JP2005505616A5 - - Google Patents
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- JP2005505616A5 JP2005505616A5 JP2003536195A JP2003536195A JP2005505616A5 JP 2005505616 A5 JP2005505616 A5 JP 2005505616A5 JP 2003536195 A JP2003536195 A JP 2003536195A JP 2003536195 A JP2003536195 A JP 2003536195A JP 2005505616 A5 JP2005505616 A5 JP 2005505616A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pent
- phenyl
- ethoxy
- ynyl
- 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.)
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- 229910052736 halogen Inorganic materials 0.000 claims 72
- 150000002367 halogens Chemical class 0.000 claims 72
- 150000001875 compounds Chemical class 0.000 claims 70
- -1 C 3-6 - alkenynyl Chemical group 0.000 claims 42
- 125000001424 substituent group Chemical group 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 19
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000732 arylene group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 6
- 239000005977 Ethylene Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
- 125000005549 heteroarylene group Chemical group 0.000 claims 6
- 230000003287 optical effect Effects 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- LMKKIEZOWSKCSP-UHFFFAOYSA-N 3-[4-[5-[3-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=CC(C#CC=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)=C1 LMKKIEZOWSKCSP-UHFFFAOYSA-N 0.000 claims 2
- UTPUMVWOJOGZEJ-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]-9-oxofluoren-2-yl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=C(C=2C(=CC(=CC=2)C#CC(C)=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)C2=O)C2=C1 UTPUMVWOJOGZEJ-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 102000006255 nuclear receptors Human genes 0.000 claims 2
- 108020004017 nuclear receptors Proteins 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- BHOWJSLAKFIFLM-UHFFFAOYSA-N 2-(2-benzoylanilino)-3-[4-[5-[4-[5-[4-[2-(2-benzoylanilino)-2-carboxyethyl]phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1NC(C(=O)O)CC(C=C1)=CC=C1OCC=CC#CC(C=C1)=CC=C1C#CC=CCOC(C=C1)=CC=C1CC(C(O)=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 BHOWJSLAKFIFLM-UHFFFAOYSA-N 0.000 claims 1
- FZZCXQUCZGBGHX-UHFFFAOYSA-N 2-[3-[5-[4-[5-[3-(2-ethoxy-2-oxoethyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]acetic acid Chemical compound CCOC(=O)CC1=CC=CC(OCC=CC#CC=2C=CC(=CC=2)C#CC=CCOC=2C=C(CC(O)=O)C=CC=2)=C1 FZZCXQUCZGBGHX-UHFFFAOYSA-N 0.000 claims 1
- MJUXCMADIDYWNI-UHFFFAOYSA-N 2-[4-[3-[3-[3-[4-(2-methoxy-2-oxoethyl)phenoxy]prop-1-ynyl]phenyl]prop-2-ynoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC#CC1=CC=CC(C#CCOC=2C=CC(CC(O)=O)=CC=2)=C1 MJUXCMADIDYWNI-UHFFFAOYSA-N 0.000 claims 1
- HKZFMPNKPKSHEJ-UHFFFAOYSA-N 2-[4-[3-[4-[4-[4-[4-(carboxymethoxy)-3-methylphenyl]sulfanylbut-2-en-2-yl]phenyl]phenyl]but-2-enylsulfanyl]-2-methylphenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=CC=1C(C)=CCSC1=CC=C(CC(O)=O)C(C)=C1 HKZFMPNKPKSHEJ-UHFFFAOYSA-N 0.000 claims 1
- XGIZHRCWEIVWOO-UHFFFAOYSA-N 2-[4-[3-[4-[4-[4-[4-(carboxymethyl)-2-chlorophenoxy]but-2-en-2-yl]phenyl]phenyl]but-2-enoxy]-3-chlorophenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(C)=CCOC=2C(=CC(CC(O)=O)=CC=2)Cl)C=CC=1C(C)=CCOC1=CC=C(CC(O)=O)C=C1Cl XGIZHRCWEIVWOO-UHFFFAOYSA-N 0.000 claims 1
- PUVFZEATGUBUAZ-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(OCC=C(C#CC=2C=C(C=CC2)C#CC(=CCOC2=CC=C(C=C2)C(C(=O)O)(C)OCC)C)C)C=C1)OCC PUVFZEATGUBUAZ-UHFFFAOYSA-N 0.000 claims 1
- QWJMWCIAPOFMMP-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC=1C=C(C=CC1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC QWJMWCIAPOFMMP-UHFFFAOYSA-N 0.000 claims 1
- AIDSGSJYUUOITO-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC=1C=C(C=CC1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC AIDSGSJYUUOITO-UHFFFAOYSA-N 0.000 claims 1
- LPCREQGGBHILJU-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC=1C=C(C=CC1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C LPCREQGGBHILJU-UHFFFAOYSA-N 0.000 claims 1
- JLDGRPBLIDIBPF-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenyl]acetic acid Chemical compound C=1C=CC(C#CC(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)=CC=1C#CC(C)=CCSC1=CC=C(CC(O)=O)C(C)=C1 JLDGRPBLIDIBPF-UHFFFAOYSA-N 0.000 claims 1
- AAUYKWOTSSMFME-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC=1C=C(C=CC1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C AAUYKWOTSSMFME-UHFFFAOYSA-N 0.000 claims 1
- TUEVAUYICVNLHE-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(carboxymethyl)-2-chlorophenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]-3-chlorophenyl]acetic acid Chemical compound C=1C=CC(C#CC(C)=CCOC=2C(=CC(CC(O)=O)=CC=2)Cl)=CC=1C#CC(C)=CCOC1=CC=C(CC(O)=O)C=C1Cl TUEVAUYICVNLHE-UHFFFAOYSA-N 0.000 claims 1
- RUUYBSUGPKIZTP-UHFFFAOYSA-N 2-[4-[5-[3-[5-[4-(carboxymethyl)-2-chlorophenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]-3-chlorophenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1OCC=CC#CC1=CC=CC(C#CC=CCOC=2C(=CC(CC(O)=O)=CC=2)Cl)=C1 RUUYBSUGPKIZTP-UHFFFAOYSA-N 0.000 claims 1
- AMKBRZNSQOOHBJ-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(OCC=C(C#CC2=CC=C(C=C2)C2=CC=C(C=C2)C#CC(=CCOC2=CC=C(C=C2)C(C(=O)O)(C)OCC)C)C)C=C1)OCC AMKBRZNSQOOHBJ-UHFFFAOYSA-N 0.000 claims 1
- NTQYBNFPDKDRCE-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C1=CC=C(C=C1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC NTQYBNFPDKDRCE-UHFFFAOYSA-N 0.000 claims 1
- VWLGCSUHALBVMX-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C1=CC=C(C=C1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC VWLGCSUHALBVMX-UHFFFAOYSA-N 0.000 claims 1
- ZZLFUWQHASOPBX-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C1=CC=C(C=C1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C ZZLFUWQHASOPBX-UHFFFAOYSA-N 0.000 claims 1
- KOZLTKXZTIBFPO-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C#CC(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=CC=1C#CC(C)=CCSC1=CC=C(CC(O)=O)C(C)=C1 KOZLTKXZTIBFPO-UHFFFAOYSA-N 0.000 claims 1
- ZHLFLHHKMQFEJB-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C1=CC=C(C=C1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C ZHLFLHHKMQFEJB-UHFFFAOYSA-N 0.000 claims 1
- OWTIKXUBXJGGOL-UHFFFAOYSA-N 2-[4-[5-[4-[4-[5-[4-(carboxymethyl)-2-chlorophenoxy]-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]-3-chlorophenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C#CC(C)=CCOC=2C(=CC(CC(O)=O)=CC=2)Cl)C=CC=1C#CC(C)=CCOC1=CC=C(CC(O)=O)C=C1Cl OWTIKXUBXJGGOL-UHFFFAOYSA-N 0.000 claims 1
- IFEKJQTWUUOPAS-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(OCC=C(C#CC2=CC=C(C=C2)C#CC(=CCOC2=CC=C(C=C2)C(C(=O)O)(C)OCC)C)C)C=C1)OCC IFEKJQTWUUOPAS-UHFFFAOYSA-N 0.000 claims 1
- QXHYZYKHNWYHQK-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC QXHYZYKHNWYHQK-UHFFFAOYSA-N 0.000 claims 1
- AOLFURDLRCHXAH-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)C(CC1=CC=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)OCC AOLFURDLRCHXAH-UHFFFAOYSA-N 0.000 claims 1
- JZAWFMKYEBDTTA-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(2-methoxy-2-oxoethoxy)-3-methylphenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]-2-methylphenoxy]acetic acid Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C=C(C)C(OCC(O)=O)=CC=2)C=C1 JZAWFMKYEBDTTA-UHFFFAOYSA-N 0.000 claims 1
- ZWNBCVYVZQSQBA-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C#CC(=CCOC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C ZWNBCVYVZQSQBA-UHFFFAOYSA-N 0.000 claims 1
- CWBJXYVTWCDXHE-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenyl]acetic acid Chemical compound C=1C=C(C#CC(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=CC=1C#CC(C)=CCSC1=CC=C(CC(O)=O)C(C)=C1 CWBJXYVTWCDXHE-UHFFFAOYSA-N 0.000 claims 1
- WGOKZGROCPCIIL-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C(=O)(O)COC1=C(C=C(C=C1)SCC=C(C#CC1=CC=C(C=C1)C#CC(=CCSC1=CC=C(C=C1)C(C(=O)O)(C)OCC)C)C)C WGOKZGROCPCIIL-UHFFFAOYSA-N 0.000 claims 1
- XZYXNIDTGVZNCN-UHFFFAOYSA-N 2-[4-[5-[4-[5-[4-(carboxymethyl)-2-chlorophenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]-3-chlorophenyl]acetic acid Chemical compound C=1C=C(C#CC(C)=CCOC=2C(=CC(CC(O)=O)=CC=2)Cl)C=CC=1C#CC(C)=CCOC1=CC=C(CC(O)=O)C=C1Cl XZYXNIDTGVZNCN-UHFFFAOYSA-N 0.000 claims 1
- XWAVVQXAJZJKJM-UHFFFAOYSA-N 2-[4-[5-[7-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9-oxofluoren-2-yl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C2=CC=C(C=C2C2=O)C#CC(C)=CCSC=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=1C#CC(C)=CCSC1=CC=C(OCC(O)=O)C(C)=C1 XWAVVQXAJZJKJM-UHFFFAOYSA-N 0.000 claims 1
- QHUVNZWSRBHWPN-UHFFFAOYSA-N 2-[4-[5-[7-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9h-carbazol-2-yl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C2=CC=C(C=C2N2)C#CC(C)=CCSC=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=1C#CC(C)=CCSC1=CC=C(OCC(O)=O)C(C)=C1 QHUVNZWSRBHWPN-UHFFFAOYSA-N 0.000 claims 1
- IWTKCDSLCHWCBP-UHFFFAOYSA-N 2-[4-[5-[7-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9h-carbazol-2-yl]pent-2-en-4-ynylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C2=CC=C(C=C2N2)C#CC=CCSC=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=1C#CC(C)=CCSC1=CC=C(OCC(O)=O)C(C)=C1 IWTKCDSLCHWCBP-UHFFFAOYSA-N 0.000 claims 1
- KHVFBHGMDMCCGX-UHFFFAOYSA-N 2-[4-[5-[7-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9h-fluoren-2-yl]-3-methylpent-2-en-4-ynyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C2=CC=C(C=C2C2)C#CC(C)=CCSC=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=1C#CC(C)=CCSC1=CC=C(OCC(O)=O)C(C)=C1 KHVFBHGMDMCCGX-UHFFFAOYSA-N 0.000 claims 1
- XPCPRYVAXIPMDP-UHFFFAOYSA-N 2-[4-[5-[7-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9h-fluoren-2-yl]pent-2-en-4-ynylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(C2=CC=C(C=C2C2)C#CC=CCSC=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=1C#CC(C)=CCSC1=CC=C(OCC(O)=O)C(C)=C1 XPCPRYVAXIPMDP-UHFFFAOYSA-N 0.000 claims 1
- DNHUVSFXLIJVBT-UHFFFAOYSA-N 3-[3-bromo-4-[5-[4-[5-[2-bromo-4-(2,3-diethoxy-3-oxopropyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C(=CC(CC(OCC)C(=O)OCC)=CC=2)Br)C=C1 DNHUVSFXLIJVBT-UHFFFAOYSA-N 0.000 claims 1
- WBNNGLSTECFJOB-UHFFFAOYSA-N 3-[4-[3-[4-[4-[4-[4-(2-carboxy-2-ethoxyethyl)phenoxy]but-2-en-2-yl]phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 WBNNGLSTECFJOB-UHFFFAOYSA-N 0.000 claims 1
- GTGLNACSGLRJKF-UHFFFAOYSA-N 3-[4-[3-[4-[4-[4-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanylbut-2-en-2-yl]phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCSC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 GTGLNACSGLRJKF-UHFFFAOYSA-N 0.000 claims 1
- CGQFHCSVHQXMGE-UHFFFAOYSA-N 3-[4-[3-[4-[4-[4-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanylbut-2-en-2-yl]phenyl]phenyl]but-2-enylsulfanyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCSC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 CGQFHCSVHQXMGE-UHFFFAOYSA-N 0.000 claims 1
- QMJIUGQLLMFEJB-UHFFFAOYSA-N 3-[4-[3-[4-[4-[4-[4-(carboxymethoxy)-3-methylphenyl]sulfanylbut-2-en-2-yl]phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=C1 QMJIUGQLLMFEJB-UHFFFAOYSA-N 0.000 claims 1
- YMJDOCQKCFJSNK-UHFFFAOYSA-N 3-[4-[3-[4-[4-[4-[4-(carboxymethoxy)-3-methylphenyl]sulfanylbut-2-en-2-yl]phenyl]phenyl]but-2-enylsulfanyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=C1 YMJDOCQKCFJSNK-UHFFFAOYSA-N 0.000 claims 1
- XSISCPYJHDFYSO-UHFFFAOYSA-N 3-[4-[5-[3-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=CC(C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)=C1 XSISCPYJHDFYSO-UHFFFAOYSA-N 0.000 claims 1
- PPPFKUZOBYDJNL-UHFFFAOYSA-N 3-[4-[5-[4-[4-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=C(C=2C=CC(=CC=2)C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 PPPFKUZOBYDJNL-UHFFFAOYSA-N 0.000 claims 1
- IBQTTYMWGHHIET-UHFFFAOYSA-N 3-[4-[5-[4-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]pent-3-en-1-ynyl]phenyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=C(C=2C=CC(=CC=2)C#CC=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 IBQTTYMWGHHIET-UHFFFAOYSA-N 0.000 claims 1
- GGGFPQBQISOYSE-UHFFFAOYSA-N 3-[4-[5-[4-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanylpent-3-en-1-ynyl]phenyl]phenyl]pent-2-en-4-ynylsulfanyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=CC#CC1=CC=C(C=2C=CC(=CC=2)C#CC=CCSC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 GGGFPQBQISOYSE-UHFFFAOYSA-N 0.000 claims 1
- WCSUANXLXLORFD-UHFFFAOYSA-N 3-[4-[5-[4-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanylpent-3-en-1-ynyl]phenyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=C(C=2C=CC(=CC=2)C#CC=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=C1 WCSUANXLXLORFD-UHFFFAOYSA-N 0.000 claims 1
- GPKRKCHDDYZQPR-UHFFFAOYSA-N 3-[4-[5-[4-[4-[5-[4-(carboxymethoxy)-3-methylphenyl]sulfanylpent-3-en-1-ynyl]phenyl]phenyl]pent-2-en-4-ynylsulfanyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=CC#CC1=CC=C(C=2C=CC(=CC=2)C#CC=CCSC=2C=C(C)C(OCC(O)=O)=CC=2)C=C1 GPKRKCHDDYZQPR-UHFFFAOYSA-N 0.000 claims 1
- DONNNMTWKHKHJE-UHFFFAOYSA-N 3-[4-[5-[4-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=C(C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 DONNNMTWKHKHJE-UHFFFAOYSA-N 0.000 claims 1
- PPRHTQAPLDSYQI-UHFFFAOYSA-N 3-[4-[5-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 PPRHTQAPLDSYQI-UHFFFAOYSA-N 0.000 claims 1
- MYIBIHBLROIABM-UHFFFAOYSA-N 3-[4-[5-[4-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanylpent-3-en-1-ynyl]phenyl]pent-2-en-4-ynylsulfanyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=CC#CC1=CC=C(C#CC=CCSC=2C=CC(CC(OCC)C(O)=O)=CC=2)C=C1 MYIBIHBLROIABM-UHFFFAOYSA-N 0.000 claims 1
- MPOCMEXRFDUBBJ-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]-9-oxofluoren-2-yl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=CC#CC1=CC=C(C=2C(=CC(=CC=2)C#CC(C)=CCOC=2C=CC(CC(OCC)C(O)=O)=CC=2)C2=O)C2=C1 MPOCMEXRFDUBBJ-UHFFFAOYSA-N 0.000 claims 1
- ITUHWOYFKZXDHG-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]-9h-carbazol-2-yl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=C2C3=CC=C(C#CC(C)=CCOC=4C=CC(CC(OCC)C(O)=O)=CC=4)C=C3NC2=C1 ITUHWOYFKZXDHG-UHFFFAOYSA-N 0.000 claims 1
- SYHLHYDHUQLNMZ-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenoxy]-3-methylpent-3-en-1-ynyl]-9h-fluoren-2-yl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC=C(C)C#CC1=CC=C2C3=CC=C(C#CC(C)=CCOC=4C=CC(CC(OCC)C(O)=O)=CC=4)C=C3CC2=C1 SYHLHYDHUQLNMZ-UHFFFAOYSA-N 0.000 claims 1
- AYJFZNNHQZPSQW-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9H-carbazol-2-yl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=C(C)C#CC1=CC=C2C3=CC=C(C#CC(C)=CCSC=4C=CC(CC(OCC)C(O)=O)=CC=4)C=C3NC2=C1 AYJFZNNHQZPSQW-UHFFFAOYSA-N 0.000 claims 1
- UXPHAGNBAZSDBK-UHFFFAOYSA-N 3-[4-[5-[7-[5-[4-(2-carboxy-2-ethoxyethyl)phenyl]sulfanyl-3-methylpent-3-en-1-ynyl]-9H-fluoren-2-yl]-3-methylpent-2-en-4-ynyl]sulfanylphenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1SCC=C(C)C#CC1=CC=C2C3=CC=C(C#CC(C)=CCSC=4C=CC(CC(OCC)C(O)=O)=CC=4)C=C3CC2=C1 UXPHAGNBAZSDBK-UHFFFAOYSA-N 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- LMBCWHWDEHGPPP-UHFFFAOYSA-N ethyl 2-[3-[5-[4-[5-[3-(2-ethoxy-2-oxoethyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OCC=CC#CC=2C=CC(=CC=2)C#CC=CCOC=2C=C(CC(=O)OCC)C=CC=2)=C1 LMBCWHWDEHGPPP-UHFFFAOYSA-N 0.000 claims 1
- JCRANWNIHQRJDR-UHFFFAOYSA-N ethyl 3-[3-bromo-4-[5-[4-[5-[2-bromo-4-(2,3-diethoxy-3-oxopropyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound BrC1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C(=CC(CC(OCC)C(=O)OCC)=CC=2)Br)C=C1 JCRANWNIHQRJDR-UHFFFAOYSA-N 0.000 claims 1
- WHFFYNUOTNZEBZ-UHFFFAOYSA-N ethyl 3-[4-[3-[4-[4-[4-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]but-2-en-2-yl]phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=C(C)C1=CC=C(C=2C=CC(=CC=2)C(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 WHFFYNUOTNZEBZ-UHFFFAOYSA-N 0.000 claims 1
- CSVWDJRRCFERKX-UHFFFAOYSA-N ethyl 3-[4-[5-[3-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=C(C)C#CC1=CC=CC(C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)=C1 CSVWDJRRCFERKX-UHFFFAOYSA-N 0.000 claims 1
- XPMMPSAWBQQBTK-UHFFFAOYSA-N ethyl 3-[4-[5-[4-[4-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=C(C)C#CC1=CC=C(C=2C=CC(=CC=2)C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 XPMMPSAWBQQBTK-UHFFFAOYSA-N 0.000 claims 1
- CUOMMBRKZDALLI-UHFFFAOYSA-N ethyl 3-[4-[5-[4-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=C(C)C#CC1=CC=C(C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 CUOMMBRKZDALLI-UHFFFAOYSA-N 0.000 claims 1
- VVGPJSVVDAOBHS-UHFFFAOYSA-N ethyl 3-[4-[5-[4-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C=C1 VVGPJSVVDAOBHS-UHFFFAOYSA-N 0.000 claims 1
- PEEGWSSFFNKOSR-UHFFFAOYSA-N ethyl 3-[4-[5-[7-[5-[4-(2,3-diethoxy-3-oxopropyl)phenoxy]-3-methylpent-3-en-1-ynyl]-9-oxofluoren-2-yl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCC=C(C)C#CC1=CC=C(C=2C(=CC(=CC=2)C#CC(C)=CCOC=2C=CC(CC(OCC)C(=O)OCC)=CC=2)C2=O)C2=C1 PEEGWSSFFNKOSR-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- NHHPYFYSDKUBBA-UHFFFAOYSA-N methyl 2-[4-[3-[3-[3-[4-(2-methoxy-2-oxoethyl)phenoxy]prop-1-ynyl]phenyl]prop-2-ynoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC#CC1=CC=CC(C#CCOC=2C=CC(CC(=O)OC)=CC=2)=C1 NHHPYFYSDKUBBA-UHFFFAOYSA-N 0.000 claims 1
- GIQLZHBNNGSTAI-UHFFFAOYSA-N methyl 2-[4-[5-[4-[5-[4-(2-methoxy-2-oxoethoxy)-3-methylphenoxy]pent-3-en-1-ynyl]phenyl]pent-2-en-4-ynoxy]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1OCC=CC#CC1=CC=C(C#CC=CCOC=2C=C(C)C(OCC(=O)OC)=CC=2)C=C1 GIQLZHBNNGSTAI-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 238000003419 tautomerization reaction Methods 0.000 claims 1
- 0 *OC(B*N[U]**I**C(O*)=O)=O Chemical compound *OC(B*N[U]**I**C(O*)=O)=O 0.000 description 2
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| US20050080115A1 (en) | 2002-10-28 | 2005-04-14 | Lone Jeppesen | Novel compounds, their preparation and use |
| DE60332860D1 (de) * | 2002-10-28 | 2010-07-15 | High Point Pharmaceuticals Llc | Neue verbindungen, die sich f r die behandlung von durch ppar vermittelten krankheiten eignen |
| AU2003287912A1 (en) * | 2002-12-20 | 2004-07-14 | Novo Nordisk A/S | Dicarboxylic acid derivatives as ppar-agonists |
| US7816385B2 (en) | 2002-12-20 | 2010-10-19 | High Point Pharmaceuticals, Llc | Dimeric dicarboxylic acid derivatives, their preparation and use |
| FR2850969B1 (fr) * | 2003-02-12 | 2005-03-25 | Genfit S A | Aminopropanediols acyles et analogues et leurs utilisations therapeutiques |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| ES2352085T3 (es) | 2004-05-05 | 2011-02-15 | High Point Pharmaceuticals, Llc | Nuevos compuestos, su preparación y uso. |
| EP1632245A1 (en) * | 2004-09-02 | 2006-03-08 | Technische Universität Dresden Medizinische Fakultät Carl Gustav Carus | ICA512 couples insulin secretion and gene expression in Beta-cells |
| ES2372617T3 (es) | 2005-06-30 | 2012-01-24 | High Point Pharmaceuticals, Llc | Ácidos fenoxiacéticos como activadores de ppar-delta. |
| EA201101085A1 (ru) | 2005-12-22 | 2012-05-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Феноксиуксусные кислоты в качестве активаторов ppar дельта |
| EP1999098A2 (en) * | 2006-03-09 | 2008-12-10 | High Point Pharmaceuticals, LLC | Compounds that modulate ppar activity, their preparation and use |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2010051206A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA2826649C (en) | 2011-02-25 | 2016-07-26 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| US20150004144A1 (en) | 2011-12-02 | 2015-01-01 | The General Hospital Corporation | Differentiation into brown adipocytes |
| US20140045746A1 (en) | 2012-08-02 | 2014-02-13 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| JP2016516004A (ja) | 2013-02-22 | 2016-06-02 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 抗糖尿病二環式化合物 |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| PL3004138T3 (pl) | 2013-06-05 | 2024-07-29 | Bausch Health Ireland Limited | Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2018106518A1 (en) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CN109200043A (zh) * | 2018-10-23 | 2019-01-15 | 华南农业大学 | 二羧酸（盐）在降低脂肪沉积和预防肥胖方面的应用 |
| CA3185909A1 (en) | 2020-07-22 | 2022-01-27 | Reneo Pharmaceuticals, Inc. | Crystalline ppar-delta agonist |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
| CN116003245B (zh) * | 2022-12-21 | 2026-03-27 | 山东瑞健生物医药科技有限公司 | 一种2-羟基-3-氧代戊烷二酸的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2331336A1 (fr) * | 1975-11-14 | 1977-06-10 | Rolland Sa A | Acides oxy-4,4' bis(phenoxy-2 alcanocarboxyliques), leurs derives et leur application comme medicament |
| US5508296A (en) * | 1991-07-30 | 1996-04-16 | Yamanouchi Pharmaceutical Co., Ltd. | Bisheterocyclic derivative or salt thereof |
| KR20020070508A (ko) * | 2000-01-28 | 2002-09-09 | 노보 노르디스크 에이/에스 | 프로피온산 유도체 및 당뇨병 및 비만의 치료에 그것의 사용 |
| PL357017A1 (en) * | 2000-01-28 | 2004-07-12 | Novo Nordisk A/S | Alkynylsubstituted propionic acid derivatives and their use against diabetes and obesity |
-
2002
- 2002-10-15 KR KR1020047005711A patent/KR20050036876A/ko not_active Withdrawn
- 2002-10-15 JP JP2003536195A patent/JP2005505616A/ja not_active Withdrawn
- 2002-10-15 EP EP02772084A patent/EP1438283A1/en not_active Withdrawn
- 2002-10-15 IL IL16117002A patent/IL161170A0/xx unknown
- 2002-10-15 RU RU2004114875/04A patent/RU2004114875A/ru not_active Application Discontinuation
- 2002-10-15 HU HU0401837A patent/HUP0401837A2/hu unknown
- 2002-10-15 WO PCT/DK2002/000692 patent/WO2003033453A1/en not_active Ceased
- 2002-10-15 CN CNA028205472A patent/CN1571766A/zh active Pending
- 2002-10-15 CA CA002462514A patent/CA2462514A1/en not_active Abandoned
- 2002-10-15 PL PL02370244A patent/PL370244A1/xx not_active Application Discontinuation
- 2002-10-15 BR BR0213253-2A patent/BR0213253A/pt not_active Application Discontinuation
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