JP2008506761A - プロテインキナーゼ阻害剤としてのチアゾールおよびイソチアゾール誘導体 - Google Patents

Info

Publication number

JP2008506761A

JP2008506761A JP2007522032A JP2007522032A JP2008506761A JP 2008506761 A JP2008506761 A JP 2008506761A JP 2007522032 A JP2007522032 A JP 2007522032A JP 2007522032 A JP2007522032 A JP 2007522032A JP 2008506761 A JP2008506761 A JP 2008506761A

Authority

JP

Japan

Prior art keywords

group

hydrogen

optionally

optionally substituted

groups

Prior art date

2004-07-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

• Espacenet
• Global Dossier
• Discuss

• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title claims description 22
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 3
• 239000003909 protein kinase inhibitor Substances 0.000 title description 3
• 150000003854 isothiazoles Chemical class 0.000 title 1
• -1 tautomers Chemical class 0.000 claims abstract description 327
• 150000001875 compounds Chemical class 0.000 claims abstract description 308
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 174
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 143
• 239000001257 hydrogen Substances 0.000 claims abstract description 143
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 106
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 104
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 96
• 150000003839 salts Chemical class 0.000 claims abstract description 81
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 76
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 76
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 55
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 51
• 239000012453 solvate Substances 0.000 claims abstract description 50
• 238000011282 treatment Methods 0.000 claims abstract description 48
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 46
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 42
• 108091007914 CDKs Proteins 0.000 claims abstract description 37
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
• 208000024891 symptom Diseases 0.000 claims abstract description 22
• 230000001404 mediated effect Effects 0.000 claims abstract description 21
• 230000002265 prevention Effects 0.000 claims abstract description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 164
• 125000001424 substituent group Chemical group 0.000 claims description 137
• 125000002837 carbocyclic group Chemical group 0.000 claims description 119
• 229910052760 oxygen Inorganic materials 0.000 claims description 101
• 229910052736 halogen Inorganic materials 0.000 claims description 89
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
• 239000011737 fluorine Substances 0.000 claims description 86
• 229910052731 fluorine Inorganic materials 0.000 claims description 86
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 150000002367 halogens Chemical class 0.000 claims description 80
• 125000001072 heteroaryl group Chemical group 0.000 claims description 78
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
• 125000005842 heteroatom Chemical group 0.000 claims description 73
• 238000000034 method Methods 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 229910005965 SO 2 Inorganic materials 0.000 claims description 66
• 206010028980 Neoplasm Diseases 0.000 claims description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 45
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 45
• 201000010099 disease Diseases 0.000 claims description 45
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 42
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 41
• 230000000694 effects Effects 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 36
• 239000000460 chlorine Substances 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 35
• 125000002950 monocyclic group Chemical group 0.000 claims description 35
• 125000004122 cyclic group Chemical group 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 34
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 32
• 125000002619 bicyclic group Chemical group 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 32
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 31
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000001153 fluoro group Chemical group F* 0.000 claims description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims description 20
• 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
• 230000002159 abnormal effect Effects 0.000 claims description 16
• 206010006187 Breast cancer Diseases 0.000 claims description 14
• 108091000080 Phosphotransferase Proteins 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 14
• 102000020233 phosphotransferase Human genes 0.000 claims description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
• 230000010261 cell growth Effects 0.000 claims description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
• 208000026310 Breast neoplasm Diseases 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 230000004770 neurodegeneration Effects 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 8
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 8
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 230000002062 proliferating effect Effects 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 208000036142 Viral infection Diseases 0.000 claims description 5
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 5
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 5
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 230000032823 cell division Effects 0.000 claims description 5
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 230000009385 viral infection Effects 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
• 230000033077 cellular process Effects 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 201000004101 esophageal cancer Diseases 0.000 claims description 4
• 229940043355 kinase inhibitor Drugs 0.000 claims description 4
• 230000007170 pathology Effects 0.000 claims description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 230000001419 dependent effect Effects 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
• 238000012216 screening Methods 0.000 claims description 3
• GNFBDRVLKIAIAI-UHFFFAOYSA-N 4-(cyclopentanecarbonylamino)-n-(5-piperazin-1-ylpyridin-2-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CCCC1C(=O)NC1=CSN=C1C(=O)NC(N=C1)=CC=C1N1CCNCC1 GNFBDRVLKIAIAI-UHFFFAOYSA-N 0.000 claims description 2
• DYIHGFOHKQDOFZ-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(1-methylpiperidin-4-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=NSC=C1NC(=O)C1=C(Cl)C=CC=C1Cl DYIHGFOHKQDOFZ-UHFFFAOYSA-N 0.000 claims description 2
• AXTNWXOQUGZQEN-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(1-methylsulfonylpiperidin-4-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC1NC(=O)C1=NSC=C1NC(=O)C1=C(Cl)C=CC=C1Cl AXTNWXOQUGZQEN-UHFFFAOYSA-N 0.000 claims description 2
• OJDSVYGVQABZKY-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(4-piperazin-1-ylphenyl)-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=C1 OJDSVYGVQABZKY-UHFFFAOYSA-N 0.000 claims description 2
• ZGAOBUVBYJMOIO-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(5-piperazin-1-ylpyridin-2-yl)-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=N1 ZGAOBUVBYJMOIO-UHFFFAOYSA-N 0.000 claims description 2
• IGQKVMFJQYYNHP-UHFFFAOYSA-N 4-benzamido-n-(4-piperazin-1-ylphenyl)-1,2-thiazole-3-carboxamide Chemical compound N=1SC=C(NC(=O)C=2C=CC=CC=2)C=1C(=O)NC(C=C1)=CC=C1N1CCNCC1 IGQKVMFJQYYNHP-UHFFFAOYSA-N 0.000 claims description 2
• RUDIFZNAIWMHCD-UHFFFAOYSA-N 5-(1-phenylethylamino)-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C(C)NC=1SC=NC=1C(=O)NC1CCNCC1 RUDIFZNAIWMHCD-UHFFFAOYSA-N 0.000 claims description 2
• JNYPMZYCAWPDQM-UHFFFAOYSA-N 5-(benzylamino)-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NCC=2C=CC=CC=2)=C1C(=O)NC1CCNCC1 JNYPMZYCAWPDQM-UHFFFAOYSA-N 0.000 claims description 2
• ZVEIEBFLWBOITR-UHFFFAOYSA-N 5-[(2,6-dichlorobenzoyl)amino]-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCNCC2)N=CS1 ZVEIEBFLWBOITR-UHFFFAOYSA-N 0.000 claims description 2
• UVPSVMSAVYAYOK-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methylamino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1CNC1=C(C(=O)NC2CCNCC2)N=CS1 UVPSVMSAVYAYOK-UHFFFAOYSA-N 0.000 claims description 2
• HEYUDERTMFOHRY-UHFFFAOYSA-N 5-[(2,6-difluorobenzoyl)amino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 HEYUDERTMFOHRY-UHFFFAOYSA-N 0.000 claims description 2
• QSXRFTZWQXQGNZ-UHFFFAOYSA-N 5-[(2-ethoxybenzoyl)amino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound CCOC1=CC=CC=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 QSXRFTZWQXQGNZ-UHFFFAOYSA-N 0.000 claims description 2
• NOIVZCHOIWNQBZ-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methylamino]-n-(5-piperazin-1-ylpyridin-2-yl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC=C1CNC1=C(C(=O)NC=2N=CC(=CC=2)N2CCNCC2)N=CS1 NOIVZCHOIWNQBZ-UHFFFAOYSA-N 0.000 claims description 2
• QSSSHSCAYCKMPX-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methylamino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC=C1CNC1=C(C(=O)NC2CCNCC2)N=CS1 QSSSHSCAYCKMPX-UHFFFAOYSA-N 0.000 claims description 2
• DHHFLNWAAJEZHD-UHFFFAOYSA-N 5-anilino-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC(C=C1)=CC=C1N1CCNCC1 DHHFLNWAAJEZHD-UHFFFAOYSA-N 0.000 claims description 2
• NRYMLBIVHGSKFQ-UHFFFAOYSA-N 5-anilino-n-(5-piperazin-1-ylpyridin-2-yl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC(N=C1)=CC=C1N1CCNCC1 NRYMLBIVHGSKFQ-UHFFFAOYSA-N 0.000 claims description 2
• CFDOJVDGZDCKBF-UHFFFAOYSA-N 5-anilino-n-phenyl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC1=CC=CC=C1 CFDOJVDGZDCKBF-UHFFFAOYSA-N 0.000 claims description 2
• JEPQOIAPDXCGNY-UHFFFAOYSA-N 5-anilino-n-pyridin-2-yl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC1=CC=CC=N1 JEPQOIAPDXCGNY-UHFFFAOYSA-N 0.000 claims description 2
• GYHGJFOIBSHDGP-UHFFFAOYSA-N 5-benzamido-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC(=O)C=2C=CC=CC=2)=C1C(=O)NC(C=C1)=CC=C1N1CCNCC1 GYHGJFOIBSHDGP-UHFFFAOYSA-N 0.000 claims description 2
• RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
• 229920002527 Glycogen Polymers 0.000 claims description 2
• 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims description 2
• 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims description 2
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
• 229940096919 glycogen Drugs 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• CZFWPBQREYHQTP-UHFFFAOYSA-N n-(2-hydroxyphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound OC1=CC=CC=C1NC(=O)C1=C(NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)SC=N1 CZFWPBQREYHQTP-UHFFFAOYSA-N 0.000 claims description 2
• GYMPJRRJQGCMMT-UHFFFAOYSA-N n-(3-hydroxyphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound OC1=CC=CC(NC(=O)C2=C(SC=N2)NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=C1 GYMPJRRJQGCMMT-UHFFFAOYSA-N 0.000 claims description 2
• XQTOTFALQIOYTR-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCOCC2)N=CS1 XQTOTFALQIOYTR-UHFFFAOYSA-N 0.000 claims description 2
• YYUPIQKOMRVZRP-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCNCC2)N=CS1 YYUPIQKOMRVZRP-UHFFFAOYSA-N 0.000 claims description 2
• SMBSJQSGNJXZGT-UHFFFAOYSA-N n-(5-piperazin-1-ylpyridin-2-yl)-4-[(2,4,6-trichlorobenzoyl)amino]-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=N1 SMBSJQSGNJXZGT-UHFFFAOYSA-N 0.000 claims description 2
• HYSBSYXHANLYEH-UHFFFAOYSA-N n-(5-piperazin-1-ylpyridin-2-yl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2N=CC(=CC=2)N2CCNCC2)N=CS1 HYSBSYXHANLYEH-UHFFFAOYSA-N 0.000 claims description 2
• ZPNBQORASPWJLW-UHFFFAOYSA-N n-[1-(oxan-4-yl)piperidin-4-yl]-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC2CCN(CC2)C2CCOCC2)N=CS1 ZPNBQORASPWJLW-UHFFFAOYSA-N 0.000 claims description 2
• ARKJZJOONVBQJC-UHFFFAOYSA-N n-[4-(methoxymethoxy)cyclohexyl]-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C1CC(OCOC)CCC1NC(=O)C1=C(NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)SC=N1 ARKJZJOONVBQJC-UHFFFAOYSA-N 0.000 claims description 2
• OUYKHNHVHUGDCD-UHFFFAOYSA-N n-phenyl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC=CC=2)N=CS1 OUYKHNHVHUGDCD-UHFFFAOYSA-N 0.000 claims description 2
• FRHSRHLFGOLDSR-UHFFFAOYSA-N n-piperidin-4-yl-5-(pyridin-3-ylamino)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=NC=CC=2)=C1C(=O)NC1CCNCC1 FRHSRHLFGOLDSR-UHFFFAOYSA-N 0.000 claims description 2
• DJJZIVUJHYIGEJ-UHFFFAOYSA-N n-piperidin-4-yl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 DJJZIVUJHYIGEJ-UHFFFAOYSA-N 0.000 claims description 2
• IBYYUUTWTXZSRR-UHFFFAOYSA-N n-pyridin-2-yl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2N=CC=CC=2)N=CS1 IBYYUUTWTXZSRR-UHFFFAOYSA-N 0.000 claims description 2
• 230000001575 pathological effect Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 16
• 229940121375 antifungal agent Drugs 0.000 claims 1
• 239000003429 antifungal agent Substances 0.000 claims 1
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 41
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 30
• 125000004076 pyridyl group Chemical group 0.000 description 29
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 28
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 21
• 108090000623 proteins and genes Proteins 0.000 description 20
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 18
• 102000016736 Cyclin Human genes 0.000 description 18
• 108050006400 Cyclin Proteins 0.000 description 18
• 108090000257 Cyclin E Proteins 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 18
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 18
• 238000009472 formulation Methods 0.000 description 18
• 239000008194 pharmaceutical composition Substances 0.000 description 18
• 102000003909 Cyclin E Human genes 0.000 description 17
• 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 description 17
• 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 description 17
• 230000026731 phosphorylation Effects 0.000 description 17
• 238000006366 phosphorylation reaction Methods 0.000 description 17
• 102000004169 proteins and genes Human genes 0.000 description 17
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 16
• 125000005843 halogen group Chemical group 0.000 description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 description 16
• 150000001408 amides Chemical class 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 15
• 239000002253 acid Substances 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 150000001721 carbon Chemical group 0.000 description 14
• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 14
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 230000014509 gene expression Effects 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• 235000018102 proteins Nutrition 0.000 description 13
• 229940124597 therapeutic agent Drugs 0.000 description 13
• 230000001225 therapeutic effect Effects 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• 125000002883 imidazolyl group Chemical group 0.000 description 12
• 230000035772 mutation Effects 0.000 description 12
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 11
• 230000022131 cell cycle Effects 0.000 description 11
• 241000894007 species Species 0.000 description 11
• 230000003827 upregulation Effects 0.000 description 11
• 101000891649 Homo sapiens Transcription elongation factor A protein-like 1 Proteins 0.000 description 10
• 101000596402 Mus musculus Neuronal vesicle trafficking-associated protein 1 Proteins 0.000 description 10
• 101000800539 Mus musculus Translationally-controlled tumor protein Proteins 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
• 101000781972 Schizosaccharomyces pombe (strain 972 / ATCC 24843) Protein wos2 Proteins 0.000 description 10
• 101001009610 Toxoplasma gondii Dense granule protein 5 Proteins 0.000 description 10
• 102100040250 Transcription elongation factor A protein-like 1 Human genes 0.000 description 10
• 102100033254 Tumor suppressor ARF Human genes 0.000 description 10
• 230000006907 apoptotic process Effects 0.000 description 10
• 238000001802 infusion Methods 0.000 description 10
• 230000005764 inhibitory process Effects 0.000 description 10
• 230000003287 optical effect Effects 0.000 description 10
• 230000037361 pathway Effects 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 239000000758 substrate Substances 0.000 description 10
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 102100029604 Interferon alpha-inducible protein 27, mitochondrial Human genes 0.000 description 9
• 108050008367 Transmembrane emp24 domain-containing protein 7 Proteins 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 230000002018 overexpression Effects 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 8
• 101000721661 Homo sapiens Cellular tumor antigen p53 Proteins 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
• 230000037396 body weight Effects 0.000 description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 description 8
• 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 8
• 238000005755 formation reaction Methods 0.000 description 8
• 230000006870 function Effects 0.000 description 8
• 238000002347 injection Methods 0.000 description 8
• 239000007924 injection Substances 0.000 description 8
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
• 229940002612 prodrug Drugs 0.000 description 8
• 239000000651 prodrug Substances 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• 238000002560 therapeutic procedure Methods 0.000 description 8
• 102100036329 Cyclin-dependent kinase 3 Human genes 0.000 description 7
• 101000715946 Homo sapiens Cyclin-dependent kinase 3 Proteins 0.000 description 7
• 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 7
• 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 7
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 7
• 102000001253 Protein Kinase Human genes 0.000 description 7
• 230000004913 activation Effects 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 229940024606 amino acid Drugs 0.000 description 7
• 235000001014 amino acid Nutrition 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 230000008901 benefit Effects 0.000 description 7
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 7
• 239000000872 buffer Substances 0.000 description 7
• 238000002648 combination therapy Methods 0.000 description 7
• 230000007812 deficiency Effects 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 238000004108 freeze drying Methods 0.000 description 7
• 239000002502 liposome Substances 0.000 description 7
• 238000004811 liquid chromatography Methods 0.000 description 7
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 7
• 201000002528 pancreatic cancer Diseases 0.000 description 7
• 208000008443 pancreatic carcinoma Diseases 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 108060006633 protein kinase Proteins 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 230000000638 stimulation Effects 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 6
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• 108010058546 Cyclin D1 Proteins 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 102100024165 G1/S-specific cyclin-D1 Human genes 0.000 description 6
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• 150000001413 amino acids Chemical class 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• 239000004067 bulking agent Substances 0.000 description 6
• 239000004202 carbamide Substances 0.000 description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
• 239000003153 chemical reaction reagent 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
• 238000005859 coupling reaction Methods 0.000 description 6
• 229960000390 fludarabine Drugs 0.000 description 6
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 6
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 6
• 208000032839 leukemia Diseases 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• 230000001105 regulatory effect Effects 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000011593 sulfur Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 230000035897 transcription Effects 0.000 description 6
• 238000013518 transcription Methods 0.000 description 6
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 5
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
• 208000024827 Alzheimer disease Diseases 0.000 description 5
• 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 5
• 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 5
• 102100024457 Cyclin-dependent kinase 9 Human genes 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
• 101000980930 Homo sapiens Cyclin-dependent kinase 9 Proteins 0.000 description 5
• 102100040243 Microtubule-associated protein tau Human genes 0.000 description 5
• 206010041067 Small cell lung cancer Diseases 0.000 description 5
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 230000033228 biological regulation Effects 0.000 description 5
• 239000011248 coating agent Substances 0.000 description 5
• 238000000576 coating method Methods 0.000 description 5
• IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
• 230000004069 differentiation Effects 0.000 description 5
• 229940088598 enzyme Drugs 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 5
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
• 238000004949 mass spectrometry Methods 0.000 description 5
• 125000001620 monocyclic carbocycle group Chemical group 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 5
• 229920000642 polymer Polymers 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 125000000168 pyrrolyl group Chemical group 0.000 description 5
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 5
• 230000022983 regulation of cell cycle Effects 0.000 description 5
• 230000004044 response Effects 0.000 description 5
• 208000000587 small cell lung carcinoma Diseases 0.000 description 5
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 4
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical group O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 4
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• 102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• 230000004707 G1/S transition Effects 0.000 description 4
• 206010018338 Glioma Diseases 0.000 description 4
• 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 description 4
• 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 4
• 101150113453 Gsk3a gene Proteins 0.000 description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• 101001060231 Homo sapiens F-box/WD repeat-containing protein 7 Proteins 0.000 description 4
• 102000004877 Insulin Human genes 0.000 description 4
• 108090001061 Insulin Proteins 0.000 description 4
• 206010025323 Lymphomas Diseases 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 229910019142 PO4 Inorganic materials 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 4
• 230000018199 S phase Effects 0.000 description 4
• 208000006011 Stroke Diseases 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 125000004423 acyloxy group Chemical group 0.000 description 4
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 4
• 125000005907 alkyl ester group Chemical group 0.000 description 4
• 239000002168 alkylating agent Substances 0.000 description 4
• 229940100198 alkylating agent Drugs 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 150000001409 amidines Chemical class 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• 239000003963 antioxidant agent Substances 0.000 description 4
• 235000006708 antioxidants Nutrition 0.000 description 4
• 239000000010 aprotic solvent Substances 0.000 description 4
• 125000003710 aryl alkyl group Chemical group 0.000 description 4
• IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 230000027455 binding Effects 0.000 description 4
• 230000008238 biochemical pathway Effects 0.000 description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
• 125000002843 carboxylic acid group Chemical group 0.000 description 4
• 230000004663 cell proliferation Effects 0.000 description 4
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• 239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 4
• 238000012217 deletion Methods 0.000 description 4
• 230000037430 deletion Effects 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 125000004185 ester group Chemical group 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 210000001035 gastrointestinal tract Anatomy 0.000 description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 4
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 4
• 230000002779 inactivation Effects 0.000 description 4
• 229940125396 insulin Drugs 0.000 description 4
• 230000003993 interaction Effects 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 125000000468 ketone group Chemical group 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 230000007246 mechanism Effects 0.000 description 4
• UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 4
• 239000003607 modifier Substances 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 235000021317 phosphate Nutrition 0.000 description 4
• 239000002798 polar solvent Substances 0.000 description 4
• 239000003755 preservative agent Substances 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
• 230000004083 survival effect Effects 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 4
• 125000001544 thienyl group Chemical group 0.000 description 4
• 230000014616 translation Effects 0.000 description 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 3
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 3
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 description 3
• 102000003737 3-Phosphoinositide-Dependent Protein Kinases Human genes 0.000 description 3
• 108010082078 3-Phosphoinositide-Dependent Protein Kinases Proteins 0.000 description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
• 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 3
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
• 208000003950 B-cell lymphoma Diseases 0.000 description 3
• 108060000903 Beta-catenin Proteins 0.000 description 3
• 102000015735 Beta-catenin Human genes 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 3
• 102100026865 Cyclin-dependent kinase 5 activator 1 Human genes 0.000 description 3
• 102100026810 Cyclin-dependent kinase 7 Human genes 0.000 description 3
• 229920000858 Cyclodextrin Polymers 0.000 description 3
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
• 230000010190 G1 phase Effects 0.000 description 3
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
• 208000032612 Glial tumor Diseases 0.000 description 3
• 108010001483 Glycogen Synthase Proteins 0.000 description 3
• 206010019196 Head injury Diseases 0.000 description 3
• 101000911952 Homo sapiens Cyclin-dependent kinase 7 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
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
• 239000000232 Lipid Bilayer Substances 0.000 description 3
• 108091054455 MAP kinase family Proteins 0.000 description 3
• 102000043136 MAP kinase family Human genes 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
• 208000012902 Nervous system disease Diseases 0.000 description 3
• 208000025966 Neurological disease Diseases 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
• 201000000582 Retinoblastoma Diseases 0.000 description 3
• 102100022828 Retinoblastoma-like protein 2 Human genes 0.000 description 3
• 108050002651 Retinoblastoma-like protein 2 Proteins 0.000 description 3
• 206010039491 Sarcoma Diseases 0.000 description 3
• 210000001744 T-lymphocyte Anatomy 0.000 description 3
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 3
• 108091023040 Transcription factor Proteins 0.000 description 3
• 102000040945 Transcription factor Human genes 0.000 description 3
• 229960000583 acetic acid Drugs 0.000 description 3
• BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 3
• 229950010817 alvocidib Drugs 0.000 description 3
• 125000004103 aminoalkyl group Chemical group 0.000 description 3
• 150000008064 anhydrides Chemical class 0.000 description 3
• 239000002246 antineoplastic agent Substances 0.000 description 3
• 229960005070 ascorbic acid Drugs 0.000 description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 150000001768 cations Chemical class 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 210000003169 central nervous system Anatomy 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 3
• 239000007822 coupling agent Substances 0.000 description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 3
• 230000002950 deficient Effects 0.000 description 3
• 230000030609 dephosphorylation Effects 0.000 description 3
• 238000006209 dephosphorylation reaction Methods 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 230000018109 developmental process Effects 0.000 description 3
• 238000003745 diagnosis Methods 0.000 description 3
• 238000002405 diagnostic procedure Methods 0.000 description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
• 206010015037 epilepsy Diseases 0.000 description 3
• 230000002068 genetic effect Effects 0.000 description 3
• 208000014829 head and neck neoplasm Diseases 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 201000005787 hematologic cancer Diseases 0.000 description 3
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 3
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
• 230000002209 hydrophobic effect Effects 0.000 description 3
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 3
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
• 125000001041 indolyl group Chemical group 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000000842 isoxazolyl group Chemical group 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
• 150000002772 monosaccharides Chemical group 0.000 description 3
• 125000006574 non-aromatic ring group Chemical group 0.000 description 3
• 125000002971 oxazolyl group Chemical group 0.000 description 3
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 125000003884 phenylalkyl group Chemical group 0.000 description 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
• 239000010452 phosphate Substances 0.000 description 3
• 125000003386 piperidinyl group Chemical group 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 230000000750 progressive effect Effects 0.000 description 3
• 230000035755 proliferation Effects 0.000 description 3
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
• 150000003246 quinazolines Chemical class 0.000 description 3
• 230000002285 radioactive effect Effects 0.000 description 3
• 125000006413 ring segment Chemical group 0.000 description 3
• 230000019491 signal transduction Effects 0.000 description 3
• 238000007920 subcutaneous administration Methods 0.000 description 3
• 125000000547 substituted alkyl group Chemical group 0.000 description 3
• 229940124530 sulfonamide Drugs 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 2
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 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
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
• OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 description 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
• ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical compound C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 2
• QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
• MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 2
• 125000006164 6-membered heteroaryl group Chemical group 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 201000001320 Atherosclerosis Diseases 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
• NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
• 229940126074 CDK kinase inhibitor Drugs 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
• 208000024172 Cardiovascular disease Diseases 0.000 description 2
• 102000003952 Caspase 3 Human genes 0.000 description 2
• 108090000397 Caspase 3 Proteins 0.000 description 2
• 206010008342 Cervix carcinoma Diseases 0.000 description 2
• 102000003910 Cyclin D Human genes 0.000 description 2
• 108090000259 Cyclin D Proteins 0.000 description 2
• 102000002435 Cyclin T Human genes 0.000 description 2
• 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 2
• 102100024456 Cyclin-dependent kinase 8 Human genes 0.000 description 2
• 102100034770 Cyclin-dependent kinase inhibitor 3 Human genes 0.000 description 2
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 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 2
• CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 108020004414 DNA Proteins 0.000 description 2
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-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
• 206010059866 Drug resistance Diseases 0.000 description 2
• 102000003951 Erythropoietin Human genes 0.000 description 2
• 108090000394 Erythropoietin Proteins 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 201000011240 Frontotemporal dementia Diseases 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 201000010915 Glioblastoma multiforme Diseases 0.000 description 2
• 206010018364 Glomerulonephritis Diseases 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
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 239000004471 Glycine Substances 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 2
• 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 2
• 101000980937 Homo sapiens Cyclin-dependent kinase 8 Proteins 0.000 description 2
• 101000733249 Homo sapiens Tumor suppressor ARF Proteins 0.000 description 2
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• 102000003746 Insulin Receptor Human genes 0.000 description 2
• 108010001127 Insulin Receptor Proteins 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 229930194542 Keto Natural products 0.000 description 2
• CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
• 229930195725 Mannitol Natural products 0.000 description 2
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 2
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoryl-L-serine Natural products OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
• 108091007960 PI3Ks Proteins 0.000 description 2
• 101150096038 PTH1R gene Proteins 0.000 description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 2
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 2
• 208000000609 Pick Disease of the Brain Diseases 0.000 description 2
• 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 2
• 229920002700 Polyoxyl 60 hydrogenated castor oil Polymers 0.000 description 2
• 108010012271 Positive Transcriptional Elongation Factor B Proteins 0.000 description 2
• 102000019014 Positive Transcriptional Elongation Factor B Human genes 0.000 description 2
• 108091008611 Protein Kinase B Proteins 0.000 description 2
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 2
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 2
• 101710149951 Protein Tat Proteins 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
• 102000009572 RNA Polymerase II Human genes 0.000 description 2
• 108010009460 RNA Polymerase II Proteins 0.000 description 2
• 206010070834 Sensitisation Diseases 0.000 description 2
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
• 229930006000 Sucrose Natural products 0.000 description 2
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 2
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 2
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
• 239000004473 Threonine Substances 0.000 description 2
• 102100023132 Transcription factor Jun Human genes 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
• 102000013814 Wnt Human genes 0.000 description 2
• 108050003627 Wnt Proteins 0.000 description 2
• 230000005856 abnormality Effects 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 239000001361 adipic acid Substances 0.000 description 2
• 235000011037 adipic acid Nutrition 0.000 description 2
• 229960000250 adipic acid Drugs 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 2
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
• 125000002009 alkene group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 230000033115 angiogenesis Effects 0.000 description 2
• 125000000129 anionic group Chemical group 0.000 description 2
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
• 230000002547 anomalous effect Effects 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• 229960005261 aspartic acid Drugs 0.000 description 2
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
• 229940092714 benzenesulfonic acid Drugs 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
• 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
• 229930188620 butyrolactone Natural products 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 150000001735 carboxylic acids Chemical class 0.000 description 2
• 230000015556 catabolic process Effects 0.000 description 2
• 230000021164 cell adhesion Effects 0.000 description 2
• 230000012820 cell cycle checkpoint Effects 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• 230000009134 cell regulation Effects 0.000 description 2
• 201000010881 cervical cancer Diseases 0.000 description 2
• 238000002512 chemotherapy Methods 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
• 238000013270 controlled release Methods 0.000 description 2
• 208000013044 corticobasal degeneration disease Diseases 0.000 description 2
• 150000003950 cyclic amides Chemical group 0.000 description 2
• 150000004292 cyclic ethers Chemical group 0.000 description 2
• 150000004294 cyclic thioethers Chemical group 0.000 description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
• RGBVWCQARBEPPW-UHFFFAOYSA-N cyclobut-3-ene-1,2-dione Chemical class O=C1C=CC1=O RGBVWCQARBEPPW-UHFFFAOYSA-N 0.000 description 2
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
• 238000006731 degradation reaction Methods 0.000 description 2
• 229950006137 dexfosfoserine Drugs 0.000 description 2
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 230000013020 embryo development Effects 0.000 description 2
• 150000002085 enols Chemical class 0.000 description 2
• 230000001973 epigenetic effect Effects 0.000 description 2
• 229940105423 erythropoietin Drugs 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
• FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 2
• 239000001530 fumaric acid Substances 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 230000030279 gene silencing Effects 0.000 description 2
• 238000010914 gene-directed enzyme pro-drug therapy Methods 0.000 description 2
• 102000034356 gene-regulatory proteins Human genes 0.000 description 2
• 108091006104 gene-regulatory proteins Proteins 0.000 description 2
• 208000005017 glioblastoma Diseases 0.000 description 2
• 229940097043 glucuronic acid Drugs 0.000 description 2
• 229960002989 glutamic acid Drugs 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 description 2
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• 229940071870 hydroiodic acid Drugs 0.000 description 2
• 230000006951 hyperphosphorylation Effects 0.000 description 2
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 239000007972 injectable composition Substances 0.000 description 2
• 230000006362 insulin response pathway Effects 0.000 description 2
• 230000002452 interceptive effect Effects 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 229940045996 isethionic acid Drugs 0.000 description 2
• 150000002540 isothiocyanates Chemical class 0.000 description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
• 229960000448 lactic acid Drugs 0.000 description 2
• 229940099563 lactobionic acid Drugs 0.000 description 2
• 150000002632 lipids Chemical class 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 210000004072 lung Anatomy 0.000 description 2
• 239000012931 lyophilized formulation Substances 0.000 description 2
• 239000011976 maleic acid Substances 0.000 description 2
• 239000001630 malic acid Substances 0.000 description 2
• 229940099690 malic acid Drugs 0.000 description 2
• 235000011090 malic acid Nutrition 0.000 description 2
• 239000000594 mannitol Substances 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 239000003550 marker Substances 0.000 description 2
• 239000011159 matrix material Substances 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
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 2
• XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
• MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical group O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
• PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
• 230000003204 osmotic effect Effects 0.000 description 2
• 229940127084 other anti-cancer agent Drugs 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 235000011007 phosphoric acid Nutrition 0.000 description 2
• 230000000865 phosphorylative effect Effects 0.000 description 2
• BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 2
• USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 0.000 description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
• 150000003053 piperidines Chemical class 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 239000008389 polyethoxylated castor oil Substances 0.000 description 2
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
• 229920000053 polysorbate 80 Polymers 0.000 description 2
• 229940068968 polysorbate 80 Drugs 0.000 description 2
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 238000004262 preparative liquid chromatography Methods 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 238000004393 prognosis Methods 0.000 description 2
• 230000000069 prophylactic effect Effects 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• 229940121649 protein inhibitor Drugs 0.000 description 2
• 239000012268 protein inhibitor Substances 0.000 description 2
• 150000003212 purines Chemical class 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
• 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 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• 238000001959 radiotherapy Methods 0.000 description 2
• 230000007115 recruitment Effects 0.000 description 2
• 238000006268 reductive amination reaction Methods 0.000 description 2
• 230000008844 regulatory mechanism Effects 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
• 230000008313 sensitization Effects 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 230000000087 stabilizing effect Effects 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 125000003107 substituted aryl group Chemical group 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 150000005846 sugar alcohols Polymers 0.000 description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
• HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
• MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical class O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 2
• 238000010189 synthetic method Methods 0.000 description 2
• 150000003512 tertiary amines Chemical class 0.000 description 2
• 150000003530 tetrahydroquinolines Chemical class 0.000 description 2
• 150000003536 tetrazoles Chemical group 0.000 description 2
• 150000003557 thiazoles Chemical class 0.000 description 2
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• 150000007970 thio esters Chemical class 0.000 description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
• 150000003568 thioethers Chemical class 0.000 description 2
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000007704 transition Effects 0.000 description 2
• 150000003852 triazoles Chemical class 0.000 description 2
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
• 229940005605 valeric acid Drugs 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 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
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
• 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-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
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• QHHHLHCCVDMOJI-UHFFFAOYSA-N 1,3-thiazol-4-amine Chemical class NC1=CSC=N1 QHHHLHCCVDMOJI-UHFFFAOYSA-N 0.000 description 1
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N 1-Pyrroline Chemical compound C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
• JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 description 1
• STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 description 1
• SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
• AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
• 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 description 1
• 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 description 1
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
• GHFDYLOGYDGRHI-UHFFFAOYSA-N 1h-indeno[1,2-c]pyrazol-4-one Chemical class C12=CC=CC=C2C(=O)C2=C1NN=C2 GHFDYLOGYDGRHI-UHFFFAOYSA-N 0.000 description 1
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical group NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
• JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 1
• JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical group C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
• CFCNTIFLYGKEIO-UHFFFAOYSA-N 2-isocyanoacetic acid Chemical compound OC(=O)C[N+]#[C-] CFCNTIFLYGKEIO-UHFFFAOYSA-N 0.000 description 1
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• IHMHRHIUJZAQDY-UHFFFAOYSA-N 2H-thiatriazine Chemical group N1SC=CN=N1 IHMHRHIUJZAQDY-UHFFFAOYSA-N 0.000 description 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
• UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
• SCHVGFGBJWBMFU-UHFFFAOYSA-N 3-sulfonylpyrazolo[3,4-b]pyridine Chemical class C1=CC=C2C(=S(=O)=O)N=NC2=N1 SCHVGFGBJWBMFU-UHFFFAOYSA-N 0.000 description 1
• XDADYJOYIMVXTH-UHFFFAOYSA-N 3h-imidazo[1,2-a]imidazole Chemical compound C1=CN2CC=NC2=N1 XDADYJOYIMVXTH-UHFFFAOYSA-N 0.000 description 1
• YCVAGNVTZICLNM-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzofuran Chemical compound C1CCCC2=C1C=CO2 YCVAGNVTZICLNM-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
• WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical group OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
• FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 102000019050 90-kDa Ribosomal Protein S6 Kinases Human genes 0.000 description 1
• 108010012196 90-kDa Ribosomal Protein S6 Kinases Proteins 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 206010065040 AIDS dementia complex Diseases 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
• 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
• 229930024421 Adenine Natural products 0.000 description 1
• 208000032467 Aplastic anaemia Diseases 0.000 description 1
• 101710095342 Apolipoprotein B Proteins 0.000 description 1
• 102100040202 Apolipoprotein B-100 Human genes 0.000 description 1
• 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 229910014033 C-OH Inorganic materials 0.000 description 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
• 102100034808 CCAAT/enhancer-binding protein alpha Human genes 0.000 description 1
• 101710168309 CCAAT/enhancer-binding protein alpha Proteins 0.000 description 1
• 101150012716 CDK1 gene Proteins 0.000 description 1
• 108050006947 CXC Chemokine Proteins 0.000 description 1
• 102000019388 CXC chemokine Human genes 0.000 description 1
• 108091008928 CXC chemokine receptors Proteins 0.000 description 1
• 102000054900 CXCR Receptors Human genes 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• 206010058019 Cancer Pain Diseases 0.000 description 1
• 102000018208 Cannabinoid Receptor Human genes 0.000 description 1
• 108050007331 Cannabinoid receptor Proteins 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
• 208000006029 Cardiomegaly Diseases 0.000 description 1
• 102000014914 Carrier Proteins Human genes 0.000 description 1
• 102000011727 Caspases Human genes 0.000 description 1
• 108010076667 Caspases Proteins 0.000 description 1
• 208000010833 Chronic myeloid leukaemia 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
• 229920002261 Corn starch Polymers 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• 102000002554 Cyclin A Human genes 0.000 description 1
• 108010068192 Cyclin A Proteins 0.000 description 1
• 102000002428 Cyclin C Human genes 0.000 description 1
• 108010068155 Cyclin C Proteins 0.000 description 1
• 102000002495 Cyclin H Human genes 0.000 description 1
• 108010068237 Cyclin H Proteins 0.000 description 1
• 108010068106 Cyclin T Proteins 0.000 description 1
• 108010009392 Cyclin-Dependent Kinase Inhibitor p16 Proteins 0.000 description 1
• 108010016777 Cyclin-Dependent Kinase Inhibitor p27 Proteins 0.000 description 1
• 102000000577 Cyclin-Dependent Kinase Inhibitor p27 Human genes 0.000 description 1
• 108091016115 Cyclin-T1 Proteins 0.000 description 1
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
• 201000003883 Cystic fibrosis Diseases 0.000 description 1
• 102000010831 Cytoskeletal Proteins Human genes 0.000 description 1
• 108010037414 Cytoskeletal Proteins Proteins 0.000 description 1
• 229910014570 C—OH Inorganic materials 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• 230000004544 DNA amplification Effects 0.000 description 1
• 230000004543 DNA replication Effects 0.000 description 1
• 230000004568 DNA-binding Effects 0.000 description 1
• 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
• 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
• 229920002307 Dextran Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 description 1
• 101001031598 Dictyostelium discoideum Probable serine/threonine-protein kinase fhkC Proteins 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• 101100457919 Drosophila melanogaster stg gene Proteins 0.000 description 1
• 102000036530 EDG receptors Human genes 0.000 description 1
• 108091007263 EDG receptors Proteins 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 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
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 229920003134 Eudragit® polymer Polymers 0.000 description 1
• 239000001263 FEMA 3042 Substances 0.000 description 1
• 108010014173 Factor X Proteins 0.000 description 1
• 108010074860 Factor Xa Proteins 0.000 description 1
• 201000008808 Fibrosarcoma Diseases 0.000 description 1
• 206010016717 Fistula Diseases 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• 208000004463 Follicular Adenocarcinoma Diseases 0.000 description 1
• 230000010337 G2 phase Effects 0.000 description 1
• 108091007911 GSKs Proteins 0.000 description 1
• DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
• 208000022072 Gallbladder Neoplasms Diseases 0.000 description 1
• 102100032863 General transcription factor IIH subunit 3 Human genes 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
• 102000004103 Glycogen Synthase Kinases Human genes 0.000 description 1
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 108010033040 Histones Proteins 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
• 101000945639 Homo sapiens Cyclin-dependent kinase inhibitor 3 Proteins 0.000 description 1
• 101000666405 Homo sapiens General transcription factor IIH subunit 1 Proteins 0.000 description 1
• 101000655398 Homo sapiens General transcription factor IIH subunit 2 Proteins 0.000 description 1
• 101000655391 Homo sapiens General transcription factor IIH subunit 3 Proteins 0.000 description 1
• 101000655406 Homo sapiens General transcription factor IIH subunit 4 Proteins 0.000 description 1
• 101000655402 Homo sapiens General transcription factor IIH subunit 5 Proteins 0.000 description 1
• 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 1
• 101100520968 Homo sapiens PPP1R1B gene Proteins 0.000 description 1
• 101000603402 Homo sapiens Protein NPAT Proteins 0.000 description 1
• 101001050288 Homo sapiens Transcription factor Jun Proteins 0.000 description 1
• 101001087394 Homo sapiens Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 description 1
• 241000701024 Human betaherpesvirus 5 Species 0.000 description 1
• 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
• 241000725303 Human immunodeficiency virus Species 0.000 description 1
• 208000031226 Hyperlipidaemia Diseases 0.000 description 1
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 102000004310 Ion Channels Human genes 0.000 description 1
• 108090000862 Ion Channels Proteins 0.000 description 1
• 208000007766 Kaposi sarcoma Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 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
• 239000002211 L-ascorbic acid Substances 0.000 description 1
• 235000000069 L-ascorbic acid Nutrition 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
• GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
• 102100027159 Membrane primary amine oxidase Human genes 0.000 description 1
• 101710132836 Membrane primary amine oxidase Proteins 0.000 description 1
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
• 102000029749 Microtubule Human genes 0.000 description 1
• 108091022875 Microtubule Proteins 0.000 description 1
• 101710115937 Microtubule-associated protein tau Proteins 0.000 description 1
• 241001024304 Mino Species 0.000 description 1
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 1
• 102100038895 Myc proto-oncogene protein Human genes 0.000 description 1
• 101710135898 Myc proto-oncogene protein Proteins 0.000 description 1
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
• 101150092630 Myt1 gene Proteins 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• DAIGNPIVBLSYCZ-UHFFFAOYSA-N N-methoxy-9H-fluoren-9-amine Chemical compound C1=CC=C2C(NOC)C3=CC=CC=C3C2=C1 DAIGNPIVBLSYCZ-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 102000007999 Nuclear Proteins Human genes 0.000 description 1
• 108010089610 Nuclear Proteins Proteins 0.000 description 1
• 102100034404 Nuclear factor of activated T-cells, cytoplasmic 1 Human genes 0.000 description 1
• 101710151542 Nuclear factor of activated T-cells, cytoplasmic 1 Proteins 0.000 description 1
• BHVRCUAHXVLSNX-UHFFFAOYSA-N O-[(4,5-dimethoxy-2-nitrophenyl)methyl]hydroxylamine Chemical compound COC1=CC(CON)=C([N+]([O-])=O)C=C1OC BHVRCUAHXVLSNX-UHFFFAOYSA-N 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 102000043276 Oncogene Human genes 0.000 description 1
• 108700020796 Oncogene Proteins 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 235000021314 Palmitic acid Nutrition 0.000 description 1
• 206010033799 Paralysis Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• 102000005877 Peptide Initiation Factors Human genes 0.000 description 1
• 108010044843 Peptide Initiation Factors Proteins 0.000 description 1
• SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
• 108010001441 Phosphopeptides Proteins 0.000 description 1
• 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
• 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
• 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 102100038870 Protein NPAT Human genes 0.000 description 1
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 1
• 102100024556 Protein phosphatase 1 regulatory subunit 1B Human genes 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 206010048829 Rectal adenoma Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• 108091027981 Response element Proteins 0.000 description 1
• 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
• 108050002653 Retinoblastoma protein Proteins 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 241000710960 Sindbis virus Species 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 229920001304 Solutol HS 15 Polymers 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000005718 Stomach Neoplasms Diseases 0.000 description 1
• 102000017299 Synapsin-1 Human genes 0.000 description 1
• 108050005241 Synapsin-1 Proteins 0.000 description 1
• 102000013265 Syntaxin 1 Human genes 0.000 description 1
• 108010090618 Syntaxin 1 Proteins 0.000 description 1
• 206010042971 T-cell lymphoma Diseases 0.000 description 1
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 229940123237 Taxane Drugs 0.000 description 1
• 108090000190 Thrombin Proteins 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 101710150448 Transcriptional regulator Myc Proteins 0.000 description 1
• 102000004243 Tubulin Human genes 0.000 description 1
• 108090000704 Tubulin Proteins 0.000 description 1
• 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
• 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
• 230000004156 Wnt signaling pathway Effects 0.000 description 1
• 101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 description 1
• 201000006083 Xeroderma Pigmentosum Diseases 0.000 description 1
• 241000607479 Yersinia pestis Species 0.000 description 1
• MIOPJNTWMNEORI-OMNKOJBGSA-N [(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-OMNKOJBGSA-N 0.000 description 1
• SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 1
• GVVWEQQBBATYME-UHFFFAOYSA-L [Na+].[Na+].[O-]N=O.[O-]N=O Chemical compound [Na+].[Na+].[O-]N=O.[O-]N=O GVVWEQQBBATYME-UHFFFAOYSA-L 0.000 description 1
• 230000001594 aberrant effect Effects 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 125000002015 acyclic group Chemical group 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 125000004442 acylamino group Chemical group 0.000 description 1
• 125000005042 acyloxymethyl group Chemical group 0.000 description 1
• 229960000643 adenine Drugs 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 229940121359 adenosine receptor antagonist Drugs 0.000 description 1
• 210000000577 adipose tissue Anatomy 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 125000003172 aldehyde group Chemical group 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 235000010443 alginic acid Nutrition 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
• 125000002723 alicyclic group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000005037 alkyl phenyl group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 238000010976 amide bond formation reaction Methods 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 229960004909 aminosalicylic acid Drugs 0.000 description 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
• 229950003476 aminothiazole Drugs 0.000 description 1
• DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 208000007502 anemia Diseases 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000454 anti-cipatory effect Effects 0.000 description 1
• 230000003474 anti-emetic effect Effects 0.000 description 1
• 230000002924 anti-infective effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 238000011319 anticancer therapy Methods 0.000 description 1
• 239000003146 anticoagulant agent Substances 0.000 description 1
• 229940127219 anticoagulant drug Drugs 0.000 description 1
• 239000002111 antiemetic agent Substances 0.000 description 1
• 229940125683 antiemetic agent Drugs 0.000 description 1
• 238000010913 antigen-directed enzyme pro-drug therapy Methods 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 230000006793 arrhythmia Effects 0.000 description 1
• 206010003119 arrhythmia Diseases 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 239000003719 aurora kinase inhibitor Substances 0.000 description 1
• 230000001363 autoimmune Effects 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• 230000035578 autophosphorylation Effects 0.000 description 1
• AAMATCKFMHVIDO-UHFFFAOYSA-N azane;1h-pyrrole Chemical compound N.C=1C=CNC=1 AAMATCKFMHVIDO-UHFFFAOYSA-N 0.000 description 1
• JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 239000000022 bacteriostatic agent Substances 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 229960004365 benzoic acid Drugs 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• 125000001743 benzylic group Chemical group 0.000 description 1
• GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
• GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
• LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 description 1
• 108091008324 binding proteins Proteins 0.000 description 1
• 230000003851 biochemical process Effects 0.000 description 1
• 230000008827 biological function Effects 0.000 description 1
• 239000012472 biological sample Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000006664 bond formation reaction Methods 0.000 description 1
• 201000000488 breast squamous cell carcinoma Diseases 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 125000005998 bromoethyl group Chemical group 0.000 description 1
• 239000007853 buffer solution Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 239000007894 caplet Substances 0.000 description 1
• 239000007963 capsule composition Substances 0.000 description 1
• 150000001718 carbodiimides Chemical class 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 150000001733 carboxylic acid esters Chemical class 0.000 description 1
• 239000003729 cation exchange resin Substances 0.000 description 1
• 150000001767 cationic compounds Chemical class 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 101150069072 cdc25 gene Proteins 0.000 description 1
• 230000025084 cell cycle arrest Effects 0.000 description 1
• 230000006369 cell cycle progression Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000009087 cell motility Effects 0.000 description 1
• 238000001516 cell proliferation assay Methods 0.000 description 1
• 230000036755 cellular response Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 208000015114 central nervous system disease Diseases 0.000 description 1
• 208000025434 cerebellar degeneration Diseases 0.000 description 1
• 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
• NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
• 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
• 235000012000 cholesterol Nutrition 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 210000000349 chromosome Anatomy 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 235000013985 cinnamic acid Nutrition 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
• 238000003776 cleavage reaction Methods 0.000 description 1
• 230000008045 co-localization Effects 0.000 description 1
• 239000008139 complexing agent Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 229920006037 cross link polymer Polymers 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
• 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• 231100000135 cytotoxicity Toxicity 0.000 description 1
• 230000003013 cytotoxicity Effects 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000001934 delay Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 230000002074 deregulated effect Effects 0.000 description 1
• 230000003831 deregulation Effects 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 125000004663 dialkyl amino group Chemical group 0.000 description 1
• 235000020805 dietary restrictions Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 230000008482 dysregulation Effects 0.000 description 1
• 239000003221 ear drop Substances 0.000 description 1
• 125000006575 electron-withdrawing group Chemical group 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• 230000006353 environmental stress Effects 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 210000003743 erythrocyte Anatomy 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 235000019439 ethyl acetate Nutrition 0.000 description 1
• 235000019325 ethyl cellulose Nutrition 0.000 description 1
• 229920001249 ethyl cellulose Polymers 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 210000003527 eukaryotic cell Anatomy 0.000 description 1
• 230000003492 excitotoxic effect Effects 0.000 description 1
• 231100000063 excitotoxicity Toxicity 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 239000007888 film coating Substances 0.000 description 1
• 238000009501 film coating Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 230000003890 fistula Effects 0.000 description 1
• 125000003709 fluoroalkyl group Chemical group 0.000 description 1
• 238000005187 foaming Methods 0.000 description 1
• 239000004088 foaming agent Substances 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 150000002244 furazanes Chemical class 0.000 description 1
• DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
• 201000010175 gallbladder cancer Diseases 0.000 description 1
• LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
• 206010017758 gastric cancer Diseases 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 229960005219 gentisic acid Drugs 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229950006191 gluconic acid Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229930182470 glycoside Natural products 0.000 description 1
• 150000002338 glycosides Chemical class 0.000 description 1
• 239000003979 granulating agent Substances 0.000 description 1
• 210000003714 granulocyte Anatomy 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
• 201000010536 head and neck cancer Diseases 0.000 description 1
• 208000014951 hematologic disease Diseases 0.000 description 1
• 230000002363 herbicidal effect Effects 0.000 description 1
• 125000006038 hexenyl group Chemical group 0.000 description 1
• 150000002402 hexoses Chemical class 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
• 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
• 229960000443 hydrochloric acid Drugs 0.000 description 1
• MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 230000006607 hypermethylation Effects 0.000 description 1
• 230000003463 hyperproliferative effect Effects 0.000 description 1
• 229960004716 idoxuridine Drugs 0.000 description 1
• 210000003405 ileum Anatomy 0.000 description 1
• UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 1
• CQQJSOXDEFZGFG-UHFFFAOYSA-N imidazo[4,5-d]imidazole Chemical compound C1=NC2=NC=NC2=N1 CQQJSOXDEFZGFG-UHFFFAOYSA-N 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 125000001841 imino group Chemical group [H]N=* 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910001411 inorganic cation Inorganic materials 0.000 description 1
• 239000002917 insecticide Substances 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 230000031146 intracellular signal transduction Effects 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 206010073095 invasive ductal breast carcinoma Diseases 0.000 description 1
• 201000010985 invasive ductal carcinoma Diseases 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound 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 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
• 229960004768 irinotecan Drugs 0.000 description 1
• FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 208000037906 ischaemic injury Diseases 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 230000000155 isotopic effect Effects 0.000 description 1
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 150000003951 lactams Chemical group 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000019423 liver disease Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 210000005228 liver tissue Anatomy 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 210000002751 lymph Anatomy 0.000 description 1
• 210000004698 lymphocyte Anatomy 0.000 description 1
• 238000012792 lyophilization process Methods 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• 210000002540 macrophage Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229940098895 maleic acid Drugs 0.000 description 1
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
• 230000036210 malignancy Effects 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 208000026037 malignant tumor of neck Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 150000002739 metals Chemical class 0.000 description 1
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 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
• 210000004688 microtubule Anatomy 0.000 description 1
• 230000008880 microtubule cytoskeleton organization Effects 0.000 description 1
• 231100000782 microtubule inhibitor Toxicity 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 230000002297 mitogenic effect Effects 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 230000011278 mitosis Effects 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
• PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
• 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 230000004899 motility Effects 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 210000002346 musculoskeletal system Anatomy 0.000 description 1
• 238000002703 mutagenesis Methods 0.000 description 1
• 231100000350 mutagenesis Toxicity 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
• GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• SJWPLOQINHZILX-UHFFFAOYSA-N n-ethoxybenzenesulfonamide Chemical compound CCONS(=O)(=O)C1=CC=CC=C1 SJWPLOQINHZILX-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound 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 compound 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
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000001613 neoplastic effect Effects 0.000 description 1
• 230000030363 nerve development Effects 0.000 description 1
• 230000001537 neural effect Effects 0.000 description 1
• 208000007538 neurilemmoma Diseases 0.000 description 1
• 230000000626 neurodegenerative effect Effects 0.000 description 1
• 230000009223 neuronal apoptosis Effects 0.000 description 1
• 230000006764 neuronal dysfunction Effects 0.000 description 1
• 239000002858 neurotransmitter agent Substances 0.000 description 1
• 208000004235 neutropenia Diseases 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• LUHFJLLCZSYACL-UHFFFAOYSA-N o-(2,2,2-trichloroethyl)hydroxylamine Chemical compound NOCC(Cl)(Cl)Cl LUHFJLLCZSYACL-UHFFFAOYSA-N 0.000 description 1
• XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
• KKVUFSINQFSJNK-UHFFFAOYSA-N o-tert-butylhydroxylamine Chemical compound CC(C)(C)ON KKVUFSINQFSJNK-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
• 229960002446 octanoic acid Drugs 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002892 organic cations Chemical class 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 229960005010 orotic acid Drugs 0.000 description 1
• 201000008968 osteosarcoma Diseases 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
• 150000002916 oxazoles Chemical class 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 238000010979 pH adjustment Methods 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 150000002972 pentoses Chemical class 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• 239000008363 phosphate buffer Substances 0.000 description 1
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
• 239000007981 phosphate-citrate buffer Substances 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 238000002428 photodynamic therapy Methods 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
• LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
• 239000003880 polar aprotic solvent Substances 0.000 description 1
• 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
• 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 208000014081 polyp of colon Diseases 0.000 description 1
• 229920001184 polypeptide 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
• 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 238000010837 poor prognosis Methods 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
• 229940098458 powder spray Drugs 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 230000000861 pro-apoptotic effect Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 230000009822 protein phosphorylation Effects 0.000 description 1
• 238000001243 protein synthesis Methods 0.000 description 1
• 239000003806 protein tyrosine phosphatase inhibitor Substances 0.000 description 1
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 1
• 230000004850 protein–protein interaction Effects 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 230000000541 pulsatile effect Effects 0.000 description 1
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical group C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 201000003780 rectum adenoma Diseases 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000031539 regulation of cell division Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 230000028617 response to DNA damage stimulus Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 229940116353 sebacic acid Drugs 0.000 description 1
• 208000011581 secondary neoplasm Diseases 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical compound C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 description 1
• 230000035939 shock Effects 0.000 description 1
• 238000009097 single-agent therapy Methods 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 201000000849 skin cancer Diseases 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000008279 sol Substances 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000007790 solid phase Substances 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 208000002320 spinal muscular atrophy Diseases 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 208000013274 squamous cell breast carcinoma Diseases 0.000 description 1
• 206010041823 squamous cell carcinoma Diseases 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 229960004274 stearic acid Drugs 0.000 description 1
• 239000008227 sterile water for injection Substances 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 201000011549 stomach cancer Diseases 0.000 description 1
• 230000035882 stress Effects 0.000 description 1
• 125000005504 styryl group Chemical group 0.000 description 1
• 239000006190 sub-lingual tablet Substances 0.000 description 1
• 238000003883 substance clean up Methods 0.000 description 1
• 125000005156 substituted alkylene group Chemical group 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003871 sulfonates Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 229940032330 sulfuric acid Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000007916 tablet composition Substances 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• 238000002626 targeted therapy Methods 0.000 description 1
• 230000008685 targeting Effects 0.000 description 1
• 230000002123 temporal effect Effects 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
• 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
• 229940033663 thimerosal Drugs 0.000 description 1
• 150000003556 thioamides Chemical class 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 229960004072 thrombin Drugs 0.000 description 1
• 230000009424 thromboembolic effect Effects 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• 210000001685 thyroid gland Anatomy 0.000 description 1
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
• 108700012359 toxins Proteins 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 238000013519 translation Methods 0.000 description 1
• 230000014621 translational initiation Effects 0.000 description 1
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 230000001960 triggered effect Effects 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 108010036927 trypsin-like serine protease Proteins 0.000 description 1
• 230000005748 tumor development Effects 0.000 description 1
• 230000007306 turnover Effects 0.000 description 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
• 241000701161 unidentified adenovirus Species 0.000 description 1
• 241001529453 unidentified herpesvirus Species 0.000 description 1
• 150000003673 urethanes Chemical class 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 125000005500 uronium group Chemical group 0.000 description 1
• 239000002966 varnish Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 239000001993 wax Substances 0.000 description 1