NO20023567L - Alkynylsubstituerte propionsyrederivater og deres anvendelse mot sukkersyke og fedme - Google Patents
Alkynylsubstituerte propionsyrederivater og deres anvendelse mot sukkersyke og fedme Download PDFInfo
- Publication number
- NO20023567L NO20023567L NO20023567A NO20023567A NO20023567L NO 20023567 L NO20023567 L NO 20023567L NO 20023567 A NO20023567 A NO 20023567A NO 20023567 A NO20023567 A NO 20023567A NO 20023567 L NO20023567 L NO 20023567L
- Authority
- NO
- Norway
- Prior art keywords
- ynyloxy
- ethoxypropionic acid
- pent
- phenyl
- methylpent
- Prior art date
Links
- 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 273
- -1 C 1 -6 -alkyl Chemical group 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 53
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 238000011321 prophylaxis Methods 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 19
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 239000003937 drug carrier Substances 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- 125000005110 aryl thio group Chemical group 0.000 claims description 17
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 15
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 15
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 125000005907 alkyl ester group Chemical group 0.000 claims description 11
- 210000004027 cell Anatomy 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 125000000732 arylene group Chemical group 0.000 claims description 8
- SHHBDKPKMFQHAH-ARHOYUFESA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-methyl-5-phenylpent-2-en-4-ynoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C#CC1=CC=CC=C1 SHHBDKPKMFQHAH-ARHOYUFESA-N 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- LTZUJPUCWXJTSU-VPVJOJIASA-N (2s)-2-ethoxy-3-[4-[(e)-5-phenylpent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC=CC=C1 LTZUJPUCWXJTSU-VPVJOJIASA-N 0.000 claims description 7
- HEYBIHPGXJXPHD-RKMMBKDRSA-N C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(\C)C#CC1=CC(Cl)=CC(Cl)=C1 Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(\C)C#CC1=CC(Cl)=CC(Cl)=C1 HEYBIHPGXJXPHD-RKMMBKDRSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 102000006255 nuclear receptors Human genes 0.000 claims description 6
- 108020004017 nuclear receptors Proteins 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- 229960002354 repaglinide Drugs 0.000 claims description 6
- 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 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
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- LDMAWMWSTCNZPV-RSAMLISRSA-N (2s)-3-[4-[(z)-5-(3,5-dichlorophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(Cl)=CC(Cl)=C1 LDMAWMWSTCNZPV-RSAMLISRSA-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
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 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
- 229940079593 drug Drugs 0.000 claims description 4
- SHHBDKPKMFQHAH-QLWWLHSCSA-N ethyl (2s)-2-ethoxy-3-[4-[(z)-3-methyl-5-phenylpent-2-en-4-ynoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(\C)C#CC1=CC=CC=C1 SHHBDKPKMFQHAH-QLWWLHSCSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 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
- MFQIQMISMHBYLM-LXKWBGADSA-N (2s)-2-ethoxy-3-[4-[(e)-3-methyl-5-phenylpent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC=CC=C1 MFQIQMISMHBYLM-LXKWBGADSA-N 0.000 claims description 3
- CFOPQWHPAUUUQY-NJQMWTHNSA-N C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(\C)C#CC1=CC=CC2=CC=CC=C12 Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(\C)C#CC1=CC=CC2=CC=CC=C12 CFOPQWHPAUUUQY-NJQMWTHNSA-N 0.000 claims description 3
- UCOOXEBUANDZQS-BVBLWJPBSA-N C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C\C#CC1=CC(Cl)=CC(Cl)=C1 Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C\C#CC1=CC(Cl)=CC(Cl)=C1 UCOOXEBUANDZQS-BVBLWJPBSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000005354 acylalkyl 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
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- GXBVRHRUODRNJN-KOZCBZIKSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-3-methyl-5-[3-(trifluoromethyl)phenyl]pent-2-en-4-ynoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C#CC1=CC=CC(C(F)(F)F)=C1 GXBVRHRUODRNJN-KOZCBZIKSA-N 0.000 claims description 3
- DZSYJXNOEAYDFC-LNLBBOMNSA-N ethyl (2s)-2-ethoxy-3-[4-[(e)-5-phenylpent-2-en-4-ynoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C\C#CC1=CC=CC=C1 DZSYJXNOEAYDFC-LNLBBOMNSA-N 0.000 claims description 3
- DZSYJXNOEAYDFC-ZJZKVMBWSA-N ethyl (2s)-2-ethoxy-3-[4-[(z)-5-phenylpent-2-en-4-ynoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C/C#CC1=CC=CC=C1 DZSYJXNOEAYDFC-ZJZKVMBWSA-N 0.000 claims description 3
- HEYBIHPGXJXPHD-VHFIJRQBSA-N ethyl (2s)-3-[4-[(e)-5-(3,5-dichlorophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OC\C=C(/C)C#CC1=CC(Cl)=CC(Cl)=C1 HEYBIHPGXJXPHD-VHFIJRQBSA-N 0.000 claims description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-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
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- VPQCGJCAUTVEKV-OEHGHSTBSA-N (2s)-2-ethoxy-3-[4-[(e)-3-methyl-5-[3-(trifluoromethyl)phenyl]pent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC=CC(C(F)(F)F)=C1 VPQCGJCAUTVEKV-OEHGHSTBSA-N 0.000 claims description 2
- QDLLZQHWSYAJFO-XNQHKPBGSA-N (2s)-2-ethoxy-3-[4-[(z)-3-methyl-5-naphthalen-1-ylpent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC=CC2=CC=CC=C12 QDLLZQHWSYAJFO-XNQHKPBGSA-N 0.000 claims description 2
- LTZUJPUCWXJTSU-DJHHFUNSSA-N (2s)-2-ethoxy-3-[4-[(z)-5-phenylpent-2-en-4-ynoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1=CC=CC=C1 LTZUJPUCWXJTSU-DJHHFUNSSA-N 0.000 claims description 2
- ONJVXORHVJQLQD-ZGAQRXBASA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-dibromocyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(Br)C=CC=C(Br)C1 ONJVXORHVJQLQD-ZGAQRXBASA-N 0.000 claims description 2
- OGJPIWNJCGRJOF-PFHJWNERSA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-dibromocyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(Br)C=CC=C(Br)C1 OGJPIWNJCGRJOF-PFHJWNERSA-N 0.000 claims description 2
- DGOYVQWFGJAWQW-RBKRILAMSA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC)C=CC=C(OCC)C1 DGOYVQWFGJAWQW-RBKRILAMSA-N 0.000 claims description 2
- MRYVXNUOPZTRGZ-VNBDLNNKSA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(OCC)C=CC=C(OCC)C1 MRYVXNUOPZTRGZ-VNBDLNNKSA-N 0.000 claims description 2
- AOJRHHPRMFYFNS-ZGAQRXBASA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-difluorocyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(F)C=CC=C(F)C1 AOJRHHPRMFYFNS-ZGAQRXBASA-N 0.000 claims description 2
- ZMTVKSNBCVBVIN-PFHJWNERSA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-difluorocyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(F)C=CC=C(F)C1 ZMTVKSNBCVBVIN-PFHJWNERSA-N 0.000 claims description 2
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- OPJJBBMEOQYQFT-VDGVVHNXSA-N (2s)-3-[3-bromo-4-[(e)-5-(1,5-dimethoxycyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(OC)C=CC=C(OC)C1 OPJJBBMEOQYQFT-VDGVVHNXSA-N 0.000 claims description 2
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- ZMKQUCYAPRDAFO-PMDNVAFQSA-N (2s)-3-[3-bromo-4-[(e)-5-(3,5-diethoxyphenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC(OCC)=CC(OCC)=C1 ZMKQUCYAPRDAFO-PMDNVAFQSA-N 0.000 claims description 2
- QKEOMYLLGRAUSN-BODNZJIQSA-N (2s)-3-[3-bromo-4-[(e)-5-(3,5-difluorophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(F)=CC(F)=C1 QKEOMYLLGRAUSN-BODNZJIQSA-N 0.000 claims description 2
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- HYZVBXLDPKGWCM-CTSWPSOHSA-N (2s)-3-[3-chloro-4-[(e)-5-(3,5-diethoxyphenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(OCC)=CC(OCC)=C1 HYZVBXLDPKGWCM-CTSWPSOHSA-N 0.000 claims description 2
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- JHFJTHMSUFFPRJ-GUWAZMKPSA-N (2s)-3-[3-chloro-4-[(e)-5-(3,5-difluorophenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC(F)=CC(F)=C1 JHFJTHMSUFFPRJ-GUWAZMKPSA-N 0.000 claims description 2
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- VBJJQXYTHAHWFY-BVBLWJPBSA-N (2s)-3-[3-chloro-4-[(e)-5-(3,5-dimethoxyphenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC(OC)=CC(OC)=C1 VBJJQXYTHAHWFY-BVBLWJPBSA-N 0.000 claims description 2
- CGIUMSLPDNNCQT-KGSFJYNRSA-N (2s)-3-[3-chloro-4-[(z)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1(OCC)C=CC=C(OCC)C1 CGIUMSLPDNNCQT-KGSFJYNRSA-N 0.000 claims description 2
- SQVQSWJKCDCBPU-YLRTXIDLSA-N (2s)-3-[3-chloro-4-[(z)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1(OCC)C=CC=C(OCC)C1 SQVQSWJKCDCBPU-YLRTXIDLSA-N 0.000 claims description 2
- UUTLGJVQZBTOTD-SYMXCSSMSA-N (2s)-3-[3-chloro-4-[(z)-5-(1,5-difluorocyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1(F)C=CC=C(F)C1 UUTLGJVQZBTOTD-SYMXCSSMSA-N 0.000 claims description 2
- BULQZLBWTLQKOJ-OPQGSUJVSA-N (2s)-3-[3-chloro-4-[(z)-5-(1,5-diiodocyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1(I)C=CC=C(I)C1 BULQZLBWTLQKOJ-OPQGSUJVSA-N 0.000 claims description 2
- FJQFFECPKVVJSY-RENKASEKSA-N (2s)-3-[3-chloro-4-[(z)-5-(1,5-dimethoxycyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1(OC)C=CC=C(OC)C1 FJQFFECPKVVJSY-RENKASEKSA-N 0.000 claims description 2
- JWKQLCDLVCMRBK-YDBYVANFSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-dibromophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(Br)=CC(Br)=C1 JWKQLCDLVCMRBK-YDBYVANFSA-N 0.000 claims description 2
- HYZVBXLDPKGWCM-WLYOPYGYSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-diethoxyphenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(OCC)=CC(OCC)=C1 HYZVBXLDPKGWCM-WLYOPYGYSA-N 0.000 claims description 2
- QBMMCBFAACTXEV-NAFJXCGOSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-diethoxyphenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1=CC(OCC)=CC(OCC)=C1 QBMMCBFAACTXEV-NAFJXCGOSA-N 0.000 claims description 2
- JHFJTHMSUFFPRJ-OMUFJYGLSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-difluorophenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1=CC(F)=CC(F)=C1 JHFJTHMSUFFPRJ-OMUFJYGLSA-N 0.000 claims description 2
- UNNGWUAZSJFQLP-YDBYVANFSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-diiodophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(I)=CC(I)=C1 UNNGWUAZSJFQLP-YDBYVANFSA-N 0.000 claims description 2
- PPAWROQXKROQNO-VVVJUMKJSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-dimethoxyphenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(OC)=CC(OC)=C1 PPAWROQXKROQNO-VVVJUMKJSA-N 0.000 claims description 2
- VBJJQXYTHAHWFY-DADDIACRSA-N (2s)-3-[3-chloro-4-[(z)-5-(3,5-dimethoxyphenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C/C#CC1=CC(OC)=CC(OC)=C1 VBJJQXYTHAHWFY-DADDIACRSA-N 0.000 claims description 2
- QGPMNFGQRRDNSS-ZGAQRXBASA-N (2s)-3-[4-[(e)-5-(1,5-dibromocyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(Br)C=CC=C(Br)C1 QGPMNFGQRRDNSS-ZGAQRXBASA-N 0.000 claims description 2
- UVFBJDARYDNVPA-UICFQJRISA-N (2s)-3-[4-[(e)-5-(1,5-dibromocyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(Br)C=CC=C(Br)C1 UVFBJDARYDNVPA-UICFQJRISA-N 0.000 claims description 2
- MQFQTKSSXLCWAT-PFHJWNERSA-N (2s)-3-[4-[(e)-5-(1,5-dibromocyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(Br)C=CC=C(Br)C1 MQFQTKSSXLCWAT-PFHJWNERSA-N 0.000 claims description 2
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- VQNSUAANTRKDPV-RBKRILAMSA-N (2s)-3-[4-[(e)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC)C=CC=C(OCC)C1 VQNSUAANTRKDPV-RBKRILAMSA-N 0.000 claims description 2
- BCOYPYVOXBCBLB-UUWYDYNASA-N (2s)-3-[4-[(e)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC)C=CC=C(OCC)C1 BCOYPYVOXBCBLB-UUWYDYNASA-N 0.000 claims description 2
- OCYBWRBQJVVWLW-VNBDLNNKSA-N (2s)-3-[4-[(e)-5-(1,5-diethoxycyclohexa-2,4-dien-1-yl)pent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(OCC)C=CC=C(OCC)C1 OCYBWRBQJVVWLW-VNBDLNNKSA-N 0.000 claims description 2
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- ZMENIYPJLAYTIQ-BODNZJIQSA-N (2s)-3-[4-[(e)-5-(3,5-difluorophenyl)-3-methylpent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(F)=CC(F)=C1 ZMENIYPJLAYTIQ-BODNZJIQSA-N 0.000 claims description 2
- ZCCSCSRAFZBLLL-VROYLXGSSA-N (2s)-3-[4-[(e)-5-(3,5-difluorophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(F)=CC(F)=C1 ZCCSCSRAFZBLLL-VROYLXGSSA-N 0.000 claims description 2
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- MENRMNPLRKIAOA-BODNZJIQSA-N (2s)-3-[4-[(e)-5-(3,5-diiodophenyl)-3-methylpent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(I)=CC(I)=C1 MENRMNPLRKIAOA-BODNZJIQSA-N 0.000 claims description 2
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- KWERIBDIKKAQTO-GUWAZMKPSA-N (2s)-3-[4-[(e)-5-(3,5-diiodophenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC(I)=CC(I)=C1 KWERIBDIKKAQTO-GUWAZMKPSA-N 0.000 claims description 2
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- KTNTXXGMMZJANZ-VHFIJRQBSA-N (2s)-3-[4-[(e)-5-(3,5-dimethoxyphenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(OC)=CC(OC)=C1 KTNTXXGMMZJANZ-VHFIJRQBSA-N 0.000 claims description 2
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- AIXJVDVWFQIOSD-BVBLWJPBSA-N (2s)-3-[4-[(e)-5-(3,5-dimethoxyphenyl)pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1=CC(OC)=CC(OC)=C1 AIXJVDVWFQIOSD-BVBLWJPBSA-N 0.000 claims description 2
- PAGYMNAMVMIZGC-HUILLMRYSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]-3-methylpent-2-en-4-ynoxy]-3-bromophenyl]-2-ethoxypropanoic acid Chemical compound BrC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 PAGYMNAMVMIZGC-HUILLMRYSA-N 0.000 claims description 2
- FTTHJJJRPZQXHM-HUILLMRYSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]-3-methylpent-2-en-4-ynoxy]-3-chlorophenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 FTTHJJJRPZQXHM-HUILLMRYSA-N 0.000 claims description 2
- IUDXGHANOWXIBO-HUILLMRYSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]-3-methylpent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 IUDXGHANOWXIBO-HUILLMRYSA-N 0.000 claims description 2
- BMJGFIKOPQZNPQ-MUSPHSLOSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 BMJGFIKOPQZNPQ-MUSPHSLOSA-N 0.000 claims description 2
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- CAQZGKQEISXDLZ-XXQPFPDHSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]pent-2-en-4-ynoxy]-3-iodophenyl]-2-ethoxypropanoic acid Chemical compound IC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 CAQZGKQEISXDLZ-XXQPFPDHSA-N 0.000 claims description 2
- FPNFGQFNVXWDCZ-XXQPFPDHSA-N (2s)-3-[4-[(e)-5-[1,5-bis(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-yl]pent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C\C#CC1(OCC(F)(F)F)C=CC=C(OCC(F)(F)F)C1 FPNFGQFNVXWDCZ-XXQPFPDHSA-N 0.000 claims description 2
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- KUUWNQVFBPYJGN-FZRLKEFVSA-N (2s)-3-[4-[(e)-5-[3,5-bis(2,2,2-trifluoroethoxy)phenyl]-3-methylpent-2-en-4-ynoxy]-3-chlorophenyl]-2-ethoxypropanoic acid Chemical compound ClC1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(OCC(F)(F)F)=CC(OCC(F)(F)F)=C1 KUUWNQVFBPYJGN-FZRLKEFVSA-N 0.000 claims description 2
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- ZMOQRERCLICEKZ-VROYLXGSSA-N (2s)-3-[4-[(e)-5-[3,5-bis(trifluoromethyl)phenyl]-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(/C)C#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZMOQRERCLICEKZ-VROYLXGSSA-N 0.000 claims description 2
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- ZCCSCSRAFZBLLL-RSAMLISRSA-N (2s)-3-[4-[(z)-5-(3,5-difluorophenyl)-3-methylpent-2-en-4-ynoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC\C=C(\C)C#CC1=CC(F)=CC(F)=C1 ZCCSCSRAFZBLLL-RSAMLISRSA-N 0.000 claims description 2
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- 230000032258 transport Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- 229960001130 urapidil Drugs 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200000137 | 2000-01-28 | ||
DKPA200001065 | 2000-07-07 | ||
DKPA200001593 | 2000-10-25 | ||
PCT/DK2001/000057 WO2001055086A1 (en) | 2000-01-28 | 2001-01-26 | Alkynylsubstituted propionic acid derivatives and their use against diabetes and obesity |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20023567D0 NO20023567D0 (no) | 2002-07-26 |
NO20023567L true NO20023567L (no) | 2002-09-25 |
Family
ID=27222337
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20023567A NO20023567L (no) | 2000-01-28 | 2002-07-26 | Alkynylsubstituerte propionsyrederivater og deres anvendelse mot sukkersyke og fedme |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1254102A1 (es) |
JP (1) | JP2003520839A (es) |
KR (1) | KR20020090211A (es) |
CN (1) | CN1396904A (es) |
AU (1) | AU2831801A (es) |
BR (1) | BR0107902A (es) |
CA (1) | CA2396372A1 (es) |
HU (1) | HUP0204247A3 (es) |
IL (1) | IL150259A0 (es) |
MX (1) | MXPA02007295A (es) |
NO (1) | NO20023567L (es) |
PL (1) | PL357017A1 (es) |
WO (1) | WO2001055086A1 (es) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI311133B (en) * | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
JPWO2003016265A1 (ja) | 2001-08-17 | 2004-12-02 | エーザイ株式会社 | 環状化合物およびpparアゴニスト |
US7220877B2 (en) | 2001-10-17 | 2007-05-22 | Novo Nordisk A/S | Compounds, their preparation and use |
EP1438283A1 (en) * | 2001-10-17 | 2004-07-21 | Novo Nordisk A/S | Dicarboxylic acid derivatives, their preparation and therapeutic use |
ITRM20020014A1 (it) * | 2002-01-15 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati di acidi a-feniltiocarbossilici e a-fenilossicarbossilici utili per il trattamento di patologie che rispondono all'attivazione del |
CN1688540A (zh) * | 2002-09-05 | 2005-10-26 | 诺沃挪第克公司 | 新颖的乙烯基羧酸衍生物以及它们的治疗用途 |
WO2005105736A1 (en) | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
US20090042781A1 (en) * | 2004-06-28 | 2009-02-12 | Novo Nordisk A/S | Methods for Treating Diabetes |
EA201101085A1 (ru) | 2005-12-22 | 2012-05-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Феноксиуксусные кислоты в качестве активаторов ppar дельта |
CA3005158A1 (en) | 2014-11-06 | 2016-05-12 | Scholar Rock, Inc. | Anti-pro/latent-myostatin antibodies and uses thereof |
CN113896789A (zh) | 2015-09-15 | 2022-01-07 | 供石公司 | 抗-原肌生长抑制素/潜伏肌生长抑制素抗体及其用途 |
EP4218817A3 (en) * | 2017-01-06 | 2023-09-06 | Scholar Rock, Inc. | Methods for treating metabolic diseases by inhibiting myostatin activation |
JP2023534835A (ja) | 2020-07-22 | 2023-08-14 | レネオ ファーマシューティカルズ,インク. | 結晶性pparデルタアゴニスト |
WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL176885B1 (pl) * | 1992-07-03 | 1999-08-31 | Smithkline Beecham Plc | Kompozycja farmaceutyczna |
FR2707989B1 (fr) * | 1993-07-22 | 1995-10-13 | Pf Medicament | Nouveaux dérivés de benzylamines silylées, leurs sels, leurs procédés de fabrication et les compositions pharmaceutiques les renfermant. |
BR9508468A (pt) * | 1994-07-29 | 1997-11-25 | Smithkline Beecham Plc | Composto processo para a preparação do mesmo composição farmacéutica processos para o tratamento e/ou profilaxia de hiperglicemia em um mamifero humano ou não humano e para o tratamento de hiperlípidemia hipertensão doença cardiovascular alguns distúrbios de alimentação o tratamento e/ou profilaxia de doença renal a prevenção revers o estabilização ou retardo da progressão de microalbuminuria em um mamifero humano ou não humano uso do composto e composto intermediário |
GB9600464D0 (en) * | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
GB9606805D0 (en) * | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
-
2001
- 2001-01-26 CN CN01804239A patent/CN1396904A/zh active Pending
- 2001-01-26 KR KR1020027009399A patent/KR20020090211A/ko not_active Application Discontinuation
- 2001-01-26 IL IL15025901A patent/IL150259A0/xx unknown
- 2001-01-26 EP EP01946845A patent/EP1254102A1/en not_active Withdrawn
- 2001-01-26 CA CA002396372A patent/CA2396372A1/en not_active Abandoned
- 2001-01-26 WO PCT/DK2001/000057 patent/WO2001055086A1/en not_active Application Discontinuation
- 2001-01-26 MX MXPA02007295A patent/MXPA02007295A/es unknown
- 2001-01-26 BR BR0107902-6A patent/BR0107902A/pt not_active IP Right Cessation
- 2001-01-26 HU HU0204247A patent/HUP0204247A3/hu unknown
- 2001-01-26 AU AU28318/01A patent/AU2831801A/en not_active Abandoned
- 2001-01-26 JP JP2001555029A patent/JP2003520839A/ja active Pending
- 2001-01-26 PL PL01357017A patent/PL357017A1/xx not_active Application Discontinuation
-
2002
- 2002-07-26 NO NO20023567A patent/NO20023567L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
NO20023567D0 (no) | 2002-07-26 |
WO2001055086A1 (en) | 2001-08-02 |
HUP0204247A3 (en) | 2003-10-28 |
MXPA02007295A (es) | 2002-11-29 |
JP2003520839A (ja) | 2003-07-08 |
HUP0204247A2 (hu) | 2003-04-28 |
BR0107902A (pt) | 2002-11-05 |
KR20020090211A (ko) | 2002-11-30 |
EP1254102A1 (en) | 2002-11-06 |
AU2831801A (en) | 2001-08-07 |
IL150259A0 (en) | 2002-12-01 |
PL357017A1 (en) | 2004-07-12 |
CN1396904A (zh) | 2003-02-12 |
CA2396372A1 (en) | 2001-08-02 |
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Legal Events
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FC2A | Withdrawal, rejection or dismissal of laid open patent application |