KR20050030624A - Hppar 활성화제로서 사용되는 페닐알칸산 및페닐옥시알칸산 유도체 - Google Patents
Hppar 활성화제로서 사용되는 페닐알칸산 및페닐옥시알칸산 유도체 Download PDFInfo
- Publication number
- KR20050030624A KR20050030624A KR1020047020583A KR20047020583A KR20050030624A KR 20050030624 A KR20050030624 A KR 20050030624A KR 1020047020583 A KR1020047020583 A KR 1020047020583A KR 20047020583 A KR20047020583 A KR 20047020583A KR 20050030624 A KR20050030624 A KR 20050030624A
- Authority
- KR
- South Korea
- Prior art keywords
- oxy
- phenyl
- pyridinyl
- acetic acid
- pentyl
- 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.)
- Ceased
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- 239000002253 acid Substances 0.000 title description 15
- 239000012190 activator Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- -1 CF 3 Chemical group 0.000 claims abstract description 154
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 270
- 238000000034 method Methods 0.000 claims description 82
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 238000002360 preparation method Methods 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 20
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 15
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 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
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 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 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 208000011580 syndromic disease 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
- 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 description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 3
- 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
- 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 description 3
- VEDQQJCAKLGCBG-DEOSSOPVSA-N 2-[2-methyl-4-[(1s)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentyl]sulfanylphenoxy]acetic acid Chemical compound S([C@@H](CCCC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 VEDQQJCAKLGCBG-DEOSSOPVSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- XMEXKBGVINSZTF-UHFFFAOYSA-N 2-[2-methyl-4-[2-[3-[4-(trifluoromethyl)phenyl]phenyl]ethyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 XMEXKBGVINSZTF-UHFFFAOYSA-N 0.000 claims description 3
- IUGGVZLWXIHYRZ-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1CSC1=CC=C(OCC(O)=O)C(C)=C1 IUGGVZLWXIHYRZ-UHFFFAOYSA-N 0.000 claims description 3
- ZTVVOMVXKYTLCV-UHFFFAOYSA-N 2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ZTVVOMVXKYTLCV-UHFFFAOYSA-N 0.000 claims description 3
- HXHWDKZOJXOMOQ-UHFFFAOYSA-N 2-[2-methyl-4-[[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2N=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HXHWDKZOJXOMOQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- IAKRYRIGNATULG-IRCUZVAFSA-N 2-[3-methoxy-4-[(1R)-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]pentoxy]phenyl]propanoic acid Chemical compound CCCC[C@H](C1=CC=CC(=N1)C2=CC=C(C=C2)C(F)(F)F)OC3=C(C=C(C=C3)C(C)C(=O)O)OC IAKRYRIGNATULG-IRCUZVAFSA-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
- CMYLYOPERJWJOD-XMMPIXPASA-N 2-[4-[(1S)-2-ethoxy-1-[6-(3-fluoro-4-methoxyphenyl)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(OC)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 CMYLYOPERJWJOD-XMMPIXPASA-N 0.000 claims description 3
- GMLZWFABMZAKMR-DEOSSOPVSA-N 2-[4-[(1r)-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-DEOSSOPVSA-N 0.000 claims description 3
- MBBXPSJABHZNDQ-VWLOTQADSA-N 2-[4-[(1r)-1-[6-(4-acetylphenyl)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(C)=O)C1=CC=C(OCC(O)=O)C(C)=C1 MBBXPSJABHZNDQ-VWLOTQADSA-N 0.000 claims description 3
- OZVOEQHCYOCEEE-AREMUKBSSA-N 2-[4-[(1r)-1-[6-(4-acetylphenyl)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(C)=O)C1=CC=C(OCC(O)=O)C(C)=C1 OZVOEQHCYOCEEE-AREMUKBSSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- CMYLYOPERJWJOD-DEOSSOPVSA-N 2-[4-[(1r)-2-ethoxy-1-[6-(3-fluoro-4-methoxyphenyl)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(OC)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 CMYLYOPERJWJOD-DEOSSOPVSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- IVNFHRCNUGHBID-SANMLTNESA-N 2-[4-[(1r)-2-ethoxy-1-[6-(4-propan-2-yloxyphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](COCC)C=1N=C(C=CC=1)C=1C=CC(OC(C)C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 IVNFHRCNUGHBID-SANMLTNESA-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
- MBBXPSJABHZNDQ-RUZDIDTESA-N 2-[4-[(1s)-1-[6-(4-acetylphenyl)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(C)=O)C1=CC=C(OCC(O)=O)C(C)=C1 MBBXPSJABHZNDQ-RUZDIDTESA-N 0.000 claims description 3
- OZVOEQHCYOCEEE-SANMLTNESA-N 2-[4-[(1s)-1-[6-(4-acetylphenyl)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(C)=O)C1=CC=C(OCC(O)=O)C(C)=C1 OZVOEQHCYOCEEE-SANMLTNESA-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
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- VCLBWRPCFOAQDX-RUZDIDTESA-N 2-[4-[(1s)-1-[6-(4-cyano-3-methoxyphenyl)pyridin-2-yl]-2-ethoxyethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=C(OC)C(C#N)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 VCLBWRPCFOAQDX-RUZDIDTESA-N 0.000 claims description 3
- 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 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
- 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 description 3
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- 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 description 3
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- IVNFHRCNUGHBID-AREMUKBSSA-N 2-[4-[(1s)-2-ethoxy-1-[6-(4-propan-2-yloxyphenyl)pyridin-2-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@H](COCC)C=1N=C(C=CC=1)C=1C=CC(OC(C)C)=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 IVNFHRCNUGHBID-AREMUKBSSA-N 0.000 claims description 3
- QUFBROUUAWJOSR-QHCPKHFHSA-N 2-[4-[(1s)-3-methoxy-1-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]propoxy]-2-methylphenoxy]acetic acid Chemical compound O([C@@H](CCOC)C=1N=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 QUFBROUUAWJOSR-QHCPKHFHSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- LANCUSUFEPLREM-UHFFFAOYSA-N 2-[4-[1-[3-(4-ethoxyphenyl)phenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OCC)=CC=2)=CC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 LANCUSUFEPLREM-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- JOUHNKLQFDTHCD-UHFFFAOYSA-N 2-[4-[1-[3-(4-methoxyphenyl)-2-methylphenyl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 JOUHNKLQFDTHCD-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- OZVOEQHCYOCEEE-UHFFFAOYSA-N 2-[4-[1-[6-(4-acetylphenyl)pyridin-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(C)=O)=NC=1C(CCCC)OC1=CC=C(OCC(O)=O)C(C)=C1 OZVOEQHCYOCEEE-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 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
- 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 description 3
- 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 description 3
- UXVPLBAVKQZKJR-UHFFFAOYSA-N 3-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UXVPLBAVKQZKJR-UHFFFAOYSA-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
- 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 description 3
- 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 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
- 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 description 3
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- 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 description 3
- 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 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-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 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
- JSKOPKBXDVUBRU-HHHXNRCGSA-N 3-[4-[(1r)-1-[6-(4-acetylphenyl)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(C)=O)C1=CC=C(CCC(O)=O)C(C)=C1 JSKOPKBXDVUBRU-HHHXNRCGSA-N 0.000 claims description 3
- 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 description 3
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- 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
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- Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Nutrition Science (AREA)
- Epidemiology (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)
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| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| PL1667964T3 (pl) | 2003-09-19 | 2010-01-29 | Janssen Pharmaceutica Nv | Kwasy 4-((fenoksyalkilo)tio)-fenoksyoctowe i analogi |
| NZ546444A (en) | 2003-11-05 | 2009-09-25 | Hoffmann La Roche | Phenyl derivatives as PPAR agonists |
| RU2006126978A (ru) * | 2003-12-25 | 2008-01-27 | Такеда Фармасьютикал Компани Лимитед (Jp) | Производные 3-(4-бензилоксифенил)пропановой кислоты |
| KR20070004769A (ko) * | 2004-02-27 | 2007-01-09 | 암젠 인코포레이션 | 대사 장애의 치료에 사용되는 화합물, 약제학적 조성물 및그 사용방법 |
| 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 |
| EP1745003B1 (en) | 2004-05-05 | 2010-10-27 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| JP4981662B2 (ja) | 2004-05-05 | 2012-07-25 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 新規の化合物、その製法と使用 |
| 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 |
| RU2412935C2 (ru) | 2005-06-30 | 2011-02-27 | Хай Пойнт Фармасьютикалс, ЛЛС | Феноксиуксусные кислоты в качестве активаторов дельта рецепторов ppar |
| EP1924546A1 (en) * | 2005-09-14 | 2008-05-28 | 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 |
| EA201101084A1 (ru) | 2005-12-22 | 2012-04-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Феноксиуксусные кислоты в качестве активаторов ppar дельта |
| US7943612B2 (en) | 2006-03-09 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds that modulate PPAR activity, their preparation and use |
| EP2001844A2 (en) * | 2006-03-14 | 2008-12-17 | Amgen, Inc | Bicyclic carboxylic acid derivatives useful for treating metabolic disorders |
| PE20080188A1 (es) | 2006-04-18 | 2008-03-10 | Janssen Pharmaceutica Nv | Derivados del acido benzoazepin-oxi-acetico 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 |
| EP2061760A1 (en) * | 2006-09-07 | 2009-05-27 | Amgen, Inc | Benzo-fused compounds for use in treating metabolic disorders |
| US7714008B2 (en) | 2006-09-07 | 2010-05-11 | Amgen Inc. | Heterocyclic GPR40 modulators |
| AU2007326114B2 (en) * | 2006-12-02 | 2011-08-25 | Seoul National University Industry Foundation | Aryl compounds as PPAR ligands and their use |
| CA2683751C (en) * | 2007-04-16 | 2013-01-08 | Amgen Inc. | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
| US8759355B2 (en) * | 2007-07-25 | 2014-06-24 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. | Aryl pyrimidine derivatives, preparation methods and pharmaceutical uses thereof |
| MX2010003876A (es) | 2007-10-10 | 2010-12-02 | Amgen Inc | Moduladores de gpr40 bifenilo- sustituidos. |
| EP2260017A1 (en) * | 2008-03-06 | 2010-12-15 | 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 |
| WO2013128378A1 (en) | 2012-02-28 | 2013-09-06 | Piramal Enterprises Limited | 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 |
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| CS175831B1 (enExample) * | 1974-12-17 | 1977-05-31 | ||
| 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 |
| CA2263721A1 (en) * | 1996-08-19 | 1998-02-26 | Satoshi Ohrui | Propionic acid derivatives and applications thereof |
| AU8750298A (en) * | 1997-08-28 | 1999-03-22 | Ono Pharmaceutical Co. Ltd. | Peroxisome proliferator-activated receptor controllers |
| US6506757B1 (en) * | 1998-03-10 | 2003-01-14 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| US6586475B1 (en) * | 1998-11-20 | 2003-07-01 | Takeda Chemical Industries, Ltd. | β-amyloid protein production/secretion inhibitors |
| EE200100558A (et) * | 1999-04-28 | 2002-12-16 | Aventis Pharma Deutschland Gmbh | Triarüülhappe derivaat, seda sisaldav farmatseutiline kompositsioon ja ühendi raviotstarbeline kasutamine |
| AU1624801A (en) * | 1999-11-19 | 2001-05-30 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists related applications |
| AU2001258771A1 (en) * | 2000-05-19 | 2001-11-26 | Takeda Chemical Industries Ltd. | -secretase inhibitors |
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- 2003-06-18 KR KR1020047020583A patent/KR20050030624A/ko not_active Ceased
- 2003-06-18 IL IL16547603A patent/IL165476A0/xx unknown
- 2003-06-18 DE DE60317326T patent/DE60317326T2/de not_active Expired - Fee Related
- 2003-06-18 EP EP03738056A patent/EP1513526B1/en not_active Expired - Lifetime
- 2003-06-18 PT PT03738056T patent/PT1513526E/pt unknown
- 2003-06-18 AT AT03738056T patent/ATE377420T1/de not_active IP Right Cessation
- 2003-06-18 MX MXPA04012857A patent/MXPA04012857A/es active IP Right Grant
- 2003-06-18 SI SI200331089T patent/SI1513526T1/sl unknown
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003245962A1 (en) | 2004-01-06 |
| GB0214149D0 (en) | 2002-07-31 |
| AU2003245962B2 (en) | 2008-07-03 |
| RU2323929C2 (ru) | 2008-05-10 |
| PL375148A1 (en) | 2005-11-28 |
| IS7574A (is) | 2004-11-30 |
| DE60317326D1 (de) | 2007-12-20 |
| HK1076712A1 (en) | 2006-01-27 |
| MXPA04012857A (es) | 2005-02-24 |
| CN1674897A (zh) | 2005-09-28 |
| NZ537210A (en) | 2006-09-29 |
| EP1513526B1 (en) | 2007-11-07 |
| WO2004000315A1 (en) | 2003-12-31 |
| JP2005534672A (ja) | 2005-11-17 |
| ATE377420T1 (de) | 2007-11-15 |
| US7338960B2 (en) | 2008-03-04 |
| CY1107168T1 (el) | 2012-10-24 |
| IL165476A0 (en) | 2006-01-15 |
| DK1513526T3 (da) | 2008-03-17 |
| DE60317326T2 (de) | 2008-08-28 |
| PT1513526E (pt) | 2008-02-12 |
| RU2004135539A (ru) | 2005-08-10 |
| NO20045328L (no) | 2005-03-09 |
| BR0311931A (pt) | 2005-04-05 |
| EP1513526A1 (en) | 2005-03-16 |
| US20060089394A1 (en) | 2006-04-27 |
| ES2295601T3 (es) | 2008-04-16 |
| SI1513526T1 (sl) | 2008-04-30 |
| ZA200410061B (en) | 2006-07-26 |
| CA2487909A1 (en) | 2003-12-31 |
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