RU2323929C2 - Производные фенилалкановой кислоты и фенилоксиалкановой кислоты, их применение и содержащая их фармацевтическая композиция - Google Patents
Производные фенилалкановой кислоты и фенилоксиалкановой кислоты, их применение и содержащая их фармацевтическая композиция Download PDFInfo
- Publication number
- RU2323929C2 RU2323929C2 RU2004135539/04A RU2004135539A RU2323929C2 RU 2323929 C2 RU2323929 C2 RU 2323929C2 RU 2004135539/04 A RU2004135539/04 A RU 2004135539/04A RU 2004135539 A RU2004135539 A RU 2004135539A RU 2323929 C2 RU2323929 C2 RU 2323929C2
- Authority
- RU
- Russia
- Prior art keywords
- oxy
- phenyl
- pyridinyl
- acetic acid
- pentyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 150000002148 esters Chemical class 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 54
- -1 ethyloxymethyl Chemical group 0.000 claims 21
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- QVOWVWHRALYOAY-UHFFFAOYSA-N 2-[2-ethyl-4-[1-(6-phenylpyridin-2-yl)pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(CC)=C1 QVOWVWHRALYOAY-UHFFFAOYSA-N 0.000 claims 1
- STULDPSRMBPGLV-RUZDIDTESA-N 2-[2-methyl-4-[(1r)-1-[4-[4-(trifluoromethyl)phenyl]phenyl]pentyl]sulfanylphenoxy]acetic acid Chemical compound S([C@H](CCCC)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 STULDPSRMBPGLV-RUZDIDTESA-N 0.000 claims 1
- STULDPSRMBPGLV-VWLOTQADSA-N 2-[2-methyl-4-[(1s)-1-[4-[4-(trifluoromethyl)phenyl]phenyl]pentyl]sulfanylphenoxy]acetic acid Chemical compound S([C@@H](CCCC)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 STULDPSRMBPGLV-VWLOTQADSA-N 0.000 claims 1
- QWRZXBILDNAXGJ-UHFFFAOYSA-N 2-[2-methyl-4-[1-(3-phenylphenyl)pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 QWRZXBILDNAXGJ-UHFFFAOYSA-N 0.000 claims 1
- STAOLRJFLROFNF-UHFFFAOYSA-N 2-[2-methyl-4-[1-(6-phenylpyridin-2-yl)pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 STAOLRJFLROFNF-UHFFFAOYSA-N 0.000 claims 1
- WABIEYMUOHYGIK-UHFFFAOYSA-N 2-[2-methyl-4-[1-[2-methyl-3-(4-methylphenyl)phenyl]pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 WABIEYMUOHYGIK-UHFFFAOYSA-N 0.000 claims 1
- DKSOICJZCFEORY-UHFFFAOYSA-N 2-[2-methyl-4-[1-[2-methyl-3-[4-(trifluoromethyl)phenyl]phenyl]pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 DKSOICJZCFEORY-UHFFFAOYSA-N 0.000 claims 1
- YIQSTTLURNHAFU-UHFFFAOYSA-N 2-[2-methyl-4-[1-[3-[4-(trifluoromethyl)phenyl]phenyl]ethylsulfanyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 YIQSTTLURNHAFU-UHFFFAOYSA-N 0.000 claims 1
- REGXSVCWPBTWDE-UHFFFAOYSA-N 2-[2-methyl-4-[1-[3-[4-(trifluoromethyl)phenyl]phenyl]pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 REGXSVCWPBTWDE-UHFFFAOYSA-N 0.000 claims 1
- GDOYXGJSEDZZCI-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-[4-(trifluoromethyl)phenyl]phenyl]ethylsulfanyl]phenoxy]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 GDOYXGJSEDZZCI-UHFFFAOYSA-N 0.000 claims 1
- LXTUOZUCBDZTPJ-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-[4-(trifluoromethyl)phenyl]phenyl]pentoxy]phenoxy]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 LXTUOZUCBDZTPJ-UHFFFAOYSA-N 0.000 claims 1
- CJFYAMCFNTXEQL-UHFFFAOYSA-N 2-[2-methyl-4-[1-[6-(4-methylphenyl)pyridin-2-yl]pentoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 CJFYAMCFNTXEQL-UHFFFAOYSA-N 0.000 claims 1
- YVXGMLLXPCEBQT-UHFFFAOYSA-N 2-[2-methyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]butoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCC)OC1=CC=C(OCC(O)=O)C(C)=C1 YVXGMLLXPCEBQT-UHFFFAOYSA-N 0.000 claims 1
- JESSSJIYHLWMRG-UHFFFAOYSA-N 2-[2-methyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]hexoxy]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 JESSSJIYHLWMRG-UHFFFAOYSA-N 0.000 claims 1
- WWRJZLQEDRPWQS-UHFFFAOYSA-N 2-[2-methyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentylsulfinyl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)C(CCCC)C(N=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 WWRJZLQEDRPWQS-UHFFFAOYSA-N 0.000 claims 1
- OESLLFMKTMFNNI-HSZRJFAPSA-N 2-[3-chloro-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1Cl OESLLFMKTMFNNI-HSZRJFAPSA-N 0.000 claims 1
- OESLLFMKTMFNNI-QHCPKHFHSA-N 2-[3-chloro-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1Cl OESLLFMKTMFNNI-QHCPKHFHSA-N 0.000 claims 1
- BURNKDPLDBHFMJ-JOCHJYFZSA-N 2-[3-methoxy-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1OC BURNKDPLDBHFMJ-JOCHJYFZSA-N 0.000 claims 1
- BURNKDPLDBHFMJ-QFIPXVFZSA-N 2-[3-methoxy-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1OC BURNKDPLDBHFMJ-QFIPXVFZSA-N 0.000 claims 1
- BFJKRJXIDFWFEU-DEOSSOPVSA-N 2-[4-[(1r)-1-[6-(4-chloro-3-methylphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=C(C)C(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 BFJKRJXIDFWFEU-DEOSSOPVSA-N 0.000 claims 1
- ONEWYKOBASGBFV-QHCPKHFHSA-N 2-[4-[(1r)-1-[6-(4-chlorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 ONEWYKOBASGBFV-QHCPKHFHSA-N 0.000 claims 1
- RCDPHQXXQWOXLJ-HSZRJFAPSA-N 2-[4-[(1r)-1-[6-(4-chlorophenyl)pyridin-2-yl]-3-methoxypropoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](CCOC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 RCDPHQXXQWOXLJ-HSZRJFAPSA-N 0.000 claims 1
- CVJOLJRBJVYABW-XMMPIXPASA-N 2-[4-[(1r)-1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 CVJOLJRBJVYABW-XMMPIXPASA-N 0.000 claims 1
- IGIUVPUKHVXRTD-DEOSSOPVSA-N 2-[4-[(1r)-1-[6-(4-cyano-2-fluorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C(=CC(=CC=1)C#N)F)C1=CC=C(OCC(O)=O)C(C)=C1 IGIUVPUKHVXRTD-DEOSSOPVSA-N 0.000 claims 1
- DDOCBBRVQCMJKL-VWLOTQADSA-N 2-[4-[(1r)-1-[6-(4-cyano-2-methylphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C(=CC(=CC=1)C#N)C)C1=CC=C(OCC(O)=O)C(C)=C1 DDOCBBRVQCMJKL-VWLOTQADSA-N 0.000 claims 1
- OXEWZSPWYGDUFH-DEOSSOPVSA-N 2-[4-[(1r)-1-[6-(4-cyano-3-fluorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=C(F)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 OXEWZSPWYGDUFH-DEOSSOPVSA-N 0.000 claims 1
- FGUOBFQYTQQIMJ-VWLOTQADSA-N 2-[4-[(1r)-1-[6-(4-cyano-3-methylphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=C(C)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 FGUOBFQYTQQIMJ-VWLOTQADSA-N 0.000 claims 1
- DVERCEKMCHOWAD-DEOSSOPVSA-N 2-[4-[(1r)-1-[6-(4-cyanophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(OCC(O)=O)C(C)=C1 DVERCEKMCHOWAD-DEOSSOPVSA-N 0.000 claims 1
- RZGGCTDQMRIIAM-RUZDIDTESA-N 2-[4-[(1r)-1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(OCC(O)=O)C(C)=C1 RZGGCTDQMRIIAM-RUZDIDTESA-N 0.000 claims 1
- QVKJBLWKZHYVHR-HSZRJFAPSA-N 2-[4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1 QVKJBLWKZHYVHR-HSZRJFAPSA-N 0.000 claims 1
- JPVCRJDULKIJNL-DEOSSOPVSA-N 2-[4-[(1r)-2-ethoxy-1-[6-(2-fluoro-4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C(=CC(C)=CC=1)F)C1=CC=C(OCC(O)=O)C(C)=C1 JPVCRJDULKIJNL-DEOSSOPVSA-N 0.000 claims 1
- SDVWUQLAUFYVMI-DEOSSOPVSA-N 2-[4-[(1r)-2-ethoxy-1-[6-(3-fluoro-4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=C(F)C(C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 SDVWUQLAUFYVMI-DEOSSOPVSA-N 0.000 claims 1
- JXNNPTTYFKZRFK-QHCPKHFHSA-N 2-[4-[(1r)-2-ethoxy-1-[6-(4-fluorophenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=CC(F)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 JXNNPTTYFKZRFK-QHCPKHFHSA-N 0.000 claims 1
- NTRHFVJVWHILJM-DEOSSOPVSA-N 2-[4-[(1r)-2-ethoxy-1-[6-(4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 NTRHFVJVWHILJM-DEOSSOPVSA-N 0.000 claims 1
- GMLZWFABMZAKMR-XMMPIXPASA-N 2-[4-[(1s)-1-[6-(3-chloro-4-cyanophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(Cl)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 GMLZWFABMZAKMR-XMMPIXPASA-N 0.000 claims 1
- BFJKRJXIDFWFEU-XMMPIXPASA-N 2-[4-[(1s)-1-[6-(4-chloro-3-methylphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(C)C(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 BFJKRJXIDFWFEU-XMMPIXPASA-N 0.000 claims 1
- ONEWYKOBASGBFV-HSZRJFAPSA-N 2-[4-[(1s)-1-[6-(4-chlorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 ONEWYKOBASGBFV-HSZRJFAPSA-N 0.000 claims 1
- RCDPHQXXQWOXLJ-QHCPKHFHSA-N 2-[4-[(1s)-1-[6-(4-chlorophenyl)pyridin-2-yl]-3-methoxypropoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](CCOC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 RCDPHQXXQWOXLJ-QHCPKHFHSA-N 0.000 claims 1
- CVJOLJRBJVYABW-DEOSSOPVSA-N 2-[4-[(1s)-1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 CVJOLJRBJVYABW-DEOSSOPVSA-N 0.000 claims 1
- IGIUVPUKHVXRTD-XMMPIXPASA-N 2-[4-[(1s)-1-[6-(4-cyano-2-fluorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C(=CC(=CC=1)C#N)F)C1=CC=C(OCC(O)=O)C(C)=C1 IGIUVPUKHVXRTD-XMMPIXPASA-N 0.000 claims 1
- OXEWZSPWYGDUFH-XMMPIXPASA-N 2-[4-[(1s)-1-[6-(4-cyano-3-fluorophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(F)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 OXEWZSPWYGDUFH-XMMPIXPASA-N 0.000 claims 1
- FGUOBFQYTQQIMJ-RUZDIDTESA-N 2-[4-[(1s)-1-[6-(4-cyano-3-methylphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(C)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 FGUOBFQYTQQIMJ-RUZDIDTESA-N 0.000 claims 1
- DVERCEKMCHOWAD-XMMPIXPASA-N 2-[4-[(1s)-1-[6-(4-cyanophenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(OCC(O)=O)C(C)=C1 DVERCEKMCHOWAD-XMMPIXPASA-N 0.000 claims 1
- RZGGCTDQMRIIAM-VWLOTQADSA-N 2-[4-[(1s)-1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(OCC(O)=O)C(C)=C1 RZGGCTDQMRIIAM-VWLOTQADSA-N 0.000 claims 1
- QVKJBLWKZHYVHR-QHCPKHFHSA-N 2-[4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CC(O)=O)C=C1 QVKJBLWKZHYVHR-QHCPKHFHSA-N 0.000 claims 1
- JPVCRJDULKIJNL-XMMPIXPASA-N 2-[4-[(1s)-2-ethoxy-1-[6-(2-fluoro-4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C(=CC(C)=CC=1)F)C1=CC=C(OCC(O)=O)C(C)=C1 JPVCRJDULKIJNL-XMMPIXPASA-N 0.000 claims 1
- SDVWUQLAUFYVMI-XMMPIXPASA-N 2-[4-[(1s)-2-ethoxy-1-[6-(3-fluoro-4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(F)C(C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 SDVWUQLAUFYVMI-XMMPIXPASA-N 0.000 claims 1
- JXNNPTTYFKZRFK-HSZRJFAPSA-N 2-[4-[(1s)-2-ethoxy-1-[6-(4-fluorophenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=CC(F)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 JXNNPTTYFKZRFK-HSZRJFAPSA-N 0.000 claims 1
- NTRHFVJVWHILJM-XMMPIXPASA-N 2-[4-[(1s)-2-ethoxy-1-[6-(4-methylphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 NTRHFVJVWHILJM-XMMPIXPASA-N 0.000 claims 1
- FVJVDYIRTVLUOJ-UHFFFAOYSA-N 2-[4-[1-[3-(4-chlorophenyl)-2-methylphenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 FVJVDYIRTVLUOJ-UHFFFAOYSA-N 0.000 claims 1
- MNPQRUZDPGZNBE-UHFFFAOYSA-N 2-[4-[1-[3-(4-chlorophenyl)phenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 MNPQRUZDPGZNBE-UHFFFAOYSA-N 0.000 claims 1
- SHYAUYDBTBFLPN-UHFFFAOYSA-N 2-[4-[1-[3-(4-cyanophenyl)-2-methylphenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 SHYAUYDBTBFLPN-UHFFFAOYSA-N 0.000 claims 1
- JWOSCXGJAGQNAA-UHFFFAOYSA-N 2-[4-[1-[3-(4-cyanophenyl)phenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 JWOSCXGJAGQNAA-UHFFFAOYSA-N 0.000 claims 1
- YJJVPNNZUMTSRF-UHFFFAOYSA-N 2-[4-[1-[3-(4-fluorophenyl)-2-methylphenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 YJJVPNNZUMTSRF-UHFFFAOYSA-N 0.000 claims 1
- QHAXONOWCFJHJD-UHFFFAOYSA-N 2-[4-[1-[4-(4-chlorophenyl)phenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 QHAXONOWCFJHJD-UHFFFAOYSA-N 0.000 claims 1
- ZXOXPWQRJOBABG-UHFFFAOYSA-N 2-[4-[1-[6-(3,4-dichlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 ZXOXPWQRJOBABG-UHFFFAOYSA-N 0.000 claims 1
- BWQCXFXWNPYNKT-UHFFFAOYSA-N 2-[4-[1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-ethylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(CC)=C1 BWQCXFXWNPYNKT-UHFFFAOYSA-N 0.000 claims 1
- CVJOLJRBJVYABW-UHFFFAOYSA-N 2-[4-[1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 CVJOLJRBJVYABW-UHFFFAOYSA-N 0.000 claims 1
- DBODMECEJJZRHI-UHFFFAOYSA-N 2-[4-[1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-ethylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(CC)=C1 DBODMECEJJZRHI-UHFFFAOYSA-N 0.000 claims 1
- RZGGCTDQMRIIAM-UHFFFAOYSA-N 2-[4-[1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 RZGGCTDQMRIIAM-UHFFFAOYSA-N 0.000 claims 1
- XBOSRGMTTQLJSY-UHFFFAOYSA-N 2-[4-[1-[6-(4-fluorophenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 XBOSRGMTTQLJSY-UHFFFAOYSA-N 0.000 claims 1
- QVKJBLWKZHYVHR-UHFFFAOYSA-N 2-[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(CC(O)=O)C=C1 QVKJBLWKZHYVHR-UHFFFAOYSA-N 0.000 claims 1
- GTWRLHKUIBLHQJ-UHFFFAOYSA-N 2-[4-[2-ethoxy-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]ethyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(COCC)SC1=CC=C(OCC(O)=O)C(C)=C1 GTWRLHKUIBLHQJ-UHFFFAOYSA-N 0.000 claims 1
- QSGYPAXVKJSUGA-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenoxy]propanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 QSGYPAXVKJSUGA-UHFFFAOYSA-N 0.000 claims 1
- CYVCHKMSBYZJQV-XMMPIXPASA-N 3-[2-chloro-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(Cl)=C1 CYVCHKMSBYZJQV-XMMPIXPASA-N 0.000 claims 1
- HMAUXJLDINVDRL-XMMPIXPASA-N 3-[2-methoxy-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(OC)=C1 HMAUXJLDINVDRL-XMMPIXPASA-N 0.000 claims 1
- HMAUXJLDINVDRL-DEOSSOPVSA-N 3-[2-methoxy-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(OC)=C1 HMAUXJLDINVDRL-DEOSSOPVSA-N 0.000 claims 1
- LHMYLAMNSGVHLV-RUZDIDTESA-N 3-[2-methyl-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(C)=C1 LHMYLAMNSGVHLV-RUZDIDTESA-N 0.000 claims 1
- LHMYLAMNSGVHLV-VWLOTQADSA-N 3-[2-methyl-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(C)=C1 LHMYLAMNSGVHLV-VWLOTQADSA-N 0.000 claims 1
- FICDKRHXRHEKKD-HSZRJFAPSA-N 3-[3,5-dimethoxy-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=C(OC)C=C(CCC(O)=O)C=C1OC FICDKRHXRHEKKD-HSZRJFAPSA-N 0.000 claims 1
- FICDKRHXRHEKKD-QHCPKHFHSA-N 3-[3,5-dimethoxy-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=C(OC)C=C(CCC(O)=O)C=C1OC FICDKRHXRHEKKD-QHCPKHFHSA-N 0.000 claims 1
- QVYNAKDPSQXICS-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=C(C)C=C(CCC(O)=O)C=C1C QVYNAKDPSQXICS-UHFFFAOYSA-N 0.000 claims 1
- IVSKYDSNNUAPMO-XMMPIXPASA-N 3-[3-chloro-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1Cl IVSKYDSNNUAPMO-XMMPIXPASA-N 0.000 claims 1
- IVSKYDSNNUAPMO-DEOSSOPVSA-N 3-[3-chloro-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1Cl IVSKYDSNNUAPMO-DEOSSOPVSA-N 0.000 claims 1
- CXGAHOVBVJDYKP-QHCPKHFHSA-N 3-[3-chloro-5-methoxy-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=C(Cl)C=C(CCC(O)=O)C=C1OC CXGAHOVBVJDYKP-QHCPKHFHSA-N 0.000 claims 1
- PAICNROLHAAMJB-UHFFFAOYSA-N 3-[3-ethoxy-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(CCC(O)=O)C=C1OCC PAICNROLHAAMJB-UHFFFAOYSA-N 0.000 claims 1
- UAAOZMSRBUKUQB-XMMPIXPASA-N 3-[3-fluoro-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1F UAAOZMSRBUKUQB-XMMPIXPASA-N 0.000 claims 1
- UAAOZMSRBUKUQB-DEOSSOPVSA-N 3-[3-fluoro-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1F UAAOZMSRBUKUQB-DEOSSOPVSA-N 0.000 claims 1
- DZLBAJFPRLTPCJ-HSZRJFAPSA-N 3-[3-methoxy-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1OC DZLBAJFPRLTPCJ-HSZRJFAPSA-N 0.000 claims 1
- DZLBAJFPRLTPCJ-QHCPKHFHSA-N 3-[3-methoxy-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1OC DZLBAJFPRLTPCJ-QHCPKHFHSA-N 0.000 claims 1
- SZFMHEAGFZOWQJ-RUZDIDTESA-N 3-[3-methyl-4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1C SZFMHEAGFZOWQJ-RUZDIDTESA-N 0.000 claims 1
- SZFMHEAGFZOWQJ-VWLOTQADSA-N 3-[3-methyl-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1C SZFMHEAGFZOWQJ-VWLOTQADSA-N 0.000 claims 1
- JTXCQVMXWGYZPB-UHFFFAOYSA-N 3-[3-propyl-4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(CCC(O)=O)C=C1CCC JTXCQVMXWGYZPB-UHFFFAOYSA-N 0.000 claims 1
- FBOOKQWOIPOPOT-RUZDIDTESA-N 3-[4-[(1r)-1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(CCC(O)=O)C(C)=C1 FBOOKQWOIPOPOT-RUZDIDTESA-N 0.000 claims 1
- WPKWHJOTUREAKT-AREMUKBSSA-N 3-[4-[(1r)-1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-methylphenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(CCC(O)=O)C(C)=C1 WPKWHJOTUREAKT-AREMUKBSSA-N 0.000 claims 1
- ZKLVAPWFNKOHNK-XMMPIXPASA-N 3-[4-[(1r)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1 ZKLVAPWFNKOHNK-XMMPIXPASA-N 0.000 claims 1
- FBOOKQWOIPOPOT-VWLOTQADSA-N 3-[4-[(1s)-1-[6-(4-chlorophenyl)pyridin-2-yl]pentoxy]-2-methylphenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(CCC(O)=O)C(C)=C1 FBOOKQWOIPOPOT-VWLOTQADSA-N 0.000 claims 1
- WPKWHJOTUREAKT-SANMLTNESA-N 3-[4-[(1s)-1-[6-(4-cyanophenyl)pyridin-2-yl]pentoxy]-2-methylphenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(CCC(O)=O)C(C)=C1 WPKWHJOTUREAKT-SANMLTNESA-N 0.000 claims 1
- ZKLVAPWFNKOHNK-DEOSSOPVSA-N 3-[4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound O([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C=C1 ZKLVAPWFNKOHNK-DEOSSOPVSA-N 0.000 claims 1
- ZKLVAPWFNKOHNK-UHFFFAOYSA-N 3-[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(CCC(O)=O)C=C1 ZKLVAPWFNKOHNK-UHFFFAOYSA-N 0.000 claims 1
- MAHDJDGDWNLNSA-UHFFFAOYSA-N 4-[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]butanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1C(CCCC)OC1=CC=C(CCCC(O)=O)C=C1 MAHDJDGDWNLNSA-UHFFFAOYSA-N 0.000 claims 1
- 229910005965 SO 2 Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 208000030172 endocrine system disease Diseases 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—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 singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Neurology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Nutrition Science (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0214149.7 | 2002-06-19 | ||
| GBGB0214149.7A GB0214149D0 (en) | 2002-06-19 | 2002-06-19 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004135539A RU2004135539A (ru) | 2005-08-10 |
| RU2323929C2 true RU2323929C2 (ru) | 2008-05-10 |
Family
ID=9938916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004135539/04A RU2323929C2 (ru) | 2002-06-19 | 2003-06-18 | Производные фенилалкановой кислоты и фенилоксиалкановой кислоты, их применение и содержащая их фармацевтическая композиция |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7338960B2 (https=) |
| EP (1) | EP1513526B1 (https=) |
| JP (1) | JP2005534672A (https=) |
| KR (1) | KR20050030624A (https=) |
| CN (1) | CN1674897A (https=) |
| AT (1) | ATE377420T1 (https=) |
| AU (1) | AU2003245962B2 (https=) |
| BR (1) | BR0311931A (https=) |
| CA (1) | CA2487909A1 (https=) |
| CY (1) | CY1107168T1 (https=) |
| DE (1) | DE60317326T2 (https=) |
| DK (1) | DK1513526T3 (https=) |
| ES (1) | ES2295601T3 (https=) |
| GB (1) | GB0214149D0 (https=) |
| IL (1) | IL165476A0 (https=) |
| IS (1) | IS7574A (https=) |
| MX (1) | MXPA04012857A (https=) |
| NO (1) | NO20045328L (https=) |
| NZ (1) | NZ537210A (https=) |
| PL (1) | PL375148A1 (https=) |
| PT (1) | PT1513526E (https=) |
| RU (1) | RU2323929C2 (https=) |
| SI (1) | SI1513526T1 (https=) |
| WO (1) | WO2004000315A1 (https=) |
| ZA (1) | ZA200410061B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| EP1667964B1 (en) | 2003-09-19 | 2009-07-22 | Janssen Pharmaceutica N.V. | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| CN1875002B (zh) | 2003-11-05 | 2011-08-03 | 霍夫曼-拉罗奇有限公司 | 作为ppar激动剂的苯基衍生物 |
| AU2004309271A1 (en) | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
| JP5299810B2 (ja) * | 2004-02-27 | 2013-09-25 | アムジエン・インコーポレーテツド | 代謝疾患の治療に使用するための、化合物、薬学的組成物及び方法 |
| AR048523A1 (es) * | 2004-04-07 | 2006-05-03 | Kalypsys Inc | Compuestos con estructura de aril sulfonamida y sulfonilo como moduladores de ppar y metodos para tratar trastornos metabolicos |
| DE602005024384D1 (de) | 2004-05-05 | 2010-12-09 | High Point Pharmaceuticals Llc | Neue verbindungen, ihre herstellung und verwendung |
| US8053598B2 (en) | 2004-05-05 | 2011-11-08 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
| MY147518A (en) | 2004-09-15 | 2012-12-31 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| US7465804B2 (en) * | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
| ES2372617T3 (es) | 2005-06-30 | 2012-01-24 | High Point Pharmaceuticals, Llc | Ácidos fenoxiacéticos como activadores de ppar-delta. |
| JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
| WO2007033002A1 (en) | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| CN103224477A (zh) | 2005-12-22 | 2013-07-31 | 高点制药有限责任公司 | 作为PPAR-δ活化剂的苯氧基乙酸 |
| US7943612B2 (en) | 2006-03-09 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds that modulate PPAR activity, their preparation and use |
| CA2646430A1 (en) * | 2006-03-14 | 2007-09-20 | Amgen Inc. | Bicyclic carboxylic acid derivatives useful for treating metabolic disorders |
| UY30288A1 (es) | 2006-04-18 | 2007-08-31 | Janssen Pharmaceutica Nv | Derivados del ácido benzoazepin-oxi-acético como agonistas de ppar-delta usados para aumentar hdl-c. reducir ldl-c y reducir colesterol |
| CN101591227B (zh) * | 2006-06-23 | 2012-09-05 | 赵昱 | 一类肉桂醇类衍生物及其制备方法和药物用途 |
| CA2662305C (en) | 2006-09-07 | 2012-04-17 | Amgen Inc. | Heterocyclic gpr40 modulators |
| AU2007292816B2 (en) * | 2006-09-07 | 2011-11-17 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
| US8519145B2 (en) | 2006-12-02 | 2013-08-27 | Seoul National University Industry Foundation | Aryl compounds as PPAR ligands and their use |
| EP2139843B1 (en) | 2007-04-16 | 2013-12-25 | Amgen, Inc | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
| JP5291708B2 (ja) * | 2007-07-25 | 2013-09-18 | 中国人民解放軍軍事医学科学院毒物薬物研究所 | アリールピリミジン誘導体、その製造方法、及び、その使用 |
| CN102083783A (zh) | 2007-10-10 | 2011-06-01 | 安姆根有限公司 | 取代的联苯gpr40调节剂 |
| WO2009111056A1 (en) * | 2008-03-06 | 2009-09-11 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| AU2009303475B2 (en) * | 2008-10-15 | 2012-09-13 | Amgen Inc. | Spirocyclic GPR40 modulators |
| EP2699569B1 (en) * | 2011-04-22 | 2017-08-30 | Jasco Pharmaceuticals, LLC | Aminopyrimidine kinase inhibitors |
| NZ631569A (en) | 2012-02-28 | 2016-10-28 | Piramal Entpr Ltd | Phenyl alkanoic acid derivatives as gpr agonists |
| KR101569522B1 (ko) | 2013-04-18 | 2015-11-17 | 현대약품 주식회사 | 신규한 3-(4-(벤질옥시)페닐)헥스-4-이노익 산 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 대사성 질환의 예방 또는 치료용 약학적 조성물 |
| EP3756661A1 (en) | 2013-09-09 | 2020-12-30 | vTv Therapeutics LLC | Use of a ppar-delta agonist for treating muscle atrophy |
| CN108503581A (zh) * | 2018-04-12 | 2018-09-07 | 苏州康润医药有限公司 | 一种3-溴-6-氟-2-吡啶乙酮的合成方法 |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221919A (en) * | 1974-12-17 | 1980-09-09 | Spofa, United Pharmaceutical Works | Antiinflammatory substituted phenylacetic acids |
| WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
| EP1067109A1 (en) * | 1998-03-10 | 2001-01-10 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| WO2001036351A2 (en) * | 1999-11-19 | 2001-05-25 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists related applications |
| EP1132376A1 (en) * | 1998-11-20 | 2001-09-12 | Takeda Chemical Industries, Ltd. | Beta-amyloid protein production/secretion inhibitors |
| RU2174121C2 (ru) * | 1996-08-19 | 2001-09-27 | Джапан Тобакко Инк. | Производные пропионовой кислоты и фармацевтическая композиция на их основе |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2401459A1 (fr) * | 1977-08-26 | 1979-03-23 | Cii Honeywell Bull | Support d'information portatif muni d'un microprocesseur et d'une memoire morte programmable |
| DE4038335A1 (de) * | 1990-12-01 | 1992-06-04 | Boehringer Mannheim Gmbh | Neue pyridinderivate, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| WO1999011255A1 (en) * | 1997-08-28 | 1999-03-11 | Ono Pharmaceutical Co., Ltd. | Peroxisome proliferator-activated receptor controllers |
| CN1251671C (zh) * | 2000-05-19 | 2006-04-19 | 武田药品工业株式会社 | β分泌酶抑制剂 |
-
2002
- 2002-06-19 GB GBGB0214149.7A patent/GB0214149D0/en not_active Ceased
-
2003
- 2003-06-18 RU RU2004135539/04A patent/RU2323929C2/ru not_active IP Right Cessation
- 2003-06-18 AT AT03738056T patent/ATE377420T1/de not_active IP Right Cessation
- 2003-06-18 EP EP03738056A patent/EP1513526B1/en not_active Expired - Lifetime
- 2003-06-18 US US10/518,679 patent/US7338960B2/en not_active Expired - Fee Related
- 2003-06-18 NZ NZ537210A patent/NZ537210A/en unknown
- 2003-06-18 CA CA002487909A patent/CA2487909A1/en not_active Abandoned
- 2003-06-18 AU AU2003245962A patent/AU2003245962B2/en not_active Ceased
- 2003-06-18 DE DE60317326T patent/DE60317326T2/de not_active Expired - Fee Related
- 2003-06-18 DK DK03738056T patent/DK1513526T3/da active
- 2003-06-18 IL IL16547603A patent/IL165476A0/xx unknown
- 2003-06-18 KR KR1020047020583A patent/KR20050030624A/ko not_active Ceased
- 2003-06-18 SI SI200331089T patent/SI1513526T1/sl unknown
- 2003-06-18 JP JP2004514761A patent/JP2005534672A/ja active Pending
- 2003-06-18 CN CNA03819290XA patent/CN1674897A/zh active Pending
- 2003-06-18 BR BR0311931-9A patent/BR0311931A/pt not_active IP Right Cessation
- 2003-06-18 PT PT03738056T patent/PT1513526E/pt unknown
- 2003-06-18 MX MXPA04012857A patent/MXPA04012857A/es active IP Right Grant
- 2003-06-18 PL PL03375148A patent/PL375148A1/xx not_active Application Discontinuation
- 2003-06-18 ES ES03738056T patent/ES2295601T3/es not_active Expired - Lifetime
- 2003-06-18 WO PCT/EP2003/006415 patent/WO2004000315A1/en not_active Ceased
-
2004
- 2004-11-30 IS IS7574A patent/IS7574A/is unknown
- 2004-12-03 NO NO20045328A patent/NO20045328L/no not_active Application Discontinuation
- 2004-12-13 ZA ZA200410061A patent/ZA200410061B/en unknown
-
2008
- 2008-01-31 CY CY20081100116T patent/CY1107168T1/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221919A (en) * | 1974-12-17 | 1980-09-09 | Spofa, United Pharmaceutical Works | Antiinflammatory substituted phenylacetic acids |
| RU2174121C2 (ru) * | 1996-08-19 | 2001-09-27 | Джапан Тобакко Инк. | Производные пропионовой кислоты и фармацевтическая композиция на их основе |
| EP1067109A1 (en) * | 1998-03-10 | 2001-01-10 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| EP1132376A1 (en) * | 1998-11-20 | 2001-09-12 | Takeda Chemical Industries, Ltd. | Beta-amyloid protein production/secretion inhibitors |
| WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
| WO2001036351A2 (en) * | 1999-11-19 | 2001-05-25 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists related applications |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2487909A1 (en) | 2003-12-31 |
| PL375148A1 (en) | 2005-11-28 |
| NZ537210A (en) | 2006-09-29 |
| ES2295601T3 (es) | 2008-04-16 |
| RU2004135539A (ru) | 2005-08-10 |
| US7338960B2 (en) | 2008-03-04 |
| US20060089394A1 (en) | 2006-04-27 |
| AU2003245962B2 (en) | 2008-07-03 |
| AU2003245962A1 (en) | 2004-01-06 |
| CY1107168T1 (el) | 2012-10-24 |
| JP2005534672A (ja) | 2005-11-17 |
| EP1513526A1 (en) | 2005-03-16 |
| MXPA04012857A (es) | 2005-02-24 |
| KR20050030624A (ko) | 2005-03-30 |
| PT1513526E (pt) | 2008-02-12 |
| WO2004000315A1 (en) | 2003-12-31 |
| CN1674897A (zh) | 2005-09-28 |
| SI1513526T1 (sl) | 2008-04-30 |
| GB0214149D0 (en) | 2002-07-31 |
| IS7574A (is) | 2004-11-30 |
| DE60317326T2 (de) | 2008-08-28 |
| ATE377420T1 (de) | 2007-11-15 |
| EP1513526B1 (en) | 2007-11-07 |
| IL165476A0 (en) | 2006-01-15 |
| DK1513526T3 (da) | 2008-03-17 |
| NO20045328L (no) | 2005-03-09 |
| BR0311931A (pt) | 2005-04-05 |
| ZA200410061B (en) | 2006-07-26 |
| HK1076712A1 (en) | 2006-01-27 |
| DE60317326D1 (de) | 2007-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2323929C2 (ru) | Производные фенилалкановой кислоты и фенилоксиалкановой кислоты, их применение и содержащая их фармацевтическая композиция | |
| JP2005534672A5 (https=) | ||
| RU2356889C2 (ru) | Соединения, являющиеся активными по отношению к рецепторам, активируемым пролифератором пероксисом | |
| CA2532313A1 (en) | Medicament for treatment of dermal pigmentation | |
| KR100815022B1 (ko) | Ppar 관련 질환을 치료하기 위한 티아졸 유도체 | |
| DK2641596T3 (en) | Use of 1,3-diphenylprop-2-en-1-one derivatives for the treatment of liver disorders | |
| US8044243B2 (en) | Compounds for the treatment of metabolic disorders | |
| ZA200308352B (en) | Furan and thiophene derivatives that activate human peroxisome proliferator activated receptors. | |
| JP2004518702A5 (https=) | ||
| JP2004532227A5 (https=) | ||
| RU2012125372A (ru) | Производные пиразола в качестве ингибиторов 11-бета-hsd1 | |
| RU2005109555A (ru) | Новые производные винилкарбоновой кислоты и их терапевтическое применение | |
| AR048306A1 (es) | Derivados de acidos carboxilicos aromaticos con capacidad moduladora de los niveles de insulina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de trastornos metabolicos que responden a la regulacion de gpr40 | |
| RU2684916C2 (ru) | Фармацевтические композиции, содержащие доноры нитроксила | |
| ZA200503989B (en) | Mandelic acid derivatives | |
| MXPA01001047A (es) | Ligandos receptores de glucocorticoide y hormona de tiroides para el tratamiento de desordenes metabolicos. | |
| JP2007525516A5 (https=) | ||
| JP2005509590A5 (https=) | ||
| JP2006518763A5 (https=) | ||
| RU2006119510A (ru) | Фенильные производные в качестве ppar агонистов | |
| RU2004137092A (ru) | Производные пропионовых кислот и их применение в качестве активаторов hppars. | |
| ZA200100983B (en) | Substituted oxazoles and thiazoles derivatives as hPPAR gamma and hPPAR alpha activators. | |
| JP2003516377A5 (https=) | ||
| ZA200507704B (en) | Compounds for the treatment of metabolic disorders | |
| JP2004517100A5 (https=) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20090619 |