CZ20031883A3 - Substituované aminové deriváty a způsoby jejich použití - Google Patents

Info

Publication number

CZ20031883A3

CZ20031883A3 CZ20031883A CZ20031883A CZ20031883A3 CZ 20031883 A3 CZ20031883 A3 CZ 20031883A3 CZ 20031883 A CZ20031883 A CZ 20031883A CZ 20031883 A CZ20031883 A CZ 20031883A CZ 20031883 A3 CZ20031883 A3 CZ 20031883A3

Authority

CZ

Czechia

Prior art keywords

optionally substituted

alkyl

substituted

group

phenyl

Prior art date

2001-01-12

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 37
• 150000001412 amines Chemical class 0.000 title abstract description 22
• 150000001875 compounds Chemical class 0.000 claims abstract description 132
• 238000011282 treatment Methods 0.000 claims abstract description 43
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 37
• 201000010099 disease Diseases 0.000 claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 230000033115 angiogenesis Effects 0.000 claims abstract description 17
• 201000011510 cancer Diseases 0.000 claims abstract description 15
• 230000008569 process Effects 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• -1 halosulfonyl Chemical group 0.000 claims description 1737
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 270
• 125000000623 heterocyclic group Chemical group 0.000 claims description 201
• 229910052739 hydrogen Inorganic materials 0.000 claims description 151
• 125000001424 substituent group Chemical group 0.000 claims description 128
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 101
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 229910052799 carbon Inorganic materials 0.000 claims description 91
• 229910052736 halogen Inorganic materials 0.000 claims description 89
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 82
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 82
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 74
• 150000002367 halogens Chemical group 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 60
• 125000004076 pyridyl group Chemical group 0.000 claims description 58
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 57
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 55
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 54
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 54
• 125000004043 oxo group Chemical group O=* 0.000 claims description 52
• 125000002883 imidazolyl group Chemical group 0.000 claims description 50
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 50
• 125000001544 thienyl group Chemical group 0.000 claims description 50
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 43
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 43
• 125000001041 indolyl group Chemical group 0.000 claims description 43
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 43
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 42
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 40
• 125000002619 bicyclic group Chemical group 0.000 claims description 38
• 125000003342 alkenyl group Chemical group 0.000 claims description 37
• 125000005493 quinolyl group Chemical group 0.000 claims description 36
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000001624 naphthyl group Chemical group 0.000 claims description 32
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000002757 morpholinyl group Chemical group 0.000 claims description 30
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 29
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 29
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 28
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
• 125000002541 furyl group Chemical group 0.000 claims description 28
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 28
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 27
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 27
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 27
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 27
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 27
• 125000000335 thiazolyl group Chemical group 0.000 claims description 27
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 26
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 26
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 26
• 239000000460 chlorine Chemical group 0.000 claims description 25
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 25
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 24
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 24
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 23
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 23
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 22
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 125000003107 substituted aryl group Chemical group 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 21
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 20
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 20
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 19
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
• 150000003857 carboxamides Chemical class 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 16
• 125000005466 alkylenyl group Chemical group 0.000 claims description 16
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 15
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 13
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 13
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 13
• 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 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000001425 triazolyl group Chemical group 0.000 claims description 12
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Chemical group 0.000 claims description 11
• 125000001246 bromo group Chemical group Br* 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 8
• 235000005152 nicotinamide Nutrition 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 238000009833 condensation Methods 0.000 claims description 6
• 230000005494 condensation Effects 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 239000011570 nicotinamide Substances 0.000 claims description 6
• 229960003966 nicotinamide Drugs 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 230000009826 neoplastic cell growth Effects 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 4
• 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 4
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 150000003053 piperidines Chemical class 0.000 claims description 4
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 239000002256 antimetabolite Substances 0.000 claims description 3
• 230000004663 cell proliferation Effects 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 2
• SJNPSFQXHBRXDH-UHFFFAOYSA-N 2-(1h-indazol-5-ylamino)-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3C=NNC3=CC=2)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 SJNPSFQXHBRXDH-UHFFFAOYSA-N 0.000 claims description 2
• BXLSUVHQGZLXJN-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(1-oxo-3,4-dihydro-2h-isoquinolin-7-yl)pyridine-3-carboxamide Chemical compound C1=C2C=NNC2=CC(NC2=NC=CC=C2C(NC=2C=C3C(=O)NCCC3=CC=2)=O)=C1 BXLSUVHQGZLXJN-UHFFFAOYSA-N 0.000 claims description 2
• XILCUKLHQBTCCD-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(3-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound CC(C)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 XILCUKLHQBTCCD-UHFFFAOYSA-N 0.000 claims description 2
• CVNCYTRSDHBYIJ-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(4-methyl-2-oxo-1h-quinolin-7-yl)pyridine-3-carboxamide Chemical compound C1=C2C=NNC2=CC(NC2=NC=CC=C2C(=O)NC=2C=C3NC(=O)C=C(C3=CC=2)C)=C1 CVNCYTRSDHBYIJ-UHFFFAOYSA-N 0.000 claims description 2
• KLUSNPWIWPSUHY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3NN=CC3=CC=2)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 KLUSNPWIWPSUHY-UHFFFAOYSA-N 0.000 claims description 2
• RHDIVPANJFAMJB-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3NN=CC3=CC=2)C=1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 RHDIVPANJFAMJB-UHFFFAOYSA-N 0.000 claims description 2
• PXPMSMKSXIIJCD-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(4-propan-2-yloxyphenyl)pyridine-3-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 PXPMSMKSXIIJCD-UHFFFAOYSA-N 0.000 claims description 2
• MEHPOJAPHCTJBE-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[1-(1-methylpiperidin-4-yl)-2,3-dihydroindol-6-yl]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1N1C2=CC(NC(=O)C=3C(=NC=CC=3)NC=3C=C4NN=CC4=CC=3)=CC=C2CC1 MEHPOJAPHCTJBE-UHFFFAOYSA-N 0.000 claims description 2
• XPVGZLJBEAYIHA-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[1-(2-morpholin-4-ylethyl)indol-6-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3NN=CC3=CC=2)C=1C(=O)NC(C=C12)=CC=C1C=CN2CCN1CCOCC1 XPVGZLJBEAYIHA-UHFFFAOYSA-N 0.000 claims description 2
• DGGRVLRUCMQLFG-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-5-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1N(C)CCC(C=2C=C(C=C(NC(=O)C=3C(=NC=CC=3)NC=3C=C4NN=CC4=CC=3)C=2)C(F)(F)F)=C1 DGGRVLRUCMQLFG-UHFFFAOYSA-N 0.000 claims description 2
• SQTNPBCRASDXPJ-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 SQTNPBCRASDXPJ-UHFFFAOYSA-N 0.000 claims description 2
• AGGXMYIKPXOFLY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(4-methylpiperazin-1-yl)phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 AGGXMYIKPXOFLY-UHFFFAOYSA-N 0.000 claims description 2
• HLUBJVRYJLGXAI-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 HLUBJVRYJLGXAI-UHFFFAOYSA-N 0.000 claims description 2
• RAIDKBBEISNMJN-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-[3-(4-methylpiperazin-1-yl)propyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCCC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 RAIDKBBEISNMJN-UHFFFAOYSA-N 0.000 claims description 2
• CYDBIHPSSNDRRY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 CYDBIHPSSNDRRY-UHFFFAOYSA-N 0.000 claims description 2
• FTMZJAHQMMCOOX-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-(1-methylpiperidin-4-yl)phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 FTMZJAHQMMCOOX-UHFFFAOYSA-N 0.000 claims description 2
• HUHNXZOWJJFJSZ-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-(2-methyl-4-morpholin-4-ylbutan-2-yl)phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=CC=1C(C)(C)CCN1CCOCC1 HUHNXZOWJJFJSZ-UHFFFAOYSA-N 0.000 claims description 2
• REQANLUVAHDLFS-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 REQANLUVAHDLFS-UHFFFAOYSA-N 0.000 claims description 2
• KXMBBWZPAJWEBK-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)CCC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 KXMBBWZPAJWEBK-UHFFFAOYSA-N 0.000 claims description 2
• VWDALHKLGLCYNS-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-[3-(4-methylpiperazin-1-yl)propyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCCC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 VWDALHKLGLCYNS-UHFFFAOYSA-N 0.000 claims description 2
• QCWGQHNAEBMKQB-UHFFFAOYSA-N 2-(2h-benzotriazol-5-ylamino)-n-(4-tert-butylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(N=NN2)C2=C1 QCWGQHNAEBMKQB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• PXZAHCRDFBLWHB-UHFFFAOYSA-N 6-fluoro-2-(1h-indazol-6-ylamino)-n-(4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=C(F)N=C1NC1=CC=C(C=NN2)C2=C1 PXZAHCRDFBLWHB-UHFFFAOYSA-N 0.000 claims description 2
• LFQBWMRUQFBYEN-UHFFFAOYSA-N 6-fluoro-2-(1h-indazol-6-ylamino)-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C=1C=C2C=NNC2=CC=1NC1=NC(F)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 LFQBWMRUQFBYEN-UHFFFAOYSA-N 0.000 claims description 2
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 2
• 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 2
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 229940125697 hormonal agent Drugs 0.000 claims description 2
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
• 239000000677 immunologic agent Substances 0.000 claims description 2
• 229940124541 immunological agent Drugs 0.000 claims description 2
• 239000012442 inert solvent Substances 0.000 claims description 2
• 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 2
• SAFXENMPHXNADP-UHFFFAOYSA-N n-(3-hydroxy-4-methoxyphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 SAFXENMPHXNADP-UHFFFAOYSA-N 0.000 claims description 2
• DRQUHVKBGYINIU-UHFFFAOYSA-N n-(3-tert-butylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 DRQUHVKBGYINIU-UHFFFAOYSA-N 0.000 claims description 2
• BHVKWDUBMNVNTL-UHFFFAOYSA-N n-(4-butan-2-ylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(C)CC)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 BHVKWDUBMNVNTL-UHFFFAOYSA-N 0.000 claims description 2
• ZOHQZKHQHNCIBN-UHFFFAOYSA-N n-(4-chloro-3-sulfamoylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 ZOHQZKHQHNCIBN-UHFFFAOYSA-N 0.000 claims description 2
• UFNQGBRICZTINI-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(1h-indazol-5-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(NN=C2)C2=C1 UFNQGBRICZTINI-UHFFFAOYSA-N 0.000 claims description 2
• KJGMIQFBFZYCRL-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 KJGMIQFBFZYCRL-UHFFFAOYSA-N 0.000 claims description 2
• CLFAYBWNJKZNDF-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(isoquinolin-5-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=CC2=CN=CC=C12 CLFAYBWNJKZNDF-UHFFFAOYSA-N 0.000 claims description 2
• OLTUKVAECQCHIS-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(quinolin-6-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(N=CC=C2)C2=C1 OLTUKVAECQCHIS-UHFFFAOYSA-N 0.000 claims description 2
• VIGDFQJHHVJZRW-UHFFFAOYSA-N n-(4-tert-butyl-1,3-thiazol-2-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CSC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=N1 VIGDFQJHHVJZRW-UHFFFAOYSA-N 0.000 claims description 2
• OFNXJPLWHSHDCA-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 OFNXJPLWHSHDCA-UHFFFAOYSA-N 0.000 claims description 2
• MNZCXLXJZARBSU-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-[[3-[2-(dimethylamino)ethoxy]-1h-indazol-6-yl]amino]pyridine-3-carboxamide Chemical compound C=1C=C2C(OCCN(C)C)=NNC2=CC=1NC1=NC=CC=C1C(=O)NC1=CC=C(C(C)(C)C)C=C1 MNZCXLXJZARBSU-UHFFFAOYSA-N 0.000 claims description 2
• GRTXLBFSFUDQJN-UHFFFAOYSA-N n-(4-tert-butylphenyl)-6-fluoro-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=C(F)N=C1NC1=CC=C(C=NN2)C2=C1 GRTXLBFSFUDQJN-UHFFFAOYSA-N 0.000 claims description 2
• LSDJFONVZRQXIJ-UHFFFAOYSA-N n-(5-tert-butyl-1-methylpyrazol-3-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(C(C)(C)C)N(C)N=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 LSDJFONVZRQXIJ-UHFFFAOYSA-N 0.000 claims description 2
• KMOVSBGWSYCXMB-UHFFFAOYSA-N n-(5-tert-butyl-2-methoxyphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 KMOVSBGWSYCXMB-UHFFFAOYSA-N 0.000 claims description 2
• ULLJLNIPYMYFQZ-UHFFFAOYSA-N n-[3,3-dimethyl-1-(1-methylpiperidin-4-yl)-2h-indol-6-yl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1N1C2=CC(NC(=O)C=3C(=NC=CC=3)NC=3C=C4NN=CC4=CC=3)=CC=C2C(C)(C)C1 ULLJLNIPYMYFQZ-UHFFFAOYSA-N 0.000 claims description 2
• SDYVHLGVQFYSBP-UHFFFAOYSA-N n-[3,3-dimethyl-1-(piperidin-4-ylmethyl)-2h-indol-6-yl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C12=CC(NC(=O)C=3C(=NC=CC=3)NC=3C=C4NN=CC4=CC=3)=CC=C2C(C)(C)CN1CC1CCNCC1 SDYVHLGVQFYSBP-UHFFFAOYSA-N 0.000 claims description 2
• XLVXYTJLUQKBFL-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(OCCN(C)C)C(OC)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 XLVXYTJLUQKBFL-UHFFFAOYSA-N 0.000 claims description 2
• MWQREZAZLQIKHP-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CN(C)CCOC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 MWQREZAZLQIKHP-UHFFFAOYSA-N 0.000 claims description 2
• NNBUGNCNZDHYCJ-UHFFFAOYSA-N n-[4-tert-butyl-2-(4-methylpiperazin-1-yl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 NNBUGNCNZDHYCJ-UHFFFAOYSA-N 0.000 claims description 2
• HVMOAZFZLXFEEH-UHFFFAOYSA-N n-[4-tert-butyl-3-(3-piperidin-3-ylpropyl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1CCCC1CCCNC1 HVMOAZFZLXFEEH-UHFFFAOYSA-N 0.000 claims description 2
• GBXLGZPJGUNDTC-UHFFFAOYSA-N n-[4-tert-butyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1CCCN1CCCC1 GBXLGZPJGUNDTC-UHFFFAOYSA-N 0.000 claims description 2
• QPSRNRMQSIAMFZ-UHFFFAOYSA-N n-[4-tert-butyl-3-(4-methylpiperazin-1-yl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=CC=C1C(C)(C)C QPSRNRMQSIAMFZ-UHFFFAOYSA-N 0.000 claims description 2
• XJKZJBHHLBUXQS-UHFFFAOYSA-N n-[5-tert-butyl-2-[2-(dimethylamino)ethoxy]phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CN(C)CCOC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 XJKZJBHHLBUXQS-UHFFFAOYSA-N 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 23
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 5
• 125000002947 alkylene group Chemical group 0.000 claims 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 2
• NBHXFCSDTHIPEH-UHFFFAOYSA-N n-[3-(2-hydroxy-3-pyrrolidin-1-ylpropoxy)-4-(1,1,2,2,2-pentafluoroethyl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=CC=C(C(F)(F)C(F)(F)F)C=1OCC(O)CN1CCCC1 NBHXFCSDTHIPEH-UHFFFAOYSA-N 0.000 claims 2
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• FMRFUKZPHGBWHF-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-1-ol Chemical compound C1=CC=C2C(O)NCCC2=C1 FMRFUKZPHGBWHF-UHFFFAOYSA-N 0.000 claims 1
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 1
• DHNYXXIKOJIAEM-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(5-phenyl-1h-pyrazol-3-yl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3NN=CC3=CC=2)C=1C(=O)NC(NN=1)=CC=1C1=CC=CC=C1 DHNYXXIKOJIAEM-UHFFFAOYSA-N 0.000 claims 1
• PMDUOJNIODWGHY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)CCC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 PMDUOJNIODWGHY-UHFFFAOYSA-N 0.000 claims 1
• UWVCZZTXUMTYKO-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 UWVCZZTXUMTYKO-UHFFFAOYSA-N 0.000 claims 1
• LAOWZCITVUTYPL-UHFFFAOYSA-N 2-[(1-methylindazol-6-yl)amino]-n-(4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2C)C2=C1 LAOWZCITVUTYPL-UHFFFAOYSA-N 0.000 claims 1
• HOKUTCLIRMVHQV-UHFFFAOYSA-N 2-[(1-pyridin-2-ylpyrrolidin-3-yl)amino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC2CN(CC2)C=2N=CC=CC=2)=C1 HOKUTCLIRMVHQV-UHFFFAOYSA-N 0.000 claims 1
• 235000007119 Ananas comosus Nutrition 0.000 claims 1
• 244000099147 Ananas comosus Species 0.000 claims 1
• VDAKZZOFSPCAPE-UHFFFAOYSA-N N'-(1H-indazol-6-yl)pyridine-3-carbohydrazide Chemical compound C(C1=CN=CC=C1)(=O)NNC1=CC=C2C=NNC2=C1 VDAKZZOFSPCAPE-UHFFFAOYSA-N 0.000 claims 1
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
• 208000035475 disorder Diseases 0.000 claims 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
• TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical group Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 claims 1
• MXBPMLKVURKQPA-UHFFFAOYSA-N n-(1-acetyl-3,3-dimethyl-2h-indol-6-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C2C=NNC2=CC(NC2=NC=CC=C2C(=O)NC2=CC=C3C(C)(C)CN(C3=C2)C(=O)C)=C1 MXBPMLKVURKQPA-UHFFFAOYSA-N 0.000 claims 1
• RKYIMIDBQFSWPW-UHFFFAOYSA-N n-(3,3-dimethyl-1,2-dihydroindol-6-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C2C=NNC2=CC(NC2=NC=CC=C2C(=O)NC=2C=C3NCC(C3=CC=2)(C)C)=C1 RKYIMIDBQFSWPW-UHFFFAOYSA-N 0.000 claims 1
• IIQAJYOAFQULOZ-UHFFFAOYSA-N n-(3-amino-4-tert-butylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(N)C(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 IIQAJYOAFQULOZ-UHFFFAOYSA-N 0.000 claims 1
• ACQCCUUIEJHOTE-UHFFFAOYSA-N n-(4-tert-butyl-3-nitrophenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C([N+]([O-])=O)C(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 ACQCCUUIEJHOTE-UHFFFAOYSA-N 0.000 claims 1
• MTNMCUMIEOXOGT-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound S1C(C(C)(C)C)=NN=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 MTNMCUMIEOXOGT-UHFFFAOYSA-N 0.000 claims 1
• HYXRNCTVFZKVFX-UHFFFAOYSA-N n-[4-tert-butyl-3-(2-hydroxyethylamino)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1=C(NCCO)C(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 HYXRNCTVFZKVFX-UHFFFAOYSA-N 0.000 claims 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
• DKHSOMZCLGZQSB-UHFFFAOYSA-N tert-butyl 4-[2-tert-butyl-5-[[2-(1h-indazol-6-ylamino)pyridine-3-carbonyl]amino]anilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=CC=C1C(C)(C)C DKHSOMZCLGZQSB-UHFFFAOYSA-N 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 7
• 230000001404 mediated effect Effects 0.000 abstract description 5
• 238000011321 prophylaxis Methods 0.000 abstract description 3
• 239000000651 prodrug Substances 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• 125000004432 carbon atom Chemical group C* 0.000 description 42
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
• 239000003054 catalyst Substances 0.000 description 23
• 239000002253 acid Substances 0.000 description 20
• 239000002904 solvent Substances 0.000 description 19
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
• 150000001448 anilines Chemical class 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 17
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 15
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 15
• 239000002246 antineoplastic agent Substances 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 229940034982 antineoplastic agent Drugs 0.000 description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
• 150000001408 amides Chemical class 0.000 description 11
• 238000005984 hydrogenation reaction Methods 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 239000012298 atmosphere Substances 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 8
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 8
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
• RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
• 108010050904 Interferons Proteins 0.000 description 7
• 102000014150 Interferons Human genes 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 230000012010 growth Effects 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 229940079322 interferon Drugs 0.000 description 7
• 150000002828 nitro derivatives Chemical class 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
• MKDCJAPHKZPKOU-UHFFFAOYSA-N 1-nitro-2,3-dihydroindole Chemical class C1=CC=C2N([N+](=O)[O-])CCC2=C1 MKDCJAPHKZPKOU-UHFFFAOYSA-N 0.000 description 6
• PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 6
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 239000013543 active substance Substances 0.000 description 6
• 230000001684 chronic effect Effects 0.000 description 6
• 229910052751 metal Inorganic materials 0.000 description 6
• 239000002184 metal Substances 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
• 108010047761 Interferon-alpha Proteins 0.000 description 5
• 102000006992 Interferon-alpha Human genes 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 208000025747 Rheumatic disease Diseases 0.000 description 5
• 206010042674 Swelling Diseases 0.000 description 5
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 5
• 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 5
• 229960002932 anastrozole Drugs 0.000 description 5
• YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical class C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 5
• 206010003246 arthritis Diseases 0.000 description 5
• 229960000684 cytarabine Drugs 0.000 description 5
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 210000002889 endothelial cell Anatomy 0.000 description 5
• 208000027866 inflammatory disease Diseases 0.000 description 5
• 230000001613 neoplastic effect Effects 0.000 description 5
• 230000008961 swelling Effects 0.000 description 5
• 238000002560 therapeutic procedure Methods 0.000 description 5
• 210000004881 tumor cell Anatomy 0.000 description 5
• 229960005486 vaccine Drugs 0.000 description 5
• 230000002792 vascular Effects 0.000 description 5
• 239000002525 vasculotropin inhibitor Substances 0.000 description 5
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• WLFGGJFWKXTOGJ-UHFFFAOYSA-N 2,3-dihydroindol-1-amine Chemical class C1=CC=C2N(N)CCC2=C1 WLFGGJFWKXTOGJ-UHFFFAOYSA-N 0.000 description 4
• IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 description 4
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• 108091000080 Phosphotransferase Proteins 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 108091008605 VEGF receptors Proteins 0.000 description 4
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 4
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
• 230000029936 alkylation Effects 0.000 description 4
• 238000005804 alkylation reaction Methods 0.000 description 4
• 238000005576 amination reaction Methods 0.000 description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• 229960002949 fluorouracil Drugs 0.000 description 4
• CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 4
• 230000002757 inflammatory effect Effects 0.000 description 4
• 208000032839 leukemia Diseases 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
• 150000005480 nicotinamides Chemical class 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• 102000020233 phosphotransferase Human genes 0.000 description 4
• 230000035755 proliferation Effects 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 150000003335 secondary amines Chemical class 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 208000011580 syndromic disease Diseases 0.000 description 4
• 229940124597 therapeutic agent Drugs 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
• LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 206010048962 Brain oedema Diseases 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• 201000009273 Endometriosis Diseases 0.000 description 3
• 206010015866 Extravasation Diseases 0.000 description 3
• 206010016654 Fibrosis Diseases 0.000 description 3
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 208000010412 Glaucoma Diseases 0.000 description 3
• 206010018338 Glioma Diseases 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
• 206010025323 Lymphomas Diseases 0.000 description 3
• 206010029113 Neovascularisation Diseases 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 229930012538 Paclitaxel Natural products 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 102000001253 Protein Kinase Human genes 0.000 description 3
• 208000017442 Retinal disease Diseases 0.000 description 3
• 206010038923 Retinopathy Diseases 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 102100039037 Vascular endothelial growth factor A Human genes 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 150000001350 alkyl halides Chemical class 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
• 239000004037 angiogenesis inhibitor Substances 0.000 description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
• 208000006752 brain edema Diseases 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229910052802 copper Inorganic materials 0.000 description 3
• 239000010949 copper Substances 0.000 description 3
• 239000002254 cytotoxic agent Substances 0.000 description 3
• 229940127089 cytotoxic agent Drugs 0.000 description 3
• 231100000599 cytotoxic agent Toxicity 0.000 description 3
• 229960004679 doxorubicin Drugs 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 230000036251 extravasation Effects 0.000 description 3
• 239000003102 growth factor Substances 0.000 description 3
• 229940093915 gynecological organic acid Drugs 0.000 description 3
• 125000004995 haloalkylthio group Chemical group 0.000 description 3
• 201000011066 hemangioma Diseases 0.000 description 3
• 201000005787 hematologic cancer Diseases 0.000 description 3
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 208000014674 injury Diseases 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 150000005181 nitrobenzenes Chemical class 0.000 description 3
• 235000005985 organic acids Nutrition 0.000 description 3
• 229960001592 paclitaxel Drugs 0.000 description 3
• 230000002265 prevention Effects 0.000 description 3
• 108060006633 protein kinase Proteins 0.000 description 3
• 150000003222 pyridines Chemical class 0.000 description 3
• 230000002829 reductive effect Effects 0.000 description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 239000000243 solution Substances 0.000 description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
• 201000004595 synovitis Diseases 0.000 description 3
• 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 3
• 210000002435 tendon Anatomy 0.000 description 3
• 229960001727 tretinoin Drugs 0.000 description 3
• 235000020138 yakult Nutrition 0.000 description 3
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
• ZZKNRXZVGOYGJT-VKHMYHEASA-N (2s)-2-[(2-phosphonoacetyl)amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)CP(O)(O)=O ZZKNRXZVGOYGJT-VKHMYHEASA-N 0.000 description 2
• FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 2
• GTADQMQBQBOJIO-UHFFFAOYSA-N 1,12-Dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone Chemical compound ON1CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC1=O GTADQMQBQBOJIO-UHFFFAOYSA-N 0.000 description 2
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 description 2
• XFNOJSQSVJKEBD-UHFFFAOYSA-N 1-chloro-7-nitro-3,4-dihydroisoquinoline Chemical compound C1CN=C(Cl)C2=CC([N+](=O)[O-])=CC=C21 XFNOJSQSVJKEBD-UHFFFAOYSA-N 0.000 description 2
• VHJWDTPKSIFZBV-UHFFFAOYSA-N 2,5,7-trihydroxy-4-(4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl)oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione Chemical compound COC1C(O)C(OC)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=C(OC)C=C3C3=O)=C3C=C2C(=O)C(C)(O)C1OC VHJWDTPKSIFZBV-UHFFFAOYSA-N 0.000 description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
• GNDKYAWHEKZHPJ-UHFFFAOYSA-N 2-nitrobenzenesulfonimidic acid Chemical class NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O GNDKYAWHEKZHPJ-UHFFFAOYSA-N 0.000 description 2
• WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical class [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
• AKJHMTWEGVYYSE-AIRMAKDCSA-N 4-HPR Chemical compound C=1C=C(O)C=CC=1NC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-AIRMAKDCSA-N 0.000 description 2
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
• XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
• 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 2
• PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
• 208000027932 Collagen disease Diseases 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• GJKXGJCSJWBJEZ-XRSSZCMZSA-N Deslorelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CNC2=CC=CC=C12 GJKXGJCSJWBJEZ-XRSSZCMZSA-N 0.000 description 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
• 208000032612 Glial tumor Diseases 0.000 description 2
• 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 206010021143 Hypoxia Diseases 0.000 description 2
• 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 2
• 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 2
• 102100040018 Interferon alpha-2 Human genes 0.000 description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 description 2
• 208000001344 Macular Edema Diseases 0.000 description 2
• 206010025415 Macular oedema Diseases 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• 206010027476 Metastases Diseases 0.000 description 2
• 101100189356 Mus musculus Papolb gene Proteins 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
• 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 2
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
• 206010029260 Neuroblastoma Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 108010082093 Placenta Growth Factor Proteins 0.000 description 2
• 102100035194 Placenta growth factor Human genes 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 2
• 206010039491 Sarcoma Diseases 0.000 description 2
• OCOKWVBYZHBHLU-UHFFFAOYSA-N Sobuzoxane Chemical compound C1C(=O)N(COC(=O)OCC(C)C)C(=O)CN1CCN1CC(=O)N(COC(=O)OCC(C)C)C(=O)C1 OCOKWVBYZHBHLU-UHFFFAOYSA-N 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 2
• RKJCLPSFLUKWQY-UHFFFAOYSA-N Tricrozarin A Chemical compound OC1=C2C(=O)C(OC)=C(OC)C(=O)C2=C(O)C2=C1OCO2 RKJCLPSFLUKWQY-UHFFFAOYSA-N 0.000 description 2
• 208000025865 Ulcer Diseases 0.000 description 2
• 229940116211 Vasopressin antagonist Drugs 0.000 description 2
• USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 2
• 229960004176 aclarubicin Drugs 0.000 description 2
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• ANVAOWXLWRTKGA-XHGAXZNDSA-N all-trans-alpha-carotene Chemical compound CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1C(C)=CCCC1(C)C ANVAOWXLWRTKGA-XHGAXZNDSA-N 0.000 description 2
• 229960000473 altretamine Drugs 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 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 2
• 229960001220 amsacrine Drugs 0.000 description 2
• 239000002870 angiogenesis inducing agent Substances 0.000 description 2
• 229940121369 angiogenesis inhibitor Drugs 0.000 description 2
• 230000001093 anti-cancer Effects 0.000 description 2
• 239000002260 anti-inflammatory agent Substances 0.000 description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 description 2
• 239000003146 anticoagulant agent Substances 0.000 description 2
• 229940127219 anticoagulant drug Drugs 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 2
• 125000001769 aryl amino group Chemical group 0.000 description 2
• 125000005110 aryl thio group Chemical group 0.000 description 2
• 208000006673 asthma Diseases 0.000 description 2
• 229940054066 benzamide antipsychotics Drugs 0.000 description 2
• 150000003936 benzamides Chemical class 0.000 description 2
• 230000033228 biological regulation Effects 0.000 description 2
• 210000004204 blood vessel Anatomy 0.000 description 2
• 125000005620 boronic acid group Chemical class 0.000 description 2
• 150000001649 bromium compounds Chemical class 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
• 230000036952 cancer formation Effects 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 229960005243 carmustine Drugs 0.000 description 2
• 230000002490 cerebral effect Effects 0.000 description 2
• 238000002512 chemotherapy Methods 0.000 description 2
• 230000006020 chronic inflammation Effects 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
• 239000000824 cytostatic agent Substances 0.000 description 2
• 230000001085 cytostatic effect Effects 0.000 description 2
• 229960000640 dactinomycin Drugs 0.000 description 2
• 229960000975 daunorubicin Drugs 0.000 description 2
• 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 2
• 230000008021 deposition Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 201000001981 dermatomyositis Diseases 0.000 description 2
• 108700025485 deslorelin Proteins 0.000 description 2
• 229960005408 deslorelin Drugs 0.000 description 2
• 125000004982 dihaloalkyl group Chemical group 0.000 description 2
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
• 229960003668 docetaxel Drugs 0.000 description 2
• NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
• ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 2
• 229950005454 doxifluridine Drugs 0.000 description 2
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 2
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 2
• 210000002744 extracellular matrix Anatomy 0.000 description 2
• 229950003662 fenretinide Drugs 0.000 description 2
• 229940012952 fibrinogen Drugs 0.000 description 2
• 230000004761 fibrosis Effects 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
• 229960005304 fludarabine phosphate Drugs 0.000 description 2
• YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 2
• 229960004783 fotemustine Drugs 0.000 description 2
• 229940044658 gallium nitrate Drugs 0.000 description 2
• 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 2
• 230000014509 gene expression Effects 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 125000004438 haloalkoxy group Chemical group 0.000 description 2
• 150000002366 halogen compounds Chemical class 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
• 125000005241 heteroarylamino group Chemical group 0.000 description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 description 2
• UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
• 230000007954 hypoxia Effects 0.000 description 2
• 229960000908 idarubicin Drugs 0.000 description 2
• 125000002632 imidazolidinyl group Chemical group 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
• 208000015181 infectious disease Diseases 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 150000004694 iodide salts Chemical class 0.000 description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
• GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 2
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
• 230000003137 locomotive effect Effects 0.000 description 2
• 206010025135 lupus erythematosus Diseases 0.000 description 2
• 208000002780 macular degeneration Diseases 0.000 description 2
• 201000010230 macular retinal edema Diseases 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
• HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 description 2
• 201000001441 melanoma Diseases 0.000 description 2
• 229940115256 melanoma vaccine Drugs 0.000 description 2
• LWYJUZBXGAFFLP-OCNCTQISSA-N menogaril Chemical compound O1[C@@]2(C)[C@H](O)[C@@H](N(C)C)[C@H](O)[C@@H]1OC1=C3C(=O)C(C=C4C[C@@](C)(O)C[C@H](C4=C4O)OC)=C4C(=O)C3=C(O)C=C12 LWYJUZBXGAFFLP-OCNCTQISSA-N 0.000 description 2
• 229950002676 menogaril Drugs 0.000 description 2
• 230000009401 metastasis Effects 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 125000006682 monohaloalkyl group Chemical group 0.000 description 2
• AYIQSOAPZKBTBL-UHFFFAOYSA-N n-(2-methylprop-2-enyl)acetamide Chemical compound CC(=C)CNC(C)=O AYIQSOAPZKBTBL-UHFFFAOYSA-N 0.000 description 2
• 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 2
• UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 description 2
• 201000003142 neovascular glaucoma Diseases 0.000 description 2
• 229910052759 nickel Inorganic materials 0.000 description 2
• 229960002715 nicotine Drugs 0.000 description 2
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
• 238000006396 nitration reaction Methods 0.000 description 2
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 201000008482 osteoarthritis Diseases 0.000 description 2
• 201000008968 osteosarcoma Diseases 0.000 description 2
• 230000002611 ovarian Effects 0.000 description 2
• 210000001672 ovary Anatomy 0.000 description 2
• DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 2
• 229960001756 oxaliplatin Drugs 0.000 description 2
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
• 230000003076 paracrine Effects 0.000 description 2
• FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 2
• 229960002340 pentostatin Drugs 0.000 description 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
• 201000010065 polycystic ovary syndrome Diseases 0.000 description 2
• 125000006684 polyhaloalkyl group Polymers 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 230000005855 radiation Effects 0.000 description 2
• 102000005962 receptors Human genes 0.000 description 2
• 108020003175 receptors Proteins 0.000 description 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
• 230000000552 rheumatic effect Effects 0.000 description 2
• 229950010372 sobuzoxane Drugs 0.000 description 2
• 108010042747 stallimycin Proteins 0.000 description 2
• 230000004936 stimulating effect Effects 0.000 description 2
• 230000008409 synovial inflammation Effects 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 229960001674 tegafur Drugs 0.000 description 2
• WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 2
• 229960004964 temozolomide Drugs 0.000 description 2
• 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 2
• 229960001278 teniposide Drugs 0.000 description 2
• ZCTJIMXXSXQXRI-UHFFFAOYSA-N thaliblastine Natural products CN1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=C(OC)C(OC2=C(CC3C4=CC(OC)=C(OC)C=C4CCN3C)C=C(C(=C2)OC)OC)=C1 ZCTJIMXXSXQXRI-UHFFFAOYSA-N 0.000 description 2
• ZCTJIMXXSXQXRI-KYJUHHDHSA-N thalicarpine Chemical compound CN1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC2=C(C[C@H]3C4=CC(OC)=C(OC)C=C4CCN3C)C=C(C(=C2)OC)OC)=C1 ZCTJIMXXSXQXRI-KYJUHHDHSA-N 0.000 description 2
• 125000001984 thiazolidinyl group Chemical group 0.000 description 2
• 210000001685 thyroid gland Anatomy 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000008733 trauma Effects 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
• 230000005747 tumor angiogenesis Effects 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 210000003932 urinary bladder Anatomy 0.000 description 2
• 230000006711 vascular endothelial growth factor production Effects 0.000 description 2
• 239000003038 vasopressin antagonist Substances 0.000 description 2
• 230000003612 virological effect Effects 0.000 description 2
• 239000011701 zinc Substances 0.000 description 2
• 229910052725 zinc Inorganic materials 0.000 description 2
• AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 1
• OTWVIYXCRFLDJW-QMVMUTFZSA-N (1-hydroxy-1-phosphonooxyethyl) dihydrogen phosphate;rhenium-186 Chemical compound [186Re].OP(=O)(O)OC(O)(C)OP(O)(O)=O OTWVIYXCRFLDJW-QMVMUTFZSA-N 0.000 description 1
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
• JLSPXOVSIVYMCY-UHFFFAOYSA-N (2,4-dichlorophenyl)methyl thiocyanate Chemical compound ClC1=CC=C(CSC#N)C(Cl)=C1 JLSPXOVSIVYMCY-UHFFFAOYSA-N 0.000 description 1
• PQZVBIJEPVKNOZ-PCLZMVHQSA-N (2R)-2-[(1S)-1-hydroxy-1-[(5R,6R,8R,9S,10R,13S,14R,17S)-5,6,14,17-tetrahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one Chemical class C1C(C)=C(C)C(=O)O[C@H]1[C@](C)(O)[C@@]1(O)[C@@]2(C)CC[C@@H]3[C@@]4(C)C(=O)C=CC[C@]4(O)[C@H](O)C[C@H]3[C@]2(O)CC1 PQZVBIJEPVKNOZ-PCLZMVHQSA-N 0.000 description 1
• FKHUGQZRBPETJR-RXSRXONKSA-N (2r)-2-[[(4r)-4-[[(2s)-2-[[(2r)-2-[(3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]-6-(octadecanoylamino)hexanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@H](C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O FKHUGQZRBPETJR-RXSRXONKSA-N 0.000 description 1
• JLCDKDGHTWGGQM-CQSZACIVSA-N (2r)-n-benzyl-1-phenylpropan-2-amine Chemical compound C([C@@H](C)NCC=1C=CC=CC=1)C1=CC=CC=C1 JLCDKDGHTWGGQM-CQSZACIVSA-N 0.000 description 1
• WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
• OKNKQPUDKRCBIK-MAVIPZKQSA-N (2r,3r,4s,5s)-2-(9-hydroxy-5,11-dimethyl-6h-pyrido[4,3-b]carbazol-2-ium-2-yl)oxane-3,4,5-triol;bromide Chemical compound [Br-].C=1C=C2C(C)=C3NC4=CC=C(O)C=C4C3=C(C)C2=C[N+]=1[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O OKNKQPUDKRCBIK-MAVIPZKQSA-N 0.000 description 1
• QJERBBQXOMUURJ-INIZCTEOSA-N (2s)-2-[(4-chlorobenzoyl)amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C1=CC=C(Cl)C=C1 QJERBBQXOMUURJ-INIZCTEOSA-N 0.000 description 1
• ZUQBAQVRAURMCL-DOMZBBRYSA-N (2s)-2-[[4-[2-[(6r)-2-amino-4-oxo-5,6,7,8-tetrahydro-1h-pyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]amino]pentanedioic acid Chemical compound C([C@@H]1CC=2C(=O)N=C(NC=2NC1)N)CC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ZUQBAQVRAURMCL-DOMZBBRYSA-N 0.000 description 1
• YEORLXJBCPPSOC-SSDOTTSWSA-N (2s)-2-amino-5-(diaminomethylideneamino)-2-(difluoromethyl)pentanoic acid Chemical compound NC(=N)NCCC[C@@](N)(C(F)F)C(O)=O YEORLXJBCPPSOC-SSDOTTSWSA-N 0.000 description 1
• LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 1
• XOYXESIZZFUVRD-UVSAJTFZSA-N (2s,3s,4r,5s,6s)-6-[(2r,3r,4r,5s,6r)-6-[(2r,3s,4r,5s,6r)-5-acetamido-6-[(2r,3r,4r,5s,6r)-4-acetyloxy-6-[(2r,3r,4r,5s,6r)-4-acetyloxy-6-[(2r,3r,4r,5s,6s)-4-acetyloxy-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]ox Chemical compound CC(=O)O[C@@H]1[C@H](O)[C@@H](OC)O[C@H](CO)[C@H]1O[C@@H]1[C@@H](O)[C@@H](OC(C)=O)[C@H](O[C@@H]2[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]3[C@H]([C@@H](O)[C@H](O[C@@H]4[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]5[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]6[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]7[C@H]([C@@H](OC(C)=O)[C@H](OC)[C@@H](CO)O7)O)[C@@H](CO)O6)O)[C@H](O5)C(O)=O)O)[C@@H](CO)O4)O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)O)[C@@H](CO)O1 XOYXESIZZFUVRD-UVSAJTFZSA-N 0.000 description 1
• JEMVIRAQUIJOCL-XURVNGJNSA-N (3r,4ar,12bs)-4a,8,12b-trihydroxy-9-[(2r,4r,5s,6r)-4-hydroxy-6-methyl-5-[(2s,5s,6s)-6-methyl-5-[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]-3-methyl-3-[(2s,5s,6s)-6-methyl-5-[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-2,4-dihydrobenzo Chemical compound O([C@H]1CC[C@@H](O[C@H]1C)O[C@H]1[C@@H](C[C@@H](O[C@@H]1C)C=1C(=C2C(=O)C3=C([C@]4(C(=O)C[C@@](C)(C[C@@]4(O)C=C3)O[C@@H]3O[C@@H](C)[C@@H](O[C@@H]4O[C@@H](C)C(=O)CC4)CC3)O)C(=O)C2=CC=1)O)O)[C@H]1CCC(=O)[C@H](C)O1 JEMVIRAQUIJOCL-XURVNGJNSA-N 0.000 description 1
• IEFNEZUQHDYNRM-UHFFFAOYSA-L (4-azanidyl-2-methylbutyl)azanide;cyclobutane-1,1-dicarboxylate;platinum(4+) Chemical compound [Pt+4].[NH-]CC(C)CC[NH-].[O-]C(=O)C1(C([O-])=O)CCC1 IEFNEZUQHDYNRM-UHFFFAOYSA-L 0.000 description 1
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-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
• KMPLYESDOZJASB-PAHRJMAXSA-N (6s,8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-6-methoxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one;(z)-n-carbamoyl-2-ethylbut-2-enamide;6-ethoxy-1,3-benzothiazole-2-sulfonamide Chemical compound CC\C(=C\C)C(=O)NC(N)=O.CCOC1=CC=C2N=C(S(N)(=O)=O)SC2=C1.C([C@@]12C)CC(=O)C=C1[C@@H](OC)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 KMPLYESDOZJASB-PAHRJMAXSA-N 0.000 description 1
• LKBBOPGQDRPCDS-YAOXHJNESA-N (7s,9r,10r)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-ethyl-4,6,9,10,11-pentahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O([C@H]1C[C@]([C@@H](C2=C(O)C=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)O)(O)CC)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 LKBBOPGQDRPCDS-YAOXHJNESA-N 0.000 description 1
• BHMLHEQFWVQAJS-IITOGVPQSA-N (7s,9s)-9-acetyl-9-amino-7-[(2s,4s,5r)-4,5-dihydroxyoxan-2-yl]oxy-6,11-dihydroxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)(N)C(=O)C)[C@H]1C[C@H](O)[C@H](O)CO1 BHMLHEQFWVQAJS-IITOGVPQSA-N 0.000 description 1
• DIPVWSTVQDONTF-NUAZBEIESA-N (8E)-2-[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-6-methoxy-8-propylidene-6,6a,7,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical compound CC\C=C1/CC2C(Nc3ccc(O[C@@H]4O[C@@H](C)[C@H](NC)[C@@H](O)[C@H]4O)cc3C(=O)N2C1)OC DIPVWSTVQDONTF-NUAZBEIESA-N 0.000 description 1
• JEZZKSQFJNWDCY-NSIKDUERSA-N (8z)-2-[3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-8-propylidene-7,9-dihydro-6ah-pyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical compound C1=C2C(=O)N3CC(=C/CC)\CC3C=NC2=CC=C1OC1OC(C)C(NC)C(C)(O)C1O JEZZKSQFJNWDCY-NSIKDUERSA-N 0.000 description 1
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
• ROBVIMPUHSLWNV-CYBMUJFWSA-N (R)-aminoglutethimide Chemical compound C=1C=C(N)C=CC=1[C@@]1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-CYBMUJFWSA-N 0.000 description 1
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
• DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
• MHFRGQHAERHWKZ-HHHXNRCGSA-N (R)-edelfosine Chemical compound CCCCCCCCCCCCCCCCCCOC[C@@H](OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-HHHXNRCGSA-N 0.000 description 1
• AJMWJDGKNKNYEW-WYMLVPIESA-N (e)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methylprop-2-en-1-one Chemical compound COC1=CC=C(OC)C(C(=O)C(\C)=C\C=2C=CC(=CC=2)N(C)C)=C1 AJMWJDGKNKNYEW-WYMLVPIESA-N 0.000 description 1
• OQMYRVPMCIOFHL-GCOHUWJYSA-N (e)-3-[(6r)-6-hydroxy-4-methoxy-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]-n,n-dimethylprop-2-enamide Chemical compound N1[C@H](O)C2CC(\C=C\C(=O)N(C)C)=CN2C(=O)C2=C1C(OC)=CC=C2 OQMYRVPMCIOFHL-GCOHUWJYSA-N 0.000 description 1
• HYNDYAQJODYUGF-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1NCCCN2CCCC=C21 HYNDYAQJODYUGF-UHFFFAOYSA-N 0.000 description 1
• 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 1
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
• ZTXDHEQQZVFGPK-UHFFFAOYSA-N 1,2,4-tris(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound C1OC1CN1C(=O)N(CC2OC2)C(=O)N1CC1CO1 ZTXDHEQQZVFGPK-UHFFFAOYSA-N 0.000 description 1
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
• 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
• QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
• QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
• DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 description 1
• HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
• OUPZKGBUJRBPGC-HLTSFMKQSA-N 1,5-bis[[(2r)-oxiran-2-yl]methyl]-3-[[(2s)-oxiran-2-yl]methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(C[C@H]2OC2)C(=O)N(C[C@H]2OC2)C(=O)N1C[C@H]1CO1 OUPZKGBUJRBPGC-HLTSFMKQSA-N 0.000 description 1
• KHWIRCOLWPNBJP-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2,6-dioxopiperidin-3-yl)-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NC1CCC(=O)NC1=O KHWIRCOLWPNBJP-UHFFFAOYSA-N 0.000 description 1
• YJZJEQBSODVMTH-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2-hydroxyethyl)-1-nitrosourea Chemical compound OCCNC(=O)N(N=O)CCCl YJZJEQBSODVMTH-UHFFFAOYSA-N 0.000 description 1
• BQIFCAGMUAMYDV-DHBOJHSNSA-N 1-(2-chloroethyl)-3-[(2r,6s)-2,6-dihydroxycyclohexyl]-1-nitrosourea Chemical compound O[C@H]1CCC[C@@H](O)C1NC(=O)N(CCCl)N=O BQIFCAGMUAMYDV-DHBOJHSNSA-N 0.000 description 1
• RCLLNBVPCJDIPX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosourea Chemical compound CN(C)S(=O)(=O)CCNC(=O)N(N=O)CCCl RCLLNBVPCJDIPX-UHFFFAOYSA-N 0.000 description 1
• WFZCJZLWNBAQDW-UHFFFAOYSA-N 1-(3,3-dimethyl-6-nitro-2h-indol-1-yl)ethanone Chemical compound C1=C([N+]([O-])=O)C=C2N(C(=O)C)CC(C)(C)C2=C1 WFZCJZLWNBAQDW-UHFFFAOYSA-N 0.000 description 1
• ICAYNKLSQSKOJZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]butan-1-one Chemical compound C=1C=C(F)C=CC=1C(O)C(CC1)CCN1CCCC(=O)C1=CC=C(F)C=C1 ICAYNKLSQSKOJZ-UHFFFAOYSA-N 0.000 description 1
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
• ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
• VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
• SQMVRFXDBRYXFQ-UHFFFAOYSA-N 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine Chemical compound C1N(C)CCC(B2OC(C)(C)C(C)(C)O2)=C1 SQMVRFXDBRYXFQ-UHFFFAOYSA-N 0.000 description 1
• HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
• NWBQMKBXBNAKQN-UHFFFAOYSA-N 1-nitro-4-(1,1,2,2,2-pentafluoroethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(C(F)(F)C(F)(F)F)C=C1 NWBQMKBXBNAKQN-UHFFFAOYSA-N 0.000 description 1
• ZLOXFEJDHGQNOG-UHFFFAOYSA-N 1-nitroindole Chemical class C1=CC=C2N([N+](=O)[O-])C=CC2=C1 ZLOXFEJDHGQNOG-UHFFFAOYSA-N 0.000 description 1
• VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
• VSWUWZJXMRATTF-UHFFFAOYSA-N 1-propan-2-yl-1h-pyrrolizine Chemical compound C1=CC=C2C(C(C)C)C=CN21 VSWUWZJXMRATTF-UHFFFAOYSA-N 0.000 description 1
• XSCPVQNNFLHGHY-UHFFFAOYSA-N 1-tert-butyl-4-nitrobenzene Chemical compound CC(C)(C)C1=CC=C([N+]([O-])=O)C=C1 XSCPVQNNFLHGHY-UHFFFAOYSA-N 0.000 description 1
• AQBUFJBHZGRZRV-NCIKYIMWSA-N 10-[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-4,6-dimethyloxan-2-yl]-11-hydroxy-5-methyl-2-[(2R,3S)-2-methyl-3-[(2R,3S)-3-methyloxiran-2-yl]oxiran-2-yl]naphtho[2,3-h]chromene-4,7,12-trione Chemical compound C[C@@H]1O[C@H]1[C@H]1[C@@](C=2OC3=C4C(=O)C5=C(O)C([C@@H]6O[C@@H](C)[C@@H](O)[C@](C)(C6)N(C)C)=CC=C5C(=O)C4=CC(C)=C3C(=O)C=2)(C)O1 AQBUFJBHZGRZRV-NCIKYIMWSA-N 0.000 description 1
• SCWWNJYIUMBQKK-UHFFFAOYSA-N 10-[4-(dimethylamino)-5,6-dihydroxy-4,6-dimethyloxan-2-yl]-8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2-[3-(3,3-dimethyloxiran-2-yl)-2-methyloxiran-2-yl]-11-hydroxy-5-methylnaphtho[2,3-h]chromene-4,7,12-trione Chemical compound C1C(N(C)C)C(O)C(C)OC1C1=CC(C2OC(C)(O)C(O)C(C)(C2)N(C)C)=C(O)C2=C1C(=O)C(C=C(C)C=1C(C=C(OC3=1)C1(C)C(O1)C1C(O1)(C)C)=O)=C3C2=O SCWWNJYIUMBQKK-UHFFFAOYSA-N 0.000 description 1
• DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
• CNQCTSLNJJVSAU-UHFFFAOYSA-N 132937-89-4 Chemical compound O.Cl.Cl.Cl.Cl.OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO.OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO CNQCTSLNJJVSAU-UHFFFAOYSA-N 0.000 description 1
• BOMZMNZEXMAQQW-UHFFFAOYSA-N 2,5,11-trimethyl-6h-pyrido[4,3-b]carbazol-2-ium-9-ol;acetate Chemical compound CC([O-])=O.C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 BOMZMNZEXMAQQW-UHFFFAOYSA-N 0.000 description 1
• QQAKKIKNNFCLEP-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(2-pyrrolidin-1-ylethoxy)-4-(trifluoromethyl)phenyl]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1OCCN1CCCC1 QQAKKIKNNFCLEP-UHFFFAOYSA-N 0.000 description 1
• FJXCUBSPQFMYKH-INIZCTEOSA-N 2-(1h-indazol-6-ylamino)-n-[4-[(1s)-1-(propan-2-ylamino)ethyl]phenyl]pyridine-3-carboxamide Chemical compound C1=CC([C@H](C)NC(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 FJXCUBSPQFMYKH-INIZCTEOSA-N 0.000 description 1
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
• TXQPXJKRNHJWAX-UHFFFAOYSA-N 2-(3-aminopropylamino)ethylsulfanylphosphonic acid;trihydrate Chemical compound O.O.O.NCCCNCCSP(O)(O)=O TXQPXJKRNHJWAX-UHFFFAOYSA-N 0.000 description 1
• LAINPTZBIXYTIZ-UHFFFAOYSA-N 2-(3-hydroxy-2,4,5,7-tetraiodo-6-oxo-9-xanthenyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C21 LAINPTZBIXYTIZ-UHFFFAOYSA-N 0.000 description 1
• RYKAUSMIMDUSLQ-UHFFFAOYSA-N 2-(cyclopropylamino)-n-(2-methoxy-4-methylpyridin-3-yl)pyridine-3-carboxamide Chemical compound COC1=NC=CC(C)=C1NC(=O)C1=CC=CN=C1NC1CC1 RYKAUSMIMDUSLQ-UHFFFAOYSA-N 0.000 description 1
• UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 1
• HGLRIYIVJRXBQM-UHFFFAOYSA-N 2-[2-[amino-[bis(2-chloroethyl)amino]phosphoryl]oxyethyl]-1,3-thiazinane-4-carboxylic acid Chemical compound ClCCN(CCCl)P(=O)(N)OCCC1NC(C(O)=O)CCS1 HGLRIYIVJRXBQM-UHFFFAOYSA-N 0.000 description 1
• JSPUCPNQXKTYRO-LWILDLIXSA-N 2-[[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]benzene-1,4-diol Chemical compound C([C@@]1(C)[C@H]2[C@](C(=CCC2)C)(C)CC[C@@H]1C)C1=CC(O)=CC=C1O JSPUCPNQXKTYRO-LWILDLIXSA-N 0.000 description 1
• PBUUPFTVAPUWDE-UGZDLDLSSA-N 2-[[(2S,4S)-2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2lambda5-oxazaphosphinan-4-yl]sulfanyl]ethanesulfonic acid Chemical compound OS(=O)(=O)CCS[C@H]1CCO[P@](=O)(N(CCCl)CCCl)N1 PBUUPFTVAPUWDE-UGZDLDLSSA-N 0.000 description 1
• RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 description 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
• OCLZPNCLRLDXJC-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)O1 OCLZPNCLRLDXJC-NTSWFWBYSA-N 0.000 description 1
• ARCHKMRCNMSPDH-UHFFFAOYSA-N 2-amino-n-pyridin-4-ylbenzamide Chemical class NC1=CC=CC=C1C(=O)NC1=CC=NC=C1 ARCHKMRCNMSPDH-UHFFFAOYSA-N 0.000 description 1
• HTPCDVLWYUXWQR-UHFFFAOYSA-N 2-aminopyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1N HTPCDVLWYUXWQR-UHFFFAOYSA-N 0.000 description 1
• QRXBTPFMCTXCRD-UHFFFAOYSA-N 2-chloropyridine-4-carbonitrile Chemical compound ClC1=CC(C#N)=CC=N1 QRXBTPFMCTXCRD-UHFFFAOYSA-N 0.000 description 1
• MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
• JVHBILBNECDYIY-UHFFFAOYSA-N 2-fluoropyridine-3-carbonyl chloride Chemical compound FC1=NC=CC=C1C(Cl)=O JVHBILBNECDYIY-UHFFFAOYSA-N 0.000 description 1
• GRCLBOGXTPXNPL-UHFFFAOYSA-N 2-fluoropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1F GRCLBOGXTPXNPL-UHFFFAOYSA-N 0.000 description 1
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
• GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 1
• RBFPKTBMLPIPMA-UHFFFAOYSA-N 2-methyl-n-phenylacridin-1-amine Chemical compound CC1=CC=C2N=C3C=CC=CC3=CC2=C1NC1=CC=CC=C1 RBFPKTBMLPIPMA-UHFFFAOYSA-N 0.000 description 1
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
• HCGYMSSYSAKGPK-UHFFFAOYSA-N 2-nitro-1h-indole Chemical compound C1=CC=C2NC([N+](=O)[O-])=CC2=C1 HCGYMSSYSAKGPK-UHFFFAOYSA-N 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
• OBRVKOVWGSBITQ-UHFFFAOYSA-N 3,3-dimethyl-6-nitro-1,2-dihydroindole Chemical compound [O-][N+](=O)C1=CC=C2C(C)(C)CNC2=C1 OBRVKOVWGSBITQ-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
• UKVFKRGLLNSVNJ-UHFFFAOYSA-L 3,5-dichloro-4-[1,2-diamino-2-(2,6-dichloro-4-hydroxyphenyl)ethyl]phenol;platinum(2+);sulfate;dihydrate Chemical compound O.O.[Pt+2].[O-]S([O-])(=O)=O.ClC=1C=C(O)C=C(Cl)C=1C(N)C(N)C1=C(Cl)C=C(O)C=C1Cl UKVFKRGLLNSVNJ-UHFFFAOYSA-L 0.000 description 1
• HQLHJCFATKAUSO-UHFFFAOYSA-N 3,7-dihydroxytropolone Chemical compound OC1=CC=CC(=O)C(O)=C1O HQLHJCFATKAUSO-UHFFFAOYSA-N 0.000 description 1
• PLZGLOKFYWUNFJ-UHFFFAOYSA-N 3-(1h-indazol-3-yloxy)-1h-indazole Chemical class C1=CC=C2C(OC=3C4=CC=CC=C4NN=3)=NNC2=C1 PLZGLOKFYWUNFJ-UHFFFAOYSA-N 0.000 description 1
• ICBQXEWYZVQCFH-UHFFFAOYSA-N 3-(4-bromoanilino)-n,n-dimethylpropanamide Chemical compound CN(C)C(=O)CCNC1=CC=C(Br)C=C1 ICBQXEWYZVQCFH-UHFFFAOYSA-N 0.000 description 1
• IOSAAWHGJUZBOG-UHFFFAOYSA-N 3-(6-amino-9h-purin-9-yl)nonan-2-ol Chemical compound N1=CN=C2N(C(C(C)O)CCCCCC)C=NC2=C1N IOSAAWHGJUZBOG-UHFFFAOYSA-N 0.000 description 1
• PWMYMKOUNYTVQN-UHFFFAOYSA-N 3-(8,8-diethyl-2-aza-8-germaspiro[4.5]decan-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C[Ge](CC)(CC)CCC11CN(CCCN(C)C)CC1 PWMYMKOUNYTVQN-UHFFFAOYSA-N 0.000 description 1
• OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
• IJOXANMNOBNNDX-UHFFFAOYSA-N 3-[(6-amino-1h-indazol-3-yl)oxy]-1h-indazol-6-amine Chemical compound NC1=CC=C2C(OC=3C4=CC=C(C=C4NN=3)N)=NNC2=C1 IJOXANMNOBNNDX-UHFFFAOYSA-N 0.000 description 1
• QNKJFXARIMSDBR-UHFFFAOYSA-N 3-[2-[bis(2-chloroethyl)amino]ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound O=C1N(CCN(CCCl)CCCl)C(=O)NC11CCCCC1 QNKJFXARIMSDBR-UHFFFAOYSA-N 0.000 description 1
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
• WUIABRMSWOKTOF-OYALTWQYSA-N 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS([O-])(=O)=O.N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C WUIABRMSWOKTOF-OYALTWQYSA-N 0.000 description 1
• USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
• ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical class N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
• OWIRCRREDNEXTA-UHFFFAOYSA-N 3-nitro-1h-indazole Chemical compound C1=CC=C2C([N+](=O)[O-])=NNC2=C1 OWIRCRREDNEXTA-UHFFFAOYSA-N 0.000 description 1
• GEALTJGFPPNOJE-UHFFFAOYSA-N 3-nitro-2-phenylpyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1C1=CC=CC=C1 GEALTJGFPPNOJE-UHFFFAOYSA-N 0.000 description 1
• PDQGEKGUTOTUNV-TZSSRYMLSA-N 4'-deoxy-4'-iododoxorubicin 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](I)[C@H](C)O1 PDQGEKGUTOTUNV-TZSSRYMLSA-N 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• JARCFMKMOFFIGZ-UHFFFAOYSA-N 4,6-dioxo-n-phenyl-2-sulfanylidene-1,3-diazinane-5-carboxamide Chemical compound O=C1NC(=S)NC(=O)C1C(=O)NC1=CC=CC=C1 JARCFMKMOFFIGZ-UHFFFAOYSA-N 0.000 description 1
• ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
• WFWMIUSHSIJAKH-DBRKOABJSA-N 4-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-oxido-1,2,4-triazin-1-ium-3-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=[N+]([O-])C=C1 WFWMIUSHSIJAKH-DBRKOABJSA-N 0.000 description 1
• YIMDLWDNDGKDTJ-ABYLTEMBSA-N 4-[(2s,3s,4s)-3-hydroxy-2-methyl-6-[[(1s,3s)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1h-tetracen-1-yl]oxy]oxan-4-yl]morpholine-3-carbonitrile Chemical compound N1([C@H]2CC(O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1C#N YIMDLWDNDGKDTJ-ABYLTEMBSA-N 0.000 description 1
• QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
• HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
• 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
• AKJHMTWEGVYYSE-FXILSDISSA-N 4-hydroxyphenyl retinamide Chemical compound C=1C=C(O)C=CC=1NC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-FXILSDISSA-N 0.000 description 1
• CSFIQHZIFKIQNO-UHFFFAOYSA-N 4-pyrazol-1-ylaniline Chemical class C1=CC(N)=CC=C1N1N=CC=C1 CSFIQHZIFKIQNO-UHFFFAOYSA-N 0.000 description 1
• NUFNKYNBZYIQDG-UHFFFAOYSA-N 5-[4-[benzyl(methyl)amino]-3-nitrophenyl]-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1C(C=C1[N+]([O-])=O)=CC=C1N(C)CC1=CC=CC=C1 NUFNKYNBZYIQDG-UHFFFAOYSA-N 0.000 description 1
• GYXOTADLHQJPIP-UHFFFAOYSA-N 5-bromo-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=CNC1=O GYXOTADLHQJPIP-UHFFFAOYSA-N 0.000 description 1
• WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 1
• UEWSIIBPZOBMBL-UHFFFAOYSA-N 5-hydroxyimidazole-4-carboxamide Chemical compound NC(=O)C1=C([O-])[NH2+]C=N1 UEWSIIBPZOBMBL-UHFFFAOYSA-N 0.000 description 1
• OZFPSOBLQZPIAV-UHFFFAOYSA-N 5-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=C2NC=CC2=C1 OZFPSOBLQZPIAV-UHFFFAOYSA-N 0.000 description 1
• SCUPIRGJNHINID-UHFFFAOYSA-N 5-o-[2-[benzyl(methyl)amino]ethyl] 3-o-methyl 2,6-dimethyl-4-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)C1=NN2C=CC=CC2=C1C1C(C(=O)OC)=C(C)NC(C)=C1C(=O)OCCN(C)CC1=CC=CC=C1 SCUPIRGJNHINID-UHFFFAOYSA-N 0.000 description 1
• MMRCWWRFYLZGAE-ZBZRSYSASA-N 533u947v6q Chemical compound O([C@]12[C@H](OC(C)=O)[C@]3(CC)C=CCN4CC[C@@]5([C@H]34)[C@H]1N(C)C1=C5C=C(C(=C1)OC)[C@]1(C(=O)OC)C3=C(C4=CC=CC=C4N3)CCN3C[C@H](C1)C[C@@](C3)(O)CC)C(=O)N(CCCl)C2=O MMRCWWRFYLZGAE-ZBZRSYSASA-N 0.000 description 1
• ATCGGEJZONJOCL-UHFFFAOYSA-N 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Cl)C=2)Cl)=N1 ATCGGEJZONJOCL-UHFFFAOYSA-N 0.000 description 1
• VJXSSYDSOJBUAV-UHFFFAOYSA-N 6-(2,5-dimethoxy-benzyl)-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound COC1=CC=C(OC)C(CC=2C(=C3C(N)=NC(N)=NC3=NC=2)C)=C1 VJXSSYDSOJBUAV-UHFFFAOYSA-N 0.000 description 1
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
• MRFRLYAOBSTHHU-MVNLRXSJSA-N 6-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydro-1,3,5-triazin-2-one;hydrochloride Chemical compound Cl.C1NC(N)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 MRFRLYAOBSTHHU-MVNLRXSJSA-N 0.000 description 1
• ORZRMRUXSPNQQL-UHFFFAOYSA-N 6-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC=C2C=NNC2=C1 ORZRMRUXSPNQQL-UHFFFAOYSA-N 0.000 description 1
• PQMIPLRIRFVQJZ-QBYYVRQOSA-N 7-[2-[(2s,4s)-4-[(2r,3r,4r,5s,6s)-3-fluoro-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethoxy]-7-oxoheptanoic acid 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)COC(=O)CCCCCC(O)=O)[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]1F PQMIPLRIRFVQJZ-QBYYVRQOSA-N 0.000 description 1
• CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical class C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 description 1
• PBCZSGKMGDDXIJ-HQCWYSJUSA-N 7-hydroxystaurosporine Chemical compound N([C@H](O)C1=C2C3=CC=CC=C3N3C2=C24)C(=O)C1=C2C1=CC=CC=C1N4[C@H]1C[C@@H](NC)[C@@H](OC)[C@]3(C)O1 PBCZSGKMGDDXIJ-HQCWYSJUSA-N 0.000 description 1
• QJSWPNBVJSANQK-UHFFFAOYSA-N 7-nitro-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1CNC(=O)C2=CC([N+](=O)[O-])=CC=C21 QJSWPNBVJSANQK-UHFFFAOYSA-N 0.000 description 1
• GOJJWDOZNKBUSR-UHFFFAOYSA-N 7-sulfamoyloxyheptyl sulfamate Chemical compound NS(=O)(=O)OCCCCCCCOS(N)(=O)=O GOJJWDOZNKBUSR-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• PBCZSGKMGDDXIJ-UHFFFAOYSA-N 7beta-hydroxystaurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3C(O)NC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 PBCZSGKMGDDXIJ-UHFFFAOYSA-N 0.000 description 1
• SRIOCKJKFXAKHK-UHFFFAOYSA-N 8-amino-10h-isoindolo[1,2-b]quinazolin-12-one Chemical compound C1=CC=C2C3=NC4=CC=C(N)C=C4CN3C(=O)C2=C1 SRIOCKJKFXAKHK-UHFFFAOYSA-N 0.000 description 1
• ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 1
• OWWBUEMWTMDEBK-UHFFFAOYSA-N 9-acetyl-7-[4-amino-5-[3-hydroxy-1-(3-hydroxy-5-oxohexan-2-yl)oxybutoxy]-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O1C(C)C(OC(OC(C)C(O)CC(C)=O)CC(O)C)C(N)CC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 OWWBUEMWTMDEBK-UHFFFAOYSA-N 0.000 description 1
• SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• PBZVIYIWLYRXNM-ZGRMKTROSA-N Acanthifolicin Chemical compound O([C@@]12[C@@H]3S[C@]3(C)C[C@H](O2)[C@H](C)/C=C/[C@H]2CC[C@@]3(CC[C@H]4O[C@@H](C([C@@H](O)[C@@H]4O3)=C)C(O)C[C@H](C)[C@@H]3[C@@H](CC[C@@]4(OCCCC4)O3)C)O2)[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]1O PBZVIYIWLYRXNM-ZGRMKTROSA-N 0.000 description 1
• 229930191984 Actinoplanone Natural products 0.000 description 1
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
• QMGUSPDJTPDFSF-UHFFFAOYSA-N Aldophosphamide Chemical class ClCCN(CCCl)P(=O)(N)OCCC=O QMGUSPDJTPDFSF-UHFFFAOYSA-N 0.000 description 1
• 201000004384 Alopecia Diseases 0.000 description 1
• 244000144725 Amygdalus communis Species 0.000 description 1
• 235000011437 Amygdalus communis Nutrition 0.000 description 1
• 206010002198 Anaphylactic reaction Diseases 0.000 description 1
• 208000003120 Angiofibroma Diseases 0.000 description 1
• 108010029748 Angiostat Proteins 0.000 description 1
• AQBUFJBHZGRZRV-UHFFFAOYSA-N Ankinomycin Natural products CC1OC1C1C(C=2OC3=C4C(=O)C5=C(O)C(C6OC(C)C(O)C(C)(C6)N(C)C)=CC=C5C(=O)C4=CC(C)=C3C(=O)C=2)(C)O1 AQBUFJBHZGRZRV-UHFFFAOYSA-N 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• TYGJUQYJMIOZLZ-VTYVZKAMSA-N Antibiotic BU 2867TA Natural products O=C(N[C@H]1C(=O)N[C@@H](C)/C=C\C(=O)NCC[C@@H](O)C1)[C@@H](NC(=O)/C=C/C=C\CCCCCCC)[C@@H](O)C TYGJUQYJMIOZLZ-VTYVZKAMSA-N 0.000 description 1
• OSEDIRANPWGFRX-BONVTDFDSA-N Antibiotic DOB 41 Natural products O([C@@H](C)c1c2nc3c(c(C(=O)O)ccc3)nc2ccc1)C(=O)[C@@H](OC)CO OSEDIRANPWGFRX-BONVTDFDSA-N 0.000 description 1
• 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
• 101100397240 Arabidopsis thaliana ISPD gene Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 206010003445 Ascites Diseases 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 208000003950 B-cell lymphoma Diseases 0.000 description 1
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
• WOVKYSAHUYNSMH-UHFFFAOYSA-N BROMODEOXYURIDINE Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-UHFFFAOYSA-N 0.000 description 1
• GTHQOPUWLHFKFZ-NNUXYFOWSA-N Baccharin Natural products CC(O)C1OCC(O)C2(C)OC2C(=O)OCC34CCC5(C)OC5C3OC6CC(OC(=O)C=C/C=C/1)C4C6=O GTHQOPUWLHFKFZ-NNUXYFOWSA-N 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• ZOXJGFHDIHLPTG-BJUDXGSMSA-N Boron-10 Chemical compound [10B] ZOXJGFHDIHLPTG-BJUDXGSMSA-N 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 206010006811 Bursitis Diseases 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• DGGZCXUXASNDAC-QQNGCVSVSA-N C-1027 chromophore Chemical compound COc1cc2OC(=C)C(=O)Nc2c(c1)C(=O)O[C@H]3COC(=O)C[C@H](N)c4cc(O)c(O[C@@H]5C#C\C=C\3/C#CC6=CC=C[C@]56O[C@@H]7OC(C)(C)[C@H]([C@@H](O)[C@H]7O)N(C)C)c(Cl)c4 DGGZCXUXASNDAC-QQNGCVSVSA-N 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• 101100439046 Caenorhabditis elegans cdk-2 gene Proteins 0.000 description 1
• 101100495314 Caenorhabditis elegans cdk-5 gene Proteins 0.000 description 1
• 108090000312 Calcium Channels Proteins 0.000 description 1
• 102000003922 Calcium Channels Human genes 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
• ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 description 1
• QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
• 102000011022 Chorionic Gonadotropin Human genes 0.000 description 1
• 108010062540 Chorionic Gonadotropin Proteins 0.000 description 1
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
• 241000723346 Cinnamomum camphora Species 0.000 description 1
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
• RNZAEKUSZHXFMR-UHFFFAOYSA-N Cl.Cl.Cl.S1C2=CC(O)=CC=C2C2=NN(CCN(CC)CC)C3=C2C1=C(NCCN)C=C3 Chemical compound Cl.Cl.Cl.S1C2=CC(O)=CC=C2C2=NN(CCN(CC)CC)C3=C2C1=C(NCCN)C=C3 RNZAEKUSZHXFMR-UHFFFAOYSA-N 0.000 description 1
• ZDJRSUWWMAYYID-ZXHXBDCOSA-N Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@]([C@@H](C3=C(O)C=4C(=O)C5=CC=CC(O)=C5C(=O)C=4C(O)=C32)O)(O)CC)CCOCC1 Chemical compound Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@]([C@@H](C3=C(O)C=4C(=O)C5=CC=CC(O)=C5C(=O)C=4C(O)=C32)O)(O)CC)CCOCC1 ZDJRSUWWMAYYID-ZXHXBDCOSA-N 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
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 229940126657 Compound 17 Drugs 0.000 description 1
• 206010010741 Conjunctivitis Diseases 0.000 description 1
• 239000005749 Copper compound Substances 0.000 description 1
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
• 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 description 1
• 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 1
• 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 description 1
• 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 description 1
• 102100023263 Cyclin-dependent kinase 10 Human genes 0.000 description 1
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
• 102100036329 Cyclin-dependent kinase 3 Human genes 0.000 description 1
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
• 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 1
• 102100026810 Cyclin-dependent kinase 7 Human genes 0.000 description 1
• 102100024456 Cyclin-dependent kinase 8 Human genes 0.000 description 1
• 102100024457 Cyclin-dependent kinase 9 Human genes 0.000 description 1
• 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 239000012624 DNA alkylating agent Substances 0.000 description 1
• 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
• 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
• 101100481408 Danio rerio tie2 gene Proteins 0.000 description 1
• 101100314281 Danio rerio trappc11 gene Proteins 0.000 description 1
• 206010054044 Diabetic microangiopathy Diseases 0.000 description 1
• 206010051392 Diapedesis Diseases 0.000 description 1
• 206010012735 Diarrhoea Diseases 0.000 description 1
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
• GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 1
• MUVMZSPKUBTGDH-UHFFFAOYSA-N Ditrisarubicin B Natural products O1C2CC(=O)C(C)OC2OC(C(C)O2)C1CC2OC(C(C)O1)C(N(C)C)CC1OC1C2=C(O)C(C(=O)C3=CC=CC(O)=C3C3=O)=C3C(O)=C2C(OC2OC(C)C(OC3OC(C)C4OC5OC(C)C(=O)CC5OC4C3)C(C2)N(C)C)CC1(O)CC MUVMZSPKUBTGDH-UHFFFAOYSA-N 0.000 description 1
• 101100066566 Drosophila melanogaster FER gene Proteins 0.000 description 1
• 208000016974 Eales' disease Diseases 0.000 description 1
• 206010063045 Effusion Diseases 0.000 description 1
• MGQRRMONVLMKJL-UHFFFAOYSA-N Elsamicin A Natural products O1C(C)C(O)C(OC)C(N)C1OC1C(O)(C)C(O)C(C)OC1OC1=CC=CC2=C(O)C(C(O3)=O)=C4C5=C3C=CC(C)=C5C(=O)OC4=C12 MGQRRMONVLMKJL-UHFFFAOYSA-N 0.000 description 1
• HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• 101150036586 FES gene Proteins 0.000 description 1
• 101150017750 FGFRL1 gene Proteins 0.000 description 1
• 101150106356 FPS gene Proteins 0.000 description 1
• 229940123583 Factor Xa inhibitor Drugs 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 101150040897 Fgr gene Proteins 0.000 description 1
• 102000009123 Fibrin Human genes 0.000 description 1
• 108010073385 Fibrin Proteins 0.000 description 1
• BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
• 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 description 1
• 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 description 1
• 102100023600 Fibroblast growth factor receptor 2 Human genes 0.000 description 1
• 101710182389 Fibroblast growth factor receptor 2 Proteins 0.000 description 1
• 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 description 1
• 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 description 1
• 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 description 1
• 102100026149 Fibroblast growth factor receptor-like 1 Human genes 0.000 description 1
• 201000008808 Fibrosarcoma Diseases 0.000 description 1
• WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 1
• VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
• 102400000921 Gastrin Human genes 0.000 description 1
• ZPLQIPFOCGIIHV-UHFFFAOYSA-N Gimeracil Chemical compound OC1=CC(=O)C(Cl)=CN1 ZPLQIPFOCGIIHV-UHFFFAOYSA-N 0.000 description 1
• 102100033299 Glia-derived nexin Human genes 0.000 description 1
• LLEUXCDZPQOJMY-AAEUAGOBSA-N Glu-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CCC(O)=O)N)C(O)=O)=CNC2=C1 LLEUXCDZPQOJMY-AAEUAGOBSA-N 0.000 description 1
• 108090000288 Glycoproteins Proteins 0.000 description 1
• 102000003886 Glycoproteins Human genes 0.000 description 1
• 206010018498 Goitre Diseases 0.000 description 1
• 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 1
• 108010069236 Goserelin Proteins 0.000 description 1
• 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
• 208000003807 Graves Disease Diseases 0.000 description 1
• 208000015023 Graves' disease Diseases 0.000 description 1
• JEMVIRAQUIJOCL-UHFFFAOYSA-N Grincamycin Natural products CC1OC(OC2C(CC(OC2C)C=2C(=C3C(=O)C4=C(C5(C(=O)CC(C)(CC5(O)C=C4)OC4OC(C)C(OC5OC(C)C(=O)CC5)CC4)O)C(=O)C3=CC=2)O)O)CCC1OC1CCC(=O)C(C)O1 JEMVIRAQUIJOCL-UHFFFAOYSA-N 0.000 description 1
• 108010091938 HLA-B7 Antigen Proteins 0.000 description 1
• 241000589989 Helicobacter Species 0.000 description 1
• 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
• 208000031953 Hereditary hemorrhagic telangiectasia Diseases 0.000 description 1
• 208000009889 Herpes Simplex Diseases 0.000 description 1
• 208000007514 Herpes zoster Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
• 101000908138 Homo sapiens Cyclin-dependent kinase 10 Proteins 0.000 description 1
• 101000715946 Homo sapiens Cyclin-dependent kinase 3 Proteins 0.000 description 1
• 101000911952 Homo sapiens Cyclin-dependent kinase 7 Proteins 0.000 description 1
• 101000980937 Homo sapiens Cyclin-dependent kinase 8 Proteins 0.000 description 1
• 101000980930 Homo sapiens Cyclin-dependent kinase 9 Proteins 0.000 description 1
• 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 description 1
• 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 description 1
• 101000628949 Homo sapiens Mitogen-activated protein kinase 10 Proteins 0.000 description 1
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 1
• 101000878540 Homo sapiens Protein-tyrosine kinase 2-beta Proteins 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 101000922131 Homo sapiens Tyrosine-protein kinase CSK Proteins 0.000 description 1
• 206010051151 Hyperviscosity syndrome Diseases 0.000 description 1
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
• MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 1
• 102000016844 Immunoglobulin-like domains Human genes 0.000 description 1
• 108050006430 Immunoglobulin-like domains Proteins 0.000 description 1
• 108010078049 Interferon alpha-2 Proteins 0.000 description 1
• 108010079944 Interferon-alpha2b Proteins 0.000 description 1
• 102000003996 Interferon-beta Human genes 0.000 description 1
• 108090000467 Interferon-beta Proteins 0.000 description 1
• 108010074328 Interferon-gamma Proteins 0.000 description 1
• 102000008070 Interferon-gamma Human genes 0.000 description 1
• 102000003777 Interleukin-1 beta Human genes 0.000 description 1
• 108090000193 Interleukin-1 beta Proteins 0.000 description 1
• 102100030694 Interleukin-11 Human genes 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 102000000588 Interleukin-2 Human genes 0.000 description 1
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
• SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
• 208000003456 Juvenile Arthritis Diseases 0.000 description 1
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
• 229930185217 Kesarirhodin Natural products 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• AEFLONBTGZFSGQ-VKHMYHEASA-N L-isoglutamine Chemical compound NC(=O)[C@@H](N)CCC(O)=O AEFLONBTGZFSGQ-VKHMYHEASA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• 108010062867 Lenograstim Proteins 0.000 description 1
• 108010000817 Leuprolide Proteins 0.000 description 1
• HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
• 208000019693 Lung disease Diseases 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 description 1
• 206010025538 Malignant ascites Diseases 0.000 description 1
• JCYZMTMYPZHVBF-UHFFFAOYSA-N Melarsoprol Chemical compound NC1=NC(N)=NC(NC=2C=CC(=CC=2)[As]2SC(CO)CS2)=N1 JCYZMTMYPZHVBF-UHFFFAOYSA-N 0.000 description 1
• 102000029749 Microtubule Human genes 0.000 description 1
• 108091022875 Microtubule Proteins 0.000 description 1
• 102100026931 Mitogen-activated protein kinase 10 Human genes 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
• 238000006751 Mitsunobu reaction Methods 0.000 description 1
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
• 208000024599 Mooren ulcer Diseases 0.000 description 1
• 101100268066 Mus musculus Zap70 gene Proteins 0.000 description 1
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• BNQSTAOJRULKNX-UHFFFAOYSA-N N-(6-acetamidohexyl)acetamide Chemical compound CC(=O)NCCCCCCNC(C)=O BNQSTAOJRULKNX-UHFFFAOYSA-N 0.000 description 1
• QJMCKEPOKRERLN-UHFFFAOYSA-N N-3,4-tridhydroxybenzamide Chemical compound ONC(=O)C1=CC=C(O)C(O)=C1 QJMCKEPOKRERLN-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• AXDLCFOOGCNDST-UHFFFAOYSA-N N-methyl-DL-tyrosine Natural products CNC(C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-UHFFFAOYSA-N 0.000 description 1
• AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
• LYPFDBRUNKHDGX-SOGSVHMOSA-N N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 Chemical compound N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 LYPFDBRUNKHDGX-SOGSVHMOSA-N 0.000 description 1
• QVBFIXHYQRHYDW-UHFFFAOYSA-N N1N=CC2=CC=C(C=C12)NC1=NC=CC=C1C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OCCC1NCCCC1 Chemical compound N1N=CC2=CC=C(C=C12)NC1=NC=CC=C1C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OCCC1NCCCC1 QVBFIXHYQRHYDW-UHFFFAOYSA-N 0.000 description 1
• 108010021717 Nafarelin Proteins 0.000 description 1
• 206010028813 Nausea Diseases 0.000 description 1
• WPMGFKKSCCXUAK-YFZUDYRPSA-N Nbeta-acetylstreptothricin D Chemical compound NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)NCCC[C@H](NC(=O)C)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1NC1=N[C@@H]2C(=O)NC[C@@H](O)[C@H]2N1 WPMGFKKSCCXUAK-YFZUDYRPSA-N 0.000 description 1
• 229930190254 Neoenactin Natural products 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• KYRVNWMVYQXFEU-UHFFFAOYSA-N Nocodazole Chemical class C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CS1 KYRVNWMVYQXFEU-UHFFFAOYSA-N 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 108010016076 Octreotide Proteins 0.000 description 1
• 206010030113 Oedema Diseases 0.000 description 1
• 108091034117 Oligonucleotide Proteins 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 101100381429 Oryza sativa subsp. japonica BADH2 gene Proteins 0.000 description 1
• 208000010191 Osteitis Deformans Diseases 0.000 description 1
• 206010031264 Osteonecrosis Diseases 0.000 description 1
• LKBBOPGQDRPCDS-UHFFFAOYSA-N Oxaunomycin Natural products C12=C(O)C=3C(=O)C4=C(O)C=CC=C4C(=O)C=3C(O)=C2C(O)C(CC)(O)CC1OC1CC(N)C(O)C(C)O1 LKBBOPGQDRPCDS-UHFFFAOYSA-N 0.000 description 1
• 239000012826 P38 inhibitor Substances 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 101150054473 PTK2 gene Proteins 0.000 description 1
• 208000027868 Paget disease Diseases 0.000 description 1
• 229910002666 PdCl2 Inorganic materials 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• 206010034277 Pemphigoid Diseases 0.000 description 1
• 108010057150 Peplomycin Proteins 0.000 description 1
• 208000008469 Peptic Ulcer Diseases 0.000 description 1
• 208000005228 Pericardial Effusion Diseases 0.000 description 1
• RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 description 1
• KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 description 1
• 108010001014 Plasminogen Activators Proteins 0.000 description 1
• 102000001938 Plasminogen Activators Human genes 0.000 description 1
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 1
• 208000002151 Pleural effusion Diseases 0.000 description 1
• 206010036030 Polyarthritis Diseases 0.000 description 1
• 206010036049 Polycystic ovaries Diseases 0.000 description 1
• 208000037062 Polyps Diseases 0.000 description 1
• 229930187104 Porothramycin Natural products 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 102100037787 Protein-tyrosine kinase 2-beta Human genes 0.000 description 1
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
• 206010037423 Pulmonary oedema Diseases 0.000 description 1
• 206010051484 Purulent synovitis Diseases 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• 108010010225 RA VII Proteins 0.000 description 1
• AHHFEZNOXOZZQA-ZEBDFXRSSA-N Ranimustine Chemical compound CO[C@H]1O[C@H](CNC(=O)N(CCCl)N=O)[C@@H](O)[C@H](O)[C@H]1O AHHFEZNOXOZZQA-ZEBDFXRSSA-N 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 208000007660 Residual Neoplasm Diseases 0.000 description 1
• 208000007135 Retinal Neovascularization Diseases 0.000 description 1
• 206010038848 Retinal detachment Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 206010038933 Retinopathy of prematurity Diseases 0.000 description 1
• OWPCHSCAPHNHAV-UHFFFAOYSA-N Rhizoxin Natural products C1C(O)C2(C)OC2C=CC(C)C(OC(=O)C2)CC2CC2OC2C(=O)OC1C(C)C(OC)C(C)=CC=CC(C)=CC1=COC(C)=N1 OWPCHSCAPHNHAV-UHFFFAOYSA-N 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• JZVJCTVXALSTOA-UHFFFAOYSA-N Rubia akane RA-I Natural products C1=CC(OC)=CC=C1CC(N(C)C(=O)C(CO)NC(=O)C(C)NC(=O)C(N(C1=O)C)C2)C(=O)NC(C)C(=O)N(C)C1CC(C=C1)=CC=C1OC1=CC2=CC=C1O JZVJCTVXALSTOA-UHFFFAOYSA-N 0.000 description 1
• YJDYDFNKCBANTM-QCWCSKBGSA-N SDZ PSC 833 Chemical compound C\C=C\C[C@@H](C)C(=O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](C(C)C)NC1=O YJDYDFNKCBANTM-QCWCSKBGSA-N 0.000 description 1
• YQLJDECYQDRSBI-UHFFFAOYSA-N SR12813 Chemical compound CCOP(=O)(OCC)C(P(=O)(OCC)OCC)=CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YQLJDECYQDRSBI-UHFFFAOYSA-N 0.000 description 1
• 102000001332 SRC Human genes 0.000 description 1
• 108060006706 SRC Proteins 0.000 description 1
• 229910052772 Samarium Inorganic materials 0.000 description 1
• 206010039705 Scleritis Diseases 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 108010005113 Serpin E2 Proteins 0.000 description 1
• JEZZKSQFJNWDCY-UHFFFAOYSA-N Sibanomicin Natural products C1=C2C(=O)N3CC(=CCC)CC3C=NC2=CC=C1OC1OC(C)C(NC)C(C)(O)C1O JEZZKSQFJNWDCY-UHFFFAOYSA-N 0.000 description 1
• 229920000519 Sizofiran Polymers 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 239000004280 Sodium formate Substances 0.000 description 1
• 208000027073 Stargardt disease Diseases 0.000 description 1
• 208000007107 Stomach Ulcer Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 102000019197 Superoxide Dismutase Human genes 0.000 description 1
• 108010012715 Superoxide dismutase Proteins 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• 101001045447 Synechocystis sp. (strain PCC 6803 / Kazusa) Sensor histidine kinase Hik2 Proteins 0.000 description 1
• 201000009594 Systemic Scleroderma Diseases 0.000 description 1
• 206010042953 Systemic sclerosis Diseases 0.000 description 1
• 206010042971 T-cell lymphoma Diseases 0.000 description 1
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
• NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 description 1
• 102000036693 Thrombopoietin Human genes 0.000 description 1
• 108010041111 Thrombopoietin Proteins 0.000 description 1
• 108010078233 Thymalfasin Proteins 0.000 description 1
• 108010066702 Thyrotropin Alfa Proteins 0.000 description 1
• 235000011941 Tilia x europaea Nutrition 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
• 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
• 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
• 201000005485 Toxoplasmosis Diseases 0.000 description 1
• YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 108010050144 Triptorelin Pamoate Proteins 0.000 description 1
• 230000010721 Tubulin Interactions Effects 0.000 description 1
• 102100031167 Tyrosine-protein kinase CSK Human genes 0.000 description 1
• GBOGMAARMMDZGR-UHFFFAOYSA-N UNPD149280 Natural products N1C(=O)C23OC(=O)C=CC(O)CCCC(C)CC=CC3C(O)C(=C)C(C)C2C1CC1=CC=CC=C1 GBOGMAARMMDZGR-UHFFFAOYSA-N 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 206010064996 Ulcerative keratitis Diseases 0.000 description 1
• 206010046851 Uveitis Diseases 0.000 description 1
• 102000009520 Vascular Endothelial Growth Factor C Human genes 0.000 description 1
• 108010073923 Vascular Endothelial Growth Factor C Proteins 0.000 description 1
• 108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 1
• 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 description 1
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 description 1
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 description 1
• 206010053648 Vascular occlusion Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 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 1
• 208000034698 Vitreous haemorrhage Diseases 0.000 description 1
• 206010047663 Vitritis Diseases 0.000 description 1
• 206010047700 Vomiting Diseases 0.000 description 1
• JAVFSUSPBIUPLW-QEWGJZFKSA-N Withanolide Natural products O=C1[C@@H](C)[C@H](C)C[C@H]([C@@H](C)[C@@H]2[C@@]3(C)[C@H]([C@@H]4[C@@H]([C@]5(C)[C@@H](CC4)CCCC5)CC3)CC2)O1 JAVFSUSPBIUPLW-QEWGJZFKSA-N 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
• ZMQRJWIYMXZORG-GZIFKOAOSA-N [(1e,3r,4r,6r,7z,9z,11e)-3,6,13-trihydroxy-3-methyl-1-[(2s)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate Chemical compound OC/C=C/C=C\C=C/[C@H](O)C[C@@H](OP(O)(O)=O)[C@@](O)(C)\C=C\[C@@H]1CC=CC(=O)O1 ZMQRJWIYMXZORG-GZIFKOAOSA-N 0.000 description 1
• VUPBDWQPEOWRQP-RTUCOMKBSA-N [(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1S,2S)-3-[[(2R,3S)-5-[[(2S,3R)-1-[[2-[4-[4-[[4-amino-6-[3-(4-aminobutylamino)propylamino]-6-oxohexyl]carbamoyl]-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]-1-[(2S,3R,4R,5S,6S)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy-2-hydroxyethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-5-oxopentan-2-yl]amino]-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate Chemical compound C[C@@H](O)[C@H](NC(=O)C[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)c1nc(nc(N)c1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@H](O[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]1O)c1cnc[nH]1)C(=O)NC(O[C@@H]1O[C@@H](C)[C@@H](N)[C@@H](O)[C@H]1O)C(O)c1nc(cs1)-c1nc(cs1)C(=O)NCCCC(N)CC(=O)NCCCNCCCCN VUPBDWQPEOWRQP-RTUCOMKBSA-N 0.000 description 1
• LJBKHHZPVCABCX-ZYUZMQFOSA-N [(2r,3r,4r,5r)-2,5-dihydroxy-3,4-dimethoxy-6-methylsulfonyloxyhexyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)[C@@H](OC)[C@H](OC)[C@H](O)COS(C)(=O)=O LJBKHHZPVCABCX-ZYUZMQFOSA-N 0.000 description 1
• DJUWKQJNJVMFIU-IHAUNJBESA-N [(2r,3r,4s,5r)-3,4,5-triacetyloxy-6-[bis(2-chloroethyl)amino]oxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC(N(CCCl)CCCl)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O DJUWKQJNJVMFIU-IHAUNJBESA-N 0.000 description 1
• YJHYHDSHHWKEIS-CJUKMMNNSA-N [(4S,6S,7R,8S)-11-(2-hydroxyethoxy)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate Chemical compound CO[C@]12[C@H]3N[C@H]3CN1C1=C([C@H]2COC(N)=O)C(=O)C(OCCO)=C(C)C1=O YJHYHDSHHWKEIS-CJUKMMNNSA-N 0.000 description 1
• IFJUINDAXYAPTO-UUBSBJJBSA-N [(8r,9s,13s,14s,17s)-17-[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4OC(=O)COC(=O)CCCC=1C=CC(=CC=1)N(CCCl)CCCl)C)CC2=CC=3OC(=O)C1=CC=CC=C1 IFJUINDAXYAPTO-UUBSBJJBSA-N 0.000 description 1
• ZUIGQZNTMIGKHP-UHFFFAOYSA-N [1-methyl-5-(methylcarbamoyloxymethyl)-2-methylsulfanylimidazol-4-yl]methyl n-methylcarbamate;hydrochloride Chemical compound Cl.CNC(=O)OCC=1N=C(SC)N(C)C=1COC(=O)NC ZUIGQZNTMIGKHP-UHFFFAOYSA-N 0.000 description 1
• XSMVECZRZBFTIZ-UHFFFAOYSA-M [2-(aminomethyl)cyclobutyl]methanamine;2-oxidopropanoate;platinum(4+) Chemical compound [Pt+4].CC([O-])C([O-])=O.NCC1CCC1CN XSMVECZRZBFTIZ-UHFFFAOYSA-M 0.000 description 1
• ODEDPKNSRBCSDO-UHFFFAOYSA-N [2-(hexadecylsulfanylmethyl)-3-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCSCC(COC)COP([O-])(=O)OCC[N+](C)(C)C ODEDPKNSRBCSDO-UHFFFAOYSA-N 0.000 description 1
• MHVFYGIQJNFWGQ-UHFFFAOYSA-N [[4,6-bis[hydroxymethyl(methyl)amino]-1,3,5-triazin-2-yl]-methylamino]methanol Chemical compound OCN(C)C1=NC(N(C)CO)=NC(N(C)CO)=N1 MHVFYGIQJNFWGQ-UHFFFAOYSA-N 0.000 description 1
• JURAJLFHWXNPHG-UHFFFAOYSA-N [acetyl(methylcarbamoyl)amino] n-methylcarbamate Chemical compound CNC(=O)ON(C(C)=O)C(=O)NC JURAJLFHWXNPHG-UHFFFAOYSA-N 0.000 description 1
• FUMLKAFCVQJVEZ-UHFFFAOYSA-N [bromo(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Br)C1=CC=CC=C1 FUMLKAFCVQJVEZ-UHFFFAOYSA-N 0.000 description 1
• AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
• 108010023617 abarelix Proteins 0.000 description 1
• 229960002184 abarelix Drugs 0.000 description 1
• 230000001594 aberrant effect Effects 0.000 description 1
• 229960005327 acemannan Drugs 0.000 description 1
• 150000001241 acetals Chemical group 0.000 description 1
• 150000003869 acetamides Chemical class 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 239000003929 acidic solution Substances 0.000 description 1
• 229960005339 acitretin Drugs 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• BYRVKDUQDLJUBX-JJCDCTGGSA-N adozelesin Chemical compound C1=CC=C2OC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)NC=C5C)=CC2=C1 BYRVKDUQDLJUBX-JJCDCTGGSA-N 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 229960005310 aldesleukin Drugs 0.000 description 1
• 108700025316 aldesleukin Proteins 0.000 description 1
• 229960000548 alemtuzumab Drugs 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229960001445 alitretinoin Drugs 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
• IHUNBGSDBOWDMA-AQFIFDHZSA-N all-trans-acitretin Chemical compound COC1=CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1C IHUNBGSDBOWDMA-AQFIFDHZSA-N 0.000 description 1
• 230000009285 allergic inflammation Effects 0.000 description 1
• 235000020224 almond Nutrition 0.000 description 1
• 102000013529 alpha-Fetoproteins Human genes 0.000 description 1
• 108010026331 alpha-Fetoproteins Proteins 0.000 description 1
• 239000011795 alpha-carotene Substances 0.000 description 1
• ANVAOWXLWRTKGA-HLLMEWEMSA-N alpha-carotene Natural products C(=C\C=C\C=C(/C=C/C=C(\C=C\C=1C(C)(C)CCCC=1C)/C)\C)(\C=C\C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)\C)/C ANVAOWXLWRTKGA-HLLMEWEMSA-N 0.000 description 1
• 235000003903 alpha-carotene Nutrition 0.000 description 1
• AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 1
• QVBOOBQEGOUUGN-RCBQFDQVSA-N alstonine Chemical compound C1=C[CH]C2=NC3=C(C[C@@H]4C(C(=O)OC)=CO[C@@H](C)[C@@H]4C4)[N+]4=CC=C3C2=C1 QVBOOBQEGOUUGN-RCBQFDQVSA-N 0.000 description 1
• WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 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
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 229950010949 ambamustine Drugs 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 229960001097 amifostine Drugs 0.000 description 1
• 229960002749 aminolevulinic acid Drugs 0.000 description 1
• 150000003927 aminopyridines Chemical class 0.000 description 1
• 229960002550 amrubicin Drugs 0.000 description 1
• VJZITPJGSQKZMX-XDPRQOKASA-N amrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)(N)C(=O)C)[C@H]1C[C@H](O)[C@H](O)CO1 VJZITPJGSQKZMX-XDPRQOKASA-N 0.000 description 1
• 229960001694 anagrelide Drugs 0.000 description 1
• OTBXOEAOVRKTNQ-UHFFFAOYSA-N anagrelide Chemical compound N1=C2NC(=O)CN2CC2=C(Cl)C(Cl)=CC=C21 OTBXOEAOVRKTNQ-UHFFFAOYSA-N 0.000 description 1
• 230000036783 anaphylactic response Effects 0.000 description 1
• 208000003455 anaphylaxis Diseases 0.000 description 1
• 229950001003 anaxirone Drugs 0.000 description 1
• 230000002491 angiogenic effect Effects 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 229940045799 anthracyclines and related substance Drugs 0.000 description 1
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
• 230000001430 anti-depressive effect Effects 0.000 description 1
• 230000003178 anti-diabetic effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• XVPSPMLUMQEEIU-PWLJWKHCSA-N antibiotic fr 900482 Chemical compound C1[C@H]2N[C@H]2[C@@]2(O)[C@@H](COC(=O)N)C3=C(O)C=C(C=O)C=C3N1O2 XVPSPMLUMQEEIU-PWLJWKHCSA-N 0.000 description 1
• 239000003472 antidiabetic agent Substances 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 108010005272 antineoplaston A2 Proteins 0.000 description 1
• 108010005286 antineoplaston A3 Proteins 0.000 description 1
• 108010005569 antineoplaston A5 Proteins 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
• GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• TWHSQQYCDVSBRK-UHFFFAOYSA-N asulacrine Chemical compound C12=CC=CC(C)=C2N=C2C(C(=O)NC)=CC=CC2=C1NC1=CC=C(NS(C)(=O)=O)C=C1OC TWHSQQYCDVSBRK-UHFFFAOYSA-N 0.000 description 1
• TXJPJZWNYUQWCP-UHFFFAOYSA-N avarol Natural products CC1CCC2(C)C(=CCCC2(C)C1(C)Cc3cc(O)ccc3O)C TXJPJZWNYUQWCP-UHFFFAOYSA-N 0.000 description 1
• KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 description 1
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• DGBITFNXKQHKLI-WXCPUVJDSA-N baccharin Chemical compound C([C@@]12[C@]3(C)[C@H]4C[C@H]1O[C@@H]1[C@@H]5O[C@]5(C)CC[C@@]13COC(=O)[C@H]1O[C@@]1(C)[C@@H](O)CO[C@H](\C=C\C=C/C(=O)O4)[C@H](O)C)O2 DGBITFNXKQHKLI-WXCPUVJDSA-N 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 229950006062 benzotript Drugs 0.000 description 1
• 229960002938 bexarotene Drugs 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 229950008548 bisantrene Drugs 0.000 description 1
• 108010014245 bisucaberin Proteins 0.000 description 1
• 229960004395 bleomycin sulfate Drugs 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 230000017531 blood circulation Effects 0.000 description 1
• 230000036770 blood supply Effects 0.000 description 1
• ZNDJOCJUBZZAMN-USYHLRJESA-N bmy-25067 Chemical compound C([C@@H]1N[C@@H]1[C@@]1([C@@H]2COC(N)=O)OC)N1C(C(C=1C)=O)=C2C(=O)C=1NCCSSC1=CC=C([N+]([O-])=O)C=C1 ZNDJOCJUBZZAMN-USYHLRJESA-N 0.000 description 1
• JSKFWUPVIZYJMR-UDOAKELVSA-N bmy-27557 Chemical compound O=C1N(CCN(CC)CC)C(=O)C(C2=C3[CH]C=CC(Cl)=C3NC2=C23)=C1C2=C1C=CC=C(Cl)[C]1N3[C@@H]1O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]1O JSKFWUPVIZYJMR-UDOAKELVSA-N 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• PZOHOALJQOFNTB-UHFFFAOYSA-M brequinar sodium Chemical compound [Na+].N1=C2C=CC(F)=CC2=C(C([O-])=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1F PZOHOALJQOFNTB-UHFFFAOYSA-M 0.000 description 1
• 229950001336 bromamide Drugs 0.000 description 1
• SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
• SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• 125000004799 bromophenyl group Chemical group 0.000 description 1
• 229950004398 broxuridine Drugs 0.000 description 1
• MJQUEDHRCUIRLF-TVIXENOKSA-N bryostatin 1 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-TVIXENOKSA-N 0.000 description 1
• 229960005539 bryostatin 1 Drugs 0.000 description 1
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 229960001948 caffeine Drugs 0.000 description 1
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
• 229960000846 camphor Drugs 0.000 description 1
• 229930008380 camphor Natural products 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 208000001969 capillary hemangioma Diseases 0.000 description 1
• 229950009338 caracemide Drugs 0.000 description 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
• 229960003261 carmofur Drugs 0.000 description 1
• 208000003295 carpal tunnel syndrome Diseases 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 229960000590 celecoxib Drugs 0.000 description 1
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 239000013592 cell lysate Substances 0.000 description 1
• 230000012292 cell migration Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 229950001357 celmoleukin Drugs 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 239000003874 central nervous system depressant Substances 0.000 description 1
• ORJRBJIJTSDUCG-UHFFFAOYSA-N cervinomycin a2 Chemical compound C1C2(C)OCCN2C(=O)C2=C(O)C3=C(C(=O)C4=C(OC=5C=C(C(=CC=5C4=O)OC)OC)C4=O)C4=CC=C3C=C21 ORJRBJIJTSDUCG-UHFFFAOYSA-N 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• SBNPWPIBESPSIF-MHWMIDJBSA-N cetrorelix Chemical compound C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 SBNPWPIBESPSIF-MHWMIDJBSA-N 0.000 description 1
• 229960003230 cetrorelix Drugs 0.000 description 1
• 108700008462 cetrorelix Proteins 0.000 description 1
• 229960005395 cetuximab Drugs 0.000 description 1
• JZVJCTVXALSTOA-XMPIZRASSA-N chembl1288988 Chemical compound C1=CC(OC)=CC=C1C[C@H](N(C)C(=O)[C@H](CO)NC(=O)[C@@H](C)NC(=O)[C@@H](N(C1=O)C)C2)C(=O)N[C@@H](C)C(=O)N(C)[C@H]1CC(C=C1)=CC=C1OC1=CC2=CC=C1O JZVJCTVXALSTOA-XMPIZRASSA-N 0.000 description 1
• QEWPVAOWLNMLRI-UHFFFAOYSA-N chembl203666 Chemical compound OCCNCCN1N=C2C3=C(O)C=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCCN QEWPVAOWLNMLRI-UHFFFAOYSA-N 0.000 description 1
• XASBSYHEEHVCSJ-UHFFFAOYSA-N chembl24329 Chemical compound OCCNCCN1N=C2C3=C(O)C=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNC XASBSYHEEHVCSJ-UHFFFAOYSA-N 0.000 description 1
• 230000003399 chemotactic effect Effects 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 238000009104 chemotherapy regimen Methods 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 208000023819 chronic asthma Diseases 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 230000007882 cirrhosis Effects 0.000 description 1
• 208000019425 cirrhosis of liver Diseases 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960002436 cladribine Drugs 0.000 description 1
• 229950005158 clanfenur Drugs 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 229960004022 clotrimazole Drugs 0.000 description 1
• VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 238000011284 combination treatment Methods 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 229940125844 compound 46 Drugs 0.000 description 1
• 210000002808 connective tissue Anatomy 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 150000004696 coordination complex Chemical class 0.000 description 1
• 150000001880 copper compounds Chemical class 0.000 description 1
• BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
• NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 238000011262 co‐therapy Methods 0.000 description 1
• SBRXTSOCZITGQG-UHFFFAOYSA-N crisnatol Chemical compound C1=CC=C2C(CNC(CO)(CO)C)=CC3=C(C=CC=C4)C4=CC=C3C2=C1 SBRXTSOCZITGQG-UHFFFAOYSA-N 0.000 description 1
• 229950007258 crisnatol Drugs 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 229940112669 cuprous oxide Drugs 0.000 description 1
• KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
• 150000004292 cyclic ethers Chemical class 0.000 description 1
• BVQPGVHVDXIPJF-UHFFFAOYSA-L cyclohexane-1,2-diamine;hydron;2-[(2-phosphonatoacetyl)amino]butanedioate;platinum(2+) Chemical compound [H+].[H+].[Pt+2].NC1CCCCC1N.[O-]C(=O)CC(C([O-])=O)NC(=O)CP([O-])([O-])=O BVQPGVHVDXIPJF-UHFFFAOYSA-L 0.000 description 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 208000031513 cyst Diseases 0.000 description 1
• GBOGMAARMMDZGR-TYHYBEHESA-N cytochalasin B Chemical compound C([C@H]1[C@@H]2[C@@H](C([C@@H](O)[C@@H]3/C=C/C[C@H](C)CCC[C@@H](O)/C=C/C(=O)O[C@@]23C(=O)N1)=C)C)C1=CC=CC=C1 GBOGMAARMMDZGR-TYHYBEHESA-N 0.000 description 1
• GBOGMAARMMDZGR-JREHFAHYSA-N cytochalasin B Natural products C[C@H]1CCC[C@@H](O)C=CC(=O)O[C@@]23[C@H](C=CC1)[C@H](O)C(=C)[C@@H](C)[C@@H]2[C@H](Cc4ccccc4)NC3=O GBOGMAARMMDZGR-JREHFAHYSA-N 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960002806 daclizumab Drugs 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 229960003603 decitabine Drugs 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000002939 deleterious effect Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 230000002074 deregulated effect Effects 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 201000009101 diabetic angiopathy Diseases 0.000 description 1
• 125000004663 dialkyl amino group Chemical group 0.000 description 1
• 150000008050 dialkyl sulfates Chemical class 0.000 description 1
• WVYXNIXAMZOZFK-UHFFFAOYSA-N diaziquone Chemical compound O=C1C(NC(=O)OCC)=C(N2CC2)C(=O)C(NC(=O)OCC)=C1N1CC1 WVYXNIXAMZOZFK-UHFFFAOYSA-N 0.000 description 1
• 125000006003 dichloroethyl group Chemical group 0.000 description 1
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
• 229960001259 diclofenac Drugs 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 238000009792 diffusion process Methods 0.000 description 1
• 125000006001 difluoroethyl group Chemical group 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 235000010300 dimethyl dicarbonate Nutrition 0.000 description 1
• FEDBYSNFQHOGCJ-UHFFFAOYSA-N dimethyl-[2-(7-oxobenzo[c]fluoren-5-yl)oxyethyl]azanium;chloride Chemical compound [Cl-].C12=CC=CC=C2C(OCC[NH+](C)C)=CC2=C1C1=CC=CC=C1C2=O FEDBYSNFQHOGCJ-UHFFFAOYSA-N 0.000 description 1
• 229950007388 dinalin Drugs 0.000 description 1
• GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical class CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
• PFWDHRASWSUTIA-KAFJHEIMSA-L disodium;(2s)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoate;2-phenylacetate Chemical compound [Na+].[Na+].[O-]C(=O)CC1=CC=CC=C1.NC(=O)CC[C@@H](C([O-])=O)NC(=O)CC1=CC=CC=C1 PFWDHRASWSUTIA-KAFJHEIMSA-L 0.000 description 1
• OSEDIRANPWGFRX-UHFFFAOYSA-N dob-41 Chemical compound C1=CC=C2N=C3C(C(C)OC(=O)C(CO)OC)=CC=CC3=NC2=C1C(O)=O OSEDIRANPWGFRX-UHFFFAOYSA-N 0.000 description 1
• 229960000735 docosanol Drugs 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960000413 doxercalciferol Drugs 0.000 description 1
• HKXBNHCUPKIYDM-CGMHZMFXSA-N doxercalciferol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C HKXBNHCUPKIYDM-CGMHZMFXSA-N 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• FSIRXIHZBIXHKT-MHTVFEQDSA-N edatrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CC(CC)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FSIRXIHZBIXHKT-MHTVFEQDSA-N 0.000 description 1
• 229950011461 edelfosine Drugs 0.000 description 1
• 229960001776 edrecolomab Drugs 0.000 description 1
• NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• 229960002759 eflornithine Drugs 0.000 description 1
• VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
• 229950000549 elliptinium acetate Drugs 0.000 description 1
• 229950003860 elmustine Drugs 0.000 description 1
• MGQRRMONVLMKJL-KWJIQSIXSA-N elsamitrucin Chemical compound O1[C@H](C)[C@H](O)[C@H](OC)[C@@H](N)[C@H]1O[C@@H]1[C@](O)(C)[C@@H](O)[C@@H](C)O[C@H]1OC1=CC=CC2=C(O)C(C(O3)=O)=C4C5=C3C=CC(C)=C5C(=O)OC4=C12 MGQRRMONVLMKJL-KWJIQSIXSA-N 0.000 description 1
• 230000013020 embryo development Effects 0.000 description 1
• 230000003511 endothelial effect Effects 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 description 1
• 229950010213 eniluracil Drugs 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 229930013356 epothilone Natural products 0.000 description 1
• HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 description 1
• SIHZWGODIRRSRA-ONEGZZNKSA-N erbstatin Chemical compound OC1=CC=C(O)C(\C=C\NC=O)=C1 SIHZWGODIRRSRA-ONEGZZNKSA-N 0.000 description 1
• OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
• 229960004943 ergotamine Drugs 0.000 description 1
• XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
• HCZKYJDFEPMADG-UHFFFAOYSA-N erythro-nordihydroguaiaretic acid Natural products C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 1
• 230000010437 erythropoiesis Effects 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• ITSGNOIFAJAQHJ-BMFNZSJVSA-N esorubicin 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[C@H](C)O1 ITSGNOIFAJAQHJ-BMFNZSJVSA-N 0.000 description 1
• 229950002017 esorubicin Drugs 0.000 description 1
• 229960001766 estramustine phosphate sodium Drugs 0.000 description 1
• IIUMCNJTGSMNRO-VVSKJQCTSA-L estramustine sodium phosphate Chemical compound [Na+].[Na+].ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP([O-])([O-])=O)[C@@H]4[C@@H]3CCC2=C1 IIUMCNJTGSMNRO-VVSKJQCTSA-L 0.000 description 1
• WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical compound OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 description 1
• 229950006566 etanidazole Drugs 0.000 description 1
• XPGDODOEEWLHOI-GSDHBNRESA-N ethyl (2s)-2-[[(2s)-2-[[(2s)-2-amino-3-(4-fluorophenyl)propanoyl]amino]-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)OCC)NC(=O)[C@@H](N)CC=1C=CC(F)=CC=1)C1=CC=CC(N(CCCl)CCCl)=C1 XPGDODOEEWLHOI-GSDHBNRESA-N 0.000 description 1
• GLFJQXMGTAJTGY-AVBZIYQWSA-N ethyl (2s,5s)-5-[[(2s)-2-amino-3-(4-fluorophenyl)propanoyl]amino]-6-[3-[bis(2-chloroethyl)amino]phenyl]-2-(2-methylsulfanylethyl)-4-oxohexanoate;hydrochloride Chemical compound Cl.C([C@@H](C(=O)C[C@@H](CCSC)C(=O)OCC)NC(=O)[C@@H](N)CC=1C=CC(F)=CC=1)C1=CC=CC(N(CCCl)CCCl)=C1 GLFJQXMGTAJTGY-AVBZIYQWSA-N 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• 125000005469 ethylenyl group Chemical group 0.000 description 1
• ISVXIZFUEUVXPG-UHFFFAOYSA-N etiopurpurin Chemical compound CC1C2(CC)C(C(=O)OCC)=CC(C3=NC(C(=C3C)CC)=C3)=C2N=C1C=C(N1)C(CC)=C(C)C1=CC1=C(CC)C(C)=C3N1 ISVXIZFUEUVXPG-UHFFFAOYSA-N 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 229960005420 etoposide Drugs 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
• 229960004945 etoricoxib Drugs 0.000 description 1
• MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
• HQMNCQVAMBCHCO-DJRRULDNSA-N etretinate Chemical compound CCOC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C=C(OC)C(C)=C1C HQMNCQVAMBCHCO-DJRRULDNSA-N 0.000 description 1
• 229960002199 etretinate Drugs 0.000 description 1
• 210000000416 exudates and transudate Anatomy 0.000 description 1
• NMUSYJAQQFHJEW-ARQDHWQXSA-N fazarabine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-ARQDHWQXSA-N 0.000 description 1
• 229950005096 fazarabine Drugs 0.000 description 1
• 210000004996 female reproductive system Anatomy 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 229950003499 fibrin Drugs 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
• FBXPCVIKIBWXAE-ZJZHAWLTSA-N fk973 Chemical compound O1N2C[C@@H]3N(C(C)=O)[C@@H]3[C@]1(OC(C)=O)[C@@H](COC(N)=O)C1=C2C=C(C=O)C=C1OC(=O)C FBXPCVIKIBWXAE-ZJZHAWLTSA-N 0.000 description 1
• 235000013312 flour Nutrition 0.000 description 1
• ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
• 229960000961 floxuridine Drugs 0.000 description 1
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 230000003325 follicular Effects 0.000 description 1
• OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
• 229960004421 formestane Drugs 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 229950010404 fostriecin Drugs 0.000 description 1
• 229960002258 fulvestrant Drugs 0.000 description 1
• 230000002538 fungal effect Effects 0.000 description 1
• 210000000232 gallbladder Anatomy 0.000 description 1
• 229950004410 galocitabine Drugs 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 201000005917 gastric ulcer Diseases 0.000 description 1
• 108010066264 gastrin 17 Proteins 0.000 description 1
• GKDWRERMBNGKCZ-RNXBIMIWSA-N gastrin-17 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 GKDWRERMBNGKCZ-RNXBIMIWSA-N 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• 229960000578 gemtuzumab Drugs 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• QKMXESBAFIKRAD-LPHDITAFSA-N genkwadaphnin Chemical compound O([C@@H]1[C@H]([C@@]23[C@H]4[C@](C(C(C)=C4)=O)(O)[C@H](O)[C@@]4(CO)O[C@H]4[C@H]3[C@H]3O[C@](O2)(O[C@]31C(C)=C)C=1C=CC=CC=1)C)C(=O)C1=CC=CC=C1 QKMXESBAFIKRAD-LPHDITAFSA-N 0.000 description 1
• QKMXESBAFIKRAD-UHFFFAOYSA-N genkwadaphnin Natural products CC(=C)C12OC(O3)(C=4C=CC=CC=4)OC1C1C4OC4(CO)C(O)C(C(C(C)=C4)=O)(O)C4C31C(C)C2OC(=O)C1=CC=CC=C1 QKMXESBAFIKRAD-UHFFFAOYSA-N 0.000 description 1
• 229950009822 gimeracil Drugs 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 229930189446 glidobactin Natural products 0.000 description 1
• 229960002913 goserelin Drugs 0.000 description 1
• 239000003119 guanylate cyclase activator Substances 0.000 description 1
• 210000002768 hair cell Anatomy 0.000 description 1
• 208000024963 hair loss Diseases 0.000 description 1
• 230000003676 hair loss Effects 0.000 description 1
• 150000003944 halohydrins Chemical class 0.000 description 1
• 201000002222 hemangioblastoma Diseases 0.000 description 1
• 230000009033 hematopoietic malignancy Effects 0.000 description 1
• 229960002897 heparin Drugs 0.000 description 1
• 229920000669 heparin Polymers 0.000 description 1
• 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
• MCAHMSDENAOJFZ-BVXDHVRPSA-N herbimycin 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](OC)[C@@H](OC)C[C@H](C)[C@@H](OC)C2=CC(=O)C=C1C2=O MCAHMSDENAOJFZ-BVXDHVRPSA-N 0.000 description 1
• 229930193320 herbimycin Natural products 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
• 229960004931 histamine dihydrochloride Drugs 0.000 description 1
• HYFHYPWGAURHIV-UHFFFAOYSA-N homoharringtonine Natural products C1=C2CCN3CCCC43C=C(OC)C(OC(=O)C(O)(CCCC(C)(C)O)CC(=O)OC)C4C2=CC2=C1OCO2 HYFHYPWGAURHIV-UHFFFAOYSA-N 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 229940084986 human chorionic gonadotropin Drugs 0.000 description 1
• 208000013653 hyalitis Diseases 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000003463 hyperproliferative effect Effects 0.000 description 1
• 229960005236 ibandronic acid Drugs 0.000 description 1
• 229960001001 ibritumomab tiuxetan Drugs 0.000 description 1
• 229960001101 ifosfamide Drugs 0.000 description 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
• 229930190064 illudin Natural products 0.000 description 1
• 229950006905 ilmofosine Drugs 0.000 description 1
• NITYDPDXAAFEIT-DYVFJYSZSA-N ilomastat Chemical compound C1=CC=C2C(C[C@@H](C(=O)NC)NC(=O)[C@H](CC(C)C)CC(=O)NO)=CNC2=C1 NITYDPDXAAFEIT-DYVFJYSZSA-N 0.000 description 1
• 229960003696 ilomastat Drugs 0.000 description 1
• 150000002460 imidazoles Chemical class 0.000 description 1
• 150000002462 imidazolines Chemical class 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 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 1
• 229960002751 imiquimod Drugs 0.000 description 1
• 230000002163 immunogen Effects 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 150000002468 indanes Chemical class 0.000 description 1
• 150000002473 indoazoles Chemical class 0.000 description 1
• 150000002475 indoles Chemical class 0.000 description 1
• 150000002476 indolines Chemical class 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
• 239000011261 inert gas Substances 0.000 description 1
• 238000003780 insertion Methods 0.000 description 1
• 230000037431 insertion Effects 0.000 description 1
• 239000000138 intercalating agent Substances 0.000 description 1
• 229960003130 interferon gamma Drugs 0.000 description 1
• 108010042414 interferon gamma-1b Proteins 0.000 description 1
• 229940028862 interferon gamma-1b Drugs 0.000 description 1
• 229960001388 interferon-beta Drugs 0.000 description 1
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 229950010897 iproplatin Drugs 0.000 description 1
• 229960004768 irinotecan Drugs 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 229960005280 isotretinoin Drugs 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• BIOSTZMAOGCGSC-CYUGEGSCSA-N kt6149 Chemical compound C1N2C(C(C(C)=C(NCCSSCCNC(=O)CC[C@H](N)C(O)=O)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 BIOSTZMAOGCGSC-CYUGEGSCSA-N 0.000 description 1
• 108010021336 lanreotide Proteins 0.000 description 1
• 229960002437 lanreotide Drugs 0.000 description 1
• 229960000681 leflunomide Drugs 0.000 description 1
• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 1
• 229960002618 lenograstim Drugs 0.000 description 1
• 108010030727 lens intermediate filament proteins Proteins 0.000 description 1
• HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
• 229960003881 letrozole Drugs 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 108010002060 leukoregulin Proteins 0.000 description 1
• 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 1
• 229960004338 leuprorelin Drugs 0.000 description 1
• 229960001614 levamisole Drugs 0.000 description 1
• UGFHIPBXIWJXNA-UHFFFAOYSA-N liarozole Chemical compound ClC1=CC=CC(C(C=2C=C3NC=NC3=CC=2)N2C=NC=C2)=C1 UGFHIPBXIWJXNA-UHFFFAOYSA-N 0.000 description 1
• 229950007056 liarozole Drugs 0.000 description 1
• 229960005535 lidamycin Drugs 0.000 description 1
• 239000004571 lime Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 229950008991 lobaplatin Drugs 0.000 description 1
• 229960002247 lomustine Drugs 0.000 description 1
• WDRYRZXSPDWGEB-UHFFFAOYSA-N lonidamine Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Cl)C=C1Cl WDRYRZXSPDWGEB-UHFFFAOYSA-N 0.000 description 1
• 229960003538 lonidamine Drugs 0.000 description 1
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
• 229960004844 lovastatin Drugs 0.000 description 1
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 210000005265 lung cell Anatomy 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 229920002521 macromolecule Polymers 0.000 description 1
• 229950000547 mafosfamide Drugs 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 208000027202 mammary Paget disease Diseases 0.000 description 1
• OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 1
• 229950008959 marimastat Drugs 0.000 description 1
• 229960003951 masoprocol Drugs 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 231100000682 maximum tolerated dose Toxicity 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 229960001728 melarsoprol Drugs 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
• AZVARJHZBXHUSO-DZQVEHCYSA-N methyl (1R,4R,12S)-4-methyl-3,7-dioxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)N[C@@](C5=O)(C)C(=O)OC)=CC2=C1 AZVARJHZBXHUSO-DZQVEHCYSA-N 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
• 229960004503 metoclopramide Drugs 0.000 description 1
• 210000004688 microtubule Anatomy 0.000 description 1
• VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 1
• 229960003248 mifepristone Drugs 0.000 description 1
• 108010087673 minactivin Proteins 0.000 description 1
• CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 229950010913 mitolactol Drugs 0.000 description 1
• VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 229960001156 mitoxantrone Drugs 0.000 description 1
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
• 229950003063 mitumomab Drugs 0.000 description 1
• 108010032806 molgramostim Proteins 0.000 description 1
• 229960003063 molgramostim Drugs 0.000 description 1
• 210000001616 monocyte Anatomy 0.000 description 1
• AARXZCZYLAFQQU-UHFFFAOYSA-N motexafin gadolinium Chemical compound [Gd].CC(O)=O.CC(O)=O.C1=C([N-]2)C(CC)=C(CC)C2=CC(C(=C2C)CCCO)=NC2=CN=C2C=C(OCCOCCOCCOC)C(OCCOCCOCCOC)=CC2=NC=C2C(C)=C(CCCO)C1=N2 AARXZCZYLAFQQU-UHFFFAOYSA-N 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 208000001491 myopia Diseases 0.000 description 1
• 230000004379 myopia Effects 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• HRKICRHARITSQS-UHFFFAOYSA-N n'-(3-aminopropyl)propane-1,3-diamine;trihydrochloride Chemical compound Cl.Cl.Cl.NCCCNCCCN HRKICRHARITSQS-UHFFFAOYSA-N 0.000 description 1
• ZJVAVRRLTFVZIP-UHFFFAOYSA-N n-(2-bromoethyl)-3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound ClCCN1CCCOP1(=O)NCCBr ZJVAVRRLTFVZIP-UHFFFAOYSA-N 0.000 description 1
• QMXHLXCMKLSGGF-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 QMXHLXCMKLSGGF-UHFFFAOYSA-N 0.000 description 1
• RERMEPXRRTZYFB-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 RERMEPXRRTZYFB-UHFFFAOYSA-N 0.000 description 1
• MJISPJQLWXETRE-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=N1 MJISPJQLWXETRE-UHFFFAOYSA-N 0.000 description 1
• OQGRFQCUGLKSAV-JTQLQIEISA-N n-[(3s)-2,6-dioxopiperidin-3-yl]-2-phenylacetamide Chemical compound N([C@@H]1C(NC(=O)CC1)=O)C(=O)CC1=CC=CC=C1 OQGRFQCUGLKSAV-JTQLQIEISA-N 0.000 description 1
• SRLPZQAEBMZCIJ-UHFFFAOYSA-N n-[(4-chlorophenyl)carbamoyl]-2-(dimethylamino)-6-fluorobenzamide Chemical compound CN(C)C1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 SRLPZQAEBMZCIJ-UHFFFAOYSA-N 0.000 description 1
• NJSMWLQOCQIOPE-OCHFTUDZSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 NJSMWLQOCQIOPE-OCHFTUDZSA-N 0.000 description 1
• XNSAINXGIQZQOO-UHFFFAOYSA-N n-[1-(2-carbamoylpyrrolidin-1-yl)-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C(NC(=O)C1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-UHFFFAOYSA-N 0.000 description 1
• TVYPSLDUBVTDIS-FUOMVGGVSA-N n-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C(=CN(C(=O)N=2)[C@H]2[C@@H]([C@H](O)[C@@H](C)O2)O)F)=C1 TVYPSLDUBVTDIS-FUOMVGGVSA-N 0.000 description 1
• XEFNBUBDJCJOGM-OUJCMCIWSA-N n-[1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 XEFNBUBDJCJOGM-OUJCMCIWSA-N 0.000 description 1
• FODMSVBVCPOQRL-UHFFFAOYSA-N n-[2-[4-(3-aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide;hydrochloride Chemical compound [Cl-].NC(N)=NCCCCCCC(=O)NC(O)C(=O)NCCCCNCCC[NH3+] FODMSVBVCPOQRL-UHFFFAOYSA-N 0.000 description 1
• KBKUHTSWUQDGFC-UHFFFAOYSA-N n-[3,3-dimethyl-1-[(1-methylpiperidin-4-yl)methyl]-2h-indol-6-yl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1CN1C2=CC(NC(=O)C=3C(=NC=CC=3)NC=3C=C4NN=CC4=CC=3)=CC=C2C(C)(C)C1 KBKUHTSWUQDGFC-UHFFFAOYSA-N 0.000 description 1
• FGKQJOUXTBECOZ-UHFFFAOYSA-N n-[4-tert-butyl-3-(3-morpholin-4-ylpropyl)phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1CCCN1CCOCC1 FGKQJOUXTBECOZ-UHFFFAOYSA-N 0.000 description 1
• YVVUIPFZEDHHDI-RUDMXATFSA-N n-[4-tert-butyl-3-[(e)-4-pyrrolidin-1-ylbut-1-enyl]phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CC(C)(C)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1\C=C\CCN1CCCC1 YVVUIPFZEDHHDI-RUDMXATFSA-N 0.000 description 1
• BLSOATWWAGIRGE-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-[[4-[bis(2-chloroethyl)amino]benzoyl]amino]-1-methylpyrrole-2-carboxamide;hydrochloride Chemical compound Cl.C1=C(C(=O)NCCC(N)=N)N(C)C=C1NC(=O)C1=CC(NC(=O)C=2N(C=C(NC(=O)C=3C=CC(=CC=3)N(CCCl)CCCl)C=2)C)=CN1C BLSOATWWAGIRGE-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• AUWFXUHWMBMPTI-UHFFFAOYSA-N n-pyrazin-2-ylnitrous amide Chemical compound O=NNC1=CN=CC=N1 AUWFXUHWMBMPTI-UHFFFAOYSA-N 0.000 description 1
• RWHUEXWOYVBUCI-ITQXDASVSA-N nafarelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C=C2C=CC=CC2=CC=1)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)NCC(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 RWHUEXWOYVBUCI-ITQXDASVSA-N 0.000 description 1
• 229960002333 nafarelin Drugs 0.000 description 1
• UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
• 229960004127 naloxone Drugs 0.000 description 1
• PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 1
• 108010032539 nartograstim Proteins 0.000 description 1
• 229950010676 nartograstim Drugs 0.000 description 1
• 210000001989 nasopharynx Anatomy 0.000 description 1
• 230000008693 nausea Effects 0.000 description 1
• IXOXBSCIXZEQEQ-UHTZMRCNSA-N nelarabine Chemical compound C1=NC=2C(OC)=NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O IXOXBSCIXZEQEQ-UHTZMRCNSA-N 0.000 description 1
• 229960000801 nelarabine Drugs 0.000 description 1
• 208000007538 neurilemmoma Diseases 0.000 description 1
• 210000004498 neuroglial cell Anatomy 0.000 description 1
• 208000004235 neutropenia Diseases 0.000 description 1
• BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
• 229960002653 nilutamide Drugs 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
• 125000006501 nitrophenyl group Chemical group 0.000 description 1
• 229950000891 nolatrexed Drugs 0.000 description 1
• XHWRWCSCBDLOLM-UHFFFAOYSA-N nolatrexed Chemical compound CC1=CC=C2NC(N)=NC(=O)C2=C1SC1=CC=NC=C1 XHWRWCSCBDLOLM-UHFFFAOYSA-N 0.000 description 1
• 229960004708 noscapine Drugs 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 235000020824 obesity Nutrition 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• YVPOTNAPPSUMJX-UHFFFAOYSA-N octadecanoic acid;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCCCCCCCCCC(O)=O YVPOTNAPPSUMJX-UHFFFAOYSA-N 0.000 description 1
• 229960002700 octreotide Drugs 0.000 description 1
• HYFHYPWGAURHIV-JFIAXGOJSA-N omacetaxine mepesuccinate Chemical compound C1=C2CCN3CCC[C@]43C=C(OC)[C@@H](OC(=O)[C@@](O)(CCCC(C)(C)O)CC(=O)OC)[C@H]4C2=CC2=C1OCO2 HYFHYPWGAURHIV-JFIAXGOJSA-N 0.000 description 1
• 229960002230 omacetaxine mepesuccinate Drugs 0.000 description 1
• 108010046821 oprelvekin Proteins 0.000 description 1
• 229960001840 oprelvekin Drugs 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• ZLLOIFNEEWYATC-XMUHMHRVSA-N osaterone Chemical compound C1=C(Cl)C2=CC(=O)OC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 ZLLOIFNEEWYATC-XMUHMHRVSA-N 0.000 description 1
• 229950006466 osaterone Drugs 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 1
• 229960003978 pamidronic acid Drugs 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 208000012111 paraneoplastic syndrome Diseases 0.000 description 1
• 229960004662 parecoxib Drugs 0.000 description 1
• TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 244000052769 pathogen Species 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 229960003931 peginterferon alfa-2b Drugs 0.000 description 1
• 108010092851 peginterferon alfa-2b Proteins 0.000 description 1
• 229960002995 pegvisomant Drugs 0.000 description 1
• 108700037519 pegvisomant Proteins 0.000 description 1
• QOFFJEBXNKRSPX-ZDUSSCGKSA-N pemetrexed Chemical compound C1=N[C]2NC(N)=NC(=O)C2=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QOFFJEBXNKRSPX-ZDUSSCGKSA-N 0.000 description 1
• 229960005079 pemetrexed Drugs 0.000 description 1
• VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
• 229960005301 pentazocine Drugs 0.000 description 1
• 229940023556 pentosan polysulphate sodium Drugs 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCCN[C@@H](C)C=1C=CC=CC=1)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 description 1
• 229950003180 peplomycin Drugs 0.000 description 1
• 208000011906 peptic ulcer disease Diseases 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
• 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 150000004885 piperazines Chemical class 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 229960001221 pirarubicin Drugs 0.000 description 1
• 229950001030 piritrexim Drugs 0.000 description 1
• 229950001746 piroxantrone Drugs 0.000 description 1
• 229940127126 plasminogen activator Drugs 0.000 description 1
• 229960003171 plicamycin Drugs 0.000 description 1
• 239000002574 poison Substances 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 208000005987 polymyositis Diseases 0.000 description 1
• 229950004406 porfiromycin Drugs 0.000 description 1
• 150000004032 porphyrins Chemical class 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 229910000160 potassium phosphate Inorganic materials 0.000 description 1
• 235000011009 potassium phosphates Nutrition 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000012910 preclinical development Methods 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 229950003608 prinomastat Drugs 0.000 description 1
• YKPYIPVDTNNYCN-INIZCTEOSA-N prinomastat Chemical compound ONC(=O)[C@H]1C(C)(C)SCCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=NC=C1 YKPYIPVDTNNYCN-INIZCTEOSA-N 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 229960003857 proglumide Drugs 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 230000017854 proteolysis Effects 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 208000005333 pulmonary edema Diseases 0.000 description 1
• ONQBBCUWASUJGE-UHFFFAOYSA-N putrebactin Natural products ON1CCCCNC(=O)CCC(=O)N(O)CCCCNC(=O)CCC1=O ONQBBCUWASUJGE-UHFFFAOYSA-N 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical class OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000000171 quenching effect Effects 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 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 1
• 229960004622 raloxifene Drugs 0.000 description 1
• 229960004432 raltitrexed Drugs 0.000 description 1
• 229960002185 ranimustine Drugs 0.000 description 1
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
• 229960000424 rasburicase Drugs 0.000 description 1
• 108010084837 rasburicase Proteins 0.000 description 1
• 208000002574 reactive arthritis Diseases 0.000 description 1
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 108010026350 restrictin-P Proteins 0.000 description 1
• 230000004264 retinal detachment Effects 0.000 description 1
• 208000032253 retinal ischemia Diseases 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• OWPCHSCAPHNHAV-LMONGJCWSA-N rhizoxin Chemical compound C/C([C@H](OC)[C@@H](C)[C@@H]1C[C@H](O)[C@]2(C)O[C@@H]2/C=C/[C@@H](C)[C@]2([H])OC(=O)C[C@@](C2)(C[C@@H]2O[C@H]2C(=O)O1)[H])=C\C=C\C(\C)=C\C1=COC(C)=N1 OWPCHSCAPHNHAV-LMONGJCWSA-N 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229960004641 rituximab Drugs 0.000 description 1
• 229960000371 rofecoxib Drugs 0.000 description 1
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
• 229950003733 romurtide Drugs 0.000 description 1
• 108700033545 romurtide Proteins 0.000 description 1
• VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 1
• 229950009213 rubitecan Drugs 0.000 description 1
• 229940081991 samarium Drugs 0.000 description 1
• KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
• 201000000306 sarcoidosis Diseases 0.000 description 1
• 108010038379 sargramostim Proteins 0.000 description 1
• 229960002530 sargramostim Drugs 0.000 description 1
• 229960005399 satraplatin Drugs 0.000 description 1
• 190014017285 satraplatin Chemical compound 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
• 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 1
• 208000007056 sickle cell anemia Diseases 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
• 229910000367 silver sulfate Inorganic materials 0.000 description 1
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
• 229960002930 sirolimus Drugs 0.000 description 1
• RQHZAASWYUEYCJ-JVWHUAOPSA-N siwenmycin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O[C@@H]3O[C@@H](C)[C@@H](O[C@@H]4O[C@@H](C)[C@H]5O[C@@H]6O[C@H](C)C(=O)C[C@@H]6O[C@H]5C4)[C@H](C3)N(C)C)C[C@@](CC)(O)[C@H](C(=O)OC)C1=C2 RQHZAASWYUEYCJ-JVWHUAOPSA-N 0.000 description 1
• 229950001403 sizofiran Drugs 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
• 235000019254 sodium formate Nutrition 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
• 229940006198 sodium phenylacetate Drugs 0.000 description 1
• CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
• 210000004872 soft tissue Anatomy 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 229950004796 sparfosic acid Drugs 0.000 description 1
• MFIWRSIQAIKKEY-DSQGJUKISA-N spatol Chemical compound O([C@H]1[C@H]2O[C@@H]2C(=C)[C@H]2[C@H]3[C@H]4[C@@H]([C@]3([C@H](O)C2)C)CC[C@H]4C)C1(C)C MFIWRSIQAIKKEY-DSQGJUKISA-N 0.000 description 1
• MFIWRSIQAIKKEY-UHFFFAOYSA-N spatol Natural products CC1CCC(C2(C(O)C3)C)C1C2C3C(=C)C1OC1C1OC1(C)C MFIWRSIQAIKKEY-UHFFFAOYSA-N 0.000 description 1
• 229950006315 spirogermanium Drugs 0.000 description 1
• 229950006050 spiromustine Drugs 0.000 description 1
• 238000011272 standard treatment Methods 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 229910001631 strontium chloride Inorganic materials 0.000 description 1
• AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
• LLWMPGSQZXZZAE-UHFFFAOYSA-N stypoldione Natural products C1C(C(C(=O)C=C2C)=O)=C2OC21C1(C)CCC3C(C)(C)C(O)CCC3(C)C1CCC2C LLWMPGSQZXZZAE-UHFFFAOYSA-N 0.000 description 1
• 210000004003 subcutaneous fat Anatomy 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 125000005864 sulfonamidyl group Chemical group 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• SRXBXVZOQNUGMC-UBOCCBBCSA-N sun-0237 Chemical compound O[C@@H]([C@]1(C)[C@@H]23)C(=O)C=C(C)[C@@H]1C[C@@H]1[C@@]43CO[C@@]2(O)[C@H](O)C(=C)[C@@H]4[C@@H](OC(=O)/C=C/CCCCCCCC)C(=O)O1 SRXBXVZOQNUGMC-UBOCCBBCSA-N 0.000 description 1
• XOCICDFNNMOAKJ-OLGFVZGESA-N sun-2071 Chemical compound O[C@@H]([C@]1(C)[C@@H]23)C(=O)C=C(C)[C@@H]1C[C@@H]1[C@@]43CO[C@@]2(O)[C@H](O)C(=C)[C@@H]4[C@@H](OC(=O)/C=C(C)/CCCCC)C(=O)O1 XOCICDFNNMOAKJ-OLGFVZGESA-N 0.000 description 1
• FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
• 229960005314 suramin Drugs 0.000 description 1
• 238000011477 surgical intervention Methods 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 108700003774 talisomycin Proteins 0.000 description 1
• 229950002687 talisomycin Drugs 0.000 description 1
• 108010021891 tallimustine Proteins 0.000 description 1
• 229950010168 tauromustine Drugs 0.000 description 1
• 229960002197 temoporfin Drugs 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• 229950008703 teroxirone Drugs 0.000 description 1
• ISTOHHFNKVUOKP-BRUMOIPRSA-N terpentecin Chemical compound O=CC(=O)[C@@]1([C@H](O)C[C@@]2(C)[C@H]3[C@](C(=CCC3)C)(C)C(=O)[C@H](O)[C@H]2C)CO1 ISTOHHFNKVUOKP-BRUMOIPRSA-N 0.000 description 1
• ISTOHHFNKVUOKP-UHFFFAOYSA-N terpentecin Natural products CC1C(O)C(=O)C(C(=CCC2)C)(C)C2C1(C)CC(O)C1(C(=O)C=O)CO1 ISTOHHFNKVUOKP-UHFFFAOYSA-N 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• CXVCSRUYMINUSF-UHFFFAOYSA-N tetrathiomolybdate(2-) Chemical compound [S-][Mo]([S-])(=S)=S CXVCSRUYMINUSF-UHFFFAOYSA-N 0.000 description 1
• 229960003433 thalidomide Drugs 0.000 description 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
• NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
• 229960004231 thymalfasin Drugs 0.000 description 1
• 229960000902 thyrotropin alfa Drugs 0.000 description 1
• MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
• 229960003087 tioguanine Drugs 0.000 description 1
• 229950002376 tirapazamine Drugs 0.000 description 1
• ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 description 1
• 229930003802 tocotrienol Natural products 0.000 description 1
• 239000011731 tocotrienol Substances 0.000 description 1
• 235000019148 tocotrienols Nutrition 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
• 229960005026 toremifene Drugs 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 229960000575 trastuzumab Drugs 0.000 description 1
• 229960003181 treosulfan Drugs 0.000 description 1
• 125000005270 trialkylamine group Chemical group 0.000 description 1
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
• KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-N 0.000 description 1
• 229960001670 trilostane Drugs 0.000 description 1
• NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
• 229960001099 trimetrexate Drugs 0.000 description 1
• VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 description 1
• 229960004824 triptorelin Drugs 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
• 239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 229960002004 valdecoxib Drugs 0.000 description 1
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
• 229960000653 valrubicin Drugs 0.000 description 1
• ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
• 229950010938 valspodar Drugs 0.000 description 1
• 108010082372 valspodar Proteins 0.000 description 1
• 230000006444 vascular growth Effects 0.000 description 1
• 208000021331 vascular occlusion disease Diseases 0.000 description 1
• 229960003895 verteporfin Drugs 0.000 description 1
• ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N verteporfin Chemical compound C=1C([C@@]2([C@H](C(=O)OC)C(=CC=C22)C(=O)OC)C)=NC2=CC(C(=C2C=C)C)=NC2=CC(C(=C2CCC(O)=O)C)=NC2=CC2=NC=1C(C)=C2CCC(=O)OC ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N 0.000 description 1
• 230000035899 viability Effects 0.000 description 1
• KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.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 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
• 229960004982 vinblastine sulfate Drugs 0.000 description 1
• 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 1
• 229960004528 vincristine Drugs 0.000 description 1
• 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 1
• UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• IQDSXWRQCKDBMW-NSFJATOBSA-N vintriptol Chemical compound C([C@@H](C[C@@](O)(CC)C1)C[C@@]2(C3=C(OC)C=C4N(C)[C@H]5[C@@]([C@@H]([C@]6(CC)C=CCN7CC[C@]5([C@H]67)C4=C3)O)(O)C(=O)N[C@@H](CC=3C4=CC=CC=C4NC=3)C(=O)OCC)C(=O)OC)N1CCC1=C2NC2=CC=CC=C12 IQDSXWRQCKDBMW-NSFJATOBSA-N 0.000 description 1
• 229950003415 vintriptol Drugs 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229950005839 vinzolidine Drugs 0.000 description 1
• 230000008673 vomiting Effects 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1
• 229960000523 zalcitabine Drugs 0.000 description 1
• FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
• 229950009233 zinostatin stimalamer Drugs 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