NZ538031A - Indoles having anti-diabetic activity - Google Patents
Indoles having anti-diabetic activityInfo
- Publication number
- NZ538031A NZ538031A NZ538031A NZ53803103A NZ538031A NZ 538031 A NZ538031 A NZ 538031A NZ 538031 A NZ538031 A NZ 538031A NZ 53803103 A NZ53803103 A NZ 53803103A NZ 538031 A NZ538031 A NZ 538031A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- indol
- phenoxy
- trifluoromethoxy
- acid
- Prior art date
Links
- 230000003178 anti-diabetic effect Effects 0.000 title claims description 3
- 150000002475 indoles Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 206
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 38
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 280
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 198
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 144
- 235000019260 propionic acid Nutrition 0.000 claims description 140
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 130
- 229910052736 halogen Inorganic materials 0.000 claims description 79
- 150000002367 halogens Chemical class 0.000 claims description 79
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- -1 3-benzisoxazolyl Chemical group 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 34
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
- 229940125396 insulin Drugs 0.000 claims description 26
- 102000004877 Insulin Human genes 0.000 claims description 25
- 108090001061 Insulin Proteins 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- ZFQAHULOEMHEDO-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 ZFQAHULOEMHEDO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims description 5
- GDSCCLCHSVBGDJ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 GDSCCLCHSVBGDJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 5
- 229960003105 metformin Drugs 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- DADJBGLOBSJHMJ-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C1=C(Cl)C(OC(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 DADJBGLOBSJHMJ-UHFFFAOYSA-N 0.000 claims description 4
- DZZZZGWJLMRFAE-UHFFFAOYSA-N 2-[2-fluoro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound C1=C(F)C(OC(CCC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 DZZZZGWJLMRFAE-UHFFFAOYSA-N 0.000 claims description 4
- HSAJHASPINXSLB-UHFFFAOYSA-N 2-[2-fluoro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=C(F)C(OC(C(C)C)C(O)=O)=C1 HSAJHASPINXSLB-UHFFFAOYSA-N 0.000 claims description 4
- NQXYBQPMKCBUKE-UHFFFAOYSA-N 2-[3-[[2-methyl-6-(trifluoromethoxy)-3-[4-(trifluoromethoxy)benzoyl]indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC(F)(F)F)=CC=3)=C2C)=C1 NQXYBQPMKCBUKE-UHFFFAOYSA-N 0.000 claims description 4
- HYVCPFNHIBPRQT-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-ethyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C(C)C)C(O)=O)C=CC=2)C(CC)=C1C(=O)C1=CC=C(Cl)C=C1 HYVCPFNHIBPRQT-UHFFFAOYSA-N 0.000 claims description 4
- ZRROQMKIVRYIRJ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)C(F)(F)F)=C1 ZRROQMKIVRYIRJ-UHFFFAOYSA-N 0.000 claims description 4
- LISVEYZVTCQAKX-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(OC)=CC=3)=C2C)=C1 LISVEYZVTCQAKX-UHFFFAOYSA-N 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- QTNLJMSTDKBAOB-XMMPIXPASA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 QTNLJMSTDKBAOB-XMMPIXPASA-N 0.000 claims description 3
- LKDQRHNNBUIDOX-UHFFFAOYSA-N 2-[2-fluoro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C1=C(F)C(OC(CC)C(O)=O)=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)C(F)(F)F)=C1 LKDQRHNNBUIDOX-UHFFFAOYSA-N 0.000 claims description 3
- ABJJNOXUYARJRD-UHFFFAOYSA-N 2-[3-[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 ABJJNOXUYARJRD-UHFFFAOYSA-N 0.000 claims description 3
- FUKPZDIJWLADCC-UHFFFAOYSA-N 2-[3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)Cl)=C2C)=C1 FUKPZDIJWLADCC-UHFFFAOYSA-N 0.000 claims description 3
- PPABEUFJNVWETL-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 PPABEUFJNVWETL-UHFFFAOYSA-N 0.000 claims description 3
- WNQXHZBHGPUSAX-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)C(F)(F)F)=C1 WNQXHZBHGPUSAX-UHFFFAOYSA-N 0.000 claims description 3
- WOWXDFSOKNMFNL-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(SC(C)C(O)=O)=C1 WOWXDFSOKNMFNL-UHFFFAOYSA-N 0.000 claims description 3
- YYKISMWXJXUZOF-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)=C1 YYKISMWXJXUZOF-UHFFFAOYSA-N 0.000 claims description 3
- XVAUIKAGDSBRLH-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(OC(C(C)C)C(O)=O)=C1 XVAUIKAGDSBRLH-UHFFFAOYSA-N 0.000 claims description 3
- YEVRZHFEOLHMAB-UHFFFAOYSA-N 2-[5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-fluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OC(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 YEVRZHFEOLHMAB-UHFFFAOYSA-N 0.000 claims description 3
- LIZRTJPNVJDDNR-UHFFFAOYSA-N 3-methyl-2-[3-[[2-methyl-6-(trifluoromethoxy)-3-[4-(trifluoromethoxy)benzoyl]indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC(C)C(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC(F)(F)F)=CC=3)=C2C)=C1 LIZRTJPNVJDDNR-UHFFFAOYSA-N 0.000 claims description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229960002855 simvastatin Drugs 0.000 claims description 3
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 3
- RQEMFSWGKBMQMR-CQSZACIVSA-N (2r)-2-[2-chloro-5-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@H](C)C(O)=O)=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 RQEMFSWGKBMQMR-CQSZACIVSA-N 0.000 claims description 2
- JAQNMRVDOVQJOB-XMMPIXPASA-N (2r)-2-[3-[(2-methyl-3-phenylsulfanylindol-1-yl)methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC=CC=C3C(SC=3C=CC=CC=3)=C2C)=C1 JAQNMRVDOVQJOB-XMMPIXPASA-N 0.000 claims description 2
- IGRNHXSVCPOZSZ-CQSZACIVSA-N (2r)-2-[3-[[2-methyl-3-(2,4,6-trichlorobenzoyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)=C2C)=C1 IGRNHXSVCPOZSZ-CQSZACIVSA-N 0.000 claims description 2
- IXMBKWLUVBDSJF-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-chloro-2-methylbenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)C)=C2C)=C1 IXMBKWLUVBDSJF-QGZVFWFLSA-N 0.000 claims description 2
- CYQLAAFBVIFOGI-XMMPIXPASA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-(fluoromethyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CF)=C1 CYQLAAFBVIFOGI-XMMPIXPASA-N 0.000 claims description 2
- RRWVTEWULIIMNQ-RUZDIDTESA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-ethyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CC)=C1 RRWVTEWULIIMNQ-RUZDIDTESA-N 0.000 claims description 2
- OTCMKZGJCNQILO-GOSISDBHSA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-4-propylphenoxy]propanoic acid Chemical compound CCCC1=CC=C(O[C@H](C)C(O)=O)C=C1CN1C2=CC(OC(F)(F)F)=CC=C2C(C(=O)C=2C=CC(Cl)=CC=2)=C1C OTCMKZGJCNQILO-GOSISDBHSA-N 0.000 claims description 2
- MVJARISIPDSITL-XMMPIXPASA-N (2r)-2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 MVJARISIPDSITL-XMMPIXPASA-N 0.000 claims description 2
- IUURWPVEMXYMPE-HSZRJFAPSA-N (2r)-2-[3-[[3-(4-chlorophenoxy)-5-iodo-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=C(I)C=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 IUURWPVEMXYMPE-HSZRJFAPSA-N 0.000 claims description 2
- AEXKFXDNMAYUKM-WXKMRPJQSA-N (2r)-2-[3-[[3-(4-chlorophenyl)sulfinyl-2-methyl-5-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC=C(OC(F)(F)F)C=C3C(S(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 AEXKFXDNMAYUKM-WXKMRPJQSA-N 0.000 claims description 2
- CCNHNUIPUCBUCG-RUZDIDTESA-N (2r)-2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 CCNHNUIPUCBUCG-RUZDIDTESA-N 0.000 claims description 2
- FNFJGCIYIRZSBN-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 FNFJGCIYIRZSBN-QGZVFWFLSA-N 0.000 claims description 2
- HNEYLYWCHIFCBH-GOSISDBHSA-N (2r)-2-[3-[[3-(4-methoxybenzoyl)-2-methylindol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=CC=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 HNEYLYWCHIFCBH-GOSISDBHSA-N 0.000 claims description 2
- JZRJHYFPUFMUCA-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-methoxyphenyl)-2-methyl-4-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C1=C(OC(F)(F)F)C=CC=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 JZRJHYFPUFMUCA-QGZVFWFLSA-N 0.000 claims description 2
- LEUKBXHFVSLKSQ-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 LEUKBXHFVSLKSQ-QGZVFWFLSA-N 0.000 claims description 2
- FILNOUSWFHAYQZ-OAHLLOKOSA-N (2r)-2-[3-fluoro-5-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC(F)=CC(O[C@H](C)C(O)=O)=C1 FILNOUSWFHAYQZ-OAHLLOKOSA-N 0.000 claims description 2
- SIVBSGPWDBIODF-MRXNPFEDSA-N (2r)-2-[4-chloro-3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC(O[C@H](C)C(O)=O)=CC=C1Cl SIVBSGPWDBIODF-MRXNPFEDSA-N 0.000 claims description 2
- LFFBLBCBXYEEHS-MRXNPFEDSA-N (2r)-2-[4-fluoro-3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC(O[C@H](C)C(O)=O)=CC=C1F LFFBLBCBXYEEHS-MRXNPFEDSA-N 0.000 claims description 2
- NDRWPQWXLPGXBK-GDLZYMKVSA-N (2r)-7-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-ethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C([C@](OC1=C2)(CC)C(O)=O)CC1=CC=C2CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 NDRWPQWXLPGXBK-GDLZYMKVSA-N 0.000 claims description 2
- RQEMFSWGKBMQMR-AWEZNQCLSA-N (2s)-2-[2-chloro-5-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 RQEMFSWGKBMQMR-AWEZNQCLSA-N 0.000 claims description 2
- MYXQQHLZVWUGMS-HNNXBMFYSA-N (2s)-2-[2-chloro-5-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=C(Cl)C(O[C@@H](C)C(O)=O)=C1 MYXQQHLZVWUGMS-HNNXBMFYSA-N 0.000 claims description 2
- DLIBHBZNTVQWRD-HNNXBMFYSA-N (2s)-2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 DLIBHBZNTVQWRD-HNNXBMFYSA-N 0.000 claims description 2
- PQXSNXWLNLLSMA-HNNXBMFYSA-N (2s)-2-[2-chloro-5-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)C(F)(F)F)=C1 PQXSNXWLNLLSMA-HNNXBMFYSA-N 0.000 claims description 2
- ATSCMWOXAMUZQA-KRWDZBQOSA-N (2s)-2-[3-[2-methyl-3-(quinoline-2-carbonyl)-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3N=C4C=CC=CC4=CC=3)=C2C)=C1 ATSCMWOXAMUZQA-KRWDZBQOSA-N 0.000 claims description 2
- IGRNHXSVCPOZSZ-AWEZNQCLSA-N (2s)-2-[3-[[2-methyl-3-(2,4,6-trichlorobenzoyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)=C2C)=C1 IGRNHXSVCPOZSZ-AWEZNQCLSA-N 0.000 claims description 2
- QSBFQUOLQNMMMZ-HNNXBMFYSA-N (2s)-2-[3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)Cl)=C2C)=C1 QSBFQUOLQNMMMZ-HNNXBMFYSA-N 0.000 claims description 2
- LGYGMOFVNHPEFQ-INIZCTEOSA-N (2s)-2-[3-[[3-(2-chloro-4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound ClC1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 LGYGMOFVNHPEFQ-INIZCTEOSA-N 0.000 claims description 2
- RRWVTEWULIIMNQ-VWLOTQADSA-N (2s)-2-[3-[[3-(4-chlorobenzoyl)-2-ethyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CC)=C1 RRWVTEWULIIMNQ-VWLOTQADSA-N 0.000 claims description 2
- DHUATBAZHILHIC-INIZCTEOSA-N (2s)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 DHUATBAZHILHIC-INIZCTEOSA-N 0.000 claims description 2
- SEPDXGCELXWFQW-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-chlorobenzoyl)-2-methylindol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 SEPDXGCELXWFQW-KRWDZBQOSA-N 0.000 claims description 2
- XRCQRZOAKNRNKA-INIZCTEOSA-N (2s)-2-[3-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 XRCQRZOAKNRNKA-INIZCTEOSA-N 0.000 claims description 2
- NISPZHOPXCGOEX-SFHVURJKSA-N (2s)-2-[3-[[3-(4-methoxy-2-methylbenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound CC1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 NISPZHOPXCGOEX-SFHVURJKSA-N 0.000 claims description 2
- NOCJVEVUKOBODD-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxybenzoyl)-2-methyl-5-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC(OC(F)(F)F)=CC=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 NOCJVEVUKOBODD-KRWDZBQOSA-N 0.000 claims description 2
- NRWLBRVSEKXSCU-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 NRWLBRVSEKXSCU-KRWDZBQOSA-N 0.000 claims description 2
- LFFBLBCBXYEEHS-INIZCTEOSA-N (2s)-2-[4-fluoro-3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC(O[C@@H](C)C(O)=O)=CC=C1F LFFBLBCBXYEEHS-INIZCTEOSA-N 0.000 claims description 2
- UDXDJXFIZOIXQL-PMERELPUSA-N (2s)-2-ethyl-7-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-3,4-dihydrochromene-2-carboxylic acid Chemical compound C([C@@](OC1=C2)(CC)C(O)=O)CC1=CC=C2CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(OC)C=C1 UDXDJXFIZOIXQL-PMERELPUSA-N 0.000 claims description 2
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- GPXYAXLTAJGERS-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound C1=C(Cl)C(OC(C)(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 GPXYAXLTAJGERS-UHFFFAOYSA-N 0.000 claims description 2
- PPQPEZPPYIDTII-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound C1=C(Cl)C(OC(CCC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 PPQPEZPPYIDTII-UHFFFAOYSA-N 0.000 claims description 2
- XRQFJGCCZJDFSB-UHFFFAOYSA-N 2-[2-fluoro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(F)C(OC(C(C)C)C(O)=O)=C1 XRQFJGCCZJDFSB-UHFFFAOYSA-N 0.000 claims description 2
- OQHDMYPNYDIVAL-UHFFFAOYSA-N 2-[3-[3-(2-chloro-6-methylpyridine-4-carbonyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC(C)=NC(Cl)=C1 OQHDMYPNYDIVAL-UHFFFAOYSA-N 0.000 claims description 2
- GXKCCOHPPSBKJF-UHFFFAOYSA-N 2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 GXKCCOHPPSBKJF-UHFFFAOYSA-N 0.000 claims description 2
- DPSLLZVRBVZESA-UHFFFAOYSA-N 2-[3-[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1OC1=CC=C(Cl)C=C1 DPSLLZVRBVZESA-UHFFFAOYSA-N 0.000 claims description 2
- FFMZCPAKRXAVAP-UHFFFAOYSA-N 2-[3-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(OC(C)(C)C(O)=O)=C1 FFMZCPAKRXAVAP-UHFFFAOYSA-N 0.000 claims description 2
- CWRFPOUTBPHTNW-UHFFFAOYSA-N 2-[3-[3-(6-chloropyridine-3-carbonyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)N=C1 CWRFPOUTBPHTNW-UHFFFAOYSA-N 0.000 claims description 2
- KHDOQCRATFDAAD-UHFFFAOYSA-N 2-[3-[[2-(bromomethyl)-3-(4-chlorobenzoyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CBr)=C1 KHDOQCRATFDAAD-UHFFFAOYSA-N 0.000 claims description 2
- GXGBRRDEODHMEN-UHFFFAOYSA-N 2-[3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)Cl)=C2C)=C1 GXGBRRDEODHMEN-UHFFFAOYSA-N 0.000 claims description 2
- RKVMKBORJBUIHT-UHFFFAOYSA-N 2-[3-[[3-(2-chloro-4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(OC)=CC=3)Cl)=C2C)=C1 RKVMKBORJBUIHT-UHFFFAOYSA-N 0.000 claims description 2
- WDYSLPXOZUXTDH-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-ethyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C)(CC)C(O)=O)C=CC=2)C(CC)=C1C(=O)C1=CC=C(Cl)C=C1 WDYSLPXOZUXTDH-UHFFFAOYSA-N 0.000 claims description 2
- FUFARUOUKIJRPY-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-cyclohexylacetic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C3CCCCC3)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 FUFARUOUKIJRPY-UHFFFAOYSA-N 0.000 claims description 2
- GMVPHJLMHPZFGH-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 GMVPHJLMHPZFGH-UHFFFAOYSA-N 0.000 claims description 2
- ROJQZJIQYRUTLZ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-propan-2-yl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C(C)C)=C1 ROJQZJIQYRUTLZ-UHFFFAOYSA-N 0.000 claims description 2
- LACJFPYFAOALLQ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-propyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(CC)C(O)=O)C=CC=2)C(CCC)=C1C(=O)C1=CC=C(Cl)C=C1 LACJFPYFAOALLQ-UHFFFAOYSA-N 0.000 claims description 2
- LHXNGQFMGXWAKC-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(OC(C)(C)C(O)=O)=C1 LHXNGQFMGXWAKC-UHFFFAOYSA-N 0.000 claims description 2
- GCMXODYEMBZISG-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(SC(C)(C)C(O)=O)=C1 GCMXODYEMBZISG-UHFFFAOYSA-N 0.000 claims description 2
- UVWQDLJYHIAYRD-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]sulfinyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(S(=O)C(C)(C)C(O)=O)=C1 UVWQDLJYHIAYRD-UHFFFAOYSA-N 0.000 claims description 2
- KHHLGORWIPKMRQ-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)C(F)(F)F)=C1 KHHLGORWIPKMRQ-UHFFFAOYSA-N 0.000 claims description 2
- KNMPRJUIANDYQF-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)Cl)=C2C)=C1 KNMPRJUIANDYQF-UHFFFAOYSA-N 0.000 claims description 2
- VACIVBAARCYWMM-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C(=CC(Cl)=CC=3)Cl)=C2C)=C1 VACIVBAARCYWMM-UHFFFAOYSA-N 0.000 claims description 2
- UWSGPEVRCRQITC-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 UWSGPEVRCRQITC-UHFFFAOYSA-N 0.000 claims description 2
- IAKDSEZOCLJQNV-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C(=CC=C(OC(C)(C)C(O)=O)C=2)Cl)C(C)=C1SC1=CC=C(Cl)C=C1 IAKDSEZOCLJQNV-UHFFFAOYSA-N 0.000 claims description 2
- LOPXRVSGPQAMQP-UHFFFAOYSA-N 2-[5-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]-2-fluorophenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C(F)=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 LOPXRVSGPQAMQP-UHFFFAOYSA-N 0.000 claims description 2
- CTTLGDYFFHUAKB-UHFFFAOYSA-N 2-[5-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-fluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OC(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 CTTLGDYFFHUAKB-UHFFFAOYSA-N 0.000 claims description 2
- WMLJWYAICKIALM-UHFFFAOYSA-N 2-methyl-2-[3-[2-methyl-3-(6-methylpyridine-2-carbonyl)-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=CC(C)=N1 WMLJWYAICKIALM-UHFFFAOYSA-N 0.000 claims description 2
- XYGMWQAYJKVJIM-UHFFFAOYSA-N 3-[3-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(CCC(O)=O)=C1 XYGMWQAYJKVJIM-UHFFFAOYSA-N 0.000 claims description 2
- FDRGVXGZXMEANK-UHFFFAOYSA-N 3-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2-phenylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(CC(C(O)=O)C=3C=CC=CC=3)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 FDRGVXGZXMEANK-UHFFFAOYSA-N 0.000 claims description 2
- OQGBTZKOUFPETG-UHFFFAOYSA-N 3-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(CC(C)C(O)=O)=C1 OQGBTZKOUFPETG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003472 antidiabetic agent Substances 0.000 claims description 2
- 229960005370 atorvastatin Drugs 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 claims description 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229960003765 fluvastatin Drugs 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229960004844 lovastatin Drugs 0.000 claims description 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound 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 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002797 pitavastatin Drugs 0.000 claims description 2
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 229960000672 rosuvastatin Drugs 0.000 claims description 2
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 2
- HUPQYPMULVBQDL-UHFFFAOYSA-N pentanoic acid Chemical compound CCCCC(O)=O.CCCCC(O)=O HUPQYPMULVBQDL-UHFFFAOYSA-N 0.000 claims 9
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 5
- JVGRUOOXEHODQJ-UHFFFAOYSA-N 2-[3-[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(Cl)=CC=3)=C2C)=C1 JVGRUOOXEHODQJ-UHFFFAOYSA-N 0.000 claims 4
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 4
- STXANKVKGVTYTM-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(C=3C=CC(Cl)=CC=3)=C2C)C(F)(F)F)=C1 STXANKVKGVTYTM-UHFFFAOYSA-N 0.000 claims 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 3
- WLVIHEZFLDLAON-UHFFFAOYSA-N 2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound OC(=O)C(C)OCC(F)(F)F WLVIHEZFLDLAON-UHFFFAOYSA-N 0.000 claims 2
- PMJAKURVMMEBEH-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C1=C(Cl)C(OC(CC)C(O)=O)=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)C(F)(F)F)=C1 PMJAKURVMMEBEH-UHFFFAOYSA-N 0.000 claims 2
- VKEGUBACPMSOAZ-UHFFFAOYSA-N 2-[2-fluoro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C1=C(F)C(OC(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 VKEGUBACPMSOAZ-UHFFFAOYSA-N 0.000 claims 2
- YPPGANUPFGNPDP-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(OC)=CC=3)=C2C(F)(F)F)=C1 YPPGANUPFGNPDP-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- QDOBTDFLGVUAAB-XMMPIXPASA-N (2r)-2-[2-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC=C1CN1C2=CC(OC(F)(F)F)=CC=C2C(C(=O)C=2C=CC(OC)=CC=2)=C1C QDOBTDFLGVUAAB-XMMPIXPASA-N 0.000 claims 1
- DLIBHBZNTVQWRD-OAHLLOKOSA-N (2r)-2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 DLIBHBZNTVQWRD-OAHLLOKOSA-N 0.000 claims 1
- YYYXCMZKYLVQPG-MRXNPFEDSA-N (2r)-2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(Cl)C(O[C@H](C)C(O)=O)=C1 YYYXCMZKYLVQPG-MRXNPFEDSA-N 0.000 claims 1
- ATSCMWOXAMUZQA-QGZVFWFLSA-N (2r)-2-[3-[2-methyl-3-(quinoline-2-carbonyl)-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3N=C4C=CC=CC4=CC=3)=C2C)=C1 ATSCMWOXAMUZQA-QGZVFWFLSA-N 0.000 claims 1
- STWITCBWQHTJFJ-XMMPIXPASA-N (2r)-2-[3-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 STWITCBWQHTJFJ-XMMPIXPASA-N 0.000 claims 1
- HAVSKLWHMJKRKI-MRXNPFEDSA-N (2r)-2-[3-[[2-methyl-6-(trifluoromethoxy)-3-[4-(trifluoromethoxy)benzoyl]indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC(F)(F)F)=CC=3)=C2C)=C1 HAVSKLWHMJKRKI-MRXNPFEDSA-N 0.000 claims 1
- SEPDXGCELXWFQW-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-methylindol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 SEPDXGCELXWFQW-QGZVFWFLSA-N 0.000 claims 1
- TVLGZNVIVKMVLG-OAHLLOKOSA-N (2r)-2-[3-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(F)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 TVLGZNVIVKMVLG-OAHLLOKOSA-N 0.000 claims 1
- MEPFPFGMQXDYDS-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-methoxyphenoxy)-2-methyl-4-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=C(C=CC=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 MEPFPFGMQXDYDS-QGZVFWFLSA-N 0.000 claims 1
- IATYGESVHLSQLR-GDLZYMKVSA-N (2r)-7-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-ethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C([C@](OC1=C2)(CC)C(O)=O)CC1=CC=C2CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(Cl)C=C1Cl IATYGESVHLSQLR-GDLZYMKVSA-N 0.000 claims 1
- MTRYXSFBTALAFQ-KRWDZBQOSA-N (2s)-2-[2-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC=C1O[C@@H](C)C(O)=O MTRYXSFBTALAFQ-KRWDZBQOSA-N 0.000 claims 1
- WFKWCLXCNCBACV-HNNXBMFYSA-N (2s)-2-[2-chloro-5-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 WFKWCLXCNCBACV-HNNXBMFYSA-N 0.000 claims 1
- CAXGOBZKWGIMCS-HNNXBMFYSA-N (2s)-2-[3-[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(Cl)=CC=3)=C2C)=C1 CAXGOBZKWGIMCS-HNNXBMFYSA-N 0.000 claims 1
- GIQQXFLSYSDTKU-INIZCTEOSA-N (2s)-2-[3-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(O[C@@H](C)C(O)=O)=C1 GIQQXFLSYSDTKU-INIZCTEOSA-N 0.000 claims 1
- OTCMKZGJCNQILO-SFHVURJKSA-N (2s)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-4-propylphenoxy]propanoic acid Chemical compound CCCC1=CC=C(O[C@@H](C)C(O)=O)C=C1CN1C2=CC(OC(F)(F)F)=CC=C2C(C(=O)C=2C=CC(Cl)=CC=2)=C1C OTCMKZGJCNQILO-SFHVURJKSA-N 0.000 claims 1
- QTNLJMSTDKBAOB-DEOSSOPVSA-N (2s)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 QTNLJMSTDKBAOB-DEOSSOPVSA-N 0.000 claims 1
- MMYILDZMWXDQMX-HNNXBMFYSA-N (2s)-2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C(CN2C3=CC(=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)C(F)(F)F)=C1 MMYILDZMWXDQMX-HNNXBMFYSA-N 0.000 claims 1
- TVLGZNVIVKMVLG-HNNXBMFYSA-N (2s)-2-[3-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 TVLGZNVIVKMVLG-HNNXBMFYSA-N 0.000 claims 1
- FNFJGCIYIRZSBN-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 FNFJGCIYIRZSBN-KRWDZBQOSA-N 0.000 claims 1
- JZRJHYFPUFMUCA-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxyphenyl)-2-methyl-4-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C1=C(OC(F)(F)F)C=CC=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 JZRJHYFPUFMUCA-KRWDZBQOSA-N 0.000 claims 1
- SIVBSGPWDBIODF-INIZCTEOSA-N (2s)-2-[4-chloro-3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC(O[C@@H](C)C(O)=O)=CC=C1Cl SIVBSGPWDBIODF-INIZCTEOSA-N 0.000 claims 1
- GPXDQOCXCPNZAS-RPBOFIJWSA-N (2s,3r)-3-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2,3-dihydroxypropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(C=CC=2)[C@@H](O)[C@H](O)C(O)=O)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 GPXDQOCXCPNZAS-RPBOFIJWSA-N 0.000 claims 1
- QVJQLBURQNHEJM-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-ethylbutanoic acid Chemical compound C1=C(Cl)C(OC(CC)(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 QVJQLBURQNHEJM-UHFFFAOYSA-N 0.000 claims 1
- VXHOGDAPLKZJOM-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=C(Cl)C(OC(C(C)C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 VXHOGDAPLKZJOM-UHFFFAOYSA-N 0.000 claims 1
- WLUAPVNPLLWZEI-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-ethylpentanoic acid Chemical compound C1=C(Cl)C(OC(CC)(CCC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 WLUAPVNPLLWZEI-UHFFFAOYSA-N 0.000 claims 1
- OZOZCDKSQVUKPX-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound C1=C(Cl)C(OC(C)(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 OZOZCDKSQVUKPX-UHFFFAOYSA-N 0.000 claims 1
- VQMUZLVFYWOKQH-UHFFFAOYSA-N 2-[3-[3-(isoquinoline-1-carbonyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound CC1=C(C(=O)C=2C3=CC=CC=C3C=CN=2)C2=CC=C(OC(F)(F)F)C=C2N1C1=CC=CC(OC(C)(C)C(O)=O)=C1 VQMUZLVFYWOKQH-UHFFFAOYSA-N 0.000 claims 1
- YWHGDOHGZMPBAP-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-(chloromethyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CCl)=C1 YWHGDOHGZMPBAP-UHFFFAOYSA-N 0.000 claims 1
- QMJBBQISUBZKNI-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-(hydroxymethyl)-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2CO)=C1 QMJBBQISUBZKNI-UHFFFAOYSA-N 0.000 claims 1
- VFNWRYGREAHJIE-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-4-fluorophenoxy]-4,4,4-trifluorobutanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C(=CC=C(OC(CC(F)(F)F)C(O)=O)C=2)F)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 VFNWRYGREAHJIE-UHFFFAOYSA-N 0.000 claims 1
- QTNLJMSTDKBAOB-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 QTNLJMSTDKBAOB-UHFFFAOYSA-N 0.000 claims 1
- QAQFTWLMDLNSCY-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 QAQFTWLMDLNSCY-UHFFFAOYSA-N 0.000 claims 1
- WABQOZYJEPWOBO-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-propan-2-ylindol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)C(C)C)=C1 WABQOZYJEPWOBO-UHFFFAOYSA-N 0.000 claims 1
- RHBSEYKHVGROIL-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C1=CC=C(Cl)C=C1 RHBSEYKHVGROIL-UHFFFAOYSA-N 0.000 claims 1
- QLSDCMUODASXIE-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(Cl)=CC=3)=C2C)=C1 QLSDCMUODASXIE-UHFFFAOYSA-N 0.000 claims 1
- BBRYQRVATHLXTE-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenyl)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(C(F)(F)F)C=C2N(CC=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C1=CC=C(Cl)C=C1 BBRYQRVATHLXTE-UHFFFAOYSA-N 0.000 claims 1
- IJUHIZIRZISITE-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(S(=O)(=O)C(C)(C)C(O)=O)=C1 IJUHIZIRZISITE-UHFFFAOYSA-N 0.000 claims 1
- HSOSFCSZXMMUPI-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(OC(C(C)C)C(O)=O)=C1 HSOSFCSZXMMUPI-UHFFFAOYSA-N 0.000 claims 1
- XCUHWHBVKMPOJY-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenyl)-2-methyl-4-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC=CC(OC(F)(F)F)=C3C(C=3C=CC(OC)=CC=3)=C2C)=C1 XCUHWHBVKMPOJY-UHFFFAOYSA-N 0.000 claims 1
- HIJVXGRZZVSZSG-UHFFFAOYSA-N 2-[4-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(OC(C)(C)C(O)=O)C=C1 HIJVXGRZZVSZSG-UHFFFAOYSA-N 0.000 claims 1
- YKZIHRDLPSPNDY-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 YKZIHRDLPSPNDY-UHFFFAOYSA-N 0.000 claims 1
- WLXBBEFWIJRZNE-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 WLXBBEFWIJRZNE-UHFFFAOYSA-N 0.000 claims 1
- ICXPBOACCXZQHL-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 ICXPBOACCXZQHL-UHFFFAOYSA-N 0.000 claims 1
- RISVWDDLZWVFBE-UHFFFAOYSA-N 2-[4-chloro-3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]pentanoic acid Chemical compound CCCC(C(O)=O)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 RISVWDDLZWVFBE-UHFFFAOYSA-N 0.000 claims 1
- RGNTWYIVWWYSFF-UHFFFAOYSA-N 2-[5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-fluorophenoxy]-3-methylbutanoic acid Chemical compound C1=C(F)C(OC(C(C)C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 RGNTWYIVWWYSFF-UHFFFAOYSA-N 0.000 claims 1
- PIERIQWYLPBFPB-UHFFFAOYSA-N 2-[[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 PIERIQWYLPBFPB-UHFFFAOYSA-N 0.000 claims 1
- NEEWOVWBHHFJTM-UHFFFAOYSA-N 2-[[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]methyl]-2-methylpropanedioic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(CC(C)(C(O)=O)C(O)=O)=C1 NEEWOVWBHHFJTM-UHFFFAOYSA-N 0.000 claims 1
- PNAJVRDSPJQECX-UHFFFAOYSA-N 2-ethoxy-3-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]propanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 PNAJVRDSPJQECX-UHFFFAOYSA-N 0.000 claims 1
- LMSNURPNCFVXRN-UHFFFAOYSA-N 3-[3-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(CC(OCC(F)(F)F)C(O)=O)=C1 LMSNURPNCFVXRN-UHFFFAOYSA-N 0.000 claims 1
- JFYQBXITEKZMJY-UHFFFAOYSA-N 3-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(CCC(O)=O)=C1 JFYQBXITEKZMJY-UHFFFAOYSA-N 0.000 claims 1
- WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 claims 1
- LNIDLPSAWCBIPB-UHFFFAOYSA-N 5-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-ethyl-3h-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(CC)(C(O)=O)CC2=CC=1CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 LNIDLPSAWCBIPB-UHFFFAOYSA-N 0.000 claims 1
- SHKJAHJMEQUXGT-UHFFFAOYSA-N 6-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-methyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(OC(C)(CC2)C(O)=O)C2=C1 SHKJAHJMEQUXGT-UHFFFAOYSA-N 0.000 claims 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract description 21
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract description 21
- 239000000556 agonist Substances 0.000 abstract description 19
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 15
- 201000001421 hyperglycemia Diseases 0.000 abstract description 11
- 206010022489 Insulin Resistance Diseases 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
- 238000005481 NMR spectroscopy Methods 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 229910001868 water Inorganic materials 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 235000019439 ethyl acetate Nutrition 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 27
- 101150041968 CDC13 gene Proteins 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- 239000012267 brine Substances 0.000 description 23
- 239000012044 organic layer Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 15
- 239000008103 glucose Substances 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 101150014691 PPARA gene Proteins 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 102100039556 Galectin-4 Human genes 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 235000020824 obesity Nutrition 0.000 description 7
- 239000004031 partial agonist Substances 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 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 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 108010016731 PPAR gamma Proteins 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 201000001320 Atherosclerosis Diseases 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 108010023302 HDL Cholesterol Proteins 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 102000000536 PPAR gamma Human genes 0.000 description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
- 230000008484 agonism Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 208000006575 hypertriglyceridemia Diseases 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000037356 lipid metabolism Effects 0.000 description 4
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- 108010039627 Aprotinin Proteins 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 208000032928 Dyslipidaemia Diseases 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 208000013016 Hypoglycemia Diseases 0.000 description 3
- 229940122199 Insulin secretagogue Drugs 0.000 description 3
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 108010028924 PPAR alpha Proteins 0.000 description 3
- 102000023984 PPAR alpha Human genes 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 210000000577 adipose tissue Anatomy 0.000 description 3
- 229960004405 aprotinin Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 150000004283 biguanides Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000013604 expression vector Substances 0.000 description 3
- 235000013861 fat-free Nutrition 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 3
- 108010052968 leupeptin Proteins 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 3
- 229960003243 phenformin Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000001890 transfection Methods 0.000 description 3
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 3
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
- NJZQOCCEDXRQJM-UHFFFAOYSA-N 1-benzylindole Chemical compound C1=CC2=CC=CC=C2N1CC1=CC=CC=C1 NJZQOCCEDXRQJM-UHFFFAOYSA-N 0.000 description 2
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 2
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DGZTZVQNZUKATJ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-6-methoxy-2-methylindol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 DGZTZVQNZUKATJ-UHFFFAOYSA-N 0.000 description 2
- GHIUCOTZNGACSG-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)C(F)(F)F)=C1 GHIUCOTZNGACSG-UHFFFAOYSA-N 0.000 description 2
- VWLCARAJHNJKAO-UHFFFAOYSA-N 2-[[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 VWLCARAJHNJKAO-UHFFFAOYSA-N 0.000 description 2
- RRLOHUDUPRNMML-UHFFFAOYSA-N 2-methyl-6-(trifluoromethoxy)-1h-indole Chemical compound C1=C(OC(F)(F)F)C=C2NC(C)=CC2=C1 RRLOHUDUPRNMML-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- DDZCDMNRXYRXAZ-UHFFFAOYSA-N 4-(trifluoromethoxy)-1h-indole Chemical class FC(F)(F)OC1=CC=CC2=C1C=CN2 DDZCDMNRXYRXAZ-UHFFFAOYSA-N 0.000 description 2
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- 239000005089 Luciferase Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- 229940126033 PPAR agonist Drugs 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- PGUYGXWLFYYEFI-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]hydrazine Chemical compound NNC1=CC=CC(OC(F)(F)F)=C1 PGUYGXWLFYYEFI-UHFFFAOYSA-N 0.000 description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 231100000304 hepatotoxicity Toxicity 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 108020001756 ligand binding domains Proteins 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 210000005228 liver tissue Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229950004994 meglitinide Drugs 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- ZICRWXFGZCVTBZ-UHFFFAOYSA-N methyl 2-hydroxy-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1O ZICRWXFGZCVTBZ-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 229960004586 rosiglitazone Drugs 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 229960002385 streptomycin sulfate Drugs 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000012134 supernatant fraction Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- UPRLOYNUXQZAPJ-LURJTMIESA-N tert-butyl (2s)-2-hydroxybutanoate Chemical compound CC[C@H](O)C(=O)OC(C)(C)C UPRLOYNUXQZAPJ-LURJTMIESA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229960001641 troglitazone Drugs 0.000 description 2
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 2
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 2
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- MTRYXSFBTALAFQ-QGZVFWFLSA-N (2r)-2-[2-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC=C1O[C@H](C)C(O)=O MTRYXSFBTALAFQ-QGZVFWFLSA-N 0.000 description 1
- OXVFVRNUVQWEPS-OAHLLOKOSA-N (2r)-2-[2-chloro-5-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 OXVFVRNUVQWEPS-OAHLLOKOSA-N 0.000 description 1
- LZBGEEPDFHHWPH-MRXNPFEDSA-N (2r)-2-[2-chloro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=C(Cl)C(O[C@H](C)C(O)=O)=C1 LZBGEEPDFHHWPH-MRXNPFEDSA-N 0.000 description 1
- VYLQLJJDGACHNN-MRXNPFEDSA-N (2r)-2-[2-fluoro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=C(F)C(O[C@H](C)C(O)=O)=C1 VYLQLJJDGACHNN-MRXNPFEDSA-N 0.000 description 1
- GXKCCOHPPSBKJF-HSZRJFAPSA-N (2r)-2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 GXKCCOHPPSBKJF-HSZRJFAPSA-N 0.000 description 1
- LGYGMOFVNHPEFQ-MRXNPFEDSA-N (2r)-2-[3-[[3-(2-chloro-4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound ClC1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 LGYGMOFVNHPEFQ-MRXNPFEDSA-N 0.000 description 1
- BDGXRMGNPNFFND-MRXNPFEDSA-N (2r)-2-[3-[[3-(4-chloro-2-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound COC1=CC(Cl)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 BDGXRMGNPNFFND-MRXNPFEDSA-N 0.000 description 1
- DHUATBAZHILHIC-MRXNPFEDSA-N (2r)-2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 DHUATBAZHILHIC-MRXNPFEDSA-N 0.000 description 1
- JBXHEUHHOADQFM-MRXNPFEDSA-N (2r)-2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 JBXHEUHHOADQFM-MRXNPFEDSA-N 0.000 description 1
- RPAKPTBGCCXKKU-MRXNPFEDSA-N (2r)-2-[3-[[3-(4-fluorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(F)=CC=3)=C2C)=C1 RPAKPTBGCCXKKU-MRXNPFEDSA-N 0.000 description 1
- MVVGRYLUCCOVBG-QGZVFWFLSA-N (2r)-2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(O[C@H](C)C(O)=O)=C1 MVVGRYLUCCOVBG-QGZVFWFLSA-N 0.000 description 1
- GQYVMWYHKZNYQQ-XMMPIXPASA-N (2r)-2-[3-[[3-(6-methoxy-1,2-benzoxazol-3-yl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CC[C@H](C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C4=CC=C(OC)C=C4ON=3)=C2C)=C1 GQYVMWYHKZNYQQ-XMMPIXPASA-N 0.000 description 1
- CJUAETLFYQRYBB-QGZVFWFLSA-N (2r)-2-[4-chloro-3-[(2-methyl-3-phenylsulfanylindol-1-yl)methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C(CN2C3=CC=CC=C3C(SC=3C=CC=CC=3)=C2C)=C1 CJUAETLFYQRYBB-QGZVFWFLSA-N 0.000 description 1
- UVYURVPMIBTGAV-OAHLLOKOSA-N (2r)-2-[4-chloro-3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 UVYURVPMIBTGAV-OAHLLOKOSA-N 0.000 description 1
- FNXFYFQZHVHQIX-OAHLLOKOSA-N (2r)-2-[5-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-fluorophenoxy]propanoic acid Chemical compound C1=C(F)C(O[C@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 FNXFYFQZHVHQIX-OAHLLOKOSA-N 0.000 description 1
- UDXDJXFIZOIXQL-SSEXGKCCSA-N (2r)-2-ethyl-7-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-3,4-dihydrochromene-2-carboxylic acid Chemical compound C([C@](OC1=C2)(CC)C(O)=O)CC1=CC=C2CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(OC)C=C1 UDXDJXFIZOIXQL-SSEXGKCCSA-N 0.000 description 1
- YYYXCMZKYLVQPG-INIZCTEOSA-N (2s)-2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(Cl)C(O[C@@H](C)C(O)=O)=C1 YYYXCMZKYLVQPG-INIZCTEOSA-N 0.000 description 1
- OVDHKMMDXCNAEC-AWEZNQCLSA-N (2s)-2-[2-chloro-5-[[3-(6-chloro-1,2-benzoxazol-3-yl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C4=CC=C(Cl)C=C4ON=3)=C2C)=C1 OVDHKMMDXCNAEC-AWEZNQCLSA-N 0.000 description 1
- VYLQLJJDGACHNN-INIZCTEOSA-N (2s)-2-[2-fluoro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=C(F)C(O[C@@H](C)C(O)=O)=C1 VYLQLJJDGACHNN-INIZCTEOSA-N 0.000 description 1
- IUCYURPIQQNGNP-AWEZNQCLSA-N (2s)-2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]-5-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC(F)=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 IUCYURPIQQNGNP-AWEZNQCLSA-N 0.000 description 1
- YJVISMHLSZOVTH-HNNXBMFYSA-N (2s)-2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 YJVISMHLSZOVTH-HNNXBMFYSA-N 0.000 description 1
- JBXHEUHHOADQFM-INIZCTEOSA-N (2s)-2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 JBXHEUHHOADQFM-INIZCTEOSA-N 0.000 description 1
- HNEYLYWCHIFCBH-SFHVURJKSA-N (2s)-2-[3-[[3-(4-methoxybenzoyl)-2-methylindol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=CC=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 HNEYLYWCHIFCBH-SFHVURJKSA-N 0.000 description 1
- MEPFPFGMQXDYDS-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxyphenoxy)-2-methyl-4-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=C(C=CC=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 MEPFPFGMQXDYDS-KRWDZBQOSA-N 0.000 description 1
- MVVGRYLUCCOVBG-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 MVVGRYLUCCOVBG-KRWDZBQOSA-N 0.000 description 1
- LEUKBXHFVSLKSQ-KRWDZBQOSA-N (2s)-2-[3-[[3-(4-methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(O[C@@H](C)C(O)=O)=C1 LEUKBXHFVSLKSQ-KRWDZBQOSA-N 0.000 description 1
- PMQGEGPWRZRLNC-INIZCTEOSA-N (2s)-2-[4-chloro-3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC(O[C@@H](C)C(O)=O)=CC=C1Cl PMQGEGPWRZRLNC-INIZCTEOSA-N 0.000 description 1
- CFIDCCBKNKLRHP-AWEZNQCLSA-N (2s)-2-[5-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]-2-fluorophenoxy]propanoic acid Chemical compound C1=C(F)C(O[C@@H](C)C(O)=O)=CC(N2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 CFIDCCBKNKLRHP-AWEZNQCLSA-N 0.000 description 1
- FNXFYFQZHVHQIX-HNNXBMFYSA-N (2s)-2-[5-[[3-(4-chlorophenyl)sulfanyl-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-fluorophenoxy]propanoic acid Chemical compound C1=C(F)C(O[C@@H](C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(SC=3C=CC(Cl)=CC=3)=C2C)=C1 FNXFYFQZHVHQIX-HNNXBMFYSA-N 0.000 description 1
- QJQYAWXIDUHOOF-UHFFFAOYSA-N (4-chlorophenyl)-[2-methyl-6-(trifluoromethoxy)-1h-indol-3-yl]methanone Chemical compound CC=1NC2=CC(OC(F)(F)F)=CC=C2C=1C(=O)C1=CC=C(Cl)C=C1 QJQYAWXIDUHOOF-UHFFFAOYSA-N 0.000 description 1
- LEIIDUGHZFUWMT-LFYBBSHMSA-N (e)-3-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]prop-2-enoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(\C=C\C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 LEIIDUGHZFUWMT-LFYBBSHMSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical compound CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 1
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
- ZKSOJQDNSNJIQW-UHFFFAOYSA-N 1-(bromomethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CBr)=C1 ZKSOJQDNSNJIQW-UHFFFAOYSA-N 0.000 description 1
- GPNGIGHFMOHMOO-UHFFFAOYSA-N 1-oxothiolan-3-one Chemical group O=C1CCS(=O)C1 GPNGIGHFMOHMOO-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ADUPGIQCDSDDIZ-UHFFFAOYSA-N 2-[2-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC=C1OC(C)(C)C(O)=O ADUPGIQCDSDDIZ-UHFFFAOYSA-N 0.000 description 1
- OXVFVRNUVQWEPS-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 OXVFVRNUVQWEPS-UHFFFAOYSA-N 0.000 description 1
- GAELHUVKAWUQLF-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpentanoic acid Chemical compound C1=C(Cl)C(OC(C)(CCC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 GAELHUVKAWUQLF-UHFFFAOYSA-N 0.000 description 1
- MOYYTWDBXYZIBK-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=C(Cl)C(OC(C(C)C)C(O)=O)=C1 MOYYTWDBXYZIBK-UHFFFAOYSA-N 0.000 description 1
- IBDNWMNLBLNUMY-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound C1=C(Cl)C(OC(C)(CC)C(O)=O)=CC(CN2C3=CC(=CC=C3C(OC=3C=CC(OC)=CC=3)=C2C)C(F)(F)F)=C1 IBDNWMNLBLNUMY-UHFFFAOYSA-N 0.000 description 1
- OGDLZMOWAVUNHU-UHFFFAOYSA-N 2-[2-chloro-5-[[3-(4-methoxyphenyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound C1=C(Cl)C(OC(CC)C(O)=O)=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C=3C=CC(OC)=CC=3)=C2C(F)(F)F)=C1 OGDLZMOWAVUNHU-UHFFFAOYSA-N 0.000 description 1
- TWQAHTMYGUDMAR-UHFFFAOYSA-N 2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]-5-fluorophenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=C(F)C=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 TWQAHTMYGUDMAR-UHFFFAOYSA-N 0.000 description 1
- AORGDTLKZTUFRX-UHFFFAOYSA-N 2-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 AORGDTLKZTUFRX-UHFFFAOYSA-N 0.000 description 1
- BUBWKCLVNDSHFC-UHFFFAOYSA-N 2-[3-[3-(6-ethoxypyridine-3-carbonyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=NC(OCC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(OC(C)(C)C(O)=O)=C1 BUBWKCLVNDSHFC-UHFFFAOYSA-N 0.000 description 1
- SUBJAJAOVHMPAV-UHFFFAOYSA-N 2-[3-[4-[(3-phenyl-7-propyl-1,2-benzoxazol-6-yl)oxy]butoxy]phenyl]acetic acid Chemical compound C1=CC=2C(C=3C=CC=CC=3)=NOC=2C(CCC)=C1OCCCCOC1=CC=CC(CC(O)=O)=C1 SUBJAJAOVHMPAV-UHFFFAOYSA-N 0.000 description 1
- GOSMZBNFNBEGPK-UHFFFAOYSA-N 2-[3-[[3-(2,4-dichlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3,3,3-trifluoropropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C(O)=O)C(F)(F)F)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1Cl GOSMZBNFNBEGPK-UHFFFAOYSA-N 0.000 description 1
- KDNBPVKYTFDSAT-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpentanoic acid Chemical compound CCCC(C)(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(Cl)=CC=3)=C2C)=C1 KDNBPVKYTFDSAT-UHFFFAOYSA-N 0.000 description 1
- UARATJHDPGSYDL-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-4,4,4-trifluorobutanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(CC(F)(F)F)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 UARATJHDPGSYDL-UHFFFAOYSA-N 0.000 description 1
- SQXYPBDVRILOBL-UHFFFAOYSA-N 2-[3-[[3-(4-chlorobenzoyl)-2-propyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C(C)C)C(O)=O)C=CC=2)C(CCC)=C1C(=O)C1=CC=C(Cl)C=C1 SQXYPBDVRILOBL-UHFFFAOYSA-N 0.000 description 1
- XZKUIKHRAXNDFP-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-4-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC=CC(OC(F)(F)F)=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 XZKUIKHRAXNDFP-UHFFFAOYSA-N 0.000 description 1
- YAEOMQXWEFNYHM-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1OC1=CC=C(Cl)C=C1 YAEOMQXWEFNYHM-UHFFFAOYSA-N 0.000 description 1
- MVJARISIPDSITL-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 MVJARISIPDSITL-UHFFFAOYSA-N 0.000 description 1
- JRTOEHXESHPTIZ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C12=CC=C(C(F)(F)F)C=C2N(CC=2C=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1OC1=CC=C(Cl)C=C1 JRTOEHXESHPTIZ-UHFFFAOYSA-N 0.000 description 1
- LWCDJIZVNNXFPJ-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenoxy)-6-fluoro-2-methylindol-1-yl]methyl]phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC(CN2C3=CC(F)=CC=C3C(OC=3C=CC(Cl)=CC=3)=C2C)=C1 LWCDJIZVNNXFPJ-UHFFFAOYSA-N 0.000 description 1
- IBCYKZKNTSVLGG-UHFFFAOYSA-N 2-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenoxy]-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)OC1=CC=CC(CN2C3=CC(OC(F)(F)F)=CC=C3C(C(=O)C=3C=CC(OC)=CC=3)=C2C)=C1 IBCYKZKNTSVLGG-UHFFFAOYSA-N 0.000 description 1
- FIERNBNZDRLQQK-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-4-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=C(C=CC=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(OC(C(C)C)C(O)=O)=C1 FIERNBNZDRLQQK-UHFFFAOYSA-N 0.000 description 1
- LICUNCUDGDUWGT-UHFFFAOYSA-N 2-[3-[[3-(4-methoxyphenoxy)-2-methyl-6-(trifluoromethyl)indol-1-yl]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=C(C=C11)C(F)(F)F)=C(C)N1CC1=CC=CC(OC(C)(C)C(O)=O)=C1 LICUNCUDGDUWGT-UHFFFAOYSA-N 0.000 description 1
- HBSUETPUJSVLGL-UHFFFAOYSA-N 2-[6-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]pyridin-2-yl]oxy-2-methylpropanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2N=C(OC(C)(C)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 HBSUETPUJSVLGL-UHFFFAOYSA-N 0.000 description 1
- KTZNLSNSBFSGOQ-UHFFFAOYSA-N 2-[6-[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]pyridin-2-yl]oxy-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1C1=CC=CC(OC(C)(C)C(O)=O)=N1 KTZNLSNSBFSGOQ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- ZHJQBUAWFQYNRI-UHFFFAOYSA-N 2-ethyl-5-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-3h-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(CC)(C(O)=O)CC2=CC=1CN(C1=CC(OC(F)(F)F)=CC=C11)C(C)=C1C(=O)C1=CC=C(OC)C=C1 ZHJQBUAWFQYNRI-UHFFFAOYSA-N 0.000 description 1
- DLGIQFOQOBITLV-UHFFFAOYSA-N 2-methyl-2-[3-[2-methyl-3-(quinoline-2-carbonyl)-6-(trifluoromethoxy)indol-1-yl]phenoxy]propanoic acid Chemical compound CC1=C(C(=O)C=2N=C3C=CC=CC3=CC=2)C2=CC=C(OC(F)(F)F)C=C2N1C1=CC=CC(OC(C)(C)C(O)=O)=C1 DLGIQFOQOBITLV-UHFFFAOYSA-N 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- WBPAQKQBUKYCJS-ZCFIWIBFSA-N 2-methylpropyl (2r)-2-hydroxypropanoate Chemical compound CC(C)COC(=O)[C@@H](C)O WBPAQKQBUKYCJS-ZCFIWIBFSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- DKWVKUXVQYGWKH-UHFFFAOYSA-N 3-[3-[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(C=2C=C(CC(OCC(F)(F)F)C(O)=O)C=CC=2)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 DKWVKUXVQYGWKH-UHFFFAOYSA-N 0.000 description 1
- KQMNQTKQVFFLOE-UHFFFAOYSA-N 3-[3-[[3-(4-chlorophenoxy)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C(CC(OCC(F)(F)F)C(O)=O)C=CC=2)C(C)=C1OC1=CC=C(Cl)C=C1 KQMNQTKQVFFLOE-UHFFFAOYSA-N 0.000 description 1
- WUROWOKBGVSMEK-UHFFFAOYSA-N 3-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(CC(OCC(F)(F)F)C(O)=O)=C1 WUROWOKBGVSMEK-UHFFFAOYSA-N 0.000 description 1
- KLWIUPSSLQAPIS-UHFFFAOYSA-N 3-[3-[[3-(4-methoxybenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]phenyl]-2-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C1=CC=C(OC(F)(F)F)C=C11)=C(C)N1CC1=CC=CC(CC(C(O)=O)C=2C=CC=CC=2)=C1 KLWIUPSSLQAPIS-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- STDKZZIKAJFATG-UHFFFAOYSA-N 5-benzyl-1,3-thiazolidine-2,4-dione Chemical class S1C(=O)NC(=O)C1CC1=CC=CC=C1 STDKZZIKAJFATG-UHFFFAOYSA-N 0.000 description 1
- DODJNBPQUZSJKO-UHFFFAOYSA-N 6-(trifluoromethoxy)-1h-indole Chemical class FC(F)(F)OC1=CC=C2C=CNC2=C1 DODJNBPQUZSJKO-UHFFFAOYSA-N 0.000 description 1
- SJNUIXDIQRRYDL-UHFFFAOYSA-N 6-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)indol-1-yl]methyl]-2-methyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C12=CC=C(OC(F)(F)F)C=C2N(CC=2C=C3CCC(C)(OC3=CC=2)C(O)=O)C(C)=C1C(=O)C1=CC=C(Cl)C=C1 SJNUIXDIQRRYDL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- 208000011732 Abnormal glucose homeostasis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010071619 Apolipoproteins Proteins 0.000 description 1
- 102000007592 Apolipoproteins Human genes 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 101150095408 CNMD gene Proteins 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008583 Chloroma Diseases 0.000 description 1
- 101100007328 Cocos nucifera COS-1 gene Proteins 0.000 description 1
- 108020004635 Complementary DNA Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 206010070901 Diabetic dyslipidaemia Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000002464 Galactosidases Human genes 0.000 description 1
- 108010093031 Galactosidases Proteins 0.000 description 1
- 108010001515 Galectin 4 Proteins 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000003746 Insulin Receptor Human genes 0.000 description 1
- 108010001127 Insulin Receptor Proteins 0.000 description 1
- 229940122355 Insulin sensitizer Drugs 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 101100355616 Mus musculus Chml gene Proteins 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 108010015181 PPAR delta Proteins 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000006601 Thymidine Kinase Human genes 0.000 description 1
- 108020004440 Thymidine kinase Proteins 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- KQXZVSQCMVKMBK-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]hydrazine;hydrochloride Chemical compound Cl.NNC1=CC=C(OC(F)(F)F)C=C1 KQXZVSQCMVKMBK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 108700010039 chimeric receptor Proteins 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 230000014101 glucose homeostasis Effects 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 238000007410 oral glucose tolerance test Methods 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000003614 peroxisome proliferator Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical group ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000000276 sedentary effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- ADURZWBRKMHZSG-UHFFFAOYSA-M sodium;n,n-dimethylformamide;hydroxide Chemical compound [OH-].[Na+].CN(C)C=O ADURZWBRKMHZSG-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UPRLOYNUXQZAPJ-ZCFIWIBFSA-N tert-butyl (2r)-2-hydroxybutanoate Chemical compound CC[C@@H](O)C(=O)OC(C)(C)C UPRLOYNUXQZAPJ-ZCFIWIBFSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 101150069452 z gene Proteins 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40674102P | 2002-08-29 | 2002-08-29 | |
| US44067203P | 2003-01-17 | 2003-01-17 | |
| PCT/US2003/026677 WO2004020408A1 (en) | 2002-08-29 | 2003-08-27 | Indoles having anti-diabetic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ538031A true NZ538031A (en) | 2007-10-26 |
Family
ID=31981430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ538031A NZ538031A (en) | 2002-08-29 | 2003-08-27 | Indoles having anti-diabetic activity |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7186746B2 (https=) |
| JP (1) | JP4377815B2 (https=) |
| KR (1) | KR20050057074A (https=) |
| CN (1) | CN100457730C (https=) |
| AU (1) | AU2003265681A1 (https=) |
| BR (1) | BR0313825A (https=) |
| CA (1) | CA2495943C (https=) |
| DE (1) | DE60332125D1 (https=) |
| DK (1) | DK1537078T3 (https=) |
| EC (1) | ECSP055632A (https=) |
| ES (1) | ES2342596T3 (https=) |
| HR (1) | HRP20050181A2 (https=) |
| IL (1) | IL166764A0 (https=) |
| IS (1) | IS7680A (https=) |
| MA (1) | MA27396A1 (https=) |
| MX (1) | MXPA05002303A (https=) |
| NO (1) | NO20051546L (https=) |
| NZ (1) | NZ538031A (https=) |
| PL (1) | PL375302A1 (https=) |
| PT (1) | PT1537078E (https=) |
| RU (1) | RU2328483C2 (https=) |
| WO (2) | WO2004020408A1 (https=) |
Families Citing this family (138)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004020408A1 (en) * | 2002-08-29 | 2004-03-11 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| WO2004019869A2 (en) * | 2002-08-29 | 2004-03-11 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| MXPA05007485A (es) | 2003-01-14 | 2006-01-30 | Arena Pharm Inc | Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia. |
| BRPI0409447A (pt) * | 2003-04-14 | 2006-04-18 | Inst For Pharm Discovery Inc | ácidos fenilalcanóicos substituìdos |
| CN1812977A (zh) | 2003-04-30 | 2006-08-02 | 药物研发有限责任公司 | 取代羧酸 |
| US7132426B2 (en) | 2003-07-14 | 2006-11-07 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| EP1744747A4 (en) * | 2004-04-26 | 2009-12-02 | Univ Vanderbilt | INDIC ACID AND INDULECTIC ACID DERIVATIVES AS THERAPEUTIC ACTIVITIES WITH REDUCED GASTROINTESTINAL TOXICITY |
| EP1758856A2 (en) * | 2004-05-04 | 2007-03-07 | Novo Nordisk A/S | Indole derivatives for the treatment of obesity |
| US20080076810A1 (en) * | 2004-05-28 | 2008-03-27 | Weiguo Lui | Benzoureas Having Anti-Diabetic Activity |
| BRPI0511676A (pt) * | 2004-05-29 | 2008-01-08 | 7Tm Pharma As | uso medicinal de ligandos receptores |
| EP1765329A2 (en) | 2004-07-02 | 2007-03-28 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| AU2005266337A1 (en) | 2004-07-30 | 2006-02-02 | Laboratorios Salvat, S.A. | Tyrosine derivatives as PPAR-gamma-modulators |
| WO2006060535A2 (en) * | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Indole derivatives for use as ppar active compounds |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| JPWO2006075638A1 (ja) * | 2005-01-14 | 2008-06-12 | 大日本住友製薬株式会社 | 新規ヘテロアリール誘導体 |
| BRPI0519774A2 (pt) * | 2005-01-19 | 2009-02-10 | Biolipox Ab | composto ou um sal farmaceuticamente aceitÁvel do mesmo, formulaÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel do mesmo, mÉtodo de tratamento de uma doenÇa em que inibiÇço da atividade de um membro da famÍlia mapeg É desejada e/ou necessÁria, produto combinado, e, processo para a preparaÇço de um composto |
| WO2006093142A1 (ja) * | 2005-03-01 | 2006-09-08 | Kowa Co., Ltd. | 光学活性ppar活性化化合物中間体及びその製造法 |
| CN101128441A (zh) | 2005-03-04 | 2008-02-20 | 默克公司 | 具有抗糖尿病活性的稠合芳香化合物 |
| EP1858844A4 (en) | 2005-03-10 | 2009-04-22 | Merck & Co Inc | NEW CRYSTALLINE FORMS OF ANTIDIABETIC COMPOUNDS |
| EP1924557A2 (en) * | 2005-09-16 | 2008-05-28 | Serenex, Inc. | Carbazole derivatives |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US8399666B2 (en) | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| US7736624B2 (en) | 2006-06-19 | 2010-06-15 | Univ Vanderbilt | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
| TW200821284A (en) * | 2006-10-03 | 2008-05-16 | Merck & Co Inc | Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use |
| KR101568799B1 (ko) | 2007-01-26 | 2015-11-12 | 카네크 파마 인코포레이티드 | 융합된 방향족 ptp-1b 억제제 |
| PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| US8338458B2 (en) | 2007-05-07 | 2012-12-25 | Merck Sharp & Dohme Corp. | Method of treatment using fused aromatic compounds having anti-diabetic activity |
| RU2361581C2 (ru) | 2007-09-14 | 2009-07-20 | Закрытое Акционерное Общество "Мастерклон" | Фармацевтическая композиция, обладающая противодиабетической, гиполипидемической, гипогликемической и гипохолестеринемической активностью, способ ее получения и способы лечения указанных заболеваний |
| TW200920369A (en) | 2007-10-26 | 2009-05-16 | Amira Pharmaceuticals Inc | 5-lipoxygenase activating protein (flap) inhibitor |
| JP5791500B2 (ja) | 2008-05-23 | 2015-10-07 | パンミラ ファーマシューティカルズ,エルエルシー. | 5−リポキシゲナーゼ活性化タンパク質阻害剤 |
| WO2010001869A1 (ja) * | 2008-06-30 | 2010-01-07 | 武田薬品工業株式会社 | 4置換ベンゼン化合物およびその用途 |
| TWI532497B (zh) * | 2008-08-11 | 2016-05-11 | 曼凱公司 | 超快起作用胰島素之用途 |
| US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| JO2870B1 (en) | 2008-11-13 | 2015-03-15 | ميرك شارب اند دوهم كورب | Amino Tetra Hydro Pirans as Inhibitors of Peptide Dipeptide IV for the Treatment or Prevention of Diabetes |
| JP5514831B2 (ja) | 2008-11-17 | 2014-06-04 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病の治療のための置換二環式アミン |
| RU2408579C2 (ru) * | 2008-12-31 | 2011-01-10 | Федеральное государственное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" (ЮФУ) | Гидрогалогениды n-[2-(1-алкил-1н-индол-3-ил)-1-(4-алкилпиперазин-1-карбонил)винил]-2-фторбензамида, обладающие местноанестезирующей и антиаритмической активностью |
| TW201028414A (en) | 2009-01-16 | 2010-08-01 | Merck Sharp & Dohme | Oxadiazole beta carboline derivatives as antidiabetic compounds |
| AU2010206789A1 (en) | 2009-01-23 | 2011-07-28 | Merck Sharp & Dohme Corp. | Bridged and fused antidiabetic compounds |
| WO2010085525A1 (en) | 2009-01-23 | 2010-07-29 | Schering Corporation | Bridged and fused heterocyclic antidiabetic compounds |
| AR075051A1 (es) | 2009-02-05 | 2011-03-02 | Schering Corp | Compuestos antidiabeticos que contienen ftalazina |
| WO2011011506A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Spirocyclic oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| CA2768577A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| EP2464228B1 (en) | 2009-08-13 | 2017-12-06 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| CA2771352A1 (en) | 2009-09-02 | 2011-03-10 | Merck Sharp & Dohme Corp. | Aminotetrahydropyrans as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes |
| CN102695414A (zh) | 2010-01-15 | 2012-09-26 | 默沙东公司 | 作为抗糖尿病化合物的噁二唑β-咔啉衍生物 |
| MX336731B (es) | 2010-01-28 | 2016-01-28 | Harvard College | Composiciones y metodos para potenciar la actividad de proteasoma. |
| US8853212B2 (en) | 2010-02-22 | 2014-10-07 | Merck Sharp & Dohme Corp | Substituted aminotetrahydrothiopyrans and derivatives thereof as dipeptidyl peptidase-IV inhibitors for the treatment of diabetes |
| JP2013100235A (ja) * | 2010-03-08 | 2013-05-23 | Dainippon Sumitomo Pharma Co Ltd | 新規インドール誘導体 |
| EP2563764B1 (en) | 2010-04-26 | 2015-02-25 | Merck Sharp & Dohme Corp. | Novel spiropiperidine prolylcarboxypeptidase inhibitors |
| US9365539B2 (en) | 2010-05-11 | 2016-06-14 | Merck Sharp & Dohme Corp. | Prolylcarboxypeptidase inhibitors |
| WO2011146358A1 (en) | 2010-05-21 | 2011-11-24 | Merck Sharp & Dohme Corp. | Substituted seven-membered heterocyclic compounds as dipeptidyl peptidase-iv inhibitors for the treatment of diabetes |
| US9006268B2 (en) | 2010-06-11 | 2015-04-14 | Merck Sharp & Dohme Corp. | Prolylcarboxypeptidase inhibitors |
| US8742110B2 (en) | 2010-08-18 | 2014-06-03 | Merck Sharp & Dohme Corp. | Spiroxazolidinone compounds |
| US9000025B2 (en) | 2010-08-20 | 2015-04-07 | Amira Pharmaceuticals, Inc. | Autotaxin inhibitors and uses thereof |
| PH12013500547A1 (en) | 2010-09-22 | 2013-06-10 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| US9108920B2 (en) | 2010-10-29 | 2015-08-18 | Merck Sharp & Dohme Corp. | Diazeniumdiolate heterocyclic derivatives |
| RU2598842C2 (ru) | 2011-01-20 | 2016-09-27 | Мерк Шарп Энд Домэ Корп. | Антагонисты рецептора минералокортикоидов |
| JO3350B1 (ar) | 2011-03-07 | 2019-03-13 | Merck Sharp & Dohme | مشتقات حلقية غير متجانسة محتوية على مجموعات أمينو أولية ومركبات داي أزينيومديولات |
| WO2012138845A1 (en) | 2011-04-08 | 2012-10-11 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| WO2012139495A1 (en) | 2011-04-13 | 2012-10-18 | Merck Sharp & Dohme Corp. | Mineralocorticoid receptor antagonists |
| US9272987B2 (en) | 2011-05-02 | 2016-03-01 | Merck Sharp & Dohme Corp. | Diazeniumdiolate cyclohexyl derivatives |
| DK2707101T3 (da) * | 2011-05-12 | 2019-05-13 | Proteostasis Therapeutics Inc | Proteostaseregulatorer |
| US9260416B2 (en) | 2011-05-27 | 2016-02-16 | Amira Pharmaceuticals, Inc. | Heterocyclic autotaxin inhibitors and uses thereof |
| US20140088124A1 (en) | 2011-06-02 | 2014-03-27 | Robert J. DeVita | Imidazole derivatives |
| US9006228B2 (en) | 2011-06-16 | 2015-04-14 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds, and methods of treatment |
| US9422266B2 (en) | 2011-09-30 | 2016-08-23 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| EP2765859B1 (en) | 2011-10-13 | 2017-01-18 | Merck Sharp & Dohme Corp. | Mineralocorticoid receptor antagonists |
| WO2013059245A1 (en) | 2011-10-17 | 2013-04-25 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
| US9018200B2 (en) | 2011-10-24 | 2015-04-28 | Merck Sharp & Dohme Corp. | Substituted piperidinyl compounds useful as GPR119 agonists |
| JO3210B1 (ar) | 2011-10-28 | 2018-03-08 | Merck Sharp & Dohme | مثبط منصهر لبروتين نقل الكوليسترليستير اوكسازوليدينون ثمائي الحلقة |
| WO2013068328A1 (en) | 2011-11-07 | 2013-05-16 | Intervet International B.V. | Bicyclo [2.2.2] octan-1-ylcarboxylic acid compounds as dgat-1 inhibitors |
| WO2013068439A1 (en) | 2011-11-09 | 2013-05-16 | Intervet International B.V. | 4-amino-5-oxo-7,8-dihydropyrimido[5, 4 -f] [1, 4] oxazepine compounds as dgat1 inhibitors |
| AU2012339870B2 (en) | 2011-11-15 | 2017-06-29 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds useful as GPR119 agonists |
| WO2013122920A1 (en) | 2012-02-17 | 2013-08-22 | Merck Sharp & Dohme Corp. | Dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes |
| JP2015516965A (ja) * | 2012-04-03 | 2015-06-18 | アポセンス リミテッドAposense Ltd. | 診断指標及び治療指標のための新規な標的指向性薬剤 |
| WO2013155600A1 (en) | 2012-04-16 | 2013-10-24 | Kaneq Pharma | Fused aromatic phosphonate derivatives as precursors to ptp-1b inhibitors |
| EP2874622A4 (en) | 2012-07-23 | 2015-12-30 | Merck Sharp & Dohme | TREATMENT OF DIABETES WITH DIPEPTIDYLPEPTIDASE IV INHIBITORS |
| EP2931734B1 (en) | 2012-12-17 | 2020-12-02 | Merck Sharp & Dohme Corp. | Novel glucokinase activator compounds, compositions containing such compounds, and methods of treatment |
| US9717714B2 (en) | 2012-12-19 | 2017-08-01 | Merck Sharp & Dohme Corp. | Spirocyclic CETP inhibitors |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| US9714240B2 (en) | 2013-09-17 | 2017-07-25 | Pharmakea, Inc. | Vinyl autotaxin inhibitor compounds |
| JP2016530210A (ja) | 2013-09-17 | 2016-09-29 | ファーマケア,インク. | ヘテロ環式ビニルオートタキシン阻害剤化合物 |
| JP2016531874A (ja) | 2013-09-26 | 2016-10-13 | ファーマケア,インク. | オートタキシン阻害剤化合物 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| KR102515248B1 (ko) | 2013-11-22 | 2023-03-29 | 사브레 테라퓨틱스 엘엘씨 | 오토탁신 억제제 화합물 |
| WO2015089809A1 (en) | 2013-12-19 | 2015-06-25 | Merck Sharp & Dohme Corp. | Antidiabetic substituted heteroaryl compounds |
| WO2015112465A1 (en) | 2014-01-24 | 2015-07-30 | Merck Sharp & Dohme Corp. | Isoquinoline derivatives as mgat2 inhibitors |
| RU2679619C2 (ru) * | 2014-05-20 | 2019-02-12 | Раквалиа Фарма Инк. | Солевое производное бензизоксазола |
| WO2015176267A1 (en) | 2014-05-22 | 2015-11-26 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2016018729A1 (en) | 2014-07-29 | 2016-02-04 | Merck Sharp & Dohme Corp. | Monocyclic isoxazolines as inhibitors of cholesterol ester transfer protein |
| WO2016022446A1 (en) | 2014-08-08 | 2016-02-11 | Merck Sharp & Dohme Corp. | [5,6]-fused bicyclic antidiabetic compounds |
| US10662171B2 (en) | 2014-08-08 | 2020-05-26 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| US10968193B2 (en) | 2014-08-08 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| CR20170164A (es) | 2014-10-24 | 2017-08-29 | Merck Sharp & Dohme | Coagonistas de los receptores de glucagón y de glp-1 |
| TW201625635A (zh) | 2014-11-21 | 2016-07-16 | 默沙東藥廠 | 作為可溶性鳥苷酸環化酶活化劑之三唑并吡基衍生物 |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| MX2017015225A (es) | 2015-05-27 | 2018-02-19 | Pharmakea Inc | Inhibidores de la autotaxina y sus usos. |
| EP3303342B1 (en) | 2015-05-27 | 2021-03-17 | Merck Sharp & Dohme Corp. | Imidazo-pyrazinyl derivatives useful as soluble guanylate cyclase activators |
| WO2016191335A1 (en) | 2015-05-28 | 2016-12-01 | Merck Sharp & Dohme Corp. | Imidazo-pyrazinyl derivatives useful as soluble guanylate cyclase activators |
| EP3939965A1 (en) | 2015-06-22 | 2022-01-19 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in sipi receptor-associated disorders |
| EP3322420B1 (en) | 2015-07-13 | 2021-12-29 | Merck Sharp & Dohme Corp. | Bicyclic heterocycles as inhibitors of cholesterol ester transfer protein |
| EP3359191A4 (en) | 2015-10-05 | 2019-05-29 | Merck Sharp & Dohme Corp. | ANTIBODY PEPTIDE CONJUGATES WITH AGONISTEACTIVITY ON GLUCAGON RECEPTORS AND GLUCAGON-LIKE PEPTIDE-1 |
| KR102667386B1 (ko) * | 2015-10-07 | 2024-05-21 | 미토브리지, 인크. | Ppar 효능제, 화합물, 제약 조성물, 및 그의 사용 방법 |
| EP3383869B1 (en) | 2015-11-30 | 2023-06-28 | Merck Sharp & Dohme LLC | Aryl sulfonamides as blt1 antagonists |
| WO2017095724A1 (en) | 2015-11-30 | 2017-06-08 | Merck Sharp & Dohme Corp. | Aryl sulfonamides as blt1 antagonists |
| WO2017107052A1 (en) | 2015-12-22 | 2017-06-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase stimulators |
| CN107286158A (zh) * | 2016-03-30 | 2017-10-24 | 中国科学院上海药物研究所 | 苯基[a]吲哚[2,3-g]并喹嗪类化合物、其制备方法、药物组合物及其应用 |
| BR112018069930B1 (pt) | 2016-04-13 | 2024-02-20 | Mitobridge, Inc | Compostos agonistas de ppar, uso dos mesmos e composição farmacêutica |
| WO2017197555A1 (en) | 2016-05-16 | 2017-11-23 | Merck Sharp & Dohme Corp. | Fused pyrazine derivatives useful as soluble guanylate cyclase stimulators |
| WO2017201683A1 (en) | 2016-05-25 | 2017-11-30 | Merck Sharp & Dohme Corp. | Substituted tetrahydroisoquinoline compounds useful as gpr120 agonists |
| WO2018034918A1 (en) | 2016-08-15 | 2018-02-22 | Merck Sharp & Dohme Corp. | Compounds useful for altering the levels of bile acids for the treatment of diabetes and cardiometabolic disease |
| EP3496715B1 (en) | 2016-08-15 | 2021-11-03 | Merck Sharp & Dohme Corp. | Compounds useful for altering the levels of bile acids for the treatment of diabetes and cardiometabolic disease |
| US11008313B2 (en) | 2016-09-20 | 2021-05-18 | Merck Sharp & Dohme Corp. | Substituted 1-methyl-1,2,3,4-tetrahydroisoquinoline molecules as PCSK9 allosteric binders |
| WO2018093698A1 (en) | 2016-11-18 | 2018-05-24 | Merck Sharp & Dohme Corp. | Indole derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| AU2017360939B2 (en) | 2016-11-18 | 2022-03-03 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| WO2018107415A1 (en) | 2016-12-15 | 2018-06-21 | Merck Sharp & Dohme Corp. | Hydroxy isoxazole compounds useful as gpr120 agonists |
| MA47504A (fr) | 2017-02-16 | 2019-12-25 | Arena Pharm Inc | Composés et méthodes de traitement de l'angiocholite biliaire primitive |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| IL279363B2 (en) | 2018-06-21 | 2025-12-01 | Merck Sharp & Dohme | Pcsk9 antagonist compounds |
| US12281109B2 (en) | 2019-04-04 | 2025-04-22 | Merck Sharp & Dohme Llc | Inhibitors of histone deacetylase-3 useful for the treatment of cancer, inflammation, neurodegeneration diseases and diabetes |
| WO2020236688A1 (en) | 2019-05-22 | 2020-11-26 | Merck Sharp & Dohme Corp. | Natriuretic peptide receptor a agonists useful for the treatment of cardiometabolic diseases, kidney disease and diabetes |
| EP3972589B1 (en) | 2019-05-22 | 2024-07-03 | Merck Sharp & Dohme LLC | Natriuretic peptide receptor a agonists useful for the treatment of cardiometabolic diseases, kidney disease and diabetes |
| EP4021919A1 (en) | 2019-08-30 | 2022-07-06 | Merck Sharp & Dohme Corp. | Pcsk9 antagonist compounds |
| EP3842061A1 (en) | 2019-12-23 | 2021-06-30 | Merck Sharp & Dohme Corp. | Stapled triazole co-agonists of the glucagon and glp-1 receptors |
| EP3842060A1 (en) | 2019-12-23 | 2021-06-30 | Merck Sharp & Dohme Corp. | Stapled lactam co-agonists of the glucagon and glp-1 receptors |
| EP3842449A1 (en) | 2019-12-23 | 2021-06-30 | Merck Sharp & Dohme Corp. | Stapled olefin co-agonists of the glucagon and glp-1 receptors |
| PY2121402A (es) | 2020-03-16 | 2022-08-09 | Norvatis Ag | Derivados de biarilo como inhibidores de la interacción proteína-proteína de yap/taz-tead |
| EP4153584A1 (en) | 2020-05-18 | 2023-03-29 | Merck Sharp & Dohme LLC | Novel diacylglyceride o-acyltransferase 2 inhibitors |
| EP4225735A1 (en) | 2020-10-08 | 2023-08-16 | Merck Sharp & Dohme LLC | Preparation of oxindole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| WO2023023245A1 (en) | 2021-08-19 | 2023-02-23 | Merck Sharp & Dohme Llc | Compounds for treating conditions related to pcsk9 activity |
| CN119866342A (zh) | 2022-06-15 | 2025-04-22 | 默沙东有限责任公司 | 用于捕获白介素-1β的环肽 |
| AR131250A1 (es) | 2022-12-02 | 2025-02-26 | Merck Sharp & Dohme Llc | Preparación de derivados condensados de azol como nuevos inhibidores de la diacilglicerol o-aciltransferasa 2 |
| CN121816339A (zh) * | 2023-09-19 | 2026-04-07 | 广东横琴新创益生物医药有限公司 | 一种六元并五元稠环衍生物及其制备方法和应用 |
| US20250152658A1 (en) | 2023-11-14 | 2025-05-15 | Merck Sharp & Dohme Llc | Cyclic peptide for trapping interleukin-1 beta |
| TW202542176A (zh) | 2023-12-15 | 2025-11-01 | 美商默沙東有限責任公司 | 用於治療動脈粥樣硬化及發炎病症之環狀肽IL-1β捕捉劑 |
| WO2026019977A1 (en) | 2024-07-19 | 2026-01-22 | Merck Sharp & Dohme Llc | Pyrrolopyridazine vegfr inhibitors |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5686481A (en) * | 1993-12-21 | 1997-11-11 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
| US5482960A (en) * | 1994-11-14 | 1996-01-09 | Warner-Lambert Company | Nonpeptide endothelin antagonists |
| FI974437A7 (fi) * | 1995-06-06 | 1997-12-05 | Pfizer | Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogee nifosforylaasi-inhibiittoreina |
| EP0922028A1 (en) | 1996-08-26 | 1999-06-16 | Genetics Institute, Inc. | Inhibitors of phospholipase enzymes |
| EE200000488A (et) | 1998-02-25 | 2002-02-15 | Genetics Institute, Inc. | Fosfolipaasensüümide inhibiitorid ja farmatseutilised kompositsioonid |
| EE200000486A (et) | 1998-02-25 | 2002-02-15 | Genetics Institute, Inc. | Fosfolipaasensüümide inhibiitorid, neid sisaldav farmatseutiline kompositsioon ning meetod põletikulise reaktsiooni raviks imetajal |
| EP1062216A1 (en) | 1998-02-25 | 2000-12-27 | Genetics Institute, Inc. | Inhibitors of phospholipase a2 |
| CA2383983C (en) * | 1998-03-31 | 2009-09-29 | The Institutes For Pharmaceutical Discovery, Llc | Substituted indolealkanoic acids |
| WO2000028188A1 (en) * | 1998-11-10 | 2000-05-18 | Baker Hughes Incorporated | Self-controlled directional drilling systems and methods |
| WO2000035886A2 (en) | 1998-12-18 | 2000-06-22 | Axys Pharmaceuticals, Inc. | (hetero)aryl-bicyclic heteroaryl derivatives, their preparation and their use as protease inhibitors |
| CA2386750A1 (en) * | 1999-10-22 | 2001-05-03 | Merck & Co. Inc. | Pharmaceuticals for treating obesity |
| WO2002008188A1 (en) * | 2000-07-25 | 2002-01-31 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
| PL366068A1 (en) | 2000-10-10 | 2005-01-24 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppar-gamma binding agents |
| US6706751B2 (en) * | 2000-12-21 | 2004-03-16 | Hoffman-La Roche Inc. | Dihydroindole and tetrahydroquinoline derivatives |
| EP1424325A4 (en) | 2001-09-07 | 2005-12-21 | Ono Pharmaceutical Co | INDOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICAMENTS CONTAINING THEM AS AN ACTIVE AGENT |
| GB0205165D0 (en) * | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| WO2003082271A2 (en) * | 2002-04-03 | 2003-10-09 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| US20040038958A1 (en) | 2002-07-11 | 2004-02-26 | Chris Rundfeldt | Topical treatment of skin diseases |
| WO2004020408A1 (en) * | 2002-08-29 | 2004-03-11 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| US7129264B2 (en) * | 2003-04-16 | 2006-10-31 | Bristol-Myers Squibb Company | Biarylmethyl indolines and indoles as antithromboembolic agents |
| EA010422B1 (ru) * | 2003-08-01 | 2008-08-29 | Янссен Фармацевтика Н.В. | Замещённые индол-о-глюкозиды |
-
2003
- 2003-08-27 WO PCT/US2003/026677 patent/WO2004020408A1/en not_active Ceased
- 2003-08-27 DK DK03791952.9T patent/DK1537078T3/da active
- 2003-08-27 ES ES03791952T patent/ES2342596T3/es not_active Expired - Lifetime
- 2003-08-27 BR BR0313825-9A patent/BR0313825A/pt not_active IP Right Cessation
- 2003-08-27 JP JP2004531948A patent/JP4377815B2/ja not_active Expired - Fee Related
- 2003-08-27 KR KR1020057003552A patent/KR20050057074A/ko not_active Abandoned
- 2003-08-27 WO PCT/US2003/027156 patent/WO2004020409A1/en not_active Ceased
- 2003-08-27 MX MXPA05002303A patent/MXPA05002303A/es active IP Right Grant
- 2003-08-27 DE DE60332125T patent/DE60332125D1/de not_active Expired - Lifetime
- 2003-08-27 AU AU2003265681A patent/AU2003265681A1/en not_active Abandoned
- 2003-08-27 NZ NZ538031A patent/NZ538031A/en unknown
- 2003-08-27 HR HR20050181A patent/HRP20050181A2/hr not_active Application Discontinuation
- 2003-08-27 US US10/524,697 patent/US7186746B2/en not_active Expired - Lifetime
- 2003-08-27 CA CA002495943A patent/CA2495943C/en not_active Expired - Fee Related
- 2003-08-27 RU RU2005108668/04A patent/RU2328483C2/ru not_active IP Right Cessation
- 2003-08-27 PT PT03791952T patent/PT1537078E/pt unknown
- 2003-08-27 PL PL03375302A patent/PL375302A1/xx not_active Application Discontinuation
- 2003-08-27 CN CNB038206919A patent/CN100457730C/zh not_active Expired - Fee Related
-
2005
- 2005-01-31 IS IS7680A patent/IS7680A/is unknown
- 2005-02-08 IL IL16676405A patent/IL166764A0/xx not_active IP Right Cessation
- 2005-02-25 EC EC2005005632A patent/ECSP055632A/es unknown
- 2005-03-16 MA MA28147A patent/MA27396A1/fr unknown
- 2005-03-23 NO NO20051546A patent/NO20051546L/no not_active Application Discontinuation
-
2007
- 2007-03-06 US US11/714,341 patent/US7345085B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN100457730C (zh) | 2009-02-04 |
| AU2003265681A1 (en) | 2004-03-19 |
| JP2006500384A (ja) | 2006-01-05 |
| ECSP055632A (es) | 2005-04-18 |
| CN1678578A (zh) | 2005-10-05 |
| RU2005108668A (ru) | 2005-08-27 |
| IS7680A (is) | 2005-01-31 |
| IL166764A0 (en) | 2006-01-15 |
| HRP20050181A2 (en) | 2006-03-31 |
| RU2328483C2 (ru) | 2008-07-10 |
| US20050277685A1 (en) | 2005-12-15 |
| WO2004020409A1 (en) | 2004-03-11 |
| US7345085B2 (en) | 2008-03-18 |
| BR0313825A (pt) | 2005-07-12 |
| CA2495943A1 (en) | 2004-03-11 |
| HK1083836A1 (zh) | 2006-07-14 |
| ES2342596T3 (es) | 2010-07-09 |
| DE60332125D1 (de) | 2010-05-27 |
| NO20051546L (no) | 2005-05-24 |
| JP4377815B2 (ja) | 2009-12-02 |
| US20070161689A1 (en) | 2007-07-12 |
| WO2004020408A1 (en) | 2004-03-11 |
| US7186746B2 (en) | 2007-03-06 |
| MXPA05002303A (es) | 2005-06-08 |
| CA2495943C (en) | 2009-07-21 |
| DK1537078T3 (da) | 2010-08-02 |
| PT1537078E (pt) | 2010-06-18 |
| KR20050057074A (ko) | 2005-06-16 |
| PL375302A1 (en) | 2005-11-28 |
| MA27396A1 (fr) | 2005-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NZ538031A (en) | Indoles having anti-diabetic activity | |
| AU2001277056B2 (en) | N-substituted indoles useful in the treatment of diabetes | |
| US7393960B2 (en) | Indoles having anti-diabetic activity | |
| AU2001277056A1 (en) | N-substituted indoles useful in the treatment of diabetes | |
| EA017800B1 (ru) | Антагонисты рецептора глюкагона, композиции, содержащие такие соединения | |
| JP2004521124A (ja) | 糖尿病および脂質障害用の2−アリールオキシ−2−アリールアルカン酸類 | |
| EP1861382B1 (en) | Fused aromatic compounds having anti-diabetic activity | |
| US20080119531A1 (en) | Indoles Having Anti-Diabetic Activity | |
| EP1537078B1 (en) | Indoles having anti-diabetic activity | |
| WO2006022954A2 (en) | Benzoureas having anti-diabetic activity | |
| HK1083836B (en) | Indoles having anti-diabetic activity | |
| TWI320781B (en) | Indoles having anti-diabetic activity | |
| US20080076810A1 (en) | Benzoureas Having Anti-Diabetic Activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |