CA2827648A1 - Tricyclic inhibitors of kinases - Google Patents
Tricyclic inhibitors of kinases Download PDFInfo
- Publication number
- CA2827648A1 CA2827648A1 CA2827648A CA2827648A CA2827648A1 CA 2827648 A1 CA2827648 A1 CA 2827648A1 CA 2827648 A CA2827648 A CA 2827648A CA 2827648 A CA2827648 A CA 2827648A CA 2827648 A1 CA2827648 A1 CA 2827648A1
- Authority
- CA
- Canada
- Prior art keywords
- pyrimido
- pyrimidin
- amino
- imidazo
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108091000080 Phosphotransferase Proteins 0.000 title abstract description 15
- 102000020233 phosphotransferase Human genes 0.000 title abstract description 15
- 239000003112 inhibitor Substances 0.000 title description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 368
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- -1 {4- [4-(2-methoxyethyl)piperazin-1-yl]phenyl} amino Chemical group 0.000 claims description 504
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 233
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 194
- 125000001072 heteroaryl group Chemical group 0.000 claims description 187
- 125000003118 aryl group Chemical group 0.000 claims description 184
- 125000005843 halogen group Chemical group 0.000 claims description 179
- 125000001424 substituent group Chemical group 0.000 claims description 168
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 145
- FAPREGZSIDHQBT-UHFFFAOYSA-N C1=NC=C2C(=O)NC3=NC=CN3C2=N1 Chemical compound C1=NC=C2C(=O)NC3=NC=CN3C2=N1 FAPREGZSIDHQBT-UHFFFAOYSA-N 0.000 claims description 133
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 131
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 81
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 47
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 41
- 125000001624 naphthyl group Chemical group 0.000 claims description 38
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 37
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 37
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 37
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000004043 oxo group Chemical group O=* 0.000 claims description 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 22
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- AOFIYKYYKPEQEY-UHFFFAOYSA-N 12-(4-aminoanilino)-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 AOFIYKYYKPEQEY-UHFFFAOYSA-N 0.000 claims description 4
- DVCFSMPQEKMGAH-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-phenyl-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=NC=CN3C2=N1 DVCFSMPQEKMGAH-UHFFFAOYSA-N 0.000 claims description 3
- VJRKBAPOWFAEMZ-RDJZCZTQSA-N 12-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl VJRKBAPOWFAEMZ-RDJZCZTQSA-N 0.000 claims description 3
- LOVNSZMZEXLULX-UHFFFAOYSA-N 12-anilino-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC=CC=3)N=C2N2C=CN=C21 LOVNSZMZEXLULX-UHFFFAOYSA-N 0.000 claims description 3
- GSDTYSPSQFWYBN-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-[(3-chlorophenyl)methyl]piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(CN2CCN(CC2)C=2C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=2)=C1 GSDTYSPSQFWYBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- WSTMFUSTYZOYDL-UHFFFAOYSA-N 12-(1,2,3-benzothiadiazol-5-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4N=NSC4=CC=3)N=C2N2C=CN=C21 WSTMFUSTYZOYDL-UHFFFAOYSA-N 0.000 claims description 2
- CFYZZUMUBPACPF-UHFFFAOYSA-N 12-(1,3-benzothiazol-6-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4SC=NC4=CC=3)N=C2N2C=CN=C21 CFYZZUMUBPACPF-UHFFFAOYSA-N 0.000 claims description 2
- LPWIXQTVUKDQPE-UHFFFAOYSA-N 12-(4-bromoanilino)-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(Br)=CC=3)N=C2N2C=CN=C21 LPWIXQTVUKDQPE-UHFFFAOYSA-N 0.000 claims description 2
- XBXHHAXUUZSAER-UHFFFAOYSA-N 12-(4-cyclohexylanilino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3CCCCC3)N=C2N2C=CN=C21 XBXHHAXUUZSAER-UHFFFAOYSA-N 0.000 claims description 2
- XQCSSURHRLCVFQ-UHFFFAOYSA-N 12-[(2-acetyl-3,4-dihydro-1H-isoquinolin-6-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2CN(C(=O)C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl XQCSSURHRLCVFQ-UHFFFAOYSA-N 0.000 claims description 2
- ZOERDVHQLNAKHE-UHFFFAOYSA-N 12-[(2-acetyl-3,4-dihydro-1H-isoquinolin-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CN(C(=O)C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl ZOERDVHQLNAKHE-UHFFFAOYSA-N 0.000 claims description 2
- QAHYGGLTHWWEOT-UHFFFAOYSA-N 12-[(2-acetyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)amino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl QAHYGGLTHWWEOT-UHFFFAOYSA-N 0.000 claims description 2
- CWGJVAOSKXUZTO-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl CWGJVAOSKXUZTO-UHFFFAOYSA-N 0.000 claims description 2
- WJRROINZDMTREW-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl WJRROINZDMTREW-UHFFFAOYSA-N 0.000 claims description 2
- CQQNPOAQLYKSME-UHFFFAOYSA-N 12-[4-(2-acetyl-2,7-diazaspiro[3.5]nonan-7-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1N(C(=O)C)CC21CCN(C=1C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=1)CC2 CQQNPOAQLYKSME-UHFFFAOYSA-N 0.000 claims description 2
- GSNIAXMXBBAXNE-UHFFFAOYSA-N 12-[4-[(1-acetylpiperidin-4-yl)amino]anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCC1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 GSNIAXMXBBAXNE-UHFFFAOYSA-N 0.000 claims description 2
- VJRKBAPOWFAEMZ-NVXWUHKLSA-N 12-[4-[(1R,4R)-2,5-diazabicyclo[2.2.1]heptan-2-yl]anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl VJRKBAPOWFAEMZ-NVXWUHKLSA-N 0.000 claims description 2
- BESVCKOFTCVZIZ-QFIPXVFZSA-N 12-[4-[[(3R)-1-azabicyclo[2.2.2]octan-3-yl]amino]anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(N[C@@H]4C5CCN(CC5)C4)=CC=3)N=C2N2C=CN=C21 BESVCKOFTCVZIZ-QFIPXVFZSA-N 0.000 claims description 2
- ZFECWWBXIJRTEA-UHFFFAOYSA-N 12-[4-[bis(2-methoxyethyl)amino]anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(CCOC)CCOC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ZFECWWBXIJRTEA-UHFFFAOYSA-N 0.000 claims description 2
- RBAMWXWJHPVUSG-UHFFFAOYSA-N 12-[[2-[(1-benzylpiperidin-4-yl)methyl]-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC(CC1)CCN1CC1=CC=CC=C1 RBAMWXWJHPVUSG-UHFFFAOYSA-N 0.000 claims description 2
- SVUNWNBQQMXLGG-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SVUNWNBQQMXLGG-UHFFFAOYSA-N 0.000 claims description 2
- RRUCAEDSIJXSMT-UHFFFAOYSA-N 7-(4-hydroxy-2-methylphenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound CC1=CC(O)=CC=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 RRUCAEDSIJXSMT-UHFFFAOYSA-N 0.000 claims description 2
- ZLLWMXBDINIIFP-UHFFFAOYSA-N 7-(4-hydroxyphenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 ZLLWMXBDINIIFP-UHFFFAOYSA-N 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- NNQKGOSIJAERJY-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)NC3CC3)N=C2N2C=CN=C21 NNQKGOSIJAERJY-UHFFFAOYSA-N 0.000 claims 2
- QXZZUBFQRVTJCD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(diethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(CC)CC)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl QXZZUBFQRVTJCD-UHFFFAOYSA-N 0.000 claims 2
- VEYHNBOUKBIXHN-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(propylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(NCCC)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl VEYHNBOUKBIXHN-UHFFFAOYSA-N 0.000 claims 2
- LAMLNRBJGRMUNN-KKFHFHRHSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-[(3S)-3-fluoropyrrolidin-1-yl]-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@@H](F)CCN1C1CC2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5F)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C1 LAMLNRBJGRMUNN-KKFHFHRHSA-N 0.000 claims 2
- XYSPAJYSNPKYPT-UHFFFAOYSA-N C=1C=C2C3(CC3)CN(CCF)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl Chemical compound C=1C=C2C3(CC3)CN(CCF)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl XYSPAJYSNPKYPT-UHFFFAOYSA-N 0.000 claims 2
- JHJDVNFDEKIOSO-GDBMZVCRSA-N (3aS,10aS)-8-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-2,3,3a,5,10,10a-hexahydro-1H-pyrrolo[3,4-c][1]benzazepin-4-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C[C@@H]5CNC[C@H]5C(=O)NC4=CC=3)N=C2N2C=CN=C21 JHJDVNFDEKIOSO-GDBMZVCRSA-N 0.000 claims 1
- MXNPKUQHTFLYOQ-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 MXNPKUQHTFLYOQ-UHFFFAOYSA-N 0.000 claims 1
- WSKYCBFAXMTTQI-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-N-methylmethanesulfonamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 WSKYCBFAXMTTQI-UHFFFAOYSA-N 0.000 claims 1
- SHIGBOIFLLIYCS-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SHIGBOIFLLIYCS-UHFFFAOYSA-N 0.000 claims 1
- KJXAQJXSJOHHLL-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 KJXAQJXSJOHHLL-UHFFFAOYSA-N 0.000 claims 1
- ZQLRREONZSVIQO-UHFFFAOYSA-N 12-[(1-acetyl-2,3-dihydroindol-6-yl)amino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2N(C(=O)C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl ZQLRREONZSVIQO-UHFFFAOYSA-N 0.000 claims 1
- GKAIUFLVMQMDHO-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GKAIUFLVMQMDHO-UHFFFAOYSA-N 0.000 claims 1
- IDVBIPAGPCIDPV-UHFFFAOYSA-N 12-[(2-cyclopropylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)S(=O)(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 IDVBIPAGPCIDPV-UHFFFAOYSA-N 0.000 claims 1
- LDPUHXKJRAXDON-UHFFFAOYSA-N 12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-propan-2-yl-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound N=1C=C2C(=O)N(C(C)C)C3=NC=CN3C2=NC=1NC(C=1)=CC=C2C=1CN(C)CC21CC1 LDPUHXKJRAXDON-UHFFFAOYSA-N 0.000 claims 1
- QVYKKSXEJXHNGJ-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 QVYKKSXEJXHNGJ-UHFFFAOYSA-N 0.000 claims 1
- PWNBRPDHBMSFSF-UHFFFAOYSA-N 12-[4-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCCN4CC3)N=C2N2C=CN=C21 PWNBRPDHBMSFSF-UHFFFAOYSA-N 0.000 claims 1
- LLLNFIQZWRXVLO-UHFFFAOYSA-N 12-[4-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CNCC4C3)N=C2N2C=CN=C21 LLLNFIQZWRXVLO-UHFFFAOYSA-N 0.000 claims 1
- SARRXSLLADDAOE-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.4]octan-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4(C3)CNCC4)N=C2N2C=CN=C21 SARRXSLLADDAOE-UHFFFAOYSA-N 0.000 claims 1
- KWDCBYJISYZLLU-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.5]nonan-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4(C3)CCNCC4)N=C2N2C=CN=C21 KWDCBYJISYZLLU-UHFFFAOYSA-N 0.000 claims 1
- PMWSRMFYNLXUOL-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.5]nonan-7-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC4(CNC4)CC3)N=C2N2C=CN=C21 PMWSRMFYNLXUOL-UHFFFAOYSA-N 0.000 claims 1
- ZJEYDTIPPFWMNI-UHFFFAOYSA-N 12-[4-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCN4CC3)N=C2N2C=CN=C21 ZJEYDTIPPFWMNI-UHFFFAOYSA-N 0.000 claims 1
- CAFTYPPLMPBFKG-UHFFFAOYSA-N 12-[4-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCN4CC3)N=C2N2C=CN=C21 CAFTYPPLMPBFKG-UHFFFAOYSA-N 0.000 claims 1
- JPQMJYUOSIHHNT-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-1-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JPQMJYUOSIHHNT-UHFFFAOYSA-N 0.000 claims 1
- BQXGAXHVZLYFLW-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-1-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 BQXGAXHVZLYFLW-UHFFFAOYSA-N 0.000 claims 1
- RAOFCVHAVATOES-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-[2-(trifluoromethoxy)phenyl]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)OC(F)(F)F)C3=NC=CN3C2=N1 RAOFCVHAVATOES-UHFFFAOYSA-N 0.000 claims 1
- ABVBVZIBDDRXHB-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-[2-(trifluoromethyl)phenyl]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)C(F)(F)F)C3=NC=CN3C2=N1 ABVBVZIBDDRXHB-UHFFFAOYSA-N 0.000 claims 1
- LTLLXUSSJDQDHM-LJQANCHMSA-N 12-[4-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]anilino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3C[C@H]4CCCN4CC3)N=C2N2C=CN=C21 LTLLXUSSJDQDHM-LJQANCHMSA-N 0.000 claims 1
- CAFTYPPLMPBFKG-HXUWFJFHSA-N 12-[4-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3C[C@H]4CCCN4CC3)N=C2N2C=CN=C21 CAFTYPPLMPBFKG-HXUWFJFHSA-N 0.000 claims 1
- CAFTYPPLMPBFKG-FQEVSTJZSA-N 12-[4-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3C[C@@H]4CCCN4CC3)N=C2N2C=CN=C21 CAFTYPPLMPBFKG-FQEVSTJZSA-N 0.000 claims 1
- UOLZCRZBSIDSIC-UHFFFAOYSA-N 12-[[2-(cyclopropanecarbonyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 UOLZCRZBSIDSIC-UHFFFAOYSA-N 0.000 claims 1
- ZPNSETQPCRFHOG-UHFFFAOYSA-N 12-[[2-(cyclopropylamino)-2,3-dihydro-1H-inden-5-yl]amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)NC3CC3)N=C2N2C=CN=C21 ZPNSETQPCRFHOG-UHFFFAOYSA-N 0.000 claims 1
- VIOAAWUARYASTN-UHFFFAOYSA-N 12-anilino-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC=CC=3)N=C2N2C=CN=C21 VIOAAWUARYASTN-UHFFFAOYSA-N 0.000 claims 1
- QIBUEKFLXRFNOZ-UHFFFAOYSA-N 12-anilino-7-(3-hydroxy-2-methylphenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound CC1=C(O)C=CC=C1N1C(=O)C2=CN=C(NC=3C=CC=CC=3)N=C2N2C=CN=C21 QIBUEKFLXRFNOZ-UHFFFAOYSA-N 0.000 claims 1
- IGCUAUFPJNLDSO-UHFFFAOYSA-N 12-anilino-7-(3-hydroxyphenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound OC1=CC=CC(N2C(C3=CN=C(NC=4C=CC=CC=4)N=C3N3C=CN=C32)=O)=C1 IGCUAUFPJNLDSO-UHFFFAOYSA-N 0.000 claims 1
- GFTMSJAEEHGADR-UHFFFAOYSA-N 12-anilino-7-(3-methoxy-2-methylphenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC=CC(N2C(C3=CN=C(NC=4C=CC=CC=4)N=C3N3C=CN=C32)=O)=C1C GFTMSJAEEHGADR-UHFFFAOYSA-N 0.000 claims 1
- MEDXOIFKFTYQIH-UHFFFAOYSA-N 2-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-5-methyl-1,3-thiazolidin-4-one Chemical compound N1C(=O)C(C)SC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 MEDXOIFKFTYQIH-UHFFFAOYSA-N 0.000 claims 1
- RAOAJMDTFNJCGT-UHFFFAOYSA-N 2-[cyclopropyl(methyl)amino]ethyl 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoate Chemical compound C1CC1N(C)CCOC(=O)C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl RAOAJMDTFNJCGT-UHFFFAOYSA-N 0.000 claims 1
- FCRXDUAFQRKDNB-UHFFFAOYSA-N 3-[4-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]piperazin-1-yl]propanenitrile Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(CCC#N)CC3)N=C2N2C=CN=C21 FCRXDUAFQRKDNB-UHFFFAOYSA-N 0.000 claims 1
- GZTCYQYXVYNDJM-UHFFFAOYSA-N 3-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-cyclopropylanilino]propanenitrile Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N(CCC#N)C3CC3)N=C2N2C=CN=C21 GZTCYQYXVYNDJM-UHFFFAOYSA-N 0.000 claims 1
- VYVOWWGXHVELTL-UHFFFAOYSA-N 3-[[4-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]piperazin-1-yl]methyl]benzonitrile Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(CC=4C=C(C=CC=4)C#N)CC3)N=C2N2C=CN=C21 VYVOWWGXHVELTL-UHFFFAOYSA-N 0.000 claims 1
- CFYRYYVJZSDUJU-UHFFFAOYSA-N 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 CFYRYYVJZSDUJU-UHFFFAOYSA-N 0.000 claims 1
- KSELMXMUDGOLFH-UHFFFAOYSA-N 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-[4-(dimethylamino)cyclohexyl]benzamide Chemical compound C1CC(N(C)C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KSELMXMUDGOLFH-UHFFFAOYSA-N 0.000 claims 1
- FDYOQRGSQDHYPS-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N,N-diethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 FDYOQRGSQDHYPS-UHFFFAOYSA-N 0.000 claims 1
- PCLRXBXXCJHMTF-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-cyclohexylbenzamide Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C(=O)NC3CCCCC3)N=C2N2C=CN=C21 PCLRXBXXCJHMTF-UHFFFAOYSA-N 0.000 claims 1
- NTFYGGCWWQYKAO-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 NTFYGGCWWQYKAO-UHFFFAOYSA-N 0.000 claims 1
- VVRKDJOZLXFMBL-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-pyridin-4-ylbenzamide Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C(=O)NC=3C=CN=CC=3)N=C2N2C=CN=C21 VVRKDJOZLXFMBL-UHFFFAOYSA-N 0.000 claims 1
- KCUNBCQXUBVYAX-UHFFFAOYSA-N 6-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-4H-1,4-benzoxazin-3-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C4NC(=O)COC4=CC=3)N=C2N2C=CN=C21 KCUNBCQXUBVYAX-UHFFFAOYSA-N 0.000 claims 1
- PBHVOWBAQKJIHE-UHFFFAOYSA-N 7-(2,4-dimethoxyphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC(OC)=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2N2C=CN=C21 PBHVOWBAQKJIHE-UHFFFAOYSA-N 0.000 claims 1
- MWFNJZACFYVWPD-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC(F)=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 MWFNJZACFYVWPD-UHFFFAOYSA-N 0.000 claims 1
- ZEJFJEZCFFBWJX-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=C(F)C=C1Cl ZEJFJEZCFFBWJX-UHFFFAOYSA-N 0.000 claims 1
- OXCFVBYWTGGOQB-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=C(F)C=C1Cl OXCFVBYWTGGOQB-UHFFFAOYSA-N 0.000 claims 1
- MHZZCSSVPOHYON-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[(6-piperazin-1-ylpyridin-3-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC(F)=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=NC(=CC=3)N3CCNCC3)N=C2N2C=CN=C21 MHZZCSSVPOHYON-UHFFFAOYSA-N 0.000 claims 1
- VFZPAFOLJAQYOG-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[3-methyl-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(F)=CC=3Cl)Cl)C3=NC=CN3C2=N1 VFZPAFOLJAQYOG-UHFFFAOYSA-N 0.000 claims 1
- COZUICJLJUGGAF-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(F)=CC=3Cl)Cl)C3=NC=CN3C2=N1 COZUICJLJUGGAF-UHFFFAOYSA-N 0.000 claims 1
- ZFLFXSHMLQGSTN-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=C(F)C=C1Cl ZFLFXSHMLQGSTN-UHFFFAOYSA-N 0.000 claims 1
- BLZMYIUFPQJWKP-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2N2C=CN=C21 BLZMYIUFPQJWKP-UHFFFAOYSA-N 0.000 claims 1
- RGHKDYZHFCXXGZ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(1H-indazol-5-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C=NNC4=CC=3)N=C2N2C=CN=C21 RGHKDYZHFCXXGZ-UHFFFAOYSA-N 0.000 claims 1
- SJKFRWBTYBCUGI-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(1H-indazol-6-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4NN=CC4=CC=3)N=C2N2C=CN=C21 SJKFRWBTYBCUGI-UHFFFAOYSA-N 0.000 claims 1
- GGAQMONGBVYRHN-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(3,5-difluoro-4-piperazin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C(F)=C(N2CCNCC2)C(F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GGAQMONGBVYRHN-UHFFFAOYSA-N 0.000 claims 1
- SPYJRXAJCSHASW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(4-piperidin-2-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3NCCCC3)N=C2N2C=CN=C21 SPYJRXAJCSHASW-UHFFFAOYSA-N 0.000 claims 1
- DNDPQMUPODMFQA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(4-pyrrolidin-2-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3NCCC3)N=C2N2C=CN=C21 DNDPQMUPODMFQA-UHFFFAOYSA-N 0.000 claims 1
- XMFGSTRFDFIUBX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 XMFGSTRFDFIUBX-UHFFFAOYSA-N 0.000 claims 1
- RVAPALZVDKEYRH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(1,1,2,3,3-pentamethylisoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2C(C)(C)N(C)C(C)(C)C2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl RVAPALZVDKEYRH-UHFFFAOYSA-N 0.000 claims 1
- XCRDWMSFUCDJCE-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(1,1,2-trimethyl-3,4-dihydroisoquinolin-6-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl XCRDWMSFUCDJCE-UHFFFAOYSA-N 0.000 claims 1
- YZMCCFLYDCAMJE-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(1,1,2-trimethyl-3H-isoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl YZMCCFLYDCAMJE-UHFFFAOYSA-N 0.000 claims 1
- FIEFUTLSNLZAGA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl FIEFUTLSNLZAGA-UHFFFAOYSA-N 0.000 claims 1
- GAGKTBMUQVXVFC-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-ethylsulfonyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(S(=O)(=O)CC)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GAGKTBMUQVXVFC-UHFFFAOYSA-N 0.000 claims 1
- LVWGYVOYZGMKSJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl LVWGYVOYZGMKSJ-UHFFFAOYSA-N 0.000 claims 1
- KFMRHPXDYPAONS-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-methylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(S(=O)(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl KFMRHPXDYPAONS-UHFFFAOYSA-N 0.000 claims 1
- YNJPXSBWVLFYNW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-propan-2-ylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(S(=O)(=O)C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl YNJPXSBWVLFYNW-UHFFFAOYSA-N 0.000 claims 1
- IWTDIBNESAUTDQ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-pyrrolidin-1-yl-2,3-dihydro-1H-inden-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)N3CCCC3)N=C2N2C=CN=C21 IWTDIBNESAUTDQ-UHFFFAOYSA-N 0.000 claims 1
- QSPFXHIREXUPNK-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(4,4-dimethyl-2,3-dihydro-1H-isoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl QSPFXHIREXUPNK-UHFFFAOYSA-N 0.000 claims 1
- FSHSRWFNFYSCTH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(4,4-dimethyl-2-methylsulfonyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(S(C)(=O)=O)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl FSHSRWFNFYSCTH-UHFFFAOYSA-N 0.000 claims 1
- KIFSZOILSBLSKH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(4-oxo-1H-cinnolin-6-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(=O)C=NNC4=CC=3)N=C2N2C=CN=C21 KIFSZOILSBLSKH-UHFFFAOYSA-N 0.000 claims 1
- NZCPVWCJDIRVSB-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(6-piperazin-1-ylpyridin-3-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=NC(=CC=3)N3CCNCC3)N=C2N2C=CN=C21 NZCPVWCJDIRVSB-UHFFFAOYSA-N 0.000 claims 1
- GTMOOJIZVADIIA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[3-(hydroxymethyl)-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)CO)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 GTMOOJIZVADIIA-UHFFFAOYSA-N 0.000 claims 1
- RBEVWQZQYFQXSN-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[3-ethyl-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(CC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl RBEVWQZQYFQXSN-UHFFFAOYSA-N 0.000 claims 1
- IPAMMJLEAOPWRH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(OC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl IPAMMJLEAOPWRH-UHFFFAOYSA-N 0.000 claims 1
- KDULFSRPAJMGSJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[3-methyl-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KDULFSRPAJMGSJ-UHFFFAOYSA-N 0.000 claims 1
- LTOCMASZGWESMF-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(1-methylpiperidin-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 LTOCMASZGWESMF-UHFFFAOYSA-N 0.000 claims 1
- STAWYSSWADGLPY-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(2-methylsulfonyl-2,7-diazaspiro[3.5]nonan-7-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1N(S(=O)(=O)C)CC21CCN(C=1C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=1)CC2 STAWYSSWADGLPY-UHFFFAOYSA-N 0.000 claims 1
- YUSACECZXYAHRO-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(3,3-difluoropiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C(F)(F)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 YUSACECZXYAHRO-UHFFFAOYSA-N 0.000 claims 1
- UYFFZUITWKYKDZ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(3-oxopiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC(=O)NCC3)N=C2N2C=CN=C21 UYFFZUITWKYKDZ-UHFFFAOYSA-N 0.000 claims 1
- JPLBPJNNOXQWAL-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4,4-difluoropiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(F)(F)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JPLBPJNNOXQWAL-UHFFFAOYSA-N 0.000 claims 1
- ZFFLPGAASPARKM-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-methylpiperazin-1-yl)-3-propan-2-ylanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(C(C)C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl ZFFLPGAASPARKM-UHFFFAOYSA-N 0.000 claims 1
- LYCVEVRCMPEROG-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 LYCVEVRCMPEROG-UHFFFAOYSA-N 0.000 claims 1
- LVGYPHJTNLSONJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-piperidin-1-ylpiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCCC3)N=C2N2C=CN=C21 LVGYPHJTNLSONJ-UHFFFAOYSA-N 0.000 claims 1
- ALGSKGHDUKFHSW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ALGSKGHDUKFHSW-UHFFFAOYSA-N 0.000 claims 1
- JUCXZLZNUPUMAX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCC3)N=C2N2C=CN=C21 JUCXZLZNUPUMAX-UHFFFAOYSA-N 0.000 claims 1
- MAIXOLYZPZODGD-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3CCC(=O)NN=3)N=C2N2C=CN=C21 MAIXOLYZPZODGD-UHFFFAOYSA-N 0.000 claims 1
- ITBIXLURBFCVLL-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(9-methyl-3,9-diazaspiro[5.5]undecan-3-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCC21CCN(C=1C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=1)CC2 ITBIXLURBFCVLL-UHFFFAOYSA-N 0.000 claims 1
- LRGFEYBMQIRJDW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(piperidin-4-ylamino)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(NC4CCNCC4)=CC=3)N=C2N2C=CN=C21 LRGFEYBMQIRJDW-UHFFFAOYSA-N 0.000 claims 1
- YAFZYVBNSGAZJR-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[(1-methylsulfonylpiperidin-4-yl)amino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(S(=O)(=O)C)CCC1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 YAFZYVBNSGAZJR-UHFFFAOYSA-N 0.000 claims 1
- FEUICBMWYFHGDZ-KDURUIRLSA-N 7-(2,6-dichlorophenyl)-12-[4-[(1R,5S)-7-ethyl-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C([C@]1(CN(CC)C[C@@](C2)(C1)[H])[H])N2C(=O)C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl FEUICBMWYFHGDZ-KDURUIRLSA-N 0.000 claims 1
- KZXXQNYTTLEMPA-GOSISDBHSA-N 7-(2,6-dichlorophenyl)-12-[4-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@H](N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KZXXQNYTTLEMPA-GOSISDBHSA-N 0.000 claims 1
- JWZIHTRIINQCRU-GASCZTMLSA-N 7-(2,6-dichlorophenyl)-12-[4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-3-fluoroanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)F)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JWZIHTRIINQCRU-GASCZTMLSA-N 0.000 claims 1
- KZXXQNYTTLEMPA-SFHVURJKSA-N 7-(2,6-dichlorophenyl)-12-[4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@@H](N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KZXXQNYTTLEMPA-SFHVURJKSA-N 0.000 claims 1
- QBLPXHRYUWXNIJ-JOCHJYFZSA-N 7-(2,6-dichlorophenyl)-12-[4-[(3S)-3-propan-2-ylpiperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN[C@@H](C(C)C)CN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 QBLPXHRYUWXNIJ-JOCHJYFZSA-N 0.000 claims 1
- DLLLKSDEZLQJHT-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[(4-methylpiperazin-1-yl)methyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 DLLLKSDEZLQJHT-UHFFFAOYSA-N 0.000 claims 1
- PJEIKZYPAJBYSN-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[1-[1-(dimethylamino)-3-methylbutyl]cyclobutyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(NC=2N=C3C(C(N(C=4C(=CC=CC=4Cl)Cl)C4=NC=CN43)=O)=CN=2)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 PJEIKZYPAJBYSN-UHFFFAOYSA-N 0.000 claims 1
- BXLDGIOMGQRMTF-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(1-methylpyrrolidin-2-yl)ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound CN1CCCC1CCNC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 BXLDGIOMGQRMTF-UHFFFAOYSA-N 0.000 claims 1
- VKZXXMSHMVGZMM-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(4-methylpiperazin-1-yl)ethyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1CCC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 VKZXXMSHMVGZMM-UHFFFAOYSA-N 0.000 claims 1
- ZCMFFRXYWPAMAF-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(dimethylamino)ethyl-ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(CCN(C)C)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZCMFFRXYWPAMAF-UHFFFAOYSA-N 0.000 claims 1
- ZSNROWXRZIHBBO-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(dimethylamino)ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(NCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZSNROWXRZIHBBO-UHFFFAOYSA-N 0.000 claims 1
- RCWBCGALBPUPRM-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[3-(diethylamino)propoxy]-3-fluoroanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(F)C(OCCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 RCWBCGALBPUPRM-UHFFFAOYSA-N 0.000 claims 1
- KXAUNTOLVMSJKJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KXAUNTOLVMSJKJ-UHFFFAOYSA-N 0.000 claims 1
- RSDUPIFHAPXDBX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[4-(dimethylamino)piperidine-1-carbonyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 RSDUPIFHAPXDBX-UHFFFAOYSA-N 0.000 claims 1
- GNCAELHTYLWVAX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[propan-2-yl-[2-(propan-2-ylamino)ethyl]amino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(C(C)C)CCNC(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 GNCAELHTYLWVAX-UHFFFAOYSA-N 0.000 claims 1
- BWUMKXXNVDKXLR-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-piperazin-1-yl-3-(trifluoromethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCNCC2)C(C(F)(F)F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl BWUMKXXNVDKXLR-UHFFFAOYSA-N 0.000 claims 1
- AZTYYNWSKUKKBY-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[1-[2-(dimethylamino)ethyl]-2,3-dihydroindol-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2N(CCN(C)C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl AZTYYNWSKUKKBY-UHFFFAOYSA-N 0.000 claims 1
- DGXXKHUWNFRAAP-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(2,2-dimethylpropanoyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C(C)(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl DGXXKHUWNFRAAP-UHFFFAOYSA-N 0.000 claims 1
- AMBRIFCKYYVDGS-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(2-methylpropanoyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl AMBRIFCKYYVDGS-UHFFFAOYSA-N 0.000 claims 1
- GEPSQLANSSBBBA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GEPSQLANSSBBBA-UHFFFAOYSA-N 0.000 claims 1
- OFMHWUQCUJRJJD-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(propylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(NCCC)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl OFMHWUQCUJRJJD-UHFFFAOYSA-N 0.000 claims 1
- NMTKRBQZRMANMZ-KKFHFHRHSA-N 7-(2,6-dichlorophenyl)-12-[[2-[(3S)-3-fluoropyrrolidin-1-yl]-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@@H](F)CCN1C1CC2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C1 NMTKRBQZRMANMZ-KKFHFHRHSA-N 0.000 claims 1
- AAXQXVYTVSHGLS-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[4,4-dimethyl-2-(2,2,2-trifluoroethyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CC(F)(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl AAXQXVYTVSHGLS-UHFFFAOYSA-N 0.000 claims 1
- WLBVSRCBCIYMAZ-UHFFFAOYSA-N 7-(2,6-difluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)F)C3=NC=CN3C2=N1 WLBVSRCBCIYMAZ-UHFFFAOYSA-N 0.000 claims 1
- SVFMGEMTWAECKS-UHFFFAOYSA-N 7-(2,6-dimethylphenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(C)C=CC=C1C SVFMGEMTWAECKS-UHFFFAOYSA-N 0.000 claims 1
- GMKXOFPMGDEEAV-UHFFFAOYSA-N 7-(2-chloro-3-hydroxyphenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound OC1=CC=CC(N2C(C3=CN=C(NC=4C=C5C(C6(CC6)CNC5)=CC=4)N=C3N3C=CN=C32)=O)=C1Cl GMKXOFPMGDEEAV-UHFFFAOYSA-N 0.000 claims 1
- MUBBWOHVMUIKIR-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=C(F)C=C1Cl MUBBWOHVMUIKIR-UHFFFAOYSA-N 0.000 claims 1
- MIUZKHQKIKYNFA-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(F)=CC=3F)Cl)C3=NC=CN3C2=N1 MIUZKHQKIKYNFA-UHFFFAOYSA-N 0.000 claims 1
- FPMBIKCMUSPCLI-UHFFFAOYSA-N 7-(2-chloro-4-methylphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(C)=CC=3)Cl)C3=NC=CN3C2=N1 FPMBIKCMUSPCLI-UHFFFAOYSA-N 0.000 claims 1
- OUVGXWNTDFYUQR-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-(5,6,7,8-tetrahydro-1,6-naphthyridin-3-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=NC=3)N=C2N2C=CN=C21 OUVGXWNTDFYUQR-UHFFFAOYSA-N 0.000 claims 1
- HZXKSYNUISSDRZ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 HZXKSYNUISSDRZ-UHFFFAOYSA-N 0.000 claims 1
- SSDVHDBNZJIQMX-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(1,1,2-trimethyl-3H-isoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl SSDVHDBNZJIQMX-UHFFFAOYSA-N 0.000 claims 1
- YFRNHMAIZOCUPR-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl YFRNHMAIZOCUPR-UHFFFAOYSA-N 0.000 claims 1
- ZSAHIYGOYSATRM-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-methylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(S(=O)(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl ZSAHIYGOYSATRM-UHFFFAOYSA-N 0.000 claims 1
- YBPDRUNRDRQNJG-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-pyrrolidin-1-yl-2,3-dihydro-1H-inden-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)N3CCCC3)N=C2N2C=CN=C21 YBPDRUNRDRQNJG-UHFFFAOYSA-N 0.000 claims 1
- VYCIWMBUYBPTLQ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(4,4-dimethyl-2-methylsulfonyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(S(C)(=O)=O)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl VYCIWMBUYBPTLQ-UHFFFAOYSA-N 0.000 claims 1
- DJCAHZKZXWQRGB-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[3-methyl-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 DJCAHZKZXWQRGB-UHFFFAOYSA-N 0.000 claims 1
- NWYGMUXHPKFFFX-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-(1,4-diazepan-1-yl)-3-methylanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCNCCC2)C(C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl NWYGMUXHPKFFFX-UHFFFAOYSA-N 0.000 claims 1
- DATCYIARXKPUBJ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-(1-methylpiperidin-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 DATCYIARXKPUBJ-UHFFFAOYSA-N 0.000 claims 1
- QUTZVOUNNKGPFD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 QUTZVOUNNKGPFD-UHFFFAOYSA-N 0.000 claims 1
- IWQIFPYCRKJXGB-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 IWQIFPYCRKJXGB-UHFFFAOYSA-N 0.000 claims 1
- BNQVPFAKFCJURC-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2,2-dimethylpropanoyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C(C)(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl BNQVPFAKFCJURC-UHFFFAOYSA-N 0.000 claims 1
- HKDAOTQPQFTQGZ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2-hydroxyacetyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(=O)CO)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl HKDAOTQPQFTQGZ-UHFFFAOYSA-N 0.000 claims 1
- AKGKWVTWFBVCPK-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2-methylpropanoyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl AKGKWVTWFBVCPK-UHFFFAOYSA-N 0.000 claims 1
- JAQWMUMGNOQMGD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopentanecarbonyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CCCC4)=CC=3)N=C2N2C=CN=C21 JAQWMUMGNOQMGD-UHFFFAOYSA-N 0.000 claims 1
- SCGBGGVRWINOLJ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropanecarbonyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(=O)C3CC3)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl SCGBGGVRWINOLJ-UHFFFAOYSA-N 0.000 claims 1
- PSVSKRQYABFVSD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropanecarbonyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 PSVSKRQYABFVSD-UHFFFAOYSA-N 0.000 claims 1
- PGUCIORNTUDLKU-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl PGUCIORNTUDLKU-UHFFFAOYSA-N 0.000 claims 1
- TVROFKVTTFPOPR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2N2C=CN=C21 TVROFKVTTFPOPR-UHFFFAOYSA-N 0.000 claims 1
- XDSGNNMNHWMDOO-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(3,5-dichloro-4-piperazin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C(Cl)C(N4CCNCC4)=C(Cl)C=3)N=C2N2C=CN=C21 XDSGNNMNHWMDOO-UHFFFAOYSA-N 0.000 claims 1
- BETMOIKLRDEYNF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(3,5-difluoro-4-piperazin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C(F)=C(N2CCNCC2)C(F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl BETMOIKLRDEYNF-UHFFFAOYSA-N 0.000 claims 1
- QGTROLNLDGHKID-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-cyclohexylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3CCCCC3)N=C2N2C=CN=C21 QGTROLNLDGHKID-UHFFFAOYSA-N 0.000 claims 1
- GRNBWTTUZPFZLG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-hydroxy-3-methylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(O)C(C)=CC(NC=2N=C3C(C(N(C=4C(=CC=CC=4)Cl)C4=NC=CN43)=O)=CN=2)=C1 GRNBWTTUZPFZLG-UHFFFAOYSA-N 0.000 claims 1
- VQEUOEOBCQPYSX-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-imidazo[1,2-a]pyridin-2-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=C4C=CC=CN4C=3)N=C2N2C=CN=C21 VQEUOEOBCQPYSX-UHFFFAOYSA-N 0.000 claims 1
- ILPBXCNMMNQGRT-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-imidazo[2,1-b][1,3]thiazol-6-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=C4SC=CN4C=3)N=C2N2C=CN=C21 ILPBXCNMMNQGRT-UHFFFAOYSA-N 0.000 claims 1
- ABMZDXLRRXTPDN-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-imidazol-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3C=NC=C3)N=C2N2C=CN=C21 ABMZDXLRRXTPDN-UHFFFAOYSA-N 0.000 claims 1
- NUEJBGYJOOBOHM-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-methylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 NUEJBGYJOOBOHM-UHFFFAOYSA-N 0.000 claims 1
- IUMYMNAILOBLJL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-morpholin-4-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)N=C2N2C=CN=C21 IUMYMNAILOBLJL-UHFFFAOYSA-N 0.000 claims 1
- WJDVIVAHSHCRQL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-piperidin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N2C=CN=C21 WJDVIVAHSHCRQL-UHFFFAOYSA-N 0.000 claims 1
- FNNOSSSVSACDCE-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-piperidin-2-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3NCCCC3)N=C2N2C=CN=C21 FNNOSSSVSACDCE-UHFFFAOYSA-N 0.000 claims 1
- QYRRHAFJBWVMFQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-piperidin-4-yloxyanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(OC4CCNCC4)=CC=3)N=C2N2C=CN=C21 QYRRHAFJBWVMFQ-UHFFFAOYSA-N 0.000 claims 1
- ONHABPWAEIKIJU-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-pyrazol-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C2N2C=CN=C21 ONHABPWAEIKIJU-UHFFFAOYSA-N 0.000 claims 1
- XNDFLXRBPQEZDO-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-pyridin-3-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3C=NC=CC=3)N=C2N2C=CN=C21 XNDFLXRBPQEZDO-UHFFFAOYSA-N 0.000 claims 1
- UFBLJWAOFPIERE-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-pyrrolidin-2-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3NCCC3)N=C2N2C=CN=C21 UFBLJWAOFPIERE-UHFFFAOYSA-N 0.000 claims 1
- JZRFEWFZXOSIDA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-pyrrolidin-3-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3CNCC3)N=C2N2C=CN=C21 JZRFEWFZXOSIDA-UHFFFAOYSA-N 0.000 claims 1
- JIXLPAFSAYXLQW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-thiomorpholin-4-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCSCC3)N=C2N2C=CN=C21 JIXLPAFSAYXLQW-UHFFFAOYSA-N 0.000 claims 1
- VCEWFIVEODTAPW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(5,6,7,8-tetrahydronaphthalen-2-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C4CCCCC4=CC=3)N=C2N2C=CN=C21 VCEWFIVEODTAPW-UHFFFAOYSA-N 0.000 claims 1
- NRAXTRPZXBZAAB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(pyridin-4-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CN=CC=3)N=C2N2C=CN=C21 NRAXTRPZXBZAAB-UHFFFAOYSA-N 0.000 claims 1
- UDARXIKVYRTRBT-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 UDARXIKVYRTRBT-UHFFFAOYSA-N 0.000 claims 1
- RXFZHVDTUZNUDK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1,1,2,3,3-pentamethylisoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2C(C)(C)N(C)C(C)(C)C2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl RXFZHVDTUZNUDK-UHFFFAOYSA-N 0.000 claims 1
- CSGZSKJHPOJUBN-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1,1,2-trimethyl-3,4-dihydroisoquinolin-6-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl CSGZSKJHPOJUBN-UHFFFAOYSA-N 0.000 claims 1
- QGYNNTMCLDQWJN-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1,1,2-trimethyl-3,4-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2C(C)(C)N(C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl QGYNNTMCLDQWJN-UHFFFAOYSA-N 0.000 claims 1
- OZEBXGJIEWGDLG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1,1,2-trimethyl-3H-isoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl OZEBXGJIEWGDLG-UHFFFAOYSA-N 0.000 claims 1
- FNGLHPVBGGVTRR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1-methyl-3,4-dihydro-2H-quinolin-6-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2N(C)CCCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl FNGLHPVBGGVTRR-UHFFFAOYSA-N 0.000 claims 1
- JAFUBIPJLRMFCG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(1-methyl-3,4-dihydro-2H-quinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2N(C)CCCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl JAFUBIPJLRMFCG-UHFFFAOYSA-N 0.000 claims 1
- MUKWAQUSFPAUGU-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl MUKWAQUSFPAUGU-UHFFFAOYSA-N 0.000 claims 1
- IEWDIQKMZRVANG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(2-ethyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CC)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl IEWDIQKMZRVANG-UHFFFAOYSA-N 0.000 claims 1
- PFAIKAPJSZVPTC-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CN(C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl PFAIKAPJSZVPTC-UHFFFAOYSA-N 0.000 claims 1
- UGDHRERXJQTXBB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl UGDHRERXJQTXBB-UHFFFAOYSA-N 0.000 claims 1
- PEUULKFEGQHWFY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(3-cyclopropyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C4CCN(CCC4=CC=3)C3CC3)N=C2N2C=CN=C21 PEUULKFEGQHWFY-UHFFFAOYSA-N 0.000 claims 1
- YHQXNFMHVVJBPZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl YHQXNFMHVVJBPZ-UHFFFAOYSA-N 0.000 claims 1
- ZGBTXCDUOKJJGB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(4,4-dimethyl-2-propan-2-yl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl ZGBTXCDUOKJJGB-UHFFFAOYSA-N 0.000 claims 1
- SRCDFSLLQZAPHB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(6-piperazin-1-ylpyridin-3-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=NC(=CC=3)N3CCNCC3)N=C2N2C=CN=C21 SRCDFSLLQZAPHB-UHFFFAOYSA-N 0.000 claims 1
- YKCNYRMBKPOZJR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl YKCNYRMBKPOZJR-UHFFFAOYSA-N 0.000 claims 1
- CUJAWNMZKOEMSZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[2-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1CCCOC(C=C1C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 CUJAWNMZKOEMSZ-UHFFFAOYSA-N 0.000 claims 1
- MLHGGHCZXJGZOR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3,5-difluoro-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)F)=C(F)C=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 MLHGGHCZXJGZOR-UHFFFAOYSA-N 0.000 claims 1
- NBWFIGVYZCDJNB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-(3-piperidin-1-ylpropoxy)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C(OCCCN4CCCCC4)C=CC=3)N=C2N2C=CN=C21 NBWFIGVYZCDJNB-UHFFFAOYSA-N 0.000 claims 1
- XTNHIIWNDNCKKF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=C3C(C(N(C=4C(=CC=CC=4)Cl)C4=NC=CN43)=O)=CN=2)=C1 XTNHIIWNDNCKKF-UHFFFAOYSA-N 0.000 claims 1
- GKAGRSUWJGSEAR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-(hydroxymethyl)-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)CO)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GKAGRSUWJGSEAR-UHFFFAOYSA-N 0.000 claims 1
- MESANKRTXWTCGC-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-(pyrrolidin-1-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=C(CN4CCCC4)C=CC=3)N=C2N2C=CN=C21 MESANKRTXWTCGC-UHFFFAOYSA-N 0.000 claims 1
- MGQYJIGVHIABLP-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-[3-(4-methylpiperazin-1-yl)propoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(NC=2N=C3C(C(N(C=4C(=CC=CC=4)Cl)C4=NC=CN43)=O)=CN=2)=C1 MGQYJIGVHIABLP-UHFFFAOYSA-N 0.000 claims 1
- NCSLSRHAGUPMIR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-chloro-4-[2-(propan-2-ylamino)ethoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(Cl)C(OCCNC(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 NCSLSRHAGUPMIR-UHFFFAOYSA-N 0.000 claims 1
- LTDJVNXPFRTHPR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-chloro-4-piperazin-1-yl-5-(trifluoromethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C(Cl)=C(N2CCNCC2)C(C(F)(F)F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl LTDJVNXPFRTHPR-UHFFFAOYSA-N 0.000 claims 1
- QEQAQSMIISYCKJ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-ethyl-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(CC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl QEQAQSMIISYCKJ-UHFFFAOYSA-N 0.000 claims 1
- SXKZCTYUUSMWNZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-fluoro-4-(4-propan-2-ylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(C)C)CCN1C(C(=C1)F)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SXKZCTYUUSMWNZ-UHFFFAOYSA-N 0.000 claims 1
- PLPDBCQEFQSXHI-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-fluoro-4-[2-(4-methylpiperazin-1-yl)ethoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1CCOC(C(=C1)F)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 PLPDBCQEFQSXHI-UHFFFAOYSA-N 0.000 claims 1
- XQJXUOKWSDUBCA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(OC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl XQJXUOKWSDUBCA-UHFFFAOYSA-N 0.000 claims 1
- HWJXZCPWQIVHCB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-methoxy-4-[2-(propan-2-ylamino)ethoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(OCCNC(C)C)C(OC)=CC(NC=2N=C3C(C(N(C=4C(=CC=CC=4)Cl)C4=NC=CN43)=O)=CN=2)=C1 HWJXZCPWQIVHCB-UHFFFAOYSA-N 0.000 claims 1
- GCFKMPJJZHGGAY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-methyl-4-(4-methyl-1,4-diazepan-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GCFKMPJJZHGGAY-UHFFFAOYSA-N 0.000 claims 1
- ODBWPJDXYDPWJA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ODBWPJDXYDPWJA-UHFFFAOYSA-N 0.000 claims 1
- HZLADDZBGLEJJV-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1,3-thiazol-2-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3SC=CN=3)N=C2N2C=CN=C21 HZLADDZBGLEJJV-UHFFFAOYSA-N 0.000 claims 1
- PAMCBQTYCXAOMS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1,3-thiazol-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=CSC=3)N=C2N2C=CN=C21 PAMCBQTYCXAOMS-UHFFFAOYSA-N 0.000 claims 1
- OONVXTKZKIAQMC-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1,8-naphthyridin-2-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=C4N=CC=CC4=CC=3)N=C2N2C=CN=C21 OONVXTKZKIAQMC-UHFFFAOYSA-N 0.000 claims 1
- HLCFJKUJLMXDCF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1-methylpiperidin-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 HLCFJKUJLMXDCF-UHFFFAOYSA-N 0.000 claims 1
- BSIGDYDOKKECNI-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1H-pyrazol-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3=CNN=C3)N=C2N2C=CN=C21 BSIGDYDOKKECNI-UHFFFAOYSA-N 0.000 claims 1
- HHSNMKMVCYOUFX-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(2,3-dihydroimidazo[2,1-b][1,3]thiazol-6-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=C4SCCN4C=3)N=C2N2C=CN=C21 HHSNMKMVCYOUFX-UHFFFAOYSA-N 0.000 claims 1
- QQJLLPSWBNUDQY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(2-morpholin-4-yl-1,3-thiazol-4-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3N=C(SC=3)N3CCOCC3)N=C2N2C=CN=C21 QQJLLPSWBNUDQY-UHFFFAOYSA-N 0.000 claims 1
- CKXFGVRIQGJCTK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(2-morpholin-4-ylethoxy)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(OCCN4CCOCC4)=CC=3)N=C2N2C=CN=C21 CKXFGVRIQGJCTK-UHFFFAOYSA-N 0.000 claims 1
- YCJSWOWKXTVETQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(2-morpholin-4-ylethylamino)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCN4CCOCC4)=CC=3)N=C2N2C=CN=C21 YCJSWOWKXTVETQ-UHFFFAOYSA-N 0.000 claims 1
- MKQPIHBOLOTWHR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(2-pyrrolidin-1-ylethylamino)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCN4CCCC4)=CC=3)N=C2N2C=CN=C21 MKQPIHBOLOTWHR-UHFFFAOYSA-N 0.000 claims 1
- RZDUUOJUVMNMFW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(3-imidazol-1-ylpropylamino)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCCN4C=NC=C4)=CC=3)N=C2N2C=CN=C21 RZDUUOJUVMNMFW-UHFFFAOYSA-N 0.000 claims 1
- WRQLVOWKUUIYKQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(3-morpholin-4-ylpropylamino)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCCN4CCOCC4)=CC=3)N=C2N2C=CN=C21 WRQLVOWKUUIYKQ-UHFFFAOYSA-N 0.000 claims 1
- ICIOPPGTCQNTNY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(3-oxo-1,2-dihydroindazol-7-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C=3C4=C(C(NN4)=O)C=CC=3)N=C2N2C=CN=C21 ICIOPPGTCQNTNY-UHFFFAOYSA-N 0.000 claims 1
- SCWRDQQXVOUYHS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-hydroxypiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SCWRDQQXVOUYHS-UHFFFAOYSA-N 0.000 claims 1
- HVRSFBMFPRDHBS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-hydroxypiperidine-1-carbonyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 HVRSFBMFPRDHBS-UHFFFAOYSA-N 0.000 claims 1
- FYUMRXXTENSYRF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)-3-propan-2-ylanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(C(C)C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl FYUMRXXTENSYRF-UHFFFAOYSA-N 0.000 claims 1
- OFLUWBFGEJMLNG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,3,4,5,7,11,13-heptazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NN=NN3C2=N1 OFLUWBFGEJMLNG-UHFFFAOYSA-N 0.000 claims 1
- YENWEOCDIMPAIL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,4,5,7,11,13-hexazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NN=CN3C2=N1 YENWEOCDIMPAIL-UHFFFAOYSA-N 0.000 claims 1
- IICGNJDSNUEEHR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 IICGNJDSNUEEHR-UHFFFAOYSA-N 0.000 claims 1
- SHECBVUSRYTIRU-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaene-8-thione Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=S)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SHECBVUSRYTIRU-UHFFFAOYSA-N 0.000 claims 1
- QOZMDPNEYXJJHY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazine-1-carbonyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 QOZMDPNEYXJJHY-UHFFFAOYSA-N 0.000 claims 1
- MFITWXWCJVWMHQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-morpholin-4-ylpiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCOCC3)N=C2N2C=CN=C21 MFITWXWCJVWMHQ-UHFFFAOYSA-N 0.000 claims 1
- GCFBDNMUIHNLIV-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-piperidin-1-ylpiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCCC3)N=C2N2C=CN=C21 GCFBDNMUIHNLIV-UHFFFAOYSA-N 0.000 claims 1
- DPGFXRUPDBRYKG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 DPGFXRUPDBRYKG-UHFFFAOYSA-N 0.000 claims 1
- XSFRKOIPMNHCSK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-pyridin-2-ylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C=3N=CC=CC=3)N=C2N2C=CN=C21 XSFRKOIPMNHCSK-UHFFFAOYSA-N 0.000 claims 1
- WZRMRABHYLDJJF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCC3)N=C2N2C=CN=C21 WZRMRABHYLDJJF-UHFFFAOYSA-N 0.000 claims 1
- STJGZOBBYGZWPX-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(hydroxymethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(CO)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 STJGZOBBYGZWPX-UHFFFAOYSA-N 0.000 claims 1
- SBFKEEHRFNMNNG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(imidazol-1-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(CN4C=NC=C4)=CC=3)N=C2N2C=CN=C21 SBFKEEHRFNMNNG-UHFFFAOYSA-N 0.000 claims 1
- MJBJKFZMPBCFBE-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(morpholin-4-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(CN4CCOCC4)=CC=3)N=C2N2C=CN=C21 MJBJKFZMPBCFBE-UHFFFAOYSA-N 0.000 claims 1
- GASZSOBCXYCKAV-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(piperidin-4-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(CC4CCNCC4)=CC=3)N=C2N2C=CN=C21 GASZSOBCXYCKAV-UHFFFAOYSA-N 0.000 claims 1
- SHDASFTVMNGMQE-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(pyrazol-1-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(CN4N=CC=C4)=CC=3)N=C2N2C=CN=C21 SHDASFTVMNGMQE-UHFFFAOYSA-N 0.000 claims 1
- LPILJTRIDGYRLT-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(pyrrolidin-1-ylmethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(CN4CCCC4)=CC=3)N=C2N2C=CN=C21 LPILJTRIDGYRLT-UHFFFAOYSA-N 0.000 claims 1
- KRQQYGJSUNKQPS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(trifluoromethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 KRQQYGJSUNKQPS-UHFFFAOYSA-N 0.000 claims 1
- ZHZHDFPEDFXLKW-LJQANCHMSA-N 7-(2-chlorophenyl)-12-[4-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC[C@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ZHZHDFPEDFXLKW-LJQANCHMSA-N 0.000 claims 1
- ZHZHDFPEDFXLKW-IBGZPJMESA-N 7-(2-chlorophenyl)-12-[4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ZHZHDFPEDFXLKW-IBGZPJMESA-N 0.000 claims 1
- ZOTWQCYFAPLVSS-QFIPXVFZSA-N 7-(2-chlorophenyl)-12-[4-[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3[C@@H](CCC3)CN3CCCC3)N=C2N2C=CN=C21 ZOTWQCYFAPLVSS-QFIPXVFZSA-N 0.000 claims 1
- OOHKMENCNVDUEZ-FQEVSTJZSA-N 7-(2-chlorophenyl)-12-[4-[(2S)-2-(trifluoromethyl)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC(F)(F)[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 OOHKMENCNVDUEZ-FQEVSTJZSA-N 0.000 claims 1
- VHEALHXMBUECJS-LJQANCHMSA-N 7-(2-chlorophenyl)-12-[4-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@H](N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 VHEALHXMBUECJS-LJQANCHMSA-N 0.000 claims 1
- OCZSMSRPDZFEBY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(1-methylpyrrolidin-2-yl)ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound CN1CCCC1CCNC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 OCZSMSRPDZFEBY-UHFFFAOYSA-N 0.000 claims 1
- AAZRWBWWHVIATQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(1H-imidazol-5-yl)ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCC=4N=CNC=4)=CC=3)N=C2N2C=CN=C21 AAZRWBWWHVIATQ-UHFFFAOYSA-N 0.000 claims 1
- TUZDSLJKMWZQQS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(6-methylquinolin-2-yl)ethyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC2=CC(C)=CC=C2N=C1CCC(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl TUZDSLJKMWZQQS-UHFFFAOYSA-N 0.000 claims 1
- SJAZUYFBVKZIHT-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(diethylamino)ethoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SJAZUYFBVKZIHT-UHFFFAOYSA-N 0.000 claims 1
- GCRIPFFAFGSGJZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(dimethylamino)ethoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GCRIPFFAFGSGJZ-UHFFFAOYSA-N 0.000 claims 1
- FWVAXLUYFOSLLD-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(dimethylamino)ethyl-ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(CCN(C)C)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 FWVAXLUYFOSLLD-UHFFFAOYSA-N 0.000 claims 1
- WOULXCXHUMPFBR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(dimethylamino)ethyl-methylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(C)CCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 WOULXCXHUMPFBR-UHFFFAOYSA-N 0.000 claims 1
- GVACRQGZFUXYFH-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(dimethylamino)ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(NCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GVACRQGZFUXYFH-UHFFFAOYSA-N 0.000 claims 1
- OOHKMENCNVDUEZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[2-(trifluoromethyl)pyrrolidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC(F)(F)C1CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 OOHKMENCNVDUEZ-UHFFFAOYSA-N 0.000 claims 1
- SYMCJHNCSLFDEE-GOSISDBHSA-N 7-(2-chlorophenyl)-12-[4-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C[C@@H]1CCCN1CCC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SYMCJHNCSLFDEE-GOSISDBHSA-N 0.000 claims 1
- QTUTZQJDHFNMIL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(2-oxopyrrolidin-1-yl)propylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NCCCN4C(CCC4)=O)=CC=3)N=C2N2C=CN=C21 QTUTZQJDHFNMIL-UHFFFAOYSA-N 0.000 claims 1
- KTBMIBCGXFCLPU-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(diethylamino)propoxy]-3-fluoroanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(F)C(OCCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 KTBMIBCGXFCLPU-UHFFFAOYSA-N 0.000 claims 1
- XFQKZYWBZGCPLZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(diethylamino)propoxy]-3-methylanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(C)C(OCCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 XFQKZYWBZGCPLZ-UHFFFAOYSA-N 0.000 claims 1
- SOZPDGNNIAKORH-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(dimethylamino)propyl-methylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(C)CCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SOZPDGNNIAKORH-UHFFFAOYSA-N 0.000 claims 1
- JZMDEGGHLUISMB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(trifluoromethyl)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C(C(F)(F)F)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 JZMDEGGHLUISMB-UHFFFAOYSA-N 0.000 claims 1
- YIFPUJOZGFNUSO-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(4-fluorophenyl)piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=2)CC1 YIFPUJOZGFNUSO-UHFFFAOYSA-N 0.000 claims 1
- PMKVKTIUZFRYPK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(cyclohexylmethyl)piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(CC4CCCCC4)CC3)N=C2N2C=CN=C21 PMKVKTIUZFRYPK-UHFFFAOYSA-N 0.000 claims 1
- ICOWOOZKFOHYEH-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ICOWOOZKFOHYEH-UHFFFAOYSA-N 0.000 claims 1
- ZIVISXMJPANONQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(oxetan-3-yl)piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C3COC3)N=C2N2C=CN=C21 ZIVISXMJPANONQ-UHFFFAOYSA-N 0.000 claims 1
- DPYHKUBAWKDQGM-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(CCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 DPYHKUBAWKDQGM-UHFFFAOYSA-N 0.000 claims 1
- GIZSAAKJRUZMGS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GIZSAAKJRUZMGS-UHFFFAOYSA-N 0.000 claims 1
- QLSQWQRZAPISIU-KRWDZBQOSA-N 7-(2-chlorophenyl)-12-[4-[[(2S)-pyrrolidin-2-yl]methoxy]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(OC[C@H]4NCCC4)=CC=3)N=C2N2C=CN=C21 QLSQWQRZAPISIU-KRWDZBQOSA-N 0.000 claims 1
- GYVYBZGLYXUARW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[propan-2-yl-[2-(propan-2-ylamino)ethyl]amino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(C(C)C)CCNC(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GYVYBZGLYXUARW-UHFFFAOYSA-N 0.000 claims 1
- QPQHXCXOUDEHOR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-piperazin-1-yl-3-(trifluoromethyl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCNCC2)C(C(F)(F)F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl QPQHXCXOUDEHOR-UHFFFAOYSA-N 0.000 claims 1
- RWJCTWYINAYMFV-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[1-[2-(dimethylamino)ethyl]-2,3-dihydroindol-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2N(CCN(C)C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl RWJCTWYINAYMFV-UHFFFAOYSA-N 0.000 claims 1
- ABALSCAZEPXGDF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(2-ethylbutyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CC(CC)CC)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl ABALSCAZEPXGDF-UHFFFAOYSA-N 0.000 claims 1
- XTNWAFVIHYHKCI-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(2-hydroxyethyl)-3,4-dihydro-1H-isoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CN(CCO)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl XTNWAFVIHYHKCI-UHFFFAOYSA-N 0.000 claims 1
- KKCUAASUFOILPL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(2-methoxyethyl)-3,4-dihydro-1H-isoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CN(CCOC)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl KKCUAASUFOILPL-UHFFFAOYSA-N 0.000 claims 1
- LWKBFYGLHVKLIW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(cyclohexylmethyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1CCCCC1 LWKBFYGLHVKLIW-UHFFFAOYSA-N 0.000 claims 1
- GWNIPMQQLSAOTM-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(cyclopropylmethyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1CC1 GWNIPMQQLSAOTM-UHFFFAOYSA-N 0.000 claims 1
- PVJFQINWMUVXBI-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl PVJFQINWMUVXBI-UHFFFAOYSA-N 0.000 claims 1
- OQHAWPBWPDOYBQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-[(4-imidazol-1-ylphenyl)methyl]-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC(C=C1)=CC=C1N1C=CN=C1 OQHAWPBWPDOYBQ-UHFFFAOYSA-N 0.000 claims 1
- DKQPDIYSKXVOFA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(2,2,2-trifluoroethyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CC(F)(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl DKQPDIYSKXVOFA-UHFFFAOYSA-N 0.000 claims 1
- FMBORYIZQRKJLK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(4,4,4-trifluorobutyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CCCC(F)(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl FMBORYIZQRKJLK-UHFFFAOYSA-N 0.000 claims 1
- UXOLVCNWZNMQMB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(pyridin-3-ylmethyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1=CC=CN=C1 UXOLVCNWZNMQMB-UHFFFAOYSA-N 0.000 claims 1
- HKBWWKPGTXQPIA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(thiophen-3-ylmethyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC=1C=CSC=1 HKBWWKPGTXQPIA-UHFFFAOYSA-N 0.000 claims 1
- XVLSHQPTPJYEAT-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-[(4-propoxyphenyl)methyl]-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(OCCC)=CC=C1CN1CC(C)(C)C2=CC=C(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)C=C2C1 XVLSHQPTPJYEAT-UHFFFAOYSA-N 0.000 claims 1
- ZUOSENQRSAWNKY-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ZUOSENQRSAWNKY-UHFFFAOYSA-N 0.000 claims 1
- LHLGMQAZACYFPV-UHFFFAOYSA-N 7-(2-chlorophenyl)-3-methyl-12-[4-(4-methylpiperazin-1-yl)anilino]-2,4,5,7,11,13-hexazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NN=C(C)N3C2=N1 LHLGMQAZACYFPV-UHFFFAOYSA-N 0.000 claims 1
- XEYIRLOQTLKFHY-UHFFFAOYSA-N 7-(2-chlorophenyl)-3-methyl-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=C(C)N3C2=N1 XEYIRLOQTLKFHY-UHFFFAOYSA-N 0.000 claims 1
- DVYLGXXGLPOVGT-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-imino-N-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-amine Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=N)C=1N1C=CN=C1N2C1=CC=CC=C1Cl DVYLGXXGLPOVGT-UHFFFAOYSA-N 0.000 claims 1
- KEPDHUGTPHFUOM-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-imino-N-[4-(4-methylpiperazin-1-yl)phenyl]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=N)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 KEPDHUGTPHFUOM-UHFFFAOYSA-N 0.000 claims 1
- MFDOYNTUZCCLIV-UHFFFAOYSA-N 7-(2-methoxyphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2N2C=CN=C21 MFDOYNTUZCCLIV-UHFFFAOYSA-N 0.000 claims 1
- XZVUXDVMSJADHH-UHFFFAOYSA-N 7-(2-methylphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)C)C3=NC=CN3C2=N1 XZVUXDVMSJADHH-UHFFFAOYSA-N 0.000 claims 1
- BVSHKIRKMXGZMN-UHFFFAOYSA-N 7-(3-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=C(Cl)C=CC=3)C3=NC=CN3C2=N1 BVSHKIRKMXGZMN-UHFFFAOYSA-N 0.000 claims 1
- GTVAFXIRKVPEGA-UHFFFAOYSA-N 7-(3-fluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=C(F)C=CC=3)C3=NC=CN3C2=N1 GTVAFXIRKVPEGA-UHFFFAOYSA-N 0.000 claims 1
- BUJBUAPLAJWDLH-UHFFFAOYSA-N 7-[2-chloro-4-(trifluoromethyl)phenyl]-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(=CC=3)C(F)(F)F)Cl)C3=NC=CN3C2=N1 BUJBUAPLAJWDLH-UHFFFAOYSA-N 0.000 claims 1
- UFUYHRZIJHDGIT-UHFFFAOYSA-N 7-[[7-(2-chloro-6-fluorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-4,4-dimethyl-1,3-dihydroisoquinoline-2-sulfonamide Chemical compound C=1C=C2C(C)(C)CN(S(N)(=O)=O)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl UFUYHRZIJHDGIT-UHFFFAOYSA-N 0.000 claims 1
- KYLYVGCGAVZINF-UHFFFAOYSA-N 7-[[7-(2-chloro-6-fluorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-2-carboxamide Chemical compound C=1C=C2C3(CC3)CN(C(=O)NC)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl KYLYVGCGAVZINF-UHFFFAOYSA-N 0.000 claims 1
- SCWAHOJJUNVFNK-UHFFFAOYSA-N 7-[[7-(2-chloro-6-fluorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-N-propan-2-ylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-2-carboxamide Chemical compound C=1C=C2C3(CC3)CN(C(=O)NC(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl SCWAHOJJUNVFNK-UHFFFAOYSA-N 0.000 claims 1
- WVNQOFKQYRFPIJ-UHFFFAOYSA-N 7-cyclohexyl-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C3CCCCC3)C3=NC=CN3C2=N1 WVNQOFKQYRFPIJ-UHFFFAOYSA-N 0.000 claims 1
- CWWLREJNRGUASV-UHFFFAOYSA-N AKI00000020a Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)N=C2N2C=CN=C21 CWWLREJNRGUASV-UHFFFAOYSA-N 0.000 claims 1
- GKGDBNYEBLXRBK-UHFFFAOYSA-N C1=C2CC(NCCF)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl Chemical compound C1=C2CC(NCCF)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GKGDBNYEBLXRBK-UHFFFAOYSA-N 0.000 claims 1
- JFAMEOZAQRJLBS-UAPYVXQJSA-N C1C[C@@H](O)CC[C@@H]1NC(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 JFAMEOZAQRJLBS-UAPYVXQJSA-N 0.000 claims 1
- QOWZEOJBRPFCFG-UHFFFAOYSA-N C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl QOWZEOJBRPFCFG-UHFFFAOYSA-N 0.000 claims 1
- MEJCDTUASJICTL-UHFFFAOYSA-N C=1C=C2C(C)(C)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl Chemical compound C=1C=C2C(C)(C)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl MEJCDTUASJICTL-UHFFFAOYSA-N 0.000 claims 1
- DWRDTRFUFLBCNX-UHFFFAOYSA-N C=1C=C2C(C)(C)CN(CCF)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl Chemical compound C=1C=C2C(C)(C)CN(CCF)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl DWRDTRFUFLBCNX-UHFFFAOYSA-N 0.000 claims 1
- YFXPXAIGNXNQIY-UHFFFAOYSA-N C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl YFXPXAIGNXNQIY-UHFFFAOYSA-N 0.000 claims 1
- HJTVIZPBTFNXGN-UHFFFAOYSA-N C=1C=C2C3(CC3)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl Chemical compound C=1C=C2C3(CC3)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl HJTVIZPBTFNXGN-UHFFFAOYSA-N 0.000 claims 1
- SAMKOIRNJNKDSB-UHFFFAOYSA-N N-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-1-methylpiperidine-4-carboxamide Chemical compound C1CN(C)CCC1C(=O)NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SAMKOIRNJNKDSB-UHFFFAOYSA-N 0.000 claims 1
- OXRSDNJFGFDKCI-UHFFFAOYSA-N N-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-4-hydroxycyclohexane-1-carboxamide Chemical compound C1CC(O)CCC1C(=O)NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 OXRSDNJFGFDKCI-UHFFFAOYSA-N 0.000 claims 1
- ZSLIZCAXMMDJTD-UHFFFAOYSA-N N-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ZSLIZCAXMMDJTD-UHFFFAOYSA-N 0.000 claims 1
- SOYSPINXUBJEKX-UHFFFAOYSA-N N-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]cyclopentanecarboxamide Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NC(=O)C4CCCC4)=CC=3)N=C2N2C=CN=C21 SOYSPINXUBJEKX-UHFFFAOYSA-N 0.000 claims 1
- WUPJPYDSZZOXNN-UHFFFAOYSA-N N-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]pyridine-4-carboxamide Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(NC(=O)C=4C=CN=CC=4)=CC=3)N=C2N2C=CN=C21 WUPJPYDSZZOXNN-UHFFFAOYSA-N 0.000 claims 1
- JKPCLADUTSTTEJ-UHFFFAOYSA-N S1C(NC)=NC(C)=C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 Chemical compound S1C(NC)=NC(C)=C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JKPCLADUTSTTEJ-UHFFFAOYSA-N 0.000 claims 1
- CLMIGLFZQQFETA-UHFFFAOYSA-N S1CC(=O)N(C(C)C)C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 Chemical compound S1CC(=O)N(C(C)C)C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 CLMIGLFZQQFETA-UHFFFAOYSA-N 0.000 claims 1
- BDDUADGEDLHERS-XMMISQBUSA-N [(1R)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl] 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoate Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C(=O)O[C@H]3C4CCCCN4CCC3)N=C2N2C=CN=C21 BDDUADGEDLHERS-XMMISQBUSA-N 0.000 claims 1
- INBLGJXWYYQNCP-UHFFFAOYSA-N methyl 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 INBLGJXWYYQNCP-UHFFFAOYSA-N 0.000 claims 1
- FHKMQEPNAVSOMS-UHFFFAOYSA-N tert-butyl 7-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound C1=C2CN(C(=O)OC(C)(C)C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl FHKMQEPNAVSOMS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 115
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
- 201000010099 disease Diseases 0.000 abstract description 11
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 261
- 238000005160 1H NMR spectroscopy Methods 0.000 description 160
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 97
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 71
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 60
- MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000004128 high performance liquid chromatography Methods 0.000 description 40
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000013058 crude material Substances 0.000 description 34
- 239000012044 organic layer Substances 0.000 description 34
- 229920006395 saturated elastomer Polymers 0.000 description 34
- 235000017557 sodium bicarbonate Nutrition 0.000 description 31
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 239000012267 brine Substances 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- BFWOXWLQVUGAMG-UHFFFAOYSA-N tert-butyl 7-aminospiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2=CC(N)=CC=C2C21CC2 BFWOXWLQVUGAMG-UHFFFAOYSA-N 0.000 description 15
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 13
- 125000004452 carbocyclyl group Chemical group 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000006413 ring segment Chemical group 0.000 description 12
- 229910052721 tungsten Inorganic materials 0.000 description 12
- DWFPZDNYWVYUMK-UHFFFAOYSA-N 1h-pyrimido[4,5-d]pyrimidine-2,4-dione Chemical compound C1=NC=C2C(=O)NC(=O)NC2=N1 DWFPZDNYWVYUMK-UHFFFAOYSA-N 0.000 description 11
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 125000004076 pyridyl group Chemical group 0.000 description 11
- 102000014914 Carrier Proteins Human genes 0.000 description 10
- 108091008324 binding proteins Proteins 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- 241000937413 Axia Species 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 125000002757 morpholinyl group Chemical group 0.000 description 9
- 125000004193 piperazinyl group Chemical group 0.000 description 9
- 125000003386 piperidinyl group Chemical group 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000427 antigen Substances 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000005959 diazepanyl group Chemical group 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 102000014150 Interferons Human genes 0.000 description 7
- 108010050904 Interferons Proteins 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
- 125000000842 isoxazolyl group Chemical group 0.000 description 7
- 229940043355 kinase inhibitor Drugs 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 7
- 125000003226 pyrazolyl group Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 125000000335 thiazolyl group Chemical group 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 210000001744 T-lymphocyte Anatomy 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 6
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
- 125000001786 isothiazolyl group Chemical group 0.000 description 6
- 230000011278 mitosis Effects 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229960005486 vaccine Drugs 0.000 description 6
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 5
- NIXCVBFXLJWUTC-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]aniline Chemical compound C1CN(C)CCN1CC1=CC=C(N)C=C1 NIXCVBFXLJWUTC-UHFFFAOYSA-N 0.000 description 5
- 102100025064 Cellular tumor antigen p53 Human genes 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
- 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 5
- ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical group O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 235000019483 Peanut oil Nutrition 0.000 description 5
- 230000006907 apoptotic process Effects 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 230000002950 deficient Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000002632 imidazolidinyl group Chemical group 0.000 description 5
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000312 peanut oil Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 5
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 5
- 125000005412 pyrazyl group Chemical group 0.000 description 5
- 125000002098 pyridazinyl group Chemical group 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 5
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 4
- CMUJYCZVTCSEPM-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-2,3-dihydroindol-5-amine Chemical compound NC1=CC=C2N(CCN(C)C)CCC2=C1 CMUJYCZVTCSEPM-UHFFFAOYSA-N 0.000 description 4
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 102000016736 Cyclin Human genes 0.000 description 4
- 108050006400 Cyclin Proteins 0.000 description 4
- 102000001301 EGF receptor Human genes 0.000 description 4
- 108060006698 EGF receptor Proteins 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002136 L01XE07 - Lapatinib Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 108091007960 PI3Ks Proteins 0.000 description 4
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 4
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 102000001253 Protein Kinase Human genes 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 4
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 4
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 description 4
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 4
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000000532 dioxanyl group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 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 4
- 239000000706 filtrate Substances 0.000 description 4
- 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 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 4
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- 229960000435 oblimersen Drugs 0.000 description 4
- MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 4
- 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 4
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920001184 polypeptide Polymers 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 108060006633 protein kinase Proteins 0.000 description 4
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 4
- RMHRRMBFHGEDSR-UHFFFAOYSA-N tert-butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=N1 RMHRRMBFHGEDSR-UHFFFAOYSA-N 0.000 description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 4
- 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 4
- 229960001670 trilostane Drugs 0.000 description 4
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 3
- PVCULFYROUOVGJ-UHFFFAOYSA-N 1-[2-chloroethyl(methylsulfonyl)amino]-3-methyl-1-methylsulfonylurea Chemical compound CNC(=O)N(S(C)(=O)=O)N(S(C)(=O)=O)CCCl PVCULFYROUOVGJ-UHFFFAOYSA-N 0.000 description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 0.000 description 3
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- 102000009058 Death Domain Receptors Human genes 0.000 description 3
- 108010049207 Death Domain Receptors Proteins 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 108091008606 PDGF receptors Proteins 0.000 description 3
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 3
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 3
- 108020004459 Small interfering RNA Proteins 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 229930013930 alkaloid Natural products 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
- 229940049595 antibody-drug conjugate Drugs 0.000 description 3
- 239000003719 aurora kinase inhibitor Substances 0.000 description 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 3
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 230000023359 cell cycle switching, meiotic to mitotic cell cycle Effects 0.000 description 3
- 230000032823 cell division Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 229960000684 cytarabine Drugs 0.000 description 3
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 3
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 description 3
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 3
- 125000004597 dihydrobenzothiopyranyl group Chemical group S1C(CCC2=C1C=CC=C2)* 0.000 description 3
- WOKPSXJEBSRSAT-UHFFFAOYSA-N dihydrobenzothiopyranyl sulfone group Chemical group S1C(CCC2=C1C=CC=C2)S(=O)(=O)C2SC1=C(CC2)C=CC=C1 WOKPSXJEBSRSAT-UHFFFAOYSA-N 0.000 description 3
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 description 3
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 3
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 description 3
- 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 3
- 208000035475 disorder Diseases 0.000 description 3
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 3
- 229960004945 etoricoxib Drugs 0.000 description 3
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 description 3
- 229950009429 exatecan Drugs 0.000 description 3
- 229960000390 fludarabine Drugs 0.000 description 3
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 3
- 229960002949 fluorouracil Drugs 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 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 3
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 3
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
- 229950003063 mitumomab Drugs 0.000 description 3
- VOWOEBADKMXUBU-UHFFFAOYSA-J molecular oxygen;tetrachlorite;hydrate Chemical compound O.O=O.[O-]Cl=O.[O-]Cl=O.[O-]Cl=O.[O-]Cl=O VOWOEBADKMXUBU-UHFFFAOYSA-J 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- FDLYAMZZIXQODN-UHFFFAOYSA-N olaparib Chemical compound FC1=CC=C(CC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CC1 FDLYAMZZIXQODN-UHFFFAOYSA-N 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 3
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 125000004590 pyridopyridyl group Chemical group N1=C(C=CC2=C1C=CC=N2)* 0.000 description 3
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 3
- 238000001959 radiotherapy Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000002336 ribonucleotide Substances 0.000 description 3
- 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 3
- 229950009213 rubitecan Drugs 0.000 description 3
- BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical compound C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 235000011803 sesame oil Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000004589 thienofuryl group Chemical group O1C(=CC2=C1C=CS2)* 0.000 description 3
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 3
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 3
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 3
- 229960004528 vincristine Drugs 0.000 description 3
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 3
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 3
- WVTKBKWTSCPRNU-KYJUHHDHSA-N (+)-Tetrandrine Chemical compound C([C@H]1C=2C=C(C(=CC=2CCN1C)OC)O1)C(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2C[C@@H]2N(C)CCC3=CC(OC)=C(OC)C1=C23 WVTKBKWTSCPRNU-KYJUHHDHSA-N 0.000 description 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 2
- LVLLALCJVJNGQQ-SEODYNFXSA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r,3e,5e)-7-ethyl-7-hydroxynona-3,5-dien-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/C=C/C(O)(CC)CC)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C LVLLALCJVJNGQQ-SEODYNFXSA-N 0.000 description 2
- IFIOUOYJVOSTFH-UHFFFAOYSA-N (2-fluoro-5-nitrophenyl)methanol Chemical compound OCC1=CC([N+]([O-])=O)=CC=C1F IFIOUOYJVOSTFH-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- 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 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
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
- ZZUBHVMHNVYXRR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1=CC2=CC=C(O)C=C2OC1 ZZUBHVMHNVYXRR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- LOCKPKWGFIBYLB-UHFFFAOYSA-N 3-chloro-4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1Cl LOCKPKWGFIBYLB-UHFFFAOYSA-N 0.000 description 2
- NOGFOWCYFNRFJG-UHFFFAOYSA-N 3-fluoro-4-(4-propan-2-ylpiperazin-1-yl)aniline Chemical compound C1CN(C(C)C)CCN1C1=CC=C(N)C=C1F NOGFOWCYFNRFJG-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- AFEAGBCLWMVRHF-UHFFFAOYSA-N 3-methoxy-4-(4-methylpiperazin-1-yl)aniline Chemical compound COC1=CC(N)=CC=C1N1CCN(C)CC1 AFEAGBCLWMVRHF-UHFFFAOYSA-N 0.000 description 2
- RWTJVGLEXNIAME-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)aniline Chemical compound C1=CC(N)=CC=C1N1CC2CCCN2CC1 RWTJVGLEXNIAME-UHFFFAOYSA-N 0.000 description 2
- CRLKNBUQRZOYSE-UHFFFAOYSA-N 4-(4-propan-2-ylpiperazin-1-yl)aniline Chemical compound C1CN(C(C)C)CCN1C1=CC=C(N)C=C1 CRLKNBUQRZOYSE-UHFFFAOYSA-N 0.000 description 2
- GRSFQNVAPVZAOV-UHFFFAOYSA-N 4-[3-(diethylamino)propoxy]-3-fluoroaniline Chemical compound CCN(CC)CCCOC1=CC=C(N)C=C1F GRSFQNVAPVZAOV-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- DQOGWKZQQBYYMW-LQGIGNHCSA-N 5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine;(2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O.COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 DQOGWKZQQBYYMW-LQGIGNHCSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 2
- GOLCXWYRSKYTSP-UHFFFAOYSA-N Arsenious Acid Chemical compound O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 2
- 108010037003 Buserelin Proteins 0.000 description 2
- 101150012716 CDK1 gene Proteins 0.000 description 2
- 101150006084 CHKB gene Proteins 0.000 description 2
- 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 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- 102000053642 Catalytic RNA Human genes 0.000 description 2
- 108090000994 Catalytic RNA Proteins 0.000 description 2
- 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 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- 102000002427 Cyclin B Human genes 0.000 description 2
- 108010068150 Cyclin B Proteins 0.000 description 2
- 229960005500 DHA-paclitaxel Drugs 0.000 description 2
- 230000012746 DNA damage checkpoint Effects 0.000 description 2
- 230000004543 DNA replication Effects 0.000 description 2
- 108010092160 Dactinomycin Proteins 0.000 description 2
- 102100033553 Delta-like protein 4 Human genes 0.000 description 2
- XXPXYPLPSDPERN-UHFFFAOYSA-N Ecteinascidin 743 Natural products COc1cc2C(NCCc2cc1O)C(=O)OCC3N4C(O)C5Cc6cc(C)c(OC)c(O)c6C(C4C(S)c7c(OC(=O)C)c(C)c8OCOc8c37)N5C XXPXYPLPSDPERN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 2
- 108010029961 Filgrastim Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 2
- 102000001398 Granzyme Human genes 0.000 description 2
- 108060005986 Granzyme Proteins 0.000 description 2
- 108010004889 Heat-Shock Proteins Proteins 0.000 description 2
- 102000002812 Heat-Shock Proteins Human genes 0.000 description 2
- 108090000353 Histone deacetylase Proteins 0.000 description 2
- 102000003964 Histone deacetylase Human genes 0.000 description 2
- 101000872077 Homo sapiens Delta-like protein 4 Proteins 0.000 description 2
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 2
- 108010023610 IL13-PE38 Proteins 0.000 description 2
- 108010047761 Interferon-alpha Proteins 0.000 description 2
- 102000006992 Interferon-alpha Human genes 0.000 description 2
- 229940121730 Janus kinase 2 inhibitor Drugs 0.000 description 2
- 102000010638 Kinesin Human genes 0.000 description 2
- 108010063296 Kinesin Proteins 0.000 description 2
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 2
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
- 239000002147 L01XE04 - Sunitinib Substances 0.000 description 2
- 239000005511 L01XE05 - Sorafenib Substances 0.000 description 2
- 108010062867 Lenograstim Proteins 0.000 description 2
- 229920001491 Lentinan Polymers 0.000 description 2
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 230000027311 M phase Effects 0.000 description 2
- 102000000424 Matrix Metalloproteinase 2 Human genes 0.000 description 2
- 108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 2
- 102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 2
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
- 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 2
- 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 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
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- SHGAZHPCJJPHSC-UHFFFAOYSA-N Panrexin Chemical compound OC(=O)C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-UHFFFAOYSA-N 0.000 description 2
- KHGNFPUMBJSZSM-UHFFFAOYSA-N Perforine Natural products COC1=C2CCC(O)C(CCC(C)(C)O)(OC)C2=NC2=C1C=CO2 KHGNFPUMBJSZSM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 108091028664 Ribonucleotide Proteins 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108700011582 TER 286 Proteins 0.000 description 2
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 description 2
- 102000002938 Thrombospondin Human genes 0.000 description 2
- 108060008245 Thrombospondin Proteins 0.000 description 2
- 108010078233 Thymalfasin Proteins 0.000 description 2
- 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 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 229940127507 Ubiquitin Ligase Inhibitors Drugs 0.000 description 2
- 108091008605 VEGF receptors Proteins 0.000 description 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
- OGQICQVSFDPSEI-UHFFFAOYSA-N Zorac Chemical compound N1=CC(C(=O)OCC)=CC=C1C#CC1=CC=C(SCCC2(C)C)C2=C1 OGQICQVSFDPSEI-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 229950009084 adecatumumab Drugs 0.000 description 2
- 208000009956 adenocarcinoma Diseases 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- 230000008484 agonism Effects 0.000 description 2
- 108700025316 aldesleukin Proteins 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 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 2
- BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 2
- 239000004037 angiogenesis inhibitor Substances 0.000 description 2
- 229940121369 angiogenesis inhibitor Drugs 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000000340 anti-metabolite Effects 0.000 description 2
- 239000000611 antibody drug conjugate Substances 0.000 description 2
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 239000003080 antimitotic agent Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 229940121357 antivirals Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940120638 avastin Drugs 0.000 description 2
- 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 2
- 229960002707 bendamustine Drugs 0.000 description 2
- YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- PYXFVCFISTUSOO-UHFFFAOYSA-N betulafolienetriol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC(C(C)(O)CCC=C(C)C)C4C(O)CC3C21C PYXFVCFISTUSOO-UHFFFAOYSA-N 0.000 description 2
- 229960000397 bevacizumab Drugs 0.000 description 2
- 229960002938 bexarotene Drugs 0.000 description 2
- 230000008512 biological response Effects 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 229960003008 blinatumomab Drugs 0.000 description 2
- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- CUWODFFVMXJOKD-UVLQAERKSA-N buserelin 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](COC(C)(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=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 CUWODFFVMXJOKD-UVLQAERKSA-N 0.000 description 2
- 229940022399 cancer vaccine Drugs 0.000 description 2
- 238000009566 cancer vaccine Methods 0.000 description 2
- OJLHWPALWODJPQ-QNWVGRARSA-N canfosfamide Chemical compound ClCCN(CCCl)P(=O)(N(CCCl)CCCl)OCCS(=O)(=O)C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 OJLHWPALWODJPQ-QNWVGRARSA-N 0.000 description 2
- 229950000772 canfosfamide Drugs 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000022131 cell cycle Effects 0.000 description 2
- 230000012820 cell cycle checkpoint Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 229950001357 celmoleukin Drugs 0.000 description 2
- 229960005395 cetuximab Drugs 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 2
- OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 229960000640 dactinomycin Drugs 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 description 2
- 229960000605 dexrazoxane Drugs 0.000 description 2
- LRCZQSDQZJBHAF-PUBGEWHCSA-N dha-paclitaxel Chemical compound N([C@H]([C@@H](OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)C(=O)O[C@@H]1C(=C2[C@@H](OC(C)=O)C(=O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]3[C@H](OC(=O)C=3C=CC=CC=3)[C@](C2(C)C)(O)C1)OC(C)=O)C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 LRCZQSDQZJBHAF-PUBGEWHCSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 description 2
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 2
- 239000003534 dna topoisomerase inhibitor Substances 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
- 229940079593 drug Drugs 0.000 description 2
- XOZIUKBZLSUILX-GIQCAXHBSA-N epothilone D Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC\C(C)=C/C[C@H]1C(\C)=C\C1=CSC(C)=N1 XOZIUKBZLSUILX-GIQCAXHBSA-N 0.000 description 2
- 229960001433 erlotinib Drugs 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- QINRQIZOBCQKAZ-UHFFFAOYSA-N ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1N QINRQIZOBCQKAZ-UHFFFAOYSA-N 0.000 description 2
- 229950000484 exisulind Drugs 0.000 description 2
- 229960004979 fampridine Drugs 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 2
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 2
- 229960005277 gemcitabine Drugs 0.000 description 2
- 229940020967 gemzar Drugs 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 238000001794 hormone therapy Methods 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 229940124541 immunological agent Drugs 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000012444 intercalating antibiotic Substances 0.000 description 2
- 229940047124 interferons Drugs 0.000 description 2
- 150000004694 iodide salts Chemical class 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
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229960004891 lapatinib Drugs 0.000 description 2
- DXOJIXGRFSHVKA-BZVZGCBYSA-N larotaxel Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@@]23[C@H]1[C@@]1(CO[C@@H]1C[C@@H]2C3)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 DXOJIXGRFSHVKA-BZVZGCBYSA-N 0.000 description 2
- 229940115286 lentinan Drugs 0.000 description 2
- 229950002884 lexatumumab Drugs 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229940115256 melanoma vaccine Drugs 0.000 description 2
- 229960001924 melphalan Drugs 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 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 2
- LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960002009 naproxen Drugs 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 2
- 229960001972 panitumumab Drugs 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229960002340 pentostatin Drugs 0.000 description 2
- 229930192851 perforin Natural products 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- IIMIOEBMYPRQGU-UHFFFAOYSA-L picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 229940069328 povidone Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- VQGISNOMGHCEPX-UHFFFAOYSA-N propanenitrile Chemical compound C[CH]C#N VQGISNOMGHCEPX-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- ITPRZAYYCJNBLF-UHFFFAOYSA-O pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=[N+]=C[CH]1 ITPRZAYYCJNBLF-UHFFFAOYSA-O 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229960004432 raltitrexed Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 125000002652 ribonucleotide group Chemical group 0.000 description 2
- 108091092562 ribozyme Proteins 0.000 description 2
- 229960004641 rituximab Drugs 0.000 description 2
- 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 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229960003787 sorafenib Drugs 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 229960000894 sulindac Drugs 0.000 description 2
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 2
- MVGSNCBCUWPVDA-MFOYZWKCSA-N sulindac sulfone Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)(=O)=O)C=C1 MVGSNCBCUWPVDA-MFOYZWKCSA-N 0.000 description 2
- 229940099419 targretin Drugs 0.000 description 2
- 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 2
- 229960004964 temozolomide Drugs 0.000 description 2
- 229960000235 temsirolimus Drugs 0.000 description 2
- USGKAXIJKNBDSV-UHFFFAOYSA-N tert-butyl 2-(4-aminophenyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1C1=CC=C(N)C=C1 USGKAXIJKNBDSV-UHFFFAOYSA-N 0.000 description 2
- OZKTUGIZGIKRBJ-UHFFFAOYSA-N tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C1=CC=C(N)C=C1 OZKTUGIZGIKRBJ-UHFFFAOYSA-N 0.000 description 2
- QSSVQUXXRYNJIZ-UHFFFAOYSA-N tert-butyl 4-(4-amino-2-methylphenyl)piperazine-1-carboxylate Chemical compound CC1=CC(N)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 QSSVQUXXRYNJIZ-UHFFFAOYSA-N 0.000 description 2
- PYQPVPBYELLURV-UHFFFAOYSA-N tert-butyl 4-[4-amino-2-(trifluoromethyl)phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1C(F)(F)F PYQPVPBYELLURV-UHFFFAOYSA-N 0.000 description 2
- AGRBXKCSGCUXST-UHFFFAOYSA-N tert-butyl 7-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1=C(N)C=C2CN(C(=O)OC(C)(C)C)CCC2=C1 AGRBXKCSGCUXST-UHFFFAOYSA-N 0.000 description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 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 2
- 229960004231 thymalfasin Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 2
- 229960005267 tositumomab Drugs 0.000 description 2
- PKVRCIRHQMSYJX-AIFWHQITSA-N trabectedin Chemical compound C([C@@]1(C(OC2)=O)NCCC3=C1C=C(C(=C3)O)OC)S[C@@H]1C3=C(OC(C)=O)C(C)=C4OCOC4=C3[C@H]2N2[C@@H](O)[C@H](CC=3C4=C(O)C(OC)=C(C)C=3)N(C)[C@H]4[C@@H]21 PKVRCIRHQMSYJX-AIFWHQITSA-N 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
- 229960000575 trastuzumab Drugs 0.000 description 2
- 229960001727 tretinoin Drugs 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- 238000001665 trituration Methods 0.000 description 2
- 229940094060 tykerb Drugs 0.000 description 2
- 229950009811 ubenimex Drugs 0.000 description 2
- 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 2
- 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 2
- 229960000241 vandetanib Drugs 0.000 description 2
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 2
- 229950000578 vatalanib Drugs 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 2
- 229960000237 vorinostat Drugs 0.000 description 2
- 229950009268 zinostatin Drugs 0.000 description 2
- AADVCYNFEREWOS-UHFFFAOYSA-N (+)-DDM Natural products C=CC=CC(C)C(OC(N)=O)C(C)C(O)C(C)CC(C)=CC(C)C(O)C(C)C=CC(O)CC1OC(=O)C(C)C(O)C1C AADVCYNFEREWOS-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- PYXFVCFISTUSOO-HKUCOEKDSA-N (20S)-protopanaxadiol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@H]([C@@](C)(O)CCC=C(C)C)[C@H]4[C@H](O)C[C@@H]3[C@]21C PYXFVCFISTUSOO-HKUCOEKDSA-N 0.000 description 1
- JMPZTWDLOGTBPM-OUQSKUGOSA-N (2e,4e,6e)-7-(3,5-ditert-butylphenyl)-3-methylocta-2,4,6-trienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 JMPZTWDLOGTBPM-OUQSKUGOSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
- RIWLPSIAFBLILR-WVNGMBSFSA-N (2s)-1-[(2s)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s,3r)-2-[[(2r,3s)-2-[[(2s)-2-[[2-[[2-[acetyl(methyl)amino]acetyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]pentanoyl]amino]-3-methylpentanoyl]amino]-5-(diaminomethy Chemical compound CC(=O)N(C)CC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC RIWLPSIAFBLILR-WVNGMBSFSA-N 0.000 description 1
- WZRFLSDVFPIXOV-LRQRDZAKSA-N (2s)-1-[(2s)-2-cyclohexyl-2-[[(2s)-2-(methylamino)propanoyl]amino]acetyl]-n-(4-phenylthiadiazol-5-yl)pyrrolidine-2-carboxamide Chemical compound C1([C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C(=O)NC2=C(N=NS2)C=2C=CC=CC=2)CCCCC1 WZRFLSDVFPIXOV-LRQRDZAKSA-N 0.000 description 1
- BXTJCSYMGFJEID-XMTADJHZSA-N (2s)-2-[[(2r,3r)-3-[(2s)-1-[(3r,4s,5s)-4-[[(2s)-2-[[(2s)-2-[6-[3-[(2r)-2-amino-2-carboxyethyl]sulfanyl-2,5-dioxopyrrolidin-1-yl]hexanoyl-methylamino]-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methoxy-5-methylheptanoyl]pyrrolidin-2-yl]-3-met Chemical compound C([C@H](NC(=O)[C@H](C)[C@@H](OC)[C@@H]1CCCN1C(=O)C[C@H]([C@H]([C@@H](C)CC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C(=O)CCCCCN1C(C(SC[C@H](N)C(O)=O)CC1=O)=O)C(C)C)OC)C(O)=O)C1=CC=CC=C1 BXTJCSYMGFJEID-XMTADJHZSA-N 0.000 description 1
- QXOPTIPQEVJERB-JQWIXIFHSA-N (2s)-2-[[5-[2-[(6s)-2-amino-4-oxo-5,6,7,8-tetrahydro-1h-pyrido[2,3-d]pyrimidin-6-yl]ethyl]-4-methylthiophene-2-carbonyl]amino]pentanedioic acid Chemical compound C1=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)SC(CC[C@H]2CC=3C(=O)N=C(N)NC=3NC2)=C1C QXOPTIPQEVJERB-JQWIXIFHSA-N 0.000 description 1
- NECZZOFFLFZNHL-XVGZVFJZSA-N (2s)-2-amino-5-[[(2r)-3-[2-[bis[bis(2-chloroethyl)amino]-oxidophosphaniumyl]oxyethylsulfonyl]-1-[[(r)-carboxy(phenyl)methyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;hydron;chloride Chemical compound Cl.ClCCN(CCCl)P(=O)(N(CCCl)CCCl)OCCS(=O)(=O)C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 NECZZOFFLFZNHL-XVGZVFJZSA-N 0.000 description 1
- MHFUWOIXNMZFIW-WNQIDUERSA-N (2s)-2-hydroxypropanoic acid;n-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound C[C@H](O)C(O)=O.C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 MHFUWOIXNMZFIW-WNQIDUERSA-N 0.000 description 1
- UFPFGVNKHCLJJO-SSKFGXFMSA-N (2s)-n-[(1s)-1-cyclohexyl-2-[(2s)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1([C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2SC=C(N=2)C(=O)C=2C=CC(F)=CC=2)CCCCC1 UFPFGVNKHCLJJO-SSKFGXFMSA-N 0.000 description 1
- HCSMRSHIIKPNAK-LSAVBLLPSA-N (2s)-n-[(1s)-2-[(3ar,7as)-6-(2-phenylethyl)-3,3a,4,5,7,7a-hexahydro-2h-pyrrolo[2,3-c]pyridin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1([C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H]3CN(CCC=4C=CC=CC=4)CC[C@@H]3CC2)CCCCC1 HCSMRSHIIKPNAK-LSAVBLLPSA-N 0.000 description 1
- GTXSRFUZSLTDFX-HRCADAONSA-N (2s)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-methyl-2-[[(2s)-2-sulfanyl-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butanoyl]amino]pentanamide Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](S)CCN1C(=O)N(C)C(C)(C)C1=O GTXSRFUZSLTDFX-HRCADAONSA-N 0.000 description 1
- PSVUJBVBCOISSP-SPFKKGSWSA-N (2s,3r,4s,5s,6r)-2-bis(2-chloroethylamino)phosphoryloxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC[C@H]1O[C@@H](OP(=O)(NCCCl)NCCCl)[C@H](O)[C@@H](O)[C@@H]1O PSVUJBVBCOISSP-SPFKKGSWSA-N 0.000 description 1
- CVCLJVVBHYOXDC-IAZSKANUSA-N (2z)-2-[(5z)-5-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-methoxypyrrol-2-ylidene]indole Chemical compound COC1=C\C(=C/2N=C3C=CC=CC3=C\2)N\C1=C/C=1NC(C)=CC=1C CVCLJVVBHYOXDC-IAZSKANUSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 1
- QYNUQALWYRSVHF-OLZOCXBDSA-N (6R)-5,10-methylenetetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1C1)N)N1C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QYNUQALWYRSVHF-OLZOCXBDSA-N 0.000 description 1
- MWWSFMDVAYGXBV-FGBSZODSSA-N (7s,9s)-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydron;chloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-FGBSZODSSA-N 0.000 description 1
- HEQRYQONNHFDHG-TZSSRYMLSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione 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](O)[C@H](O)[C@H](C)O1 HEQRYQONNHFDHG-TZSSRYMLSA-N 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-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
- BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- ZOABYUFOTSJETH-UHFFFAOYSA-N 1,1,2,3,3-pentamethylisoindol-5-amine Chemical compound C1=C(N)C=C2C(C)(C)N(C)C(C)(C)C2=C1 ZOABYUFOTSJETH-UHFFFAOYSA-N 0.000 description 1
- QAWIGFGJXOCTRI-UHFFFAOYSA-N 1,1,2-trimethyl-3h-isoindol-5-amine Chemical compound NC1=CC=C2C(C)(C)N(C)CC2=C1 QAWIGFGJXOCTRI-UHFFFAOYSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
- BJJCTTWAVRELGA-UHFFFAOYSA-N 1,3-dichloro-5-fluoro-2-isocyanatobenzene Chemical compound FC1=CC(Cl)=C(N=C=O)C(Cl)=C1 BJJCTTWAVRELGA-UHFFFAOYSA-N 0.000 description 1
- YXHDLKWTPVMIOH-UHFFFAOYSA-N 1,3-difluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC(F)=C1N=C=O YXHDLKWTPVMIOH-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 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
- BJXPIIDUCADEKU-UHFFFAOYSA-N 1-(4-aminophenyl)piperidin-4-ol Chemical compound C1=CC(N)=CC=C1N1CCC(O)CC1 BJXPIIDUCADEKU-UHFFFAOYSA-N 0.000 description 1
- LOZKZWIQDVEDCQ-UHFFFAOYSA-N 1-(6-amino-2,3-dihydroindol-1-yl)ethanone Chemical compound C1=C(N)C=C2N(C(=O)C)CCC2=C1 LOZKZWIQDVEDCQ-UHFFFAOYSA-N 0.000 description 1
- SWQQELWGJDXCFT-PNHWDRBUSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylimidazole-4-carboxamide Chemical compound C#CC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 SWQQELWGJDXCFT-PNHWDRBUSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- AFVUJJNEILZYJQ-UHFFFAOYSA-N 1-[4-(4-aminophenyl)-1-piperazinyl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N)C=C1 AFVUJJNEILZYJQ-UHFFFAOYSA-N 0.000 description 1
- WPHKIQPVPYJNAX-UHFFFAOYSA-N 1-[4-[4-amino-7-[1-(2-hydroxyethyl)pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=2SC=C(C=3C=CC(NC(=O)NC=4C=C(F)C=CC=4)=CC=3)C=2C(N)=NC=C1C=1C=NN(CCO)C=1 WPHKIQPVPYJNAX-UHFFFAOYSA-N 0.000 description 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- KMDUNDOCWFAOSP-UHFFFAOYSA-N 1-chloro-3-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC(Cl)=C1N=C=O KMDUNDOCWFAOSP-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
- OOSXXMRVOYQUBM-UHFFFAOYSA-N 1-isocyanato-3-methoxy-2-methylbenzene Chemical compound COC1=CC=CC(N=C=O)=C1C OOSXXMRVOYQUBM-UHFFFAOYSA-N 0.000 description 1
- JACWZQMCSAIZBF-UHFFFAOYSA-N 1-methyl-3,4-dihydro-2h-quinolin-6-amine Chemical compound NC1=CC=C2N(C)CCCC2=C1 JACWZQMCSAIZBF-UHFFFAOYSA-N 0.000 description 1
- OMGAOBAAEGMMTF-UHFFFAOYSA-N 1-methyl-3,4-dihydro-2h-quinolin-7-amine Chemical compound C1=C(N)C=C2N(C)CCCC2=C1 OMGAOBAAEGMMTF-UHFFFAOYSA-N 0.000 description 1
- HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 description 1
- CZDWSKBKCZWXFI-UHFFFAOYSA-N 1-morpholin-4-yl-3-[4-oxo-3-[4-[2-oxo-2-(4-propan-2-ylpiperazin-1-yl)ethoxy]phenyl]-1h-indeno[1,2-c]pyrazol-5-yl]urea Chemical compound C1CN(C(C)C)CCN1C(=O)COC1=CC=C(C=2C=3C(=O)C4=C(NC(=O)NN5CCOCC5)C=CC=C4C=3NN=2)C=C1 CZDWSKBKCZWXFI-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- HAWSQZCWOQZXHI-FQEVSTJZSA-N 10-Hydroxycamptothecin Chemical compound C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-FQEVSTJZSA-N 0.000 description 1
- UEQZOEVKMMEQFQ-UHFFFAOYSA-N 12-[(2-acetyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl UEQZOEVKMMEQFQ-UHFFFAOYSA-N 0.000 description 1
- WYUGYFWIJUABRJ-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichloro-4-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=C(F)C=C1Cl WYUGYFWIJUABRJ-UHFFFAOYSA-N 0.000 description 1
- KUFRQPKVAWMTJO-QSTRRNJOSA-N 17-dmag Chemical compound N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(NCCN(C)C)C(=O)C=C1C2=O KUFRQPKVAWMTJO-QSTRRNJOSA-N 0.000 description 1
- QMVPQBFHUJZJCS-NTKFZFFISA-N 1v8x590xdp Chemical compound O=C1N(NC(CO)CO)C(=O)C(C2=C3[CH]C=C(O)C=C3NC2=C23)=C1C2=C1C=CC(O)=C[C]1N3[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QMVPQBFHUJZJCS-NTKFZFFISA-N 0.000 description 1
- ROZCIVXTLACYNY-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F ROZCIVXTLACYNY-UHFFFAOYSA-N 0.000 description 1
- QSFOQOITYRPHOQ-UHFFFAOYSA-N 2,3,4,5,7,11,13-heptazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound N1=NN=C2N1C1=C(C(N2)=O)C=NC=N1 QSFOQOITYRPHOQ-UHFFFAOYSA-N 0.000 description 1
- NEJDXOOWUAFPLR-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-2-benzazepin-7-amine Chemical compound C1NCCCC2=CC(N)=CC=C21 NEJDXOOWUAFPLR-UHFFFAOYSA-N 0.000 description 1
- CLRYRILYDTUXHZ-UHFFFAOYSA-N 2-(2,2-dimethoxyethylamino)-3-(2-methylphenyl)-7-methylsulfanylpyrimido[4,5-d]pyrimidin-4-one Chemical compound COC(OC)CNC1=NC2=NC(SC)=NC=C2C(=O)N1C1=CC=CC=C1C CLRYRILYDTUXHZ-UHFFFAOYSA-N 0.000 description 1
- FSONZROLZYQJDD-UHFFFAOYSA-N 2-(2,2-dimethoxyethylamino)-7-methylsulfanyl-3-[2-(trifluoromethyl)phenyl]pyrimido[4,5-d]pyrimidin-4-one Chemical compound COC(OC)CNC1=NC2=NC(SC)=NC=C2C(=O)N1C1=CC=CC=C1C(F)(F)F FSONZROLZYQJDD-UHFFFAOYSA-N 0.000 description 1
- MOEMSQNDONSILH-UHFFFAOYSA-N 2-(2,2-dimethoxyethylamino)-7-methylsulfanyl-3-phenylpyrimido[4,5-d]pyrimidin-4-one Chemical compound COC(OC)CNC1=NC2=NC(SC)=NC=C2C(=O)N1C1=CC=CC=C1 MOEMSQNDONSILH-UHFFFAOYSA-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
- JNAHVYVRKWKWKQ-UHFFFAOYSA-N 2-(2-methyl-2-pyrrolidinyl)-1H-benzimidazole-4-carboxamide Chemical compound N=1C2=C(C(N)=O)C=CC=C2NC=1C1(C)CCCN1 JNAHVYVRKWKWKQ-UHFFFAOYSA-N 0.000 description 1
- XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- OZLADJXIVNANRO-UHFFFAOYSA-N 2-(7-amino-3,4-dihydro-1h-isoquinolin-2-yl)ethanol Chemical compound C1CN(CCO)CC2=CC(N)=CC=C21 OZLADJXIVNANRO-UHFFFAOYSA-N 0.000 description 1
- PADGNZFOVSZIKZ-UHFFFAOYSA-N 2-(chloromethyl)oxirane;hydrogen carbonate;prop-2-enylazanium Chemical compound NCC=C.OC(O)=O.ClCC1CO1 PADGNZFOVSZIKZ-UHFFFAOYSA-N 0.000 description 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- QXLQZLBNPTZMRK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2,4-dimethylphenyl)prop-2-en-1-one Chemical compound CN(C)CC(=C)C(=O)C1=CC=C(C)C=C1C QXLQZLBNPTZMRK-UHFFFAOYSA-N 0.000 description 1
- OTLLEIBWKHEHGU-UHFFFAOYSA-N 2-[5-[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-4-phosphonooxyhexanedioic acid Chemical compound C1=NC=2C(N)=NC=NC=2N1C(C(C1O)O)OC1COC1C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C1O OTLLEIBWKHEHGU-UHFFFAOYSA-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
- PJKVJJYMWOCLIJ-UHFFFAOYSA-N 2-amino-6-methyl-5-pyridin-4-ylsulfanyl-1h-quinazolin-4-one;hydron;dichloride Chemical compound Cl.Cl.CC1=CC=C2NC(N)=NC(=O)C2=C1SC1=CC=NC=C1 PJKVJJYMWOCLIJ-UHFFFAOYSA-N 0.000 description 1
- RGHYDLZMTYDBDT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1H-pyrazol-5-yl)-7-pyrido[2,3-d]pyrimidinone Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 RGHYDLZMTYDBDT-UHFFFAOYSA-N 0.000 description 1
- QINPEPAQOBZPOF-UHFFFAOYSA-N 2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-methylpropanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C(C)(C)N)C=CC=2)=C1 QINPEPAQOBZPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- QVCZOTVTRWNPAF-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-methylbenzene Chemical compound CC1=CC=C(N=C=O)C(Cl)=C1 QVCZOTVTRWNPAF-UHFFFAOYSA-N 0.000 description 1
- YXJXXNNYSZIEMK-UHFFFAOYSA-N 2-chloro-3-(2-methylphenyl)-7-methylsulfanylpyrimido[4,5-d]pyrimidin-4-one Chemical compound N=1C(SC)=NC=C(C2=O)C=1N=C(Cl)N2C1=CC=CC=C1C YXJXXNNYSZIEMK-UHFFFAOYSA-N 0.000 description 1
- YRUBIFAMCRFPPC-UHFFFAOYSA-N 2-chloro-7-fluoro-1h-quinazolin-4-one Chemical compound N1C(Cl)=NC(=O)C=2C1=CC(F)=CC=2 YRUBIFAMCRFPPC-UHFFFAOYSA-N 0.000 description 1
- AZEDBPKYJRCMBB-UHFFFAOYSA-N 2-chloro-7-methylsulfanyl-3-[2-(trifluoromethyl)phenyl]pyrimido[4,5-d]pyrimidin-4-one Chemical compound N=1C(SC)=NC=C(C2=O)C=1N=C(Cl)N2C1=CC=CC=C1C(F)(F)F AZEDBPKYJRCMBB-UHFFFAOYSA-N 0.000 description 1
- KJKDUZBUUZDFJM-UHFFFAOYSA-N 2-chloro-7-methylsulfanyl-3-phenylpyrimido[4,5-d]pyrimidin-4-one Chemical compound N=1C(SC)=NC=C(C2=O)C=1N=C(Cl)N2C1=CC=CC=C1 KJKDUZBUUZDFJM-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- LUYPGLRYFIVYTH-UHFFFAOYSA-N 2-methoxy-4-(4-methylpiperazin-1-yl)aniline Chemical compound C1=C(N)C(OC)=CC(N2CCN(C)CC2)=C1 LUYPGLRYFIVYTH-UHFFFAOYSA-N 0.000 description 1
- QTEUFEDZEJZEBZ-UHFFFAOYSA-N 2-methylsulfanyl-6-[2-(trifluoromethyl)phenyl]-8h-pyrimido[4,5-d]pyrimidine-5,7-dione Chemical compound N=1C(SC)=NC=C(C2=O)C=1NC(=O)N2C1=CC=CC=C1C(F)(F)F QTEUFEDZEJZEBZ-UHFFFAOYSA-N 0.000 description 1
- PWPYUMYIYHZMDX-UHFFFAOYSA-N 2-methylsulfanyl-6-phenyl-8h-pyrimido[4,5-d]pyrimidine-5,7-dione Chemical compound N=1C(SC)=NC=C(C2=O)C=1NC(=O)N2C1=CC=CC=C1 PWPYUMYIYHZMDX-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MJUHIAWSJRKXSH-UHFFFAOYSA-N 2-pyridin-3-ylacetaldehyde Chemical compound O=CCC1=CC=CN=C1 MJUHIAWSJRKXSH-UHFFFAOYSA-N 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- GHWSMQHJFMAATF-DSHMRAQASA-N 20(S)-protopanaxadiol Natural products CC(=CCC[C@@](O)(CO)[C@H]1CC[C@]2(C)[C@@H]1CC[C@H]3[C@@]2(C)CC[C@H]4C(C)(C)[C@@H](O)CC[C@]34CO)C GHWSMQHJFMAATF-DSHMRAQASA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- AXRCEOKUDYDWLF-UHFFFAOYSA-N 3-(1-methyl-3-indolyl)-4-[1-[1-(2-pyridinylmethyl)-4-piperidinyl]-3-indolyl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=CC=C11)=CN1C(CC1)CCN1CC1=CC=CC=N1 AXRCEOKUDYDWLF-UHFFFAOYSA-N 0.000 description 1
- BJVRNXSHJLDZJR-UHFFFAOYSA-N 3-(1-methyl-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)phenol Chemical compound N1=C2N(C)N=CC2=C(N2CCOCC2)N=C1C1=CC=CC(O)=C1 BJVRNXSHJLDZJR-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- GYJREHMTTLYKRJ-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1C=CC=CC=1COC(=O)NC(C(=O)O)CC1=CC=CC=C1F GYJREHMTTLYKRJ-UHFFFAOYSA-N 0.000 description 1
- NWYSNUTTYKBUKB-UHFFFAOYSA-N 3-(3-piperidin-1-ylpropoxy)aniline Chemical compound NC1=CC=CC(OCCCN2CCCCC2)=C1 NWYSNUTTYKBUKB-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- RJGHJWKQCJAJEP-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=CC(N)=C1 RJGHJWKQCJAJEP-UHFFFAOYSA-N 0.000 description 1
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
- RZDBCURLSQNEAD-UHFFFAOYSA-N 3-(pyrrolidin-1-ylmethyl)aniline Chemical compound NC1=CC=CC(CN2CCCC2)=C1 RZDBCURLSQNEAD-UHFFFAOYSA-N 0.000 description 1
- HXHAJRMTJXHJJZ-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HXHAJRMTJXHJJZ-UHFFFAOYSA-N 0.000 description 1
- DIYQKNOQRDOHAI-UHFFFAOYSA-N 3-[3-(4-methylpiperazin-1-yl)propoxy]aniline Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(N)=C1 DIYQKNOQRDOHAI-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SGXSPGWRBBQBDR-UHFFFAOYSA-N 3-[[4-(4-aminophenyl)piperazin-1-yl]methyl]benzonitrile Chemical compound C1=CC(N)=CC=C1N1CCN(CC=2C=C(C=CC=2)C#N)CC1 SGXSPGWRBBQBDR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- JGBYLNAUFSKQTE-UHFFFAOYSA-N 3-fluoro-4-[2-(4-methylpiperazin-1-yl)ethoxy]aniline Chemical compound C1CN(C)CCN1CCOC1=CC=C(N)C=C1F JGBYLNAUFSKQTE-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- QUICNJMNPNNIIX-UHFFFAOYSA-N 3-methoxy-4-[2-(4-methylpiperazin-1-yl)ethoxy]aniline Chemical compound COC1=CC(N)=CC=C1OCCN1CCN(C)CC1 QUICNJMNPNNIIX-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- SCJCDNUXDWFVFI-UHFFFAOYSA-N 4,4,4-trifluorobutanal Chemical compound FC(F)(F)CCC=O SCJCDNUXDWFVFI-UHFFFAOYSA-N 0.000 description 1
- BNYVBWBKNDWCQW-UHFFFAOYSA-N 4-(1-methylpiperidin-4-yl)aniline Chemical compound C1CN(C)CCC1C1=CC=C(N)C=C1 BNYVBWBKNDWCQW-UHFFFAOYSA-N 0.000 description 1
- WJRRGYBTGDJBFX-UHFFFAOYSA-N 4-(2-methyl-3-propan-2-yl-4-imidazolyl)-N-(4-methylsulfonylphenyl)-2-pyrimidinamine Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=N1 WJRRGYBTGDJBFX-UHFFFAOYSA-N 0.000 description 1
- ZHFFNLQQANCJEQ-UHFFFAOYSA-N 4-(2-morpholin-4-ylethoxy)aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCOCC1 ZHFFNLQQANCJEQ-UHFFFAOYSA-N 0.000 description 1
- ZWZGOWOOBNARBJ-UHFFFAOYSA-N 4-(3,3-difluoropiperidin-1-yl)aniline Chemical compound C1=CC(N)=CC=C1N1CC(F)(F)CCC1 ZWZGOWOOBNARBJ-UHFFFAOYSA-N 0.000 description 1
- DOMCPPNXYDFOQU-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)aniline Chemical compound C1=CC(N)=CC=C1N1CCC(F)(F)CC1 DOMCPPNXYDFOQU-UHFFFAOYSA-N 0.000 description 1
- PZAWODZZVTUFBG-UHFFFAOYSA-N 4-(4-aminophenyl)piperazin-2-one Chemical compound C1=CC(N)=CC=C1N1CC(=O)NCC1 PZAWODZZVTUFBG-UHFFFAOYSA-N 0.000 description 1
- CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
- DGHAOTHIDTUSJY-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1C=NC=C1 DGHAOTHIDTUSJY-UHFFFAOYSA-N 0.000 description 1
- WNYFVEFUHMDIRQ-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCOCC1 WNYFVEFUHMDIRQ-UHFFFAOYSA-N 0.000 description 1
- ISRYTHBRUSOVAB-UHFFFAOYSA-N 4-(pyrazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1N=CC=C1 ISRYTHBRUSOVAB-UHFFFAOYSA-N 0.000 description 1
- SFEAIUCOZWDYMJ-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCCC1 SFEAIUCOZWDYMJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 description 1
- HEUVRFNVTLGKMZ-SANMLTNESA-N 4-[(2s)-2-(4-cyanophenyl)-2-hydroxy-2-(3-methylimidazol-4-yl)ethoxy]-3-[4-(trifluoromethoxy)phenyl]benzonitrile Chemical compound CN1C=NC=C1[C@@](O)(C=1C=CC(=CC=1)C#N)COC1=CC=C(C#N)C=C1C1=CC=C(OC(F)(F)F)C=C1 HEUVRFNVTLGKMZ-SANMLTNESA-N 0.000 description 1
- XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 description 1
- BKUWHZDNFSRARB-UHFFFAOYSA-N 4-[2-(4-methylpiperazin-1-yl)ethyl]aniline Chemical compound C1CN(C)CCN1CCC1=CC=C(N)C=C1 BKUWHZDNFSRARB-UHFFFAOYSA-N 0.000 description 1
- LFJGGGIWERIGNX-UHFFFAOYSA-N 4-[2-(diethylamino)ethoxy]aniline Chemical compound CCN(CC)CCOC1=CC=C(N)C=C1 LFJGGGIWERIGNX-UHFFFAOYSA-N 0.000 description 1
- CCCVQPGAXZNTIL-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline Chemical compound CN(C)CCOC1=CC=C(N)C=C1 CCCVQPGAXZNTIL-UHFFFAOYSA-N 0.000 description 1
- LZYIXSDJJBZCEM-UHFFFAOYSA-N 4-[4-(2-methoxyethyl)piperazin-1-yl]aniline Chemical compound C1CN(CCOC)CCN1C1=CC=C(N)C=C1 LZYIXSDJJBZCEM-UHFFFAOYSA-N 0.000 description 1
- RGAYBGMAQWESJW-UHFFFAOYSA-N 4-[4-(cyclohexylmethyl)piperazin-1-yl]aniline Chemical compound C1=CC(N)=CC=C1N1CCN(CC2CCCCC2)CC1 RGAYBGMAQWESJW-UHFFFAOYSA-N 0.000 description 1
- FCMBRZHFQVDAMS-UHFFFAOYSA-N 4-[4-[(3-chlorophenyl)methyl]piperazin-1-yl]aniline Chemical compound C1=CC(N)=CC=C1N1CCN(CC=2C=C(Cl)C=CC=2)CC1 FCMBRZHFQVDAMS-UHFFFAOYSA-N 0.000 description 1
- ZHSKUOZOLHMKEA-UHFFFAOYSA-N 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydron;chloride Chemical compound Cl.ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 ZHSKUOZOLHMKEA-UHFFFAOYSA-N 0.000 description 1
- HHFBDROWDBDFBR-UHFFFAOYSA-N 4-[[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(CN=C(C=2C3=CC=C(Cl)C=2)C=2C(=CC=CC=2F)F)C3=N1 HHFBDROWDBDFBR-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- LVOASPZGXNAHJI-UHFFFAOYSA-N 4-imidazol-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1C=NC=C1 LVOASPZGXNAHJI-UHFFFAOYSA-N 0.000 description 1
- MDOJTZQKHMAPBK-UHFFFAOYSA-N 4-iodo-3-nitrobenzamide Chemical compound NC(=O)C1=CC=C(I)C([N+]([O-])=O)=C1 MDOJTZQKHMAPBK-UHFFFAOYSA-N 0.000 description 1
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
- TVOSOIXYPHKEAR-UHFFFAOYSA-N 4-piperidin-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCCCC1 TVOSOIXYPHKEAR-UHFFFAOYSA-N 0.000 description 1
- CSFIQHZIFKIQNO-UHFFFAOYSA-N 4-pyrazol-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1N=CC=C1 CSFIQHZIFKIQNO-UHFFFAOYSA-N 0.000 description 1
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
- WUUGFSXJNOTRMR-IOSLPCCCSA-N 5'-S-methyl-5'-thioadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-IOSLPCCCSA-N 0.000 description 1
- MOXOFSFWYLTCFU-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-2-amine Chemical compound C1CCCC2=CC(N)=CC=C21 MOXOFSFWYLTCFU-UHFFFAOYSA-N 0.000 description 1
- HUNAOTXNHVALTN-UHFFFAOYSA-N 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)pyrazole-3-carboxamide Chemical compound CCNC(=O)C1=NNC(C=2C(=CC(O)=C(Cl)C=2)O)=C1C1=CC=C(OC)C=C1 HUNAOTXNHVALTN-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- UPALIKSFLSVKIS-UHFFFAOYSA-N 5-amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione Chemical compound NC1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=CC3=C1 UPALIKSFLSVKIS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
- SESRNPLDGLRJDH-UHFFFAOYSA-N 6-(2-methylphenyl)-2-methylsulfanyl-8h-pyrimido[4,5-d]pyrimidine-5,7-dione Chemical compound N=1C(SC)=NC=C(C2=O)C=1NC(=O)N2C1=CC=CC=C1C SESRNPLDGLRJDH-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- GEPGYMHEMLZMBC-UHFFFAOYSA-N 6-amino-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(N)=CC=C21 GEPGYMHEMLZMBC-UHFFFAOYSA-N 0.000 description 1
- DOCINCLJNAXZQF-LBPRGKRZSA-N 6-fluoro-3-phenyl-2-[(1s)-1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound C1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)=NC2=CC=C(F)C=C2C(=O)N1C1=CC=CC=C1 DOCINCLJNAXZQF-LBPRGKRZSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 description 1
- WLCZTRVUXYALDD-IBGZPJMESA-N 7-[[(2s)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid Chemical compound COCCOC(=O)NCCCC[C@H](NC(=O)OCCOC)C(=O)NCCCCCCCOP(C)(O)=O WLCZTRVUXYALDD-IBGZPJMESA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- UKAFWJUARMVPPH-UHFFFAOYSA-N 8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)N=CNC2=N1 UKAFWJUARMVPPH-UHFFFAOYSA-N 0.000 description 1
- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NKGPJODWTZCHGF-UHFFFAOYSA-N 9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound OC1C(O)C(CO)OC1N1C(NC=NC2=S)=C2N=C1 NKGPJODWTZCHGF-UHFFFAOYSA-N 0.000 description 1
- TUOSCZDRWRYPRS-UHFFFAOYSA-N 9-butyl-8-(3,4,5-trimethoxybenzyl)-9h-purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCC)C=1CC1=CC(OC)=C(OC)C(OC)=C1 TUOSCZDRWRYPRS-UHFFFAOYSA-N 0.000 description 1
- 229940127124 90Y-ibritumomab tiuxetan Drugs 0.000 description 1
- OONFNUWBHFSNBT-HXUWFJFHSA-N AEE788 Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)C=C1 OONFNUWBHFSNBT-HXUWFJFHSA-N 0.000 description 1
- BUROJSBIWGDYCN-GAUTUEMISA-N AP 23573 Chemical compound C1C[C@@H](OP(C)(C)=O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 BUROJSBIWGDYCN-GAUTUEMISA-N 0.000 description 1
- GBJVVSCPOBPEIT-UHFFFAOYSA-N AZT-1152 Chemical compound N=1C=NC2=CC(OCCCN(CC)CCOP(O)(O)=O)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 GBJVVSCPOBPEIT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010000830 Acute leukaemia Diseases 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- ZGCSNRKSJLVANE-UHFFFAOYSA-N Aglycone-Rebeccamycin Natural products N1C2=C3NC4=C(Cl)C=CC=C4C3=C(C(=O)NC3=O)C3=C2C2=C1C(Cl)=CC=C2 ZGCSNRKSJLVANE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 201000003076 Angiosarcoma Diseases 0.000 description 1
- MXPOCMVWFLDDLZ-NSCUHMNNSA-N Apaziquone Chemical compound CN1C(\C=C\CO)=C(CO)C(C2=O)=C1C(=O)C=C2N1CC1 MXPOCMVWFLDDLZ-NSCUHMNNSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 108010024976 Asparaginase Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- YUXMAKUNSXIEKN-BTJKTKAUSA-N BGT226 Chemical compound OC(=O)\C=C/C(O)=O.C1=NC(OC)=CC=C1C1=CC=C(N=CC2=C3N(C=4C=C(C(N5CCNCC5)=CC=4)C(F)(F)F)C(=O)N2C)C3=C1 YUXMAKUNSXIEKN-BTJKTKAUSA-N 0.000 description 1
- QULDDKSCVCJTPV-UHFFFAOYSA-N BIIB021 Chemical compound COC1=C(C)C=NC(CN2C3=NC(N)=NC(Cl)=C3N=C2)=C1C QULDDKSCVCJTPV-UHFFFAOYSA-N 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010004593 Bile duct cancer Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 241000283690 Bos taurus Species 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 101150013553 CD40 gene Proteins 0.000 description 1
- 102000009728 CDC2 Protein Kinase Human genes 0.000 description 1
- 108010034798 CDC2 Protein Kinase Proteins 0.000 description 1
- HAWSQZCWOQZXHI-UHFFFAOYSA-N CPT-OH Natural products C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-UHFFFAOYSA-N 0.000 description 1
- 229940045513 CTLA4 antagonist Drugs 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 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
- 241000283707 Capra Species 0.000 description 1
- SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 1
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
- 229940123587 Cell cycle inhibitor Drugs 0.000 description 1
- 102100025832 Centromere-associated protein E Human genes 0.000 description 1
- 229940124957 Cervarix Drugs 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 241001233914 Chelidonium majus Species 0.000 description 1
- 241001227713 Chiron Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000005243 Chondrosarcoma Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 108010060123 Conjugate Vaccines Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000009798 Craniopharyngioma Diseases 0.000 description 1
- 108010068192 Cyclin A Proteins 0.000 description 1
- 102100025191 Cyclin-A2 Human genes 0.000 description 1
- 102100021906 Cyclin-O Human genes 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 230000033616 DNA repair Effects 0.000 description 1
- 101100481408 Danio rerio tie2 gene Proteins 0.000 description 1
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 description 1
- 108010002156 Depsipeptides Proteins 0.000 description 1
- GJKXGJCSJWBJEZ-XRSSZCMZSA-N Deslorelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CNC2=CC=CC=C12 GJKXGJCSJWBJEZ-XRSSZCMZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 102000016607 Diphtheria Toxin Human genes 0.000 description 1
- 108010053187 Diphtheria Toxin Proteins 0.000 description 1
- AADVCYNFEREWOS-OBRABYBLSA-N Discodermolide Chemical compound C=C\C=C/[C@H](C)[C@H](OC(N)=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C/[C@H](C)[C@@H](O)[C@@H](C)\C=C/[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C AADVCYNFEREWOS-OBRABYBLSA-N 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 206010058314 Dysplasia Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 201000009051 Embryonal Carcinoma Diseases 0.000 description 1
- 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
- 101000877447 Enterobacteria phage T4 Endonuclease V Proteins 0.000 description 1
- 206010014967 Ependymoma Diseases 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
- XOZIUKBZLSUILX-SDMHVBBESA-N Epothilone D Natural products O=C1[C@H](C)[C@@H](O)[C@@H](C)CCC/C(/C)=C/C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C XOZIUKBZLSUILX-SDMHVBBESA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 102000056372 ErbB-3 Receptor Human genes 0.000 description 1
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 1
- 208000036566 Erythroleukaemia Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 description 1
- 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 1
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 230000010337 G2 phase Effects 0.000 description 1
- 108700012941 GNRH1 Proteins 0.000 description 1
- 229940032072 GVAX vaccine Drugs 0.000 description 1
- RVAQIUULWULRNW-UHFFFAOYSA-N Ganetespib Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O RVAQIUULWULRNW-UHFFFAOYSA-N 0.000 description 1
- 229940124897 Gardasil Drugs 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 206010018338 Glioma Diseases 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
- 108010053070 Glutathione Disulfide Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
- 108010069236 Goserelin Proteins 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
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
- 102100031547 HLA class II histocompatibility antigen, DO alpha chain Human genes 0.000 description 1
- 102100032510 Heat shock protein HSP 90-beta Human genes 0.000 description 1
- 208000001258 Hemangiosarcoma Diseases 0.000 description 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 101000914247 Homo sapiens Centromere-associated protein E Proteins 0.000 description 1
- 101000897441 Homo sapiens Cyclin-O Proteins 0.000 description 1
- 101500025419 Homo sapiens Epidermal growth factor Proteins 0.000 description 1
- 101000866278 Homo sapiens HLA class II histocompatibility antigen, DO alpha chain Proteins 0.000 description 1
- 101001016856 Homo sapiens Heat shock protein HSP 90-beta Proteins 0.000 description 1
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- 101000621390 Homo sapiens Wee1-like protein kinase Proteins 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-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
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 1
- 102100023915 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 description 1
- 102100040018 Interferon alpha-2 Human genes 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
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 239000002118 L01XE12 - Vandetanib Substances 0.000 description 1
- 239000002144 L01XE18 - Ruxolitinib Substances 0.000 description 1
- UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 description 1
- CZQHHVNHHHRRDU-UHFFFAOYSA-N LY294002 Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1C1=CC=CC=C1 CZQHHVNHHHRRDU-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 1
- 208000018142 Leiomyosarcoma Diseases 0.000 description 1
- 101000988090 Leishmania donovani Heat shock protein 83 Proteins 0.000 description 1
- 108010000817 Leuprolide Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- 239000012819 MDM2-Inhibitor Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102000008135 Mechanistic Target of Rapamycin Complex 1 Human genes 0.000 description 1
- 108010035196 Mechanistic Target of Rapamycin Complex 1 Proteins 0.000 description 1
- 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 description 1
- 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 description 1
- 208000007054 Medullary Carcinoma Diseases 0.000 description 1
- 208000000172 Medulloblastoma Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 108700011259 MicroRNAs Proteins 0.000 description 1
- VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 1
- 208000003445 Mouth Neoplasms Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100481410 Mus musculus Tek gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241001467552 Mycobacterium bovis BCG Species 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- NFIXBCVWIPOYCD-UHFFFAOYSA-N N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1CC1=CC=CC=C1 NFIXBCVWIPOYCD-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical compound CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- WOKDGCSTFUDXQF-UHFFFAOYSA-N N-pyridin-4-ylbenzohydrazide Chemical compound N1=CC=C(C=C1)N(N)C(C1=CC=CC=C1)=O WOKDGCSTFUDXQF-UHFFFAOYSA-N 0.000 description 1
- 108010072915 NAc-Sar-Gly-Val-(d-allo-Ile)-Thr-Nva-Ile-Arg-ProNEt Proteins 0.000 description 1
- 102100031911 NEDD8 Human genes 0.000 description 1
- 108700004934 NEDD8 Proteins 0.000 description 1
- 101150107958 NEDD8 gene Proteins 0.000 description 1
- 101710204212 Neocarzinostatin Proteins 0.000 description 1
- 206010029260 Neuroblastoma Diseases 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- AFLXUQUGROGEFA-UHFFFAOYSA-N Nitrogen mustard N-oxide Chemical compound ClCC[N+]([O-])(C)CCCl AFLXUQUGROGEFA-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- MHQJUHSHQGQVTM-HNENSFHCSA-N Octadecyl fumarate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O MHQJUHSHQGQVTM-HNENSFHCSA-N 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 208000035327 Oestrogen receptor positive breast cancer Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 201000010133 Oligodendroglioma Diseases 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 101100532088 Oryza sativa subsp. japonica RUB2 gene Proteins 0.000 description 1
- 101100532090 Oryza sativa subsp. japonica RUB3 gene Proteins 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000012661 PARP inhibitor Substances 0.000 description 1
- SUDAHWBOROXANE-SECBINFHSA-N PD 0325901 Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-SECBINFHSA-N 0.000 description 1
- 108010025700 PR-171 Proteins 0.000 description 1
- QIUASFSNWYMDFS-NILGECQDSA-N PX-866 Chemical compound CC(=O)O[C@@H]1C[C@]2(C)C(=O)CC[C@H]2C2=C1[C@@]1(C)[C@@H](COC)OC(=O)\C(=C\N(CC=C)CC=C)C1=C(O)C2=O QIUASFSNWYMDFS-NILGECQDSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 108010057150 Peplomycin Proteins 0.000 description 1
- 208000007641 Pinealoma Diseases 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
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100025067 Potassium voltage-gated channel subfamily H member 4 Human genes 0.000 description 1
- 101710163352 Potassium voltage-gated channel subfamily H member 4 Proteins 0.000 description 1
- 208000009052 Precursor T-Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 102100033237 Pro-epidermal growth factor Human genes 0.000 description 1
- 101100528525 Prochlorococcus marinus (strain SARG / CCMP1375 / SS120) rnc gene Proteins 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229940079156 Proteasome inhibitor Drugs 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 238000012228 RNA interference-mediated gene silencing Methods 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 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
- 241000700159 Rattus Species 0.000 description 1
- QEHOIJJIZXRMAN-UHFFFAOYSA-N Rebeccamycin Natural products OC1C(O)C(OC)C(CO)OC1N1C2=C3NC4=C(Cl)C=CC=C4C3=C3C(=O)NC(=O)C3=C2C2=CC=CC(Cl)=C21 QEHOIJJIZXRMAN-UHFFFAOYSA-N 0.000 description 1
- 229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 description 1
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
- 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 201000000582 Retinoblastoma Diseases 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
- 230000018199 S phase Effects 0.000 description 1
- BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 229920000519 Sizofiran Polymers 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- OCOKWVBYZHBHLU-UHFFFAOYSA-N Sobuzoxane Chemical compound C1C(=O)N(COC(=O)OCC(C)C)C(=O)CN1CCN1CC(=O)N(COC(=O)OCC(C)C)C(=O)C1 OCOKWVBYZHBHLU-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 108010008038 Synthetic Vaccines Proteins 0.000 description 1
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 description 1
- 108010000449 TNF-Related Apoptosis-Inducing Ligand Receptors Proteins 0.000 description 1
- 102000002259 TNF-Related Apoptosis-Inducing Ligand Receptors Human genes 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 229930189037 Trapoxin Natural products 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
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 108010050144 Triptorelin Pamoate Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 102100040245 Tumor necrosis factor receptor superfamily member 5 Human genes 0.000 description 1
- 206010054094 Tumour necrosis Diseases 0.000 description 1
- 102000044159 Ubiquitin Human genes 0.000 description 1
- 108090000848 Ubiquitin Proteins 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 1
- 208000014070 Vestibular schwannoma Diseases 0.000 description 1
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 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
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
- 208000008383 Wilms tumor Diseases 0.000 description 1
- 101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 1
- RTJVUHUGTUDWRK-CSLCKUBZSA-N [(2r,4ar,6r,7r,8s,8ar)-6-[[(5s,5ar,8ar,9r)-9-(3,5-dimethoxy-4-phosphonooxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]oxy]-2-methyl-7-[2-(2,3,4,5,6-pentafluorophenoxy)acetyl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]d 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](OC(=O)COC=4C(=C(F)C(F)=C(F)C=4F)F)[C@@H]4O[C@H](C)OC[C@H]4O3)OC(=O)COC=3C(=C(F)C(F)=C(F)C=3F)F)[C@@H]3[C@@H]2C(OC3)=O)=C1 RTJVUHUGTUDWRK-CSLCKUBZSA-N 0.000 description 1
- JMNXSNUXDHHTKQ-QVMSTPCGSA-N [(3r,6r)-6-[(3s,5r,7r,8r,9s,10s,13r,14s,17r)-3-[3-(4-aminobutylamino)propylamino]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] hydrogen sulfate;(2s)-2-hydroxypropanoic ac Chemical compound C[C@H](O)C(O)=O.C([C@@H]1C[C@H]2O)[C@@H](NCCCNCCCCN)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C(C)C)OS(O)(=O)=O)[C@@]2(C)CC1 JMNXSNUXDHHTKQ-QVMSTPCGSA-N 0.000 description 1
- XJXKGUZINMNEDK-GPJOBVNKSA-L [(4r,5r)-5-(aminomethyl)-2-propan-2-yl-1,3-dioxolan-4-yl]methanamine;platinum(2+);propanedioate Chemical compound [Pt+2].[O-]C(=O)CC([O-])=O.CC(C)C1O[C@H](CN)[C@@H](CN)O1 XJXKGUZINMNEDK-GPJOBVNKSA-L 0.000 description 1
- XMYKNCNAZKMVQN-NYYWCZLTSA-N [(e)-(3-aminopyridin-2-yl)methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=NC=CC=C1N XMYKNCNAZKMVQN-NYYWCZLTSA-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
- 108010023617 abarelix Proteins 0.000 description 1
- AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
- 229960002184 abarelix Drugs 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 108010052004 acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ILys-prolyl-alaninamide Proteins 0.000 description 1
- 108010014659 acetyl-glycyl-valyl-allo-isoleucyl-seryl-glutaminyl-isoleucyl-arginyl-prolyl-cysteinamide Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960005339 acitretin Drugs 0.000 description 1
- 208000004064 acoustic neuroma Diseases 0.000 description 1
- 208000017733 acquired polycythemia vera Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 201000011186 acute T cell leukemia Diseases 0.000 description 1
- 208000021841 acute erythroid leukemia Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 125000001980 alanyl group Chemical group 0.000 description 1
- 229960005310 aldesleukin Drugs 0.000 description 1
- 229960000548 alemtuzumab Drugs 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229940110282 alimta Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940098174 alkeran Drugs 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical group 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940024545 aluminum hydroxide Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229960004701 amonafide Drugs 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
- 229960001220 amsacrine Drugs 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CIDNKDMVSINJCG-GKXONYSUSA-N annamycin Chemical compound I[C@@H]1[C@H](O)[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(=O)CO)C1 CIDNKDMVSINJCG-GKXONYSUSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940124650 anti-cancer therapies Drugs 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- 229950002465 apaziquone Drugs 0.000 description 1
- UVJYAKBJSGRTHA-ZCRGAIPPSA-N arglabin Chemical compound C1C[C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(C)=CC[C@]32O[C@]31C UVJYAKBJSGRTHA-ZCRGAIPPSA-N 0.000 description 1
- UVJYAKBJSGRTHA-UHFFFAOYSA-N arglabin Natural products C1CC2C(=C)C(=O)OC2C2C(C)=CCC32OC31C UVJYAKBJSGRTHA-UHFFFAOYSA-N 0.000 description 1
- 229940087620 aromasin Drugs 0.000 description 1
- MCGDSOGUHLTADD-UHFFFAOYSA-N arzoxifene Chemical compound C1=CC(OC)=CC=C1C1=C(OC=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 MCGDSOGUHLTADD-UHFFFAOYSA-N 0.000 description 1
- 229950005529 arzoxifene Drugs 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 229950004810 atamestane Drugs 0.000 description 1
- PEPMWUSGRKINHX-TXTPUJOMSA-N atamestane Chemical compound C1C[C@@H]2[C@@]3(C)C(C)=CC(=O)C=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C PEPMWUSGRKINHX-TXTPUJOMSA-N 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 229950010993 atrasentan Drugs 0.000 description 1
- MOTJMGVDPWRKOC-QPVYNBJUSA-N atrasentan Chemical compound C1([C@H]2[C@@H]([C@H](CN2CC(=O)N(CCCC)CCCC)C=2C=C3OCOC3=CC=2)C(O)=O)=CC=C(OC)C=C1 MOTJMGVDPWRKOC-QPVYNBJUSA-N 0.000 description 1
- 239000005441 aurora Substances 0.000 description 1
- 229940054720 avage Drugs 0.000 description 1
- 229960003005 axitinib Drugs 0.000 description 1
- RITAVMQDGBJQJZ-FMIVXFBMSA-N axitinib Chemical compound CNC(=O)C1=CC=CC=C1SC1=CC=C(C(\C=C\C=2N=CC=CC=2)=NN2)C2=C1 RITAVMQDGBJQJZ-FMIVXFBMSA-N 0.000 description 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
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 229960000190 bacillus calmette–guérin vaccine Drugs 0.000 description 1
- 229950001429 batabulin Drugs 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 229950008356 becatecarin Drugs 0.000 description 1
- LNHWXBUNXOXMRL-VWLOTQADSA-N belotecan Chemical compound C1=CC=C2C(CCNC(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 LNHWXBUNXOXMRL-VWLOTQADSA-N 0.000 description 1
- 229950011276 belotecan Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 229940110331 bextra Drugs 0.000 description 1
- XQVVPGYIWAGRNI-JOCHJYFZSA-N bi-2536 Chemical compound N1([C@@H](C(N(C)C2=CN=C(NC=3C(=CC(=CC=3)C(=O)NC3CCN(C)CC3)OC)N=C21)=O)CC)C1CCCC1 XQVVPGYIWAGRNI-JOCHJYFZSA-N 0.000 description 1
- 229960000997 bicalutamide Drugs 0.000 description 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
- 201000007180 bile duct carcinoma Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ACWZRVQXLIRSDF-UHFFFAOYSA-N binimetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1F ACWZRVQXLIRSDF-UHFFFAOYSA-N 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 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
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
- 229960001467 bortezomib Drugs 0.000 description 1
- 229960003065 bosentan Drugs 0.000 description 1
- 238000002725 brachytherapy Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229960000455 brentuximab vedotin Drugs 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 229950004271 brostallicin Drugs 0.000 description 1
- RXOVOXFAAGIKDQ-UHFFFAOYSA-N brostallicin Chemical compound C1=C(C(=O)NCCN=C(N)N)N(C)C=C1NC(=O)C1=CC(NC(=O)C=2N(C=C(NC(=O)C=3N(C=C(NC(=O)C(Br)=C)C=3)C)C=2)C)=CN1C RXOVOXFAAGIKDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229960002719 buserelin Drugs 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940112129 campath Drugs 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229940088954 camptosar Drugs 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- OMZCMEYTWSXEPZ-UHFFFAOYSA-N canertinib Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CC(OCCCN3CCOCC3)=C(NC(=O)C=C)C=C12 OMZCMEYTWSXEPZ-UHFFFAOYSA-N 0.000 description 1
- 229960004117 capecitabine Drugs 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 229960002115 carboquone Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 description 1
- 229960003261 carmofur Drugs 0.000 description 1
- 229960005243 carmustine Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960000419 catumaxomab Drugs 0.000 description 1
- 229960002412 cediranib Drugs 0.000 description 1
- 229940047495 celebrex Drugs 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 108700008462 cetrorelix Proteins 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
- IQCIQDNWBGEGRL-UHFFFAOYSA-N chembl1614651 Chemical compound O=C1C2=C(O)C=CC(O)=C2N2N=C(CNCCO)C3=CC=C(NCCCN)C1=C32 IQCIQDNWBGEGRL-UHFFFAOYSA-N 0.000 description 1
- ZFVRYNYOPQZKDG-MQMHXKEQSA-N chembl560895 Chemical compound O=C1CC(C)(C)CC2=C1C(C(F)(F)F)=NN2C(C=1)=CC=C(C(N)=O)C=1N[C@H]1CC[C@H](O)CC1 ZFVRYNYOPQZKDG-MQMHXKEQSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 230000024321 chromosome segregation Effects 0.000 description 1
- 208000024207 chronic leukemia Diseases 0.000 description 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
- 229950010810 cintredekin besudotox Drugs 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
- 229940001468 citrate Drugs 0.000 description 1
- 229960002436 cladribine Drugs 0.000 description 1
- 229960000928 clofarabine Drugs 0.000 description 1
- WDDPHFBMKLOVOX-AYQXTPAHSA-N clofarabine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F WDDPHFBMKLOVOX-AYQXTPAHSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229950007276 conatumumab Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940031670 conjugate vaccine Drugs 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- CZZLLDDFQKSALH-UHFFFAOYSA-N cpg 8954 Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C(OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OCC2C(CC(O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 CZZLLDDFQKSALH-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000026374 cyclin catabolic process Effects 0.000 description 1
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 208000002445 cystadenocarcinoma Diseases 0.000 description 1
- 229950006614 cytarabine ocfosfate Drugs 0.000 description 1
- YJTVZHOYBAOUTO-URBBEOKESA-N cytarabine ocfosfate Chemical compound O[C@H]1[C@H](O)[C@@H](COP(O)(=O)OCCCCCCCCCCCCCCCCCC)O[C@H]1N1C(=O)N=C(N)C=C1 YJTVZHOYBAOUTO-URBBEOKESA-N 0.000 description 1
- 230000001461 cytolytic effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 229960003901 dacarbazine Drugs 0.000 description 1
- 229960002806 daclizumab Drugs 0.000 description 1
- 229950006418 dactolisib Drugs 0.000 description 1
- JOGKUKXHTYWRGZ-UHFFFAOYSA-N dactolisib Chemical compound O=C1N(C)C2=CN=C3C=CC(C=4C=C5C=CC=CC5=NC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C=C1 JOGKUKXHTYWRGZ-UHFFFAOYSA-N 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 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
- 230000008260 defense mechanism Effects 0.000 description 1
- 229960000958 deferoxamine Drugs 0.000 description 1
- 229960002272 degarelix Drugs 0.000 description 1
- MEUCPCLKGZSHTA-XYAYPHGZSA-N degarelix Chemical compound C([C@H](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)NC(=O)[C@H](CC=1C=CC(NC(=O)[C@H]2NC(=O)NC(=O)C2)=CC=1)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(NC(N)=O)C=C1 MEUCPCLKGZSHTA-XYAYPHGZSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229960001251 denosumab Drugs 0.000 description 1
- 229960003314 deracoxib Drugs 0.000 description 1
- 229940051427 deramaxx Drugs 0.000 description 1
- 229960005408 deslorelin Drugs 0.000 description 1
- 108700025485 deslorelin Proteins 0.000 description 1
- XOZIUKBZLSUILX-UHFFFAOYSA-N desoxyepothilone B Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC(C)=CCC1C(C)=CC1=CSC(C)=N1 XOZIUKBZLSUILX-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 229960001259 diclofenac Drugs 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
- KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine 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
- 230000004069 differentiation Effects 0.000 description 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical class CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- NYDXNILOWQXUOF-UHFFFAOYSA-L disodium;2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioate Chemical compound [Na+].[Na+].C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)NC(CCC([O-])=O)C([O-])=O)C=C1 NYDXNILOWQXUOF-UHFFFAOYSA-L 0.000 description 1
- 229960003668 docetaxel 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
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940072701 dolobid Drugs 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
- 229960004679 doxorubicin Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- GVGYEFKIHJTNQZ-RFQIPJPRSA-N ecgonine benzoate Chemical compound O([C@@H]1[C@@H]([C@H]2CC[C@@H](C1)N2C)C(O)=O)C(=O)C1=CC=CC=C1 GVGYEFKIHJTNQZ-RFQIPJPRSA-N 0.000 description 1
- 229950001287 edotecarin Drugs 0.000 description 1
- 229960001776 edrecolomab Drugs 0.000 description 1
- BNFRJXLZYUTIII-UHFFFAOYSA-N efaproxiral Chemical compound CC1=CC(C)=CC(NC(=O)CC=2C=CC(OC(C)(C)C(O)=O)=CC=2)=C1 BNFRJXLZYUTIII-UHFFFAOYSA-N 0.000 description 1
- 229960000925 efaproxiral Drugs 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
- 229940121647 egfr inhibitor Drugs 0.000 description 1
- 229940120655 eloxatin 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
- 229950002339 elsamitrucin Drugs 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000003511 endothelial effect Effects 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
- 229950011487 enocitabine Drugs 0.000 description 1
- HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
- INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 description 1
- 229950002189 enzastaurin Drugs 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 208000037828 epithelial carcinoma Diseases 0.000 description 1
- 229930013356 epothilone Natural products 0.000 description 1
- HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 1
- QXRSDHAAWVKZLJ-PVYNADRNSA-N epothilone B Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 QXRSDHAAWVKZLJ-PVYNADRNSA-N 0.000 description 1
- 150000003883 epothilone derivatives Chemical class 0.000 description 1
- 229950009760 epratuzumab Drugs 0.000 description 1
- 229950006835 eptaplatin Drugs 0.000 description 1
- 229940082789 erbitux Drugs 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 229960001842 estramustine Drugs 0.000 description 1
- FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
- 201000007281 estrogen-receptor positive breast cancer Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229960005293 etodolac Drugs 0.000 description 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-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
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
- 229960005167 everolimus Drugs 0.000 description 1
- 229960000255 exemestane Drugs 0.000 description 1
- 230000031376 exit from mitosis Effects 0.000 description 1
- 230000028023 exocytosis Effects 0.000 description 1
- 231100000776 exotoxin Toxicity 0.000 description 1
- 239000002095 exotoxin Substances 0.000 description 1
- 229950011548 fadrozole Drugs 0.000 description 1
- 229940043168 fareston Drugs 0.000 description 1
- 229950003662 fenretinide Drugs 0.000 description 1
- 229950000133 filanesib Drugs 0.000 description 1
- LLXISKGBWFTGEI-FQEVSTJZSA-N filanesib Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)N(C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 LLXISKGBWFTGEI-FQEVSTJZSA-N 0.000 description 1
- 229960004177 filgrastim Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229960000961 floxuridine Drugs 0.000 description 1
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
- 235000008191 folinic acid Nutrition 0.000 description 1
- 239000011672 folinic acid Substances 0.000 description 1
- 201000003444 follicular lymphoma Diseases 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229960004421 formestane Drugs 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960004783 fotemustine Drugs 0.000 description 1
- YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 150000002270 gangliosides Chemical class 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 108010063604 gastrin immunogen Proteins 0.000 description 1
- 229960002584 gefitinib Drugs 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical compound N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 description 1
- 229960003297 gemtuzumab ozogamicin Drugs 0.000 description 1
- 230000030279 gene silencing Effects 0.000 description 1
- 230000009368 gene silencing by RNA Effects 0.000 description 1
- 238000012226 gene silencing method Methods 0.000 description 1
- 210000004602 germ cell Anatomy 0.000 description 1
- UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 description 1
- 229950009073 gimatecan Drugs 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 229940080856 gleevec Drugs 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229950011595 glufosfamide Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 description 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- 229960002913 goserelin Drugs 0.000 description 1
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- LVASCWIMLIKXLA-LSDHHAIUSA-N halofuginone Chemical compound O[C@@H]1CCCN[C@H]1CC(=O)CN1C(=O)C2=CC(Cl)=C(Br)C=C2N=C1 LVASCWIMLIKXLA-LSDHHAIUSA-N 0.000 description 1
- 229950010152 halofuginone Drugs 0.000 description 1
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 1
- 208000025750 heavy chain disease Diseases 0.000 description 1
- 201000002222 hemangioblastoma Diseases 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229940022353 herceptin Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 108010040030 histidinoalanine Proteins 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 108700020746 histrelin Proteins 0.000 description 1
- 229960002193 histrelin Drugs 0.000 description 1
- HHXHVIJIIXKSOE-QILQGKCVSA-N histrelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(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=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC(N=C1)=CN1CC1=CC=CC=C1 HHXHVIJIIXKSOE-QILQGKCVSA-N 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 102000045973 human WEE1 Human genes 0.000 description 1
- 229940116978 human epidermal growth factor Drugs 0.000 description 1
- 229940124866 human papillomavirus vaccine Drugs 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
- 229960004171 hydroxychloroquine Drugs 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
- 229960000908 idarubicin 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
- 229960002411 imatinib Drugs 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229960002751 imiquimod Drugs 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
- 239000000367 immunologic factor Substances 0.000 description 1
- 230000001024 immunotherapeutic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000006882 induction of apoptosis Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229960001388 interferon-beta Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229960005386 ipilimumab Drugs 0.000 description 1
- 229940084651 iressa Drugs 0.000 description 1
- 229960000779 irinotecan hydrochloride Drugs 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
- 125000005438 isoindazolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- FABUFPQFXZVHFB-PVYNADRNSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-PVYNADRNSA-N 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 229960004752 ketorolac Drugs 0.000 description 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 108010021336 lanreotide Proteins 0.000 description 1
- 229960002437 lanreotide Drugs 0.000 description 1
- 229950000340 laromustine Drugs 0.000 description 1
- 229950005692 larotaxel Drugs 0.000 description 1
- 229960002367 lasofoxifene Drugs 0.000 description 1
- GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 description 1
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 description 1
- 229960002618 lenograstim Drugs 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 229960003881 letrozole Drugs 0.000 description 1
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
- 229960001691 leucovorin Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 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
- 230000000670 limiting effect Effects 0.000 description 1
- MPVGZUGXCQEXTM-UHFFFAOYSA-N linifanib Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C=CC=2)=C1 MPVGZUGXCQEXTM-UHFFFAOYSA-N 0.000 description 1
- 229950002950 lintuzumab Drugs 0.000 description 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 206010024627 liposarcoma Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 229950008991 lobaplatin Drugs 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- DHMTURDWPRKSOA-RUZDIDTESA-N lonafarnib Chemical compound C1CN(C(=O)N)CCC1CC(=O)N1CCC([C@@H]2C3=C(Br)C=C(Cl)C=C3CCC3=CC(Br)=CN=C32)CC1 DHMTURDWPRKSOA-RUZDIDTESA-N 0.000 description 1
- 229950001750 lonafarnib Drugs 0.000 description 1
- 239000006210 lotion Substances 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
- 239000000314 lubricant Substances 0.000 description 1
- 229960000994 lumiracoxib Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
- 229950002654 lurtotecan Drugs 0.000 description 1
- 208000012804 lymphangiosarcoma Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229940124302 mTOR inhibitor Drugs 0.000 description 1
- 229940092110 macugen Drugs 0.000 description 1
- 229950000547 mafosfamide Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229950002736 marizomib Drugs 0.000 description 1
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 206010027191 meningioma Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BRWZPVRDOUWXKE-UHFFFAOYSA-N methylsulfanylmethane;trifluoroborane Chemical compound CSC.FB(F)F BRWZPVRDOUWXKE-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 229940099246 mevacor Drugs 0.000 description 1
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
- 239000002679 microRNA Substances 0.000 description 1
- 229960005225 mifamurtide Drugs 0.000 description 1
- 108700007621 mifamurtide Proteins 0.000 description 1
- 229960003248 mifepristone Drugs 0.000 description 1
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 1
- UQRORFVVSGFNRO-UTINFBMNSA-N miglustat Chemical compound CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO UQRORFVVSGFNRO-UTINFBMNSA-N 0.000 description 1
- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 description 1
- 229960005485 mitobronitol Drugs 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor 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
- 230000006618 mitotic catastrophe Effects 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 229960003063 molgramostim Drugs 0.000 description 1
- 108010032806 molgramostim Proteins 0.000 description 1
- VYGYNVZNSSTDLJ-HKCOAVLJSA-N monorden Natural products CC1CC2OC2C=C/C=C/C(=O)CC3C(C(=CC(=C3Cl)O)O)C(=O)O1 VYGYNVZNSSTDLJ-HKCOAVLJSA-N 0.000 description 1
- 229940072709 motrin Drugs 0.000 description 1
- ZTFBIUXIQYRUNT-MDWZMJQESA-N mubritinib Chemical compound C1=CC(C(F)(F)F)=CC=C1\C=C\C1=NC(COC=2C=CC(CCCCN3N=NC=C3)=CC=2)=CO1 ZTFBIUXIQYRUNT-MDWZMJQESA-N 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
- 229960000951 mycophenolic acid Drugs 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 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
- 208000001611 myxosarcoma Diseases 0.000 description 1
- ISGGVCWFTPTHIX-UHFFFAOYSA-N n'-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidamide;dihydrochloride Chemical compound Cl.Cl.C1CCCCN1CC(O)CONC(=N)C1=CC=CN=C1 ISGGVCWFTPTHIX-UHFFFAOYSA-N 0.000 description 1
- SMFXSYMLJDHGIE-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N=1C=2SN=C(C)C=2C(=O)N(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 SMFXSYMLJDHGIE-UHFFFAOYSA-N 0.000 description 1
- ARDNTAZQAKTAJQ-UHFFFAOYSA-N n-cyclohexylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)N(N)C1CCCCC1 ARDNTAZQAKTAJQ-UHFFFAOYSA-N 0.000 description 1
- 229960004270 nabumetone Drugs 0.000 description 1
- 229950007221 nedaplatin Drugs 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
- 229950010159 nemorubicin Drugs 0.000 description 1
- CTMCWCONSULRHO-UHQPFXKFSA-N nemorubicin Chemical compound C1CO[C@H](OC)CN1[C@@H]1[C@H](O)[C@H](C)O[C@@H](O[C@@H]2C3=C(O)C=4C(=O)C5=C(OC)C=CC=C5C(=O)C=4C(O)=C3C[C@](O)(C2)C(=O)CO)C1 CTMCWCONSULRHO-UHQPFXKFSA-N 0.000 description 1
- GVUGOAYIVIDWIO-UFWWTJHBSA-N nepidermin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)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](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C(C)C)C(C)C)C1=CC=C(O)C=C1 GVUGOAYIVIDWIO-UFWWTJHBSA-N 0.000 description 1
- 229940029345 neupogen Drugs 0.000 description 1
- 229940063708 neutrexin Drugs 0.000 description 1
- 229940080607 nexavar Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960002653 nilutamide 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
- 229960001420 nimustine Drugs 0.000 description 1
- VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 1
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 1
- 229940109551 nipent Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 229950000891 nolatrexed Drugs 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 229950006584 obatoclax Drugs 0.000 description 1
- 229960002450 ofatumumab Drugs 0.000 description 1
- 229960000572 olaparib Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229950003600 ombrabulin Drugs 0.000 description 1
- IXWNTLSTOZFSCM-YVACAVLKSA-N ombrabulin Chemical compound C1=C(NC(=O)[C@@H](N)CO)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 IXWNTLSTOZFSCM-YVACAVLKSA-N 0.000 description 1
- 229950007283 oregovomab Drugs 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- 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 1
- 229960002739 oxaprozin Drugs 0.000 description 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 108700025694 p53 Genes Proteins 0.000 description 1
- 229960002239 paclitaxel poliglumex Drugs 0.000 description 1
- 108700027936 paclitaxel poliglumex Proteins 0.000 description 1
- 229960003978 pamidronic acid Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229940096763 panretin Drugs 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 208000004019 papillary adenocarcinoma Diseases 0.000 description 1
- 201000010198 papillary carcinoma 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
- 230000001575 pathological effect Effects 0.000 description 1
- 229950007460 patupilone Drugs 0.000 description 1
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 description 1
- 229960001744 pegaspargase Drugs 0.000 description 1
- 108010001564 pegaspargase Proteins 0.000 description 1
- WVUNYSQLFKLYNI-AATRIKPKSA-N pelitinib Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 WVUNYSQLFKLYNI-AATRIKPKSA-N 0.000 description 1
- 229950003819 pelitrexol Drugs 0.000 description 1
- WBXPDJSOTKVWSJ-ZDUSSCGKSA-N pemetrexed Chemical compound C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 WBXPDJSOTKVWSJ-ZDUSSCGKSA-N 0.000 description 1
- 229960003349 pemetrexed disodium Drugs 0.000 description 1
- NYDXNILOWQXUOF-GXKRWWSZSA-L pemetrexed disodium Chemical compound [Na+].[Na+].C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 NYDXNILOWQXUOF-GXKRWWSZSA-L 0.000 description 1
- 229960005570 pemtumomab 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229950005566 picoplatin Drugs 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- LHNIIDJUOCFXAP-UHFFFAOYSA-N pictrelisib Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 LHNIIDJUOCFXAP-UHFFFAOYSA-N 0.000 description 1
- 208000024724 pineal body neoplasm Diseases 0.000 description 1
- 201000004123 pineal gland cancer Diseases 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
- 229960001221 pirarubicin Drugs 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229960004403 pixantrone Drugs 0.000 description 1
- PEZPMAYDXJQYRV-UHFFFAOYSA-N pixantrone Chemical compound O=C1C2=CN=CC=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN PEZPMAYDXJQYRV-UHFFFAOYSA-N 0.000 description 1
- 239000002770 polo like kinase inhibitor Substances 0.000 description 1
- 208000037244 polycythemia vera Diseases 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108010001062 polysaccharide-K Proteins 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MREOOEFUTWFQOC-UHFFFAOYSA-M potassium;5-chloro-4-hydroxy-1h-pyridin-2-one;4,6-dioxo-1h-1,3,5-triazine-2-carboxylate;5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione Chemical compound [K+].OC1=CC(=O)NC=C1Cl.[O-]C(=O)C1=NC(=O)NC(=O)N1.O=C1NC(=O)C(F)=CN1C1OCCC1 MREOOEFUTWFQOC-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 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
- 229940087463 proleukin Drugs 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229940030749 prostate cancer vaccine Drugs 0.000 description 1
- 239000003207 proteasome inhibitor Substances 0.000 description 1
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- SHCBCKBYTHZQGZ-CJPZEJHVSA-N protopanaxatriol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2[C@@H](O)C[C@@]3(C)[C@]4(C)CC[C@H]([C@@](C)(O)CCC=C(C)C)[C@H]4[C@H](O)C[C@@H]3[C@]21C SHCBCKBYTHZQGZ-CJPZEJHVSA-N 0.000 description 1
- BBEUDPAEKGPXDG-UHFFFAOYSA-N protopanaxatriol Natural products CC(CCC=C(C)C)C1CCC2(C)C1C(O)CC3C4(C)CCC(O)C(C)(C)C4C(O)CC23C BBEUDPAEKGPXDG-UHFFFAOYSA-N 0.000 description 1
- 229940034080 provenge Drugs 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 229940117820 purinethol Drugs 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- WVTKBKWTSCPRNU-UHFFFAOYSA-N rac-Tetrandrin Natural products O1C(C(=CC=2CCN3C)OC)=CC=2C3CC(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2CC2N(C)CCC3=CC(OC)=C(OC)C1=C23 WVTKBKWTSCPRNU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- AECPBJMOGBFQDN-YMYQVXQQSA-N radicicol Chemical compound C1CCCC(=O)C[C@H]2[C@H](Cl)C(=O)CC(=O)[C@H]2C(=O)O[C@H](C)C[C@H]2O[C@@H]21 AECPBJMOGBFQDN-YMYQVXQQSA-N 0.000 description 1
- 229930192524 radicicol Natural products 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 229960004622 raloxifene Drugs 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
- 229960002185 ranimustine Drugs 0.000 description 1
- 108010061338 ranpirnase Proteins 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 229960005567 rebeccamycin Drugs 0.000 description 1
- INSACQSBHKIWNS-QZQSLCQPSA-N rebeccamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](OC)[C@@H](CO)O[C@H]1N1C2=C3N=C4[C](Cl)C=CC=C4C3=C3C(=O)NC(=O)C3=C2C2=CC=CC(Cl)=C21 INSACQSBHKIWNS-QZQSLCQPSA-N 0.000 description 1
- 229950005950 rebimastat Drugs 0.000 description 1
- 108091006082 receptor inhibitors Proteins 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229940124551 recombinant vaccine Drugs 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229940087462 relafen Drugs 0.000 description 1
- OAKGNIRUXAZDQF-TXHRRWQRSA-N retaspimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(O)C1=CC(O)=C2NCC=C OAKGNIRUXAZDQF-TXHRRWQRSA-N 0.000 description 1
- 229940002683 retin-a Drugs 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
- 101150024074 rub1 gene Proteins 0.000 description 1
- FCCGJTKEKXUBFZ-UHFFFAOYSA-N rucaparib phosphate Chemical compound OP(O)(O)=O.C1=CC(CNC)=CC=C1C(N1)=C2CCNC(=O)C3=C2C1=CC(F)=C3 FCCGJTKEKXUBFZ-UHFFFAOYSA-N 0.000 description 1
- HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical compound C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 description 1
- 229960000215 ruxolitinib Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- NGWSFRIPKNWYAO-SHTIJGAHSA-N salinosporamide A Chemical compound C([C@@H]1[C@H](O)[C@]23C(=O)O[C@]2([C@H](C(=O)N3)CCCl)C)CCC=C1 NGWSFRIPKNWYAO-SHTIJGAHSA-N 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 229960005399 satraplatin Drugs 0.000 description 1
- 190014017285 satraplatin Chemical compound 0.000 description 1
- 201000008407 sebaceous adenocarcinoma Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229950000055 seliciclib Drugs 0.000 description 1
- CYOHGALHFOKKQC-UHFFFAOYSA-N selumetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl CYOHGALHFOKKQC-UHFFFAOYSA-N 0.000 description 1
- 229950009921 seocalcitol Drugs 0.000 description 1
- 229960005441 sevelamer carbonate Drugs 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229960000714 sipuleucel-t Drugs 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 229950001403 sizofiran Drugs 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229950010372 sobuzoxane Drugs 0.000 description 1
- NGIYLSFJGRLEMI-MHTUOZSYSA-M sodium 2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethyl [(2R)-2,3-di(hexadecanoyloxy)propyl] phosphate hydrate Chemical compound O.[Na+].CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCCNC(=O)[C@H](C)NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)C(N)=O)OC(=O)CCCCCCCCCCCCCCC NGIYLSFJGRLEMI-MHTUOZSYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229940072291 soriatane Drugs 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 229940071138 stearyl fumarate Drugs 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- MPUQHZXIXSTTDU-QXGSTGNESA-N sulfamic acid [(1S,2S,4R)-4-[4-[[(1S)-2,3-dihydro-1H-inden-1-yl]amino]-7-pyrrolo[2,3-d]pyrimidinyl]-2-hydroxycyclopentyl]methyl ester Chemical compound C1[C@H](O)[C@H](COS(=O)(=O)N)C[C@H]1N1C2=NC=NC(N[C@@H]3C4=CC=CC=C4CC3)=C2C=C1 MPUQHZXIXSTTDU-QXGSTGNESA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 1
- 229960001796 sunitinib Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229940034785 sutent Drugs 0.000 description 1
- 201000010965 sweat gland carcinoma Diseases 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 206010042863 synovial sarcoma Diseases 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 229950003999 tafluposide Drugs 0.000 description 1
- 108010009573 talabostat Proteins 0.000 description 1
- 229950010637 talabostat Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960003454 tamoxifen citrate Drugs 0.000 description 1
- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
- 229950007866 tanespimycin Drugs 0.000 description 1
- 229940120982 tarceva Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229960003102 tasonermin Drugs 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- 229960000565 tazarotene Drugs 0.000 description 1
- 229950001699 teceleukin Drugs 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229940061353 temodar Drugs 0.000 description 1
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-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
- PUSREPRJUUKVOZ-ZDUSSCGKSA-N tert-butyl (2s)-2-[(4-aminophenoxy)methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1COC1=CC=C(N)C=C1 PUSREPRJUUKVOZ-ZDUSSCGKSA-N 0.000 description 1
- QUBNPUPUCMVUFI-UHFFFAOYSA-N tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C1=CC=C(N)C=C1 QUBNPUPUCMVUFI-UHFFFAOYSA-N 0.000 description 1
- IPISOFJLWYBCAV-UHFFFAOYSA-N tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate Chemical compound C1=NN(C(=O)OC(C)(C)C)C=C1B1OC(C)(C)C(C)(C)O1 IPISOFJLWYBCAV-UHFFFAOYSA-N 0.000 description 1
- SKNCMVAICXALKM-UHFFFAOYSA-N tert-butyl 4-(4-amino-2,6-difluorophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=C(F)C=C(N)C=C1F SKNCMVAICXALKM-UHFFFAOYSA-N 0.000 description 1
- KYORUZMJUKHKFS-UHFFFAOYSA-N tert-butyl 4-aminobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(N)C=C1 KYORUZMJUKHKFS-UHFFFAOYSA-N 0.000 description 1
- OLOIFCYZWOTWRO-UHFFFAOYSA-N tert-butyl 6-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound NC1=CC=C2CN(C(=O)OC(C)(C)C)CCC2=C1 OLOIFCYZWOTWRO-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
- FVADBMKSOPRMLP-UHFFFAOYSA-N tert-butyl n-[2-(4-amino-2-chlorophenoxy)ethyl]-n-propan-2-ylcarbamate Chemical compound CC(C)(C)OC(=O)N(C(C)C)CCOC1=CC=C(N)C=C1Cl FVADBMKSOPRMLP-UHFFFAOYSA-N 0.000 description 1
- LRRSULACZVLEIN-UHFFFAOYSA-N tert-butyl n-[2-(4-amino-2-methoxyphenoxy)ethyl]-n-propan-2-ylcarbamate Chemical compound COC1=CC(N)=CC=C1OCCN(C(C)C)C(=O)OC(C)(C)C LRRSULACZVLEIN-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950007967 tesmilifene Drugs 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
- 229940110675 theracys Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 229960003723 tiazofurine Drugs 0.000 description 1
- FVRDYQYEVDDKCR-DBRKOABJSA-N tiazofurine Chemical compound NC(=O)C1=CSC([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 FVRDYQYEVDDKCR-DBRKOABJSA-N 0.000 description 1
- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- AKCRNFFTGXBONI-UHFFFAOYSA-N torin 1 Chemical compound C1CN(C(=O)CC)CCN1C1=CC=C(N2C(C=CC3=C2C2=CC(=CC=C2N=C3)C=2C=C3C=CC=CC3=NC=2)=O)C=C1C(F)(F)F AKCRNFFTGXBONI-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 229960000977 trabectedin Drugs 0.000 description 1
- 229940118436 tracleer Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 108010060597 trapoxin A Proteins 0.000 description 1
- 229940066958 treanda Drugs 0.000 description 1
- 229940032510 trelstar Drugs 0.000 description 1
- 229960003181 treosulfan Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960005526 triapine Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- PUMSLVXNEXVCIC-UHFFFAOYSA-N tributyl(prop-1-en-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C(C)=C PUMSLVXNEXVCIC-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960001099 trimetrexate 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
- 229960000538 trimetrexate glucuronate Drugs 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical class [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940086984 trisenox Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229950010147 troxacitabine Drugs 0.000 description 1
- RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000002628 unsealed source radiotherapy Methods 0.000 description 1
- AUFUWRKPQLGTGF-FMKGYKFTSA-N uridine triacetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=C1 AUFUWRKPQLGTGF-FMKGYKFTSA-N 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- XGOYIMQSIKSOBS-UHFFFAOYSA-N vadimezan Chemical compound C1=CC=C2C(=O)C3=CC=C(C)C(C)=C3OC2=C1CC(O)=O XGOYIMQSIKSOBS-UHFFFAOYSA-N 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- 229940054937 valstar Drugs 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229960003636 vidarabine Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940087652 vioxx Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 108010069784 vitespin Proteins 0.000 description 1
- 229940063674 voltaren Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 description 1
- QDLHCMPXEPAAMD-UHFFFAOYSA-N wortmannin Natural products COCC1OC(=O)C2=COC(C3=O)=C2C1(C)C1=C3C2CCC(=O)C2(C)CC1OC(C)=O QDLHCMPXEPAAMD-UHFFFAOYSA-N 0.000 description 1
- 229940053867 xeloda Drugs 0.000 description 1
- ZPUHVPYXSITYDI-HEUWMMRCSA-N xyotax Chemical compound OC(=O)[C@@H](N)CCC(O)=O.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 ZPUHVPYXSITYDI-HEUWMMRCSA-N 0.000 description 1
- 229940004212 yondelis Drugs 0.000 description 1
- 229950009002 zanolimumab Drugs 0.000 description 1
- 229940099072 zavesca Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 229940002005 zometa Drugs 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161447405P | 2011-02-28 | 2011-02-28 | |
| US61/447,405 | 2011-02-28 | ||
| PCT/US2012/026685 WO2012161812A1 (en) | 2011-02-28 | 2012-02-27 | Tricyclic inhibitors of kinases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2827648A1 true CA2827648A1 (en) | 2012-11-29 |
Family
ID=46000328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2827648A Abandoned CA2827648A1 (en) | 2011-02-28 | 2012-02-27 | Tricyclic inhibitors of kinases |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8710065B2 (enExample) |
| EP (1) | EP2681221B1 (enExample) |
| JP (1) | JP5886326B2 (enExample) |
| CN (1) | CN103703005A (enExample) |
| AR (1) | AR085502A1 (enExample) |
| CA (1) | CA2827648A1 (enExample) |
| ES (1) | ES2587514T3 (enExample) |
| MX (1) | MX340402B (enExample) |
| TW (1) | TWI532742B (enExample) |
| UY (1) | UY33925A (enExample) |
| WO (1) | WO2012161812A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015154191A1 (en) * | 2014-04-10 | 2015-10-15 | Dalhousie University | Treatment of parkinson's disease through arfgap1 inhibition using substituted piperazine derivatives |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| RS61089B1 (sr) | 2012-06-13 | 2020-12-31 | Incyte Holdings Corp | Supstituisana triciklična jedinjenja kao inhibitori fgfr |
| WO2014026125A1 (en) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Pyrazine derivatives as fgfr inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| DK2986610T5 (en) | 2013-04-19 | 2018-12-10 | Incyte Holdings Corp | BICYCLIC HETEROCYCLES AS FGFR INHIBITORS |
| JPWO2015029447A1 (ja) * | 2013-08-30 | 2017-03-02 | 興和株式会社 | 光学活性カルビノール化合物の製造方法 |
| GB201322602D0 (en) * | 2013-12-19 | 2014-02-05 | Almac Discovery Ltd | Pharmaceutical compounds |
| EP3185860A4 (en) | 2014-08-29 | 2018-08-29 | The Board of Regents of the University of Texas System | Novel capsazepine analogs for the treatment of cancer and other proliferative diseases |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| SG11201706287PA (en) | 2015-02-20 | 2017-09-28 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| CN109906227B (zh) * | 2016-11-16 | 2022-03-11 | 上海瑛派药业有限公司 | 8,9-二氢咪唑[1,2-a]嘧啶并[5,4-e]嘧啶-5(6H)-酮类化合物 |
| CN110198943B (zh) * | 2017-01-23 | 2021-04-16 | 石家庄智康弘仁新药开发有限公司 | 作为Wee1抑制剂的1,2-二氢-3H-吡唑[3,4-d]嘧啶-3-酮衍生物 |
| AU2018243667A1 (en) | 2017-03-31 | 2019-10-17 | Seagen Inc. | Combinations of Chk1- and Wee1 - inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| US11345710B2 (en) | 2017-07-10 | 2022-05-31 | Impact Therapeutics (Shanghai), Inc | Imidazo[1,2-b]pyrimido[4,5-d]pyridazin-5(6H)-ones and the use thereof |
| CA3071795A1 (en) | 2017-08-04 | 2019-02-07 | Bayer Aktiengesellschaft | 6-phenyl-4,5-dihydropyridazin-3(2h)-one derivatives as pde3a and pde3b inhibitors for treating cancer |
| JOP20200024A1 (ar) | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
| CN107821390A (zh) * | 2017-10-13 | 2018-03-23 | 南京扬子鸿利源化学品有限责任公司 | 一种甲基磺草酮油悬浮剂及其制备方法 |
| PL3712150T3 (pl) | 2017-11-01 | 2024-09-02 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Związek makrocykliczny służący jako inhibitor wee1 i jego zastosowania |
| KR20210018264A (ko) | 2018-05-04 | 2021-02-17 | 인사이트 코포레이션 | Fgfr 억제제의 염 |
| WO2019213544A2 (en) | 2018-05-04 | 2019-11-07 | Incyte Corporation | Solid forms of an fgfr inhibitor and processes for preparing the same |
| CN108727249A (zh) * | 2018-07-07 | 2018-11-02 | 台州学院 | 3-二氟甲基哌啶盐酸盐及其衍生物的合成方法 |
| KR20210066839A (ko) * | 2018-09-27 | 2021-06-07 | 베타 파머수티컬 컴퍼니 리미티드 | Fgfr4 저해제 및 그것의 용도 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020083404A1 (zh) | 2018-10-26 | 2020-04-30 | 南京明德新药研发有限公司 | 作为Wee1抑制剂的嘧啶并吡唑酮类衍生物及其应用 |
| CA3128293A1 (en) | 2019-02-01 | 2020-08-06 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2h)-one compounds for the treatment of hyperproliferative diseases |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| US11472791B2 (en) | 2019-03-05 | 2022-10-18 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as CDK2 inhibitors |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| PT3964510T (pt) | 2019-04-30 | 2024-07-29 | Wuxi Biocity Biopharmaceutics Co Ltd | Forma cristalina do composto inibidor de wee1 e sua utilização |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223558A1 (en) * | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| EP4013750A1 (en) | 2019-08-14 | 2022-06-22 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| CN112442049A (zh) * | 2019-09-03 | 2021-03-05 | 微境生物医药科技(上海)有限公司 | 作为Wee1抑制剂的嘧啶衍生物 |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| GEAP202516803A (en) | 2019-10-11 | 2025-10-10 | Incyte Corp | Bicyclic amines as cdk2 inhibitors |
| EP4045151A1 (en) | 2019-10-14 | 2022-08-24 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN114502559B (zh) * | 2019-10-16 | 2024-02-02 | 上海瑛派药业有限公司 | 二氢咪唑并嘧啶并嘧啶酮类化合物 |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| IL293001A (en) | 2019-12-04 | 2022-07-01 | Incyte Corp | Derivatives of fgfr repressors |
| WO2021113479A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| JP7796674B2 (ja) | 2020-06-17 | 2026-01-09 | ウィゲン・バイオメディシン・テクノロジー・（シャンハイ）・カンパニー・リミテッド | Ｗｅｅ－１阻害剤としてのピラゾロ［３，４－ｄ］ピリミジン－３－オン誘導体 |
| US20240182447A1 (en) * | 2021-02-19 | 2024-06-06 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Fused ring compound as wee-1 inhibitor |
| JP2024513575A (ja) | 2021-04-12 | 2024-03-26 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤及びネクチン－４標的化剤を含む併用療法 |
| BR112023022236A2 (pt) * | 2021-04-30 | 2024-02-06 | Wigen Biomedicine Tech Shanghai Co Ltd | Composto de fórmula geral (1) ou seu isômero, forma cristalina, sal farmaceuticamente aceitável, hidrato ou solvato; composição farmacêutica; e; uso do composto ou seu isômero, forma cristalina, sal farmaceuticamente aceitável, hidrato ou solvato |
| WO2022261160A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313610A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US20250049798A1 (en) * | 2021-11-09 | 2025-02-13 | Hangzhou Glubio Pharmaceutical Co. Ltd. | Wee1 protein kinase degradation agent and use thereof |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN116836184B (zh) * | 2022-03-25 | 2025-07-25 | 药雅科技(上海)有限公司 | Wee1激酶抑制剂的制备及其应用 |
| WO2024199388A1 (zh) * | 2023-03-29 | 2024-10-03 | 微境生物医药科技(上海)有限公司 | 作为myt1抑制剂的化合物 |
| CN119039287A (zh) * | 2023-05-29 | 2024-11-29 | 中国药科大学 | 一类四氢吡啶并嘧啶酮衍生物及其制备方法与应用 |
| KR20250136774A (ko) * | 2024-03-08 | 2025-09-16 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2534990A1 (en) | 2003-07-25 | 2005-02-10 | Novartis Ag | P-38 kinase inhibitors |
| US20050070554A1 (en) * | 2003-08-27 | 2005-03-31 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| US20050250836A1 (en) * | 2004-05-03 | 2005-11-10 | Pfizer Inc | Inhibitors of checkpoint kinases (Wee1 and Chk1) |
| AR058277A1 (es) | 2005-12-09 | 2008-01-30 | Solvay Pharm Gmbh | N- sulfamoil - piperidin - amidas, composiciones farmaceuticas que las comprenden y procedimiento para su preparacion |
| CN101553491B (zh) * | 2006-12-13 | 2013-05-29 | Aska制药株式会社 | 喹喔啉衍生物 |
| WO2009054332A1 (ja) * | 2007-10-23 | 2009-04-30 | Banyu Pharmaceutical Co., Ltd. | ピリドン置換ジヒドロピラゾロピリミジノン誘導体 |
| US8507504B2 (en) | 2008-06-12 | 2013-08-13 | Merck Sharp & Dohme Corp. | Process for producing bicycloaniline derivatives |
| AU2009325398A1 (en) * | 2008-12-12 | 2010-06-17 | Msd K.K. | Dihydropyrimidopyrimidine derivative |
-
2012
- 2012-02-24 TW TW101106325A patent/TWI532742B/zh not_active IP Right Cessation
- 2012-02-27 WO PCT/US2012/026685 patent/WO2012161812A1/en not_active Ceased
- 2012-02-27 MX MX2013009873A patent/MX340402B/es active IP Right Grant
- 2012-02-27 CN CN201280018862.6A patent/CN103703005A/zh active Pending
- 2012-02-27 JP JP2013556755A patent/JP5886326B2/ja not_active Expired - Fee Related
- 2012-02-27 CA CA2827648A patent/CA2827648A1/en not_active Abandoned
- 2012-02-27 ES ES12716781.5T patent/ES2587514T3/es active Active
- 2012-02-27 UY UY0001033925A patent/UY33925A/es not_active Application Discontinuation
- 2012-02-27 EP EP12716781.5A patent/EP2681221B1/en not_active Not-in-force
- 2012-02-28 AR ARP120100641A patent/AR085502A1/es unknown
- 2012-02-28 US US13/406,937 patent/US8710065B2/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015154191A1 (en) * | 2014-04-10 | 2015-10-15 | Dalhousie University | Treatment of parkinson's disease through arfgap1 inhibition using substituted piperazine derivatives |
| AU2015245901B2 (en) * | 2014-04-10 | 2017-05-25 | Dalhousie University | Treatment of Parkinson's disease through ArfGAP1 inhibition using substituted piperazine derivatives |
| US10300055B2 (en) | 2014-04-10 | 2019-05-28 | Dalhousie University | Treatment of parkinson's disease through ARFGAP1 inhibition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2681221B1 (en) | 2016-05-18 |
| MX340402B (es) | 2016-07-07 |
| AR085502A1 (es) | 2013-10-09 |
| TWI532742B (zh) | 2016-05-11 |
| CN103703005A (zh) | 2014-04-02 |
| ES2587514T3 (es) | 2016-10-25 |
| JP2014506929A (ja) | 2014-03-20 |
| EP2681221A1 (en) | 2014-01-08 |
| UY33925A (es) | 2012-09-28 |
| WO2012161812A1 (en) | 2012-11-29 |
| US8710065B2 (en) | 2014-04-29 |
| US20120220572A1 (en) | 2012-08-30 |
| JP5886326B2 (ja) | 2016-03-16 |
| TW201247675A (en) | 2012-12-01 |
| MX2013009873A (es) | 2014-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8710065B2 (en) | Tricyclic inhibitors of kinases | |
| US9051327B2 (en) | Pyridazino[4,5-D]pyrimidin-5(6H)-one inhibitors of kinases | |
| US9718821B2 (en) | Pyridopyrimidinone inhibitors of kinases | |
| US8716297B2 (en) | Chemical entities to be used for Wee1 inhibition for the treatment of cancer | |
| EP2569316B1 (en) | Pyrrolopyridine and pyrrolopyrimidine inhibitors of kinases | |
| EP2454257B1 (en) | Pyrrolopyridine inhibitors of kinases | |
| US9181239B2 (en) | Pyridopyrimidinone inhibitors of kinases | |
| CA2824871A1 (en) | Bicyclic inhibitors of alk | |
| CA2794859A1 (en) | Phthalazin-(2h)-one inhibitors of kinases | |
| CA2794861A1 (en) | Pyrrolopyrazinone inhibitors of kinases | |
| HK1196370A (en) | Tricyclic inhibitors of kinases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180227 |