JP4234431B2 - ヒトペルオキシソーム増殖因子活性化受容体の活性化剤としてのチアゾール及びオキサゾール誘導体 - Google Patents

Info

Publication number

JP4234431B2

JP4234431B2 JP2002559400A JP2002559400A JP4234431B2 JP 4234431 B2 JP4234431 B2 JP 4234431B2 JP 2002559400 A JP2002559400 A JP 2002559400A JP 2002559400 A JP2002559400 A JP 2002559400A JP 4234431 B2 JP4234431 B2 JP 4234431B2

Authority

JP

Japan

Prior art keywords

methyl

phenyl

trifluoromethyl

sulfanyl

thiazol

Prior art date

2000-12-20

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.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title abstract description 20
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title abstract description 20
• 239000012190 activator Substances 0.000 title description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
• 150000007978 oxazole derivatives Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 115
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
• 238000011282 treatment Methods 0.000 claims abstract description 12
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 4
• -1 perfluoro Chemical group 0.000 claims description 143
• 239000000460 chlorine Substances 0.000 claims description 74
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 17
• 239000000556 agonist Substances 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• BCTQCGIKVZFCLS-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 BCTQCGIKVZFCLS-UHFFFAOYSA-N 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 7
• UTNZGBCCVVRBIW-UHFFFAOYSA-N 2-[4-[[4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1CC1=C(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 UTNZGBCCVVRBIW-UHFFFAOYSA-N 0.000 claims description 6
• JMZLZYWSHIVYQV-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(OC(F)(F)F)=CC=2)=C1 JMZLZYWSHIVYQV-UHFFFAOYSA-N 0.000 claims description 6
• 208000024891 symptom Diseases 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• BMNBRVGQZHPKHG-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2N=CC=CN=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BMNBRVGQZHPKHG-UHFFFAOYSA-N 0.000 claims description 5
• XGTZMXYQJTZSCP-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(4-propan-2-yloxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 XGTZMXYQJTZSCP-UHFFFAOYSA-N 0.000 claims description 5
• GWTXBGBDOIAZPQ-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 GWTXBGBDOIAZPQ-UHFFFAOYSA-N 0.000 claims description 5
• LPOBICWXXUKVPK-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)CC1 LPOBICWXXUKVPK-UHFFFAOYSA-N 0.000 claims description 5
• FVVACHCAVRTOQE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC2=CSC=C2)=C1 FVVACHCAVRTOQE-UHFFFAOYSA-N 0.000 claims description 5
• MVAGRNCLYNRSIU-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[(4-pyrazin-2-ylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2N=CC=NC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 MVAGRNCLYNRSIU-UHFFFAOYSA-N 0.000 claims description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
• CESIUPFUCGHEPP-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(OC)=CC=2)=C1 CESIUPFUCGHEPP-UHFFFAOYSA-N 0.000 claims description 4
• UQFYXXUDIYNDQH-UHFFFAOYSA-N 2-[4-[[4-[(4-tert-butylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(=CC=2)C(C)(C)C)=C1 UQFYXXUDIYNDQH-UHFFFAOYSA-N 0.000 claims description 4
• XEFHJCXVIGBXQV-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-4-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(=CC=2)C(F)(F)F)=C1 XEFHJCXVIGBXQV-UHFFFAOYSA-N 0.000 claims description 4
• NDWIOURNMFSYDN-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[4-[(4-methylsulfanylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(SC)=CC=C1CC1=C(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 NDWIOURNMFSYDN-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• 206010022489 Insulin Resistance Diseases 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• HTMZJWVLXDBHJQ-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(OC)=CC=2)=C1 HTMZJWVLXDBHJQ-UHFFFAOYSA-N 0.000 claims description 3
• SKLCSSUNBRUUHI-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(2-phenylethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COCCC=2C=CC=CC=2)=C1 SKLCSSUNBRUUHI-UHFFFAOYSA-N 0.000 claims description 3
• AMWLERATXBSGQY-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=CC=CC=2)=C1 AMWLERATXBSGQY-UHFFFAOYSA-N 0.000 claims description 3
• UPUYRFKRWFCGHL-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(3-phenylpropyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CCCC=2C=CC=CC=2)=C1 UPUYRFKRWFCGHL-UHFFFAOYSA-N 0.000 claims description 3
• FHWSXRDTCDHVOY-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(thiophen-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2SC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FHWSXRDTCDHVOY-UHFFFAOYSA-N 0.000 claims description 3
• JYYLSMURAYLXRE-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC2=CSC=C2)=C1 JYYLSMURAYLXRE-UHFFFAOYSA-N 0.000 claims description 3
• KXHADIZVDLVLAB-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC2=CSC=C2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KXHADIZVDLVLAB-UHFFFAOYSA-N 0.000 claims description 3
• DIFNTPAWTGWFIQ-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-methylthiophen-2-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1=CSC(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)=C1 DIFNTPAWTGWFIQ-UHFFFAOYSA-N 0.000 claims description 3
• GQDOHCPKHIILRT-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-phenylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 GQDOHCPKHIILRT-UHFFFAOYSA-N 0.000 claims description 3
• KRCKWKMHZJNRMT-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-pyrazin-2-ylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2N=CC=NC=2)=C1 KRCKWKMHZJNRMT-UHFFFAOYSA-N 0.000 claims description 3
• GQSJMGIYTCKJFG-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-thiophen-3-ylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(=CC=2)C2=CSC=C2)=C1 GQSJMGIYTCKJFG-UHFFFAOYSA-N 0.000 claims description 3
• LKFODONVGVFCOU-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OCC(O)=O)=CC=3)=CC=2)=N1 LKFODONVGVFCOU-UHFFFAOYSA-N 0.000 claims description 3
• FTUDUVKEOPPRET-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(F)=CC=2)CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 FTUDUVKEOPPRET-UHFFFAOYSA-N 0.000 claims description 3
• QUMUTAZYSUGGAM-UHFFFAOYSA-N 2-[4-[[4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1CC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QUMUTAZYSUGGAM-UHFFFAOYSA-N 0.000 claims description 3
• ZFXOVULAKVMWEM-UHFFFAOYSA-N 2-[4-[[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)CC1 ZFXOVULAKVMWEM-UHFFFAOYSA-N 0.000 claims description 3
• NAVWFKOQMRRKDH-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OCC(O)=O)=CC=3)CC2)=C1 NAVWFKOQMRRKDH-UHFFFAOYSA-N 0.000 claims description 3
• QDJZVWSCXMIPBV-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OC(C)C(O)=O)=CC=3)CC2)=C1 QDJZVWSCXMIPBV-UHFFFAOYSA-N 0.000 claims description 3
• RJTOGUMCAKAOAU-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-(4-fluorophenyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(F)=CC=2)CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 RJTOGUMCAKAOAU-UHFFFAOYSA-N 0.000 claims description 3
• CDGSHEMZRIDQKR-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-ethylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 CDGSHEMZRIDQKR-UHFFFAOYSA-N 0.000 claims description 3
• LTCMMBCLNPSLPT-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 LTCMMBCLNPSLPT-UHFFFAOYSA-N 0.000 claims description 3
• YQHDHUBEHGJCEC-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 YQHDHUBEHGJCEC-UHFFFAOYSA-N 0.000 claims description 3
• KEGPZSDHNALZCV-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 KEGPZSDHNALZCV-UHFFFAOYSA-N 0.000 claims description 3
• LVRFCQZNPPFUEA-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)CC1 LVRFCQZNPPFUEA-UHFFFAOYSA-N 0.000 claims description 3
• SEBPJYGLJAJFTA-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(Cl)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 SEBPJYGLJAJFTA-UHFFFAOYSA-N 0.000 claims description 3
• BOWUBEIOBIVSPN-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-ethoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OCC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 BOWUBEIOBIVSPN-UHFFFAOYSA-N 0.000 claims description 3
• NLAXBTJTOIJUJI-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 NLAXBTJTOIJUJI-UHFFFAOYSA-N 0.000 claims description 3
• VQLASPLXTBNGKV-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VQLASPLXTBNGKV-UHFFFAOYSA-N 0.000 claims description 3
• JAQAQHYBXFOQIS-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C(OC(C)C(O)=O)=CC=2)C(C)C)CC1 JAQAQHYBXFOQIS-UHFFFAOYSA-N 0.000 claims description 3
• QVTXXICAWVRHIE-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(OC)=CC=2)=C1 QVTXXICAWVRHIE-UHFFFAOYSA-N 0.000 claims description 3
• BUAJHSRYONGTBZ-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2,3-dimethylphenoxy]propanoic acid Chemical compound CC1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BUAJHSRYONGTBZ-UHFFFAOYSA-N 0.000 claims description 3
• SCIDMMOXVKXKRB-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2,5-dimethylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC=CC=2)=C1C SCIDMMOXVKXKRB-UHFFFAOYSA-N 0.000 claims description 3
• HAPTWYMLJSEMBH-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-fluorophenoxy]propanoic acid Chemical compound C1=C(F)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 HAPTWYMLJSEMBH-UHFFFAOYSA-N 0.000 claims description 3
• LTRFCDNYOSUIJC-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC=CC=2)=C1 LTRFCDNYOSUIJC-UHFFFAOYSA-N 0.000 claims description 3
• DOILTLCYLUZUHD-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DOILTLCYLUZUHD-UHFFFAOYSA-N 0.000 claims description 3
• YYHCUCBXPXQCCE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[4-[(4-phenoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(=O)OC=2C=CC=CC=2)=C1 YYHCUCBXPXQCCE-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
• 206010019280 Heart failures Diseases 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
• JXDFCRWRZXYIJF-UHFFFAOYSA-N 2-[2,5-dimethyl-4-[[4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC2=CSC=C2)=C1C JXDFCRWRZXYIJF-UHFFFAOYSA-N 0.000 claims description 2
• NBNVSJPAESGXAG-UHFFFAOYSA-N 2-[4-[[2-(4-chlorophenyl)-4-methyl-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(Cl)=CC=2)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 NBNVSJPAESGXAG-UHFFFAOYSA-N 0.000 claims description 2
• YCXWJKRXQBQMJQ-UHFFFAOYSA-N 2-[4-[[4-[(2,4-difluorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C(=CC(F)=CC=2)F)=C1 YCXWJKRXQBQMJQ-UHFFFAOYSA-N 0.000 claims description 2
• HEEZGJXCZRGDLD-UHFFFAOYSA-N 2-[4-[[4-[[4-(2,4-difluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C(=CC(F)=CC=2)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 HEEZGJXCZRGDLD-UHFFFAOYSA-N 0.000 claims description 2
• WHHYTFSKYVBOTI-UHFFFAOYSA-N 2-[4-[[4-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound COC1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 WHHYTFSKYVBOTI-UHFFFAOYSA-N 0.000 claims description 2
• TWEKCBPXLSVTAH-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 TWEKCBPXLSVTAH-UHFFFAOYSA-N 0.000 claims description 2
• GIIBXWSTEIQLJA-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C(OCC(O)=O)=CC=2)C(C)C)CC1 GIIBXWSTEIQLJA-UHFFFAOYSA-N 0.000 claims description 2
• QSZGAFBRFCJZIO-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2,3-dimethylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=C(C)C(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC=CC=2)=C1 QSZGAFBRFCJZIO-UHFFFAOYSA-N 0.000 claims description 2
• PSMIREUAPIEEPC-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=C(C(F)(F)F)C(OCC(=O)O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 PSMIREUAPIEEPC-UHFFFAOYSA-N 0.000 claims description 2
• KFGWQADDVBAOAA-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-bromophenoxy]acetic acid Chemical compound C1=C(Br)C(OCC(=O)O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KFGWQADDVBAOAA-UHFFFAOYSA-N 0.000 claims description 2
• WQNLZERBNDHNEG-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-5-chloro-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC=CC=2)=C1Cl WQNLZERBNDHNEG-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 238000005481 NMR spectroscopy Methods 0.000 description 459
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 229
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 228
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 199
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 135
• 235000019439 ethyl acetate Nutrition 0.000 description 98
• 238000004128 high performance liquid chromatography Methods 0.000 description 87
• 239000007787 solid Substances 0.000 description 81
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 54
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 49
• 125000003396 thiol group Chemical group [H]S* 0.000 description 47
• 239000000203 mixture Substances 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 239000000243 solution Substances 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
• 239000010410 layer Substances 0.000 description 28
• 239000003921 oil Substances 0.000 description 28
• 235000019198 oils Nutrition 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• 238000000746 purification Methods 0.000 description 26
• 239000011734 sodium Substances 0.000 description 26
• 238000000034 method Methods 0.000 description 25
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• 238000009472 formulation Methods 0.000 description 20
• 239000012267 brine Substances 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
• 239000000543 intermediate Substances 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 238000003556 assay Methods 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
• 235000019260 propionic acid Nutrition 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 108010016731 PPAR gamma Proteins 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 11
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 10
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 230000029936 alkylation Effects 0.000 description 8
• 238000005804 alkylation reaction Methods 0.000 description 8
• 238000000921 elemental analysis Methods 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• 238000001890 transfection Methods 0.000 description 8
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 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 7
• 230000004913 activation Effects 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000003446 ligand Substances 0.000 description 7
• 238000010898 silica gel chromatography Methods 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• 108010015181 PPAR delta Proteins 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 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 6
• 239000006071 cream Substances 0.000 description 6
• 239000004615 ingredient Substances 0.000 description 6
• FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 239000003039 volatile agent Substances 0.000 description 6
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
• FDKHJORLCLBJOQ-UHFFFAOYSA-N 2-methyl-4-[[4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC2=CSC=C2)=C1 FDKHJORLCLBJOQ-UHFFFAOYSA-N 0.000 description 5
• 0 C*(CCC1)CCC1(C)/C(/C)=[N+](\*)/[O-] Chemical compound C*(CCC1)CCC1(C)/C(/C)=[N+](\*)/[O-] 0.000 description 5
• 102000023984 PPAR alpha Human genes 0.000 description 5
• 229940123464 Thiazolidinedione Drugs 0.000 description 5
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 108020001756 ligand binding domains Proteins 0.000 description 5
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 5
• 108090000623 proteins and genes Proteins 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
• ZFRNJDBMBRHWQS-UHFFFAOYSA-N 5-(chloromethyl)-4-(furan-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC2=COC=C2)=C(CCl)S1 ZFRNJDBMBRHWQS-UHFFFAOYSA-N 0.000 description 4
• JIHXIIASVRYSCS-UHFFFAOYSA-N 5-(chloromethyl)-4-(thiophen-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2SC=CC=2)=C(CCl)S1 JIHXIIASVRYSCS-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 108010062497 VLDL Lipoproteins Proteins 0.000 description 4
• 239000012223 aqueous fraction Substances 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• 238000010828 elution Methods 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• ITFYRMFWHALAIV-UHFFFAOYSA-N ethyl 2-(4-chlorosulfonylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(S(Cl)(=O)=O)C=C1 ITFYRMFWHALAIV-UHFFFAOYSA-N 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• 239000008103 glucose Substances 0.000 description 4
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
• 229940011051 isopropyl acetate Drugs 0.000 description 4
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 239000013641 positive control Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 102000005962 receptors Human genes 0.000 description 4
• 108020003175 receptors Proteins 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 210000002966 serum Anatomy 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• 229940124597 therapeutic agent Drugs 0.000 description 4
• 150000003626 triacylglycerols Chemical class 0.000 description 4
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
• OAXUIOCBTUSKBN-UHFFFAOYSA-N 4-[(4-tert-butylphenyl)methyl]-5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 OAXUIOCBTUSKBN-UHFFFAOYSA-N 0.000 description 3
• IYLSTQCRBXLXKS-UHFFFAOYSA-N 4-[[4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=CC(OC)=CC=C1CC1=C(CSC=2C=C(C)C(O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 IYLSTQCRBXLXKS-UHFFFAOYSA-N 0.000 description 3
• CVCRXGQSKWMOSZ-UHFFFAOYSA-N 4-[[4-[(4-tert-butylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(=CC=2)C(C)(C)C)=C1 CVCRXGQSKWMOSZ-UHFFFAOYSA-N 0.000 description 3
• GKSDNJQXHMLJKN-UHFFFAOYSA-N 5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-4-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 GKSDNJQXHMLJKN-UHFFFAOYSA-N 0.000 description 3
• GPSNDIQQYQKJBA-UHFFFAOYSA-N 5-(chloromethyl)-4-(furan-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2OC=CC=2)=C(CCl)S1 GPSNDIQQYQKJBA-UHFFFAOYSA-N 0.000 description 3
• CJIKKJWKDZIRPQ-UHFFFAOYSA-N 5-(chloromethyl)-4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(COC2OCCCC2)=C(CCl)S1 CJIKKJWKDZIRPQ-UHFFFAOYSA-N 0.000 description 3
• MWYGKZONPOLGOF-UHFFFAOYSA-N 5-(chloromethyl)-4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC2=CSC=C2)=C(CCl)S1 MWYGKZONPOLGOF-UHFFFAOYSA-N 0.000 description 3
• BFBKHWGKBCLGAD-UHFFFAOYSA-N 5-(chloromethyl)-4-[(2,4-difluorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound FC1=CC(F)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 BFBKHWGKBCLGAD-UHFFFAOYSA-N 0.000 description 3
• MCGDQLUFDZZHTG-UHFFFAOYSA-N 5-(chloromethyl)-4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 MCGDQLUFDZZHTG-UHFFFAOYSA-N 0.000 description 3
• PSUPPEWMGNJEOD-UHFFFAOYSA-N 5-(chloromethyl)-4-[(4-methylsulfanylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(SC)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 PSUPPEWMGNJEOD-UHFFFAOYSA-N 0.000 description 3
• NNUCHANAAZBALD-UHFFFAOYSA-N 5-(chloromethyl)-4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1CC1=C(CCl)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 NNUCHANAAZBALD-UHFFFAOYSA-N 0.000 description 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• 102100026189 Beta-galactosidase Human genes 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
• YDBLKRPLXZNVNB-UHFFFAOYSA-N GW 501516 Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 YDBLKRPLXZNVNB-UHFFFAOYSA-N 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
• 240000007472 Leucaena leucocephala Species 0.000 description 3
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 3
• 102000043296 Lipoprotein lipases Human genes 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
• 239000011324 bead Substances 0.000 description 3
• 108010005774 beta-Galactosidase Proteins 0.000 description 3
• 230000027455 binding Effects 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• WGIIOGRUHSJKMI-UHFFFAOYSA-N ethyl 2-methyl-2-phenoxypropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1 WGIIOGRUHSJKMI-UHFFFAOYSA-N 0.000 description 3
• OLKAXZSJWCHIEG-UHFFFAOYSA-N ethyl 4-[tert-butyl(diphenyl)silyl]oxy-2-chloro-3-oxobutanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(=O)C(Cl)C(=O)OCC)C1=CC=CC=C1 OLKAXZSJWCHIEG-UHFFFAOYSA-N 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 229920000159 gelatin Polymers 0.000 description 3
• 235000019322 gelatine Nutrition 0.000 description 3
• 235000011852 gelatine desserts Nutrition 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
• 239000000825 pharmaceutical preparation Substances 0.000 description 3
• 125000006678 phenoxycarbonyl group Chemical group 0.000 description 3
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 229960004586 rosiglitazone Drugs 0.000 description 3
• 238000002821 scintillation proximity assay Methods 0.000 description 3
• 239000000377 silicon dioxide Substances 0.000 description 3
• 239000000600 sorbitol Substances 0.000 description 3
• 235000010356 sorbitol Nutrition 0.000 description 3
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• 150000001467 thiazolidinediones Chemical class 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 238000003146 transient transfection Methods 0.000 description 3
• 238000005292 vacuum distillation Methods 0.000 description 3
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
• KHFFISHIUHVFJN-UHFFFAOYSA-M (4-methoxy-3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(C)C(OC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KHFFISHIUHVFJN-UHFFFAOYSA-M 0.000 description 2
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 description 2
• IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
• ZJKHVJPSEZNOHQ-UHFFFAOYSA-N 2-[tert-butyl(diphenyl)silyl]oxyacetyl chloride Chemical compound C=1C=CC=CC=1[Si](OCC(Cl)=O)(C(C)(C)C)C1=CC=CC=C1 ZJKHVJPSEZNOHQ-UHFFFAOYSA-N 0.000 description 2
• HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 2
• DSUSTPNWSJQKBI-UHFFFAOYSA-N 4-(bromomethyl)-5-[2-(4-methoxy-3-methylphenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=C(C)C(OC)=CC=C1CCC1=C(CBr)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DSUSTPNWSJQKBI-UHFFFAOYSA-N 0.000 description 2
• BHEHNICAPZVKRH-UHFFFAOYSA-N 4-(chloromethyl)-1-methoxy-2-methylbenzene Chemical compound COC1=CC=C(CCl)C=C1C BHEHNICAPZVKRH-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• HYCAKCPKXJBRSE-UHFFFAOYSA-N 4-[2-[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenol Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=C(C)C(O)=CC=2)CC1 HYCAKCPKXJBRSE-UHFFFAOYSA-N 0.000 description 2
• RWQATMQHIDWCDG-UHFFFAOYSA-N 5-(chloromethyl)-4-[(4-methylthiophen-2-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound CC1=CSC(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CCl)=C1 RWQATMQHIDWCDG-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
• 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
• 208000000103 Anorexia Nervosa Diseases 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• 230000004568 DNA-binding Effects 0.000 description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
• 102000008946 Fibrinogen Human genes 0.000 description 2
• 108010049003 Fibrinogen Proteins 0.000 description 2
• 102100039556 Galectin-4 Human genes 0.000 description 2
• 208000002705 Glucose Intolerance Diseases 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 2
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 2
• NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
• 108010007622 LDL Lipoproteins Proteins 0.000 description 2
• 102000007330 LDL Lipoproteins Human genes 0.000 description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 description 2
• 238000006751 Mitsunobu reaction Methods 0.000 description 2
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
• 102000000536 PPAR gamma Human genes 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
• 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
• 229920001615 Tragacanth Polymers 0.000 description 2
• 102000040945 Transcription factor Human genes 0.000 description 2
• 108091023040 Transcription factor Proteins 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• WEQCMUUITSOWJS-UHFFFAOYSA-N [2-[4-(trifluoromethyl)phenyl]-4-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(C(F)(F)F)C=C1 WEQCMUUITSOWJS-UHFFFAOYSA-N 0.000 description 2
• CTTSZMAVJXHGBN-UHFFFAOYSA-N [4-(furan-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CO1 CTTSZMAVJXHGBN-UHFFFAOYSA-N 0.000 description 2
• WTIFPYXPFJULRA-UHFFFAOYSA-N [4-(furan-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC=1C=COC=1 WTIFPYXPFJULRA-UHFFFAOYSA-N 0.000 description 2
• PGBDROHECATIBR-UHFFFAOYSA-N [4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COC1CCCCO1 PGBDROHECATIBR-UHFFFAOYSA-N 0.000 description 2
• XBRYYDITNVUSPZ-UHFFFAOYSA-N [4-(thiophen-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CS1 XBRYYDITNVUSPZ-UHFFFAOYSA-N 0.000 description 2
• DIGVCBGJISDJIG-UHFFFAOYSA-N [4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC=1C=CSC=1 DIGVCBGJISDJIG-UHFFFAOYSA-N 0.000 description 2
• DOURTZKWRZKLLR-UHFFFAOYSA-N [4-[(2,4-difluorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(F)C=C1F DOURTZKWRZKLLR-UHFFFAOYSA-N 0.000 description 2
• SNXCDTDLVIASJB-UHFFFAOYSA-N [4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound C1=CC(OC)=CC=C1CC1=C(CO)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 SNXCDTDLVIASJB-UHFFFAOYSA-N 0.000 description 2
• CWLXMNJWCVOVMD-UHFFFAOYSA-N [4-[(4-methylsulfanylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound C1=CC(SC)=CC=C1CC1=C(CO)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 CWLXMNJWCVOVMD-UHFFFAOYSA-N 0.000 description 2
• HSQMJJVGLPIFDS-UHFFFAOYSA-N [4-[(4-methylthiophen-2-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound CC1=CSC(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CO)=C1 HSQMJJVGLPIFDS-UHFFFAOYSA-N 0.000 description 2
• XMELQURBDJJQAD-UHFFFAOYSA-N [4-[(4-tert-butylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound C1=CC(C(C)(C)C)=CC=C1CC1=C(CO)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XMELQURBDJJQAD-UHFFFAOYSA-N 0.000 description 2
• XJGIMIPCADNSCN-UHFFFAOYSA-N [4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(OC(F)(F)F)C=C1 XJGIMIPCADNSCN-UHFFFAOYSA-N 0.000 description 2
• IUZSDFXHPXEGQQ-UHFFFAOYSA-N [5-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methanol Chemical compound S1C(CO)=C(CO)N=C1C1=CC=C(C(F)(F)F)C=C1 IUZSDFXHPXEGQQ-UHFFFAOYSA-N 0.000 description 2
• SNAIIUAMCSVMOA-UHFFFAOYSA-N [5-[2-(4-methoxy-3-methylphenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methanol Chemical compound C1=C(C)C(OC)=CC=C1CCC1=C(CO)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 SNAIIUAMCSVMOA-UHFFFAOYSA-N 0.000 description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N acetone chloroform Natural products CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 150000001412 amines Chemical group 0.000 description 2
• 230000003178 anti-diabetic effect Effects 0.000 description 2
• 239000003472 antidiabetic agent Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
• 125000005997 bromomethyl group Chemical group 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 239000001569 carbon dioxide Substances 0.000 description 2
• 229910002092 carbon dioxide Inorganic materials 0.000 description 2
• 235000011089 carbon dioxide Nutrition 0.000 description 2
• 150000001735 carboxylic acids Chemical class 0.000 description 2
• 238000012512 characterization method Methods 0.000 description 2
• 238000004296 chiral HPLC Methods 0.000 description 2
• 235000012000 cholesterol Nutrition 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 235000008504 concentrate Nutrition 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 230000003247 decreasing effect Effects 0.000 description 2
• IVVXZXFSPQFIFM-UHFFFAOYSA-N diethyl 2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4,5-dicarboxylate Chemical compound S1C(C(=O)OCC)=C(C(=O)OCC)N=C1C1=CC=C(C(F)(F)F)C=C1 IVVXZXFSPQFIFM-UHFFFAOYSA-N 0.000 description 2
• JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
• LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
• 239000003937 drug carrier Substances 0.000 description 2
• 239000008157 edible vegetable oil Substances 0.000 description 2
• GVTZEFUSFMIKKH-UHFFFAOYSA-N ethyl 2-(2-ethylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC=C1CC GVTZEFUSFMIKKH-UHFFFAOYSA-N 0.000 description 2
• NMUGTJBYDIIXLB-UHFFFAOYSA-N ethyl 2-[4-[[4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CO)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NMUGTJBYDIIXLB-UHFFFAOYSA-N 0.000 description 2
• GXLRAOJWDXCLLJ-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 GXLRAOJWDXCLLJ-UHFFFAOYSA-N 0.000 description 2
• XKXFFBNTNKBWEN-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC)=CC=2)N=C(C=2C=CC=CC=2)S1 XKXFFBNTNKBWEN-UHFFFAOYSA-N 0.000 description 2
• UYPFXKLOKZZJSA-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC)=CC=2)N=C(C=2C=CC=CC=2)S1 UYPFXKLOKZZJSA-UHFFFAOYSA-N 0.000 description 2
• ITCFSFKETFWVSU-UHFFFAOYSA-N ethyl 2-methyl-2-(4-sulfanylphenoxy)propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(S)C=C1 ITCFSFKETFWVSU-UHFFFAOYSA-N 0.000 description 2
• COJCPXKSCDROHW-UHFFFAOYSA-N ethyl 4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COC1CCCCO1 COJCPXKSCDROHW-UHFFFAOYSA-N 0.000 description 2
• LZIBNHYKXPTZKL-UHFFFAOYSA-N ethyl 4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CO[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 LZIBNHYKXPTZKL-UHFFFAOYSA-N 0.000 description 2
• YWYNNQLHBSXWJV-UHFFFAOYSA-N ethyl 4-[tert-butyl(diphenyl)silyl]oxy-3-oxobutanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(=O)CC(=O)OCC)C1=CC=CC=C1 YWYNNQLHBSXWJV-UHFFFAOYSA-N 0.000 description 2
• 229940125753 fibrate Drugs 0.000 description 2
• 229940012952 fibrinogen Drugs 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 239000012467 final product Substances 0.000 description 2
• 239000001530 fumaric acid Substances 0.000 description 2
• 125000001072 heteroaryl group Chemical group 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• 102000054223 human PPARA Human genes 0.000 description 2
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 2
• 201000008980 hyperinsulinism Diseases 0.000 description 2
• 208000006575 hypertriglyceridemia Diseases 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• 239000002198 insoluble material Substances 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000012669 liquid formulation Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 238000000465 moulding Methods 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
• 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 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
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 201000009104 prediabetes syndrome Diseases 0.000 description 2
• 230000002265 prevention Effects 0.000 description 2
• 238000000159 protein binding assay Methods 0.000 description 2
• 239000002287 radioligand Substances 0.000 description 2
• 239000000376 reactant Substances 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 239000005720 sucrose Substances 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
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• 239000000196 tragacanth Substances 0.000 description 2
• 235000010487 tragacanth Nutrition 0.000 description 2
• 229940116362 tragacanth Drugs 0.000 description 2
• BCTQCGIKVZFCLS-JOCHJYFZSA-N (2r)-2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(O[C@H](C)C(O)=O)=CC=2)CC1 BCTQCGIKVZFCLS-JOCHJYFZSA-N 0.000 description 1
• BCTQCGIKVZFCLS-QFIPXVFZSA-N (2s)-2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(O[C@@H](C)C(O)=O)=CC=2)CC1 BCTQCGIKVZFCLS-QFIPXVFZSA-N 0.000 description 1
• UVIIQYUUEVQCOR-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1C UVIIQYUUEVQCOR-UHFFFAOYSA-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
• UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
• HFJDUYKRPHHPAX-UHFFFAOYSA-N 1-(4-methoxyphenyl)piperazine;hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[NH+]1CCNCC1 HFJDUYKRPHHPAX-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
• JUZVNCYMSRBUPV-UHFFFAOYSA-N 1-[4-[4-[[5-[2-(4-hydroxy-3-methylphenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=C(C)C(O)=CC=2)CC1 JUZVNCYMSRBUPV-UHFFFAOYSA-N 0.000 description 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
• QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 description 1
• PXBXTSIVRBNLSF-UHFFFAOYSA-N 2-(2-phenylethoxy)acetyl chloride Chemical compound ClC(=O)COCCC1=CC=CC=C1 PXBXTSIVRBNLSF-UHFFFAOYSA-N 0.000 description 1
• VQVBNWUUKLBHGI-UHFFFAOYSA-N 2-(4-bromophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Br)C=C1 VQVBNWUUKLBHGI-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• PJEZOBALGIZSEU-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 PJEZOBALGIZSEU-UHFFFAOYSA-N 0.000 description 1
• CHCDSWQSMBVFMK-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 CHCDSWQSMBVFMK-UHFFFAOYSA-N 0.000 description 1
• JPCUJEQTVLZHOG-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=C(OC)C=CC=2)=C1 JPCUJEQTVLZHOG-UHFFFAOYSA-N 0.000 description 1
• IUCFRKURSUQBEL-UHFFFAOYSA-N 2-[2-ethyl-4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 IUCFRKURSUQBEL-UHFFFAOYSA-N 0.000 description 1
• WVGPVWARTXBCRP-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(C=CC=2)C(F)(F)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WVGPVWARTXBCRP-UHFFFAOYSA-N 0.000 description 1
• XDJKATFFHPRHCY-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-4-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(F)(F)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 XDJKATFFHPRHCY-UHFFFAOYSA-N 0.000 description 1
• KQIGDGPULBUSDW-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-4-[[4-[4-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KQIGDGPULBUSDW-UHFFFAOYSA-N 0.000 description 1
• NBIBZBHPPFXMJP-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 NBIBZBHPPFXMJP-UHFFFAOYSA-N 0.000 description 1
• FRKIDCIHVFYHAR-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCOCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FRKIDCIHVFYHAR-UHFFFAOYSA-N 0.000 description 1
• QAWKUUROWPHHRG-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(phenoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=CC=CC=2)=C1 QAWKUUROWPHHRG-UHFFFAOYSA-N 0.000 description 1
• OYZXQLCEKVQSOZ-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(phenylmethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COCC=2C=CC=CC=2)=C1 OYZXQLCEKVQSOZ-UHFFFAOYSA-N 0.000 description 1
• CQVFKICRGJBVPX-UHFFFAOYSA-N 2-[2-methyl-4-[[4-(piperazin-1-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCNCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CQVFKICRGJBVPX-UHFFFAOYSA-N 0.000 description 1
• GQNLVEWZAONIDM-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(2-methylphenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1=CC=CC=C1OCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 GQNLVEWZAONIDM-UHFFFAOYSA-N 0.000 description 1
• CBUWZQAUUQHHTK-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(3-methylphenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(OCC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)=C1 CBUWZQAUUQHHTK-UHFFFAOYSA-N 0.000 description 1
• XGZDRSLCBAMTFI-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-methylphenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1OCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XGZDRSLCBAMTFI-UHFFFAOYSA-N 0.000 description 1
• QVGGQLJNPSVVHY-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-methylpiperidin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1CC(C)CCN1CC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QVGGQLJNPSVVHY-UHFFFAOYSA-N 0.000 description 1
• RQAOALNVZSSUHW-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-pentanoylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)CCCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 RQAOALNVZSSUHW-UHFFFAOYSA-N 0.000 description 1
• WECQTKCUYZYVGA-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-phenylmethoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OCC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WECQTKCUYZYVGA-UHFFFAOYSA-N 0.000 description 1
• AERPCBVTMOTXCF-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-phenylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC=CC=2)=C1 AERPCBVTMOTXCF-UHFFFAOYSA-N 0.000 description 1
• DQYBTLAAQZOAPL-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-phenylpiperidin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCC(CC2)C=2C=CC=CC=2)=C1 DQYBTLAAQZOAPL-UHFFFAOYSA-N 0.000 description 1
• CKCOTCKEJDVMJG-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-pyrazin-2-ylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2N=CC=NC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CKCOTCKEJDVMJG-UHFFFAOYSA-N 0.000 description 1
• NEPNQRPYGQJXPI-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(4-pyridin-4-ylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CN=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NEPNQRPYGQJXPI-UHFFFAOYSA-N 0.000 description 1
• SCZNGRSSJCDZKO-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(pentylamino)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CCCCCNCC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 SCZNGRSSJCDZKO-UHFFFAOYSA-N 0.000 description 1
• ZGNGEZJXXUKJRC-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[(pyridin-3-ylmethylamino)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CNCC=2C=NC=CC=2)=C1 ZGNGEZJXXUKJRC-UHFFFAOYSA-N 0.000 description 1
• ITTKDFDCZBOVPO-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[(2-methylcyclohexyl)amino]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1CCCCC1NCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 ITTKDFDCZBOVPO-UHFFFAOYSA-N 0.000 description 1
• AYPVAGCLNQMBMU-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[(3-methylcyclohexyl)amino]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1C(C)CCCC1NCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 AYPVAGCLNQMBMU-UHFFFAOYSA-N 0.000 description 1
• JDESFTKVFLBNJV-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[(4-methylcyclohexyl)amino]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1CC(C)CCC1NCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 JDESFTKVFLBNJV-UHFFFAOYSA-N 0.000 description 1
• KJBVPPRFJLABDA-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=C(OCC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OCC(O)=O)=CC=3)C=CC=2)=N1 KJBVPPRFJLABDA-UHFFFAOYSA-N 0.000 description 1
• JGRYNNOSDMOLHP-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=C(C=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 JGRYNNOSDMOLHP-UHFFFAOYSA-N 0.000 description 1
• LXNPUVFIJQZZJF-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=C(OCC3=C(SC(=N3)C=3C=CC=CC=3)CSC=3C=C(C)C(OCC(O)=O)=CC=3)C=CC=2)=N1 LXNPUVFIJQZZJF-UHFFFAOYSA-N 0.000 description 1
• LXWCFECQSVLAON-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=C(C=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC=CC=2)S1 LXWCFECQSVLAON-UHFFFAOYSA-N 0.000 description 1
• IYAROQTVNKPCEM-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(2-methylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C(=CC=CC=2)C)=C1 IYAROQTVNKPCEM-UHFFFAOYSA-N 0.000 description 1
• RDFWYQXBUNKSTA-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(2-methylpropanoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)C(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 RDFWYQXBUNKSTA-UHFFFAOYSA-N 0.000 description 1
• QVEQDOBLGDKILW-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(2-methylpropoxycarbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)OCC(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QVEQDOBLGDKILW-UHFFFAOYSA-N 0.000 description 1
• VVWFSDMTRNOJDO-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC(=O)N3CCCC3)CC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VVWFSDMTRNOJDO-UHFFFAOYSA-N 0.000 description 1
• NTZHFRFTKOZYLM-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(2-phenylethylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)NCCC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NTZHFRFTKOZYLM-UHFFFAOYSA-N 0.000 description 1
• XATJBSJFHZONKH-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(3-methylbutanoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)CC(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XATJBSJFHZONKH-UHFFFAOYSA-N 0.000 description 1
• WJGYRUIOFUTHKV-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(3-methylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OCC(O)=O)=CC=3)CC2)=C1 WJGYRUIOFUTHKV-UHFFFAOYSA-N 0.000 description 1
• SENWKCOFWRCBCU-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)CC1 SENWKCOFWRCBCU-UHFFFAOYSA-N 0.000 description 1
• PZJRAGKAHZRLRK-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(4-propoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OCCC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 PZJRAGKAHZRLRK-UHFFFAOYSA-N 0.000 description 1
• PHUWKTDUGLUUAI-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=CC(=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 PHUWKTDUGLUUAI-UHFFFAOYSA-N 0.000 description 1
• FOAYBXQRTMXKTB-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC=CC=3)CSC=3C=C(C)C(OCC(O)=O)=CC=3)=CC=2)=N1 FOAYBXQRTMXKTB-UHFFFAOYSA-N 0.000 description 1
• JKBHEUDBKVEXBG-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=CC(=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC=CC=2)S1 JKBHEUDBKVEXBG-UHFFFAOYSA-N 0.000 description 1
• UKDOWMJSYJDTOQ-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(methylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)NC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 UKDOWMJSYJDTOQ-UHFFFAOYSA-N 0.000 description 1
• FGGDWAVQHQPPDV-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(propan-2-ylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)NC(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 FGGDWAVQHQPPDV-UHFFFAOYSA-N 0.000 description 1
• CUPHOQFJGXUIEW-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(propylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)NCCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 CUPHOQFJGXUIEW-UHFFFAOYSA-N 0.000 description 1
• SINBGYROBOWRDQ-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(thiophene-2-carbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C=2SC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 SINBGYROBOWRDQ-UHFFFAOYSA-N 0.000 description 1
• QXIMCOXCEWQVSK-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC(OC(F)(F)F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 QXIMCOXCEWQVSK-UHFFFAOYSA-N 0.000 description 1
• KVPAQMKQJGDCMV-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(=O)OC(C)(C)C)=C1 KVPAQMKQJGDCMV-UHFFFAOYSA-N 0.000 description 1
• NVFASKTVZNBFGL-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NVFASKTVZNBFGL-UHFFFAOYSA-N 0.000 description 1
• VFCVZQOLYBGRNA-UHFFFAOYSA-N 2-[2-methyl-4-[[4-[[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC(F)(F)F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VFCVZQOLYBGRNA-UHFFFAOYSA-N 0.000 description 1
• DSHZQLTWBMTKEW-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1C1=CC=C(C(F)(F)F)C=C1 DSHZQLTWBMTKEW-UHFFFAOYSA-N 0.000 description 1
• JZVKMPJMTAXOBC-UHFFFAOYSA-N 2-[4-[2-[(4-fluorophenyl)carbamoyl-heptylamino]ethyl]phenoxy]-2-methylpropanoic acid Chemical group C=1C=C(F)C=CC=1NC(=O)N(CCCCCCC)CCC1=CC=C(OC(C)(C)C(O)=O)C=C1 JZVKMPJMTAXOBC-UHFFFAOYSA-N 0.000 description 1
• JLDYNVZUFGEHHG-UHFFFAOYSA-N 2-[4-[2-[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CCC=3C=C(C)C(OC(C)(C)C(O)=O)=CC=3)CC2)=C1 JLDYNVZUFGEHHG-UHFFFAOYSA-N 0.000 description 1
• VQKXEDGDBAVINH-UHFFFAOYSA-N 2-[4-[2-[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 VQKXEDGDBAVINH-UHFFFAOYSA-N 0.000 description 1
• UJBKHWKHDHTSSH-UHFFFAOYSA-N 2-[4-[2-[4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(Cl)=CC=2)=C1 UJBKHWKHDHTSSH-UHFFFAOYSA-N 0.000 description 1
• MDYHIAIUBAPDPR-UHFFFAOYSA-N 2-[4-[2-[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC1 MDYHIAIUBAPDPR-UHFFFAOYSA-N 0.000 description 1
• RHRXTMGTCBXHQQ-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[(4-phenoxycarbonylpiperazin-1-yl)methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(F)=CC=2)CN2CCN(CC2)C(=O)OC=2C=CC=CC=2)=C1 RHRXTMGTCBXHQQ-UHFFFAOYSA-N 0.000 description 1
• APLMQNUSDYKSPB-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[(4-phenoxycarbonylpiperazin-1-yl)methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC=2C=CC=CC=2)N=C(C=2C=CC(F)=CC=2)S1 APLMQNUSDYKSPB-UHFFFAOYSA-N 0.000 description 1
• IBFUBORIQLRVNQ-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[(4-propan-2-yloxycarbonylpiperazin-1-yl)methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1CN(C(=O)OC(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(F)=CC=2)=N1 IBFUBORIQLRVNQ-UHFFFAOYSA-N 0.000 description 1
• MOOMFRMMZXZGHT-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[(4-propan-2-yloxycarbonylpiperazin-1-yl)methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)OC(C)C)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(F)=CC=2)=N1 MOOMFRMMZXZGHT-UHFFFAOYSA-N 0.000 description 1
• WEJHXXJRYGYZIF-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(F)=CC=3)CSC=3C=C(C)C(OC(C)(C)C(O)=O)=CC=3)CC2)=C1 WEJHXXJRYGYZIF-UHFFFAOYSA-N 0.000 description 1
• CHCSXFXUFAVADK-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(F)=CC=3)CSC=3C=C(C)C(OC(C)C(O)=O)=CC=3)CC2)=C1 CHCSXFXUFAVADK-UHFFFAOYSA-N 0.000 description 1
• PUZRWSIAISEBAE-UHFFFAOYSA-N 2-[4-[[2-(4-fluorophenyl)-4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(F)=CC=2)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 PUZRWSIAISEBAE-UHFFFAOYSA-N 0.000 description 1
• IQRZRCJFOUDKPL-UHFFFAOYSA-N 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 IQRZRCJFOUDKPL-UHFFFAOYSA-N 0.000 description 1
• YUVHXTJYCLSSII-UHFFFAOYSA-N 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 YUVHXTJYCLSSII-UHFFFAOYSA-N 0.000 description 1
• VIIWOQVLFHWMLR-UHFFFAOYSA-N 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 VIIWOQVLFHWMLR-UHFFFAOYSA-N 0.000 description 1
• SZFPQYRZVRWXKD-UHFFFAOYSA-N 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 SZFPQYRZVRWXKD-UHFFFAOYSA-N 0.000 description 1
• CBCHFYNKMFFTEQ-UHFFFAOYSA-N 2-[4-[[4-[(3,5-dimethylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CC(C)NC(C)C2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CBCHFYNKMFFTEQ-UHFFFAOYSA-N 0.000 description 1
• RPRWZZCCNGBOTB-UHFFFAOYSA-N 2-[4-[[4-[(3-cyanophenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=C(C=CC=2)C#N)=C1 RPRWZZCCNGBOTB-UHFFFAOYSA-N 0.000 description 1
• DBMCIOKSULTMRF-UHFFFAOYSA-N 2-[4-[[4-[(3-hydroxypiperidin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CC(O)CCC2)=C1 DBMCIOKSULTMRF-UHFFFAOYSA-N 0.000 description 1
• KYRKJFMTKARTDI-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-ethylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 KYRKJFMTKARTDI-UHFFFAOYSA-N 0.000 description 1
• VZAWUGJJBOYQHR-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-ethylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 VZAWUGJJBOYQHR-UHFFFAOYSA-N 0.000 description 1
• DXNJGLWTXRAVRL-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(C)=O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DXNJGLWTXRAVRL-UHFFFAOYSA-N 0.000 description 1
• DRKRKTKZYBRKFX-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 DRKRKTKZYBRKFX-UHFFFAOYSA-N 0.000 description 1
• RFHGBUOWULRNSA-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 RFHGBUOWULRNSA-UHFFFAOYSA-N 0.000 description 1
• BVADKLZHNHVTIR-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 BVADKLZHNHVTIR-UHFFFAOYSA-N 0.000 description 1
• MWGAMFWCPTVIGV-UHFFFAOYSA-N 2-[4-[[4-[(4-acetylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(C)=O)=C1 MWGAMFWCPTVIGV-UHFFFAOYSA-N 0.000 description 1
• GZMPBFCMLUVGAJ-UHFFFAOYSA-N 2-[4-[[4-[(4-benzoylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 GZMPBFCMLUVGAJ-UHFFFAOYSA-N 0.000 description 1
• SABDOBBIFWPWTD-UHFFFAOYSA-N 2-[4-[[4-[(4-benzylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC=3C=CC=CC=3)CC2)=C1 SABDOBBIFWPWTD-UHFFFAOYSA-N 0.000 description 1
• WZQMWHBNHHYADQ-UHFFFAOYSA-N 2-[4-[[4-[(4-bromophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CC=2C=CC(Br)=CC=2)=C1 WZQMWHBNHHYADQ-UHFFFAOYSA-N 0.000 description 1
• QKTHZNOMEZJJSS-UHFFFAOYSA-N 2-[4-[[4-[(4-butanoylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)CCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QKTHZNOMEZJJSS-UHFFFAOYSA-N 0.000 description 1
• JQPOPADKHYZAFR-UHFFFAOYSA-N 2-[4-[[4-[(4-carbamoylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(N)=O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 JQPOPADKHYZAFR-UHFFFAOYSA-N 0.000 description 1
• KOTSRXLNWWCRCN-UHFFFAOYSA-N 2-[4-[[4-[(4-cyanophenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=CC(=CC=2)C#N)=C1 KOTSRXLNWWCRCN-UHFFFAOYSA-N 0.000 description 1
• CAJJQUHNVHYTDU-UHFFFAOYSA-N 2-[4-[[4-[(4-ethoxycarbonylpiperazin-1-yl)methyl]-2-(4-fluorophenyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(F)=CC=2)=N1 CAJJQUHNVHYTDU-UHFFFAOYSA-N 0.000 description 1
• VUYUQTXMYZSAJG-UHFFFAOYSA-N 2-[4-[[4-[(4-ethoxycarbonylpiperazin-1-yl)methyl]-2-(4-fluorophenyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(F)=CC=2)=N1 VUYUQTXMYZSAJG-UHFFFAOYSA-N 0.000 description 1
• KWBKATNWLMYUTI-UHFFFAOYSA-N 2-[4-[[4-[(4-ethoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 KWBKATNWLMYUTI-UHFFFAOYSA-N 0.000 description 1
• YBNGNCJGERSWDQ-UHFFFAOYSA-N 2-[4-[[4-[(4-ethoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 YBNGNCJGERSWDQ-UHFFFAOYSA-N 0.000 description 1
• XUPZMZXCDYCCJM-UHFFFAOYSA-N 2-[4-[[4-[(4-ethoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XUPZMZXCDYCCJM-UHFFFAOYSA-N 0.000 description 1
• WWDABNVPGVBSLX-UHFFFAOYSA-N 2-[4-[[4-[(4-ethylsulfonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(S(=O)(=O)CC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 WWDABNVPGVBSLX-UHFFFAOYSA-N 0.000 description 1
• IMBWADCWXUFFBV-UHFFFAOYSA-N 2-[4-[[4-[(4-hydroxypiperidin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCC(O)CC2)=C1 IMBWADCWXUFFBV-UHFFFAOYSA-N 0.000 description 1
• VCPHBHIHQDLGJK-UHFFFAOYSA-N 2-[4-[[4-[(4-methoxycarbonylpiperazin-1-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)OC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 VCPHBHIHQDLGJK-UHFFFAOYSA-N 0.000 description 1
• KKRCGPOTAYWLJT-UHFFFAOYSA-N 2-[4-[[4-[(cyclohexylamino)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CNC2CCCCC2)=C1 KKRCGPOTAYWLJT-UHFFFAOYSA-N 0.000 description 1
• QXXMFTOWHQRCEN-UHFFFAOYSA-N 2-[4-[[4-[(cyclopropylmethylamino)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CNCC2CC2)=C1 QXXMFTOWHQRCEN-UHFFFAOYSA-N 0.000 description 1
• AYWMSQSSXYCGPL-UHFFFAOYSA-N 2-[4-[[4-[[2-(hydroxymethyl)piperidin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2C(CCCC2)CO)=C1 AYWMSQSSXYCGPL-UHFFFAOYSA-N 0.000 description 1
• HGXPJBCATAFTSP-UHFFFAOYSA-N 2-[4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=C(OCC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=CC(OCC(O)=O)=CC=3)C=CC=2)=N1 HGXPJBCATAFTSP-UHFFFAOYSA-N 0.000 description 1
• DTMFFHOQGXZTMH-UHFFFAOYSA-N 2-[4-[[4-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=C(C=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DTMFFHOQGXZTMH-UHFFFAOYSA-N 0.000 description 1
• BYIMKVCDPYFJKL-UHFFFAOYSA-N 2-[4-[[4-[[4-(2,2-dimethylpropanoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BYIMKVCDPYFJKL-UHFFFAOYSA-N 0.000 description 1
• IJQSCRMTRMKPFD-UHFFFAOYSA-N 2-[4-[[4-[[4-(2-hydroxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C(=CC=CC=2)O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 IJQSCRMTRMKPFD-UHFFFAOYSA-N 0.000 description 1
• OYOKJOSOEZTDCW-UHFFFAOYSA-N 2-[4-[[4-[[4-(2-methoxyacetyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)COC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 OYOKJOSOEZTDCW-UHFFFAOYSA-N 0.000 description 1
• NWKGKEMBGJCXPC-UHFFFAOYSA-N 2-[4-[[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 NWKGKEMBGJCXPC-UHFFFAOYSA-N 0.000 description 1
• XCKPJNAPFWCJTH-UHFFFAOYSA-N 2-[4-[[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)CC1 XCKPJNAPFWCJTH-UHFFFAOYSA-N 0.000 description 1
• KAPYCXHSFSCJHK-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-hydroxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(O)C=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KAPYCXHSFSCJHK-UHFFFAOYSA-N 0.000 description 1
• UZBWBGQOXOSHAN-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OC(C)(C)C(O)=O)=CC=3)CC2)=C1 UZBWBGQOXOSHAN-UHFFFAOYSA-N 0.000 description 1
• BXLGZSUXGPWRPR-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C(OC(C)C(O)=O)=CC=3)C(C)C)CC2)=C1 BXLGZSUXGPWRPR-UHFFFAOYSA-N 0.000 description 1
• PNUXNBNLUJDOEN-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=C(OC)C=CC=2)=C1 PNUXNBNLUJDOEN-UHFFFAOYSA-N 0.000 description 1
• MDEWBFLLOVBYCF-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=C(OC)C=CC=2)=C1 MDEWBFLLOVBYCF-UHFFFAOYSA-N 0.000 description 1
• DIIFZKIXVANVEF-UHFFFAOYSA-N 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=CC(OC(C)(C)C(O)=O)=CC=3)CC2)=C1 DIIFZKIXVANVEF-UHFFFAOYSA-N 0.000 description 1
• LSVADSAGOSKFRC-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetamidophenyl)sulfonylpiperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)S(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 LSVADSAGOSKFRC-UHFFFAOYSA-N 0.000 description 1
• FRSQHCHRFOAAHO-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-(4-fluorophenyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)N=C(C=2C=CC(F)=CC=2)S1 FRSQHCHRFOAAHO-UHFFFAOYSA-N 0.000 description 1
• WLGXWUJNRLZBFP-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-ethylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 WLGXWUJNRLZBFP-UHFFFAOYSA-N 0.000 description 1
• OBSMMZBJVWIPEC-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)CC1 OBSMMZBJVWIPEC-UHFFFAOYSA-N 0.000 description 1
• HAAYSUTXPMTWMO-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 HAAYSUTXPMTWMO-UHFFFAOYSA-N 0.000 description 1
• YVHVUABNXGWUQM-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)=C1 YVHVUABNXGWUQM-UHFFFAOYSA-N 0.000 description 1
• KJUKUZHZNHGGAI-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(Cl)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KJUKUZHZNHGGAI-UHFFFAOYSA-N 0.000 description 1
• PPBIFQSAOYLDNU-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorobenzoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 PPBIFQSAOYLDNU-UHFFFAOYSA-N 0.000 description 1
• VPZBLPYFGKVDRM-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 VPZBLPYFGKVDRM-UHFFFAOYSA-N 0.000 description 1
• OZTZQCLKOSRHEJ-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 OZTZQCLKOSRHEJ-UHFFFAOYSA-N 0.000 description 1
• IXQCMSONVVGFCN-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 IXQCMSONVVGFCN-UHFFFAOYSA-N 0.000 description 1
• CLBSAGQBAAJVIU-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]propanoic acid Chemical compound C1=C(OC(C)C(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 CLBSAGQBAAJVIU-UHFFFAOYSA-N 0.000 description 1
• LJWTZRGTWRUTHS-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)S(=O)(=O)C=2C=CC(F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 LJWTZRGTWRUTHS-UHFFFAOYSA-N 0.000 description 1
• PMOOQZRAGMVISH-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-hydroxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(O)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 PMOOQZRAGMVISH-UHFFFAOYSA-N 0.000 description 1
• WDAAZUXXVJQYTG-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxybenzoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 WDAAZUXXVJQYTG-UHFFFAOYSA-N 0.000 description 1
• QBOVHWPMBYPCIT-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)CC1 QBOVHWPMBYPCIT-UHFFFAOYSA-N 0.000 description 1
• LSWWIJOARBXJLH-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(OC)=CC=2)=C1 LSWWIJOARBXJLH-UHFFFAOYSA-N 0.000 description 1
• GARKUBMBOPATRK-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OCC(O)=O)=CC=2)CC1 GARKUBMBOPATRK-UHFFFAOYSA-N 0.000 description 1
• FLLWGUNOYFUTJB-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OC(C)C(O)=O)=CC=2)CC1 FLLWGUNOYFUTJB-UHFFFAOYSA-N 0.000 description 1
• GEIMXGVJGUVYKZ-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC=CC=2)CSC=2C=C(C)C(OCC(O)=O)=CC=2)CC1 GEIMXGVJGUVYKZ-UHFFFAOYSA-N 0.000 description 1
• OMYYHCCNUOALMF-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC=CC=2)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 OMYYHCCNUOALMF-UHFFFAOYSA-N 0.000 description 1
• SOLVIQUPUWBLDP-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC=CC=2)CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)CC1 SOLVIQUPUWBLDP-UHFFFAOYSA-N 0.000 description 1
• FFSWTBHEPQOLGP-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC=CC=2)CSC=2C=CC(OCC(O)=O)=CC=2)CC1 FFSWTBHEPQOLGP-UHFFFAOYSA-N 0.000 description 1
• YYDFIRSXWYWOEG-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC=CC=2)CSC=2C=CC(OC(C)C(O)=O)=CC=2)CC1 YYDFIRSXWYWOEG-UHFFFAOYSA-N 0.000 description 1
• GNBIIIDDVQEYDO-UHFFFAOYSA-N 2-[4-[[4-[[4-(4-methoxyphenyl)sulfonylpiperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)CC1 GNBIIIDDVQEYDO-UHFFFAOYSA-N 0.000 description 1
• OGROKRAISXRTPD-UHFFFAOYSA-N 2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=CC(OCC(O)=O)=CC=3)=CC=2)=N1 OGROKRAISXRTPD-UHFFFAOYSA-N 0.000 description 1
• MEURHFLDTNVWSX-UHFFFAOYSA-N 2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=CC(=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 MEURHFLDTNVWSX-UHFFFAOYSA-N 0.000 description 1
• ZDEOXEJBWISVSX-UHFFFAOYSA-N 2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC=CC=3)CSC=3C=CC(OCC(O)=O)=CC=3)=CC=2)=N1 ZDEOXEJBWISVSX-UHFFFAOYSA-N 0.000 description 1
• SYCQPUUMRJTHGH-UHFFFAOYSA-N 2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1SCC1=C(COC=2C=CC(=CC=2)C=2N=C(C)ON=2)N=C(C=2C=CC=CC=2)S1 SYCQPUUMRJTHGH-UHFFFAOYSA-N 0.000 description 1
• XFXPLHSFFWZEDR-UHFFFAOYSA-N 2-[4-[[4-[[4-(cyclobutanecarbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C2CCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 XFXPLHSFFWZEDR-UHFFFAOYSA-N 0.000 description 1
• NZJMIAGIUAWFRA-UHFFFAOYSA-N 2-[4-[[4-[[4-(cyclohexanecarbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C2CCCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NZJMIAGIUAWFRA-UHFFFAOYSA-N 0.000 description 1
• ZDBSRGKFERZNLK-UHFFFAOYSA-N 2-[4-[[4-[[4-(cyclohexylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)NC2CCCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ZDBSRGKFERZNLK-UHFFFAOYSA-N 0.000 description 1
• QUHFFOBLKSEONN-UHFFFAOYSA-N 2-[4-[[4-[[4-(cyclopentanecarbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C2CCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 QUHFFOBLKSEONN-UHFFFAOYSA-N 0.000 description 1
• ICJOHWMKOAZPEL-UHFFFAOYSA-N 2-[4-[[4-[[4-(cyclopropanecarbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C2CC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ICJOHWMKOAZPEL-UHFFFAOYSA-N 0.000 description 1
• CACCETOJSLPSSM-UHFFFAOYSA-N 2-[4-[[4-[[4-(ethylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1CN(C(=O)NCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 CACCETOJSLPSSM-UHFFFAOYSA-N 0.000 description 1
• CGCJOFPADBBCAY-UHFFFAOYSA-N 2-[4-[[4-[[4-(furan-2-carbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C(=O)C=2OC=CC=2)=C1 CGCJOFPADBBCAY-UHFFFAOYSA-N 0.000 description 1
• FXFHGSCAFHSJHR-UHFFFAOYSA-N 2-[4-[[4-[[4-(furan-2-carbonyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C=2OC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FXFHGSCAFHSJHR-UHFFFAOYSA-N 0.000 description 1
• ONTADJFYLLETTI-UHFFFAOYSA-N 2-[4-[[4-[[4-(hydroxymethyl)piperidin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCC(CO)CC2)=C1 ONTADJFYLLETTI-UHFFFAOYSA-N 0.000 description 1
• VDVBFPHWNFNFKB-UHFFFAOYSA-N 2-[4-[[4-[[4-(tert-butylcarbamoyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)NC(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VDVBFPHWNFNFKB-UHFFFAOYSA-N 0.000 description 1
• RLCFVKWCRVYPCY-UHFFFAOYSA-N 2-[4-[[4-[[4-[(3-methoxyphenyl)carbamoyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound COC1=CC=CC(NC(=O)N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=C(C)C(OC(C)C(O)=O)=CC=3)CC2)=C1 RLCFVKWCRVYPCY-UHFFFAOYSA-N 0.000 description 1
• JFHFDLJVEXNFAQ-UHFFFAOYSA-N 2-[4-[[4-[[4-[(4-chlorophenyl)methyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC=3C=CC(Cl)=CC=3)CC2)=C1 JFHFDLJVEXNFAQ-UHFFFAOYSA-N 0.000 description 1
• LVJDILZSJHKDHY-UHFFFAOYSA-N 2-[4-[[4-[[4-[(4-fluorophenyl)carbamoyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)NC=2C=CC(F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 LVJDILZSJHKDHY-UHFFFAOYSA-N 0.000 description 1
• BQJHXBJKJFGGHF-UHFFFAOYSA-N 2-[4-[[4-[[4-[4-(dimethylamino)benzoyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]propanoic acid Chemical compound C1=C(C)C(OC(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)C=2C=CC(=CC=2)N(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BQJHXBJKJFGGHF-UHFFFAOYSA-N 0.000 description 1
• LLTSCZSIMXIDCC-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 LLTSCZSIMXIDCC-UHFFFAOYSA-N 0.000 description 1
• XACWTGQKGDPIDW-UHFFFAOYSA-N 2-[4-[[4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 XACWTGQKGDPIDW-UHFFFAOYSA-N 0.000 description 1
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
• BVFWSLSPABQQFE-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(C=CC=2)C(F)(F)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BVFWSLSPABQQFE-UHFFFAOYSA-N 0.000 description 1
• WHWQJBZBNJFKAK-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[(4-methylthiophen-2-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound CC1=CSC(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)=C1 WHWQJBZBNJFKAK-UHFFFAOYSA-N 0.000 description 1
• KYOBNZAPUWQWPL-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CSC=3C=CC(OC(C)(C)C(O)=O)=CC=3)=CC=2)=N1 KYOBNZAPUWQWPL-UHFFFAOYSA-N 0.000 description 1
• ZURKJLWQDSDCNM-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl]-2-phenyl-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound O1C(C)=NC(C=2C=CC(OCC3=C(SC(=N3)C=3C=CC=CC=3)CSC=3C=CC(OC(C)(C)C(O)=O)=CC=3)=CC=2)=N1 ZURKJLWQDSDCNM-UHFFFAOYSA-N 0.000 description 1
• FIXUWUNATGCQSZ-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=C(CC=2C=CC(OC(F)(F)F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FIXUWUNATGCQSZ-UHFFFAOYSA-N 0.000 description 1
• WXZBONIBEJMYCR-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=C(CSC=2C=CC(OC(C)(C)C(O)=O)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 WXZBONIBEJMYCR-UHFFFAOYSA-N 0.000 description 1
• HEWFEKZXMZTSRN-UHFFFAOYSA-N 2-methyl-4-[[4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC2OCCCC2)=C1 HEWFEKZXMZTSRN-UHFFFAOYSA-N 0.000 description 1
• CLTOJAMTVBYIGF-UHFFFAOYSA-N 2-methylpropyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OCC(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CLTOJAMTVBYIGF-UHFFFAOYSA-N 0.000 description 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
• DDCBVFRRESFKMF-UHFFFAOYSA-N 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol Chemical compound O1C(C)=NC(C=2C=C(O)C=CC=2)=N1 DDCBVFRRESFKMF-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
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
• MSLYUOCLIQQWQK-UHFFFAOYSA-N 4,4,4-trichlorobutan-2-ol Chemical compound CC(O)CC(Cl)(Cl)Cl MSLYUOCLIQQWQK-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
• HSUZXBZGZUHECK-UHFFFAOYSA-N 4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(COC2OCCCC2)=C(C=O)S1 HSUZXBZGZUHECK-UHFFFAOYSA-N 0.000 description 1
• IPRFNMJROWWFBH-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarbothioamide Chemical compound NC(=S)C1=CC=C(C(F)(F)F)C=C1 IPRFNMJROWWFBH-UHFFFAOYSA-N 0.000 description 1
• QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
• IYWOFDMPWNSQMH-UHFFFAOYSA-N 4-[(4-bromophenyl)methyl]-5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC(Br)=CC=2)=C(CCl)S1 IYWOFDMPWNSQMH-UHFFFAOYSA-N 0.000 description 1
• DWXBVELVHFKLAA-UHFFFAOYSA-N 4-[2-[4-(bromomethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CBr)=C1 DWXBVELVHFKLAA-UHFFFAOYSA-N 0.000 description 1
• LKIOAPSLGPGKAB-UHFFFAOYSA-N 4-[2-[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenol Chemical compound COC1=CC=CC(N2CCN(CC3=C(SC(=N3)C=3C=CC(=CC=3)C(F)(F)F)CCC=3C=C(C)C(O)=CC=3)CC2)=C1 LKIOAPSLGPGKAB-UHFFFAOYSA-N 0.000 description 1
• RIJSSKBVOKAWOU-UHFFFAOYSA-N 4-[2-[4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCN(CC2)C=2C=CC(Cl)=CC=2)=C1 RIJSSKBVOKAWOU-UHFFFAOYSA-N 0.000 description 1
• ZSQRFZDUCBUJOO-UHFFFAOYSA-N 4-[[2-(4-fluorophenyl)-4-(oxan-2-yloxymethyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(F)=CC=2)COC2OCCCC2)=C1 ZSQRFZDUCBUJOO-UHFFFAOYSA-N 0.000 description 1
• UUWPFYNVTPJZBV-UHFFFAOYSA-N 4-[[4-(bromomethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CBr)=C1 UUWPFYNVTPJZBV-UHFFFAOYSA-N 0.000 description 1
• QUFMZFXTBKFLIB-UHFFFAOYSA-N 4-[[4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CO)=C1 QUFMZFXTBKFLIB-UHFFFAOYSA-N 0.000 description 1
• IQDLCSAVHNFSHL-UHFFFAOYSA-N 4-[[4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCC1=C(COC2OCCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 IQDLCSAVHNFSHL-UHFFFAOYSA-N 0.000 description 1
• AFLNKRAUDSRAPZ-UHFFFAOYSA-N 4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenol Chemical compound C1=CC(OC)=CC=C1N1CCN(CC2=C(SC(=N2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(O)=CC=2)CC1 AFLNKRAUDSRAPZ-UHFFFAOYSA-N 0.000 description 1
• OLJYARRXCQEMDH-UHFFFAOYSA-N 4-benzyl-5-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC=CC=2)=C(CCl)S1 OLJYARRXCQEMDH-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• VQFOHZWOKJQOGO-UHFFFAOYSA-N 4-fluorobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(F)C=C1 VQFOHZWOKJQOGO-UHFFFAOYSA-N 0.000 description 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
• VQDQISMDUHBUFF-UHFFFAOYSA-N 4-phenylbutanoyl chloride Chemical compound ClC(=O)CCCC1=CC=CC=C1 VQDQISMDUHBUFF-UHFFFAOYSA-N 0.000 description 1
• 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• QRVMSLFFWRPHME-UHFFFAOYSA-N 5-(chloromethyl)-2-(4-fluorophenyl)-4-(oxan-2-yloxymethyl)-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=NC(COC2OCCCC2)=C(CCl)S1 QRVMSLFFWRPHME-UHFFFAOYSA-N 0.000 description 1
• DBMWNYLLBUUZDY-UHFFFAOYSA-N 5-(chloromethyl)-4-(2-phenylethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(COCCC=2C=CC=CC=2)=C(CCl)S1 DBMWNYLLBUUZDY-UHFFFAOYSA-N 0.000 description 1
• VNGUJFPYMUFJIW-UHFFFAOYSA-N 5-(chloromethyl)-4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CCC=2C=CC=CC=2)=C(CCl)S1 VNGUJFPYMUFJIW-UHFFFAOYSA-N 0.000 description 1
• UTTPQMMEQHJXJH-UHFFFAOYSA-N 5-(chloromethyl)-4-(3-phenylpropyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CCCC=2C=CC=CC=2)=C(CCl)S1 UTTPQMMEQHJXJH-UHFFFAOYSA-N 0.000 description 1
• JEIWNLNXCGIXKL-UHFFFAOYSA-N 5-(chloromethyl)-4-(oxan-2-yloxymethyl)-2-phenyl-1,3-thiazole Chemical compound ClCC=1SC(C=2C=CC=CC=2)=NC=1COC1CCCCO1 JEIWNLNXCGIXKL-UHFFFAOYSA-N 0.000 description 1
• ZZFSKBDESOOOIC-UHFFFAOYSA-N 5-(chloromethyl)-4-(phenylmethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(COCC=2C=CC=CC=2)=C(CCl)S1 ZZFSKBDESOOOIC-UHFFFAOYSA-N 0.000 description 1
• MBLHEWGCRHREBO-UHFFFAOYSA-N 5-(chloromethyl)-4-[(4-phenylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC(=CC=2)C=2C=CC=CC=2)=C(CCl)S1 MBLHEWGCRHREBO-UHFFFAOYSA-N 0.000 description 1
• FBMZGWDXJVZFMZ-UHFFFAOYSA-N 5-(chloromethyl)-4-[(4-thiophen-3-ylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(CC=2C=CC(=CC=2)C2=CSC=C2)=C(CCl)S1 FBMZGWDXJVZFMZ-UHFFFAOYSA-N 0.000 description 1
• YAIMAVCMQVNVPU-NTUHNPAUSA-N 5-[(e)-2-(4-methoxy-3-methylphenyl)ethenyl]-4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=C(C)C(OC)=CC=C1\C=C\C1=C(COC2OCCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 YAIMAVCMQVNVPU-NTUHNPAUSA-N 0.000 description 1
• LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
• 239000005541 ACE inhibitor Substances 0.000 description 1
• 102100024321 Alkaline phosphatase, placental type Human genes 0.000 description 1
• 235000019489 Almond oil Nutrition 0.000 description 1
• 229940123073 Angiotensin antagonist Drugs 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 239000004342 Benzoyl peroxide Substances 0.000 description 1
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• 229910000906 Bronze Inorganic materials 0.000 description 1
• 206010006550 Bulimia nervosa Diseases 0.000 description 1
• 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
• 101100168093 Caenorhabditis elegans cogc-2 gene Proteins 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
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 229920002261 Corn starch Polymers 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
• 201000004624 Dermatitis Diseases 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
• 206010070901 Diabetic dyslipidaemia Diseases 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 239000001263 FEMA 3042 Substances 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
• 101001051093 Homo sapiens Low-density lipoprotein receptor Proteins 0.000 description 1
• 101000741797 Homo sapiens Peroxisome proliferator-activated receptor delta Proteins 0.000 description 1
• 101000741790 Homo sapiens Peroxisome proliferator-activated receptor gamma Proteins 0.000 description 1
• 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
• 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
• 206010020772 Hypertension 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
• 206010061218 Inflammation Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 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
• 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
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 102100024640 Low-density lipoprotein receptor Human genes 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 101100221487 Mus musculus Cog2 gene Proteins 0.000 description 1
• 101000741778 Mus musculus Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 108091028043 Nucleic acid sequence Proteins 0.000 description 1
• 102000016978 Orphan receptors Human genes 0.000 description 1
• 108070000031 Orphan receptors Proteins 0.000 description 1
• 108010028924 PPAR alpha Proteins 0.000 description 1
• 229940124754 PPAR-alpha/gamma agonist Drugs 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• 101710117029 Peroxisome proliferator-activated receptor delta Proteins 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 108091027981 Response element Proteins 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 108010085012 Steroid Receptors Proteins 0.000 description 1
• 102000007451 Steroid Receptors Human genes 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 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
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
• ZYFPDBDWFKGJAP-UHFFFAOYSA-N [2-(4-fluorophenyl)-4-(oxan-2-yloxymethyl)-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(F)=CC=2)=NC=1COC1CCCCO1 ZYFPDBDWFKGJAP-UHFFFAOYSA-N 0.000 description 1
• ZPJBZYIVWHPPHL-UHFFFAOYSA-N [4-(2-phenylethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COCCC1=CC=CC=C1 ZPJBZYIVWHPPHL-UHFFFAOYSA-N 0.000 description 1
• FEAIKOHMWJIKPV-UHFFFAOYSA-N [4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CCC1=CC=CC=C1 FEAIKOHMWJIKPV-UHFFFAOYSA-N 0.000 description 1
• IWUSAYKCXKEMQT-UHFFFAOYSA-N [4-(3-phenylpropyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CCCC1=CC=CC=C1 IWUSAYKCXKEMQT-UHFFFAOYSA-N 0.000 description 1
• ZAGXSLXLZMSHOE-UHFFFAOYSA-N [4-(oxan-2-yloxymethyl)-2-phenyl-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC=CC=2)=NC=1COC1CCCCO1 ZAGXSLXLZMSHOE-UHFFFAOYSA-N 0.000 description 1
• GOGVIFGBOTVWTA-UHFFFAOYSA-N [4-(phenylmethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COCC1=CC=CC=C1 GOGVIFGBOTVWTA-UHFFFAOYSA-N 0.000 description 1
• ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 description 1
• FNPQURCLWPEVJV-UHFFFAOYSA-N [4-[(4-bromophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(Br)C=C1 FNPQURCLWPEVJV-UHFFFAOYSA-N 0.000 description 1
• AOQBCQZSLFGNFP-UHFFFAOYSA-N [4-[(4-thiophen-3-ylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC(C=C1)=CC=C1C=1C=CSC=1 AOQBCQZSLFGNFP-UHFFFAOYSA-N 0.000 description 1
• CKNNGYVLOIHAOL-UHFFFAOYSA-N [4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC(=C(S1)CO)N=C1C1=CC=C(C(F)(F)F)C=C1 CKNNGYVLOIHAOL-UHFFFAOYSA-N 0.000 description 1
• DVSSAIKXMLWWLL-UHFFFAOYSA-N [4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CC=C1 DVSSAIKXMLWWLL-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• 230000002293 adipogenic effect Effects 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 239000008168 almond oil Substances 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
• 235000010210 aluminium Nutrition 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
• 229940063655 aluminum stearate Drugs 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 239000002369 angiotensin antagonist Substances 0.000 description 1
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 229940127003 anti-diabetic drug Drugs 0.000 description 1
• 229940030600 antihypertensive agent Drugs 0.000 description 1
• 239000002220 antihypertensive agent Substances 0.000 description 1
• 239000003524 antilipemic agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 230000000923 atherogenic effect Effects 0.000 description 1
• 208000010668 atopic eczema Diseases 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
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229960004365 benzoic acid Drugs 0.000 description 1
• 235000019400 benzoyl peroxide Nutrition 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
• 239000011230 binding agent Substances 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 229960002685 biotin Drugs 0.000 description 1
• 235000020958 biotin Nutrition 0.000 description 1
• 239000011616 biotin Substances 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 125000006267 biphenyl group Chemical group 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• 239000010974 bronze Substances 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• 239000000872 buffer 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
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000007910 chewable tablet Substances 0.000 description 1
• 108700010039 chimeric receptor Proteins 0.000 description 1
• 150000001805 chlorine compounds Chemical group 0.000 description 1
• VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
• 229960002023 chloroprocaine Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 230000009137 competitive binding Effects 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 230000021615 conjugation Effects 0.000 description 1
• 239000012050 conventional carrier Substances 0.000 description 1
• KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 229940043237 diethanolamine Drugs 0.000 description 1
• JNQWFLVFHCCWPV-UHFFFAOYSA-N diethyl 2-chloro-3-oxobutanedioate Chemical compound CCOC(=O)C(Cl)C(=O)C(=O)OCC JNQWFLVFHCCWPV-UHFFFAOYSA-N 0.000 description 1
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 150000002019 disulfides Chemical class 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
• 229940125542 dual agonist 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
• 229960000873 enalapril Drugs 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 238000011067 equilibration Methods 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
• RNBKDBPVBYEJOR-UHFFFAOYSA-N ethyl 2-(2-ethyl-4-sulfanylphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(S)C=C1CC RNBKDBPVBYEJOR-UHFFFAOYSA-N 0.000 description 1
• BINPMGQAUALOPK-UHFFFAOYSA-N ethyl 2-(2-methyl-4-sulfanylphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(S)C=C1C BINPMGQAUALOPK-UHFFFAOYSA-N 0.000 description 1
• AFCLTTVCXFWNSS-UHFFFAOYSA-N ethyl 2-(2-propan-2-yl-4-sulfanylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(S)C=C1C(C)C AFCLTTVCXFWNSS-UHFFFAOYSA-N 0.000 description 1
• YXTABYFNKFUIEW-UHFFFAOYSA-N ethyl 2-(2-propyl-4-sulfanylphenoxy)propanoate Chemical compound CCCC1=CC(S)=CC=C1OC(C)C(=O)OCC YXTABYFNKFUIEW-UHFFFAOYSA-N 0.000 description 1
• OSRPEGMCOXIYJR-UHFFFAOYSA-N ethyl 2-(4-chlorosulfonyl-2-ethylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(S(Cl)(=O)=O)C=C1CC OSRPEGMCOXIYJR-UHFFFAOYSA-N 0.000 description 1
• BXENIYIGPPXPNY-UHFFFAOYSA-N ethyl 2-(4-chlorosulfonyl-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(S(Cl)(=O)=O)C=C1C BXENIYIGPPXPNY-UHFFFAOYSA-N 0.000 description 1
• NZWJXSGPECGFJN-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-(oxan-2-yloxymethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(F)=CC=2)=NC=1COC1CCCCO1 NZWJXSGPECGFJN-UHFFFAOYSA-N 0.000 description 1
• FKXLBALOGKPRIA-UHFFFAOYSA-N ethyl 2-[2-ethyl-4-[[4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(CC)C(OCC(=O)OCC)=CC=C1SCC1=C(CO)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FKXLBALOGKPRIA-UHFFFAOYSA-N 0.000 description 1
• FKMCGVNNSDYJLO-UHFFFAOYSA-N ethyl 2-[2-ethyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(CC)C(OCC(=O)OCC)=CC=C1SCC1=C(CN2CCOCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FKMCGVNNSDYJLO-UHFFFAOYSA-N 0.000 description 1
• KSVVMKKSYKYEQC-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(CN2CCOCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 KSVVMKKSYKYEQC-UHFFFAOYSA-N 0.000 description 1
• ZFZZHGGJCATVDV-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[4-(oxan-2-yloxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(COC2OCCCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ZFZZHGGJCATVDV-UHFFFAOYSA-N 0.000 description 1
• IOXPNIYASQMHPZ-UHFFFAOYSA-N ethyl 2-[4-(trifluoromethyl)phenyl]-4-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(C(F)(F)F)C=C1 IOXPNIYASQMHPZ-UHFFFAOYSA-N 0.000 description 1
• ALYBYBNSOOLVJT-UHFFFAOYSA-N ethyl 2-[4-[[2-(4-fluorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(OC)C=CC=2)N=C(C=2C=CC(F)=CC=2)S1 ALYBYBNSOOLVJT-UHFFFAOYSA-N 0.000 description 1
• HBWBRZWUEUESSR-UHFFFAOYSA-N ethyl 2-[4-[[2-(4-fluorophenyl)-4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC)=CC=2)N=C(C=2C=CC(F)=CC=2)S1 HBWBRZWUEUESSR-UHFFFAOYSA-N 0.000 description 1
• JQINDCROMWOBBV-UHFFFAOYSA-N ethyl 2-[4-[[4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(CO)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 JQINDCROMWOBBV-UHFFFAOYSA-N 0.000 description 1
• ZMRRJNFBKMMNGO-UHFFFAOYSA-N ethyl 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propylphenoxy]acetate Chemical compound C1=C(OCC(=O)OCC)C(CCC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CN2CCOCC2)=C1 ZMRRJNFBKMMNGO-UHFFFAOYSA-N 0.000 description 1
• DDSSIHMSVNEUEL-UHFFFAOYSA-N ethyl 2-[4-[[4-[(2,4-difluorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(CC=2C(=CC(F)=CC=2)F)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DDSSIHMSVNEUEL-UHFFFAOYSA-N 0.000 description 1
• CCASPDORVYFQLY-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C(=CC=CC=2)OC)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CCASPDORVYFQLY-UHFFFAOYSA-N 0.000 description 1
• WOALJTSWPXTRPB-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(OC)C=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WOALJTSWPXTRPB-UHFFFAOYSA-N 0.000 description 1
• NYMLQCYOBOBBAC-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=C(OC)C=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NYMLQCYOBOBBAC-UHFFFAOYSA-N 0.000 description 1
• MPAJNJRCNBEJNL-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-(4-fluorophenyl)-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)N=C(C=2C=CC(F)=CC=2)S1 MPAJNJRCNBEJNL-UHFFFAOYSA-N 0.000 description 1
• NMHDBLPCGMFPED-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NMHDBLPCGMFPED-UHFFFAOYSA-N 0.000 description 1
• JXAMESYPHLHMSV-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(=CC=2)C(C)=O)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 JXAMESYPHLHMSV-UHFFFAOYSA-N 0.000 description 1
• OTWAYAIYWCVHLT-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(Cl)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 OTWAYAIYWCVHLT-UHFFFAOYSA-N 0.000 description 1
• SADGKXGQHJQWQC-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(F)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 SADGKXGQHJQWQC-UHFFFAOYSA-N 0.000 description 1
• FUBPBUZNRDBPDT-UHFFFAOYSA-N ethyl 2-[4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C=2C=CC(OC)=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FUBPBUZNRDBPDT-UHFFFAOYSA-N 0.000 description 1
• QVSJNHCPNBUOJE-UHFFFAOYSA-N ethyl 2-[tert-butyl(diphenyl)silyl]oxyacetate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(=O)OCC)C1=CC=CC=C1 QVSJNHCPNBUOJE-UHFFFAOYSA-N 0.000 description 1
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
• JMTJAPHJNNZWII-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-4-(2-phenylethoxy)butanoate Chemical compound CCOC(=O)C(Cl)C(=O)COCCC1=CC=CC=C1 JMTJAPHJNNZWII-UHFFFAOYSA-N 0.000 description 1
• RBJYBVPPUKQOQO-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(Cl)C(=O)CC1=CC=CC=C1 RBJYBVPPUKQOQO-UHFFFAOYSA-N 0.000 description 1
• AXESJJDMDNBIBX-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-4-phenylmethoxybutanoate Chemical compound CCOC(=O)C(Cl)C(=O)COCC1=CC=CC=C1 AXESJJDMDNBIBX-UHFFFAOYSA-N 0.000 description 1
• RICCWHIBTQBAMF-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-5-phenylpentanoate Chemical compound CCOC(=O)C(Cl)C(=O)CCC1=CC=CC=C1 RICCWHIBTQBAMF-UHFFFAOYSA-N 0.000 description 1
• SNYLAIMJNLIMHA-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-6-phenylhexanoate Chemical compound CCOC(=O)C(Cl)C(=O)CCCC1=CC=CC=C1 SNYLAIMJNLIMHA-UHFFFAOYSA-N 0.000 description 1
• ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
• FOZKDFDRNKDMRN-UHFFFAOYSA-N ethyl 3-oxo-4-(2-phenylethoxy)butanoate Chemical compound CCOC(=O)CC(=O)COCCC1=CC=CC=C1 FOZKDFDRNKDMRN-UHFFFAOYSA-N 0.000 description 1
• BOZNWXQZCYZCSH-UHFFFAOYSA-N ethyl 3-oxo-4-phenylbutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=CC=C1 BOZNWXQZCYZCSH-UHFFFAOYSA-N 0.000 description 1
• DXUTWLTWGKEWJA-UHFFFAOYSA-N ethyl 3-oxo-4-phenylmethoxybutanoate Chemical compound CCOC(=O)CC(=O)COCC1=CC=CC=C1 DXUTWLTWGKEWJA-UHFFFAOYSA-N 0.000 description 1
• PRDJGEFZGPKCSG-UHFFFAOYSA-N ethyl 3-oxo-5-phenylpentanoate Chemical compound CCOC(=O)CC(=O)CCC1=CC=CC=C1 PRDJGEFZGPKCSG-UHFFFAOYSA-N 0.000 description 1
• IPZRCWYMWIOAIH-UHFFFAOYSA-N ethyl 3-oxo-6-phenylhexanoate Chemical compound CCOC(=O)CC(=O)CCCC1=CC=CC=C1 IPZRCWYMWIOAIH-UHFFFAOYSA-N 0.000 description 1
• YKCBAOPAEIVXLK-UHFFFAOYSA-N ethyl 4-(2-phenylethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COCCC1=CC=CC=C1 YKCBAOPAEIVXLK-UHFFFAOYSA-N 0.000 description 1
• SESNWHGFRVSVQK-UHFFFAOYSA-N ethyl 4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CCC1=CC=CC=C1 SESNWHGFRVSVQK-UHFFFAOYSA-N 0.000 description 1
• YHKFPUGUCAHCFL-UHFFFAOYSA-N ethyl 4-(3-phenylpropyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CCCC1=CC=CC=C1 YHKFPUGUCAHCFL-UHFFFAOYSA-N 0.000 description 1
• FOJBYSXPVXTANJ-UHFFFAOYSA-N ethyl 4-(4-bromophenyl)-2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(=O)CC1=CC=C(Br)C=C1 FOJBYSXPVXTANJ-UHFFFAOYSA-N 0.000 description 1
• BRYNITBKFYVFBV-UHFFFAOYSA-N ethyl 4-(4-bromophenyl)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=C(Br)C=C1 BRYNITBKFYVFBV-UHFFFAOYSA-N 0.000 description 1
• OYZWGBDTWXSQGN-UHFFFAOYSA-N ethyl 4-(bromomethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound BrCC1=C(C(=O)OCC)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 OYZWGBDTWXSQGN-UHFFFAOYSA-N 0.000 description 1
• UIBKHCBQYJSUIW-UHFFFAOYSA-N ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylate Chemical compound BrCC1=C(C(=O)OCC)SC(C=2C=CC=CC=2)=N1 UIBKHCBQYJSUIW-UHFFFAOYSA-N 0.000 description 1
• YURWUZLFVQPVLW-UHFFFAOYSA-N ethyl 4-(furan-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CO1 YURWUZLFVQPVLW-UHFFFAOYSA-N 0.000 description 1
• JENNEPKYTRKKPL-UHFFFAOYSA-N ethyl 4-(furan-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC=1C=COC=1 JENNEPKYTRKKPL-UHFFFAOYSA-N 0.000 description 1
• ISZTXANXLGWBBD-UHFFFAOYSA-N ethyl 4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound OCC1=C(C(=O)OCC)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 ISZTXANXLGWBBD-UHFFFAOYSA-N 0.000 description 1
• SZSKRILFGVWSJY-UHFFFAOYSA-N ethyl 4-(hydroxymethyl)-2-phenyl-1,3-thiazole-5-carboxylate Chemical compound OCC1=C(C(=O)OCC)SC(C=2C=CC=CC=2)=N1 SZSKRILFGVWSJY-UHFFFAOYSA-N 0.000 description 1
• OAJDVUNBPCAYAL-UHFFFAOYSA-N ethyl 4-(oxan-2-yloxymethyl)-2-phenyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC=CC=2)=NC=1COC1CCCCO1 OAJDVUNBPCAYAL-UHFFFAOYSA-N 0.000 description 1
• ZWBRRCVKSVZELM-UHFFFAOYSA-N ethyl 4-(phenylmethoxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1COCC1=CC=CC=C1 ZWBRRCVKSVZELM-UHFFFAOYSA-N 0.000 description 1
• ZLXOPPMFQXOTON-UHFFFAOYSA-N ethyl 4-(thiophen-2-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CS1 ZLXOPPMFQXOTON-UHFFFAOYSA-N 0.000 description 1
• UJJLSWGKWDOACF-UHFFFAOYSA-N ethyl 4-(thiophen-3-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC=1C=CSC=1 UJJLSWGKWDOACF-UHFFFAOYSA-N 0.000 description 1
• OCYQJLFZDMUKPJ-UHFFFAOYSA-N ethyl 4-[(2,4-difluorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(F)C=C1F OCYQJLFZDMUKPJ-UHFFFAOYSA-N 0.000 description 1
• XNOVEQSCORYMQY-UHFFFAOYSA-N ethyl 4-[(4-bromophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(Br)C=C1 XNOVEQSCORYMQY-UHFFFAOYSA-N 0.000 description 1
• QNIXLXZYJKZBSP-UHFFFAOYSA-N ethyl 4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(OC)C=C1 QNIXLXZYJKZBSP-UHFFFAOYSA-N 0.000 description 1
• TXTGVBVBTNQPDY-UHFFFAOYSA-N ethyl 4-[(4-methylsulfanylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(SC)C=C1 TXTGVBVBTNQPDY-UHFFFAOYSA-N 0.000 description 1
• GHAHTFUSFCCZEM-UHFFFAOYSA-N ethyl 4-[(4-methylthiophen-2-yl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC(C)=CS1 GHAHTFUSFCCZEM-UHFFFAOYSA-N 0.000 description 1
• CIZYJXOXRIVBFO-UHFFFAOYSA-N ethyl 4-[(4-tert-butylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(C(C)(C)C)C=C1 CIZYJXOXRIVBFO-UHFFFAOYSA-N 0.000 description 1
• DVPJHAOMXQIOLE-UHFFFAOYSA-N ethyl 4-[[4-(trifluoromethoxy)phenyl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=C(OC(F)(F)F)C=C1 DVPJHAOMXQIOLE-UHFFFAOYSA-N 0.000 description 1
• YULIOYUQBMAQDS-UHFFFAOYSA-N ethyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-(4-fluorophenyl)-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OCC)N=C(C=2C=CC(F)=CC=2)S1 YULIOYUQBMAQDS-UHFFFAOYSA-N 0.000 description 1
• FVIWPBQPDYZMOL-UHFFFAOYSA-N ethyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OCC)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 FVIWPBQPDYZMOL-UHFFFAOYSA-N 0.000 description 1
• LIZBJDKCDLSEPZ-UHFFFAOYSA-N ethyl 4-[[5-[[4-(1-ethoxy-2-methyl-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-(4-fluorophenyl)-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OC(C)(C)C(=O)OCC)=CC=2)SC(C=2C=CC(F)=CC=2)=N1 LIZBJDKCDLSEPZ-UHFFFAOYSA-N 0.000 description 1
• DRDLLUTUMAEDHS-UHFFFAOYSA-N ethyl 4-[[5-[[4-(1-ethoxy-2-methyl-1-oxopropan-2-yl)oxyphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=CC(OC(C)(C)C(=O)OCC)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 DRDLLUTUMAEDHS-UHFFFAOYSA-N 0.000 description 1
• BRRNNVGTPDPGSU-UHFFFAOYSA-N ethyl 4-[[5-[[4-(2-ethoxy-2-oxoethoxy)-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OCC)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BRRNNVGTPDPGSU-UHFFFAOYSA-N 0.000 description 1
• QXRJBLNEPZIMDP-UHFFFAOYSA-N ethyl 4-[[5-[[4-(2-methoxy-2-oxoethoxy)-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=C(CSC=2C=C(C)C(OCC(=O)OC)=CC=2)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 QXRJBLNEPZIMDP-UHFFFAOYSA-N 0.000 description 1
• ZXBFODHUQJAOAK-UHFFFAOYSA-N ethyl 4-benzyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CC1=CC=CC=C1 ZXBFODHUQJAOAK-UHFFFAOYSA-N 0.000 description 1
• LPIXRQSYBTUXOQ-UHFFFAOYSA-N ethyl 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C=CC(=CC=2)C(F)(F)F)=N1 LPIXRQSYBTUXOQ-UHFFFAOYSA-N 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000013604 expression vector Substances 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000004136 fatty acid synthesis Effects 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 239000012894 fetal calf serum Substances 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000012631 food intake Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 229960002598 fumaric acid Drugs 0.000 description 1
• 108020001507 fusion proteins Proteins 0.000 description 1
• 102000037865 fusion proteins Human genes 0.000 description 1
• LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 229940014259 gelatin Drugs 0.000 description 1
• 230000004190 glucose uptake Effects 0.000 description 1
• 239000003292 glue Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 229960002989 glutamic acid Drugs 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229940116364 hard fat Drugs 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000003463 hyperproliferative effect Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000002513 implantation Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 230000000266 injurious effect Effects 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical group 0.000 description 1
• GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
• 229960004340 lacidipine Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 230000004322 lipid homeostasis Effects 0.000 description 1
• 230000037356 lipid metabolism Effects 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000006193 liquid solution Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 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
• 230000007246 mechanism Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 238000003328 mesylation reaction Methods 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 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
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• XQCGDCADMUOSCD-UHFFFAOYSA-N methyl 2-[4-[[4-(morpholin-4-ylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetate Chemical compound C1=C(C(C)C)C(OCC(=O)OC)=CC=C1SCC1=C(CN2CCOCC2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 XQCGDCADMUOSCD-UHFFFAOYSA-N 0.000 description 1
• WCCXGOLROFBYKU-UHFFFAOYSA-N methyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WCCXGOLROFBYKU-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 229940057867 methyl lactate Drugs 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 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
• 239000007932 molded tablet Substances 0.000 description 1
• 238000012544 monitoring process Methods 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
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 235000006408 oxalic acid Nutrition 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
• MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• QFZVVXAWDZIORD-UHFFFAOYSA-N phenyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-(4-fluorophenyl)-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC=2C=CC=CC=2)N=C(C=2C=CC(F)=CC=2)S1 QFZVVXAWDZIORD-UHFFFAOYSA-N 0.000 description 1
• OSOFCVXWGRXGNQ-UHFFFAOYSA-N phenyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC=2C=CC=CC=2)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 OSOFCVXWGRXGNQ-UHFFFAOYSA-N 0.000 description 1
• AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 108010031345 placental alkaline phosphatase Proteins 0.000 description 1
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• CGTZEMSKDKZHJA-UHFFFAOYSA-N propan-2-yl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-(4-fluorophenyl)-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC(C)C)N=C(C=2C=CC(F)=CC=2)S1 CGTZEMSKDKZHJA-UHFFFAOYSA-N 0.000 description 1
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
• ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 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
• 230000003893 regulation of appetite Effects 0.000 description 1
• 102000027483 retinoid hormone receptors Human genes 0.000 description 1
• 108091008679 retinoid hormone receptors Proteins 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 235000020374 simple syrup Nutrition 0.000 description 1
• 210000002027 skeletal muscle Anatomy 0.000 description 1
• 108091008012 small dense LDL Proteins 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 229960002920 sorbitol Drugs 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 229940032147 starch Drugs 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229960005187 telmisartan Drugs 0.000 description 1
• AAIMAILGXHNHFT-UHFFFAOYSA-N tert-butyl 4-[[5-[[4-(1-ethoxy-1-oxopropan-2-yl)oxy-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OC(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 AAIMAILGXHNHFT-UHFFFAOYSA-N 0.000 description 1
• CMXRYHWVUOYEFN-UHFFFAOYSA-N tert-butyl 4-[[5-[[4-(1-ethoxy-2-methyl-1-oxopropan-2-yl)oxyphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 CMXRYHWVUOYEFN-UHFFFAOYSA-N 0.000 description 1
• DWGNORJGZURHSW-UHFFFAOYSA-N tert-butyl 4-[[5-[[4-(2-methoxy-2-oxoethoxy)-3-methylphenyl]sulfanylmethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1SCC1=C(CN2CCN(CC2)C(=O)OC(C)(C)C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DWGNORJGZURHSW-UHFFFAOYSA-N 0.000 description 1
• MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
• 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 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
• 229940116269 uric acid Drugs 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 230000003442 weekly effect Effects 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1