DE60110262T2 - Thiazol und oxazol-derivate als aktivatoren von menschlichen peroxisom proliferator aktivierten rezeptoren - Google Patents

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Publication number

DE60110262T2

DE60110262T2 DE60110262T DE60110262T DE60110262T2 DE 60110262 T2 DE60110262 T2 DE 60110262T2 DE 60110262 T DE60110262 T DE 60110262T DE 60110262 T DE60110262 T DE 60110262T DE 60110262 T2 DE60110262 T2 DE 60110262T2

Authority

DE

Germany

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 - Lifetime

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• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 3
• 150000007978 oxazole derivatives Chemical class 0.000 title 1
• 210000002824 peroxisome Anatomy 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 105
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 6
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 3
• -1 bromo, phenyl Chemical group 0.000 claims description 167
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 147
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 87
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 35
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 32
• 235000019260 propionic acid Nutrition 0.000 claims description 31
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 18
• 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 239000000556 agonist Substances 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
• 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 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 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 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
• 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 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
• 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 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
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 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 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
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 4
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 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 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
• 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
• 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
• 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
• 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 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
• 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
• 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
• 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 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
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• 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
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• 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
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• 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
• BZGISGMEFSCFEJ-UHFFFAOYSA-N ethyl 2-[2-ethyl-4-[[4-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(CC)C(OCC(=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 BZGISGMEFSCFEJ-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
• JBYKJVHIUUPQRH-UHFFFAOYSA-N ethyl 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]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=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 JBYKJVHIUUPQRH-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
• 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
• 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
• 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
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