ZA200501273B - N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes - Google Patents
N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes Download PDFInfo
- Publication number
- ZA200501273B ZA200501273B ZA200501273A ZA200501273A ZA200501273B ZA 200501273 B ZA200501273 B ZA 200501273B ZA 200501273 A ZA200501273 A ZA 200501273A ZA 200501273 A ZA200501273 A ZA 200501273A ZA 200501273 B ZA200501273 B ZA 200501273B
- Authority
- ZA
- South Africa
- Prior art keywords
- anyone
- methyl
- phenyl
- indol
- propionic acid
- Prior art date
Links
- -1 N-substituted-1H-indol-5-propionic acid compounds Chemical class 0.000 title claims description 30
- 238000011282 treatment Methods 0.000 title claims description 22
- 239000000556 agonist Substances 0.000 title claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 10
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 9
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 19
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 229960001243 orlistat Drugs 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 101150014691 PPARA gene Proteins 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000013256 coordination polymer Substances 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 150000002632 lipids Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 230000036772 blood pressure Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 5
- 230000003143 atherosclerotic effect Effects 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- MMOLYSUHEKSQBL-QHCPKHFHSA-N (2s)-2-ethoxy-3-[1-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(F)C(C)=C1 MMOLYSUHEKSQBL-QHCPKHFHSA-N 0.000 claims description 2
- ZYXIXLCLHFATLN-QFIPXVFZSA-N (2s)-2-ethoxy-3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 ZYXIXLCLHFATLN-QFIPXVFZSA-N 0.000 claims description 2
- WSRMUNNNZQAXOU-UHFFFAOYSA-N 2-ethoxy-3-[1-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-3-methylindol-5-yl]propanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(F)C(C)=C1 WSRMUNNNZQAXOU-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- UVONRKUHROLAFB-QHCPKHFHSA-N (2s)-2-ethoxy-3-[1-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1OC UVONRKUHROLAFB-QHCPKHFHSA-N 0.000 claims 1
- HNJWXXUWEWHCGB-UHFFFAOYSA-N 2-but-3-enoxy-3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound N=1C(CN2C3=CC=C(CC(OCCC=C)C(O)=O)C=C3C=C2)=C(C)OC=1C1=CC=C(C(F)(F)F)C=C1 HNJWXXUWEWHCGB-UHFFFAOYSA-N 0.000 claims 1
- BAGMLPPSRATBGO-UHFFFAOYSA-N 2-ethoxy-3-[4-methyl-1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=C(C)C(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 BAGMLPPSRATBGO-UHFFFAOYSA-N 0.000 claims 1
- SNELYVVCHDOVFP-UHFFFAOYSA-N 3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-propoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 SNELYVVCHDOVFP-UHFFFAOYSA-N 0.000 claims 1
- 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 description 16
- 102000004877 Insulin Human genes 0.000 description 8
- 108090001061 Insulin Proteins 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229940125396 insulin Drugs 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 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 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229940122355 Insulin sensitizer Drugs 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- 239000004367 Lipase Substances 0.000 description 3
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 235000019421 lipase Nutrition 0.000 description 3
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 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 2
- 229940127470 Lipase Inhibitors Drugs 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940123464 Thiazolidinedione Drugs 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 210000000496 pancreas Anatomy 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000001467 thiazolidinediones Chemical class 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- RTXIDZKNOYTSIW-XMMPIXPASA-N (2r)-2-ethoxy-3-[1-[[2-(4-ethylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(CC)C=C1 RTXIDZKNOYTSIW-XMMPIXPASA-N 0.000 description 1
- SOUNJDHGUGDNBB-QFIPXVFZSA-N (2s)-2-ethoxy-3-[1-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1 SOUNJDHGUGDNBB-QFIPXVFZSA-N 0.000 description 1
- PAWOPJKHTZCKMT-QFIPXVFZSA-N (2s)-3-(1-{[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}-1h-indol-5-yl)-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl PAWOPJKHTZCKMT-QFIPXVFZSA-N 0.000 description 1
- PMZZWDLQGMUYFU-DEOSSOPVSA-N (2s)-3-[1-[[2-(3,5-dimethoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(OC)=CC(OC)=C1 PMZZWDLQGMUYFU-DEOSSOPVSA-N 0.000 description 1
- YSXCYICRWYJVDH-BKUYFWCQSA-N (z)-2-methoxy-3-[1-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]indol-5-yl]prop-2-enoic acid Chemical compound C1=CC2=CC(\C=C(/OC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1 YSXCYICRWYJVDH-BKUYFWCQSA-N 0.000 description 1
- QQXYDGFPNGZZQG-JCMHNJIXSA-N (z)-2-methoxy-3-[1-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]indol-5-yl]prop-2-enoic acid Chemical compound C1=CC2=CC(\C=C(/OC)C(O)=O)=CC=C2N1CCC(=C(O1)C)N=C1C1=CC=CC=C1 QQXYDGFPNGZZQG-JCMHNJIXSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SOUNJDHGUGDNBB-UHFFFAOYSA-N 2-ethoxy-3-[1-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1 SOUNJDHGUGDNBB-UHFFFAOYSA-N 0.000 description 1
- OEAWGOQTYLNWOU-UHFFFAOYSA-N 2-ethoxy-3-[1-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1F OEAWGOQTYLNWOU-UHFFFAOYSA-N 0.000 description 1
- UVONRKUHROLAFB-UHFFFAOYSA-N 2-ethoxy-3-[1-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1OC UVONRKUHROLAFB-UHFFFAOYSA-N 0.000 description 1
- MMOLYSUHEKSQBL-UHFFFAOYSA-N 2-ethoxy-3-[1-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(F)C(C)=C1 MMOLYSUHEKSQBL-UHFFFAOYSA-N 0.000 description 1
- VKXXMTBEMZTIPR-UHFFFAOYSA-N 2-ethoxy-3-[1-[[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(F)C=C1 VKXXMTBEMZTIPR-UHFFFAOYSA-N 0.000 description 1
- QWORIWQTCIYNKN-UHFFFAOYSA-N 2-ethoxy-3-[1-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1C QWORIWQTCIYNKN-UHFFFAOYSA-N 0.000 description 1
- JLVNHOJWHCMXNK-UHFFFAOYSA-N 2-ethoxy-3-[1-[[5-methyl-2-(2-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1OC(C)C JLVNHOJWHCMXNK-UHFFFAOYSA-N 0.000 description 1
- YZLXZCYNUYYXDW-UHFFFAOYSA-N 2-ethoxy-3-[1-[[5-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(OC)=C(OC)C(OC)=C1 YZLXZCYNUYYXDW-UHFFFAOYSA-N 0.000 description 1
- UDXHXODNGSKQKU-UHFFFAOYSA-N 2-ethoxy-3-[1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 UDXHXODNGSKQKU-UHFFFAOYSA-N 0.000 description 1
- ZYXIXLCLHFATLN-UHFFFAOYSA-N 2-ethoxy-3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 ZYXIXLCLHFATLN-UHFFFAOYSA-N 0.000 description 1
- TZXIEDKSSWDAEG-UHFFFAOYSA-N 2-ethoxy-3-[2-methyl-1-[(2-phenyl-1,3-thiazol-4-yl)methyl]indol-5-yl]propanoic acid Chemical compound CC1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(N=1)=CSC=1C1=CC=CC=C1 TZXIEDKSSWDAEG-UHFFFAOYSA-N 0.000 description 1
- VHDZXMLOJYTMRT-UHFFFAOYSA-N 2-ethoxy-3-[2-methyl-1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound CC1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 VHDZXMLOJYTMRT-UHFFFAOYSA-N 0.000 description 1
- SRGMASRXXKNDLX-UHFFFAOYSA-N 2-ethoxy-3-[3-methyl-1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 SRGMASRXXKNDLX-UHFFFAOYSA-N 0.000 description 1
- KWGGIRZLUSNBCK-UHFFFAOYSA-N 2-ethoxy-3-[3-methyl-1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 KWGGIRZLUSNBCK-UHFFFAOYSA-N 0.000 description 1
- PHFVTWXRIIMDMG-UHFFFAOYSA-N 2-methoxy-3-[1-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(CC(OC)C(O)=O)=CC=C2N1CCC(=C(O1)C)N=C1C1=CC=CC=C1 PHFVTWXRIIMDMG-UHFFFAOYSA-N 0.000 description 1
- ANWCTRCWTSJEPV-UHFFFAOYSA-N 3-[1-[[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]-2-ethoxypropanoic acid Chemical compound CC1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl ANWCTRCWTSJEPV-UHFFFAOYSA-N 0.000 description 1
- HWGSDOIOQSFRBG-UHFFFAOYSA-N 3-[1-[[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-3-methylindol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl HWGSDOIOQSFRBG-UHFFFAOYSA-N 0.000 description 1
- PAWOPJKHTZCKMT-UHFFFAOYSA-N 3-[1-[[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl PAWOPJKHTZCKMT-UHFFFAOYSA-N 0.000 description 1
- ROQOWYZQXBBSNU-UHFFFAOYSA-N 3-[1-[[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C(=CC=CC=2)Cl)=NC=1CN(C1=CC=2)C=CC1=CC=2CC(C(O)=O)OC1=CC=CC=C1 ROQOWYZQXBBSNU-UHFFFAOYSA-N 0.000 description 1
- ODDSUBSZXDLXCP-UHFFFAOYSA-N 3-[1-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-propoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1OC ODDSUBSZXDLXCP-UHFFFAOYSA-N 0.000 description 1
- RQMKNZHMAWCBJL-UHFFFAOYSA-N 3-[1-[[2-(3,5-dichlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(Cl)=CC(Cl)=C1 RQMKNZHMAWCBJL-UHFFFAOYSA-N 0.000 description 1
- CXYFQEHVRVKAPR-UHFFFAOYSA-N 3-[1-[[2-(3,5-difluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(F)=CC(F)=C1 CXYFQEHVRVKAPR-UHFFFAOYSA-N 0.000 description 1
- DSKLBNZCCNQVBC-UHFFFAOYSA-N 3-[1-[[2-(3,5-dimethylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(C)=CC(C)=C1 DSKLBNZCCNQVBC-UHFFFAOYSA-N 0.000 description 1
- FCIBDTJPPCRIJB-UHFFFAOYSA-N 3-[1-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 FCIBDTJPPCRIJB-UHFFFAOYSA-N 0.000 description 1
- TYOWMJWLKHBYRL-UHFFFAOYSA-N 3-[1-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C)C(F)=CC=2)=NC=1CN(C1=CC=2)C=CC1=CC=2CC(C(O)=O)OC1=CC=CC=C1 TYOWMJWLKHBYRL-UHFFFAOYSA-N 0.000 description 1
- KCEBJCYTZWGCEX-UHFFFAOYSA-N 3-[1-[[2-(4-tert-butylphenyl)-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]-2-ethoxypropanoic acid Chemical compound CC1=CC2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(N=1)=COC=1C1=CC=C(C(C)(C)C)C=C1 KCEBJCYTZWGCEX-UHFFFAOYSA-N 0.000 description 1
- GZWLHVYQGHFRDW-UHFFFAOYSA-N 3-[1-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-propoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1C GZWLHVYQGHFRDW-UHFFFAOYSA-N 0.000 description 1
- OOAVVRXSCVRARK-UHFFFAOYSA-N 3-[1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-phenoxypropanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(CN2C3=CC=C(CC(OC=4C=CC=CC=4)C(O)=O)C=C3C=C2)=C(C)O1 OOAVVRXSCVRARK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- QYOVMAREBTZLBT-KTKRTIGZSA-N CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO QYOVMAREBTZLBT-KTKRTIGZSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 206010048554 Endothelial dysfunction Diseases 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010022489 Insulin Resistance Diseases 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 238000008214 LDL Cholesterol Methods 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
- 208000017170 Lipid metabolism disease Diseases 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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 239000005913 Maltodextrin Substances 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000001708 anti-dyslipidemic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000003963 antioxidant agent 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
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 229940062310 avandia Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000007211 cardiovascular event Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 238000011291 current first-line treatment Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008694 endothelial dysfunction Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000014101 glucose homeostasis Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic 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
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 239000000543 intermediate Substances 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000004322 lipid homeostasis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- 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 1
- 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 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
- 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
- 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
- A61P3/06—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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- 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
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02020477 | 2002-09-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200501273B true ZA200501273B (en) | 2006-08-30 |
Family
ID=31985028
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200501273A ZA200501273B (en) | 2002-09-12 | 2005-02-11 | N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes |
Country Status (29)
Country | Link |
---|---|
US (1) | US6890947B2 (ru) |
EP (1) | EP1539746B1 (ru) |
JP (1) | JP4286782B2 (ru) |
KR (1) | KR100645684B1 (ru) |
CN (1) | CN100577660C (ru) |
AR (1) | AR041218A1 (ru) |
AT (1) | ATE345340T1 (ru) |
AU (1) | AU2003267041B2 (ru) |
BR (1) | BR0314261A (ru) |
CA (1) | CA2494601C (ru) |
DE (1) | DE60309719T2 (ru) |
DK (1) | DK1539746T3 (ru) |
ES (1) | ES2275105T3 (ru) |
GT (1) | GT200300194A (ru) |
HR (1) | HRP20050212A2 (ru) |
MX (1) | MXPA05002704A (ru) |
MY (1) | MY135646A (ru) |
NO (1) | NO20050667L (ru) |
NZ (1) | NZ537979A (ru) |
PA (1) | PA8581701A1 (ru) |
PE (1) | PE20050050A1 (ru) |
PL (1) | PL375878A1 (ru) |
PT (1) | PT1539746E (ru) |
RU (1) | RU2296759C2 (ru) |
SI (1) | SI1539746T1 (ru) |
TW (1) | TWI248933B (ru) |
UY (1) | UY27975A1 (ru) |
WO (1) | WO2004024726A1 (ru) |
ZA (1) | ZA200501273B (ru) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10022925A1 (de) * | 2000-05-11 | 2001-11-15 | Basf Ag | Substituierte Indole als PARP-Inhibitoren |
ATE339205T1 (de) * | 2003-04-17 | 2006-10-15 | Kalypsys Inc | (3-ä3-'(2,4-bis-trifluormethyl-benzyl)-(5-ethyl pyrimidin-2-yl)-amino)-propoxyü-phenyl)- essigsäure und verwandte verbindungen als modulatoren von ppars und verfahren zur behandlung von stoffwechselstörungen |
WO2005060958A1 (en) * | 2003-12-19 | 2005-07-07 | Kalypsys, Inc. | (5- (2-phenyl)-thiazol-5-ylmethoxy)-indol-1-yl) -acetic acid derivatives and related compounds as modulators of the human ppar-delta receptor for the treatment of metabolic disorders such as type 2 diabetes |
US7405236B2 (en) * | 2004-08-16 | 2008-07-29 | Hoffman-La Roche Inc. | Indole derivatives comprising an acetylene group |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
NO20083270L (no) * | 2008-07-23 | 2010-01-25 | Thia Medica As | Indolforbindelser |
WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4011326A (en) * | 1975-07-29 | 1977-03-08 | Merck & Co., Inc. | 2-Substituted oxazolo[4,5-b]pyridine anti-inflammatory agents |
CA1247547A (en) * | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
CA1270837A (en) | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
CA1328881C (en) | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
CA2035972C (en) | 1990-02-23 | 2006-07-11 | Martin Karpf | Process for the preparation of oxetanones |
US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
US5274143A (en) | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
PL174610B1 (pl) | 1992-07-03 | 1998-08-31 | Smithkline Beecham Plc | Nowe związki heterocykliczne |
GB9225386D0 (en) | 1992-12-04 | 1993-01-27 | Smithkline Beecham Plc | Novel compounds |
DE4317320A1 (de) * | 1993-05-25 | 1994-12-01 | Boehringer Mannheim Gmbh | Neue Thiazolidindione und diese enthaltende Arzneimittel |
GB9326171D0 (en) | 1993-12-22 | 1994-02-23 | Smithkline Beecham Plc | Novel compounds |
IL117208A0 (en) * | 1995-02-23 | 1996-06-18 | Nissan Chemical Ind Ltd | Indole type thiazolidines |
US6069156A (en) * | 1995-04-10 | 2000-05-30 | Fujisawa Pharmaceutical Co., Ltd. | Indole derivatives as cGMP-PDE inhibitors |
JPH09176162A (ja) * | 1995-12-22 | 1997-07-08 | Toubishi Yakuhin Kogyo Kk | チアゾリジンジオン誘導体及びその製造法並びにそれを含む医薬組成物 |
GB9600464D0 (en) | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
ES2217392T3 (es) * | 1996-02-02 | 2004-11-01 | MERCK & CO., INC. | Agentes antidiabeticos. |
IL129999A (en) * | 1996-12-10 | 2004-06-20 | Bristol Myers Squibb Co | Melatonergic agents which are benzodioxole, benzopuran, dihydrobenzopuran and benzodioxane |
US6004996A (en) * | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
DE19711616A1 (de) * | 1997-03-20 | 1998-09-24 | Boehringer Mannheim Gmbh | Verbessertes Verfahren zur Herstellung von Thiazolidindionen |
US6121397A (en) * | 1997-07-14 | 2000-09-19 | Xerox Corporation | Polymerization processes using oligomeric compound, monomer and surfactant |
HN1998000118A (es) | 1997-08-27 | 1999-02-09 | Pfizer Prod Inc | 2 - aminopiridinas que contienen sustituyentes de anillos condensados. |
DE69815008T2 (de) | 1997-09-19 | 2004-04-01 | Ssp Co., Ltd. | Alfa-substituierte Phenylpropionsäurederivate und diese enthaltende Arzneimittel |
WO1999008501A2 (en) | 1998-04-23 | 1999-02-25 | Dr. Reddy's Research Foundation | New heterocyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
GB9817118D0 (en) | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
TR200100472T2 (tr) | 1998-08-14 | 2001-07-23 | F.Hoffmann-La Roche Ag | Lipaz inhibitörleri ile sitozan içeren farmasötik bileşimler |
CN1170534C (zh) | 1998-08-14 | 2004-10-13 | 霍夫曼-拉罗奇有限公司 | 含有脂酶抑制剂的药物组合物 |
GB9914977D0 (en) | 1999-06-25 | 1999-08-25 | Glaxo Group Ltd | Chemical compounds |
DK1078923T3 (da) | 1999-08-02 | 2006-07-10 | Hoffmann La Roche | Fremgangsmåde til fremstilling af benzothiophenderivater |
ATE362468T1 (de) * | 2000-07-25 | 2007-06-15 | Merck & Co Inc | N-substituierte indole mit anwendung in der behandlung von diabetes |
DE60128239T2 (de) | 2000-08-23 | 2008-01-10 | Eli Lilly And Co., Indianapolis | Oxazolylarylpropionsäure derivate und ihre verwendung als ppar agonisten |
DE10117090B4 (de) * | 2001-04-06 | 2013-08-14 | Dr. Ing. H.C. F. Porsche Aktiengesellschaft | Wassergekühlte, mehrzylindrige Brennkraftmaschine |
WO2003005025A1 (en) | 2001-07-03 | 2003-01-16 | Biovitrum Ab | Methods for identifying compounds modulating the activity of ppar-gamma |
WO2003040114A1 (en) * | 2001-11-06 | 2003-05-15 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
AU2002359160A1 (en) | 2001-12-20 | 2003-07-09 | Biovitrum Ab | PIPAZOLO (1,5-a) PYRIMIDINE DERIVATIVES AS MODULATORS OF PPAR |
-
2003
- 2003-09-04 SI SI200330631T patent/SI1539746T1/sl unknown
- 2003-09-04 RU RU2005110921/04A patent/RU2296759C2/ru not_active IP Right Cessation
- 2003-09-04 DE DE60309719T patent/DE60309719T2/de not_active Expired - Lifetime
- 2003-09-04 WO PCT/EP2003/009819 patent/WO2004024726A1/en active IP Right Grant
- 2003-09-04 BR BR0314261-2A patent/BR0314261A/pt not_active IP Right Cessation
- 2003-09-04 AT AT03747962T patent/ATE345340T1/de not_active IP Right Cessation
- 2003-09-04 PT PT03747962T patent/PT1539746E/pt unknown
- 2003-09-04 EP EP03747962A patent/EP1539746B1/en not_active Expired - Lifetime
- 2003-09-04 CA CA002494601A patent/CA2494601C/en not_active Expired - Fee Related
- 2003-09-04 PL PL03375878A patent/PL375878A1/xx not_active Application Discontinuation
- 2003-09-04 AU AU2003267041A patent/AU2003267041B2/en not_active Ceased
- 2003-09-04 KR KR1020057004166A patent/KR100645684B1/ko not_active IP Right Cessation
- 2003-09-04 ES ES03747962T patent/ES2275105T3/es not_active Expired - Lifetime
- 2003-09-04 JP JP2004535427A patent/JP4286782B2/ja not_active Expired - Fee Related
- 2003-09-04 DK DK03747962T patent/DK1539746T3/da active
- 2003-09-04 NZ NZ537979A patent/NZ537979A/en unknown
- 2003-09-04 MX MXPA05002704A patent/MXPA05002704A/es active IP Right Grant
- 2003-09-04 CN CN03821483A patent/CN100577660C/zh not_active Expired - Fee Related
- 2003-09-08 TW TW092124737A patent/TWI248933B/zh not_active IP Right Cessation
- 2003-09-09 PA PA20038581701A patent/PA8581701A1/es unknown
- 2003-09-10 GT GT200300194A patent/GT200300194A/es unknown
- 2003-09-10 AR ARP030103266A patent/AR041218A1/es unknown
- 2003-09-10 US US10/659,664 patent/US6890947B2/en not_active Expired - Fee Related
- 2003-09-10 PE PE2003000917A patent/PE20050050A1/es not_active Application Discontinuation
- 2003-09-10 MY MYPI20033416A patent/MY135646A/en unknown
- 2003-09-11 UY UY27975A patent/UY27975A1/es not_active Application Discontinuation
-
2005
- 2005-02-08 NO NO20050667A patent/NO20050667L/no not_active Application Discontinuation
- 2005-02-11 ZA ZA200501273A patent/ZA200501273B/en unknown
- 2005-03-04 HR HR20050212A patent/HRP20050212A2/hr not_active Application Discontinuation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200501273B (en) | N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes | |
JP2010043098A (ja) | エステル化合物及びその医薬用途 | |
TW201835081A (zh) | 具有體抑素受體促效活性之化合物及其醫藥用途 | |
US20070105959A1 (en) | Cynnamyl alcohol derivative compounds and drugs containing the compounds as active ingredient | |
JP4774995B2 (ja) | アシルアミノチアゾール誘導体を有効成分とする医薬組成物 | |
KR20010080144A (ko) | 카르복실산 유도체 및 이 유도체를 활성 성분으로서포함하는 약제 | |
US6924295B2 (en) | Tetrahydroquinoline derivative compound and drug containing the compound as active ingredient | |
JPWO2005021486A1 (ja) | エステル誘導体及びその医薬用途 | |
WO2000012491A1 (fr) | Derives d'acide carboxylique et medicaments dont ils sont le principe actif | |
US7560475B2 (en) | Phenylacetic acid derivative, process for producing the same, and use | |
US8101774B2 (en) | Ester derivatives and medicinal use thereof | |
JP3662566B2 (ja) | エステル化合物及びその医薬用途 | |
US7323456B2 (en) | Carboxylic acid derivatives compounds and agents comprising the compounds as active ingredient | |
US20040235866A1 (en) | Lymphocytic activation inhibitor and remedial agent for autoimmune disease | |
JP4290648B2 (ja) | オキサゾール誘導体及びインスリン感作物質としてのそれらの使用 | |
AU2003262286B2 (en) | Novel Effectors of Dipeptidyl Peptidase IV | |
JP2004026679A (ja) | ジヒドロナフタレン誘導体 | |
JP2005220133A (ja) | エステル化合物及びその医薬用途 |