |
CA2554463C (en) | 2004-02-06 | 2013-06-11 | Threshold Pharmaceuticals, Inc. | Anti-cancer therapies |
WO2006057946A2 (en) | 2004-11-22 | 2006-06-01 | Threshold Pharmaceuticals, Inc. | Tubulin binding anti cancer agents and prodrugs thereof |
WO2008011588A2 (en) | 2006-07-20 | 2008-01-24 | Threshold Pharmaceuticals, Inc. | Glycoconjugates of phosphoramidate alkylators for treatment of cancer |
WO2008076826A1 (en) | 2006-12-13 | 2008-06-26 | Threshold Pharmaceuticals, Inc. | Pyrophosphoramide alkylators |
WO2008083101A1 (en) | 2006-12-26 | 2008-07-10 | Threshold Pharmaceuticals, Inc. | Phosphoramidate alkylator prodrugs for the treatment of cancer |
-
2004
- 2004-03-28 ZA ZA200507752A patent/ZA200507752B/en unknown
- 2004-03-29 CA CA2520000A patent/CA2520000C/en not_active Expired - Lifetime
- 2004-03-29 AU AU2004226338A patent/AU2004226338C1/en not_active Expired
- 2004-03-29 US US10/549,545 patent/US7550496B2/en active Active
- 2004-03-29 NZ NZ543223A patent/NZ543223A/en not_active IP Right Cessation
- 2004-03-29 JP JP2006509466A patent/JP2006521409A/ja not_active Ceased
- 2004-03-29 EP EP04749522A patent/EP1622608A4/en not_active Withdrawn
- 2004-03-29 KR KR1020127002215A patent/KR101198526B1/ko active IP Right Grant
- 2004-03-29 MX MXPA05010407A patent/MXPA05010407A/es active IP Right Grant
- 2004-03-29 CN CNA2004800132768A patent/CN1791403A/zh active Pending
- 2004-03-29 WO PCT/US2004/009667 patent/WO2004087075A2/en active Application Filing
- 2004-03-29 EP EP13178249.2A patent/EP2671581B8/en not_active Expired - Lifetime
- 2004-03-29 ES ES13178249T patent/ES2759176T3/es not_active Expired - Lifetime
- 2004-03-29 KR KR1020057018367A patent/KR20050113670A/ko not_active IP Right Cessation
- 2004-03-29 CN CN2010105956028A patent/CN102161679A/zh active Pending
-
2005
- 2005-09-19 IL IL170970A patent/IL170970A/en active IP Right Grant
- 2005-10-26 NO NO20054988A patent/NO336266B1/no not_active IP Right Cessation
-
2009
- 2009-06-12 US US12/484,104 patent/US8299088B2/en active Active
-
2012
- 2012-01-26 JP JP2012014178A patent/JP5572644B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR20120035198A (ko) | 2012-04-13 |
CA2520000A1 (en) | 2004-10-14 |
NO20054988D0 (no) | 2005-10-26 |
US7550496B2 (en) | 2009-06-23 |
EP1622608A4 (en) | 2010-11-10 |
MXPA05010407A (es) | 2006-05-31 |
US20090312276A1 (en) | 2009-12-17 |
IL170970A (en) | 2012-01-31 |
JP5572644B2 (ja) | 2014-08-13 |
NZ543223A (en) | 2008-11-28 |
KR101198526B1 (ko) | 2012-11-06 |
EP2671581A3 (en) | 2014-01-01 |
EP1622608A2 (en) | 2006-02-08 |
AU2004226338A1 (en) | 2004-10-14 |
AU2004226338B2 (en) | 2011-05-19 |
CA2520000C (en) | 2012-06-05 |
CN102161679A (zh) | 2011-08-24 |
EP2671581A2 (en) | 2013-12-11 |
US20060258656A1 (en) | 2006-11-16 |
US8299088B2 (en) | 2012-10-30 |
EP2671581B8 (en) | 2019-11-13 |
CN1791403A (zh) | 2006-06-21 |
WO2004087075A2 (en) | 2004-10-14 |
AU2004226338C1 (en) | 2012-01-12 |
NO20054988L (no) | 2005-12-23 |
ES2759176T3 (es) | 2020-05-07 |
EP2671581B1 (en) | 2019-10-02 |
WO2004087075A3 (en) | 2005-03-24 |
JP2012082227A (ja) | 2012-04-26 |
JP2006521409A (ja) | 2006-09-21 |
KR20050113670A (ko) | 2005-12-02 |
NO336266B1 (no) | 2015-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200507752B (en) | Compositions and methods for treating cancer | |
US8664204B2 (en) | Phosphoramidate alkylator prodrugs | |
US20080132458A1 (en) | Hypoxia-Activated Anti-Cancer Agents | |
Vrudhula et al. | Reductively activated disulfide prodrugs of paclitaxel | |
JP2006521409A5 (ko) | ||
WO2006065448A2 (en) | Topoisomerase inhibitors and prodrugs | |
WO2007137196A2 (en) | Tubulin binding anti cancer compounds and prodrugs thereof |