SK1962001A3 - Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators - Google Patents

Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators Download PDF

Info

Publication number: SK1962001A3
Authority: SK; Slovakia
Prior art keywords: phenyl; methyl; amino; propenyl; oxo
Prior art date: 1998-08-07

Application number

SK196-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Jon Loren Collins

Milana Dezube

Jeffrey Alan Oplinger

Timothy Mark Willson

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

1998-08-07

Filing date

1999-08-05

Publication date

2001-11-06

1999-08-05 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-11-06 Publication of SK1962001A3 publication Critical patent/SK1962001A3/sk

Links

239000012190 activator Substances 0.000 title claims abstract description 7
150000002916 oxazoles Chemical class 0.000 title 1
150000003557 thiazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 191
150000003839 salts Chemical class 0.000 claims abstract description 21
239000012453 solvate Substances 0.000 claims abstract description 11
-1 4-isopropoxy-phenyl Chemical group 0.000 claims description 254
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 134
235000019260 propionic acid Nutrition 0.000 claims description 134
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 124
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 77
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 69
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 63
125000005843 halogen group Chemical group 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 43
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 35
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 21
150000007979 thiazole derivatives Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 19
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
239000001294 propane Substances 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
MULZWPFQTUDZPD-UHFFFAOYSA-N 5-methyl-2-phenyl-1,3-oxazole Chemical compound O1C(C)=CN=C1C1=CC=CC=C1 MULZWPFQTUDZPD-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 9
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
208000032928 Dyslipidaemia Diseases 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
201000001421 hyperglycemia Diseases 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
BTLDXHPFOJBBPH-IOBJKCMUSA-N (2s)-2-[[(z)-4-(4-chlorophenyl)-4-oxobut-2-en-2-yl]amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC(Cl)=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BTLDXHPFOJBBPH-IOBJKCMUSA-N 0.000 claims description 2
GLKFRLXPZQIEMM-XSQYIDMWSA-N (2s)-2-[[(z)-4-(furan-2-yl)-4-oxobut-2-en-2-yl]amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1OC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GLKFRLXPZQIEMM-XSQYIDMWSA-N 0.000 claims description 2
KDJNNSGSZDHHCO-AYTQJLEDSA-N (2s)-3-[4-[2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-(4-fluorophenyl)-1-oxopent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(F)=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(F)C=C1 KDJNNSGSZDHHCO-AYTQJLEDSA-N 0.000 claims description 2
KTFQEYQGYFXTGI-IOBJKCMUSA-N (2s)-3-[4-[2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 KTFQEYQGYFXTGI-IOBJKCMUSA-N 0.000 claims description 2
AFVGSPOPBBKZGX-NCUSEZQPSA-N (2s)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCCC(=C(O1)C)N=C1C1=CC=CC=C1 AFVGSPOPBBKZGX-NCUSEZQPSA-N 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
206010070901 Diabetic dyslipidaemia Diseases 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
PCQRUQUPNKJTCA-WRQMMDRMSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-(3-methylphenyl)-4-oxobut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=C(C)C=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 PCQRUQUPNKJTCA-WRQMMDRMSA-N 0.000 claims 2
SSNLSQABALSQCY-IOBJKCMUSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-(4-nitrophenyl)-4-oxobut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC(=CC=1)[N+]([O-])=O)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 SSNLSQABALSQCY-IOBJKCMUSA-N 0.000 claims 2
HKKYUVLSVOGQRI-IOBJKCMUSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 HKKYUVLSVOGQRI-IOBJKCMUSA-N 0.000 claims 2
DHFDEUADFLFVFH-GDZDTEGPSA-N (2s)-2-[[(z)-1-(4-fluorophenyl)-1-oxopent-2-en-3-yl]amino]-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(F)=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC)C=C1 DHFDEUADFLFVFH-GDZDTEGPSA-N 0.000 claims 1
ZWUMOAUKSWTBQL-PBXLQVBZSA-N (2s)-2-[[(z)-4-(2,4-difluorophenyl)-4-oxobut-2-en-2-yl]amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C(=CC(F)=CC=1)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZWUMOAUKSWTBQL-PBXLQVBZSA-N 0.000 claims 1
QBEXADHAUHWNJM-IOBJKCMUSA-N (2s)-2-[[(z)-4-(2-fluorophenyl)-4-oxobut-2-en-2-yl]amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C(=CC=CC=1)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 QBEXADHAUHWNJM-IOBJKCMUSA-N 0.000 claims 1
CCLJXIIYSLMFSF-DRHYMTNESA-N (2s)-2-[[(z)-4-(2-hydroxyphenyl)-4-oxobut-2-en-2-yl]amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C(=CC=CC=1)O)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 CCLJXIIYSLMFSF-DRHYMTNESA-N 0.000 claims 1
SFZLBFMWVKXWSG-XNQHKPBGSA-N (2s)-3-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 SFZLBFMWVKXWSG-XNQHKPBGSA-N 0.000 claims 1
SUHOFKTYTHPPLR-FURYHQJQSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenyldec-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CCCCCCC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 SUHOFKTYTHPPLR-FURYHQJQSA-N 0.000 claims 1
DFDXKBOCANUROQ-BRCBANJSSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenylhept-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CCCC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 DFDXKBOCANUROQ-BRCBANJSSA-N 0.000 claims 1
DOZQYTYQLPMDJC-LSXFBCNXSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-(2,3,4-trifluorophenyl)but-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C(=C(F)C(F)=CC=1)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 DOZQYTYQLPMDJC-LSXFBCNXSA-N 0.000 claims 1
WIJWHLJLGOXYRH-RGYAHYCTSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-(2,4,5-trifluorophenyl)but-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C(=CC(F)=C(F)C=1)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 WIJWHLJLGOXYRH-RGYAHYCTSA-N 0.000 claims 1
HYVKNHZIMAPMEA-ZABXAGCJSA-N (2s)-3-[4-[2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC(F)=CC=1)C(O)=O)\C(C(F)(F)F)=C/C(=O)C1=CC=CC=C1 HYVKNHZIMAPMEA-ZABXAGCJSA-N 0.000 claims 1
DYVQSUVALMCCNY-AYTQJLEDSA-N (2s)-3-[4-[2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-[4-(trifluoromethyl)phenyl]pent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(F)C=C1 DYVQSUVALMCCNY-AYTQJLEDSA-N 0.000 claims 1
PULSYZRPJNPKOR-RWDZFFNTSA-N (2s)-3-[4-[2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenylpent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(F)C=C1 PULSYZRPJNPKOR-RWDZFFNTSA-N 0.000 claims 1
ADFCHMHRJJUJOS-GDZDTEGPSA-N (2s)-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-[4-(trifluoromethyl)phenyl]pent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC)C=C1 ADFCHMHRJJUJOS-GDZDTEGPSA-N 0.000 claims 1
FVMQSLWPDQCUIO-WRGQJZOISA-N (2s)-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenylpent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC)C=C1 FVMQSLWPDQCUIO-WRGQJZOISA-N 0.000 claims 1
ZUQPUWNIOXRPLJ-FMHRATFFSA-N (2s)-3-[4-[2-[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenylpent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC(C)C)C=C1 ZUQPUWNIOXRPLJ-FMHRATFFSA-N 0.000 claims 1
ZFDMAZJLFFBJMQ-FSTGKQFXSA-N (2s)-3-[4-[2-[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C1=CC(OC(C)C)=CC=C1C1=NC(CCOC=2C=CC(C[C@H](N\C(C)=C/C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=C(C)O1 ZFDMAZJLFFBJMQ-FSTGKQFXSA-N 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 abstract description 3
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102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 abstract 2
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 454
238000002360 preparation method Methods 0.000 description 401
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 352
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238000000034 method Methods 0.000 description 184
238000005160 1H NMR spectroscopy Methods 0.000 description 180
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 152
238000004809 thin layer chromatography Methods 0.000 description 134
235000019439 ethyl acetate Nutrition 0.000 description 108
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239000000203 mixture Substances 0.000 description 76
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
239000007787 solid Substances 0.000 description 66
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
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UKMQDGHXLCURSG-DVVXKZABSA-N (2s)-2-[[(z)-1-(4-fluorophenyl)-1-oxopent-2-en-3-yl]amino]-3-[4-[2-[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(F)=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC(C)C)C=C1 UKMQDGHXLCURSG-DVVXKZABSA-N 0.000 description 1
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APXAKENWRLGYAH-SFHVURJKSA-N (2s)-2-amino-3-[4-[2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1CCOC1=CC=C(C[C@H](N)C(O)=O)C=C1 APXAKENWRLGYAH-SFHVURJKSA-N 0.000 description 1
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NDRUBNPPVUUQML-KRWDZBQOSA-N (2s)-2-amino-3-[4-[[5-ethyl-2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoic acid Chemical compound CCC=1OC(C=2C=CC(F)=CC=2)=NC=1COC1=CC=C(C[C@H](N)C(O)=O)C=C1 NDRUBNPPVUUQML-KRWDZBQOSA-N 0.000 description 1
AWPQHYJLJBMICS-LKSMXUKOSA-N (2s)-3-[4-[(5-ethyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]-2-[[(z)-1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound N([C@@H](CC1=CC=C(C=C1)OCC=1N=C(OC=1CC)C=1C=CC=CC=1)C(O)=O)\C(C(F)(F)F)=C/C(=O)C1=CC=CC=C1 AWPQHYJLJBMICS-LKSMXUKOSA-N 0.000 description 1
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VKPUQMUINFYKEZ-CTTMAIQESA-N (2s)-3-[4-[2-(5-ethyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1CC)C=1C=CC=CC=1)C(O)=O)\C(C(F)(F)F)=C/C(=O)C1=CC=CC=C1 VKPUQMUINFYKEZ-CTTMAIQESA-N 0.000 description 1
LUTCXWWBPSPGNW-YGAUKUSGSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-1-oxo-1-phenylhex-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CCC)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 LUTCXWWBPSPGNW-YGAUKUSGSA-N 0.000 description 1
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MHGXGRCUCDKZCA-FSTGKQFXSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-(4-propan-2-yloxyphenyl)but-2-en-2-yl]amino]propanoic acid Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)\C=C(\C)N[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 MHGXGRCUCDKZCA-FSTGKQFXSA-N 0.000 description 1
KARYPYMAPUXYRH-DRHYMTNESA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-pyridin-2-ylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1N=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 KARYPYMAPUXYRH-DRHYMTNESA-N 0.000 description 1
OQWLIMVTFAMQQL-DHAULRCESA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-thiophen-3-ylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C1=CSC=C1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 OQWLIMVTFAMQQL-DHAULRCESA-N 0.000 description 1
SMZGSTOCDPPNGF-WMVCGJOFSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(S1)C)N=C1C1=CC=CC=C1 SMZGSTOCDPPNGF-WMVCGJOFSA-N 0.000 description 1
PJWQMWNCRBRKBG-AYTQJLEDSA-N (2s)-3-[4-[2-[2-(4-fluorophenyl)-5-methyl-1,3-thiazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-[4-(trifluoromethyl)phenyl]pent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(S1)C)N=C1C1=CC=C(F)C=C1 PJWQMWNCRBRKBG-AYTQJLEDSA-N 0.000 description 1
JYMQOPFLUNOZBH-BPSBXAKXSA-N (2s)-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl]amino]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(CCOC=2C=CC(C[C@H](N\C(C)=C/C(=O)C=3C=CC(=CC=3)C(F)(F)F)C(O)=O)=CC=2)=C(C)O1 JYMQOPFLUNOZBH-BPSBXAKXSA-N 0.000 description 1
LRWJGLZQKBDWBM-NPAMNNGVSA-N (2s)-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(CCOC=2C=CC(C[C@H](N\C(C)=C/C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=C(C)O1 LRWJGLZQKBDWBM-NPAMNNGVSA-N 0.000 description 1
WNCPVWPKDFXQSG-QICHVEDASA-N (2s)-3-[4-[2-[5-ethyl-2-(4-fluorophenyl)-1,3-thiazol-4-yl]ethoxy]phenyl]-2-[[(e)-1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl]amino]propanoic acid Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(SC=1CC)C=1C=CC(F)=CC=1)C(O)=O)\C(C(F)(F)F)=C\C(=O)C1=CC=CC=C1 WNCPVWPKDFXQSG-QICHVEDASA-N 0.000 description 1
OGVMNHAXDDFKJA-RWDZFFNTSA-N (2s)-3-[4-[2-[5-ethyl-2-(4-fluorophenyl)-1,3-thiazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-[4-(trifluoromethyl)phenyl]pent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(S1)CC)N=C1C1=CC=C(F)C=C1 OGVMNHAXDDFKJA-RWDZFFNTSA-N 0.000 description 1
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AAQIALLSQXGHHT-UHFFFAOYSA-N (5-methyl-2-phenyl-1,3-oxazol-4-yl)methanol Chemical compound OCC1=C(C)OC(C=2C=CC=CC=2)=N1 AAQIALLSQXGHHT-UHFFFAOYSA-N 0.000 description 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
FDCYCXNERGCRHF-NVRXJJJQSA-N (Z)-3-[[(2S)-1-[4-[(5-ethyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl]propan-2-yl]amino]-4,4,4-trifluoro-1-phenylbut-2-en-1-one Chemical compound C(C)C1=C(N=C(S1)C1=CC=CC=C1)COC1=CC=C(C=C1)C[C@H](C)N\C(=C/C(C1=CC=CC=C1)=O)\C(F)(F)F FDCYCXNERGCRHF-NVRXJJJQSA-N 0.000 description 1
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RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK196-2001A 1998-08-07 1999-08-05 Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators SK1962001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9817118.4A GB9817118D0 (en)	1998-08-07	1998-08-07	Pharmaceutical compounds
PCT/EP1999/005666 WO2000008002A1 (fr)	1998-08-07	1999-08-05	OXAZOLES SUBSTITUES ET DERIVES DE THIAZOLES COMME ACTIVATEURS DE ALPHA hPPAR ET DE GAMMA hPPAR

Publications (1)

Publication Number	Publication Date
SK1962001A3 true SK1962001A3 (en)	2001-11-06

Family

ID=10836805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK196-2001A SK1962001A3 (en)	1998-08-07	1999-08-05	Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators

Country Status (31)

Country	Link
US (1)	US6498174B1 (fr)
EP (1)	EP1102757B1 (fr)
JP (1)	JP2002522426A (fr)
KR (1)	KR20010085340A (fr)
CN (1)	CN1321152A (fr)
AP (1)	AP2001002066A0 (fr)
AR (1)	AR020001A1 (fr)
AT (1)	ATE264313T1 (fr)
AU (1)	AU5731099A (fr)
BR (1)	BR9912866A (fr)
CA (1)	CA2339773A1 (fr)
CO (1)	CO5070570A1 (fr)
CZ (1)	CZ2001490A3 (fr)
DE (1)	DE69916457T2 (fr)
EA (1)	EA200100105A1 (fr)
EE (1)	EE200100074A (fr)
ES (1)	ES2220110T3 (fr)
GB (1)	GB9817118D0 (fr)
HR (1)	HRP20010095A2 (fr)
HU (1)	HUP0103469A3 (fr)
ID (1)	ID29543A (fr)
IL (1)	IL141248A0 (fr)
IS (1)	IS5840A (fr)
MA (1)	MA26668A1 (fr)
NO (1)	NO20010628L (fr)
PE (1)	PE20000947A1 (fr)
PL (1)	PL345882A1 (fr)
SK (1)	SK1962001A3 (fr)
TR (1)	TR200100372T2 (fr)
WO (1)	WO2000008002A1 (fr)
ZA (1)	ZA200100983B (fr)

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US6417212B1 (en)	1999-08-27	2002-07-09	Eli Lilly & Company	Modulators of peroxisome proliferator activated receptors
EP1939188A1 (fr) *	1999-09-22	2008-07-02	Bristol-Myers Squibb Company	Dérivés d'oxa et thiazole utiles en tant qu'agents antidiabétiques et anti-obésité
US6414002B1 (en)	1999-09-22	2002-07-02	Bristol-Myers Squibb Company	Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
TWI302149B (en)	1999-09-22	2008-10-21	Bristol Myers Squibb Co	Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method
GB0002667D0 (en) *	2000-02-04	2000-03-29	Glaxo Group Ltd	medicamesnts
GB0031103D0 (en) *	2000-12-20	2001-01-31	Glaxo Group Ltd	Chemical compounds
US20040072838A1 (en)	2000-12-20	2004-04-15	Pierette Banker	Thiazole and oxazole derivatives as activators of human peroxisome proliferator activated receptors
WO2002076959A1 (fr) *	2001-03-23	2002-10-03	Takeda Chemical Industries, Ltd.	Derive heterocyclique a cinq membres d'acide alcanoique
GB0111523D0 (en) *	2001-05-11	2001-07-04	Glaxo Group Ltd	Chemical compounds
DE60211891T2 (de) *	2001-05-15	2007-05-24	F. Hoffmann-La Roche Ag	Carbonsäure-substituierte oxazol-derivate zur verwendung als ppar-alpha und -gamma aktivatoren zur behandlung von diabetes
PL367676A1 (en) *	2001-05-29	2005-03-07	Kyoto Pharmaceutical Industries, Ltd.	Novel heterocyclic derivatives and medicinal use thereof
JP4279136B2 (ja) *	2001-05-29	2009-06-17	京都薬品工業株式会社	新規複素環化合物およびその医薬用途
US6861440B2 (en)	2001-10-26	2005-03-01	Hoffmann-La Roche Inc.	DPP IV inhibitors
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1998
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1999
- 1999-08-04 AR ARP990103874A patent/AR020001A1/es not_active Application Discontinuation
- 1999-08-04 CO CO99049333A patent/CO5070570A1/es unknown
- 1999-08-05 CA CA002339773A patent/CA2339773A1/fr not_active Abandoned
- 1999-08-05 AT AT99944335T patent/ATE264313T1/de not_active IP Right Cessation
- 1999-08-05 HR HR20010095A patent/HRP20010095A2/hr not_active Application Discontinuation
- 1999-08-05 US US09/762,445 patent/US6498174B1/en not_active Expired - Fee Related
- 1999-08-05 ID IDW20010541A patent/ID29543A/id unknown
- 1999-08-05 SK SK196-2001A patent/SK1962001A3/sk unknown
- 1999-08-05 TR TR2001/00372T patent/TR200100372T2/xx unknown
- 1999-08-05 BR BR9912866-7A patent/BR9912866A/pt not_active Application Discontinuation
- 1999-08-05 IL IL14124899A patent/IL141248A0/xx unknown
- 1999-08-05 WO PCT/EP1999/005666 patent/WO2000008002A1/fr not_active Ceased
- 1999-08-05 DE DE69916457T patent/DE69916457T2/de not_active Expired - Lifetime
- 1999-08-05 AU AU57310/99A patent/AU5731099A/en not_active Abandoned
- 1999-08-05 EE EEP200100074A patent/EE200100074A/xx unknown
- 1999-08-05 KR KR1020017001617A patent/KR20010085340A/ko not_active Withdrawn
- 1999-08-05 MA MA25716A patent/MA26668A1/fr unknown
- 1999-08-05 PE PE1999000790A patent/PE20000947A1/es not_active Application Discontinuation
- 1999-08-05 EA EA200100105A patent/EA200100105A1/ru unknown
- 1999-08-05 JP JP2000563635A patent/JP2002522426A/ja active Pending
- 1999-08-05 CN CN99811640A patent/CN1321152A/zh active Pending
- 1999-08-05 ES ES99944335T patent/ES2220110T3/es not_active Expired - Lifetime
- 1999-08-05 PL PL99345882A patent/PL345882A1/xx not_active Application Discontinuation
- 1999-08-05 HU HU0103469A patent/HUP0103469A3/hu unknown
- 1999-08-05 CZ CZ2001490A patent/CZ2001490A3/cs unknown
- 1999-08-05 AP APAP/P/2001/002066A patent/AP2001002066A0/en unknown
- 1999-08-05 EP EP99944335A patent/EP1102757B1/fr not_active Expired - Lifetime
2001
- 2001-02-05 IS IS5840A patent/IS5840A/is unknown
- 2001-02-05 ZA ZA200100983A patent/ZA200100983B/en unknown
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Also Published As

Publication number	Publication date
CN1321152A (zh)	2001-11-07
EA200100105A1 (ru)	2001-08-27
HUP0103469A2 (hu)	2002-01-28
KR20010085340A (ko)	2001-09-07
EP1102757A1 (fr)	2001-05-30
AP2001002066A0 (en)	2001-03-31
IS5840A (is)	2001-02-05
NO20010628D0 (no)	2001-02-06
AU5731099A (en)	2000-02-28
PL345882A1 (en)	2002-01-14
HRP20010095A2 (en)	2002-02-28
WO2000008002A1 (fr)	2000-02-17
JP2002522426A (ja)	2002-07-23
TR200100372T2 (tr)	2001-09-21
CZ2001490A3 (cs)	2001-08-15
DE69916457D1 (de)	2004-05-19
CO5070570A1 (es)	2001-08-28
PE20000947A1 (es)	2000-09-22
ES2220110T3 (es)	2004-12-01
EP1102757B1 (fr)	2004-04-14
BR9912866A (pt)	2001-10-30
GB9817118D0 (en)	1998-10-07
HUP0103469A3 (en)	2002-08-28
US6498174B1 (en)	2002-12-24
MA26668A1 (fr)	2004-12-20
NO20010628L (no)	2001-04-06
ZA200100983B (en)	2002-03-05
ID29543A (id)	2001-09-06
EE200100074A (et)	2002-06-17
AR020001A1 (es)	2002-03-27
IL141248A0 (en)	2002-03-10
DE69916457T2 (de)	2005-04-14
CA2339773A1 (fr)	2000-02-17
ATE264313T1 (de)	2004-04-15

Publication	Publication Date	Title
SK1962001A3 (en)	2001-11-06	Substituted oxazoles and thiazoles derivatives as hppar gamma and hppar alpha activators
JP3490704B2 (ja)	2004-01-26	チアゾールおよびオキサゾール誘導体ならびにそれらの医薬的使用
US6518290B1 (en)	2003-02-11	Substituted oxazoles and thiazoles derivatives as HPPAr alpha activators
CZ20033250A3 (en)	2004-03-17	Thiazole or oxazole derivatives which are useful in the treatment of cardiovascular and related diseases
CZ20031737A3 (cs)	2003-10-15	Thiazolové deriváty
EP1513796B1 (fr)	2008-02-13	Composes chimiques
JP2005528348A (ja)	2005-09-22	Ｐｐａｒ活性を変調するチアゾールおよびオキサゾール誘導体
CZ20033252A3 (en)	2004-03-17	Oxazol/ thiazol-derivatives activators of the hppar-alpha receptor
US7141591B2 (en)	2006-11-28	1,2,4-oxadiazole derivatives as hPPAR alpha agonists
MXPA01001419A (en)	2001-12-13	SUBSTITUTED OXAZOLES AND THIAZOLES DERIVATIVES AS hPPAR GAMMA AND hPPAR ALPHA ACTIVATORS