NO20023566L - Propionsyrederivater og deres anvendelse ved behandling av sukkkersyke og fedme - Google Patents
Propionsyrederivater og deres anvendelse ved behandling av sukkkersyke og fedme Download PDFInfo
- Publication number
- NO20023566L NO20023566L NO20023566A NO20023566A NO20023566L NO 20023566 L NO20023566 L NO 20023566L NO 20023566 A NO20023566 A NO 20023566A NO 20023566 A NO20023566 A NO 20023566A NO 20023566 L NO20023566 L NO 20023566L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- enyloxy
- allyloxy
- ethoxy
- optionally substituted
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 36
- 208000008589 Obesity Diseases 0.000 title claims description 21
- 235000020824 obesity Nutrition 0.000 title claims description 21
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 6
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 title 1
- 150000005599 propionic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 414
- -1 cyan Chemical group 0.000 claims description 214
- 238000000034 method Methods 0.000 claims description 195
- 239000000203 mixture Substances 0.000 claims description 136
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical class 0.000 claims description 133
- 125000001424 substituent group Chemical group 0.000 claims description 130
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 122
- 125000003118 aryl group Chemical group 0.000 claims description 110
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 97
- 125000001072 heteroaryl group Chemical group 0.000 claims description 78
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 76
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 66
- 150000003839 salts Chemical class 0.000 claims description 58
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000004104 aryloxy group Chemical group 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000002252 acyl group Chemical group 0.000 claims description 43
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 43
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000005110 aryl thio group Chemical group 0.000 claims description 39
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 39
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 36
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000001769 aryl amino group Chemical group 0.000 claims description 25
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 20
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 19
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
- 206010022489 Insulin Resistance Diseases 0.000 claims description 18
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 239000003937 drug carrier Substances 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 14
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- IFPAIAWCQICHGW-XGLNBYONSA-N ethyl (2s)-3-[4-[(e)-3-[4-(4-bromophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 IFPAIAWCQICHGW-XGLNBYONSA-N 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- XUDBETVSFKGDDL-VROYLXGSSA-N ethyl (2s)-3-[4-[(e)-3-[3,5-bis(trifluoromethyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XUDBETVSFKGDDL-VROYLXGSSA-N 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 8
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 8
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 8
- VHQYXHXLMLYEAY-KGLAKQQASA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-(4-phenoxyphenyl)but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C(C=C1)=CC=C1OC1=CC=CC=C1 VHQYXHXLMLYEAY-KGLAKQQASA-N 0.000 claims description 8
- ADNBKVARKIDQCI-KGLAKQQASA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-(4-phenylphenyl)but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC=CC=2)C=C1 ADNBKVARKIDQCI-KGLAKQQASA-N 0.000 claims description 8
- PIZWOICFXMVMPB-DIQKFAEUSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-(9h-fluoren-2-yl)but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C2C3=CC=CC=C3CC2=C1 PIZWOICFXMVMPB-DIQKFAEUSA-N 0.000 claims description 8
- WITNUYNGONORCE-QMPJNXRZSA-N ethyl (2s)-3-[4-[(e)-3-(4-bromophenyl)but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(Br)C=C1 WITNUYNGONORCE-QMPJNXRZSA-N 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- RXYCRTPUOHFIKR-SHTLVRLNSA-N (2s)-3-[4-[(e)-3-[3,5-bis(2,2,2-trifluoroethoxy)phenyl]prop-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C1=CC(OCC(F)(F)F)=CC(OCC(F)(F)F)=C1 RXYCRTPUOHFIKR-SHTLVRLNSA-N 0.000 claims description 7
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- VOEOZTUVKKWHGW-WFTVZMDTSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-naphthalen-2-ylbut-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=CC=C2)C2=C1 VOEOZTUVKKWHGW-WFTVZMDTSA-N 0.000 claims description 7
- AATIYNGGQQQKDT-ZDJZVTAXSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-pyridin-2-ylbut-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=CC=N1 AATIYNGGQQQKDT-ZDJZVTAXSA-N 0.000 claims description 7
- PJJNKODENMRBTR-KPUQOTSHSA-N ethyl (2s)-3-[4-[(e)-3-(3,4-dimethoxyphenyl)but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(OC)C(OC)=C1 PJJNKODENMRBTR-KPUQOTSHSA-N 0.000 claims description 7
- LXENEDLGVRAEAE-IKKBDJOUSA-N ethyl (2s)-3-[4-[(e)-3-[3,5-bis(phenylmethoxy)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC(OCC=2C=CC=CC=2)=CC(OCC=2C=CC=CC=2)=C1 LXENEDLGVRAEAE-IKKBDJOUSA-N 0.000 claims description 7
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 7
- 229960003105 metformin Drugs 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 6
- BEWUJQFMSPHMKQ-SQAMQDMYSA-N C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C(C)=C(/C)C1=CC=C(Br)C=C1 Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C(C)=C(/C)C1=CC=C(Br)C=C1 BEWUJQFMSPHMKQ-SQAMQDMYSA-N 0.000 claims description 6
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 claims description 6
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- TWIRFULTOJJYMS-VROYLXGSSA-N ethyl (2s)-3-[4-[(e)-3-(3,5-dibromophenyl)but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC(Br)=CC(Br)=C1 TWIRFULTOJJYMS-VROYLXGSSA-N 0.000 claims description 6
- PXHUOXDQKPNLMZ-ZCQLBKDISA-N ethyl (2s)-3-[4-[(e)-3-(4-bromophenyl)-2-ethylbut-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C(CC)=C(/C)C1=CC=C(Br)C=C1 PXHUOXDQKPNLMZ-ZCQLBKDISA-N 0.000 claims description 6
- CEGIJQVKAZKLEU-XGLNBYONSA-N ethyl (2s)-3-[4-[(e)-3-[4-(4-chlorophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 CEGIJQVKAZKLEU-XGLNBYONSA-N 0.000 claims description 6
- GONMODFHNGXRJZ-QRNOMBBYSA-N ethyl (e)-3-[3-[4-[(e)-4-[4-[(2s)-2,3-diethoxy-3-oxopropyl]phenoxy]but-2-en-2-yl]phenyl]phenyl]but-2-enoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=CC=2)C(\C)=C\C(=O)OCC)C=C1 GONMODFHNGXRJZ-QRNOMBBYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 102000006255 nuclear receptors Human genes 0.000 claims description 6
- 108020004017 nuclear receptors Proteins 0.000 claims description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 6
- 229960002354 repaglinide Drugs 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- IARLQHYKUDROPT-GDNFTRMYSA-N (2s)-2-ethoxy-3-[4-[(e)-3-(4-phenylphenyl)but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC=CC=2)C=C1 IARLQHYKUDROPT-GDNFTRMYSA-N 0.000 claims description 5
- ROLRCAYFGOZPJS-IURSYISVSA-N (2s)-3-[4-[(e)-3-(4-bromophenyl)but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(Br)C=C1 ROLRCAYFGOZPJS-IURSYISVSA-N 0.000 claims description 5
- LQMBEQFFHTZGQS-ZUZKWDDASA-N (2s)-3-[4-[(e)-3-[4-(3-acetylphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=CC=2)C(C)=O)C=C1 LQMBEQFFHTZGQS-ZUZKWDDASA-N 0.000 claims description 5
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 5
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- ICHNHWLNJDKITM-IADSKUHDSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(2-methylphenyl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 ICHNHWLNJDKITM-IADSKUHDSA-N 0.000 claims description 5
- HSLCHPQKAGAJCF-FBRNXRPFSA-N ethyl (2s)-3-[4-[(e)-3-[4-(4-acetylphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(=CC=2)C(C)=O)C=C1 HSLCHPQKAGAJCF-FBRNXRPFSA-N 0.000 claims description 5
- PXHUOXDQKPNLMZ-QAACRSNZSA-N ethyl (2s)-3-[4-[(z)-3-(4-bromophenyl)-2-ethylbut-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C(CC)=C(\C)C1=CC=C(Br)C=C1 PXHUOXDQKPNLMZ-QAACRSNZSA-N 0.000 claims description 5
- 229950004994 meglitinide Drugs 0.000 claims description 5
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 claims description 5
- 229960000698 nateglinide Drugs 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- MOWUMDHIGSBTPB-GDNFTRMYSA-N (2s)-2-ethoxy-3-[4-[(e)-3-(4-phenoxyphenyl)but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C(C=C1)=CC=C1OC1=CC=CC=C1 MOWUMDHIGSBTPB-GDNFTRMYSA-N 0.000 claims description 4
- WLPGILKMLHCUGT-ZICGYBOYSA-N (2s)-2-ethoxy-3-[4-[(e)-3-(9h-fluoren-2-yl)but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C2C3=CC=CC=C3CC2=C1 WLPGILKMLHCUGT-ZICGYBOYSA-N 0.000 claims description 4
- JUUYCOVYGJZSGL-BHAFLUAZSA-N (2s)-2-ethoxy-3-[4-[(e)-3-[4-(3-methylphenyl)phenyl]but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C)C=CC=2)C=C1 JUUYCOVYGJZSGL-BHAFLUAZSA-N 0.000 claims description 4
- WZUVVRPGDMAKDS-YJRBMFNESA-N (2s)-2-ethoxy-3-[4-[(e)-3-[4-(4-methoxyphenoxy)phenyl]but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C(C=C1)=CC=C1OC1=CC=C(OC)C=C1 WZUVVRPGDMAKDS-YJRBMFNESA-N 0.000 claims description 4
- BWKSZMDJFHVSOW-KPUQOTSHSA-N (2s)-2-ethoxy-3-[4-[(e)-3-naphthalen-2-ylbut-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=CC=C2)C2=C1 BWKSZMDJFHVSOW-KPUQOTSHSA-N 0.000 claims description 4
- KPSQYBAFXWJKEC-LSSBLYJVSA-N (2s)-2-ethoxy-3-[4-[(e)-3-pyridin-2-ylbut-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=CC=N1 KPSQYBAFXWJKEC-LSSBLYJVSA-N 0.000 claims description 4
- LOJKKUXKHXGMTQ-KFGZODLXSA-N (2s)-3-[4-[(e)-3-(3,4-dimethoxyphenyl)but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(OC)C(OC)=C1 LOJKKUXKHXGMTQ-KFGZODLXSA-N 0.000 claims description 4
- HOKXPQQTEFAKOO-MXECYCPESA-N (2s)-3-[4-[(e)-3-(3,5-dibromophenyl)but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC(Br)=CC(Br)=C1 HOKXPQQTEFAKOO-MXECYCPESA-N 0.000 claims description 4
- FVNMATFYGNOSRW-RTLBZRNLSA-N (2s)-3-[4-[(e)-3-(3,5-dibromophenyl)prop-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C1=CC(Br)=CC(Br)=C1 FVNMATFYGNOSRW-RTLBZRNLSA-N 0.000 claims description 4
- UYCPRTLGKJHLLA-BKELBIJQSA-N (2s)-3-[4-[(e)-3-(4-bromophenyl)-2-ethylbut-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C(CC)=C(/C)C1=CC=C(Br)C=C1 UYCPRTLGKJHLLA-BKELBIJQSA-N 0.000 claims description 4
- MTZBHPWHBSWQDG-ANUWBXLYSA-N (2s)-3-[4-[(e)-3-(4-bromophenyl)-2-methylbut-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C(C)=C(/C)C1=CC=C(Br)C=C1 MTZBHPWHBSWQDG-ANUWBXLYSA-N 0.000 claims description 4
- NREWHBJYCMXWNO-ATKMGCRQSA-N (2s)-3-[4-[(e)-3-[3,5-bis(phenylmethoxy)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC(OCC=2C=CC=CC=2)=CC(OCC=2C=CC=CC=2)=C1 NREWHBJYCMXWNO-ATKMGCRQSA-N 0.000 claims description 4
- SQMMICVOHGJTPK-MXECYCPESA-N (2s)-3-[4-[(e)-3-[3,5-bis(trifluoromethyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SQMMICVOHGJTPK-MXECYCPESA-N 0.000 claims description 4
- WPFPQIFEMJEMHY-YJRBMFNESA-N (2s)-3-[4-[(e)-3-[4-(2,6-dimethoxyphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=CC=2OC)OC)C=C1 WPFPQIFEMJEMHY-YJRBMFNESA-N 0.000 claims description 4
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 claims description 4
- 125000006017 1-propenyl group Chemical group 0.000 claims description 4
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000027455 binding Effects 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- DTSCMTRWAMRMAS-IADSKUHDSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(4-methoxyphenoxy)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C(C=C1)=CC=C1OC1=CC=C(OC)C=C1 DTSCMTRWAMRMAS-IADSKUHDSA-N 0.000 claims description 4
- DIQVQKCKWOJJRT-GTKPELIYSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(4-propan-2-ylphenyl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(=CC=2)C(C)C)C=C1 DIQVQKCKWOJJRT-GTKPELIYSA-N 0.000 claims description 4
- JRZRZZKUXZNYMJ-FKCOHSBYSA-N ethyl (2s)-3-[4-[(e)-3-[4-[3,5-bis(trifluoromethyl)phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 JRZRZZKUXZNYMJ-FKCOHSBYSA-N 0.000 claims description 4
- BEWUJQFMSPHMKQ-VMZYVOJKSA-N ethyl (2s)-3-[4-[(z)-3-(4-bromophenyl)-2-methylbut-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C(C)=C(\C)C1=CC=C(Br)C=C1 BEWUJQFMSPHMKQ-VMZYVOJKSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- AZECXLPMVGCGEX-FOTOHYBBSA-N methyl 4-[[3-[(e)-3-[4-[(2s)-2,3-diethoxy-3-oxopropyl]phenoxy]prop-1-enyl]phenoxy]methyl]benzoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C\C1=CC=CC(OCC=2C=CC(=CC=2)C(=O)OC)=C1 AZECXLPMVGCGEX-FOTOHYBBSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- CVWRSHGCTHVISM-ICCXZJDVSA-N (2s)-3-[4-[(e)-3-[4-(3,5-dichlorophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(Cl)C=C(Cl)C=2)C=C1 CVWRSHGCTHVISM-ICCXZJDVSA-N 0.000 claims description 3
- JUGYTNFPNMKCML-YJWXQWNFSA-N (2s)-3-[4-[(e)-3-[4-(4-acetylphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(=CC=2)C(C)=O)C=C1 JUGYTNFPNMKCML-YJWXQWNFSA-N 0.000 claims description 3
- IGTJNXAGJKEBCJ-ICCXZJDVSA-N (2s)-3-[4-[(e)-3-[4-[3,5-bis(trifluoromethyl)phenyl]phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 IGTJNXAGJKEBCJ-ICCXZJDVSA-N 0.000 claims description 3
- UYCPRTLGKJHLLA-KNIWAEIXSA-N (2s)-3-[4-[(z)-3-(4-bromophenyl)-2-ethylbut-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C(CC)=C(\C)C1=CC=C(Br)C=C1 UYCPRTLGKJHLLA-KNIWAEIXSA-N 0.000 claims description 3
- MTZBHPWHBSWQDG-QZJMSCLXSA-N (2s)-3-[4-[(z)-3-(4-bromophenyl)-2-methylbut-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C(C)=C(\C)C1=CC=C(Br)C=C1 MTZBHPWHBSWQDG-QZJMSCLXSA-N 0.000 claims description 3
- XOZKBWWTEFOGIT-JFAKYYBVSA-N 4-[[3-[(e)-3-[4-[(2s)-2-carboxy-2-ethoxyethyl]phenoxy]prop-1-enyl]phenoxy]methyl]benzoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C1=CC=CC(OCC=2C=CC(=CC=2)C(O)=O)=C1 XOZKBWWTEFOGIT-JFAKYYBVSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- KFWNNPKVINTIIR-QMPJNXRZSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-(4-iodophenyl)but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(I)C=C1 KFWNNPKVINTIIR-QMPJNXRZSA-N 0.000 claims description 3
- JDPRQAKUEQKHEL-SICPGDBSSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(2-methoxy-5-propan-2-ylphenyl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=C(C=2)C(C)C)OC)C=C1 JDPRQAKUEQKHEL-SICPGDBSSA-N 0.000 claims description 3
- BJIUHLSEPDDBOJ-WFTVZMDTSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(furan-2-yl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2OC=CC=2)C=C1 BJIUHLSEPDDBOJ-WFTVZMDTSA-N 0.000 claims description 3
- FSXLXOUBEPPSTF-VHFIJRQBSA-N ethyl (2s)-3-[4-[(e)-3-(3,5-dimethoxyphenyl)but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC(OC)=CC(OC)=C1 FSXLXOUBEPPSTF-VHFIJRQBSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- RKSIATIUVLOPOM-YJRBMFNESA-N (2s)-2-ethoxy-3-[4-[(e)-3-[4-(2-methylphenyl)phenyl]but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 RKSIATIUVLOPOM-YJRBMFNESA-N 0.000 claims description 2
- NVESKTBASVLICE-ONDKDMNRSA-N (2s)-2-ethoxy-3-[4-[(e)-3-[4-(3-methoxyphenyl)phenyl]but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(OC)C=CC=2)C=C1 NVESKTBASVLICE-ONDKDMNRSA-N 0.000 claims description 2
- FCJMQXABXSLUAX-ZRDAINHMSA-N (2s)-2-ethoxy-3-[4-[(e)-3-[4-(4-propan-2-ylphenyl)phenyl]but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(=CC=2)C(C)C)C=C1 FCJMQXABXSLUAX-ZRDAINHMSA-N 0.000 claims description 2
- UOSPOUZBTLIOER-ZUZKWDDASA-N (2s)-3-[4-[(e)-3-[4-(2,5-dimethoxyphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=C(OC)C=2)OC)C=C1 UOSPOUZBTLIOER-ZUZKWDDASA-N 0.000 claims description 2
- SXMKJRHFJCITER-ICCXZJDVSA-N (2s)-3-[4-[(e)-3-[4-(3,5-dibromophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(Br)C=C(Br)C=2)C=C1 SXMKJRHFJCITER-ICCXZJDVSA-N 0.000 claims description 2
- UQASGQKTWOQLGL-DXCHCPKQSA-N (2s)-3-[4-[(e)-3-[4-(4-bromophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 UQASGQKTWOQLGL-DXCHCPKQSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- GQZVJVKRDDVSMV-BVONYCCWSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(3-methylphenyl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C)C=CC=2)C=C1 GQZVJVKRDDVSMV-BVONYCCWSA-N 0.000 claims description 2
- VBLPUJWOTUZGPN-XGLNBYONSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-[4-(4-fluorophenyl)phenyl]but-2-enoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 VBLPUJWOTUZGPN-XGLNBYONSA-N 0.000 claims description 2
- KQTIEVQIGYUMCP-IADSKUHDSA-N ethyl (2s)-3-[4-[(e)-3-[4-(2,6-dimethoxyphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=CC=2OC)OC)C=C1 KQTIEVQIGYUMCP-IADSKUHDSA-N 0.000 claims description 2
- FECQVLGNMGVWNN-FKCOHSBYSA-N ethyl (2s)-3-[4-[(e)-3-[4-(3,5-dibromophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(Br)C=C(Br)C=2)C=C1 FECQVLGNMGVWNN-FKCOHSBYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 36
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 5
- 230000003914 insulin secretion Effects 0.000 claims 3
- OWHHWFGJJYMEBL-DXCHCPKQSA-N (2s)-3-[4-[(e)-3-[4-(4-chlorophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 OWHHWFGJJYMEBL-DXCHCPKQSA-N 0.000 claims 2
- ZHRAZTKXXAVGAQ-XPGGBCAFSA-N (2s)-3-[4-[(e)-3-[4-(2,3-dichlorophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=C(Cl)C=CC=2)Cl)C=C1 ZHRAZTKXXAVGAQ-XPGGBCAFSA-N 0.000 claims 1
- YNOLMVSZQAQUSR-YJRBMFNESA-N ethyl (2s)-3-[4-[(e)-3-[4-(2,3-dichlorophenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=C(Cl)C=CC=2)Cl)C=C1 YNOLMVSZQAQUSR-YJRBMFNESA-N 0.000 claims 1
- IHMFXLMJHJHJKQ-GTALTYTBSA-N ethyl (2s)-3-[4-[(e)-3-[4-(3,5-ditert-butylphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)C=C1 IHMFXLMJHJHJKQ-GTALTYTBSA-N 0.000 claims 1
- ANIJZFZYHNAHGB-ALSNVVLCSA-N ethyl (2s)-3-[4-[(e)-3-[4-(3-acetylphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C=C(C=CC=2)C(C)=O)C=C1 ANIJZFZYHNAHGB-ALSNVVLCSA-N 0.000 claims 1
- SAOOIYTUYFWOIN-YDLQAMFKSA-N ethyl (2s)-3-[4-[(e)-3-[4-(5-chloro-2-methoxyphenyl)phenyl]but-2-enoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C1=CC=C(C=2C(=CC=C(Cl)C=2)OC)C=C1 SAOOIYTUYFWOIN-YDLQAMFKSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 295
- 238000005481 NMR spectroscopy Methods 0.000 description 233
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 159
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 127
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 87
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 76
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 60
- 239000007787 solid Substances 0.000 description 59
- 239000011734 sodium Substances 0.000 description 55
- 238000004949 mass spectrometry Methods 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 229910052799 carbon Inorganic materials 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 37
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 37
- 239000000047 product Substances 0.000 description 37
- NEJJCKFYYBEQRQ-LBPRGKRZSA-N ethyl (2s)-2-ethoxy-3-(4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)[C@@H](OCC)CC1=CC=C(O)C=C1 NEJJCKFYYBEQRQ-LBPRGKRZSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 239000012267 brine Substances 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 239000003480 eluent Substances 0.000 description 25
- 238000004452 microanalysis Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
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Classifications
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
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- 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
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
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- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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PCT/DK2001/000058 WO2001055085A1 (en) | 2000-01-28 | 2001-01-26 | Propionic acid derivatives and their use in the treatment of diabetes and obesity |
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NO20023566A NO20023566L (no) | 2000-01-28 | 2002-07-26 | Propionsyrederivater og deres anvendelse ved behandling av sukkkersyke og fedme |
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JP (1) | JP2003520838A (zh) |
KR (1) | KR20020070508A (zh) |
CN (1) | CN1396903A (zh) |
AU (1) | AU2831901A (zh) |
BR (1) | BR0107901A (zh) |
CA (1) | CA2395298A1 (zh) |
HU (1) | HUP0204574A3 (zh) |
IL (1) | IL150260A0 (zh) |
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NO (1) | NO20023566L (zh) |
PL (1) | PL357010A1 (zh) |
WO (1) | WO2001055085A1 (zh) |
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JP4170214B2 (ja) | 2001-03-08 | 2008-10-22 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルベニア | 抗感染用剤としての表面両親媒性ポリマー |
TWI311133B (en) * | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
US6869967B2 (en) | 2001-07-30 | 2005-03-22 | Novo Nordisk A/S | Peroxisome proliferator-activated receptor (PPAR) active vinyl carboxylic acid derivatives |
US7067530B2 (en) | 2001-07-30 | 2006-06-27 | Novo Nordisk A/S | Compounds, their preparation and use |
WO2003011807A1 (en) * | 2001-07-30 | 2003-02-13 | Novo Nordisk A/S | Novel vinyl carboxylic acid derivatives and their use as antidiabetics etc. |
WO2003016265A1 (fr) | 2001-08-17 | 2003-02-27 | Eisai Co., Ltd. | Compose cyclique et agoniste du recepteur ppar |
KR20050035142A (ko) | 2001-10-11 | 2005-04-15 | 카네카 코포레이션 | 페록시좀 증식제 응답성 수용체 리간드제 및 그 제조 방법 |
US7220877B2 (en) | 2001-10-17 | 2007-05-22 | Novo Nordisk A/S | Compounds, their preparation and use |
PL370244A1 (en) * | 2001-10-17 | 2005-05-16 | Novo Nordisk A/S | Dicarboxylic acid derivatives, their preparation and therapeutic use |
KR20050057178A (ko) | 2002-09-05 | 2005-06-16 | 노보 노르디스크 에이/에스 | 신규 비닐 카르복실산 유도체 및 그들의 치료에의 사용 |
US20050080115A1 (en) | 2002-10-28 | 2005-04-14 | Lone Jeppesen | Novel compounds, their preparation and use |
BR0315667A (pt) | 2002-10-28 | 2005-09-06 | Novo Nordisk As | Composto, uso de um composto, composição farmacêutica, e, método para o tratamento |
WO2004041266A1 (ja) | 2002-11-08 | 2004-05-21 | Takeda Pharmaceutical Company Limited | 受容体機能調節剤 |
US7268157B2 (en) | 2002-11-26 | 2007-09-11 | Shenzhen Chipscreen Biosciences, Ltd. | Substituted arylalcanoic acid derivatives as PPAR pan agonists with potent antihyperglycemic and antihyperlipidemic activity |
US7192970B2 (en) | 2002-11-26 | 2007-03-20 | Chipscreen Biosciences, Ltd. | Noncyclic 1,3-dicarbonyl compounds as dual PPAR agonists with potent antihyperglycemic and antihyperlipidemic activity |
EP2471526A3 (en) | 2003-03-17 | 2012-12-12 | The Trustees Of The University Of Pennsylvania | Facially amphiphillic polymers and oligomers and uses thereof |
ITRM20030305A1 (it) * | 2003-06-20 | 2004-12-21 | Sigma Tau Ind Farmaceuti | Preparazione di nuovi derivati di acidi fenil o fenossialchil mono e dicarbossilici utili nel trattamento dell'iperglicemia e dell'ipertrigliceridemia tipiche del diabete del tipo ii. |
JP4922615B2 (ja) | 2003-11-26 | 2012-04-25 | 武田薬品工業株式会社 | 受容体機能調節剤 |
RU2006126978A (ru) | 2003-12-25 | 2008-01-27 | Такеда Фармасьютикал Компани Лимитед (Jp) | Производные 3-(4-бензилоксифенил)пропановой кислоты |
EP1698624B1 (en) | 2003-12-26 | 2012-06-27 | Takeda Pharmaceutical Company Limited | Phenylpropanoic acid derivatives |
EP2468711A3 (en) * | 2004-01-23 | 2012-09-19 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polyaryl and polarylalkynyl polymers and oligomers and uses thereof |
GB0403148D0 (en) * | 2004-02-12 | 2004-03-17 | Smithkline Beecham Corp | Chemical compounds |
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 |
RU2006144121A (ru) * | 2004-05-14 | 2008-06-20 | Айрм Ллк (Us) | Соединения и композиции в качестве модуляторов ppar рецепторов, активируемых пролифератором пероксисом |
CA2570800A1 (en) | 2004-06-18 | 2006-01-26 | Wyeth | Processes for preparing 6-alkyl-5-arylsulfonyl- dihydrophenanthridines |
NZ568488A (en) | 2005-12-22 | 2011-07-29 | High Point Pharmaceuticals Llc | Phenoxy acetic acids as PPAR delta activators |
KR100788454B1 (ko) * | 2006-06-15 | 2007-12-24 | 대원제약주식회사 | 속효성이 증진된 나테글리니드를 유효성분으로 함유하는약제학적 조성물 |
KR101497577B1 (ko) * | 2012-07-31 | 2015-03-02 | 서울대학교산학협력단 | 2-에톡시프로피온산 유도체 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 일주기 연관성 질환의 예방 또는 치료용 약학적 조성물 |
US11267795B2 (en) | 2020-07-22 | 2022-03-08 | Reneo Pharmaceuticals, Inc. | Crystalline PPAR-delta agonist |
CN114349723B (zh) * | 2021-12-23 | 2024-02-02 | 中山大学 | 多烯炔类化合物及其制备方法和应用 |
WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (7)
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ES2200248T3 (es) * | 1997-09-19 | 2004-03-01 | Ssp Co., Ltd. | Derivados de acudi fenilpropionico sustituido en alfa y medicamento que los contienen. |
CN1280574A (zh) * | 1997-10-27 | 2001-01-17 | 雷迪研究基金会 | 新的杂环化合物及其在医药中的应用、它们的制备方法和含有它们的药物组合物 |
WO1999019313A1 (en) * | 1997-10-27 | 1999-04-22 | Dr. Reddy's Research Foundation | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
JP2002501909A (ja) * | 1998-01-29 | 2002-01-22 | ドクター・レディーズ・リサーチ・ファウンデーション | 新規なアルカン酸およびその医薬における使用、並びにその製造方法、およびそれを含有する薬学的組成物 |
AU1120599A (en) * | 1998-04-23 | 1999-03-08 | Dr. Reddy's Research Foundation | New heterocyclic compounds and their use in medicine, process for their reparation and pharmaceutical compositions containing them |
NZ504106A (en) * | 1998-05-27 | 2003-02-28 | Dr | Fused Oxazine, Thiazine and pipyridine compounds, process for their preparation and pharmaceutical compositions containing them |
RU2001131111A (ru) * | 1999-04-20 | 2003-08-10 | Ново Нордиск А/С (DK) | Новые соединения, их получение и применение |
-
2001
- 2001-01-26 EP EP01946844A patent/EP1254101A1/en not_active Withdrawn
- 2001-01-26 MX MXPA02007286A patent/MXPA02007286A/es unknown
- 2001-01-26 WO PCT/DK2001/000058 patent/WO2001055085A1/en not_active Application Discontinuation
- 2001-01-26 HU HU0204574A patent/HUP0204574A3/hu unknown
- 2001-01-26 PL PL01357010A patent/PL357010A1/xx not_active Application Discontinuation
- 2001-01-26 AU AU28319/01A patent/AU2831901A/en not_active Abandoned
- 2001-01-26 JP JP2001555028A patent/JP2003520838A/ja active Pending
- 2001-01-26 KR KR1020027009463A patent/KR20020070508A/ko not_active Application Discontinuation
- 2001-01-26 IL IL15026001A patent/IL150260A0/xx unknown
- 2001-01-26 BR BR0107901-8A patent/BR0107901A/pt not_active IP Right Cessation
- 2001-01-26 CA CA002395298A patent/CA2395298A1/en not_active Abandoned
- 2001-01-26 CN CN01804241A patent/CN1396903A/zh active Pending
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2002
- 2002-07-26 NO NO20023566A patent/NO20023566L/no not_active Application Discontinuation
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HUP0204574A3 (en) | 2003-08-28 |
CA2395298A1 (en) | 2001-08-02 |
BR0107901A (pt) | 2002-11-05 |
MXPA02007286A (es) | 2002-11-29 |
HUP0204574A2 (en) | 2003-05-28 |
PL357010A1 (en) | 2004-07-12 |
AU2831901A (en) | 2001-08-07 |
KR20020070508A (ko) | 2002-09-09 |
NO20023566D0 (no) | 2002-07-26 |
EP1254101A1 (en) | 2002-11-06 |
IL150260A0 (en) | 2002-12-01 |
WO2001055085A1 (en) | 2001-08-02 |
JP2003520838A (ja) | 2003-07-08 |
CN1396903A (zh) | 2003-02-12 |
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