CA2770194A1 - Sphingosine-1-phosphate receptor agonists - Google Patents

Info

Publication number

CA2770194A1

CA2770194A1 CA2770194A CA2770194A CA2770194A1 CA 2770194 A1 CA2770194 A1 CA 2770194A1 CA 2770194 A CA2770194 A CA 2770194A CA 2770194 A CA2770194 A CA 2770194A CA 2770194 A1 CA2770194 A1 CA 2770194A1

Authority

CA

Canada

Prior art keywords

phenyl

oxadiazol

trifluoromethyl

ethyl

hydroxy

Prior art date

2009-08-07

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 title description 16
• 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 title description 16
• 239000000018 receptor agonist Substances 0.000 title description 2
• 229940044601 receptor agonist Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 269
• 150000003839 salts Chemical class 0.000 claims abstract description 124
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 33
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• -1 -OH Chemical group 0.000 claims description 82
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 57
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
• 125000004122 cyclic group Chemical group 0.000 claims description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 23
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• 125000001544 thienyl group Chemical group 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 17
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• WPGIIIKQVNEYLG-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]azetidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(C2)C(O)=O)=NOC=1C1=CC=CC=C1 WPGIIIKQVNEYLG-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 12
• VPZDEAUZHGLOPF-KKFHFHRHSA-N (3s)-1-[2-hydroxy-2-[4-[5-[3-(6-methylpyridin-2-yl)-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)C(O)CN3C[C@H](CCC3)C(O)=O)ON=2)C(F)(F)F)=N1 VPZDEAUZHGLOPF-KKFHFHRHSA-N 0.000 claims description 11
• RCJRFCCXCZJHQL-UCFFOFKASA-N (3s)-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]-3-(trifluoromethyl)phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C(C(F)(F)F)=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 RCJRFCCXCZJHQL-UCFFOFKASA-N 0.000 claims description 11
• LTIXIGNBOHGXDX-BHWOMJMDSA-N (3s)-1-[2-hydroxy-2-[4-[5-[5-(2-methylpropyl)-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound FC(F)(F)C1=C(CC(C)C)ON=C1C1=NC(C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)=NO1 LTIXIGNBOHGXDX-BHWOMJMDSA-N 0.000 claims description 11
• HRMZOHUUKHMBOJ-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CC(C(O)=O)C1 HRMZOHUUKHMBOJ-UHFFFAOYSA-N 0.000 claims description 11
• YBQLZPRLWZZECJ-QRIPLOBPSA-N 2-[(3r)-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCC[C@H](CC(O)=O)C1 YBQLZPRLWZZECJ-QRIPLOBPSA-N 0.000 claims description 11
• PGFMWCFCZOEQFY-UHFFFAOYSA-N 4-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]morpholine-2-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCOC(C(O)=O)C1 PGFMWCFCZOEQFY-UHFFFAOYSA-N 0.000 claims description 11
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
• RUWIEFVLBVHOMD-VQCQRNETSA-N (2r)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]azetidine-2-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2[C@H](CC2)C(O)=O)=NOC=1C1=CC=CC=C1 RUWIEFVLBVHOMD-VQCQRNETSA-N 0.000 claims description 10
• KEQLVIFRZVZQOA-RBUKOAKNSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(C(=NO1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 KEQLVIFRZVZQOA-RBUKOAKNSA-N 0.000 claims description 10
• SXEARXGUIYUIFF-BBQAJUCSSA-N (3s)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)=NOC=1C1=CC=CC=C1 SXEARXGUIYUIFF-BBQAJUCSSA-N 0.000 claims description 10
• FBAFENRHYYUUFT-MDYZWHIJSA-N (3s)-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]propyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)(C)CN1CCC[C@H](C(O)=O)C1 FBAFENRHYYUUFT-MDYZWHIJSA-N 0.000 claims description 10
• NYZZVISKNPNJAD-BBQAJUCSSA-N 2-[(2s)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]pyrrolidin-2-yl]acetic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2[C@@H](CCC2)CC(O)=O)=NOC=1C1=CC=CC=C1 NYZZVISKNPNJAD-BBQAJUCSSA-N 0.000 claims description 10
• HLZSDCGIRNHZFD-QRIPLOBPSA-N 2-[(3r)-1-[2-hydroxy-2-[4-[5-[5-phenyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCC[C@H](CC(O)=O)C1 HLZSDCGIRNHZFD-QRIPLOBPSA-N 0.000 claims description 10
• FTIRVEBTARAWRH-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]pyrrolidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(CC2)C(O)=O)=NOC=1C1=CC=CC=C1 FTIRVEBTARAWRH-UHFFFAOYSA-N 0.000 claims description 9
• ZMUBLNWRVTYIDY-UHFFFAOYSA-N 3-fluoro-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCCC(F)(C(O)=O)C1 ZMUBLNWRVTYIDY-UHFFFAOYSA-N 0.000 claims description 9
• SXEARXGUIYUIFF-FKHAVUOCSA-N (3r)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@@H](CCC2)C(O)=O)=NOC=1C1=CC=CC=C1 SXEARXGUIYUIFF-FKHAVUOCSA-N 0.000 claims description 8
• KEQLVIFRZVZQOA-OALUTQOASA-N (3s)-1-[(2r)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(C(=NO1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 KEQLVIFRZVZQOA-OALUTQOASA-N 0.000 claims description 8
• QFMFMLVBWMLNIV-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-ol Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(O)CCC2)=NOC=1C1=CC=CC=C1 QFMFMLVBWMLNIV-UHFFFAOYSA-N 0.000 claims description 8
• JMKXTJZWBTVYGQ-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-3-methylpiperidine-3-carboxylic acid Chemical compound C1C(C)(C(O)=O)CCCN1CC(O)C1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 JMKXTJZWBTVYGQ-UHFFFAOYSA-N 0.000 claims description 8
• YNXRXFSUFSBGFK-UHFFFAOYSA-N 2-[1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(CC(O)=O)CCC2)=NOC=1C1=CC=CC=C1 YNXRXFSUFSBGFK-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• SNDOUFIGQKTFES-ATNAJCNCSA-N (3s)-1-[2-hydroxy-2-[4-[5-[3-pyridin-2-yl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2N=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 SNDOUFIGQKTFES-ATNAJCNCSA-N 0.000 claims description 7
• JDQQWZLAVFZPBI-OYKVQYDMSA-N (3s)-1-[2-hydroxy-2-[4-[5-[5-phenyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 JDQQWZLAVFZPBI-OYKVQYDMSA-N 0.000 claims description 7
• ZXVMCGJQAUKOBZ-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-2-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C(CCCC2)C(O)=O)=NOC=1C1=CC=CC=C1 ZXVMCGJQAUKOBZ-UHFFFAOYSA-N 0.000 claims description 7
• SXEARXGUIYUIFF-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(CCC2)C(O)=O)=NOC=1C1=CC=CC=C1 SXEARXGUIYUIFF-UHFFFAOYSA-N 0.000 claims description 7
• YNXRXFSUFSBGFK-XGLRFROISA-N 2-[(3s)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CC(O)=O)CCC2)=NOC=1C1=CC=CC=C1 YNXRXFSUFSBGFK-XGLRFROISA-N 0.000 claims description 7
• LPGMFSCVYIJNNA-UHFFFAOYSA-N 2-[1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]azetidin-3-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CC(CC(O)=O)C1 LPGMFSCVYIJNNA-UHFFFAOYSA-N 0.000 claims description 7
• CXNANLOOTYJTIE-UHFFFAOYSA-N 4-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]morpholine-2-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(OCC2)C(O)=O)=NOC=1C1=CC=CC=C1 CXNANLOOTYJTIE-UHFFFAOYSA-N 0.000 claims description 7
• WPAXHVDZIROVIQ-UHFFFAOYSA-N 4-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperazine-2-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2CC(NCC2)C(O)=O)=NOC=1C1=CC=CC=C1 WPAXHVDZIROVIQ-UHFFFAOYSA-N 0.000 claims description 7
• ZDFKJCZJWMALGB-UHFFFAOYSA-N 5-hydroxy-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CC(O)CC(C(O)=O)C1 ZDFKJCZJWMALGB-UHFFFAOYSA-N 0.000 claims description 7
• FOLYEQMBFAIKNS-UHFFFAOYSA-N 2-[3-(2-hydroxyethyl)piperidin-1-yl]-1-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethanol Chemical compound C1C(CCO)CCCN1CC(O)C1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 FOLYEQMBFAIKNS-UHFFFAOYSA-N 0.000 claims description 6
• PYANEAOOIPMWGW-UHFFFAOYSA-N 2-[3-(hydroxymethyl)piperidin-1-yl]-1-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethanol Chemical compound C1C(CO)CCCN1CC(O)C1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 PYANEAOOIPMWGW-UHFFFAOYSA-N 0.000 claims description 6
• HHLFDHHZRJJZOP-UHFFFAOYSA-N 2-[4-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]morpholin-2-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCOC(CC(O)=O)C1 HHLFDHHZRJJZOP-UHFFFAOYSA-N 0.000 claims description 6
• IYMYJRSILZWGPD-UHFFFAOYSA-N 2-[4-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]morpholin-3-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCOCC1CC(O)=O IYMYJRSILZWGPD-UHFFFAOYSA-N 0.000 claims description 6
• KIWRFMLROJOCPY-UHFFFAOYSA-N 3-[1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]propanoic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCCC(CCC(O)=O)C1 KIWRFMLROJOCPY-UHFFFAOYSA-N 0.000 claims description 6
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
• YNXRXFSUFSBGFK-PHSANKKPSA-N 2-[(3r)-1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@@H](CC(O)=O)CCC2)=NOC=1C1=CC=CC=C1 YNXRXFSUFSBGFK-PHSANKKPSA-N 0.000 claims description 5
• YHBSXEKWVZPAAS-NYRJJRHWSA-N 2-[(3r)-1-[2-hydroxy-2-[4-[5-[3-pyridin-2-yl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2N=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCC[C@H](CC(O)=O)C1 YHBSXEKWVZPAAS-NYRJJRHWSA-N 0.000 claims description 5
• LHTVETFHXOGXNI-UHFFFAOYSA-N 3-hydroxy-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCCC(O)(C(O)=O)C1 LHTVETFHXOGXNI-UHFFFAOYSA-N 0.000 claims description 5
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 5
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• RYZYNQIRCSGPMZ-QFBILLFUSA-N (3s)-1-[(2s)-2-[4-[5-[1-(5-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(Cl)=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 RYZYNQIRCSGPMZ-QFBILLFUSA-N 0.000 claims description 4
• SJYFMUOMOHKHBR-GHTZIAJQSA-N (3s)-1-[(2s)-2-[4-[5-[1-cyclohexyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(C2CCCCC2)N=C1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 SJYFMUOMOHKHBR-GHTZIAJQSA-N 0.000 claims description 4
• RHYCULYFTJPPMK-SIKLNZKXSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(3-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CC1=CC=CC(N2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)[C@H](O)CN3C[C@H](CCC3)C(O)=O)C=N2)C(F)(F)F)=C1 RHYCULYFTJPPMK-SIKLNZKXSA-N 0.000 claims description 4
• CHEHHINOCGQWKO-AZUAARDMSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(5-methylpyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound N1=CC(C)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@H](CCC2)C(O)=O)C=N1 CHEHHINOCGQWKO-AZUAARDMSA-N 0.000 claims description 4
• YECQGGUYVNGSQW-GHTZIAJQSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 YECQGGUYVNGSQW-GHTZIAJQSA-N 0.000 claims description 4
• SEAGFIRIYDHDEZ-PKOBYXMFSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[1-pyridin-2-yl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 SEAGFIRIYDHDEZ-PKOBYXMFSA-N 0.000 claims description 4
• NBAJVVQKVFSPLV-YDNXMHBPSA-N (3s)-1-[2-[4-[5-(5-ethyl-1-pyridin-2-ylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound CCC1=C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)C=NN1C1=CC=CC=N1 NBAJVVQKVFSPLV-YDNXMHBPSA-N 0.000 claims description 4
• AHULNQGXTUEURY-LBOXEOMUSA-N (3s)-1-[2-[4-[5-[3-(2-chlorophenyl)-1h-pyrazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C=2NN=C(C=2)C=2C(=CC=CC=2)Cl)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 AHULNQGXTUEURY-LBOXEOMUSA-N 0.000 claims description 4
• IXUPWWKYGWRAAD-HXBUSHRASA-N (3s)-1-[2-[4-[5-[3-(4-chlorophenyl)-1h-pyrazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C=2NN=C(C=2)C=2C=CC(Cl)=CC=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 IXUPWWKYGWRAAD-HXBUSHRASA-N 0.000 claims description 4
• ZAPDJMUOBGZNEG-YMXDCFFPSA-N (3s)-1-[2-[4-[5-[5-(4-chlorophenyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=NOC(=C2)C=2C=CC(Cl)=CC=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 ZAPDJMUOBGZNEG-YMXDCFFPSA-N 0.000 claims description 4
• MEHLDAAHMPABRE-BWDMCYIDSA-N (3s)-1-[2-hydroxy-2-[4-[5-(1-phenyl-5-propylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CCCC1=C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)C=NN1C1=CC=CC=C1 MEHLDAAHMPABRE-BWDMCYIDSA-N 0.000 claims description 4
• RCAXPPQJUXLEDW-YDNXMHBPSA-N (3s)-1-[2-hydroxy-2-[4-[5-(1-phenylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=CN(N=C2)C=2C=CC=CC=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 RCAXPPQJUXLEDW-YDNXMHBPSA-N 0.000 claims description 4
• XWNYRQCNTYBSGA-AJZOCDQUSA-N (3s)-1-[2-hydroxy-2-[4-[5-(2-methyl-5-phenylpyrazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CN1N=C(C=2C=CC=CC=2)C=C1C(ON=1)=NC=1C(C=C1)=CC=C1C(O)CN1CCC[C@H](C(O)=O)C1 XWNYRQCNTYBSGA-AJZOCDQUSA-N 0.000 claims description 4
• JJQRUMAWHZZQBX-AJZOCDQUSA-N (3s)-1-[2-hydroxy-2-[4-[5-(5-methyl-1-phenylpyrazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)=NN1C1=CC=CC=C1 JJQRUMAWHZZQBX-AJZOCDQUSA-N 0.000 claims description 4
• RZXFMXPSDKCPPH-AJZOCDQUSA-N (3s)-1-[2-hydroxy-2-[4-[5-(5-methyl-1-phenylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CC1=C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C[C@H](CCC2)C(O)=O)C=NN1C1=CC=CC=C1 RZXFMXPSDKCPPH-AJZOCDQUSA-N 0.000 claims description 4
• DWPIIZNSHBHXIM-UHFFFAOYSA-N 1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-6-methylpiperidine-2-carboxylic acid Chemical compound CC1CCCC(C(O)=O)N1CC(O)C1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 DWPIIZNSHBHXIM-UHFFFAOYSA-N 0.000 claims description 4
• GXNVIOTXBLFULH-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-bromophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC(Br)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 GXNVIOTXBLFULH-OPAMFIHVSA-N 0.000 claims description 4
• ZDBIBQUTMFNXTR-IIBYNOLFSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-chlorophenyl)-5-(trifluoromethyl)imidazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(C=N1)C=1C=CC(Cl)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 ZDBIBQUTMFNXTR-IIBYNOLFSA-N 0.000 claims description 4
• NPGPDNHISZFRSA-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-chlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC(Cl)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 NPGPDNHISZFRSA-OPAMFIHVSA-N 0.000 claims description 4
• WLSLSTGNQRRUSK-JLTOFOAXSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-[5-chloro-3-(trifluoromethyl)pyridin-2-yl]-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(Cl)=CN=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 WLSLSTGNQRRUSK-JLTOFOAXSA-N 0.000 claims description 4
• QUVDAYCPTOVHAD-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[5-(3-chlorophenyl)-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C=1C(=C(ON=1)C=1C=C(Cl)C=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 QUVDAYCPTOVHAD-FOIQADDNSA-N 0.000 claims description 4
• RMOQISUDDHAYIY-WZONZLPQSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(2-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CC1=CC=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 RMOQISUDDHAYIY-WZONZLPQSA-N 0.000 claims description 4
• PXZNTMIDRVHIKC-UZUQRXQVSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(4-methoxyphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 PXZNTMIDRVHIKC-UZUQRXQVSA-N 0.000 claims description 4
• BFBKHGAZEBRFGK-WZONZLPQSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(4-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 BFBKHGAZEBRFGK-WZONZLPQSA-N 0.000 claims description 4
• ZTVXCSBZECDKMU-KBMIEXCESA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(4-propan-2-ylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 ZTVXCSBZECDKMU-KBMIEXCESA-N 0.000 claims description 4
• MHLHEMWGFXEBBN-DYESRHJHSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(5-methylpyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound N1=CC(C)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 MHLHEMWGFXEBBN-DYESRHJHSA-N 0.000 claims description 4
• RUXWUUSWKUJZFD-IIBYNOLFSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-pyridin-3-yl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=NC=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 RUXWUUSWKUJZFD-IIBYNOLFSA-N 0.000 claims description 4
• FDHQLGJZHAZCPJ-DNVCBOLYSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC=CN=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 FDHQLGJZHAZCPJ-DNVCBOLYSA-N 0.000 claims description 4
• AAMQECSNTHSBOY-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(trifluoromethyl)-1-[4-(trifluoromethyl)phenyl]pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC(=CC=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 AAMQECSNTHSBOY-OPAMFIHVSA-N 0.000 claims description 4
• MLPNIDYTMUWPCN-UHFFFAOYSA-N 2-[1-[2-hydroxy-2-[4-[5-(5-phenyl-4-propyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-2-yl]acetic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(O)CN2C(CCCC2)CC(O)=O)=NOC=1C1=CC=CC=C1 MLPNIDYTMUWPCN-UHFFFAOYSA-N 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• VEYWMSKEPZXKDS-MRTLOADZSA-N (2r)-1-[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-2-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)CN1CCCC[C@@H]1C(O)=O VEYWMSKEPZXKDS-MRTLOADZSA-N 0.000 claims description 3
• MGYRRSGSTPKUJA-BGERDNNASA-N (3s)-1-[2-hydroxy-2-[4-[5-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound CC=1N=C(C=2C=CC=CC=2)SC=1C(ON=1)=NC=1C(C=C1)=CC=C1C(O)CN1CCC[C@H](C(O)=O)C1 MGYRRSGSTPKUJA-BGERDNNASA-N 0.000 claims description 3
• ILFVECNSERUOQV-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-fluorophenyl)-3-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C=1C(=NN(C=1)C=1C=CC(F)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 ILFVECNSERUOQV-OPAMFIHVSA-N 0.000 claims description 3
• DDMMTMFOAHJDMP-HRAATJIYSA-N (3s)-1-[(2s)-2-[4-[5-[1-(2,4-difluorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(F)=CC=1)F)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 DDMMTMFOAHJDMP-HRAATJIYSA-N 0.000 claims description 2
• BIOZRLQECBVCSR-HNAYVOBHSA-N (3s)-1-[(2s)-2-[4-[5-[1-(3,5-dichloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(Cl)=CN=1)Cl)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 BIOZRLQECBVCSR-HNAYVOBHSA-N 0.000 claims description 2
• VTZFMIRYVNPKSO-QFBILLFUSA-N (3s)-1-[(2s)-2-[4-[5-[1-(5-fluoropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(F)=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 VTZFMIRYVNPKSO-QFBILLFUSA-N 0.000 claims description 2
• AUCBHMIKXDZCKK-PGRDOPGGSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(4-methoxyphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@H](CCC2)C(O)=O)C=N1 AUCBHMIKXDZCKK-PGRDOPGGSA-N 0.000 claims description 2
• RKPKRPQAUKWECJ-RBUKOAKNSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-thiazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(C(=NS1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 RKPKRPQAUKWECJ-RBUKOAKNSA-N 0.000 claims description 2
• RMUTVQJKINESCA-QFBILLFUSA-N (3s)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(trifluoromethyl)-1-[5-(trifluoromethyl)pyridin-2-yl]pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(=CC=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](C(O)=O)C1 RMUTVQJKINESCA-QFBILLFUSA-N 0.000 claims description 2
• HSNUECYKWCDNDF-HSTJUUNISA-N (3s)-1-[1-hydroxy-2-methyl-1-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]propan-2-yl]piperidine-3-carboxylic acid Chemical compound C([C@H](CCC1)C(O)=O)N1C(C)(C)C(O)C(C=C1)=CC=C1C(N=1)=NOC=1C(=C1C(F)(F)F)ON=C1C1=CC=CC=C1 HSNUECYKWCDNDF-HSTJUUNISA-N 0.000 claims description 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• KXIJRCWBWLZKGL-IVZQSRNASA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(2,4-dichlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(Cl)=CC=1)Cl)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 KXIJRCWBWLZKGL-IVZQSRNASA-N 0.000 claims description 2
• WMXHBNBDBNAOQS-IVZQSRNASA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(2,4-difluorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(F)=CC=1)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 WMXHBNBDBNAOQS-IVZQSRNASA-N 0.000 claims description 2
• CSTKEHKVSZQINQ-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(2-chlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC=CC=1)Cl)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 CSTKEHKVSZQINQ-OPAMFIHVSA-N 0.000 claims description 2
• QOZKDPPGKUWYLO-IVZQSRNASA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(3,4-dichlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=C(Cl)C(Cl)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 QOZKDPPGKUWYLO-IVZQSRNASA-N 0.000 claims description 2
• HFSLAGPHKHVGJM-JLTOFOAXSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(3,5-dichloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(Cl)=CN=1)Cl)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 HFSLAGPHKHVGJM-JLTOFOAXSA-N 0.000 claims description 2
• SBEXUXKNKORBJB-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=C(Cl)C=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 SBEXUXKNKORBJB-OPAMFIHVSA-N 0.000 claims description 2
• UGFHPDPAZZCZHB-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC=CN=1)Cl)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 UGFHPDPAZZCZHB-FOIQADDNSA-N 0.000 claims description 2
• BPGFDHAVIDTFAD-UZUQRXQVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-chloro-2-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound CC1=CC(Cl)=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 BPGFDHAVIDTFAD-UZUQRXQVSA-N 0.000 claims description 2
• GCMFJDSBOLNEPE-UZUQRXQVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-chloro-3-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C1=C(Cl)C(C)=CC(N2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)[C@H](O)CN3C[C@@H](CC(O)=O)CCC3)C=N2)C(F)(F)F)=C1 GCMFJDSBOLNEPE-UZUQRXQVSA-N 0.000 claims description 2
• DUFGKRTXLOFQEZ-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(4-fluorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC(F)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 DUFGKRTXLOFQEZ-OPAMFIHVSA-N 0.000 claims description 2
• OYMHZYYAUVSJDE-JLTOFOAXSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(5-chloro-3-fluoropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC(Cl)=CN=1)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 OYMHZYYAUVSJDE-JLTOFOAXSA-N 0.000 claims description 2
• BPUJDZRCBMFZLS-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(5-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(Cl)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 BPUJDZRCBMFZLS-FOIQADDNSA-N 0.000 claims description 2
• KXPZQOHYAFETOE-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(5-ethoxy-3-fluoropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound FC1=CC(OCC)=CN=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 KXPZQOHYAFETOE-OPAMFIHVSA-N 0.000 claims description 2
• GMIJHEPKYKBSCR-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(5-fluoropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(F)=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 GMIJHEPKYKBSCR-FOIQADDNSA-N 0.000 claims description 2
• OBYCSDNPWIRQRB-DNVCBOLYSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-(6-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=C(Cl)C=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 OBYCSDNPWIRQRB-DNVCBOLYSA-N 0.000 claims description 2
• LHCFJZHDQHZDEW-VGOFRKELSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[1-cyclohexyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(C2CCCCC2)N=C1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 LHCFJZHDQHZDEW-VGOFRKELSA-N 0.000 claims description 2
• CHZSVWKXONAVDK-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[5-(2-chlorophenyl)-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C=1C(=C(ON=1)C=1C(=CC=CC=1)Cl)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 CHZSVWKXONAVDK-FOIQADDNSA-N 0.000 claims description 2
• XZCCIKSOORLLDT-OXQOHEQNSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[5-cyclohexyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C=1C(=C(C2CCCCC2)ON=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 XZCCIKSOORLLDT-OXQOHEQNSA-N 0.000 claims description 2
• SRAWHOFAUDTCLR-RHSMWYFYSA-N 2-[(3r)-1-[(2s)-2-[4-[5-[5-tert-butyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidin-3-yl]acetic acid Chemical compound FC(F)(F)C1=C(C(C)(C)C)ON=C1C1=NC(C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)=NO1 SRAWHOFAUDTCLR-RHSMWYFYSA-N 0.000 claims description 2
• BABPICUSEUPSLR-WZONZLPQSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(3-methylphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CC1=CC=CC(N2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)[C@H](O)CN3C[C@@H](CC(O)=O)CCC3)C=N2)C(F)(F)F)=C1 BABPICUSEUPSLR-WZONZLPQSA-N 0.000 claims description 2
• NIUWSPOOMRXBBA-DYESRHJHSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(4-methylpyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CC1=CC=NC(N2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)[C@H](O)CN3C[C@@H](CC(O)=O)CCC3)C=N2)C(F)(F)F)=C1 NIUWSPOOMRXBBA-DYESRHJHSA-N 0.000 claims description 2
• PIAMAGYGPYATKA-IIBYNOLFSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-[6-methyl-4-(trifluoromethyl)pyridin-2-yl]-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound CC1=CC(C(F)(F)F)=CC(N2C(=C(C=3ON=C(N=3)C=3C=CC(=CC=3)[C@H](O)CN3C[C@@H](CC(O)=O)CCC3)C=N2)C(F)(F)F)=N1 PIAMAGYGPYATKA-IIBYNOLFSA-N 0.000 claims description 2
• VHCDOWYWHIDGET-VGOFRKELSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 VHCDOWYWHIDGET-VGOFRKELSA-N 0.000 claims description 2
• KUQLVOCPMLBBBL-VQIMIIECSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-pyridin-2-yl-5-(trifluoromethyl)imidazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(C=N1)C=1N=CC=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 KUQLVOCPMLBBBL-VQIMIIECSA-N 0.000 claims description 2
• MBGYEWFSDZABGZ-OXQOHEQNSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-pyridin-2-yl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 MBGYEWFSDZABGZ-OXQOHEQNSA-N 0.000 claims description 2
• JDPHPEUIQJNULE-CRAIPNDOSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(2-methylpropyl)-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound FC(F)(F)C1=C(CC(C)C)ON=C1C1=NC(C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)=NO1 JDPHPEUIQJNULE-CRAIPNDOSA-N 0.000 claims description 2
• CEYRFFPLOYTJMF-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(trifluoromethyl)-1-[2-(trifluoromethyl)phenyl]pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C(=CC=CC=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 CEYRFFPLOYTJMF-OPAMFIHVSA-N 0.000 claims description 2
• QVKSDCBIQVYHLQ-OPAMFIHVSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(trifluoromethyl)-1-[3-(trifluoromethyl)phenyl]pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1C=C(C=CC=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 QVKSDCBIQVYHLQ-OPAMFIHVSA-N 0.000 claims description 2
• FBLIVARBAKENLM-FOIQADDNSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-(trifluoromethyl)-1-[5-(trifluoromethyl)pyridin-2-yl]pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(N=C1)C=1N=CC(=CC=1)C(F)(F)F)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 FBLIVARBAKENLM-FOIQADDNSA-N 0.000 claims description 2
• WQOAODKWNVPLPY-RHSMWYFYSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[5-propan-2-yl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound FC(F)(F)C1=C(C(C)C)ON=C1C1=NC(C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)=NO1 WQOAODKWNVPLPY-RHSMWYFYSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims 5
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
• MOFNVCHJYHWJMD-LROBGIAVSA-N (3s)-1-[2-hydroxy-2-[4-[5-(5-pyridin-2-ylthiophen-2-yl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(ON=2)C=2SC(=CC=2)C=2N=CC=CC=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 MOFNVCHJYHWJMD-LROBGIAVSA-N 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
• JZIWCSWKUHCCAM-VGOFRKELSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(2-methoxyphenyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound COC1=CC=CC=C1N1C(C(F)(F)F)=C(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](O)CN2C[C@@H](CC(O)=O)CCC2)C=N1 JZIWCSWKUHCCAM-VGOFRKELSA-N 0.000 claims 2
• BWIJAIFJJYVYQA-IIBYNOLFSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(oxan-4-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(C2CCOCC2)N=C1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 BWIJAIFJJYVYQA-IIBYNOLFSA-N 0.000 claims 2
• BLFHQXOSHLOIDK-VGOFRKELSA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C=1SC(=C(C=1)C=1C=CC=CC=1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 BLFHQXOSHLOIDK-VGOFRKELSA-N 0.000 claims 2
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 2
• XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 1
• OBYYZTVCYQIGAP-CXAGYDPISA-N 2-[(3r)-1-[(2s)-2-hydroxy-2-[4-[5-[1-(2,2,2-trifluoroethyl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]piperidin-3-yl]acetic acid Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1N=C(ON=1)C1=C(N(CC(F)(F)F)N=C1)C(F)(F)F)N1CCC[C@H](CC(O)=O)C1 OBYYZTVCYQIGAP-CXAGYDPISA-N 0.000 claims 1
• 125000003831 tetrazolyl group Chemical group 0.000 claims 1
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