KR20110031367A - 화합물 251 - Google Patents

Info

Publication number

KR20110031367A

KR20110031367A KR1020117002754A KR20117002754A KR20110031367A KR 20110031367 A KR20110031367 A KR 20110031367A KR 1020117002754 A KR1020117002754 A KR 1020117002754A KR 20117002754 A KR20117002754 A KR 20117002754A KR 20110031367 A KR20110031367 A KR 20110031367A

Authority

KR

South Korea

Prior art keywords

thiazolidine

dione

methylidene

phenyl

methyl

Prior art date

2008-07-02

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 124
• 150000003839 salts Chemical class 0.000 claims abstract description 62
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 30
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 101000595531 Homo sapiens Serine/threonine-protein kinase pim-1 Proteins 0.000 claims abstract description 26
• 102100036077 Serine/threonine-protein kinase pim-1 Human genes 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• -1 nitro, cyano, hydroxy, amino, mercapto, formyl Chemical group 0.000 claims description 497
• 125000000217 alkyl group Chemical group 0.000 claims description 98
• 238000000034 method Methods 0.000 claims description 93
• 239000000203 mixture Substances 0.000 claims description 69
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims description 45
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 27
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 22
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 21
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 19
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 18
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 17
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
• 125000001589 carboacyl group Chemical group 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 12
• 238000002156 mixing Methods 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• HFCDVSYUOXEJNS-UHFFFAOYSA-N 5-[[2-(2,6-dichloro-3-methylanilino)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C=C2C(NC(=O)S2)=O)=C1Cl HFCDVSYUOXEJNS-UHFFFAOYSA-N 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 230000026731 phosphorylation Effects 0.000 claims description 5
• 238000006366 phosphorylation reaction Methods 0.000 claims description 5
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
• CWZULMCFFVJFEY-UHFFFAOYSA-N 5-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)NC(=O)S1 CWZULMCFFVJFEY-UHFFFAOYSA-N 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 229940054066 benzamide antipsychotics Drugs 0.000 claims description 4
• 150000003936 benzamides Chemical class 0.000 claims description 4
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• ZLDXTUTZYPVCKG-VPMLRQHESA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ZLDXTUTZYPVCKG-VPMLRQHESA-N 0.000 claims description 3
• STVUNYMVAGCJLS-OKSBFYSISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(dipropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N(CCC)CCC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 STVUNYMVAGCJLS-OKSBFYSISA-N 0.000 claims description 3
• MAXWYVPUCAYEHZ-ZSOIEALJSA-N (5z)-5-[[5-amino-2-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C)CCN1C1=CC=C(N)C=C1\C=C/1C(=O)NC(=O)S\1 MAXWYVPUCAYEHZ-ZSOIEALJSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
• ZWOZZWHFSDSLOU-UHFFFAOYSA-N 5-[(5-nitro-2-piperidin-1-ylphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC([N+](=O)[O-])=CC=C1N1CCCCC1 ZWOZZWHFSDSLOU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 230000001747 exhibiting effect Effects 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 229910001507 metal halide Inorganic materials 0.000 claims description 3
• 150000005309 metal halides Chemical class 0.000 claims description 3
• VWJNQFFHSJTVGQ-CJAAZZPWSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-1-methylimidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)N[C@@H]1CN(C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)CC1 VWJNQFFHSJTVGQ-CJAAZZPWSA-N 0.000 claims description 3
• HVMFXMXOKHYZGH-QPEQYQDCSA-N (5z)-5-[[2-(3-amino-4-methylpiperidin-1-yl)-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N)C(C)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 HVMFXMXOKHYZGH-QPEQYQDCSA-N 0.000 claims description 2
• JXSNYJNREMWSDJ-DKBJHAQFSA-N (5z)-5-[[2-[(3r)-3-(aminomethyl)pyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](CN)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 JXSNYJNREMWSDJ-DKBJHAQFSA-N 0.000 claims description 2
• MDFJCKNNJJLLKS-HDOAHBKWSA-N (5z)-5-[[2-[(3r)-3-[[4-(aminomethyl)phenyl]methylamino]piperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(CN)=CC=C1CN[C@H]1CN(C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)CCC1 MDFJCKNNJJLLKS-HDOAHBKWSA-N 0.000 claims description 2
• DXTSXAULWQSFNT-NUBYWOLOSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2,2,2-trifluoroethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(OCC(F)(F)F)C=CC=C1\C=C/1C(=O)NC(=O)S\1 DXTSXAULWQSFNT-NUBYWOLOSA-N 0.000 claims description 2
• NQPRGWXCFHMQPV-NWFCWYBLSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2-methoxyethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCCOC)=CC=CC=1\C=C1/SC(=O)NC1=O NQPRGWXCFHMQPV-NWFCWYBLSA-N 0.000 claims description 2
• FBEUTZRQCSCWQM-SLVCOGOPSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(2-methylpropoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O FBEUTZRQCSCWQM-SLVCOGOPSA-N 0.000 claims description 2
• PYWZTKODXYPZLR-VPMLRQHESA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-bromophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 PYWZTKODXYPZLR-VPMLRQHESA-N 0.000 claims description 2
• ILDFZJPHSLRCEK-YDRQLGOLSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclobutyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCC1 ILDFZJPHSLRCEK-YDRQLGOLSA-N 0.000 claims description 2
• YCYIBOYEPOLGSN-PWDRBQJJSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclohexyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCCCC1 YCYIBOYEPOLGSN-PWDRBQJJSA-N 0.000 claims description 2
• BVHIMRZDAQRPHV-RQNDZEIBSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-cyclopentyloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OC1CCCC1 BVHIMRZDAQRPHV-RQNDZEIBSA-N 0.000 claims description 2
• YPGUAMCIYVJFOJ-OJLMPMFISA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-ethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OCC)=CC=CC=1\C=C1/SC(=O)NC1=O YPGUAMCIYVJFOJ-OJLMPMFISA-N 0.000 claims description 2
• GJSKIXCETHIGQQ-JYVXZMADSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OC)=CC=CC=1\C=C1/SC(=O)NC1=O GJSKIXCETHIGQQ-JYVXZMADSA-N 0.000 claims description 2
• MCUJKPPARUPFJM-UWCCDQBKSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-phenylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)C=2C=CC=CC=2)=C1\C=C/1C(=O)NC(=O)S\1 MCUJKPPARUPFJM-UWCCDQBKSA-N 0.000 claims description 2
• ULMRMVZQMKZWKJ-MLJKTZRHSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-propan-2-yloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](N)CCC1)N1C=1C(OC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O ULMRMVZQMKZWKJ-MLJKTZRHSA-N 0.000 claims description 2
• WLJWSUVXFQUAHY-JYVXZMADSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 WLJWSUVXFQUAHY-JYVXZMADSA-N 0.000 claims description 2
• NJYIOPRYGAGQCB-NJQKBMNKSA-N (5z)-5-[[2-[(3r)-3-aminopyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 NJYIOPRYGAGQCB-NJQKBMNKSA-N 0.000 claims description 2
• DGGXDXTZQQQTKL-OYHMZJHOSA-N (5z)-5-[[2-[(3r,4r)-3-amino-4-hydroxypiperidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C[C@@H](O)[C@H](N)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 DGGXDXTZQQQTKL-OYHMZJHOSA-N 0.000 claims description 2
• JXSNYJNREMWSDJ-TXEUWIOXSA-N (5z)-5-[[2-[(3s)-3-(aminomethyl)pyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](CN)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 JXSNYJNREMWSDJ-TXEUWIOXSA-N 0.000 claims description 2
• GSCZVAZFVSJNDT-OGGBREFQSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2,2,2-trifluoroethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(OCC(F)(F)F)C=CC=C1\C=C/1C(=O)NC(=O)S\1 GSCZVAZFVSJNDT-OGGBREFQSA-N 0.000 claims description 2
• LPJHRWXRKNBEMC-CJAAZZPWSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2-methoxyethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OCCOC)=CC=CC=1\C=C1/SC(=O)NC1=O LPJHRWXRKNBEMC-CJAAZZPWSA-N 0.000 claims description 2
• LRGBUXCKVLHMRX-ISAHRAOESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-bromophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 LRGBUXCKVLHMRX-ISAHRAOESA-N 0.000 claims description 2
• FCICTBXGGPCMIE-SYUPGTOSSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 FCICTBXGGPCMIE-SYUPGTOSSA-N 0.000 claims description 2
• JZCLSXXFXYSNOS-LFTLCWSBSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-ethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OCC)=CC=CC=1\C=C1/SC(=O)NC1=O JZCLSXXFXYSNOS-LFTLCWSBSA-N 0.000 claims description 2
• YALFZHPIDBMBTI-QENILXLESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-propan-2-yloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OC(C)C)=CC=CC=1\C=C1/SC(=O)NC1=O YALFZHPIDBMBTI-QENILXLESA-N 0.000 claims description 2
• OINUTZGUCFIHAF-BZPKPHBRSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 OINUTZGUCFIHAF-BZPKPHBRSA-N 0.000 claims description 2
• QFGNATOKKPXYOF-DKKOHOGUSA-N (5z)-5-[[2-[(3s,4s)-3-amino-4-hydroxypyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](N)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 QFGNATOKKPXYOF-DKKOHOGUSA-N 0.000 claims description 2
• NJJGZBDOINCOFY-SSZFMOIBSA-N (5z)-5-[[3-(3-piperidin-1-ylpropoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)\C1=C\C1=CC=CC(OCCCN2CCCCC2)=C1 NJJGZBDOINCOFY-SSZFMOIBSA-N 0.000 claims description 2
• SUPIJQUDABPQAC-UVTDQMKNSA-N (5z)-5-[[3-[(4-methylpiperazin-1-yl)methyl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1CC1=CC=CC(\C=C/2C(NC(=O)S\2)=O)=C1 SUPIJQUDABPQAC-UVTDQMKNSA-N 0.000 claims description 2
• SZQWWFBBLCIGLS-SSZFMOIBSA-N (5z)-5-[[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(\C=C/2C(NC(=O)S\2)=O)=C1 SZQWWFBBLCIGLS-SSZFMOIBSA-N 0.000 claims description 2
• DMKSNYHOCJFURT-XFXZXTDPSA-N (5z)-5-[[3-chloro-2-(1,4-diazepan-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CCNCCN1C=1C(Cl)=CC=CC=1\C=C1/SC(=O)NC1=O DMKSNYHOCJFURT-XFXZXTDPSA-N 0.000 claims description 2
• OBZOMRZVUQXCFA-OJLMPMFISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(3,3,3-trifluoropropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCC(F)(F)F)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 OBZOMRZVUQXCFA-OJLMPMFISA-N 0.000 claims description 2
• ZEZRLGPUJDQXJR-NWFCWYBLSA-N (5z)-5-[[3-chloro-2-[(3r)-3-[2-(methylamino)ethylamino]piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](NCCNC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ZEZRLGPUJDQXJR-NWFCWYBLSA-N 0.000 claims description 2
• OBDFOJUJSKEDRO-ZSOIEALJSA-N (5z)-5-[[3-chloro-2-[4-methyl-3-(methylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(C)C(NC)CN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 OBDFOJUJSKEDRO-ZSOIEALJSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• XNMZHEQSIZCWTO-NUBYWOLOSA-N 4-[(3r)-3-aminopiperidin-1-yl]-3-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid Chemical compound C1[C@H](N)CCCN1C1=CC=C(C(O)=O)C=C1\C=C/1C(=O)NC(=O)S\1 XNMZHEQSIZCWTO-NUBYWOLOSA-N 0.000 claims description 2
• MVKANCZREUZKOU-OGGBREFQSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-3-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid Chemical compound C1[C@@H](N)CCN1C1=CC=C(C(O)=O)C=C1\C=C/1C(=O)NC(=O)S\1 MVKANCZREUZKOU-OGGBREFQSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• FAKIMWQMJWWTMG-UHFFFAOYSA-N 5-[(2-amino-4,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC(N)=C1C=C1C(=O)NC(=O)S1 FAKIMWQMJWWTMG-UHFFFAOYSA-N 0.000 claims description 2
• GAHMOOOPIAAIJZ-UHFFFAOYSA-N 5-[[2-(3-aminopropoxy)-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCN)C(C=C2C(NC(=O)S2)=O)=C1 GAHMOOOPIAAIJZ-UHFFFAOYSA-N 0.000 claims description 2
• QIYASANSQHZITK-UHFFFAOYSA-N 5-[[2-(4-aminopiperidin-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(N)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 QIYASANSQHZITK-UHFFFAOYSA-N 0.000 claims description 2
• ACBLHHDMVMZOHV-UHFFFAOYSA-N 5-[[2-(4-tert-butylpiperazin-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical class C1CN(C(C)(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 ACBLHHDMVMZOHV-UHFFFAOYSA-N 0.000 claims description 2
• UXHVFDZYEHJJKH-SNVBAGLBSA-N 5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 UXHVFDZYEHJJKH-SNVBAGLBSA-N 0.000 claims description 2
• XFFVJWMEBMHIMO-AOOOYVTPSA-N 5-[[2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 XFFVJWMEBMHIMO-AOOOYVTPSA-N 0.000 claims description 2
• JXEQKRLOKRCMML-NSHDSACASA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-3-fluorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=C(F)C=CC=C1C=C1C(=O)NC(=O)S1 JXEQKRLOKRCMML-NSHDSACASA-N 0.000 claims description 2
• TYDHOLYQNCKTJR-ZDUSSCGKSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-4-methylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC(C)=CC=C1C=C1C(=O)NC(=O)S1 TYDHOLYQNCKTJR-ZDUSSCGKSA-N 0.000 claims description 2
• PMEOSYUJHIYVKZ-LBPRGKRZSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 PMEOSYUJHIYVKZ-LBPRGKRZSA-N 0.000 claims description 2
• ZBFCRJCZTNEIOW-LBPRGKRZSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-fluorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(F)C=C1C=C1C(=O)NC(=O)S1 ZBFCRJCZTNEIOW-LBPRGKRZSA-N 0.000 claims description 2
• HGDRAPHCOZVBTC-LBPRGKRZSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(OC)=CC=C1N1CC[C@H](N(C)C)C1 HGDRAPHCOZVBTC-LBPRGKRZSA-N 0.000 claims description 2
• XMUVMSZMRFGXIB-ZDUSSCGKSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(C)C=C1C=C1C(=O)NC(=O)S1 XMUVMSZMRFGXIB-ZDUSSCGKSA-N 0.000 claims description 2
• UXHVFDZYEHJJKH-JTQLQIEISA-N 5-[[2-[(3s)-3-aminopiperidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 UXHVFDZYEHJJKH-JTQLQIEISA-N 0.000 claims description 2
• NQXBUJUICQUFIT-UHFFFAOYSA-N 5-[[2-[3-(aminomethyl)piperidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(CN)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 NQXBUJUICQUFIT-UHFFFAOYSA-N 0.000 claims description 2
• XKUPCQKNBPHFSG-UHFFFAOYSA-N 5-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(F)(F)F)=CC(Cl)=C(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)C=1C=C1SC(=O)NC1=O XKUPCQKNBPHFSG-UHFFFAOYSA-N 0.000 claims description 2
• UOQBYMVOOVBVNZ-JTQLQIEISA-N 5-[[2-chloro-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=CC(Cl)=C1C=C1C(=O)NC(=O)S1 UOQBYMVOOVBVNZ-JTQLQIEISA-N 0.000 claims description 2
• PAANXPLSXFIGMW-NSHDSACASA-N 5-[[3-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=C(Br)C=CC=C1C=C1C(=O)NC(=O)S1 PAANXPLSXFIGMW-NSHDSACASA-N 0.000 claims description 2
• ZHPWHZMWMYLZQV-UHFFFAOYSA-N 5-[[3-chloro-2-(1,4-diazepan-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N1CCCNCC1 ZHPWHZMWMYLZQV-UHFFFAOYSA-N 0.000 claims description 2
• AJXNMNOJEYROEA-UHFFFAOYSA-N 5-[[3-chloro-2-(4-cyclopentylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1C1CCCC1 AJXNMNOJEYROEA-UHFFFAOYSA-N 0.000 claims description 2
• SPIKHWFAEGMMHR-UHFFFAOYSA-N 5-[[3-chloro-2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 SPIKHWFAEGMMHR-UHFFFAOYSA-N 0.000 claims description 2
• JYTYMNCPLFGMLM-UHFFFAOYSA-N 5-[[3-chloro-2-(4-morpholin-4-ylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCC1N1CCOCC1 JYTYMNCPLFGMLM-UHFFFAOYSA-N 0.000 claims description 2
• RWDBZLUKAAUSHC-UHFFFAOYSA-N 5-[[3-chloro-2-(4-piperidin-1-ylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCC1N1CCCCC1 RWDBZLUKAAUSHC-UHFFFAOYSA-N 0.000 claims description 2
• FTXLPRHUMRLOFM-UHFFFAOYSA-N 5-[[3-chloro-2-(4-propan-2-ylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 FTXLPRHUMRLOFM-UHFFFAOYSA-N 0.000 claims description 2
• SNMVUVIOJOQAHG-UHFFFAOYSA-N 5-[[3-chloro-2-(4-pyrrolidin-1-ylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCC1N1CCCC1 SNMVUVIOJOQAHG-UHFFFAOYSA-N 0.000 claims description 2
• CSEZPMGYTAKIOJ-NSHDSACASA-N 5-[[3-chloro-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 CSEZPMGYTAKIOJ-NSHDSACASA-N 0.000 claims description 2
• WCLDBXFEJREFNS-UHFFFAOYSA-N 5-[[3-chloro-2-[3-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=NOC(C2CN(CCC2)C=2C(=CC(=CC=2Cl)C(F)(F)F)C=C2C(NC(=O)S2)=O)=N1 WCLDBXFEJREFNS-UHFFFAOYSA-N 0.000 claims description 2
• VMPTWAXWYYZFGU-UHFFFAOYSA-N 5-[[3-chloro-2-[3-(dimethylamino)propyl-methylamino]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CN(C)CCCN(C)C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 VMPTWAXWYYZFGU-UHFFFAOYSA-N 0.000 claims description 2
• CZBMOCKXUDMRED-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCC1N1CCN(C=2C(=CC(=CC=2Cl)C(F)(F)F)C=C2C(NC(=O)S2)=O)CC1 CZBMOCKXUDMRED-UHFFFAOYSA-N 0.000 claims description 2
• RLUWZNJWIKLKCP-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCO)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 RLUWZNJWIKLKCP-UHFFFAOYSA-N 0.000 claims description 2
• SDMSSSNUMQIPGL-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-hydroxyethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 SDMSSSNUMQIPGL-UHFFFAOYSA-N 0.000 claims description 2
• RZBQYBODURYYCR-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-hydroxyethyl)piperidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(CCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 RZBQYBODURYYCR-UHFFFAOYSA-N 0.000 claims description 2
• KGOAOQWVVJTDQT-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-methylpropyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CC(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 KGOAOQWVVJTDQT-UHFFFAOYSA-N 0.000 claims description 2
• CYIADNCOTLOBMG-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-morpholin-4-ylethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1CCN1CCOCC1 CYIADNCOTLOBMG-UHFFFAOYSA-N 0.000 claims description 2
• LEVWFFKJNVUTMF-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(3-hydroxypropyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 LEVWFFKJNVUTMF-UHFFFAOYSA-N 0.000 claims description 2
• ZBBNKWGLUVVHOU-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=NOC(C2CCN(CC2)C=2C(=CC(=CC=2Cl)C(F)(F)F)C=C2C(NC(=O)S2)=O)=N1 ZBBNKWGLUVVHOU-UHFFFAOYSA-N 0.000 claims description 2
• FOAJUOHPNZLOCM-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(4-chloro-2-fluorophenyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound FC1=CC(Cl)=CC=C1N1CCN(C=2C(=CC(=CC=2Cl)C(F)(F)F)C=C2C(NC(=O)S2)=O)CC1 FOAJUOHPNZLOCM-UHFFFAOYSA-N 0.000 claims description 2
• QZNLFERGYQSRSW-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(4-fluorophenyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C(=CC(=CC=2Cl)C(F)(F)F)C=C2C(NC(=O)S2)=O)CC1 QZNLFERGYQSRSW-UHFFFAOYSA-N 0.000 claims description 2
• GHWDQWIMBBQROR-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(cyclopropylmethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1CC1CC1 GHWDQWIMBBQROR-UHFFFAOYSA-N 0.000 claims description 2
• XCVBSBVWFUJZJN-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(dimethylamino)piperidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(N(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 XCVBSBVWFUJZJN-UHFFFAOYSA-N 0.000 claims description 2
• SVKBAJHSSBBKLM-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(pyridin-4-ylmethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1CC1=CC=NC=C1 SVKBAJHSSBBKLM-UHFFFAOYSA-N 0.000 claims description 2
• VCZKRRHUKGXBLG-UHFFFAOYSA-N 5-[[3-chloro-2-[4-[(2-chlorophenyl)methyl]piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1CC1=CC=CC=C1Cl VCZKRRHUKGXBLG-UHFFFAOYSA-N 0.000 claims description 2
• OBQBTGCGTZKBCJ-UHFFFAOYSA-N 5-[[3-chloro-2-morpholin-4-yl-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(C(F)(F)F)=CC(Cl)=C1N1CCOCC1 OBQBTGCGTZKBCJ-UHFFFAOYSA-N 0.000 claims description 2
• GQZNMLNYZBPJEJ-LBPRGKRZSA-N 5-[[5-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(Br)C=C1C=C1C(=O)NC(=O)S1 GQZNMLNYZBPJEJ-LBPRGKRZSA-N 0.000 claims description 2
• ZLKXQCKKQVCPKO-LBPRGKRZSA-N 5-[[5-chloro-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(Cl)C=C1C=C1C(=O)NC(=O)S1 ZLKXQCKKQVCPKO-LBPRGKRZSA-N 0.000 claims description 2
• MZMOEKLRSIIVAX-UHFFFAOYSA-N 5-[[5-methoxy-2-[3-(propan-2-ylamino)propoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCNC(C)C)C(C=C2C(NC(=O)S2)=O)=C1 MZMOEKLRSIIVAX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
• 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• QFRNXHAYSYBVKI-ZENNRRHLSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-1-methylpyrazole-3-carboxamide Chemical compound CN1C=CC(C(=O)N[C@@H]2CN(CC2)C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)=N1 QFRNXHAYSYBVKI-ZENNRRHLSA-N 0.000 claims description 2
• KHRUUQWZCIYNKB-XKBFBRDOSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-1-methylpyrazole-4-carboxamide Chemical compound C1=NN(C)C=C1C(=O)N[C@@H]1CN(C=2C(=CC=CC=2Cl)\C=C/2C(NC(=O)S\2)=O)CC1 KHRUUQWZCIYNKB-XKBFBRDOSA-N 0.000 claims description 2
• ZIGBBKSLDXMKKW-LFTLCWSBSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-2-cyanoacetamide Chemical compound C([C@H](CC1)NC(=O)CC#N)N1C=1C(Cl)=CC=CC=1\C=C1/SC(=O)NC1=O ZIGBBKSLDXMKKW-LFTLCWSBSA-N 0.000 claims description 2
• FPNLPOQYPFTGCE-HAKPAVFJSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-2-pyridin-3-ylacetamide Chemical compound C([C@H](CC1)NC(=O)CC=2C=NC=CC=2)N1C=1C(Cl)=CC=CC=1\C=C1/SC(=O)NC1=O FPNLPOQYPFTGCE-HAKPAVFJSA-N 0.000 claims description 2
• DGFOYAGXKGPDEC-ZCQLHAAUSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-2-pyridin-4-ylacetamide Chemical compound C([C@H](CC1)NC(=O)CC=2C=CN=CC=2)N1C=1C(Cl)=CC=CC=1\C=C1/SC(=O)NC1=O DGFOYAGXKGPDEC-ZCQLHAAUSA-N 0.000 claims description 2
• ACYSHADFNCYUSL-CJAAZZPWSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-4-sulfamoylbutanamide Chemical compound C1[C@@H](NC(=O)CCCS(=O)(=O)N)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 ACYSHADFNCYUSL-CJAAZZPWSA-N 0.000 claims description 2
• TZLCLYRLBKRXCX-OJNRTJSBSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-n',n'-dimethylbutanediamide Chemical compound C1[C@@H](NC(=O)CCC(=O)N(C)C)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 TZLCLYRLBKRXCX-OJNRTJSBSA-N 0.000 claims description 2
• JIDWIAWAFBHNSW-RGEXLXHISA-N n-[2-(dimethylamino)ethyl]-4-[2-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)CCN(C)C)=CC=C1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 JIDWIAWAFBHNSW-RGEXLXHISA-N 0.000 claims description 2
• WAHVGCWMFGAKGI-SXGWCWSVSA-N n-[4-[3-(dimethylamino)pyrrolidin-1-yl]-3-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]acetamide Chemical compound C1C(N(C)C)CCN1C1=CC=C(NC(C)=O)C=C1\C=C/1C(=O)NC(=O)S\1 WAHVGCWMFGAKGI-SXGWCWSVSA-N 0.000 claims description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• 230000001093 anti-cancer Effects 0.000 claims 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 19
• 102000004190 Enzymes Human genes 0.000 abstract description 9
• 108090000790 Enzymes Proteins 0.000 abstract description 9
• 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 abstract description 8
• 230000002265 prevention Effects 0.000 abstract description 8
• 238000011282 treatment Methods 0.000 abstract description 8
• 201000010099 disease Diseases 0.000 abstract description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
• 230000000694 effects Effects 0.000 abstract description 6
• 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 abstract description 5
• 101100297651 Mus musculus Pim2 gene Proteins 0.000 abstract description 5
• 102000001253 Protein Kinase Human genes 0.000 abstract description 5
• 108060006633 protein kinase Proteins 0.000 abstract description 5
• 230000009471 action Effects 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 239000007858 starting material Substances 0.000 description 26
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 238000005481 NMR spectroscopy Methods 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 238000003756 stirring Methods 0.000 description 12
• 239000000047 product Substances 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 10
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• 229940088598 enzyme Drugs 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 239000000284 extract Substances 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 6
• ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
• 101001064870 Homo sapiens Lon protease homolog, mitochondrial Proteins 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000002253 acid Substances 0.000 description 5
• 150000003840 hydrochlorides Chemical class 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 238000004007 reversed phase HPLC Methods 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
• ROQSCVKICOMOQP-UHFFFAOYSA-N 5-[(2-morpholin-4-yl-5-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC([N+](=O)[O-])=CC=C1N1CCOCC1 ROQSCVKICOMOQP-UHFFFAOYSA-N 0.000 description 4
• 0 CC(C)(C**)C(C)(C)*c1c(C=C(C(N2)=O)SC2=O)cc(*)c(*)c1* Chemical compound CC(C)(C**)C(C)(C)*c1c(C=C(C(N2)=O)SC2=O)cc(*)c(*)c1* 0.000 description 4
• 102000004127 Cytokines Human genes 0.000 description 4
• 108090000695 Cytokines Proteins 0.000 description 4
• 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 4
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
• 239000007995 HEPES buffer Substances 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 235000019441 ethanol Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 238000001802 infusion Methods 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 229960005419 nitrogen Drugs 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 235000019198 oils Nutrition 0.000 description 4
• 239000001301 oxygen Chemical group 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 238000000926 separation method Methods 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 239000003981 vehicle Substances 0.000 description 4
• SYFAMQSVMVHCIS-NSHDSACASA-N 3-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]benzaldehyde Chemical compound C1[C@@H](N(C)C)CCN1C1=C(Br)C=CC=C1C=O SYFAMQSVMVHCIS-NSHDSACASA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 206010060862 Prostate cancer Diseases 0.000 description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 230000002159 abnormal effect Effects 0.000 description 3
• 150000001299 aldehydes Chemical class 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 230000000692 anti-sense effect Effects 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 125000002837 carbocyclic group Chemical group 0.000 description 3
• 238000002512 chemotherapy Methods 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
• YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 3
• 239000000839 emulsion Substances 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
• 238000001415 gene therapy Methods 0.000 description 3
• 239000003102 growth factor Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 239000012074 organic phase Substances 0.000 description 3
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• 108010083755 proto-oncogene proteins pim Proteins 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 239000012258 stirred mixture Substances 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 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 2
• OOYZNZPKFQSWHZ-XFXZXTDPSA-N (5z)-5-[(2-piperazin-1-ylphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)\C1=C\C1=CC=CC=C1N1CCNCC1 OOYZNZPKFQSWHZ-XFXZXTDPSA-N 0.000 description 2
• RKESULACCHMSQL-FBUJANLLSA-N (5z)-5-[[2-[(3s)-3-(3-aminopropylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](NCCCN)CCN1C1=CC=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 RKESULACCHMSQL-FBUJANLLSA-N 0.000 description 2
• DTAUNSRLBNWGKO-GGKUHZQSSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-4-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=CC(Cl)=CC=C1\C=C/1C(=O)NC(=O)S\1 DTAUNSRLBNWGKO-GGKUHZQSSA-N 0.000 description 2
• YFDFJFPVYTYJGZ-CMGLLUGASA-N (5z)-5-[[3-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N(C)C)CCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 YFDFJFPVYTYJGZ-CMGLLUGASA-N 0.000 description 2
• IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 2
• CVJVSXKZGFQWJK-UHFFFAOYSA-N 2-fluoro-3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1F CVJVSXKZGFQWJK-UHFFFAOYSA-N 0.000 description 2
• FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 2
• 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 2
• MSZTVIFIFJCNRQ-UHFFFAOYSA-N 3-chloro-2-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=C(Cl)C=C(C(F)(F)F)C=C1C=O MSZTVIFIFJCNRQ-UHFFFAOYSA-N 0.000 description 2
• NMKZYUJCLQVHSM-UHFFFAOYSA-N 3-ethoxy-2-fluorobenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1F NMKZYUJCLQVHSM-UHFFFAOYSA-N 0.000 description 2
• PUJJEFSJHCGITR-UHFFFAOYSA-N 5-[[2-(dipropylamino)-5-nitrophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCCN(CCC)C1=CC=C([N+]([O-])=O)C=C1C=C1C(=O)NC(=O)S1 PUJJEFSJHCGITR-UHFFFAOYSA-N 0.000 description 2
• FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• 101001001648 Homo sapiens Serine/threonine-protein kinase pim-2 Proteins 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 2
• 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 2
• 206010025323 Lymphomas Diseases 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
• 108091007960 PI3Ks Proteins 0.000 description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 2
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
• 108091008611 Protein Kinase B Proteins 0.000 description 2
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 2
• 102100036120 Serine/threonine-protein kinase pim-2 Human genes 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 206010042971 T-cell lymphoma Diseases 0.000 description 2
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 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 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 239000003708 ampul Substances 0.000 description 2
• 239000002246 antineoplastic agent Substances 0.000 description 2
• 230000006907 apoptotic process Effects 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• FZDACFZWWMAUBO-UHFFFAOYSA-N benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate Chemical compound C1C2OC2CN1C(=O)OCC1=CC=CC=C1 FZDACFZWWMAUBO-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 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 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
• 230000004663 cell proliferation Effects 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 235000010980 cellulose Nutrition 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 235000008504 concentrate Nutrition 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 229960001433 erlotinib Drugs 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• 230000014509 gene expression Effects 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 150000002460 imidazoles Chemical class 0.000 description 2
• 238000009169 immunotherapy Methods 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 229940043355 kinase inhibitor Drugs 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• 201000002528 pancreatic cancer Diseases 0.000 description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 230000000069 prophylactic effect Effects 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 238000001959 radiotherapy Methods 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• CBWPIAQEJKRGGB-LJQANCHMSA-N tert-butyl n-[(3r)-1-(2-formyl-6-phenylphenyl)piperidin-3-yl]carbamate Chemical compound C1[C@H](NC(=O)OC(C)(C)C)CCCN1C1=C(C=O)C=CC=C1C1=CC=CC=C1 CBWPIAQEJKRGGB-LJQANCHMSA-N 0.000 description 2
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 2
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 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
• 210000004881 tumor cell Anatomy 0.000 description 2
• 230000007306 turnover Effects 0.000 description 2
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 2
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 2
• 238000011144 upstream manufacturing Methods 0.000 description 2
• RVNSAAIWCWTCTJ-ZPQYLTHOSA-N (2s,3s,4r)-2-(1,2-dihydroxyethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)[C@@H]1NC[C@@H](O)[C@H]1O RVNSAAIWCWTCTJ-ZPQYLTHOSA-N 0.000 description 1
• AVAWMINJNRAQFS-LURJTMIESA-N (3s)-n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)[C@H]1CCNC1 AVAWMINJNRAQFS-LURJTMIESA-N 0.000 description 1
• SSZDRQAJNXJKPL-DQMXGCRQSA-N (5z)-5-[(2-piperazin-1-ylpyridin-3-yl)methylidene]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.S1C(=O)NC(=O)\C1=C\C1=CC=CN=C1N1CCNCC1 SSZDRQAJNXJKPL-DQMXGCRQSA-N 0.000 description 1
• VZGVRCKEYGUWSX-UVTDQMKNSA-N (5z)-5-[[2-(4-acetylpiperazin-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 VZGVRCKEYGUWSX-UVTDQMKNSA-N 0.000 description 1
• NWNVFJTUPWJIKT-UEXNTNOUSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-(cyclohexylmethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)\C=C/2C(NC(=O)S\2)=O)=C1OCC1CCCCC1 NWNVFJTUPWJIKT-UEXNTNOUSA-N 0.000 description 1
• BKLKVDYSEWXDBQ-GGKUHZQSSA-N (5z)-5-[[2-[(3s)-3-aminopiperidin-1-yl]-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 BKLKVDYSEWXDBQ-GGKUHZQSSA-N 0.000 description 1
• NJYIOPRYGAGQCB-ISAHRAOESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 NJYIOPRYGAGQCB-ISAHRAOESA-N 0.000 description 1
• DCEQRIXNZLRPRR-PXNMLYILSA-N (5z)-5-[[2-[3-(2-hydroxyethylamino)pyrrolidin-1-yl]-4,5-dimethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(NCCO)CN1C=1C=C(OC)C(OC)=CC=1\C=C1/SC(=O)NC1=O DCEQRIXNZLRPRR-PXNMLYILSA-N 0.000 description 1
• XRBNMEONYZCOLM-ZSOIEALJSA-N (5z)-5-[[2-[3-(dimethylamino)pyrrolidin-1-yl]-5-nitrophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1\C=C/1C(=O)NC(=O)S\1 XRBNMEONYZCOLM-ZSOIEALJSA-N 0.000 description 1
• FEYAXNXLUOQQML-HYMQDMCPSA-N (5z)-5-[[3-chloro-2-(4-cyclopentylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.S\1C(=O)NC(=O)C/1=C/C1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1C1CCCC1 FEYAXNXLUOQQML-HYMQDMCPSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
• HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• PVMCQBPJKPMOKM-UHFFFAOYSA-N 1-cyclopentylpiperazine Chemical compound C1CCCC1N1CCNCC1 PVMCQBPJKPMOKM-UHFFFAOYSA-N 0.000 description 1
• WLDPWZQYAVZTTP-UHFFFAOYSA-N 1-methyl-imidazole-2-carboxylic acid Chemical compound CN1C=CN=C1C(O)=O WLDPWZQYAVZTTP-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
• RTMMSCJWQYWMNK-UHFFFAOYSA-N 2,2,2-trifluoroethyl trifluoromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(F)(F)F RTMMSCJWQYWMNK-UHFFFAOYSA-N 0.000 description 1
• 125000006069 2,3-dimethyl-2-butenyl group Chemical group 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
• DNNSTFZKIHYBLG-UHFFFAOYSA-N 2-(3-amino-4-methylpiperidin-1-yl)-3-chlorobenzaldehyde Chemical compound C1C(N)C(C)CCN1C1=C(Cl)C=CC=C1C=O DNNSTFZKIHYBLG-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• UQQROBHFUDBOOK-UHFFFAOYSA-N 2-bromo-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(Br)=C(C=O)C=C1OC UQQROBHFUDBOOK-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
• VJJAJKPDBXQYRJ-UHFFFAOYSA-N 2-fluoro-3-(2,2,2-trifluoroethoxy)benzonitrile Chemical compound FC1=C(OCC(F)(F)F)C=CC=C1C#N VJJAJKPDBXQYRJ-UHFFFAOYSA-N 0.000 description 1
• QBBVBWBSWAEEPP-UHFFFAOYSA-N 2-fluoro-3-(2-methylpropoxy)benzonitrile Chemical compound CC(C)COC1=CC=CC(C#N)=C1F QBBVBWBSWAEEPP-UHFFFAOYSA-N 0.000 description 1
• 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-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
• WCFJUSRQHZPVKY-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NCCC(O)=O WCFJUSRQHZPVKY-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
• OUAZPCKRSSEQKB-UHFFFAOYSA-N 3-bromo-2-fluorobenzaldehyde Chemical compound FC1=C(Br)C=CC=C1C=O OUAZPCKRSSEQKB-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• NRUNOKNBZYDSTD-UHFFFAOYSA-N 3-ethoxy-2-fluorobenzonitrile Chemical compound CCOC1=CC=CC(C#N)=C1F NRUNOKNBZYDSTD-UHFFFAOYSA-N 0.000 description 1
• 125000006027 3-methyl-1-butenyl group Chemical group 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
• IZHHKPVWRPAHGE-UHFFFAOYSA-N 4,5-dimethoxy-2-pyridin-3-ylbenzaldehyde Chemical compound C1=C(OC)C(OC)=CC(C=O)=C1C1=CC=CN=C1 IZHHKPVWRPAHGE-UHFFFAOYSA-N 0.000 description 1
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• QMQYGDZSNITFMM-UHFFFAOYSA-N 5-[[2-(4-butyl-1,4-diazepan-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCCC)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 QMQYGDZSNITFMM-UHFFFAOYSA-N 0.000 description 1
• ULRQIAAFERRGRG-UHFFFAOYSA-N 5-methoxy-2-(2-piperidin-1-ylethoxy)benzaldehyde Chemical compound O=CC1=CC(OC)=CC=C1OCCN1CCCCC1 ULRQIAAFERRGRG-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
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 235000019489 Almond oil Nutrition 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
• 102000012936 Angiostatins Human genes 0.000 description 1
• 108010079709 Angiostatins Proteins 0.000 description 1
• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
• 108010011485 Aspartame Proteins 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• 102000036365 BRCA1 Human genes 0.000 description 1
• 108700020463 BRCA1 Proteins 0.000 description 1
• 101150072950 BRCA1 gene Proteins 0.000 description 1
• 102000052609 BRCA2 Human genes 0.000 description 1
• 108700020462 BRCA2 Proteins 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 241000167854 Bourreria succulenta Species 0.000 description 1
• 101150008921 Brca2 gene Proteins 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 108010037003 Buserelin Proteins 0.000 description 1
• CAHSFWYLIXESSJ-CYBMUJFWSA-N CC(C)(C)OC(N[C@H](CCC1)CN1c1c(C=O)cccc1Br)=O Chemical compound CC(C)(C)OC(N[C@H](CCC1)CN1c1c(C=O)cccc1Br)=O CAHSFWYLIXESSJ-CYBMUJFWSA-N 0.000 description 1
• DLKDEVCJRCPTLN-UHFFFAOYSA-N CCCCN(C(c1c2cccc1)=O)C2=O Chemical compound CCCCN(C(c1c2cccc1)=O)C2=O DLKDEVCJRCPTLN-UHFFFAOYSA-N 0.000 description 1
• 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
• 241000282988 Capreolus Species 0.000 description 1
• 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 1
• HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 102000000311 Cytosine Deaminase Human genes 0.000 description 1
• 108010080611 Cytosine Deaminase Proteins 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
• 108010092160 Dactinomycin 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
• WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
• 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
• 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
• 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
• 108010041308 Endothelial Growth Factors Proteins 0.000 description 1
• 102400001368 Epidermal growth factor Human genes 0.000 description 1
• 101800003838 Epidermal growth factor Proteins 0.000 description 1
• HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• 229930091371 Fructose Natural products 0.000 description 1
• 239000005715 Fructose Substances 0.000 description 1
• RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
• VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
• 108010069236 Goserelin Proteins 0.000 description 1
• 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 1
• 102100021866 Hepatocyte growth factor Human genes 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-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
• JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 description 1
• 108010047852 Integrin alphaVbeta3 Proteins 0.000 description 1
• 102000000588 Interleukin-2 Human genes 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 102000004388 Interleukin-4 Human genes 0.000 description 1
• 108090000978 Interleukin-4 Proteins 0.000 description 1
• 241000764238 Isis Species 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
• 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
• 229940124041 Luteinizing hormone releasing hormone (LHRH) antagonist Drugs 0.000 description 1
• 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
• 108700041567 MDR Genes Proteins 0.000 description 1
• 229940124647 MEK inhibitor Drugs 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 244000246386 Mentha pulegium Species 0.000 description 1
• 235000016257 Mentha pulegium Nutrition 0.000 description 1
• 235000004357 Mentha x piperita Nutrition 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 241000713869 Moloney murine leukemia virus Species 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• 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 1
• BNKHVTBGCCMURF-PQRLVGIHSA-N NCCC/N=C\C(CC1)CN1c1c(/C=C(/C(N2)=O)\SC2=O)cc(C(F)(F)F)cc1 Chemical compound NCCC/N=C\C(CC1)CN1c1c(/C=C(/C(N2)=O)\SC2=O)cc(C(F)(F)F)cc1 BNKHVTBGCCMURF-PQRLVGIHSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• STBSPFJJNLGUBL-WQLSENKSSA-N O=C(/C(/S1)=C/c(cc(C(F)(F)F)cc2)c2N2CCCC2)NC1=O Chemical compound O=C(/C(/S1)=C/c(cc(C(F)(F)F)cc2)c2N2CCCC2)NC1=O STBSPFJJNLGUBL-WQLSENKSSA-N 0.000 description 1
• NYOAHPMRMDEDGG-UHFFFAOYSA-N O=Cc(cccc1S)c1N1CCCC1 Chemical compound O=Cc(cccc1S)c1N1CCCC1 NYOAHPMRMDEDGG-UHFFFAOYSA-N 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 229910004298 SiO 2 Inorganic materials 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 description 1
• 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 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
• 102000006601 Thymidine Kinase Human genes 0.000 description 1
• 108020004440 Thymidine kinase Proteins 0.000 description 1
• IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
• 108010042352 Urokinase Plasminogen Activator Receptors Chemical group 0.000 description 1
• 102000004504 Urokinase Plasminogen Activator Receptors Human genes 0.000 description 1
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
• 108010019530 Vascular Endothelial Growth Factors Proteins 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
• 229940122803 Vinca alkaloid Drugs 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 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 1
• 239000013543 active substance Substances 0.000 description 1
• 125000002015 acyclic group Chemical group 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• 229940009456 adriamycin Drugs 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 229940060238 agrylin Drugs 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 239000008168 almond oil Substances 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• OTBXOEAOVRKTNQ-UHFFFAOYSA-N anagrelide Chemical compound N1=C2NC(=O)CN2CC2=C(Cl)C(Cl)=CC=C21 OTBXOEAOVRKTNQ-UHFFFAOYSA-N 0.000 description 1
• 229960002932 anastrozole Drugs 0.000 description 1
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• 229940045799 anthracyclines and related substance Drugs 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 230000003432 anti-folate effect Effects 0.000 description 1
• 230000003302 anti-idiotype Effects 0.000 description 1
• 230000001028 anti-proliverative effect Effects 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 230000002137 anti-vascular effect Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 238000011394 anticancer treatment Methods 0.000 description 1
• 229940127074 antifolate Drugs 0.000 description 1
• 239000003080 antimitotic agent Substances 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 239000012062 aqueous buffer Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 239000000605 aspartame Substances 0.000 description 1
• IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
• 235000010357 aspartame Nutrition 0.000 description 1
• 229960003438 aspartame Drugs 0.000 description 1
• FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 1
• 229940120638 avastin Drugs 0.000 description 1
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229960004365 benzoic acid Drugs 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• IXPLJRREJIUKLG-GHMZBOCLSA-N benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate Chemical compound C1[C@@H](O)[C@H](N)CN1C(=O)OCC1=CC=CC=C1 IXPLJRREJIUKLG-GHMZBOCLSA-N 0.000 description 1
• RIMVJYHSULPFSY-GHMZBOCLSA-N benzyl (3r,4r)-3-azido-4-hydroxypyrrolidine-1-carboxylate Chemical compound C1[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCC1=CC=CC=C1 RIMVJYHSULPFSY-GHMZBOCLSA-N 0.000 description 1
• CMXBVXJSFDXHTE-ZIAGYGMSSA-N benzyl (3r,4r)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate Chemical compound C1[C@@H](O)[C@H](NC(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 CMXBVXJSFDXHTE-ZIAGYGMSSA-N 0.000 description 1
• XSKKIFJNZPNVGO-UHFFFAOYSA-N benzyl 2,5-dihydropyrrole-1-carboxylate Chemical compound C1C=CCN1C(=O)OCC1=CC=CC=C1 XSKKIFJNZPNVGO-UHFFFAOYSA-N 0.000 description 1
• IXPLJRREJIUKLG-UHFFFAOYSA-N benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate Chemical compound C1C(O)C(N)CN1C(=O)OCC1=CC=CC=C1 IXPLJRREJIUKLG-UHFFFAOYSA-N 0.000 description 1
• RIMVJYHSULPFSY-UHFFFAOYSA-N benzyl 3-azido-4-hydroxypyrrolidine-1-carboxylate Chemical compound C1C(N=[N+]=[N-])C(O)CN1C(=O)OCC1=CC=CC=C1 RIMVJYHSULPFSY-UHFFFAOYSA-N 0.000 description 1
• CMXBVXJSFDXHTE-UHFFFAOYSA-N benzyl 3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate Chemical compound C1C(O)C(NC(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 CMXBVXJSFDXHTE-UHFFFAOYSA-N 0.000 description 1
• 229960000397 bevacizumab Drugs 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 239000000090 biomarker Substances 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
• BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• 239000000337 buffer salt Substances 0.000 description 1
• 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 1
• 229960002719 buserelin Drugs 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 210000001217 buttock Anatomy 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
• 229950002826 canertinib Drugs 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 229960005395 cetuximab Drugs 0.000 description 1
• 235000019693 cherries Nutrition 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
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 239000013066 combination product Substances 0.000 description 1
• 229940127555 combination product Drugs 0.000 description 1
• 238000011284 combination treatment Methods 0.000 description 1
• 229940046044 combinations of antineoplastic agent Drugs 0.000 description 1
• 229960005537 combretastatin A-4 Drugs 0.000 description 1
• HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 description 1
• 238000012790 confirmation Methods 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 238000004132 cross linking Methods 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 125000004093 cyano group Chemical group *C#N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 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 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
• 229960000640 dactinomycin 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
• 238000007872 degassing Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 210000004443 dendritic cell Anatomy 0.000 description 1
• 238000002405 diagnostic procedure Methods 0.000 description 1
• 125000005265 dialkylamine group Chemical group 0.000 description 1
• 235000019700 dicalcium phosphate Nutrition 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([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
• 239000007884 disintegrant Substances 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 238000001952 enzyme assay Methods 0.000 description 1
• 229940116977 epidermal growth factor Drugs 0.000 description 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 229940082789 erbitux Drugs 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 239000000328 estrogen antagonist Substances 0.000 description 1
• 102000015694 estrogen receptors Human genes 0.000 description 1
• 108010038795 estrogen receptors Proteins 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000005469 ethylenyl group Chemical group 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
• 229960000255 exemestane Drugs 0.000 description 1
• 239000000945 filler 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
• 235000019634 flavors Nutrition 0.000 description 1
• 150000005699 fluoropyrimidines Chemical class 0.000 description 1
• 229960002949 fluorouracil Drugs 0.000 description 1
• 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 1
• 229960002074 flutamide Drugs 0.000 description 1
• 239000004052 folic acid antagonist Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 229960002737 fructose Drugs 0.000 description 1
• 229960002258 fulvestrant Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 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 1
• 229940080856 gleevec Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 229960002989 glutamic acid Drugs 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-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
• 239000008187 granular material Substances 0.000 description 1
• 201000005787 hematologic cancer Diseases 0.000 description 1
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
• 229940022353 herceptin Drugs 0.000 description 1
• 235000001050 hortel pimenta Nutrition 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 229960000908 idarubicin Drugs 0.000 description 1
• 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
• 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 1
• 229960002411 imatinib Drugs 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000002519 immonomodulatory effect Effects 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 230000005847 immunogenicity Effects 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 238000012739 integrated shape imaging system Methods 0.000 description 1
• 229940028885 interleukin-4 Drugs 0.000 description 1
• 229910052742 iron Inorganic materials 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
• 125000005468 isobutylenyl group Chemical group 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
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000004816 latex Substances 0.000 description 1
• 229920000126 latex Polymers 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 229960004942 lenalidomide Drugs 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
• 208000032839 leukemia Diseases 0.000 description 1
• 229960004194 lidocaine Drugs 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 239000003589 local anesthetic agent Substances 0.000 description 1
• 229960005015 local anesthetics Drugs 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 208000003747 lymphoid leukemia Diseases 0.000 description 1
• 239000008176 lyophilized powder Substances 0.000 description 1
• OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
• 229910001623 magnesium bromide Inorganic materials 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 235000014380 magnesium carbonate Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical group CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 1
• 229950008959 marimastat Drugs 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 229960004961 mechlorethamine Drugs 0.000 description 1
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
• 229960004296 megestrol acetate Drugs 0.000 description 1
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
• 229960001924 melphalan Drugs 0.000 description 1
• 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 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• KDCUMFPVKRDKEZ-UHFFFAOYSA-N methyl n-[1-(2-chloro-6-formylphenyl)-4-methylpiperidin-3-yl]carbamate Chemical compound C1CC(C)C(NC(=O)OC)CN1C1=C(Cl)C=CC=C1C=O KDCUMFPVKRDKEZ-UHFFFAOYSA-N 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 208000025113 myeloid leukemia Diseases 0.000 description 1
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
• NXKZGTGNGAQWGA-HKMIMPICSA-N n-[(3s)-1-[2-chloro-6-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]pyrrolidin-3-yl]-2-methoxyacetamide Chemical compound C1[C@@H](NC(=O)COC)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 NXKZGTGNGAQWGA-HKMIMPICSA-N 0.000 description 1
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
• 229960002653 nilutamide Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000004533 oil dispersion Substances 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229960003171 plicamycin Drugs 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 230000001566 pro-viral effect Effects 0.000 description 1
• 229940002612 prodrug Drugs 0.000 description 1
• 239000000651 prodrug Substances 0.000 description 1
• 239000000583 progesterone congener Substances 0.000 description 1
• 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 125000005470 propylenyl group Chemical group 0.000 description 1
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
• 229960004432 raltitrexed Drugs 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000008261 resistance mechanism Effects 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 229940120975 revlimid Drugs 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229950009919 saracatinib Drugs 0.000 description 1
• OUKYUETWWIPKQR-UHFFFAOYSA-N saracatinib Chemical compound C1CN(C)CCN1CCOC1=CC(OC2CCOCC2)=C(C(NC=2C(=CC=C3OCOC3=2)Cl)=NC=N2)C2=C1 OUKYUETWWIPKQR-UHFFFAOYSA-N 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 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
• 238000009097 single-agent therapy Methods 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 102000009076 src-Family Kinases Human genes 0.000 description 1
• 108010087686 src-Family Kinases Proteins 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 229940032147 starch Drugs 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 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 1
• 229940063683 taxotere Drugs 0.000 description 1
• NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
• 229960001278 teniposide Drugs 0.000 description 1
• ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 1
• QAZVTJCOYJOJGO-UHFFFAOYSA-N tert-butyl n-(4-hydroxypyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CNCC1O QAZVTJCOYJOJGO-UHFFFAOYSA-N 0.000 description 1
• SBXFEKMSOOXLAP-ZDUSSCGKSA-N tert-butyl n-[(3s)-1-(5-chloro-2-formylphenyl)pyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=CC(Cl)=CC=C1C=O SBXFEKMSOOXLAP-ZDUSSCGKSA-N 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
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 229960003433 thalidomide Drugs 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229940044693 topoisomerase inhibitor 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
• 229960000303 topotecan Drugs 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
• 238000001890 transfection Methods 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 241000701447 unidentified baculovirus Species 0.000 description 1
• 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(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]([C@@H](C)O)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](CCCNC(N)=N)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)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)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=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229940099039 velcade 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
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1