JP2009519965A5 - - Google Patents

Info

Publication number

JP2009519965A5

JP2009519965A5 JP2008545947A JP2008545947A JP2009519965A5 JP 2009519965 A5 JP2009519965 A5 JP 2009519965A5 JP 2008545947 A JP2008545947 A JP 2008545947A JP 2008545947 A JP2008545947 A JP 2008545947A JP 2009519965 A5 JP2009519965 A5 JP 2009519965A5

Authority

JP

Japan

Prior art keywords

compound

treatment

methyl

dichlorophenyl

phenyl

Prior art date

2006-12-13

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.)

Granted

Links

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• 150000001875 compounds Chemical class 0.000 claims 40
• 239000003814 drug Substances 0.000 claims 7
• 125000000217 alkyl group Chemical group 0.000 claims 6
• 150000003839 salts Chemical class 0.000 claims 6
• 125000001475 halogen functional group Chemical group 0.000 claims 4
• 238000000034 method Methods 0.000 claims 4
• 239000000203 mixture Substances 0.000 claims 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
• LSKNUTNLADXZFJ-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound OCC(N)(CO)CO.C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl LSKNUTNLADXZFJ-UHFFFAOYSA-N 0.000 claims 3
• TUOXXRMLFZBSTB-UHFFFAOYSA-N 6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl TUOXXRMLFZBSTB-UHFFFAOYSA-N 0.000 claims 3
• 239000002253 acid Substances 0.000 claims 3
• 125000003342 alkenyl group Chemical group 0.000 claims 3
• 230000001404 mediated effect Effects 0.000 claims 3
• 239000012453 solvate Substances 0.000 claims 3
• 208000024891 symptom Diseases 0.000 claims 3
• 206010008635 Cholestasis Diseases 0.000 claims 2
• 206010016654 Fibrosis Diseases 0.000 claims 2
• 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
• 208000008589 Obesity Diseases 0.000 claims 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
• 208000019425 cirrhosis of liver Diseases 0.000 claims 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims 2
• 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
• 206010012601 diabetes mellitus Diseases 0.000 claims 2
• 230000004761 fibrosis Effects 0.000 claims 2
• 235000020824 obesity Nutrition 0.000 claims 2
• 210000000056 organ Anatomy 0.000 claims 2
• KNQWLANNMODPOI-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-propan-2-yl-4-[[4-[5-(2h-tetrazol-5-yl)naphthalen-2-yl]phenoxy]methyl]-1,2-oxazole Chemical compound CC(C)C=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1)=CC=C1C(C=C1C=CC=2)=CC=C1C=2C1=NN=NN1 KNQWLANNMODPOI-UHFFFAOYSA-N 0.000 claims 1
• DVZSPFZSZKKWIK-UHFFFAOYSA-N 6-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(O)=O)C(Cl)=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl DVZSPFZSZKKWIK-UHFFFAOYSA-N 0.000 claims 1
• NWFKPERKLYEWII-UHFFFAOYSA-N 6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carbonitrile Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C#N)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl NWFKPERKLYEWII-UHFFFAOYSA-N 0.000 claims 1
• FMCUKPUIJFXDAZ-UHFFFAOYSA-N 6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxamide Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(N)=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl FMCUKPUIJFXDAZ-UHFFFAOYSA-N 0.000 claims 1
• ZGRHLDTXNJVJLX-UHFFFAOYSA-N 6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-2-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=CC(=CC3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl ZGRHLDTXNJVJLX-UHFFFAOYSA-N 0.000 claims 1
• ZHXAPIVBWDJTLN-UHFFFAOYSA-N 6-[4-[[3-[(2,6-dichlorophenyl)methyl]-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1CC1=C(Cl)C=CC=C1Cl ZHXAPIVBWDJTLN-UHFFFAOYSA-N 0.000 claims 1
• KTLMJKKEKJASFK-UHFFFAOYSA-N 6-[4-[[3-[2-(2,6-dichlorophenyl)ethyl]-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1CCC1=C(Cl)C=CC=C1Cl KTLMJKKEKJASFK-UHFFFAOYSA-N 0.000 claims 1
• MPCDMRMAXXSILO-UHFFFAOYSA-N 6-[4-[[5-cyclobutyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C2C(C(=O)O)=CC=CC2=CC=1C(C=C1)=CC=C1OCC1=C(C2CCC2)ON=C1C1=C(Cl)C=CC=C1Cl MPCDMRMAXXSILO-UHFFFAOYSA-N 0.000 claims 1
• KVNUJCGFGCPUOA-UHFFFAOYSA-N 7-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C(C(O)=O)=CC=CC3=CC=2)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl KVNUJCGFGCPUOA-UHFFFAOYSA-N 0.000 claims 1
• GSTNOFVRIRGPDE-UHFFFAOYSA-N 7-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-2-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=C(C=CC3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl GSTNOFVRIRGPDE-UHFFFAOYSA-N 0.000 claims 1
• YEOXFVQGKAJALY-UHFFFAOYSA-N 7-[4-[[3-[2-(2,6-dichlorophenyl)ethyl]-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(C=2C=C3C(C(O)=O)=CC=CC3=CC=2)C=CC=1OCC1=C(C(C)C)ON=C1CCC1=C(Cl)C=CC=C1Cl YEOXFVQGKAJALY-UHFFFAOYSA-N 0.000 claims 1
• MXNUTDJISLUBCR-UHFFFAOYSA-N 7-[4-[[3-[2-(2,6-dichlorophenyl)ethyl]-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-2-carboxylic acid Chemical compound C=1C=C(C=2C=C3C=C(C=CC3=CC=2)C(O)=O)C=CC=1OCC1=C(C(C)C)ON=C1CCC1=C(Cl)C=CC=C1Cl MXNUTDJISLUBCR-UHFFFAOYSA-N 0.000 claims 1
• 101100347612 Arabidopsis thaliana VIII-B gene Proteins 0.000 claims 1
• 125000004450 alkenylene group Chemical group 0.000 claims 1
• 125000002947 alkylene group Chemical group 0.000 claims 1
• 150000001408 amides Chemical class 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 150000002148 esters Chemical class 0.000 claims 1
• 125000001188 haloalkyl group Chemical group 0.000 claims 1
• NBYFMFAXGSZXDW-UHFFFAOYSA-N methyl 6-[4-[[3-[2-(2,6-dichlorophenyl)ethyl]-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C(C=C1)=CC=C1OCC(=C(ON=1)C(C)C)C=1CCC1=C(Cl)C=CC=C1Cl NBYFMFAXGSZXDW-UHFFFAOYSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• XHGMGDRRDBNXIR-UHFFFAOYSA-M sodium;6-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]naphthalene-1-carboxylate Chemical compound [Na+].C=1C=C(C=2C=C3C=CC=C(C3=CC=2)C([O-])=O)C=CC=1OCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl XHGMGDRRDBNXIR-UHFFFAOYSA-M 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1