NO318083B1 - Pyrrolsubstituert 2-indolinon protein kinase inhibitorer - Google Patents

Info

Publication number

NO318083B1

NO318083B1 NO20005916A NO20005916A NO318083B1 NO 318083 B1 NO318083 B1 NO 318083B1 NO 20005916 A NO20005916 A NO 20005916A NO 20005916 A NO20005916 A NO 20005916A NO 318083 B1 NO318083 B1 NO 318083B1

Authority

NO

Norway

Prior art keywords

dimethyl

pyrrol

dihydroindol

oxindole

oxo

Prior art date

1998-05-29

Links

• Espacenet
• Global Dossier
• Discuss

• -1 Pyrrole-substituted 2-indolinone Chemical class 0.000 title claims description 47
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
• 239000003909 protein kinase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 232
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 42
• 102000001253 Protein Kinase Human genes 0.000 claims description 33
• 108060006633 protein kinase Proteins 0.000 claims description 33
• 102000005962 receptors Human genes 0.000 claims description 32
• 108020003175 receptors Proteins 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 30
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 28
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 230000033115 angiogenesis Effects 0.000 claims description 22
• 229940079593 drug Drugs 0.000 claims description 21
• 239000000126 substance Substances 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 206010006187 Breast cancer Diseases 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 11
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 206010012601 diabetes mellitus Diseases 0.000 claims description 11
• 208000020816 lung neoplasm Diseases 0.000 claims description 11
• 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 10
• 201000005202 lung cancer Diseases 0.000 claims description 10
• 206010033128 Ovarian cancer Diseases 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 9
• 208000005017 glioblastoma Diseases 0.000 claims description 9
• NHFDRBXTEDBWCZ-ZROIWOOFSA-N 3-[2,4-dimethyl-5-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=CC=C3NC\2=O)=C1C NHFDRBXTEDBWCZ-ZROIWOOFSA-N 0.000 claims description 8
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 230000003463 hyperproliferative effect Effects 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 206010005003 Bladder cancer Diseases 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 7
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 7
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 7
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 6
• 230000001900 immune effect Effects 0.000 claims description 6
• 230000004968 inflammatory condition Effects 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 206010016654 Fibrosis Diseases 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 230000004761 fibrosis Effects 0.000 claims description 5
• 201000010536 head and neck cancer Diseases 0.000 claims description 5
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
• TWMZFPSODZCNLQ-UHFFFAOYSA-N 3-[5-[(5-iodo-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC(I)=CC=C3NC2=O)=C1C TWMZFPSODZCNLQ-UHFFFAOYSA-N 0.000 claims description 4
• 206010003571 Astrocytoma Diseases 0.000 claims description 4
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 206010018338 Glioma Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• JWFUKWLQYWSUOU-UHFFFAOYSA-N 3-[2,4-dimethyl-5-[(6-morpholin-4-yl-2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC=C(C=C3NC2=O)N2CCOCC2)=C1C JWFUKWLQYWSUOU-UHFFFAOYSA-N 0.000 claims description 3
• LUOFXVYSCYRHFS-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrol-2-yl]methylidene]-6-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=C3NC(=O)C(=CC4=C(C(CCCN5CCOCC5)=C(C)N4)C)C3=CC=2)=C1 LUOFXVYSCYRHFS-UHFFFAOYSA-N 0.000 claims description 3
• KXDDHRYCUUEICK-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-6-(2-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC=C1C1=CC=C(C(=CC2=C(C(CCCN(C)C)=C(C)N2)C)C(=O)N2)C2=C1 KXDDHRYCUUEICK-UHFFFAOYSA-N 0.000 claims description 3
• HGJHMUJDVHGDFS-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-6-methoxy-1h-indol-2-one Chemical compound O=C1NC2=CC(OC)=CC=C2C1=CC=1NC(C)=C(CCCN(C)C)C=1C HGJHMUJDVHGDFS-UHFFFAOYSA-N 0.000 claims description 3
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
• 208000032612 Glial tumor Diseases 0.000 claims description 3
• 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 3
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• YEVBDKUJUCJAMN-UHFFFAOYSA-N 3-[5-[(6-hydroxy-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC=C(O)C=C3NC2=O)=C1C YEVBDKUJUCJAMN-UHFFFAOYSA-N 0.000 claims description 2
• XLHWOGDAUMWGHR-UHFFFAOYSA-N 3-[5-[[6-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound COC1=CC=CC(C=2C=C3NC(=O)C(=CC4=C(C(CCC(O)=O)=C(C)N4)C)C3=CC=2)=C1 XLHWOGDAUMWGHR-UHFFFAOYSA-N 0.000 claims description 2
• BCRNCFOBRHFGBC-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrol-2-yl]methylidene]-6-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=CC2=C(C(CCCN3CCOCC3)=C(C)N2)C)C(=O)N2)C2=C1 BCRNCFOBRHFGBC-UHFFFAOYSA-N 0.000 claims description 2
• VRSDIXKBDMNAJU-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-2-oxo-1h-indole-5-sulfonamide Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(=CC=C3NC2=O)S(N)(=O)=O)=C1C VRSDIXKBDMNAJU-UHFFFAOYSA-N 0.000 claims description 2
• VIRGIOQJECYOKB-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-4-(2-hydroxyethyl)-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=C(CCO)C=CC=C3NC2=O)=C1C VIRGIOQJECYOKB-UHFFFAOYSA-N 0.000 claims description 2
• LSYZZVKELDHCDH-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-n,n-dimethyl-2-oxo-1h-indole-5-sulfonamide Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(=CC=C3NC2=O)S(=O)(=O)N(C)C)=C1C LSYZZVKELDHCDH-UHFFFAOYSA-N 0.000 claims description 2
• 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 2
• 230000001363 autoimmune Effects 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 3
• APYYTEJNOZQZNA-UHFFFAOYSA-N 3-[2,4-dimethyl-5-[(2-oxo-6-phenyl-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC=C(C=C3NC2=O)C=2C=CC=CC=2)=C1C APYYTEJNOZQZNA-UHFFFAOYSA-N 0.000 claims 1
• CUQJCVAMGWHJPW-UHFFFAOYSA-N 3-[5-[(5-chloro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC(Cl)=CC=C3NC2=O)=C1C CUQJCVAMGWHJPW-UHFFFAOYSA-N 0.000 claims 1
• MPBRWFJYTOVGPY-UHFFFAOYSA-N 3-[5-[[6-(2-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(=CC2=C(C(CCC(O)=O)=C(C)N2)C)C(=O)N2)C2=C1 MPBRWFJYTOVGPY-UHFFFAOYSA-N 0.000 claims 1
• KFUOUFXHFQOQAG-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-2-oxo-n-propan-2-yl-1h-indole-5-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC(C)C)=CC=C2NC(=O)C1=CC=1NC(C)=C(CCCN(C)C)C=1C KFUOUFXHFQOQAG-UHFFFAOYSA-N 0.000 claims 1
• PPTVYGAPIZYPBT-UHFFFAOYSA-N 5-bromo-3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(Br)=CC=C3NC2=O)=C1C PPTVYGAPIZYPBT-UHFFFAOYSA-N 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 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 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 333
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 288
• 239000007787 solid Substances 0.000 description 226
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 217
• 239000000203 mixture Substances 0.000 description 210
• 229910001868 water Inorganic materials 0.000 description 187
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 166
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 166
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
• 239000002244 precipitate Substances 0.000 description 106
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 103
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 101
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 98
• 210000004027 cell Anatomy 0.000 description 97
• 239000011541 reaction mixture Substances 0.000 description 94
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• 239000000243 solution Substances 0.000 description 79
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
• 238000000034 method Methods 0.000 description 68
• 201000010099 disease Diseases 0.000 description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 67
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
• 238000003828 vacuum filtration Methods 0.000 description 63
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 61
• 229920002554 vinyl polymer Polymers 0.000 description 56
• 230000000694 effects Effects 0.000 description 50
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 47
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 46
• 239000012267 brine Substances 0.000 description 46
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 46
• 206010028980 Neoplasm Diseases 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 43
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 43
• 239000000741 silica gel Substances 0.000 description 43
• 229910002027 silica gel Inorganic materials 0.000 description 43
• 239000000706 filtrate Substances 0.000 description 42
• 229960000583 acetic acid Drugs 0.000 description 38
• 201000011510 cancer Diseases 0.000 description 31
• 230000003197 catalytic effect Effects 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 31
• 239000003921 oil Substances 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 31
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
• 239000000047 product Substances 0.000 description 27
• 238000001914 filtration Methods 0.000 description 26
• 150000003839 salts Chemical class 0.000 description 26
• 239000000725 suspension Substances 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 24
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 24
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
• 238000002965 ELISA Methods 0.000 description 23
• PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 23
• 239000012043 crude product Substances 0.000 description 23
• WEMKCIPNUIQYSM-UHFFFAOYSA-N 3-(5-formyl-4-methyl-1h-pyrrol-3-yl)propanoic acid Chemical compound CC=1C(CCC(O)=O)=CNC=1C=O WEMKCIPNUIQYSM-UHFFFAOYSA-N 0.000 description 22
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
• 239000010410 layer Substances 0.000 description 22
• RUILENPFHDHTRC-UHFFFAOYSA-N 3-(5-formyl-2,4-dimethyl-1h-pyrrol-3-yl)propanoic acid Chemical compound CC=1NC(C=O)=C(C)C=1CCC(O)=O RUILENPFHDHTRC-UHFFFAOYSA-N 0.000 description 21
• 230000019491 signal transduction Effects 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• 238000007792 addition Methods 0.000 description 20
• 239000005457 ice water Substances 0.000 description 20
• 230000008859 change Effects 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 229940002612 prodrug Drugs 0.000 description 18
• 239000000651 prodrug Substances 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 230000015572 biosynthetic process Effects 0.000 description 16
• 230000001413 cellular effect Effects 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 15
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 15
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 15
• BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 15
• 239000003446 ligand Substances 0.000 description 15
• 108090000623 proteins and genes Proteins 0.000 description 15
• 239000012312 sodium hydride Substances 0.000 description 15
• 229910000104 sodium hydride Inorganic materials 0.000 description 15
• 238000004809 thin layer chromatography Methods 0.000 description 15
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
• 238000003556 assay Methods 0.000 description 14
• 150000005623 oxindoles Chemical class 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 13
• 108091000080 Phosphotransferase Proteins 0.000 description 13
• 150000001299 aldehydes Chemical class 0.000 description 13
• 230000004663 cell proliferation Effects 0.000 description 13
• 239000000463 material Substances 0.000 description 13
• 239000002609 medium Substances 0.000 description 13
• 102000020233 phosphotransferase Human genes 0.000 description 13
• UQEANKGXXSENNF-UHFFFAOYSA-N 4-bromo-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1F UQEANKGXXSENNF-UHFFFAOYSA-N 0.000 description 12
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 230000003993 interaction Effects 0.000 description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
• 235000018102 proteins Nutrition 0.000 description 12
• 102000004169 proteins and genes Human genes 0.000 description 12
• 229910000029 sodium carbonate Inorganic materials 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 230000004862 vasculogenesis Effects 0.000 description 12
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 11
• 230000002159 abnormal effect Effects 0.000 description 11
• 238000009472 formulation Methods 0.000 description 11
• 230000001404 mediated effect Effects 0.000 description 11
• 230000002062 proliferating effect Effects 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• DFGZEOUBIHLXFD-UHFFFAOYSA-N 5-methoxy-1,3-dihydroindol-2-one Chemical class COC1=CC=C2NC(=O)CC2=C1 DFGZEOUBIHLXFD-UHFFFAOYSA-N 0.000 description 10
• JARRYVQFBQVOBE-UHFFFAOYSA-N 6-bromo-1,3-dihydroindol-2-one Chemical class BrC1=CC=C2CC(=O)NC2=C1 JARRYVQFBQVOBE-UHFFFAOYSA-N 0.000 description 10
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 10
• 102100037787 Protein-tyrosine kinase 2-beta Human genes 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 239000000654 additive Substances 0.000 description 10
• 125000003118 aryl group Chemical group 0.000 description 10
• 238000006366 phosphorylation reaction Methods 0.000 description 10
• 239000011550 stock solution Substances 0.000 description 10
• 230000001225 therapeutic effect Effects 0.000 description 10
• LLLKBUWXODIMEW-UHFFFAOYSA-N 2-oxo-1,3-dihydroindole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(=O)CC2=C1 LLLKBUWXODIMEW-UHFFFAOYSA-N 0.000 description 9
• USRZZPHRQZGXFH-UHFFFAOYSA-N 4-methyl-1,3-dihydroindol-2-one Chemical compound CC1=CC=CC2=C1CC(=O)N2 USRZZPHRQZGXFH-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 102000009465 Growth Factor Receptors Human genes 0.000 description 9
• 108010009202 Growth Factor Receptors Proteins 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 230000024245 cell differentiation Effects 0.000 description 9
• 230000010261 cell growth Effects 0.000 description 9
• 230000001086 cytosolic effect Effects 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 238000001727 in vivo Methods 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
• 230000026731 phosphorylation Effects 0.000 description 9
• 235000019260 propionic acid Nutrition 0.000 description 9
• 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 9
• 239000000758 substrate Substances 0.000 description 9
• FYBNVKMJOOYPGI-UHFFFAOYSA-N 2-oxo-1,3-dihydroindole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2NC(=O)CC2=C1 FYBNVKMJOOYPGI-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 101710098940 Pro-epidermal growth factor Proteins 0.000 description 8
• 102100033237 Pro-epidermal growth factor Human genes 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 239000006180 TBST buffer Substances 0.000 description 8
• 150000001413 amino acids Chemical group 0.000 description 8
• OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 239000000969 carrier Substances 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 230000003834 intracellular effect Effects 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 238000010907 mechanical stirring Methods 0.000 description 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• 239000002243 precursor Substances 0.000 description 8
• 239000011780 sodium chloride Substances 0.000 description 8
• 238000012546 transfer Methods 0.000 description 8
• VIMNAEVMZXIKFL-UHFFFAOYSA-N 5-bromo-1,3-dihydroindol-2-one Chemical class BrC1=CC=C2NC(=O)CC2=C1 VIMNAEVMZXIKFL-UHFFFAOYSA-N 0.000 description 7
• FAIHEVFTQPMOLE-UHFFFAOYSA-N 5-iodo-1,3-dihydroindol-2-one Chemical compound IC1=CC=C2NC(=O)CC2=C1 FAIHEVFTQPMOLE-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 7
• 108010031794 IGF Type 1 Receptor Proteins 0.000 description 7
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 7
• 238000013459 approach Methods 0.000 description 7
• 229910002092 carbon dioxide Inorganic materials 0.000 description 7
• 229910002091 carbon monoxide Inorganic materials 0.000 description 7
• 238000010790 dilution Methods 0.000 description 7
• 239000012895 dilution Substances 0.000 description 7
• 230000014509 gene expression Effects 0.000 description 7
• 239000003102 growth factor Substances 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 238000010898 silica gel chromatography Methods 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• FAPIBOYLMCVQRF-UHFFFAOYSA-N 1-fluoro-4-(2-methoxyphenyl)-2-nitrobenzene Chemical group COC1=CC=CC=C1C1=CC=C(F)C([N+]([O-])=O)=C1 FAPIBOYLMCVQRF-UHFFFAOYSA-N 0.000 description 6
• WXJWBEAGVWVEDM-UHFFFAOYSA-N 5-(2-chloroacetyl)-1,3-dihydroindol-2-one Chemical compound ClCC(=O)C1=CC=C2NC(=O)CC2=C1 WXJWBEAGVWVEDM-UHFFFAOYSA-N 0.000 description 6
• WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical class ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 6
• HXQDSHSATAEREW-UHFFFAOYSA-N 5-methyl-1,3-dihydroindol-2-one Chemical compound CC1=CC=C2NC(=O)CC2=C1 HXQDSHSATAEREW-UHFFFAOYSA-N 0.000 description 6
• OXOQGUGIJKUSRP-UHFFFAOYSA-N 6-methoxy-1,3-dihydroindol-2-one Chemical class COC1=CC=C2CC(=O)NC2=C1 OXOQGUGIJKUSRP-UHFFFAOYSA-N 0.000 description 6
• BRTXRFCARXOWJV-UHFFFAOYSA-N 6-phenyl-1,3-dihydroindol-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1C1=CC=CC=C1 BRTXRFCARXOWJV-UHFFFAOYSA-N 0.000 description 6
• 208000023275 Autoimmune disease Diseases 0.000 description 6
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
• 239000012591 Dulbecco’s Phosphate Buffered Saline Substances 0.000 description 6
• 108010010803 Gelatin Proteins 0.000 description 6
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 6
• 102000003746 Insulin Receptor Human genes 0.000 description 6
• 108010001127 Insulin Receptor Proteins 0.000 description 6
• 241000699666 Mus <mouse, genus> Species 0.000 description 6
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 6
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 6
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
• UOIFTOBIGNZZSO-UHFFFAOYSA-N acetic acid;ethyl acetate;hexane Chemical compound CC(O)=O.CCCCCC.CCOC(C)=O UOIFTOBIGNZZSO-UHFFFAOYSA-N 0.000 description 6
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 238000004113 cell culture Methods 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 230000018109 developmental process Effects 0.000 description 6
• 239000012091 fetal bovine serum Substances 0.000 description 6
• 239000007789 gas Substances 0.000 description 6
• 229920000159 gelatin Polymers 0.000 description 6
• 239000008273 gelatin Substances 0.000 description 6
• 235000019322 gelatine Nutrition 0.000 description 6
• 235000011852 gelatine desserts Nutrition 0.000 description 6
• 235000003642 hunger Nutrition 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• 230000000670 limiting effect Effects 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 230000037361 pathway Effects 0.000 description 6
• 229920001223 polyethylene glycol Polymers 0.000 description 6
• 230000011664 signaling Effects 0.000 description 6
• 230000037351 starvation Effects 0.000 description 6
• 235000002374 tyrosine Nutrition 0.000 description 6
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
• HPXJIGZLXHQSGU-UHFFFAOYSA-N 5-(2-chloroethyl)-1,3-dihydroindol-2-one Chemical compound ClCCC1=CC=C2NC(=O)CC2=C1 HPXJIGZLXHQSGU-UHFFFAOYSA-N 0.000 description 5
• HRMQSJQDTTZJPC-UHFFFAOYSA-N 5-acetyl-1,3-dihydroindol-2-one Chemical compound CC(=O)C1=CC=C2NC(=O)CC2=C1 HRMQSJQDTTZJPC-UHFFFAOYSA-N 0.000 description 5
• CRPVKCLICXWDGA-UHFFFAOYSA-N 5-chloro-4-methyl-1,3-dihydroindol-2-one Chemical compound C1=C(Cl)C(C)=C2CC(=O)NC2=C1 CRPVKCLICXWDGA-UHFFFAOYSA-N 0.000 description 5
• YCIHQDVIAISDPS-UHFFFAOYSA-N 5-formyl-2,4-dimethyl-1h-pyrrole-3-carboxylic acid Chemical compound CC=1NC(C=O)=C(C)C=1C(O)=O YCIHQDVIAISDPS-UHFFFAOYSA-N 0.000 description 5
• OPHFPDJTRBPFFC-UHFFFAOYSA-N 6-(2-methoxyphenyl)-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC=C1C1=CC=C(CC(=O)N2)C2=C1 OPHFPDJTRBPFFC-UHFFFAOYSA-N 0.000 description 5
• IUPFDSDZXMXHJK-UHFFFAOYSA-N 6-(3-ethoxyphenyl)-1,3-dihydroindol-2-one Chemical compound CCOC1=CC=CC(C=2C=C3NC(=O)CC3=CC=2)=C1 IUPFDSDZXMXHJK-UHFFFAOYSA-N 0.000 description 5
• IRQBUMYFAYXEGV-UHFFFAOYSA-N 6-(3-methoxyphenyl)-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC(C=2C=C3NC(=O)CC3=CC=2)=C1 IRQBUMYFAYXEGV-UHFFFAOYSA-N 0.000 description 5
• OCOCBVKMMMIDLI-UHFFFAOYSA-N 6-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2CC(=O)NC2=C1 OCOCBVKMMMIDLI-UHFFFAOYSA-N 0.000 description 5
• PKQNTFAOZIVXCE-UHFFFAOYSA-N 6-fluoro-1,3-dihydroindol-2-one Chemical class FC1=CC=C2CC(=O)NC2=C1 PKQNTFAOZIVXCE-UHFFFAOYSA-N 0.000 description 5
• 206010039491 Sarcoma Diseases 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 239000004480 active ingredient Substances 0.000 description 5
• 235000001014 amino acid Nutrition 0.000 description 5
• 239000002246 antineoplastic agent Substances 0.000 description 5
• 238000004166 bioassay Methods 0.000 description 5
• 230000004071 biological effect Effects 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 208000019425 cirrhosis of liver Diseases 0.000 description 5
• 229940127089 cytotoxic agent Drugs 0.000 description 5
• 210000002889 endothelial cell Anatomy 0.000 description 5
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
• 230000002209 hydrophobic effect Effects 0.000 description 5
• 239000002198 insoluble material Substances 0.000 description 5
• 208000032839 leukemia Diseases 0.000 description 5
• 210000003584 mesangial cell Anatomy 0.000 description 5
• 230000002503 metabolic effect Effects 0.000 description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 description 5
• 230000036470 plasma concentration Effects 0.000 description 5
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 235000000346 sugar Nutrition 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 4
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
• LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
• PBPINVZBVWMQCT-UHFFFAOYSA-N 2-(2-nitro-4-phenylphenyl)acetic acid Chemical compound C1=C([N+]([O-])=O)C(CC(=O)O)=CC=C1C1=CC=CC=C1 PBPINVZBVWMQCT-UHFFFAOYSA-N 0.000 description 4
• LBZPHZBNFDOCCR-UHFFFAOYSA-N 2-(4-bromo-2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Br)C=C1[N+]([O-])=O LBZPHZBNFDOCCR-UHFFFAOYSA-N 0.000 description 4
• CLOUBWLUOFJGML-UHFFFAOYSA-N 2-(5-amino-2-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=C(N)C=C1CC(=O)NN CLOUBWLUOFJGML-UHFFFAOYSA-N 0.000 description 4
• VMUNVLRBZWDDHR-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-2-nitrophenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(CC(O)=O)C([N+]([O-])=O)=C1 VMUNVLRBZWDDHR-UHFFFAOYSA-N 0.000 description 4
• PJRWVQFEVVSTKZ-UHFFFAOYSA-N 2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C2NC(=O)CC2=C1 PJRWVQFEVVSTKZ-UHFFFAOYSA-N 0.000 description 4
• BAAJNXQYDCMIFO-UHFFFAOYSA-N 3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrole-2-carbaldehyde Chemical compound N1C(C=O)=C(C)C(CCCN2CCOCC2)=C1C BAAJNXQYDCMIFO-UHFFFAOYSA-N 0.000 description 4
• JVCREVCBOGOWCL-UHFFFAOYSA-N 3-pyrrolidin-1-yl-1,3-dihydroindol-2-one Chemical class O=C1NC2=CC=CC=C2C1N1CCCC1 JVCREVCBOGOWCL-UHFFFAOYSA-N 0.000 description 4
• XWDKOXPQYRNLOO-UHFFFAOYSA-N 4-(3-ethoxyphenyl)-1-fluoro-2-nitrobenzene Chemical group CCOC1=CC=CC(C=2C=C(C(F)=CC=2)[N+]([O-])=O)=C1 XWDKOXPQYRNLOO-UHFFFAOYSA-N 0.000 description 4
• PFZOPWMHTMNDMV-UHFFFAOYSA-N 5-ethyl-1,3-dihydroindol-2-one Chemical compound CCC1=CC=C2NC(=O)CC2=C1 PFZOPWMHTMNDMV-UHFFFAOYSA-N 0.000 description 4
• MYUNWQZTMMYCCB-UHFFFAOYSA-N 6-(4-methoxyphenyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(CC(=O)N2)C2=C1 MYUNWQZTMMYCCB-UHFFFAOYSA-N 0.000 description 4
• ZOJZYAPVVOLQQB-UHFFFAOYSA-N 6-hydroxy-1,3-dihydroindol-2-one Chemical compound OC1=CC=C2CC(=O)NC2=C1 ZOJZYAPVVOLQQB-UHFFFAOYSA-N 0.000 description 4
• ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate 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-N 0.000 description 4
• 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 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• 241000283707 Capra Species 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
• 102100039137 Insulin receptor-related protein Human genes 0.000 description 4
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
• 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 4
• 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 4
• 241000220317 Rosa Species 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 230000003305 autocrine Effects 0.000 description 4
• 210000004204 blood vessel Anatomy 0.000 description 4
• 210000000481 breast Anatomy 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 235000011089 carbon dioxide Nutrition 0.000 description 4
• 230000032823 cell division Effects 0.000 description 4
• 239000013592 cell lysate Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• FSADKQTZVABRCO-UHFFFAOYSA-N dimethyl 2-(2-nitro-4-phenylphenyl)propanedioate Chemical compound C1=C([N+]([O-])=O)C(C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=CC=C1 FSADKQTZVABRCO-UHFFFAOYSA-N 0.000 description 4
• NJAONFWUEGWOPG-UHFFFAOYSA-N dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=CC=C(Br)C=C1[N+]([O-])=O NJAONFWUEGWOPG-UHFFFAOYSA-N 0.000 description 4
• 239000003937 drug carrier Substances 0.000 description 4
• 230000002255 enzymatic effect Effects 0.000 description 4
• 238000013265 extended release Methods 0.000 description 4
• 239000004744 fabric Substances 0.000 description 4
• 230000003176 fibrotic effect Effects 0.000 description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 206010017758 gastric cancer Diseases 0.000 description 4
• 230000012010 growth Effects 0.000 description 4
• 239000001963 growth medium Substances 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 108010054372 insulin receptor-related receptor Proteins 0.000 description 4
• 229910052742 iron Inorganic materials 0.000 description 4
• 239000002502 liposome Substances 0.000 description 4
• 230000007246 mechanism Effects 0.000 description 4
• XFOSBARPNHJHHD-UHFFFAOYSA-N n-methyl-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2NC(=O)CC2=C1 XFOSBARPNHJHHD-UHFFFAOYSA-N 0.000 description 4
• DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 4
• 229920001184 polypeptide Polymers 0.000 description 4
• 108090000765 processed proteins & peptides Proteins 0.000 description 4
• 102000004196 processed proteins & peptides Human genes 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 150000008163 sugars Chemical class 0.000 description 4
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 4
• IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 4
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
• ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 3
• FCHZACFMGHJGEE-UHFFFAOYSA-N 1-fluoro-2-nitro-4-phenylbenzene Chemical group C1=C(F)C([N+](=O)[O-])=CC(C=2C=CC=CC=2)=C1 FCHZACFMGHJGEE-UHFFFAOYSA-N 0.000 description 3
• OWVXRMWQDIKWMO-UHFFFAOYSA-N 2-[4-(3-ethoxyphenyl)-2-nitrophenyl]acetic acid Chemical compound CCOC1=CC=CC(C=2C=C(C(CC(O)=O)=CC=2)[N+]([O-])=O)=C1 OWVXRMWQDIKWMO-UHFFFAOYSA-N 0.000 description 3
• MDEHFNBKDPLEEJ-UHFFFAOYSA-N 2-hydroxyimino-n-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(=O)C=NO)C=C1 MDEHFNBKDPLEEJ-UHFFFAOYSA-N 0.000 description 3
• SAGABBLUUSFKNW-UHFFFAOYSA-N 3-(2,4-dimethyl-1h-pyrrol-3-yl)propanoic acid Chemical compound CC1=CNC(C)=C1CCC(O)=O SAGABBLUUSFKNW-UHFFFAOYSA-N 0.000 description 3
• SOFWMZAVOINJGR-UHFFFAOYSA-N 3-(2-oxo-1,3-dihydroindol-5-yl)propanenitrile Chemical compound N#CCCC1=CC=C2NC(=O)CC2=C1 SOFWMZAVOINJGR-UHFFFAOYSA-N 0.000 description 3
• LDNTUJJLQVCEQX-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrole-2-carbaldehyde Chemical compound CN(C)CCCC1=C(C)NC(C=O)=C1C LDNTUJJLQVCEQX-UHFFFAOYSA-N 0.000 description 3
• BKTIIWWGWJQMPF-UHFFFAOYSA-N 5,7-dibromo-4-methyl-1,3-dihydroindol-2-one Chemical compound C1=C(Br)C(C)=C2CC(=O)NC2=C1Br BKTIIWWGWJQMPF-UHFFFAOYSA-N 0.000 description 3
• JPUYXUBUJJDJNL-UHFFFAOYSA-N 5-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2NC(=O)CC2=C1 JPUYXUBUJJDJNL-UHFFFAOYSA-N 0.000 description 3
• WSOSXQWLCFAZGI-UHFFFAOYSA-N 5-bromo-4-methyl-1,3-dihydroindol-2-one Chemical compound C1=C(Br)C(C)=C2CC(=O)NC2=C1 WSOSXQWLCFAZGI-UHFFFAOYSA-N 0.000 description 3
• FUZSPEICNULOGO-UHFFFAOYSA-N 5-ethoxycarbonyl-3-(3-ethoxy-3-oxopropyl)-4-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CCOC(=O)CCC=1C(C)=C(C(=O)OCC)NC=1C(O)=O FUZSPEICNULOGO-UHFFFAOYSA-N 0.000 description 3
• DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical class FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 3
• LZPKWQOLOCLSBO-UHFFFAOYSA-N 6-(trifluoromethyl)-1,3-dihydroindol-2-one Chemical class FC(F)(F)C1=CC=C2CC(=O)NC2=C1 LZPKWQOLOCLSBO-UHFFFAOYSA-N 0.000 description 3
• CENVPIZOTHULGJ-UHFFFAOYSA-N 6-chloro-1,3-dihydroindol-2-one Chemical class ClC1=CC=C2CC(=O)NC2=C1 CENVPIZOTHULGJ-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 201000009030 Carcinoma Diseases 0.000 description 3
• 208000024172 Cardiovascular disease Diseases 0.000 description 3
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 description 3
• 208000017604 Hodgkin disease Diseases 0.000 description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 3
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 3
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 3
• 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 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• 102000052575 Proto-Oncogene Human genes 0.000 description 3
• 108700020978 Proto-Oncogene Proteins 0.000 description 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
• 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 3
• 101000852966 Rattus norvegicus Interleukin-1 receptor-like 1 Proteins 0.000 description 3
• 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 3
• 102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 description 3
• 102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 description 3
• 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 description 3
• 230000001154 acute effect Effects 0.000 description 3
• 230000000996 additive effect Effects 0.000 description 3
• 238000010171 animal model Methods 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 206010003246 arthritis Diseases 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• 230000009286 beneficial effect Effects 0.000 description 3
• 230000000903 blocking effect Effects 0.000 description 3
• 210000000170 cell membrane Anatomy 0.000 description 3
• 230000036755 cellular response Effects 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 235000010980 cellulose Nutrition 0.000 description 3
• 239000011248 coating agent Substances 0.000 description 3
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• YGMYINIHIYQFHB-UHFFFAOYSA-N dimethyl 2-(4-fluoro-2-nitrophenyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=CC=C(F)C=C1[N+]([O-])=O YGMYINIHIYQFHB-UHFFFAOYSA-N 0.000 description 3
• YSGMYMHSGKXDPG-UHFFFAOYSA-N dimethyl 2-[4-(2-methoxyphenyl)-2-nitrophenyl]propanedioate Chemical compound C1=C([N+]([O-])=O)C(C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=CC=C1OC YSGMYMHSGKXDPG-UHFFFAOYSA-N 0.000 description 3
• ZGSOIPAJGLECGE-UHFFFAOYSA-N dimethyl 2-[4-(3-ethoxyphenyl)-2-nitrophenyl]propanedioate Chemical compound CCOC1=CC=CC(C=2C=C(C(C(C(=O)OC)C(=O)OC)=CC=2)[N+]([O-])=O)=C1 ZGSOIPAJGLECGE-UHFFFAOYSA-N 0.000 description 3
• NIXVEKYSWIWAGT-UHFFFAOYSA-N dimethyl 2-[4-(4-methoxyphenyl)-2-nitrophenyl]propanedioate Chemical compound C1=C([N+]([O-])=O)C(C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=C(OC)C=C1 NIXVEKYSWIWAGT-UHFFFAOYSA-N 0.000 description 3
• 235000021186 dishes Nutrition 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 210000002744 extracellular matrix Anatomy 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 201000011066 hemangioma Diseases 0.000 description 3
• 208000026278 immune system disease Diseases 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• 150000007529 inorganic bases Chemical class 0.000 description 3
• 208000017169 kidney disease Diseases 0.000 description 3
• 238000002372 labelling Methods 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 210000004072 lung Anatomy 0.000 description 3
• 239000006166 lysate Substances 0.000 description 3
• 230000003211 malignant effect Effects 0.000 description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• CYBPPDZFRDSSME-UHFFFAOYSA-N methyl 2-oxo-1,3-dihydroindole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC(=O)CC2=C1 CYBPPDZFRDSSME-UHFFFAOYSA-N 0.000 description 3
• KKCOXRJQIIYHCQ-UHFFFAOYSA-N methyl 4-[(2-oxo-1,3-dihydroindol-5-yl)carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC=C(NC(=O)C2)C2=C1 KKCOXRJQIIYHCQ-UHFFFAOYSA-N 0.000 description 3
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 3
• 239000013642 negative control Substances 0.000 description 3
• 210000002569 neuron Anatomy 0.000 description 3
• 230000002611 ovarian Effects 0.000 description 3
• 230000002018 overexpression Effects 0.000 description 3
• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
• 201000002528 pancreatic cancer Diseases 0.000 description 3
• 230000002265 prevention Effects 0.000 description 3
• 239000003586 protic polar solvent Substances 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 125000000168 pyrrolyl group Chemical group 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 239000002002 slurry Substances 0.000 description 3
• 239000000600 sorbitol Substances 0.000 description 3
• 238000001228 spectrum Methods 0.000 description 3
• 239000008107 starch Substances 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 201000011549 stomach cancer Diseases 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• 231100000419 toxicity Toxicity 0.000 description 3
• 230000001988 toxicity Effects 0.000 description 3
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 3
• 230000029663 wound healing Effects 0.000 description 3
• CHCWUTJYLUBETR-UHFFFAOYSA-N (3-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC(B(O)O)=C1 CHCWUTJYLUBETR-UHFFFAOYSA-N 0.000 description 2
• NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 2
• VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 2
• YUZGGDGIGDSVPA-UHFFFAOYSA-N 1,3,5-trimethyl-4-(3-morpholin-4-yl-3-oxopropyl)pyrrole-2-carbaldehyde Chemical compound CN1C(C=O)=C(C)C(CCC(=O)N2CCOCC2)=C1C YUZGGDGIGDSVPA-UHFFFAOYSA-N 0.000 description 2
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
• UOXZPEGXZWCOPR-UHFFFAOYSA-N 1-fluoro-4-(3-methoxyphenyl)-2-nitrobenzene Chemical group COC1=CC=CC(C=2C=C(C(F)=CC=2)[N+]([O-])=O)=C1 UOXZPEGXZWCOPR-UHFFFAOYSA-N 0.000 description 2
• MXFZNWJJUITGAC-UHFFFAOYSA-N 1-fluoro-4-(4-methoxyphenyl)-2-nitrobenzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(F)C([N+]([O-])=O)=C1 MXFZNWJJUITGAC-UHFFFAOYSA-N 0.000 description 2
• ROGHUJUFCRFUSO-UHFFFAOYSA-N 1h-indole-4-carboxylic acid Chemical class OC(=O)C1=CC=CC2=C1C=CN2 ROGHUJUFCRFUSO-UHFFFAOYSA-N 0.000 description 2
• WFKNETIJXXWRHO-UHFFFAOYSA-N 2-(2-methyl-6-nitrophenyl)acetic acid Chemical compound CC1=CC=CC([N+]([O-])=O)=C1CC(O)=O WFKNETIJXXWRHO-UHFFFAOYSA-N 0.000 description 2
• LAFOTQFKZXKMFD-UHFFFAOYSA-N 2-(4-fluoro-2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1[N+]([O-])=O LAFOTQFKZXKMFD-UHFFFAOYSA-N 0.000 description 2
• JBRBLYXXQZRQOQ-UHFFFAOYSA-N 2-[2-nitro-4-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]phenyl]acetic acid Chemical compound C1=C([N+]([O-])=O)C(CC(=O)O)=CC=C1C1=CC=CC(NC(=O)C(F)(F)F)=C1 JBRBLYXXQZRQOQ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• SOEWWIDREFDEJC-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)-2-nitrophenyl]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=C(CC(O)=O)C([N+]([O-])=O)=C1 SOEWWIDREFDEJC-UHFFFAOYSA-N 0.000 description 2
• MWTVRSIFCMGCDS-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)-3-nitrophenyl]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=C(CC(O)=O)C=C1[N+]([O-])=O MWTVRSIFCMGCDS-UHFFFAOYSA-N 0.000 description 2
• UHFXANYMAIRBOF-UHFFFAOYSA-N 2-[4-(3-methoxyphenyl)-2-nitrophenyl]acetic acid Chemical compound COC1=CC=CC(C=2C=C(C(CC(O)=O)=CC=2)[N+]([O-])=O)=C1 UHFXANYMAIRBOF-UHFFFAOYSA-N 0.000 description 2
• IKEMNOMJHMIJNL-UHFFFAOYSA-N 2-[4-(3-methoxyphenyl)-3-nitrophenyl]acetic acid Chemical compound COC1=CC=CC(C=2C(=CC(CC(O)=O)=CC=2)[N+]([O-])=O)=C1 IKEMNOMJHMIJNL-UHFFFAOYSA-N 0.000 description 2
• ALXJUSWINGKGAW-UHFFFAOYSA-N 2-oxo-1,3-dihydroindole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1CC(=O)N2 ALXJUSWINGKGAW-UHFFFAOYSA-N 0.000 description 2
• AEJCJSGFTXNMLX-UHFFFAOYSA-N 2-oxo-n-[4-(trifluoromethyl)phenyl]-1,3-dihydroindole-5-sulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)C2)C2=C1 AEJCJSGFTXNMLX-UHFFFAOYSA-N 0.000 description 2
• ZDZVVSVVBTXHJX-UHFFFAOYSA-N 2-oxo-n-propan-2-yl-1,3-dihydroindole-5-sulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=C2NC(=O)CC2=C1 ZDZVVSVVBTXHJX-UHFFFAOYSA-N 0.000 description 2
• BKVSCRLYGVMHFD-UHFFFAOYSA-N 3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrole-2-carbaldehyde Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=O)=C1C BKVSCRLYGVMHFD-UHFFFAOYSA-N 0.000 description 2
• QSGALCFLGKPSHR-UHFFFAOYSA-N 3-(2,4-dimethyl-1h-pyrrol-3-yl)-1-morpholin-4-ylpropan-1-one Chemical compound CC1=CNC(C)=C1CCC(=O)N1CCOCC1 QSGALCFLGKPSHR-UHFFFAOYSA-N 0.000 description 2
• XANKLCNGFQBQPL-UHFFFAOYSA-N 3-(2-oxo-1,3-dihydroindol-4-yl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC2=C1CC(=O)N2 XANKLCNGFQBQPL-UHFFFAOYSA-N 0.000 description 2
• NEBLVPRYSZZNEF-UHFFFAOYSA-N 3-(2-oxo-1,3-dihydroindol-5-yl)propanoic acid Chemical compound OC(=O)CCC1=CC=C2NC(=O)CC2=C1 NEBLVPRYSZZNEF-UHFFFAOYSA-N 0.000 description 2
• NQWCWPNNZSFZGL-UHFFFAOYSA-N 3-(4-fluoro-3-nitrophenyl)aniline Chemical compound NC1=CC=CC(C=2C=C(C(F)=CC=2)[N+]([O-])=O)=C1 NQWCWPNNZSFZGL-UHFFFAOYSA-N 0.000 description 2
• FYMPIGRRSUORAR-UHFFFAOYSA-N 3-(4-methyl-1h-pyrrol-3-yl)propanoic acid Chemical compound CC1=CNC=C1CCC(O)=O FYMPIGRRSUORAR-UHFFFAOYSA-N 0.000 description 2
• OMJBYYJQTBHLOG-UHFFFAOYSA-N 3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)-n-(2-morpholin-4-ylethyl)propanamide Chemical compound CN1C(C=O)=C(C)C(CCC(=O)NCCN2CCOCC2)=C1C OMJBYYJQTBHLOG-UHFFFAOYSA-N 0.000 description 2
• YYDKBZZXKDZMAR-UHFFFAOYSA-N 3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)-n-(4-methoxyphenyl)propanamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CCC1=C(C)N(C)C(C=O)=C1C YYDKBZZXKDZMAR-UHFFFAOYSA-N 0.000 description 2
• HPOXJAOEPQODRF-UHFFFAOYSA-N 3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)-n-phenylpropanamide Chemical compound CN1C(C=O)=C(C)C(CCC(=O)NC=2C=CC=CC=2)=C1C HPOXJAOEPQODRF-UHFFFAOYSA-N 0.000 description 2
• PQTLMRNITSYCAL-UHFFFAOYSA-N 3-[1-(cyclohexylmethyl)-5-formyl-2,4-dimethylpyrrol-3-yl]propanoic acid Chemical compound O=CC1=C(C)C(CCC(O)=O)=C(C)N1CC1CCCCC1 PQTLMRNITSYCAL-UHFFFAOYSA-N 0.000 description 2
• ACGXXKQLAPXTBG-UHFFFAOYSA-N 3-[5-[(6-hydroxy-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC=C(O)C=C3NC2=O)=C1C ACGXXKQLAPXTBG-UHFFFAOYSA-N 0.000 description 2
• MAUJBIMARUNWBM-UHFFFAOYSA-N 3-[5-[[6-(3-ethoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound CCOC1=CC=CC(C=2C=C3NC(=O)C(=CC4=C(C(CCC(O)=O)=C(C)N4)C)C3=CC=2)=C1 MAUJBIMARUNWBM-UHFFFAOYSA-N 0.000 description 2
• GNDPWHKLEXPOKK-UHFFFAOYSA-N 3-[5-formyl-1-(2-methoxy-2-oxoethyl)-2,4-dimethylpyrrol-3-yl]propanoic acid Chemical compound COC(=O)CN1C(C)=C(CCC(O)=O)C(C)=C1C=O GNDPWHKLEXPOKK-UHFFFAOYSA-N 0.000 description 2
• QXZLRPVSNYQHNF-UHFFFAOYSA-N 3-[5-formyl-1-[(3-methoxyphenyl)methyl]-2,4-dimethylpyrrol-3-yl]propanoic acid Chemical compound COC1=CC=CC(CN2C(=C(C)C(CCC(O)=O)=C2C)C=O)=C1 QXZLRPVSNYQHNF-UHFFFAOYSA-N 0.000 description 2
• UMHJYAYUHPOHQO-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound CC=1NC(C=C2C3=CC=CC=C3NC2=O)=C(C)C=1CCCN1CCOCC1 UMHJYAYUHPOHQO-UHFFFAOYSA-N 0.000 description 2
• CPZVUWMFRDBPCS-UHFFFAOYSA-N 4-butyl-1,3-dihydroindol-2-one Chemical compound CCCCC1=CC=CC2=C1CC(=O)N2 CPZVUWMFRDBPCS-UHFFFAOYSA-N 0.000 description 2
• SLEITZPBBNQRTC-UHFFFAOYSA-N 5-bromo-3-[[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound CC=1NC(C=C2C3=CC(Br)=CC=C3NC2=O)=C(C)C=1CCCN1CCOCC1 SLEITZPBBNQRTC-UHFFFAOYSA-N 0.000 description 2
• DYTNNGQPYKZMNF-UHFFFAOYSA-N 5-ethoxy-1,3-dihydroindol-2-one Chemical compound CCOC1=CC=C2NC(=O)CC2=C1 DYTNNGQPYKZMNF-UHFFFAOYSA-N 0.000 description 2
• ZGTUSQAQXWSMDW-UHFFFAOYSA-N 5-hydroxy-1,3-dihydroindol-2-one Chemical class OC1=CC=C2NC(=O)CC2=C1 ZGTUSQAQXWSMDW-UHFFFAOYSA-N 0.000 description 2
• VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 2
• SESKLCQTEFAMPM-UHFFFAOYSA-N 5-morpholin-4-ylsulfonyl-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1S(=O)(=O)N1CCOCC1 SESKLCQTEFAMPM-UHFFFAOYSA-N 0.000 description 2
• JQCGHRDKVZPCRO-UHFFFAOYSA-N 5-nitro-1,3-dihydroindol-2-one Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)CC2=C1 JQCGHRDKVZPCRO-UHFFFAOYSA-N 0.000 description 2
• ULFMXQCBEHNLMZ-UHFFFAOYSA-N 7-bromo-5-chloro-1,3-dihydroindol-2-one Chemical compound BrC1=CC(Cl)=CC2=C1NC(=O)C2 ULFMXQCBEHNLMZ-UHFFFAOYSA-N 0.000 description 2
• VMUIOEOYZHJLEZ-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one Chemical class FC1=CC=CC2=C1NC(=O)C2 VMUIOEOYZHJLEZ-UHFFFAOYSA-N 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
• 208000003174 Brain Neoplasms Diseases 0.000 description 2
• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 2
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 238000012286 ELISA Assay Methods 0.000 description 2
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 101000818543 Homo sapiens Tyrosine-protein kinase ZAP-70 Proteins 0.000 description 2
• 108010001336 Horseradish Peroxidase Proteins 0.000 description 2
• 229930182816 L-glutamine Natural products 0.000 description 2
• 102100027754 Mast/stem cell growth factor receptor Kit Human genes 0.000 description 2
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
• 101100268066 Mus musculus Zap70 gene Proteins 0.000 description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• 108091008606 PDGF receptors Proteins 0.000 description 2
• 241000609499 Palicourea Species 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 description 2
• 102000018967 Platelet-Derived Growth Factor beta Receptor Human genes 0.000 description 2
• 241000276498 Pollachius virens Species 0.000 description 2
• 239000004743 Polypropylene Substances 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 241000700159 Rattus Species 0.000 description 2
• 102000014400 SH2 domains Human genes 0.000 description 2
• 108050003452 SH2 domains Proteins 0.000 description 2
• 108060006706 SRC Proteins 0.000 description 2
• 102000001332 SRC Human genes 0.000 description 2
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
• 210000001744 T-lymphocyte Anatomy 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
• 208000024313 Testicular Neoplasms Diseases 0.000 description 2
• 206010057644 Testis cancer Diseases 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• 239000013504 Triton X-100 Substances 0.000 description 2
• 229920004890 Triton X-100 Polymers 0.000 description 2
• 102100021125 Tyrosine-protein kinase ZAP-70 Human genes 0.000 description 2
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
• 239000012346 acetyl chloride Substances 0.000 description 2
• YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-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
• 230000009471 action Effects 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 235000019270 ammonium chloride Nutrition 0.000 description 2
• 239000000908 ammonium hydroxide Substances 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 230000035578 autophosphorylation Effects 0.000 description 2
• RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 2
• 230000008827 biological function Effects 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
• 239000012888 bovine serum Substances 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 229910000389 calcium phosphate Inorganic materials 0.000 description 2
• 235000011010 calcium phosphates Nutrition 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 239000001569 carbon dioxide Substances 0.000 description 2
• 229960004424 carbon dioxide Drugs 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 108700010039 chimeric receptor Proteins 0.000 description 2
• RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
• 229960002327 chloral hydrate Drugs 0.000 description 2
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
• 210000001072 colon Anatomy 0.000 description 2
• 208000029742 colonic neoplasm Diseases 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 235000008504 concentrate Nutrition 0.000 description 2
• 210000004246 corpus luteum Anatomy 0.000 description 2
• 239000006184 cosolvent Substances 0.000 description 2
• 239000006071 cream Substances 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 210000000172 cytosol Anatomy 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 229940075894 denatured ethanol Drugs 0.000 description 2
• 238000001514 detection method Methods 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• 125000000950 dibromo group Chemical group Br* 0.000 description 2
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 238000006471 dimerization reaction Methods 0.000 description 2
• UIRNQCRCSAYHKC-UHFFFAOYSA-N dimethyl 2-(2-methoxycarbonyl-6-nitrophenyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=C(C(=O)OC)C=CC=C1[N+]([O-])=O UIRNQCRCSAYHKC-UHFFFAOYSA-N 0.000 description 2
• FTMKVOQBYTWJFN-UHFFFAOYSA-N dimethyl 2-[2-nitro-4-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]phenyl]propanedioate Chemical compound C1=C([N+]([O-])=O)C(C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=CC(NC(=O)C(F)(F)F)=C1 FTMKVOQBYTWJFN-UHFFFAOYSA-N 0.000 description 2
• KEGXRXDQFPQJPZ-UHFFFAOYSA-N dimethyl 2-[4-(3-methoxyphenyl)-2-nitrophenyl]propanedioate Chemical compound C1=C([N+]([O-])=O)C(C(C(=O)OC)C(=O)OC)=CC=C1C1=CC=CC(OC)=C1 KEGXRXDQFPQJPZ-UHFFFAOYSA-N 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 230000013020 embryo development Effects 0.000 description 2
• 230000032692 embryo implantation Effects 0.000 description 2
• MLUBCFKZELZSHV-UHFFFAOYSA-N ethyl 5-methyl-4,6-dioxoheptanoate Chemical compound CCOC(=O)CCC(=O)C(C)C(C)=O MLUBCFKZELZSHV-UHFFFAOYSA-N 0.000 description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000010685 fatty oil Substances 0.000 description 2
• 210000002950 fibroblast Anatomy 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 229960002949 fluorouracil Drugs 0.000 description 2
• 230000002496 gastric effect Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 238000000099 in vitro assay Methods 0.000 description 2
• 208000027866 inflammatory disease Diseases 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 230000031146 intracellular signal transduction Effects 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 210000004698 lymphocyte Anatomy 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• WFQOIJIXNFOYCM-UHFFFAOYSA-N methyl 2-[2-nitro-4-(trifluoromethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O WFQOIJIXNFOYCM-UHFFFAOYSA-N 0.000 description 2
• JBCQPBVZKBEHNF-UHFFFAOYSA-N methyl 2-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JBCQPBVZKBEHNF-UHFFFAOYSA-N 0.000 description 2
• UZAFMJPJIDIXTG-UHFFFAOYSA-N methyl 3-[1-(2,2-dimethylpropyl)-5-formyl-2,4-dimethylpyrrol-3-yl]propanoate Chemical compound COC(=O)CCC=1C(C)=C(C=O)N(CC(C)(C)C)C=1C UZAFMJPJIDIXTG-UHFFFAOYSA-N 0.000 description 2
• RQMGRMCOFPLXIY-UHFFFAOYSA-N methyl 3-[1-(cyclohexylmethyl)-5-formyl-2,4-dimethylpyrrol-3-yl]propanoate Chemical compound CC1=C(CCC(=O)OC)C(C)=C(C=O)N1CC1CCCCC1 RQMGRMCOFPLXIY-UHFFFAOYSA-N 0.000 description 2
• FIJRVYHHOYXJSG-UHFFFAOYSA-N methyl 3-[1-[(4-fluorophenyl)methyl]-5-formyl-2,4-dimethylpyrrol-3-yl]propanoate Chemical compound CC1=C(CCC(=O)OC)C(C)=C(C=O)N1CC1=CC=C(F)C=C1 FIJRVYHHOYXJSG-UHFFFAOYSA-N 0.000 description 2
• TXEFZVUGRUTDQT-UHFFFAOYSA-N methyl 3-[5-formyl-1-[(3-methoxyphenyl)methyl]-2,4-dimethylpyrrol-3-yl]propanoate Chemical compound CC1=C(CCC(=O)OC)C(C)=C(C=O)N1CC1=CC=CC(OC)=C1 TXEFZVUGRUTDQT-UHFFFAOYSA-N 0.000 description 2
• MSYGVTQVRNLPMW-UHFFFAOYSA-N n,n-dimethyl-2-oxo-3h-indole-1-sulfonamide Chemical compound C1=CC=C2N(S(=O)(=O)N(C)C)C(=O)CC2=C1 MSYGVTQVRNLPMW-UHFFFAOYSA-N 0.000 description 2
• UQRSFMWYCLZIMU-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-6-yl)benzamide Chemical compound C=1C=C2CC(=O)NC2=CC=1NC(=O)C1=CC=CC=C1 UQRSFMWYCLZIMU-UHFFFAOYSA-N 0.000 description 2
• HWRRRQBVCDXNKB-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-6-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C2CC(=O)NC2=C1 HWRRRQBVCDXNKB-UHFFFAOYSA-N 0.000 description 2
• UZVVIMFOBRKSOV-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-5-formyl-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CN(C)CCNC(=O)C1=C(C)NC(C=O)=C1C UZVVIMFOBRKSOV-UHFFFAOYSA-N 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• 238000010899 nucleation Methods 0.000 description 2
• 230000033667 organ regeneration Effects 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• 230000001717 pathogenic effect Effects 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
• 230000035790 physiological processes and functions Effects 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• 239000011505 plaster Substances 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 239000003880 polar aprotic solvent Substances 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920001155 polypropylene Polymers 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• 229950008882 polysorbate Drugs 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
• 238000001556 precipitation Methods 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 230000035755 proliferation Effects 0.000 description 2
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
• 125000001453 quaternary ammonium group Chemical group 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• 238000002390 rotary evaporation Methods 0.000 description 2
• 239000012266 salt solution Substances 0.000 description 2
• 231100000241 scar Toxicity 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• 239000010802 sludge Substances 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 229940048086 sodium pyrophosphate Drugs 0.000 description 2
• 239000012265 solid product Substances 0.000 description 2
• 239000012258 stirred mixture Substances 0.000 description 2
• 125000001424 substituent group Chemical group 0.000 description 2
• 230000004083 survival effect Effects 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• 235000012222 talc Nutrition 0.000 description 2
• ALOFLJUGJDMERX-UHFFFAOYSA-N tert-butyl 2-hydroxyimino-3-oxobutanoate Chemical compound CC(=O)C(=NO)C(=O)OC(C)(C)C ALOFLJUGJDMERX-UHFFFAOYSA-N 0.000 description 2
• 201000003120 testicular cancer Diseases 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
• 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
• 230000001052 transient effect Effects 0.000 description 2
• 239000006163 transport media Substances 0.000 description 2
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 210000004881 tumor cell Anatomy 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 2
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 2
• 208000006542 von Hippel-Lindau disease Diseases 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
• YVCYOVLYYZRNJC-UHFFFAOYSA-N (2-methoxyphenoxy)boronic acid Chemical compound COC1=CC=CC=C1OB(O)O YVCYOVLYYZRNJC-UHFFFAOYSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• OGUSQFGGNLZTKG-BCLLBKCYSA-N (2s)-2,5-diamino-5-oxopentanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC(=O)[C@@H](N)CCC(N)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O OGUSQFGGNLZTKG-BCLLBKCYSA-N 0.000 description 1
• PBQQBKGLQWKLKQ-QPEQYQDCSA-N (3z)-3-[[4-(2-carboxyethyl)-3-methyl-1h-pyrrol-2-yl]methylidene]-2-oxo-1h-indole-5-carboxylic acid Chemical compound OC(=O)CCC1=CNC(\C=C/2C3=CC(=CC=C3NC\2=O)C(O)=O)=C1C PBQQBKGLQWKLKQ-QPEQYQDCSA-N 0.000 description 1
• OMJKFYKNWZZKTK-POHAHGRESA-N (5z)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide Chemical compound CN(C)N\N=C1/N=CN=C1C(N)=O OMJKFYKNWZZKTK-POHAHGRESA-N 0.000 description 1
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
• DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
• FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
• JQOBFOUVKCTYEP-UHFFFAOYSA-N 1,3,5-trimethyl-4-(3-oxo-3-piperidin-1-ylpropyl)pyrrole-2-carbaldehyde Chemical compound CN1C(C=O)=C(C)C(CCC(=O)N2CCCCC2)=C1C JQOBFOUVKCTYEP-UHFFFAOYSA-N 0.000 description 1
• XNJAYQHWXYJBBD-UHFFFAOYSA-N 1,4-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1F XNJAYQHWXYJBBD-UHFFFAOYSA-N 0.000 description 1
• CCAWDIFJOBKBSE-UHFFFAOYSA-N 1-(chloromethyl)-3,5-dimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1 CCAWDIFJOBKBSE-UHFFFAOYSA-N 0.000 description 1
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
• OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
• 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
• PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• VFERJFHPHSUIHY-UHFFFAOYSA-N 1-methyl-2-nitro-4-(trifluoromethyl)benzene Chemical compound CC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O VFERJFHPHSUIHY-UHFFFAOYSA-N 0.000 description 1
• DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
• QHIGJGOWDRZLHX-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-(4-fluoro-3-nitrophenyl)phenyl]acetamide Chemical compound C1=C(F)C([N+](=O)[O-])=CC(C=2C=C(NC(=O)C(F)(F)F)C=CC=2)=C1 QHIGJGOWDRZLHX-UHFFFAOYSA-N 0.000 description 1
• ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
• FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
• KCNISYPADDTFDO-UHFFFAOYSA-N 2,4-dinitrophenylacetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O KCNISYPADDTFDO-UHFFFAOYSA-N 0.000 description 1
• RHELIKWEKJQBMB-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)-2-nitrophenyl]propanedioic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(C(O)=O)C(O)=O)C([N+]([O-])=O)=C1 RHELIKWEKJQBMB-UHFFFAOYSA-N 0.000 description 1
• ZVMRVJMSSDJXJD-UHFFFAOYSA-N 2-[4-(3-methoxyphenyl)-2-nitrophenyl]propanedioic acid Chemical compound COC1=CC=CC(C=2C=C(C(C(C(O)=O)C(O)=O)=CC=2)[N+]([O-])=O)=C1 ZVMRVJMSSDJXJD-UHFFFAOYSA-N 0.000 description 1
• AVHSJBXMJCAJIT-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-2-nitrophenyl]propanedioic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(C(O)=O)C(O)=O)C([N+]([O-])=O)=C1 AVHSJBXMJCAJIT-UHFFFAOYSA-N 0.000 description 1
• PJBFHGHMMOGYNF-UHFFFAOYSA-N 2-amino-3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(N)C(O)=O PJBFHGHMMOGYNF-UHFFFAOYSA-N 0.000 description 1
• UQKYXSFVOIMJCD-UHFFFAOYSA-N 2-fluoro-1-nitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC(C=2C=CC=CC=2)=C1F UQKYXSFVOIMJCD-UHFFFAOYSA-N 0.000 description 1
• HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
• CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical class CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 description 1
• PFCMHOLHFDZWRN-UHFFFAOYSA-N 2-oxo-n-phenyl-1,3-dihydroindole-5-sulfonamide Chemical class C=1C=C2NC(=O)CC2=CC=1S(=O)(=O)NC1=CC=CC=C1 PFCMHOLHFDZWRN-UHFFFAOYSA-N 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• JHDQERQROBFSSO-UHFFFAOYSA-N 3,3-dibromo-1h-pyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CC=C2C(Br)(Br)C(=O)NC2=N1 JHDQERQROBFSSO-UHFFFAOYSA-N 0.000 description 1
• NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
• ORHYERPPJXHNIJ-UHFFFAOYSA-N 3-(1-benzyl-5-formyl-2,4-dimethylpyrrol-3-yl)propanoic acid Chemical compound O=CC1=C(C)C(CCC(O)=O)=C(C)N1CC1=CC=CC=C1 ORHYERPPJXHNIJ-UHFFFAOYSA-N 0.000 description 1
• RYCSNJCJOVQGBC-UHFFFAOYSA-N 3-(1-cyclopropyl-2h-pyridin-4-yl)-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1C(C=C1)=CCN1C1CC1 RYCSNJCJOVQGBC-UHFFFAOYSA-N 0.000 description 1
• PAGJUJSCMPSQRY-UHFFFAOYSA-N 3-(4-ethyl-5-formyl-1h-pyrrol-3-yl)propanoic acid Chemical compound CCC=1C(CCC(O)=O)=CNC=1C=O PAGJUJSCMPSQRY-UHFFFAOYSA-N 0.000 description 1
• VGVPFRRWNPRXJX-UHFFFAOYSA-N 3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)-n-[4-(trifluoromethyl)phenyl]propanamide Chemical compound CN1C(C=O)=C(C)C(CCC(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VGVPFRRWNPRXJX-UHFFFAOYSA-N 0.000 description 1
• DAWSVCYPGVSKSH-UHFFFAOYSA-N 3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)propanoic acid Chemical compound CC=1C(CCC(O)=O)=C(C)N(C)C=1C=O DAWSVCYPGVSKSH-UHFFFAOYSA-N 0.000 description 1
• VFLYEFSTBSBGAY-UHFFFAOYSA-N 3-[1-[(3-fluorophenyl)methyl]-5-formyl-2,4-dimethylpyrrol-3-yl]propanoic acid Chemical compound O=CC1=C(C)C(CCC(O)=O)=C(C)N1CC1=CC=CC(F)=C1 VFLYEFSTBSBGAY-UHFFFAOYSA-N 0.000 description 1
• HTJNLVJFTCEGCR-UHFFFAOYSA-N 3-[2,4-dimethyl-5-[(4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=C(C)C=CC=C3NC2=O)=C1C HTJNLVJFTCEGCR-UHFFFAOYSA-N 0.000 description 1
• WLRWNSHJNWQJBI-UHFFFAOYSA-N 3-[2,4-dimethyl-5-[(5-methyl-2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC(C)=CC=C3NC2=O)=C1C WLRWNSHJNWQJBI-UHFFFAOYSA-N 0.000 description 1
• CUYCEBZNBCKUCD-UHFFFAOYSA-N 3-[3-[[4-(2-carboxyethyl)-3-methyl-1h-pyrrol-2-yl]methylidene]-2-oxo-1h-indol-5-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC(CCC(O)=O)=CC=C3NC2=O)=C1C CUYCEBZNBCKUCD-UHFFFAOYSA-N 0.000 description 1
• YLOCIDYFMMJTMC-UHFFFAOYSA-N 3-[4-methyl-5-[(2-oxo-5-sulfamoyl-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC(=CC=C3NC2=O)S(N)(=O)=O)=C1C YLOCIDYFMMJTMC-UHFFFAOYSA-N 0.000 description 1
• CEFJMJRPRONXNH-UNOMPAQXSA-N 3-[4-methyl-5-[(z)-(2-oxo-6-phenyl-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(\C=C/2C3=CC=C(C=C3NC\2=O)C=2C=CC=CC=2)=C1C CEFJMJRPRONXNH-UNOMPAQXSA-N 0.000 description 1
• WNNYWBXPUXYLGT-UHFFFAOYSA-N 3-[5-[(5,6-dimethoxy-2-oxo-1H-indol-3-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid 3-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid Chemical compound C(=O)(O)CCC=1C(=C(NC1)C=O)C.COC=1C=C2C(C(NC2=CC1OC)=O)=CC1=C(C(=CN1)CCC(=O)O)C WNNYWBXPUXYLGT-UHFFFAOYSA-N 0.000 description 1
• CQXPYMNBBOWLME-UHFFFAOYSA-N 3-[5-[(5-bromo-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=CC(Br)=CC=C3NC2=O)=C1C CQXPYMNBBOWLME-UHFFFAOYSA-N 0.000 description 1
• IJTQZRFOGIWTCI-UHFFFAOYSA-N 3-[5-[(5-bromo-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC(Br)=CC=C3NC2=O)=C1C IJTQZRFOGIWTCI-UHFFFAOYSA-N 0.000 description 1
• KJTYTLSMFCQANO-UHFFFAOYSA-N 3-[5-[(5-chloro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrol-3-yl]propanoic acid 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic acid Chemical compound C(=O)(O)CCC1=C(NC(=C1C)C=O)C.ClC=1C=C2C(C(NC2=CC1)=O)=CC1=C(C(=C(N1)C)CCC(=O)O)C KJTYTLSMFCQANO-UHFFFAOYSA-N 0.000 description 1
• SQISXLYGNHYPKD-UHFFFAOYSA-N 3-[5-[(5-chloro-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC(Cl)=CC=C3NC2=O)=C1C SQISXLYGNHYPKD-UHFFFAOYSA-N 0.000 description 1
• IIWYUYODLPITHL-UHFFFAOYSA-N 3-[5-[(5-chloro-4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(C=C2C3=C(C)C(Cl)=CC=C3NC2=O)=C1C IIWYUYODLPITHL-UHFFFAOYSA-N 0.000 description 1
• LZCUBQASVPMVEA-UHFFFAOYSA-N 3-[5-[(5-chloro-4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=C(C)C(Cl)=CC=C3NC2=O)=C1C LZCUBQASVPMVEA-UHFFFAOYSA-N 0.000 description 1
• ZNOWLXVEKYCWBE-UHFFFAOYSA-N 3-[5-[(5-iodo-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC(I)=CC=C3NC2=O)=C1C ZNOWLXVEKYCWBE-UHFFFAOYSA-N 0.000 description 1
• PUFZOSHTFRHZGE-UHFFFAOYSA-N 3-[5-[(5-methoxy-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound C12=CC(OC)=CC=C2NC(=O)C1=CC=1NC=C(CCC(O)=O)C=1C PUFZOSHTFRHZGE-UHFFFAOYSA-N 0.000 description 1
• GGPNSZWDDIDANF-UHFFFAOYSA-N 3-[5-[(6-bromo-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=CNC(C=C2C3=CC=C(Br)C=C3NC2=O)=C1C GGPNSZWDDIDANF-UHFFFAOYSA-N 0.000 description 1
• FTYXAWPLQFJPBB-ZSOIEALJSA-N 3-[5-[(z)-(6-methoxy-2-oxo-1h-indol-3-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound O=C1NC2=CC(OC)=CC=C2\C1=C\C=1NC=C(CCC(O)=O)C=1C FTYXAWPLQFJPBB-ZSOIEALJSA-N 0.000 description 1
• IZKQKZYHPAYOKJ-UNOMPAQXSA-N 3-[5-[(z)-[6-(2-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(\C(=C\C2=C(C(CCC(O)=O)=CN2)C)C(=O)N2)C2=C1 IZKQKZYHPAYOKJ-UNOMPAQXSA-N 0.000 description 1
• YAHVZVQVATYZMK-NDENLUEZSA-N 3-[5-[(z)-[6-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound COC1=CC=CC(C=2C=C3NC(=O)C(=C\C4=C(C(CCC(O)=O)=CN4)C)/C3=CC=2)=C1 YAHVZVQVATYZMK-NDENLUEZSA-N 0.000 description 1
• RDIYTLWMJLEVPM-NDENLUEZSA-N 3-[5-[(z)-[6-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrol-3-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(\C(=C\C2=C(C(CCC(O)=O)=CN2)C)C(=O)N2)C2=C1 RDIYTLWMJLEVPM-NDENLUEZSA-N 0.000 description 1
• JAKZLBJBNMIQMP-UHFFFAOYSA-N 3-[5-[[6-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=CC2=C(C(CCC(O)=O)=C(C)N2)C)C(=O)N2)C2=C1 JAKZLBJBNMIQMP-UHFFFAOYSA-N 0.000 description 1
• UHKITYTXCXBLNM-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(3-morpholin-4-ylpropyl)-1h-pyrrol-2-yl]methylidene]-6-phenyl-1h-indol-2-one Chemical compound CC=1C(CCCN2CCOCC2)=C(C)NC=1C=C(C1=CC=2)C(=O)NC1=CC=2C1=CC=CC=C1 UHKITYTXCXBLNM-UHFFFAOYSA-N 0.000 description 1
• VWZUQMYAXGZACH-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methyl]-6-(3-methoxyphenyl)-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC(C=2C=C3NC(=O)C(CC4=C(C(CCCN(C)C)=C(C)N4)C)C3=CC=2)=C1 VWZUQMYAXGZACH-UHFFFAOYSA-N 0.000 description 1
• RTHKPDGJBJRDHW-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC=CC=C3NC2=O)=C1C RTHKPDGJBJRDHW-UHFFFAOYSA-N 0.000 description 1
• MUXXCDNBCFYJQY-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-4-methyl-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=C(C)C=CC=C3NC2=O)=C1C MUXXCDNBCFYJQY-UHFFFAOYSA-N 0.000 description 1
• BCMUPCKWGCURKL-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-5-methoxy-1h-indol-2-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C1=CC=1NC(C)=C(CCCN(C)C)C=1C BCMUPCKWGCURKL-UHFFFAOYSA-N 0.000 description 1
• MQGRHUQMDUWCTN-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-5-methyl-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(C)=CC=C3NC2=O)=C1C MQGRHUQMDUWCTN-UHFFFAOYSA-N 0.000 description 1
• QZNBWVZFYJHFCN-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-5-morpholin-4-ylsulfonyl-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(=CC=C3NC2=O)S(=O)(=O)N2CCOCC2)=C1C QZNBWVZFYJHFCN-UHFFFAOYSA-N 0.000 description 1
• AGYUVURRUUXGGG-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-6-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=CC2=C(C(CCCN(C)C)=C(C)N2)C)C(=O)N2)C2=C1 AGYUVURRUUXGGG-UHFFFAOYSA-N 0.000 description 1
• VTRZRDRDYBDPQL-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-6-phenyl-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC=C(C=C3NC2=O)C=2C=CC=CC=2)=C1C VTRZRDRDYBDPQL-UHFFFAOYSA-N 0.000 description 1
• HQFLTUZKIRYQSP-UHFFFAOYSA-N 3-ethyl-2h-1,3-benzothiazole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2N(CC)CSC2=C1 HQFLTUZKIRYQSP-UHFFFAOYSA-N 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• JRQDVRIQJJPHEQ-UHFFFAOYSA-N 3970-35-2 Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1Cl JRQDVRIQJJPHEQ-UHFFFAOYSA-N 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• PTNLMYKCABVKOZ-UHFFFAOYSA-N 4,5-dimethoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=C2NC(=O)CC2=C1OC PTNLMYKCABVKOZ-UHFFFAOYSA-N 0.000 description 1
• QRTHVOUKWCEPKJ-UHFFFAOYSA-N 4-(2-hydroxyethyl)-1,3-dihydroindol-2-one Chemical compound OCCC1=CC=CC2=C1CC(=O)N2 QRTHVOUKWCEPKJ-UHFFFAOYSA-N 0.000 description 1
• URUYZLLTRAUSHV-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroindol-5-yl)carbamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)NC1=CC=C(NC(=O)C2)C2=C1 URUYZLLTRAUSHV-UHFFFAOYSA-N 0.000 description 1
• ZYSKQDWGVBAZAE-UHFFFAOYSA-N 4-[2-(2-propan-2-ylphenoxy)ethyl]-1,3-dihydroindol-2-one Chemical class CC(C)C1=CC=CC=C1OCCC1=CC=CC2=C1CC(=O)N2 ZYSKQDWGVBAZAE-UHFFFAOYSA-N 0.000 description 1
• GDZVODBMOJRKRS-UHFFFAOYSA-N 4-[2-(3-propan-2-ylphenoxy)ethyl]-1,3-dihydroindol-2-one Chemical class CC(C)C1=CC=CC(OCCC=2C=3CC(=O)NC=3C=CC=2)=C1 GDZVODBMOJRKRS-UHFFFAOYSA-N 0.000 description 1
• XTEAGYUOVWCQGA-UHFFFAOYSA-N 4-[2-(4-propan-2-ylphenoxy)ethyl]-1,3-dihydroindol-2-one Chemical class C1=CC(C(C)C)=CC=C1OCCC1=CC=CC2=C1CC(=O)N2 XTEAGYUOVWCQGA-UHFFFAOYSA-N 0.000 description 1
• TVGJPIIDWGXRAG-UHFFFAOYSA-N 4-[3-(2,4-dimethyl-1h-pyrrol-3-yl)propyl]morpholine Chemical compound CC1=CNC(C)=C1CCCN1CCOCC1 TVGJPIIDWGXRAG-UHFFFAOYSA-N 0.000 description 1
• YSGWLWLRMYTFIK-UHFFFAOYSA-N 4-butanoyl-1,3-dihydroindol-2-one Chemical compound CCCC(=O)C1=CC=CC2=C1CC(=O)N2 YSGWLWLRMYTFIK-UHFFFAOYSA-N 0.000 description 1
• ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
• GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 description 1
• IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 description 1
• WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 1
• FIYRYZIFOKMBOE-UHFFFAOYSA-N 5-butanoyl-1,3-dihydroindol-2-one Chemical compound CCCC(=O)C1=CC=C2NC(=O)CC2=C1 FIYRYZIFOKMBOE-UHFFFAOYSA-N 0.000 description 1
• WESRTMMUHCBTED-UHFFFAOYSA-N 5-chloro-3-[[4-[3-(dimethylamino)propyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound CN(C)CCCC1=C(C)NC(C=C2C3=CC(Cl)=CC=C3NC2=O)=C1C WESRTMMUHCBTED-UHFFFAOYSA-N 0.000 description 1
• FYMGXBGSTYKVGE-UHFFFAOYSA-N 5-iodo-4-methyl-1,3-dihydroindol-2-one Chemical compound C1=C(I)C(C)=C2CC(=O)NC2=C1 FYMGXBGSTYKVGE-UHFFFAOYSA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
• ONVQJRUWAVVUHE-UHFFFAOYSA-N 6-[3-(2,2,2-trifluoroacetyl)phenyl]-1,3-dihydroindol-2-one Chemical compound FC(F)(F)C(=O)C1=CC=CC(C=2C=C3NC(=O)CC3=CC=2)=C1 ONVQJRUWAVVUHE-UHFFFAOYSA-N 0.000 description 1
• PHKHSQVVCIIMNR-UHFFFAOYSA-N 6-morpholin-4-yl-1,3-dihydroindol-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1N1CCOCC1 PHKHSQVVCIIMNR-UHFFFAOYSA-N 0.000 description 1
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• 108010024976 Asparaginase Proteins 0.000 description 1
• 241000182988 Assa Species 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 201000004569 Blindness Diseases 0.000 description 1
• 206010005949 Bone cancer Diseases 0.000 description 1
• 208000018084 Bone neoplasm Diseases 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
• 208000006332 Choriocarcinoma Diseases 0.000 description 1
• 206010063209 Chronic allograft nephropathy Diseases 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
• 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
• 230000006820 DNA synthesis Effects 0.000 description 1
• 108010092160 Dactinomycin Proteins 0.000 description 1
• 206010011953 Decreased activity Diseases 0.000 description 1
• 229920002307 Dextran Polymers 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
• 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
• 240000006497 Dianthus caryophyllus Species 0.000 description 1
• 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
• 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
• 101100015729 Drosophila melanogaster drk gene Proteins 0.000 description 1
• 101150029707 ERBB2 gene Proteins 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• 102100030013 Endoribonuclease Human genes 0.000 description 1
• 101710199605 Endoribonuclease Proteins 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes 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
• 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
• 108091008794 FGF receptors Proteins 0.000 description 1
• 241000287828 Gallus gallus Species 0.000 description 1
• 101000993347 Gallus gallus Ciliary neurotrophic factor Proteins 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• 108090000288 Glycoproteins Proteins 0.000 description 1
• 102000003886 Glycoproteins Human genes 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 238000010268 HPLC based assay Methods 0.000 description 1
• 239000012981 Hank's balanced salt solution Substances 0.000 description 1
• 101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• 101000808011 Homo sapiens Vascular endothelial growth factor A Proteins 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102000048143 Insulin-Like Growth Factor II Human genes 0.000 description 1
• 108090001117 Insulin-Like Growth Factor II Proteins 0.000 description 1
• 102100037852 Insulin-like growth factor I Human genes 0.000 description 1
• 239000005909 Kieselgur Substances 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
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 108010058398 Macrophage Colony-Stimulating Factor Receptor Proteins 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 102000018697 Membrane Proteins Human genes 0.000 description 1
• 108010052285 Membrane Proteins Proteins 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• 208000034578 Multiple myelomas Diseases 0.000 description 1
• 101000808007 Mus musculus Vascular endothelial growth factor A Proteins 0.000 description 1
• 101000851005 Mus musculus Vascular endothelial growth factor receptor 2 Proteins 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 208000007727 Muscle Tissue Neoplasms Diseases 0.000 description 1
• 241000204031 Mycoplasma Species 0.000 description 1
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
• MKBYLRYHZMDKGY-UHFFFAOYSA-N N[N+](C([O-])=O)(C#N)[N+]([O-])=O Chemical compound N[N+](C([O-])=O)(C#N)[N+]([O-])=O MKBYLRYHZMDKGY-UHFFFAOYSA-N 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 208000022873 Ocular disease Diseases 0.000 description 1
• 108700020796 Oncogene Proteins 0.000 description 1
• 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 102000016979 Other receptors Human genes 0.000 description 1
• 101150038994 PDGFRA gene Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 208000034038 Pathologic Neovascularization Diseases 0.000 description 1
• 102000004422 Phospholipase C gamma Human genes 0.000 description 1
• 108010056751 Phospholipase C gamma Proteins 0.000 description 1
• 108010064785 Phospholipases Proteins 0.000 description 1
• 102000015439 Phospholipases Human genes 0.000 description 1
• 206010035226 Plasma cell myeloma Diseases 0.000 description 1
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 1
• 102000001393 Platelet-Derived Growth Factor alpha Receptor Human genes 0.000 description 1
• 108010068588 Platelet-Derived Growth Factor alpha Receptor Proteins 0.000 description 1
• 229920001213 Polysorbate 20 Polymers 0.000 description 1
• 239000004793 Polystyrene Substances 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
• 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
• 102000003901 Ras GTPase-activating proteins Human genes 0.000 description 1
• 108090000231 Ras GTPase-activating proteins Proteins 0.000 description 1
• 108091005682 Receptor kinases Proteins 0.000 description 1
• 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 208000021712 Soft tissue sarcoma Diseases 0.000 description 1
• 229920002125 Sokalan® Polymers 0.000 description 1
• 240000006394 Sorghum bicolor Species 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
• PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
• 239000004473 Threonine Substances 0.000 description 1
• 208000007536 Thrombosis Diseases 0.000 description 1
• 208000034841 Thrombotic Microangiopathies Diseases 0.000 description 1
• IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 1
• 208000033781 Thyroid carcinoma Diseases 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010052779 Transplant rejections Diseases 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
• GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 238000005411 Van der Waals force Methods 0.000 description 1
• 108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 1
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 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
• 208000036142 Viral infection Diseases 0.000 description 1
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
• 208000008383 Wilms tumor Diseases 0.000 description 1
• FMSRMLMJROGIGA-UHFFFAOYSA-N [Na].CC=1C(=CNC1C=C1C(NC2=CC=CC=C12)=O)CCC(=O)O Chemical compound [Na].CC=1C(=CNC1C=C1C(NC2=CC=CC=C12)=O)CCC(=O)O FMSRMLMJROGIGA-UHFFFAOYSA-N 0.000 description 1
• USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
• AIRISBCKFSLMOW-UHFFFAOYSA-N acetic acid;1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound CC(O)=O.C1=CN=C2NC(=O)CC2=C1 AIRISBCKFSLMOW-UHFFFAOYSA-N 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
• 230000006978 adaptation Effects 0.000 description 1
• GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
• 210000001789 adipocyte Anatomy 0.000 description 1
• 230000001780 adrenocortical effect Effects 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 235000010419 agar Nutrition 0.000 description 1
• 229940040563 agaric acid Drugs 0.000 description 1
• 206010064930 age-related macular degeneration Diseases 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 229960000473 altretamine Drugs 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 125000000539 amino acid group Chemical group 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229960003437 aminoglutethimide Drugs 0.000 description 1
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 230000003321 amplification Effects 0.000 description 1
• 229960002932 anastrozole Drugs 0.000 description 1
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
• 239000003098 androgen Substances 0.000 description 1
• 229940030486 androgens Drugs 0.000 description 1
• 230000001656 angiogenetic effect Effects 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 description 1
• 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
• 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 1
• 150000001541 aziridines Chemical class 0.000 description 1
• 229910052788 barium Inorganic materials 0.000 description 1
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 208000021592 benign granular cell tumor Diseases 0.000 description 1
• ZIQCCIAIROIHHR-UHFFFAOYSA-N benzene;boric acid Chemical compound OB(O)O.C1=CC=CC=C1 ZIQCCIAIROIHHR-UHFFFAOYSA-N 0.000 description 1
• 229950005567 benzodepa Drugs 0.000 description 1
• VFIUCBTYGKMLCM-UHFFFAOYSA-N benzyl n-[bis(aziridin-1-yl)phosphoryl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NP(=O)(N1CC1)N1CC1 VFIUCBTYGKMLCM-UHFFFAOYSA-N 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 238000012925 biological evaluation Methods 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000001851 biosynthetic effect Effects 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
• 210000001185 bone marrow Anatomy 0.000 description 1
• 201000008275 breast carcinoma Diseases 0.000 description 1
• 229960002092 busulfan Drugs 0.000 description 1
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 239000006229 carbon black Substances 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 210000000845 cartilage Anatomy 0.000 description 1
• 208000015100 cartilage disease Diseases 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 238000000423 cell based assay Methods 0.000 description 1
• 239000006143 cell culture medium Substances 0.000 description 1
• 230000012292 cell migration Effects 0.000 description 1
• 230000019522 cellular metabolic process Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 210000003679 cervix uteri Anatomy 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
• 210000001612 chondrocyte Anatomy 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 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
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
• 239000003245 coal Substances 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 201000010989 colorectal carcinoma Diseases 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 230000006552 constitutive activation Effects 0.000 description 1
• 238000011109 contamination Methods 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 229940099112 cornstarch Drugs 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 230000009089 cytolysis Effects 0.000 description 1
• 210000000805 cytoplasm Anatomy 0.000 description 1
• 210000004292 cytoskeleton Anatomy 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• 208000033679 diabetic kidney disease Diseases 0.000 description 1
• KPUNOVLMCQQCSK-UHFFFAOYSA-N diazomethane;ethoxyethane Chemical compound C=[N+]=[N-].CCOCC KPUNOVLMCQQCSK-UHFFFAOYSA-N 0.000 description 1
• 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
• 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
• 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
• 150000005690 diesters Chemical class 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 239000000539 dimer Substances 0.000 description 1
• MBAQGFLNQDHQCE-UHFFFAOYSA-N dimethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O MBAQGFLNQDHQCE-UHFFFAOYSA-N 0.000 description 1
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
• 230000006806 disease prevention Effects 0.000 description 1
• 208000037765 diseases and disorders Diseases 0.000 description 1
• 229910000397 disodium phosphate Inorganic materials 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 238000001548 drop coating Methods 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000002888 effect on disease Effects 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940079360 enema for constipation Drugs 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 210000002919 epithelial cell Anatomy 0.000 description 1
• 230000008472 epithelial growth Effects 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 229960001842 estramustine Drugs 0.000 description 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 239000000328 estrogen antagonist Substances 0.000 description 1
• ZYNJVGCLOFPWFZ-UHFFFAOYSA-N ethyl 4-(3-ethoxy-3-oxopropyl)-3,5-dimethyl-1h-pyrrole-2-carboxylate Chemical compound CCOC(=O)CCC1=C(C)NC(C(=O)OCC)=C1C ZYNJVGCLOFPWFZ-UHFFFAOYSA-N 0.000 description 1
• GDISALBEIGGPER-UHFFFAOYSA-N ethyl 5-formyl-2,4-dimethyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=O)=C1C GDISALBEIGGPER-UHFFFAOYSA-N 0.000 description 1
• XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 229960005420 etoposide Drugs 0.000 description 1
• 210000003527 eukaryotic cell Anatomy 0.000 description 1
• 208000030533 eye disease Diseases 0.000 description 1
• 235000013861 fat-free Nutrition 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 description 1
• 238000005187 foaming Methods 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• 150000002224 folic acids Chemical class 0.000 description 1
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 208000010749 gastric carcinoma Diseases 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 210000003714 granulocyte Anatomy 0.000 description 1
• 101150098203 grb2 gene Proteins 0.000 description 1
• 208000037824 growth disorder Diseases 0.000 description 1
• 239000003324 growth hormone secretagogue Substances 0.000 description 1
• 238000003306 harvesting Methods 0.000 description 1
• 201000005787 hematologic cancer Diseases 0.000 description 1
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
• 230000023597 hemostasis Effects 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• 125000001072 heteroaryl group Chemical group 0.000 description 1
• UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
• 231100000171 higher toxicity Toxicity 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 239000003667 hormone antagonist Substances 0.000 description 1
• 102000058223 human VEGFA Human genes 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 229920001600 hydrophobic polymer Polymers 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 229960002899 hydroxyprogesterone 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
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
• 230000000521 hyperimmunizing effect Effects 0.000 description 1
• 229960001101 ifosfamide Drugs 0.000 description 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 238000002513 implantation Methods 0.000 description 1
• DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
• 229950008097 improsulfan Drugs 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000007914 intraventricular administration Methods 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
• 150000002605 large molecules Chemical class 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• 108020001756 ligand binding domains Proteins 0.000 description 1
• 229940057995 liquid paraffin Drugs 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005296 lung carcinoma Diseases 0.000 description 1
• 208000037841 lung tumor Diseases 0.000 description 1
• 238000012792 lyophilization process Methods 0.000 description 1
• 239000012139 lysis buffer Substances 0.000 description 1
• JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
• 229920002521 macromolecule Polymers 0.000 description 1
• 208000002780 macular degeneration Diseases 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 230000014759 maintenance of location Effects 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
• 230000036210 malignancy Effects 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 206010027191 meningioma Diseases 0.000 description 1
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• XLKMOMJQAMBSRB-UHFFFAOYSA-N methyl 3-[1-[(3-fluorophenyl)methyl]-5-formyl-2,4-dimethylpyrrol-3-yl]propanoate Chemical compound CC1=C(CCC(=O)OC)C(C)=C(C=O)N1CC1=CC=CC(F)=C1 XLKMOMJQAMBSRB-UHFFFAOYSA-N 0.000 description 1
• CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• QTFKTBRIGWJQQL-UHFFFAOYSA-N meturedepa Chemical compound C1C(C)(C)N1P(=O)(NC(=O)OCC)N1CC1(C)C QTFKTBRIGWJQQL-UHFFFAOYSA-N 0.000 description 1
• 229950009847 meturedepa Drugs 0.000 description 1
• 238000000520 microinjection Methods 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 235000013336 milk Nutrition 0.000 description 1
• 239000008267 milk Substances 0.000 description 1
• 210000004080 milk Anatomy 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 230000011278 mitosis Effects 0.000 description 1
• 229960000350 mitotane Drugs 0.000 description 1
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
• 229960001156 mitoxantrone Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 238000012544 monitoring process Methods 0.000 description 1
• HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical class CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 201000005962 mycosis fungoides Diseases 0.000 description 1
• 210000000066 myeloid cell Anatomy 0.000 description 1
• 201000004130 myoblastoma Diseases 0.000 description 1
• SBULNBMWGLBIMA-UHFFFAOYSA-N n,n-dimethyl-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C2NC(=O)CC2=C1 SBULNBMWGLBIMA-UHFFFAOYSA-N 0.000 description 1
• WJBXUAIGXKXYLO-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(5-formyl-1,2,4-trimethylpyrrol-3-yl)propanamide Chemical compound CN1C(C=O)=C(C)C(CCC(=O)NC=2C=CC(F)=CC=2)=C1C WJBXUAIGXKXYLO-UHFFFAOYSA-N 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 239000006225 natural substrate Substances 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 230000014399 negative regulation of angiogenesis Effects 0.000 description 1
• 230000009826 neoplastic cell growth Effects 0.000 description 1
• 201000009925 nephrosclerosis Diseases 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 230000004770 neurodegeneration Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 101150009274 nhr-1 gene Proteins 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 238000003199 nucleic acid amplification method Methods 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• 235000021231 nutrient uptake Nutrition 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 229940078552 o-xylene Drugs 0.000 description 1
• 231100000590 oncogenic Toxicity 0.000 description 1
• 230000002246 oncogenic effect Effects 0.000 description 1
• 102000027450 oncoproteins Human genes 0.000 description 1
• 108091008819 oncoproteins Proteins 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 210000003463 organelle Anatomy 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 125000001477 organic nitrogen group Chemical group 0.000 description 1
• 229920000620 organic polymer Polymers 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 210000000963 osteoblast Anatomy 0.000 description 1
• 210000002997 osteoclast Anatomy 0.000 description 1
• 230000002642 osteogeneic effect Effects 0.000 description 1
• 229940045681 other alkylating agent in atc Drugs 0.000 description 1
• 229940127075 other antimetabolite Drugs 0.000 description 1
• 230000016087 ovulation Effects 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 238000012856 packing Methods 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• 230000000149 penetrating effect Effects 0.000 description 1
• 229940127557 pharmaceutical product Drugs 0.000 description 1
• 238000001050 pharmacotherapy Methods 0.000 description 1
• 235000021317 phosphate Nutrition 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• DCWXELXMIBXGTH-QMMMGPOBSA-N phosphonotyrosine Chemical group OC(=O)[C@@H](N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-QMMMGPOBSA-N 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 239000002504 physiological saline solution Substances 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 1
• 229950001100 piposulfan Drugs 0.000 description 1
• 230000003169 placental effect Effects 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 150000004804 polysaccharides Chemical class 0.000 description 1
• 229920002223 polystyrene Polymers 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 229940116317 potato starch Drugs 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 1
• 230000035935 pregnancy Effects 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 239000000583 progesterone congener Substances 0.000 description 1
• 230000009696 proliferative response Effects 0.000 description 1
• XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
• 229940080818 propionamide Drugs 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 201000001514 prostate carcinoma Diseases 0.000 description 1
• 230000029983 protein stabilization Effects 0.000 description 1
• WOLQREOUPKZMEX-UHFFFAOYSA-N pteroyltriglutamic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C=C1 WOLQREOUPKZMEX-UHFFFAOYSA-N 0.000 description 1
• 238000010298 pulverizing process Methods 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000004076 pyridyl group Chemical class 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical class O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
• 150000003233 pyrroles Chemical class 0.000 description 1
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 102000016914 ras Proteins Human genes 0.000 description 1
• 230000027272 reproductive process Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000002207 retinal effect Effects 0.000 description 1
• 210000003705 ribosome Anatomy 0.000 description 1
• 229940100486 rice starch Drugs 0.000 description 1
• 229950000366 roxindole Drugs 0.000 description 1
• 238000007790 scraping Methods 0.000 description 1
• 150000003346 selenoethers Chemical class 0.000 description 1
• 239000012679 serum free medium Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 230000007480 spreading Effects 0.000 description 1
• 238000003892 spreading Methods 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 239000001119 stannous chloride Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 201000000498 stomach carcinoma Diseases 0.000 description 1
• 125000005504 styryl group Chemical group 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 238000000967 suction filtration Methods 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 230000008685 targeting Effects 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 238000003419 tautomerization reaction Methods 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
• 229960004964 temozolomide 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
• 240000003177 tenweeks stock Species 0.000 description 1
• JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
• 229960001712 testosterone propionate Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
• 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• 210000001685 thyroid gland Anatomy 0.000 description 1
• 208000013077 thyroid gland carcinoma Diseases 0.000 description 1
• MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
• 229960003087 tioguanine Drugs 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 102000027257 transmembrane receptors Human genes 0.000 description 1
• 108091008578 transmembrane receptors Proteins 0.000 description 1
• IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
• 229950001353 tretamine Drugs 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 150000003918 triazines Chemical class 0.000 description 1
• 229940029284 trichlorofluoromethane Drugs 0.000 description 1
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 230000005748 tumor development Effects 0.000 description 1
• 230000005740 tumor formation Effects 0.000 description 1
• JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
• 229960001055 uracil mustard Drugs 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
• 229950006929 uredepa Drugs 0.000 description 1
• 210000003932 urinary bladder Anatomy 0.000 description 1
• 239000002966 varnish Substances 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
• 239000003981 vehicle Substances 0.000 description 1
• 230000007998 vessel formation Effects 0.000 description 1
• 230000035899 viability Effects 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
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• HHJUWIANJFBDHT-KOTLKJBCSA-N vindesine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(N)=O)N4C)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 HHJUWIANJFBDHT-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 229940100445 wheat starch Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1