JP2005501012A5 - - Google Patents
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- JP2005501012A5 JP2005501012A5 JP2003503168A JP2003503168A JP2005501012A5 JP 2005501012 A5 JP2005501012 A5 JP 2005501012A5 JP 2003503168 A JP2003503168 A JP 2003503168A JP 2003503168 A JP2003503168 A JP 2003503168A JP 2005501012 A5 JP2005501012 A5 JP 2005501012A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ring
- carbon atoms
- phenyl
- cycloalkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 224
- 125000004432 carbon atom Chemical group C* 0.000 claims 206
- 125000000753 cycloalkyl group Chemical group 0.000 claims 116
- 125000000217 alkyl group Chemical group 0.000 claims 107
- 239000003795 chemical substances by application Substances 0.000 claims 91
- 125000001072 heteroaryl group Chemical group 0.000 claims 89
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 67
- 125000005843 halogen group Chemical group 0.000 claims 62
- 125000003545 alkoxy group Chemical group 0.000 claims 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 58
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 57
- 229910052799 carbon Inorganic materials 0.000 claims 56
- 229910052739 hydrogen Inorganic materials 0.000 claims 54
- 239000001257 hydrogen Substances 0.000 claims 54
- -1 perfluoromethoxy Chemical group 0.000 claims 53
- 125000005842 heteroatom Chemical group 0.000 claims 51
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 50
- 229910052717 sulfur Inorganic materials 0.000 claims 50
- 238000000034 method Methods 0.000 claims 49
- 229910052757 nitrogen Inorganic materials 0.000 claims 49
- 229910052760 oxygen Inorganic materials 0.000 claims 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 34
- 239000003814 drug Substances 0.000 claims 29
- 229940079593 drug Drugs 0.000 claims 22
- 239000013543 active substance Substances 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 13
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 7
- 206010012601 diabetes mellitus Diseases 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 150000003254 radicals Chemical class 0.000 claims 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 5
- 208000008589 Obesity Diseases 0.000 claims 5
- 235000020824 obesity Nutrition 0.000 claims 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims 4
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000031773 Insulin resistance syndrome Diseases 0.000 claims 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 4
- 159000000000 sodium salts Chemical class 0.000 claims 4
- IDBQCNOWFLIFPM-UHFFFAOYSA-N 4-[3-[(2,6-difluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(OCC=2C(=CC=CC=2F)F)=C1 IDBQCNOWFLIFPM-UHFFFAOYSA-N 0.000 claims 3
- HFVDIZNJYLODRP-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C(=O)CCC(O)=O)=C1 HFVDIZNJYLODRP-UHFFFAOYSA-N 0.000 claims 3
- RKNUZODTBHBVDS-UHFFFAOYSA-N 4-[4-[(2,6-difluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=C(F)C=CC=C1F RKNUZODTBHBVDS-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 3
- ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 claims 3
- 208000010706 fatty liver disease Diseases 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- ZRLYRWYSWSKQAT-UHFFFAOYSA-N 1-[4-[(2,6-difluorophenyl)methoxy]phenyl]-2-(1h-1,2,4-triazol-5-ylsulfanyl)ethanone Chemical compound FC1=CC=CC(F)=C1COC1=CC=C(C(=O)CSC2=NNC=N2)C=C1 ZRLYRWYSWSKQAT-UHFFFAOYSA-N 0.000 claims 2
- WTGWNWGXYQQSBM-UHFFFAOYSA-N 3-[[4-[(2,6-difluorophenyl)methoxy]phenyl]methylsulfanyl]propanoic acid Chemical compound C1=CC(CSCCC(=O)O)=CC=C1OCC1=C(F)C=CC=C1F WTGWNWGXYQQSBM-UHFFFAOYSA-N 0.000 claims 2
- MTYCLIQVKSXZNI-UHFFFAOYSA-N 3-[[4-[(2-fluorophenyl)methoxy]phenyl]methylsulfanyl]propanoic acid Chemical compound C1=CC(CSCCC(=O)O)=CC=C1OCC1=CC=CC=C1F MTYCLIQVKSXZNI-UHFFFAOYSA-N 0.000 claims 2
- ZZKJZIUCLOKLOT-UHFFFAOYSA-N 4-(2,6-difluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=C(F)C=CC=C1F ZZKJZIUCLOKLOT-UHFFFAOYSA-N 0.000 claims 2
- PYEMFJAZILFLEZ-UHFFFAOYSA-N 4-[2-[(2,6-difluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1OCC1=C(F)C=CC=C1F PYEMFJAZILFLEZ-UHFFFAOYSA-N 0.000 claims 2
- SXKZIRGKCPDSJS-UHFFFAOYSA-N 4-[3-(cyclobutylmethoxy)phenyl]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(OCC2CCC2)=C1 SXKZIRGKCPDSJS-UHFFFAOYSA-N 0.000 claims 2
- WTEYVRDKSWAGRY-UHFFFAOYSA-N 4-[3-(cyclopropylmethoxy)phenyl]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(OCC2CC2)=C1 WTEYVRDKSWAGRY-UHFFFAOYSA-N 0.000 claims 2
- RXZRQBLNAOLBLK-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C(=O)CC(C)(C)C(O)=O)=C1 RXZRQBLNAOLBLK-UHFFFAOYSA-N 0.000 claims 2
- WBVJSANXEOFELZ-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-4-oxobut-2-enoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C(=O)C=CC(O)=O)=C1 WBVJSANXEOFELZ-UHFFFAOYSA-N 0.000 claims 2
- HCMDUZDOYGHGHA-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]but-3-enoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C=CCC(O)=O)=C1 HCMDUZDOYGHGHA-UHFFFAOYSA-N 0.000 claims 2
- FMWZELKYUWYZRY-UHFFFAOYSA-N 4-[3-[(2-fluoro-6-methylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=CC(F)=C1COC1=CC=CC(C(=O)CCC(O)=O)=C1 FMWZELKYUWYZRY-UHFFFAOYSA-N 0.000 claims 2
- BPNPEIBOTNDLQS-UHFFFAOYSA-N 4-[3-[(2-methylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1COC1=CC=CC(C(=O)CCC(O)=O)=C1 BPNPEIBOTNDLQS-UHFFFAOYSA-N 0.000 claims 2
- UJDZBVRDKDTYOK-UHFFFAOYSA-N 4-[4-(cyclopropylmethoxy)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1CC1 UJDZBVRDKDTYOK-UHFFFAOYSA-N 0.000 claims 2
- YWICWJIZWROWLT-UHFFFAOYSA-N 4-[4-[(2,4-difluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=C(F)C=C1F YWICWJIZWROWLT-UHFFFAOYSA-N 0.000 claims 2
- IIMUHSVNELGECO-UHFFFAOYSA-N 4-[4-[(2,5-difluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC(F)=CC=C1F IIMUHSVNELGECO-UHFFFAOYSA-N 0.000 claims 2
- PHMAORJRWUGBPH-UHFFFAOYSA-N 4-[4-[(2,5-dimethylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=C(C)C(COC=2C=CC(=CC=2)C(=O)CCC(O)=O)=C1 PHMAORJRWUGBPH-UHFFFAOYSA-N 0.000 claims 2
- RUZNKCMDWMGNMH-UHFFFAOYSA-N 4-[4-[(2-fluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC=C1F RUZNKCMDWMGNMH-UHFFFAOYSA-N 0.000 claims 2
- TYMHUUBNSLQDHP-UHFFFAOYSA-N 4-[4-[(2-methoxyphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound COC1=CC=CC=C1COC1=CC=C(C(=O)CCC(O)=O)C=C1 TYMHUUBNSLQDHP-UHFFFAOYSA-N 0.000 claims 2
- YADLQEFRHHBMGQ-UHFFFAOYSA-N 4-[4-[(2-methylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1COC1=CC=C(C(=O)CCC(O)=O)C=C1 YADLQEFRHHBMGQ-UHFFFAOYSA-N 0.000 claims 2
- ZCIVADXEDZSLOX-UHFFFAOYSA-N 4-[4-[(3-fluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC(F)=C1 ZCIVADXEDZSLOX-UHFFFAOYSA-N 0.000 claims 2
- MDLPYASYXFVKIX-UHFFFAOYSA-N 4-[4-[(4-fluorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=C(F)C=C1 MDLPYASYXFVKIX-UHFFFAOYSA-N 0.000 claims 2
- BASURFQVOZJAFE-UHFFFAOYSA-N 4-oxo-4-(4-phenylmethoxyphenyl)butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC=C1 BASURFQVOZJAFE-UHFFFAOYSA-N 0.000 claims 2
- PQESJEIAPIVSIE-UHFFFAOYSA-N 4-oxo-4-[3-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(OCC=2C=CC(=CC=2)C(F)(F)F)=C1 PQESJEIAPIVSIE-UHFFFAOYSA-N 0.000 claims 2
- PNDZWGOLDKGBQI-UHFFFAOYSA-N 4-oxo-4-[4-(2-thiophen-2-ylethoxy)phenyl]butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCCC1=CC=CS1 PNDZWGOLDKGBQI-UHFFFAOYSA-N 0.000 claims 2
- VDHNOKVRILUICI-UHFFFAOYSA-N 4-oxo-4-[4-(pyridin-2-ylmethoxy)phenyl]butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC=N1 VDHNOKVRILUICI-UHFFFAOYSA-N 0.000 claims 2
- ZGYBTRJTTITVRP-UHFFFAOYSA-N 4-oxo-4-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC=C1C(F)(F)F ZGYBTRJTTITVRP-UHFFFAOYSA-N 0.000 claims 2
- LBUKEYAVZKPGSA-UHFFFAOYSA-N 5-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-n-hydroxy-5-oxopentanamide Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C(=O)CCCC(=O)NO)=C1 LBUKEYAVZKPGSA-UHFFFAOYSA-N 0.000 claims 2
- YYRQECAOVDIPKD-UHFFFAOYSA-N 5-[[4-[(2,6-difluorophenyl)methoxy]phenyl]methyl]-2h-tetrazole Chemical compound FC1=CC=CC(F)=C1COC(C=C1)=CC=C1CC1=NN=NN1 YYRQECAOVDIPKD-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 125000003047 N-acetyl group Chemical group 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- GKXFLBOJFVMQMC-UHFFFAOYSA-N ethyl 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)C1=CC=CC(OCC=2C(=CC=CC=2C)C)=C1 GKXFLBOJFVMQMC-UHFFFAOYSA-N 0.000 claims 2
- QRWZIMJKESHEIK-UHFFFAOYSA-N ethyl 4-[3-[(2-fluorophenyl)methoxy]phenyl]-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)C1=CC=CC(OCC=2C(=CC=CC=2)F)=C1 QRWZIMJKESHEIK-UHFFFAOYSA-N 0.000 claims 2
- RBQRGKLDPWTLBI-UHFFFAOYSA-N ethyl 4-[4-[(2,6-difluorophenyl)methoxy]phenyl]-3-oxobutanoate Chemical compound C1=CC(CC(=O)CC(=O)OCC)=CC=C1OCC1=C(F)C=CC=C1F RBQRGKLDPWTLBI-UHFFFAOYSA-N 0.000 claims 2
- LOFPPLZWUJAFSF-UHFFFAOYSA-N ethyl 4-[4-[(2,6-difluorophenyl)methoxy]phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OCC)=CC=C1OCC1=C(F)C=CC=C1F LOFPPLZWUJAFSF-UHFFFAOYSA-N 0.000 claims 2
- IHPRBYXMSSECDE-UHFFFAOYSA-N ethyl 4-[4-[(2-fluorophenyl)methoxy]phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OCC)=CC=C1OCC1=CC=CC=C1F IHPRBYXMSSECDE-UHFFFAOYSA-N 0.000 claims 2
- DDRNZSBOEUQHSX-UHFFFAOYSA-N ethyl 4-[4-[(2-methylphenyl)methoxy]phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OCC)=CC=C1OCC1=CC=CC=C1C DDRNZSBOEUQHSX-UHFFFAOYSA-N 0.000 claims 2
- 229960004580 glibenclamide Drugs 0.000 claims 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 2
- 229960003105 metformin Drugs 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- VGIIILXIQLXVLC-UHFFFAOYSA-N 1-(2,6-difluorophenyl)ethanone Chemical compound CC(=O)C1=C(F)C=CC=C1F VGIIILXIQLXVLC-UHFFFAOYSA-N 0.000 claims 1
- GMSFOWMGHGGASO-UHFFFAOYSA-N 4-[3-[(2,6-dimethoxyphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound COC1=CC=CC(OC)=C1COC1=CC=CC(C(=O)CCC(O)=O)=C1 GMSFOWMGHGGASO-UHFFFAOYSA-N 0.000 claims 1
- KXSGVMUZQVYWGQ-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]-4-oxobutanamide Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(C(=O)CCC(N)=O)=C1 KXSGVMUZQVYWGQ-UHFFFAOYSA-N 0.000 claims 1
- UVELCWAZKCIXFE-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]but-2-enoic acid Chemical compound CC1=C(COC=2C=C(C=CC2)CC=CC(=O)O)C(=CC=C1)C UVELCWAZKCIXFE-UHFFFAOYSA-N 0.000 claims 1
- AGNWHTQVIMPQMA-UHFFFAOYSA-N 4-[3-[(2,6-dimethylphenyl)methoxy]phenyl]butanoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=CC(CCCC(O)=O)=C1 AGNWHTQVIMPQMA-UHFFFAOYSA-N 0.000 claims 1
- ZUYMGXNRJNNFRU-UHFFFAOYSA-N 4-[4-[(2,6-dimethylphenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound CC1=CC=CC(C)=C1COC1=CC=C(C(=O)CCC(O)=O)C=C1 ZUYMGXNRJNNFRU-UHFFFAOYSA-N 0.000 claims 1
- OYDBQEXJQFGKRI-UHFFFAOYSA-N 4-[4-[(2-chlorophenyl)methoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCC1=CC=CC=C1Cl OYDBQEXJQFGKRI-UHFFFAOYSA-N 0.000 claims 1
- YAEMFPUTWSADIK-UHFFFAOYSA-N 4-[4-[2-(2-fluorophenyl)ethoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCCC1=CC=CC=C1F YAEMFPUTWSADIK-UHFFFAOYSA-N 0.000 claims 1
- HCEQQASHRRPQFE-UHFFFAOYSA-N 5-chloro-n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide;3-(diaminomethylidene)-1,1-dimethylguanidine;hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N.COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 HCEQQASHRRPQFE-UHFFFAOYSA-N 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 1
- VXBMOSYMNUYPJW-UHFFFAOYSA-N CCC(CC)C(=O)NC(CC(=O)O)(C(=O)O)O Chemical compound CCC(CC)C(=O)NC(CC(=O)O)(C(=O)O)O VXBMOSYMNUYPJW-UHFFFAOYSA-N 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- HLMXBKPSIINQMN-UHFFFAOYSA-N FC1=C(C=CC=C1)CCOC1=CC=C(C=C1)C(CCC(=O)O)=O.ClC1=C(COC2=CC=C(C=C2)C(CCC(=O)O)=O)C=CC=C1 Chemical compound FC1=C(C=CC=C1)CCOC1=CC=C(C=C1)C(CCC(=O)O)=O.ClC1=C(COC2=CC=C(C=C2)C(CCC(=O)O)=O)C=CC=C1 HLMXBKPSIINQMN-UHFFFAOYSA-N 0.000 claims 1
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2007
- 2007-06-28 AU AU2007203009A patent/AU2007203009B2/en not_active Ceased
- 2007-07-02 US US11/772,560 patent/US8604083B2/en not_active Expired - Fee Related
- 2007-07-02 US US11/772,556 patent/US20070265323A1/en not_active Abandoned
- 2007-07-02 US US11/772,501 patent/US20070249696A1/en not_active Abandoned
- 2007-07-02 US US11/772,511 patent/US20070249719A1/en not_active Abandoned
- 2007-07-02 US US11/772,520 patent/US20070244141A1/en not_active Abandoned
- 2007-07-02 US US11/772,504 patent/US7851494B2/en not_active Expired - Fee Related
- 2007-07-02 US US11/772,515 patent/US20070244171A1/en not_active Abandoned
- 2007-08-20 US US11/841,508 patent/US20080015209A1/en not_active Abandoned
- 2007-08-24 US US11/844,431 patent/US7547802B2/en not_active Expired - Fee Related
- 2007-08-24 US US11/844,432 patent/US7863475B2/en not_active Expired - Fee Related
-
2008
- 2008-08-04 RU RU2008132204/04A patent/RU2502723C2/ru not_active IP Right Cessation
-
2009
- 2009-07-07 JP JP2009161270A patent/JP2009221232A/ja active Pending
- 2009-07-07 JP JP2009161269A patent/JP5477893B2/ja not_active Expired - Fee Related
-
2010
- 2010-12-08 IL IL209842A patent/IL209842A0/en unknown
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2011
- 2011-03-08 AU AU2011201016A patent/AU2011201016B2/en not_active Ceased
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2012
- 2012-04-24 IL IL219397A patent/IL219397A/en not_active IP Right Cessation
- 2012-04-24 IL IL219396A patent/IL219396A0/en unknown
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2013
- 2013-02-08 NO NO20130218A patent/NO20130218L/no not_active Application Discontinuation
- 2013-03-06 JP JP2013043951A patent/JP2013129665A/ja not_active Withdrawn
- 2013-06-18 US US13/920,579 patent/US9133073B2/en not_active Expired - Fee Related
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