JP2010501567A - 代謝系、心血管系および他の障害の処置のためのステアロイル−ＣｏＡ不飽和化酵素（ＳＣＤ）阻害剤としての２−（ピラジン−２−イル）−チアゾールおよび２−（１Ｈ−ピラゾール−３−イル）チアゾール誘導体ならびに関連化合物 - Google Patents

Info

Publication number

JP2010501567A

JP2010501567A JP2009525617A JP2009525617A JP2010501567A JP 2010501567 A JP2010501567 A JP 2010501567A JP 2009525617 A JP2009525617 A JP 2009525617A JP 2009525617 A JP2009525617 A JP 2009525617A JP 2010501567 A JP2010501567 A JP 2010501567A

Authority

JP

Japan

Prior art keywords

methyl

thiazole

carboxylic acid

pyrazol

fluoro

Prior art date

2006-08-24

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

Pending

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 279
• 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 97
• 239000003112 inhibitor Substances 0.000 title claims abstract description 24
• 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims 7
• 230000002503 metabolic effect Effects 0.000 title description 2
• OGINRMMVESEAEM-UHFFFAOYSA-N 2-pyrazin-2-yl-1,3-thiazole Chemical compound C1=CSC(C=2N=CC=NC=2)=N1 OGINRMMVESEAEM-UHFFFAOYSA-N 0.000 title 1
• 230000002526 effect on cardiovascular system Effects 0.000 title 1
• 150000007979 thiazole derivatives Chemical class 0.000 title 1
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 113
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 109
• 201000010099 disease Diseases 0.000 claims abstract description 80
• 230000001404 mediated effect Effects 0.000 claims abstract description 36
• 208000008589 Obesity Diseases 0.000 claims abstract description 15
• 235000020824 obesity Nutrition 0.000 claims abstract description 15
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 11
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 11
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 185
• 125000003118 aryl group Chemical group 0.000 claims description 151
• -1 trifluoromethoxyl Chemical group 0.000 claims description 119
• 125000001072 heteroaryl group Chemical group 0.000 claims description 114
• 239000001257 hydrogen Substances 0.000 claims description 110
• 229910052739 hydrogen Inorganic materials 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 106
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 100
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 98
• 150000002431 hydrogen Chemical class 0.000 claims description 74
• 238000000034 method Methods 0.000 claims description 73
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 59
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 59
• 230000000694 effects Effects 0.000 claims description 48
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 47
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 39
• 125000002947 alkylene group Chemical group 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 239000008194 pharmaceutical composition Substances 0.000 claims description 32
• 208000035475 disorder Diseases 0.000 claims description 28
• 125000004450 alkenylene group Chemical group 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• MBALKBRJRNEXCS-UHFFFAOYSA-N n-benzyl-4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=CC=C1 MBALKBRJRNEXCS-UHFFFAOYSA-N 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• 239000000651 prodrug Substances 0.000 claims description 20
• 229940002612 prodrug Drugs 0.000 claims description 20
• 125000004419 alkynylene group Chemical group 0.000 claims description 19
• 125000003367 polycyclic group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 17
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 8
• 239000003446 ligand Substances 0.000 claims description 7
• WVYLATFUURTLHK-UHFFFAOYSA-N 2-[3-[4-methyl-5-(pyridin-3-ylmethylcarbamoyl)-1,3-thiazol-2-yl]pyrazol-1-yl]ethyl methanesulfonate Chemical compound CC=1N=C(C2=NN(CCOS(C)(=O)=O)C=C2)SC=1C(=O)NCC1=CC=CN=C1 WVYLATFUURTLHK-UHFFFAOYSA-N 0.000 claims description 6
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](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(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 6
• 206010022489 Insulin Resistance Diseases 0.000 claims description 6
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
• 101000631826 Homo sapiens Stearoyl-CoA desaturase Proteins 0.000 claims description 5
• 102000055981 human SCD1 Human genes 0.000 claims description 5
• RRLZEMBDKSCPJD-UHFFFAOYSA-N n-benzyl-2-(5-bromopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(Br)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 RRLZEMBDKSCPJD-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 4
• 206010023330 Keloid scar Diseases 0.000 claims description 4
• 239000008103 glucose Substances 0.000 claims description 4
• OHNWRCKCGSXMOS-UHFFFAOYSA-N n-benzyl-2-(6-chloropyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(Cl)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 OHNWRCKCGSXMOS-UHFFFAOYSA-N 0.000 claims description 4
• 230000036573 scar formation Effects 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• JROCFBGRHZCVEM-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCO)C=C2)SC=1C(=O)NCC1=CC=CN=C1 JROCFBGRHZCVEM-UHFFFAOYSA-N 0.000 claims description 3
• PASYEHCKCRQQPU-UHFFFAOYSA-N 2-[1-[(3,5-difluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(F)C=C(F)C=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 PASYEHCKCRQQPU-UHFFFAOYSA-N 0.000 claims description 3
• QLUWINQMTXITCQ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(2-pyridin-3-ylethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCCC1=CC=CN=C1 QLUWINQMTXITCQ-UHFFFAOYSA-N 0.000 claims description 3
• GSMOTFYLIZJFSZ-UHFFFAOYSA-N 2-[1-[2-[(4-fluorophenyl)sulfonylamino]ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNS(=O)(=O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 GSMOTFYLIZJFSZ-UHFFFAOYSA-N 0.000 claims description 3
• IHQVUTRLMXEZMM-UHFFFAOYSA-N 2-[6-[2-(4-fluorophenoxy)ethyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(O)=O)=NC=1N(C)CCOC1=CC=C(F)C=C1 IHQVUTRLMXEZMM-UHFFFAOYSA-N 0.000 claims description 3
• COHIABZYSSAWPB-UHFFFAOYSA-N 2-[6-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=C(F)C=C1 COHIABZYSSAWPB-UHFFFAOYSA-N 0.000 claims description 3
• ANIJWYCYCAMXLW-UHFFFAOYSA-N 4-methyl-2-[1-[(4-methylsulfonylphenyl)methyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)S(C)(=O)=O)C=C2)SC=1C(=O)NCC1=CC=CN=C1 ANIJWYCYCAMXLW-UHFFFAOYSA-N 0.000 claims description 3
• GRCRTBQDOQHLNV-UHFFFAOYSA-N 4-methyl-2-[1-[(4-pyrazol-1-ylphenyl)methyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)N3N=CC=C3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 GRCRTBQDOQHLNV-UHFFFAOYSA-N 0.000 claims description 3
• XRDMAXCBXHZAJS-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[[4-(trifluoromethoxy)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(OC(F)(F)F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 XRDMAXCBXHZAJS-UHFFFAOYSA-N 0.000 claims description 3
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 102000016267 Leptin Human genes 0.000 claims description 3
• 108010092277 Leptin Proteins 0.000 claims description 3
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 3
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 3
• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 3
• 229940039781 leptin Drugs 0.000 claims description 3
• PDHGYOLSCBGQBD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 PDHGYOLSCBGQBD-UHFFFAOYSA-N 0.000 claims description 3
• SNSYNTMEUZSUJK-UHFFFAOYSA-N n-benzyl-2-(6-benzylpyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 SNSYNTMEUZSUJK-UHFFFAOYSA-N 0.000 claims description 3
• CYNQYUQKILVCSY-FQEVSTJZSA-N n-benzyl-2-[1-[(2r)-2-hydroxy-2-phenylethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(C[C@H](O)C=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 CYNQYUQKILVCSY-FQEVSTJZSA-N 0.000 claims description 3
• BOSVIHWMSQFDEA-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-methoxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)C=C1 BOSVIHWMSQFDEA-UHFFFAOYSA-N 0.000 claims description 3
• HDSGUOKYJJDUFO-UHFFFAOYSA-N n-benzyl-2-[5-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(CCC=3C=CC(F)=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 HDSGUOKYJJDUFO-UHFFFAOYSA-N 0.000 claims description 3
• WUJOIVVXTOFJRU-UHFFFAOYSA-N n-benzyl-2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=NC=1N(C)CC1=CC=C(F)C=C1 WUJOIVVXTOFJRU-UHFFFAOYSA-N 0.000 claims description 3
• DUPJSRQEIOJXIB-FMIVXFBMSA-N n-benzyl-2-[6-[(e)-2-(4-fluorophenyl)ethenyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 DUPJSRQEIOJXIB-FMIVXFBMSA-N 0.000 claims description 3
• AEVBIYNSSLOWIE-UHFFFAOYSA-N n-benzyl-2-[6-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 AEVBIYNSSLOWIE-UHFFFAOYSA-N 0.000 claims description 3
• UHZOCHGUMDRKFR-UHFFFAOYSA-N n-benzyl-4-methyl-2-[5-(3-phenylpropyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(CCCC=3C=CC=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 UHZOCHGUMDRKFR-UHFFFAOYSA-N 0.000 claims description 3
• KQYPATXQBASHAJ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-(3-phenylpropyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 KQYPATXQBASHAJ-UHFFFAOYSA-N 0.000 claims description 3
• WCUJIXRJEZFGKN-FMIVXFBMSA-N n-benzyl-4-methyl-2-[6-[(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC(=CC=3)C(F)(F)F)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 WCUJIXRJEZFGKN-FMIVXFBMSA-N 0.000 claims description 3
• MPLHKNJNLFDAOB-OUKQBFOZSA-N n-benzyl-4-methyl-2-[6-[(e)-2-phenylethenyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 MPLHKNJNLFDAOB-OUKQBFOZSA-N 0.000 claims description 3
• OOQMPRBWXAJUFF-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-[2-[4-(trifluoromethyl)phenyl]ethyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(=CC=3)C(F)(F)F)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 OOQMPRBWXAJUFF-UHFFFAOYSA-N 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 208000017520 skin disease Diseases 0.000 claims description 3
• 201000005665 thrombophilia Diseases 0.000 claims description 3
• 208000016261 weight loss Diseases 0.000 claims description 3
• 230000004580 weight loss Effects 0.000 claims description 3
• COFXNWIKPNAICQ-UHFFFAOYSA-N 2-[1-(2-anilinoethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 COFXNWIKPNAICQ-UHFFFAOYSA-N 0.000 claims description 2
• DESUOBUOHOUZSF-UHFFFAOYSA-N 2-[1-(2-cyclopropylethyl)pyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC3CC3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 DESUOBUOHOUZSF-UHFFFAOYSA-N 0.000 claims description 2
• OGBAAAIKRBXTIV-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(Cl)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 OGBAAAIKRBXTIV-UHFFFAOYSA-N 0.000 claims description 2
• OKMKIHSFKTXQHZ-UHFFFAOYSA-N 2-[1-[(3-cyanophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(C=CC=3)C#N)C=C2)SC=1C(=O)NCC1=CC=CN=C1 OKMKIHSFKTXQHZ-UHFFFAOYSA-N 0.000 claims description 2
• FUJCGBTZOLHJSE-UHFFFAOYSA-N 2-[1-[(3-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(F)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 FUJCGBTZOLHJSE-UHFFFAOYSA-N 0.000 claims description 2
• WDABMXCIUPNKCF-UHFFFAOYSA-N 2-[1-[(4-chloro-2-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C(=CC(Cl)=CC=3)F)C=C2)SC=1C(=O)NCC1=CC=CN=C1 WDABMXCIUPNKCF-UHFFFAOYSA-N 0.000 claims description 2
• NVNBSOWRMZEZCP-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(Cl)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 NVNBSOWRMZEZCP-UHFFFAOYSA-N 0.000 claims description 2
• AKWDNTBINCFIOL-UHFFFAOYSA-N 2-[1-[(4-cyanophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)C#N)C=C2)SC=1C(=O)NCC1=CC=CN=C1 AKWDNTBINCFIOL-UHFFFAOYSA-N 0.000 claims description 2
• UNFYXLDSTKSWOV-UHFFFAOYSA-N 2-[1-[(4-ethylphenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(CC)=CC=C1CN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)C=C1 UNFYXLDSTKSWOV-UHFFFAOYSA-N 0.000 claims description 2
• LJCCIMKJGXIMGS-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LJCCIMKJGXIMGS-UHFFFAOYSA-N 0.000 claims description 2
• HUPGKCGSDFOLNY-UHFFFAOYSA-N 2-[1-[(4-tert-butylphenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)C(C)(C)C)C=C2)SC=1C(=O)NCC1=CC=CN=C1 HUPGKCGSDFOLNY-UHFFFAOYSA-N 0.000 claims description 2
• LYHDTGAYMNXTQQ-UHFFFAOYSA-N 2-[1-[2-(4-fluoroanilino)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LYHDTGAYMNXTQQ-UHFFFAOYSA-N 0.000 claims description 2
• ZLTCYIDFMSNXKL-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenoxy)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 ZLTCYIDFMSNXKL-UHFFFAOYSA-N 0.000 claims description 2
• IBJROADCWLUKIU-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)=NN1CCC1=CC=C(F)C=C1 IBJROADCWLUKIU-UHFFFAOYSA-N 0.000 claims description 2
• LWOSUYHAPVQEBO-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LWOSUYHAPVQEBO-UHFFFAOYSA-N 0.000 claims description 2
• XOHQYXIUZYTVJI-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NC1=CC=CN=C1 XOHQYXIUZYTVJI-UHFFFAOYSA-N 0.000 claims description 2
• IMFXAWNWSAISIS-UHFFFAOYSA-N 2-[1-[2-(4-methoxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)C=C1 IMFXAWNWSAISIS-UHFFFAOYSA-N 0.000 claims description 2
• QTKLPOWQQUEGNX-UHFFFAOYSA-N 2-[1-[2-[(4-fluorobenzoyl)amino]ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC(=O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 QTKLPOWQQUEGNX-UHFFFAOYSA-N 0.000 claims description 2
• FBQDWBGOZONRTQ-UHFFFAOYSA-N 2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)=NC=1N(C)CC1=CC=C(F)C=C1 FBQDWBGOZONRTQ-UHFFFAOYSA-N 0.000 claims description 2
• NWAKIDXIIAQAQW-UHFFFAOYSA-N 4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 NWAKIDXIIAQAQW-UHFFFAOYSA-N 0.000 claims description 2
• XCNRBOGRGUYICM-UHFFFAOYSA-N 4-methyl-2-[1-(2-phenylpropyl)pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C(C)CN(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-UHFFFAOYSA-N 0.000 claims description 2
• XCNRBOGRGUYICM-INIZCTEOSA-N 4-methyl-2-[1-[(2r)-2-phenylpropyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C([C@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-INIZCTEOSA-N 0.000 claims description 2
• XCNRBOGRGUYICM-MRXNPFEDSA-N 4-methyl-2-[1-[(2s)-2-phenylpropyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-MRXNPFEDSA-N 0.000 claims description 2
• SVALBOALYAAMBS-UHFFFAOYSA-N 4-methyl-2-[1-[2-(n-methylanilino)ethyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1N(C)CCN(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 SVALBOALYAAMBS-UHFFFAOYSA-N 0.000 claims description 2
• BJOYXMHHMOVLRF-UHFFFAOYSA-N 4-methyl-2-[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=NN(CC=2C=CC(=CC=2)N2N=CN=C2)C=C1 BJOYXMHHMOVLRF-UHFFFAOYSA-N 0.000 claims description 2
• PLIMZFASPVYCBJ-UHFFFAOYSA-N 4-methyl-2-[5-methyl-1-[[4-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)=NN1CC1=CC=C(C(F)(F)F)C=C1 PLIMZFASPVYCBJ-UHFFFAOYSA-N 0.000 claims description 2
• YUWUXPNAEHVSGN-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[(4-pyrrol-1-ylphenyl)methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)N3C=CC=C3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 YUWUXPNAEHVSGN-UHFFFAOYSA-N 0.000 claims description 2
• YKLLRTGAZGTGLM-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(OC(F)(F)F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 YKLLRTGAZGTGLM-UHFFFAOYSA-N 0.000 claims description 2
• JXZFXILVYUEBNU-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(C=CC=3)C(F)(F)F)C=C2)SC=1C(=O)NCC1=CC=CN=C1 JXZFXILVYUEBNU-UHFFFAOYSA-N 0.000 claims description 2
• XJEWZWJRMRJFBU-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[[4-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)C(F)(F)F)C=C2)SC=1C(=O)NCC1=CC=CN=C1 XJEWZWJRMRJFBU-UHFFFAOYSA-N 0.000 claims description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
• 229940123208 Biguanide Drugs 0.000 claims description 2
• 206010006895 Cachexia Diseases 0.000 claims description 2
• 229920001268 Cholestyramine Polymers 0.000 claims description 2
• 201000004624 Dermatitis Diseases 0.000 claims description 2
• 208000002249 Diabetes Complications Diseases 0.000 claims description 2
• 206010012655 Diabetic complications Diseases 0.000 claims description 2
• 201000001431 Hyperuricemia Diseases 0.000 claims description 2
• 102000004877 Insulin Human genes 0.000 claims description 2
• 108090001061 Insulin Proteins 0.000 claims description 2
• 229940122199 Insulin secretagogue Drugs 0.000 claims description 2
• 229940122355 Insulin sensitizer Drugs 0.000 claims description 2
• VBEBTNRIGINJJA-UHFFFAOYSA-N N-benzyl-4-methyl-2-[1-(1-phenylethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=NN1C(C)C1=CC=CC=C1 VBEBTNRIGINJJA-UHFFFAOYSA-N 0.000 claims description 2
• 206010033307 Overweight Diseases 0.000 claims description 2
• 208000004210 Pressure Ulcer Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• 102000018692 Sulfonylurea Receptors Human genes 0.000 claims description 2
• 108010091821 Sulfonylurea Receptors Proteins 0.000 claims description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
• 208000022531 anorexia Diseases 0.000 claims description 2
• 208000010668 atopic eczema Diseases 0.000 claims description 2
• 206010061428 decreased appetite Diseases 0.000 claims description 2
• JLLGRBZBHZHPSL-UHFFFAOYSA-N ethyl 4-[[3-[4-methyl-5-(2-pyridin-3-ylacetyl)-2,5-dihydro-1,3-thiazol-2-yl]pyrazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1CN1N=C(C2N=C(C)C(C(=O)CC=3C=NC=CC=3)S2)C=C1 JLLGRBZBHZHPSL-UHFFFAOYSA-N 0.000 claims description 2
• 229940125753 fibrate Drugs 0.000 claims description 2
• 229940125396 insulin Drugs 0.000 claims description 2
• 230000002473 insulinotropic effect Effects 0.000 claims description 2
• IKNFPSAIMOUEFA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC2CC2)=NC=1N(C)CC1=CC=C(F)C=C1 IKNFPSAIMOUEFA-UHFFFAOYSA-N 0.000 claims description 2
• KMYXKKYXCVUMSG-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[1-[2-(1h-indol-3-yl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C4=CC=CC=C4NC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 KMYXKKYXCVUMSG-UHFFFAOYSA-N 0.000 claims description 2
• VBAAUGQBYHBVNT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[1-[2-(4-methoxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)C=C1 VBAAUGQBYHBVNT-UHFFFAOYSA-N 0.000 claims description 2
• ZREBOAPYAYXSLR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[(3-methoxyphenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(CN(C)C=2N=C(C=NC=2)C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=C1 ZREBOAPYAYXSLR-UHFFFAOYSA-N 0.000 claims description 2
• GYTQYZNZOVHTSR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=C(F)C=C1 GYTQYZNZOVHTSR-UHFFFAOYSA-N 0.000 claims description 2
• FWFCXCFSXJCUKS-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[(4-methoxyphenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=N1 FWFCXCFSXJCUKS-UHFFFAOYSA-N 0.000 claims description 2
• FDZCLWLNBFSEPN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[2-(4-methoxyphenoxy)ethyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1OCCN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=N1 FDZCLWLNBFSEPN-UHFFFAOYSA-N 0.000 claims description 2
• NVHZOGAOUCBLSC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-(6-phenylmethoxypyrazin-2-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(OCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=C(F)C=C1 NVHZOGAOUCBLSC-UHFFFAOYSA-N 0.000 claims description 2
• WAFCJISNXFCULQ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[1-(2-methyl-2-phenylpropyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC(C)(C)C=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 WAFCJISNXFCULQ-UHFFFAOYSA-N 0.000 claims description 2
• VCZSMYRQDLCBBV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[3-(2-phenylethyl)pyrrolidin-1-yl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(C=NC=2)N2CC(CCC=3C=CC=CC=3)CC2)SC=1C(=O)NCC1=CC=C(F)C=C1 VCZSMYRQDLCBBV-UHFFFAOYSA-N 0.000 claims description 2
• GQJRNMMMKLSKQW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(3-phenylpropyl)amino]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CCCC1=CC=CC=C1 GQJRNMMMKLSKQW-UHFFFAOYSA-N 0.000 claims description 2
• XWFGOQZOFHUJKO-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=CN=C1 XWFGOQZOFHUJKO-UHFFFAOYSA-N 0.000 claims description 2
• JJAPIHHTKWABOL-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(pyridin-4-ylmethyl)amino]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=NC=C1 JJAPIHHTKWABOL-UHFFFAOYSA-N 0.000 claims description 2
• HPFATVYVQHYBJP-UHFFFAOYSA-N n-benzyl-2-[1-(2-cyclohexylethyl)pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC3CCCCC3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 HPFATVYVQHYBJP-UHFFFAOYSA-N 0.000 claims description 2
• CYNQYUQKILVCSY-HXUWFJFHSA-N n-benzyl-2-[1-[(2s)-2-hydroxy-2-phenylethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(C[C@@H](O)C=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 CYNQYUQKILVCSY-HXUWFJFHSA-N 0.000 claims description 2
• VAIMBEBJDMUXRS-UHFFFAOYSA-N n-benzyl-2-[1-[2-(3-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=C(F)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 VAIMBEBJDMUXRS-UHFFFAOYSA-N 0.000 claims description 2
• AXBXPJURPLQSPM-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-fluorophenoxy)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 AXBXPJURPLQSPM-UHFFFAOYSA-N 0.000 claims description 2
• HGRDKYCIEAYSPA-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 HGRDKYCIEAYSPA-UHFFFAOYSA-N 0.000 claims description 2
• UGCNUNBCUZTXOW-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-hydroxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(O)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 UGCNUNBCUZTXOW-UHFFFAOYSA-N 0.000 claims description 2
• JYLRTPHRXNYQKP-UHFFFAOYSA-N n-benzyl-2-[6-(dimethylamino)pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=N1 JYLRTPHRXNYQKP-UHFFFAOYSA-N 0.000 claims description 2
• CGLGLWNFCHPFKN-UHFFFAOYSA-N n-benzyl-2-[6-[2-(4-fluorophenoxy)ethyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=NC=1N(C)CCOC1=CC=C(F)C=C1 CGLGLWNFCHPFKN-UHFFFAOYSA-N 0.000 claims description 2
• KPNNJUWSPXKUQZ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 KPNNJUWSPXKUQZ-UHFFFAOYSA-N 0.000 claims description 2
• AXGKNLBSHYSJBH-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(2-phenylpropyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C(C)CN(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CC=C1 AXGKNLBSHYSJBH-UHFFFAOYSA-N 0.000 claims description 2
• VQJKYGUXJPUYEY-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(3-methylbutyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC(C)CCN1C=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=N1 VQJKYGUXJPUYEY-UHFFFAOYSA-N 0.000 claims description 2
• WPQXFAXZKZFIOX-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(3-phenylpropyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCCC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 WPQXFAXZKZFIOX-UHFFFAOYSA-N 0.000 claims description 2
• AXGKNLBSHYSJBH-KRWDZBQOSA-N n-benzyl-4-methyl-2-[1-[(2r)-2-phenylpropyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CC=C1 AXGKNLBSHYSJBH-KRWDZBQOSA-N 0.000 claims description 2
• AXGKNLBSHYSJBH-QGZVFWFLSA-N n-benzyl-4-methyl-2-[1-[(2s)-2-phenylpropyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CC=C1 AXGKNLBSHYSJBH-QGZVFWFLSA-N 0.000 claims description 2
• GTMQESWOUJKROP-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-(2-phenylethyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 GTMQESWOUJKROP-UHFFFAOYSA-N 0.000 claims description 2
• 239000004059 squalene synthase inhibitor Substances 0.000 claims description 2
• GWJWYIOSBVKWFI-UHFFFAOYSA-N tert-butyl n-[2-[3-[4-methyl-5-(pyridin-3-ylmethylcarbamoyl)-1,3-thiazol-2-yl]pyrazol-1-yl]ethyl]carbamate Chemical compound CC=1N=C(C2=NN(CCNC(=O)OC(C)(C)C)C=C2)SC=1C(=O)NCC1=CC=CN=C1 GWJWYIOSBVKWFI-UHFFFAOYSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 10
• CGTPBDCTPXABEE-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NN1CCC1=CC=C(F)C=C1 CGTPBDCTPXABEE-UHFFFAOYSA-N 0.000 claims 1
• LUBYVOZPGKDWPF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 LUBYVOZPGKDWPF-UHFFFAOYSA-N 0.000 claims 1
• LFQXILYITNIVCS-UHFFFAOYSA-N 2-[6-[[4-(difluoromethoxy)phenyl]methyl-methylamino]pyrazin-2-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=C(OC(F)F)C=C1 LFQXILYITNIVCS-UHFFFAOYSA-N 0.000 claims 1
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims 1
• 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 claims 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
• 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 claims 1
• 230000003247 decreasing effect Effects 0.000 claims 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
• 239000004026 insulin derivative Substances 0.000 claims 1
• KOPOJJSSNIWROC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(2-pyridin-2-ylethyl)amino]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CCC1=CC=CC=N1 KOPOJJSSNIWROC-UHFFFAOYSA-N 0.000 claims 1
• CQVMYDXXMQCOLT-FQEVSTJZSA-N n-benzyl-2-[1-[(2r)-2-(4-fluorophenyl)-2-hydroxyethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(C[C@H](O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 CQVMYDXXMQCOLT-FQEVSTJZSA-N 0.000 claims 1
• 102100028897 Stearoyl-CoA desaturase Human genes 0.000 abstract description 91
• 150000002632 lipids Chemical class 0.000 abstract description 27
• 101100041816 Homo sapiens SCD gene Proteins 0.000 abstract description 10
• 239000000126 substance Substances 0.000 abstract description 9
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
• 101150097713 SCD1 gene Proteins 0.000 abstract 1
• 230000006806 disease prevention Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
• 230000015572 biosynthetic process Effects 0.000 description 124
• 238000003786 synthesis reaction Methods 0.000 description 123
• 238000005481 NMR spectroscopy Methods 0.000 description 96
• 239000011541 reaction mixture Substances 0.000 description 85
• 239000007787 solid Substances 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 55
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• 239000011734 sodium Substances 0.000 description 50
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 41
• 239000000203 mixture Substances 0.000 description 40
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• 229910052757 nitrogen Inorganic materials 0.000 description 36
• 239000012267 brine Substances 0.000 description 34
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• VOMYHJXMICIBNF-UHFFFAOYSA-N 4-methyl-2-(1h-pyrazol-5-yl)-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=CN=C1 VOMYHJXMICIBNF-UHFFFAOYSA-N 0.000 description 30
• 239000012074 organic phase Substances 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 241000700605 Viruses Species 0.000 description 28
• 125000004432 carbon atom Chemical group C* 0.000 description 27
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 24
• 239000012043 crude product Substances 0.000 description 24
• 239000002904 solvent Substances 0.000 description 23
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 125000005843 halogen group Chemical group 0.000 description 22
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 235000014113 dietary fatty acids Nutrition 0.000 description 18
• 239000000194 fatty acid Substances 0.000 description 18
• 229930195729 fatty acid Natural products 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 17
• 241001465754 Metazoa Species 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 17
• 150000004665 fatty acids Chemical class 0.000 description 17
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 229910004298 SiO 2 Inorganic materials 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 238000012746 preparative thin layer chromatography Methods 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• 101710159293 Acyl-CoA desaturase 1 Proteins 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 14
• 230000004048 modification Effects 0.000 description 14
• 238000012986 modification Methods 0.000 description 14
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 14
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• 239000011701 zinc Substances 0.000 description 12
• 229910052725 zinc Inorganic materials 0.000 description 12
• SZJIQLSCDIEJFC-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(F)C=C1 SZJIQLSCDIEJFC-UHFFFAOYSA-N 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 150000003626 triacylglycerols Chemical class 0.000 description 11
• 241000699670 Mus sp. Species 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 235000012000 cholesterol Nutrition 0.000 description 10
• 229940124597 therapeutic agent Drugs 0.000 description 10
• 102000004190 Enzymes Human genes 0.000 description 9
• 108090000790 Enzymes Proteins 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 238000003556 assay Methods 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• IQTQSDXJUJUFNT-UHFFFAOYSA-N n-benzyl-2-bromo-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=C(Br)SC(C(=O)NCC=2C=CC=CC=2)=C1C IQTQSDXJUJUFNT-UHFFFAOYSA-N 0.000 description 9
• 238000002953 preparative HPLC Methods 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 101150003085 Pdcl gene Proteins 0.000 description 8
• 230000004071 biological effect Effects 0.000 description 8
• 125000001183 hydrocarbyl group Chemical group 0.000 description 8
• 238000001727 in vivo Methods 0.000 description 8
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 241000282412 Homo Species 0.000 description 7
• 241000699666 Mus <mouse, genus> Species 0.000 description 7
• 230000002159 abnormal effect Effects 0.000 description 7
• 238000006880 cross-coupling reaction Methods 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 208000006575 hypertriglyceridemia Diseases 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 230000037356 lipid metabolism Effects 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• JUWRQDATTZQDKY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=C(F)C=C1 JUWRQDATTZQDKY-UHFFFAOYSA-N 0.000 description 7
• 230000036470 plasma concentration Effects 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• NEUWPDLMDVINSN-UHFFFAOYSA-N 1h-pyrazol-5-ylboronic acid Chemical compound OB(O)C=1C=CNN=1 NEUWPDLMDVINSN-UHFFFAOYSA-N 0.000 description 6
• HMSQZHBSTZZNGI-UHFFFAOYSA-N 2-bromo-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=C(Br)SC=1C(O)=O HMSQZHBSTZZNGI-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 239000003085 diluting agent Substances 0.000 description 6
• KLBIMFBTWSVHJX-UHFFFAOYSA-N ethyl 4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2NN=CC=2)=N1 KLBIMFBTWSVHJX-UHFFFAOYSA-N 0.000 description 6
• 210000004185 liver Anatomy 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• IFUFIXVEIBDHAU-UHFFFAOYSA-N n-benzyl-2-(6-iodopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(I)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 IFUFIXVEIBDHAU-UHFFFAOYSA-N 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• OQFBNFVTGUSVEQ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=NN(CCC=2C=CC(F)=CC=2)C=C1 OQFBNFVTGUSVEQ-UHFFFAOYSA-N 0.000 description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 210000001853 liver microsome Anatomy 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 210000001589 microsome Anatomy 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• SLZIHPKCNBTZQC-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(O)=O)=NN1CCC1=CC=C(F)C=C1 SLZIHPKCNBTZQC-UHFFFAOYSA-N 0.000 description 4
• 206010019708 Hepatic steatosis Diseases 0.000 description 4
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
• 235000021355 Stearic acid Nutrition 0.000 description 4
• 108010062497 VLDL Lipoproteins Proteins 0.000 description 4
• 238000010171 animal model Methods 0.000 description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 235000005911 diet Nutrition 0.000 description 4
• 208000037765 diseases and disorders Diseases 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• HBXOVOUGHCHRFU-UHFFFAOYSA-N ethyl 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)=N1 HBXOVOUGHCHRFU-UHFFFAOYSA-N 0.000 description 4
• 208000006454 hepatitis Diseases 0.000 description 4
• 231100000283 hepatitis Toxicity 0.000 description 4
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• KGNFDKHCWKAFGJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-(6-iodopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(I)C=NC=2)SC=1C(=O)NCC1=CC=C(F)C=C1 KGNFDKHCWKAFGJ-UHFFFAOYSA-N 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• 239000012038 nucleophile Substances 0.000 description 4
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 238000000926 separation method Methods 0.000 description 4
• 239000012453 solvate Substances 0.000 description 4
• 239000008117 stearic acid Substances 0.000 description 4
• SIARJEKBADXQJG-LFZQUHGESA-N stearoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SIARJEKBADXQJG-LFZQUHGESA-N 0.000 description 4
• 239000006228 supernatant Substances 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• 210000001519 tissue Anatomy 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• 229910052721 tungsten Inorganic materials 0.000 description 4
• 229910052727 yttrium Inorganic materials 0.000 description 4
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 3
• YQYDIMZEGLFTJT-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-3-iodo-5-methylpyrazole Chemical compound CC1=CC(I)=NN1CCC1=CC=C(F)C=C1 YQYDIMZEGLFTJT-UHFFFAOYSA-N 0.000 description 3
• YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 3
• XJWVCWQKZQENDS-UHFFFAOYSA-N 1-bromopropan-2-ylbenzene Chemical compound BrCC(C)C1=CC=CC=C1 XJWVCWQKZQENDS-UHFFFAOYSA-N 0.000 description 3
• XDGFMLMNWQGILQ-UHFFFAOYSA-N 2,6-diiodopyrazine Chemical compound IC1=CN=CC(I)=N1 XDGFMLMNWQGILQ-UHFFFAOYSA-N 0.000 description 3
• HLFSFSUGAMRNSL-UHFFFAOYSA-N 2-[1-(2-aminoethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCN)C=C2)SC=1C(=O)NCC1=CC=CN=C1 HLFSFSUGAMRNSL-UHFFFAOYSA-N 0.000 description 3
• CQTRKGSINIWSNH-UHFFFAOYSA-N 2-bromo-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=C(Br)SC(C(=O)NCC=2C=CC(F)=CC=2)=C1C CQTRKGSINIWSNH-UHFFFAOYSA-N 0.000 description 3
• JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 3
• FPLNGDMFVSCNHK-UHFFFAOYSA-N 3,4-diiodo-5-methyl-1h-pyrazole Chemical compound CC=1NN=C(I)C=1I FPLNGDMFVSCNHK-UHFFFAOYSA-N 0.000 description 3
• ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 3
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
• JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical class CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 0 Cc1n[n](*[Re])cc1 Chemical compound Cc1n[n](*[Re])cc1 0.000 description 3
• RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 3
• 241000711573 Coronaviridae Species 0.000 description 3
• 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 3
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 108010010234 HDL Lipoproteins Proteins 0.000 description 3
• 102000015779 HDL Lipoproteins Human genes 0.000 description 3
• 241000725303 Human immunodeficiency virus Species 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 3
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• GBNJRIQSFJFDII-AATRIKPKSA-N [(e)-2-(4-fluorophenyl)ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(F)C=C1 GBNJRIQSFJFDII-AATRIKPKSA-N 0.000 description 3
• 239000003524 antilipemic agent Substances 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 125000002619 bicyclic group Chemical group 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 150000001720 carbohydrates Chemical class 0.000 description 3
• 235000014633 carbohydrates Nutrition 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• 150000001840 cholesterol esters Chemical class 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
• RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 3
• 239000005516 coenzyme A Substances 0.000 description 3
• 229940093530 coenzyme a Drugs 0.000 description 3
• 230000007423 decrease Effects 0.000 description 3
• 230000007812 deficiency Effects 0.000 description 3
• KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 3
• 230000037213 diet Effects 0.000 description 3
• CFBIOWPDDZPIDP-UHFFFAOYSA-N ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=NC=1C CFBIOWPDDZPIDP-UHFFFAOYSA-N 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• 239000004041 inotropic agent Substances 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
• HPSSZFFAYWBIPY-UHFFFAOYSA-N malvalic acid Chemical compound CCCCCCCCC1=C(CCCCCCC(O)=O)C1 HPSSZFFAYWBIPY-UHFFFAOYSA-N 0.000 description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 description 3
• 150000007530 organic bases Chemical class 0.000 description 3
• 150000003904 phospholipids Chemical class 0.000 description 3
• 230000003389 potentiating effect Effects 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 239000000376 reactant Substances 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 238000005556 structure-activity relationship Methods 0.000 description 3
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 229920002554 vinyl polymer Polymers 0.000 description 3
• CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
• GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
• GLVSPVSJMYQIPJ-UHFFFAOYSA-N 1-(2-bromoethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCBr)=C1 GLVSPVSJMYQIPJ-UHFFFAOYSA-N 0.000 description 2
• FLRUNCJXOVYWDH-UHFFFAOYSA-N 1-(2-bromoethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCBr)C=C1 FLRUNCJXOVYWDH-UHFFFAOYSA-N 0.000 description 2
• OXHPTABOQVHKLN-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1 OXHPTABOQVHKLN-UHFFFAOYSA-N 0.000 description 2
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
• FEKMROKPPFZVRV-UHFFFAOYSA-N 2-(6-iodopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=CN=CC(I)=N1 FEKMROKPPFZVRV-UHFFFAOYSA-N 0.000 description 2
• KXJQNTKWWQQERE-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-(trifluoromethyl)pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=NN(CCC=2C=CC(F)=CC=2)C(C(F)(F)F)=C1 KXJQNTKWWQQERE-UHFFFAOYSA-N 0.000 description 2
• ZWTPMANNJISYQG-UHFFFAOYSA-N 2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(O)=O)=NC=1N(C)CC1=CC=C(F)C=C1 ZWTPMANNJISYQG-UHFFFAOYSA-N 0.000 description 2
• METLDSYYZSNANU-UHFFFAOYSA-N 2-bromo-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound N1=C(Br)SC(C(=O)NCC=2C=NC=CC=2)=C1C METLDSYYZSNANU-UHFFFAOYSA-N 0.000 description 2
• OHTQHZVNZWWYFD-UHFFFAOYSA-N 2-bromo-5-iodopyrazine Chemical compound BrC1=CN=C(I)C=N1 OHTQHZVNZWWYFD-UHFFFAOYSA-N 0.000 description 2
• 125000005999 2-bromoethyl group Chemical group 0.000 description 2
• WSFSJXBURLJOFD-UHFFFAOYSA-N 2-bromopropan-2-ylbenzene Chemical compound CC(C)(Br)C1=CC=CC=C1 WSFSJXBURLJOFD-UHFFFAOYSA-N 0.000 description 2
• NAHHNSMHYCLMON-UHFFFAOYSA-N 2-pyridin-3-ylethanamine Chemical compound NCCC1=CC=CN=C1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 description 2
• CZMRCDWAGMRECN-UHFFFAOYSA-N 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 2
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
• SOPCMQAOTNXTBK-UHFFFAOYSA-N 3-iodo-5-methyl-1h-pyrazole Chemical compound CC1=CC(I)=NN1 SOPCMQAOTNXTBK-UHFFFAOYSA-N 0.000 description 2
• QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 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
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
• 241000710929 Alphavirus Species 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
• 239000004072 C09CA03 - Valsartan Substances 0.000 description 2
• 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 2
• 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
• LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 208000004930 Fatty Liver Diseases 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 102000001267 GSK3 Human genes 0.000 description 2
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 241000711549 Hepacivirus C Species 0.000 description 2
• 208000031226 Hyperlipidaemia Diseases 0.000 description 2
• 208000032382 Ischaemic stroke Diseases 0.000 description 2
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
• 108010007622 LDL Lipoproteins Proteins 0.000 description 2
• 208000021642 Muscular disease Diseases 0.000 description 2
• 201000009623 Myopathy Diseases 0.000 description 2
• PBVIVSVJHKCHHF-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-2-methyl-1,3-thiazole-5-carboxamide Chemical compound FC1=CC=C(CNC(=O)C2=CN=C(S2)C)C=C1 PBVIVSVJHKCHHF-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
• 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 description 2
• 239000005642 Oleic acid Substances 0.000 description 2
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
• 235000021314 Palmitic acid Nutrition 0.000 description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
• 241000315672 SARS coronavirus Species 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 102100033930 Stearoyl-CoA desaturase 5 Human genes 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 241000282898 Sus scrofa Species 0.000 description 2
• 241000534944 Thia Species 0.000 description 2
• 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 2
• 208000036142 Viral infection Diseases 0.000 description 2
• GMGWFDHLFMBIDS-XBXARRHUSA-N [(e)-3-phenylprop-1-enyl]boronic acid Chemical compound OB(O)\C=C\CC1=CC=CC=C1 GMGWFDHLFMBIDS-XBXARRHUSA-N 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 239000000783 alginic acid Substances 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229960001126 alginic acid Drugs 0.000 description 2
• 150000004781 alginic acids Chemical class 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 230000001668 ameliorated effect Effects 0.000 description 2
• 238000010976 amide bond formation reaction Methods 0.000 description 2
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
• 239000000883 anti-obesity agent Substances 0.000 description 2
• 239000003472 antidiabetic agent Substances 0.000 description 2
• 229940030600 antihypertensive agent Drugs 0.000 description 2
• 239000002220 antihypertensive agent Substances 0.000 description 2
• 229940125710 antiobesity agent Drugs 0.000 description 2
• 125000004104 aryloxy group Chemical group 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 229960001948 caffeine Drugs 0.000 description 2
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
• 159000000007 calcium salts Chemical class 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 125000003636 chemical group Chemical group 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 208000019425 cirrhosis of liver Diseases 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
• 238000003745 diagnosis Methods 0.000 description 2
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 2
• 229960005156 digoxin Drugs 0.000 description 2
• LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 206010014599 encephalitis Diseases 0.000 description 2
• PDZIQFWYMDQLGG-UHFFFAOYSA-N ethyl 2-(6-chloropyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2N=C(Cl)C=NC=2)=N1 PDZIQFWYMDQLGG-UHFFFAOYSA-N 0.000 description 2
• SEEIASMNZMRFQX-UHFFFAOYSA-N ethyl 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C2=NN(CCC=3C=CC(F)=CC=3)C(C)=C2)=N1 SEEIASMNZMRFQX-UHFFFAOYSA-N 0.000 description 2
• RLATXPRBWDQWGN-UHFFFAOYSA-N ethyl 2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2N=C(C=NC=2)N(C)CC=2C=CC(F)=CC=2)=N1 RLATXPRBWDQWGN-UHFFFAOYSA-N 0.000 description 2
• WISQBJLUORKXNY-UHFFFAOYSA-N ethyl 4-methyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC=NC=1C WISQBJLUORKXNY-UHFFFAOYSA-N 0.000 description 2
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
• 125000004494 ethyl ester group Chemical group 0.000 description 2
• 208000010706 fatty liver disease Diseases 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 210000003494 hepatocyte Anatomy 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
• 150000004677 hydrates Chemical class 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
• 102000004311 liver X receptors Human genes 0.000 description 2
• 108090000865 liver X receptors Proteins 0.000 description 2
• 244000144972 livestock Species 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 159000000003 magnesium salts Chemical class 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 230000003228 microsomal effect Effects 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
• 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
• 210000003205 muscle Anatomy 0.000 description 2
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
• CZZLTUURMCPIMX-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NCC=2C=CC(F)=CC=2)=C1C CZZLTUURMCPIMX-UHFFFAOYSA-N 0.000 description 2
• HDFQZRAJGYXLEJ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(2-pyridin-2-ylethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3N=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 HDFQZRAJGYXLEJ-UHFFFAOYSA-N 0.000 description 2
• SZVVACUPCFRAEZ-RIYZIHGNSA-N n-benzyl-4-methyl-2-[5-[(e)-3-phenylprop-1-enyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(\C=C\CC=3C=CC=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 SZVVACUPCFRAEZ-RIYZIHGNSA-N 0.000 description 2
• JFTLSBXAKACERR-RIYZIHGNSA-N n-benzyl-4-methyl-2-[6-[(e)-3-phenylprop-1-enyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\CC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 JFTLSBXAKACERR-RIYZIHGNSA-N 0.000 description 2
• XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
• DNXXUUPUQXSUFH-UHFFFAOYSA-N neophyl chloride Chemical compound ClCC(C)(C)C1=CC=CC=C1 DNXXUUPUQXSUFH-UHFFFAOYSA-N 0.000 description 2
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
• 235000001968 nicotinic acid Nutrition 0.000 description 2
• 239000011664 nicotinic acid Substances 0.000 description 2
• 229960003512 nicotinic acid Drugs 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 2
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 2
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
• PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
• 239000001301 oxygen Chemical group 0.000 description 2
• MNBKLUUYKPBKDU-BBECNAHFSA-N palmitoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MNBKLUUYKPBKDU-BBECNAHFSA-N 0.000 description 2
• 229940124531 pharmaceutical excipient Drugs 0.000 description 2
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
• 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 150000003216 pyrazines Chemical class 0.000 description 2
• 150000003217 pyrazoles Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000012047 saturated solution Substances 0.000 description 2
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
• 150000003384 small molecules Chemical class 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
• 235000019345 sodium thiosulphate Nutrition 0.000 description 2
• 238000012453 sprague-dawley rat model Methods 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 231100000240 steatosis hepatitis Toxicity 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• 238000011287 therapeutic dose Methods 0.000 description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 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
• 229960004699 valsartan Drugs 0.000 description 2
• SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 108010017342 very high density lipoproteins Proteins 0.000 description 2
• 230000009385 viral infection Effects 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• 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
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
• BOOOLEGQBVUTKC-NVQSDHBMSA-N (2e,4e)-3-methyl-5-[(1s,2s)-2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\[C@@H]1C[C@]1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 BOOOLEGQBVUTKC-NVQSDHBMSA-N 0.000 description 1
• FONCZICQWCUXEB-RUZDIDTESA-N (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C(Br)=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 FONCZICQWCUXEB-RUZDIDTESA-N 0.000 description 1
• LPUDGHQMOAHMMF-JBACZVJFSA-N (2s)-2-[[[(2s)-6-amino-2-(methanesulfonamido)hexanoyl]amino]methyl]-3-[1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl]cyclopentyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C(=O)C1(C[C@@H](CNC(=O)[C@H](CCCCN)NS(=O)(=O)C)C(O)=O)CCCC1 LPUDGHQMOAHMMF-JBACZVJFSA-N 0.000 description 1
• BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• ZGGHKIMDNBDHJB-RPQBTBOMSA-M (3S,5R)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@H](O)C[C@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-RPQBTBOMSA-M 0.000 description 1
• VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 description 1
• METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-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
• JXSPKRUNMHMICQ-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-fluorobenzene Chemical compound FC1=CC=C(OCCBr)C=C1 JXSPKRUNMHMICQ-UHFFFAOYSA-N 0.000 description 1
• FIFKRPFWLHBMHL-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC(OC)=C1 FIFKRPFWLHBMHL-UHFFFAOYSA-N 0.000 description 1
• AIJFPNKGGAPZFJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(OC)C=C1 AIJFPNKGGAPZFJ-UHFFFAOYSA-N 0.000 description 1
• KVSVNRFSKRFPIL-UHFFFAOYSA-N 1-(bromomethyl)-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(CBr)=C1 KVSVNRFSKRFPIL-UHFFFAOYSA-N 0.000 description 1
• MYYYZNVAUZVXBO-UHFFFAOYSA-N 1-(bromomethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CBr)=C1 MYYYZNVAUZVXBO-UHFFFAOYSA-N 0.000 description 1
• LZIYAIRGDHSVED-UHFFFAOYSA-N 1-(bromomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(CBr)=C1 LZIYAIRGDHSVED-UHFFFAOYSA-N 0.000 description 1
• SCBZBMXPJYMXRC-UHFFFAOYSA-N 1-(bromomethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CBr)=C1 SCBZBMXPJYMXRC-UHFFFAOYSA-N 0.000 description 1
• JDNPUJCKXLOHOW-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(CBr)C=C1 JDNPUJCKXLOHOW-UHFFFAOYSA-N 0.000 description 1
• IKSNDOVDVVPSMA-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CBr)C=C1 IKSNDOVDVVPSMA-UHFFFAOYSA-N 0.000 description 1
• UFCSSWZQROEFBZ-UHFFFAOYSA-N 1-(bromomethyl)-4-chloro-2-fluorobenzene Chemical compound FC1=CC(Cl)=CC=C1CBr UFCSSWZQROEFBZ-UHFFFAOYSA-N 0.000 description 1
• YYPPFEKHXPADAV-UHFFFAOYSA-N 1-(bromomethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CBr)C=C1 YYPPFEKHXPADAV-UHFFFAOYSA-N 0.000 description 1
• NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
• HGKPAXHJTMHWAH-UHFFFAOYSA-N 1-(bromomethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CBr)C=C1 HGKPAXHJTMHWAH-UHFFFAOYSA-N 0.000 description 1
• QZNQSIHCDAGZIA-UHFFFAOYSA-N 1-(bromomethyl)-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(CBr)C=C1 QZNQSIHCDAGZIA-UHFFFAOYSA-N 0.000 description 1
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
• NOUAEJFAVOHNSY-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]-1,2,4-triazole Chemical compound C1=CC(CBr)=CC=C1N1N=CN=C1 NOUAEJFAVOHNSY-UHFFFAOYSA-N 0.000 description 1
• PHNRBSHOFSWNII-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]pyrazole Chemical compound C1=CC(CBr)=CC=C1N1N=CC=C1 PHNRBSHOFSWNII-UHFFFAOYSA-N 0.000 description 1
• ADVNJHFDDUGRHL-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]pyrrole Chemical compound C1=CC(CBr)=CC=C1N1C=CC=C1 ADVNJHFDDUGRHL-UHFFFAOYSA-N 0.000 description 1
• OZLPONSQVQLJSI-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(OC(F)F)C=C1 OZLPONSQVQLJSI-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 1
• SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
• RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
• 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 description 1
• FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
• VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
• ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
• LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical compound ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
• HWUZQODGTCVVBO-UHFFFAOYSA-N 2-(4-methoxyphenoxy)-n-methylethanamine Chemical compound CNCCOC1=CC=C(OC)C=C1 HWUZQODGTCVVBO-UHFFFAOYSA-N 0.000 description 1
• LMCVPMMOAPDQOG-UHFFFAOYSA-N 2-[1-(2-aminoethyl)pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=NN(CCN)C=C1 LMCVPMMOAPDQOG-UHFFFAOYSA-N 0.000 description 1
• LKTKBYUFFKUWHX-QPJJXVBHSA-N 2-[6-[(E)-2-(4-fluorophenyl)ethenyl]pyrazin-2-yl]-4-methyl-1,3-thiazole Chemical compound CC1=CSC(=N1)C2=NC(=CN=C2)/C=C/C3=CC=C(C=C3)F LKTKBYUFFKUWHX-QPJJXVBHSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• 125000006016 2-bromoethoxy group Chemical group 0.000 description 1
• RIYFONBSYWACFF-UHFFFAOYSA-N 2-bromoethylcyclopropane Chemical compound BrCCC1CC1 RIYFONBSYWACFF-UHFFFAOYSA-N 0.000 description 1
• OBTWHVVHJBRISW-UHFFFAOYSA-N 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=CC(Cl)=N1 OBTWHVVHJBRISW-UHFFFAOYSA-N 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 description 1
• 125000006088 2-oxoazepinyl group Chemical group 0.000 description 1
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• NTLAICDKHHQUGC-UHFFFAOYSA-N 3-(2-bromoethyl)-1h-indole Chemical compound C1=CC=C2C(CCBr)=CNC2=C1 NTLAICDKHHQUGC-UHFFFAOYSA-N 0.000 description 1
• GLZRMVTXAKDQMC-UHFFFAOYSA-N 3-(2-phenylethyl)pyrrolidine Chemical compound C1CNCC1CCC1=CC=CC=C1 GLZRMVTXAKDQMC-UHFFFAOYSA-N 0.000 description 1
• CVKOOKPNCVYHNY-UHFFFAOYSA-N 3-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC(C#N)=C1 CVKOOKPNCVYHNY-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
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
• UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 1
• DYYVTFCYVZEQDG-UHFFFAOYSA-N 4-(2-bromoethyl)phenol Chemical compound OC1=CC=C(CCBr)C=C1 DYYVTFCYVZEQDG-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 1
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 1
• WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
• CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
• ZGWGSEUMABQEMD-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=CSC=1C(O)=O ZGWGSEUMABQEMD-UHFFFAOYSA-N 0.000 description 1
• FCNBTSRANHBJAG-UHFFFAOYSA-N 4-methyl-2-[1-(2-methyl-2-phenylpropyl)pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC(C)(C)C=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 FCNBTSRANHBJAG-UHFFFAOYSA-N 0.000 description 1
• BSXIGERZJMTVML-UHFFFAOYSA-N 4-methyl-2-[5-methyl-1-[[4-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxylic acid Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(O)=O)=NN1CC1=CC=C(C(F)(F)F)C=C1 BSXIGERZJMTVML-UHFFFAOYSA-N 0.000 description 1
• 125000005986 4-piperidonyl group Chemical group 0.000 description 1
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
• KRRTXVSBTPCDOS-UHFFFAOYSA-N 5-bromopyrazin-2-amine Chemical compound NC1=CN=C(Br)C=N1 KRRTXVSBTPCDOS-UHFFFAOYSA-N 0.000 description 1
• XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
• RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• IYDVFMFKIKZKEK-UHFFFAOYSA-N 8-nonylsulfanyloctanoic acid Chemical compound CCCCCCCCCSCCCCCCCC(O)=O IYDVFMFKIKZKEK-UHFFFAOYSA-N 0.000 description 1
• 102100034542 Acyl-CoA (8-3)-desaturase Human genes 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• 241000234282 Allium Species 0.000 description 1
• 208000023434 Alpers-Huttenlocher syndrome Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• 206010002091 Anaesthesia Diseases 0.000 description 1
• 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
• 108010071619 Apolipoproteins Proteins 0.000 description 1
• 102000007592 Apolipoproteins Human genes 0.000 description 1
• 102000013918 Apolipoproteins E Human genes 0.000 description 1
• 108010025628 Apolipoproteins E Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241001533362 Astroviridae Species 0.000 description 1
• 206010003591 Ataxia Diseases 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• 241000271566 Aves Species 0.000 description 1
• XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
• 208000020925 Bipolar disease Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• 241001503592 Bovine calicivirus Species 0.000 description 1
• 241000711443 Bovine coronavirus Species 0.000 description 1
• 241000710780 Bovine viral diarrhea virus 1 Species 0.000 description 1
• BWBXHTORZSRZBH-UHFFFAOYSA-N BrC=1SC(=C(N1)C)C(=O)O.BrC=1SC(=C(N1)C)C(=O)NCC1=CC=C(C=C1)F Chemical compound BrC=1SC(=C(N1)C)C(=O)O.BrC=1SC(=C(N1)C)C(=O)NCC1=CC=C(C=C1)F BWBXHTORZSRZBH-UHFFFAOYSA-N 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 239000002083 C09CA01 - Losartan Substances 0.000 description 1
• 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
• 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
• 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
• 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
• IRYIKJRCUFLLMY-ZDUSSCGKSA-N CC1=C(SC(=N1)C2=NN(C=C2)C[C@@H](C3=CC=C(C=C3)F)O)C(=O)O Chemical compound CC1=C(SC(=N1)C2=NN(C=C2)C[C@@H](C3=CC=C(C=C3)F)O)C(=O)O IRYIKJRCUFLLMY-ZDUSSCGKSA-N 0.000 description 1
• ZJUFRFPKTQJEOS-XOHWUJONSA-N CCC/N=C(/C)\C=N/CC Chemical compound CCC/N=C(/C)\C=N/CC ZJUFRFPKTQJEOS-XOHWUJONSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 229940127291 Calcium channel antagonist Drugs 0.000 description 1
• 241000714198 Caliciviridae Species 0.000 description 1
• LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• 241000711506 Canine coronavirus Species 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
• 208000005623 Carcinogenesis Diseases 0.000 description 1
• 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 1
• 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 1
• 102100027943 Carnitine O-palmitoyltransferase 1, liver isoform Human genes 0.000 description 1
• 101710120614 Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 description 1
• 101710108984 Carnitine O-palmitoyltransferase 1, muscle isoform Proteins 0.000 description 1
• 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 description 1
• 206010050215 Carnitine palmitoyltransferase deficiency Diseases 0.000 description 1
• 239000005973 Carvone Substances 0.000 description 1
• QNJFJXHJTFSQFV-UHFFFAOYSA-N Cc1c(C(NCc2cccnc2)=O)[s]c(-c2nc(N(C)CCOc(cc3)ccc3F)cnc2)n1 Chemical compound Cc1c(C(NCc2cccnc2)=O)[s]c(-c2nc(N(C)CCOc(cc3)ccc3F)cnc2)n1 QNJFJXHJTFSQFV-UHFFFAOYSA-N 0.000 description 1
• CAWHJQAVHZEVTJ-UHFFFAOYSA-N Cc1nccnc1 Chemical compound Cc1nccnc1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
• 208000037404 Central European encephalitis Diseases 0.000 description 1
• 206010008027 Cerebellar atrophy Diseases 0.000 description 1
• 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 description 1
• 241001502567 Chikungunya virus Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 206010008631 Cholera Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 241000709687 Coxsackievirus Species 0.000 description 1
• 241000699800 Cricetinae Species 0.000 description 1
• 201000003883 Cystic fibrosis Diseases 0.000 description 1
• 102100031655 Cytochrome b5 Human genes 0.000 description 1
• 102100033149 Cytochrome b5 reductase 4 Human genes 0.000 description 1
• 108030005700 Cytochrome-b5 reductases Proteins 0.000 description 1
• 108010007167 Cytochromes b5 Proteins 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 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-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• 206010011985 Decubitus ulcer Diseases 0.000 description 1
• 108010073542 Delta-5 Fatty Acid Desaturase Proteins 0.000 description 1
• 241000710829 Dengue virus group Species 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 description 1
• JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 1
• 201000010374 Down Syndrome Diseases 0.000 description 1
• 206010072268 Drug-induced liver injury Diseases 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 239000004097 EU approved flavor enhancer Substances 0.000 description 1
• 241000710945 Eastern equine encephalitis virus Species 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• 206010014596 Encephalitis Japanese B Diseases 0.000 description 1
• 241000710188 Encephalomyocarditis virus Species 0.000 description 1
• 102000005593 Endopeptidases Human genes 0.000 description 1
• 108010059378 Endopeptidases Proteins 0.000 description 1
• 241000709661 Enterovirus Species 0.000 description 1
• 241000991587 Enterovirus C Species 0.000 description 1
• 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• 102000015303 Fatty Acid Synthases Human genes 0.000 description 1
• 108010039731 Fatty Acid Synthases Proteins 0.000 description 1
• 102000009114 Fatty acid desaturases Human genes 0.000 description 1
• 241000711475 Feline infectious peritonitis virus Species 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• 241000710781 Flaviviridae Species 0.000 description 1
• 241000710831 Flavivirus Species 0.000 description 1
• 241000531123 GB virus C Species 0.000 description 1
• DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
• 208000005577 Gastroenteritis Diseases 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
• 208000002705 Glucose Intolerance Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
• 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
• 108010023302 HDL Cholesterol Proteins 0.000 description 1
• 208000036066 Hemophagocytic Lymphohistiocytosis Diseases 0.000 description 1
• 241000700721 Hepatitis B virus Species 0.000 description 1
• 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
• 241000709721 Hepatovirus A Species 0.000 description 1
• 208000033981 Hereditary haemochromatosis Diseases 0.000 description 1
• 206010063491 Herpes zoster oticus Diseases 0.000 description 1
• 101100309604 Homo sapiens SCD5 gene Proteins 0.000 description 1
• 101000639987 Homo sapiens Stearoyl-CoA desaturase 5 Proteins 0.000 description 1
• 244000309467 Human Coronavirus Species 0.000 description 1
• 241001479210 Human astrovirus Species 0.000 description 1
• 241001428935 Human coronavirus OC43 Species 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 208000001021 Hyperlipoproteinemia Type I Diseases 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 241000711450 Infectious bronchitis virus Species 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 206010065973 Iron Overload Diseases 0.000 description 1
• 102000008133 Iron-Binding Proteins Human genes 0.000 description 1
• 108010035210 Iron-Binding Proteins Proteins 0.000 description 1
• 241000726306 Irus Species 0.000 description 1
• 241000764238 Isis Species 0.000 description 1
• 201000005807 Japanese encephalitis Diseases 0.000 description 1
• 241000710767 Kumlinge virus Species 0.000 description 1
• PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• 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
• 108010028554 LDL Cholesterol Proteins 0.000 description 1
• 238000008214 LDL Cholesterol Methods 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
• 241000710770 Langat virus Species 0.000 description 1
• 239000005639 Lauric acid Substances 0.000 description 1
• 208000009829 Lewy Body Disease Diseases 0.000 description 1
• 201000002832 Lewy body dementia Diseases 0.000 description 1
• 108010007859 Lisinopril Proteins 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 241000608292 Mayaro virus Species 0.000 description 1
• 241000710185 Mengo virus Species 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
• 241000711466 Murine hepatitis virus Species 0.000 description 1
• 241000710908 Murray Valley encephalitis virus Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• 101100309601 Mus musculus Scd3 gene Proteins 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 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
• ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
• 208000012902 Nervous system disease Diseases 0.000 description 1
• 208000025966 Neurological disease Diseases 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 241000714209 Norwalk virus Species 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 208000022873 Ocular disease Diseases 0.000 description 1
• 241000725177 Omsk hemorrhagic fever virus Species 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 102000004316 Oxidoreductases Human genes 0.000 description 1
• 108090000854 Oxidoreductases Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 102000000536 PPAR gamma Human genes 0.000 description 1
• 108010016731 PPAR gamma Proteins 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 208000018262 Peripheral vascular disease Diseases 0.000 description 1
• 241000710778 Pestivirus Species 0.000 description 1
• 241000709664 Picornaviridae Species 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 241001135549 Porcine epidemic diarrhea virus Species 0.000 description 1
• 241000156302 Porcine hemagglutinating encephalomyelitis virus Species 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 241000710078 Potyvirus Species 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• 206010036618 Premenstrual syndrome Diseases 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-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
• 241000903330 Rabbit coronavirus Species 0.000 description 1
• 241001428933 Rat coronavirus Species 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• 208000006289 Rett Syndrome Diseases 0.000 description 1
• 241001147432 Rio Bravo virus group Species 0.000 description 1
• 241000710942 Ross River virus Species 0.000 description 1
• 241000710799 Rubella virus Species 0.000 description 1
• SIARJEKBADXQJG-UDVGOQGCSA-N S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 9,10-ditritiooctadecanethioate Chemical compound C(CCCCCCCC(C(CCCCCCCC)[3H])[3H])(=O)SCCNC(CCNC([C@@H](C(COP(OP(OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC1=2)O)OP(=O)(O)O)(=O)O)(=O)O)(C)C)O)=O)=O SIARJEKBADXQJG-UDVGOQGCSA-N 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
• 101100101423 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBI4 gene Proteins 0.000 description 1
• 101150042597 Scd2 gene Proteins 0.000 description 1
• 241000710961 Semliki Forest virus Species 0.000 description 1
• 241000008910 Severe acute respiratory syndrome-related coronavirus Species 0.000 description 1
• 241000710960 Sindbis virus Species 0.000 description 1
• 102100037202 Sodium/myo-inositol cotransporter 2 Human genes 0.000 description 1
• 101710090560 Sodium/myo-inositol cotransporter 2 Proteins 0.000 description 1
• 241000256248 Spodoptera Species 0.000 description 1
• 241000710888 St. Louis encephalitis virus Species 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 239000004809 Teflon Substances 0.000 description 1
• 229920006362 Teflon® Polymers 0.000 description 1
• 229940123464 Thiazolidinedione Drugs 0.000 description 1
• 208000004006 Tick-borne encephalitis Diseases 0.000 description 1
• 241000710924 Togaviridae Species 0.000 description 1
• NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 241000711508 Turkey coronavirus Species 0.000 description 1
• 241000907508 Uganda S virus Species 0.000 description 1
• 239000003875 Wang resin Substances 0.000 description 1
• 239000004164 Wax ester Substances 0.000 description 1
• 241000710886 West Nile virus Species 0.000 description 1
• 241000710951 Western equine encephalitis virus Species 0.000 description 1
• 241000710772 Yellow fever virus Species 0.000 description 1
• 241000120645 Yellow fever virus group Species 0.000 description 1
• BBNQFBHQOPZKTI-AATRIKPKSA-N [(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(C(F)(F)F)C=C1 BBNQFBHQOPZKTI-AATRIKPKSA-N 0.000 description 1
• VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
• NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
• 230000003187 abdominal effect Effects 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 229960002632 acarbose Drugs 0.000 description 1
• XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• 229960002122 acebutolol Drugs 0.000 description 1
• GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 229960004308 acetylcysteine Drugs 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• 229960000250 adipic acid Drugs 0.000 description 1
• 210000001789 adipocyte Anatomy 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 235000010419 agar Nutrition 0.000 description 1
• 208000002353 alcoholic hepatitis Diseases 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229960004909 aminosalicylic acid Drugs 0.000 description 1
• HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
• 229960000528 amlodipine Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000037005 anaesthesia Effects 0.000 description 1
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
• JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
• 230000003178 anti-diabetic effect Effects 0.000 description 1
• 229940125708 antidiabetic agent Drugs 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229960005261 aspartic acid Drugs 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 239000000305 astragalus gummifer gum Substances 0.000 description 1
• 244000309743 astrovirus Species 0.000 description 1
• 229960002274 atenolol Drugs 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 229960004530 benazepril Drugs 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• YINMBLWEHNCLFF-UHFFFAOYSA-N benzenesulfonic acid;benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 YINMBLWEHNCLFF-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 description 1
• 229960003665 bepridil Drugs 0.000 description 1
• 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
• 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• 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 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• UUQMNUMQCIQDMZ-UHFFFAOYSA-N betahistine Chemical compound CNCCC1=CC=CC=N1 UUQMNUMQCIQDMZ-UHFFFAOYSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 229960004324 betaxolol Drugs 0.000 description 1
• NWIUTZDMDHAVTP-UHFFFAOYSA-N betaxolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-UHFFFAOYSA-N 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229960002781 bisoprolol Drugs 0.000 description 1
• VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 238000006664 bond formation reaction Methods 0.000 description 1
• 229940098773 bovine serum albumin Drugs 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 125000005998 bromoethyl group Chemical group 0.000 description 1
• 239000007853 buffer solution 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
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000000480 calcium channel blocker Substances 0.000 description 1
• LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 208000035269 cancer or benign tumor Diseases 0.000 description 1
• 229960000932 candesartan Drugs 0.000 description 1
• SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
• KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
• 229960000830 captopril Drugs 0.000 description 1
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 231100000504 carcinogenesis Toxicity 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 208000026106 cerebrovascular disease Diseases 0.000 description 1
• 229960005110 cerivastatin Drugs 0.000 description 1
• SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
• GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=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](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)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(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000012069 chiral reagent Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 230000007882 cirrhosis Effects 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 208000010877 cognitive disease Diseases 0.000 description 1
• 230000000052 comparative effect Effects 0.000 description 1
• 230000006957 competitive inhibition Effects 0.000 description 1
• 229940108924 conjugated linoleic acid Drugs 0.000 description 1
• 238000011109 contamination Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• 208000029078 coronary artery disease Diseases 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
• 229950003040 dalvastatin Drugs 0.000 description 1
• 229960002887 deanol Drugs 0.000 description 1
• 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 230000000593 degrading effect Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 230000000378 dietary effect Effects 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 150000004683 dihydrates Chemical class 0.000 description 1
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
• 229960004166 diltiazem Drugs 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 125000005879 dioxolanyl group Chemical group 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 231100000676 disease causative agent Toxicity 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 229960001089 dobutamine Drugs 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 201000008865 drug-induced hepatitis Diseases 0.000 description 1
• 241001493065 dsRNA viruses Species 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 229960000873 enalapril Drugs 0.000 description 1
• GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
• 229960004563 eprosartan Drugs 0.000 description 1
• 201000008220 erythropoietic protoporphyria Diseases 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 description 1
• 229960003199 etacrynic acid Drugs 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
• 239000012259 ether extract Substances 0.000 description 1
• TWQLMAJROCNXEA-UHFFFAOYSA-N ethyl 4-(bromomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CBr)C=C1 TWQLMAJROCNXEA-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 229960001519 exenatide Drugs 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 208000029944 familial hemophagocytic lymphohistiocytosis type 1 Diseases 0.000 description 1
• 235000019197 fats Nutrition 0.000 description 1
• 230000004129 fatty acid metabolism Effects 0.000 description 1
• 229960003580 felodipine Drugs 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 235000019264 food flavour enhancer Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 150000004675 formic acid derivatives Chemical class 0.000 description 1
• 229960002490 fosinopril Drugs 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000003844 furanonyl group Chemical group 0.000 description 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
• 229960003883 furosemide Drugs 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 201000011349 geniculate herpes zoster Diseases 0.000 description 1
• 229960005219 gentisic acid Drugs 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
• 229960001381 glipizide Drugs 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000000262 haloalkenyl group Chemical group 0.000 description 1
• BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
• 229960003132 halothane Drugs 0.000 description 1
• 208000019622 heart disease Diseases 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 201000010284 hepatitis E Diseases 0.000 description 1
• TZTFFIFDGZOKCS-UHFFFAOYSA-N heptadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCCCC(O)=S TZTFFIFDGZOKCS-UHFFFAOYSA-N 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• 238000004128 high performance liquid chromatography 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
• 229960002885 histidine Drugs 0.000 description 1
• 238000000265 homogenisation Methods 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
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 1
• 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
• 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000002458 infectious effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 238000012739 integrated shape imaging system Methods 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229960002198 irbesartan Drugs 0.000 description 1
• YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 159000000014 iron salts Chemical class 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000000644 isotonic solution Substances 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 230000009191 jumping Effects 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940099563 lactobionic acid Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 239000010410 layer Substances 0.000 description 1
• 208000036546 leukodystrophy Diseases 0.000 description 1
• 238000011694 lewis rat Methods 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 230000004322 lipid homeostasis Effects 0.000 description 1
• 230000008604 lipoprotein metabolism Effects 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 229960002394 lisinopril Drugs 0.000 description 1
• CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
• 229910003002 lithium salt Inorganic materials 0.000 description 1
• 159000000002 lithium salts Chemical class 0.000 description 1
• 239000002171 loop diuretic Substances 0.000 description 1
• 229960004773 losartan Drugs 0.000 description 1
• KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
• 229960004844 lovastatin Drugs 0.000 description 1
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
• 235000015263 low fat diet Nutrition 0.000 description 1
• 235000004213 low-fat Nutrition 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 150000002696 manganese Chemical class 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 235000013622 meat product Nutrition 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 229950004994 meglitinide Drugs 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
• 229960003105 metformin Drugs 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical class COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
• 229960002237 metoprolol Drugs 0.000 description 1
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
• 229950009116 mevastatin Drugs 0.000 description 1
• AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
• BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
• 208000027061 mild cognitive impairment Diseases 0.000 description 1
• PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 1
• 229960003574 milrinone Drugs 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 210000003470 mitochondria Anatomy 0.000 description 1
• 201000011540 mitochondrial DNA depletion syndrome 4a Diseases 0.000 description 1
• 230000002438 mitochondrial effect Effects 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 229960005170 moexipril Drugs 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 238000010172 mouse model Methods 0.000 description 1
• 210000003097 mucus Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• QOMQZGGZBVHJBD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-(5-methyl-1h-pyrazol-3-yl)-1,3-thiazole-5-carboxamide Chemical compound N1N=C(C)C=C1C1=NC(C)=C(C(=O)NCC=2C=CC(F)=CC=2)S1 QOMQZGGZBVHJBD-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• JNHZPXFARRJZQR-UHFFFAOYSA-N n-ethylpyridin-3-amine Chemical compound CCNC1=CC=CN=C1 JNHZPXFARRJZQR-UHFFFAOYSA-N 0.000 description 1
• MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
• MCSAQVGDZLPTBS-UHFFFAOYSA-N n-methyl-1-pyridin-3-ylmethanamine Chemical compound CNCC1=CC=CN=C1 MCSAQVGDZLPTBS-UHFFFAOYSA-N 0.000 description 1
• DNBWGFKLIBQQSL-UHFFFAOYSA-N n-methyl-1-pyridin-4-ylmethanamine Chemical compound CNCC1=CC=NC=C1 DNBWGFKLIBQQSL-UHFFFAOYSA-N 0.000 description 1
• MLHBZVFOTDJTPK-UHFFFAOYSA-N n-methyl-3-phenylpropan-1-amine Chemical compound CNCCCC1=CC=CC=C1 MLHBZVFOTDJTPK-UHFFFAOYSA-N 0.000 description 1
• DBGFNLVRAFYZBI-UHFFFAOYSA-N n-methylpyridin-3-amine Chemical compound CNC1=CC=CN=C1 DBGFNLVRAFYZBI-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
• 229960004255 nadolol Drugs 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
• 229960000698 nateglinide Drugs 0.000 description 1
• PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
• 230000004770 neurodegeneration Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 229960001783 nicardipine Drugs 0.000 description 1
• BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
• 229960001597 nifedipine Drugs 0.000 description 1
• 229960000715 nimodipine Drugs 0.000 description 1
• 229960000227 nisoldipine Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 235000021590 normal diet Nutrition 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
• 229960002446 octanoic acid Drugs 0.000 description 1
• 229960002969 oleic acid Drugs 0.000 description 1
• XDUHQPOXLUAVEE-BPMMELMSSA-N oleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDUHQPOXLUAVEE-BPMMELMSSA-N 0.000 description 1
• LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
• 229950000973 omapatrilat Drugs 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
• 229960001243 orlistat Drugs 0.000 description 1
• 229960005010 orotic acid Drugs 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 229940116315 oxalic acid Drugs 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 150000002924 oxiranes Chemical class 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229940098695 palmitic acid Drugs 0.000 description 1
• QBYOCCWNZAOZTL-MDMKAECGSA-N palmitoleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QBYOCCWNZAOZTL-MDMKAECGSA-N 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 229960002582 perindopril Drugs 0.000 description 1
• IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229960002797 pitavastatin Drugs 0.000 description 1
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 239000002952 polymeric resin Substances 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000008057 potassium phosphate buffer Substances 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• 201000009104 prediabetes syndrome Diseases 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 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
• NPUSXSOBPNHOPH-UHFFFAOYSA-N propan-2-yl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-4,7-dihydrofuro[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N(CC)C(COC2=O)=C2C1C1=CC=CC=C1Cl NPUSXSOBPNHOPH-UHFFFAOYSA-N 0.000 description 1
• 125000006410 propenylene group Chemical group 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 229960003712 propranolol Drugs 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 208000020016 psychiatric disease Diseases 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 229960001455 quinapril Drugs 0.000 description 1
• JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 229960003401 ramipril Drugs 0.000 description 1
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 230000010076 replication Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 230000006965 reversible inhibition Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 229960000672 rosuvastatin Drugs 0.000 description 1
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229950001780 sampatrilat Drugs 0.000 description 1
• 150000004671 saturated fatty acids Chemical class 0.000 description 1
• 201000000980 schizophrenia Diseases 0.000 description 1
• 238000007423 screening assay Methods 0.000 description 1
• 229940116353 sebacic acid Drugs 0.000 description 1
• 210000002374 sebum Anatomy 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 239000008137 solubility enhancer Substances 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
• 229960002370 sotalol Drugs 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 229960004274 stearic acid Drugs 0.000 description 1
• 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• PQRKPYLNZGDCFH-UHFFFAOYSA-N sterculic acid Chemical compound CCCCCCCCC1=C(CCCCCCCC(O)=O)C1 PQRKPYLNZGDCFH-UHFFFAOYSA-N 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 229920003002 synthetic resin Polymers 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 229960001367 tartaric acid Drugs 0.000 description 1
• 229960005187 telmisartan Drugs 0.000 description 1
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
• 150000004685 tetrahydrates Chemical class 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 231100001274 therapeutic index Toxicity 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 150000001467 thiazolidinediones Chemical class 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 229960004605 timolol Drugs 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229960005461 torasemide Drugs 0.000 description 1
• 231100000816 toxic dose Toxicity 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 229960002051 trandolapril Drugs 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 230000001052 transient effect Effects 0.000 description 1
• 230000032258 transport Effects 0.000 description 1
• 125000004665 trialkylsilyl group Chemical group 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 150000004684 trihydrates Chemical class 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 125000005455 trithianyl group Chemical group 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
• 229960001641 troglitazone Drugs 0.000 description 1
• GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
• 229960004418 trolamine Drugs 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 229960002703 undecylenic acid Drugs 0.000 description 1
• 238000011144 upstream manufacturing Methods 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 235000019386 wax ester Nutrition 0.000 description 1
• 229940051021 yellow-fever virus Drugs 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1