ES2438998T3 - Terapias combinadas que comprenden un inhibidor de quinaxolina de PI3K alfa para utilizar en el tratamiento del cáncer - Google Patents
Terapias combinadas que comprenden un inhibidor de quinaxolina de PI3K alfa para utilizar en el tratamiento del cáncer Download PDFInfo
- Publication number
- ES2438998T3 ES2438998T3 ES08742674.8T ES08742674T ES2438998T3 ES 2438998 T3 ES2438998 T3 ES 2438998T3 ES 08742674 T ES08742674 T ES 08742674T ES 2438998 T3 ES2438998 T3 ES 2438998T3
- Authority
- ES
- Spain
- Prior art keywords
- nhc
- compound
- treatment
- amino
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 603
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 166
- 201000011510 cancer Diseases 0.000 title claims abstract description 162
- 239000003112 inhibitor Substances 0.000 title description 38
- 108091007960 PI3Ks Proteins 0.000 title description 2
- 238000002648 combination therapy Methods 0.000 title description 2
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 436
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 242
- 229940127089 cytotoxic agent Drugs 0.000 claims abstract description 241
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims abstract description 33
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims abstract description 27
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229960002930 sirolimus Drugs 0.000 claims abstract description 27
- 239000012453 solvate Substances 0.000 claims abstract description 26
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 21
- 229960001433 erlotinib Drugs 0.000 claims abstract description 20
- 229940123237 Taxane Drugs 0.000 claims abstract description 16
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims abstract description 16
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical group [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 24
- 229930012538 Paclitaxel Natural products 0.000 claims description 23
- 229960004562 carboplatin Drugs 0.000 claims description 23
- 229960001592 paclitaxel Drugs 0.000 claims description 23
- 206010006187 Breast cancer Diseases 0.000 claims description 20
- 208000026310 Breast neoplasm Diseases 0.000 claims description 20
- 206010060862 Prostate cancer Diseases 0.000 claims description 14
- 208000005017 glioblastoma Diseases 0.000 claims description 12
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 12
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 12
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 11
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 11
- 206010033128 Ovarian cancer Diseases 0.000 claims description 11
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 11
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
- 201000001441 melanoma Diseases 0.000 claims description 9
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 8
- 206010009944 Colon cancer Diseases 0.000 claims description 8
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 8
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 8
- 201000010881 cervical cancer Diseases 0.000 claims description 8
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 7
- 206010014733 Endometrial cancer Diseases 0.000 claims description 7
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 7
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 7
- 208000029742 colonic neoplasm Diseases 0.000 claims description 7
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 7
- 206010038038 rectal cancer Diseases 0.000 claims description 7
- 201000001275 rectum cancer Diseases 0.000 claims description 7
- 206010007279 Carcinoid tumour of the gastrointestinal tract Diseases 0.000 claims description 6
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 4
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 208000033781 Thyroid carcinoma Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 201000001514 prostate carcinoma Diseases 0.000 claims description 3
- 201000002510 thyroid cancer Diseases 0.000 claims description 3
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims description 3
- 125000002456 taxol group Chemical group 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- -1 hydroxy, cyano, amino Chemical group 0.000 description 522
- 238000000034 method Methods 0.000 description 402
- 125000000217 alkyl group Chemical group 0.000 description 232
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 173
- 239000001257 hydrogen Substances 0.000 description 163
- 229910052739 hydrogen Inorganic materials 0.000 description 163
- 229910052740 iodine Inorganic materials 0.000 description 144
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 116
- 125000003342 alkenyl group Chemical group 0.000 description 90
- 125000003545 alkoxy group Chemical group 0.000 description 83
- 125000002947 alkylene group Chemical group 0.000 description 83
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 78
- 125000005843 halogen group Chemical group 0.000 description 67
- 125000003118 aryl group Chemical group 0.000 description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 63
- 125000001072 heteroaryl group Chemical group 0.000 description 59
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 56
- 239000003795 chemical substances by application Substances 0.000 description 53
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 47
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 37
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 36
- 230000005855 radiation Effects 0.000 description 35
- NCTHHJRIJGFPTG-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)-4-[7-[[6,7-bis(aziridin-1-yl)-5,8-dioxoquinazolin-4-yl]amino]heptylamino]quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=C(NCCCCCCCNC=3C=4C(=O)C(N5CC5)=C(N5CC5)C(=O)C=4N=CN=3)N=CN=C2C(=O)C=1N1CC1 NCTHHJRIJGFPTG-UHFFFAOYSA-N 0.000 description 34
- 125000000753 cycloalkyl group Chemical group 0.000 description 34
- 125000001188 haloalkyl group Chemical group 0.000 description 34
- 125000003282 alkyl amino group Chemical group 0.000 description 32
- 238000001356 surgical procedure Methods 0.000 description 32
- 125000004663 dialkyl amino group Chemical group 0.000 description 30
- 125000004438 haloalkoxy group Chemical group 0.000 description 30
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 29
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 29
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 28
- 238000001794 hormone therapy Methods 0.000 description 28
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 27
- 125000004103 aminoalkyl group Chemical group 0.000 description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
- 125000003710 aryl alkyl group Chemical group 0.000 description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 22
- 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 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 21
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 20
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 18
- 229960004316 cisplatin Drugs 0.000 description 18
- 201000010099 disease Diseases 0.000 description 18
- 125000004446 heteroarylalkyl group Chemical group 0.000 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 description 17
- 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 description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 16
- 125000004043 oxo group Chemical group O=* 0.000 description 16
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 16
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 15
- 229960000241 vandetanib Drugs 0.000 description 15
- 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 description 14
- 239000002253 acid Substances 0.000 description 14
- 125000003302 alkenyloxy group Chemical group 0.000 description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 14
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 14
- 238000009169 immunotherapy Methods 0.000 description 14
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 14
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 14
- 229960001756 oxaliplatin Drugs 0.000 description 14
- 239000002136 L01XE07 - Lapatinib Substances 0.000 description 13
- 108091000080 Phosphotransferase Proteins 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 13
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 13
- 102000020233 phosphotransferase Human genes 0.000 description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 12
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 12
- 229960003668 docetaxel Drugs 0.000 description 12
- 229940121647 egfr inhibitor Drugs 0.000 description 12
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 12
- 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 description 12
- 229960004528 vincristine Drugs 0.000 description 12
- 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 description 12
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 11
- 239000005511 L01XE05 - Sorafenib Substances 0.000 description 11
- 125000004414 alkyl thio group Chemical group 0.000 description 11
- 239000003886 aromatase inhibitor Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 11
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 11
- 229960003787 sorafenib Drugs 0.000 description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 10
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 10
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 10
- 239000002147 L01XE04 - Sunitinib Substances 0.000 description 10
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 10
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 229960000397 bevacizumab Drugs 0.000 description 10
- 229960002949 fluorouracil Drugs 0.000 description 10
- 229960000578 gemtuzumab Drugs 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 9
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 description 9
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 229960004397 cyclophosphamide Drugs 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 9
- 229960004891 lapatinib Drugs 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 9
- 229960004964 temozolomide Drugs 0.000 description 9
- 229960000575 trastuzumab Drugs 0.000 description 9
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 8
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 8
- 229940122815 Aromatase inhibitor Drugs 0.000 description 8
- 208000009956 adenocarcinoma Diseases 0.000 description 8
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000002431 aminoalkoxy group Chemical group 0.000 description 8
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 8
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 8
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 8
- 229960001796 sunitinib Drugs 0.000 description 8
- 208000011580 syndromic disease Diseases 0.000 description 8
- 238000002560 therapeutic procedure Methods 0.000 description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 7
- 201000009030 Carcinoma Diseases 0.000 description 7
- 241001024304 Mino Species 0.000 description 7
- 206010039491 Sarcoma Diseases 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229960005395 cetuximab Drugs 0.000 description 7
- 229960004679 doxorubicin Drugs 0.000 description 7
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 7
- 229960005277 gemcitabine Drugs 0.000 description 7
- 229940036571 iodine therapy Drugs 0.000 description 7
- 229940090004 megace Drugs 0.000 description 7
- 229960004296 megestrol acetate Drugs 0.000 description 7
- 229960001972 panitumumab Drugs 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 230000002285 radioactive effect Effects 0.000 description 7
- 229960001603 tamoxifen Drugs 0.000 description 7
- 229940120982 tarceva Drugs 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- 206010025323 Lymphomas Diseases 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 102100038332 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Human genes 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 6
- 229950002826 canertinib Drugs 0.000 description 6
- OMZCMEYTWSXEPZ-UHFFFAOYSA-N canertinib Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CC(OCCCN3CCOCC3)=C(NC(=O)C=C)C=C12 OMZCMEYTWSXEPZ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 6
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 6
- 235000008191 folinic acid Nutrition 0.000 description 6
- 239000011672 folinic acid Substances 0.000 description 6
- 235000019256 formaldehyde Nutrition 0.000 description 6
- 229940080856 gleevec Drugs 0.000 description 6
- 125000000262 haloalkenyl group Chemical group 0.000 description 6
- 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 description 6
- 229960002411 imatinib Drugs 0.000 description 6
- 229960001691 leucovorin Drugs 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 6
- WVUNYSQLFKLYNI-AATRIKPKSA-N pelitinib Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 WVUNYSQLFKLYNI-AATRIKPKSA-N 0.000 description 6
- 125000003373 pyrazinyl group Chemical group 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- 229960004641 rituximab Drugs 0.000 description 6
- 229960004889 salicylic acid Drugs 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 6
- 229960002066 vinorelbine Drugs 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- NPSLABWCQNFJHJ-GOOCMWNKSA-N 7-[[(3as,6ar)-2-methyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-5-yl]methoxy]-n-(4-bromo-3-chloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine Chemical compound N1=CN=C2C=C(OCC3C[C@@H]4CN(C)C[C@@H]4C3)C(OC)=CC2=C1NC1=CC=C(Br)C(Cl)=C1F NPSLABWCQNFJHJ-GOOCMWNKSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 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 description 5
- 108700012941 GNRH1 Proteins 0.000 description 5
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 5
- 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 description 5
- 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 description 5
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 5
- 239000012828 PI3K inhibitor Substances 0.000 description 5
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 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 description 5
- 238000002679 ablation Methods 0.000 description 5
- 229960000548 alemtuzumab Drugs 0.000 description 5
- 229940120638 avastin Drugs 0.000 description 5
- 230000000973 chemotherapeutic effect Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229960002584 gefitinib Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 5
- 229960001101 ifosfamide Drugs 0.000 description 5
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 5
- 229960000485 methotrexate Drugs 0.000 description 5
- BMGQWWVMWDBQGC-IIFHNQTCSA-N midostaurin Chemical compound CN([C@H]1[C@H]([C@]2(C)O[C@@H](N3C4=CC=CC=C4C4=C5C(=O)NCC5=C5C6=CC=CC=C6N2C5=C43)C1)OC)C(=O)C1=CC=CC=C1 BMGQWWVMWDBQGC-IIFHNQTCSA-N 0.000 description 5
- 229950010895 midostaurin Drugs 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 description 5
- 229950008835 neratinib Drugs 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 description 5
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 5
- 238000002271 resection Methods 0.000 description 5
- 206010041823 squamous cell carcinoma Diseases 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 229960000303 topotecan Drugs 0.000 description 5
- 229960005267 tositumomab Drugs 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- 229960003048 vinblastine Drugs 0.000 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 description 5
- RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 description 4
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- OONFNUWBHFSNBT-HXUWFJFHSA-N AEE788 Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)C=C1 OONFNUWBHFSNBT-HXUWFJFHSA-N 0.000 description 4
- 229940126638 Akt inhibitor Drugs 0.000 description 4
- QULDDKSCVCJTPV-UHFFFAOYSA-N BIIB021 Chemical compound COC1=C(C)C=NC(CN2C3=NC(N)=NC(Cl)=C3N=C2)=C1C QULDDKSCVCJTPV-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 206010024612 Lipoma Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 108700020796 Oncogene Proteins 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 108091008611 Protein Kinase B Proteins 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 206010041067 Small cell lung cancer Diseases 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229940124674 VEGF-R inhibitor Drugs 0.000 description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 4
- 229960002932 anastrozole Drugs 0.000 description 4
- 229940078010 arimidex Drugs 0.000 description 4
- 229940087620 aromasin Drugs 0.000 description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 4
- 229960004117 capecitabine Drugs 0.000 description 4
- 229940082789 erbitux Drugs 0.000 description 4
- 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 description 4
- 229960005420 etoposide Drugs 0.000 description 4
- 229960000255 exemestane Drugs 0.000 description 4
- 229940087476 femara Drugs 0.000 description 4
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 4
- 229940022353 herceptin Drugs 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229960001001 ibritumomab tiuxetan Drugs 0.000 description 4
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 4
- 229940084651 iressa Drugs 0.000 description 4
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 4
- 229960004768 irinotecan Drugs 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229960003881 letrozole Drugs 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical group OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- JWNPDZNEKVCWMY-VQHVLOKHSA-N neratinib Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 JWNPDZNEKVCWMY-VQHVLOKHSA-N 0.000 description 4
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 4
- 239000003197 protein kinase B inhibitor Substances 0.000 description 4
- 208000000587 small cell lung carcinoma Diseases 0.000 description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 description 4
- 229940063683 taxotere Drugs 0.000 description 4
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- 229940094060 tykerb Drugs 0.000 description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 description 3
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 3
- YABJJWZLRMPFSI-UHFFFAOYSA-N 1-methyl-5-[[2-[5-(trifluoromethyl)-1H-imidazol-2-yl]-4-pyridinyl]oxy]-N-[4-(trifluoromethyl)phenyl]-2-benzimidazolamine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1 YABJJWZLRMPFSI-UHFFFAOYSA-N 0.000 description 3
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 description 3
- KUFRQPKVAWMTJO-QSTRRNJOSA-N 17-dmag Chemical compound N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(NCCN(C)C)C(=O)C=C1C2=O KUFRQPKVAWMTJO-QSTRRNJOSA-N 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 208000001446 Anaplastic Thyroid Carcinoma Diseases 0.000 description 3
- 206010002240 Anaplastic thyroid cancer Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 201000005262 Chondroma Diseases 0.000 description 3
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 201000008808 Fibrosarcoma Diseases 0.000 description 3
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 3
- 101710113436 GTPase KRas Proteins 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 3
- 108010069236 Goserelin Proteins 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 102000014150 Interferons Human genes 0.000 description 3
- 108010050904 Interferons Proteins 0.000 description 3
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
- 239000002067 L01XE06 - Dasatinib Substances 0.000 description 3
- UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 description 3
- 108010000817 Leuprolide Proteins 0.000 description 3
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 description 3
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 description 3
- 206010033701 Papillary thyroid cancer Diseases 0.000 description 3
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 3
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 206010043276 Teratoma Diseases 0.000 description 3
- IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 3
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 3
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 3
- QTQAWLPCGQOSGP-VKNBREQOSA-N [(3r,5r,6s,7r,8e,10r,11r,12z,14e)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate Chemical compound N1C(=O)\C(C)=C\C=C/[C@@H](OC)[C@H](OC(N)=O)\C(C)=C\[C@@H](C)[C@H](O)[C@H](OC)C[C@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-VKNBREQOSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 229940125681 anticonvulsant agent Drugs 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229940046844 aromatase inhibitors Drugs 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229960005243 carmustine Drugs 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229960002412 cediranib Drugs 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 229960001231 choline Drugs 0.000 description 3
- 238000002681 cryosurgery Methods 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229960002448 dasatinib Drugs 0.000 description 3
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940012017 ethylenediamine Drugs 0.000 description 3
- 229940043168 fareston Drugs 0.000 description 3
- 229960003297 gemtuzumab ozogamicin Drugs 0.000 description 3
- 229960002913 goserelin Drugs 0.000 description 3
- 201000011066 hemangioma Diseases 0.000 description 3
- 230000003054 hormonal effect Effects 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229940079322 interferon Drugs 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 3
- 201000010260 leiomyoma Diseases 0.000 description 3
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 3
- 229960004338 leuprorelin Drugs 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229950010203 nimotuzumab Drugs 0.000 description 3
- 230000002611 ovarian Effects 0.000 description 3
- 210000005259 peripheral blood Anatomy 0.000 description 3
- 239000011886 peripheral blood Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229960004622 raloxifene Drugs 0.000 description 3
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000011476 stem cell transplantation Methods 0.000 description 3
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 3
- 229960001052 streptozocin Drugs 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)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-XAZOAEDWSA-N 0.000 description 3
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 3
- 208000019179 thyroid gland undifferentiated (anaplastic) carcinoma Diseases 0.000 description 3
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 3
- 229960005026 toremifene Drugs 0.000 description 3
- SVNJBEMPMKWDCO-KCHLEUMXSA-N (2s)-2-[[(2s)-3-carboxy-2-[[2-[[(2s)-5-(diaminomethylideneamino)-2-[[4-oxo-4-[[4-(4-oxo-8-phenylchromen-2-yl)morpholin-4-ium-4-yl]methoxy]butanoyl]amino]pentanoyl]amino]acetyl]amino]propanoyl]amino]-3-hydroxypropanoate Chemical compound C=1C(=O)C2=CC=CC(C=3C=CC=CC=3)=C2OC=1[N+]1(COC(=O)CCC(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C([O-])=O)CCOCC1 SVNJBEMPMKWDCO-KCHLEUMXSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- 125000004477 1-amino-cycloprop-1-yl group Chemical group NC1(CC1)* 0.000 description 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- XLZYKTYMLBOINK-UHFFFAOYSA-N 3-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 XLZYKTYMLBOINK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- SYYMNUFXRFAELA-BTQNPOSSSA-N 4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol;hydrobromide Chemical compound Br.N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(O)C=C1 SYYMNUFXRFAELA-BTQNPOSSSA-N 0.000 description 2
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- BUROJSBIWGDYCN-GAUTUEMISA-N AP 23573 Chemical compound C1C[C@@H](OP(C)(C)=O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 BUROJSBIWGDYCN-GAUTUEMISA-N 0.000 description 2
- 206010001233 Adenoma benign Diseases 0.000 description 2
- 101001015038 Albizia kalkora Kunitz-type trypsin inhibitor alpha chain Proteins 0.000 description 2
- 108010012934 Albumin-Bound Paclitaxel Proteins 0.000 description 2
- 201000003076 Angiosarcoma Diseases 0.000 description 2
- 101100297694 Arabidopsis thaliana PIP2-7 gene Proteins 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229940124204 C-kit inhibitor Drugs 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Chemical group OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- 230000005778 DNA damage Effects 0.000 description 2
- 231100000277 DNA damage Toxicity 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 2
- MPJKWIXIYCLVCU-UHFFFAOYSA-N Folinic acid Natural products NC1=NC2=C(N(C=O)C(CNc3ccc(cc3)C(=O)NC(CCC(=O)O)CC(=O)O)CN2)C(=O)N1 MPJKWIXIYCLVCU-UHFFFAOYSA-N 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 208000002927 Hamartoma Diseases 0.000 description 2
- 208000001258 Hemangiosarcoma Diseases 0.000 description 2
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 description 2
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 2
- 102000006992 Interferon-alpha Human genes 0.000 description 2
- 108010047761 Interferon-alpha Proteins 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000005536 L01XE08 - Nilotinib Substances 0.000 description 2
- 239000003798 L01XE11 - Pazopanib Substances 0.000 description 2
- 208000018142 Leiomyosarcoma Diseases 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Chemical group OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 2
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910003827 NRaRb Inorganic materials 0.000 description 2
- TUVCWJQQGGETHL-UHFFFAOYSA-N PI-103 Chemical compound OC1=CC=CC(C=2N=C3C4=CC=CN=C4OC3=C(N3CCOCC3)N=2)=C1 TUVCWJQQGGETHL-UHFFFAOYSA-N 0.000 description 2
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 2
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 description 2
- 101100456541 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MEC3 gene Proteins 0.000 description 2
- 101100483663 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UFD1 gene Proteins 0.000 description 2
- 102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 2
- 102100022596 Tyrosine-protein kinase ABL1 Human genes 0.000 description 2
- 208000008383 Wilms tumor Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009167 androgen deprivation therapy Methods 0.000 description 2
- 230000000340 anti-metabolite Effects 0.000 description 2
- 229940044684 anti-microtubule agent Drugs 0.000 description 2
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 238000003782 apoptosis assay Methods 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 0.000 description 2
- 229960003005 axitinib Drugs 0.000 description 2
- RITAVMQDGBJQJZ-FMIVXFBMSA-N axitinib Chemical compound CNC(=O)C1=CC=CC=C1SC1=CC=C(C(\C=C\C=2N=CC=CC=2)=NN2)C2=C1 RITAVMQDGBJQJZ-FMIVXFBMSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 208000002458 carcinoid tumor Diseases 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 2
- 229960004630 chlorambucil Drugs 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 229960000684 cytarabine Drugs 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 229960003901 dacarbazine Drugs 0.000 description 2
- 229960000975 daunorubicin Drugs 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 230000007783 downstream signaling Effects 0.000 description 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 206010016629 fibroma Diseases 0.000 description 2
- 229960000390 fludarabine Drugs 0.000 description 2
- 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 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229960004421 formestane Drugs 0.000 description 2
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- 206010017758 gastric cancer Diseases 0.000 description 2
- 208000010749 gastric carcinoma Diseases 0.000 description 2
- 239000000174 gluconic acid Chemical group 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Chemical group 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- 229960003685 imatinib mesylate Drugs 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229960002247 lomustine Drugs 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229950008001 matuzumab Drugs 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 2
- 229960001924 melphalan Drugs 0.000 description 2
- 206010027191 meningioma Diseases 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ONDPWWDPQDCQNJ-UHFFFAOYSA-N n-(3,3-dimethyl-1,2-dihydroindol-6-yl)-2-(pyridin-4-ylmethylamino)pyridine-3-carboxamide;phosphoric acid Chemical compound OP(O)(O)=O.OP(O)(O)=O.C=1C=C2C(C)(C)CNC2=CC=1NC(=O)C1=CC=CN=C1NCC1=CC=NC=C1 ONDPWWDPQDCQNJ-UHFFFAOYSA-N 0.000 description 2
- LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- 229940086322 navelbine Drugs 0.000 description 2
- 229960001346 nilotinib Drugs 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 201000008968 osteosarcoma Diseases 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229960000639 pazopanib Drugs 0.000 description 2
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 description 2
- 229950006299 pelitinib Drugs 0.000 description 2
- QOFFJEBXNKRSPX-ZDUSSCGKSA-N pemetrexed Chemical compound C1=N[C]2NC(N)=NC(=O)C2=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QOFFJEBXNKRSPX-ZDUSSCGKSA-N 0.000 description 2
- 229960005079 pemetrexed Drugs 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Chemical group 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 2
- 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 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- 229960004919 procaine Drugs 0.000 description 2
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 2
- 229960000624 procarbazine Drugs 0.000 description 2
- 230000005522 programmed cell death Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
- 229960001302 ridaforolimus Drugs 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 229950003647 semaxanib Drugs 0.000 description 2
- WUWDLXZGHZSWQZ-WQLSENKSSA-N semaxanib Chemical compound N1C(C)=CC(C)=C1\C=C/1C2=CC=CC=C2NC\1=O WUWDLXZGHZSWQZ-WQLSENKSSA-N 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000008117 stearic acid Chemical group 0.000 description 2
- 201000000498 stomach carcinoma Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229940034785 sutent Drugs 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- UXXQOJXBIDBUAC-UHFFFAOYSA-N tandutinib Chemical compound COC1=CC2=C(N3CCN(CC3)C(=O)NC=3C=CC(OC(C)C)=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 UXXQOJXBIDBUAC-UHFFFAOYSA-N 0.000 description 2
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 2
- 229950007866 tanespimycin Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 229960000235 temsirolimus Drugs 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 229960003087 tioguanine Drugs 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BNGJQCLBRJABBI-OAHLLOKOSA-N (2r)-2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]-4-methylphenyl]propanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C(=CC=C(NC(=O)[C@@H](C)N)C=2)C)=C1 BNGJQCLBRJABBI-OAHLLOKOSA-N 0.000 description 1
- OHPHISVCULBWCQ-CQSZACIVSA-N (2r)-2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]propanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)[C@@H](C)N)C=CC=2)=C1 OHPHISVCULBWCQ-CQSZACIVSA-N 0.000 description 1
- JMMDNYWWXFPTGF-JOCHJYFZSA-N (2r)-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]pyrrolidine-2-carboxamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)[C@@H]3NCCC3)C=CC=2)=C1 JMMDNYWWXFPTGF-JOCHJYFZSA-N 0.000 description 1
- YXTKHLHCVFUPPT-YYFJYKOTSA-N (2s)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid;(1r,2r)-1,2-dimethanidylcyclohexane;5-fluoro-1h-pyrimidine-2,4-dione;oxalic acid;platinum(2+) Chemical compound [Pt+2].OC(=O)C(O)=O.[CH2-][C@@H]1CCCC[C@H]1[CH2-].FC1=CNC(=O)NC1=O.C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 YXTKHLHCVFUPPT-YYFJYKOTSA-N 0.000 description 1
- MGOGKPMIZGEGOZ-REOHCLBHSA-N (2s)-2-amino-3-hydroxypropanamide Chemical compound OC[C@H](N)C(N)=O MGOGKPMIZGEGOZ-REOHCLBHSA-N 0.000 description 1
- MHFUWOIXNMZFIW-WNQIDUERSA-N (2s)-2-hydroxypropanoic acid;n-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound C[C@H](O)C(O)=O.C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 MHFUWOIXNMZFIW-WNQIDUERSA-N 0.000 description 1
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
- PUDHBTGHUJUUFI-SCTWWAJVSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2r)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-p Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](N)CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(N)=O)=O)C(C)C)C1=CC=C(O)C=C1 PUDHBTGHUJUUFI-SCTWWAJVSA-N 0.000 description 1
- SWDZPNJZKUGIIH-QQTULTPQSA-N (5z)-n-ethyl-5-(4-hydroxy-6-oxo-3-propan-2-ylcyclohexa-2,4-dien-1-ylidene)-4-[4-(morpholin-4-ylmethyl)phenyl]-2h-1,2-oxazole-3-carboxamide Chemical compound O1NC(C(=O)NCC)=C(C=2C=CC(CN3CCOCC3)=CC=2)\C1=C1/C=C(C(C)C)C(O)=CC1=O SWDZPNJZKUGIIH-QQTULTPQSA-N 0.000 description 1
- MWWSFMDVAYGXBV-MYPASOLCSA-N (7r,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.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 MWWSFMDVAYGXBV-MYPASOLCSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- GEHGBJVCVGLZQW-SDNWHVSQSA-N (e)-3-[3-[[3-[(4-methylphenyl)sulfonylamino]quinoxalin-2-yl]amino]phenyl]prop-2-enoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(\C=C\C(O)=O)=C1 GEHGBJVCVGLZQW-SDNWHVSQSA-N 0.000 description 1
- VXZCUHNJXSIJIM-MEBGWEOYSA-N (z)-but-2-enedioic acid;(e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound OC(=O)\C=C/C(O)=O.C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VXZCUHNJXSIJIM-MEBGWEOYSA-N 0.000 description 1
- XLOVPKCQAPHUKK-UHFFFAOYSA-N 1,2,3,4,4a,5,8,8a-octahydronaphthalene Chemical compound C1C=CCC2CCCCC21 XLOVPKCQAPHUKK-UHFFFAOYSA-N 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- NCLXVXYGUBFOQD-UHFFFAOYSA-N 1-(3-methylphenyl)-3-(3-nitrophenyl)sulfonyl-2h-imidazo[4,5-b]quinoxaline Chemical compound CC1=CC=CC(N2C3=NC4=CC=CC=C4N=C3N(C2)S(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 NCLXVXYGUBFOQD-UHFFFAOYSA-N 0.000 description 1
- LBGCXZFAWMNACS-UHFFFAOYSA-N 1-(4-methylphenyl)-3-(3-nitrophenyl)sulfonyl-2h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC(C)=CC=C1N1C2=NC3=CC=CC=C3N=C2N(S(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C1 LBGCXZFAWMNACS-UHFFFAOYSA-N 0.000 description 1
- SNKDCTFPQUHAPR-UHFFFAOYSA-N 1-fluoropyrimidine-2,4-dione Chemical compound FN1C=CC(=O)NC1=O SNKDCTFPQUHAPR-UHFFFAOYSA-N 0.000 description 1
- RELUQOFVQCRUDB-UHFFFAOYSA-N 1-naphthalen-2-yl-3-(3-nitrophenyl)sulfonyl-2h-imidazo[4,5-b]quinoxaline Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)N2C3=NC4=CC=CC=C4N=C3N(C2)C=2C=C3C=CC=CC3=CC=2)=C1 RELUQOFVQCRUDB-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- UZURTQHPMXADGG-UHFFFAOYSA-N 2,3,3a,4,7,7a-hexahydro-1h-indene Chemical compound C1C=CCC2CCCC21 UZURTQHPMXADGG-UHFFFAOYSA-N 0.000 description 1
- PHXGAJLBHUUAKB-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound O1CCC2OCCC21 PHXGAJLBHUUAKB-UHFFFAOYSA-N 0.000 description 1
- ABBADGFSRBWENF-UHFFFAOYSA-N 2-[(3-bromo-5-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile Chemical compound CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(Br)=C1O ABBADGFSRBWENF-UHFFFAOYSA-N 0.000 description 1
- QINPEPAQOBZPOF-UHFFFAOYSA-N 2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-methylpropanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C(C)(C)N)C=CC=2)=C1 QINPEPAQOBZPOF-UHFFFAOYSA-N 0.000 description 1
- SXUJZNARUXIKPT-UHFFFAOYSA-N 2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-n-ethylacetamide Chemical compound NCC(=O)N(CC)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C(=CC=C(OC)C=2)Cl)=C1 SXUJZNARUXIKPT-UHFFFAOYSA-N 0.000 description 1
- GWYNOBDJTBDANS-UHFFFAOYSA-N 2-amino-n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-n-propan-2-ylacetamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(C=CC=2)N(C(C)C)C(=O)CN)=C1 GWYNOBDJTBDANS-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- QRESMFSWXLFXDA-UHFFFAOYSA-N 2-hydroxy-4-[[3-[(3-nitrophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 QRESMFSWXLFXDA-UHFFFAOYSA-N 0.000 description 1
- NKRAYEVPROGAIE-UHFFFAOYSA-N 2-hydroxy-4-[[3-[(4-methylphenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C(O)=O)C(O)=C1 NKRAYEVPROGAIE-UHFFFAOYSA-N 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical compound NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 description 1
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BFSDWUQWQXBCPR-UHFFFAOYSA-N 3,4-dichloro-n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC2=CC=CC=C12 BFSDWUQWQXBCPR-UHFFFAOYSA-N 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- MZBYEFXSXQGVHI-UHFFFAOYSA-N 3-(benzenesulfonyl)-1-(4-pyrrolidin-1-ylsulfonylphenyl)-2h-imidazo[4,5-b]quinoxaline Chemical compound C=1C=C(N2C3=NC4=CC=CC=C4N=C3N(C2)S(=O)(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)N1CCCC1 MZBYEFXSXQGVHI-UHFFFAOYSA-N 0.000 description 1
- DUIGINIRZZKWJC-UHFFFAOYSA-N 3-[[3-[(4-chlorophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 DUIGINIRZZKWJC-UHFFFAOYSA-N 0.000 description 1
- DWKPZTIHSIMXGM-UHFFFAOYSA-N 3-[[3-[[4-(dihydroxyamino)phenyl]sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(N(O)O)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(C(O)=O)=C1 DWKPZTIHSIMXGM-UHFFFAOYSA-N 0.000 description 1
- RJNXVPXGZKENJD-UHFFFAOYSA-N 3-bromo-n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(Br)C=CC=2)=C1 RJNXVPXGZKENJD-UHFFFAOYSA-N 0.000 description 1
- KFMBARNUQDOHFJ-UHFFFAOYSA-N 3-bromo-n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(Br)C=CC=2)=C1 KFMBARNUQDOHFJ-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- KUSPKTGYJLPTSN-UHFFFAOYSA-N 3-nitro-n-[3-[(1-oxo-3h-2-benzofuran-5-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C=C3COC(=O)C3=CC=2)=C1 KUSPKTGYJLPTSN-UHFFFAOYSA-N 0.000 description 1
- BZKNSDDAJRDGTE-UHFFFAOYSA-N 4-[3-(4-acetamidophenyl)sulfonyl-2h-imidazo[4,5-b]quinoxalin-1-yl]benzoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N1C2=NC3=CC=CC=C3N=C2N(C=2C=CC(=CC=2)C(O)=O)C1 BZKNSDDAJRDGTE-UHFFFAOYSA-N 0.000 description 1
- DDQIXURDMYCSBD-UHFFFAOYSA-N 4-[4-[3-(benzenesulfonyl)-2h-imidazo[4,5-b]quinoxalin-1-yl]phenyl]morpholine Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C1=NC2=CC=CC=C2N=C11)CN1C(C=C1)=CC=C1N1CCOCC1 DDQIXURDMYCSBD-UHFFFAOYSA-N 0.000 description 1
- RXGNLKDXFQJQCN-UHFFFAOYSA-N 4-[[3-(benzenesulfonamido)quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 RXGNLKDXFQJQCN-UHFFFAOYSA-N 0.000 description 1
- AZYFTAYNMPTQPL-UHFFFAOYSA-N 4-[[3-[(4-acetamidophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C(O)=O)C=C1 AZYFTAYNMPTQPL-UHFFFAOYSA-N 0.000 description 1
- YXNMKLBKSSVUBF-UHFFFAOYSA-N 4-[[3-[(4-bromophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Br)C=C1 YXNMKLBKSSVUBF-UHFFFAOYSA-N 0.000 description 1
- MLJIRLRVKIXZGD-UHFFFAOYSA-N 4-[[3-[(4-chlorophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 MLJIRLRVKIXZGD-UHFFFAOYSA-N 0.000 description 1
- QDQSHWYDGZAZAV-UHFFFAOYSA-N 4-[[3-[(4-methylphenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C(O)=O)C=C1 QDQSHWYDGZAZAV-UHFFFAOYSA-N 0.000 description 1
- DDXGVJZZGJETMI-UHFFFAOYSA-N 4-[[3-[(4-nitrophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 DDXGVJZZGJETMI-UHFFFAOYSA-N 0.000 description 1
- DBJNWSDMGVPJFX-UHFFFAOYSA-N 4-bromo-n-[3-(2,4-dichloroanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Br)C=C1 DBJNWSDMGVPJFX-UHFFFAOYSA-N 0.000 description 1
- PBHBDGBULFUYPA-UHFFFAOYSA-N 4-bromo-n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Br)=CC=2)=C1 PBHBDGBULFUYPA-UHFFFAOYSA-N 0.000 description 1
- XHKSJZVJAJDJDS-UHFFFAOYSA-N 4-bromo-n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Br)=CC=2)=C1 XHKSJZVJAJDJDS-UHFFFAOYSA-N 0.000 description 1
- JUSNHPOIXFOUFX-UHFFFAOYSA-N 4-bromo-n-[3-(4-fluoroanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Br)C=C1 JUSNHPOIXFOUFX-UHFFFAOYSA-N 0.000 description 1
- XOFSWAQROOMZRT-UHFFFAOYSA-N 4-bromo-n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC2=CC=CC=C12 XOFSWAQROOMZRT-UHFFFAOYSA-N 0.000 description 1
- SLUDYFNSOTYWCC-UHFFFAOYSA-N 4-bromo-n-[3-[3-(trifluoromethyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Br)=CC=2)=C1 SLUDYFNSOTYWCC-UHFFFAOYSA-N 0.000 description 1
- FUOAXSYJICYJKI-UHFFFAOYSA-N 4-chloro-n-[3-(2,3-dimethylanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1C FUOAXSYJICYJKI-UHFFFAOYSA-N 0.000 description 1
- PBIMKMRJKCSYLG-UHFFFAOYSA-N 4-chloro-n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 PBIMKMRJKCSYLG-UHFFFAOYSA-N 0.000 description 1
- KHEBGFOCEDPDIJ-UHFFFAOYSA-N 4-chloro-n-[3-(2-methylanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 KHEBGFOCEDPDIJ-UHFFFAOYSA-N 0.000 description 1
- OGGGOGYGFBAGOI-UHFFFAOYSA-N 4-chloro-n-[3-(3,4-dimethylanilino)-6-methylquinoxalin-2-yl]benzenesulfonamide Chemical compound C=1C=C(C)C(C)=CC=1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 OGGGOGYGFBAGOI-UHFFFAOYSA-N 0.000 description 1
- WIPUHRFVFYHYTI-UHFFFAOYSA-N 4-chloro-n-[3-(3,4-dimethylanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 WIPUHRFVFYHYTI-UHFFFAOYSA-N 0.000 description 1
- PCDODSKVFJDIDY-UHFFFAOYSA-N 4-chloro-n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 PCDODSKVFJDIDY-UHFFFAOYSA-N 0.000 description 1
- KCUNDWXAEXGZLO-UHFFFAOYSA-N 4-chloro-n-[3-(4-chloroanilino)-6-methylquinoxalin-2-yl]benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 KCUNDWXAEXGZLO-UHFFFAOYSA-N 0.000 description 1
- PGFLKHUPXLJVNM-UHFFFAOYSA-N 4-chloro-n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC2=CC=CC=C12 PGFLKHUPXLJVNM-UHFFFAOYSA-N 0.000 description 1
- KSSSTCBGGJYWJG-UHFFFAOYSA-N 4-chloro-n-[3-(naphthalen-2-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C=CC=C2)C2=C1 KSSSTCBGGJYWJG-UHFFFAOYSA-N 0.000 description 1
- UQWFIPBHZVVWNR-UHFFFAOYSA-N 4-chloro-n-[3-[(1-oxo-3h-2-benzofuran-5-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C(=O)OC2)C2=C1 UQWFIPBHZVVWNR-UHFFFAOYSA-N 0.000 description 1
- LUGQWQBLRXPSJD-UHFFFAOYSA-N 4-chloro-n-[3-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(NC(=O)N2)C2=C1 LUGQWQBLRXPSJD-UHFFFAOYSA-N 0.000 description 1
- PROJTOHGMZDQLH-UHFFFAOYSA-N 4-chloro-n-[3-[(3,5-dimethyl-1h-pyrazol-4-yl)amino]-6-methylquinoxalin-2-yl]benzenesulfonamide Chemical compound CC1=NNC(C)=C1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 PROJTOHGMZDQLH-UHFFFAOYSA-N 0.000 description 1
- WNJNGTUJKVHXBG-UHFFFAOYSA-N 4-chloro-n-[3-[3-(4-nitrophenyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 WNJNGTUJKVHXBG-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FXEPWAVZRPMRQN-UHFFFAOYSA-N 4-methyl-n-[3-(3-methylpyridin-1-ium-1-yl)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1[N+]1=CC=CC(C)=C1 FXEPWAVZRPMRQN-UHFFFAOYSA-N 0.000 description 1
- ZMYQUJUKXFGZNY-UHFFFAOYSA-N 4-methyl-n-[3-(4-sulfamoylanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(S(N)(=O)=O)C=C1 ZMYQUJUKXFGZNY-UHFFFAOYSA-N 0.000 description 1
- PAYVHUIMNFYDRM-UHFFFAOYSA-N 4-methyl-n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC2=CC=CC=C12 PAYVHUIMNFYDRM-UHFFFAOYSA-N 0.000 description 1
- ZUGZDPNCDSQZBI-UHFFFAOYSA-N 4-methyl-n-[3-[3-(4-nitrophenyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1 ZUGZDPNCDSQZBI-UHFFFAOYSA-N 0.000 description 1
- ZIQNLBNFOUZYCM-UHFFFAOYSA-N 4-methyl-n-[3-[3-(trifluoromethyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(C(F)(F)F)=C1 ZIQNLBNFOUZYCM-UHFFFAOYSA-N 0.000 description 1
- YTUCSPSSQSVBEJ-UHFFFAOYSA-N 4-nitro-n-[3-[3-(trifluoromethyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(C(F)(F)F)=C1 YTUCSPSSQSVBEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005986 4-piperidonyl group Chemical group 0.000 description 1
- IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 description 1
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WLNBQNXELZHTAX-UHFFFAOYSA-N 8-(2-methylpropyl)-6-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=C(C)C(C(CC(C)(C)C2)=O)=C2N1C(C=C1CC(C)C)=CC2=C1C(=O)NCC2 WLNBQNXELZHTAX-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 108090000644 Angiozyme Proteins 0.000 description 1
- 229930182670 Astin Natural products 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- OVGHFJKSZBUFCZ-UHFFFAOYSA-N C1=C(O)C(C(=O)O)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 Chemical compound C1=C(O)C(C(=O)O)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 OVGHFJKSZBUFCZ-UHFFFAOYSA-N 0.000 description 1
- XJCFWZTVRCXDDA-UHFFFAOYSA-N C1=C(O)C(C(=O)O)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 Chemical compound C1=C(O)C(C(=O)O)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 XJCFWZTVRCXDDA-UHFFFAOYSA-N 0.000 description 1
- BZOPIXHIHBEHNK-UHFFFAOYSA-N C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(O)C(C(O)=O)=C1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(O)C(C(O)=O)=C1 BZOPIXHIHBEHNK-UHFFFAOYSA-N 0.000 description 1
- 102100024217 CAMPATH-1 antigen Human genes 0.000 description 1
- 108010065524 CD52 Antigen Proteins 0.000 description 1
- 239000005461 Canertinib Substances 0.000 description 1
- 208000009458 Carcinoma in Situ Diseases 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 208000005243 Chondrosarcoma Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 1
- 206010048832 Colon adenoma Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 208000007033 Dysgerminoma Diseases 0.000 description 1
- 208000000471 Dysplastic Nevus Syndrome Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010014967 Ependymoma Diseases 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- 208000007659 Fibroadenoma Diseases 0.000 description 1
- 206010053717 Fibrous histiocytoma Diseases 0.000 description 1
- 108010029961 Filgrastim Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000000527 Germinoma Diseases 0.000 description 1
- 208000007569 Giant Cell Tumors Diseases 0.000 description 1
- 201000005409 Gliomatosis cerebri Diseases 0.000 description 1
- 206010018404 Glucagonoma Diseases 0.000 description 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- 101710113864 Heat shock protein 90 Proteins 0.000 description 1
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 description 1
- 206010019629 Hepatic adenoma Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 101000934338 Homo sapiens Myeloid cell surface antigen CD33 Proteins 0.000 description 1
- 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000005045 Interdigitating dendritic cell sarcoma Diseases 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 102100020873 Interleukin-2 Human genes 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 239000002118 L01XE12 - Vandetanib Substances 0.000 description 1
- 208000002404 Liver Cell Adenoma Diseases 0.000 description 1
- 102000009151 Luteinizing Hormone Human genes 0.000 description 1
- 108010073521 Luteinizing Hormone Proteins 0.000 description 1
- 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
- 208000000172 Medulloblastoma Diseases 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
- 102100025243 Myeloid cell surface antigen CD33 Human genes 0.000 description 1
- 208000014767 Myeloproliferative disease Diseases 0.000 description 1
- HAZUHRDUFRVPJU-UHFFFAOYSA-N N-[3-(4-hydroxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(O)C=C1 HAZUHRDUFRVPJU-UHFFFAOYSA-N 0.000 description 1
- GCIKSSRWRFVXBI-UHFFFAOYSA-N N-[4-[[4-(4-methyl-1-piperazinyl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide Chemical compound C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 GCIKSSRWRFVXBI-UHFFFAOYSA-N 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 201000004404 Neurofibroma Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108010016076 Octreotide Proteins 0.000 description 1
- 206010031149 Osteitis Diseases 0.000 description 1
- 208000000035 Osteochondroma Diseases 0.000 description 1
- 229940124607 PI3Kα inhibitor Drugs 0.000 description 1
- 101150073900 PTEN gene Proteins 0.000 description 1
- 208000034038 Pathologic Neovascularization Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
- 101710093328 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 description 1
- 208000007641 Pinealoma Diseases 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 description 1
- 208000005678 Rhabdomyoma Diseases 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 208000003274 Sertoli cell tumor Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 101710183280 Topoisomerase Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 108010040002 Tumor Suppressor Proteins Proteins 0.000 description 1
- 102000001742 Tumor Suppressor Proteins Human genes 0.000 description 1
- 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
- 208000009311 VIPoma Diseases 0.000 description 1
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 1
- 206010048214 Xanthoma Diseases 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- RTQLGGYCJBBNQX-UHFFFAOYSA-N [4-[[3-[(4-acetamidophenyl)sulfonylamino]quinoxalin-2-yl]amino]phenyl] thiocyanate Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(SC#N)C=C1 RTQLGGYCJBBNQX-UHFFFAOYSA-N 0.000 description 1
- DSODRWWHAUGSGD-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)thiophen-2-yl]methyl carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.NC(=N)SCC1=CC=C(CSC(N)=N)S1 DSODRWWHAUGSGD-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 229940028652 abraxane Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000002718 adenomatoid tumor Diseases 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 229940060265 aldara Drugs 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960003437 aminoglutethimide Drugs 0.000 description 1
- ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 208000001119 benign fibrous histiocytoma Diseases 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000018339 bone inflammation disease Diseases 0.000 description 1
- 201000009480 botryoid rhabdomyosarcoma Diseases 0.000 description 1
- 238000002725 brachytherapy Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 201000003149 breast fibroadenoma Diseases 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 201000002143 bronchus adenoma Diseases 0.000 description 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004709 cell invasion Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- QKJBNXQNGGHPGN-UHFFFAOYSA-N chembl1348971 Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(O)C(C(O)=O)=C1 QKJBNXQNGGHPGN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000010109 chemoembolization Effects 0.000 description 1
- 239000012829 chemotherapy agent Substances 0.000 description 1
- 208000006990 cholangiocarcinoma Diseases 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229960002436 cladribine Drugs 0.000 description 1
- 208000009060 clear cell adenocarcinoma Diseases 0.000 description 1
- WDDPHFBMKLOVOX-AYQXTPAHSA-N clofarabine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F WDDPHFBMKLOVOX-AYQXTPAHSA-N 0.000 description 1
- 229960000928 clofarabine Drugs 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 201000010305 cutaneous fibrous histiocytoma Diseases 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 description 1
- 229950011148 cyclopropane Drugs 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 229960001140 cyproheptadine Drugs 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 230000003436 cytoskeletal effect Effects 0.000 description 1
- 229940026692 decadron Drugs 0.000 description 1
- 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 229940064790 dilantin Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229940115080 doxil Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000010102 embolization Effects 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- DGICRVZVQQUJSF-UHFFFAOYSA-N ethyl 4-[[3-[(4-chlorophenyl)sulfonylamino]quinoxalin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 DGICRVZVQQUJSF-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=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 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
- 229960000752 etoposide phosphate Drugs 0.000 description 1
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 description 1
- 229950009429 exatecan Drugs 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
- 201000000052 gastrinoma Diseases 0.000 description 1
- 229940020967 gemzar Drugs 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 201000003115 germ cell cancer Diseases 0.000 description 1
- 230000036433 growing body Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 210000002767 hepatic artery Anatomy 0.000 description 1
- 208000006359 hepatoblastoma Diseases 0.000 description 1
- 201000002735 hepatocellular adenoma Diseases 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940096120 hydrea Drugs 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000009802 hysterectomy Methods 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
- 201000004933 in situ carcinoma Diseases 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 206010022498 insulinoma Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000002570 interstitial cell Anatomy 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 201000010985 invasive ductal carcinoma Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- XMBWDFGMSWQBCA-RNFDNDRNSA-M iodine-131(1-) Chemical group [131I-] XMBWDFGMSWQBCA-RNFDNDRNSA-M 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960005386 ipilimumab Drugs 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000022013 kidney Wilms tumor Diseases 0.000 description 1
- 229960002437 lanreotide Drugs 0.000 description 1
- 108010021336 lanreotide Proteins 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 238000002430 laser surgery Methods 0.000 description 1
- 229940087875 leukine Drugs 0.000 description 1
- 206010024627 liposarcoma Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229950005069 luminespib Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
- 229950002654 lurtotecan Drugs 0.000 description 1
- 229940040129 luteinizing hormone Drugs 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 201000000289 malignant teratoma Diseases 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 1
- 229960001786 megestrol Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QIAWINYTQLHVGB-UHFFFAOYSA-N methyl 2-[[3-(benzenesulfonamido)quinoxalin-2-yl]amino]-4,5-dimethylthiophene-3-carboxylate Chemical compound CC1=C(C)SC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1C(=O)OC QIAWINYTQLHVGB-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ZDZOTLJHXYCWBA-BSEPLHNVSA-N molport-006-823-826 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-BSEPLHNVSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000010492 mucinous cystadenocarcinoma Diseases 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 208000009091 myxoma Diseases 0.000 description 1
- FQCZFCSTVFTJNJ-UHFFFAOYSA-N n-(3-anilino-6-methylquinoxalin-2-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=C(C)C=C2N=C1NC1=CC=CC=C1 FQCZFCSTVFTJNJ-UHFFFAOYSA-N 0.000 description 1
- YOYOPDYBSGIAEE-UHFFFAOYSA-N n-(3-anilinoquinoxalin-2-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC=C1 YOYOPDYBSGIAEE-UHFFFAOYSA-N 0.000 description 1
- PKCSGOHBWGFZJZ-UHFFFAOYSA-N n-(3-anilinoquinoxalin-2-yl)benzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC=C1 PKCSGOHBWGFZJZ-UHFFFAOYSA-N 0.000 description 1
- FETGPVCOKCJWGB-UHFFFAOYSA-N n-[3-(1,3-benzodioxol-5-ylamino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(OCO2)C2=C1 FETGPVCOKCJWGB-UHFFFAOYSA-N 0.000 description 1
- SGZQJVZMZPYKOW-UHFFFAOYSA-N n-[3-(2,3-dihydro-1,4-benzodioxin-6-ylamino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C=C3OCCOC3=CC=2)=C1 SGZQJVZMZPYKOW-UHFFFAOYSA-N 0.000 description 1
- JRDCGRSVUNUHIX-UHFFFAOYSA-N n-[3-(2,3-dihydro-1,4-benzodioxin-6-ylamino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(OCCO2)C2=C1 JRDCGRSVUNUHIX-UHFFFAOYSA-N 0.000 description 1
- KPEABRDBMKZDMF-UHFFFAOYSA-N n-[3-(2,3-dimethylanilino)-6-methylquinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=C(C)C=C2N=C1NC1=CC=CC(C)=C1C KPEABRDBMKZDMF-UHFFFAOYSA-N 0.000 description 1
- ZOYLXNNOCCOXRM-UHFFFAOYSA-N n-[3-(2,4-dichloroanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(Cl)C=C1Cl ZOYLXNNOCCOXRM-UHFFFAOYSA-N 0.000 description 1
- LAJDXOIYMJJISO-UHFFFAOYSA-N n-[3-(2,4-dimethylanilino)-6-methylquinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=C(C)C=C2N=C1NC1=CC=C(C)C=C1C LAJDXOIYMJJISO-UHFFFAOYSA-N 0.000 description 1
- PEAFOUHADOOIMF-UHFFFAOYSA-N n-[3-(2,5-dimethoxyanilino)-7-methylquinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC(C)=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 PEAFOUHADOOIMF-UHFFFAOYSA-N 0.000 description 1
- DXKNNTPDJCRGNF-UHFFFAOYSA-N n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]-3-fluorobenzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(F)C=CC=2)=C1 DXKNNTPDJCRGNF-UHFFFAOYSA-N 0.000 description 1
- KFPGXSWDOMGULE-UHFFFAOYSA-N n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 KFPGXSWDOMGULE-UHFFFAOYSA-N 0.000 description 1
- AVBKJIKARKEJJY-UHFFFAOYSA-N n-[3-(2,5-dimethoxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound COC1=CC=C(OC)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 AVBKJIKARKEJJY-UHFFFAOYSA-N 0.000 description 1
- XJWOLTBRPFHOPK-UHFFFAOYSA-N n-[3-(2,5-dimethylanilino)-6-methylquinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=C(C)C=C2N=C1NC1=CC(C)=CC=C1C XJWOLTBRPFHOPK-UHFFFAOYSA-N 0.000 description 1
- FBVARRFIBFKCMK-UHFFFAOYSA-N n-[3-(2,5-dimethylanilino)-6-nitroquinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=C([N+]([O-])=O)C=C2N=C1NC1=CC(C)=CC=C1C FBVARRFIBFKCMK-UHFFFAOYSA-N 0.000 description 1
- VKPXTOCRYLWGIV-UHFFFAOYSA-N n-[3-(2-bromo-4-methylanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound BrC1=CC(C)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 VKPXTOCRYLWGIV-UHFFFAOYSA-N 0.000 description 1
- XPEBIAOZZKOSIA-UHFFFAOYSA-N n-[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 XPEBIAOZZKOSIA-UHFFFAOYSA-N 0.000 description 1
- WEBLIBNQYKLNTD-UHFFFAOYSA-N n-[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 WEBLIBNQYKLNTD-UHFFFAOYSA-N 0.000 description 1
- YFLNMDSORXCPQN-UHFFFAOYSA-N n-[3-(2-chloroanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound ClC1=CC=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 YFLNMDSORXCPQN-UHFFFAOYSA-N 0.000 description 1
- YMZCUAVAHLJASG-UHFFFAOYSA-N n-[3-(3,4-dihydro-1h-isoquinolin-2-yl)quinoxalin-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1N1CC2=CC=CC=C2CC1 YMZCUAVAHLJASG-UHFFFAOYSA-N 0.000 description 1
- LLPRNTUQPSAOEZ-UHFFFAOYSA-N n-[3-(3,4-dimethylanilino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 LLPRNTUQPSAOEZ-UHFFFAOYSA-N 0.000 description 1
- ZNRYTTCTUBWKFX-UHFFFAOYSA-N n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]-2-fluorobenzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C(=CC=CC=2)F)=C1 ZNRYTTCTUBWKFX-UHFFFAOYSA-N 0.000 description 1
- BWLPXMKWMRGOKV-UHFFFAOYSA-N n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 BWLPXMKWMRGOKV-UHFFFAOYSA-N 0.000 description 1
- KQFBBGKLBVZGAK-UHFFFAOYSA-N n-[3-(3-acetylanilino)quinoxalin-2-yl]-4-chlorobenzenesulfonamide Chemical compound CC(=O)C1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 KQFBBGKLBVZGAK-UHFFFAOYSA-N 0.000 description 1
- BNDGOTGKFXPONZ-UHFFFAOYSA-N n-[3-(3-aminoanilino)quinoxalin-2-yl]-4-chlorobenzenesulfonamide Chemical compound NC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 BNDGOTGKFXPONZ-UHFFFAOYSA-N 0.000 description 1
- FRSZAUCYEJBYBX-UHFFFAOYSA-N n-[3-(3-butoxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound CCCCOC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 FRSZAUCYEJBYBX-UHFFFAOYSA-N 0.000 description 1
- PEDJTIDVGVQOFR-UHFFFAOYSA-N n-[3-(3-chloro-4-fluoroanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 PEDJTIDVGVQOFR-UHFFFAOYSA-N 0.000 description 1
- DMPONDUTVVYLQB-UHFFFAOYSA-N n-[3-(3-chloro-4-methoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 DMPONDUTVVYLQB-UHFFFAOYSA-N 0.000 description 1
- ADHBDIDXBZHQCL-UHFFFAOYSA-N n-[3-(3-chloro-5-methylanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC(C)=CC(Cl)=C1 ADHBDIDXBZHQCL-UHFFFAOYSA-N 0.000 description 1
- MZVYQBNAYWUBIT-UHFFFAOYSA-N n-[3-(3-fluoroanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound FC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 MZVYQBNAYWUBIT-UHFFFAOYSA-N 0.000 description 1
- FLYJQQMLYRWBSQ-UHFFFAOYSA-N n-[3-(3-hydroxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(O)=C1 FLYJQQMLYRWBSQ-UHFFFAOYSA-N 0.000 description 1
- BNHZFBKIEIPSHA-UHFFFAOYSA-N n-[3-(3-hydroxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound OC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 BNHZFBKIEIPSHA-UHFFFAOYSA-N 0.000 description 1
- ZQFGETWRRQSXRZ-UHFFFAOYSA-N n-[3-(4-anilinoanilino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 ZQFGETWRRQSXRZ-UHFFFAOYSA-N 0.000 description 1
- UWPZHDGCPLJNQF-UHFFFAOYSA-N n-[3-(4-bromoanilino)quinoxalin-2-yl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(Br)C=C1 UWPZHDGCPLJNQF-UHFFFAOYSA-N 0.000 description 1
- MBXBAQKGWCXTKR-UHFFFAOYSA-N n-[3-(4-bromoanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(Br)C=C1 MBXBAQKGWCXTKR-UHFFFAOYSA-N 0.000 description 1
- HXLYFWBBAJKYQR-UHFFFAOYSA-N n-[3-(4-butylanilino)quinoxalin-2-yl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(CCCC)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 HXLYFWBBAJKYQR-UHFFFAOYSA-N 0.000 description 1
- DMVHRWNRXXTPFN-UHFFFAOYSA-N n-[3-(4-chloro-2,5-dimethoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1OC DMVHRWNRXXTPFN-UHFFFAOYSA-N 0.000 description 1
- DVBCTPSEVZPJQD-UHFFFAOYSA-N n-[3-(4-chloro-3-methoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC=CC=2)=C1 DVBCTPSEVZPJQD-UHFFFAOYSA-N 0.000 description 1
- DBXGCOVTUVEWFR-UHFFFAOYSA-N n-[3-(4-ethoxyanilino)-6-methylquinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OCC)=CC=C1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(C)C=C1 DBXGCOVTUVEWFR-UHFFFAOYSA-N 0.000 description 1
- WYNCOSFPFNDWAF-UHFFFAOYSA-N n-[3-(4-ethoxyanilino)quinoxalin-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OCC)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(C)C=C1 WYNCOSFPFNDWAF-UHFFFAOYSA-N 0.000 description 1
- YEDTXANEJQRYDX-UHFFFAOYSA-N n-[3-(4-octoxyanilino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=CC(OCCCCCCCC)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 YEDTXANEJQRYDX-UHFFFAOYSA-N 0.000 description 1
- UUYBKAGYSYXLMP-UHFFFAOYSA-N n-[3-(cyclohexylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1CCCCC1 UUYBKAGYSYXLMP-UHFFFAOYSA-N 0.000 description 1
- IPECZHPUCSKOFI-UHFFFAOYSA-N n-[3-(dibenzylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 IPECZHPUCSKOFI-UHFFFAOYSA-N 0.000 description 1
- VVMHPAGDGIVPAF-UHFFFAOYSA-N n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C3=CC=CC=C3C=CC=2)=C1 VVMHPAGDGIVPAF-UHFFFAOYSA-N 0.000 description 1
- QZVRBOHELCXCOK-UHFFFAOYSA-N n-[3-(naphthalen-1-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound N=1C2=CC=CC=C2N=C(NC=2C3=CC=CC=C3C=CC=2)C=1NS(=O)(=O)C1=CC=CC=C1 QZVRBOHELCXCOK-UHFFFAOYSA-N 0.000 description 1
- ZVJPQWSQRUEECT-UHFFFAOYSA-N n-[3-(naphthalen-2-ylamino)quinoxalin-2-yl]-4-nitrobenzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C=CC=C2)C2=C1 ZVJPQWSQRUEECT-UHFFFAOYSA-N 0.000 description 1
- VNQIQBZTUBWDON-UHFFFAOYSA-N n-[3-(quinolin-6-ylamino)quinoxalin-2-yl]benzenesulfonamide Chemical compound N=1C2=CC=CC=C2N=C(NC=2C=C3C=CC=NC3=CC=2)C=1NS(=O)(=O)C1=CC=CC=C1 VNQIQBZTUBWDON-UHFFFAOYSA-N 0.000 description 1
- KTDPLYAVINTGMU-UHFFFAOYSA-N n-[3-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 KTDPLYAVINTGMU-UHFFFAOYSA-N 0.000 description 1
- TYPVGZFHAZUVFH-UHFFFAOYSA-N n-[3-[(1-oxo-3h-2-benzofuran-5-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 TYPVGZFHAZUVFH-UHFFFAOYSA-N 0.000 description 1
- ZVSXYEGKRORXGW-UHFFFAOYSA-N n-[3-[(2-methyl-1,3-dioxoisoindol-5-yl)amino]quinoxalin-2-yl]benzenesulfonamide Chemical compound C1=C2C(=O)N(C)C(=O)C2=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 ZVSXYEGKRORXGW-UHFFFAOYSA-N 0.000 description 1
- ULAHJJWSCMFXKO-UHFFFAOYSA-N n-[3-[(9-ethylcarbazol-3-yl)amino]quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ULAHJJWSCMFXKO-UHFFFAOYSA-N 0.000 description 1
- OBYCPLWKXIPUQG-UHFFFAOYSA-N n-[3-[2-(difluoromethoxy)anilino]quinoxalin-2-yl]-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=NC3=CC=CC=C3N=2)NC=2C(=CC=CC=2)OC(F)F)=C1 OBYCPLWKXIPUQG-UHFFFAOYSA-N 0.000 description 1
- OTVYGWGTRXEEPV-UHFFFAOYSA-N n-[3-[2-(trifluoromethylsulfanyl)anilino]quinoxalin-2-yl]benzenesulfonamide Chemical compound FC(F)(F)SC1=CC=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 OTVYGWGTRXEEPV-UHFFFAOYSA-N 0.000 description 1
- NSGOWEJBESJWAK-UHFFFAOYSA-N n-[3-[4-(4-aminophenoxy)anilino]quinoxalin-2-yl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 NSGOWEJBESJWAK-UHFFFAOYSA-N 0.000 description 1
- QXFSYJZDIWHXAD-UHFFFAOYSA-N n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]piperidine-3-carboxamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C3CNCCC3)C=CC=2)=C1 QXFSYJZDIWHXAD-UHFFFAOYSA-N 0.000 description 1
- LBINZOMSHLUZSF-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-1-methylpiperidine-4-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C3CCN(C)CC3)C=CC=2)=C1 LBINZOMSHLUZSF-UHFFFAOYSA-N 0.000 description 1
- BRIGZTFNBVGXST-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-morpholin-4-ylacetamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)CN3CCOCC3)C=CC=2)=C1 BRIGZTFNBVGXST-UHFFFAOYSA-N 0.000 description 1
- YAOFBXFURDKMAN-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-pyrrolidin-1-ylacetamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)CN3CCCC3)C=CC=2)=C1 YAOFBXFURDKMAN-UHFFFAOYSA-N 0.000 description 1
- KZNMNIYTYMECKD-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-3-piperidin-1-ylpropanamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)CCN3CCCCC3)C=CC=2)=C1 KZNMNIYTYMECKD-UHFFFAOYSA-N 0.000 description 1
- HQTOOQVCMOVKNA-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(C)=O)C=CC=2)=C1 HQTOOQVCMOVKNA-UHFFFAOYSA-N 0.000 description 1
- JWJJHVMCWYFBSD-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]azetidine-3-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C3CNC3)C=CC=2)=C1 JWJJHVMCWYFBSD-UHFFFAOYSA-N 0.000 description 1
- HLJHGQPYASCEBX-UHFFFAOYSA-N n-[3-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]piperidine-2-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C3NCCCC3)C=CC=2)=C1 HLJHGQPYASCEBX-UHFFFAOYSA-N 0.000 description 1
- AYAYKAAOUJLLTO-UHFFFAOYSA-N n-[3-[[3-[(4-chlorophenyl)sulfonylamino]-7-methoxyquinoxalin-2-yl]amino]phenyl]acetamide Chemical compound C=1C=CC(NC(C)=O)=CC=1NC1=NC2=CC(OC)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 AYAYKAAOUJLLTO-UHFFFAOYSA-N 0.000 description 1
- QDNUSAXRFWKUBW-UHFFFAOYSA-N n-[3-[[3-[(4-chlorophenyl)sulfonylamino]-7-methylquinoxalin-2-yl]amino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NC=2C(=NC3=CC=C(C)C=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 QDNUSAXRFWKUBW-UHFFFAOYSA-N 0.000 description 1
- VJQWVVVZGYXVRK-UHFFFAOYSA-N n-[3-[[3-[(4-chlorophenyl)sulfonylamino]quinoxalin-2-yl]amino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 VJQWVVVZGYXVRK-UHFFFAOYSA-N 0.000 description 1
- VODSFGJCZHSMJU-UHFFFAOYSA-N n-[3-[[3-[(4-methylphenyl)sulfonylamino]quinoxalin-2-yl]amino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 VODSFGJCZHSMJU-UHFFFAOYSA-N 0.000 description 1
- LFNHDAZQNPDACV-UHFFFAOYSA-N n-[4-[(1-phenyl-2h-imidazo[4,5-b]quinoxalin-3-yl)sulfonyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N1C2=NC3=CC=CC=C3N=C2N(C=2C=CC=CC=2)C1 LFNHDAZQNPDACV-UHFFFAOYSA-N 0.000 description 1
- FPXQZVJZASSVMU-UHFFFAOYSA-N n-[4-[[1-(2-methoxyphenyl)-2h-imidazo[4,5-b]quinoxalin-3-yl]sulfonyl]phenyl]acetamide Chemical compound COC1=CC=CC=C1N1C2=NC3=CC=CC=C3N=C2N(S(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)C1 FPXQZVJZASSVMU-UHFFFAOYSA-N 0.000 description 1
- BBUSVWACSMBAQU-UHFFFAOYSA-N n-[4-[[1-(2-methylphenyl)-2h-imidazo[4,5-b]quinoxalin-3-yl]sulfonyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N1C2=NC3=CC=CC=C3N=C2N(C=2C(=CC=CC=2)C)C1 BBUSVWACSMBAQU-UHFFFAOYSA-N 0.000 description 1
- NJYQNQSLXGKGIL-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)-2h-imidazo[4,5-b]quinoxalin-3-yl]sulfonyl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC3=CC=CC=C3N=C2N(S(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)C1 NJYQNQSLXGKGIL-UHFFFAOYSA-N 0.000 description 1
- JZFPBLINSYTRPK-UHFFFAOYSA-N n-[4-[[3-(2,1,3-benzothiadiazol-5-ylamino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC2=NSN=C2C=C1 JZFPBLINSYTRPK-UHFFFAOYSA-N 0.000 description 1
- ITFRDFBCXXLZIJ-UHFFFAOYSA-N n-[4-[[3-(2-bromo-4-methylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C)C=C1Br ITFRDFBCXXLZIJ-UHFFFAOYSA-N 0.000 description 1
- LAQHXBQXJIOLKK-UHFFFAOYSA-N n-[4-[[3-(2-ethylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound CCC1=CC=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 LAQHXBQXJIOLKK-UHFFFAOYSA-N 0.000 description 1
- BXPXZCZZYPGKHX-UHFFFAOYSA-N n-[4-[[3-(2-methylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC=C1C BXPXZCZZYPGKHX-UHFFFAOYSA-N 0.000 description 1
- NBXVUYMDIIZUKS-UHFFFAOYSA-N n-[4-[[3-(3-methylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(C)=C1 NBXVUYMDIIZUKS-UHFFFAOYSA-N 0.000 description 1
- KBRZWOYMKKUDMV-UHFFFAOYSA-N n-[4-[[3-(3-sulfamoylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC(S(N)(=O)=O)=C1 KBRZWOYMKKUDMV-UHFFFAOYSA-N 0.000 description 1
- IMZAHEHTUBHDIE-UHFFFAOYSA-N n-[4-[[3-(4-bromoanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(Br)C=C1 IMZAHEHTUBHDIE-UHFFFAOYSA-N 0.000 description 1
- WEOHILQJNAZMNX-UHFFFAOYSA-N n-[4-[[3-(4-methylanilino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C)C=C1 WEOHILQJNAZMNX-UHFFFAOYSA-N 0.000 description 1
- FYKLPRKNJSPGON-UHFFFAOYSA-O n-[4-[[3-(4-methylpyridin-1-ium-1-yl)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1[N+]1=CC=C(C)C=C1 FYKLPRKNJSPGON-UHFFFAOYSA-O 0.000 description 1
- CUWFKQGJMRIMRI-UHFFFAOYSA-N n-[4-[[3-(benzenesulfonamido)quinoxalin-2-yl]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC2=CC=CC=C2N=C1NS(=O)(=O)C1=CC=CC=C1 CUWFKQGJMRIMRI-UHFFFAOYSA-N 0.000 description 1
- NCZQTIRXSCXOKR-UHFFFAOYSA-N n-[4-[[3-(naphthalen-1-ylamino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=CC2=CC=CC=C12 NCZQTIRXSCXOKR-UHFFFAOYSA-N 0.000 description 1
- CNIOWSJRNNAWFF-UHFFFAOYSA-N n-[4-[[3-(naphthalen-2-ylamino)quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC1=CC=C(C=CC=C2)C2=C1 CNIOWSJRNNAWFF-UHFFFAOYSA-N 0.000 description 1
- JMYYAYUGVOCACC-UHFFFAOYSA-N n-[4-[[3-[(4-chlorophenyl)sulfonylamino]-7-methoxyquinoxalin-2-yl]amino]phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1NC1=NC2=CC(OC)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 JMYYAYUGVOCACC-UHFFFAOYSA-N 0.000 description 1
- KYLDCJDFSFAKRJ-UHFFFAOYSA-N n-[4-[[3-[(4-chlorophenyl)sulfonylamino]-7-methylquinoxalin-2-yl]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 KYLDCJDFSFAKRJ-UHFFFAOYSA-N 0.000 description 1
- UFRBYXUUCMYGBP-UHFFFAOYSA-N n-[4-[[3-[4-(4-aminophenoxy)anilino]quinoxalin-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC2=CC=CC=C2N=C1NC(C=C1)=CC=C1OC1=CC=C(N)C=C1 UFRBYXUUCMYGBP-UHFFFAOYSA-N 0.000 description 1
- RWSCXGXJSHTBAF-UHFFFAOYSA-N n-[4-[[7-methyl-3-[(4-methylphenyl)sulfonylamino]quinoxalin-2-yl]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC2=CC(C)=CC=C2N=C1NS(=O)(=O)C1=CC=C(C)C=C1 RWSCXGXJSHTBAF-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 201000008026 nephroblastoma Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229940029345 neupogen Drugs 0.000 description 1
- 201000004662 neurofibroma of spinal cord Diseases 0.000 description 1
- 208000004649 neutrophil actin dysfunction Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- 229960002700 octreotide Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 208000003388 osteoid osteoma Diseases 0.000 description 1
- 208000008798 osteoma Diseases 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000021255 pancreatic insulinoma Diseases 0.000 description 1
- 229960005415 pasireotide Drugs 0.000 description 1
- 108700017947 pasireotide Proteins 0.000 description 1
- NEEFMPSSNFRRNC-HQUONIRXSA-N pasireotide aspartate Chemical compound OC(=O)[C@@H](N)CC(O)=O.OC(=O)[C@@H](N)CC(O)=O.C([C@H]1C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@H](C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@H](C(N[C@@H](CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)N1)=O)CCCCN)C=1C=CC=CC=1)OC(=O)NCCN)C1=CC=CC=C1 NEEFMPSSNFRRNC-HQUONIRXSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229940046159 pegylated liposomal doxorubicin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 150000003911 phosphatidylinositol 4-phosphates Chemical class 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 208000024724 pineal body neoplasm Diseases 0.000 description 1
- 201000004123 pineal gland cancer Diseases 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940063179 platinol Drugs 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940063222 provera Drugs 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 238000009803 radical hysterectomy Methods 0.000 description 1
- 238000007674 radiofrequency ablation Methods 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 108010038379 sargramostim Proteins 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 208000004548 serous cystadenocarcinoma Diseases 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000002719 stereotactic radiosurgery Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940061353 temodar Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- 208000001608 teratocarcinoma Diseases 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-M thiophene-3-carboxylate Chemical compound [O-]C(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-M 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 208000022271 tubular adenoma Diseases 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229960001055 uracil mustard Drugs 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229950000578 vatalanib Drugs 0.000 description 1
- YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92316407P | 2007-04-11 | 2007-04-11 | |
| US923164P | 2007-04-11 | ||
| PCT/US2008/004570 WO2008127594A2 (en) | 2007-04-11 | 2008-04-08 | Combination therapies comprising quinoxaline inhibitors of pi3k-alpha for use in the treatment of cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2438998T3 true ES2438998T3 (es) | 2014-01-21 |
Family
ID=39864581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08742674.8T Active ES2438998T3 (es) | 2007-04-11 | 2008-04-08 | Terapias combinadas que comprenden un inhibidor de quinaxolina de PI3K alfa para utilizar en el tratamiento del cáncer |
Country Status (33)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ594628A (en) * | 2005-10-07 | 2013-04-26 | Exelixis Inc | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Ka |
| RS53627B1 (sr) * | 2005-10-07 | 2015-04-30 | Exelixis Inc. | Derivati n-(3-amino-hinoksalin-2-il)-sulfonamida i njihova upotreba kao inhibitora fosfatidilinozitol3-kinaze |
| WO2008021389A2 (en) | 2006-08-16 | 2008-02-21 | Exelixis, Inc. | Using pi3k and mek modulators in treatments of cancer |
| RS52939B (sr) * | 2007-04-10 | 2014-02-28 | Exelixis Inc. | Postupci za lečenje kancera upotrebom piridopirimidinonskih inhibitora pi3k alfa |
| EP2374802B1 (en) | 2008-11-10 | 2014-04-23 | Kyowa Hakko Kirin Co., Ltd. | Kynurenine production inhibitor |
| DE102009049679A1 (de) | 2009-10-19 | 2011-04-21 | Merck Patent Gmbh | Pyrazolopyrimidinderivate |
| AR080151A1 (es) | 2010-02-09 | 2012-03-14 | Exelixis Inc | Metodos para tratar cancer usando inhibidores de piridopirimidinona de pi 3k y mtor en combinacion con inhibidores de autofagia |
| CA2803900A1 (en) | 2010-07-09 | 2012-01-12 | Exelixis, Inc. | Combinations of kinase inhibitors for the treatment of cancer |
| JP5792819B2 (ja) | 2010-09-14 | 2015-10-14 | エクセリクシス， インク． | Ｐｉ３ｋ−デルタの阻害剤ならびにそれらの使用法および製造法 |
| DE102010048800A1 (de) * | 2010-10-20 | 2012-05-10 | Merck Patent Gmbh | Chinoxalinderivate |
| JP2013540141A (ja) | 2010-10-20 | 2013-10-31 | メルク セローノ ソシエテ アノニム ジュネーブ | 置換ｎ−（３−アミノ−キノキサリン−２−イル）−スルホンアミドおよびそれらの中間体ｎ−（３−クロロ−キノキサリン−２−イル）スルホンアミドを調製する方法 |
| DE102010049595A1 (de) | 2010-10-26 | 2012-04-26 | Merck Patent Gmbh | Chinazolinderivate |
| WO2012065057A2 (en) | 2010-11-12 | 2012-05-18 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors and methods of their use |
| AU2012308414A1 (en) * | 2011-09-14 | 2014-05-01 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors for the treatment of cancer |
| US20140235643A1 (en) * | 2011-10-04 | 2014-08-21 | Gilead Calistoga Llc | Novel quinoxaline inhibitors of pi3k |
| WO2013056067A1 (en) | 2011-10-13 | 2013-04-18 | Exelixis, Inc. | Compounds for use in the treatment of basal cell carcinoma |
| CA2853095A1 (en) * | 2011-10-28 | 2013-05-02 | Novartis Ag | Method of treating gastrointestinal stromal tumors |
| EA201490905A1 (ru) * | 2011-11-01 | 2014-11-28 | Экселиксис, Инк. | N-(3-{[(3-{[2-хлор-5-(метокси)фенил]амино}хиноксалин-2-ил)амино]сульфонил}фенил)-2-метилаланинамид как ингибитор фосфатидилинозитол-3-киназы для лечения лимфопролиферативных злокачественных заболеваний |
| WO2013067306A1 (en) * | 2011-11-02 | 2013-05-10 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors for the treatment of childhood cancers |
| JP2015503568A (ja) * | 2011-12-27 | 2015-02-02 | カドモン コーポレイション，リミティド ライアビリティ カンパニー | トラスツズマブに不応性の乳癌の治療方法 |
| JP6077642B2 (ja) | 2012-04-10 | 2017-02-08 | シャンハイ インリ ファーマシューティカル カンパニー リミティド | 縮合ピリミジン化合物、その調製法、中間体、組成物、及び使用 |
| JP6193374B2 (ja) | 2012-08-13 | 2017-09-06 | 武田薬品工業株式会社 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
| EP3053926B1 (en) | 2013-09-30 | 2018-08-08 | Shanghai Yingli Pharmaceutical Co. Ltd. | Fused pyrimidine compound, intermediate, preparation method therefor, and composition and application thereof |
| JP6139789B2 (ja) | 2013-10-16 | 2017-05-31 | シャンハイ インリ ファーマシューティカル カンパニー リミティド | 縮合複素環化合物、その調製方法、医薬組成物及びその使用 |
| WO2015123505A1 (en) | 2014-02-14 | 2015-08-20 | Takeda Pharmaceutical Company Limited | Pyridopyrazines modulators of gpr6 |
| US9950194B2 (en) | 2014-09-09 | 2018-04-24 | Mevion Medical Systems, Inc. | Patient positioning system |
| WO2019119206A1 (en) * | 2017-12-18 | 2019-06-27 | Merck Sharp & Dohme Corp. | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006515885A (ja) * | 2003-01-17 | 2006-06-08 | スレッシュオールド ファーマシューティカルズ， インコーポレイテッド | 癌の処置のための併用療法 |
| EA015937B1 (ru) * | 2005-08-26 | 2011-12-30 | Мерк Сероно С.А. | Производные пиразина и их применение в качестве ингибиторов pi3k |
| NZ594628A (en) | 2005-10-07 | 2013-04-26 | Exelixis Inc | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Ka |
| RS53627B1 (sr) | 2005-10-07 | 2015-04-30 | Exelixis Inc. | Derivati n-(3-amino-hinoksalin-2-il)-sulfonamida i njihova upotreba kao inhibitora fosfatidilinozitol3-kinaze |
| WO2008021389A2 (en) * | 2006-08-16 | 2008-02-21 | Exelixis, Inc. | Using pi3k and mek modulators in treatments of cancer |
| EP2118076B1 (en) * | 2007-02-22 | 2019-09-04 | Merck Serono S.A. | Quinoxaline compounds and use thereof |
| RS52939B (sr) | 2007-04-10 | 2014-02-28 | Exelixis Inc. | Postupci za lečenje kancera upotrebom piridopirimidinonskih inhibitora pi3k alfa |
| JP4623164B2 (ja) * | 2008-08-21 | 2011-02-02 | セイコーエプソン株式会社 | プロジェクタ |
-
2008
- 2008-04-08 HR HRP20131081AT patent/HRP20131081T1/hr unknown
- 2008-04-08 ME MEP-2009-304A patent/ME00937B/me unknown
- 2008-04-08 JP JP2010503043A patent/JP5726515B2/ja active Active
- 2008-04-08 MY MYPI20094215 patent/MY150797A/en unknown
- 2008-04-08 PT PT87426748T patent/PT2139483E/pt unknown
- 2008-04-08 UA UAA200911452A patent/UA98141C2/ru unknown
- 2008-04-08 NZ NZ580009A patent/NZ580009A/xx not_active IP Right Cessation
- 2008-04-08 EP EP08742674.8A patent/EP2139483B9/en active Active
- 2008-04-08 CA CA002684056A patent/CA2684056A1/en not_active Abandoned
- 2008-04-08 CN CN2008800173944A patent/CN101959516B/zh not_active Expired - Fee Related
- 2008-04-08 ES ES08742674.8T patent/ES2438998T3/es active Active
- 2008-04-08 PL PL08742674T patent/PL2139483T3/pl unknown
- 2008-04-08 CN CN2013101161222A patent/CN103202842A/zh active Pending
- 2008-04-08 MX MX2009010929A patent/MX2009010929A/es active IP Right Grant
- 2008-04-08 WO PCT/US2008/004570 patent/WO2008127594A2/en not_active Ceased
- 2008-04-08 US US12/595,236 patent/US8481001B2/en not_active Expired - Fee Related
- 2008-04-08 BR BRPI0810208-2A2A patent/BRPI0810208A2/pt not_active IP Right Cessation
- 2008-04-08 DK DK08742674.8T patent/DK2139483T3/da active
- 2008-04-08 SI SI200831061T patent/SI2139483T1/sl unknown
- 2008-04-08 RS RS20130486A patent/RS53020B/sr unknown
- 2008-04-08 AU AU2008239668A patent/AU2008239668B2/en not_active Ceased
- 2008-04-08 EA EA200970935A patent/EA019064B1/ru not_active IP Right Cessation
- 2008-04-08 KR KR1020097023536A patent/KR101586774B1/ko not_active Expired - Fee Related
-
2009
- 2009-09-29 IL IL201211A patent/IL201211A/en active IP Right Grant
- 2009-09-29 ZA ZA200906765A patent/ZA200906765B/xx unknown
- 2009-09-30 TN TNP2009000399A patent/TN2009000399A1/fr unknown
- 2009-10-09 NI NI200900184A patent/NI200900184A/es unknown
- 2009-10-09 SV SV2009003390A patent/SV2009003390A/es unknown
- 2009-10-09 GT GT200900263A patent/GT200900263A/es unknown
- 2009-10-30 MA MA32313A patent/MA31335B1/fr unknown
- 2009-11-09 EC EC2009009723A patent/ECSP099723A/es unknown
- 2009-11-09 CO CO09126923A patent/CO6140024A2/es unknown
- 2009-11-09 CR CR11099A patent/CR11099A/es unknown
-
2013
- 2013-11-01 JP JP2013228684A patent/JP2014074031A/ja active Pending
- 2013-11-15 CY CY20131101016T patent/CY1114608T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2438998T3 (es) | Terapias combinadas que comprenden un inhibidor de quinaxolina de PI3K alfa para utilizar en el tratamiento del cáncer | |
| ES2430614T3 (es) | Métodos de tratamiento del cáncer usando inhibidores de piridopirimidinona de PI3K alfa | |
| CA2671982C (en) | Methods of using mek inhibitors | |
| ES2513165T3 (es) | Derivados de N-(3-amino-quinoxalin-2-il)-sulfonamida y su uso como inhibidores de la fosfatidilinositol-3-quinasa | |
| RU2650895C2 (ru) | Соединения замещенных пиразолонов и способы использования | |
| US9598400B2 (en) | Substituted quinoline compounds and methods of use | |
| AU2007284562B2 (en) | Using PI3K and MEK modulators in treatments of cancer | |
| WO2009017838A2 (en) | Combinations of jak-2 inhibitors and other agents | |
| WO2012065057A2 (en) | Phosphatidylinositol 3-kinase inhibitors and methods of their use | |
| JP2010523677A (ja) | 癌の治療のためのＰＩ３Ｋα阻害剤としてのピリド［２，３−Ｄ］ピリミジン−７−オン | |
| TW202400163A (zh) | 使用ｂｃｌ－２抑制劑治療髓性惡性腫瘤之方法 | |
| HK1140141B (en) | Combination therapies comprising a quinoxaline inhibitors of pi3k-alpha for use in the treatment of cancer |