ES2295601T3 - Acido fenilalcanoico y derivados de acido feniloxialcanoico como activadores de hppar. - Google Patents
Acido fenilalcanoico y derivados de acido feniloxialcanoico como activadores de hppar. Download PDFInfo
- Publication number
- ES2295601T3 ES2295601T3 ES03738056T ES03738056T ES2295601T3 ES 2295601 T3 ES2295601 T3 ES 2295601T3 ES 03738056 T ES03738056 T ES 03738056T ES 03738056 T ES03738056 T ES 03738056T ES 2295601 T3 ES2295601 T3 ES 2295601T3
- Authority
- ES
- Spain
- Prior art keywords
- oxy
- phenyl
- pyridinyl
- pentyl
- methylphenyl
- 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.)
- Expired - Lifetime
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- 239000002253 acid Substances 0.000 title claims description 145
- 239000012190 activator Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 845
- -1 ethyloxymethyl Chemical group 0.000 claims description 309
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 258
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 122
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 120
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 36
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 35
- 235000019260 propionic acid Nutrition 0.000 claims description 33
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 15
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 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 description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- CYVCHKMSBYZJQV-DEOSSOPVSA-N 3-[2-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(Cl)=C1 CYVCHKMSBYZJQV-DEOSSOPVSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- OJDXNTGSVYCBRA-UHFFFAOYSA-N 3-[3-methoxy-5-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=C(CCC)C=C(CCC(O)=O)C=C1OC OJDXNTGSVYCBRA-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 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 description 2
- 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 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 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 description 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
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- 229910005965 SO 2 Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 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
- 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
- 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
- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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| JP4745244B2 (ja) | 2003-11-05 | 2011-08-10 | エフ.ホフマン−ラ ロシュ アーゲー | Pparアゴニストとしてのフェニル誘導体 |
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| US7465804B2 (en) | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
| EP2298742B1 (en) | 2005-06-30 | 2014-01-08 | High Point Pharmaceuticals, LLC | phenoxy acetic acids as PPAR delta activators |
| CA2621949A1 (en) * | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
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| WO2007106469A2 (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 |
| US7687526B2 (en) * | 2006-09-07 | 2010-03-30 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
| US7714008B2 (en) | 2006-09-07 | 2010-05-11 | Amgen Inc. | Heterocyclic GPR40 modulators |
| WO2008066356A1 (en) | 2006-12-02 | 2008-06-05 | 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 |
| EP2184277B1 (en) * | 2007-07-25 | 2015-07-01 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | Aryl pyrimidine derivatives, preparation methods and pharmaceutical uses thereof |
| EP2205548A1 (en) | 2007-10-10 | 2010-07-14 | Amgen, Inc | Substituted biphenyl gpr40 modulators |
| CA2716352C (en) | 2008-03-06 | 2013-05-28 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| EP2358656B1 (en) * | 2008-10-15 | 2014-01-01 | Amgen, Inc | Spirocyclic gpr40 modulators |
| AU2012245344B2 (en) * | 2011-04-22 | 2017-11-09 | 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 |
| WO2015035171A1 (en) | 2013-09-09 | 2015-03-12 | High Point Pharmaceuticals, 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 |
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| MXPA04012857A (es) | 2005-02-24 |
| CN1674897A (zh) | 2005-09-28 |
| CA2487909A1 (en) | 2003-12-31 |
| US20060089394A1 (en) | 2006-04-27 |
| JP2005534672A (ja) | 2005-11-17 |
| GB0214149D0 (en) | 2002-07-31 |
| PT1513526E (pt) | 2008-02-12 |
| US7338960B2 (en) | 2008-03-04 |
| EP1513526B1 (en) | 2007-11-07 |
| IS7574A (is) | 2004-11-30 |
| WO2004000315A1 (en) | 2003-12-31 |
| IL165476A0 (en) | 2006-01-15 |
| DE60317326D1 (de) | 2007-12-20 |
| PL375148A1 (en) | 2005-11-28 |
| AU2003245962B2 (en) | 2008-07-03 |
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