MXPA05003084A - Nuevos compuestos para la inhibicion de rotamasas y usos de los mismos. - Google Patents
Nuevos compuestos para la inhibicion de rotamasas y usos de los mismos.Info
- Publication number
- MXPA05003084A MXPA05003084A MXPA05003084A MXPA05003084A MXPA05003084A MX PA05003084 A MXPA05003084 A MX PA05003084A MX PA05003084 A MXPA05003084 A MX PA05003084A MX PA05003084 A MXPA05003084 A MX PA05003084A MX PA05003084 A MXPA05003084 A MX PA05003084A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- hydroxy
- chloro
- phenol
- urea
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 350
- 101710103508 FK506-binding protein Proteins 0.000 title claims description 48
- 101710104425 FK506-binding protein 2 Proteins 0.000 title claims description 48
- 101710104423 FK506-binding protein 3 Proteins 0.000 title claims description 48
- 101710104333 FK506-binding protein 4 Proteins 0.000 title claims description 48
- 101710104342 FK506-binding protein 5 Proteins 0.000 title claims description 48
- 101710149710 FKBP-type 16 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710121306 FKBP-type 22 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710180800 FKBP-type peptidyl-prolyl cis-trans isomerase FkpA Proteins 0.000 title claims description 48
- 101710104030 Long-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710114693 Outer membrane protein MIP Proteins 0.000 title claims description 48
- 101710116692 Peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710111764 Peptidyl-prolyl cis-trans isomerase FKBP10 Proteins 0.000 title claims description 48
- 101710111749 Peptidyl-prolyl cis-trans isomerase FKBP11 Proteins 0.000 title claims description 48
- 101710111747 Peptidyl-prolyl cis-trans isomerase FKBP12 Proteins 0.000 title claims description 48
- 101710111757 Peptidyl-prolyl cis-trans isomerase FKBP14 Proteins 0.000 title claims description 48
- 101710111682 Peptidyl-prolyl cis-trans isomerase FKBP1A Proteins 0.000 title claims description 48
- 101710111689 Peptidyl-prolyl cis-trans isomerase FKBP1B Proteins 0.000 title claims description 48
- 101710147154 Peptidyl-prolyl cis-trans isomerase FKBP2 Proteins 0.000 title claims description 48
- 101710147149 Peptidyl-prolyl cis-trans isomerase FKBP3 Proteins 0.000 title claims description 48
- 101710147152 Peptidyl-prolyl cis-trans isomerase FKBP4 Proteins 0.000 title claims description 48
- 101710147150 Peptidyl-prolyl cis-trans isomerase FKBP5 Proteins 0.000 title claims description 48
- 101710147138 Peptidyl-prolyl cis-trans isomerase FKBP7 Proteins 0.000 title claims description 48
- 101710147137 Peptidyl-prolyl cis-trans isomerase FKBP8 Proteins 0.000 title claims description 48
- 101710147136 Peptidyl-prolyl cis-trans isomerase FKBP9 Proteins 0.000 title claims description 48
- 101710174853 Peptidyl-prolyl cis-trans isomerase Mip Proteins 0.000 title claims description 48
- 101710200991 Peptidyl-prolyl cis-trans isomerase, rhodopsin-specific isozyme Proteins 0.000 title claims description 48
- 101710092145 Peptidyl-prolyl cis-trans isomerase-like 1 Proteins 0.000 title claims description 48
- 101710092146 Peptidyl-prolyl cis-trans isomerase-like 2 Proteins 0.000 title claims description 48
- 101710092148 Peptidyl-prolyl cis-trans isomerase-like 3 Proteins 0.000 title claims description 48
- 101710092149 Peptidyl-prolyl cis-trans isomerase-like 4 Proteins 0.000 title claims description 48
- 101710113444 Probable parvulin-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710090737 Probable peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710133309 Putative peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 101710124237 Short-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 title claims description 48
- 102100038809 Peptidyl-prolyl cis-trans isomerase FKBP9 Human genes 0.000 title claims 9
- 230000005764 inhibitory process Effects 0.000 title description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 128
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 116
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 82
- 125000001072 heteroaryl group Chemical class 0.000 claims abstract description 77
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 71
- 125000003118 aryl group Chemical class 0.000 claims abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 34
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 24
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 23
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000006850 spacer group Chemical group 0.000 claims abstract description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 41
- 125000003107 substituted aryl group Chemical class 0.000 claims abstract 31
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 29
- -1 OR16 Chemical group 0.000 claims description 363
- 239000004202 carbamide Substances 0.000 claims description 116
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 103
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 99
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 76
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 44
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 44
- 201000010099 disease Diseases 0.000 claims description 41
- 239000003112 inhibitor Substances 0.000 claims description 40
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 39
- 210000004027 cell Anatomy 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- 238000004519 manufacturing process Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 230000004663 cell proliferation Effects 0.000 claims description 24
- 235000019260 propionic acid Nutrition 0.000 claims description 22
- 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 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 208000015181 infectious disease Diseases 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 230000011278 mitosis Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 230000002062 proliferating effect Effects 0.000 claims description 13
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 11
- 241000700605 Viruses Species 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 230000022131 cell cycle Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 206010017533 Fungal infection Diseases 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 206010037660 Pyrexia Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 230000002159 abnormal effect Effects 0.000 claims description 5
- 230000001413 cellular effect Effects 0.000 claims description 5
- 210000005170 neoplastic cell Anatomy 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 3
- 206010005098 Blastomycosis Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 102100039250 Essential MCU regulator, mitochondrial Human genes 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 101000813097 Homo sapiens Essential MCU regulator, mitochondrial Proteins 0.000 claims description 3
- 206010020880 Hypertrophy Diseases 0.000 claims description 3
- 208000030852 Parasitic disease Diseases 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000002255 enzymatic effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000003176 fibrotic effect Effects 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
- 210000001519 tissue Anatomy 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 241000242722 Cestoda Species 0.000 claims description 2
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 2
- 206010018612 Gonorrhoea Diseases 0.000 claims description 2
- 101000891031 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP10 Proteins 0.000 claims description 2
- 101000891028 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP11 Proteins 0.000 claims description 2
- 101000891014 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP14 Proteins 0.000 claims description 2
- 101001060744 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP1A Proteins 0.000 claims description 2
- 101001060736 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP1B Proteins 0.000 claims description 2
- 101000914053 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP2 Proteins 0.000 claims description 2
- 101000827313 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP3 Proteins 0.000 claims description 2
- 101000932178 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP4 Proteins 0.000 claims description 2
- 101000878253 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP5 Proteins 0.000 claims description 2
- 101000878215 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP7 Proteins 0.000 claims description 2
- 101000878221 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP8 Proteins 0.000 claims description 2
- 101001031398 Homo sapiens Peptidyl-prolyl cis-trans isomerase FKBP9 Proteins 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 241000589248 Legionella Species 0.000 claims description 2
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000010315 Mastoiditis Diseases 0.000 claims description 2
- 241000041810 Mycetoma Species 0.000 claims description 2
- 208000001738 Nervous System Trauma Diseases 0.000 claims description 2
- 241000187654 Nocardia Species 0.000 claims description 2
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 claims description 2
- 206010035148 Plague Diseases 0.000 claims description 2
- 208000024777 Prion disease Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 206010038563 Reocclusion Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010043376 Tetanus Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 201000006824 bubonic plague Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 208000001848 dysentery Diseases 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 208000001786 gonorrhea Diseases 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 208000028412 nervous system injury Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- 230000003582 thrombocytopenic effect Effects 0.000 claims description 2
- 230000017423 tissue regeneration Effects 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 31
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 28
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 8
- 229960001755 resorcinol Drugs 0.000 claims 7
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 6
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 4
- 208000035473 Communicable disease Diseases 0.000 claims 4
- 150000001336 alkenes Chemical class 0.000 claims 4
- GGNQRNBDZQJCCN-UHFFFAOYSA-N hydroxyhydroquinone Natural products OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims 4
- 230000002757 inflammatory effect Effects 0.000 claims 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- 230000001613 neoplastic effect Effects 0.000 claims 3
- NIQGNGRQHWJKQE-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-(4-chlorophenyl)urea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1O NIQGNGRQHWJKQE-UHFFFAOYSA-N 0.000 claims 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 2
- VTCDZPUMZAZMSB-UHFFFAOYSA-N 3,4,5-trimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1OC VTCDZPUMZAZMSB-UHFFFAOYSA-N 0.000 claims 2
- DXOSJQLIRGXWCF-UHFFFAOYSA-N 3-fluorocatechol Chemical compound OC1=CC=CC(F)=C1O DXOSJQLIRGXWCF-UHFFFAOYSA-N 0.000 claims 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 claims 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 claims 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 claims 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims 2
- 241001139947 Mida Species 0.000 claims 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 229940097275 indigo Drugs 0.000 claims 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims 2
- RNYURNUANACIKS-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)methanamine Chemical compound NCC1=CC=CC=C1N1CCOCC1 RNYURNUANACIKS-UHFFFAOYSA-N 0.000 claims 1
- BNJARXOEVLYKDN-UHFFFAOYSA-N (3,5-dichlorophenyl)thiourea Chemical compound NC(=S)NC1=CC(Cl)=CC(Cl)=C1 BNJARXOEVLYKDN-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- IHFUPINOVHTFNO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-(3,5-dichloro-4-hydroxyphenyl)urea Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=O)NC1=CC=C(OCO2)C2=C1 IHFUPINOVHTFNO-UHFFFAOYSA-N 0.000 claims 1
- UFYXKZJEHYFEQL-UHFFFAOYSA-N 1-(1-adamantyl)-3-(3-fluoro-2-hydroxyphenyl)urea Chemical compound OC1=C(F)C=CC=C1NC(=O)NC1(C2)CC(C3)CC2CC3C1 UFYXKZJEHYFEQL-UHFFFAOYSA-N 0.000 claims 1
- UDJSKCOXUGHMQA-UHFFFAOYSA-N 1-(1-adamantyl)-3-(5-chloro-2-hydroxyphenyl)urea Chemical compound OC1=CC=C(Cl)C=C1NC(=O)NC1(C2)CC(C3)CC2CC3C1 UDJSKCOXUGHMQA-UHFFFAOYSA-N 0.000 claims 1
- NGEZPJSWVHIODO-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC=C(O)C=C1O NGEZPJSWVHIODO-UHFFFAOYSA-N 0.000 claims 1
- HGEZORLIEPPJTR-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(3-fluoro-4-hydroxyphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC=C(O)C(F)=C1 HGEZORLIEPPJTR-UHFFFAOYSA-N 0.000 claims 1
- QQXZEQLVVRCIDL-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)-3-pentylurea Chemical compound CCCCCNC(=O)NC1=CC=C(C)C=C1O QQXZEQLVVRCIDL-UHFFFAOYSA-N 0.000 claims 1
- QFSODHRAGZNEPF-UHFFFAOYSA-N 1-(3,4-difluoro-2-hydroxyphenyl)-3-(2,4,4-trimethylpentan-2-yl)thiourea Chemical compound CC(C)(C)CC(C)(C)NC(=S)NC1=CC=C(F)C(F)=C1O QFSODHRAGZNEPF-UHFFFAOYSA-N 0.000 claims 1
- BIRVERCDWRAWOI-UHFFFAOYSA-N 1-(3,4-difluoro-2-hydroxyphenyl)-3-phenylthiourea Chemical compound OC1=C(F)C(F)=CC=C1NC(=S)NC1=CC=CC=C1 BIRVERCDWRAWOI-UHFFFAOYSA-N 0.000 claims 1
- HAEVNGWSGXYBEL-UHFFFAOYSA-N 1-(3,5-dibromo-4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)NC=2C=C(Br)C(O)=C(Br)C=2)=C1 HAEVNGWSGXYBEL-UHFFFAOYSA-N 0.000 claims 1
- FOYGPMWFMKLMDX-UHFFFAOYSA-N 1-(3,5-dibromo-4-hydroxyphenyl)-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=C(Br)C(O)=C(Br)C=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 FOYGPMWFMKLMDX-UHFFFAOYSA-N 0.000 claims 1
- URFKQEYSQSLKGL-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxy-4-methylphenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C(=C(Cl)C(C)=C(Cl)C=2)O)=C1 URFKQEYSQSLKGL-UHFFFAOYSA-N 0.000 claims 1
- XJDNHVFNNFSYFB-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxy-4-methylphenyl)-3-(4-phenoxyphenyl)urea Chemical compound OC1=C(Cl)C(C)=C(Cl)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 XJDNHVFNNFSYFB-UHFFFAOYSA-N 0.000 claims 1
- WWNJPJSMHUODNZ-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxy-4-methylphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound OC1=C(Cl)C(C)=C(Cl)C=C1NC(=O)NCC1=CC=C(C(F)(F)F)C=C1 WWNJPJSMHUODNZ-UHFFFAOYSA-N 0.000 claims 1
- KUEHCAPQHXOHLN-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxyphenyl)-3-(2-phenylethyl)urea Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)NCCC1=CC=CC=C1 KUEHCAPQHXOHLN-UHFFFAOYSA-N 0.000 claims 1
- XKJNBJNDZDNVHA-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxyphenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C(=C(Cl)C=C(Cl)C=2)O)=C1 XKJNBJNDZDNVHA-UHFFFAOYSA-N 0.000 claims 1
- GVYMCUZDVYMSQX-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxyphenyl)-3-phenylurea Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)NC1=CC=CC=C1 GVYMCUZDVYMSQX-UHFFFAOYSA-N 0.000 claims 1
- HCPVYDLEUIKZSE-UHFFFAOYSA-N 1-(3,5-dichloro-4-hydroxyphenyl)-3-(3,5-dichlorophenyl)thiourea Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=S)NC1=CC(Cl)=CC(Cl)=C1 HCPVYDLEUIKZSE-UHFFFAOYSA-N 0.000 claims 1
- KRQYCDOWPOEVHZ-UHFFFAOYSA-N 1-(3,5-dichloro-4-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=O)NCC1=CC=C(C(F)(F)F)C=C1 KRQYCDOWPOEVHZ-UHFFFAOYSA-N 0.000 claims 1
- NQKFIGAPZOVSRL-UHFFFAOYSA-N 1-(3,5-dichloro-4-hydroxyphenyl)-3-phenylthiourea Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=S)NC1=CC=CC=C1 NQKFIGAPZOVSRL-UHFFFAOYSA-N 0.000 claims 1
- LSNIYCUAPHIQHF-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-(3,5-difluoro-4-hydroxyphenyl)thiourea Chemical compound C1=C(F)C(O)=C(F)C=C1NC(=S)NC1=CC(Cl)=CC(Cl)=C1 LSNIYCUAPHIQHF-UHFFFAOYSA-N 0.000 claims 1
- CZKHXJKWCFEDJL-UHFFFAOYSA-N 1-(3,5-difluoro-4-hydroxyphenyl)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(F)=C(O)C(F)=C1 CZKHXJKWCFEDJL-UHFFFAOYSA-N 0.000 claims 1
- YWNDDHAKSNGUTK-UHFFFAOYSA-N 1-(3,5-difluoro-4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)NC=2C=C(F)C(O)=C(F)C=2)=C1 YWNDDHAKSNGUTK-UHFFFAOYSA-N 0.000 claims 1
- QEXCDSWJPMBUCA-UHFFFAOYSA-N 1-(3,5-difluoro-4-hydroxyphenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(F)C(O)=C(F)C=2)=C1 QEXCDSWJPMBUCA-UHFFFAOYSA-N 0.000 claims 1
- GTAPXYLCRVWOPJ-UHFFFAOYSA-N 1-(3,5-difluoro-4-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]thiourea Chemical compound C1=C(F)C(O)=C(F)C=C1NC(=S)NC1=CC=CC=C1C(F)(F)F GTAPXYLCRVWOPJ-UHFFFAOYSA-N 0.000 claims 1
- QZEQWBIEZBZSHZ-UHFFFAOYSA-N 1-(3,5-difluoro-4-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound C1=C(F)C(O)=C(F)C=C1NC(=O)NCC1=CC=C(C(F)(F)F)C=C1 QZEQWBIEZBZSHZ-UHFFFAOYSA-N 0.000 claims 1
- MPAYBRCDPJKSQT-UHFFFAOYSA-N 1-(3-amino-5-chloro-4-hydroxyphenyl)-3-(2,4,4-trimethylpentan-2-yl)urea Chemical compound CC(C)(C)CC(C)(C)NC(=O)NC1=CC(N)=C(O)C(Cl)=C1 MPAYBRCDPJKSQT-UHFFFAOYSA-N 0.000 claims 1
- IUIANQVUMKRYBF-UHFFFAOYSA-N 1-(3-chloro-2-hydroxyphenyl)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC=CC(Cl)=C1O IUIANQVUMKRYBF-UHFFFAOYSA-N 0.000 claims 1
- MIYKUZLNYDYGPM-UHFFFAOYSA-N 1-(3-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)urea 1-(3-chloro-2-hydroxyphenyl)-3-(3,5-dichlorophenyl)urea 1-(3-chloro-2-hydroxyphenyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)Cl)O.ClC=1C(=C(C=CC1)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O MIYKUZLNYDYGPM-UHFFFAOYSA-N 0.000 claims 1
- GMQMVTWVWUWVFO-UHFFFAOYSA-N 1-(3-chloro-2-hydroxyphenyl)-3-(4-cyanophenyl)urea Chemical compound OC1=C(Cl)C=CC=C1NC(=O)NC1=CC=C(C#N)C=C1 GMQMVTWVWUWVFO-UHFFFAOYSA-N 0.000 claims 1
- KJMDYCHMZQVOBZ-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-(4-chlorophenyl)thiourea Chemical compound C1=C(Cl)C(O)=CC=C1NC(=S)NC1=CC=C(Cl)C=C1 KJMDYCHMZQVOBZ-UHFFFAOYSA-N 0.000 claims 1
- NMMMHVCPHJMROU-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-(4-phenoxyphenyl)urea Chemical compound C1=C(Cl)C(O)=CC=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 NMMMHVCPHJMROU-UHFFFAOYSA-N 0.000 claims 1
- AILHZIBRDZGPTI-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-[(2-methylphenyl)methyl]thiourea Chemical compound CC1=CC=CC=C1CNC(=S)NC1=CC=C(O)C(Cl)=C1 AILHZIBRDZGPTI-UHFFFAOYSA-N 0.000 claims 1
- SIWHXZJRWGACER-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]thiourea Chemical compound C1=C(Cl)C(O)=CC=C1NC(=S)NCC1=CC=C(C(F)(F)F)C=C1 SIWHXZJRWGACER-UHFFFAOYSA-N 0.000 claims 1
- GHCOLQVWUMJESJ-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-cyclohexylthiourea Chemical compound C1=C(Cl)C(O)=CC=C1NC(=S)NC1CCCCC1 GHCOLQVWUMJESJ-UHFFFAOYSA-N 0.000 claims 1
- ACEIYXCKKMAJEN-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)-3-naphthalen-1-ylurea Chemical compound C1=C(Cl)C(O)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 ACEIYXCKKMAJEN-UHFFFAOYSA-N 0.000 claims 1
- VLTYOEWMUZCCBG-UHFFFAOYSA-N 1-(3-fluoro-2-hydroxyphenyl)-3-phenylurea Chemical compound OC1=C(F)C=CC=C1NC(=O)NC1=CC=CC=C1 VLTYOEWMUZCCBG-UHFFFAOYSA-N 0.000 claims 1
- XFYUKCFDEKTISJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(2,4-dihydroxyphenyl)thiourea Chemical compound OC1=CC(O)=CC=C1NC(=S)NC1=CC=C(Cl)C=C1 XFYUKCFDEKTISJ-UHFFFAOYSA-N 0.000 claims 1
- LAQHORKUXHZQLH-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)thiourea Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=S)NC1=CC=C(Cl)C=C1 LAQHORKUXHZQLH-UHFFFAOYSA-N 0.000 claims 1
- STLHKONQFNVDBS-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-fluoro-4-hydroxyphenyl)urea Chemical compound C1=C(F)C(O)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 STLHKONQFNVDBS-UHFFFAOYSA-N 0.000 claims 1
- SYRCKWNQALOPEW-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-(3,5-dichloro-2-hydroxy-4-methylphenyl)urea Chemical compound OC1=C(Cl)C(C)=C(Cl)C=C1NC(=O)NC1=CC=C(C#N)C=C1 SYRCKWNQALOPEW-UHFFFAOYSA-N 0.000 claims 1
- ZZSZMLXKJITMMF-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)NC1=CC=C(C#N)C=C1 ZZSZMLXKJITMMF-UHFFFAOYSA-N 0.000 claims 1
- DAGDJAYERAUBFF-UHFFFAOYSA-N 1-(4-hydroxy-3-nitrophenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(C(O)=CC=2)[N+]([O-])=O)=C1 DAGDJAYERAUBFF-UHFFFAOYSA-N 0.000 claims 1
- OTXNZNSHUXSOGI-UHFFFAOYSA-N 1-(4-hydroxy-3-nitrophenyl)-3-phenylthiourea Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1NC(=S)NC1=CC=CC=C1 OTXNZNSHUXSOGI-UHFFFAOYSA-N 0.000 claims 1
- ALXAXCSWEXSYSG-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(2,6-dimethylphenyl)urea 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)urea Chemical compound BrC=1C=C(C(=C(C1)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC)O)F.BrC=1C=C(C(=C(C1)NC(=O)NC1=C(C=CC=C1C)C)O)F ALXAXCSWEXSYSG-UHFFFAOYSA-N 0.000 claims 1
- AOMSNGUNXOWYAT-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(2-phenylethyl)thiourea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=S)NCCC1=CC=CC=C1 AOMSNGUNXOWYAT-UHFFFAOYSA-N 0.000 claims 1
- DEKLDFTZGJHOJC-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(3,5-dichlorophenyl)urea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 DEKLDFTZGJHOJC-UHFFFAOYSA-N 0.000 claims 1
- XGNWIOGWONIGKM-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(4-chlorophenyl)thiourea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=S)NC1=CC=C(Cl)C=C1 XGNWIOGWONIGKM-UHFFFAOYSA-N 0.000 claims 1
- BOPUNWNOSNSCOG-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(4-chlorophenyl)urea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC1=CC=C(Cl)C=C1 BOPUNWNOSNSCOG-UHFFFAOYSA-N 0.000 claims 1
- GKLALIDBDVGZPD-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(4-phenoxyphenyl)urea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 GKLALIDBDVGZPD-UHFFFAOYSA-N 0.000 claims 1
- HMRNHOIYUSKYNJ-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-cyclohexylurea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC1CCCCC1 HMRNHOIYUSKYNJ-UHFFFAOYSA-N 0.000 claims 1
- XUJBAOSTPPOQAO-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-naphthalen-1-ylurea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC1=CC=CC2=CC=CC=C12 XUJBAOSTPPOQAO-UHFFFAOYSA-N 0.000 claims 1
- FAAZGDKWLYPFPJ-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NC1=CC(Br)=CC(F)=C1O FAAZGDKWLYPFPJ-UHFFFAOYSA-N 0.000 claims 1
- MGVVAWGHSGVJAU-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)urea Chemical compound OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C=C1 MGVVAWGHSGVJAU-UHFFFAOYSA-N 0.000 claims 1
- LFSLVCXEZGKIRD-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)-3-(4-cyanophenyl)urea 1-(5-chloro-2-hydroxyphenyl)-3-cyclohexylurea 1-(5-chloro-2-hydroxyphenyl)-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound ClC=1C=CC(=C(C1)NC(=O)NC1=CC=C(C=C1)C#N)O.ClC=1C=CC(=C(C1)NC(=O)NC1=CC=C(C=C1)OC(F)(F)F)O.ClC=1C=CC(=C(C1)NC(=O)NC1CCCCC1)O LFSLVCXEZGKIRD-UHFFFAOYSA-N 0.000 claims 1
- NTNLFKHDLDXGJL-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)-3-[(2-methylphenyl)methyl]thiourea Chemical compound CC1=CC=CC=C1CNC(=S)NC1=CC(Cl)=CC=C1O NTNLFKHDLDXGJL-UHFFFAOYSA-N 0.000 claims 1
- LPFJVSHOZSFTGG-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)-3-phenylthiourea 1-(5-chloro-2-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]thiourea 1-(3,5-dichloro-2-hydroxyphenyl)-3-pentylthiourea Chemical compound ClC=1C(=C(C=C(C1)Cl)NC(=S)NCCCCC)O.ClC=1C=CC(=C(C1)NC(=S)NC1=CC=CC=C1)O.ClC=1C=CC(=C(C1)NC(=S)NC1=C(C=CC=C1)C(F)(F)F)O LPFJVSHOZSFTGG-UHFFFAOYSA-N 0.000 claims 1
- LXSBTRRSQWEWNB-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-(3,4-difluoro-2-hydroxyphenyl)thiourea 1-(3,4-difluoro-2-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]thiourea Chemical compound FC=1C(=C(C=CC1F)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F)O.FC=1C(=C(C=CC1F)NC(=S)NCC1CCCCC1)O LXSBTRRSQWEWNB-UHFFFAOYSA-N 0.000 claims 1
- DKYVBHQDMJFSPM-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-(3,5-dibromo-4-hydroxyphenyl)thiourea Chemical compound C1=C(Br)C(O)=C(Br)C=C1NC(=S)NCC1CCCCC1 DKYVBHQDMJFSPM-UHFFFAOYSA-N 0.000 claims 1
- KGHJSKCTLZVRGF-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-(3,5-dibromo-4-hydroxyphenyl)urea Chemical compound C1=C(Br)C(O)=C(Br)C=C1NC(=O)NCC1CCCCC1 KGHJSKCTLZVRGF-UHFFFAOYSA-N 0.000 claims 1
- BRTOPERTMLJUFM-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-(3,5-dichloro-4-hydroxyphenyl)thiourea Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=S)NCC1CCCCC1 BRTOPERTMLJUFM-UHFFFAOYSA-N 0.000 claims 1
- VHLDOSWVAPQQNQ-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yl)-5-chloro-4-hydroxyphenyl]-3-benzylurea Chemical compound Oc1c(Cl)cc(NC(=O)NCc2ccccc2)cc1-c1nc2ccccc2s1 VHLDOSWVAPQQNQ-UHFFFAOYSA-N 0.000 claims 1
- HNHOKJGTTOKEEC-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yl)-5-chloro-4-hydroxyphenyl]-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)Nc1cc(Cl)c(O)c(c1)-c1nc2ccccc2s1 HNHOKJGTTOKEEC-UHFFFAOYSA-N 0.000 claims 1
- JXLXKYCZHFVZNC-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-(2,6-dimethylphenyl)urea Chemical compound ClC1=C(O)C(C(O)C)=CC(NC(=O)NC=2C(=CC=CC=2C)C)=C1 JXLXKYCZHFVZNC-UHFFFAOYSA-N 0.000 claims 1
- YASKBUSGIFKFQX-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)NC=2C=C(C(O)=C(Cl)C=2)C(C)O)=C1 YASKBUSGIFKFQX-UHFFFAOYSA-N 0.000 claims 1
- UAEVDKVRLVZNLC-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(C(O)=C(Cl)C=2)C(C)O)=C1 UAEVDKVRLVZNLC-UHFFFAOYSA-N 0.000 claims 1
- DICICGYYWPEEDT-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-(4-chlorophenyl)urea Chemical compound ClC1=C(O)C(C(O)C)=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1 DICICGYYWPEEDT-UHFFFAOYSA-N 0.000 claims 1
- IOKSXJGZYXFDJG-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-(4-cyanophenyl)urea Chemical compound ClC1=C(O)C(C(O)C)=CC(NC(=O)NC=2C=CC(=CC=2)C#N)=C1 IOKSXJGZYXFDJG-UHFFFAOYSA-N 0.000 claims 1
- HQROETGRINEAAI-UHFFFAOYSA-N 1-[3-chloro-4-hydroxy-5-(1-hydroxyethyl)phenyl]-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NC1=CC(Cl)=C(O)C(C(C)O)=C1 HQROETGRINEAAI-UHFFFAOYSA-N 0.000 claims 1
- IIRRBSGXZNGNME-UHFFFAOYSA-N 1-[3-chloro-5-[[2-(4-chlorophenyl)sulfanylphenyl]methylamino]-4-hydroxyphenyl]-3-(2-phenylethyl)urea Chemical compound C1=C(NCC=2C(=CC=CC=2)SC=2C=CC(Cl)=CC=2)C(O)=C(Cl)C=C1NC(=O)NCCC1=CC=CC=C1 IIRRBSGXZNGNME-UHFFFAOYSA-N 0.000 claims 1
- RYULOUWAHRKREX-UHFFFAOYSA-N 1-[5-(1,3-benzothiazol-2-yl)-3-chloro-2-hydroxyphenyl]-3-propan-2-ylthiourea Chemical compound ClC1=C(O)C(NC(=S)NC(C)C)=CC(C=2SC3=CC=CC=C3N=2)=C1 RYULOUWAHRKREX-UHFFFAOYSA-N 0.000 claims 1
- MIDZOHCDAQLPMW-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-(3,5-dichlorophenyl)thiourea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=S)NC=2C=C(Cl)C=C(Cl)C=2)=C1O MIDZOHCDAQLPMW-UHFFFAOYSA-N 0.000 claims 1
- FZNLSQBIOGHUBS-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-(4-chlorophenyl)thiourea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=S)NC=2C=CC(Cl)=CC=2)=C1O FZNLSQBIOGHUBS-UHFFFAOYSA-N 0.000 claims 1
- XXVROCIHTPSKIJ-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=O)NC=2C=CC(OC(F)(F)F)=CC=2)=C1O XXVROCIHTPSKIJ-UHFFFAOYSA-N 0.000 claims 1
- CGZIKVNDGLGIKT-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-cyclohexylthiourea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=S)NC2CCCCC2)=C1O CGZIKVNDGLGIKT-UHFFFAOYSA-N 0.000 claims 1
- FUIZEKJZBMBJHH-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-pentylthiourea Chemical compound CCCCCNC(=S)NC1=CC(Cl)=CC(C(C)O)=C1O FUIZEKJZBMBJHH-UHFFFAOYSA-N 0.000 claims 1
- PWRMVSMADPPVCB-UHFFFAOYSA-N 1-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]-3-pentylurea Chemical compound CCCCCNC(=O)NC1=CC(Cl)=CC(C(C)O)=C1O PWRMVSMADPPVCB-UHFFFAOYSA-N 0.000 claims 1
- ZSKZVVIVKBIJNP-UHFFFAOYSA-N 1-benzyl-3-(3,5-dibromo-4-hydroxyphenyl)urea Chemical compound C1=C(Br)C(O)=C(Br)C=C1NC(=O)NCC1=CC=CC=C1 ZSKZVVIVKBIJNP-UHFFFAOYSA-N 0.000 claims 1
- QZQINQGYEHDUIC-UHFFFAOYSA-N 1-benzyl-3-(3,5-dichloro-2-hydroxy-4-methylphenyl)thiourea Chemical compound OC1=C(Cl)C(C)=C(Cl)C=C1NC(=S)NCC1=CC=CC=C1 QZQINQGYEHDUIC-UHFFFAOYSA-N 0.000 claims 1
- IMTHPJSBHIVPGE-UHFFFAOYSA-N 1-benzyl-3-(3,5-difluoro-2-hydroxyphenyl)urea Chemical compound OC1=C(F)C=C(F)C=C1NC(=O)NCC1=CC=CC=C1 IMTHPJSBHIVPGE-UHFFFAOYSA-N 0.000 claims 1
- VGPXOZJAJMZKCB-UHFFFAOYSA-N 1-benzyl-3-(3-fluoro-4-hydroxyphenyl)thiourea Chemical compound C1=C(F)C(O)=CC=C1NC(=S)NCC1=CC=CC=C1 VGPXOZJAJMZKCB-UHFFFAOYSA-N 0.000 claims 1
- XYDZPADBJUSGCS-UHFFFAOYSA-N 1-benzyl-3-(3-fluoro-4-hydroxyphenyl)urea Chemical compound C1=C(F)C(O)=CC=C1NC(=O)NCC1=CC=CC=C1 XYDZPADBJUSGCS-UHFFFAOYSA-N 0.000 claims 1
- TYQRNFAHUPNEQC-UHFFFAOYSA-N 1-benzyl-3-(4-hydroxy-3-nitrophenyl)thiourea Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1NC(=S)NCC1=CC=CC=C1 TYQRNFAHUPNEQC-UHFFFAOYSA-N 0.000 claims 1
- ZZUQSIVCPJRAEP-UHFFFAOYSA-N 1-benzyl-3-(5-bromo-3-fluoro-2-hydroxyphenyl)urea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NCC1=CC=CC=C1 ZZUQSIVCPJRAEP-UHFFFAOYSA-N 0.000 claims 1
- UJUNYZISAQAWMP-UHFFFAOYSA-N 1-tert-butyl-3-(3,5-dichloro-2-hydroxyphenyl)urea 1-(cyclohexylmethyl)-3-(3,5-dichloro-2-hydroxyphenyl)urea 1-(3,5-dichloro-2-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound ClC=1C(=C(C=C(C1)Cl)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C(=C(C=C(C1)Cl)NC(=O)NCC1CCCCC1)O.C(C)(C)(C)NC(=O)NC1=C(C(=CC(=C1)Cl)Cl)O UJUNYZISAQAWMP-UHFFFAOYSA-N 0.000 claims 1
- KMOFCEZOJJTCEC-UHFFFAOYSA-N 1-tert-butyl-3-(3,5-dichloro-4-hydroxyphenyl)thiourea Chemical compound CC(C)(C)NC(=S)NC1=CC(Cl)=C(O)C(Cl)=C1 KMOFCEZOJJTCEC-UHFFFAOYSA-N 0.000 claims 1
- KOVIBQJQEHRMJN-UHFFFAOYSA-N 1-tert-butyl-3-(3,5-difluoro-2-hydroxyphenyl)urea Chemical compound CC(C)(C)NC(=O)NC1=CC(F)=CC(F)=C1O KOVIBQJQEHRMJN-UHFFFAOYSA-N 0.000 claims 1
- HPUHCRRVOJIFGK-UHFFFAOYSA-N 1-tert-butyl-3-(3-chloro-2-hydroxyphenyl)urea 1-(3-chloro-2-hydroxyphenyl)-3-(cyclohexylmethyl)urea 1-(3-chloro-2-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound ClC=1C(=C(C=CC1)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C(=C(C=CC1)NC(=O)NCC1CCCCC1)O.C(C)(C)(C)NC(=O)NC1=C(C(=CC=C1)Cl)O HPUHCRRVOJIFGK-UHFFFAOYSA-N 0.000 claims 1
- RRAIGMLJGNJOBE-UHFFFAOYSA-N 1-tert-butyl-3-(3-fluoro-4-hydroxyphenyl)thiourea Chemical compound CC(C)(C)NC(=S)NC1=CC=C(O)C(F)=C1 RRAIGMLJGNJOBE-UHFFFAOYSA-N 0.000 claims 1
- VCVHFAYHZOVDPE-UHFFFAOYSA-N 1-tert-butyl-3-(3-fluoro-4-hydroxyphenyl)urea 1-(cyclohexylmethyl)-3-(3-fluoro-4-hydroxyphenyl)urea 1-(3-fluoro-4-hydroxyphenyl)-3-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound FC=1C=C(C=CC1O)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F.FC=1C=C(C=CC1O)NC(=O)NCC1CCCCC1.C(C)(C)(C)NC(=O)NC1=CC(=C(C=C1)O)F VCVHFAYHZOVDPE-UHFFFAOYSA-N 0.000 claims 1
- KYIQABKHNOOHJF-UHFFFAOYSA-N 1-tert-butyl-3-[3-chloro-2-hydroxy-5-(2-phenylethylcarbamoylamino)phenyl]urea Chemical compound ClC1=C(O)C(NC(=O)NC(C)(C)C)=CC(NC(=O)NCCC=2C=CC=CC=2)=C1 KYIQABKHNOOHJF-UHFFFAOYSA-N 0.000 claims 1
- IRYBHNKMSLNJIN-UHFFFAOYSA-N 1-tert-butyl-3-[5-chloro-2-hydroxy-3-(1-hydroxyethyl)phenyl]thiourea Chemical compound CC(O)C1=CC(Cl)=CC(NC(=S)NC(C)(C)C)=C1O IRYBHNKMSLNJIN-UHFFFAOYSA-N 0.000 claims 1
- UBISHFDUDQLKCY-UHFFFAOYSA-N 2,3-difluoro-6-[(2-phenylmethoxyphenyl)methylamino]phenol Chemical compound OC1=C(F)C(F)=CC=C1NCC1=CC=CC=C1OCC1=CC=CC=C1 UBISHFDUDQLKCY-UHFFFAOYSA-N 0.000 claims 1
- KWABMVAAFXBNHB-UHFFFAOYSA-N 2,4-dichloro-3-ethyl-6-[[2-(4-methylphenyl)sulfanyl-5-nitrophenyl]methylamino]phenol Chemical compound OC1=C(Cl)C(CC)=C(Cl)C=C1NCC1=CC([N+]([O-])=O)=CC=C1SC1=CC=C(C)C=C1 KWABMVAAFXBNHB-UHFFFAOYSA-N 0.000 claims 1
- UWNUDJDXLGAMSX-UHFFFAOYSA-N 2,4-dichloro-6-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]phenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 UWNUDJDXLGAMSX-UHFFFAOYSA-N 0.000 claims 1
- CLLVQMWBECZMPE-UHFFFAOYSA-N 2,6-dibromo-4-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 CLLVQMWBECZMPE-UHFFFAOYSA-N 0.000 claims 1
- MHTZOBBQOIRSIK-UHFFFAOYSA-N 2,6-dibromo-4-[[2-(4-methylphenyl)sulfanylphenyl]methylamino]phenol Chemical compound C1=CC(C)=CC=C1SC1=CC=CC=C1CNC1=CC(Br)=C(O)C(Br)=C1 MHTZOBBQOIRSIK-UHFFFAOYSA-N 0.000 claims 1
- FJNHTOXPHUZMFE-UHFFFAOYSA-N 2,6-dichloro-4-[(2-phenylsulfanylphenyl)methylamino]phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NCC1=CC=CC=C1SC1=CC=CC=C1 FJNHTOXPHUZMFE-UHFFFAOYSA-N 0.000 claims 1
- MZJIMFNCZNAWCW-UHFFFAOYSA-N 2,6-dichloro-4-[[2-(4-chlorophenyl)sulfanylphenyl]methylamino]phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C=C1 MZJIMFNCZNAWCW-UHFFFAOYSA-N 0.000 claims 1
- QQAHQUBHRBQWBL-UHFFFAOYSA-N 2,6-dichlorohydroquinone Chemical compound OC1=CC(Cl)=C(O)C(Cl)=C1 QQAHQUBHRBQWBL-UHFFFAOYSA-N 0.000 claims 1
- OOWXTXIFDVKTCV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-(3,5-dichloro-4-hydroxyphenyl)acetamide Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=O)CC1=CC=C(OCO2)C2=C1 OOWXTXIFDVKTCV-UHFFFAOYSA-N 0.000 claims 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 claims 1
- LHLANUOLDRRKBM-UHFFFAOYSA-N 2-[(5-bromothiophen-2-yl)methylamino]-4,6-dichloro-3-methylphenol Chemical compound CC1=C(Cl)C=C(Cl)C(O)=C1NCC1=CC=C(Br)S1 LHLANUOLDRRKBM-UHFFFAOYSA-N 0.000 claims 1
- HSFGWWDTKKYSIV-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)sulfanylphenyl]methylamino]-6-fluoro-4-nitrophenol Chemical compound OC1=C(F)C=C([N+]([O-])=O)C=C1NCC1=CC=CC=C1SC1=CC=CC=C1Cl HSFGWWDTKKYSIV-UHFFFAOYSA-N 0.000 claims 1
- XFGJPRISTICEKQ-UHFFFAOYSA-N 2-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]-6-fluoro-4-nitrophenol Chemical compound OC1=C(F)C=C([N+]([O-])=O)C=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 XFGJPRISTICEKQ-UHFFFAOYSA-N 0.000 claims 1
- VEGGACMLVUEMFD-UHFFFAOYSA-N 2-[[2-(3-chlorophenyl)sulfanylphenyl]methylamino]-6-fluorophenol Chemical compound OC1=C(F)C=CC=C1NCC1=CC=CC=C1SC1=CC=CC(Cl)=C1 VEGGACMLVUEMFD-UHFFFAOYSA-N 0.000 claims 1
- LUGDNZRJRGFJFK-UHFFFAOYSA-N 2-[[2-(4-chlorophenyl)sulfonylphenyl]methylamino]-6-fluoro-4-nitrophenol Chemical compound OC1=C(F)C=C([N+]([O-])=O)C=C1NCC1=CC=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 LUGDNZRJRGFJFK-UHFFFAOYSA-N 0.000 claims 1
- QUIIUKFPLUUSGQ-UHFFFAOYSA-N 2-amino-6-chlorophenol Chemical compound NC1=CC=CC(Cl)=C1O QUIIUKFPLUUSGQ-UHFFFAOYSA-N 0.000 claims 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims 1
- CQKGSWKOACZOSY-UHFFFAOYSA-N 2-chloro-6-[(2-ethylsulfanylphenyl)methylamino]phenol Chemical compound CCSC1=CC=CC=C1CNC1=CC=CC(Cl)=C1O CQKGSWKOACZOSY-UHFFFAOYSA-N 0.000 claims 1
- HYIUHBGFDFSEMH-UHFFFAOYSA-N 2-chloro-6-[[2-(3-chlorophenyl)sulfanylphenyl]methylamino]phenol Chemical compound OC1=C(Cl)C=CC=C1NCC1=CC=CC=C1SC1=CC=CC(Cl)=C1 HYIUHBGFDFSEMH-UHFFFAOYSA-N 0.000 claims 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims 1
- OGXBMVJNIUQJCU-UHFFFAOYSA-N 2-fluoro-4-nitro-6-[(2-phenylsulfanylphenyl)methylamino]phenol Chemical compound OC1=C(F)C=C([N+]([O-])=O)C=C1NCC1=CC=CC=C1SC1=CC=CC=C1 OGXBMVJNIUQJCU-UHFFFAOYSA-N 0.000 claims 1
- HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 claims 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims 1
- UBFALTGHGHULNL-UHFFFAOYSA-N 3-(hydroxymethyl)benzene-1,2-diol Chemical compound OCC1=CC=CC(O)=C1O UBFALTGHGHULNL-UHFFFAOYSA-N 0.000 claims 1
- VHFVNOXNDJLGAP-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)sulfanyl-5-nitrophenyl]methylamino]-2-hydroxybenzoic acid 2-hydroxy-3-[[2-(4-methylphenyl)sulfanyl-5-nitrophenyl]methylamino]benzoic acid Chemical compound Cc1ccc(Sc2ccc(cc2CNc2cccc(C(O)=O)c2O)[N+]([O-])=O)cc1.OC(=O)c1cccc(NCc2cc(ccc2Sc2ccc(Cl)cc2)[N+]([O-])=O)c1O VHFVNOXNDJLGAP-UHFFFAOYSA-N 0.000 claims 1
- GQKDZDYQXPOXEM-UHFFFAOYSA-N 3-chlorocatechol Chemical compound OC1=CC=CC(Cl)=C1O GQKDZDYQXPOXEM-UHFFFAOYSA-N 0.000 claims 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims 1
- OOGOFUKAJDPHDJ-UHFFFAOYSA-N 3-fluoro-4-hydroxy-5-methoxybenzaldehyde Chemical group COC1=CC(C=O)=CC(F)=C1O OOGOFUKAJDPHDJ-UHFFFAOYSA-N 0.000 claims 1
- YQTIEJVWCBHMMX-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methylamino]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1NCC1=C(F)C=CC=C1Cl YQTIEJVWCBHMMX-UHFFFAOYSA-N 0.000 claims 1
- AARNMTKNHSWUQI-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methylamino]-2-fluorophenol Chemical compound C1=C(F)C(O)=CC=C1NCC1=C(F)C=CC=C1Cl AARNMTKNHSWUQI-UHFFFAOYSA-N 0.000 claims 1
- QEDYXLZBTXJJEI-UHFFFAOYSA-N 4-[(2-quinolin-7-ylsulfanylphenyl)methylamino]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1NCC1=CC=CC=C1SC1=CC=C(C=CC=N2)C2=C1 QEDYXLZBTXJJEI-UHFFFAOYSA-N 0.000 claims 1
- QHIVCSHTRZXTBC-UHFFFAOYSA-N 4-[(5-bromothiophen-2-yl)methylamino]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1NCC1=CC=C(Br)S1 QHIVCSHTRZXTBC-UHFFFAOYSA-N 0.000 claims 1
- UARJNDAWDYZNNV-UHFFFAOYSA-N 4-[[2-(2-chlorophenyl)sulfanylphenyl]methylamino]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1NCC1=CC=CC=C1SC1=CC=CC=C1Cl UARJNDAWDYZNNV-UHFFFAOYSA-N 0.000 claims 1
- WCBZWYYQITVUMX-UHFFFAOYSA-N 4-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]-2-fluoro-6-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=C(F)C=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 WCBZWYYQITVUMX-UHFFFAOYSA-N 0.000 claims 1
- APXLXRYQRJANHU-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)sulfanyl-5-nitrophenyl]methylamino]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1NCC1=CC([N+]([O-])=O)=CC=C1SC1=CC=C(Cl)C=C1 APXLXRYQRJANHU-UHFFFAOYSA-N 0.000 claims 1
- KULODCSDLMVIBG-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)sulfonylphenyl]methylamino]-2-fluorophenol Chemical compound C1=C(F)C(O)=CC=C1NCC1=CC=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 KULODCSDLMVIBG-UHFFFAOYSA-N 0.000 claims 1
- OIJSWIWAHBMJLN-UHFFFAOYSA-N 4-[[3-(4-chlorophenoxy)phenyl]methylamino]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1NCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 OIJSWIWAHBMJLN-UHFFFAOYSA-N 0.000 claims 1
- HFYPXERYZGFDBD-UHFFFAOYSA-N 4-amino-2,6-dibromophenol Chemical compound NC1=CC(Br)=C(O)C(Br)=C1 HFYPXERYZGFDBD-UHFFFAOYSA-N 0.000 claims 1
- VZYJAINFEYBBOU-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol 2,6-dichloro-4-[[2-(trifluoromethyl)phenyl]methylamino]phenol Chemical compound NC(C=C1Cl)=CC(Cl)=C1O.OC(C(Cl)=CC(NCC1=C(C(F)(F)F)C=CC=C1)=C1)=C1Cl VZYJAINFEYBBOU-UHFFFAOYSA-N 0.000 claims 1
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 claims 1
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims 1
- NYTTXMAYPKMYIG-UHFFFAOYSA-N 4-bromo-2-fluoro-6-[(2-quinolin-7-ylsulfanylphenyl)methylamino]phenol Chemical compound OC1=C(F)C=C(Br)C=C1NCC1=CC=CC=C1SC1=CC=C(C=CC=N2)C2=C1 NYTTXMAYPKMYIG-UHFFFAOYSA-N 0.000 claims 1
- QBDZGCALXJDKTB-UHFFFAOYSA-N 4-bromo-2-fluoro-6-[[2-(4-methylphenyl)sulfanyl-5-nitrophenyl]methylamino]phenol Chemical compound C1=CC(C)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1CNC1=CC(Br)=CC(F)=C1O QBDZGCALXJDKTB-UHFFFAOYSA-N 0.000 claims 1
- JNKSIJFKWXMFEY-UHFFFAOYSA-N 4-bromo-2-fluoro-6-[[2-(4-nitrophenyl)sulfanylphenyl]methylamino]phenol Chemical compound OC1=C(F)C=C(Br)C=C1NCC1=CC=CC=C1SC1=CC=C([N+]([O-])=O)C=C1 JNKSIJFKWXMFEY-UHFFFAOYSA-N 0.000 claims 1
- CKMNDZOFXIEAOG-UHFFFAOYSA-N 4-chloro-2-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]-6-(1-hydroxyethyl)phenol Chemical compound CC(O)C1=CC(Cl)=CC(NCC=2C(=CC=CC=2)SC=2C=C(Cl)C(Cl)=CC=2)=C1O CKMNDZOFXIEAOG-UHFFFAOYSA-N 0.000 claims 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 claims 1
- SWBNNVNRRMKZCQ-UHFFFAOYSA-N 5-[[2-(4-chlorophenyl)sulfanyl-5-nitrophenyl]methylamino]-2-hydroxybenzoic acid;2-hydroxy-5-[[2-(4-methylphenyl)sulfanyl-5-nitrophenyl]methylamino]benzoic acid Chemical compound C1=CC(C)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1CNC1=CC=C(O)C(C(O)=O)=C1.C1=C(O)C(C(=O)O)=CC(NCC=2C(=CC=C(C=2)[N+]([O-])=O)SC=2C=CC(Cl)=CC=2)=C1 SWBNNVNRRMKZCQ-UHFFFAOYSA-N 0.000 claims 1
- NTMLYGHAJRXVMB-UHFFFAOYSA-N 5-bromo-3-fluorobenzene-1,2-diol Chemical compound OC1=CC(Br)=CC(F)=C1O NTMLYGHAJRXVMB-UHFFFAOYSA-N 0.000 claims 1
- VTKFEGVSNJEEMX-UHFFFAOYSA-N 6-[(2-chloro-6-fluorophenyl)methylamino]-2,3-difluorophenol Chemical compound OC1=C(F)C(F)=CC=C1NCC1=C(F)C=CC=C1Cl VTKFEGVSNJEEMX-UHFFFAOYSA-N 0.000 claims 1
- XZKRJTKXGOBEEQ-UHFFFAOYSA-N 6-[[2-(3,4-dichlorophenyl)sulfanylphenyl]methylamino]-2,3-difluorophenol Chemical compound OC1=C(F)C(F)=CC=C1NCC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 XZKRJTKXGOBEEQ-UHFFFAOYSA-N 0.000 claims 1
- 241000235389 Absidia Species 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 241000670727 Amida Species 0.000 claims 1
- 201000002909 Aspergillosis Diseases 0.000 claims 1
- 241000228212 Aspergillus Species 0.000 claims 1
- 208000036641 Aspergillus infections Diseases 0.000 claims 1
- 241000193830 Bacillus <bacterium> Species 0.000 claims 1
- 241000193738 Bacillus anthracis Species 0.000 claims 1
- 241001235574 Balantidium Species 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 241000335423 Blastomyces Species 0.000 claims 1
- OLVSKCQOJWVGPG-UHFFFAOYSA-N BrC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)Br)O.ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.NC=1C=CC(=C(CNC2=C(C=C(C=C2)O)O)C1)SC1=CC=C(C=C1)Cl Chemical compound BrC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)Br)O.ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.NC=1C=CC(=C(CNC2=C(C=C(C=C2)O)O)C1)SC1=CC=C(C=C1)Cl OLVSKCQOJWVGPG-UHFFFAOYSA-N 0.000 claims 1
- DDDJRYYIYSQERM-UHFFFAOYSA-N BrC1=CC(=C(C(=C1)F)O)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl.BrC1=CC(=C(C(=C1)F)O)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl Chemical compound BrC1=CC(=C(C(=C1)F)O)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl.BrC1=CC(=C(C(=C1)F)O)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl DDDJRYYIYSQERM-UHFFFAOYSA-N 0.000 claims 1
- ZJFREDVZFTUTIQ-UHFFFAOYSA-N BrC=1C=C(C(=C(C1)NC(=O)NC1=CC(=CC=C1)OC)O)F.BrC=1C=C(C(=C(C1)NC(=O)NC1=C(C=CC=C1)C)O)F.O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C(=CC(=C2)Br)F)O Chemical compound BrC=1C=C(C(=C(C1)NC(=O)NC1=CC(=CC=C1)OC)O)F.BrC=1C=C(C(=C(C1)NC(=O)NC1=C(C=CC=C1)C)O)F.O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C(=CC(=C2)Br)F)O ZJFREDVZFTUTIQ-UHFFFAOYSA-N 0.000 claims 1
- GYSKNHCFFCRUIQ-UHFFFAOYSA-N BrC=1C=C(C(=C(C1)NC(=S)NC1=CC(=CC(=C1)Cl)Cl)O)F.BrC=1C=C(C(=C(C1)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F)O)F Chemical compound BrC=1C=C(C(=C(C1)NC(=S)NC1=CC(=CC(=C1)Cl)Cl)O)F.BrC=1C=C(C(=C(C1)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F)O)F GYSKNHCFFCRUIQ-UHFFFAOYSA-N 0.000 claims 1
- BMSMGSVDLQQMSV-UHFFFAOYSA-N BrC=1C=C(C=C(C1O)Br)NC(=O)NC1=C(C=CC=C1C)C.BrC=1C=C(C=C(C1O)Br)NC(=O)NC1=CC(=CC=C1)OC Chemical compound BrC=1C=C(C=C(C1O)Br)NC(=O)NC1=C(C=CC=C1C)C.BrC=1C=C(C=C(C1O)Br)NC(=O)NC1=CC(=CC=C1)OC BMSMGSVDLQQMSV-UHFFFAOYSA-N 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- YJIQEIDIFHKENM-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)NC(=O)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=O)NC1=CC=C(C=C1)OC(F)(F)F.C1(CCCCC1)NC(=O)NC1=C(C=C(C=C1)O)O Chemical compound C(#N)C1=CC=C(C=C1)NC(=O)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=O)NC1=CC=C(C=C1)OC(F)(F)F.C1(CCCCC1)NC(=O)NC1=C(C=C(C=C1)O)O YJIQEIDIFHKENM-UHFFFAOYSA-N 0.000 claims 1
- WUGXDSCWKPJZLW-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1.ClC=1C=C(C=CC1Cl)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1 Chemical compound C(C)(=O)NC1=CC=C(C=C1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1.ClC=1C=C(C=CC1Cl)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1 WUGXDSCWKPJZLW-UHFFFAOYSA-N 0.000 claims 1
- OWJCKDNSCABVCA-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=C(C=C3)F)F)O)C=CC2)C=C1.FC1=C(C(=CC=C1F)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O Chemical compound C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=C(C=C3)F)F)O)C=CC2)C=C1.FC1=C(C(=CC=C1F)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O OWJCKDNSCABVCA-UHFFFAOYSA-N 0.000 claims 1
- UFYLEWXUJBDIDN-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=CC(=C(C(=C3)Cl)O)Cl)C=CC2)C=C1.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=CC=C1)Cl)O Chemical compound C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=CC(=C(C(=C3)Cl)O)Cl)C=CC2)C=C1.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=CC=C1)Cl)O UFYLEWXUJBDIDN-UHFFFAOYSA-N 0.000 claims 1
- ZHVSKDDKLJDRGP-UHFFFAOYSA-N C(C)(C)(C)NC(=O)NC1=C(C(=C(C(=C1)Cl)C)Cl)O.ClC=1C(=C(C=C(C1C)Cl)NC(=O)NC(CC(C)(C)C)(C)C)O Chemical compound C(C)(C)(C)NC(=O)NC1=C(C(=C(C(=C1)Cl)C)Cl)O.ClC=1C(=C(C=C(C1C)Cl)NC(=O)NC(CC(C)(C)C)(C)C)O ZHVSKDDKLJDRGP-UHFFFAOYSA-N 0.000 claims 1
- OBFFSXWTQPTOTG-UHFFFAOYSA-N C(C)(C)(C)NC(=S)NC1=CC(=C(C(=C1)C(C)O)O)Cl.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NC(CC(C)(C)C)(C)C Chemical compound C(C)(C)(C)NC(=S)NC1=CC(=C(C(=C1)C(C)O)O)Cl.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NC(CC(C)(C)C)(C)C OBFFSXWTQPTOTG-UHFFFAOYSA-N 0.000 claims 1
- ORFPHICUHAXRBE-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=S)NC1=CC(=C(C(=C1)C(C)O)O)Cl.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCCCCC Chemical compound C(C1=CC=CC=C1)NC(=S)NC1=CC(=C(C(=C1)C(C)O)O)Cl.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCCCCC ORFPHICUHAXRBE-UHFFFAOYSA-N 0.000 claims 1
- ZDEZGSXNNOFRQC-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=S)NC1=CC(=C(C=C1)O)Cl.ClC=1C=C(C=CC1O)NC(=S)NCCCCC.ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)NC(=S)NC1=CC(=C(C=C1)O)Cl.ClC=1C=C(C=CC1O)NC(=S)NCCCCC.ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NC1=CC=CC=C1 ZDEZGSXNNOFRQC-UHFFFAOYSA-N 0.000 claims 1
- DKBJQAJEWIJRET-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C(CNC2=C(C(=CC(=C2)Cl)Cl)O)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=CC(=C3)Cl)Cl)O)C=CC2)C=C1.ClC1=C(C(=CC(=C1)Cl)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O Chemical compound C(C1=CC=CC=C1)OC=1C=C(CNC2=C(C(=CC(=C2)Cl)Cl)O)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=CC(=C3)Cl)Cl)O)C=CC2)C=C1.ClC1=C(C(=CC(=C1)Cl)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O DKBJQAJEWIJRET-UHFFFAOYSA-N 0.000 claims 1
- WUEQQQRSHMPIPB-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C(CNC2=C(C(=CC=C2)F)O)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=CC=C3)F)O)C=CC2)C=C1.FC1=C(C(=CC=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O Chemical compound C(C1=CC=CC=C1)OC=1C=C(CNC2=C(C(=CC=C2)F)O)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=C(C(=CC=C3)F)O)C=CC2)C=C1.FC1=C(C(=CC=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O WUEQQQRSHMPIPB-UHFFFAOYSA-N 0.000 claims 1
- PGJLPQJFDPRMGV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C(CNC2=CC(=C(C=C2)O)Cl)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=CC(=C(C=C3)O)Cl)C=CC2)C=C1.ClC1=C(C=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O Chemical compound C(C1=CC=CC=C1)OC=1C=C(CNC2=CC(=C(C=C2)O)Cl)C=CC1.C(C)(C)(C)C1=CC=C(OC=2C=C(CNC3=CC(=C(C=C3)O)Cl)C=CC2)C=C1.ClC1=C(C=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)Cl)O PGJLPQJFDPRMGV-UHFFFAOYSA-N 0.000 claims 1
- BPVKBTVSLJDXGW-UHFFFAOYSA-N C1(CCCCC1)CNC(=S)NC1=CC(=C(C=C1)O)[N+](=O)[O-].OC1=C(C=C(C=C1)NC(=S)NC(C)C)[N+](=O)[O-].C(C)(C)(C)NC(=S)NC1=CC(=C(C=C1)O)[N+](=O)[O-] Chemical compound C1(CCCCC1)CNC(=S)NC1=CC(=C(C=C1)O)[N+](=O)[O-].OC1=C(C=C(C=C1)NC(=S)NC(C)C)[N+](=O)[O-].C(C)(C)(C)NC(=S)NC1=CC(=C(C=C1)O)[N+](=O)[O-] BPVKBTVSLJDXGW-UHFFFAOYSA-N 0.000 claims 1
- GAHMYMRLTYPGDC-UHFFFAOYSA-N CC(C)S(=O)(=O)O.ClC=1C(=C(C=C(C1C)Cl)NS(=O)(=O)CCCCCCCC)O.ClC=1C(=C(C=C(C1C)Cl)NS(=O)(=O)CCCC)O Chemical compound CC(C)S(=O)(=O)O.ClC=1C(=C(C=C(C1C)Cl)NS(=O)(=O)CCCCCCCC)O.ClC=1C(=C(C=C(C1C)Cl)NS(=O)(=O)CCCC)O GAHMYMRLTYPGDC-UHFFFAOYSA-N 0.000 claims 1
- JRQGPFFVWUQKFU-UHFFFAOYSA-N CC=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1.COC1=CC=C(OC=2C=C(CNC3=C(C=C(C=C3)O)O)C=CC2)C=C1.BrC1=CC=C(S1)CNC1=C(C(=CC(=C1C)Cl)Cl)O Chemical compound CC=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1.COC1=CC=C(OC=2C=C(CNC3=C(C=C(C=C3)O)O)C=CC2)C=C1.BrC1=CC=C(S1)CNC1=C(C(=CC(=C1C)Cl)Cl)O JRQGPFFVWUQKFU-UHFFFAOYSA-N 0.000 claims 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
- 241000222122 Candida albicans Species 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- 206010008631 Cholera Diseases 0.000 claims 1
- 208000005243 Chondrosarcoma Diseases 0.000 claims 1
- 206010008803 Chromoblastomycosis Diseases 0.000 claims 1
- 208000015116 Chromomycosis Diseases 0.000 claims 1
- USPUHJNBRNPLDH-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O Chemical compound ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O USPUHJNBRNPLDH-UHFFFAOYSA-N 0.000 claims 1
- VRNKUTFKYXXGDE-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O Chemical compound ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O VRNKUTFKYXXGDE-UHFFFAOYSA-N 0.000 claims 1
- HCUCNAXBDHLQNH-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)S(=O)(=O)C1=CC=C(C=C1)Cl.NC=1C=CC(=C(CNC2=C(C=CC(=C2)Cl)O)C1)SC1=CC=C(C=C1)Cl Chemical compound ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)S(=O)(=O)C1=CC=C(C=C1)Cl.NC=1C=CC(=C(CNC2=C(C=CC(=C2)Cl)O)C1)SC1=CC=C(C=C1)Cl HCUCNAXBDHLQNH-UHFFFAOYSA-N 0.000 claims 1
- QSHDMNZOGQYYAU-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)Cl)NCC1=CC=C(C=C1)SC)O.ClC1=C(C(=CC(=C1)Cl)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=C(C(=CC(=C2)Cl)Cl)O)C=CC=C1 Chemical compound ClC1=C(C(=CC(=C1)Cl)NCC1=CC=C(C=C1)SC)O.ClC1=C(C(=CC(=C1)Cl)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=C(C(=CC(=C2)Cl)Cl)O)C=CC=C1 QSHDMNZOGQYYAU-UHFFFAOYSA-N 0.000 claims 1
- UZEWBZNYNKFAQK-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)C(C)O)O.ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)C(C)O)O Chemical compound ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)C(C)O)O.ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)C(C)O)O UZEWBZNYNKFAQK-UHFFFAOYSA-N 0.000 claims 1
- XVYIVAPNVGBQME-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)Cl)O Chemical compound ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)Cl)O XVYIVAPNVGBQME-UHFFFAOYSA-N 0.000 claims 1
- STRBZHRYCYMWNL-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)C)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)OC)Cl)O.BrC1=CC=C(S1)CNC1=CC(=C(C(=C1)Cl)O)Cl Chemical compound ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)C)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)OC)Cl)O.BrC1=CC=C(S1)CNC1=CC(=C(C(=C1)Cl)O)Cl STRBZHRYCYMWNL-UHFFFAOYSA-N 0.000 claims 1
- LDRLWMRDMOFBBY-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)NCC1=CC=CC2=CC=CC=C12)Cl)O.C(C1=CC=CC=C1)OC1=C(CNC2=CC(=C(C(=C2)Cl)O)Cl)C=CC=C1.C(C1=CC=CC=C1)OC=1C=C(CNC2=CC(=C(C(=C2)Cl)O)Cl)C=CC1 Chemical compound ClC1=C(C(=CC(=C1)NCC1=CC=CC2=CC=CC=C12)Cl)O.C(C1=CC=CC=C1)OC1=C(CNC2=CC(=C(C(=C2)Cl)O)Cl)C=CC=C1.C(C1=CC=CC=C1)OC=1C=C(CNC2=CC(=C(C(=C2)Cl)O)Cl)C=CC1 LDRLWMRDMOFBBY-UHFFFAOYSA-N 0.000 claims 1
- VESDVJAKXCZDOQ-UHFFFAOYSA-N ClC1=C(C(=CC(=C1C)Cl)NCC1=CC=C(C=C1)SC)O.ClC1=C(C(=CC(=C1C)Cl)NCC1=CC=CC2=CC=CC=C12)O Chemical compound ClC1=C(C(=CC(=C1C)Cl)NCC1=CC=C(C=C1)SC)O.ClC1=C(C(=CC(=C1C)Cl)NCC1=CC=CC2=CC=CC=C12)O VESDVJAKXCZDOQ-UHFFFAOYSA-N 0.000 claims 1
- LEUWEYNBBRXUHS-UHFFFAOYSA-N ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)O Chemical compound ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)O LEUWEYNBBRXUHS-UHFFFAOYSA-N 0.000 claims 1
- OLCVQRJKLFIAHV-UHFFFAOYSA-N ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O Chemical compound ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O OLCVQRJKLFIAHV-UHFFFAOYSA-N 0.000 claims 1
- OPYWWLBOUIONDQ-UHFFFAOYSA-N ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O Chemical compound ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C(=CC(=C1CC)Cl)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O OPYWWLBOUIONDQ-UHFFFAOYSA-N 0.000 claims 1
- YDKUCYZLXFVALS-UHFFFAOYSA-N ClC1=C(C(=CC=C1)NCC1=CC(=CC=C1)C)O.ClC1=C(C(=CC=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)OC)O.BrC1=CC=C(S1)CNC1=C(C(=CC=C1)Cl)O Chemical compound ClC1=C(C(=CC=C1)NCC1=CC(=CC=C1)C)O.ClC1=C(C(=CC=C1)NCC1=CC(=CC=C1)OC1=CC=C(C=C1)OC)O.BrC1=CC=C(S1)CNC1=C(C(=CC=C1)Cl)O YDKUCYZLXFVALS-UHFFFAOYSA-N 0.000 claims 1
- WOFBEKZNPBWIHN-UHFFFAOYSA-N ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)O Chemical compound ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=C(C=C1)Cl)Cl)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl)O WOFBEKZNPBWIHN-UHFFFAOYSA-N 0.000 claims 1
- IQSJVRMSOXKVBC-UHFFFAOYSA-N ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O Chemical compound ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O.ClC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O IQSJVRMSOXKVBC-UHFFFAOYSA-N 0.000 claims 1
- PHCGLSKGFOGFIQ-UHFFFAOYSA-N ClC1=C(C=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=CC=C1)O.ClC1=C(CNC2=C(C=C(C=C2)O)O)C(=CC=C1)F.FC(C=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1)(F)F Chemical compound ClC1=C(C=CC(=C1)NCC1=CC(=CC=C1)OC1=CC=CC=C1)O.ClC1=C(CNC2=C(C=C(C=C2)O)O)C(=CC=C1)F.FC(C=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1)(F)F PHCGLSKGFOGFIQ-UHFFFAOYSA-N 0.000 claims 1
- SEUMMSRGQOMSJO-UHFFFAOYSA-N ClC1=C(C=CC(=C1)NCC1=CC=C(C=C1)SC)O.ClC1=C(C=CC(=C1)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=CC(=C(C=C2)O)Cl)C=CC=C1 Chemical compound ClC1=C(C=CC(=C1)NCC1=CC=C(C=C1)SC)O.ClC1=C(C=CC(=C1)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=CC(=C(C=C2)O)Cl)C=CC=C1 SEUMMSRGQOMSJO-UHFFFAOYSA-N 0.000 claims 1
- WXTJXICXGCQILX-UHFFFAOYSA-N ClC1=C(C=CC=C1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.OCC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O Chemical compound ClC1=C(C=CC=C1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.OCC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O WXTJXICXGCQILX-UHFFFAOYSA-N 0.000 claims 1
- RRCJNHLWOADVLO-UHFFFAOYSA-N ClC1=C(C=CC=C1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1.OC1=C(C(=O)O)C=CC=C1NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC Chemical compound ClC1=C(C=CC=C1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1.OC1=C(C(=O)O)C=CC=C1NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC RRCJNHLWOADVLO-UHFFFAOYSA-N 0.000 claims 1
- DPSXRUNWNBEXMX-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)S(=O)(=O)C1=CC=C(C=C1)Cl.NC=1C=CC(=C(CNC2=C(C(=CC(=C2)Cl)C(C)O)O)C1)SC1=CC=C(C=C1)Cl Chemical compound ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)S(=O)(=O)C1=CC=C(C=C1)Cl.NC=1C=CC(=C(CNC2=C(C(=CC(=C2)Cl)C(C)O)O)C1)SC1=CC=C(C=C1)Cl DPSXRUNWNBEXMX-UHFFFAOYSA-N 0.000 claims 1
- AFHLSFWIIBCYTD-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl.ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl Chemical compound ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=CC(=CC=C1)Cl.ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=C(C=CC=C1)Cl AFHLSFWIIBCYTD-UHFFFAOYSA-N 0.000 claims 1
- MTPWVRJYOGODEG-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O)C(C)O Chemical compound ClC1=CC(=C(C(=C1)C(C)O)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O)C(C)O MTPWVRJYOGODEG-UHFFFAOYSA-N 0.000 claims 1
- FJNIUHBEIAOLIM-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O)C(C)O.ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O)C(C)O Chemical compound ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O)C(C)O.ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O)C(C)O FJNIUHBEIAOLIM-UHFFFAOYSA-N 0.000 claims 1
- LDJJAPBWTSBPOU-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O)C(C)O.ClC=1C=C(C(=C(C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)NC(C)=O)O)C(C)O Chemical compound ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O)C(C)O.ClC=1C=C(C(=C(C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)NC(C)=O)O)C(C)O LDJJAPBWTSBPOU-UHFFFAOYSA-N 0.000 claims 1
- LLGPTIROYJITMG-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O)C(C)O.ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=CC=C(C(=C2O)F)F)C=CC=C1 Chemical compound ClC1=CC(=C(C(=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O)C(C)O.ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=CC=C(C(=C2O)F)F)C=CC=C1 LLGPTIROYJITMG-UHFFFAOYSA-N 0.000 claims 1
- GQYIOWDGXTUQFU-UHFFFAOYSA-N ClC1=CC(=C(C=C1)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1 Chemical compound ClC1=CC(=C(C=C1)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1 GQYIOWDGXTUQFU-UHFFFAOYSA-N 0.000 claims 1
- GZBLYWJKBUOLEA-UHFFFAOYSA-N ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=CC=C1 Chemical compound ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C.ClC1=CC(=C(C=C1)O)NCC1=C(C=CC=C1)SC1=CC=CC=C1 GZBLYWJKBUOLEA-UHFFFAOYSA-N 0.000 claims 1
- RDUKKWKCRCCUAP-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=C(C(=CC=C2)CO)O)C=CC=C1.NC=1C=CC(=C(CNC2=C(C(=CC=C2)CO)O)C1)SC1=CC=C(C=C1)Cl Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)C1=C(CNC2=C(C(=CC=C2)CO)O)C=CC=C1.NC=1C=CC(=C(CNC2=C(C(=CC=C2)CO)O)C1)SC1=CC=C(C=C1)Cl RDUKKWKCRCCUAP-UHFFFAOYSA-N 0.000 claims 1
- KNGFTXYNXZLDDS-UHFFFAOYSA-N ClC1=CC=C(C=C1)SC1=C(CNC2=C(C(=CC(=C2)[N+](=O)[O-])F)O)C=C(C=C1)[N+](=O)[O-].FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O Chemical compound ClC1=CC=C(C=C1)SC1=C(CNC2=C(C(=CC(=C2)[N+](=O)[O-])F)O)C=C(C=C1)[N+](=O)[O-].FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O KNGFTXYNXZLDDS-UHFFFAOYSA-N 0.000 claims 1
- BWGDTYHTCHWJDH-UHFFFAOYSA-N ClC1=CC=C(C=C1)SC1=C(CNC2=C(C(=CC=C2)CO)O)C=CC=C1.OCC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O.OCC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O Chemical compound ClC1=CC=C(C=C1)SC1=C(CNC2=C(C(=CC=C2)CO)O)C=CC=C1.OCC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O.OCC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=CC=C1)O BWGDTYHTCHWJDH-UHFFFAOYSA-N 0.000 claims 1
- XRMDQDNHRLFDMO-UHFFFAOYSA-N ClC1=CC=C(C=C1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.OCC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O Chemical compound ClC1=CC=C(C=C1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.OCC1=C(C=CC(=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O XRMDQDNHRLFDMO-UHFFFAOYSA-N 0.000 claims 1
- BXNZANAUMCKFSN-UHFFFAOYSA-N ClC=1C(=C(C=C(C1)Cl)NC(=O)NC1=CC=C(C=C1)Cl)O.ClC=1C(=C(C=C(C1)Cl)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O Chemical compound ClC=1C(=C(C=C(C1)Cl)NC(=O)NC1=CC=C(C=C1)Cl)O.ClC=1C(=C(C=C(C1)Cl)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O BXNZANAUMCKFSN-UHFFFAOYSA-N 0.000 claims 1
- FRIMNDGYMBRRFL-UHFFFAOYSA-N ClC=1C(=C(C=C(C1)Cl)NC(=S)NCCC1=CC=CC=C1)O.ClC=1C(=C(C=C(C1)Cl)NC(=S)NCC1=C(C=CC=C1)C)O.C(C1=CC=CC=C1)NC(=S)NC1=C(C(=CC(=C1)Cl)Cl)O Chemical compound ClC=1C(=C(C=C(C1)Cl)NC(=S)NCCC1=CC=CC=C1)O.ClC=1C(=C(C=C(C1)Cl)NC(=S)NCC1=C(C=CC=C1)C)O.C(C1=CC=CC=C1)NC(=S)NC1=C(C(=CC(=C1)Cl)Cl)O FRIMNDGYMBRRFL-UHFFFAOYSA-N 0.000 claims 1
- MJDUOMYWDMGYPW-UHFFFAOYSA-N ClC=1C(=C(C=C(C1C)Cl)NC(=O)NCCC1=CC=CC=C1)O.ClC=1C(=C(C=C(C1C)Cl)NC(=O)NCC1=C(C=CC=C1)C)O Chemical compound ClC=1C(=C(C=C(C1C)Cl)NC(=O)NCCC1=CC=CC=C1)O.ClC=1C(=C(C=C(C1C)Cl)NC(=O)NCC1=C(C=CC=C1)C)O MJDUOMYWDMGYPW-UHFFFAOYSA-N 0.000 claims 1
- FHVXQWYRUORENQ-UHFFFAOYSA-N ClC=1C=C(C(=C(C1)C(C)=O)O)NCC1=C(C=CC=C1)SC1=CC=CC=C1.S1C(=NC2=C1C=CC=C2)C=2C=C(C(=C(C2)NC(=S)NC2CCCC2)O)Cl Chemical compound ClC=1C=C(C(=C(C1)C(C)=O)O)NCC1=C(C=CC=C1)SC1=CC=CC=C1.S1C(=NC2=C1C=CC=C2)C=2C=C(C(=C(C2)NC(=S)NC2CCCC2)O)Cl FHVXQWYRUORENQ-UHFFFAOYSA-N 0.000 claims 1
- DQDRXMFDEFYLFJ-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)NC(=S)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F.C1(CCCCC1)CNC(=S)NC1=C(C=C(C=C1)O)O Chemical compound ClC=1C=C(C=C(C1)Cl)NC(=S)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F.C1(CCCCC1)CNC(=S)NC1=C(C=C(C=C1)O)O DQDRXMFDEFYLFJ-UHFFFAOYSA-N 0.000 claims 1
- ZHSQXWCZMMCPDT-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NC1=CC=C(C=C1)OC1=CC=CC=C1.C12(CC3CC(CC(C1)C3)C2)NC(=O)NC2=CC(=C(C(=C2)C(C)O)O)Cl Chemical compound ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NC1=CC=C(C=C1)OC1=CC=CC=C1.C12(CC3CC(CC(C1)C3)C2)NC(=O)NC2=CC(=C(C(=C2)C(C)O)O)Cl ZHSQXWCZMMCPDT-UHFFFAOYSA-N 0.000 claims 1
- WVVSLIMBYZQFRU-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCC1CCCCC1.C(C)(C)(C)NC(=O)NC1=CC(=C(C(=C1)C(C)O)O)Cl Chemical compound ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCC1CCCCC1.C(C)(C)(C)NC(=O)NC1=CC(=C(C(=C1)C(C)O)O)Cl WVVSLIMBYZQFRU-UHFFFAOYSA-N 0.000 claims 1
- MKQWVNRELYTVHX-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCCC1=CC=CC=C1.ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCC1=C(C=CC=C1)C Chemical compound ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCCC1=CC=CC=C1.ClC=1C=C(C=C(C1O)C(C)O)NC(=O)NCC1=C(C=CC=C1)C MKQWVNRELYTVHX-UHFFFAOYSA-N 0.000 claims 1
- YYBOBZJVYBZPIY-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCCC1=CC=CC=C1.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCC1=C(C=CC=C1)C Chemical compound ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCCC1=CC=CC=C1.ClC=1C=C(C=C(C1O)C(C)O)NC(=S)NCC1=C(C=CC=C1)C YYBOBZJVYBZPIY-UHFFFAOYSA-N 0.000 claims 1
- OFUJQQUKZYINMT-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)Cl)NC(=O)NC1=CC=C(C=C1)C#N.ClC=1C=C(C=C(C1O)Cl)NC(=O)NC1=CC=C(C=C1)OC(F)(F)F Chemical compound ClC=1C=C(C=C(C1O)Cl)NC(=O)NC1=CC=C(C=C1)C#N.ClC=1C=C(C=C(C1O)Cl)NC(=O)NC1=CC=C(C=C1)OC(F)(F)F OFUJQQUKZYINMT-UHFFFAOYSA-N 0.000 claims 1
- KNVSINFYWBZUFY-UHFFFAOYSA-N ClC=1C=C(C=C(C1O)NCC1=C(C=CC=C1F)Cl)NC(=O)NC1CCCCC1.C1(=C(C=CC=C1)CNC=1C=C(C=C(C1O)Cl)NC(=O)NC1CCCCC1)C1=CC=CC=C1 Chemical compound ClC=1C=C(C=C(C1O)NCC1=C(C=CC=C1F)Cl)NC(=O)NC1CCCCC1.C1(=C(C=CC=C1)CNC=1C=C(C=C(C1O)Cl)NC(=O)NC1CCCCC1)C1=CC=CC=C1 KNVSINFYWBZUFY-UHFFFAOYSA-N 0.000 claims 1
- NRBLFYBPLGMWGA-UHFFFAOYSA-N ClC=1C=C(C=CC1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1.ClC1=C(C=CC=C1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1 Chemical compound ClC=1C=C(C=CC1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1.ClC1=C(C=CC=C1)SC1=C(CNC=2C=CC(=C(C(=O)O)C2)O)C=CC=C1 NRBLFYBPLGMWGA-UHFFFAOYSA-N 0.000 claims 1
- FNGWSQZBJGZQSG-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.ClC=1C=C(C=CC1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1 Chemical compound ClC=1C=C(C=CC1Cl)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1.ClC=1C=C(C=CC1)SC1=C(CNC2=CC(=C(C=C2)O)CO)C=CC=C1 FNGWSQZBJGZQSG-UHFFFAOYSA-N 0.000 claims 1
- NVRGEGXKJPIQFP-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1.ClC=1C=C(C=CC1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1 Chemical compound ClC=1C=C(C=CC1Cl)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1.ClC=1C=C(C=CC1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1 NVRGEGXKJPIQFP-UHFFFAOYSA-N 0.000 claims 1
- XNZRELTWQNVGIJ-UHFFFAOYSA-N ClC=1C=C(C=CC1O)NC(=O)NC1=C(C=CC=C1)C.O1COC2=C1C=CC(=C2)NC(=O)NC2=CC(=C(C=C2)O)Cl.ClC=2C=C(C=CC2O)NC(=O)NC2=CC=C(C=C2)C#N Chemical compound ClC=1C=C(C=CC1O)NC(=O)NC1=C(C=CC=C1)C.O1COC2=C1C=CC(=C2)NC(=O)NC2=CC(=C(C=C2)O)Cl.ClC=2C=C(C=CC2O)NC(=O)NC2=CC=C(C=C2)C#N XNZRELTWQNVGIJ-UHFFFAOYSA-N 0.000 claims 1
- IPIBPPBWMIOZGY-UHFFFAOYSA-N ClC=1C=C(C=CC1O)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC.ClC=1C=C(C=CC1O)NC(=O)NC1=C(C=CC=C1C)C.ClC=1C=C(C=CC1O)NC(=O)NC1=CC(=CC=C1)OC Chemical compound ClC=1C=C(C=CC1O)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC.ClC=1C=C(C=CC1O)NC(=O)NC1=C(C=CC=C1C)C.ClC=1C=C(C=CC1O)NC(=O)NC1=CC(=CC=C1)OC IPIBPPBWMIOZGY-UHFFFAOYSA-N 0.000 claims 1
- MFJJNAFUKKUZQI-UHFFFAOYSA-N ClC=1C=C(C=CC1O)NC(=S)NCC1CCCCC1.ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=CC(=C(C=C1)O)Cl Chemical compound ClC=1C=C(C=CC1O)NC(=S)NCC1CCCCC1.ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=CC(=C(C=C1)O)Cl MFJJNAFUKKUZQI-UHFFFAOYSA-N 0.000 claims 1
- YXWWGDCOAGMICJ-UHFFFAOYSA-N ClC=1C=CC(=C(C1)NC(=O)NC1=CC=CC2=CC=CC=C12)O.ClC=1C=CC(=C(C1)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC)O.ClC=1C=CC(=C(C1)NC(=O)NC1=C(C=CC=C1C)C)O Chemical compound ClC=1C=CC(=C(C1)NC(=O)NC1=CC=CC2=CC=CC=C12)O.ClC=1C=CC(=C(C1)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC)O.ClC=1C=CC(=C(C1)NC(=O)NC1=C(C=CC=C1C)C)O YXWWGDCOAGMICJ-UHFFFAOYSA-N 0.000 claims 1
- QGUPZHFEBIXOIW-UHFFFAOYSA-N ClC=1C=CC(=C(C1)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C=CC(=C(C1)NC(=O)NCC1CCCCC1)O.C(C)(C)(C)NC(=O)NC1=C(C=CC(=C1)Cl)O Chemical compound ClC=1C=CC(=C(C1)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C=CC(=C(C1)NC(=O)NCC1CCCCC1)O.C(C)(C)(C)NC(=O)NC1=C(C=CC(=C1)Cl)O QGUPZHFEBIXOIW-UHFFFAOYSA-N 0.000 claims 1
- AEDVMDASUKZRSU-UHFFFAOYSA-N ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=C(C(=CC(=C1)Cl)Cl)O.ClC=1C(=C(C=C(C1)Cl)NC(=S)NC(CC(C)(C)C)(C)C)O Chemical compound ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=C(C(=CC(=C1)Cl)Cl)O.ClC=1C(=C(C=C(C1)Cl)NC(=S)NC(CC(C)(C)C)(C)C)O AEDVMDASUKZRSU-UHFFFAOYSA-N 0.000 claims 1
- GJXCBHGNFZSTBK-UHFFFAOYSA-N ClC=1C=CC(=C(C1)NC(=S)NC1CCCCC1)O.ClC=1C=CC(=C(C1)NC(=S)NC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C=CC(=C(C1)NC(=S)NC1=CC=C(C=C1)Cl)O Chemical compound ClC=1C=CC(=C(C1)NC(=S)NC1CCCCC1)O.ClC=1C=CC(=C(C1)NC(=S)NC1=CC=C(C=C1)C(F)(F)F)O.ClC=1C=CC(=C(C1)NC(=S)NC1=CC=C(C=C1)Cl)O GJXCBHGNFZSTBK-UHFFFAOYSA-N 0.000 claims 1
- QXRCLZSELQZTIY-UHFFFAOYSA-N ClC=1C=CC(=C(C1)NC(=S)NCC1CCCCC1)O.ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=C(C=CC(=C1)Cl)O Chemical compound ClC=1C=CC(=C(C1)NC(=S)NCC1CCCCC1)O.ClC=1C=CC(=C(C1)NC(=S)NC(C)C)O.C(C)(C)(C)NC(=S)NC1=C(C=CC(=C1)Cl)O QXRCLZSELQZTIY-UHFFFAOYSA-N 0.000 claims 1
- 241000193403 Clostridium Species 0.000 claims 1
- 241000223203 Coccidioides Species 0.000 claims 1
- 241000223205 Coccidioides immitis Species 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims 1
- 201000007336 Cryptococcosis Diseases 0.000 claims 1
- 241000221204 Cryptococcus neoformans Species 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 241000244160 Echinococcus Species 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 241000224431 Entamoeba Species 0.000 claims 1
- 241000588914 Enterobacter Species 0.000 claims 1
- 241000194033 Enterococcus Species 0.000 claims 1
- 241000991587 Enterovirus C Species 0.000 claims 1
- 241001480035 Epidermophyton Species 0.000 claims 1
- YBCRIHBZZOTMEB-UHFFFAOYSA-N FC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SCC)F)O.FC1=C(C(=CC(=C1)NCC1=CC=C(C=C1)SC)F)O Chemical compound FC1=C(C(=CC(=C1)NCC1=C(C=CC=C1)SCC)F)O.FC1=C(C(=CC(=C1)NCC1=CC=C(C=C1)SC)F)O YBCRIHBZZOTMEB-UHFFFAOYSA-N 0.000 claims 1
- WIWWSOSXJXORND-UHFFFAOYSA-N FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O.FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O Chemical compound FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C(C=C1)OC)O.FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-])O WIWWSOSXJXORND-UHFFFAOYSA-N 0.000 claims 1
- XODRIZHXKOPHGJ-UHFFFAOYSA-N FC1=C(C(=CC=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O.FC1=C(C(=CC=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)Cl)O.FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O Chemical compound FC1=C(C(=CC=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O.FC1=C(C(=CC=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)Cl)O.FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1)O XODRIZHXKOPHGJ-UHFFFAOYSA-N 0.000 claims 1
- VTGCQUFXOAMDFK-UHFFFAOYSA-N FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O.FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O Chemical compound FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)Cl)O.FC1=C(C(=CC=C1)NCC1=C(C=CC=C1)SC1=CC=C(C=C1)C)O VTGCQUFXOAMDFK-UHFFFAOYSA-N 0.000 claims 1
- OMFOGDHULJDABC-UHFFFAOYSA-N FC1=C(C(=CC=C1)NCC1=CC=C(C=C1)SC)O.FC1=C(C(=CC=C1)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=C(C(=CC=C2)F)O)C=CC=C1 Chemical compound FC1=C(C(=CC=C1)NCC1=CC=C(C=C1)SC)O.FC1=C(C(=CC=C1)NCC1=CC=CC2=CC=CC=C12)O.C(C1=CC=CC=C1)OC1=C(CNC2=C(C(=CC=C2)F)O)C=CC=C1 OMFOGDHULJDABC-UHFFFAOYSA-N 0.000 claims 1
- VBTILZNUWHBEIR-UHFFFAOYSA-N FC1=C(C(=CC=C1F)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O.ClC1=CC=C(C=C1)SC1=C(CNC2=CC=C(C(=C2O)F)F)C=C(C=C1)[N+](=O)[O-] Chemical compound FC1=C(C(=CC=C1F)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O.ClC1=CC=C(C=C1)SC1=C(CNC2=CC=C(C(=C2O)F)F)C=C(C=C1)[N+](=O)[O-] VBTILZNUWHBEIR-UHFFFAOYSA-N 0.000 claims 1
- QHKZXOPAYGISDF-UHFFFAOYSA-N FC1=C(C(=CC=C1F)NCC1=C(C=CC=C1)C(F)(F)F)O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)C(F)(F)F)O.ClC1=C(C(=CC(=C1C)Cl)NCC1=C(C=CC=C1)C(F)(F)F)O Chemical compound FC1=C(C(=CC=C1F)NCC1=C(C=CC=C1)C(F)(F)F)O.ClC1=C(C(=CC(=C1)Cl)NCC1=C(C=CC=C1)C(F)(F)F)O.ClC1=C(C(=CC(=C1C)Cl)NCC1=C(C=CC=C1)C(F)(F)F)O QHKZXOPAYGISDF-UHFFFAOYSA-N 0.000 claims 1
- JGFHFLAQZVJLGX-UHFFFAOYSA-N FC1=C(C(=CC=C1F)NCC1=C(C=CC=C1)SCC)O.FC1=C(C(=CC=C1F)NCC1=CC=C(C=C1)SC)O Chemical compound FC1=C(C(=CC=C1F)NCC1=C(C=CC=C1)SCC)O.FC1=C(C(=CC=C1F)NCC1=CC=C(C=C1)SC)O JGFHFLAQZVJLGX-UHFFFAOYSA-N 0.000 claims 1
- FPXWAIDLOIMEKO-UHFFFAOYSA-N FC=1C(=C(C=C(C1)F)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O.FC=1C(=C(C=C(C1)F)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O Chemical compound FC=1C(=C(C=C(C1)F)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O.FC=1C(=C(C=C(C1)F)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)O FPXWAIDLOIMEKO-UHFFFAOYSA-N 0.000 claims 1
- DNKWEXATICFTNQ-UHFFFAOYSA-N FC=1C(=C(C=CC1)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC)O.FC=1C(=C(C=CC1)NC(=O)NC1=C(C=CC=C1C)C)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC(=CC=C1)OC)O Chemical compound FC=1C(=C(C=CC1)NC(=O)NC1=CC(=C(C(=C1)OC)OC)OC)O.FC=1C(=C(C=CC1)NC(=O)NC1=C(C=CC=C1C)C)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC(=CC=C1)OC)O DNKWEXATICFTNQ-UHFFFAOYSA-N 0.000 claims 1
- HENVDMWQNXOAIM-UHFFFAOYSA-N FC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)C(F)(F)F)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)Cl)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O Chemical compound FC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)C(F)(F)F)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC=C(C=C1)Cl)O.FC=1C(=C(C=CC1)NC(=O)NC1=CC(=CC(=C1)Cl)Cl)O HENVDMWQNXOAIM-UHFFFAOYSA-N 0.000 claims 1
- VNNQXLLTRZEJIF-UHFFFAOYSA-N FC=1C(=C(C=CC1F)NC(=S)NC1=CC=C(C=C1)Cl)O.FC=1C(=C(C=CC1F)NC(=S)NC1=CC(=CC(=C1)Cl)Cl)O Chemical compound FC=1C(=C(C=CC1F)NC(=S)NC1=CC=C(C=C1)Cl)O.FC=1C(=C(C=CC1F)NC(=S)NC1=CC(=CC(=C1)Cl)Cl)O VNNQXLLTRZEJIF-UHFFFAOYSA-N 0.000 claims 1
- PKZPJNUAGUSXAU-UHFFFAOYSA-N FC=1C(=C(C=CC1F)NC(=S)NCCC1=CC=CC=C1)O.FC=1C(=C(C=CC1F)NC(=S)NCC1=C(C=CC=C1)C)O Chemical compound FC=1C(=C(C=CC1F)NC(=S)NCCC1=CC=CC=C1)O.FC=1C(=C(C=CC1F)NC(=S)NCC1=C(C=CC=C1)C)O PKZPJNUAGUSXAU-UHFFFAOYSA-N 0.000 claims 1
- UKHXIHMOOVYIRS-UHFFFAOYSA-N FC=1C=C(C=C(C1O)F)NC(=O)NCC1CCCCC1.C(C)(C)(C)NC(=O)NC1=CC(=C(C(=C1)F)O)F.FC=1C=C(C=C(C1O)F)NC(=O)NC(CC(C)(C)C)(C)C Chemical compound FC=1C=C(C=C(C1O)F)NC(=O)NCC1CCCCC1.C(C)(C)(C)NC(=O)NC1=CC(=C(C(=C1)F)O)F.FC=1C=C(C=C(C1O)F)NC(=O)NC(CC(C)(C)C)(C)C UKHXIHMOOVYIRS-UHFFFAOYSA-N 0.000 claims 1
- IXSKMMDYYWATGO-UHFFFAOYSA-N FC=1C=C(C=C(C1O)F)NC(=O)NCCC1=CC=CC=C1.FC=1C=C(C=C(C1O)F)NC(=O)NCC1=C(C=CC=C1)C.C(C1=CC=CC=C1)NC(=O)NC1=CC(=C(C(=C1)F)O)F Chemical compound FC=1C=C(C=C(C1O)F)NC(=O)NCCC1=CC=CC=C1.FC=1C=C(C=C(C1O)F)NC(=O)NCC1=C(C=CC=C1)C.C(C1=CC=CC=C1)NC(=O)NC1=CC(=C(C(=C1)F)O)F IXSKMMDYYWATGO-UHFFFAOYSA-N 0.000 claims 1
- FIWDIIDMRFTQPU-UHFFFAOYSA-N FC=1C=C(C=C(C1O)F)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F.FC=1C=C(C=C(C1O)F)NC(=S)NCC1CCCCC1 Chemical compound FC=1C=C(C=C(C1O)F)NC(=S)NCC1=CC=C(C=C1)C(F)(F)F.FC=1C=C(C=C(C1O)F)NC(=S)NCC1CCCCC1 FIWDIIDMRFTQPU-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000014260 Fungal keratitis Diseases 0.000 claims 1
- 208000005577 Gastroenteritis Diseases 0.000 claims 1
- 206010061977 Genital infection female Diseases 0.000 claims 1
- 241000224466 Giardia Species 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 206010061192 Haemorrhagic fever Diseases 0.000 claims 1
- 241000589989 Helicobacter Species 0.000 claims 1
- 241000228402 Histoplasma Species 0.000 claims 1
- 241000441510 Hormodendrum Species 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 241000222722 Leishmania <genus> Species 0.000 claims 1
- 241000186781 Listeria Species 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241000940612 Medina Species 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 241001123862 Mico Species 0.000 claims 1
- 241001480037 Microsporum Species 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 241001524040 Monogenea Species 0.000 claims 1
- 241000235395 Mucor Species 0.000 claims 1
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- CODJYMACOBJBFY-UHFFFAOYSA-N N-[3-(1,3-benzothiazol-2-yl)-5-chloro-4-hydroxyphenyl]-3-phenylpropanamide Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=C(C=1O)Cl)NC(CCC1=CC=CC=C1)=O CODJYMACOBJBFY-UHFFFAOYSA-N 0.000 claims 1
- CCQDYDXZFGLDOK-UHFFFAOYSA-N N1C(=NC2=C1C=CC=C2)CCNC(=O)NC2=C(C(=C(C(=C2)Cl)C)Cl)O.C(C2=CC=CC=C2)NC2=CC(=C(C(=C2O)Cl)C)Cl Chemical compound N1C(=NC2=C1C=CC=C2)CCNC(=O)NC2=C(C(=C(C(=C2)Cl)C)Cl)O.C(C2=CC=CC=C2)NC2=CC(=C(C(=C2O)Cl)C)Cl CCQDYDXZFGLDOK-UHFFFAOYSA-N 0.000 claims 1
- ZYYJNIFNAMJOPB-UHFFFAOYSA-N NC(C=CC(O)=C1)=C1O.OC(C=C1)=CC(O)=C1NCC1=CC=CO1.OC(C(Cl)=CC(NCC1=CC=CO1)=C1)=C1Cl.OC(C(Cl)=CC(NC(C(C=C1)=CC=C1C1=CC=CC=C1)=O)=C1)=C1Cl Chemical compound NC(C=CC(O)=C1)=C1O.OC(C=C1)=CC(O)=C1NCC1=CC=CO1.OC(C(Cl)=CC(NCC1=CC=CO1)=C1)=C1Cl.OC(C(Cl)=CC(NC(C(C=C1)=CC=C1C1=CC=CC=C1)=O)=C1)=C1Cl ZYYJNIFNAMJOPB-UHFFFAOYSA-N 0.000 claims 1
- JHJYNFWQERCVAU-UHFFFAOYSA-N NC=1C=CC(=C(CNC2=C(C(=CC(=C2)[N+](=O)[O-])F)O)C1)SC1=CC=C(C=C1)Cl.FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O Chemical compound NC=1C=CC(=C(CNC2=C(C(=CC(=C2)[N+](=O)[O-])F)O)C1)SC1=CC=C(C=C1)Cl.FC1=C(C(=CC(=C1)[N+](=O)[O-])NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O JHJYNFWQERCVAU-UHFFFAOYSA-N 0.000 claims 1
- CWAVNKMNTBLCDO-UHFFFAOYSA-N NC=1C=CC(=C(CNC2=CC(=C(C(=C2)C(C)O)O)Cl)C1)SC1=CC=C(C=C1)Cl.ClC1=C(C(=CC(=C1)C(C)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O Chemical compound NC=1C=CC(=C(CNC2=CC(=C(C(=C2)C(C)O)O)Cl)C1)SC1=CC=C(C=C1)Cl.ClC1=C(C(=CC(=C1)C(C)O)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)O CWAVNKMNTBLCDO-UHFFFAOYSA-N 0.000 claims 1
- QRFABUSMRIHPBT-UHFFFAOYSA-N NC=1C=CC(=C(CNC2=CC(=C(C(=C2)[N+](=O)[O-])O)F)C1)SC1=CC=C(C=C1)Cl.FC1=C(C(=CC(=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)[N+](=O)[O-])O Chemical compound NC=1C=CC(=C(CNC2=CC(=C(C(=C2)[N+](=O)[O-])O)F)C1)SC1=CC=C(C=C1)Cl.FC1=C(C(=CC(=C1)NCC1=C(C=CC(=C1)[N+](=O)[O-])SC1=CC=C(C=C1)C)[N+](=O)[O-])O QRFABUSMRIHPBT-UHFFFAOYSA-N 0.000 claims 1
- 241000588653 Neisseria Species 0.000 claims 1
- 241000244206 Nematoda Species 0.000 claims 1
- FEFIFTNEYQQNNL-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1.ClC=1C(C(C=CC1)(NCC1=C(C=CC=C1F)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)C(F)(F)F)Cl)O Chemical compound O(C1=CC=CC=C1)C=1C=C(CNC2=C(C=C(C=C2)O)O)C=CC1.ClC=1C(C(C=CC1)(NCC1=C(C=CC=C1F)Cl)Cl)O.ClC1=C(C(=CC(=C1)NCC1=CC(=CC=C1)C(F)(F)F)Cl)O FEFIFTNEYQQNNL-UHFFFAOYSA-N 0.000 claims 1
- RSHIHVGNEHOZRY-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C(=CC=C2)F)O.FC=2C(=C(C=CC2)NC(=O)NC2=CC=C(C=C2)C#N)O.FC=2C(=C(C=CC2)NC(=O)NC2=CC=C(C=C2)OC(F)(F)F)O Chemical compound O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C(=CC=C2)F)O.FC=2C(=C(C=CC2)NC(=O)NC2=CC=C(C=C2)C#N)O.FC=2C(=C(C=CC2)NC(=O)NC2=CC=C(C=C2)OC(F)(F)F)O RSHIHVGNEHOZRY-UHFFFAOYSA-N 0.000 claims 1
- JGSFJYSOBDOJFX-UHFFFAOYSA-N OC1=C(C(=O)O)C=CC=C1NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1.C(C)(=O)NC1=CC=C(C=C1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1 Chemical compound OC1=C(C(=O)O)C=CC=C1NCC1=C(C=CC=C1)SC1=CC=C2C=CC=NC2=C1.C(C)(=O)NC1=CC=C(C=C1)SC1=C(CNC=2C(=C(C(=O)O)C=CC2)O)C=CC=C1 JGSFJYSOBDOJFX-UHFFFAOYSA-N 0.000 claims 1
- SFHNYWQLSFWGEM-UHFFFAOYSA-N OC1=C(C=C(C=C1)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)[N+](=O)[O-].C1(CCCCC1)CNC(=O)NC1=CC(=C(C=C1)O)[N+](=O)[O-].C(C)(C)(C)NC(=O)NC1=CC(=C(C=C1)O)[N+](=O)[O-] Chemical compound OC1=C(C=C(C=C1)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F)[N+](=O)[O-].C1(CCCCC1)CNC(=O)NC1=CC(=C(C=C1)O)[N+](=O)[O-].C(C)(C)(C)NC(=O)NC1=CC(=C(C=C1)O)[N+](=O)[O-] SFHNYWQLSFWGEM-UHFFFAOYSA-N 0.000 claims 1
- DHKRYFLOOJRWLC-UHFFFAOYSA-N OC1=C(C=CC(=C1)O)NC(=O)NC1=CC(=CC=C1)OC.OC1=C(C=CC(=C1)O)NC(=O)NC1=C(C=CC=C1)C.O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C=C(C=C2)O)O Chemical compound OC1=C(C=CC(=C1)O)NC(=O)NC1=CC(=CC=C1)OC.OC1=C(C=CC(=C1)O)NC(=O)NC1=C(C=CC=C1)C.O1COC2=C1C=CC(=C2)NC(=O)NC2=C(C=C(C=C2)O)O DHKRYFLOOJRWLC-UHFFFAOYSA-N 0.000 claims 1
- WKODJVQQYPRLAQ-UHFFFAOYSA-N OC1=C(C=CC(=C1)O)NC(=O)NC1=CC=C(C=C1)C(F)(F)F.ClC1=CC=C(C=C1)NC(=O)NC1=C(C=C(C=C1)O)O.ClC=1C=C(C=C(C1)Cl)NC(=O)NC1=C(C=C(C=C1)O)O Chemical compound OC1=C(C=CC(=C1)O)NC(=O)NC1=CC=C(C=C1)C(F)(F)F.ClC1=CC=C(C=C1)NC(=O)NC1=C(C=C(C=C1)O)O.ClC=1C=C(C=C(C1)Cl)NC(=O)NC1=C(C=C(C=C1)O)O WKODJVQQYPRLAQ-UHFFFAOYSA-N 0.000 claims 1
- XUBQQMKTJARHIP-UHFFFAOYSA-N OC1=C(C=CC(=C1)O)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F.C1(CCCCC1)CNC(=O)NC1=C(C=C(C=C1)O)O.C(C)(C)(C)NC(=O)NC1=C(C=C(C=C1)O)O Chemical compound OC1=C(C=CC(=C1)O)NC(=O)NCC1=CC=C(C=C1)C(F)(F)F.C1(CCCCC1)CNC(=O)NC1=C(C=C(C=C1)O)O.C(C)(C)(C)NC(=O)NC1=C(C=C(C=C1)O)O XUBQQMKTJARHIP-UHFFFAOYSA-N 0.000 claims 1
- IVTHJJWWEBJYJR-UHFFFAOYSA-N OC1=C(C=CC(=C1)O)NC(=O)NCCC1=CC=CC=C1.OC1=C(C=CC(=C1)O)NC(=O)NCC1=C(C=CC=C1)C.C(C1=CC=CC=C1)NC(=O)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=O)NCCCCC Chemical compound OC1=C(C=CC(=C1)O)NC(=O)NCCC1=CC=CC=C1.OC1=C(C=CC(=C1)O)NC(=O)NCC1=C(C=CC=C1)C.C(C1=CC=CC=C1)NC(=O)NC1=C(C=C(C=C1)O)O.OC1=C(C=CC(=C1)O)NC(=O)NCCCCC IVTHJJWWEBJYJR-UHFFFAOYSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 241001631646 Papillomaviridae Species 0.000 claims 1
- 241001537205 Paracoccidioides Species 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 241000223785 Paramecium Species 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 241000224016 Plasmodium Species 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 241000588769 Proteus <enterobacteria> Species 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010037394 Pulmonary haemorrhage Diseases 0.000 claims 1
- 206010037742 Rabies Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 241000235527 Rhizopus Species 0.000 claims 1
- AZPGYESKBCKTRS-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=2C=C(C(=C(C2)NC(=S)NC2CCCC2)O)Cl.ClC=2C=C(C=C(C2O)NCC2=C(C=CC=C2)SC2=CC=C(C=C2)Cl)NC(=O)NC2=CC(=NC(=C2)Cl)Cl Chemical compound S1C(=NC2=C1C=CC=C2)C=2C=C(C(=C(C2)NC(=S)NC2CCCC2)O)Cl.ClC=2C=C(C=C(C2O)NCC2=C(C=CC=C2)SC2=CC=C(C=C2)Cl)NC(=O)NC2=CC(=NC(=C2)Cl)Cl AZPGYESKBCKTRS-UHFFFAOYSA-N 0.000 claims 1
- 241000607142 Salmonella Species 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 241000607720 Serratia Species 0.000 claims 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 1
- 241001149962 Sporothrix Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 208000032859 Synucleinopathies Diseases 0.000 claims 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 241000223996 Toxoplasma Species 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 241000242541 Trematoda Species 0.000 claims 1
- 241000243774 Trichinella Species 0.000 claims 1
- 241000223104 Trypanosoma Species 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 206010053648 Vascular occlusion Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 241000607734 Yersinia <bacteria> Species 0.000 claims 1
- 206010061418 Zygomycosis Diseases 0.000 claims 1
- QNSJRYXZVQVXKP-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methylthiourea Chemical compound NC(=S)NCC1=CC=C(C(F)(F)F)C=C1 QNSJRYXZVQVXKP-UHFFFAOYSA-N 0.000 claims 1
- OWTDDZMFRLUBQI-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(C(F)(F)F)C=C1 OWTDDZMFRLUBQI-UHFFFAOYSA-N 0.000 claims 1
- FXSXKIDBZWTMFR-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.ClC1=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.C1(=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1)C Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.ClC1=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1.C1(=CC=C(C=C1)SC1=C(CNC2=C(C=C(C=C2)O)O)C=CC=C1)C FXSXKIDBZWTMFR-UHFFFAOYSA-N 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000003984 candidiasis Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 201000003486 coccidioidomycosis Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 208000002528 coronary thrombosis Diseases 0.000 claims 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 230000002949 hemolytic effect Effects 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000006506 lobomycosis Diseases 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- ZQHJAAMMKABEBS-UHFFFAOYSA-N morpholin-2-one Chemical compound O=C1CNCCO1 ZQHJAAMMKABEBS-UHFFFAOYSA-N 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 201000007524 mucormycosis Diseases 0.000 claims 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- GUGQEIYXOGLKKY-UHFFFAOYSA-N n-(3,5-dichloro-4-hydroxyphenyl)-3-phenylpropanamide Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC(=O)CCC1=CC=CC=C1 GUGQEIYXOGLKKY-UHFFFAOYSA-N 0.000 claims 1
- UGKJRTOCCDRLFQ-UHFFFAOYSA-N n-[3-chloro-2-hydroxy-5-(2-phenylethylcarbamoylamino)phenyl]cyclohexanecarboxamide Chemical compound C1=C(NC(=O)C2CCCCC2)C(O)=C(Cl)C=C1NC(=O)NCCC1=CC=CC=C1 UGKJRTOCCDRLFQ-UHFFFAOYSA-N 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 208000008798 osteoma Diseases 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 208000021090 palsy Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 230000022983 regulation of cell cycle Effects 0.000 claims 1
- 230000031539 regulation of cell division Effects 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 230000000472 traumatic effect Effects 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 241001529453 unidentified herpesvirus Species 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
- 241001430294 unidentified retrovirus Species 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 208000021331 vascular occlusion disease Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 130
- 238000000034 method Methods 0.000 description 105
- 102100037026 Peptidyl-prolyl cis-trans isomerase FKBP5 Human genes 0.000 description 43
- 239000000243 solution Substances 0.000 description 39
- 235000013877 carbamide Nutrition 0.000 description 29
- 229940121392 rotamase inhibitor Drugs 0.000 description 24
- 230000000694 effects Effects 0.000 description 21
- 102000004190 Enzymes Human genes 0.000 description 20
- 108090000790 Enzymes Proteins 0.000 description 20
- 229940088598 enzyme Drugs 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 16
- 239000004793 Polystyrene Substances 0.000 description 15
- 239000004365 Protease Substances 0.000 description 15
- 229920002223 polystyrene Polymers 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- 108091005804 Peptidases Proteins 0.000 description 13
- 102000035195 Peptidases Human genes 0.000 description 13
- 238000003556 assay Methods 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000010494 dissociation reaction Methods 0.000 description 12
- 230000005593 dissociations Effects 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 230000033228 biological regulation Effects 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000035755 proliferation Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 6
- 235000019419 proteases Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000006907 apoptotic process Effects 0.000 description 5
- 239000003593 chromogenic compound Substances 0.000 description 5
- 231100000433 cytotoxic Toxicity 0.000 description 5
- 230000001472 cytotoxic effect Effects 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 102000004195 Isomerases Human genes 0.000 description 4
- 108090000769 Isomerases Proteins 0.000 description 4
- 108010020062 Peptidylprolyl Isomerase Proteins 0.000 description 4
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 230000032823 cell division Effects 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 238000001943 fluorescence-activated cell sorting Methods 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 108090000526 Papain Proteins 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 108010027179 Tacrolimus Binding Proteins Proteins 0.000 description 3
- 102000018679 Tacrolimus Binding Proteins Human genes 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 102000004142 Trypsin Human genes 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- CPELXLSAUQHCOX-DYCDLGHISA-N deuterium bromide Chemical compound [2H]Br CPELXLSAUQHCOX-DYCDLGHISA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 231100000676 disease causative agent Toxicity 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 235000019834 papain Nutrition 0.000 description 3
- 229940055729 papain Drugs 0.000 description 3
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- IHBLBMDDUQOYLA-UHFFFAOYSA-N 1-octadecyl-3-[4-[[4-(octadecylcarbamoylamino)phenyl]methyl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCCCCCCCCCCCCCCCC)=CC=C1CC1=CC=C(NC(=O)NCCCCCCCCCCCCCCCCCC)C=C1 IHBLBMDDUQOYLA-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 102000014914 Carrier Proteins Human genes 0.000 description 2
- 102000005600 Cathepsins Human genes 0.000 description 2
- 108010084457 Cathepsins Proteins 0.000 description 2
- 102000016736 Cyclin Human genes 0.000 description 2
- 108050006400 Cyclin Proteins 0.000 description 2
- 108010068682 Cyclophilins Proteins 0.000 description 2
- 102000001493 Cyclophilins Human genes 0.000 description 2
- 229930105110 Cyclosporin A Natural products 0.000 description 2
- 108010036949 Cyclosporine Proteins 0.000 description 2
- 238000000116 DAPI staining Methods 0.000 description 2
- 208000001640 Fibromyalgia Diseases 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 101001128814 Pandinus imperator Pandinin-1 Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 230000001640 apoptogenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 108091008324 binding proteins Proteins 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 229960001265 ciclosporin Drugs 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000009137 competitive binding Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 2
- OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 239000012636 effector Substances 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 210000003527 eukaryotic cell Anatomy 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 210000001236 prokaryotic cell Anatomy 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000006965 reversible inhibition Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- YVQDKKPSEQCCDP-UHFFFAOYSA-N 2,4-bis(3-fluoro-4-methoxyphenyl)-6-methylpyridine Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C)=NC(C=2C=C(F)C(OC)=CC=2)=C1 YVQDKKPSEQCCDP-UHFFFAOYSA-N 0.000 description 1
- OHUCCDUIZOBQTD-UHFFFAOYSA-N 2-(5-nitropyridin-2-yl)sulfanyl-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound N1=CC([N+](=O)[O-])=CC=C1SCC(=O)NC1=CC=CC(C(F)(F)F)=C1 OHUCCDUIZOBQTD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- BRUZQRBVNRKLJG-UHFFFAOYSA-N 2-methylpropyl carbamate Chemical compound CC(C)COC(N)=O BRUZQRBVNRKLJG-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N Amide-Cyclohexanecarboxylic acid Natural products NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FVDVKIINWXWIEU-UHFFFAOYSA-N CC#N.S(=O)(=O)(Cl)Cl Chemical compound CC#N.S(=O)(=O)(Cl)Cl FVDVKIINWXWIEU-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108090000712 Cathepsin B Proteins 0.000 description 1
- 102000004225 Cathepsin B Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 102000006311 Cyclin D1 Human genes 0.000 description 1
- 108010058546 Cyclin D1 Proteins 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 102100038026 DNA fragmentation factor subunit alpha Human genes 0.000 description 1
- 101710182628 DNA fragmentation factor subunit alpha Proteins 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241001115402 Ebolavirus Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 102000003951 Erythropoietin Human genes 0.000 description 1
- 108090000394 Erythropoietin Proteins 0.000 description 1
- 238000012413 Fluorescence activated cell sorting analysis Methods 0.000 description 1
- 241000287227 Fringillidae Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 101710088172 HTH-type transcriptional regulator RipA Proteins 0.000 description 1
- 208000025309 Hair disease Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000270347 Iguania Species 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000283891 Kobus Species 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000283953 Lagomorpha Species 0.000 description 1
- 241000270322 Lepidosauria Species 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 241001460074 Microsporum distortum Species 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 101710111214 Peptidyl-prolyl cis-trans isomerase C Proteins 0.000 description 1
- 102100031653 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 4 Human genes 0.000 description 1
- 206010048724 Pericardial fibrosis Diseases 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 241001115903 Raphus cucullatus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 102100032491 Serine protease 1 Human genes 0.000 description 1
- 101710151387 Serine protease 1 Proteins 0.000 description 1
- 206010042135 Stomatitis necrotising Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000012288 TUNEL assay Methods 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 101710119665 Trypsin-1 Proteins 0.000 description 1
- 206010046798 Uterine leiomyoma Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical class [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000005128 aryl amino alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 108010054843 cyclosporin receptor Proteins 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000004163 cytometry Methods 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 208000034653 disorder of pilosebaceous unit Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 229940105423 erythropoietin Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 238000012933 kinetic analysis Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 201000010260 leiomyoma Diseases 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 208000026037 malignant tumor of neck Diseases 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 230000036456 mitotic arrest Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000036473 myasthenia Effects 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- ZLWWRJRPZBUTHG-FRKPEAEDSA-N n-[(e)-(5-bromo-2-fluorophenyl)methylideneamino]-2-methylfuran-3-carboxamide Chemical compound O1C=CC(C(=O)N\N=C\C=2C(=CC=C(Br)C=2)F)=C1C ZLWWRJRPZBUTHG-FRKPEAEDSA-N 0.000 description 1
- LJYPDEUZDGXMAP-LZYBPNLTSA-N n-[(e)-(5-bromo-2-fluorophenyl)methylideneamino]-2-thiophen-2-ylacetamide Chemical compound FC1=CC=C(Br)C=C1\C=N\NC(=O)CC1=CC=CS1 LJYPDEUZDGXMAP-LZYBPNLTSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 201000008585 noma Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000009701 normal cell proliferation Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 102000013415 peroxidase activity proteins Human genes 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 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 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010814 radioimmunoprecipitation assay Methods 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 102200082890 rs33972047 Human genes 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-M sodium;(1z)-n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylethanimidate Chemical compound [Na+].CC(=O)[N-]S(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-M 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- DSLBDAPZIGYINM-UHFFFAOYSA-N sulfanium;chloride Chemical class S.Cl DSLBDAPZIGYINM-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Biotechnology (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20020020987 EP1402888A1 (en) | 2002-09-18 | 2002-09-18 | The use of substituted carbocyclic compounds as rotamases inhibitors |
| PCT/EP2003/010406 WO2004026815A2 (en) | 2002-09-18 | 2003-09-18 | Phenol derivatives and their use as rotamase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05003084A true MXPA05003084A (es) | 2005-11-17 |
Family
ID=31970282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05003084A MXPA05003084A (es) | 2002-09-18 | 2003-09-18 | Nuevos compuestos para la inhibicion de rotamasas y usos de los mismos. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20070054904A1 (enExample) |
| EP (3) | EP1402888A1 (enExample) |
| JP (2) | JP2005539072A (enExample) |
| KR (1) | KR20050053673A (enExample) |
| CN (1) | CN100546977C (enExample) |
| AU (1) | AU2003271619A1 (enExample) |
| BR (1) | BR0314544A (enExample) |
| CA (1) | CA2498662A1 (enExample) |
| MX (1) | MXPA05003084A (enExample) |
| PL (1) | PL374846A1 (enExample) |
| RU (2) | RU2005111256A (enExample) |
| SG (1) | SG165995A1 (enExample) |
| WO (1) | WO2004026815A2 (enExample) |
| ZA (1) | ZA200501913B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004071447A2 (en) * | 2003-02-12 | 2004-08-26 | Transtech Pharma Inc. | Substituted azole derivatives as therapeutic agents |
| EP1608319A4 (en) | 2003-04-03 | 2007-02-28 | Univ California | IMPROVED HEMMER FOR SOLUBLE EPOXY HYDROLASE |
| AU2004303461B2 (en) * | 2003-12-23 | 2011-04-28 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-benzyl amine derivatives as SSRI |
| EP1713780B1 (en) * | 2004-02-05 | 2012-01-18 | Probiodrug AG | Novel inhibitors of glutaminyl cyclase |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| KR20070011475A (ko) * | 2004-05-12 | 2007-01-24 | 쉐링 코포레이션 | Cxcr1 및 cxcr2 케모카인 길항제 |
| US7550499B2 (en) | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| CN101084216B (zh) | 2004-10-20 | 2011-09-14 | 加利福尼亚大学董事会 | 可溶性环氧化物水解酶的改进抑制剂 |
| AU2006206611A1 (en) | 2005-01-19 | 2006-07-27 | Bristol-Myers Squibb Company | 2-phenoxy-N- (1, 3 , 4-thiadizol-2-yl) pyridin-3-amine derivatives and related compounds as P2Y1 receptor inhibitors for the treatment of thromboembolic disorders |
| CA2605508A1 (en) * | 2005-05-12 | 2006-11-23 | Wisconsin Alumni Research Foundation | Blockade of pin1 prevents cytokine production by activated immune cells |
| AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) * | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| AR056867A1 (es) | 2005-06-27 | 2007-10-31 | Bristol Myers Squibb Co | Antagonistas heterociclicos n- enlazados del receptor de p2y1 utiles en el tratamiento de condiciones tromboticas. composiciones farmaceuticas. |
| EP1896417B1 (en) | 2005-06-27 | 2011-03-23 | Bristol-Myers Squibb Company | Linear urea mimics antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| ATE485269T1 (de) | 2005-06-27 | 2010-11-15 | Bristol Myers Squibb Co | C-verknüpfte zyklische antagonisten des p2y1- rezeptors mit eignung bei der behandlung thrombotischer leiden |
| WO2007002634A1 (en) | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| ZA200805648B (en) | 2006-01-30 | 2009-09-30 | Transtech Pharma Inc | Substituted imidazole derivatives and their use as PTPase inhibitors |
| US20080081210A1 (en) | 2006-09-29 | 2008-04-03 | General Electric Company | Authenticatable articles and methods therefor |
| US20080081913A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Benzoxazole and benzothiazole compounds and methods therefor |
| US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| WO2008112164A2 (en) * | 2007-03-08 | 2008-09-18 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| US20110110958A1 (en) * | 2007-09-11 | 2011-05-12 | University Of Florida Research Foundation | Compositions and methods for the treatment of neoplasia |
| EP2062578A1 (en) * | 2007-11-12 | 2009-05-27 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Novel use of chemical compounds for the treatment of AIDS |
| JP2012502048A (ja) | 2008-09-08 | 2012-01-26 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼ活性のモジュレーターおよびその使用方法 |
| WO2010062308A1 (en) | 2008-10-28 | 2010-06-03 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
| WO2010057101A2 (en) * | 2008-11-17 | 2010-05-20 | Schering Corporation | Compounds useful as hiv blockers |
| SG10201400957UA (en) | 2009-03-25 | 2014-09-26 | Abbott Lab | Antiviral Compounds And Uses Thereof |
| US20120289602A1 (en) * | 2009-04-06 | 2012-11-15 | Byoung-Joo Gwag | Pharmaceutical composition for treating or preventing burn injuries |
| EP2712655B1 (en) | 2011-04-28 | 2019-12-18 | The Broad Institute, Inc. | Inhibitors of histone deacetylase |
| WO2012149106A1 (en) | 2011-04-29 | 2012-11-01 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| WO2012156531A2 (en) * | 2011-05-19 | 2012-11-22 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| US20140296255A1 (en) * | 2011-05-19 | 2014-10-02 | Oryzong Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
| RU2014143242A (ru) * | 2012-03-28 | 2016-05-20 | Ньюропор Терапис, Инк. | Производные фенилмочевины и фенилкарбаматов в качестве ингибиторов агрегации белка |
| KR20130118612A (ko) * | 2012-04-20 | 2013-10-30 | (주)네오믹스 | 신규한 아미노피리딘 유도체 및 이의 용도 |
| US9790184B2 (en) | 2012-07-27 | 2017-10-17 | The Broad Institute, Inc. | Inhibitors of histone deacetylase |
| US9914717B2 (en) | 2012-12-20 | 2018-03-13 | The Broad Institute, Inc. | Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors |
| EP2970124B1 (en) | 2013-03-14 | 2019-05-22 | The Board of Trustees of the Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| CA2998647A1 (en) * | 2014-10-03 | 2016-04-07 | The Royal Institution For The Advancement Of Learning/Mcgill University | Urea and bis-urea based compounds and analogues thereof useful in the treatment of androgen receptor mediated diseases or disorders |
| LT3319969T (lt) * | 2015-07-06 | 2024-06-10 | Turning Point Therapeutics, Inc. | Diarilo makrociklo polimorfas |
| CN107417578B (zh) * | 2017-08-23 | 2020-02-07 | 沈阳海诺威医药科技有限公司 | N-(3,5-二甲基金刚烷-1-基)-n’-取代苯基脲类化合物及其制备方法和用途 |
| JP2021510733A (ja) | 2018-01-12 | 2021-04-30 | ケーディーエーシー セラピューティクス,インコーポレーテッドKdac Therapeutics, Inc. | がんの処置のための選択的ヒストンデアセチラーゼ3(hdac3)インヒビターと免疫治療剤との組み合わせ |
| CN111233692A (zh) * | 2020-01-19 | 2020-06-05 | 江西农业大学 | 一种香茅酸酰胺类衍生物及其制备方法与应用 |
| WO2023003468A1 (en) | 2021-07-23 | 2023-01-26 | Rijksuniversiteit Groningen | Novel inhibitors of histone deacetylase (hdac), and methods, compositions and uses related thereto. |
| WO2024067560A1 (zh) * | 2022-09-26 | 2024-04-04 | 中国药科大学 | 磺酰胺类化合物及其医药用途 |
| CN116942649B (zh) * | 2023-08-01 | 2025-09-16 | 华中农业大学 | 一种苯基脲类化合物作为巴贝斯虫生长抑制剂的应用 |
| CN117224515A (zh) * | 2023-10-31 | 2023-12-15 | 首都医科大学附属北京朝阳医院 | Coh-sr4在制备预防和/或治疗缺血性心脏病的药物中的应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK41193D0 (da) * | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| US5744485A (en) * | 1994-03-25 | 1998-04-28 | Vertex Pharmaceuticals Incorporated | Carbamates and ureas as modifiers of multi-drug resistance |
| US5696135A (en) * | 1995-06-07 | 1997-12-09 | Gpi Nil Holdings, Inc. | Inhibitors of rotamase enzyme activity effective at stimulating neuronal growth |
| EA002401B1 (ru) * | 1996-12-31 | 2002-04-25 | Джи Пи Ай Нил Холдингс, Инк. | N-связанные мочевины и карбаматы сложных гетероциклических тиоэфиров |
| US6242468B1 (en) * | 1997-02-27 | 2001-06-05 | Jia-He Li | Carbamate and urea compositions and neurotrophic uses |
| ZA98825B (en) * | 1997-02-27 | 1998-10-19 | Guilford Pharm Inc | Method of using neurotrophic carbamates and ureas |
| US6093742A (en) * | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| WO2001017953A1 (en) * | 1999-09-08 | 2001-03-15 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| EP1339668A2 (en) * | 2000-11-28 | 2003-09-03 | Guilford Pharmaceuticals Inc. | Bisubstituted carbocyclic cyclophilin binding compounds and theirus |
| JP2004532187A (ja) * | 2001-01-25 | 2004-10-21 | ギルフォード ファーマシュウティカルズ インコーポレイテッド | 三置換カルボサイクリックサイクロフィリン結合化合物とその用途 |
| JP2002241273A (ja) * | 2001-02-13 | 2002-08-28 | Sumitomo Pharmaceut Co Ltd | ベンズアミド誘導体およびその利用 |
| WO2002064139A1 (en) * | 2001-02-15 | 2002-08-22 | Neurosearch A/S | Treatment of parkinson's disease by the combined action of a compound with neurotrophic activity and a compound enhancing the dopamine activity |
| WO2002064128A1 (en) * | 2001-02-15 | 2002-08-22 | Neurosearch A/S | Treatment of diseases characterized by excessive or insufficient cell death |
-
2002
- 2002-09-18 EP EP20020020987 patent/EP1402888A1/en not_active Withdrawn
-
2003
- 2003-09-18 AU AU2003271619A patent/AU2003271619A1/en not_active Abandoned
- 2003-09-18 CA CA002498662A patent/CA2498662A1/en not_active Abandoned
- 2003-09-18 WO PCT/EP2003/010406 patent/WO2004026815A2/en not_active Ceased
- 2003-09-18 US US10/528,139 patent/US20070054904A1/en not_active Abandoned
- 2003-09-18 BR BR0314544-1A patent/BR0314544A/pt not_active IP Right Cessation
- 2003-09-18 RU RU2005111256/04A patent/RU2005111256A/ru not_active Application Discontinuation
- 2003-09-18 SG SG200702382-3A patent/SG165995A1/en unknown
- 2003-09-18 MX MXPA05003084A patent/MXPA05003084A/es not_active Application Discontinuation
- 2003-09-18 EP EP09007837A patent/EP2100876A3/en not_active Withdrawn
- 2003-09-18 EP EP03753427A patent/EP1539683A2/en not_active Ceased
- 2003-09-18 JP JP2004537125A patent/JP2005539072A/ja not_active Withdrawn
- 2003-09-18 KR KR1020057004693A patent/KR20050053673A/ko not_active Ceased
- 2003-09-18 CN CNB038252651A patent/CN100546977C/zh not_active Expired - Fee Related
- 2003-09-18 PL PL03374846A patent/PL374846A1/xx not_active Application Discontinuation
-
2005
- 2005-03-07 ZA ZA2005/01913A patent/ZA200501913B/en unknown
-
2009
- 2009-11-23 US US12/624,308 patent/US20110065760A1/en not_active Abandoned
-
2010
- 2010-09-02 RU RU2010136779/04A patent/RU2010136779A/ru not_active Application Discontinuation
- 2010-09-29 JP JP2010219856A patent/JP2011037869A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1402888A1 (en) | 2004-03-31 |
| EP2100876A3 (en) | 2010-02-24 |
| PL374846A1 (en) | 2005-11-14 |
| KR20050053673A (ko) | 2005-06-08 |
| EP2100876A2 (en) | 2009-09-16 |
| CN100546977C (zh) | 2009-10-07 |
| JP2011037869A (ja) | 2011-02-24 |
| ZA200501913B (en) | 2005-07-27 |
| RU2010136779A (ru) | 2012-03-10 |
| EP1539683A2 (en) | 2005-06-15 |
| WO2004026815A2 (en) | 2004-04-01 |
| CN1701061A (zh) | 2005-11-23 |
| US20110065760A1 (en) | 2011-03-17 |
| WO2004026815A3 (en) | 2004-12-02 |
| RU2005111256A (ru) | 2006-10-27 |
| US20070054904A1 (en) | 2007-03-08 |
| AU2003271619A1 (en) | 2004-04-08 |
| BR0314544A (pt) | 2005-08-16 |
| CA2498662A1 (en) | 2004-04-01 |
| SG165995A1 (en) | 2010-11-29 |
| JP2005539072A (ja) | 2005-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MXPA05003084A (es) | Nuevos compuestos para la inhibicion de rotamasas y usos de los mismos. | |
| US10597381B2 (en) | Compounds, compositions, and methods for modulating ferroptosis and treating excitotoxic disorders | |
| EA001436B1 (ru) | Антагонисты рецептора il-8 | |
| US10259775B2 (en) | Compounds, compositions, and methods for modulating ferroptosis and treating excitotoxic disorders | |
| US8207228B2 (en) | Calixarene-based peptide conformation mimetics, methods of use, and methods of making | |
| US5728718A (en) | 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same | |
| US20060004041A1 (en) | Compounds for treatment of neurodegenerative diseases | |
| SE408794B (sv) | Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper | |
| EP1402887A1 (en) | New compounds for the inhibition of undesired cell proliferation and use thereof | |
| CA3129131A1 (en) | Charged ion channel blockers and methods for use | |
| US6677376B1 (en) | Non-peptidic cyclophilin binding compounds and their use | |
| US11439608B2 (en) | Roles of modulators of intersectin-CDC42 signaling in Alzheimer's disease | |
| WO2008068170A1 (en) | Hdac inhibitors | |
| WO2008003800A1 (es) | Derivados de benzo[d]isotiazoles como inhibidores de las histone desacetilasas | |
| US20060252813A1 (en) | Apparatus for curing a composite laminate | |
| ES2300330T3 (es) | Inhibidores de peptido desformilasa. | |
| CN105237444B (zh) | 异羟肟酸类化合物及其制备方法和用途 | |
| Sun et al. | activity of colon carcinoma cells” | |
| Felton | Sulfur Compounds Antagonistic to Growth Factors for Bacteria | |
| WO2003087127A2 (en) | Antimicrobial compounds against staphylococci, mycobacteria, and other infectious agents | |
| WO2004106292A1 (en) | Haloethyl urea compounds and their use to attenuate, inhibit or prevent non-cancerous pathogenic cellular proliferation and diseases associated therewith |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |