HRP20050437A2 - Phenyl substituted piperidine compounds for the use as ppar activators - Google Patents

Info

Publication number

HRP20050437A2

HRP20050437A2 HR20050437A HRP20050437A HRP20050437A2 HR P20050437 A2 HRP20050437 A2 HR P20050437A2 HR 20050437 A HR20050437 A HR 20050437A HR P20050437 A HRP20050437 A HR P20050437A HR P20050437 A2 HRP20050437 A2 HR P20050437A2

Authority

HR

Croatia

Prior art keywords

methyl

phenyl

piperidin

phenoxy

trifluoromethyl

Prior art date

2002-11-26

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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 32
• 150000003053 piperidines Chemical class 0.000 title description 3
• 239000012190 activator Substances 0.000 title description 2
• 101150014691 PPARA gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 636
• 239000000651 prodrug Substances 0.000 claims description 156
• 229940002612 prodrug Drugs 0.000 claims description 156
• -1 hydroxyaminocarbonyl Chemical group 0.000 claims description 123
• 238000000034 method Methods 0.000 claims description 109
• 150000003839 salts Chemical class 0.000 claims description 97
• 239000003112 inhibitor Substances 0.000 claims description 94
• 241000124008 Mammalia Species 0.000 claims description 77
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 65
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
• 125000005843 halogen group Chemical group 0.000 claims description 55
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 52
• 229910052799 carbon Inorganic materials 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 239000003085 diluting agent Substances 0.000 claims description 38
• 229910052731 fluorine Inorganic materials 0.000 claims description 38
• 239000003937 drug carrier Substances 0.000 claims description 37
• 229910052720 vanadium Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 36
• 229910052727 yttrium Inorganic materials 0.000 claims description 36
• 125000004414 alkyl thio group Chemical group 0.000 claims description 35
• 206010012601 diabetes mellitus Diseases 0.000 claims description 35
• 229910052717 sulfur Chemical group 0.000 claims description 35
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
• 239000011593 sulfur Chemical group 0.000 claims description 34
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 32
• 229920006395 saturated elastomer Polymers 0.000 claims description 31
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 201000001320 Atherosclerosis Diseases 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• 235000019000 fluorine Nutrition 0.000 claims description 21
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 208000008589 Obesity Diseases 0.000 claims description 18
• 125000003386 piperidinyl group Chemical group 0.000 claims description 18
• 239000002552 dosage form Substances 0.000 claims description 17
• 235000020824 obesity Nutrition 0.000 claims description 17
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims description 16
• 108010038232 microsomal triglyceride transfer protein Proteins 0.000 claims description 16
• 230000001225 therapeutic effect Effects 0.000 claims description 16
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 15
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
• 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 14
• 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 14
• 206010020772 Hypertension Diseases 0.000 claims description 14
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
• 208000001132 Osteoporosis Diseases 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
• 108010000775 Hydroxymethylglutaryl-CoA synthase Proteins 0.000 claims description 12
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 12
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 12
• 229940119502 Squalene cyclase inhibitor Drugs 0.000 claims description 12
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
• 235000001968 nicotinic acid Nutrition 0.000 claims description 11
• 239000011664 nicotinic acid Substances 0.000 claims description 11
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 10
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 10
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
• 229940123185 Squalene epoxidase inhibitor Drugs 0.000 claims description 10
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 10
• 229960003512 nicotinic acid Drugs 0.000 claims description 10
• 230000028327 secretion Effects 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 claims description 9
• 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 claims description 9
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
• 206010022489 Insulin Resistance Diseases 0.000 claims description 9
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 9
• 229940122498 Gene expression inhibitor Drugs 0.000 claims description 8
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 8
• 206010021024 Hypolipidaemia Diseases 0.000 claims description 8
• 238000010521 absorption reaction Methods 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 201000008980 hyperinsulinism Diseases 0.000 claims description 8
• 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 8
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
• 206010019280 Heart failures Diseases 0.000 claims description 7
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 208000029078 coronary artery disease Diseases 0.000 claims description 7
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 239000004059 squalene synthase inhibitor Substances 0.000 claims description 7
• 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 description 6
• 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 description 6
• 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 description 6
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 6
• 102000005782 Squalene Monooxygenase Human genes 0.000 claims description 6
• 229940123495 Squalene synthetase inhibitor Drugs 0.000 claims description 6
• 229940125753 fibrate Drugs 0.000 claims description 6
• 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims description 5
• 108010054082 Sterol O-acyltransferase Proteins 0.000 claims description 5
• 208000007536 Thrombosis Diseases 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 239000003963 antioxidant agent Substances 0.000 claims description 5
• 229920000080 bile acid sequestrant Polymers 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 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 description 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 claims description 4
• 206010033307 Overweight Diseases 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 230000003078 antioxidant effect Effects 0.000 claims description 4
• 239000003613 bile acid Substances 0.000 claims description 4
• 239000003456 ion exchange resin Substances 0.000 claims description 4
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 150000003536 tetrazoles Chemical class 0.000 claims description 4
• 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 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• QGFRHYZBADTZDK-LJQANCHMSA-N 2-methyl-2-[2-methyl-5-[(3s)-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-LJQANCHMSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 102000002284 Hydroxymethylglutaryl-CoA Synthase Human genes 0.000 claims 2
• 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
• 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
• 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
• 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
• 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
• CKQSLVDWKFKDOP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-5-[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=C1C1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CKQSLVDWKFKDOP-UHFFFAOYSA-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
• 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
• 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
• 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
• 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
• UVILUUWUTHCPSG-UHFFFAOYSA-N 2-methyl-5-[1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1C1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 UVILUUWUTHCPSG-UHFFFAOYSA-N 0.000 claims 1
• WDRJNKMAZMEYOF-UHFFFAOYSA-N 4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1 WDRJNKMAZMEYOF-UHFFFAOYSA-N 0.000 claims 1
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
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