AU2005308575A1 - 7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as HMG Co-A reductase inhibitors for the treatment of lipidemia - Google Patents

Info

Publication number

AU2005308575A1

AU2005308575A1 AU2005308575A AU2005308575A AU2005308575A1 AU 2005308575 A1 AU2005308575 A1 AU 2005308575A1 AU 2005308575 A AU2005308575 A AU 2005308575A AU 2005308575 A AU2005308575 A AU 2005308575A AU 2005308575 A1 AU2005308575 A1 AU 2005308575A1

Authority

AU

Australia

Prior art keywords

fluoro

phenyl

dihydroxy

isopropyl

pyrazol

Prior art date

2004-11-23

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
• Discuss

• 239000003112 inhibitor Substances 0.000 title claims description 31
• 238000011282 treatment Methods 0.000 title description 32
• 150000001875 compounds Chemical class 0.000 claims description 332
• -1 6-trifluoromethyl-piperidin-3-ylmethyl Chemical group 0.000 claims description 206
• 238000000034 method Methods 0.000 claims description 144
• 125000000217 alkyl group Chemical group 0.000 claims description 139
• 125000003118 aryl group Chemical group 0.000 claims description 117
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 93
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
• 229940002612 prodrug Drugs 0.000 claims description 46
• 239000000651 prodrug Substances 0.000 claims description 46
• 150000002148 esters Chemical class 0.000 claims description 38
• 150000001408 amides Chemical class 0.000 claims description 36
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 239000002904 solvent Substances 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
• 206010012601 diabetes mellitus Diseases 0.000 claims description 14
• 208000024827 Alzheimer disease Diseases 0.000 claims description 12
• 235000012000 cholesterol Nutrition 0.000 claims description 12
• JTGHBEFBQXGABE-UHFFFAOYSA-N 2,2-dihydroxyheptanoic acid Chemical compound CCCCCC(O)(O)C(O)=O JTGHBEFBQXGABE-UHFFFAOYSA-N 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• 208000001132 Osteoporosis Diseases 0.000 claims description 11
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 10
• RWNJOXUVHRXHSD-UHFFFAOYSA-N hept-6-enoic acid Chemical compound OC(=O)CCCCC=C RWNJOXUVHRXHSD-UHFFFAOYSA-N 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 230000000707 stereoselective effect Effects 0.000 claims description 8
• 239000003981 vehicle Substances 0.000 claims description 8
• RWZYEKXHAQMRIO-UHFFFAOYSA-N 2,2-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C(O)(O)CCCC=C RWZYEKXHAQMRIO-UHFFFAOYSA-N 0.000 claims description 7
• 239000012190 activator Substances 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000005647 linker group Chemical group 0.000 claims description 7
• 230000028327 secretion Effects 0.000 claims description 7
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 6
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• PDBMVYIMAMQDCW-UHFFFAOYSA-N 3,5-dihydroxyheptanoic acid Chemical compound CCC(O)CC(O)CC(O)=O PDBMVYIMAMQDCW-UHFFFAOYSA-N 0.000 claims description 5
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 229940030600 antihypertensive agent Drugs 0.000 claims description 5
• 239000002220 antihypertensive agent Substances 0.000 claims description 5
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 claims description 4
• 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 4
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 4
• 150000001450 anions Chemical class 0.000 claims description 4
• AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims description 4
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
• HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
• ZXWCKKSSCIFVBT-UHFFFAOYSA-N 1-(3-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC(F)=C1 ZXWCKKSSCIFVBT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 3
• 108010023302 HDL Cholesterol Proteins 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 229920000080 bile acid sequestrant Polymers 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims description 3
• 229940125753 fibrate Drugs 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 159000000000 sodium salts Chemical group 0.000 claims description 3
• FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 claims description 2
• FOKZKVHFKJGDPQ-NHCUHLMSSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-[[5-(trifluoromethyl)pyridin-2-yl]methylcarbamoyl]pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=C(C(F)(F)F)C=N1 FOKZKVHFKJGDPQ-NHCUHLMSSA-N 0.000 claims description 2
• QUONIPBKORDMFV-WOJBJXKFSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-[[6-(trifluoromethyl)pyridin-3-yl]methylcarbamoyl]pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=C(C(F)(F)F)N=C1 QUONIPBKORDMFV-WOJBJXKFSA-N 0.000 claims description 2
• DGPVRQDECQBJDH-YFHSQZFMSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpiperidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCCCC1C1=CC=CC=C1 DGPVRQDECQBJDH-YFHSQZFMSA-N 0.000 claims description 2
• BKOCYFTZOYVYRU-FGZHOGPDSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[[3-(trifluoromethoxy)phenyl]methyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=CC=CC(OC(F)(F)F)=C1 BKOCYFTZOYVYRU-FGZHOGPDSA-N 0.000 claims description 2
• UNLLOSFOBSEAHC-FGZHOGPDSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[[4-(trifluoromethoxy)phenyl]methyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=CC=C(OC(F)(F)F)C=C1 UNLLOSFOBSEAHC-FGZHOGPDSA-N 0.000 claims description 2
• LNHDIVHKXKALGR-RTBURBONSA-N (3r,5r)-7-[5-(cyclopropylmethylcarbamoyl)-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1CC1 LNHDIVHKXKALGR-RTBURBONSA-N 0.000 claims description 2
• UOQDDDHVXGODON-DHIUTWEWSA-N (3r,5r)-7-[5-[(4-cyanophenyl)methylcarbamoyl]-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=C(C#N)C=C1 UOQDDDHVXGODON-DHIUTWEWSA-N 0.000 claims description 2
• OTMXXXNXTHWXTC-DNQXCXABSA-N (3r,5r)-7-[5-[benzyl(ethyl)carbamoyl]-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound N=1N(C=2C=CC(F)=CC=2)C(CC[C@@H](O)C[C@@H](O)CC(O)=O)=C(C(C)C)C=1C(=O)N(CC)CC1=CC=CC=C1 OTMXXXNXTHWXTC-DNQXCXABSA-N 0.000 claims description 2
• 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 2
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• FZOXQCRZKSQGCX-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-5-[methyl-[(2,3,5-trifluorophenyl)methyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CCC(O)CC(O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=CC(F)=CC(F)=C1F FZOXQCRZKSQGCX-UHFFFAOYSA-N 0.000 claims description 2
• ANCCCBGIKLEEPD-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-5-[methyl-[(2,3,6-trifluorophenyl)methyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CCC(O)CC(O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=C(F)C=CC(F)=C1F ANCCCBGIKLEEPD-UHFFFAOYSA-N 0.000 claims description 2
• MXXSOOUZBWIHDT-UHFFFAOYSA-N 7-[5-[(2,3-difluoro-4-methoxyphenyl)methyl-methylcarbamoyl]-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound FC1=C(F)C(OC)=CC=C1CN(C)C(=O)C1=NN(C=2C=CC(F)=CC=2)C(CCC(O)CC(O)CC(O)=O)=C1C(C)C MXXSOOUZBWIHDT-UHFFFAOYSA-N 0.000 claims description 2
• BIRRDXBSICICJO-UHFFFAOYSA-N 7-[5-[(2,3-difluoro-6-methoxyphenyl)methyl-methylcarbamoyl]-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound COC1=CC=C(F)C(F)=C1CN(C)C(=O)C1=NN(C=2C=CC(F)=CC=2)C(CCC(O)CC(O)CC(O)=O)=C1C(C)C BIRRDXBSICICJO-UHFFFAOYSA-N 0.000 claims description 2
• 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 claims description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
• 239000003963 antioxidant agent Substances 0.000 claims description 2
• 230000003078 antioxidant effect Effects 0.000 claims description 2
• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 235000010855 food raising agent Nutrition 0.000 claims description 2
• 239000003456 ion exchange resin Substances 0.000 claims description 2
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
• AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 claims description 2
• 229960003512 nicotinic acid Drugs 0.000 claims description 2
• 235000001968 nicotinic acid Nutrition 0.000 claims description 2
• 239000011664 nicotinic acid Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 37
• FTWSRGZZXBAIMY-FCHUYYIVSA-N (3R,5R)-7-[5-(cyclohexylmethylcarbamoyl)-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCC2CCCCC2)=NN1C1=CC=C(F)C=C1 FTWSRGZZXBAIMY-FCHUYYIVSA-N 0.000 claims 1
• WOIWYAXSQWDKMG-ZWKOTPCHSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(propan-2-ylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NC(C)C)=NN1C1=CC=C(F)C=C1 WOIWYAXSQWDKMG-ZWKOTPCHSA-N 0.000 claims 1
• OZUQXCFEFOFUED-RBUKOAKNSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-methylpropylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCC(C)C)=NN1C1=CC=C(F)C=C1 OZUQXCFEFOFUED-RBUKOAKNSA-N 0.000 claims 1
• VPBKAPKIGWAXHB-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpropan-2-ylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC(C)(C)C1=CC=CC=C1 VPBKAPKIGWAXHB-DHIUTWEWSA-N 0.000 claims 1
• JDNNJMMIANDJER-AEAWWFNXSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpyrrolidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCCC1C1=CC=CC=C1 JDNNJMMIANDJER-AEAWWFNXSA-N 0.000 claims 1
• YLAVHPQPEFUCRY-FLZRTACHSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(3-phenylpiperidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C1)CCCC1C1=CC=CC=C1 YLAVHPQPEFUCRY-FLZRTACHSA-N 0.000 claims 1
• ZVIGYIARKWWQTG-JKSUJKDBSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(methylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NC)=NN1C1=CC=C(F)C=C1 ZVIGYIARKWWQTG-JKSUJKDBSA-N 0.000 claims 1
• UCPFWXTXESQPTQ-HZPDHXFCSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(methylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NC)=NN1C1=CC=C(F)C=C1 UCPFWXTXESQPTQ-HZPDHXFCSA-N 0.000 claims 1
• XNGHJMJEQHCIOC-LEWJYISDSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(phenylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(C=C[C@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC1=CC=CC=C1 XNGHJMJEQHCIOC-LEWJYISDSA-N 0.000 claims 1
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