JP2007508382A5 - - Google Patents
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- Publication number
- JP2007508382A5 JP2007508382A5 JP2006535505A JP2006535505A JP2007508382A5 JP 2007508382 A5 JP2007508382 A5 JP 2007508382A5 JP 2006535505 A JP2006535505 A JP 2006535505A JP 2006535505 A JP2006535505 A JP 2006535505A JP 2007508382 A5 JP2007508382 A5 JP 2007508382A5
- Authority
- JP
- Japan
- Prior art keywords
- phenoxy
- methyl
- compound
- phenyl
- propionic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 73
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 24
- -1 Cyano, Hydroxyl Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- 102000004877 Insulin Human genes 0.000 claims description 2
- 108090001061 Insulin Proteins 0.000 claims description 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims description 2
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002404 acyltransferase inhibitor Substances 0.000 claims description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 2
- 230000003579 anti-obesity Effects 0.000 claims description 2
- 239000003524 antilipemic agent Substances 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 229940125396 insulin Drugs 0.000 claims description 2
- 229950004994 meglitinide Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 26
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- ZTXCKVXIMNUYPZ-UHFFFAOYSA-N 2-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 ZTXCKVXIMNUYPZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims 2
- KTYRLONATYWFHZ-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-phenoxyphenoxy)-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(Cl)=CC=2)OC=2C=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 KTYRLONATYWFHZ-UHFFFAOYSA-N 0.000 claims 2
- PHNUJEYPGONSJD-UHFFFAOYSA-N 3-[4-[3-(4-ethyl-2-phenoxyphenoxy)-5-fluorophenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C=CC=CC=1OC1=CC(CC)=CC=C1OC(C=1)=CC(F)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 PHNUJEYPGONSJD-UHFFFAOYSA-N 0.000 claims 2
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000004452 carbocyclyl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical class 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- 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 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- VRGGHOWUQGDEEH-UHFFFAOYSA-N 2-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 VRGGHOWUQGDEEH-UHFFFAOYSA-N 0.000 claims 1
- ZPLBAMYKLHRLRC-UHFFFAOYSA-N 2-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-methylphenyl]sulfanylacetic acid Chemical compound C1=C(SCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 ZPLBAMYKLHRLRC-UHFFFAOYSA-N 0.000 claims 1
- ACRDSYPLXKXWLA-UHFFFAOYSA-N 2-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OC1=CC=CC(OC=2C(=CC(Cl)=CC=2)OC=2C=CC=CC=2)=C1 ACRDSYPLXKXWLA-UHFFFAOYSA-N 0.000 claims 1
- OJLXSVZICLWSGY-UHFFFAOYSA-N 3-[2-methyl-4-[3-(2-phenoxyphenoxy)phenoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 OJLXSVZICLWSGY-UHFFFAOYSA-N 0.000 claims 1
- GCZDIKOYHNCZSJ-UHFFFAOYSA-N 3-[2-methyl-4-[3-[2-phenoxy-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(=CC=3)C(F)(F)F)OC=3C=CC=CC=3)C=CC=2)=C1 GCZDIKOYHNCZSJ-UHFFFAOYSA-N 0.000 claims 1
- GYMZFOUNXANSFP-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-(2-methylphenoxy)-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)OC=2C(=CC=CC=2)C)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 GYMZFOUNXANSFP-UHFFFAOYSA-N 0.000 claims 1
- YSYDOWKOVAQTCA-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-(2-oxopyridin-1-yl)-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)N2C(C=CC=C2)=O)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 YSYDOWKOVAQTCA-UHFFFAOYSA-N 0.000 claims 1
- IJDWFWVUSNFROE-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-(3-methylphenoxy)-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound CC1=CC=CC(OC=2C(=CC=C(C=2)C(F)(F)F)OC=2C=C(OC=3C=C(C)C(CCC(O)=O)=CC=3)C=C(C)C=2)=C1 IJDWFWVUSNFROE-UHFFFAOYSA-N 0.000 claims 1
- GXTOZOBPAWNCAX-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-(4-methylphenoxy)-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(C)=CC=C1OC1=CC(C(F)(F)F)=CC=C1OC1=CC(C)=CC(OC=2C=C(C)C(CCC(O)=O)=CC=2)=C1 GXTOZOBPAWNCAX-UHFFFAOYSA-N 0.000 claims 1
- HNIUTDUFLHVKDN-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-(4-methylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 HNIUTDUFLHVKDN-UHFFFAOYSA-N 0.000 claims 1
- ORGVZLGSORRYAH-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-[2-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)C=2C(=CC=CC=2)OC(F)(F)F)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 ORGVZLGSORRYAH-UHFFFAOYSA-N 0.000 claims 1
- IFOVCSPJPYBGBZ-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-phenoxy-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)OC=2C=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 IFOVCSPJPYBGBZ-UHFFFAOYSA-N 0.000 claims 1
- DWYCPMURCNROKV-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-pyridin-2-yl-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)C=2N=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 DWYCPMURCNROKV-UHFFFAOYSA-N 0.000 claims 1
- HUKHUMICYNRPML-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-pyridin-2-yloxy-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)OC=2N=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 HUKHUMICYNRPML-UHFFFAOYSA-N 0.000 claims 1
- NOPMFQODGUOTHI-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-pyridin-3-yl-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)C=2C=NC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 NOPMFQODGUOTHI-UHFFFAOYSA-N 0.000 claims 1
- TYDKZCUZAZKRRB-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[2-pyridin-3-yloxy-4-(trifluoromethyl)phenoxy]phenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)OC=2C=NC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 TYDKZCUZAZKRRB-UHFFFAOYSA-N 0.000 claims 1
- RJXYAPMKHIHNER-UHFFFAOYSA-N 3-[2-methyl-4-[3-methyl-5-[3-phenoxy-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]phenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CN=2)C(F)(F)F)OC=2C=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 RJXYAPMKHIHNER-UHFFFAOYSA-N 0.000 claims 1
- BLUDIGJSODTDPE-UHFFFAOYSA-N 3-[4-[3-(2-benzoyl-4-chlorophenoxy)-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(Cl)=CC=2)C(=O)C=2C=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 BLUDIGJSODTDPE-UHFFFAOYSA-N 0.000 claims 1
- YTLDTPXLEXSZCZ-UHFFFAOYSA-N 3-[4-[3-(2-benzoyl-4-chlorophenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)C(=O)C=3C=CC=CC=3)C=CC=2)=C1 YTLDTPXLEXSZCZ-UHFFFAOYSA-N 0.000 claims 1
- WVYLKFAMRNNFMC-UHFFFAOYSA-N 3-[4-[3-(2-benzoyl-4-ethylphenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C=CC=CC=1C(=O)C1=CC(CC)=CC=C1OC(C=1)=CC=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 WVYLKFAMRNNFMC-UHFFFAOYSA-N 0.000 claims 1
- XIBTVVCUSZLMMG-UHFFFAOYSA-N 3-[4-[3-(2-benzoylphenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC=CC=3)C(=O)C=3C=CC=CC=3)C=CC=2)=C1 XIBTVVCUSZLMMG-UHFFFAOYSA-N 0.000 claims 1
- RFQWVKBETZJMOF-UHFFFAOYSA-N 3-[4-[3-(2-benzyl-4-chlorophenoxy)-5-fluorophenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)CC=3C=CC=CC=3)C=C(F)C=2)=C1 RFQWVKBETZJMOF-UHFFFAOYSA-N 0.000 claims 1
- AUFRACIKWQSDKZ-UHFFFAOYSA-N 3-[4-[3-(2-benzyl-4-chlorophenoxy)-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(Cl)=CC=2)CC=2C=CC=CC=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 AUFRACIKWQSDKZ-UHFFFAOYSA-N 0.000 claims 1
- HGYPNXJHDPSSCZ-UHFFFAOYSA-N 3-[4-[3-(2-benzyl-4-chlorophenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)CC=3C=CC=CC=3)C=CC=2)=C1 HGYPNXJHDPSSCZ-UHFFFAOYSA-N 0.000 claims 1
- XDBOGDHMDIYEIL-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-cyclohexylphenoxy)-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(Cl)=CC=2)C2CCCCC2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 XDBOGDHMDIYEIL-UHFFFAOYSA-N 0.000 claims 1
- XGCVZFGHASJIGX-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-phenoxyphenoxy)-5-fluorophenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=C(F)C=2)=C1 XGCVZFGHASJIGX-UHFFFAOYSA-N 0.000 claims 1
- HNWWPZFVXYHLCE-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-ethylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(CC)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 HNWWPZFVXYHLCE-UHFFFAOYSA-N 0.000 claims 1
- YUDJUHIYCSUZBS-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-fluorophenyl]propanoic acid Chemical compound C1=C(F)C(CCC(=O)O)=CC=C1OC1=CC=CC(OC=2C(=CC(Cl)=CC=2)OC=2C=CC=CC=2)=C1 YUDJUHIYCSUZBS-UHFFFAOYSA-N 0.000 claims 1
- PVCDNEALOANKMZ-UHFFFAOYSA-N 3-[4-[3-(4-chloro-2-phenoxyphenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(Cl)=CC=3)OC=3C=CC=CC=3)C=CC=2)=C1 PVCDNEALOANKMZ-UHFFFAOYSA-N 0.000 claims 1
- GYCQWUHIKHFRNE-UHFFFAOYSA-N 3-[4-[3-(4-ethyl-2-phenoxyphenoxy)phenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C=CC=CC=1OC1=CC(CC)=CC=C1OC(C=1)=CC=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 GYCQWUHIKHFRNE-UHFFFAOYSA-N 0.000 claims 1
- FLBWZQJFOWYLOZ-UHFFFAOYSA-N 3-[4-[3-[2-(2-acetylphenyl)-4-(trifluoromethyl)phenoxy]-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound CC(=O)C1=CC=CC=C1C1=CC(C(F)(F)F)=CC=C1OC1=CC(C)=CC(OC=2C=C(C)C(CCC(O)=O)=CC=2)=C1 FLBWZQJFOWYLOZ-UHFFFAOYSA-N 0.000 claims 1
- FWGPMZGNEVCHET-UHFFFAOYSA-N 3-[4-[3-[2-(3,5-difluorophenoxy)-4-(trifluoromethyl)phenoxy]-5-methylphenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C(OC=2C(=CC(=CC=2)C(F)(F)F)OC=2C=C(F)C=C(F)C=2)=CC(C)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 FWGPMZGNEVCHET-UHFFFAOYSA-N 0.000 claims 1
- GPSZVUFVMUABMO-UHFFFAOYSA-N 3-[4-[3-[4-ethyl-2-(2-phenylpropan-2-yl)phenoxy]-5-fluorophenoxy]-2-methylphenyl]propanoic acid Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC(CC)=CC=C1OC(C=1)=CC(F)=CC=1OC1=CC=C(CCC(O)=O)C(C)=C1 GPSZVUFVMUABMO-UHFFFAOYSA-N 0.000 claims 1
- WBIJSJHLSRGDKQ-UHFFFAOYSA-N 3-[4-[3-chloro-5-[2-(3-fluorophenoxy)-4-(trifluoromethyl)phenoxy]phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OC=2C=C(OC=3C(=CC(=CC=3)C(F)(F)F)OC=3C=C(F)C=CC=3)C=C(Cl)C=2)=C1 WBIJSJHLSRGDKQ-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2004/030911 WO2005037763A1 (en) | 2003-10-14 | 2004-10-08 | Phenoxyether derivatives as ppar modulators |
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| KR101415503B1 (ko) | 2003-07-17 | 2014-07-04 | 플렉시콘, 인코퍼레이티드 | Ｐｐａｒ 활성 화합물 |
| US7348338B2 (en) | 2003-07-17 | 2008-03-25 | Plexxikon, Inc. | PPAR active compounds |
| AU2005245386B2 (en) * | 2004-05-07 | 2008-11-27 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
| US7550499B2 (en) | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| CN101065388B (zh) | 2004-11-23 | 2011-12-21 | 西巴特殊化学品控股有限公司 | 制备酰基磷烷及其衍生物的方法 |
| US7531568B2 (en) | 2004-11-30 | 2009-05-12 | Plexxikon, Inc. | PPAR active compounds |
| WO2007002563A1 (en) | 2005-06-27 | 2007-01-04 | Exelixis, Inc. | Imidazole based lxr modulators |
| US7714002B2 (en) * | 2005-06-27 | 2010-05-11 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| EP1940767A2 (en) * | 2005-09-07 | 2008-07-09 | Plexxikon, Inc. | Pparactive compounds |
| WO2008073825A1 (en) | 2006-12-08 | 2008-06-19 | Exelixis, Inc. | Lxr and fxr modulators |
| WO2008096769A1 (ja) * | 2007-02-08 | 2008-08-14 | Daiichi Sankyo Company, Limited | 置換されたセルコスポラミド誘導体を含有する医薬 |
| PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| JP2010520303A (ja) * | 2007-03-08 | 2010-06-10 | プレキシコン，インコーポレーテッド | Ｐｐａｒ活性化合物 |
| BRPI0809643A2 (pt) | 2007-04-05 | 2014-11-11 | Daiichi Sankyo Co Ltd | Derivados de heteroarila bicíclica fundida |
| EP2240276B1 (en) * | 2007-12-06 | 2020-12-02 | Centre National de la Recherche Scientifique (CNRS) | Iron and copper catalytic systems for cross-coupling reactions |
| RU2527177C2 (ru) | 2007-12-20 | 2014-08-27 | Энвиво Фармасьютикалз, Инк. | Четырехзамещенные бензолы |
| BRPI1006113A2 (pt) | 2009-03-05 | 2016-02-16 | Daiichi Sankyo Co Ltd | "derivado de piridina". |
| AU2011296737A1 (en) | 2010-08-31 | 2013-04-11 | Snu R&Db Foundation | Use of the fetal reprogramming of a PPAR delta agonist |
| JP6699011B2 (ja) * | 2014-07-04 | 2020-05-27 | 国立大学法人 東京大学 | 脂肪酸サロゲートを含むリゾホスファチジルセリン誘導体 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1563871A (en) * | 1977-04-07 | 1980-04-02 | Lafon Labor | Derivatives of 4-(4-(4-chlorophenoxy)phenoxy)phenol |
| ES2059527T3 (es) * | 1987-09-09 | 1994-11-16 | Zeneca Ltd | Fungicidas. |
| DK0597102T3 (da) * | 1991-07-30 | 1999-08-09 | Yamanouchi Pharma Co Ltd | Nyt bisheterocyklisk derivat og salt heraf samt hypoglykæmisk sammensætning |
| DK0696585T3 (da) | 1993-04-30 | 1999-08-23 | Yamanouchi Pharma Co Ltd | Nyt bisoxadiazolidinderivat |
| US5424280A (en) * | 1993-10-07 | 1995-06-13 | American Cyanamid Company | Aryloxybenzene herbicidal agents |
| JPH0859638A (ja) * | 1994-08-26 | 1996-03-05 | Yamanouchi Pharmaceut Co Ltd | 新規なヘテロ環誘導体又はその塩 |
| AU2002230057A1 (en) * | 2001-01-29 | 2002-08-12 | Insight Strategy And Marketing Ltd | Diphenyl ether derivatives and their uses as heparanase inhibitors |
| NZ529351A (en) * | 2001-06-07 | 2006-01-27 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors |
| US7557143B2 (en) | 2003-04-18 | 2009-07-07 | Bristol-Myers Squibb Company | Thyroid receptor ligands |
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2004
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- 2004-10-08 EP EP04793892A patent/EP1675814A1/en not_active Withdrawn
- 2004-10-08 WO PCT/US2004/030911 patent/WO2005037763A1/en not_active Ceased
- 2004-10-08 US US10/571,961 patent/US7608639B2/en not_active Expired - Fee Related
- 2004-10-08 CA CA002541751A patent/CA2541751A1/en not_active Abandoned
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