HRP20041173A2 - Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use - Google Patents

Info

Publication number

HRP20041173A2

HRP20041173A2 HR20041173A HRP20041173A HRP20041173A2 HR P20041173 A2 HRP20041173 A2 HR P20041173A2 HR 20041173 A HR20041173 A HR 20041173A HR P20041173 A HRP20041173 A HR P20041173A HR P20041173 A2 HRP20041173 A2 HR P20041173A2

Authority

HR

Croatia

Prior art keywords

mmol

image

alkyl

aryl

carboxylic acid

Prior art date

2002-06-14

Links

• Espacenet
• Global Dossier
• Discuss

• -1 heteroaryl amide Chemical class 0.000 title claims description 123
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 12
• 238000000034 method Methods 0.000 title description 46
• 239000003814 drug Substances 0.000 title description 10
• 229940124597 therapeutic agent Drugs 0.000 title description 2
• 229940125670 thienopyridine Drugs 0.000 title description 2
• 239000002175 thienopyridine Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 210
• 238000011282 treatment Methods 0.000 claims description 81
• 150000003839 salts Chemical class 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 68
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
• 239000012453 solvate Substances 0.000 claims description 37
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 35
• 241000124008 Mammalia Species 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 21
• 201000011510 cancer Diseases 0.000 claims description 19
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 16
• 208000035475 disorder Diseases 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• 230000003463 hyperproliferative effect Effects 0.000 claims description 13
• 125000002757 morpholinyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
• 230000033115 angiogenesis Effects 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 9
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000004069 aziridinyl group Chemical group 0.000 claims description 9
• 210000000481 breast Anatomy 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 210000002307 prostate Anatomy 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 210000004072 lung Anatomy 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 230000004862 vasculogenesis Effects 0.000 claims description 8
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 7
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
• 210000001072 colon Anatomy 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 210000000496 pancreas Anatomy 0.000 claims description 6
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• 208000032612 Glial tumor Diseases 0.000 claims description 5
• 206010018338 Glioma Diseases 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 229940030600 antihypertensive agent Drugs 0.000 claims description 5
• 239000002220 antihypertensive agent Substances 0.000 claims description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 201000011066 hemangioma Diseases 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 208000017442 Retinal disease Diseases 0.000 claims description 4
• 206010038923 Retinopathy Diseases 0.000 claims description 4
• 230000032683 aging Effects 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
• 208000017520 skin disease Diseases 0.000 claims description 4
• 230000005747 tumor angiogenesis Effects 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 230000000366 juvenile effect Effects 0.000 claims 3
• 201000001514 prostate carcinoma Diseases 0.000 claims 3
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 294
• 238000005160 1H NMR spectroscopy Methods 0.000 description 285
• 239000000463 material Substances 0.000 description 216
• 239000007787 solid Substances 0.000 description 204
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 199
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 144
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 131
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 124
• 238000006243 chemical reaction Methods 0.000 description 122
• 239000000243 solution Substances 0.000 description 117
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 106
• 239000000203 mixture Substances 0.000 description 102
• 229910000024 caesium carbonate Inorganic materials 0.000 description 101
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 75
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
• 239000000651 prodrug Substances 0.000 description 67
• 229940002612 prodrug Drugs 0.000 description 67
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
• 239000011541 reaction mixture Substances 0.000 description 63
• 235000019439 ethyl acetate Nutrition 0.000 description 62
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 60
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 58
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 239000003795 chemical substances by application Substances 0.000 description 40
• 210000004027 cell Anatomy 0.000 description 35
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• 238000012360 testing method Methods 0.000 description 34
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• 239000012044 organic layer Substances 0.000 description 31
• 229910015845 BBr3 Inorganic materials 0.000 description 29
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
• 235000019341 magnesium sulphate Nutrition 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• 239000010410 layer Substances 0.000 description 25
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 24
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• RQNYQQDHUOLGQZ-UHFFFAOYSA-N 6-hydroxy-n,1,2-trimethylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C)N(C)C2=C1 RQNYQQDHUOLGQZ-UHFFFAOYSA-N 0.000 description 23
• 239000007832 Na2SO4 Substances 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 238000003818 flash chromatography Methods 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 21
• 239000000741 silica gel Substances 0.000 description 21
• 229910002027 silica gel Inorganic materials 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 20
• 230000002159 abnormal effect Effects 0.000 description 20
• 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 20
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 19
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 19
• 239000003112 inhibitor Substances 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 18
• LJYQFQKUXOCPNI-UHFFFAOYSA-N 7-chloro-2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridine Chemical compound CN1C=CN=C1C1=CC2=NC=CC(Cl)=C2S1 LJYQFQKUXOCPNI-UHFFFAOYSA-N 0.000 description 17
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 17
• WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 17
• 239000002609 medium Substances 0.000 description 17
• 239000002207 metabolite Substances 0.000 description 17
• 239000000284 extract Substances 0.000 description 16
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
• 230000010261 cell growth Effects 0.000 description 15
• RXKGVJSYESLRAK-MRVPVSSYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3r)-3-methoxypyrrolidin-1-yl]methanone Chemical compound C1[C@H](OC)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 RXKGVJSYESLRAK-MRVPVSSYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 230000002401 inhibitory effect Effects 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 230000000694 effects Effects 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 238000004809 thin layer chromatography Methods 0.000 description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• 238000004587 chromatography analysis Methods 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 239000013543 active substance Substances 0.000 description 11
• 238000003556 assay Methods 0.000 description 11
• 238000009833 condensation Methods 0.000 description 11
• 230000005494 condensation Effects 0.000 description 11
• 235000003642 hunger Nutrition 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 230000037351 starvation Effects 0.000 description 11
• IZNKTHMRXJRKFB-UHFFFAOYSA-N 6-methoxy-1,2-dimethylindole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=C(C)N(C)C2=C1 IZNKTHMRXJRKFB-UHFFFAOYSA-N 0.000 description 10
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
• 108091000080 Phosphotransferase Proteins 0.000 description 10
• 102000020233 phosphotransferase Human genes 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
• LNSDBFHIMSCIQB-SSDOTTSWSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3r)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound C1[C@H](O)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 LNSDBFHIMSCIQB-SSDOTTSWSA-N 0.000 description 9
• AVZZCZSFTGUOPZ-UHFFFAOYSA-N 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxylic acid Chemical compound C=1C=C2C(C(O)=O)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 AVZZCZSFTGUOPZ-UHFFFAOYSA-N 0.000 description 9
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 9
• 102000001301 EGF receptor Human genes 0.000 description 9
• 108060006698 EGF receptor Proteins 0.000 description 9
• 102000004190 Enzymes Human genes 0.000 description 9
• 108090000790 Enzymes Proteins 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 9
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 9
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 9
• 230000010933 acylation Effects 0.000 description 9
• 238000005917 acylation reaction Methods 0.000 description 9
• 150000001412 amines Chemical group 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• GIJGJGRRRASIPR-UHFFFAOYSA-N azetidin-1-yl-(7-chlorothieno[3,2-b]pyridin-2-yl)methanone Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C(=O)N1CCC1 GIJGJGRRRASIPR-UHFFFAOYSA-N 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 239000006184 cosolvent Substances 0.000 description 9
• IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 9
• 238000010828 elution Methods 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 239000012091 fetal bovine serum Substances 0.000 description 9
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 9
• 239000003981 vehicle Substances 0.000 description 9
• MTMHBQNHFZUJPE-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-trimethylstannane Chemical compound C1=CC(Cl)=C2SC([Sn](C)(C)C)=CC2=N1 MTMHBQNHFZUJPE-UHFFFAOYSA-N 0.000 description 8
• OACQHLMJJRQAPO-UHFFFAOYSA-N 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CC(Cl)=C2SC(C(=O)O)=CC2=N1 OACQHLMJJRQAPO-UHFFFAOYSA-N 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 239000012230 colorless oil Substances 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 239000007924 injection Substances 0.000 description 8
• 238000002347 injection Methods 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 8
• 125000006413 ring segment Chemical group 0.000 description 8
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 8
• IXXYDEFBBIUGNN-UHFFFAOYSA-N 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carbonyl chloride Chemical compound C=1C=C2C(C(Cl)=O)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 IXXYDEFBBIUGNN-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 102000001253 Protein Kinase Human genes 0.000 description 7
• 239000008346 aqueous phase Substances 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 239000003102 growth factor Substances 0.000 description 7
• XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
• PJOJKBUEADULSE-UHFFFAOYSA-M lithium;7-chlorothieno[3,2-b]pyridine-2-carboxylate Chemical compound [Li+].C1=CC(Cl)=C2SC(C(=O)[O-])=CC2=N1 PJOJKBUEADULSE-UHFFFAOYSA-M 0.000 description 7
• 230000003211 malignant effect Effects 0.000 description 7
• VXGPRUODUDSSME-UHFFFAOYSA-N methyl 6-hydroxy-2-methyl-1-benzothiophene-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=C(C)SC2=C1 VXGPRUODUDSSME-UHFFFAOYSA-N 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 108060006633 protein kinase Proteins 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
• GNCACOWVHHUSQD-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzofuran-3-carboxylic acid Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(O)=O)C4=CC=3)=C2S1 GNCACOWVHHUSQD-UHFFFAOYSA-N 0.000 description 6
• XPQBBKHYAXUBIC-CQSZACIVSA-N 6-[2-[(3r)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylic acid Chemical compound C1[C@H](OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4SC(C)=C(C(O)=O)C4=CC=3)=C2S1 XPQBBKHYAXUBIC-CQSZACIVSA-N 0.000 description 6
• STJUIIXFIQVGML-UHFFFAOYSA-N 7-chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=NC=CS1 STJUIIXFIQVGML-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 6
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 6
• 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 6
• 229910006124 SOCl2 Inorganic materials 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 230000035578 autophosphorylation Effects 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000008298 dragée Substances 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 238000011534 incubation Methods 0.000 description 6
• 230000005764 inhibitory process Effects 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 239000010802 sludge Substances 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 239000000758 substrate Substances 0.000 description 6
• 239000006188 syrup Substances 0.000 description 6
• 235000020357 syrup Nutrition 0.000 description 6
• JVELFLPOFDICQP-UHFFFAOYSA-N 6-hydroxy-2-methyl-1-benzofuran-3-carboxylic acid Chemical compound OC1=CC=C2C(C(O)=O)=C(C)OC2=C1 JVELFLPOFDICQP-UHFFFAOYSA-N 0.000 description 5
• NUAOQCHBPXUPID-UHFFFAOYSA-N 6-hydroxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C)OC2=C1 NUAOQCHBPXUPID-UHFFFAOYSA-N 0.000 description 5
• QKINARAKCBGGSY-UHFFFAOYSA-N 6-methoxy-1-methylindole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=CN(C)C2=C1 QKINARAKCBGGSY-UHFFFAOYSA-N 0.000 description 5
• AHAVOXPDABUPJT-UHFFFAOYSA-N 6-methoxy-2-methyl-1-benzofuran Chemical compound COC1=CC=C2C=C(C)OC2=C1 AHAVOXPDABUPJT-UHFFFAOYSA-N 0.000 description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• 108010010803 Gelatin Proteins 0.000 description 5
• 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 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 5
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
• 201000004681 Psoriasis Diseases 0.000 description 5
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 5
• ZVSQDIBBODASJX-UHFFFAOYSA-N [2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazol-4-yl]methanol Chemical compound OCC1=CSC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 ZVSQDIBBODASJX-UHFFFAOYSA-N 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 235000001014 amino acid Nutrition 0.000 description 5
• 235000011114 ammonium hydroxide Nutrition 0.000 description 5
• 238000004458 analytical method Methods 0.000 description 5
• 230000001028 anti-proliverative effect Effects 0.000 description 5
• 239000002246 antineoplastic agent Substances 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 230000004663 cell proliferation Effects 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 210000001508 eye Anatomy 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 239000006260 foam Substances 0.000 description 5
• 239000008273 gelatin Substances 0.000 description 5
• 229920000159 gelatin Polymers 0.000 description 5
• 229940014259 gelatin Drugs 0.000 description 5
• 235000019322 gelatine Nutrition 0.000 description 5
• 235000011852 gelatine desserts Nutrition 0.000 description 5
• 239000011521 glass Substances 0.000 description 5
• 230000012010 growth Effects 0.000 description 5
• 239000001963 growth medium Substances 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 230000002209 hydrophobic effect Effects 0.000 description 5
• 239000008101 lactose Substances 0.000 description 5
• 239000002480 mineral oil Substances 0.000 description 5
• 235000010446 mineral oil Nutrition 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 210000003739 neck Anatomy 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 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
• 235000018102 proteins Nutrition 0.000 description 5
• 102000004169 proteins and genes Human genes 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 5
• JZVXCSRSYPZURP-VIFPVBQESA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 JZVXCSRSYPZURP-VIFPVBQESA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• ZQKMJXFOTPREDJ-UHFFFAOYSA-N 2-[2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazol-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CSC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 ZQKMJXFOTPREDJ-UHFFFAOYSA-N 0.000 description 4
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
• WWPQDLIBXNJNPT-UHFFFAOYSA-N 2-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxylic acid Chemical compound C=1C=C2C(C(O)=O)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C WWPQDLIBXNJNPT-UHFFFAOYSA-N 0.000 description 4
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
• AXISSHQKGFHKRO-UHFFFAOYSA-N 6-methoxy-2-methyl-1-benzothiophene Chemical compound COC1=CC=C2C=C(C)SC2=C1 AXISSHQKGFHKRO-UHFFFAOYSA-N 0.000 description 4
• RJPAVFGIMBUXEF-UHFFFAOYSA-N 6-methoxy-n,1-dimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=CN(C)C2=C1 RJPAVFGIMBUXEF-UHFFFAOYSA-N 0.000 description 4
• GYQUXKQLCNFKQT-UHFFFAOYSA-N 7-chlorothieno[3,2-b]pyridine Chemical compound ClC1=CC=NC2=C1SC=C2 GYQUXKQLCNFKQT-UHFFFAOYSA-N 0.000 description 4
• 102100026802 72 kDa type IV collagenase Human genes 0.000 description 4
• ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 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
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 4
• 102400001368 Epidermal growth factor Human genes 0.000 description 4
• 101800003838 Epidermal growth factor Proteins 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 4
• 102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 4
• 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 4
• 229910020700 Na3VO4 Inorganic materials 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 239000002202 Polyethylene glycol Substances 0.000 description 4
• WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 4
• 102000013009 Pyruvate Kinase Human genes 0.000 description 4
• 108020005115 Pyruvate Kinase Proteins 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 description 4
• WZVNWUSFJDAZIO-ZDUSSCGKSA-N [(2s)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-1-yl]-(7-chlorothieno[3,2-b]pyridin-2-yl)methanone Chemical compound CC(C)(C)[Si](C)(C)OC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 WZVNWUSFJDAZIO-ZDUSSCGKSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 150000001413 amino acids Chemical class 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 229940127089 cytotoxic agent Drugs 0.000 description 4
• VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 4
• 239000003937 drug carrier Substances 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 229940116977 epidermal growth factor Drugs 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 239000007903 gelatin capsule Substances 0.000 description 4
• 125000005842 heteroatom Chemical group 0.000 description 4
• 150000002431 hydrogen Chemical class 0.000 description 4
• WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
• 208000017169 kidney disease Diseases 0.000 description 4
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• 229910003002 lithium salt Inorganic materials 0.000 description 4
• 159000000002 lithium salts Chemical class 0.000 description 4
• 229910001629 magnesium chloride Inorganic materials 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• KTZLKQDMVFYBJI-OAHLLOKOSA-N methyl 6-[2-[(3r)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylate Chemical compound C1[C@H](OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4SC(C)=C(C(=O)OC)C4=CC=3)=C2S1 KTZLKQDMVFYBJI-OAHLLOKOSA-N 0.000 description 4
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 4
• 230000026731 phosphorylation Effects 0.000 description 4
• 238000006366 phosphorylation reaction Methods 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000012545 processing Methods 0.000 description 4
• 230000035755 proliferation Effects 0.000 description 4
• 102000005962 receptors Human genes 0.000 description 4
• 108020003175 receptors Proteins 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• 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 4
• IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 4
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 4
• 239000002525 vasculotropin inhibitor Substances 0.000 description 4
• DYFQHTIPBXYCJO-UHFFFAOYSA-N (2-methyl-1-benzothiophen-6-yl) acetate Chemical compound CC(=O)OC1=CC=C2C=C(C)SC2=C1 DYFQHTIPBXYCJO-UHFFFAOYSA-N 0.000 description 3
• UUCKNXORXAJSNF-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-(3-hydroxyazetidin-1-yl)methanone Chemical compound C1C(O)CN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 UUCKNXORXAJSNF-UHFFFAOYSA-N 0.000 description 3
• JZVXCSRSYPZURP-SECBINFHSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@H]1CCCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 JZVXCSRSYPZURP-SECBINFHSA-N 0.000 description 3
• OKCMGTGQOJQMOW-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-pyrrolidin-1-ylmethanone Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C(=O)N1CCCC1 OKCMGTGQOJQMOW-UHFFFAOYSA-N 0.000 description 3
• SLHSIMWMMUCNQI-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)methanol Chemical compound C1=CC(Cl)=C2SC(CO)=CC2=N1 SLHSIMWMMUCNQI-UHFFFAOYSA-N 0.000 description 3
• IUKZBTYADSHFFL-UHFFFAOYSA-N 1-(7-chlorothieno[3,2-b]pyridin-2-yl)propan-1-one Chemical compound C1=CC(Cl)=C2SC(C(=O)CC)=CC2=N1 IUKZBTYADSHFFL-UHFFFAOYSA-N 0.000 description 3
• MMAJXKGUZYDTHV-UHFFFAOYSA-N 1-benzhydrylazetidin-3-ol Chemical compound C1C(O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MMAJXKGUZYDTHV-UHFFFAOYSA-N 0.000 description 3
• LFRFVBLYYIOVFP-UHFFFAOYSA-N 2-ethyl-1-benzothiophen-6-ol Chemical compound C1=C(O)C=C2SC(CC)=CC2=C1 LFRFVBLYYIOVFP-UHFFFAOYSA-N 0.000 description 3
• IXPLAJKKEWRHEM-UHFFFAOYSA-N 2-ethyl-6-hydroxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(CC)OC2=C1 IXPLAJKKEWRHEM-UHFFFAOYSA-N 0.000 description 3
• UEKVFLARUBVPKA-UHFFFAOYSA-N 2-iodo-5-methoxyphenol Chemical compound COC1=CC=C(I)C(O)=C1 UEKVFLARUBVPKA-UHFFFAOYSA-N 0.000 description 3
• BZVDECJPSBQGSG-UHFFFAOYSA-N 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yl)oxy-1-benzothiophene-3-carbonyl chloride Chemical compound C1=C2C(C(Cl)=O)=C(C)SC2=CC(OC=2C=CN=C3C=C(SC3=2)C)=C1 BZVDECJPSBQGSG-UHFFFAOYSA-N 0.000 description 3
• UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 3
• MSQMPJBCTXMTTC-UHFFFAOYSA-N 6-[2-[4-(hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylic acid Chemical class C=1C=C2C(C(O)=O)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC(CO)=CS1 MSQMPJBCTXMTTC-UHFFFAOYSA-N 0.000 description 3
• WGDVDMKNSDCNGB-UHFFFAOYSA-N 6-methoxy-1-benzothiophene Chemical compound COC1=CC=C2C=CSC2=C1 WGDVDMKNSDCNGB-UHFFFAOYSA-N 0.000 description 3
• GYHAKTKQWPBADS-UHFFFAOYSA-N 7-chloro-2-iodothieno[3,2-b]pyridine Chemical compound ClC1=CC=NC2=C1SC(I)=C2 GYHAKTKQWPBADS-UHFFFAOYSA-N 0.000 description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 206010006187 Breast cancer Diseases 0.000 description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
• 239000007995 HEPES buffer Substances 0.000 description 3
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 3
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 3
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 3
• 108700020796 Oncogene Proteins 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 description 3
• 230000001594 aberrant effect Effects 0.000 description 3
• 238000002835 absorbance Methods 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 150000001263 acyl chlorides Chemical class 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 125000000539 amino acid group Chemical group 0.000 description 3
• 239000000908 ammonium hydroxide Substances 0.000 description 3
• 239000004037 angiogenesis inhibitor Substances 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 229940121647 egfr inhibitor Drugs 0.000 description 3
• 210000002889 endothelial cell Anatomy 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 210000003128 head Anatomy 0.000 description 3
• 150000007529 inorganic bases Chemical class 0.000 description 3
• 239000011630 iodine Substances 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 210000003734 kidney Anatomy 0.000 description 3
• 210000001853 liver microsome Anatomy 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• FTAUMDMYOZCRMM-UHFFFAOYSA-N n-cyclopropyl-6-hydroxy-2-methyl-1-benzothiophene-3-carboxamide Chemical compound CC=1SC2=CC(O)=CC=C2C=1C(=O)NC1CC1 FTAUMDMYOZCRMM-UHFFFAOYSA-N 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 230000002611 ovarian Effects 0.000 description 3
• 235000021317 phosphate Nutrition 0.000 description 3
• 239000002953 phosphate buffered saline Substances 0.000 description 3
• DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 description 3
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
• 229920000053 polysorbate 80 Polymers 0.000 description 3
• 229940068968 polysorbate 80 Drugs 0.000 description 3
• 230000002062 proliferating effect Effects 0.000 description 3
• 230000005855 radiation Effects 0.000 description 3
• 238000001959 radiotherapy Methods 0.000 description 3
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 3
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 3
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
• 239000000600 sorbitol Substances 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 210000002784 stomach Anatomy 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 150000008163 sugars Chemical class 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• GWDIKEWVKKWNPS-UHFFFAOYSA-N tert-butyl n-[[1-(7-chlorothieno[3,2-b]pyridine-2-carbonyl)pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 GWDIKEWVKKWNPS-UHFFFAOYSA-N 0.000 description 3
• XYKYUXYNQDXZTD-MRVPVSSYSA-N tert-butyl n-methyl-n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@@H]1CCNC1 XYKYUXYNQDXZTD-MRVPVSSYSA-N 0.000 description 3
• 201000002510 thyroid cancer Diseases 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• 210000004881 tumor cell Anatomy 0.000 description 3
• 210000003932 urinary bladder Anatomy 0.000 description 3
• 210000004291 uterus Anatomy 0.000 description 3
• WXASBPDWRZNCLF-UHFFFAOYSA-N (2-ethyl-1-benzothiophen-6-yl) acetate Chemical compound C1=C(OC(C)=O)C=C2SC(CC)=CC2=C1 WXASBPDWRZNCLF-UHFFFAOYSA-N 0.000 description 2
• JSMBJYBJBSYGIN-UHFFFAOYSA-N (2-methyl-1-benzofuran-6-yl) acetate Chemical compound CC(=O)OC1=CC=C2C=C(C)OC2=C1 JSMBJYBJBSYGIN-UHFFFAOYSA-N 0.000 description 2
• CROOPTGQTSCWCM-OLQVQODUSA-N (3s,4r)-3,4-dimethoxypyrrolidine Chemical compound CO[C@@H]1CNC[C@@H]1OC CROOPTGQTSCWCM-OLQVQODUSA-N 0.000 description 2
• GZPHAADPTWFIJF-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-(3-methoxyazetidin-1-yl)methanone Chemical compound C1C(OC)CN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 GZPHAADPTWFIJF-UHFFFAOYSA-N 0.000 description 2
• AVWISDFBCUMZIC-QMMMGPOBSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound OC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 AVWISDFBCUMZIC-QMMMGPOBSA-N 0.000 description 2
• LLFHLWJSTQTAAM-SECBINFHSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 LLFHLWJSTQTAAM-SECBINFHSA-N 0.000 description 2
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• YFRMPXZVDSXEIQ-UHFFFAOYSA-N 1,2,4-trimethylindole-3-carboxamide Chemical compound CC1=C2C(=C(N(C2=CC=C1)C)C)C(=O)N YFRMPXZVDSXEIQ-UHFFFAOYSA-N 0.000 description 2
• SKZAPOOLQQGQEM-UHFFFAOYSA-N 1-(1-ethyl-6-methoxy-2-methylindol-3-yl)-2,2,2-trifluoroethanone Chemical compound C1=C(OC)C=C2N(CC)C(C)=C(C(=O)C(F)(F)F)C2=C1 SKZAPOOLQQGQEM-UHFFFAOYSA-N 0.000 description 2
• DXMQCYBZTUPOFT-UHFFFAOYSA-N 1-(2,2-diethoxyethylsulfanyl)-3-methoxybenzene Chemical compound CCOC(OCC)CSC1=CC=CC(OC)=C1 DXMQCYBZTUPOFT-UHFFFAOYSA-N 0.000 description 2
• CMNZOTFKRZYIFJ-UHFFFAOYSA-N 1-(2-ethyl-6-methoxy-1-methylindol-3-yl)-2,2,2-trifluoroethanone Chemical compound C1=C(OC)C=C2N(C)C(CC)=C(C(=O)C(F)(F)F)C2=C1 CMNZOTFKRZYIFJ-UHFFFAOYSA-N 0.000 description 2
• NJNWJBLHIZOVGU-UHFFFAOYSA-N 1-[6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridin-2-yl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 NJNWJBLHIZOVGU-UHFFFAOYSA-N 0.000 description 2
• GBJQFXRPQYYFOX-UHFFFAOYSA-N 1-benzhydryl-3-methoxyazetidine Chemical compound C1C(OC)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GBJQFXRPQYYFOX-UHFFFAOYSA-N 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• AZBJZTQRMDNKCL-UHFFFAOYSA-N 1-ethyl-6-hydroxy-n,2-dimethylindole-3-carboxamide Chemical compound C1=C(O)C=C2N(CC)C(C)=C(C(=O)NC)C2=C1 AZBJZTQRMDNKCL-UHFFFAOYSA-N 0.000 description 2
• MSSRJILGIGREJP-UHFFFAOYSA-N 1-ethyl-6-methoxy-2-methylindole-3-carboxylic acid Chemical compound C1=C(OC)C=C2N(CC)C(C)=C(C(O)=O)C2=C1 MSSRJILGIGREJP-UHFFFAOYSA-N 0.000 description 2
• FMASMAFRSBLSOL-UHFFFAOYSA-N 1-ethyl-6-methoxy-n,2-dimethylindole-3-carboxamide Chemical compound C1=C(OC)C=C2N(CC)C(C)=C(C(=O)NC)C2=C1 FMASMAFRSBLSOL-UHFFFAOYSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• ZGEIVXLZDIAAIY-UHFFFAOYSA-N 2,2,2-trifluoro-1-(6-methoxy-2-methyl-1h-indol-3-yl)ethanone Chemical compound COC1=CC=C2C(C(=O)C(F)(F)F)=C(C)NC2=C1 ZGEIVXLZDIAAIY-UHFFFAOYSA-N 0.000 description 2
• BFDXRCSYUBIFGO-UHFFFAOYSA-N 2,2,2-trifluoro-n-(2-iodo-5-methoxyphenyl)acetamide Chemical compound COC1=CC=C(I)C(NC(=O)C(F)(F)F)=C1 BFDXRCSYUBIFGO-UHFFFAOYSA-N 0.000 description 2
• UMPASXGMRYHSBB-UHFFFAOYSA-N 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 UMPASXGMRYHSBB-UHFFFAOYSA-N 0.000 description 2
• SDKLDMSGBCPKCX-UHFFFAOYSA-N 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)C1=CSC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 SDKLDMSGBCPKCX-UHFFFAOYSA-N 0.000 description 2
• BCEYTKTWCUGURA-UHFFFAOYSA-N 2-[2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-oxazol-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=COC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 BCEYTKTWCUGURA-UHFFFAOYSA-N 0.000 description 2
• PGBKYHUKKGRENX-UHFFFAOYSA-N 2-[2-(7-chlorothieno[3,2-b]pyridin-2-yl)-4,5-dihydro-1,3-oxazol-4-yl]propan-2-ol Chemical compound CC(C)(O)C1COC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 PGBKYHUKKGRENX-UHFFFAOYSA-N 0.000 description 2
• YIHCOAQBOVLHAF-UHFFFAOYSA-N 2-chloro-6-hydroxy-n,1-dimethylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(Cl)N(C)C2=C1 YIHCOAQBOVLHAF-UHFFFAOYSA-N 0.000 description 2
• CBVBKGITBAPGJQ-UHFFFAOYSA-N 2-chloro-6-methoxy-n,1-dimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(Cl)N(C)C2=C1 CBVBKGITBAPGJQ-UHFFFAOYSA-N 0.000 description 2
• ABHKECZBPQBTAB-UHFFFAOYSA-N 2-ethyl-6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 ABHKECZBPQBTAB-UHFFFAOYSA-N 0.000 description 2
• YPANGGCALNHKKK-UHFFFAOYSA-N 2-ethyl-6-hydroxy-n,1-dimethylindole-3-carboxamide Chemical compound C1=C(O)C=C2N(C)C(CC)=C(C(=O)NC)C2=C1 YPANGGCALNHKKK-UHFFFAOYSA-N 0.000 description 2
• DSLWVYYNXWAYRS-UHFFFAOYSA-N 2-ethyl-6-methoxy-1-benzofuran Chemical compound C1=C(OC)C=C2OC(CC)=CC2=C1 DSLWVYYNXWAYRS-UHFFFAOYSA-N 0.000 description 2
• JKWBIMITBWEIHG-UHFFFAOYSA-N 2-ethyl-6-methoxy-1-methylindole-3-carboxylic acid Chemical compound C1=C(OC)C=C2N(C)C(CC)=C(C(O)=O)C2=C1 JKWBIMITBWEIHG-UHFFFAOYSA-N 0.000 description 2
• RYAQCNHJMANEED-UHFFFAOYSA-N 2-ethyl-6-methoxy-1h-indole Chemical compound C1=C(OC)C=C2NC(CC)=CC2=C1 RYAQCNHJMANEED-UHFFFAOYSA-N 0.000 description 2
• IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
• CYDBBGSUZRDOPE-UHFFFAOYSA-N 2-iodo-5-methoxyaniline Chemical compound COC1=CC=C(I)C(N)=C1 CYDBBGSUZRDOPE-UHFFFAOYSA-N 0.000 description 2
• ASUDREWVUSTLJP-UHFFFAOYSA-N 2-methyl-1-benzofuran-6-ol Chemical compound C1=C(O)C=C2OC(C)=CC2=C1 ASUDREWVUSTLJP-UHFFFAOYSA-N 0.000 description 2
• BKPRMQSXMIWJAV-UHFFFAOYSA-N 2-methyl-1-benzothiophen-6-ol Chemical compound C1=C(O)C=C2SC(C)=CC2=C1 BKPRMQSXMIWJAV-UHFFFAOYSA-N 0.000 description 2
• YFMGNVFHKMQRBH-UHFFFAOYSA-N 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yl)oxy-1-benzothiophene-3-carboxylic acid Chemical compound C1=C2C(C(O)=O)=C(C)SC2=CC(OC=2C=CN=C3C=C(SC3=2)C)=C1 YFMGNVFHKMQRBH-UHFFFAOYSA-N 0.000 description 2
• LRTRIKKCTKORGD-UHFFFAOYSA-N 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzothiophene-3-carboxylic acid Chemical compound C=1C=C2C(C(O)=O)=C(C)SC2=CC=1OC1=CC=NC2=C1SC=C2 LRTRIKKCTKORGD-UHFFFAOYSA-N 0.000 description 2
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
• QOGPNCUTXVZQSL-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinolin-4-one Chemical compound C1=CC(O)=C2C=C(OC)C(OC)=CC2=N1 QOGPNCUTXVZQSL-UHFFFAOYSA-N 0.000 description 2
• CQXLWUCURYPRKC-UHFFFAOYSA-N 6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridine-2-carbaldehyde Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=CC=CC(C=O)=N1 CQXLWUCURYPRKC-UHFFFAOYSA-N 0.000 description 2
• ZPKYFRRESRSBOE-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 ZPKYFRRESRSBOE-UHFFFAOYSA-N 0.000 description 2
• FUMVOOMVAQKCFY-AWEZNQCLSA-N 6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylic acid Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(OC=3C=C4SC(C)=C(C(O)=O)C4=CC=3)=C2S1 FUMVOOMVAQKCFY-AWEZNQCLSA-N 0.000 description 2
• DUXFGNICEHKZSD-GFCCVEGCSA-N 6-[2-[(3r)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylic acid Chemical compound C=1C=C2C(C(O)=O)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](O)C1 DUXFGNICEHKZSD-GFCCVEGCSA-N 0.000 description 2
• WBKRSCLZYPSJDO-UHFFFAOYSA-N 6-hydroxy-2-methyl-1-benzothiophene-3-carboxylic acid Chemical compound OC1=CC=C2C(C(O)=O)=C(C)SC2=C1 WBKRSCLZYPSJDO-UHFFFAOYSA-N 0.000 description 2
• SLQBNPOQFHUOEV-UHFFFAOYSA-N 6-hydroxy-n,1-dimethyl-2-(trifluoromethyl)indole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C(F)(F)F)N(C)C2=C1 SLQBNPOQFHUOEV-UHFFFAOYSA-N 0.000 description 2
• OKNDOAVVCQNACN-UHFFFAOYSA-N 6-hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C)SC2=C1 OKNDOAVVCQNACN-UHFFFAOYSA-N 0.000 description 2
• HMDOCOCTAOPHLB-UHFFFAOYSA-N 6-methoxy-1,2-dimethyl-n-(3-morpholin-4-ylpropyl)indole-3-carboxamide Chemical compound CC=1N(C)C2=CC(OC)=CC=C2C=1C(=O)NCCCN1CCOCC1 HMDOCOCTAOPHLB-UHFFFAOYSA-N 0.000 description 2
• ORKQBYABRQNYIG-UHFFFAOYSA-N 6-methoxy-1,2-dimethyl-n-propan-2-ylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC(C)C)=C(C)N(C)C2=C1 ORKQBYABRQNYIG-UHFFFAOYSA-N 0.000 description 2
• GZRZBGSFUXNRJK-UHFFFAOYSA-N 6-methoxy-1-methyl-2-(trifluoromethyl)indole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=C(C(F)(F)F)N(C)C2=C1 GZRZBGSFUXNRJK-UHFFFAOYSA-N 0.000 description 2
• DZMIJVGDZXEDRK-UHFFFAOYSA-N 6-methoxy-2-methyl-1-benzothiophene-3-carbonyl chloride Chemical compound COC1=CC=C2C(C(Cl)=O)=C(C)SC2=C1 DZMIJVGDZXEDRK-UHFFFAOYSA-N 0.000 description 2
• NFQLMUSRHJTMTB-UHFFFAOYSA-N 6-methoxy-2-methyl-1h-indole Chemical compound COC1=CC=C2C=C(C)NC2=C1 NFQLMUSRHJTMTB-UHFFFAOYSA-N 0.000 description 2
• YFKHLJFVTWBKKU-UHFFFAOYSA-N 6-methoxy-2-methyl-n-(2-methylpropyl)-1-benzofuran-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NCC(C)C)=C(C)OC2=C1 YFKHLJFVTWBKKU-UHFFFAOYSA-N 0.000 description 2
• PKQPCEGGJPWRDZ-UHFFFAOYSA-N 6-methoxy-2-methyl-n-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC(C)C)=C(C)OC2=C1 PKQPCEGGJPWRDZ-UHFFFAOYSA-N 0.000 description 2
• YEZWECDZSNKRBQ-UHFFFAOYSA-N 6-methoxy-2-propan-2-yl-1-benzofuran Chemical compound COC1=CC=C2C=C(C(C)C)OC2=C1 YEZWECDZSNKRBQ-UHFFFAOYSA-N 0.000 description 2
• FKYBHANYFHZPPT-UHFFFAOYSA-N 6-methoxy-n,1,2-trimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C)N(C)C2=C1 FKYBHANYFHZPPT-UHFFFAOYSA-N 0.000 description 2
• QLDCFCVMWPPGRX-UHFFFAOYSA-N 6-methoxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C)OC2=C1 QLDCFCVMWPPGRX-UHFFFAOYSA-N 0.000 description 2
• PDXWKGQTDMFWAL-UHFFFAOYSA-N 6-methoxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C)SC2=C1 PDXWKGQTDMFWAL-UHFFFAOYSA-N 0.000 description 2
• MFOGUSOFNCBEGC-UHFFFAOYSA-N 6-methoxy-n,2-dimethyl-1h-indole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C)NC2=C1 MFOGUSOFNCBEGC-UHFFFAOYSA-N 0.000 description 2
• PZCPBDXHSBOYTA-UHFFFAOYSA-N 6-methoxy-n-methyl-2-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C(C)C)OC2=C1 PZCPBDXHSBOYTA-UHFFFAOYSA-N 0.000 description 2
• QPOGNWIRJUUBIT-UHFFFAOYSA-N 7-chloro-2-(2-methylpyrazol-3-yl)thieno[3,2-b]pyridine Chemical compound CN1N=CC=C1C1=CC2=NC=CC(Cl)=C2S1 QPOGNWIRJUUBIT-UHFFFAOYSA-N 0.000 description 2
• BVGWGBJYYYXNIV-UHFFFAOYSA-N 7-chloro-2-(2-pyrrolidin-1-ylethoxymethyl)thieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1COCCN1CCCC1 BVGWGBJYYYXNIV-UHFFFAOYSA-N 0.000 description 2
• AXAYGPPMSNHPRY-UHFFFAOYSA-N 7-chloro-2-(5-methoxypyridin-2-yl)thieno[3,2-b]pyridine Chemical compound N1=CC(OC)=CC=C1C1=CC2=NC=CC(Cl)=C2S1 AXAYGPPMSNHPRY-UHFFFAOYSA-N 0.000 description 2
• ZGTPNJQKMOHUOD-UHFFFAOYSA-N 7-chloro-2-(6-methoxypyridin-2-yl)thieno[3,2-b]pyridine Chemical compound COC1=CC=CC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 ZGTPNJQKMOHUOD-UHFFFAOYSA-N 0.000 description 2
• VTZVXWZQMPNDJJ-UHFFFAOYSA-N 7-chloro-2-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1CN1CCCC1 VTZVXWZQMPNDJJ-UHFFFAOYSA-N 0.000 description 2
• SPIQAGPALJODCN-UHFFFAOYSA-N 7-chloro-2-methylthieno[3,2-b]pyridine Chemical compound C1=CC(Cl)=C2SC(C)=CC2=N1 SPIQAGPALJODCN-UHFFFAOYSA-N 0.000 description 2
• QXTGCVQFPAXCDJ-UHFFFAOYSA-N 7-chloro-2-pyridin-2-ylthieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=CC=CC=N1 QXTGCVQFPAXCDJ-UHFFFAOYSA-N 0.000 description 2
• SYMZTTSAQCAUKC-UHFFFAOYSA-N 7-chloro-2-pyridin-4-ylthieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=CC=NC=C1 SYMZTTSAQCAUKC-UHFFFAOYSA-N 0.000 description 2
• MLVBKAYTTXFZRL-UHFFFAOYSA-N 7-chloro-2-pyrimidin-2-ylthieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=NC=CC=N1 MLVBKAYTTXFZRL-UHFFFAOYSA-N 0.000 description 2
• FFZFHLRCBXLGKR-UHFFFAOYSA-N 7-chloro-2-pyrimidin-5-ylthieno[3,2-b]pyridine Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C1=CN=CN=C1 FFZFHLRCBXLGKR-UHFFFAOYSA-N 0.000 description 2
• ZFVBOLLDXJZHQP-UHFFFAOYSA-N 7-chloro-n,n-dimethylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=C2SC(C(=O)N(C)C)=CC2=N1 ZFVBOLLDXJZHQP-UHFFFAOYSA-N 0.000 description 2
• HXYNAZQKXFLDRK-UHFFFAOYSA-N 7-chloro-n-(2-hydroxyethyl)-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=C2SC(C(=O)N(CCO)C)=CC2=N1 HXYNAZQKXFLDRK-UHFFFAOYSA-N 0.000 description 2
• DFAFPLDCEUZLEP-UHFFFAOYSA-N 7-chloro-n-[2-(dimethylamino)ethyl]-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=C2SC(C(=O)N(C)CCN(C)C)=CC2=N1 DFAFPLDCEUZLEP-UHFFFAOYSA-N 0.000 description 2
• KFNPELSUZJONTC-UHFFFAOYSA-N 7-chloro-n-[3-(dimethylamino)propyl]-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=C2SC(C(=O)N(C)CCCN(C)C)=CC2=N1 KFNPELSUZJONTC-UHFFFAOYSA-N 0.000 description 2
• PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• 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 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 241000283707 Capra Species 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 108090000994 Catalytic RNA Proteins 0.000 description 2
• 102000053642 Catalytic RNA Human genes 0.000 description 2
• 229940123587 Cell cycle inhibitor Drugs 0.000 description 2
• 241001227713 Chiron Species 0.000 description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• 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
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-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
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 229920000084 Gum arabic Polymers 0.000 description 2
• 239000012981 Hank's balanced salt solution Substances 0.000 description 2
• 241000238631 Hexapoda Species 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 241000701806 Human papillomavirus Species 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 229940124761 MMP inhibitor Drugs 0.000 description 2
• 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 2
• 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• 206010033645 Pancreatitis Diseases 0.000 description 2
• 102000003992 Peroxidases Human genes 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 229920001213 Polysorbate 20 Polymers 0.000 description 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• 208000015634 Rectal Neoplasms Diseases 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 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 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• 108091008605 VEGF receptors Proteins 0.000 description 2
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 2
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 239000000205 acacia gum Substances 0.000 description 2
• 229960000583 acetic acid Drugs 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
• 230000004913 activation Effects 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 239000008272 agar Substances 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 125000005907 alkyl ester group Chemical group 0.000 description 2
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 2
• 230000002280 anti-androgenic effect Effects 0.000 description 2
• 230000003388 anti-hormonal effect Effects 0.000 description 2
• 230000000340 anti-metabolite Effects 0.000 description 2
• 239000000051 antiandrogen Substances 0.000 description 2
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 2
• 229940100197 antimetabolite Drugs 0.000 description 2
• 239000002256 antimetabolite Substances 0.000 description 2
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 2
• 210000002403 aortic endothelial cell Anatomy 0.000 description 2
• 210000001742 aqueous humor Anatomy 0.000 description 2
• 239000008135 aqueous vehicle Substances 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
• GPLYNTQEYZSUCL-OAHLLOKOSA-N benzyl (3r)-3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrrolidine-1-carboxylate Chemical compound C1[C@H](N(C)C(=O)OC(C)(C)C)CCN1C(=O)OCC1=CC=CC=C1 GPLYNTQEYZSUCL-OAHLLOKOSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 230000000740 bleeding effect Effects 0.000 description 2
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
• 210000004556 brain Anatomy 0.000 description 2
• YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 description 2
• KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
• 150000007942 carboxylates Chemical class 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 239000013592 cell lysate Substances 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 235000010980 cellulose Nutrition 0.000 description 2
• 238000005119 centrifugation Methods 0.000 description 2
• 235000015165 citric acid Nutrition 0.000 description 2
• 238000002648 combination therapy Methods 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 238000013461 design Methods 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 239000013024 dilution buffer Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 229940088598 enzyme Drugs 0.000 description 2
• 210000003238 esophagus Anatomy 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• MJMGTBSHBUNTEJ-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-(2-iodo-5-methoxyanilino)but-2-enoate Chemical compound CCOC(=O)C=C(C(F)(F)F)NC1=CC(OC)=CC=C1I MJMGTBSHBUNTEJ-UHFFFAOYSA-N 0.000 description 2
• ZGMYLXSJXWKMOZ-UHFFFAOYSA-N ethyl 6-methoxy-1-methyl-2-(trifluoromethyl)indole-3-carboxylate Chemical compound COC1=CC=C2C(C(=O)OCC)=C(C(F)(F)F)N(C)C2=C1 ZGMYLXSJXWKMOZ-UHFFFAOYSA-N 0.000 description 2
• CNBCFCOLVZEMJF-UHFFFAOYSA-N ethyl 6-methoxy-2-(trifluoromethyl)-1h-indole-3-carboxylate Chemical compound COC1=CC=C2C(C(=O)OCC)=C(C(F)(F)F)NC2=C1 CNBCFCOLVZEMJF-UHFFFAOYSA-N 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000010685 fatty oil Substances 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 229930195712 glutamate Natural products 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 102000055590 human KDR Human genes 0.000 description 2
• 238000007327 hydrogenolysis reaction Methods 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
• 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 2
• 206010020718 hyperplasia Diseases 0.000 description 2
• 239000000367 immunologic factor Substances 0.000 description 2
• 238000002513 implantation Methods 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 239000012444 intercalating antibiotic Substances 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• 150000002500 ions Chemical class 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 239000012139 lysis buffer Substances 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• MELCKLCRGBBQTL-UHFFFAOYSA-N methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 MELCKLCRGBBQTL-UHFFFAOYSA-N 0.000 description 2
• KRARALQZKFZKOV-UHFFFAOYSA-N methyl 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yl)oxy-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=C(C)SC2=CC=1OC1=CC=NC2=C1SC(C)=C2 KRARALQZKFZKOV-UHFFFAOYSA-N 0.000 description 2
• XPDZZFIQJAYANF-UHFFFAOYSA-N methyl 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 XPDZZFIQJAYANF-UHFFFAOYSA-N 0.000 description 2
• FPJFTVZFHSPRGC-UHFFFAOYSA-N methyl 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzofuran-3-carboxylate Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)OC)C4=CC=3)=C2S1 FPJFTVZFHSPRGC-UHFFFAOYSA-N 0.000 description 2
• BGVDLUMJVUUXFO-HNNXBMFYSA-N methyl 6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxylate Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(OC=3C=C4SC(C)=C(C(=O)OC)C4=CC=3)=C2S1 BGVDLUMJVUUXFO-HNNXBMFYSA-N 0.000 description 2
• ODAVTXGNQNWWJZ-UHFFFAOYSA-N methyl 6-hydroxy-2-methyl-1-benzofuran-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=C(C)OC2=C1 ODAVTXGNQNWWJZ-UHFFFAOYSA-N 0.000 description 2
• 230000011278 mitosis Effects 0.000 description 2
• 239000011259 mixed solution Substances 0.000 description 2
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• RMUQABBSGOSZIF-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-hydroxy-1,2-dimethylindole-3-carboxamide Chemical compound C12=CC=C(O)C=C2N(C)C(C)=C1C(=O)NCC1CC1 RMUQABBSGOSZIF-UHFFFAOYSA-N 0.000 description 2
• IVTJLOKNLWIFGB-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-methoxy-1,2-dimethylindole-3-carboxamide Chemical compound CC=1N(C)C2=CC(OC)=CC=C2C=1C(=O)NCC1CC1 IVTJLOKNLWIFGB-UHFFFAOYSA-N 0.000 description 2
• DZIXZFXPBGNXSU-UHFFFAOYSA-N n-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-7-chloro-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(Cl)=C2SC(C(=O)N(CCO[Si](C)(C)C(C)(C)C)C)=CC2=N1 DZIXZFXPBGNXSU-UHFFFAOYSA-N 0.000 description 2
• ORGHIIWZXPZEKY-UHFFFAOYSA-N n-butyl-6-methoxy-1,2-dimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NCCCC)=C(C)N(C)C2=C1 ORGHIIWZXPZEKY-UHFFFAOYSA-N 0.000 description 2
• QIYIVKWWWZXUMS-UHFFFAOYSA-N n-cyclopropyl-6-hydroxy-1,2-dimethylindole-3-carboxamide Chemical compound C12=CC=C(O)C=C2N(C)C(C)=C1C(=O)NC1CC1 QIYIVKWWWZXUMS-UHFFFAOYSA-N 0.000 description 2
• KURVNRZOXBLXNM-UHFFFAOYSA-N n-cyclopropyl-6-methoxy-1,2-dimethylindole-3-carboxamide Chemical compound CC=1N(C)C2=CC(OC)=CC=C2C=1C(=O)NC1CC1 KURVNRZOXBLXNM-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 210000001672 ovary Anatomy 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• 239000008188 pellet Substances 0.000 description 2
• 108040007629 peroxidase activity proteins Proteins 0.000 description 2
• 235000020030 perry Nutrition 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• 229930029653 phosphoenolpyruvate Natural products 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229940068886 polyethylene glycol 300 Drugs 0.000 description 2
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
• 229920001184 polypeptide Polymers 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 238000001556 precipitation Methods 0.000 description 2
• 102000004196 processed proteins & peptides Human genes 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• 201000008171 proliferative glomerulonephritis Diseases 0.000 description 2
• 239000003909 protein kinase inhibitor Substances 0.000 description 2
• 238000003908 quality control method Methods 0.000 description 2
• 102000016914 ras Proteins Human genes 0.000 description 2
• 108010014186 ras Proteins Proteins 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 206010038038 rectal cancer Diseases 0.000 description 2
• 201000001275 rectum cancer Diseases 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 2
• 108091092562 ribozyme Proteins 0.000 description 2
• 239000012047 saturated solution Substances 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 239000008117 stearic acid Substances 0.000 description 2
• 229960004274 stearic acid Drugs 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 150000003871 sulfonates Chemical class 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
• 235000011149 sulphuric acid Nutrition 0.000 description 2
• 239000006228 supernatant Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 238000013268 sustained release Methods 0.000 description 2
• 239000012730 sustained-release form Substances 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
• XRRXRQJQQKMFBC-UHFFFAOYSA-N tert-butyl 3-hydroxyazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(O)C1 XRRXRQJQQKMFBC-UHFFFAOYSA-N 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• WIEJVMZWPIUWHO-UHFFFAOYSA-N tert-butyl n-(pyrrolidin-3-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNC1 WIEJVMZWPIUWHO-UHFFFAOYSA-N 0.000 description 2
• DOODNMIWSKIHRX-LLVKDONJSA-N tert-butyl n-[(3r)-1-(7-chlorothieno[3,2-b]pyridine-2-carbonyl)pyrrolidin-3-yl]-n-methylcarbamate Chemical compound C1[C@H](N(C)C(=O)OC(C)(C)C)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 DOODNMIWSKIHRX-LLVKDONJSA-N 0.000 description 2
• DAJUXRDBUUJICX-GOSISDBHSA-N tert-butyl n-[(3r)-1-[7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxythieno[3,2-b]pyridine-2-carbonyl]pyrrolidin-3-yl]-n-methylcarbamate Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](N(C)C(=O)OC(C)(C)C)C1 DAJUXRDBUUJICX-GOSISDBHSA-N 0.000 description 2
• KTNXJCYGUPINEV-UHFFFAOYSA-N tert-butyl n-[[1-[7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxythieno[3,2-b]pyridine-2-carbonyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(CNC(=O)OC(C)(C)C)C1 KTNXJCYGUPINEV-UHFFFAOYSA-N 0.000 description 2
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 230000036962 time dependent Effects 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• ZMELLUBESPPMPK-UHFFFAOYSA-N trimethyl-(2-methylpyrazol-3-yl)stannane Chemical compound CN1N=CC=C1[Sn](C)(C)C ZMELLUBESPPMPK-UHFFFAOYSA-N 0.000 description 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• 241000701447 unidentified baculovirus Species 0.000 description 2
• 210000000626 ureter Anatomy 0.000 description 2
• 238000003828 vacuum filtration Methods 0.000 description 2
• 210000004127 vitreous body Anatomy 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• 238000003260 vortexing Methods 0.000 description 2
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
• LTVIJEFEZVFIST-AZUAARDMSA-N (2r,3r)-1-[4-[(2-chloro-4-fluorophenyl)methoxy]phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1Cl LTVIJEFEZVFIST-AZUAARDMSA-N 0.000 description 1
• ZHCXOELPVFPGHI-PZJWPPBQSA-N (2r,3r)-1-[4-[(4-fluoro-2-methylphenyl)methoxy]phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound CC1=CC(F)=CC=C1COC1=CC=C(S(=O)(=O)N2[C@H]([C@](C)(O)CCC2)C(=O)NO)C=C1 ZHCXOELPVFPGHI-PZJWPPBQSA-N 0.000 description 1
• HFKPAXQHQKDLSU-MCDZGGTQSA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;pyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1.C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HFKPAXQHQKDLSU-MCDZGGTQSA-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
• 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 1
• PXCNTHIZLLJSKA-OLQVQODUSA-N (3S,4R)-3,4-dimethoxypyrrolidine-1-carboxylic acid Chemical compound CO[C@@H]1CN(C[C@@H]1OC)C(=O)O PXCNTHIZLLJSKA-OLQVQODUSA-N 0.000 description 1
• DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
• JJSAEDOMTCNEQL-GOSISDBHSA-N (3r)-3-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-n-hydroxyoxane-3-carboxamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)N[C@]1(C(=O)NO)CCCOC1 JJSAEDOMTCNEQL-GOSISDBHSA-N 0.000 description 1
• YZIGEYGKVJNXSU-QGZVFWFLSA-N (3r)-3-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxyoxolane-3-carboxamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N[C@]1(C(=O)NO)CCOC1 YZIGEYGKVJNXSU-QGZVFWFLSA-N 0.000 description 1
• JHHZLHWJQPUNKB-SCSAIBSYSA-N (3r)-pyrrolidin-3-ol Chemical compound O[C@@H]1CCNC1 JHHZLHWJQPUNKB-SCSAIBSYSA-N 0.000 description 1
• GTHULXKWBRQZMH-ZXZARUISSA-N (3s,4r)-3,4-dihydroxypyrrolidine-1-carboxylic acid Chemical compound O[C@H]1CN(C(O)=O)C[C@H]1O GTHULXKWBRQZMH-ZXZARUISSA-N 0.000 description 1
• KMPLYESDOZJASB-PAHRJMAXSA-N (6s,8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-6-methoxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one;(z)-n-carbamoyl-2-ethylbut-2-enamide;6-ethoxy-1,3-benzothiazole-2-sulfonamide Chemical compound CC\C(=C\C)C(=O)NC(N)=O.CCOC1=CC=C2N=C(S(N)(=O)=O)SC2=C1.C([C@@]12C)CC(=O)C=C1[C@@H](OC)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 KMPLYESDOZJASB-PAHRJMAXSA-N 0.000 description 1
• LNSDBFHIMSCIQB-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound C1C(O)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 LNSDBFHIMSCIQB-UHFFFAOYSA-N 0.000 description 1
• GOJMXNVZLAXITF-PHIMTYICSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3s,4r)-3,4-dimethoxypyrrolidin-1-yl]methanone Chemical compound C1[C@H](OC)[C@H](OC)CN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 GOJMXNVZLAXITF-PHIMTYICSA-N 0.000 description 1
• AGIIYFRQDNBXNJ-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound C1C(CO)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 AGIIYFRQDNBXNJ-UHFFFAOYSA-N 0.000 description 1
• LJLCYEPYHXEHII-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[3-(methylaminomethyl)pyrrolidin-1-yl]methanone Chemical compound C1C(CNC)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 LJLCYEPYHXEHII-UHFFFAOYSA-N 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 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
• XTPQJPAHSJAEAP-UHFFFAOYSA-N 1,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-n-propylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C XTPQJPAHSJAEAP-UHFFFAOYSA-N 0.000 description 1
• ZVPLCPWHWAWLFV-UHFFFAOYSA-N 1,2-dimethyl-n-(2-methylpropyl)-6-[2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCC(C)C)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CS1 ZVPLCPWHWAWLFV-UHFFFAOYSA-N 0.000 description 1
• WPYZXRYDNCHLNB-UHFFFAOYSA-N 1,2-dimethyl-n-(3-morpholin-4-ylpropyl)-6-(2-propanoylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C=12SC(C(=O)CC)=CC2=NC=CC=1OC(C=C1N(C)C=2C)=CC=C1C=2C(=O)NCCCN1CCOCC1 WPYZXRYDNCHLNB-UHFFFAOYSA-N 0.000 description 1
• VVVFEFLIDOEXLP-UHFFFAOYSA-N 1,2-dimethyl-n-propan-2-yl-6-[2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC(C)C)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CS1 VVVFEFLIDOEXLP-UHFFFAOYSA-N 0.000 description 1
• PVZFGKSEVZJXQQ-UHFFFAOYSA-N 1,2-dimethyl-n-propyl-6-[2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CS1 PVZFGKSEVZJXQQ-UHFFFAOYSA-N 0.000 description 1
• PPCUMMCZFIZQFI-UHFFFAOYSA-N 1,2-dimethylindole-3-carboxamide Chemical compound C1=CC=C2N(C)C(C)=C(C(N)=O)C2=C1 PPCUMMCZFIZQFI-UHFFFAOYSA-N 0.000 description 1
• RPMVELKOENZIBB-UHFFFAOYSA-N 1,2-dimethylpyrrolidin-3-amine Chemical compound CC1C(N)CCN1C RPMVELKOENZIBB-UHFFFAOYSA-N 0.000 description 1
• FSNGFFWICFYWQC-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine;hydron;chloride Chemical compound Cl.ClCCN1CCCC1 FSNGFFWICFYWQC-UHFFFAOYSA-N 0.000 description 1
• GCSZJMUFYOAHFY-UHFFFAOYSA-N 1-(3-ethyl-5-hydroxy-1,3-benzothiazol-2-ylidene)propan-2-one Chemical compound C1=C(O)C=C2N(CC)C(=CC(C)=O)SC2=C1 GCSZJMUFYOAHFY-UHFFFAOYSA-N 0.000 description 1
• HLCSRMAYXHSUPK-UHFFFAOYSA-N 1-(7-chlorothieno[3,2-b]pyridin-2-yl)-n,n-dimethylmethanamine Chemical compound C1=CC(Cl)=C2SC(CN(C)C)=CC2=N1 HLCSRMAYXHSUPK-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
• RDYMMGZVRCJRLD-UHFFFAOYSA-N 1-ethyl-n,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C1=C2N(CC)C(C)=C(C(=O)NC)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C RDYMMGZVRCJRLD-UHFFFAOYSA-N 0.000 description 1
• JWZODIRSJJQOKY-UHFFFAOYSA-N 1-iodo-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(I)C([N+]([O-])=O)=C1 JWZODIRSJJQOKY-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
• NBHKOXMOIRGJAI-UHFFFAOYSA-N 1-phenylbut-2-yne-1,4-diol Chemical compound OCC#CC(O)C1=CC=CC=C1 NBHKOXMOIRGJAI-UHFFFAOYSA-N 0.000 description 1
• DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
• ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 description 1
• HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
• PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 description 1
• BQTOKMYKZPCPRW-UHFFFAOYSA-N 2-(6-fluoro-1h-indol-3-yl)ethanamine Chemical compound FC1=CC=C2C(CCN)=CNC2=C1 BQTOKMYKZPCPRW-UHFFFAOYSA-N 0.000 description 1
• FZNJTQCVNFBTEG-UHFFFAOYSA-N 2-[7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxythieno[3,2-b]pyridin-2-yl]-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)C1=CSC(C=2SC3=C(OC=4C=C5N(C)C(C)=C(C(=O)NC)C5=CC=4)C=CN=C3C=2)=N1 FZNJTQCVNFBTEG-UHFFFAOYSA-N 0.000 description 1
• VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 1
• LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
• RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 1
• KMODISUYWZPVGV-UHFFFAOYSA-N 2-bromo-6-methoxypyridine Chemical compound COC1=CC=CC(Br)=N1 KMODISUYWZPVGV-UHFFFAOYSA-N 0.000 description 1
• IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
• PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
• XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
• STKLLNSPUBALDD-UHFFFAOYSA-N 2-ethyl-4-methoxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=CC(OC)=C2C(C(=O)NC)=C(CC)OC2=C1 STKLLNSPUBALDD-UHFFFAOYSA-N 0.000 description 1
• QTMDNNYMTGCCSS-UHFFFAOYSA-N 2-ethyl-6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1-dimethylindole-3-carboxamide Chemical compound C1=C2N(C)C(CC)=C(C(=O)NC)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 QTMDNNYMTGCCSS-UHFFFAOYSA-N 0.000 description 1
• IHGSREVUBHDWRV-UHFFFAOYSA-N 2-ethyl-6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 IHGSREVUBHDWRV-UHFFFAOYSA-N 0.000 description 1
• QGOIOPDLQPCMTJ-AWEZNQCLSA-N 2-ethyl-6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1CO QGOIOPDLQPCMTJ-AWEZNQCLSA-N 0.000 description 1
• JMGZGYQTBYYBGH-HNNXBMFYSA-N 2-ethyl-6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1COC JMGZGYQTBYYBGH-HNNXBMFYSA-N 0.000 description 1
• JMGZGYQTBYYBGH-UHFFFAOYSA-N 2-ethyl-6-[2-[2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCCC1COC JMGZGYQTBYYBGH-UHFFFAOYSA-N 0.000 description 1
• OTJJAEXQYFXRAP-UHFFFAOYSA-N 2-ethyl-6-hydroxy-1-benzothiophene-3-carboxylic acid Chemical compound CCc1sc2cc(O)ccc2c1C(O)=O OTJJAEXQYFXRAP-UHFFFAOYSA-N 0.000 description 1
• ARGYNMKYEZDWNC-UHFFFAOYSA-N 2-ethyl-6-hydroxy-n-methyl-1-benzothiophene-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(CC)SC2=C1 ARGYNMKYEZDWNC-UHFFFAOYSA-N 0.000 description 1
• GURGNAOREUTWGP-UHFFFAOYSA-N 2-ethyl-6-methoxy-1-benzothiophene Chemical compound C1=C(OC)C=C2SC(CC)=CC2=C1 GURGNAOREUTWGP-UHFFFAOYSA-N 0.000 description 1
• DHVGRRZINVZNKC-UHFFFAOYSA-N 2-ethyl-6-methoxy-n,1-dimethylindole-3-carboxamide Chemical compound C1=C(OC)C=C2N(C)C(CC)=C(C(=O)NC)C2=C1 DHVGRRZINVZNKC-UHFFFAOYSA-N 0.000 description 1
• GDZIDWWHBJLMRP-UHFFFAOYSA-N 2-ethyl-6-methoxy-n-methyl-1-benzofuran-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(CC)OC2=C1 GDZIDWWHBJLMRP-UHFFFAOYSA-N 0.000 description 1
• HROXIYGKBAAAOG-UHFFFAOYSA-N 2-ethyl-n,1-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C1=C2N(C)C(CC)=C(C(=O)NC)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C HROXIYGKBAAAOG-UHFFFAOYSA-N 0.000 description 1
• HGPLZMQMVPEWIE-UHFFFAOYSA-N 2-ethyl-n-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C HGPLZMQMVPEWIE-UHFFFAOYSA-N 0.000 description 1
• SBDIRQUIIQPALR-UHFFFAOYSA-N 2-ethyl-n-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C SBDIRQUIIQPALR-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
• PTKTXYDJIOBEOD-UHFFFAOYSA-N 2-iodo-5-methoxypyridine Chemical compound COC1=CC=C(I)N=C1 PTKTXYDJIOBEOD-UHFFFAOYSA-N 0.000 description 1
• QNMGYGHSTHUNJI-UHFFFAOYSA-N 2-methyl-1-benzofuran-3-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C)OC2=C1 QNMGYGHSTHUNJI-UHFFFAOYSA-N 0.000 description 1
• OGXMJWAGXCEGHL-UHFFFAOYSA-N 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yl)oxy-n-(2-morpholin-4-ylethyl)-1-benzothiophene-3-carboxamide Chemical compound C=12SC(C)=CC2=NC=CC=1OC(C=C1SC=2C)=CC=C1C=2C(=O)NCCN1CCOCC1 OGXMJWAGXCEGHL-UHFFFAOYSA-N 0.000 description 1
• LDWWCABGDLOZAT-UHFFFAOYSA-N 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yl)oxy-n-(3-morpholin-4-ylpropyl)-1-benzothiophene-3-carboxamide Chemical compound C=12SC(C)=CC2=NC=CC=1OC(C=C1SC=2C)=CC=C1C=2C(=O)NCCCN1CCOCC1 LDWWCABGDLOZAT-UHFFFAOYSA-N 0.000 description 1
• LUOOCKLPLUTBGB-UHFFFAOYSA-N 2-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-n-(2-methylpropyl)-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCC(C)C)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C LUOOCKLPLUTBGB-UHFFFAOYSA-N 0.000 description 1
• OODXOZOXRGGTPB-UHFFFAOYSA-N 2-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-n-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC(C)C)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C OODXOZOXRGGTPB-UHFFFAOYSA-N 0.000 description 1
• WZNXMSCLPTVBDG-UHFFFAOYSA-N 2-methyl-n-(2-morpholin-4-ylethyl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CC=1OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C2C=1C(=O)NCCN1CCOCC1 WZNXMSCLPTVBDG-UHFFFAOYSA-N 0.000 description 1
• KRUQYOKCCSITJU-UHFFFAOYSA-N 2-methyl-n-(2-propan-2-yloxyethyl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCOC(C)C)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 KRUQYOKCCSITJU-UHFFFAOYSA-N 0.000 description 1
• ZOVJPLMXHWYIGQ-UHFFFAOYSA-N 2-methyl-n-(3-morpholin-4-ylpropyl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CC=1OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C2C=1C(=O)NCCCN1CCOCC1 ZOVJPLMXHWYIGQ-UHFFFAOYSA-N 0.000 description 1
• OGNXHWCMIGXLFU-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound N1C(C)=CC(NC(=O)C=2C3=CC=C(OC=4C=5SC=CC=5N=CC=4)C=C3OC=2C)=N1 OGNXHWCMIGXLFU-UHFFFAOYSA-N 0.000 description 1
• LZZYWTGYPJSFMC-UHFFFAOYSA-N 2-methyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CC=1OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C2C=1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 LZZYWTGYPJSFMC-UHFFFAOYSA-N 0.000 description 1
• DOOWHGNLESJONB-UHFFFAOYSA-N 2-methyl-n-(6-morpholin-4-ylpyridin-3-yl)-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CC=1OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C2C=1C(=O)NC(C=N1)=CC=C1N1CCOCC1 DOOWHGNLESJONB-UHFFFAOYSA-N 0.000 description 1
• BCAADYNUWUVWCP-UHFFFAOYSA-N 2-methyl-n-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CN1CCCC1CCNC(=O)C1=C(C)OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C12 BCAADYNUWUVWCP-UHFFFAOYSA-N 0.000 description 1
• LNUQJMCGFZEWGG-UHFFFAOYSA-N 2-methyl-n-[2-(4-sulfamoylphenyl)ethyl]-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound CC=1OC2=CC(OC=3C=4SC=CC=4N=CC=3)=CC=C2C=1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 LNUQJMCGFZEWGG-UHFFFAOYSA-N 0.000 description 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
• USECIYVEPXUVHT-UHFFFAOYSA-N 2-propan-2-yloxyethanamine Chemical compound CC(C)OCCN USECIYVEPXUVHT-UHFFFAOYSA-N 0.000 description 1
• AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
• NMDUJEUWNLCXSB-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]amino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N(CCC(O)=O)C(C)(C)C(=O)NO)=CC=C1OC1=CC=C(F)C=C1 NMDUJEUWNLCXSB-UHFFFAOYSA-N 0.000 description 1
• PDCBVHDMAFCHPK-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxycarbamoyl)cyclobutyl]amino]propanoic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCC1 PDCBVHDMAFCHPK-UHFFFAOYSA-N 0.000 description 1
• WARXYAHFCARUNH-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[4-(hydroxycarbamoyl)oxan-4-yl]amino]propanoic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCOCC1 WARXYAHFCARUNH-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 1
• USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical compound CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 description 1
• ROAOTXVXLMMSRG-UHFFFAOYSA-N 3-tert-butyl-7-chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine Chemical compound S1C2=C(Cl)C=CN=C2C(C(C)(C)C)=C1C1=NC=CS1 ROAOTXVXLMMSRG-UHFFFAOYSA-N 0.000 description 1
• UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 1
• CYZMUIMLRBJSRO-UHFFFAOYSA-N 4-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-n-hydroxyoxane-4-carboxamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCOCC1 CYZMUIMLRBJSRO-UHFFFAOYSA-N 0.000 description 1
• ZBRHTUMWSDPCMI-UHFFFAOYSA-N 4-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxyoxane-4-carboxamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCOCC1 ZBRHTUMWSDPCMI-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• CJXMVKYNVIGQBS-OWOJBTEDSA-N 4-hydroxycinnamaldehyde Chemical compound OC1=CC=C(\C=C\C=O)C=C1 CJXMVKYNVIGQBS-OWOJBTEDSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
• FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 1
• GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
• UHZHEOAEJRHUBW-UHFFFAOYSA-N 5-phenyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC=C1 UHZHEOAEJRHUBW-UHFFFAOYSA-N 0.000 description 1
• JKPCLIFXFZHQAA-UHFFFAOYSA-N 6-[2-(3,4-dihydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC(O)C(O)C1 JKPCLIFXFZHQAA-UHFFFAOYSA-N 0.000 description 1
• CAEUYOFTFBZCEO-UHFFFAOYSA-N 6-[2-(3,4-dimethoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC(OC)C(OC)C1 CAEUYOFTFBZCEO-UHFFFAOYSA-N 0.000 description 1
• INLDCZPTNFOEPP-UHFFFAOYSA-N 6-[2-(3-hydroxyazetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC(O)C1 INLDCZPTNFOEPP-UHFFFAOYSA-N 0.000 description 1
• OBVDFRNCNVQQPL-UHFFFAOYSA-N 6-[2-(3-hydroxyazetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC(O)C1 OBVDFRNCNVQQPL-UHFFFAOYSA-N 0.000 description 1
• JKMYXNDDGKUAQA-UHFFFAOYSA-N 6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-1,2-dimethyl-n-propyl-2,3-dihydroindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCC)C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 JKMYXNDDGKUAQA-UHFFFAOYSA-N 0.000 description 1
• AAMYJCNPJICIBB-UHFFFAOYSA-N 6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-(2-methylpropyl)-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCC(C)C)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 AAMYJCNPJICIBB-UHFFFAOYSA-N 0.000 description 1
• ZEOXXZRILKIKRK-UHFFFAOYSA-N 6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 ZEOXXZRILKIKRK-UHFFFAOYSA-N 0.000 description 1
• AJHYVPPLFSOEHN-UHFFFAOYSA-N 6-[2-(3-hydroxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1h-indole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)NC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(O)C1 AJHYVPPLFSOEHN-UHFFFAOYSA-N 0.000 description 1
• ZHSCKNOFFWWXPI-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-(2-methylpropyl)-1-benzofuran-3-carboxamide Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NCC(C)C)C4=CC=3)=C2S1 ZHSCKNOFFWWXPI-UHFFFAOYSA-N 0.000 description 1
• KQYSAKDGXSYUIU-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-(2-morpholin-4-ylethyl)-1-benzofuran-3-carboxamide Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NCCN5CCOCC5)C4=CC=3)=C2S1 KQYSAKDGXSYUIU-UHFFFAOYSA-N 0.000 description 1
• XAOPWLMVFUVSGV-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-propyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 XAOPWLMVFUVSGV-UHFFFAOYSA-N 0.000 description 1
• LVJCPNGUASRZQF-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1-dimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=CN(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 LVJCPNGUASRZQF-UHFFFAOYSA-N 0.000 description 1
• OJQIFKDYTGSYKR-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 OJQIFKDYTGSYKR-UHFFFAOYSA-N 0.000 description 1
• VGFNVFSXGSUNFE-UHFFFAOYSA-N 6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-methyl-2-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C(C)C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(OC)C1 VGFNVFSXGSUNFE-UHFFFAOYSA-N 0.000 description 1
• OEXCFIURBHZEKJ-UHFFFAOYSA-N 6-[2-(5-methoxypyridin-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=C(OC)C=N1 OEXCFIURBHZEKJ-UHFFFAOYSA-N 0.000 description 1
• GKZBOCSNBKWVNO-UHFFFAOYSA-N 6-[2-(6-methoxypyridin-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=CC(OC)=N1 GKZBOCSNBKWVNO-UHFFFAOYSA-N 0.000 description 1
• NSQDAFVQDBHZOO-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-1-ethyl-n,2-dimethylindole-3-carboxamide Chemical compound C1=C2N(CC)C(C)=C(C(=O)NC)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 NSQDAFVQDBHZOO-UHFFFAOYSA-N 0.000 description 1
• FEPWMICNVIWXDJ-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-ethyl-n-methyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 FEPWMICNVIWXDJ-UHFFFAOYSA-N 0.000 description 1
• SLLOYHODSWDXBZ-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-ethyl-n-methyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(CC)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 SLLOYHODSWDXBZ-UHFFFAOYSA-N 0.000 description 1
• UPUZOHHNYSDYNC-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethyl-2,3-dihydroindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 UPUZOHHNYSDYNC-UHFFFAOYSA-N 0.000 description 1
• LCXGETGLFMFVBW-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 LCXGETGLFMFVBW-UHFFFAOYSA-N 0.000 description 1
• RWHRNPSCCGNCGJ-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-(3-hydroxypropyl)-1,2-dimethylindole-3-carboxamide Chemical compound C1=C2N(C)C(C)=C(C(=O)NCCCO)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 RWHRNPSCCGNCGJ-UHFFFAOYSA-N 0.000 description 1
• WEEZQZJWVSOKTD-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-(cyclopropylmethyl)-2-methyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCC3CC3)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 WEEZQZJWVSOKTD-UHFFFAOYSA-N 0.000 description 1
• APKQFPRQZSLGMW-UHFFFAOYSA-N 6-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-n-cyclopropyl-2-methyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC3CC3)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 APKQFPRQZSLGMW-UHFFFAOYSA-N 0.000 description 1
• BMHCSVLPIOLXAO-KRWDZBQOSA-N 6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-1,2-dimethyl-n-propylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1CO BMHCSVLPIOLXAO-KRWDZBQOSA-N 0.000 description 1
• ASPNXNNUFHGNHT-AWEZNQCLSA-N 6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1CO ASPNXNNUFHGNHT-AWEZNQCLSA-N 0.000 description 1
• BWBGNAWDQPVAFL-AWEZNQCLSA-N 6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1CO BWBGNAWDQPVAFL-AWEZNQCLSA-N 0.000 description 1
• OQLXJTYAPDFGQH-KRWDZBQOSA-N 6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NC(C)C)C4=CC=3)=C2S1 OQLXJTYAPDFGQH-KRWDZBQOSA-N 0.000 description 1
• LTYXBFLEJQZHJW-HNNXBMFYSA-N 6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1COC LTYXBFLEJQZHJW-HNNXBMFYSA-N 0.000 description 1
• FLOZCQBCARZKPU-HNNXBMFYSA-N 6-[2-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1COC FLOZCQBCARZKPU-HNNXBMFYSA-N 0.000 description 1
• GERLGVGXZBWFNJ-MRXNPFEDSA-N 6-[2-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](N(C)C)C1 GERLGVGXZBWFNJ-MRXNPFEDSA-N 0.000 description 1
• YTTULRAJXYMOQE-CYBMUJFWSA-N 6-[2-[(3r)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,1-dimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=CN(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](O)C1 YTTULRAJXYMOQE-CYBMUJFWSA-N 0.000 description 1
• KKGOMHQLUWLEQT-CYBMUJFWSA-N 6-[2-[(3r)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](O)C1 KKGOMHQLUWLEQT-CYBMUJFWSA-N 0.000 description 1
• XPOXSTQZQZYNNG-OAHLLOKOSA-N 6-[2-[(3r)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CC[C@@H](OC)C1 XPOXSTQZQZYNNG-OAHLLOKOSA-N 0.000 description 1
• QMHXYRADUPLVMB-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC1=CC=NC2=C1SC(CN(C)C)=C2 QMHXYRADUPLVMB-UHFFFAOYSA-N 0.000 description 1
• XACOPEGPFNDTFU-UHFFFAOYSA-N 6-[2-[2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCCC1CO XACOPEGPFNDTFU-UHFFFAOYSA-N 0.000 description 1
• CRBVDFOWRRJNFD-UHFFFAOYSA-N 6-[2-[2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-n-(2-methylpropyl)-1-benzofuran-3-carboxamide Chemical compound COCC1CCCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NCC(C)C)C4=CC=3)=C2S1 CRBVDFOWRRJNFD-UHFFFAOYSA-N 0.000 description 1
• LTYXBFLEJQZHJW-UHFFFAOYSA-N 6-[2-[2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCCC1COC LTYXBFLEJQZHJW-UHFFFAOYSA-N 0.000 description 1
• AJFCFHUIFUPHBV-UHFFFAOYSA-N 6-[2-[3-(aminomethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC(CN)C1 AJFCFHUIFUPHBV-UHFFFAOYSA-N 0.000 description 1
• KIEMCZYCRBKQSL-UHFFFAOYSA-N 6-[2-[4-(hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC(CO)=CS1 KIEMCZYCRBKQSL-UHFFFAOYSA-N 0.000 description 1
• AIKCOVPTNKRTJF-UHFFFAOYSA-N 6-[2-[4-(hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl]oxy-n,2-dimethyl-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC(CO)=CS1 AIKCOVPTNKRTJF-UHFFFAOYSA-N 0.000 description 1
• QOLUNNAJXNLRIN-UHFFFAOYSA-N 6-[2-[6-[(dimethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxy-n,1,2-trimethylindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=CC(CN(C)C)=N1 QOLUNNAJXNLRIN-UHFFFAOYSA-N 0.000 description 1
• QWFHFNGMCPMOCD-UHFFFAOYSA-N 6-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=CC(C=O)=N1 QWFHFNGMCPMOCD-UHFFFAOYSA-N 0.000 description 1
• YEDLUSPFNVLIRI-UHFFFAOYSA-N 6-hydroxy-1,2-dimethyl-n-(2-methylpropyl)indole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NCC(C)C)=C(C)N(C)C2=C1 YEDLUSPFNVLIRI-UHFFFAOYSA-N 0.000 description 1
• YJCYDFKFRPVUAA-UHFFFAOYSA-N 6-hydroxy-1,2-dimethyl-n-(3-morpholin-4-ylpropyl)indole-3-carboxamide Chemical compound C12=CC=C(O)C=C2N(C)C(C)=C1C(=O)NCCCN1CCOCC1 YJCYDFKFRPVUAA-UHFFFAOYSA-N 0.000 description 1
• WHVVNWQNHGSUIO-UHFFFAOYSA-N 6-hydroxy-1,2-dimethyl-n-propan-2-ylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC(C)C)=C(C)N(C)C2=C1 WHVVNWQNHGSUIO-UHFFFAOYSA-N 0.000 description 1
• IRKSQJUXWKTBEB-UHFFFAOYSA-N 6-hydroxy-1,2-dimethyl-n-propylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NCCC)=C(C)N(C)C2=C1 IRKSQJUXWKTBEB-UHFFFAOYSA-N 0.000 description 1
• NJXMAYPYUIBZFT-UHFFFAOYSA-N 6-hydroxy-1,2-dimethyl-n-pyridin-2-ylindole-3-carboxamide Chemical compound C12=CC=C(O)C=C2N(C)C(C)=C1C(=O)NC1=CC=CC=N1 NJXMAYPYUIBZFT-UHFFFAOYSA-N 0.000 description 1
• VVKFCWFCQBZDSU-UHFFFAOYSA-N 6-hydroxy-2-methyl-n-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC(C)C)=C(C)OC2=C1 VVKFCWFCQBZDSU-UHFFFAOYSA-N 0.000 description 1
• ALTIHNKZQMTOFA-UHFFFAOYSA-N 6-hydroxy-n,1-dimethylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=CN(C)C2=C1 ALTIHNKZQMTOFA-UHFFFAOYSA-N 0.000 description 1
• GDRDXCAJCDWESK-UHFFFAOYSA-N 6-hydroxy-n,2-dimethyl-1h-indole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C)NC2=C1 GDRDXCAJCDWESK-UHFFFAOYSA-N 0.000 description 1
• YNHOCCULFYKDQK-UHFFFAOYSA-N 6-hydroxy-n-(3-hydroxypropyl)-1,2-dimethylindole-3-carboxamide Chemical compound C1=C(O)C=C2N(C)C(C)=C(C(=O)NCCCO)C2=C1 YNHOCCULFYKDQK-UHFFFAOYSA-N 0.000 description 1
• CJKOPQYDJGVFKS-UHFFFAOYSA-N 6-hydroxy-n-methyl-2-propan-2-yl-1-benzofuran-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C(C)C)OC2=C1 CJKOPQYDJGVFKS-UHFFFAOYSA-N 0.000 description 1
• VRISXXPVJDWXMH-UHFFFAOYSA-N 6-methoxy-1,2-dimethyl-n-(2-methylpropyl)indole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NCC(C)C)=C(C)N(C)C2=C1 VRISXXPVJDWXMH-UHFFFAOYSA-N 0.000 description 1
• QJRWYBIKLXNYLF-UHFFFAOYSA-N 6-methoxy-1h-indole Chemical compound COC1=CC=C2C=CNC2=C1 QJRWYBIKLXNYLF-UHFFFAOYSA-N 0.000 description 1
• LPBGVZVDBKMWFS-UHFFFAOYSA-N 6-methoxy-1h-indole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=CNC2=C1 LPBGVZVDBKMWFS-UHFFFAOYSA-N 0.000 description 1
• DSCFTVXYEPVMNZ-UHFFFAOYSA-N 6-methoxy-n,1-dimethyl-2-(trifluoromethyl)indole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NC)=C(C(F)(F)F)N(C)C2=C1 DSCFTVXYEPVMNZ-UHFFFAOYSA-N 0.000 description 1
• CHEHTPAPQRVRKE-UHFFFAOYSA-N 6-methoxy-n-(3-methoxypropyl)-1,2-dimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NCCCOC)=C(C)N(C)C2=C1 CHEHTPAPQRVRKE-UHFFFAOYSA-N 0.000 description 1
• VVTSPTCBHTWXMD-UHFFFAOYSA-N 6-morpholin-4-ylpyridin-3-amine Chemical compound N1=CC(N)=CC=C1N1CCOCC1 VVTSPTCBHTWXMD-UHFFFAOYSA-N 0.000 description 1
• 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
• 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
• NRURIWCKJQEYJW-UHFFFAOYSA-N 7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxy-n,n-dimethylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC1=CC=NC2=C1SC(C(=O)N(C)C)=C2 NRURIWCKJQEYJW-UHFFFAOYSA-N 0.000 description 1
• KFSKMSDCXAFGSO-UHFFFAOYSA-N 7-[[2,3-dimethyl-1-(methylcarbamoyl)-3h-inden-5-yl]oxy]-n-(2-hydroxyethyl)-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)C(C)C2=CC=1OC1=CC=NC2=C1SC(C(=O)N(C)CCO)=C2 KFSKMSDCXAFGSO-UHFFFAOYSA-N 0.000 description 1
• OFDOSCIMSYHCLS-UHFFFAOYSA-N 7-chlorothieno[3,2-b]pyridine-2-carbonyl chloride Chemical compound C1=CC(Cl)=C2SC(C(=O)Cl)=CC2=N1 OFDOSCIMSYHCLS-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 206010000830 Acute leukaemia Diseases 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 108090000644 Angiozyme Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 229910015900 BF3 Inorganic materials 0.000 description 1
• 108010081589 Becaplermin Proteins 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• 206010005949 Bone cancer Diseases 0.000 description 1
• 208000018084 Bone neoplasm Diseases 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010006143 Brain stem glioma Diseases 0.000 description 1
• 206010006417 Bronchial carcinoma Diseases 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• 208000017897 Carcinoma of esophagus Diseases 0.000 description 1
• 206010007953 Central nervous system lymphoma Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 102100027995 Collagenase 3 Human genes 0.000 description 1
• 108050005238 Collagenase 3 Proteins 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• VHHGUBHZBLPTKL-UHFFFAOYSA-N Cp-471358 Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCCC1 VHHGUBHZBLPTKL-UHFFFAOYSA-N 0.000 description 1
• 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
• 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
• 102000010907 Cyclooxygenase 2 Human genes 0.000 description 1
• 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
• NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-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
• AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
• 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
• 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 229920002307 Dextran Polymers 0.000 description 1
• 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
• 239000001856 Ethyl cellulose Substances 0.000 description 1
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
• 108091008794 FGF receptors Proteins 0.000 description 1
• 201000001342 Fallopian tube cancer Diseases 0.000 description 1
• 208000013452 Fallopian tube neoplasm Diseases 0.000 description 1
• 208000009849 Female Genital Neoplasms Diseases 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
• VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
• 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 102100031547 HLA class II histocompatibility antigen, DO alpha chain Human genes 0.000 description 1
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101000866278 Homo sapiens HLA class II histocompatibility antigen, DO alpha chain Proteins 0.000 description 1
• 101100519721 Homo sapiens PDGFRB gene Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 208000005016 Intestinal Neoplasms Diseases 0.000 description 1
• 206010061252 Intraocular melanoma Diseases 0.000 description 1
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
• SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
• FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
• UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
• 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
• 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
• UCUNFLYVYCGDHP-BYPYZUCNSA-N L-methionine sulfone Chemical compound CS(=O)(=O)CC[C@H](N)C(O)=O UCUNFLYVYCGDHP-BYPYZUCNSA-N 0.000 description 1
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
• SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 206010023774 Large cell lung cancer Diseases 0.000 description 1
• 244000178870 Lavandula angustifolia Species 0.000 description 1
• 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 102100027998 Macrophage metalloelastase Human genes 0.000 description 1
• 101710187853 Macrophage metalloelastase Proteins 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000032271 Malignant tumor of penis Diseases 0.000 description 1
• 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
• GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 102100030417 Matrilysin Human genes 0.000 description 1
• 108090000855 Matrilysin Proteins 0.000 description 1
• 102000002274 Matrix Metalloproteinases Human genes 0.000 description 1
• 108010000684 Matrix Metalloproteinases Proteins 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 101100288142 Mus musculus Klkb1 gene Proteins 0.000 description 1
• JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 description 1
• KNHGSSFKDIQHNP-UHFFFAOYSA-N N,1,2-trimethylindole-3-carboxamide Chemical compound CNC(=O)C1=C(N(C2=CC=CC=C12)C)C KNHGSSFKDIQHNP-UHFFFAOYSA-N 0.000 description 1
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
• UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
• FTFRZXFNZVCRSK-UHFFFAOYSA-N N4-(3-chloro-4-fluorophenyl)-N6-(1-methyl-4-piperidinyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1CN(C)CCC1NC1=NC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=N1 FTFRZXFNZVCRSK-UHFFFAOYSA-N 0.000 description 1
• 238000005481 NMR spectroscopy Methods 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical class COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
• 102000043276 Oncogene Human genes 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 208000000821 Parathyroid Neoplasms Diseases 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 208000002471 Penile Neoplasms Diseases 0.000 description 1
• 206010034299 Penile cancer Diseases 0.000 description 1
• IGVPBCZDHMIOJH-UHFFFAOYSA-N Phenyl butyrate Chemical class CCCC(=O)OC1=CC=CC=C1 IGVPBCZDHMIOJH-UHFFFAOYSA-N 0.000 description 1
• 208000007913 Pituitary Neoplasms Diseases 0.000 description 1
• 201000005746 Pituitary adenoma Diseases 0.000 description 1
• 206010061538 Pituitary tumour benign Diseases 0.000 description 1
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• 229920002642 Polysorbate 65 Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 108700020978 Proto-Oncogene Proteins 0.000 description 1
• 102000052575 Proto-Oncogene Human genes 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 208000006265 Renal cell carcinoma Diseases 0.000 description 1
• LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
• QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
• 102000001332 SRC Human genes 0.000 description 1
• 108060006706 SRC Proteins 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 206010070834 Sensitisation Diseases 0.000 description 1
• 208000000453 Skin Neoplasms 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
• 102100030416 Stromelysin-1 Human genes 0.000 description 1
• 101710108790 Stromelysin-1 Proteins 0.000 description 1
• 102100028848 Stromelysin-2 Human genes 0.000 description 1
• 101710108792 Stromelysin-2 Proteins 0.000 description 1
• 102100028847 Stromelysin-3 Human genes 0.000 description 1
• 108050005271 Stromelysin-3 Proteins 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
• 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
• 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 102000004243 Tubulin Human genes 0.000 description 1
• 108090000704 Tubulin Proteins 0.000 description 1
• 206010046431 Urethral cancer Diseases 0.000 description 1
• 206010046458 Urethral neoplasms Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 208000002495 Uterine Neoplasms Diseases 0.000 description 1
• 201000005969 Uveal melanoma Diseases 0.000 description 1
• 208000004354 Vulvar Neoplasms Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• DSOITGJEUKHAJN-UHFFFAOYSA-N Zinnimidine Chemical compound CC(C)=CCOC1=C(C)C(OC)=C2CNC(=O)C2=C1 DSOITGJEUKHAJN-UHFFFAOYSA-N 0.000 description 1
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• TTWYZDPBDWHJOR-IDIVVRGQSA-L adenosine triphosphate disodium Chemical compound [Na+].[Na+].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 TTWYZDPBDWHJOR-IDIVVRGQSA-L 0.000 description 1
• 238000009098 adjuvant therapy Methods 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 208000024447 adrenal gland neoplasm Diseases 0.000 description 1
• 238000012382 advanced drug delivery Methods 0.000 description 1
• 230000002411 adverse Effects 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
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 230000003113 alkalizing effect Effects 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000010976 amide bond formation reaction Methods 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 238000010640 amide synthesis reaction Methods 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229940124277 aminobutyric acid Drugs 0.000 description 1
• HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 210000002159 anterior chamber Anatomy 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 238000011394 anticancer treatment Methods 0.000 description 1
• 230000005975 antitumor immune response Effects 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 159000000032 aromatic acids Chemical class 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical class OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 1
• BVXMBOAVHLBDKI-UHFFFAOYSA-N azetidin-3-ol;2,2,2-trifluoroacetic acid Chemical compound OC1CNC1.OC(=O)C(F)(F)F BVXMBOAVHLBDKI-UHFFFAOYSA-N 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• OSDPRBVIIIGHPO-PHIMTYICSA-N benzyl (3r,4s)-3,4-dihydroxypyrrolidine-1-carboxylate Chemical compound C1[C@@H](O)[C@@H](O)CN1C(=O)OCC1=CC=CC=C1 OSDPRBVIIIGHPO-PHIMTYICSA-N 0.000 description 1
• POZQTSVBFIYXQI-BETUJISGSA-N benzyl (3s,4r)-3,4-dimethoxypyrrolidine-1-carboxylate Chemical compound C1[C@H](OC)[C@H](OC)CN1C(=O)OCC1=CC=CC=C1 POZQTSVBFIYXQI-BETUJISGSA-N 0.000 description 1
• XSKKIFJNZPNVGO-UHFFFAOYSA-N benzyl 2,5-dihydropyrrole-1-carboxylate Chemical compound C1C=CCN1C(=O)OCC1=CC=CC=C1 XSKKIFJNZPNVGO-UHFFFAOYSA-N 0.000 description 1
• CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 229920000249 biocompatible polymer Polymers 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 210000001109 blastomere Anatomy 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 230000036772 blood pressure Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 150000001649 bromium compounds Chemical class 0.000 description 1
• 210000000621 bronchi Anatomy 0.000 description 1
• 201000005200 bronchus cancer Diseases 0.000 description 1
• 239000007975 buffered saline Substances 0.000 description 1
• 239000001273 butane Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Chemical class 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 229960004424 carbon dioxide Drugs 0.000 description 1
• 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 210000000170 cell membrane Anatomy 0.000 description 1
• 238000001516 cell proliferation assay Methods 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
• 210000003161 choroid Anatomy 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000024207 chronic leukemia Diseases 0.000 description 1
• 210000004240 ciliary body Anatomy 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 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
• 229940001468 citrate Drugs 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 229960002173 citrulline Drugs 0.000 description 1
• 235000013477 citrulline Nutrition 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 230000030944 contact inhibition Effects 0.000 description 1
• 229940124558 contraceptive agent Drugs 0.000 description 1
• 239000003433 contraceptive agent Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 229940099112 cornstarch Drugs 0.000 description 1
• 150000001907 coumarones Chemical class 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 108010044165 crotoxin drug combination cardiotoxin Proteins 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 210000000695 crystalline len Anatomy 0.000 description 1
• 208000030381 cutaneous melanoma Diseases 0.000 description 1
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• 230000001086 cytosolic effect Effects 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 239000002254 cytotoxic agent Substances 0.000 description 1
• 231100000599 cytotoxic agent Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000032459 dedifferentiation Effects 0.000 description 1
• 230000007850 degeneration Effects 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
• 230000017858 demethylation Effects 0.000 description 1
• 238000010520 demethylation reaction Methods 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
• 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
• ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
• 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
• 235000011180 diphosphates Nutrition 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000009509 drug development Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 230000032692 embryo implantation Effects 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 210000000750 endocrine system Anatomy 0.000 description 1
• 230000003511 endothelial effect Effects 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940079360 enema for constipation Drugs 0.000 description 1
• 230000007613 environmental effect Effects 0.000 description 1
• 229930013356 epothilone Natural products 0.000 description 1
• 150000003883 epothilone derivatives Chemical class 0.000 description 1
• YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 239000002038 ethyl acetate fraction Substances 0.000 description 1
• 235000019325 ethyl cellulose Nutrition 0.000 description 1
• 229920001249 ethyl cellulose Polymers 0.000 description 1
• 229940035423 ethyl ether Drugs 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-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
• 238000013265 extended release Methods 0.000 description 1
• 208000024519 eye neoplasm Diseases 0.000 description 1
• 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 description 1
• 229960002949 fluorouracil Drugs 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 229940050411 fumarate Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 229960002598 fumaric acid Drugs 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• 230000002538 fungal effect Effects 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 210000005095 gastrointestinal system Anatomy 0.000 description 1
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229940097043 glucuronic acid Drugs 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 229960005150 glycerol Drugs 0.000 description 1
• 229940074045 glyceryl distearate Drugs 0.000 description 1
• 229940075507 glyceryl monostearate Drugs 0.000 description 1
• 239000008202 granule composition Substances 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 229920000591 gum Polymers 0.000 description 1
• 201000010536 head and neck cancer Diseases 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 229960002897 heparin Drugs 0.000 description 1
• 229920000669 heparin Polymers 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229940125697 hormonal agent Drugs 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229920001600 hydrophobic polymer Polymers 0.000 description 1
• QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
• 229960002591 hydroxyproline Drugs 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000009169 immunotherapy Methods 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 150000002475 indoles Chemical class 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• KLEAIHJJLUAXIQ-JDRGBKBRSA-N irinotecan hydrochloride hydrate Chemical compound O.O.O.Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 KLEAIHJJLUAXIQ-JDRGBKBRSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
• 229940045996 isethionic acid Drugs 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
• 239000004922 lacquer Substances 0.000 description 1
• 150000003893 lactate salts Chemical class 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229960000448 lactic acid Drugs 0.000 description 1
• 239000001102 lavandula vera Substances 0.000 description 1
• 235000018219 lavender Nutrition 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 238000012417 linear regression Methods 0.000 description 1
• 229940057995 liquid paraffin Drugs 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 201000009546 lung large cell carcinoma Diseases 0.000 description 1
• 210000004698 lymphocyte Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 229940098895 maleic acid Drugs 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000011565 manganese chloride Substances 0.000 description 1
• 235000002867 manganese chloride Nutrition 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 1
• 239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 125000005341 metaphosphate group Chemical group 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• NDBQJIBNNUJNHA-DFWYDOINSA-N methyl (2s)-2-amino-3-hydroxypropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CO NDBQJIBNNUJNHA-DFWYDOINSA-N 0.000 description 1
• HVEQRTHCFLCTLP-UHFFFAOYSA-N methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(C=2SC3=C(Cl)C=CN=C3C=2)=N1 HVEQRTHCFLCTLP-UHFFFAOYSA-N 0.000 description 1
• NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
• UHRJTYPHPQDSJY-UHFFFAOYSA-N methyl 2-methyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C UHRJTYPHPQDSJY-UHFFFAOYSA-N 0.000 description 1
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
• CQDOXZJEWYPOLH-UHFFFAOYSA-N n,1,2-trimethyl-6-(2-propanoylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C)N(C)C2=CC(OC=2C=CN=C3C=C(SC3=2)C(=O)CC)=C1 CQDOXZJEWYPOLH-UHFFFAOYSA-N 0.000 description 1
• PTGOKSHFOJCAIP-UHFFFAOYSA-N n,1,2-trimethyl-6-(2-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 PTGOKSHFOJCAIP-UHFFFAOYSA-N 0.000 description 1
• IWOSEHXSWRCQDI-UHFFFAOYSA-N n,1,2-trimethyl-6-(2-pyridin-4-ylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=NC=C1 IWOSEHXSWRCQDI-UHFFFAOYSA-N 0.000 description 1
• DPGMYCMPARDEDI-UHFFFAOYSA-N n,1,2-trimethyl-6-(2-pyrimidin-2-ylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CC=N1 DPGMYCMPARDEDI-UHFFFAOYSA-N 0.000 description 1
• CTOSEWGMFOKQDP-UHFFFAOYSA-N n,1,2-trimethyl-6-(2-pyrimidin-5-ylthieno[3,2-b]pyridin-7-yl)oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CN=CN=C1 CTOSEWGMFOKQDP-UHFFFAOYSA-N 0.000 description 1
• REBFFXZAYDITIO-UHFFFAOYSA-N n,1,2-trimethyl-6-[2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CS1 REBFFXZAYDITIO-UHFFFAOYSA-N 0.000 description 1
• UPHOCKTZLFGXRW-UHFFFAOYSA-N n,1,2-trimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C UPHOCKTZLFGXRW-UHFFFAOYSA-N 0.000 description 1
• DWGMOMJPVSKYJV-UHFFFAOYSA-N n,1,2-trimethyl-6-[2-(pyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCCC1 DWGMOMJPVSKYJV-UHFFFAOYSA-N 0.000 description 1
• AWSKQZFMBPYJFW-UHFFFAOYSA-N n,1,2-trimethyl-6-[2-[3-(methylamino)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C1C(NC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4N(C)C(C)=C(C(=O)NC)C4=CC=3)=C2S1 AWSKQZFMBPYJFW-UHFFFAOYSA-N 0.000 description 1
• OHCLUFIPHVJKMM-UHFFFAOYSA-N n,1,2-trimethyl-6-[2-[3-(methylaminomethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C1C(CNC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4N(C)C(C)=C(C(=O)NC)C4=CC=3)=C2S1 OHCLUFIPHVJKMM-UHFFFAOYSA-N 0.000 description 1
• IVXFHKXSHHAIJT-UHFFFAOYSA-N n,1-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-2-(trifluoromethyl)indole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C(F)(F)F)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C IVXFHKXSHHAIJT-UHFFFAOYSA-N 0.000 description 1
• WRUIQPGQBCNOHD-UHFFFAOYSA-N n,1-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=CN(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C WRUIQPGQBCNOHD-UHFFFAOYSA-N 0.000 description 1
• WOORFKRMEJEZGG-UHFFFAOYSA-N n,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C WOORFKRMEJEZGG-UHFFFAOYSA-N 0.000 description 1
• MNPIYFNULMJMIM-UHFFFAOYSA-N n,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CN1C MNPIYFNULMJMIM-UHFFFAOYSA-N 0.000 description 1
• OKWNWYAGTZNJMG-UHFFFAOYSA-N n,2-dimethyl-6-[2-(2-methylpyrazol-3-yl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=CC=NN1C OKWNWYAGTZNJMG-UHFFFAOYSA-N 0.000 description 1
• IYLANZRWJUEYBV-UHFFFAOYSA-N n,2-dimethyl-6-[2-(2-pyrrolidin-1-ylethoxymethyl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2COCCN1CCCC1 IYLANZRWJUEYBV-UHFFFAOYSA-N 0.000 description 1
• YYGNQHKLPFKJCL-UHFFFAOYSA-N n,2-dimethyl-6-[2-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyridin-7-yl]oxy-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2CN1CCCC1 YYGNQHKLPFKJCL-UHFFFAOYSA-N 0.000 description 1
• VLOPQYDQZNXZFW-UHFFFAOYSA-N n,2-dimethyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 VLOPQYDQZNXZFW-UHFFFAOYSA-N 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• YMHHOAPNIQWTEK-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound C1=C2NC=CC2=CC(NC(=O)C=2C3=CC=C(OC=4C=5SC=CC=5N=CC=4)C=C3OC=2C)=C1 YMHHOAPNIQWTEK-UHFFFAOYSA-N 0.000 description 1
• GBCVQULYIPXTMS-UHFFFAOYSA-N n-(3-hydroxypropyl)-1,2-dimethyl-6-[2-(pyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C1=C2N(C)C(C)=C(C(=O)NCCCO)C2=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCCC1 GBCVQULYIPXTMS-UHFFFAOYSA-N 0.000 description 1
• KSDYVFWIDNCSIO-UHFFFAOYSA-N n-(3-hydroxypropyl)-6-methoxy-1,2-dimethylindole-3-carboxamide Chemical compound COC1=CC=C2C(C(=O)NCCCO)=C(C)N(C)C2=C1 KSDYVFWIDNCSIO-UHFFFAOYSA-N 0.000 description 1
• PTPNGUVFAXFRCO-UHFFFAOYSA-N n-(cyclopropylmethyl)-1,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C12=CC=C(OC=3C=4SC(=CC=4N=CC=3)C=3N(C=CN=3)C)C=C2N(C)C(C)=C1C(=O)NCC1CC1 PTPNGUVFAXFRCO-UHFFFAOYSA-N 0.000 description 1
• ZZSQQAOJVHMOTJ-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzofuran-3-carboxamide Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NCC5CC5)C4=CC=3)=C2S1 ZZSQQAOJVHMOTJ-UHFFFAOYSA-N 0.000 description 1
• RWALXQMZANWHCR-QGZVFWFLSA-N n-(cyclopropylmethyl)-6-[2-[(3r)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-1,2-dimethylindole-3-carboxamide Chemical compound C12=CC=C(OC=3C=4SC(=CC=4N=CC=3)C(=O)N3C[C@H](O)CC3)C=C2N(C)C(C)=C1C(=O)NCC1CC1 RWALXQMZANWHCR-QGZVFWFLSA-N 0.000 description 1
• HUWCCPSRSXXDPO-UHFFFAOYSA-N n-[2-(6-fluoro-1h-indol-3-yl)ethyl]-2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound FC1=CC=C2C(CCNC(=O)C=3C4=CC=C(OC=5C=6SC=CC=6N=CC=5)C=C4OC=3C)=CNC2=C1 HUWCCPSRSXXDPO-UHFFFAOYSA-N 0.000 description 1
• XPPADWUERXKHRO-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxy-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC1=CC=NC2=C1SC(C(=O)N(C)CCN(C)C)=C2 XPPADWUERXKHRO-UHFFFAOYSA-N 0.000 description 1
• DDCLENQRZGFSDA-UHFFFAOYSA-N n-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxy-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC1=CC=NC2=C1SC(C(=O)N(C)CCO[Si](C)(C)C(C)(C)C)=C2 DDCLENQRZGFSDA-UHFFFAOYSA-N 0.000 description 1
• LQPGBRXMTDAKPA-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-7-[1,2-dimethyl-3-(methylcarbamoyl)indol-6-yl]oxy-n-methylthieno[3,2-b]pyridine-2-carboxamide Chemical compound C=1C=C2C(C(=O)NC)=C(C)N(C)C2=CC=1OC1=CC=NC2=C1SC(C(=O)N(C)CCCN(C)C)=C2 LQPGBRXMTDAKPA-UHFFFAOYSA-N 0.000 description 1
• IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
• GEQJHHLWIDHTKG-UHFFFAOYSA-N n-butyl-1,2-dimethyl-6-[2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCCC)=C(C)N(C)C2=CC=1OC(C=1S2)=CC=NC=1C=C2C1=NC=CS1 GEQJHHLWIDHTKG-UHFFFAOYSA-N 0.000 description 1
• KNLMHNGNYAEMCK-UHFFFAOYSA-N n-butyl-2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxamide Chemical compound C=1C=C2C(C(=O)NCCCC)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 KNLMHNGNYAEMCK-UHFFFAOYSA-N 0.000 description 1
• OFJPRJFJYATTGE-UHFFFAOYSA-N n-butyl-6-hydroxy-1,2-dimethylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NCCCC)=C(C)N(C)C2=C1 OFJPRJFJYATTGE-UHFFFAOYSA-N 0.000 description 1
• GSMPSKWDIFSIAR-UHFFFAOYSA-N n-cyclohexyl-1-(4-nitrophenyl)methanimine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=NC1CCCCC1 GSMPSKWDIFSIAR-UHFFFAOYSA-N 0.000 description 1
• HVJVXXLWPPPQCS-UHFFFAOYSA-N n-cyclopropyl-1,2-dimethyl-6-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyindole-3-carboxamide Chemical compound C12=CC=C(OC=3C=4SC(=CC=4N=CC=3)C=3N(C=CN=3)C)C=C2N(C)C(C)=C1C(=O)NC1CC1 HVJVXXLWPPPQCS-UHFFFAOYSA-N 0.000 description 1
• VWPGPKVCOPQAPF-UHFFFAOYSA-N n-cyclopropyl-6-[2-(3-methoxypyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzofuran-3-carboxamide Chemical compound C1C(OC)CCN1C(=O)C1=CC2=NC=CC(OC=3C=C4OC(C)=C(C(=O)NC5CC5)C4=CC=3)=C2S1 VWPGPKVCOPQAPF-UHFFFAOYSA-N 0.000 description 1
• HKWAGNYOODDZAR-KRWDZBQOSA-N n-cyclopropyl-6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-1,2-dimethylindole-3-carboxamide Chemical compound C12=CC=C(OC=3C=4SC(=CC=4N=CC=3)C(=O)N3[C@@H](CCC3)CO)C=C2N(C)C(C)=C1C(=O)NC1CC1 HKWAGNYOODDZAR-KRWDZBQOSA-N 0.000 description 1
• OUYIBIZVWMZHBK-INIZCTEOSA-N n-cyclopropyl-6-[2-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-2-methyl-1-benzothiophene-3-carboxamide Chemical compound C=1C=C2C(C(=O)NC3CC3)=C(C)SC2=CC=1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC[C@H]1CO OUYIBIZVWMZHBK-INIZCTEOSA-N 0.000 description 1
• DOJRSTPBUUGXEW-MRXNPFEDSA-N n-cyclopropyl-6-[2-[(3r)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-1,2-dimethylindole-3-carboxamide Chemical compound C12=CC=C(OC=3C=4SC(=CC=4N=CC=3)C(=O)N3C[C@H](O)CC3)C=C2N(C)C(C)=C1C(=O)NC1CC1 DOJRSTPBUUGXEW-MRXNPFEDSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 238000009099 neoadjuvant therapy Methods 0.000 description 1
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229940036132 norvasc Drugs 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 229940078552 o-xylene Drugs 0.000 description 1
• 201000008106 ocular cancer Diseases 0.000 description 1
• 201000002575 ocular melanoma Diseases 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 229920000620 organic polymer Polymers 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 229960003104 ornithine Drugs 0.000 description 1
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
• 239000012285 osmium tetroxide Substances 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 150000002913 oxalic acids Chemical class 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000000849 parathyroid Effects 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000008024 pharmaceutical diluent Substances 0.000 description 1
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical group C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
• DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 125000005541 phosphonamide group Chemical group 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 150000003014 phosphoric acid esters Chemical class 0.000 description 1
• DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
• 125000005498 phthalate group Chemical class 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 208000021310 pituitary gland adenoma Diseases 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
• 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
• 229920001155 polypropylene Polymers 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
• 229940099511 polysorbate 65 Drugs 0.000 description 1
• 230000035409 positive regulation of cell proliferation Effects 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229910000160 potassium phosphate Inorganic materials 0.000 description 1
• 235000011009 potassium phosphates Nutrition 0.000 description 1
• 159000000001 potassium salts Chemical class 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
• 239000002243 precursor Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 208000016800 primary central nervous system lymphoma Diseases 0.000 description 1
• 229950003608 prinomastat Drugs 0.000 description 1
• YKPYIPVDTNNYCN-INIZCTEOSA-N prinomastat Chemical compound ONC(=O)[C@H]1C(C)(C)SCCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=NC=C1 YKPYIPVDTNNYCN-INIZCTEOSA-N 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 229940095574 propionic acid Drugs 0.000 description 1
• 229960004063 propylene glycol Drugs 0.000 description 1
• 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
• 230000006920 protein precipitation Effects 0.000 description 1
• 230000029983 protein stabilization Effects 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• 210000001747 pupil Anatomy 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 108700042226 ras Genes Proteins 0.000 description 1
• 229940124617 receptor tyrosine kinase inhibitor Drugs 0.000 description 1
• 230000001172 regenerating effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008844 regulatory mechanism Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
• 229960003147 reserpine Drugs 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 210000001525 retina Anatomy 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229940100486 rice starch Drugs 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
• 229960000371 rofecoxib Drugs 0.000 description 1
• MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 210000003786 sclera Anatomy 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 229950003647 semaxanib Drugs 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 230000008313 sensitization Effects 0.000 description 1
• 230000001235 sensitizing effect Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 238000009097 single-agent therapy Methods 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 201000003708 skin melanoma Diseases 0.000 description 1
• 210000000813 small intestine Anatomy 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
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 239000012439 solid excipient Substances 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 206010062261 spinal cord neoplasm Diseases 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 239000012089 stop solution Substances 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 150000003892 tartrate salts Chemical class 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
• MHRKPCRXBAHJGS-UHFFFAOYSA-N tert-butyl n-[(1-benzylpyrrolidin-3-yl)methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 MHRKPCRXBAHJGS-UHFFFAOYSA-N 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• YNVOMSDITJMNET-UHFFFAOYSA-M thiophene-3-carboxylate Chemical compound [O-]C(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-M 0.000 description 1
• 239000003734 thymidylate synthase inhibitor Substances 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 229940029284 trichlorofluoromethane Drugs 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 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 1
• 238000000825 ultraviolet detection Methods 0.000 description 1
• 210000003606 umbilical vein Anatomy 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000037965 uterine sarcoma Diseases 0.000 description 1
• 208000013139 vaginal neoplasm Diseases 0.000 description 1
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
• 229960002004 valdecoxib Drugs 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 230000000007 visual effect Effects 0.000 description 1
• 238000012800 visualization Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 229940100445 wheat starch Drugs 0.000 description 1
• GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1