JP2005534673A - 化学化合物 - Google Patents
化学化合物 Download PDFInfo
- Publication number
- JP2005534673A JP2005534673A JP2004514762A JP2004514762A JP2005534673A JP 2005534673 A JP2005534673 A JP 2005534673A JP 2004514762 A JP2004514762 A JP 2004514762A JP 2004514762 A JP2004514762 A JP 2004514762A JP 2005534673 A JP2005534673 A JP 2005534673A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- acetic acid
- methylphenoxy
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 221
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- -1 methoxyethyl Chemical group 0.000 claims description 154
- 238000000034 method Methods 0.000 claims description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- YGHHZEFCBIZSSB-UHFFFAOYSA-N 2-[2-methyl-4-[[n-propylsulfonyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(S(=O)(=O)CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 YGHHZEFCBIZSSB-UHFFFAOYSA-N 0.000 claims description 6
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- PEAWRZYPKVFBPF-UHFFFAOYSA-N 2-[2-methyl-4-[[n-pentyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PEAWRZYPKVFBPF-UHFFFAOYSA-N 0.000 claims description 4
- HRQANTBARMMGIA-UHFFFAOYSA-N 2-[2-methyl-4-[[prop-2-enyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CN(CC=C)C=2N=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HRQANTBARMMGIA-UHFFFAOYSA-N 0.000 claims description 4
- IJYQDIOFQBLRMI-UHFFFAOYSA-N 2-[4-[2-cyclopropylethyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(S(=O)(=O)N(CCC2CC2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 IJYQDIOFQBLRMI-UHFFFAOYSA-N 0.000 claims description 4
- YSMHQYZKUOJMKJ-UHFFFAOYSA-N 2-[4-[[[4-(4-chlorophenyl)pyrimidin-2-yl]-(2-methoxyethyl)amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 YSMHQYZKUOJMKJ-UHFFFAOYSA-N 0.000 claims description 4
- IJHBSKLFWNWLAT-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 IJHBSKLFWNWLAT-UHFFFAOYSA-N 0.000 claims description 4
- IADOHFNPFBVSGF-UHFFFAOYSA-N 2-[4-[[n-butyl-2-methyl-3-(4-methylphenyl)anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 IADOHFNPFBVSGF-UHFFFAOYSA-N 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- UVNNBABQBZZBNO-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-methoxyethyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(CN(CCOC)C=2N=C(C=CN=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UVNNBABQBZZBNO-UHFFFAOYSA-N 0.000 claims description 3
- KNOPTCHXVXPURE-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-3-(4-methylphenyl)-n-propylanilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KNOPTCHXVXPURE-UHFFFAOYSA-N 0.000 claims description 3
- GOPJHQJXIVHRQS-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-n-propyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 GOPJHQJXIVHRQS-UHFFFAOYSA-N 0.000 claims description 3
- VDKVCJMUCCAMMG-UHFFFAOYSA-N 2-[2-methyl-4-[[[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]-propylamino]methyl]phenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 VDKVCJMUCCAMMG-UHFFFAOYSA-N 0.000 claims description 3
- ZDYXOCIDDCFARL-UHFFFAOYSA-N 2-[2-methyl-4-[[[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]-propylamino]methyl]phenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 ZDYXOCIDDCFARL-UHFFFAOYSA-N 0.000 claims description 3
- RRCPLRUPTKQMHM-UHFFFAOYSA-N 2-[2-methyl-4-[[n-propyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 RRCPLRUPTKQMHM-UHFFFAOYSA-N 0.000 claims description 3
- XSJSAVYSMORDHC-UHFFFAOYSA-N 2-[2-methyl-4-[[propyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 XSJSAVYSMORDHC-UHFFFAOYSA-N 0.000 claims description 3
- PRKYXPRHKQIKBQ-UHFFFAOYSA-N 2-[2-methyl-4-[[propyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PRKYXPRHKQIKBQ-UHFFFAOYSA-N 0.000 claims description 3
- OGIZWBGYLHQGQE-UHFFFAOYSA-N 2-[2-methyl-4-[pentyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCCC)C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 OGIZWBGYLHQGQE-UHFFFAOYSA-N 0.000 claims description 3
- HBFDXJXPMJPDGU-UHFFFAOYSA-N 2-[4-[[2-methoxyethyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 HBFDXJXPMJPDGU-UHFFFAOYSA-N 0.000 claims description 3
- KNOLRYLXOFIMIC-UHFFFAOYSA-N 2-[4-[[2-methoxyethyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 KNOLRYLXOFIMIC-UHFFFAOYSA-N 0.000 claims description 3
- GJJIZDVLTCBHKV-UHFFFAOYSA-N 2-[4-[[3-(4-chlorophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 GJJIZDVLTCBHKV-UHFFFAOYSA-N 0.000 claims description 3
- WLPNPIDPJYCYBO-UHFFFAOYSA-N 2-[4-[[3-(4-chlorophenyl)-n-(2-methoxyethyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 WLPNPIDPJYCYBO-UHFFFAOYSA-N 0.000 claims description 3
- VENARYATHGDLAJ-UHFFFAOYSA-N 2-[4-[[3-(4-cyanophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 VENARYATHGDLAJ-UHFFFAOYSA-N 0.000 claims description 3
- PGEUUOYZXAXZAZ-UHFFFAOYSA-N 2-[4-[[3-(4-fluorophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PGEUUOYZXAXZAZ-UHFFFAOYSA-N 0.000 claims description 3
- MUMOEDHFUPBHAZ-UHFFFAOYSA-N 2-[4-[[3-(4-methoxyphenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MUMOEDHFUPBHAZ-UHFFFAOYSA-N 0.000 claims description 3
- MXNYXSHIAHNYNW-UHFFFAOYSA-N 2-[4-[[[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MXNYXSHIAHNYNW-UHFFFAOYSA-N 0.000 claims description 3
- YMCNXXXIEVJJAB-UHFFFAOYSA-N 2-[4-[[[6-(4-chlorophenyl)pyrazin-2-yl]-(2-methoxyethyl)amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 YMCNXXXIEVJJAB-UHFFFAOYSA-N 0.000 claims description 3
- KGCILICKONKQJI-UHFFFAOYSA-N 2-[4-[[[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KGCILICKONKQJI-UHFFFAOYSA-N 0.000 claims description 3
- HKXPKBPNHDYJCY-UHFFFAOYSA-N 2-[4-[[butyl-[4-(4-chlorophenyl)pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 HKXPKBPNHDYJCY-UHFFFAOYSA-N 0.000 claims description 3
- QURKGEHGLGJPRN-UHFFFAOYSA-N 2-[4-[[butyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 QURKGEHGLGJPRN-UHFFFAOYSA-N 0.000 claims description 3
- HPOJZOUKBUUIFU-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 HPOJZOUKBUUIFU-UHFFFAOYSA-N 0.000 claims description 3
- KJJUOYZUPWKUFR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KJJUOYZUPWKUFR-UHFFFAOYSA-N 0.000 claims description 3
- ZGSKFRBNMTYPHR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 ZGSKFRBNMTYPHR-UHFFFAOYSA-N 0.000 claims description 3
- MPYIHZGPRROZIR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MPYIHZGPRROZIR-UHFFFAOYSA-N 0.000 claims description 3
- SBAZZTXQGDFQLR-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 SBAZZTXQGDFQLR-UHFFFAOYSA-N 0.000 claims description 3
- YURCSFYCXRYRBB-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 YURCSFYCXRYRBB-UHFFFAOYSA-N 0.000 claims description 3
- FBZXXHOWTFOFRV-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 FBZXXHOWTFOFRV-UHFFFAOYSA-N 0.000 claims description 3
- ASRAFPYPVQCHCA-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-methylphenyl)pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(C)=CC=2)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 ASRAFPYPVQCHCA-UHFFFAOYSA-N 0.000 claims description 3
- MENHQMYKCSUBHI-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 MENHQMYKCSUBHI-UHFFFAOYSA-N 0.000 claims description 3
- SBOOXZMRYAEKJJ-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 SBOOXZMRYAEKJJ-UHFFFAOYSA-N 0.000 claims description 3
- CBCQOWIYROCGPP-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 CBCQOWIYROCGPP-UHFFFAOYSA-N 0.000 claims description 3
- LNIZHEWUDRFHHK-UHFFFAOYSA-N 2-[4-[[n-(2-cyclopropylethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CN(CCC2CC2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 LNIZHEWUDRFHHK-UHFFFAOYSA-N 0.000 claims description 3
- VAYOMOVBKJCJNQ-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 VAYOMOVBKJCJNQ-UHFFFAOYSA-N 0.000 claims description 3
- UMJHPUYANMIRNB-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-3-(4-methoxyphenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 UMJHPUYANMIRNB-UHFFFAOYSA-N 0.000 claims description 3
- UGSMMDAQHBSSAD-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 UGSMMDAQHBSSAD-UHFFFAOYSA-N 0.000 claims description 3
- LRGPFBCSWCOXRN-UHFFFAOYSA-N 2-[4-[[n-butanoyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(C(=O)CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 LRGPFBCSWCOXRN-UHFFFAOYSA-N 0.000 claims description 3
- WFZQERNBKRHAIN-UHFFFAOYSA-N 2-[4-[[n-butyl-2-methyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 WFZQERNBKRHAIN-UHFFFAOYSA-N 0.000 claims description 3
- XYUNARUZUYIHQQ-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-chlorophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 XYUNARUZUYIHQQ-UHFFFAOYSA-N 0.000 claims description 3
- PCZJCGPQUZKIRC-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-cyanophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PCZJCGPQUZKIRC-UHFFFAOYSA-N 0.000 claims description 3
- NQSRVOZQRCJMFK-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-fluorophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 NQSRVOZQRCJMFK-UHFFFAOYSA-N 0.000 claims description 3
- QPYMSJJYJSJLDH-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-methoxyphenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 QPYMSJJYJSJLDH-UHFFFAOYSA-N 0.000 claims description 3
- PKSVTAGTVUPRTI-UHFFFAOYSA-N 2-[4-[[n-butyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PKSVTAGTVUPRTI-UHFFFAOYSA-N 0.000 claims description 3
- DJPKXZIMROQBTG-UHFFFAOYSA-N 2-[4-[butyl-[2-methyl-3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCC)C(C=1C)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 DJPKXZIMROQBTG-UHFFFAOYSA-N 0.000 claims description 3
- IBRDZTWPODVPSV-UHFFFAOYSA-N 2-[4-[butyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCC)C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 IBRDZTWPODVPSV-UHFFFAOYSA-N 0.000 claims description 3
- KXEDACREUUFVAI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[4-(trifluoromethyl)phenyl]methyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CN(CC=2C=CC(=CC=2)C(F)(F)F)C=2N=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 KXEDACREUUFVAI-UHFFFAOYSA-N 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- MJEXFSLFJSRENW-UHFFFAOYSA-N 2-[2-methyl-4-[[n-(2-methylsulfanylethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCSC)CC1=CC=C(OCC(O)=O)C(C)=C1 MJEXFSLFJSRENW-UHFFFAOYSA-N 0.000 claims description 2
- XQADWKSWAZXWCW-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-2-methyl-3-(4-methylphenyl)anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 XQADWKSWAZXWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 482
- 235000019439 ethyl acetate Nutrition 0.000 description 223
- 239000000243 solution Substances 0.000 description 172
- 239000000543 intermediate Substances 0.000 description 138
- 238000001819 mass spectrum Methods 0.000 description 138
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 134
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 126
- 239000002904 solvent Substances 0.000 description 124
- 239000000203 mixture Substances 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 72
- 238000000746 purification Methods 0.000 description 71
- 239000000377 silicon dioxide Substances 0.000 description 66
- 229910052757 nitrogen Inorganic materials 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- 239000007787 solid Substances 0.000 description 62
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 56
- 230000002209 hydrophobic effect Effects 0.000 description 50
- 238000004587 chromatography analysis Methods 0.000 description 48
- 239000003921 oil Substances 0.000 description 45
- 235000019198 oils Nutrition 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 239000000284 extract Substances 0.000 description 35
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 30
- 239000012230 colorless oil Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- 239000011734 sodium Substances 0.000 description 23
- 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 21
- 238000003756 stirring Methods 0.000 description 21
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 18
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 238000003556 assay Methods 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 14
- 239000000556 agonist Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 108010016731 PPAR gamma Proteins 0.000 description 12
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 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 8
- 239000004480 active ingredient Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- 238000001890 transfection Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 102000023984 PPAR alpha Human genes 0.000 description 7
- 230000004913 activation Effects 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 6
- SJLPRKVKCMCIKV-UHFFFAOYSA-N 2-chloro-6-[4-(trifluoromethyl)phenyl]pyrazine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=CC(Cl)=N1 SJLPRKVKCMCIKV-UHFFFAOYSA-N 0.000 description 6
- RTSCKIULIJLTHO-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]aniline Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 RTSCKIULIJLTHO-UHFFFAOYSA-N 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 108010015181 PPAR delta Proteins 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 5
- DRDUGYIPUFVJGO-UHFFFAOYSA-N 2-bromo-6-[4-(trifluoromethyl)phenyl]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC(Br)=N1 DRDUGYIPUFVJGO-UHFFFAOYSA-N 0.000 description 5
- IILVSKMKMOJHMA-UHFFFAOYSA-N 3-bromo-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Br IILVSKMKMOJHMA-UHFFFAOYSA-N 0.000 description 5
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000013641 positive control Substances 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- HTFXWAOSQODIBI-UHFFFAOYSA-N 2-benzyl-1,3-dihydropyrrolo[3,4-c]pyridine Chemical compound C1C2=CC=NC=C2CN1CC1=CC=CC=C1 HTFXWAOSQODIBI-UHFFFAOYSA-N 0.000 description 4
- XFNGSFGXNXDKOL-UHFFFAOYSA-N 2-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XFNGSFGXNXDKOL-UHFFFAOYSA-N 0.000 description 4
- NUEYDUKUIXVKNB-UHFFFAOYSA-N 4,6-dichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=CN=C1Cl NUEYDUKUIXVKNB-UHFFFAOYSA-N 0.000 description 4
- DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 4
- PKRDCFOIQMGNGY-UHFFFAOYSA-N 4-chloro-5-methyl-6-(4-methylphenyl)pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC=NC(Cl)=C1C PKRDCFOIQMGNGY-UHFFFAOYSA-N 0.000 description 4
- YTHKHTLLTQHLNM-UHFFFAOYSA-N 4-chloro-6-(4-chlorophenyl)-5-methylpyrimidine Chemical compound CC1=C(Cl)N=CN=C1C1=CC=C(Cl)C=C1 YTHKHTLLTQHLNM-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 4
- LEOHBKZQGMANCG-UHFFFAOYSA-N C=1C=CC(Br)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 Chemical compound C=1C=CC(Br)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 LEOHBKZQGMANCG-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
- 229920000084 Gum arabic Polymers 0.000 description 4
- 108010007622 LDL Lipoproteins Proteins 0.000 description 4
- 102000007330 LDL Lipoproteins Human genes 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 229940123464 Thiazolidinedione Drugs 0.000 description 4
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- 150000001299 aldehydes Chemical group 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- LFQVAPPPNNRBAH-UHFFFAOYSA-N ethyl 2-[4-(bromomethyl)-2-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(CBr)C=C1C LFQVAPPPNNRBAH-UHFFFAOYSA-N 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 108020001756 ligand binding domains Proteins 0.000 description 4
- 238000006268 reductive amination reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 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 4
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 3
- DYOZNCVZPFIXLU-UHFFFAOYSA-N 1,1,2-trimethoxyethane Chemical compound COCC(OC)OC DYOZNCVZPFIXLU-UHFFFAOYSA-N 0.000 description 3
- LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical compound ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 3
- OEFKDVLPYNVBHQ-UHFFFAOYSA-N 2-bromo-6-[4-(trifluoromethyl)phenyl]pyrazine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=CC(Br)=N1 OEFKDVLPYNVBHQ-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- FXJOWVORINHRAB-UHFFFAOYSA-N 2-methyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CC1=C(N)C=CC=C1C1=CC=C(C(F)(F)F)C=C1 FXJOWVORINHRAB-UHFFFAOYSA-N 0.000 description 3
- TYMBZAFFYUTXMW-UHFFFAOYSA-N 2-methylsulfanyl-4-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CSC1=NC=CC(C=2C=CC(=CC=2)C(F)(F)F)=N1 TYMBZAFFYUTXMW-UHFFFAOYSA-N 0.000 description 3
- GOXDPARPMAHJSL-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(C=2C=CC(Cl)=CC=2)=N1 GOXDPARPMAHJSL-UHFFFAOYSA-N 0.000 description 3
- BAKYASSDAXQKKY-UHFFFAOYSA-N 4-Hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1O BAKYASSDAXQKKY-UHFFFAOYSA-N 0.000 description 3
- FWHNFPGLIDMZBO-UHFFFAOYSA-N 4-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CC1=C(Cl)N=CN=C1C1=CC=C(C(F)(F)F)C=C1 FWHNFPGLIDMZBO-UHFFFAOYSA-N 0.000 description 3
- AABNLLGCOOPFGZ-UHFFFAOYSA-N 4-chloro-6-(4-methoxyphenyl)-5-methylpyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC=NC(Cl)=C1C AABNLLGCOOPFGZ-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 102100026189 Beta-galactosidase Human genes 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 3
- 102000043296 Lipoprotein lipases Human genes 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 108010005774 beta-Galactosidase Proteins 0.000 description 3
- 125000006309 butyl amino group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 210000004027 cell Anatomy 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
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 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 3
- LGFLIRUIOHPEKX-UHFFFAOYSA-N ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C=O)C=C1C LGFLIRUIOHPEKX-UHFFFAOYSA-N 0.000 description 3
- CMLGOHXFHRGELV-UHFFFAOYSA-N ethyl 2-(4-formyl-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C=O)C=C1C CMLGOHXFHRGELV-UHFFFAOYSA-N 0.000 description 3
- GXLGIYBBQXTODC-UHFFFAOYSA-N ethyl 2-[4-(butylaminomethyl)-2-methylphenoxy]acetate Chemical compound CCCCNCC1=CC=C(OCC(=O)OCC)C(C)=C1 GXLGIYBBQXTODC-UHFFFAOYSA-N 0.000 description 3
- 238000011010 flushing procedure Methods 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
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- ZSJXYVKUEPEZFK-UHFFFAOYSA-N n-(2-cyclopropylethyl)-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC(NCCC2CC2)=C1 ZSJXYVKUEPEZFK-UHFFFAOYSA-N 0.000 description 3
- IHPZNLRBNNXJNI-UHFFFAOYSA-N n-[2-methyl-3-(4-methylphenyl)phenyl]butanamide Chemical compound CCCC(=O)NC1=CC=CC(C=2C=CC(C)=CC=2)=C1C IHPZNLRBNNXJNI-UHFFFAOYSA-N 0.000 description 3
- HLAQWMQUTDHVRC-UHFFFAOYSA-N n-butyl-2-methyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CCCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1C HLAQWMQUTDHVRC-UHFFFAOYSA-N 0.000 description 3
- MOIQYKAGXIKGIT-UHFFFAOYSA-N n-butyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CCCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 MOIQYKAGXIKGIT-UHFFFAOYSA-N 0.000 description 3
- YGDDSWMCADDCTP-UHFFFAOYSA-N n-pentyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CCCCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 YGDDSWMCADDCTP-UHFFFAOYSA-N 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 229960004586 rosiglitazone Drugs 0.000 description 3
- 238000002821 scintillation proximity assay Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000003146 transient transfection Methods 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 2
- CXXLMBYQEQWGTM-UHFFFAOYSA-N 2-bromo-6-(4-chlorophenyl)pyrazine Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(Br)=N1 CXXLMBYQEQWGTM-UHFFFAOYSA-N 0.000 description 2
- CGCKXIMIKJDOAG-UHFFFAOYSA-N 2-bromo-6-(4-methylphenyl)pyrazine Chemical compound C1=CC(C)=CC=C1C1=CN=CC(Br)=N1 CGCKXIMIKJDOAG-UHFFFAOYSA-N 0.000 description 2
- IXNZYIPBGXYXFS-UHFFFAOYSA-N 2-chloro-6-(4-chlorophenyl)pyrazine Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(Cl)=N1 IXNZYIPBGXYXFS-UHFFFAOYSA-N 0.000 description 2
- SPNHICMLNGTAFL-UHFFFAOYSA-N 2-chloro-6-(4-methylphenyl)pyrazine Chemical compound C1=CC(C)=CC=C1C1=CN=CC(Cl)=N1 SPNHICMLNGTAFL-UHFFFAOYSA-N 0.000 description 2
- LSGNENXQYZJBCJ-UHFFFAOYSA-N 2-ethyl-4-(hydroxymethyl)phenol Chemical compound CCC1=CC(CO)=CC=C1O LSGNENXQYZJBCJ-UHFFFAOYSA-N 0.000 description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
- ZJUPPUMPLNHTCB-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1C1=CC=CC(N)=C1C ZJUPPUMPLNHTCB-UHFFFAOYSA-N 0.000 description 2
- DYYQACNIJYWARH-UHFFFAOYSA-N 3-bromo-2-methyl-n-propylaniline Chemical compound CCCNC1=CC=CC(Br)=C1C DYYQACNIJYWARH-UHFFFAOYSA-N 0.000 description 2
- HUQSTGAEJDIFFU-UHFFFAOYSA-N 3-bromo-n-(2-methoxyethyl)-2-methylaniline Chemical compound COCCNC1=CC=CC(Br)=C1C HUQSTGAEJDIFFU-UHFFFAOYSA-N 0.000 description 2
- LKGPBEYAKNOFQM-UHFFFAOYSA-N 3-bromo-n-butyl-2-methylaniline Chemical compound CCCCNC1=CC=CC(Br)=C1C LKGPBEYAKNOFQM-UHFFFAOYSA-N 0.000 description 2
- HSKGHUJMBLYPDO-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methylphenol Chemical compound CC1=CC(CO)=CC=C1O HSKGHUJMBLYPDO-UHFFFAOYSA-N 0.000 description 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000004568 DNA-binding Effects 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
- 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 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
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 239000000305 astragalus gummifer gum Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- PLQICMRAXWGOHS-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]-propylamino]methyl]phenoxy]acetate Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 PLQICMRAXWGOHS-UHFFFAOYSA-N 0.000 description 2
- YLIKWNPDJSLLTB-UHFFFAOYSA-N ethyl 2-[4-(butylaminomethyl)-2-methylphenoxy]-2-methylpropanoate Chemical compound CCCCNCC1=CC=C(OC(C)(C)C(=O)OCC)C(C)=C1 YLIKWNPDJSLLTB-UHFFFAOYSA-N 0.000 description 2
- OZLNMXVIVLDHQU-UHFFFAOYSA-N ethyl 2-[4-[(2-methoxyethylamino)methyl]-2-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(CNCCOC)C=C1C OZLNMXVIVLDHQU-UHFFFAOYSA-N 0.000 description 2
- YNAJTUAUZSBTGX-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1CNCC1=CC=C(C(F)(F)F)C=C1 YNAJTUAUZSBTGX-UHFFFAOYSA-N 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 229940012952 fibrinogen Drugs 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 102000054223 human PPARA Human genes 0.000 description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JJOUCAIPYVMXIE-UHFFFAOYSA-N methyl 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]-2-methylphenoxy]acetate Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(=O)OC)C(C)=C1 JJOUCAIPYVMXIE-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- VIYJOTCQCGPMGV-UHFFFAOYSA-N n-(2-methoxyethyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound COCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1C VIYJOTCQCGPMGV-UHFFFAOYSA-N 0.000 description 2
- RTRCAWJATTXBLG-UHFFFAOYSA-N n-(2-methylsulfanylethyl)-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CSCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 RTRCAWJATTXBLG-UHFFFAOYSA-N 0.000 description 2
- CXYXZCROQMNLGU-UHFFFAOYSA-N n-butyl-2-methyl-3-(4-methylphenyl)aniline Chemical compound CCCCNC1=CC=CC(C=2C=CC(C)=CC=2)=C1C CXYXZCROQMNLGU-UHFFFAOYSA-N 0.000 description 2
- ROEGDUSNBMJZIB-UHFFFAOYSA-N n-prop-2-enyl-6-[4-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC(NCC=C)=N1 ROEGDUSNBMJZIB-UHFFFAOYSA-N 0.000 description 2
- PXGMHKICHWQWAE-UHFFFAOYSA-N n-propyl-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound CCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 PXGMHKICHWQWAE-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-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
- 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
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 201000009104 prediabetes syndrome Diseases 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 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
- 150000001467 thiazolidinediones Chemical class 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VHFJQHIIRCYEPN-UHFFFAOYSA-N (4-cyanophenyl)boron Chemical compound [B]C1=CC=C(C#N)C=C1 VHFJQHIIRCYEPN-UHFFFAOYSA-N 0.000 description 1
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- YGGMQWSJXSNGDT-UHFFFAOYSA-N (4-fluorophenyl)boron Chemical compound [B]C1=CC=C(F)C=C1 YGGMQWSJXSNGDT-UHFFFAOYSA-N 0.000 description 1
- NQMRYYAAICMHPE-UHFFFAOYSA-N (4-methoxyphenyl)boron Chemical compound [B]C1=CC=C(OC)C=C1 NQMRYYAAICMHPE-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
- FMRPQNGHKPJXCZ-UHFFFAOYSA-N 1,1-diethoxy-2-methylsulfanylethane Chemical compound CCOC(CSC)OCC FMRPQNGHKPJXCZ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-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
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- MLCNOCRGSBCAGH-UHFFFAOYSA-N 2,3-dichloropyrazine Chemical compound ClC1=NC=CN=C1Cl MLCNOCRGSBCAGH-UHFFFAOYSA-N 0.000 description 1
- YQHSRAQHJSBAEO-UHFFFAOYSA-N 2-(4-methylphenyl)pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC=CC=N1 YQHSRAQHJSBAEO-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
- CTWRFFSUIKIDKK-UHFFFAOYSA-N 2-[2-ethyl-4-[[n-(2-methoxyethyl)-2-methyl-3-(4-methylphenyl)anilino]methyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(CN(CCOC)C=2C(=C(C=CC=2)C=2C=CC(C)=CC=2)C)=C1 CTWRFFSUIKIDKK-UHFFFAOYSA-N 0.000 description 1
- RWDBWNUDGQKLSL-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC=N1 RWDBWNUDGQKLSL-UHFFFAOYSA-N 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- LUNMJRJMSXZSLC-UHFFFAOYSA-N 2-cyclopropylethanol Chemical compound OCCC1CC1 LUNMJRJMSXZSLC-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
- ILUPZUOBHCUBKB-UHFFFAOYSA-N 2-methyl-2-(4-{[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}carbonyl)amino]methyl}phenoxy)propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C=C1 ILUPZUOBHCUBKB-UHFFFAOYSA-N 0.000 description 1
- FVKORRJUEDJXCF-UHFFFAOYSA-N 2-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]pyrimidine;pyrimidine Chemical compound C1=CN=CN=C1.CS(=O)(=O)C1=NC=CC(C=2C=CC(=CC=2)C(F)(F)F)=N1 FVKORRJUEDJXCF-UHFFFAOYSA-N 0.000 description 1
- OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-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
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-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
- GANMHEZDTJWGJW-UHFFFAOYSA-N 3-ethyl-4-hydroxybenzaldehyde Chemical compound CCC1=CC(C=O)=CC=C1O GANMHEZDTJWGJW-UHFFFAOYSA-N 0.000 description 1
- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical class ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-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
- ADGRYYARNGJCIR-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(C=2C=CC(Cl)=CC=2)=N1 ADGRYYARNGJCIR-UHFFFAOYSA-N 0.000 description 1
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 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
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229940123073 Angiotensin antagonist Drugs 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- OZZCTIIDZSKGRP-UHFFFAOYSA-N CCCCCN(Cc(cc1C)ccc1OCC(OCC)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1 Chemical compound CCCCCN(Cc(cc1C)ccc1OCC(OCC)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1 OZZCTIIDZSKGRP-UHFFFAOYSA-N 0.000 description 1
- HOBRJGIFKMDUCU-UHFFFAOYSA-N CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1c(C)c(-c2ccc(C)cc2)ncn1 Chemical compound CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1c(C)c(-c2ccc(C)cc2)ncn1 HOBRJGIFKMDUCU-UHFFFAOYSA-N 0.000 description 1
- CZEYADKWNSPQCA-UHFFFAOYSA-N CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1 Chemical compound CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1 CZEYADKWNSPQCA-UHFFFAOYSA-N 0.000 description 1
- IQQRTISHVKAVSB-UHFFFAOYSA-N CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1nc(-c2ccc(C)cc2)cnc1 Chemical compound CCCCN(Cc(cc1)cc(C)c1OCC(OCC)=O)c1nc(-c2ccc(C)cc2)cnc1 IQQRTISHVKAVSB-UHFFFAOYSA-N 0.000 description 1
- MVSSQXKTUYQSOH-UHFFFAOYSA-N CCCCNCC1=CC=C(OCC(O)=O)C(C)=C1 Chemical compound CCCCNCC1=CC=C(OCC(O)=O)C(C)=C1 MVSSQXKTUYQSOH-UHFFFAOYSA-N 0.000 description 1
- YZNFMCBNAUNFBW-UHFFFAOYSA-N CCCS(N(Cc(cc1CC)ccc1OCC(O)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1)(=O)=O Chemical compound CCCS(N(Cc(cc1CC)ccc1OCC(O)=O)c1cccc(-c2ccc(C(F)(F)F)cc2)c1)(=O)=O YZNFMCBNAUNFBW-UHFFFAOYSA-N 0.000 description 1
- UYKCKHAVXOMPNZ-UHFFFAOYSA-N CCOC(COc1ccc(CN(CCOC)c2c(C)c(-c3ccc(C(F)(F)F)cc3)ccc2)cc1C)=O Chemical compound CCOC(COc1ccc(CN(CCOC)c2c(C)c(-c3ccc(C(F)(F)F)cc3)ccc2)cc1C)=O UYKCKHAVXOMPNZ-UHFFFAOYSA-N 0.000 description 1
- RWFRBWVVFSKKEW-UHFFFAOYSA-N CCc(cc(CNCCOC)cc1)c1OCC(OCC)=O Chemical compound CCc(cc(CNCCOC)cc1)c1OCC(OCC)=O RWFRBWVVFSKKEW-UHFFFAOYSA-N 0.000 description 1
- 0 CS(c1nc(*)ccn1)(=O)=O Chemical compound CS(c1nc(*)ccn1)(=O)=O 0.000 description 1
- QVYPJRBQILVKET-UHFFFAOYSA-N CSc1nc([AlH2])ccn1 Chemical compound CSc1nc([AlH2])ccn1 QVYPJRBQILVKET-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000028698 Cognitive impairment Diseases 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 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 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
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010060378 Hyperinsulinaemia 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
- 241000282560 Macaca mulatta Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 101000741778 Mus musculus Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 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
- 229940124754 PPAR-alpha/gamma agonist Drugs 0.000 description 1
- 108010044210 PPAR-beta Proteins 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 208000019802 Sexually transmitted disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-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
- 108010090804 Streptavidin Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 description 1
- AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000010210 aluminium Nutrition 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
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 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
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 229940125708 antidiabetic agent 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
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000923 atherogenic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group 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
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 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
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004067 bulking agent 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
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-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
- 201000011510 cancer Diseases 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 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
- 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
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical class OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- MQYQOVYIJOLTNX-UHFFFAOYSA-N dichloromethane;n,n-dimethylformamide Chemical compound ClCCl.CN(C)C=O MQYQOVYIJOLTNX-UHFFFAOYSA-N 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
- 230000004069 differentiation Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940125542 dual agonist Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 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
- 125000004185 ester group Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- GSHNDMOUSPLZPF-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1CNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 GSHNDMOUSPLZPF-UHFFFAOYSA-N 0.000 description 1
- UBMDOJVGQBAMCK-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[propyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]phenoxy]acetate Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 UBMDOJVGQBAMCK-UHFFFAOYSA-N 0.000 description 1
- QVFHBWKYSCLWOG-UHFFFAOYSA-N ethyl 2-[4-[[[4-(4-chlorophenyl)pyrimidin-2-yl]-(2-methoxyethyl)amino]methyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1CN(CCOC)C1=NC=CC(C=2C=CC(Cl)=CC=2)=N1 QVFHBWKYSCLWOG-UHFFFAOYSA-N 0.000 description 1
- ZVKVQUSWYRLGQJ-UHFFFAOYSA-N ethyl 2-[4-[[[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetate Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 ZVKVQUSWYRLGQJ-UHFFFAOYSA-N 0.000 description 1
- HCQWXMHSFLYPLY-UHFFFAOYSA-N ethyl 2-[4-[[[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetate Chemical compound N=1C=NC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 HCQWXMHSFLYPLY-UHFFFAOYSA-N 0.000 description 1
- LOXMDJKCIXUBLA-UHFFFAOYSA-N ethyl 2-[4-[[butyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetate Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 LOXMDJKCIXUBLA-UHFFFAOYSA-N 0.000 description 1
- IHNGZKGQWIFDBW-UHFFFAOYSA-N ethyl 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-ethylphenoxy]acetate Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(=O)OCC)C(CC)=C1 IHNGZKGQWIFDBW-UHFFFAOYSA-N 0.000 description 1
- VDKJNEOZUQDEAZ-UHFFFAOYSA-N ethyl 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetate Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(=O)OCC)C(C)=C1 VDKJNEOZUQDEAZ-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
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 239000013604 expression vector 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 230000004190 glucose uptake Effects 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
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect 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
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 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
- 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
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 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
- 239000012669 liquid formulation 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 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
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- ZWGOYXFAJNCEQA-UHFFFAOYSA-N methyl 2-[2-methyl-4-[[n-(2-methylsulfanylethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1CN(CCSC)C1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 ZWGOYXFAJNCEQA-UHFFFAOYSA-N 0.000 description 1
- MKSNIDXOIKVDBG-UHFFFAOYSA-N methyl 2-[4-(bromomethyl)-2-methylphenoxy]acetate Chemical compound COC(=O)COC1=CC=C(CBr)C=C1C MKSNIDXOIKVDBG-UHFFFAOYSA-N 0.000 description 1
- YCEVCPYPTVJXNE-UHFFFAOYSA-N methyl 2-[4-(butylaminomethyl)-2-methylphenoxy]acetate Chemical compound CCCCNCC1=CC=C(OCC(=O)OC)C(C)=C1 YCEVCPYPTVJXNE-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- RANMPVZMNXIUMP-UHFFFAOYSA-N n-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]aniline Chemical compound COCCNC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 RANMPVZMNXIUMP-UHFFFAOYSA-N 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
- 239000002687 nonaqueous vehicle Substances 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
- 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
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 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
- 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
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 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
- 239000002594 sorbent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form 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
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0214254.5A GB0214254D0 (en) | 2002-06-20 | 2002-06-20 | Chemical compounds |
| PCT/EP2003/006416 WO2004000762A2 (en) | 2002-06-20 | 2003-06-18 | Propionic acid derivatives and their use as hppars activators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005534673A true JP2005534673A (ja) | 2005-11-17 |
| JP2005534673A5 JP2005534673A5 (enExample) | 2006-06-15 |
Family
ID=9938981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004514762A Pending JP2005534673A (ja) | 2002-06-20 | 2003-06-18 | 化学化合物 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7199239B2 (enExample) |
| EP (1) | EP1513795A2 (enExample) |
| JP (1) | JP2005534673A (enExample) |
| KR (1) | KR20050013590A (enExample) |
| CN (1) | CN100349856C (enExample) |
| AU (1) | AU2003245963C1 (enExample) |
| BR (1) | BR0311935A (enExample) |
| CA (1) | CA2489359A1 (enExample) |
| GB (1) | GB0214254D0 (enExample) |
| IL (1) | IL165477A0 (enExample) |
| IS (1) | IS7575A (enExample) |
| MX (1) | MXPA04012858A (enExample) |
| NO (1) | NO20045327L (enExample) |
| NZ (1) | NZ537209A (enExample) |
| PL (1) | PL375075A1 (enExample) |
| RU (1) | RU2316539C2 (enExample) |
| WO (1) | WO2004000762A2 (enExample) |
| ZA (1) | ZA200410054B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1599468E (pt) | 2003-01-14 | 2008-01-14 | Arena Pharm Inc | Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia |
| GB2423781B (en) | 2003-03-19 | 2007-03-28 | Varco Int | Apparatus and method for moving drilled cuttings |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP2287165A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| WO2005007627A1 (ja) * | 2003-07-18 | 2005-01-27 | Nihon Nohyaku Co., Ltd. | フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤 |
| EP1745014B1 (en) | 2004-05-05 | 2011-07-06 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| WO2005105726A1 (en) | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
| BR122017014864B1 (pt) | 2004-06-22 | 2018-06-05 | Varco I/P, Inc. | Método e sistema para processamento de material de detritos de perfuração |
| DE102004046623A1 (de) * | 2004-09-25 | 2006-03-30 | Bayer Healthcare Ag | Neue Pyrimidin-Derivate und ihre Verwendung |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| US7301033B2 (en) | 2005-01-27 | 2007-11-27 | Kowa Co., Ltd. | PPAR-activating compound |
| EP2298742B1 (en) | 2005-06-30 | 2014-01-08 | High Point Pharmaceuticals, LLC | phenoxy acetic acids as PPAR delta activators |
| EP2386540A1 (en) | 2005-12-22 | 2011-11-16 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| CA2645719A1 (en) | 2006-03-09 | 2007-09-13 | High Point Pharmaceuticals, Llc | Compounds that modulate ppar activity, their preparation and use |
| RU2538276C2 (ru) * | 2009-04-23 | 2015-01-10 | Пирамал Имэджинг СА | Новые прекурсорные молекулы для меченных f-18 пэт радиоактивных индикаторов |
| WO2011002814A2 (en) * | 2009-06-30 | 2011-01-06 | Ligand Pharmaceuticals Inc. | Biaryl oxyacetic acid compounds |
| JP2012041325A (ja) | 2010-08-23 | 2012-03-01 | Bayer Cropscience Ag | オキサジアゾリノン誘導体およびその有害生物の防除用途 |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ, インコーポレイテッド | Gpr119レセプターのモジュレーターおよびそれに関連する障害の処置 |
| WO2015035171A1 (en) | 2013-09-09 | 2015-03-12 | High Point Pharmaceuticals, Llc | Use of a ppar-delta agonist for treating muscle atrophy |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| DK3310760T3 (da) | 2015-06-22 | 2022-10-24 | Arena Pharm Inc | Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320387A1 (de) * | 1973-04-21 | 1974-10-31 | Boehringer Mannheim Gmbh | Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben |
| GB1503953A (en) * | 1974-06-04 | 1978-03-15 | Fujisawa Pharmaceutical Co | Substituted-phenyl substituted-alkyl ethers and the preparation thereof |
| US4214094A (en) * | 1977-03-30 | 1980-07-22 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-phenyl substituted-alkyl ethers and the preparation thereof |
| GB9306453D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Heterocyclic derivatives |
| AU3275999A (en) * | 1998-03-10 | 1999-09-27 | Ono Pharmaceutical Co. Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| GB9822473D0 (en) | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
| NZ525119A (en) | 2000-10-05 | 2005-04-29 | Bayer Ag | Propionic acid derivatives |
-
2002
- 2002-06-20 GB GBGB0214254.5A patent/GB0214254D0/en not_active Ceased
-
2003
- 2003-06-18 RU RU2004137092/04A patent/RU2316539C2/ru not_active IP Right Cessation
- 2003-06-18 BR BR0311935-1A patent/BR0311935A/pt not_active IP Right Cessation
- 2003-06-18 JP JP2004514762A patent/JP2005534673A/ja active Pending
- 2003-06-18 PL PL03375075A patent/PL375075A1/xx not_active Application Discontinuation
- 2003-06-18 CA CA002489359A patent/CA2489359A1/en not_active Abandoned
- 2003-06-18 EP EP03738057A patent/EP1513795A2/en not_active Withdrawn
- 2003-06-18 US US10/518,778 patent/US7199239B2/en not_active Expired - Fee Related
- 2003-06-18 MX MXPA04012858A patent/MXPA04012858A/es active IP Right Grant
- 2003-06-18 IL IL16547703A patent/IL165477A0/xx unknown
- 2003-06-18 AU AU2003245963A patent/AU2003245963C1/en not_active Ceased
- 2003-06-18 CN CNB038193221A patent/CN100349856C/zh not_active Expired - Fee Related
- 2003-06-18 NZ NZ537209A patent/NZ537209A/en unknown
- 2003-06-18 WO PCT/EP2003/006416 patent/WO2004000762A2/en not_active Ceased
- 2003-06-18 KR KR10-2004-7020767A patent/KR20050013590A/ko not_active Ceased
-
2004
- 2004-11-30 IS IS7575A patent/IS7575A/is unknown
- 2004-12-03 NO NO20045327A patent/NO20045327L/no not_active Application Discontinuation
- 2004-12-13 ZA ZA200410054A patent/ZA200410054B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0311935A (pt) | 2005-03-22 |
| NZ537209A (en) | 2006-10-27 |
| MXPA04012858A (es) | 2005-06-08 |
| PL375075A1 (en) | 2005-11-14 |
| RU2004137092A (ru) | 2005-09-10 |
| CA2489359A1 (en) | 2003-12-31 |
| US20060074111A1 (en) | 2006-04-06 |
| IL165477A0 (en) | 2006-01-15 |
| WO2004000762A3 (en) | 2004-10-14 |
| RU2316539C2 (ru) | 2008-02-10 |
| IS7575A (is) | 2004-11-30 |
| US7199239B2 (en) | 2007-04-03 |
| EP1513795A2 (en) | 2005-03-16 |
| AU2003245963B2 (en) | 2008-06-26 |
| CN100349856C (zh) | 2007-11-21 |
| AU2003245963C1 (en) | 2008-12-11 |
| NO20045327L (no) | 2005-03-10 |
| ZA200410054B (en) | 2006-02-22 |
| WO2004000762A2 (en) | 2003-12-31 |
| AU2003245963A1 (en) | 2004-01-06 |
| GB0214254D0 (en) | 2002-07-31 |
| KR20050013590A (ko) | 2005-02-04 |
| CN1675168A (zh) | 2005-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005534673A (ja) | 化学化合物 | |
| JP4234431B2 (ja) | 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 | |
| KR100815022B1 (ko) | Ppar 관련 질환을 치료하기 위한 티아졸 유도체 | |
| JP3490704B2 (ja) | チアゾールおよびオキサゾール誘導体ならびにそれらの医薬的使用 | |
| AU2002246713A1 (en) | Thiazole derivatives for treating PPAR related disorders | |
| JP2004532266A (ja) | 心血管系疾患の治療に有用なチアゾールまたはオキサゾール誘導体 | |
| JP2005534672A (ja) | hPPAR活性化物質としてのフェニルアルカン酸及びフェニルオキシアルカン酸誘導体 | |
| US7091225B2 (en) | Substituted oxazoles and thiazoles as hPPAR alpha agonists | |
| EP1343772A1 (en) | Thia- and oxazoles and their use as ppars activators | |
| JP2005529965A (ja) | hPPAR活性化物質としてのフェニルオキシアルカン酸誘導体 | |
| US20070155805A1 (en) | Benzofuran and bezothiophene derivatives useful for the treatment of cardiovascular disease | |
| JP2004532267A (ja) | hPPARα受容体のオキサゾール/チアゾール誘導体アクチベーター | |
| US7439259B2 (en) | Thiazole derivatives for treating PPAR related disorders | |
| JP2007508270A (ja) | I.a.ジスリピデミアの治療におけるhppar作用物質として使用するためのチアゾール−2−カルボキシアミド誘導体 | |
| HK1059925B (en) | Thiazole derivatives for treating ppar related disorders |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060424 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060424 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090210 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090630 |