JP2006509001A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006509001A5 JP2006509001A5 JP2004554809A JP2004554809A JP2006509001A5 JP 2006509001 A5 JP2006509001 A5 JP 2006509001A5 JP 2004554809 A JP2004554809 A JP 2004554809A JP 2004554809 A JP2004554809 A JP 2004554809A JP 2006509001 A5 JP2006509001 A5 JP 2006509001A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- piperidin
- phenoxy
- trifluoromethyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- MSCPQIOJMWIYAF-SFHVURJKSA-N 2-methyl-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(C(O)=O)=C1 MSCPQIOJMWIYAF-SFHVURJKSA-N 0.000 claims 3
- MSCPQIOJMWIYAF-GOSISDBHSA-N 2-methyl-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(C(O)=O)=C1 MSCPQIOJMWIYAF-GOSISDBHSA-N 0.000 claims 3
- MSCPQIOJMWIYAF-UHFFFAOYSA-N 2-methyl-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=C(C)C(C(O)=O)=C1 MSCPQIOJMWIYAF-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 239000002552 dosage form Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- -1 1-carboxy-1-methyl-ethoxy Chemical group 0.000 claims 2
- DJXBOEOWRNXBIT-FQEVSTJZSA-N 2-methyl-2-[3-[(3r)-1-(4-propan-2-ylphenoxy)carbonylpiperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 DJXBOEOWRNXBIT-FQEVSTJZSA-N 0.000 claims 2
- DJXBOEOWRNXBIT-HXUWFJFHSA-N 2-methyl-2-[3-[(3s)-1-(4-propan-2-ylphenoxy)carbonylpiperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 DJXBOEOWRNXBIT-HXUWFJFHSA-N 0.000 claims 2
- DJXBOEOWRNXBIT-UHFFFAOYSA-N 2-methyl-2-[3-[1-(4-propan-2-ylphenoxy)carbonylpiperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 DJXBOEOWRNXBIT-UHFFFAOYSA-N 0.000 claims 2
- OISHBINQIFNIPV-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 OISHBINQIFNIPV-UHFFFAOYSA-N 0.000 claims 2
- CHYZNDMDRQIKKJ-KRWDZBQOSA-N 2-methyl-5-[(3r)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CHYZNDMDRQIKKJ-KRWDZBQOSA-N 0.000 claims 2
- CHYZNDMDRQIKKJ-QGZVFWFLSA-N 2-methyl-5-[(3s)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CHYZNDMDRQIKKJ-QGZVFWFLSA-N 0.000 claims 2
- CHYZNDMDRQIKKJ-UHFFFAOYSA-N 2-methyl-5-[1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1C1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CHYZNDMDRQIKKJ-UHFFFAOYSA-N 0.000 claims 2
- 229940122498 Gene expression inhibitor Drugs 0.000 claims 2
- 229940119502 Squalene cyclase inhibitor Drugs 0.000 claims 2
- 229940123185 Squalene epoxidase inhibitor Drugs 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- 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
- LWWWPSWKAKYIKX-IBGZPJMESA-N 2-[2-methyl-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(OCC(O)=O)=C1 LWWWPSWKAKYIKX-IBGZPJMESA-N 0.000 claims 1
- YABYZEHDUYSKQO-SFHVURJKSA-N 2-[2-methyl-5-[(3r)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 YABYZEHDUYSKQO-SFHVURJKSA-N 0.000 claims 1
- LWWWPSWKAKYIKX-LJQANCHMSA-N 2-[2-methyl-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(OCC(O)=O)=C1 LWWWPSWKAKYIKX-LJQANCHMSA-N 0.000 claims 1
- YABYZEHDUYSKQO-GOSISDBHSA-N 2-[2-methyl-5-[(3s)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 YABYZEHDUYSKQO-GOSISDBHSA-N 0.000 claims 1
- LWWWPSWKAKYIKX-UHFFFAOYSA-N 2-[2-methyl-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=C(C)C(OCC(O)=O)=C1 LWWWPSWKAKYIKX-UHFFFAOYSA-N 0.000 claims 1
- YABYZEHDUYSKQO-UHFFFAOYSA-N 2-[2-methyl-5-[1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC=C1C1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 YABYZEHDUYSKQO-UHFFFAOYSA-N 0.000 claims 1
- DQUSRRVOIHKKLD-QFIPXVFZSA-N 2-[3-[(3r)-1-[(4-cyclopropylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C2CC2)=C1 DQUSRRVOIHKKLD-QFIPXVFZSA-N 0.000 claims 1
- SAPWBAPTTIETIY-NRFANRHFSA-N 2-[3-[(3r)-1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1C[C@@H](C=2C=C(OCC(O)=O)C=CC=2)CCC1 SAPWBAPTTIETIY-NRFANRHFSA-N 0.000 claims 1
- AURMUMTWMBDRCI-NRFANRHFSA-N 2-[3-[(3r)-1-[2-(4-tert-butylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 AURMUMTWMBDRCI-NRFANRHFSA-N 0.000 claims 1
- DQUSRRVOIHKKLD-JOCHJYFZSA-N 2-[3-[(3s)-1-[(4-cyclopropylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C2CC2)=C1 DQUSRRVOIHKKLD-JOCHJYFZSA-N 0.000 claims 1
- SAPWBAPTTIETIY-OAQYLSRUSA-N 2-[3-[(3s)-1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1C[C@H](C=2C=C(OCC(O)=O)C=CC=2)CCC1 SAPWBAPTTIETIY-OAQYLSRUSA-N 0.000 claims 1
- AURMUMTWMBDRCI-OAQYLSRUSA-N 2-[3-[(3s)-1-[2-(4-tert-butylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 AURMUMTWMBDRCI-OAQYLSRUSA-N 0.000 claims 1
- DQUSRRVOIHKKLD-UHFFFAOYSA-N 2-[3-[1-[(4-cyclopropylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C2CC2)=C1 DQUSRRVOIHKKLD-UHFFFAOYSA-N 0.000 claims 1
- SAPWBAPTTIETIY-UHFFFAOYSA-N 2-[3-[1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1CC(C=2C=C(OCC(O)=O)C=CC=2)CCC1 SAPWBAPTTIETIY-UHFFFAOYSA-N 0.000 claims 1
- AURMUMTWMBDRCI-UHFFFAOYSA-N 2-[3-[1-[2-(4-tert-butylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 AURMUMTWMBDRCI-UHFFFAOYSA-N 0.000 claims 1
- HSEKAJDCQVYQHU-INIZCTEOSA-N 2-fluoro-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(F)C(C(O)=O)=C1 HSEKAJDCQVYQHU-INIZCTEOSA-N 0.000 claims 1
- HSEKAJDCQVYQHU-MRXNPFEDSA-N 2-fluoro-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(F)C(C(O)=O)=C1 HSEKAJDCQVYQHU-MRXNPFEDSA-N 0.000 claims 1
- HSEKAJDCQVYQHU-UHFFFAOYSA-N 2-fluoro-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=C(F)C(C(O)=O)=C1 HSEKAJDCQVYQHU-UHFFFAOYSA-N 0.000 claims 1
- BOVPFLQCUFHNGO-KRWDZBQOSA-N 2-methoxy-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1[C@@H]1CN(C(=O)C2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)CCC1 BOVPFLQCUFHNGO-KRWDZBQOSA-N 0.000 claims 1
- BOVPFLQCUFHNGO-QGZVFWFLSA-N 2-methoxy-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1[C@H]1CN(C(=O)C2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)CCC1 BOVPFLQCUFHNGO-QGZVFWFLSA-N 0.000 claims 1
- BOVPFLQCUFHNGO-UHFFFAOYSA-N 2-methoxy-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1C1CN(C(=O)C2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)CCC1 BOVPFLQCUFHNGO-UHFFFAOYSA-N 0.000 claims 1
- CKQSLVDWKFKDOP-FQEVSTJZSA-N 2-methyl-2-[2-methyl-5-[(3r)-1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CKQSLVDWKFKDOP-FQEVSTJZSA-N 0.000 claims 1
- WGYNJHJHEBFBSN-FQEVSTJZSA-N 2-methyl-2-[2-methyl-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(OC(C)(C)C(O)=O)=C1 WGYNJHJHEBFBSN-FQEVSTJZSA-N 0.000 claims 1
- QGFRHYZBADTZDK-IBGZPJMESA-N 2-methyl-2-[2-methyl-5-[(3r)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 QGFRHYZBADTZDK-IBGZPJMESA-N 0.000 claims 1
- CKQSLVDWKFKDOP-HXUWFJFHSA-N 2-methyl-2-[2-methyl-5-[(3s)-1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CKQSLVDWKFKDOP-HXUWFJFHSA-N 0.000 claims 1
- WGYNJHJHEBFBSN-HXUWFJFHSA-N 2-methyl-2-[2-methyl-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(OC(C)(C)C(O)=O)=C1 WGYNJHJHEBFBSN-HXUWFJFHSA-N 0.000 claims 1
- WGYNJHJHEBFBSN-UHFFFAOYSA-N 2-methyl-2-[2-methyl-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=C(C)C(OC(C)(C)C(O)=O)=C1 WGYNJHJHEBFBSN-UHFFFAOYSA-N 0.000 claims 1
- QGFRHYZBADTZDK-UHFFFAOYSA-N 2-methyl-2-[2-methyl-5-[1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1C1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 QGFRHYZBADTZDK-UHFFFAOYSA-N 0.000 claims 1
- SUBHDJVQXQSZFZ-FQEVSTJZSA-N 2-methyl-2-[3-[(3r)-1-[(4-propan-2-ylphenyl)carbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 SUBHDJVQXQSZFZ-FQEVSTJZSA-N 0.000 claims 1
- CSLFIHDRJSTULR-QFIPXVFZSA-N 2-methyl-2-[3-[(3r)-1-[(4-propan-2-ylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 CSLFIHDRJSTULR-QFIPXVFZSA-N 0.000 claims 1
- VQRZVXMYBJYLNT-QFIPXVFZSA-N 2-methyl-2-[3-[(3r)-1-[(4-propan-2-ylphenyl)methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CNC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 VQRZVXMYBJYLNT-QFIPXVFZSA-N 0.000 claims 1
- LRNJNCUFTWHRGZ-NRFANRHFSA-N 2-methyl-2-[3-[(3r)-1-[2-(4-propan-2-ylphenoxy)acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OCC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 LRNJNCUFTWHRGZ-NRFANRHFSA-N 0.000 claims 1
- OISHBINQIFNIPV-QFIPXVFZSA-N 2-methyl-2-[3-[(3r)-1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 OISHBINQIFNIPV-QFIPXVFZSA-N 0.000 claims 1
- HDLYBKTVFXZHKS-KRWDZBQOSA-N 2-methyl-2-[3-[(3r)-1-[2-[4-(trifluoromethoxy)phenoxy]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)COC=2C=CC(OC(F)(F)F)=CC=2)=C1 HDLYBKTVFXZHKS-KRWDZBQOSA-N 0.000 claims 1
- VRZLWWGJVNWPSI-SFHVURJKSA-N 2-methyl-2-[3-[(3r)-1-[2-[4-(trifluoromethoxy)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)=C1 VRZLWWGJVNWPSI-SFHVURJKSA-N 0.000 claims 1
- YPKNWLYJBPENNO-SFHVURJKSA-N 2-methyl-2-[3-[(3r)-1-[2-[4-(trifluoromethyl)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)CC=2C=CC(=CC=2)C(F)(F)F)=C1 YPKNWLYJBPENNO-SFHVURJKSA-N 0.000 claims 1
- XMBVPVMESQLAGJ-QFIPXVFZSA-N 2-methyl-2-[3-[(3r)-1-[2-methyl-2-(4-propan-2-ylphenoxy)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(C)(C)C(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 XMBVPVMESQLAGJ-QFIPXVFZSA-N 0.000 claims 1
- NGICSUQHSDXERJ-QHCPKHFHSA-N 2-methyl-2-[3-[(3r)-1-[3-(4-propan-2-ylphenyl)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 NGICSUQHSDXERJ-QHCPKHFHSA-N 0.000 claims 1
- ZBRSLWVVBNXGRW-IBGZPJMESA-N 2-methyl-2-[3-[(3r)-1-[3-[4-(trifluoromethyl)phenyl]propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)CCC=2C=CC(=CC=2)C(F)(F)F)=C1 ZBRSLWVVBNXGRW-IBGZPJMESA-N 0.000 claims 1
- ULVQKCCUGBHUJX-IBGZPJMESA-N 2-methyl-2-[3-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(OC(C)(C)C(O)=O)=C1 ULVQKCCUGBHUJX-IBGZPJMESA-N 0.000 claims 1
- FVMDWBAJYXYDSO-SFHVURJKSA-N 2-methyl-2-[3-[(3r)-1-[[3-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)OCC=2C=C(C=CC=2)C(F)(F)F)=C1 FVMDWBAJYXYDSO-SFHVURJKSA-N 0.000 claims 1
- FNHRBQZBESRXDZ-SFHVURJKSA-N 2-methyl-2-[3-[(3r)-1-[[4-(trifluoromethoxy)phenyl]methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)NCC=2C=CC(OC(F)(F)F)=CC=2)=C1 FNHRBQZBESRXDZ-SFHVURJKSA-N 0.000 claims 1
- CHXFZRUQFRYVEM-SFHVURJKSA-N 2-methyl-2-[3-[(3r)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)=C1 CHXFZRUQFRYVEM-SFHVURJKSA-N 0.000 claims 1
- SUBHDJVQXQSZFZ-HXUWFJFHSA-N 2-methyl-2-[3-[(3s)-1-[(4-propan-2-ylphenyl)carbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 SUBHDJVQXQSZFZ-HXUWFJFHSA-N 0.000 claims 1
- CSLFIHDRJSTULR-JOCHJYFZSA-N 2-methyl-2-[3-[(3s)-1-[(4-propan-2-ylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 CSLFIHDRJSTULR-JOCHJYFZSA-N 0.000 claims 1
- VQRZVXMYBJYLNT-JOCHJYFZSA-N 2-methyl-2-[3-[(3s)-1-[(4-propan-2-ylphenyl)methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CNC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 VQRZVXMYBJYLNT-JOCHJYFZSA-N 0.000 claims 1
- LRNJNCUFTWHRGZ-OAQYLSRUSA-N 2-methyl-2-[3-[(3s)-1-[2-(4-propan-2-ylphenoxy)acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OCC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 LRNJNCUFTWHRGZ-OAQYLSRUSA-N 0.000 claims 1
- HDLYBKTVFXZHKS-QGZVFWFLSA-N 2-methyl-2-[3-[(3s)-1-[2-[4-(trifluoromethoxy)phenoxy]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)COC=2C=CC(OC(F)(F)F)=CC=2)=C1 HDLYBKTVFXZHKS-QGZVFWFLSA-N 0.000 claims 1
- VRZLWWGJVNWPSI-GOSISDBHSA-N 2-methyl-2-[3-[(3s)-1-[2-[4-(trifluoromethoxy)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)=C1 VRZLWWGJVNWPSI-GOSISDBHSA-N 0.000 claims 1
- YPKNWLYJBPENNO-GOSISDBHSA-N 2-methyl-2-[3-[(3s)-1-[2-[4-(trifluoromethyl)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)CC=2C=CC(=CC=2)C(F)(F)F)=C1 YPKNWLYJBPENNO-GOSISDBHSA-N 0.000 claims 1
- XMBVPVMESQLAGJ-JOCHJYFZSA-N 2-methyl-2-[3-[(3s)-1-[2-methyl-2-(4-propan-2-ylphenoxy)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(C)(C)C(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 XMBVPVMESQLAGJ-JOCHJYFZSA-N 0.000 claims 1
- NGICSUQHSDXERJ-HSZRJFAPSA-N 2-methyl-2-[3-[(3s)-1-[3-(4-propan-2-ylphenyl)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 NGICSUQHSDXERJ-HSZRJFAPSA-N 0.000 claims 1
- ZBRSLWVVBNXGRW-LJQANCHMSA-N 2-methyl-2-[3-[(3s)-1-[3-[4-(trifluoromethyl)phenyl]propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)CCC=2C=CC(=CC=2)C(F)(F)F)=C1 ZBRSLWVVBNXGRW-LJQANCHMSA-N 0.000 claims 1
- ULVQKCCUGBHUJX-LJQANCHMSA-N 2-methyl-2-[3-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(OC(C)(C)C(O)=O)=C1 ULVQKCCUGBHUJX-LJQANCHMSA-N 0.000 claims 1
- FVMDWBAJYXYDSO-GOSISDBHSA-N 2-methyl-2-[3-[(3s)-1-[[3-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)OCC=2C=C(C=CC=2)C(F)(F)F)=C1 FVMDWBAJYXYDSO-GOSISDBHSA-N 0.000 claims 1
- FNHRBQZBESRXDZ-GOSISDBHSA-N 2-methyl-2-[3-[(3s)-1-[[4-(trifluoromethoxy)phenyl]methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)NCC=2C=CC(OC(F)(F)F)=CC=2)=C1 FNHRBQZBESRXDZ-GOSISDBHSA-N 0.000 claims 1
- CHXFZRUQFRYVEM-GOSISDBHSA-N 2-methyl-2-[3-[(3s)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)=C1 CHXFZRUQFRYVEM-GOSISDBHSA-N 0.000 claims 1
- SUBHDJVQXQSZFZ-UHFFFAOYSA-N 2-methyl-2-[3-[1-[(4-propan-2-ylphenyl)carbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 SUBHDJVQXQSZFZ-UHFFFAOYSA-N 0.000 claims 1
- CSLFIHDRJSTULR-UHFFFAOYSA-N 2-methyl-2-[3-[1-[(4-propan-2-ylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 CSLFIHDRJSTULR-UHFFFAOYSA-N 0.000 claims 1
- VQRZVXMYBJYLNT-UHFFFAOYSA-N 2-methyl-2-[3-[1-[(4-propan-2-ylphenyl)methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CNC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 VQRZVXMYBJYLNT-UHFFFAOYSA-N 0.000 claims 1
- LRNJNCUFTWHRGZ-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-(4-propan-2-ylphenoxy)acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OCC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 LRNJNCUFTWHRGZ-UHFFFAOYSA-N 0.000 claims 1
- HDLYBKTVFXZHKS-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-[4-(trifluoromethoxy)phenoxy]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)COC=2C=CC(OC(F)(F)F)=CC=2)=C1 HDLYBKTVFXZHKS-UHFFFAOYSA-N 0.000 claims 1
- VRZLWWGJVNWPSI-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-[4-(trifluoromethoxy)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)=C1 VRZLWWGJVNWPSI-UHFFFAOYSA-N 0.000 claims 1
- YPKNWLYJBPENNO-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-[4-(trifluoromethyl)phenyl]acetyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)CC=2C=CC(=CC=2)C(F)(F)F)=C1 YPKNWLYJBPENNO-UHFFFAOYSA-N 0.000 claims 1
- XMBVPVMESQLAGJ-UHFFFAOYSA-N 2-methyl-2-[3-[1-[2-methyl-2-(4-propan-2-ylphenoxy)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(C)(C)C(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 XMBVPVMESQLAGJ-UHFFFAOYSA-N 0.000 claims 1
- NGICSUQHSDXERJ-UHFFFAOYSA-N 2-methyl-2-[3-[1-[3-(4-propan-2-ylphenyl)propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 NGICSUQHSDXERJ-UHFFFAOYSA-N 0.000 claims 1
- ZBRSLWVVBNXGRW-UHFFFAOYSA-N 2-methyl-2-[3-[1-[3-[4-(trifluoromethyl)phenyl]propanoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)CCC=2C=CC(=CC=2)C(F)(F)F)=C1 ZBRSLWVVBNXGRW-UHFFFAOYSA-N 0.000 claims 1
- ULVQKCCUGBHUJX-UHFFFAOYSA-N 2-methyl-2-[3-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=CC(OC(C)(C)C(O)=O)=C1 ULVQKCCUGBHUJX-UHFFFAOYSA-N 0.000 claims 1
- FVMDWBAJYXYDSO-UHFFFAOYSA-N 2-methyl-2-[3-[1-[[3-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)OCC=2C=C(C=CC=2)C(F)(F)F)=C1 FVMDWBAJYXYDSO-UHFFFAOYSA-N 0.000 claims 1
- FNHRBQZBESRXDZ-UHFFFAOYSA-N 2-methyl-2-[3-[1-[[4-(trifluoromethoxy)phenyl]methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)NCC=2C=CC(OC(F)(F)F)=CC=2)=C1 FNHRBQZBESRXDZ-UHFFFAOYSA-N 0.000 claims 1
- CHXFZRUQFRYVEM-UHFFFAOYSA-N 2-methyl-2-[3-[1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2CN(CCC2)C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)=C1 CHXFZRUQFRYVEM-UHFFFAOYSA-N 0.000 claims 1
- UVILUUWUTHCPSG-SFHVURJKSA-N 2-methyl-5-[(3r)-1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 UVILUUWUTHCPSG-SFHVURJKSA-N 0.000 claims 1
- BHZLSMJVEWOZAQ-SFHVURJKSA-N 2-methyl-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzamide Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(C(N)=O)=C1 BHZLSMJVEWOZAQ-SFHVURJKSA-N 0.000 claims 1
- UVILUUWUTHCPSG-GOSISDBHSA-N 2-methyl-5-[(3s)-1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 UVILUUWUTHCPSG-GOSISDBHSA-N 0.000 claims 1
- BHZLSMJVEWOZAQ-GOSISDBHSA-N 2-methyl-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzamide Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(C)C(C(N)=O)=C1 BHZLSMJVEWOZAQ-GOSISDBHSA-N 0.000 claims 1
- BHZLSMJVEWOZAQ-UHFFFAOYSA-N 2-methyl-5-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzamide Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)N(C1)CCCC1C1=CC=C(C)C(C(N)=O)=C1 BHZLSMJVEWOZAQ-UHFFFAOYSA-N 0.000 claims 1
- 102000018616 Apolipoproteins B Human genes 0.000 claims 1
- 108010027006 Apolipoproteins B Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 claims 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 claims 1
- 108010000775 Hydroxymethylglutaryl-CoA synthase Proteins 0.000 claims 1
- 102100028888 Hydroxymethylglutaryl-CoA synthase, cytoplasmic Human genes 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010021024 Hypolipidaemia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 229940086609 Lipase inhibitor Drugs 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033307 Overweight Diseases 0.000 claims 1
- 102000005782 Squalene Monooxygenase Human genes 0.000 claims 1
- 229940123495 Squalene synthetase inhibitor Drugs 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- YVPOVOVZCOOSBQ-AXHZAXLDSA-N [(1s,3r,7s,8s,8ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2s)-2-methylbutanoate;pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1.C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 YVPOVOVZCOOSBQ-AXHZAXLDSA-N 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 239000003613 bile acid Substances 0.000 claims 1
- 229920000080 bile acid sequestrant Polymers 0.000 claims 1
- 229940096699 bile acid sequestrants Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 1
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940125753 fibrate Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 239000004059 squalene synthase inhibitor Substances 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42950602P | 2002-11-26 | 2002-11-26 | |
| PCT/IB2003/005235 WO2004048334A1 (en) | 2002-11-26 | 2003-11-14 | Phenyl substituted piperidine compounds for use as ppar activators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006509001A JP2006509001A (ja) | 2006-03-16 |
| JP2006509001A5 true JP2006509001A5 (enExample) | 2006-10-19 |
| JP4029091B2 JP4029091B2 (ja) | 2008-01-09 |
Family
ID=32393563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004554809A Expired - Fee Related JP4029091B2 (ja) | 2002-11-26 | 2003-11-14 | Ｐｐａｒ活性化剤として使用するためのフェニル置換ピペリジン化合物 |
Country Status (33)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA008928B1 (ru) * | 2002-11-26 | 2007-08-31 | Пфайзер Продактс Инк. | Активаторы рецепторов, активируемых пролифератором пероксисом (ppar ) |
| JP2008500328A (ja) * | 2004-05-25 | 2008-01-10 | ファイザー・プロダクツ・インク | 新規な使用 |
| WO2005115389A2 (en) * | 2004-05-25 | 2005-12-08 | Pfizer Products Inc. | Specific ppar agonists for treating negative energy balance |
| BRPI0515015A (pt) * | 2004-08-11 | 2008-07-01 | Kyorin Seiyaku Kk | derivado cìclico de ácido aminobenzóico; medicamento; agonista ppar(alpha); agonista duplo ppar(alpha), y; agonista duplo ppar(alpha), (delta); modulador ppar; agente lipìdeo; agente profilático ou terapêutico compreendendo pelo menos um dos derivados cìclicos de ácido aminobenzóico ou sal do mesmo farmacêuticamente aceitável |
| WO2006056845A1 (en) * | 2004-11-23 | 2006-06-01 | Warner-Lambert Company Llc | 7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as hmg co-a reductase inhibitors for the treatment of lipidemia |
| CN101189231B (zh) * | 2005-03-23 | 2011-05-18 | 杏林制药株式会社 | 环状氨基苯基链烷酸衍生物 |
| GB0510141D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| CN101296914B (zh) * | 2005-08-26 | 2012-07-18 | 盐野义制药株式会社 | 具有ppar激动活性的衍生物 |
| US9173875B2 (en) * | 2006-04-11 | 2015-11-03 | Los Angeles Biomedical Research Institute At Harbor-Ucla Medical Center | Treatment for nicotine-induced lung disease using peroxisome proliferator-activated receptor gamma agonists |
| EP2094685B1 (en) * | 2006-12-01 | 2011-01-19 | Actelion Pharmaceuticals Ltd. | 3-heteroaryl (amino or amido)-1- (biphenyl or phenylthiazolyl) carbonylpiperdine derivatives as orexin receptor inhibitors |
| EP2178534A4 (en) * | 2007-07-17 | 2011-03-30 | Merck Sharp & Dohme | SOLUBLE EPOXYHYDROLASE HEMMER, COMPOSITIONS WITH SUCH COMPOUNDS AND TREATMENT METHODS THEREWITH |
| ES2551095T3 (es) * | 2007-07-19 | 2015-11-16 | Lundbeck, H., A/S | Amidas heterocíclicas de 5 miembros y compuestos relacionados |
| TW201006816A (en) | 2008-05-15 | 2010-02-16 | Organon Nv | Hexafluoroisopropanol derivatives |
| FR2935510B1 (fr) | 2008-08-28 | 2010-12-10 | Oberthur Technologies | Procede d'echange de donnees entre deux entites electroniques |
| FR2935511B1 (fr) | 2008-08-28 | 2010-12-10 | Oberthur Technologies | Procede d'echange de donnees entre deux entites electroniques |
| UA107938C2 (en) * | 2009-08-12 | 2015-03-10 | Syngenta Participations Ag | Heterocycles with microbicidal properties |
| WO2011037793A1 (en) * | 2009-09-25 | 2011-03-31 | Merck Sharp & Dohme Corp. | Substituted aminopiperidines as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes |
| TWI513695B (zh) * | 2009-10-27 | 2015-12-21 | Merck Sharp & Dohme | （１，１，１，３，３，３－六氟－２－羥基丙－２－基）苯基衍生物 |
| EP2363825B1 (fr) | 2010-03-04 | 2016-04-27 | Inside Secure | Procédé pour conduire une transaction au moyen d'un dispositif NFC |
| EP2680874A2 (en) | 2011-03-04 | 2014-01-08 | Pfizer Inc | Edn3-like peptides and uses thereof |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| RU2615769C2 (ru) * | 2015-07-29 | 2017-04-11 | Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Образования "Уфимский Государственный Университет Экономики И Сервиса" | Средство для ингибирования фермента альфа-амилазы |
| US20220411372A1 (en) * | 2019-09-20 | 2022-12-29 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Small-molecule inhibitors for the b-catenin/b-cell lymphoma 9 protein-protein interaction |
| CN116162056A (zh) * | 2021-11-24 | 2023-05-26 | 上海医药工业研究院 | β-catenin/BCL9蛋白-蛋白相互作用的小分子抑制剂及其应用 |
| WO2024022521A1 (zh) * | 2022-07-28 | 2024-02-01 | 南通环聚泰生物科技有限公司 | 靶向BCL9/β-连环蛋白互相作用的小分子化合物 |
| WO2024145931A1 (zh) * | 2023-01-06 | 2024-07-11 | 上海医药工业研究院有限公司 | β-catenin/BCL9蛋白蛋白相互作用的小分子抑制剂及其应用 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2025518A1 (enExample) * | 1969-06-05 | 1970-12-10 | ||
| US4476311A (en) * | 1980-03-12 | 1984-10-09 | The Purdue Frederick Company | Analgesic 4-carboxy-pyrrolidin-2-one compound |
| EP0077607A1 (en) * | 1981-09-17 | 1983-04-27 | Beecham Group Plc | N-substituted 3-aryl piperidines and derivatives thereof |
| EP0115607A1 (de) * | 1983-01-04 | 1984-08-15 | MERCK PATENT GmbH | Tetrahydrocarbazolderivate |
| GB9027023D0 (en) * | 1990-12-12 | 1991-01-30 | Wellcome Found | Anti-atherosclerotic aryl compounds |
| PT100441A (pt) | 1991-05-02 | 1993-09-30 | Smithkline Beecham Corp | Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso |
| US5274143A (en) * | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
| AU2869092A (en) | 1991-10-11 | 1993-05-03 | Smithkline Beecham Corporation | Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production |
| WO1993012086A1 (fr) * | 1991-12-11 | 1993-06-24 | Ss Pharmaceutical Co., Ltd. | Derive d'arylamide |
| JPH05255089A (ja) * | 1991-12-18 | 1993-10-05 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| JP3233991B2 (ja) * | 1992-06-26 | 2001-12-04 | 株式会社ソフィア | 遊技機 |
| EP0607536B1 (en) * | 1992-12-08 | 2001-01-24 | Ss Pharmaceutical Co., Ltd. | Arylamide derivatives |
| WO1996002250A1 (en) | 1994-07-20 | 1996-02-01 | Acea Pharmaceuticals Inc. | Haloperidol analogs and the use thereof |
| GB9606805D0 (en) | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
| DE19614204A1 (de) * | 1996-04-10 | 1997-10-16 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| JPH09312086A (ja) * | 1996-05-22 | 1997-12-02 | Matsushita Electric Ind Co Ltd | 光ディスク再生システム、光ディスク再生方法および光ディスク |
| WO1998005331A2 (en) | 1996-08-02 | 1998-02-12 | Ligand Pharmaceuticals Incorporated | Prevention or treatment of type 2 diabetes or cardiovascular disease with ppar modulators |
| IT1286497B1 (it) * | 1996-11-20 | 1998-07-15 | Italfarmaco Sud Spa | Difosfine di tipo misto eteroariliche-ariliche come leganti chirali, relativi complessi con metalli di transizione e impiego di detti |
| PL340958A1 (en) * | 1997-12-19 | 2001-03-12 | Merck & Co Inc | Derivatives of aryl thiazolydinone |
| DK0952154T3 (da) * | 1998-04-16 | 2004-12-13 | Pfizer Prod Inc | N-acyl- og N-aroylaralkylamider |
| US6376494B1 (en) * | 1998-06-15 | 2002-04-23 | American Home Products Corporation | Cycloalkyl-substituted aryl-piperazines, piperidines and tetrahydropyridines as serotonergic agents |
| HN1999000149A (es) | 1998-09-09 | 2000-01-12 | Pfizer Prod Inc | Derivados de 4,4-biarilpiperidina |
| GB9822473D0 (en) | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
| US6303637B1 (en) * | 1998-10-30 | 2001-10-16 | Merck & Co., Inc. | Heterocyclic potassium channel inhibitors |
| CA2324330A1 (en) * | 1999-11-08 | 2001-05-08 | Ssp Co., Ltd. | 4-hydroxy-4-phenylpiperidine derivatives and pharmaceuticals containing the same |
| US20020045613A1 (en) | 2000-04-27 | 2002-04-18 | Heinz Pauls | 1-aroyl-piperidinyl benzamidines |
| AU2000258650A1 (en) | 2000-05-11 | 2001-11-20 | Eli Lilly And Co | 2-piperidone compounds for the treatment of cancer |
| AU2001257413B2 (en) | 2000-05-22 | 2007-01-18 | Aventisub Llc | Arylmethylamine derivatives for use as tryptase inhibitors |
| WO2002028834A1 (en) | 2000-10-06 | 2002-04-11 | Smithkline Beecham P.L.C. | Process for the preparation of aryl-piperidine carbinols and intermediates thereof |
| CN1469862A (zh) | 2000-10-12 | 2004-01-21 | Ss制药株式会社 | 2,2-二苯基丁酰胺衍生物和含有它的药物 |
| JP2002173426A (ja) | 2000-12-05 | 2002-06-21 | Ss Pharmaceut Co Ltd | 血糖低下剤 |
| WO2002064549A1 (en) * | 2001-02-15 | 2002-08-22 | Pfizer Products Inc. | Ppar agonists |
| JP2004523543A (ja) * | 2001-02-15 | 2004-08-05 | ニューロサーチ、アクティーゼルスカブ | 神経栄養活性を有する化合物とドパミン活性を増加させる化合物の組み合わせ作用によるパーキンソン病の治療法 |
| EA008928B1 (ru) * | 2002-11-26 | 2007-08-31 | Пфайзер Продактс Инк. | Активаторы рецепторов, активируемых пролифератором пероксисом (ppar ) |
-
2003
- 2003-11-14 EA EA200500629A patent/EA008928B1/ru not_active IP Right Cessation
- 2003-11-14 CN CNB200380104275XA patent/CN100439337C/zh not_active Expired - Fee Related
- 2003-11-14 PL PL378268A patent/PL378268A1/pl not_active Application Discontinuation
- 2003-11-14 CA CA002507465A patent/CA2507465C/en not_active Expired - Fee Related
- 2003-11-14 WO PCT/IB2003/005235 patent/WO2004048334A1/en not_active Ceased
- 2003-11-14 HR HR20050437A patent/HRP20050437A2/hr not_active Application Discontinuation
- 2003-11-14 MX MXPA05005583A patent/MXPA05005583A/es active IP Right Grant
- 2003-11-14 DK DK03811832T patent/DK1567493T3/da active
- 2003-11-14 PT PT03811832T patent/PT1567493E/pt unknown
- 2003-11-14 ES ES03811832T patent/ES2321509T3/es not_active Expired - Lifetime
- 2003-11-14 KR KR1020057009389A patent/KR100760055B1/ko not_active Expired - Fee Related
- 2003-11-14 JP JP2004554809A patent/JP4029091B2/ja not_active Expired - Fee Related
- 2003-11-14 SI SI200331552T patent/SI1567493T1/sl unknown
- 2003-11-14 DE DE60326752T patent/DE60326752D1/de not_active Expired - Lifetime
- 2003-11-14 AT AT03811832T patent/ATE425966T1/de not_active IP Right Cessation
- 2003-11-14 AU AU2003276596A patent/AU2003276596B8/en not_active Ceased
- 2003-11-14 EP EP03811832A patent/EP1567493B1/en not_active Expired - Lifetime
- 2003-11-14 KR KR1020077012457A patent/KR100875318B1/ko not_active Expired - Fee Related
- 2003-11-14 UA UAA200505008A patent/UA83202C2/ru unknown
- 2003-11-14 BR BR0316521-3A patent/BR0316521A/pt not_active IP Right Cessation
- 2003-11-14 NZ NZ539546A patent/NZ539546A/en unknown
- 2003-11-24 AR ARP030104332A patent/AR042131A1/es unknown
- 2003-11-24 US US10/720,942 patent/US7199243B2/en not_active Expired - Fee Related
- 2003-11-25 PE PE2003001197A patent/PE20040699A1/es not_active Application Discontinuation
- 2003-11-25 TW TW092133036A patent/TW200424172A/zh unknown
- 2003-11-26 UY UY28097A patent/UY28097A1/es not_active Application Discontinuation
- 2003-11-26 GT GT200300258A patent/GT200300258A/es unknown
- 2003-11-26 NL NL1024881A patent/NL1024881C2/nl not_active IP Right Cessation
-
2005
- 2005-04-18 ZA ZA200503104A patent/ZA200503104B/en unknown
- 2005-04-20 IS IS7816A patent/IS7816A/is unknown
- 2005-05-19 CO CO05048657A patent/CO5570701A2/es not_active Application Discontinuation
- 2005-05-26 MA MA28299A patent/MA27532A1/fr unknown
- 2005-05-26 TN TNP2005000146A patent/TNSN05146A1/fr unknown
- 2005-06-15 NO NO20052921A patent/NO20052921L/no not_active Application Discontinuation
-
2007
- 2007-03-30 US US11/694,337 patent/US20070191429A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006509001A5 (enExample) | ||
| US7465804B2 (en) | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders | |
| US7932290B2 (en) | Method for the treatment of metabolic disorders | |
| US7084164B2 (en) | Triazole derivative | |
| US7820721B2 (en) | Compounds for the treatment of metabolic disorders | |
| US8513229B2 (en) | 4-Azetidinyl-1-phenyl-cyclohexane antagonists of CCR2 | |
| US7935689B2 (en) | Compounds for the treatment of metabolic disorders | |
| ZA200503104B (en) | Phenyl substituted piperidine compounds for use as PPAR activators | |
| US20130261108A1 (en) | Compositions and methods for modulating farnesoid x receptors | |
| JP2008528700A (ja) | Ｐｐａｒモジュレーターとしての化合物および組成物 | |
| US7514555B2 (en) | Compounds for the treatment of metabolic disorders | |
| JP2007511485A5 (enExample) | ||
| IL190920A (en) | Compounds and their use in the treatment of metabolic disorders | |
| JP2007513890A (ja) | カテプシンシステインプロテアーゼ阻害剤 | |
| US10077241B2 (en) | Tetrahydro-benzoimidazolyl modulators of TGR5 | |
| CN101304993A (zh) | 作为ppar调节剂的化合物和组合物 | |
| KR101972619B1 (ko) | 페닐 유도체 | |
| US7034047B2 (en) | Triazole derivative | |
| CN101102989B (zh) | 用于治疗高眼压的取代的环戊烷或环戊酮 | |
| US20090192203A1 (en) | Compounds and compositions as ppar modulators | |
| US8022249B2 (en) | Compounds for the treatment of metabolic disorders | |
| US7915429B2 (en) | Compounds for the treatment of metabolic disorders | |
| CN104995188B (zh) | 2-((1r,4r)-4-(4-(5-(苯并噁唑-2-基氨基)吡啶-2-基)苯基)环己基)乙酸的葡甲胺盐形式和它们作为dgat1抑制剂的用途 | |
| KR20080073721A (ko) | 헤테로사이클-치환된 3-알킬 아제티딘 유도체 | |
| CN101304984A (zh) | 唑和噻唑ppar调节剂 |