NZ552284A - Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 - Google Patents

Info

Publication number

NZ552284A

NZ552284A NZ552284A NZ55228405A NZ552284A NZ 552284 A NZ552284 A NZ 552284A NZ 552284 A NZ552284 A NZ 552284A NZ 55228405 A NZ55228405 A NZ 55228405A NZ 552284 A NZ552284 A NZ 552284A

Authority

NZ

New Zealand

Prior art keywords

alkyl

thiazol

methyl

ylamino

aryl

Prior art date

2004-05-24

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003112 inhibitor Substances 0.000 title description 16
• 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title description 3
• 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 359
• 150000001875 compounds Chemical class 0.000 claims abstract description 286
• 238000011282 treatment Methods 0.000 claims abstract description 83
• 102000004190 Enzymes Human genes 0.000 claims abstract description 38
• 108090000790 Enzymes Proteins 0.000 claims abstract description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
• 208000035475 disorder Diseases 0.000 claims abstract description 23
• 238000002360 preparation method Methods 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• -1 aryl-Ci-a-alkyI Chemical group 0.000 claims description 141
• 239000000203 mixture Substances 0.000 claims description 131
• 125000003118 aryl group Chemical group 0.000 claims description 116
• 125000000623 heterocyclic group Chemical group 0.000 claims description 100
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 92
• 238000006243 chemical reaction Methods 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 48
• 239000003862 glucocorticoid Substances 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 230000029663 wound healing Effects 0.000 claims description 37
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 230000003287 optical effect Effects 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 27
• 229940037128 systemic glucocorticoids Drugs 0.000 claims description 27
• 150000001204 N-oxides Chemical class 0.000 claims description 26
• 125000001475 halogen functional group Chemical group 0.000 claims description 26
• 206010012601 diabetes mellitus Diseases 0.000 claims description 25
• 101710088194 Dehydrogenase Proteins 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 150000002431 hydrogen Chemical class 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 230000001771 impaired effect Effects 0.000 claims description 19
• 206010052428 Wound Diseases 0.000 claims description 18
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 230000003111 delayed effect Effects 0.000 claims description 18
• 150000004677 hydrates Chemical class 0.000 claims description 18
• 208000001132 Osteoporosis Diseases 0.000 claims description 16
• 208000027418 Wounds and injury Diseases 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 208000008589 Obesity Diseases 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 230000002519 immonomodulatory effect Effects 0.000 claims description 15
• 235000020824 obesity Nutrition 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• WTAYWTBOEQYGOG-QPJJXVBHSA-N 2-Nonen-4-one Chemical compound CCCCCC(=O)\C=C\C WTAYWTBOEQYGOG-QPJJXVBHSA-N 0.000 claims description 14
• 206010020772 Hypertension Diseases 0.000 claims description 14
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 230000001404 mediated effect Effects 0.000 claims description 14
• 238000011321 prophylaxis Methods 0.000 claims description 14
• 239000004480 active ingredient Substances 0.000 claims description 13
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
• 208000010412 Glaucoma Diseases 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 9
• 206010012289 Dementia Diseases 0.000 claims description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• 241000236488 Lepra Species 0.000 claims description 8
• 206010024229 Leprosy Diseases 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 201000001421 hyperglycemia Diseases 0.000 claims description 8
• 201000008827 tuberculosis Diseases 0.000 claims description 8
• 206010056340 Diabetic ulcer Diseases 0.000 claims description 7
• 208000004210 Pressure Ulcer Diseases 0.000 claims description 7
• 208000000558 Varicose Ulcer Diseases 0.000 claims description 7
• 241000700605 Viruses Species 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 5
• UAXDBJVXVXJQFJ-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCCC1 UAXDBJVXVXJQFJ-UHFFFAOYSA-N 0.000 claims description 4
• JRXIMHQYNOCOAW-UHFFFAOYSA-N 2-(cyclooctylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound S1C2(CCCC2)C(=O)N=C1NC1CCCCCCC1 JRXIMHQYNOCOAW-UHFFFAOYSA-N 0.000 claims description 4
• CFPUUJOXOXNDQW-UHFFFAOYSA-N 2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound CC1(C)C(C)(C)C1NC(S1)=NC(=O)C11CCCC1 CFPUUJOXOXNDQW-UHFFFAOYSA-N 0.000 claims description 4
• SKXWISZNEAWCJW-UHFFFAOYSA-N 6-(cyclooctylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound S1C2(CCC2)C(=O)N=C1NC1CCCCCCC1 SKXWISZNEAWCJW-UHFFFAOYSA-N 0.000 claims description 4
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 4
• 229910052744 lithium Inorganic materials 0.000 claims description 4
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• GLUAKGKNBDZINR-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(C)SC(NC2C3CCC(C3)C2)=N1 GLUAKGKNBDZINR-UHFFFAOYSA-N 0.000 claims description 3
• UALRGBIQMCFAQH-UHFFFAOYSA-N 2-[(2,2-difluoro-5-bicyclo[2.2.1]heptanyl)amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2C3CC(C(C3)(F)F)C2)=N1 UALRGBIQMCFAQH-UHFFFAOYSA-N 0.000 claims description 3
• YNBPGJSIXHBKLU-UHFFFAOYSA-N 6-(2-methylanilino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound CC1=CC=CC=C1NC(S1)=NC(=O)C11CCC1 YNBPGJSIXHBKLU-UHFFFAOYSA-N 0.000 claims description 3
• YNNSXEVWOODRDZ-UHFFFAOYSA-N 6-(cycloheptylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound S1C2(CCC2)C(=O)N=C1NC1CCCCCC1 YNNSXEVWOODRDZ-UHFFFAOYSA-N 0.000 claims description 3
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 238000009472 formulation Methods 0.000 claims description 3
• 150000004820 halides Chemical class 0.000 claims description 3
• FTBSPSRDJAAHNV-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)(F)C)(C)SC(NC2C3CCC(C3)C2)=N1 FTBSPSRDJAAHNV-UHFFFAOYSA-N 0.000 claims description 2
• BALONPGGQKBAOK-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[(4-hydroxyphenyl)methyl]-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)N=C(NC2C3CCC(C3)C2)S1 BALONPGGQKBAOK-UHFFFAOYSA-N 0.000 claims description 2
• YCNCXQNUXCHRRX-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2C3CCC(C3)C2)=N1 YCNCXQNUXCHRRX-UHFFFAOYSA-N 0.000 claims description 2
• PERAPCUCBBSZOT-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(C)SC(NCC2CCCCC2)=N1 PERAPCUCBBSZOT-UHFFFAOYSA-N 0.000 claims description 2
• AONBTHXPMRRKRA-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethylamino]-5-methyl-5-(oxan-4-ylmethyl)-1,3-thiazol-4-one Chemical compound C=1C=C(F)C=CC=1C(C)NC(S1)=NC(=O)C1(C)CC1CCOCC1 AONBTHXPMRRKRA-UHFFFAOYSA-N 0.000 claims description 2
• UJVKQQXEPKQLAX-UHFFFAOYSA-N 2-methyl-1,3-thiazol-4-one Chemical compound CC1=NC(=O)CS1 UJVKQQXEPKQLAX-UHFFFAOYSA-N 0.000 claims description 2
• GYTLQUPMHLFAKH-UHFFFAOYSA-N 5-(1,1-difluoroethyl)-2-[1-(4-fluorophenyl)ethylamino]-5-methyl-1,3-thiazol-4-one Chemical compound C=1C=C(F)C=CC=1C(C)NC1=NC(=O)C(C)(C(C)(F)F)S1 GYTLQUPMHLFAKH-UHFFFAOYSA-N 0.000 claims 2
• VIUFACJHUKLXPL-UHFFFAOYSA-N 5-ethyl-2-(2-propan-2-ylanilino)-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC=2C(=CC=CC=2)C(C)C)=N1 VIUFACJHUKLXPL-UHFFFAOYSA-N 0.000 claims 2
• 201000005577 familial hyperlipidemia Diseases 0.000 claims 2
• XSTQWNZHFKKBBT-KKSJPVRNSA-N (5s)-2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[(2s)-1-hydroxypropan-2-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)[C@](C)([C@@H](C)CO)S1 XSTQWNZHFKKBBT-KKSJPVRNSA-N 0.000 claims 1
• VXWZKCPEMUMBQL-RJRLTIMHSA-N (5s)-2-[[(1r,4r,5s)-2-hydroxy-5-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@H]1C[C@@]2(C(C[C@@]1([H])C2)O)[H])C1=NC(=O)[C@](C)(C(C)C)S1 VXWZKCPEMUMBQL-RJRLTIMHSA-N 0.000 claims 1
• FBNOGYSMLZDVRI-UJLDYHAWSA-N (5s)-2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound C1([C@@]2(C)C(=O)N=C(S2)NC2[C@@]3([H])CC[C@](C3)(C2)[H])CCOCC1 FBNOGYSMLZDVRI-UJLDYHAWSA-N 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• GUBZNFIBCFUHPQ-UHFFFAOYSA-N 2-(2-chloroanilino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC=2C(=CC=CC=2)Cl)=N1 GUBZNFIBCFUHPQ-UHFFFAOYSA-N 0.000 claims 1
• SIDMUSMJMIZMKV-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2C3CCC(C3)C2)=N1 SIDMUSMJMIZMKV-UHFFFAOYSA-N 0.000 claims 1
• GGORYKZZMPJCCW-UHFFFAOYSA-N 2-(cycloheptylamino)-5-[(3,4-dihydroxyphenyl)methyl]-1,3-thiazol-4-one Chemical compound C1=C(O)C(O)=CC=C1CC1C(=O)N=C(NC2CCCCCC2)S1 GGORYKZZMPJCCW-UHFFFAOYSA-N 0.000 claims 1
• CQFQVCIVLSZFFM-UHFFFAOYSA-N 2-(cycloheptylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2CCCCCC2)=N1 CQFQVCIVLSZFFM-UHFFFAOYSA-N 0.000 claims 1
• OAYIHEQHDOSMAD-UHFFFAOYSA-N 2-(cycloheptylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC2CCCCCC2)=N1 OAYIHEQHDOSMAD-UHFFFAOYSA-N 0.000 claims 1
• ZJLZAARQHWXLMC-UHFFFAOYSA-N 2-(cyclooctylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical group O=C1C(C)(C)SC(NC2CCCCCCC2)=N1 ZJLZAARQHWXLMC-UHFFFAOYSA-N 0.000 claims 1
• RQCIJBSJBFMYBX-UHFFFAOYSA-N 2-(cyclooctylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2CCCCCCC2)=N1 RQCIJBSJBFMYBX-UHFFFAOYSA-N 0.000 claims 1
• UNJGDEQMIBHKEY-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)ethylamino]-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound C=1C=CC=C(F)C=1C(C)NC1=NC(=O)C(C)(C(C)(C)F)S1 UNJGDEQMIBHKEY-UHFFFAOYSA-N 0.000 claims 1
• YVKWHHTZGBZLPX-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)ethylamino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound C=1C=CC=C(F)C=1C(C)NC(S1)=NC(=O)C1(C)C1=CC=NC=C1 YVKWHHTZGBZLPX-UHFFFAOYSA-N 0.000 claims 1
• KEXZDVDUHKKDBN-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethylamino]-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound C=1C=C(F)C=CC=1C(C)NC1=NC(=O)C(C)(C(C)(C)F)S1 KEXZDVDUHKKDBN-UHFFFAOYSA-N 0.000 claims 1
• XUISZKCZKNCBNJ-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethylamino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound C=1C=C(F)C=CC=1C(C)NC1=NC(=O)C(C)(C(F)(F)F)S1 XUISZKCZKNCBNJ-UHFFFAOYSA-N 0.000 claims 1
• HWVCGKOGMAXCRS-UHFFFAOYSA-N 5-(cyclohexylmethylamino)-4-thia-6-azaspiro[2.4]hept-5-en-7-one Chemical compound S1C2(CC2)C(=O)N=C1NCC1CCCCC1 HWVCGKOGMAXCRS-UHFFFAOYSA-N 0.000 claims 1
• HLVDSASBWZLNNO-UHFFFAOYSA-N 5-propan-2-yl-2-(2-propan-2-ylanilino)-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=CC=2)C(C)C)=N1 HLVDSASBWZLNNO-UHFFFAOYSA-N 0.000 claims 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 239000003814 drug Substances 0.000 abstract description 8
• 108090000874 11-beta-hydroxysteroid dehydrogenases Proteins 0.000 abstract description 6
• 102000004277 11-beta-hydroxysteroid dehydrogenases Human genes 0.000 abstract description 6
• 102000011145 Hydroxysteroid Dehydrogenases Human genes 0.000 abstract description 5
• 108010062875 Hydroxysteroid Dehydrogenases Proteins 0.000 abstract description 5
• 238000004949 mass spectrometry Methods 0.000 description 203
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 143
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 124
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 113
• 239000000243 solution Substances 0.000 description 111
• 230000015572 biosynthetic process Effects 0.000 description 108
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 94
• 238000003786 synthesis reaction Methods 0.000 description 89
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• 239000007787 solid Substances 0.000 description 82
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 77
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
• 229910001868 water Inorganic materials 0.000 description 76
• 239000011541 reaction mixture Substances 0.000 description 74
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
• 235000019439 ethyl acetate Nutrition 0.000 description 71
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
• 239000002904 solvent Substances 0.000 description 54
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 50
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 48
• 235000002639 sodium chloride Nutrition 0.000 description 45
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 44
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 239000002585 base Substances 0.000 description 42
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
• 239000000047 product Substances 0.000 description 39
• 238000003818 flash chromatography Methods 0.000 description 37
• 238000003756 stirring Methods 0.000 description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 35
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 239000012267 brine Substances 0.000 description 33
• 229940088598 enzyme Drugs 0.000 description 33
• 238000000746 purification Methods 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 230000000694 effects Effects 0.000 description 30
• 150000001412 amines Chemical class 0.000 description 29
• 235000019441 ethanol Nutrition 0.000 description 28
• 150000002500 ions Chemical class 0.000 description 28
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 229910052757 nitrogen Inorganic materials 0.000 description 27
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
• 239000003921 oil Substances 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 26
• 235000019198 oils Nutrition 0.000 description 25
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 22
• 239000002253 acid Substances 0.000 description 21
• 239000012043 crude product Substances 0.000 description 21
• 229940093499 ethyl acetate Drugs 0.000 description 21
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
• NNFCIYWJLLJEMN-UHFFFAOYSA-N dec-2-en-4-one Chemical compound CCCCCCC(=O)C=CC NNFCIYWJLLJEMN-UHFFFAOYSA-N 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 238000010992 reflux Methods 0.000 description 20
• 238000004128 high performance liquid chromatography Methods 0.000 description 19
• 150000002148 esters Chemical class 0.000 description 18
• 230000005764 inhibitory process Effects 0.000 description 18
• 238000004007 reversed phase HPLC Methods 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
• IHDKBHLTKNUCCW-UHFFFAOYSA-N 1,3-thiazole 1-oxide Chemical compound O=S1C=CN=C1 IHDKBHLTKNUCCW-UHFFFAOYSA-N 0.000 description 16
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 210000001519 tissue Anatomy 0.000 description 14
• 238000001914 filtration Methods 0.000 description 13
• 229960000890 hydrocortisone Drugs 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 13
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 239000000651 prodrug Chemical group 0.000 description 13
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
• 150000001721 carbon Chemical group 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 150000003585 thioureas Chemical class 0.000 description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
• 229960000583 acetic acid Drugs 0.000 description 11
• 230000014509 gene expression Effects 0.000 description 11
• 239000011593 sulfur Substances 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
• 238000010511 deprotection reaction Methods 0.000 description 10
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 229910021529 ammonia Inorganic materials 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• 229960004544 cortisone Drugs 0.000 description 9
• 101150047356 dec-1 gene Proteins 0.000 description 9
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 210000004556 brain Anatomy 0.000 description 8
• 230000031709 bromination Effects 0.000 description 8
• 238000005893 bromination reaction Methods 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
• UTVNSHXHFRIXMM-UHFFFAOYSA-N ethyl 1-bromocyclobutane-1-carboxylate Chemical compound CCOC(=O)C1(Br)CCC1 UTVNSHXHFRIXMM-UHFFFAOYSA-N 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 8
• 229910000162 sodium phosphate Inorganic materials 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 238000002560 therapeutic procedure Methods 0.000 description 8
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
• MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 7
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
• 241000700159 Rattus Species 0.000 description 7
• 230000009471 action Effects 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 208000010877 cognitive disease Diseases 0.000 description 7
• 239000012230 colorless oil Substances 0.000 description 7
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
• 239000003098 androgen Substances 0.000 description 6
• 239000011324 bead Substances 0.000 description 6
• 230000009286 beneficial effect Effects 0.000 description 6
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 125000004093 cyano group Chemical group *C#N 0.000 description 6
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 6
• 201000008980 hyperinsulinism Diseases 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 238000004519 manufacturing process Methods 0.000 description 6
• IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
• 238000002821 scintillation proximity assay Methods 0.000 description 6
• 238000010898 silica gel chromatography Methods 0.000 description 6
• 210000003491 skin Anatomy 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 5
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
• 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 5
• UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 5
• APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
• 208000031226 Hyperlipidaemia Diseases 0.000 description 5
• 108010044467 Isoenzymes Proteins 0.000 description 5
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 230000029936 alkylation Effects 0.000 description 5
• 238000005804 alkylation reaction Methods 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 5
• 238000009835 boiling Methods 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 230000008878 coupling Effects 0.000 description 5
• 238000010168 coupling process Methods 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• WBNUBZZHHXFAGK-UHFFFAOYSA-N cycloheptylthiourea Chemical compound NC(=S)NC1CCCCCC1 WBNUBZZHHXFAGK-UHFFFAOYSA-N 0.000 description 5
• RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 5
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
• 230000006870 function Effects 0.000 description 5
• 239000007789 gas Substances 0.000 description 5
• 230000002440 hepatic effect Effects 0.000 description 5
• 208000026278 immune system disease Diseases 0.000 description 5
• 238000001727 in vivo Methods 0.000 description 5
• 150000002540 isothiocyanates Chemical class 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 210000004185 liver Anatomy 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
• 235000015320 potassium carbonate Nutrition 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 238000002953 preparative HPLC Methods 0.000 description 5
• 235000011149 sulphuric acid Nutrition 0.000 description 5
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• HXTOTKHBSWGCMX-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanylthiourea Chemical compound C1CC2C(NC(=S)N)CC1C2 HXTOTKHBSWGCMX-UHFFFAOYSA-N 0.000 description 4
• HGBRBTBMLVMYPC-UHFFFAOYSA-N 4-amino-3h-1,3-oxazol-2-one Chemical compound NC1=COC(=O)N1 HGBRBTBMLVMYPC-UHFFFAOYSA-N 0.000 description 4
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
• 241001024304 Mino Species 0.000 description 4
• 241000699666 Mus <mouse, genus> Species 0.000 description 4
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• NHRCTOSRUASFLK-QMMMGPOBSA-N [(2r)-2-phenylpropyl]thiourea Chemical compound NC(=S)NC[C@H](C)C1=CC=CC=C1 NHRCTOSRUASFLK-QMMMGPOBSA-N 0.000 description 4
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 4
• AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 4
• 229960005471 androstenedione Drugs 0.000 description 4
• AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• 239000012131 assay buffer Substances 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
• WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-UHFFFAOYSA-N 0.000 description 4
• 239000003925 fat Substances 0.000 description 4
• 235000019197 fats Nutrition 0.000 description 4
• 210000002950 fibroblast Anatomy 0.000 description 4
• 230000037406 food intake Effects 0.000 description 4
• 239000008103 glucose Substances 0.000 description 4
• 230000009229 glucose formation Effects 0.000 description 4
• 230000035876 healing Effects 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 235000011167 hydrochloric acid Nutrition 0.000 description 4
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
• 210000000987 immune system Anatomy 0.000 description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
• 238000003760 magnetic stirring Methods 0.000 description 4
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
• RNWRVPVPLQMTAP-UHFFFAOYSA-N methyl 1-bromocyclohexane-1-carboxylate Chemical compound COC(=O)C1(Br)CCCCC1 RNWRVPVPLQMTAP-UHFFFAOYSA-N 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 235000019260 propionic acid Nutrition 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 239000012047 saturated solution Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
• 150000003431 steroids Chemical class 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 239000006188 syrup Substances 0.000 description 4
• 235000020357 syrup Nutrition 0.000 description 4
• 210000001550 testis Anatomy 0.000 description 4
• SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical group O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 3
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 3
• YHMWNWCXIPRUOA-UHFFFAOYSA-N 1-(1-adamantyl)-3-(2-methoxyethyl)thiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NCCOC)C3 YHMWNWCXIPRUOA-UHFFFAOYSA-N 0.000 description 3
• JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 3
• HKUKNCCRHCMALS-UHFFFAOYSA-N 1-oxo-1,3-thiazol-2-amine Chemical class NC1=NC=CS1=O HKUKNCCRHCMALS-UHFFFAOYSA-N 0.000 description 3
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
• PBOZAHAHLGEZDH-UHFFFAOYSA-N 2-(cycloheptylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound S1C2(CCCCC2)C(=O)N=C1NC1CCCCCC1 PBOZAHAHLGEZDH-UHFFFAOYSA-N 0.000 description 3
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
• 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 3
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 3
• JCXABKUTAMQXNE-UHFFFAOYSA-N 5-cyclopentyl-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1NC1=NC(=O)C(C2CCCC2)S1 JCXABKUTAMQXNE-UHFFFAOYSA-N 0.000 description 3
• 208000004611 Abdominal Obesity Diseases 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 206010065941 Central obesity Diseases 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• 102000008186 Collagen Human genes 0.000 description 3
• 108010035532 Collagen Proteins 0.000 description 3
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
• 102000003638 Glucose-6-Phosphatase Human genes 0.000 description 3
• 108010086800 Glucose-6-Phosphatase Proteins 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• 241000235058 Komagataella pastoris Species 0.000 description 3
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
• 241001529936 Murinae Species 0.000 description 3
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
• NHRCTOSRUASFLK-MRVPVSSYSA-N [(2s)-2-phenylpropyl]thiourea Chemical compound NC(=S)NC[C@@H](C)C1=CC=CC=C1 NHRCTOSRUASFLK-MRVPVSSYSA-N 0.000 description 3
• LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 229940024606 amino acid Drugs 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
• 150000003936 benzamides Chemical class 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
• 230000033228 biological regulation Effects 0.000 description 3
• 210000000988 bone and bone Anatomy 0.000 description 3
• 125000001246 bromo group Chemical group Br* 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• OBZHEBDUNPOCJG-SZTGPWMUSA-N carbenoxolone Chemical compound C([C@H]1C2=CC(=O)[C@@H]34)[C@](C)(C(O)=O)CC[C@@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@H]1[C@@]3(C)CC[C@@H](OC(=O)CCC(O)=O)C1(C)C OBZHEBDUNPOCJG-SZTGPWMUSA-N 0.000 description 3
• 229960000530 carbenoxolone Drugs 0.000 description 3
• 239000001569 carbon dioxide Substances 0.000 description 3
• 229910002092 carbon dioxide Inorganic materials 0.000 description 3
• 150000001728 carbonyl compounds Chemical class 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229920001436 collagen Polymers 0.000 description 3
• 238000004440 column chromatography Methods 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 3
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
• 229910001873 dinitrogen Inorganic materials 0.000 description 3
• 238000009826 distribution Methods 0.000 description 3
• 230000002526 effect on cardiovascular system Effects 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 229960003720 enoxolone Drugs 0.000 description 3
• 238000001952 enzyme assay Methods 0.000 description 3
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 3
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 239000012065 filter cake Substances 0.000 description 3
• 235000012631 food intake Nutrition 0.000 description 3
• 239000011521 glass Substances 0.000 description 3
• 235000011187 glycerol Nutrition 0.000 description 3
• 229960004198 guanidine Drugs 0.000 description 3
• 230000008348 humoral response Effects 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
• 230000002218 hypoglycaemic effect Effects 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 230000028993 immune response Effects 0.000 description 3
• 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 230000004410 intraocular pressure Effects 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 230000007246 mechanism Effects 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 125000002757 morpholinyl group Chemical group 0.000 description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 239000012299 nitrogen atmosphere Substances 0.000 description 3
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
• 238000003953 normal phase liquid chromatography Methods 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 125000004043 oxo group Chemical group O=* 0.000 description 3
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
• 125000005936 piperidyl group Chemical group 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
• 238000006798 ring closing metathesis reaction Methods 0.000 description 3
• 238000007363 ring formation reaction Methods 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
• 235000019345 sodium thiosulphate Nutrition 0.000 description 3
• 239000000600 sorbitol Substances 0.000 description 3
• 235000010356 sorbitol Nutrition 0.000 description 3
• 229960003604 testosterone Drugs 0.000 description 3
• 239000010409 thin film Substances 0.000 description 3
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
• IDKGPXDVVKOQIT-UHFFFAOYSA-N (1-oxo-1,3-thiazol-5-yl)methanol Chemical class OCC1=CN=CS1=O IDKGPXDVVKOQIT-UHFFFAOYSA-N 0.000 description 2
• YOBWYLCYNUIVKF-SDUJUNFKSA-N (1s)-3-bromobicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2(C(O)=O)C(Br)C[C@]1([H])C2 YOBWYLCYNUIVKF-SDUJUNFKSA-N 0.000 description 2
• FUKKXMVIGCLNGG-UHFFFAOYSA-N (2-propan-2-ylphenyl)thiourea Chemical compound CC(C)C1=CC=CC=C1NC(N)=S FUKKXMVIGCLNGG-UHFFFAOYSA-N 0.000 description 2
• LESGKWOTXMFHMB-XHDPSFHLSA-N (5r)-5-methyl-2-[[(1s)-1-phenylethyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@](C(C)C)(C)SC(N[C@@H](C)C=2C=CC=CC=2)=N1 LESGKWOTXMFHMB-XHDPSFHLSA-N 0.000 description 2
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
• GHNWTKBRMNRUFT-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)bicyclo[2.2.2]octan-4-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1(CC2)CCC2(N)CC1 GHNWTKBRMNRUFT-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• FUFLCEKSBBHCMO-KJQYFISQSA-N 11-dehydrocorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 FUFLCEKSBBHCMO-KJQYFISQSA-N 0.000 description 2
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
• VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 2
• MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
• JXIPHTFNPSUXSG-UHFFFAOYSA-N 2-(2-chloroanilino)-5-cyclopentyl-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC1=NC(=O)C(C2CCCC2)S1 JXIPHTFNPSUXSG-UHFFFAOYSA-N 0.000 description 2
• SWDLLIWJYZSVOA-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CN=CC=2)SC=1NC1=CC=CC=C1Cl SWDLLIWJYZSVOA-UHFFFAOYSA-N 0.000 description 2
• OLLIGTNPTVJPAX-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=CC=C1Cl OLLIGTNPTVJPAX-UHFFFAOYSA-N 0.000 description 2
• PGETWDIRWDVJSR-YMNIQAILSA-N 2-(2-fluoroanilino)-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)C([C@@H]2COCC2)S1 PGETWDIRWDVJSR-YMNIQAILSA-N 0.000 description 2
• YZDLNOVQXOSMBO-UHFFFAOYSA-N 2-(cycloheptylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound S1C2(CCCC2)C(=O)N=C1NC1CCCCCC1 YZDLNOVQXOSMBO-UHFFFAOYSA-N 0.000 description 2
• SLTOJUMZRHENNT-UHFFFAOYSA-N 2-(cycloheptylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NC2CCCCCC2)=N1 SLTOJUMZRHENNT-UHFFFAOYSA-N 0.000 description 2
• NRVZPJUAZVHNMN-UHFFFAOYSA-N 2-(cyclohexylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2CCCCC2)=N1 NRVZPJUAZVHNMN-UHFFFAOYSA-N 0.000 description 2
• JDCYBYKALPQUCN-SFVWDYPZSA-N 2-(cyclohexylmethylamino)-5-methyl-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)([C@@H]2COCC2)SC=1NCC1CCCCC1 JDCYBYKALPQUCN-SFVWDYPZSA-N 0.000 description 2
• RVCGRXLHMCBEQB-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-phenyl-1,3-oxazol-4-one Chemical compound O1C(C=2C=CC=CC=2)C(=O)N=C1NCC1CCCCC1 RVCGRXLHMCBEQB-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• PKOUEAKRBUYDJE-INHVJJQHSA-N 2-[[(1r)-1-(2-fluorophenyl)ethyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(N[C@H](C)C=2C(=CC=CC=2)F)=N1 PKOUEAKRBUYDJE-INHVJJQHSA-N 0.000 description 2
• VQYLKQGNSKBIKT-INHVJJQHSA-N 2-[[(1r)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(N[C@H](C)C=2C=CC(F)=CC=2)=N1 VQYLKQGNSKBIKT-INHVJJQHSA-N 0.000 description 2
• YVKWHHTZGBZLPX-PIJUOJQZSA-N 2-[[(1s)-1-(2-fluorophenyl)ethyl]amino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C(=CC=CC=1)F)C(S1)=NC(=O)C1(C)C1=CC=NC=C1 YVKWHHTZGBZLPX-PIJUOJQZSA-N 0.000 description 2
• RTQSUSWTUGCXER-VPHXOMNUSA-N 2-[[(1s)-1-cyclohexylethyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(N[C@@H](C)C2CCCCC2)=N1 RTQSUSWTUGCXER-VPHXOMNUSA-N 0.000 description 2
• MSZHOSYAGVBHPO-XBZGWKTJSA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propyl-1,3-thiazol-4-one Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C1=NC(=O)C(C)(CCC)S1 MSZHOSYAGVBHPO-XBZGWKTJSA-N 0.000 description 2
• GUGBDNQGYWHFSW-HBNTYKKESA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C(S1)=NC(=O)C21CCOCC2 GUGBDNQGYWHFSW-HBNTYKKESA-N 0.000 description 2
• ZAWTZALBLQKRAW-UHFFFAOYSA-N 2-amino-5-propan-2-yl-1,3-oxazol-4-one Chemical compound CC(C)C1OC(N)=NC1=O ZAWTZALBLQKRAW-UHFFFAOYSA-N 0.000 description 2
• JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 2
• KRXAVBPUAIKSFF-UHFFFAOYSA-N 3,4-dihydrodithiine Chemical compound C1CC=CSS1 KRXAVBPUAIKSFF-UHFFFAOYSA-N 0.000 description 2
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
• USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 2
• IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
• ITFSJIDPPAPJGI-UHFFFAOYSA-N 5-cyclopentyl-2-(2-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)C(C2CCCC2)S1 ITFSJIDPPAPJGI-UHFFFAOYSA-N 0.000 description 2
• GBHCRZABOYORSW-UHFFFAOYSA-N 6-(3-bicyclo[2.2.1]heptanylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCC1 GBHCRZABOYORSW-UHFFFAOYSA-N 0.000 description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 208000035143 Bacterial infection Diseases 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• 101150041968 CDC13 gene Proteins 0.000 description 2
• OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
• 238000006969 Curtius rearrangement reaction Methods 0.000 description 2
• 208000014311 Cushing syndrome Diseases 0.000 description 2
• 108090000385 Fibroblast growth factor 7 Proteins 0.000 description 2
• 230000005526 G1 to G0 transition Effects 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 208000002705 Glucose Intolerance Diseases 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 229910004373 HOAc Inorganic materials 0.000 description 2
• 208000013016 Hypoglycemia Diseases 0.000 description 2
• 102100037852 Insulin-like growth factor I Human genes 0.000 description 2
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
• 240000007472 Leucaena leucocephala Species 0.000 description 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
• 102000002274 Matrix Metalloproteinases Human genes 0.000 description 2
• 108010000684 Matrix Metalloproteinases Proteins 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 2
• 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
• 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• 241000283984 Rodentia Species 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• KRWTWSSMURUMDE-UHFFFAOYSA-N [1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane Chemical group COC1=CC=C2C=CC=CC2=C1C(C1=CC=CC=C1C=C1)=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KRWTWSSMURUMDE-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
• 239000000654 additive Substances 0.000 description 2
• 210000001789 adipocyte Anatomy 0.000 description 2
• 210000000577 adipose tissue Anatomy 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• 235000011114 ammonium hydroxide Nutrition 0.000 description 2
• 102000001307 androgen receptors Human genes 0.000 description 2
• 108010080146 androgen receptors Proteins 0.000 description 2
• 229940030486 androgens Drugs 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 230000001837 anti-cortisol effect Effects 0.000 description 2
• 230000009118 appropriate response Effects 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 229910052786 argon Inorganic materials 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• 208000022362 bacterial infectious disease Diseases 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 210000000481 breast Anatomy 0.000 description 2
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
• RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 2
• FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• 230000001886 ciliary effect Effects 0.000 description 2
• 238000010367 cloning Methods 0.000 description 2
• OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 description 2
• LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
• AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 2
• GZZUQNWMRFWSAD-UHFFFAOYSA-N cyclohexylmethylthiourea Chemical compound NC(=S)NCC1CCCCC1 GZZUQNWMRFWSAD-UHFFFAOYSA-N 0.000 description 2
• HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 2
• RWTUIVXJWXJSIK-UHFFFAOYSA-N cyclooctylthiourea Chemical compound NC(=S)NC1CCCCCCC1 RWTUIVXJWXJSIK-UHFFFAOYSA-N 0.000 description 2
• JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
• 230000003247 decreasing effect Effects 0.000 description 2
• 229960003957 dexamethasone Drugs 0.000 description 2
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 2
• 235000019700 dicalcium phosphate Nutrition 0.000 description 2
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000001177 diphosphate Substances 0.000 description 2
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
• 235000011180 diphosphates Nutrition 0.000 description 2
• 238000004090 dissolution Methods 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 239000003937 drug carrier Substances 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 229940010344 estradiol / estrone Drugs 0.000 description 2
• 108010038795 estrogen receptors Proteins 0.000 description 2
• 102000015694 estrogen receptors Human genes 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• ALHOFXQMBUWICK-UHFFFAOYSA-N ethyl 2-bromo-2-methylbutanoate Chemical compound CCOC(=O)C(C)(Br)CC ALHOFXQMBUWICK-UHFFFAOYSA-N 0.000 description 2
• XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 2
• BPICUFAWVCELSX-UHFFFAOYSA-N ethyl 4-oxo-2-[2-(trifluoromethyl)anilino]-1,3-thiazole-5-carboxylate Chemical compound O=C1C(C(=O)OCC)SC(NC=2C(=CC=CC=2)C(F)(F)F)=N1 BPICUFAWVCELSX-UHFFFAOYSA-N 0.000 description 2
• VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 description 2
• BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
• 239000012530 fluid Substances 0.000 description 2
• 238000003682 fluorination reaction Methods 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 230000004110 gluconeogenesis Effects 0.000 description 2
• 239000003163 gonadal steroid hormone Substances 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• BNSYGCKJOAPBCM-UHFFFAOYSA-N heptan-2-ol Chemical compound [CH2]C(O)CCCCC BNSYGCKJOAPBCM-UHFFFAOYSA-N 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 230000003914 insulin secretion Effects 0.000 description 2
• 230000002452 interceptive effect Effects 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 239000007791 liquid phase Substances 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
• 210000004072 lung Anatomy 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
• 230000011987 methylation Effects 0.000 description 2
• 238000007069 methylation reaction Methods 0.000 description 2
• 239000003607 modifier Substances 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• 210000003205 muscle Anatomy 0.000 description 2
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 102000006255 nuclear receptors Human genes 0.000 description 2
• 108020004017 nuclear receptors Proteins 0.000 description 2
• RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 235000011007 phosphoric acid Nutrition 0.000 description 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 201000009395 primary hyperaldosteronism Diseases 0.000 description 2
• 230000035755 proliferation Effects 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• 239000012363 selectfluor Substances 0.000 description 2
• 238000013207 serial dilution Methods 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 239000008109 sodium starch glycolate Substances 0.000 description 2
• 229940079832 sodium starch glycolate Drugs 0.000 description 2
• 229920003109 sodium starch glycolate Polymers 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 235000010265 sodium sulphite Nutrition 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 125000003003 spiro group Chemical group 0.000 description 2
• 239000012258 stirred mixture Substances 0.000 description 2
• 125000003107 substituted aryl group Chemical group 0.000 description 2
• 238000004808 supercritical fluid chromatography Methods 0.000 description 2
• 238000001356 surgical procedure Methods 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• 229960001367 tartaric acid Drugs 0.000 description 2
• 230000002123 temporal effect Effects 0.000 description 2
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• 239000011701 zinc Substances 0.000 description 2
• XAYFCRMNDLYHKZ-MQYQWHSLSA-N (1r,2s,4r,5s)-2-phenylmethoxybicyclo[2.2.1]heptan-5-ol Chemical compound O([C@H]1C[C@@]2([C@H](C[C@@]1([H])C2)O)[H])CC1=CC=CC=C1 XAYFCRMNDLYHKZ-MQYQWHSLSA-N 0.000 description 1
• YHUQPGPXJUVMNN-JWXFUTCRSA-N (1r,2s,4r,5s)-bicyclo[2.2.1]heptane-2,5-diol Chemical compound C1[C@H](O)[C@@]2([H])C[C@H](O)[C@]1([H])C2 YHUQPGPXJUVMNN-JWXFUTCRSA-N 0.000 description 1
• RBGDFYZLQKZUCO-CSMHCCOUSA-N (1r,3s,4s)-3-isothiocyanatobicyclo[2.2.1]heptane Chemical compound C1C[C@@H]2[C@@H](N=C=S)C[C@H]1C2 RBGDFYZLQKZUCO-CSMHCCOUSA-N 0.000 description 1
• VTTCLFDTPTVOED-RFZPGFLSSA-N (1r,4r)-2,2-difluorobicyclo[2.2.1]heptan-5-one Chemical compound C1[C@]2([H])CC(=O)[C@@]1([H])CC2(F)F VTTCLFDTPTVOED-RFZPGFLSSA-N 0.000 description 1
• KAGFXFNGZHHSMN-UPJWGTAASA-N (1r,4r,5s)-2,2-difluoro-5-phenylmethoxybicyclo[2.2.1]heptane Chemical compound O([C@H]1C[C@]2(C[C@@]1(CC2(F)F)[H])[H])CC1=CC=CC=C1 KAGFXFNGZHHSMN-UPJWGTAASA-N 0.000 description 1
• MXWBAAFCUCTYCO-PBXRRBTRSA-N (1r,4r,5s)-2,2-difluorobicyclo[2.2.1]heptan-5-ol Chemical compound C1[C@]2([H])C[C@H](O)[C@@]1([H])CC2(F)F MXWBAAFCUCTYCO-PBXRRBTRSA-N 0.000 description 1
• ONJJWHNYLNPTMA-BZPMIXESSA-N (1r,4r,5s)-5-phenylmethoxybicyclo[2.2.1]heptan-2-one Chemical compound O([C@H]1C[C@@]2(C(=O)C[C@]1(C2)[H])[H])CC1=CC=CC=C1 ONJJWHNYLNPTMA-BZPMIXESSA-N 0.000 description 1
• DSSYKIVIOFKYAU-XVKPBYJWSA-N (1s,4r)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1C[C@@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-XVKPBYJWSA-N 0.000 description 1
• FGZGYIQTJWGEEZ-UHFFFAOYSA-N (2,2,3,3-tetramethylcyclopropyl)thiourea Chemical compound CC1(C)C(NC(N)=S)C1(C)C FGZGYIQTJWGEEZ-UHFFFAOYSA-N 0.000 description 1
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
• YZUKKTCDYSIWKJ-UHFFFAOYSA-N (2-chlorophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1Cl YZUKKTCDYSIWKJ-UHFFFAOYSA-N 0.000 description 1
• WYVZQQOFMQRNPF-UHFFFAOYSA-N (2-fluorophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1F WYVZQQOFMQRNPF-UHFFFAOYSA-N 0.000 description 1
• RWBRUCCWZPSBFC-RXRZZTMXSA-N (20S)-20-hydroxypregn-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](O)C)[C@@]1(C)CC2 RWBRUCCWZPSBFC-RXRZZTMXSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• UEBARDWJXBGYEJ-SCSAIBSYSA-N (2r)-2-bromo-3-methylbutanoic acid Chemical compound CC(C)[C@@H](Br)C(O)=O UEBARDWJXBGYEJ-SCSAIBSYSA-N 0.000 description 1
• MVYUMPZRKNBHOP-SCSAIBSYSA-N (2r)-2-bromo-3-methylbutanoyl chloride Chemical compound CC(C)[C@@H](Br)C(Cl)=O MVYUMPZRKNBHOP-SCSAIBSYSA-N 0.000 description 1
• MONMFXREYOKQTI-UWTATZPHSA-N (2r)-2-bromopropanoic acid Chemical compound C[C@@H](Br)C(O)=O MONMFXREYOKQTI-UWTATZPHSA-N 0.000 description 1
• MONMFXREYOKQTI-REOHCLBHSA-N (2s)-2-bromopropanoic acid Chemical compound C[C@H](Br)C(O)=O MONMFXREYOKQTI-REOHCLBHSA-N 0.000 description 1
• YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
• TULNEJCEVLHZMZ-CYBMUJFWSA-N (5r)-2-(2-chloroanilino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@](C(C)C)(C)SC(NC=2C(=CC=CC=2)Cl)=N1 TULNEJCEVLHZMZ-CYBMUJFWSA-N 0.000 description 1
• XKBLDWFSRUSDEZ-CYBMUJFWSA-N (5r)-2-(2-fluoroanilino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@](C(C)C)(C)SC(NC=2C(=CC=CC=2)F)=N1 XKBLDWFSRUSDEZ-CYBMUJFWSA-N 0.000 description 1
• PRRJSBHQHDXENB-IWXRYERYSA-N (5r)-2-(4-bicyclo[2.2.1]heptanylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@](C(C)C)(C)SC(NC23CCC(CC2)C3)=N1 PRRJSBHQHDXENB-IWXRYERYSA-N 0.000 description 1
• FTBSPSRDJAAHNV-MAGOMRGPSA-N (5r)-2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)[C@](C)(C(C)(C)F)S1 FTBSPSRDJAAHNV-MAGOMRGPSA-N 0.000 description 1
• QSDFLOWHPNTKRK-DVJFUJMWSA-N (5r)-2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(oxan-4-ylmethyl)-1,3-thiazol-4-one Chemical compound C([C@@]1(C(=O)N=C(S1)NC1[C@@]2([H])CC[C@](C2)(C1)[H])C)C1CCOCC1 QSDFLOWHPNTKRK-DVJFUJMWSA-N 0.000 description 1
• SUBUXFVWUBEELD-WCQYABFASA-N (5r)-2-[[(2r)-2-phenylpropyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@@H](C(C)C)SC(NC[C@H](C)C=2C=CC=CC=2)=N1 SUBUXFVWUBEELD-WCQYABFASA-N 0.000 description 1
• KMJISCSUVGMRLG-ZYHUDNBSSA-N (5r)-5-ethyl-2-[[(2s)-2-phenylpropyl]amino]-1,3-thiazol-4-one Chemical compound O=C1[C@@H](CC)SC(NC[C@@H](C)C=2C=CC=CC=2)=N1 KMJISCSUVGMRLG-ZYHUDNBSSA-N 0.000 description 1
• PRRJSBHQHDXENB-AWAWDMARSA-N (5s)-2-(4-bicyclo[2.2.1]heptanylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@@](C(C)C)(C)SC(NC23CCC(CC2)C3)=N1 PRRJSBHQHDXENB-AWAWDMARSA-N 0.000 description 1
• AQSLWHYOQRIJJE-YRORDHRNSA-N (5s)-2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-7,7-dimethyl-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)[C@]21CCOC(C)(C)C2 AQSLWHYOQRIJJE-YRORDHRNSA-N 0.000 description 1
• VQYLKQGNSKBIKT-BONVTDFDSA-N (5s)-2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@@](C(C)C)(C)SC(N[C@@H](C)C=2C=CC(F)=CC=2)=N1 VQYLKQGNSKBIKT-BONVTDFDSA-N 0.000 description 1
• SUBUXFVWUBEELD-YPMHNXCESA-N (5s)-2-[[(2s)-2-phenylpropyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@H](C(C)C)SC(NC[C@@H](C)C=2C=CC=CC=2)=N1 SUBUXFVWUBEELD-YPMHNXCESA-N 0.000 description 1
• MCDAKVSVFGTCMR-CTZHQLGESA-N (5s)-5-[(1-acetylpiperidin-4-yl)methyl]-2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-1,3-thiazol-4-one Chemical compound C([C@]1(C(=O)N=C(S1)NC1[C@@]2([H])CC[C@](C2)(C1)[H])C)C1CCN(C(C)=O)CC1 MCDAKVSVFGTCMR-CTZHQLGESA-N 0.000 description 1
• LESGKWOTXMFHMB-NHYWBVRUSA-N (5s)-5-methyl-2-[[(1s)-1-phenylethyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@@](C(C)C)(C)SC(N[C@@H](C)C=2C=CC=CC=2)=N1 LESGKWOTXMFHMB-NHYWBVRUSA-N 0.000 description 1
• RSFNBXGYMLAMAH-PBHICJAKSA-N (5s,7r)-2-(cyclooctylamino)-7-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1[C@H](OC)CCC[C@]21C(=O)N=C(NC1CCCCCCC1)S2 RSFNBXGYMLAMAH-PBHICJAKSA-N 0.000 description 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
• 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
• NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
• AMNURQPTXNTGRJ-UHFFFAOYSA-N 1,2,3a,4-tetrahydro-[1,3]thiazolo[5,4-c]pyridine Chemical class C1=NCC2SCNC2=C1 AMNURQPTXNTGRJ-UHFFFAOYSA-N 0.000 description 1
• DMMFOSKAKXLTFP-UHFFFAOYSA-N 1,2-difluorobicyclo[2.2.1]heptane Chemical compound C1CC2(F)C(F)CC1C2 DMMFOSKAKXLTFP-UHFFFAOYSA-N 0.000 description 1
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 description 1
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
• ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 1
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• ONUXKKJOQDKPOT-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1(CC2)CCC2(C(O)=O)CC1 ONUXKKJOQDKPOT-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• MUSCLEBGQGXIBI-UHFFFAOYSA-N 1-bromocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1(Br)CCCC1 MUSCLEBGQGXIBI-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• YPKFLUARLJRPQM-UHFFFAOYSA-N 1-isothiocyanatoadamantane Chemical compound C1C(C2)CC3CC2CC1(N=C=S)C3 YPKFLUARLJRPQM-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 108010082514 17-Hydroxysteroid Dehydrogenases Proteins 0.000 description 1
• 102000004026 17-Hydroxysteroid Dehydrogenases Human genes 0.000 description 1
• 102100022586 17-beta-hydroxysteroid dehydrogenase type 2 Human genes 0.000 description 1
• 101710147297 17-beta-hydroxysteroid dehydrogenase type 2 Proteins 0.000 description 1
• 102000054917 17-beta-hydroxysteroid dehydrogenase type 3 Human genes 0.000 description 1
• 108010084625 17-beta-hydroxysteroid dehydrogenase type 3 Proteins 0.000 description 1
• NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
• JERGUCIJOXJXHF-TVWVXWENSA-N 17alpha-hydroxypregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JERGUCIJOXJXHF-TVWVXWENSA-N 0.000 description 1
• DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• AYTPIVIDHMVGSX-UHFFFAOYSA-N 2,1,3-benzoselenadiazole Chemical compound C1=CC=CC2=N[se]N=C21 AYTPIVIDHMVGSX-UHFFFAOYSA-N 0.000 description 1
• AWKGSDHAFGPBIM-UHFFFAOYSA-N 2-(1-adamantylamino)-1-oxa-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC23CC4CC(CC(C4)C2)C3)OC11CCCC1 AWKGSDHAFGPBIM-UHFFFAOYSA-N 0.000 description 1
• ATEMBPLAADSXGS-UHFFFAOYSA-N 2-(1-adamantylamino)-5-(2-anilinoethyl)-1,3-thiazol-4-one Chemical compound O=C1N=C(NC23CC4CC(CC(C4)C2)C3)SC1CCNC1=CC=CC=C1 ATEMBPLAADSXGS-UHFFFAOYSA-N 0.000 description 1
• GMXBRMGHFYMYRS-UHFFFAOYSA-N 2-(1-adamantylamino)-5-benzyl-1,3-oxazol-4-one Chemical compound O=C1N=C(NC23CC4CC(CC(C4)C2)C3)OC1CC1=CC=CC=C1 GMXBRMGHFYMYRS-UHFFFAOYSA-N 0.000 description 1
• UQQIZAZNOWZONL-UHFFFAOYSA-N 2-(1-adamantylamino)-5-cyclopentyl-1,3-thiazol-4-one Chemical compound O=C1N=C(NC23CC4CC(CC(C4)C2)C3)SC1C1CCCC1 UQQIZAZNOWZONL-UHFFFAOYSA-N 0.000 description 1
• PCERCPJNLGNJKG-UHFFFAOYSA-N 2-(1-adamantylamino)-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound S1C(NC23CC4CC(CC(C4)C2)C3)=NC(=O)C1(C)C1=CC=NC=C1 PCERCPJNLGNJKG-UHFFFAOYSA-N 0.000 description 1
• FDDFTTXYTHKLRY-UHFFFAOYSA-N 2-(1-adamantylamino)-5-phenyl-1,3-oxazol-4-one Chemical compound O=C1N=C(NC23CC4CC(CC(C4)C2)C3)OC1C1=CC=CC=C1 FDDFTTXYTHKLRY-UHFFFAOYSA-N 0.000 description 1
• JSXQUKCFYAPBIL-UHFFFAOYSA-N 2-(1-adamantylamino)-5-propan-2-yl-1,3-oxazol-4-one Chemical compound O=C1C(C(C)C)OC(NC23CC4CC(CC(C4)C2)C3)=N1 JSXQUKCFYAPBIL-UHFFFAOYSA-N 0.000 description 1
• ABMACIBWUWXYOZ-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-ylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CCN(CC3)C2)SC11CCCC1 ABMACIBWUWXYOZ-UHFFFAOYSA-N 0.000 description 1
• RTQSUSWTUGCXER-UHFFFAOYSA-N 2-(1-cyclohexylethylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC(C)C2CCCCC2)=N1 RTQSUSWTUGCXER-UHFFFAOYSA-N 0.000 description 1
• DTWWUJYHZSUGDH-UHFFFAOYSA-N 2-(1-oxo-1,3-thiazol-5-yl)acetic acid Chemical class OC(=O)CC1=CN=CS1=O DTWWUJYHZSUGDH-UHFFFAOYSA-N 0.000 description 1
• ADIGBQPNAAISHL-UHFFFAOYSA-N 2-(1h-indazol-5-ylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C=C3C=NNC3=CC=2)=N1 ADIGBQPNAAISHL-UHFFFAOYSA-N 0.000 description 1
• INFQCFCUBZJGTN-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CN=CC=2)SC=1NC1=CC=C(Cl)C=C1Cl INFQCFCUBZJGTN-UHFFFAOYSA-N 0.000 description 1
• GTWJHNJIPBWSHB-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 GTWJHNJIPBWSHB-UHFFFAOYSA-N 0.000 description 1
• IFBQDAZXUSEWMA-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC(F)=CC=2)F)=N1 IFBQDAZXUSEWMA-UHFFFAOYSA-N 0.000 description 1
• HTTPORZDMTZXKZ-UHFFFAOYSA-N 2-(2,5-difluoroanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=C(F)C=2)F)=N1 HTTPORZDMTZXKZ-UHFFFAOYSA-N 0.000 description 1
• HQIDCVHKJRUBNS-UHFFFAOYSA-N 2-(2,5-dimethylanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=C(C)C=2)C)=N1 HQIDCVHKJRUBNS-UHFFFAOYSA-N 0.000 description 1
• VFQIZPSQHCJETJ-UHFFFAOYSA-N 2-(2-adamantylamino)-1-oxa-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CC4CC(C3)CC2C4)OC11CCCC1 VFQIZPSQHCJETJ-UHFFFAOYSA-N 0.000 description 1
• OGAAFDDGSBGDEL-UHFFFAOYSA-N 2-(2-adamantylamino)-5-propan-2-yl-1,3-oxazol-4-one Chemical compound O=C1C(C(C)C)OC(NC2C3CC4CC(C3)CC2C4)=N1 OGAAFDDGSBGDEL-UHFFFAOYSA-N 0.000 description 1
• UWCUQHYESVQVLY-UHFFFAOYSA-N 2-(2-chloro-4-methylanilino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound ClC1=CC(C)=CC=C1NC(S1)=NC(=O)C11CCCC1 UWCUQHYESVQVLY-UHFFFAOYSA-N 0.000 description 1
• VGZUUEHTLRIUFY-UHFFFAOYSA-N 2-(2-chloroanilino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound ClC1=CC=CC=C1NC(S1)=NC(=O)C11CCCC1 VGZUUEHTLRIUFY-UHFFFAOYSA-N 0.000 description 1
• KRPUWAYZJMACIR-UHFFFAOYSA-N 2-(2-chloroanilino)-5-(2-methoxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(CCOC)(C)SC(NC=2C(=CC=CC=2)Cl)=N1 KRPUWAYZJMACIR-UHFFFAOYSA-N 0.000 description 1
• ZPAKBZLRVFBZCH-UHFFFAOYSA-N 2-(2-chloroanilino)-5-(methoxymethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(COC)(C)SC(NC=2C(=CC=CC=2)Cl)=N1 ZPAKBZLRVFBZCH-UHFFFAOYSA-N 0.000 description 1
• IUHKCWLWIGKMAE-UHFFFAOYSA-N 2-(2-chloroanilino)-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC1=NC(=O)C(C2CCOCC2)S1 IUHKCWLWIGKMAE-UHFFFAOYSA-N 0.000 description 1
• AIWLBRBWOINARN-RZZZFEHKSA-N 2-(2-chloroanilino)-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC1=NC(=O)C([C@H]2COCC2)S1 AIWLBRBWOINARN-RZZZFEHKSA-N 0.000 description 1
• AIWLBRBWOINARN-YMNIQAILSA-N 2-(2-chloroanilino)-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC1=NC(=O)C([C@@H]2COCC2)S1 AIWLBRBWOINARN-YMNIQAILSA-N 0.000 description 1
• CLXNATXQZSWKOJ-UHFFFAOYSA-N 2-(2-chloroanilino)-5-cyclohexyl-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC1=NC(=O)C(C2CCCCC2)S1 CLXNATXQZSWKOJ-UHFFFAOYSA-N 0.000 description 1
• JOEVFCJNZCDHCR-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C)SC(NC=2C(=CC=CC=2)Cl)=N1 JOEVFCJNZCDHCR-UHFFFAOYSA-N 0.000 description 1
• YSFISAYQFIMXAP-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C2CCOCC2)SC=1NC1=CC=CC=C1Cl YSFISAYQFIMXAP-UHFFFAOYSA-N 0.000 description 1
• GQKKOZQCOSJMHM-UCWRFOARSA-N 2-(2-chloroanilino)-5-methyl-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)([C@H]2COCC2)SC=1NC1=CC=CC=C1Cl GQKKOZQCOSJMHM-UCWRFOARSA-N 0.000 description 1
• GQKKOZQCOSJMHM-CUVJYRNJSA-N 2-(2-chloroanilino)-5-methyl-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)([C@@H]2COCC2)SC=1NC1=CC=CC=C1Cl GQKKOZQCOSJMHM-CUVJYRNJSA-N 0.000 description 1
• BLCVOENUVFUILL-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-phenyl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CC=CC=2)SC=1NC1=CC=CC=C1Cl BLCVOENUVFUILL-UHFFFAOYSA-N 0.000 description 1
• TULNEJCEVLHZMZ-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC=2C(=CC=CC=2)Cl)=N1 TULNEJCEVLHZMZ-UHFFFAOYSA-N 0.000 description 1
• JSJTUVGFSKZNAN-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)(C)SC(NC=2C(=CC=CC=2)Cl)=N1 JSJTUVGFSKZNAN-UHFFFAOYSA-N 0.000 description 1
• WEHPXJIGZAUURB-UHFFFAOYSA-N 2-(2-chloroanilino)-5-methyl-5-pyridin-3-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=NC=CC=2)SC=1NC1=CC=CC=C1Cl WEHPXJIGZAUURB-UHFFFAOYSA-N 0.000 description 1
• BDYZHMXXMQJFQU-UHFFFAOYSA-N 2-(2-chloroanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=CC=2)Cl)=N1 BDYZHMXXMQJFQU-UHFFFAOYSA-N 0.000 description 1
• IKFBKWMPUIGMTL-UHFFFAOYSA-N 2-(2-chloroanilino)-7,7-dimethyl-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1COC(C)(C)CC21C(=O)N=C(NC=1C(=CC=CC=1)Cl)S2 IKFBKWMPUIGMTL-UHFFFAOYSA-N 0.000 description 1
• PGEDMYLVWQDUMM-UHFFFAOYSA-N 2-(2-chloroanilino)-8-methoxy-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound C1C(OC)CCC21C(=O)N=C(NC=1C(=CC=CC=1)Cl)S2 PGEDMYLVWQDUMM-UHFFFAOYSA-N 0.000 description 1
• MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 description 1
• REVWJENPLGEDLM-UHFFFAOYSA-N 2-(2-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)CS1 REVWJENPLGEDLM-UHFFFAOYSA-N 0.000 description 1
• ZDQQIWCCCTWNNV-UHFFFAOYSA-N 2-(2-fluoroanilino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound FC1=CC=CC=C1NC(S1)=NC(=O)C11CCCC1 ZDQQIWCCCTWNNV-UHFFFAOYSA-N 0.000 description 1
• SNKJBAFFBLMNLM-UHFFFAOYSA-N 2-(2-fluoroanilino)-5-(2-hydroxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(CCO)SC(NC=2C(=CC=CC=2)F)=N1 SNKJBAFFBLMNLM-UHFFFAOYSA-N 0.000 description 1
• VWAATNPSTWMSCL-UHFFFAOYSA-N 2-(2-fluoroanilino)-5-(methoxymethyl)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(COC)(C(C)C)SC(NC=2C(=CC=CC=2)F)=N1 VWAATNPSTWMSCL-UHFFFAOYSA-N 0.000 description 1
• MDBQJIDSJBSFTQ-UHFFFAOYSA-N 2-(2-fluoroanilino)-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)C(C2CCOCC2)S1 MDBQJIDSJBSFTQ-UHFFFAOYSA-N 0.000 description 1
• PGETWDIRWDVJSR-RZZZFEHKSA-N 2-(2-fluoroanilino)-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)C([C@H]2COCC2)S1 PGETWDIRWDVJSR-RZZZFEHKSA-N 0.000 description 1
• VXNIUVJEBHMFMT-UHFFFAOYSA-N 2-(2-fluoroanilino)-5-methyl-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C2CCOCC2)SC=1NC1=CC=CC=C1F VXNIUVJEBHMFMT-UHFFFAOYSA-N 0.000 description 1
• WSPPCQBCXVTELW-UCWRFOARSA-N 2-(2-fluoroanilino)-5-methyl-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)([C@H]2COCC2)SC=1NC1=CC=CC=C1F WSPPCQBCXVTELW-UCWRFOARSA-N 0.000 description 1
• WSPPCQBCXVTELW-CUVJYRNJSA-N 2-(2-fluoroanilino)-5-methyl-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)([C@@H]2COCC2)SC=1NC1=CC=CC=C1F WSPPCQBCXVTELW-CUVJYRNJSA-N 0.000 description 1
• MSGQYHQDAIPUAP-UHFFFAOYSA-N 2-(2-methylanilino)-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1NC1=NC(=O)C(C2CCOCC2)S1 MSGQYHQDAIPUAP-UHFFFAOYSA-N 0.000 description 1
• TZNNYIJBKGFDIY-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-1,3-thiazol-4-one Chemical compound O=C1CSC(NC2C3CCC(C3)C2)=N1 TZNNYIJBKGFDIY-UHFFFAOYSA-N 0.000 description 1
• PRVHDKPRUSEWRS-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-1-oxa-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)OC11CCCC1 PRVHDKPRUSEWRS-UHFFFAOYSA-N 0.000 description 1
• FVVSPKYPMHIDPY-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5,5-diethyl-1,3-oxazol-4-one Chemical compound O=C1C(CC)(CC)OC(NC2C3CCC(C3)C2)=N1 FVVSPKYPMHIDPY-UHFFFAOYSA-N 0.000 description 1
• WICQKEYGGLISEK-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NC2C3CCC(C3)C2)=N1 WICQKEYGGLISEK-UHFFFAOYSA-N 0.000 description 1
• GGUNPMYUNSUWBF-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-(2-hydroxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(CCO)SC(NC2C3CCC(C3)C2)=N1 GGUNPMYUNSUWBF-UHFFFAOYSA-N 0.000 description 1
• HBUQZMSTNZFHKF-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-(3,3-difluoropiperidin-1-yl)ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCN1CCCC(F)(F)C1 HBUQZMSTNZFHKF-UHFFFAOYSA-N 0.000 description 1
• FUTTWXMLSHSNQM-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-(3-chloroanilino)ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCNC1=CC=CC(Cl)=C1 FUTTWXMLSHSNQM-UHFFFAOYSA-N 0.000 description 1
• ZXOJPBJRMJNVSX-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-(3-fluoropiperidin-1-yl)ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCN1CCCC(F)C1 ZXOJPBJRMJNVSX-UHFFFAOYSA-N 0.000 description 1
• JECKNJKMOLDARJ-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-(4,4-difluoropiperidin-1-yl)ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCN1CCC(F)(F)CC1 JECKNJKMOLDARJ-UHFFFAOYSA-N 0.000 description 1
• HTPBSTGVMHKCHQ-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-(4-fluoropiperidin-1-yl)ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCN1CCC(F)CC1 HTPBSTGVMHKCHQ-UHFFFAOYSA-N 0.000 description 1
• JBNDAXKKFNGWHP-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[2-[(6-methoxypyridin-3-yl)amino]ethyl]-5-methyl-1,3-thiazol-4-one Chemical compound C1=NC(OC)=CC=C1NCCC1(C)C(=O)N=C(NC2C3CCC(C3)C2)S1 JBNDAXKKFNGWHP-UHFFFAOYSA-N 0.000 description 1
• NBPIPLOZRMIXQO-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-methyl-5-[2-(n-methylanilino)ethyl]-1,3-thiazol-4-one Chemical compound S1C(NC2C3CCC(C3)C2)=NC(=O)C1(C)CCN(C)C1=CC=CC=C1 NBPIPLOZRMIXQO-UHFFFAOYSA-N 0.000 description 1
• MSZHOSYAGVBHPO-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-methyl-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)(C)SC(NC2C3CCC(C3)C2)=N1 MSZHOSYAGVBHPO-UHFFFAOYSA-N 0.000 description 1
• VHIMODHBQCPQMU-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-phenyl-1,3-oxazol-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)OC1C1=CC=CC=C1 VHIMODHBQCPQMU-UHFFFAOYSA-N 0.000 description 1
• PEIBWLRHGWKYIG-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-6-oxa-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCCO1 PEIBWLRHGWKYIG-UHFFFAOYSA-N 0.000 description 1
• XHHNQNUBGZMNHR-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-8-(2-methylpropyl)-1-thia-3,8-diazaspiro[4.5]dec-2-en-4-one Chemical compound C1CN(CC(C)C)CCC21C(=O)N=C(NC1C3CCC(C3)C1)S2 XHHNQNUBGZMNHR-UHFFFAOYSA-N 0.000 description 1
• UXDRRCAEMMFMQC-UHFFFAOYSA-N 2-(3-chloro-2-methylanilino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC=2C(=C(Cl)C=CC=2)C)=N1 UXDRRCAEMMFMQC-UHFFFAOYSA-N 0.000 description 1
• KRUFUDAUCGKGCA-UHFFFAOYSA-N 2-(3-chloro-2-methylanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=C(Cl)C=CC=2)C)=N1 KRUFUDAUCGKGCA-UHFFFAOYSA-N 0.000 description 1
• VWPWFJPWCRNVST-UHFFFAOYSA-N 2-(4-bicyclo[2.2.1]heptanylamino)-5-methyl-5-(2,2,2-trifluoroethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(CC(F)(F)F)SC(NC23CCC(CC2)C3)=N1 VWPWFJPWCRNVST-UHFFFAOYSA-N 0.000 description 1
• WKGAOJMJJXUEQD-UHFFFAOYSA-N 2-(4-bicyclo[2.2.1]heptanylamino)-5-methyl-5-(piperidin-4-ylmethyl)-1,3-thiazol-4-one Chemical compound S1C(NC23CCC(CC2)C3)=NC(=O)C1(C)CC1CCNCC1 WKGAOJMJJXUEQD-UHFFFAOYSA-N 0.000 description 1
• RQFYBESOGWPDPJ-UHFFFAOYSA-N 2-(4-bicyclo[2.2.1]heptanylamino)-7,7-dimethyl-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1COC(C)(C)CC21C(=O)N=C(NC13CCC(CC1)C3)S2 RQFYBESOGWPDPJ-UHFFFAOYSA-N 0.000 description 1
• KCPXXPAUXJLANH-UHFFFAOYSA-N 2-(4-cyclohexylanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C=CC(=CC=2)C2CCCCC2)=N1 KCPXXPAUXJLANH-UHFFFAOYSA-N 0.000 description 1
• NACOMKOHQVQPTQ-UHFFFAOYSA-N 2-(4-fluoroanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C=CC(F)=CC=2)=N1 NACOMKOHQVQPTQ-UHFFFAOYSA-N 0.000 description 1
• RAOMHAAOTHBUKQ-UHFFFAOYSA-N 2-(5-chloro-2-methylanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=C(Cl)C=2)C)=N1 RAOMHAAOTHBUKQ-UHFFFAOYSA-N 0.000 description 1
• OLQNCCGJFVHOTQ-UHFFFAOYSA-N 2-(7-bicyclo[2.2.1]heptanylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NC2C3CCC2CC3)=N1 OLQNCCGJFVHOTQ-UHFFFAOYSA-N 0.000 description 1
• HSKJYRWLPMTLSI-UHFFFAOYSA-N 2-(azepan-1-ylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NN2CCCCCC2)=N1 HSKJYRWLPMTLSI-UHFFFAOYSA-N 0.000 description 1
• IUURRDZAZOQTCE-UHFFFAOYSA-N 2-(benzylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NCC=2C=CC=CC=2)=N1 IUURRDZAZOQTCE-UHFFFAOYSA-N 0.000 description 1
• GZHHHSYXSBNBBH-UHFFFAOYSA-N 2-(benzylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NCC=2C=CC=CC=2)=N1 GZHHHSYXSBNBBH-UHFFFAOYSA-N 0.000 description 1
• JKHYMNPBDNZGMP-UHFFFAOYSA-N 2-(cycloheptylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(C)SC(NC2CCCCCC2)=N1 JKHYMNPBDNZGMP-UHFFFAOYSA-N 0.000 description 1
• YNCZKBHQXKCTGN-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(2-hydroxyethyl)-1,3-thiazol-4-one Chemical compound O=C1C(CCO)SC(NC2CCCCCC2)=N1 YNCZKBHQXKCTGN-UHFFFAOYSA-N 0.000 description 1
• HADJBXRGCKAYAI-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(2-hydroxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(CCO)SC(NC2CCCCCC2)=N1 HADJBXRGCKAYAI-UHFFFAOYSA-N 0.000 description 1
• RROAAULHCKWULD-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-4-one Chemical compound C1COCCN1C(=O)CC(C(N=1)=O)SC=1NC1CCCCCC1 RROAAULHCKWULD-UHFFFAOYSA-N 0.000 description 1
• NVGJVCSYTWQYNY-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(pyridin-3-ylmethyl)-1,3-thiazol-4-one Chemical compound S1C(CC=2C=NC=CC=2)C(=O)N=C1NC1CCCCCC1 NVGJVCSYTWQYNY-UHFFFAOYSA-N 0.000 description 1
• GEEKYISDSIZJJQ-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methoxy-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)(OC)SC(NC2CCCCCC2)=N1 GEEKYISDSIZJJQ-UHFFFAOYSA-N 0.000 description 1
• BBDXDPPRHSMORY-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-(2-phenoxyethoxy)-1,3-thiazol-4-one Chemical compound S1C(NC2CCCCCC2)=NC(=O)C1(C)OCCOC1=CC=CC=C1 BBDXDPPRHSMORY-UHFFFAOYSA-N 0.000 description 1
• UFETWWSMCODKED-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-(3-morpholin-4-ylpropylamino)-1,3-thiazol-4-one Chemical compound S1C(NC2CCCCCC2)=NC(=O)C1(C)NCCCN1CCOCC1 UFETWWSMCODKED-UHFFFAOYSA-N 0.000 description 1
• DNUMTXJODQCJTQ-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-(4-morpholin-4-ylbutyl)-1,3-thiazol-4-one Chemical compound S1C(NC2CCCCCC2)=NC(=O)C1(C)CCCCN1CCOCC1 DNUMTXJODQCJTQ-UHFFFAOYSA-N 0.000 description 1
• PLJMSDUDUOABRH-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-(oxolan-3-yloxy)-1,3-thiazol-4-one Chemical compound S1C(NC2CCCCCC2)=NC(=O)C1(C)OC1CCOC1 PLJMSDUDUOABRH-UHFFFAOYSA-N 0.000 description 1
• TVFMXZVRNNZTNM-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-piperidin-1-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(N2CCCCC2)SC=1NC1CCCCCC1 TVFMXZVRNNZTNM-UHFFFAOYSA-N 0.000 description 1
• CTIXPLDSPSLGMC-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2CCCCCC2)=N1 CTIXPLDSPSLGMC-UHFFFAOYSA-N 0.000 description 1
• FAZLCCLGXPDGMB-UHFFFAOYSA-N 2-(cycloheptylamino)-5-methyl-5-propan-2-yloxy-1,3-thiazol-4-one Chemical compound O=C1C(OC(C)C)(C)SC(NC2CCCCCC2)=N1 FAZLCCLGXPDGMB-UHFFFAOYSA-N 0.000 description 1
• NDVSYUBQFPPTGC-UHFFFAOYSA-N 2-(cycloheptylamino)-5-phenyl-1,3-oxazol-4-one Chemical compound O1C(C=2C=CC=CC=2)C(=O)N=C1NC1CCCCCC1 NDVSYUBQFPPTGC-UHFFFAOYSA-N 0.000 description 1
• AXHZMXXVTPLRPO-UHFFFAOYSA-N 2-(cycloheptylamino)-5-propan-2-yl-1,3-oxazol-4-one Chemical compound O=C1C(C(C)C)OC(NC2CCCCCC2)=N1 AXHZMXXVTPLRPO-UHFFFAOYSA-N 0.000 description 1
• JBLVNQWKBRKTTO-UHFFFAOYSA-N 2-(cycloheptylamino)-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)SC(NC2CCCCCC2)=N1 JBLVNQWKBRKTTO-UHFFFAOYSA-N 0.000 description 1
• AZLMIMMPODEGSS-UHFFFAOYSA-N 2-(cycloheptylamino)-7-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1C(OC)CCCC21C(=O)N=C(NC1CCCCCC1)S2 AZLMIMMPODEGSS-UHFFFAOYSA-N 0.000 description 1
• GZOFPSMLNDAKAT-UHFFFAOYSA-N 2-(cycloheptylamino)-8-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1CC(OC)CCC21C(=O)N=C(NC1CCCCCC1)S2 GZOFPSMLNDAKAT-UHFFFAOYSA-N 0.000 description 1
• CRVWLHKHBYJXFE-UHFFFAOYSA-N 2-(cyclohexylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NC2CCCCC2)=N1 CRVWLHKHBYJXFE-UHFFFAOYSA-N 0.000 description 1
• WXHGIFYWZPLJTN-UHFFFAOYSA-N 2-(cyclohexylamino)-5-cyclopentyl-1,3-thiazol-4-one Chemical compound S1C(C2CCCC2)C(=O)N=C1NC1CCCCC1 WXHGIFYWZPLJTN-UHFFFAOYSA-N 0.000 description 1
• HUSBDBOEELVCKP-UHFFFAOYSA-N 2-(cyclohexylamino)-5-ethyl-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(C)SC(NC2CCCCC2)=N1 HUSBDBOEELVCKP-UHFFFAOYSA-N 0.000 description 1
• FWRJTNMWZBRLMG-UHFFFAOYSA-N 2-(cyclohexylamino)-5-methyl-5-(2,2,2-trifluoroethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(CC(F)(F)F)SC(NC2CCCCC2)=N1 FWRJTNMWZBRLMG-UHFFFAOYSA-N 0.000 description 1
• NSCDVAPHBMDBSY-UHFFFAOYSA-N 2-(cyclohexylamino)-5-methyl-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)(C)SC(NC2CCCCC2)=N1 NSCDVAPHBMDBSY-UHFFFAOYSA-N 0.000 description 1
• YXYYHVQHCAIYHX-UHFFFAOYSA-N 2-(cyclohexylamino)-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CN=CC=2)SC=1NC1CCCCC1 YXYYHVQHCAIYHX-UHFFFAOYSA-N 0.000 description 1
• HURKRURJMVUMMC-UHFFFAOYSA-N 2-(cyclohexylamino)-7-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1C(OC)CCCC21C(=O)N=C(NC1CCCCC1)S2 HURKRURJMVUMMC-UHFFFAOYSA-N 0.000 description 1
• BARWHNDDDRCRJT-UHFFFAOYSA-N 2-(cyclohexylamino)-8-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1CC(OC)CCC21C(=O)N=C(NC1CCCCC1)S2 BARWHNDDDRCRJT-UHFFFAOYSA-N 0.000 description 1
• XZGNHSGZILTBSZ-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5,5-diethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(CC)SC(NCC2CCCCC2)=N1 XZGNHSGZILTBSZ-UHFFFAOYSA-N 0.000 description 1
• WHDXXIFUPMIJHB-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-(2-hydroxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(CCO)SC(NCC2CCCCC2)=N1 WHDXXIFUPMIJHB-UHFFFAOYSA-N 0.000 description 1
• GEBPNTWJWIQJDO-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound S1C(C2CCOCC2)C(=O)N=C1NCC1CCCCC1 GEBPNTWJWIQJDO-UHFFFAOYSA-N 0.000 description 1
• IPMYUKDCXSHYLJ-JHJMLUEUSA-N 2-(cyclohexylmethylamino)-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound S1C([C@H]2COCC2)C(=O)N=C1NCC1CCCCC1 IPMYUKDCXSHYLJ-JHJMLUEUSA-N 0.000 description 1
• IPMYUKDCXSHYLJ-PXYINDEMSA-N 2-(cyclohexylmethylamino)-5-[(3s)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound S1C([C@@H]2COCC2)C(=O)N=C1NCC1CCCCC1 IPMYUKDCXSHYLJ-PXYINDEMSA-N 0.000 description 1
• OJYIACSBZOBKQT-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-cyclopentyl-1,3-thiazol-4-one Chemical compound S1C(C2CCCC2)C(=O)N=C1NCC1CCCCC1 OJYIACSBZOBKQT-UHFFFAOYSA-N 0.000 description 1
• GTQGEQUWUJUZPN-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-ethyl-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)(C)SC(NCC2CCCCC2)=N1 GTQGEQUWUJUZPN-UHFFFAOYSA-N 0.000 description 1
• OAJXUCFTNFBZFV-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-methyl-5-(2,2,2-trifluoroethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(CC(F)(F)F)SC(NCC2CCCCC2)=N1 OAJXUCFTNFBZFV-UHFFFAOYSA-N 0.000 description 1
• WEIKJEBFFFGSDP-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-methyl-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C2CCOCC2)SC=1NCC1CCCCC1 WEIKJEBFFFGSDP-UHFFFAOYSA-N 0.000 description 1
• QFAZDDSXCQFUSQ-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-methyl-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)(C)SC(NCC2CCCCC2)=N1 QFAZDDSXCQFUSQ-UHFFFAOYSA-N 0.000 description 1
• QELRIBXXICOJCJ-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CN=CC=2)SC=1NCC1CCCCC1 QELRIBXXICOJCJ-UHFFFAOYSA-N 0.000 description 1
• VHXOLQMEIFRMGU-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5-propyl-1,3-thiazol-4-one Chemical compound O=C1C(CCC)SC(NCC2CCCCC2)=N1 VHXOLQMEIFRMGU-UHFFFAOYSA-N 0.000 description 1
• WXIGPANRSYTVRJ-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-8-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound C1CC(OC)CCC21C(=O)N=C(NCC1CCCCC1)S2 WXIGPANRSYTVRJ-UHFFFAOYSA-N 0.000 description 1
• SYCVBWXLSPQIQS-UHFFFAOYSA-N 2-(cyclooctylamino)-1-oxa-3-azaspiro[4.4]non-2-en-4-one Chemical compound O1C2(CCCC2)C(=O)N=C1NC1CCCCCCC1 SYCVBWXLSPQIQS-UHFFFAOYSA-N 0.000 description 1
• JXZFSCOJZRFNMB-UHFFFAOYSA-N 2-(cyclooctylamino)-1-oxa-3-azaspiro[4.5]dec-2-en-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O1C2(CCCCC2)C(=O)N=C1NC1CCCCCCC1 JXZFSCOJZRFNMB-UHFFFAOYSA-N 0.000 description 1
• AOPPTZIKPLJWDF-UHFFFAOYSA-N 2-(cyclooctylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound S1C2(CCCCC2)C(=O)N=C1NC1CCCCCCC1 AOPPTZIKPLJWDF-UHFFFAOYSA-N 0.000 description 1
• QDKIOQRCNWZVGW-UHFFFAOYSA-N 2-(cyclooctylamino)-5-(methylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(NC)(C(C)C)SC(NC2CCCCCCC2)=N1 QDKIOQRCNWZVGW-UHFFFAOYSA-N 0.000 description 1
• GXKJVFUOQIPFIP-UHFFFAOYSA-N 2-(cyclooctylamino)-5-cyclopentyl-1,3-thiazol-4-one Chemical compound S1C(C2CCCC2)C(=O)N=C1NC1CCCCCCC1 GXKJVFUOQIPFIP-UHFFFAOYSA-N 0.000 description 1
• XPBCBRVKRNYMGP-UHFFFAOYSA-N 2-(cyclooctylamino)-5-methoxy-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(OC)(C(C)C)SC(NC2CCCCCCC2)=N1 XPBCBRVKRNYMGP-UHFFFAOYSA-N 0.000 description 1
• YYMCKBFQLIZMRY-UHFFFAOYSA-N 2-(cyclooctylamino)-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(C(F)(F)F)SC(NC2CCCCCCC2)=N1 YYMCKBFQLIZMRY-UHFFFAOYSA-N 0.000 description 1
• DTWXRTUFLVTQOA-UHFFFAOYSA-N 2-(cyclooctylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2CCCCCCC2)=N1 DTWXRTUFLVTQOA-UHFFFAOYSA-N 0.000 description 1
• UNUWSRCQXRZZAT-UHFFFAOYSA-N 2-(cyclooctylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC2CCCCCCC2)=N1 UNUWSRCQXRZZAT-UHFFFAOYSA-N 0.000 description 1
• MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
• OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
• LPSQXBYXJOMNOG-UHFFFAOYSA-N 2-[(2,2-difluoro-5-bicyclo[2.2.1]heptanyl)amino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(C(F)(F)F)SC(NC2C3CC(C(C3)(F)F)C2)=N1 LPSQXBYXJOMNOG-UHFFFAOYSA-N 0.000 description 1
• BJNJNOPSANJBIS-UHFFFAOYSA-N 2-[(2,6-dimethylpiperidin-1-yl)amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NN2C(CCCC2C)C)=N1 BJNJNOPSANJBIS-UHFFFAOYSA-N 0.000 description 1
• QCKUKWFUODFIEO-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylamino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NCC=2C(=CC=CC=2)Cl)=N1 QCKUKWFUODFIEO-UHFFFAOYSA-N 0.000 description 1
• GBIIDYNJVWDKCT-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylamino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NCC=2C(=CC=CC=2)Cl)=N1 GBIIDYNJVWDKCT-UHFFFAOYSA-N 0.000 description 1
• KXONOLVYEVIDIL-UHFFFAOYSA-N 2-[(3,3-difluoro-5-bicyclo[2.2.1]heptanyl)amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2C3CC(CC3(F)F)C2)=N1 KXONOLVYEVIDIL-UHFFFAOYSA-N 0.000 description 1
• KWQLPYUFRGSDOA-UHFFFAOYSA-N 2-[(3-hydroxy-1-adamantyl)amino]-1-oxa-3-azaspiro[4.4]non-2-en-4-one Chemical compound C1C(O)(C2)CC(C3)CC1CC32NC(O1)=NC(=O)C21CCCC2 KWQLPYUFRGSDOA-UHFFFAOYSA-N 0.000 description 1
• BSSFDRUUNCJRQO-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylamino]-5-propan-2-yl-1,3-oxazol-4-one Chemical compound O=C1C(C(C)C)OC(NCC=2C=CC(Cl)=CC=2)=N1 BSSFDRUUNCJRQO-UHFFFAOYSA-N 0.000 description 1
• JMJCYSOOSXBHOV-UHFFFAOYSA-N 2-[(6,6-difluoro-3-bicyclo[3.1.0]hexanyl)amino]-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound C1C2C(F)(F)C2CC1NC(S1)=NC(=O)C21CCCC2 JMJCYSOOSXBHOV-UHFFFAOYSA-N 0.000 description 1
• PVLBUFRXQZKRIM-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)ethylamino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NCCC=2C(=CC=CC=2)Cl)=N1 PVLBUFRXQZKRIM-UHFFFAOYSA-N 0.000 description 1
• WHCQGYGGSUZYPF-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)ethylamino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NCCC=2C(=CC=CC=2)Cl)=N1 WHCQGYGGSUZYPF-UHFFFAOYSA-N 0.000 description 1
• GSJZZCBMTDMJAY-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)propan-2-ylamino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC(C)(C)C=2C(=CC=CC=2)Cl)=N1 GSJZZCBMTDMJAY-UHFFFAOYSA-N 0.000 description 1
• UFZYOUNJCYUIQA-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)propan-2-ylamino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound C=1C=CC=C(Cl)C=1C(C)(C)NC(S1)=NC(=O)C1(C)C1=CC=NC=C1 UFZYOUNJCYUIQA-UHFFFAOYSA-N 0.000 description 1
• BWYQYYPAPOWPJK-UHFFFAOYSA-N 2-[2-(3-bicyclo[2.2.1]heptanylamino)-4-oxo-1,3-thiazol-5-yl]acetic acid Chemical compound O=C1C(CC(=O)O)SC(NC2C3CCC(C3)C2)=N1 BWYQYYPAPOWPJK-UHFFFAOYSA-N 0.000 description 1
• ASXHRNMJWODOPU-UHFFFAOYSA-N 2-[2-(cyclohexylmethylamino)-4-oxo-1,3-thiazol-5-yl]-n-(cyclopropylmethyl)-n-propylacetamide Chemical compound S1C(NCC2CCCCC2)=NC(=O)C1CC(=O)N(CCC)CC1CC1 ASXHRNMJWODOPU-UHFFFAOYSA-N 0.000 description 1
• MQLFIIHYTYASSA-UHFFFAOYSA-N 2-[2-(trifluoromethyl)anilino]-1-thia-3,9-diazaspiro[4.5]dec-2-ene-4,10-dione Chemical compound FC(F)(F)C1=CC=CC=C1NC(S1)=NC(=O)C11C(=O)NCCC1 MQLFIIHYTYASSA-UHFFFAOYSA-N 0.000 description 1
• QWRVJBHMRTXNOK-PKEIRNPWSA-N 2-[[(1r)-1-(2-fluorophenyl)ethyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(N[C@H](C)C=2C(=CC=CC=2)F)=N1 QWRVJBHMRTXNOK-PKEIRNPWSA-N 0.000 description 1
• LYYNMFHQJSSQIT-RWANSRKNSA-N 2-[[(1r)-1-cyclohexylethyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(N[C@H](C)C2CCCCC2)=N1 LYYNMFHQJSSQIT-RWANSRKNSA-N 0.000 description 1
• MWALCPLMKFAAPN-WOPDTQHZSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCCCC2 MWALCPLMKFAAPN-WOPDTQHZSA-N 0.000 description 1
• WICQKEYGGLISEK-VWYCJHECSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5,5-diethyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)C(CC)(CC)S1 WICQKEYGGLISEK-VWYCJHECSA-N 0.000 description 1
• ZFHXTTXOXBEJIP-RWGUQGFDSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(1-cyclopentylpiperidin-4-yl)-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C1CCCC1 ZFHXTTXOXBEJIP-RWGUQGFDSA-N 0.000 description 1
• FTBSPSRDJAAHNV-KIWYXKPISA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)C(C)(C(C)(C)F)S1 FTBSPSRDJAAHNV-KIWYXKPISA-N 0.000 description 1
• PMBVXYDUOGFLMR-KIWYXKPISA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(2-hydroxypropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)C(C)(C(C)(C)O)S1 PMBVXYDUOGFLMR-KIWYXKPISA-N 0.000 description 1
• OQNLHYAZYQGCIO-CXJJLCSMSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(cyclohexylmethyl)-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1CC1CCCCC1 OQNLHYAZYQGCIO-CXJJLCSMSA-N 0.000 description 1
• WBHZAMLXYDCXEE-OGZKGVCFSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[(3r)-oxolan-3-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1[C@@H]1CCOC1 WBHZAMLXYDCXEE-OGZKGVCFSA-N 0.000 description 1
• FKFBEYDDOFAIOY-NTCSTIOSSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(2,2-difluoropropanoyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCN(C(=O)C(C)(F)F)CC1 FKFBEYDDOFAIOY-NTCSTIOSSA-N 0.000 description 1
• BTGPXDALBDUWGZ-PCQWOLHHSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(2-fluoro-2-methylpropanoyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCN(C(=O)C(C)(C)F)CC1 BTGPXDALBDUWGZ-PCQWOLHHSA-N 0.000 description 1
• RWWGZPAUVSTNAG-XIDMDKDRSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(4-fluorobenzoyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1=CC=C(F)C=C1 RWWGZPAUVSTNAG-XIDMDKDRSA-N 0.000 description 1
• WBJASXXJJGPHHP-CYXXXYAASA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(cyclobutanecarbonyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1CCC1 WBJASXXJJGPHHP-CYXXXYAASA-N 0.000 description 1
• PXHVSYVIIXKGQD-AIBNTIPSSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(cyclopropanecarbonyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1CC1 PXHVSYVIIXKGQD-AIBNTIPSSA-N 0.000 description 1
• DCLCGGBYOQPHGD-BNVZJSHZSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[1-(furan-3-carbonyl)piperidin-4-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C=1C=COC=1 DCLCGGBYOQPHGD-BNVZJSHZSA-N 0.000 description 1
• JMSRRLOOKLNXQZ-KXLLHITNSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(2,6-difluorophenyl)sulfonylpiperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1S(=O)(=O)C1=C(F)C=CC=C1F JMSRRLOOKLNXQZ-KXLLHITNSA-N 0.000 description 1
• OXNHSZVKKKYGIT-NNZUZZEFSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(2-chlorophenyl)sulfonylpiperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1S(=O)(=O)C1=CC=CC=C1Cl OXNHSZVKKKYGIT-NNZUZZEFSA-N 0.000 description 1
• HTPZQJIKLRYGFZ-IPLINKKNSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(2-methoxyacetyl)piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCN(C(=O)COC)CC1 HTPZQJIKLRYGFZ-IPLINKKNSA-N 0.000 description 1
• RPYMLACLYLSWMB-RFOOQNRRSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(3,5-dimethyl-1,2-oxazole-4-carbonyl)piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C=1C(C)=NOC=1C RPYMLACLYLSWMB-RFOOQNRRSA-N 0.000 description 1
• OAQUGWVTYZAQCA-YKJUXTDWSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(4-hydroxybenzoyl)piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C1=CC=C(O)C=C1 OAQUGWVTYZAQCA-YKJUXTDWSA-N 0.000 description 1
• CIHZFDKGMNOOKU-WSDGFUFPSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(furan-2-carbonyl)piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C1=CC=CO1 CIHZFDKGMNOOKU-WSDGFUFPSA-N 0.000 description 1
• SDSPWEWAXMPXGX-UBQUEKSESA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-(furan-3-carbonyl)piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C=1C=COC=1 SDSPWEWAXMPXGX-UBQUEKSESA-N 0.000 description 1
• UOLDJBYDVUDMQV-LJEUNREKSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-[2-(dimethylamino)acetyl]piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCN(C(=O)CN(C)C)CC1 UOLDJBYDVUDMQV-LJEUNREKSA-N 0.000 description 1
• RNEDWBJEBPVFEB-KFMLXFHDSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[[1-[4-(dimethylamino)butanoyl]piperidin-4-yl]methyl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCN(C(=O)CCCN(C)C)CC1 RNEDWBJEBPVFEB-KFMLXFHDSA-N 0.000 description 1
• LLNOOWCZYTUVOR-QNDAJOIBSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-cyclohexyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1C1CCCCC1 LLNOOWCZYTUVOR-QNDAJOIBSA-N 0.000 description 1
• MUTHEKYABVQWBP-PWHRYJHASA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-cyclopentyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1C1CCCC1 MUTHEKYABVQWBP-PWHRYJHASA-N 0.000 description 1
• VMIOREUJTFHJQY-ATUXAFSHSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-ethyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)C(CC)(C(C)C)S1 VMIOREUJTFHJQY-ATUXAFSHSA-N 0.000 description 1
• SIHHTGKQHHWZRM-UXGQUHLOSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)C(C)S1 SIHHTGKQHHWZRM-UXGQUHLOSA-N 0.000 description 1
• YAMIVMRMKKSMKI-NAHFHFTKSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(1-propanoylpiperidin-4-yl)-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCN(C(=O)CC)CC1 YAMIVMRMKKSMKI-NAHFHFTKSA-N 0.000 description 1
• QSDFLOWHPNTKRK-MDVAVASXSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(oxan-4-ylmethyl)-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCOCC1 QSDFLOWHPNTKRK-MDVAVASXSA-N 0.000 description 1
• ASBZQLGWQMFJHP-KOKZCLCDSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(oxolan-3-ylmethyl)-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCOC1 ASBZQLGWQMFJHP-KOKZCLCDSA-N 0.000 description 1
• QJPVRJATZSSZOH-IPLINKKNSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[(1-propanoylpiperidin-4-yl)methyl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCN(C(=O)CC)CC1 QJPVRJATZSSZOH-IPLINKKNSA-N 0.000 description 1
• LCHJISSYBYDYRF-PCQWOLHHSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(1,3-thiazole-4-carbonyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1=CSC=N1 LCHJISSYBYDYRF-PCQWOLHHSA-N 0.000 description 1
• OWHFGZICALLPQU-NNZUZZEFSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(2-pyridin-4-ylacetyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)CC1=CC=NC=C1 OWHFGZICALLPQU-NNZUZZEFSA-N 0.000 description 1
• LSRVVMPSXDFIIA-CUJIZOOUSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(3-phenylprop-2-enoyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C=CC1=CC=CC=C1 LSRVVMPSXDFIIA-CUJIZOOUSA-N 0.000 description 1
• PWTJROJIFNAMTJ-GIQMZNDGSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(3-pyridin-3-ylpropanoyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)CCC1=CC=CN=C1 PWTJROJIFNAMTJ-GIQMZNDGSA-N 0.000 description 1
• JFERYMPZUQLEQP-GTNJCADHSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(pyridine-3-carbonyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1=CC=CN=C1 JFERYMPZUQLEQP-GTNJCADHSA-N 0.000 description 1
• DCNIPTVGAVABRY-OQTGFFOVSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[[1-(1,2-oxazole-5-carbonyl)piperidin-4-yl]methyl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C1=CC=NO1 DCNIPTVGAVABRY-OQTGFFOVSA-N 0.000 description 1
• ITKVLMRCYDVITG-WSDGFUFPSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[[1-(5-methyl-1,2-oxazole-3-carbonyl)piperidin-4-yl]methyl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C=1C=C(C)ON=1 ITKVLMRCYDVITG-WSDGFUFPSA-N 0.000 description 1
• JSASRJVBGPIJJP-DVOPDICFSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[[1-[5-methyl-2-(trifluoromethyl)furan-3-carbonyl]piperidin-4-yl]methyl]-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC(CC1)CCN1C(=O)C=1C=C(C)OC=1C(F)(F)F JSASRJVBGPIJJP-DVOPDICFSA-N 0.000 description 1
• IDWRLSRDENSFKM-MCYFVWBLSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-piperidin-4-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCNCC1 IDWRLSRDENSFKM-MCYFVWBLSA-N 0.000 description 1
• YQNHEXJBCWQWGL-CTFWAZLMSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-pyridin-2-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1=CC=CC=N1 YQNHEXJBCWQWGL-CTFWAZLMSA-N 0.000 description 1
• MZWHVMXECLRQCT-MCYFVWBLSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-pyridin-3-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1=CC=CN=C1 MZWHVMXECLRQCT-MCYFVWBLSA-N 0.000 description 1
• PCWIBBOQMGCMJB-MCYFVWBLSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1=CC=NC=C1 PCWIBBOQMGCMJB-MCYFVWBLSA-N 0.000 description 1
• AQSLWHYOQRIJJE-CTFWAZLMSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-7,7-dimethyl-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCOC(C)(C)C2 AQSLWHYOQRIJJE-CTFWAZLMSA-N 0.000 description 1
• BMENXHZHJJWVEL-OTBBMYEOSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-7-oxa-1-thia-3-azaspiro[4.4]non-2-ene-4,6-dione Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCOC2=O BMENXHZHJJWVEL-OTBBMYEOSA-N 0.000 description 1
• UAZFHWLXONSKAB-BUXKNELBSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-8-methoxy-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCC(OC)C2 UAZFHWLXONSKAB-BUXKNELBSA-N 0.000 description 1
• GGKKSNOIQSVVBI-QXLLTNDWSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-8-methoxy-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCC(OC)CC2 GGKKSNOIQSVVBI-QXLLTNDWSA-N 0.000 description 1
• GUGBDNQGYWHFSW-VWYCJHECSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCOCC2 GUGBDNQGYWHFSW-VWYCJHECSA-N 0.000 description 1
• GQUDBDBWDOVADX-DCSOJXMASA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-9-methyl-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CCCC2C GQUDBDBWDOVADX-DCSOJXMASA-N 0.000 description 1
• JORPEIMVTCFENA-GRYCIOLGSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]methylamino]-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound C([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])NC(S1)=NC(=O)C21CCCC2 JORPEIMVTCFENA-GRYCIOLGSA-N 0.000 description 1
• PFNMFIKUEIHOIJ-FWKUWYBHSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]methylamino]-5-methyl-1,3-thiazol-4-one Chemical compound C([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])NC1=NC(=O)C(C)S1 PFNMFIKUEIHOIJ-FWKUWYBHSA-N 0.000 description 1
• QSTPGGFFBRCNNM-GJXMVACYSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]methylamino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound C([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])NC1=NC(=O)C(C)(C(F)(F)F)S1 QSTPGGFFBRCNNM-GJXMVACYSA-N 0.000 description 1
• LTKVBAFREODHQH-FBTJUVTCSA-N 2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]methylamino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound C([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])NC1=NC(=O)C(C(C)C)S1 LTKVBAFREODHQH-FBTJUVTCSA-N 0.000 description 1
• RYHHQHRAADYATN-HNJRMYHASA-N 2-[[(1r,4r,5s)-2,2-difluoro-5-bicyclo[2.2.1]heptanyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@H]1C[C@]2(C[C@@]1(CC2(F)F)[H])[H])C1=NC(=O)C(C(C)C)S1 RYHHQHRAADYATN-HNJRMYHASA-N 0.000 description 1
• UPNIHGYNBGGMFK-YSNIEIRRSA-N 2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-[1-(5-methyl-1,2-oxazole-3-carbonyl)piperidin-4-yl]-1,3-thiazol-4-one Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NC(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C=1C=C(C)ON=1 UPNIHGYNBGGMFK-YSNIEIRRSA-N 0.000 description 1
• CXDBYDSTDQGLHI-KAJCPDDVSA-N 2-[[(1s)-1-(2-chlorophenyl)ethyl]amino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C(=CC=CC=1)Cl)C1=NC(=O)C(C)(C(F)(F)F)S1 CXDBYDSTDQGLHI-KAJCPDDVSA-N 0.000 description 1
• XKYVVOVQZIONJM-JAMMHHFISA-N 2-[[(1s)-1-(2-fluorophenyl)ethyl]amino]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C(=CC=CC=1)F)C1=NC(=O)C(C)S1 XKYVVOVQZIONJM-JAMMHHFISA-N 0.000 description 1
• QWRVJBHMRTXNOK-QHGLUPRGSA-N 2-[[(1s)-1-(2-fluorophenyl)ethyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(N[C@@H](C)C=2C(=CC=CC=2)F)=N1 QWRVJBHMRTXNOK-QHGLUPRGSA-N 0.000 description 1
• GOOACXKEDTUBGL-JAMMHHFISA-N 2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C1=NC(=O)C(C)S1 GOOACXKEDTUBGL-JAMMHHFISA-N 0.000 description 1
• XUISZKCZKNCBNJ-KAJCPDDVSA-N 2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C1=NC(=O)C(C)(C(F)(F)F)S1 XUISZKCZKNCBNJ-KAJCPDDVSA-N 0.000 description 1
• XADQLNINUBEDSO-PIJUOJQZSA-N 2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-pyridin-3-yl-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(S1)=NC(=O)C1(C)C1=CC=CN=C1 XADQLNINUBEDSO-PIJUOJQZSA-N 0.000 description 1
• MWNAPXWHHGHKAK-PIJUOJQZSA-N 2-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(S1)=NC(=O)C1(C)C1=CC=NC=C1 MWNAPXWHHGHKAK-PIJUOJQZSA-N 0.000 description 1
• OFNWCGKHMFWXKI-NSHDSACASA-N 2-[[(1s)-1-phenylethyl]amino]-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(S1)=NC(=O)C21CCCC2 OFNWCGKHMFWXKI-NSHDSACASA-N 0.000 description 1
• ZEOGLLNIIFLDEN-NOWMRDAKSA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-1-thia-3,9-diazaspiro[4.5]dec-2-ene-4,10-dione Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C(S1)=NC(=O)C21CCCNC2=O ZEOGLLNIIFLDEN-NOWMRDAKSA-N 0.000 description 1
• DWMZBMYRLFPACC-QPFYHTCHSA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-(2,2,2-trifluoroethyl)-1,3-thiazol-4-one Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C1=NC(=O)C(C)(CC(F)(F)F)S1 DWMZBMYRLFPACC-QPFYHTCHSA-N 0.000 description 1
• YCNCXQNUXCHRRX-XBZGWKTJSA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C1=NC(=O)C(C)(C(C)C)S1 YCNCXQNUXCHRRX-XBZGWKTJSA-N 0.000 description 1
• CCAYBDKUKFQXNR-JZQNTNKLSA-N 2-[[(1s,5r)-6,6-difluoro-3-bicyclo[3.1.0]hexanyl]amino]-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4-one Chemical compound O=C1C(C)(C(F)(F)F)SC(NC2C[C@@H]3[C@@H](C3(F)F)C2)=N1 CCAYBDKUKFQXNR-JZQNTNKLSA-N 0.000 description 1
• GYKFIDMPVJMDJR-CYGRTENRSA-N 2-[[(3s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(1,1-difluoroethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C(F)(F)C)(C)SC(N[C@@H]2C3CCC(C3)C2)=N1 GYKFIDMPVJMDJR-CYGRTENRSA-N 0.000 description 1
• YEODMTDHKMBPFS-QRFNQIEMSA-N 2-[[(3s)-3-bicyclo[2.2.1]heptanyl]amino]-5-(1-hydroxyethyl)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1C(C(O)C)(C)SC(N[C@@H]2C3CCC(C3)C2)=N1 YEODMTDHKMBPFS-QRFNQIEMSA-N 0.000 description 1
• TVPJHTCXCYOUCD-UHFFFAOYSA-N 2-[[1-(2-chlorophenyl)cyclopropyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2(CC2)C=2C(=CC=CC=2)Cl)=N1 TVPJHTCXCYOUCD-UHFFFAOYSA-N 0.000 description 1
• QYZVXJGBLCLUFQ-UHFFFAOYSA-N 2-[[1-(2-chlorophenyl)cyclopropyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC2(CC2)C=2C(=CC=CC=2)Cl)=N1 QYZVXJGBLCLUFQ-UHFFFAOYSA-N 0.000 description 1
• YEOSIVYGKVBJEJ-UHFFFAOYSA-N 2-[[5-hydroxy-5-(trifluoromethyl)cyclooctyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC2CCCC(O)(CCC2)C(F)(F)F)=N1 YEOSIVYGKVBJEJ-UHFFFAOYSA-N 0.000 description 1
• NPZJSEJERYFKGV-UHFFFAOYSA-N 2-anilino-8-benzyl-1-oxa-3,8-diazaspiro[4.5]dec-2-en-4-one Chemical compound O1C2(CCN(CC=3C=CC=CC=3)CC2)C(=O)N=C1NC1=CC=CC=C1 NPZJSEJERYFKGV-UHFFFAOYSA-N 0.000 description 1
• GPYTYOMSQHBYTK-UHFFFAOYSA-N 2-azaniumyl-2,3-dimethylbutanoate Chemical compound CC(C)C(C)(N)C(O)=O GPYTYOMSQHBYTK-UHFFFAOYSA-N 0.000 description 1
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
• YSPQXGIXRXQMJY-UHFFFAOYSA-N 2-bromo-2,3-dimethylbutanoyl isothiocyanate Chemical compound CC(C)C(C)(Br)C(=O)N=C=S YSPQXGIXRXQMJY-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• QCKRFEBWZBKGTR-UHFFFAOYSA-N 2-hydroxy-2,3-dimethylbutanenitrile Chemical compound CC(C)C(C)(O)C#N QCKRFEBWZBKGTR-UHFFFAOYSA-N 0.000 description 1
• JRQZJRDOZAJRTN-UHFFFAOYSA-N 2-hydroxy-2,3-dimethylbutanoic acid Chemical compound CC(C)C(C)(O)C(O)=O JRQZJRDOZAJRTN-UHFFFAOYSA-N 0.000 description 1
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
• VFNUTEMVQGLDAG-NKVSQWTQSA-N 2-methoxy-4-[(Z)-(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol Chemical compound COC1=CC(\C=N/NC2=NC=NC3=C2C2=C(CCCC2)S3)=CC=C1O VFNUTEMVQGLDAG-NKVSQWTQSA-N 0.000 description 1
• PGQTYXFMSZUGOW-UHFFFAOYSA-N 2-methyl-2-phenylpropanenitrile Chemical class N#CC(C)(C)C1=CC=CC=C1 PGQTYXFMSZUGOW-UHFFFAOYSA-N 0.000 description 1
• MIVHEVIWHMEELG-UHFFFAOYSA-N 2-morpholin-4-ylethylthiourea Chemical compound NC(=S)NCCN1CCOCC1 MIVHEVIWHMEELG-UHFFFAOYSA-N 0.000 description 1
• IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• KDFDOINBXBEOLZ-UHFFFAOYSA-N 2-phenylpropan-2-amine Chemical class CC(C)(N)C1=CC=CC=C1 KDFDOINBXBEOLZ-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• OOXKSUTUUWFMBF-UHFFFAOYSA-N 2-pyridin-4-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=NC=C1 OOXKSUTUUWFMBF-UHFFFAOYSA-N 0.000 description 1
• 108010040136 20-alpha-Hydroxysteroid Dehydrogenase Proteins 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
• BSDWXRGFOKSDJR-UHFFFAOYSA-N 3,4-difluorobicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(F)C(O)(F)CC1C2 BSDWXRGFOKSDJR-UHFFFAOYSA-N 0.000 description 1
• ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
• MOKRVTJHHQAODB-UHFFFAOYSA-N 3-[4-oxo-2-[2-(trifluoromethyl)anilino]-1,3-thiazol-5-yl]-n-phenylpropanamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(S1)=NC(=O)C1CCC(=O)NC1=CC=CC=C1 MOKRVTJHHQAODB-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• GVPDRYJFYUWXQK-UHFFFAOYSA-N 3-bromopyrrolidin-2-one Chemical compound BrC1CCNC1=O GVPDRYJFYUWXQK-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
• LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
• MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
• 101710172561 3alpha-hydroxysteroid dehydrogenase Proteins 0.000 description 1
• XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
• WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 description 1
• QLBOLZFNTJLVFO-UHFFFAOYSA-N 4,4-dibromobutanoyl chloride Chemical compound ClC(=O)CCC(Br)Br QLBOLZFNTJLVFO-UHFFFAOYSA-N 0.000 description 1
• ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
• CHTKLUUMJHBAKM-UHFFFAOYSA-N 4-[2-(4-methyl-3-nitrophenoxy)ethyl]morpholine Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1OCCN1CCOCC1 CHTKLUUMJHBAKM-UHFFFAOYSA-N 0.000 description 1
• ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 1
• OVSRWEMAYCEBGU-UHFFFAOYSA-N 4-bicyclo[2.2.1]heptanylcarbamic acid Chemical compound C1CC2CCC1(NC(=O)O)C2 OVSRWEMAYCEBGU-UHFFFAOYSA-N 0.000 description 1
• BQEXDUKMTVYBRK-UHFFFAOYSA-N 4-methyl-3-nitrophenol Chemical compound CC1=CC=C(O)C=C1[N+]([O-])=O BQEXDUKMTVYBRK-UHFFFAOYSA-N 0.000 description 1
• LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
• 208000035116 46 XY Disorder of Sex Development Diseases 0.000 description 1
• VERUFXOALATMPS-UHFFFAOYSA-N 5,5-diamino-2-(2-phenylethenyl)cyclohex-3-ene-1,1-disulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)(S(O)(=O)=O)C1C=CC1=CC=CC=C1 VERUFXOALATMPS-UHFFFAOYSA-N 0.000 description 1
• FLDSMVTWEZKONL-AWEZNQCLSA-N 5,5-dimethyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound CC1(CC2=C(NN=C2C(=O)N[C@@H]2C(N(C3=C(OC2)C=CC=C3)C)=O)CCO1)C FLDSMVTWEZKONL-AWEZNQCLSA-N 0.000 description 1
• LMWZTKZCBPOQTN-UHFFFAOYSA-N 5-(fluoromethyl)-1,3-thiazole 1-oxide Chemical class FCC1=CN=CS1=O LMWZTKZCBPOQTN-UHFFFAOYSA-N 0.000 description 1
• PPKPQSDUKUKRMO-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3-thiazole 1-oxide Chemical class FC(F)(F)C1=CN=CS1=O PPKPQSDUKUKRMO-UHFFFAOYSA-N 0.000 description 1
• UVFIXEGOSUKAPD-UHFFFAOYSA-N 5-(trifluoromethyl)dibenzothiophen-5-ium Chemical class C1=CC=C2[S+](C(F)(F)F)C3=CC=CC=C3C2=C1 UVFIXEGOSUKAPD-UHFFFAOYSA-N 0.000 description 1
• MAAZDBJRZKJGIM-UHFFFAOYSA-N 5-(trifluoromethyl)dibenzothiophen-5-ium-3-sulfonate Chemical compound C1=CC=C2C3=CC=C(S(=O)(=O)[O-])C=C3[S+](C(F)(F)F)C2=C1 MAAZDBJRZKJGIM-UHFFFAOYSA-N 0.000 description 1
• QPQOFPGLOGNXET-VGMNWLOBSA-N 5-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-4-thia-6-azaspiro[2.4]hept-5-en-7-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C21CC2 QPQOFPGLOGNXET-VGMNWLOBSA-N 0.000 description 1
• LNTPIJKTSOLDCO-UHFFFAOYSA-N 5-cyclohexyl-2-(2-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1NC1=NC(=O)C(C2CCCCC2)S1 LNTPIJKTSOLDCO-UHFFFAOYSA-N 0.000 description 1
• XKZANCUHQCMXMV-UHFFFAOYSA-N 5-cyclohexyl-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1NC1=NC(=O)C(C2CCCCC2)S1 XKZANCUHQCMXMV-UHFFFAOYSA-N 0.000 description 1
• LGZXMFCWODHCSZ-UHFFFAOYSA-N 5-cyclopentyl-5-fluoro-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1NC1=NC(=O)C(F)(C2CCCC2)S1 LGZXMFCWODHCSZ-UHFFFAOYSA-N 0.000 description 1
• SFOXTLANYKLVOA-UHFFFAOYSA-N 5-fluoro-1,3-thiazole 1-oxide Chemical class FC1=CN=CS1=O SFOXTLANYKLVOA-UHFFFAOYSA-N 0.000 description 1
• LZPOXWGBMNSAQJ-UHFFFAOYSA-N 5-methyl-2-(2-methylanilino)-5-(oxan-4-yl)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1NC1=NC(=O)C(C)(C2CCOCC2)S1 LZPOXWGBMNSAQJ-UHFFFAOYSA-N 0.000 description 1
• DBVGTDLVURLHDV-UHFFFAOYSA-N 5-methyl-5-pyridin-4-yl-2-[2-(trifluoromethyl)anilino]-1,3-thiazol-4-one Chemical compound N=1C(=O)C(C)(C=2C=CN=CC=2)SC=1NC1=CC=CC=C1C(F)(F)F DBVGTDLVURLHDV-UHFFFAOYSA-N 0.000 description 1
• FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 1
• SWBBIJZMIGAZHW-UHFFFAOYSA-N 6-fluoro-2,3-dihydrochromen-4-one Chemical compound O1CCC(=O)C2=CC(F)=CC=C21 SWBBIJZMIGAZHW-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• LKQJZFVPKSQSLH-UHFFFAOYSA-N 8-(2-adamantyl)-2-(3-bicyclo[2.2.1]heptanylamino)-1-thia-3,8-diazaspiro[4.5]dec-2-en-4-one Chemical compound C1C(CC2C3)CC3CC1C2N(CC1)CCC21SC(NC1C3CCC(C3)C1)=NC2=O LKQJZFVPKSQSLH-UHFFFAOYSA-N 0.000 description 1
• JEQOZNSJCJLYDE-UHFFFAOYSA-N 8-benzyl-2-(tert-butylamino)-1-oxa-3,8-diazaspiro[4.5]dec-2-en-4-one Chemical compound O1C(NC(C)(C)C)=NC(=O)C11CCN(CC=2C=CC=CC=2)CC1 JEQOZNSJCJLYDE-UHFFFAOYSA-N 0.000 description 1
• GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 102100024090 Aldo-keto reductase family 1 member C3 Human genes 0.000 description 1
• 235000019489 Almond oil Nutrition 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
• 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 208000006386 Bone Resorption Diseases 0.000 description 1
• 206010065687 Bone loss Diseases 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• ZENYXRPZZASCQM-UHFFFAOYSA-N C1(CCCCC1)C=1SCC(N1)=O Chemical compound C1(CCCCC1)C=1SCC(N1)=O ZENYXRPZZASCQM-UHFFFAOYSA-N 0.000 description 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
• 108091007914 CDKs Proteins 0.000 description 1
• 101001078593 Caenorhabditis elegans 3beta-hydroxysteroid dehydrogenase/Delta(5)-Delta(4) isomerase 1 Proteins 0.000 description 1
• 241001286462 Caio Species 0.000 description 1
• 101100172290 Candida albicans (strain SC5314 / ATCC MYA-2876) ENG1 gene Proteins 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 206010008635 Cholestasis Diseases 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 208000028698 Cognitive impairment Diseases 0.000 description 1
• 102000029816 Collagenase Human genes 0.000 description 1
• 108060005980 Collagenase Proteins 0.000 description 1
• 206010009944 Colon cancer Diseases 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
• 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical class NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• 102100036504 Dehydrogenase/reductase SDR family member 9 Human genes 0.000 description 1
• 108020005199 Dehydrogenases Proteins 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• 239000004150 EU approved colour Substances 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 108050009340 Endothelin Proteins 0.000 description 1
• 102000002045 Endothelin Human genes 0.000 description 1
• 229940118365 Endothelin receptor antagonist Drugs 0.000 description 1
• 102400001368 Epidermal growth factor Human genes 0.000 description 1
• 101800003838 Epidermal growth factor Proteins 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 101710174214 Estradiol 17-beta-dehydrogenase 2 Proteins 0.000 description 1
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 102000003972 Fibroblast growth factor 7 Human genes 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
• VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
• 102400000321 Glucagon Human genes 0.000 description 1
• 108060003199 Glucagon Proteins 0.000 description 1
• 102000003676 Glucocorticoid Receptors Human genes 0.000 description 1
• 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
• 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
• MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 229910004721 HSiCl3 Inorganic materials 0.000 description 1
• 241000463109 Haloprofundus marisrubri Species 0.000 description 1
• 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
• 101000845090 Homo sapiens 11-beta-hydroxysteroid dehydrogenase type 2 Proteins 0.000 description 1
• 101000618112 Homo sapiens Sperm-associated antigen 8 Proteins 0.000 description 1
• 206010062767 Hypophysitis Diseases 0.000 description 1
• 206010022489 Insulin Resistance Diseases 0.000 description 1
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
• 102000004374 Insulin-like growth factor binding protein 3 Human genes 0.000 description 1
• 108090000965 Insulin-like growth factor binding protein 3 Proteins 0.000 description 1
• 108010002352 Interleukin-1 Proteins 0.000 description 1
• 102000000589 Interleukin-1 Human genes 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
• 229910010084 LiAlH4 Inorganic materials 0.000 description 1
• 235000019759 Maize starch Nutrition 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 101710151321 Melanostatin Proteins 0.000 description 1
• 102000005741 Metalloproteases Human genes 0.000 description 1
• 108010006035 Metalloproteases Proteins 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• 206010062575 Muscle contracture Diseases 0.000 description 1
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
• 150000007945 N-acyl ureas Chemical class 0.000 description 1
• PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 102400000064 Neuropeptide Y Human genes 0.000 description 1
• 206010029350 Neurotoxicity Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• RBYZXELNUKHAAL-UHFFFAOYSA-N O=C1N=C(NC2CCCCC2)OC11CCNCC1 Chemical compound O=C1N=C(NC2CCCCC2)OC11CCNCC1 RBYZXELNUKHAAL-UHFFFAOYSA-N 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 229910020667 PBr3 Inorganic materials 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
• 240000006711 Pistacia vera Species 0.000 description 1
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 206010037124 Pseudohermaphroditism male Diseases 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 102100021913 Sperm-associated antigen 8 Human genes 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 210000001744 T-lymphocyte Anatomy 0.000 description 1
• 229920002253 Tannate Polymers 0.000 description 1
• 206010044221 Toxic encephalopathy Diseases 0.000 description 1
• 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
• 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
• 102100040247 Tumor necrosis factor Human genes 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 108010062497 VLDL Lipoproteins Proteins 0.000 description 1
• 206010048038 Wound infection Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• FVXFFFHGYOYYQX-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC=C1C(F)(F)F FVXFFFHGYOYYQX-UHFFFAOYSA-N 0.000 description 1
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
• FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 1
• QKNDAUTYSODFJV-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;sodium Chemical compound [Na].C[Si](C)(C)N[Si](C)(C)C QKNDAUTYSODFJV-UHFFFAOYSA-N 0.000 description 1
• PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
• 150000008065 acid anhydrides Chemical class 0.000 description 1
• 239000003377 acid catalyst Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 210000004404 adrenal cortex Anatomy 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 238000007605 air drying Methods 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• VFRROHXSMXFLSN-KCDKBNATSA-N aldehydo-D-galactose 6-phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O VFRROHXSMXFLSN-KCDKBNATSA-N 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 150000001351 alkyl iodides Chemical class 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 125000002947 alkylene group Chemical group 0.000 description 1
• 239000008168 almond oil Substances 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 230000001668 ameliorated effect Effects 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229950003476 aminothiazole Drugs 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 229950003153 amsonate Drugs 0.000 description 1
• 230000000202 analgesic effect Effects 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 229940094957 androgens and estrogen Drugs 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 230000000845 anti-microbial effect Effects 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 230000003190 augmentative effect Effects 0.000 description 1
• OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
• 239000003899 bactericide agent Substances 0.000 description 1
• 210000000270 basal cell Anatomy 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
• 150000008331 benzenesulfonamides Chemical class 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 150000008359 benzonitriles Chemical class 0.000 description 1
• 239000012964 benzotriazole Substances 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• SLOPJPLJISGXPG-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3-carboxamide Chemical compound C1CC2C(C(=O)N)CC1C2 SLOPJPLJISGXPG-UHFFFAOYSA-N 0.000 description 1
• LKXGYGYFPTZHLC-UHFFFAOYSA-N bicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2CCC1(C(=O)O)C2 LKXGYGYFPTZHLC-UHFFFAOYSA-N 0.000 description 1
• 239000003613 bile acid Substances 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229960000074 biopharmaceutical Drugs 0.000 description 1
• 230000036983 biotransformation Effects 0.000 description 1
• 230000002051 biphasic effect Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 230000024279 bone resorption Effects 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000000337 buffer salt Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229910052792 caesium Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 238000004364 calculation method Methods 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 150000005323 carbonate salts Chemical class 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
• 230000007870 cholestasis Effects 0.000 description 1
• 231100000359 cholestasis Toxicity 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
• 238000011097 chromatography purification Methods 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 230000019771 cognition Effects 0.000 description 1
• 230000003920 cognitive function Effects 0.000 description 1
• 230000007691 collagen metabolic process Effects 0.000 description 1
• 230000037319 collagen production Effects 0.000 description 1
• 229960002424 collagenase Drugs 0.000 description 1
• 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 208000006111 contracture Diseases 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000013256 coordination polymer Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000010779 crude oil Substances 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
• 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• FOYWGUOQMYJRRR-UHFFFAOYSA-N dec-4-ene Chemical compound [CH2]CCC=CCCCCC FOYWGUOQMYJRRR-UHFFFAOYSA-N 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 238000005695 dehalogenation reaction Methods 0.000 description 1
• FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
• 230000002939 deleterious effect Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• 229940039227 diagnostic agent Drugs 0.000 description 1
• 239000000032 diagnostic agent Substances 0.000 description 1
• ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
• 230000003292 diminished effect Effects 0.000 description 1
• XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
• 229960002986 dinoprostone Drugs 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 230000008846 dynamic interplay Effects 0.000 description 1
• 229940009662 edetate Drugs 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 230000004821 effect on bone Effects 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 230000002124 endocrine Effects 0.000 description 1
• 230000002357 endometrial effect Effects 0.000 description 1
• 210000004696 endometrium Anatomy 0.000 description 1
• 239000002308 endothelin receptor antagonist Substances 0.000 description 1
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 1
• 210000000871 endothelium corneal Anatomy 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 229940116977 epidermal growth factor Drugs 0.000 description 1
• 210000000981 epithelium Anatomy 0.000 description 1
• 210000003560 epithelium corneal Anatomy 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 229950000206 estolate Drugs 0.000 description 1
• 229960005309 estradiol Drugs 0.000 description 1
• 229930182833 estradiol Natural products 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• CWVWVCGMEKVQMQ-XHHQTKHESA-N ethyl 2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-4-oxo-1,3-thiazole-5-carboxylate Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NC1=NC(=O)C(C(=O)OCC)S1 CWVWVCGMEKVQMQ-XHHQTKHESA-N 0.000 description 1
• RPEUEJTZHRHZQD-UHFFFAOYSA-N ethyl 2-pyridin-3-ylpropanoate Chemical compound CCOC(=O)C(C)C1=CC=CN=C1 RPEUEJTZHRHZQD-UHFFFAOYSA-N 0.000 description 1
• QVLJLWHOILVHJJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylacetate Chemical compound CCOC(=O)CC1=CC=NC=C1 QVLJLWHOILVHJJ-UHFFFAOYSA-N 0.000 description 1
• AILXLHFYUYKBML-UHFFFAOYSA-N ethyl 2-pyridin-4-ylpropanoate Chemical compound CCOC(=O)C(C)C1=CC=NC=C1 AILXLHFYUYKBML-UHFFFAOYSA-N 0.000 description 1
• YRILNHRWSGIDSN-UHFFFAOYSA-N ethyl 5-(3-ethoxy-3-oxopropyl)-4-oxo-2-[2-(trifluoromethyl)anilino]-1,3-thiazole-5-carboxylate Chemical compound O=C1C(CCC(=O)OCC)(C(=O)OCC)SC(NC=2C(=CC=CC=2)C(F)(F)F)=N1 YRILNHRWSGIDSN-UHFFFAOYSA-N 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical compound C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 206010016629 fibroma Diseases 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001207 fluorophenyl group Chemical group 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• GOLHZPOXCLTFRB-UHFFFAOYSA-N furan-3-carboxamide Chemical compound NC(=O)C=1C=COC=1 GOLHZPOXCLTFRB-UHFFFAOYSA-N 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
• 229960004666 glucagon Drugs 0.000 description 1
• 229960001731 gluceptate Drugs 0.000 description 1
• 229940126013 glucocorticoid receptor antagonist Drugs 0.000 description 1
• 239000003850 glucocorticoid receptor antagonist Substances 0.000 description 1
• 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 description 1
• KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 229940049906 glutamate Drugs 0.000 description 1
• 230000004116 glycogenolysis Effects 0.000 description 1
• 210000002149 gonad Anatomy 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 229960000789 guanidine hydrochloride Drugs 0.000 description 1
• PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 235000015220 hamburgers Nutrition 0.000 description 1
• JOPQZCZKKFHRNT-UHFFFAOYSA-N heptan-2-amine;hydrochloride Chemical compound Cl.CCCCCC(C)N JOPQZCZKKFHRNT-UHFFFAOYSA-N 0.000 description 1
• 239000008241 heterogeneous mixture Substances 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 150000002429 hydrazines Chemical class 0.000 description 1
• 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 208000006575 hypertriglyceridemia Diseases 0.000 description 1
• 230000002267 hypothalamic effect Effects 0.000 description 1
• 230000008105 immune reaction Effects 0.000 description 1
• 238000002649 immunization Methods 0.000 description 1
• 230000003053 immunization Effects 0.000 description 1
• 230000002163 immunogen Effects 0.000 description 1
• 238000007901 in situ hybridization Methods 0.000 description 1
• 206010021654 increased appetite Diseases 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 238000002329 infrared spectrum Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
• NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical class O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 150000002545 isoxazoles Chemical class 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
• 229940099584 lactobionate Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229940070765 laurate Drugs 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
• QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 239000006193 liquid solution Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 210000002540 macrophage Anatomy 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 238000007726 management method Methods 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000003550 marker Substances 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 238000010907 mechanical stirring Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000006993 memory improvement Effects 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000007102 metabolic function Effects 0.000 description 1
• 230000037353 metabolic pathway Effects 0.000 description 1
• TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• YGWINKVROAENAL-UHFFFAOYSA-N methyl 1-bromocyclopentane-1-carboxylate Chemical compound COC(=O)C1(Br)CCCC1 YGWINKVROAENAL-UHFFFAOYSA-N 0.000 description 1
• QAWIJSYVAVBHPB-UHFFFAOYSA-N methyl 2-(2-fluoroanilino)-4-oxo-1,3-thiazole-5-carboxylate Chemical compound O=C1C(C(=O)OC)SC(NC=2C(=CC=CC=2)F)=N1 QAWIJSYVAVBHPB-UHFFFAOYSA-N 0.000 description 1
• AQZRATSFTMXYLW-UHFFFAOYSA-N methyl 2-(oxan-4-yl)acetate Chemical compound COC(=O)CC1CCOCC1 AQZRATSFTMXYLW-UHFFFAOYSA-N 0.000 description 1
• NHFBYYMNJUMVOT-UHFFFAOYSA-N methyl 2-bromo-2-phenylacetate Chemical compound COC(=O)C(Br)C1=CC=CC=C1 NHFBYYMNJUMVOT-UHFFFAOYSA-N 0.000 description 1
• 229940102396 methyl bromide Drugs 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 210000001589 microsome Anatomy 0.000 description 1
• 239000002395 mineralocorticoid Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 150000004712 monophosphates Chemical class 0.000 description 1
• 210000004457 myocytus nodalis Anatomy 0.000 description 1
• WJQWUUGAAKRBIG-UHFFFAOYSA-N n-(2,3-dichlorophenyl)-2-[4-oxo-2-(propylamino)-1,3-thiazol-5-yl]acetamide Chemical compound S1C(NCCC)=NC(=O)C1CC(=O)NC1=CC=CC(Cl)=C1Cl WJQWUUGAAKRBIG-UHFFFAOYSA-N 0.000 description 1
• IQDJYFFOLQFOIB-UHFFFAOYSA-N n-(cyclooctylcarbamothioyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NC1CCCCCCC1 IQDJYFFOLQFOIB-UHFFFAOYSA-N 0.000 description 1
• OVYUVAHOBFWXBS-FVHHZMEASA-N n-[3-[4-[2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]piperidine-1-carbonyl]phenyl]acetamide Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NC(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1=CC=CC(NC(C)=O)=C1 OVYUVAHOBFWXBS-FVHHZMEASA-N 0.000 description 1
• GVCUNRFASRMDNM-GRMSHEEJSA-N n-[4-[4-[2-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]piperidine-1-carbonyl]phenyl]acetamide Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NC(S1)=NC(=O)C1(C)C(CC1)CCN1C(=O)C1=CC=C(NC(C)=O)C=C1 GVCUNRFASRMDNM-GRMSHEEJSA-N 0.000 description 1
• QCJJFBMDQGAACH-KFMLXFHDSA-N n-[4-[4-[[2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidin-1-yl]-4-oxobutyl]acetamide Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)CC1CCN(C(=O)CCCNC(C)=O)CC1 QCJJFBMDQGAACH-KFMLXFHDSA-N 0.000 description 1
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
• 125000006606 n-butoxy group Chemical group 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006608 n-octyloxy group Chemical group 0.000 description 1
• VYULNXGSBYCABA-UHFFFAOYSA-N n-phenyl-5-propan-2-yl-1,3-thiazol-2-amine Chemical compound S1C(C(C)C)=CN=C1NC1=CC=CC=C1 VYULNXGSBYCABA-UHFFFAOYSA-N 0.000 description 1
• 230000003955 neuronal function Effects 0.000 description 1
• 230000006576 neuronal survival Effects 0.000 description 1
• 230000007135 neurotoxicity Effects 0.000 description 1
• 231100000228 neurotoxicity Toxicity 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 150000002829 nitrogen Chemical class 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 230000024121 nodulation Effects 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000005485 noradamantyl group Chemical group 0.000 description 1
• SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• KPMKEVXVVHNIEY-UHFFFAOYSA-N norcamphor Chemical compound C1CC2C(=O)CC1C2 KPMKEVXVVHNIEY-UHFFFAOYSA-N 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
• 230000000269 nucleophilic effect Effects 0.000 description 1
• SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
• ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 description 1
• LVBXEMGDVWVTGY-UHFFFAOYSA-N oct-2-enal Chemical compound CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
• 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 230000011164 ossification Effects 0.000 description 1
• 210000000963 osteoblast Anatomy 0.000 description 1
• 210000002997 osteoclast Anatomy 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 239000006179 pH buffering agent Substances 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 239000003182 parenteral nutrition solution Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000008447 perception Effects 0.000 description 1
• 239000008196 pharmacological composition Substances 0.000 description 1
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
• DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 0.000 description 1
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
• 230000035479 physiological effects, processes and functions Effects 0.000 description 1
• 239000002504 physiological saline solution Substances 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 1
• LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
• LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
• 230000001817 pituitary effect Effects 0.000 description 1
• 210000003635 pituitary gland Anatomy 0.000 description 1
• 210000002826 placenta Anatomy 0.000 description 1
• 229940037129 plain mineralocorticoids for systemic use Drugs 0.000 description 1
• 230000036470 plasma concentration Effects 0.000 description 1
• 239000002985 plastic film Substances 0.000 description 1
• 229920006255 plastic film Polymers 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 235000011164 potassium chloride Nutrition 0.000 description 1
• VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 210000000229 preadipocyte Anatomy 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 201000009104 prediabetes syndrome Diseases 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 239000000186 progesterone Substances 0.000 description 1
• 229960003387 progesterone Drugs 0.000 description 1
• 239000000583 progesterone congener Substances 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
• XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• 230000007420 reactivation Effects 0.000 description 1
• 230000008707 rearrangement Effects 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000007634 remodeling Methods 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 239000011369 resultant mixture Substances 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 230000006965 reversible inhibition Effects 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 230000036186 satiety Effects 0.000 description 1
• 235000019627 satiety Nutrition 0.000 description 1
• 238000006748 scratching Methods 0.000 description 1
• 230000002393 scratching effect Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 229910052711 selenium Inorganic materials 0.000 description 1
• 239000011669 selenium Substances 0.000 description 1
• 229910000077 silane Inorganic materials 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 229920002545 silicone oil Polymers 0.000 description 1
• 230000012488 skeletal system development Effects 0.000 description 1
• 210000001626 skin fibroblast Anatomy 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000001593 sorbitan monooleate Substances 0.000 description 1
• 235000011069 sorbitan monooleate Nutrition 0.000 description 1
• 229940035049 sorbitan monooleate Drugs 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 210000005070 sphincter Anatomy 0.000 description 1
• LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
• 229960002256 spironolactone Drugs 0.000 description 1
• 239000003270 steroid hormone Substances 0.000 description 1
• 102000005969 steroid hormone receptors Human genes 0.000 description 1
• 108020003113 steroid hormone receptors Proteins 0.000 description 1
• 239000011550 stock solution Substances 0.000 description 1
• 239000012089 stop solution Substances 0.000 description 1
• 210000002536 stromal cell Anatomy 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 239000002278 tabletting lubricant Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 229950002757 teoclate Drugs 0.000 description 1
• UHSIAPDNRWLFDK-UHFFFAOYSA-N tert-butyl 3-[2-(2-chloroanilino)-5-methyl-4-oxo-1,3-thiazol-5-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C1(C)C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 UHSIAPDNRWLFDK-UHFFFAOYSA-N 0.000 description 1
• JUKOZKNMOKDRAC-QLENWOADSA-N tert-butyl 3-[2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]pyrrolidine-1-carboxylate Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCN(C(=O)OC(C)(C)C)C1 JUKOZKNMOKDRAC-QLENWOADSA-N 0.000 description 1
• YGJXBTRLYHCWGD-UHFFFAOYSA-N tert-butyl 4-(bromomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CBr)CC1 YGJXBTRLYHCWGD-UHFFFAOYSA-N 0.000 description 1
• DQPMMEVNTLSSTD-SZUMHKGVSA-N tert-butyl 4-[2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]piperidine-1-carboxylate Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(S1)=NC(=O)C1(C)C1CCN(C(=O)OC(C)(C)C)CC1 DQPMMEVNTLSSTD-SZUMHKGVSA-N 0.000 description 1
• VLPXLRJTLVBPSX-UHFFFAOYSA-N tert-butyl 4-[[2-(4-bicyclo[2.2.1]heptanylamino)-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC1(C)C(=O)N=C(NC23CCC(CC2)C3)S1 VLPXLRJTLVBPSX-UHFFFAOYSA-N 0.000 description 1
• ZRIBMKAZTAMBMY-UHFFFAOYSA-N tert-butyl 4-[[2-(cycloheptylamino)-5-methyl-4-oxo-1,3-thiazol-5-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1(C)C(=O)N=C(NC2CCCCCC2)S1 ZRIBMKAZTAMBMY-UHFFFAOYSA-N 0.000 description 1
• BRHGIZYMRTYNPG-UHFFFAOYSA-N tert-butyl n-(4-bicyclo[2.2.1]heptanyl)carbamate Chemical compound C1CC2CCC1(NC(=O)OC(C)(C)C)C2 BRHGIZYMRTYNPG-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• 150000003557 thiazoles Chemical class 0.000 description 1
• 125000004149 thio group Chemical group *S* 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 150000003577 thiophenes Chemical class 0.000 description 1
• 230000009772 tissue formation Effects 0.000 description 1
• 230000017423 tissue regeneration Effects 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 210000001585 trabecular meshwork Anatomy 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 239000005052 trichlorosilane Substances 0.000 description 1
• PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical group Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• 238000006692 trifluoromethylation reaction Methods 0.000 description 1
• KFJIQDILQUIILE-NDBYEHHHSA-N trimethoxy-[(1r,2s,4r,5s)-2-trimethoxysilyl-5-bicyclo[2.2.1]heptanyl]silane Chemical compound C1[C@H]([Si](OC)(OC)OC)[C@@]2([H])C[C@H]([Si](OC)(OC)OC)[C@]1([H])C2 KFJIQDILQUIILE-NDBYEHHHSA-N 0.000 description 1
• 239000001226 triphosphate Substances 0.000 description 1
• 235000011178 triphosphate Nutrition 0.000 description 1
• UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
• 230000007306 turnover Effects 0.000 description 1
• AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960004295 valine Drugs 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1
• 230000010388 wound contraction Effects 0.000 description 1
• 230000037314 wound repair Effects 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1