UA77987C2 - Substituted derivatives of phenylpropionic acid as agonists of peroxisome proliferators activated alpha receptor, method for synthesis, pharmaceutical composition, intermediate (variants) - Google Patents
Substituted derivatives of phenylpropionic acid as agonists of peroxisome proliferators activated alpha receptor, method for synthesis, pharmaceutical composition, intermediate (variants) Download PDFInfo
- Publication number
- UA77987C2 UA77987C2 UA20040604245A UA20040604245A UA77987C2 UA 77987 C2 UA77987 C2 UA 77987C2 UA 20040604245 A UA20040604245 A UA 20040604245A UA 20040604245 A UA20040604245 A UA 20040604245A UA 77987 C2 UA77987 C2 UA 77987C2
- Authority
- UA
- Ukraine
- Prior art keywords
- phenyl
- methylthio
- dioxo
- tetrahydro
- carbamoyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 239000000556 agonist Substances 0.000 title description 8
- 239000003614 peroxisome proliferator Substances 0.000 title description 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 150000003839 salts Chemical class 0.000 claims abstract description 78
- 239000012453 solvate Substances 0.000 claims abstract description 67
- 239000000651 prodrug Substances 0.000 claims abstract description 43
- 229940002612 prodrug Drugs 0.000 claims abstract description 43
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 23
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 12
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 150000002632 lipids Chemical class 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 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 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
- 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 4
- 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 4
- 239000003529 anticholesteremic agent Substances 0.000 claims description 4
- 229940127226 anticholesterol agent Drugs 0.000 claims description 4
- 229960005370 atorvastatin Drugs 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([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
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- -1 for example Chemical group 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 208000001145 Metabolic Syndrome Diseases 0.000 description 8
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 108010007622 LDL Lipoproteins Proteins 0.000 description 7
- 102000007330 LDL Lipoproteins Human genes 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 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 7
- 239000012074 organic phase Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 description 4
- 108020004414 DNA Proteins 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 229960004580 glibenclamide Drugs 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 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 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- 108060001084 Luciferase Proteins 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000013604 expression vector Substances 0.000 description 3
- 229960004346 glimepiride Drugs 0.000 description 3
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 3
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 description 3
- 229940125396 insulin Drugs 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 208000030159 metabolic disease Diseases 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229960003401 ramipril Drugs 0.000 description 3
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 3
- 229960002231 ramiprilat Drugs 0.000 description 3
- KEDYTOTWMPBSLG-HILJTLORSA-N ramiprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 KEDYTOTWMPBSLG-HILJTLORSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 239000013598 vector Substances 0.000 description 3
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 125000003345 AMP group Chemical group 0.000 description 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 239000002053 C09CA06 - Candesartan Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 230000004568 DNA-binding Effects 0.000 description 2
- 108010061435 Enalapril Proteins 0.000 description 2
- 108010066671 Enalaprilat Proteins 0.000 description 2
- 206010060378 Hyperinsulinaemia Diseases 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
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- 108010007859 Lisinopril Proteins 0.000 description 2
- BWRVBFMWWHWLBW-UHFFFAOYSA-N Lyciumin B Chemical compound C12=CC=CC=C2N2C=C1CC(C(O)=O)NC(=O)C(CO)NC(=O)CNC(=O)C(C(C)C)NC(=O)C2NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCCN1C(=O)C1CCC(=O)N1 BWRVBFMWWHWLBW-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- 102000004316 Oxidoreductases Human genes 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
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 2
- 239000000674 adrenergic antagonist Substances 0.000 description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229960000932 candesartan Drugs 0.000 description 2
- 229960004349 candesartan cilexetil Drugs 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000011284 combination treatment Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000004520 electroporation Methods 0.000 description 2
- 229960000873 enalapril Drugs 0.000 description 2
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 2
- 229960002680 enalaprilat Drugs 0.000 description 2
- LZFZMUMEGBBDTC-QEJZJMRPSA-N enalaprilat (anhydrous) Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 LZFZMUMEGBBDTC-QEJZJMRPSA-N 0.000 description 2
- 229920006227 ethylene-grafted-maleic anhydride Polymers 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229960002490 fosinopril Drugs 0.000 description 2
- WOIWWYDXDVSWAZ-RTWAWAEBSA-N fosinoprilat Chemical compound C([C@@H](C[C@H]1C(=O)O)C2CCCCC2)N1C(=O)CP(O)(=O)CCCCC1=CC=CC=C1 WOIWWYDXDVSWAZ-RTWAWAEBSA-N 0.000 description 2
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 2
- 201000008980 hyperinsulinism Diseases 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960002394 lisinopril Drugs 0.000 description 2
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 206010062198 microangiopathy Diseases 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 230000030648 nucleus localization Effects 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 229960005095 pioglitazone Drugs 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229940083542 sodium Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- TVTJZMHAIQQZTL-WATAJHSMSA-M sodium;(2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate Chemical compound [Na+].C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C([O-])=O)CCCC1=CC=CC=C1 TVTJZMHAIQQZTL-WATAJHSMSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229960002909 spirapril Drugs 0.000 description 2
- 108700035424 spirapril Proteins 0.000 description 2
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
- 229960004084 temocapril Drugs 0.000 description 2
- FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 2
- 238000003146 transient transfection Methods 0.000 description 2
- QKIVRALZQSUWHH-SFYZADRCSA-N (1s,2r)-2-[[2-(hydroxyamino)-2-oxoethyl]-methylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)CN(C)C(=O)[C@@H]1CCCC[C@@H]1C(O)=O QKIVRALZQSUWHH-SFYZADRCSA-N 0.000 description 1
- QDZZDVQGBKTLHV-UHFFFAOYSA-N (2,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1F QDZZDVQGBKTLHV-UHFFFAOYSA-N 0.000 description 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical group O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- DEEOVDONDDERBX-MUDWFXPSSA-N (2S)-6-amino-2-[[(1S,4R,10S,19S,22S,25S,28S,31S,34R,37S,43S,46S,47S,50R,53S,56S,62S)-50-amino-43-(2-amino-2-oxoethyl)-56-(3-amino-3-oxopropyl)-10-benzyl-37-(carboxymethyl)-31-(hydroxymethyl)-28-(1H-indol-3-ylmethyl)-47,62-dimethyl-7-methylidene-22-(2-methylpropyl)-2,5,8,11,14,20,23,26,29,32,35,38,41,44,51,54,57-heptadecaoxo-53-propan-2-yl-48,60,63-trithia-3,6,9,12,15,21,24,27,30,33,36,39,42,45,52,55,58-heptadecazatetracyclo[32.24.3.34,25.015,19]tetrahexacontane-46-carbonyl]amino]hexanoic acid Chemical compound CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)C(=C)NC(=O)[C@@H]2CS[C@@H](C)[C@@H](NC1=O)C(=O)N[C@@H](Cc1c[nH]c3ccccc13)C(=O)N[C@@H](CO)C(=O)N[C@H]1CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CS[C@@H](C)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC1=O)C(=O)N[C@@H](CCCCN)C(O)=O)C(C)C)C(=O)N2 DEEOVDONDDERBX-MUDWFXPSSA-N 0.000 description 1
- NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 description 1
- QIJLJZOGPPQCOG-NFAWXSAZSA-N (2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(=O)C1CCCCC1 QIJLJZOGPPQCOG-NFAWXSAZSA-N 0.000 description 1
- QHRDRNITQKNXNS-JGYLIOAXSA-N (2s)-10-[[(2r)-1-[[(2s)-2-[2-[(2s,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoylamino]propanoyl]-[(1r)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-2,9-diamino-6-(1,2-diamino-2-oxoethyl)-5,10-dioxodecanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)C(C(N)C(N)=O)CCC(N)C(=O)N[C@H](C)C(=O)N([C@H](C)C(O)=O)C(=O)[C@H](C)NC(=O)C(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O QHRDRNITQKNXNS-JGYLIOAXSA-N 0.000 description 1
- PHASTBJLWIZXKB-KKSFZXQISA-N (2s)-2-[[(2s)-1-[carboxymethyl(2,3-dihydro-1h-inden-2-yl)amino]-1-oxopropan-2-yl]amino]-4-phenylbutanoic acid Chemical compound C([C@H](N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 PHASTBJLWIZXKB-KKSFZXQISA-N 0.000 description 1
- GKYIONYOYVKKQI-MPGHIAIKSA-N (2s)-2-[[(2s,3r)-2-(benzoylsulfanylmethyl)-3-phenylbutanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C(O)=O)[C@@H](C)C=1C=CC=CC=1)SC(=O)C1=CC=CC=C1 GKYIONYOYVKKQI-MPGHIAIKSA-N 0.000 description 1
- WMUIIGVAWPWQAW-DEOSSOPVSA-N (2s)-2-ethoxy-3-{4-[2-(10h-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OC2=CC=CC=C21 WMUIIGVAWPWQAW-DEOSSOPVSA-N 0.000 description 1
- HBZJVGFXZTUXNI-XMQLQKOFSA-N (2s)-3-[(2s)-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]propanoyl]-3-azabicyclo[2.2.2]octane-2-carboxylic acid Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C2CCC1CC2)C(O)=O)C(O)=O)CC1=CC=CC=C1 HBZJVGFXZTUXNI-XMQLQKOFSA-N 0.000 description 1
- OMGPCTGQLHHVDU-SSXGPBTGSA-N (2s)-3-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3-azabicyclo[2.2.2]octane-2-carboxylic acid Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C2CCC1CC2)C(O)=O)CC1=CC=CC=C1 OMGPCTGQLHHVDU-SSXGPBTGSA-N 0.000 description 1
- FTYVYAGWBXTWTN-ZVZYQTTQSA-N (2s)-5-tert-butyl-3-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-2h-1,3,4-thiadiazole-2-carboxylic acid Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](SC(=N1)C(C)(C)C)C(O)=O)CC1=CC=CC=C1 FTYVYAGWBXTWTN-ZVZYQTTQSA-N 0.000 description 1
- AHYHTSYNOHNUSH-GBBGEASQSA-N (2s,3as,7as)-1-[(2s)-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-GBBGEASQSA-N 0.000 description 1
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
- FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound 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 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 description 1
- VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 description 1
- NZFXQRHFBLVEQA-GXOSTJLWSA-N (6r)-2-[[(4s)-4-[[(2s)-2-[2-[(2s,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoylamino]propanoyl]amino]-4-carboxybutanoyl]amino]-6,7-diamino-7-oxoheptanoic acid Chemical compound NC(=O)[C@H](N)CCCC(C(O)=O)NC(=O)CC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)C(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O NZFXQRHFBLVEQA-GXOSTJLWSA-N 0.000 description 1
- CICPSCXBPAGDJY-UHFFFAOYSA-N 1,2,5-benzothiadiazepine Chemical class S1N=CC=NC2=CC=CC=C12 CICPSCXBPAGDJY-UHFFFAOYSA-N 0.000 description 1
- KYVHGCKMVJDCNV-UHFFFAOYSA-N 1,4-benzothiazepine Chemical class S1C=CN=CC2=CC=CC=C12 KYVHGCKMVJDCNV-UHFFFAOYSA-N 0.000 description 1
- KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 description 1
- FAKRSMQSSFJEIM-BQBZGAKWSA-N 1-(3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid Chemical compound SC[C@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-BQBZGAKWSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
- IFYLTXNCFVRALQ-UHFFFAOYSA-N 1-[6-amino-2-[hydroxy(4-phenylbutyl)phosphoryl]oxyhexanoyl]pyrrolidine-2-carboxylic acid Chemical compound C1CCC(C(O)=O)N1C(=O)C(CCCCN)OP(O)(=O)CCCCC1=CC=CC=C1 IFYLTXNCFVRALQ-UHFFFAOYSA-N 0.000 description 1
- NIGNBCLEMMGDQP-UHFFFAOYSA-N 1-benzothiepine Chemical class S1C=CC=CC2=CC=CC=C12 NIGNBCLEMMGDQP-UHFFFAOYSA-N 0.000 description 1
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 1
- LLJFMFZYVVLQKT-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea Chemical compound C=1C(OC)=CC=C(C(C2=O)(C)C)C=1C(=O)N2CCC(C=C1)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 LLJFMFZYVVLQKT-UHFFFAOYSA-N 0.000 description 1
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 description 1
- XRKXJJYSKUIIEN-UHFFFAOYSA-N 2-[cyclopentyl-[3-(2,2-dimethylpropanoylsulfanyl)-2-methylpropanoyl]amino]acetic acid Chemical compound CC(C)(C)C(=O)SCC(C)C(=O)N(CC(O)=O)C1CCCC1 XRKXJJYSKUIIEN-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-UHFFFAOYSA-N 0.000 description 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
- 101800000734 Angiotensin-1 Proteins 0.000 description 1
- 102400000344 Angiotensin-1 Human genes 0.000 description 1
- 102000018616 Apolipoproteins B Human genes 0.000 description 1
- 108010027006 Apolipoproteins B Proteins 0.000 description 1
- 206010062542 Arterial insufficiency Diseases 0.000 description 1
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- NEEBNBLVYKFVTK-VGMNWLOBSA-N Captopril-cysteine disulfide Chemical compound OC(=O)[C@@H](N)CSSC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O NEEBNBLVYKFVTK-VGMNWLOBSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- IFYLTXNCFVRALQ-OALUTQOASA-N Ceronapril Chemical compound O([C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)P(O)(=O)CCCCC1=CC=CC=C1 IFYLTXNCFVRALQ-OALUTQOASA-N 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 1
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 1
- UVAUYSRYXACKSC-ULQDDVLXSA-N Cilazaprilat Chemical compound C([C@@H](C(=O)O)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 UVAUYSRYXACKSC-ULQDDVLXSA-N 0.000 description 1
- KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical group C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 102000015779 HDL Lipoproteins Human genes 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- WEGGKZQIJMQCGR-RECQUVTISA-N Hemorphin-4 Chemical compound C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H]([C@H](O)C)C(O)=O)C1=CC=C(O)C=C1 WEGGKZQIJMQCGR-RECQUVTISA-N 0.000 description 1
- 208000031773 Insulin resistance syndrome Diseases 0.000 description 1
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 1
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- IPOLXDNCMOVXCP-UHFFFAOYSA-N Lyciumin A Chemical compound C12=CC=CC=C2N2C=C1CC(C(O)=O)NC(=O)C(CO)NC(=O)CNC(=O)C(C(C)C)NC(=O)C2NC(=O)C(NC(=O)C1N(CCC1)C(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 IPOLXDNCMOVXCP-UHFFFAOYSA-N 0.000 description 1
- IPOLXDNCMOVXCP-YZVVJARPSA-N Lyciumin A Natural products O=C(N[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](C(=O)O)Cc2c3c(n1c2)cccc3)[C@H](NC(=O)[C@H]1N(C(=O)[C@@H]2NC(=O)CC2)CCC1)Cc1ccc(O)cc1 IPOLXDNCMOVXCP-YZVVJARPSA-N 0.000 description 1
- BARYJIKIMHXXOI-UHFFFAOYSA-N Lyciumin A methylate Natural products O=C1NC(C(C)C)C(=O)NCC(=O)NC(CO)C(=O)NC(C(=O)OC)CC(C2=CC=CC=C22)=CN2C1NC(=O)C(NC(=O)C1N(CCC1)C(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 BARYJIKIMHXXOI-UHFFFAOYSA-N 0.000 description 1
- 206010054805 Macroangiopathy Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
- 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 description 1
- NZFXQRHFBLVEQA-UHFFFAOYSA-N Muracein A Natural products NC(=O)C(N)CCCC(C(O)=O)NC(=O)CCC(C(O)=O)NC(=O)C(C)NC(=O)C(C)OC1C(O)C(CO)OC(O)C1NC(C)=O NZFXQRHFBLVEQA-UHFFFAOYSA-N 0.000 description 1
- BNEJUCHZSDIIEH-UHFFFAOYSA-N Muracein B Natural products OC(=O)C(C)NC(=O)C(C)NC(=O)C(CCCC(N)C(N)=O)NC(=O)CCC(C(O)=O)NC(=O)C(C)NC(=O)C(C)OC1C(O)C(CO)OC(O)C1NC(C)=O BNEJUCHZSDIIEH-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-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
- XDMCWZFLLGVIID-SXPRBRBTSA-N O-(3-O-D-galactosyl-N-acetyl-beta-D-galactosaminyl)-L-serine Chemical compound CC(=O)N[C@H]1[C@H](OC[C@H]([NH3+])C([O-])=O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 XDMCWZFLLGVIID-SXPRBRBTSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- XRKXJJYSKUIIEN-LLVKDONJSA-N Pivopril Chemical compound CC(C)(C)C(=O)SC[C@@H](C)C(=O)N(CC(O)=O)C1CCCC1 XRKXJJYSKUIIEN-LLVKDONJSA-N 0.000 description 1
- 241000514450 Podocarpus latifolius Species 0.000 description 1
- 241001505332 Polyomavirus sp. Species 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- 108091007187 Reductases Proteins 0.000 description 1
- 206010057430 Retinal injury Diseases 0.000 description 1
- 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 description 1
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
- UUUHXMGGBIUAPW-CSCXCSGISA-N Teprotide Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(O)=O)C(=O)[C@@H]1CCC(=O)N1 UUUHXMGGBIUAPW-CSCXCSGISA-N 0.000 description 1
- 108010045759 Teprotide 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
- 206010060755 Type V hyperlipidaemia Diseases 0.000 description 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
- YVPOVOVZCOOSBQ-AXHZAXLDSA-N [(1s,3r,7s,8s,8ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2s)-2-methylbutanoate;pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1.C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 YVPOVOVZCOOSBQ-AXHZAXLDSA-N 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 229960001466 acetohexamide Drugs 0.000 description 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
- 229960003526 acipimox Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 108010055869 ancovenin Proteins 0.000 description 1
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000001708 anti-dyslipidemic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000923 atherogenic effect Effects 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960004530 benazepril Drugs 0.000 description 1
- VPSRQEHTHIMDQM-FKLPMGAJSA-N benazepril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 VPSRQEHTHIMDQM-FKLPMGAJSA-N 0.000 description 1
- 229960003619 benazepril hydrochloride Drugs 0.000 description 1
- 229960004067 benazeprilat Drugs 0.000 description 1
- MADRIHWFJGRSBP-ROUUACIJSA-N benazeprilat Chemical compound C([C@H](N[C@H]1CCC2=CC=CC=C2N(C1=O)CC(=O)O)C(O)=O)CC1=CC=CC=C1 MADRIHWFJGRSBP-ROUUACIJSA-N 0.000 description 1
- KKBIUAUSZKGNOA-HNAYVOBHSA-N benzyl (2s)-2-[[(2s)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate Chemical compound O=C([C@@H](NC(=O)[C@@H](CSC(C)=O)CC=1C=C2OCOC2=CC=1)C)OCC1=CC=CC=C1 KKBIUAUSZKGNOA-HNAYVOBHSA-N 0.000 description 1
- IVBOFTGCTWVBLF-GOSISDBHSA-N benzyl 2-[[(2s)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]acetate Chemical compound O=C([C@H](CC=1C=C2OCOC2=CC=1)CSC(=O)C)NCC(=O)OCC1=CC=CC=C1 IVBOFTGCTWVBLF-GOSISDBHSA-N 0.000 description 1
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
- 229950005357 bervastatin Drugs 0.000 description 1
- 229960000516 bezafibrate Drugs 0.000 description 1
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- CUZMQPZYCDIHQL-VCTVXEGHSA-L calcium;(2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate Chemical compound [Ca+2].N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1.N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1 CUZMQPZYCDIHQL-VCTVXEGHSA-L 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960003362 carbutamide Drugs 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000012578 cell culture reagent Substances 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229960005110 cerivastatin Drugs 0.000 description 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound 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 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
- 229950005749 ceronapril Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
- 229950009226 ciglitazone Drugs 0.000 description 1
- 229960005025 cilazapril Drugs 0.000 description 1
- HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
- 229950010233 cilazaprilat Drugs 0.000 description 1
- 229960002174 ciprofibrate Drugs 0.000 description 1
- KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229950003040 dalvastatin Drugs 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 229960005227 delapril Drugs 0.000 description 1
- WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000000667 effect on insulin Effects 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 229960004563 eprosartan Drugs 0.000 description 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- ZADJRRFMOOACHL-WQICJITCSA-N ethyl (e,3s,5r)-7-[4-(4-fluorophenyl)spiro[chromene-2,1'-cyclopentane]-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C12=CC=CC=C2OC2(CCCC2)C(/C=C/[C@H](O)C[C@H](O)CC(=O)OCC)=C1C1=CC=C(F)C=C1 ZADJRRFMOOACHL-WQICJITCSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 229960001880 fosinopril sodium Drugs 0.000 description 1
- 229960003018 fosinoprilat Drugs 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 208000004104 gestational diabetes Diseases 0.000 description 1
- 229960000346 gliclazide Drugs 0.000 description 1
- 229960001381 glipizide Drugs 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
- 229960003468 gliquidone Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- NFRPNQDSKJJQGV-UHFFFAOYSA-N glyhexamide Chemical compound C=1C=C2CCCC2=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 NFRPNQDSKJJQGV-UHFFFAOYSA-N 0.000 description 1
- 229950008290 glyhexamide Drugs 0.000 description 1
- 108010047748 hemorphin 4 Proteins 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 229950010375 idrapril Drugs 0.000 description 1
- 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 description 1
- KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
- 229960001195 imidapril Drugs 0.000 description 1
- 229950009810 indolapril Drugs 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- AXTCRUUITQKBAV-KBPBESRZSA-N libenzapril Chemical compound OC(=O)CN1C(=O)[C@@H](N[C@@H](CCCCN)C(O)=O)CCC2=CC=CC=C21 AXTCRUUITQKBAV-KBPBESRZSA-N 0.000 description 1
- 229950001218 libenzapril Drugs 0.000 description 1
- 108020001756 ligand binding domains Proteins 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- 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 description 1
- 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 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
- 229950009116 mevastatin Drugs 0.000 description 1
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 229960001110 miglitol Drugs 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 229960005170 moexipril Drugs 0.000 description 1
- 229950006549 moveltipril Drugs 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 108700005507 muracein A Proteins 0.000 description 1
- 108700005515 muracein B Proteins 0.000 description 1
- 108700005514 muracein C Proteins 0.000 description 1
- LLYKPZOWCPVRPD-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine;n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=CC=N1 LLYKPZOWCPVRPD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QWRYRQKHCGBRGW-NJJVJDFKSA-N n-[(3r,4r,5s,6r)-2,5-dihydroxy-6-(hydroxymethyl)-4-(1-oxopropan-2-yloxy)oxan-3-yl]acetamide Chemical compound O=CC(C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O QWRYRQKHCGBRGW-NJJVJDFKSA-N 0.000 description 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
- 229960000698 nateglinide Drugs 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229960000827 niceritrol Drugs 0.000 description 1
- 150000005830 nonesterified fatty acids Chemical class 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound 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 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229950008492 pentopril Drugs 0.000 description 1
- 229960002582 perindopril Drugs 0.000 description 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
- 229960005226 perindoprilat Drugs 0.000 description 1
- ODAIHABQVKJNIY-PEDHHIEDSA-N perindoprilat Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(O)=O)[C@H]21 ODAIHABQVKJNIY-PEDHHIEDSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000079 pharmacotherapeutic effect Effects 0.000 description 1
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 1
- 229950008557 phenbutamide Drugs 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 229960002797 pitavastatin Drugs 0.000 description 1
- 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 description 1
- 229950008688 pivopril Drugs 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229960001455 quinapril Drugs 0.000 description 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
- 229960003042 quinapril hydrochloride Drugs 0.000 description 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
- 229960001007 quinaprilat Drugs 0.000 description 1
- FLSLEGPOVLMJMN-YSSFQJQWSA-N quinaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)C(O)=O)CC1=CC=CC=C1 FLSLEGPOVLMJMN-YSSFQJQWSA-N 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
- 229950008257 ragaglitazar Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- 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 description 1
- 229950006297 spiraprilat Drugs 0.000 description 1
- 108700006892 spiraprilat Proteins 0.000 description 1
- FMMDBLMCSDRUPA-BPUTZDHNSA-N spiraprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)C(O)=O)CC1=CC=CC=C1 FMMDBLMCSDRUPA-BPUTZDHNSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- 229950010186 teprotide Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- AHYHTSYNOHNUSH-HXFGRODQSA-N trandolaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-HXFGRODQSA-N 0.000 description 1
- 229960002651 trandolaprilat Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-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
- 229950005696 utibapril Drugs 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 229950009999 zabicipril Drugs 0.000 description 1
- 229950005973 zabiciprilat Drugs 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- UQWLOWFDKAFKAP-WXHSDQCUSA-N zofenoprilat Chemical compound C1[C@@H](C(O)=O)N(C(=O)[C@@H](CS)C)C[C@H]1SC1=CC=CC=C1 UQWLOWFDKAFKAP-WXHSDQCUSA-N 0.000 description 1
- 229950001300 zofenoprilat Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0104334A SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Therapeutic agents |
| PCT/GB2002/005744 WO2003051822A1 (en) | 2001-12-19 | 2002-12-18 | Substituted phenylpropionic acid derivatives as agonists to human peroxisome proliferator-activated receptor alpha (ppar) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77987C2 true UA77987C2 (en) | 2007-02-15 |
Family
ID=20286433
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604245A UA77987C2 (en) | 2001-12-19 | 2002-12-18 | Substituted derivatives of phenylpropionic acid as agonists of peroxisome proliferators activated alpha receptor, method for synthesis, pharmaceutical composition, intermediate (variants) |
| UA20040604246A UA77460C2 (en) | 2001-12-19 | 2002-12-18 | Substituted derivatives of phenylpropionic acid as agonists of alpha-receptor activated by peroxysome proliferator, method of preparation, pharmaceutical composition, intermediate (variants) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604246A UA77460C2 (en) | 2001-12-19 | 2002-12-18 | Substituted derivatives of phenylpropionic acid as agonists of alpha-receptor activated by peroxysome proliferator, method of preparation, pharmaceutical composition, intermediate (variants) |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US7256307B2 (de) |
| EP (2) | EP1458672B1 (de) |
| JP (4) | JP3784804B2 (de) |
| KR (2) | KR20040074094A (de) |
| CN (3) | CN1620423A (de) |
| AR (2) | AR038045A1 (de) |
| AT (2) | ATE338743T1 (de) |
| AU (2) | AU2002366315A1 (de) |
| BR (2) | BR0214988A (de) |
| CA (2) | CA2469302A1 (de) |
| CY (2) | CY1106276T1 (de) |
| DE (2) | DE60214594T2 (de) |
| DK (2) | DK1458673T3 (de) |
| ES (2) | ES2271381T3 (de) |
| HK (2) | HK1068604A1 (de) |
| HU (2) | HUP0402133A3 (de) |
| IL (3) | IL162330A0 (de) |
| IS (2) | IS7309A (de) |
| MX (2) | MXPA04006004A (de) |
| MY (1) | MY132565A (de) |
| NO (2) | NO20043023L (de) |
| NZ (2) | NZ533276A (de) |
| PL (2) | PL370672A1 (de) |
| PT (2) | PT1458672E (de) |
| RU (2) | RU2300517C2 (de) |
| SE (1) | SE0104334D0 (de) |
| SI (2) | SI1458672T1 (de) |
| TW (2) | TWI255807B (de) |
| UA (2) | UA77987C2 (de) |
| WO (2) | WO2003051821A1 (de) |
| ZA (2) | ZA200404657B (de) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1159266B1 (de) | 1999-03-05 | 2004-11-03 | Duke University | C-16 ungesätigte fp-selektive prostaglandin analoge |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| GB0314079D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0229931D0 (en) * | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| SE0104333D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0209467D0 (en) * | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| EP1517882A1 (de) | 2002-06-19 | 2005-03-30 | Eli Lilly And Company | Amidlinker-modulatoren des peroxisom-proliferator-aktivierten rezeptors |
| DK1517883T3 (da) | 2002-06-20 | 2008-05-26 | Astrazeneca Ab | Ortho-substituerede benzoesyrederivater til behandling af insulinresistens |
| FR2848452B1 (fr) * | 2002-12-12 | 2007-04-06 | Aventis Pharma Sa | Application des inhibiteurs de recapture intestinale des acides biliaires pour la prevention et le traitement de la maladie d'alzheimer |
| NZ540612A (en) | 2003-01-14 | 2008-02-29 | Arena Pharm Inc | 1,2,3-Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| GB0304194D0 (en) | 2003-02-25 | 2003-03-26 | Astrazeneca Ab | Chemical compounds |
| GB0314136D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314134D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314129D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| AU2004257267B2 (en) | 2003-07-14 | 2009-12-03 | Arena Pharmaceuticals,Inc | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| WO2005053683A1 (en) | 2003-11-26 | 2005-06-16 | Duke University | A method of preventing or treating glaucoma |
| SI1697306T1 (sl) * | 2003-12-15 | 2008-02-29 | Lilly Co Eli | Selektivni modulatorji peroksisomskih proliferator aktivirajocih receptorjev |
| KR20070050475A (ko) | 2004-08-11 | 2007-05-15 | 교린 세이야꾸 가부시키 가이샤 | 신규 환상 아미노 안식향산 유도체 |
| SE0403072D0 (sv) * | 2004-12-16 | 2004-12-16 | Astrazeneca Ab | Pharmaceutically useful salts of carboxylic acid derivates |
| WO2006129164A1 (en) | 2005-05-31 | 2006-12-07 | Pfizer Japan Inc. | Substituted aryloxy-n-bicyclomethyl acetamide compounds as vr1 antagonists |
| WO2007004957A1 (en) * | 2005-07-05 | 2007-01-11 | Astrazeneca Ab | Novel crystalline form |
| AR055073A1 (es) * | 2005-07-11 | 2007-08-01 | Astrazeneca Ab | Agentes terapeuticos |
| TWI331523B (en) * | 2005-12-08 | 2010-10-11 | Nat Health Research Institutes | Vinylsulfonate compounds |
| CN101054372B (zh) * | 2006-04-11 | 2010-10-13 | 中国科学院上海药物研究所 | 嘧啶取代苯丙酸衍生化合物、其制法和在治疗多囊肾疾病中的用途 |
| KR100847780B1 (ko) * | 2006-10-26 | 2008-07-23 | 재단법인서울대학교산학협력재단 | 2-에톡시프로피온산 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로함유하는 당뇨병 예방 및 치료제 |
| 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 |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| EP2619198A1 (de) | 2010-09-22 | 2013-07-31 | Arena Pharmaceuticals, Inc. | Modulatoren des gpr119-rezeptors und behandlung von damit assoziierten erkrankungen |
| AU2011326871B2 (en) | 2010-11-08 | 2015-02-12 | Albireo Ab | IBAT inhibitors for the treatment of liver diseases |
| JO3301B1 (ar) * | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| JP6751020B2 (ja) | 2014-06-25 | 2020-09-02 | Ｅａファーマ株式会社 | 固形製剤及びその着色防止又は着色低減方法 |
| EP3012252A1 (de) | 2014-10-24 | 2016-04-27 | Ferring BV | Kristalline Form von elobixibat |
| EP4445956A2 (de) | 2015-01-06 | 2024-10-16 | Arena Pharmaceuticals, Inc. | Wirkstoff zur behandlung von mit s1p1-rezeptor zusammenhängenden erkrankungen |
| WO2016209809A1 (en) | 2015-06-22 | 2016-12-29 | 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(compound1) for use in sipi receptor-associated disorders |
| US10786529B2 (en) | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| CN111032019B (zh) | 2017-08-09 | 2022-07-05 | 阿尔比里奥公司 | 考来烯胺颗粒、口服考来烯胺制剂及其用途 |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| ES2942443T3 (es) | 2018-06-05 | 2023-06-01 | Albireo Ab | Compuestos de benzotia(di)azepina y su uso como moduladores de ácidos biliares |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| TWI823954B (zh) | 2018-06-20 | 2023-12-01 | 瑞典商艾爾比瑞歐公司 | 奧德維希百(odevixibat)之結晶修飾物 |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| JP2023504647A (ja) | 2019-12-04 | 2023-02-06 | アルビレオ・アクチボラグ | ベンゾチア（ジ）アゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| JP2023504643A (ja) | 2019-12-04 | 2023-02-06 | アルビレオ・アクチボラグ | ベンゾチア（ジ）アゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| JP2023504644A (ja) | 2019-12-04 | 2023-02-06 | アルビレオ・アクチボラグ | ベンゾチアジアゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| MX2022006731A (es) | 2019-12-04 | 2022-06-09 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como moduladores del acido biliar. |
| CN116157389A (zh) | 2020-08-03 | 2023-05-23 | 阿尔比里奥公司 | 苯并硫杂(二)氮杂环庚三烯化合物及其作为胆汁酸调节剂的用途 |
| KR20230106651A (ko) | 2020-11-12 | 2023-07-13 | 알비레오 에이비 | 진행성 가족성 간내 담즙정체증(pfic)을 치료하기 위한 오데빅시바트 |
| CA3198216A1 (en) | 2020-12-04 | 2022-06-09 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| WO2023039276A1 (en) * | 2021-09-13 | 2023-03-16 | Curtails Llc | Use of ibat inhibitors and antimicrobials for the treatment of diseases |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE266121C (de) | ||||
| BE489216A (de) | 1948-06-05 | 1900-01-01 | ||
| US2928840A (en) * | 1958-11-26 | 1960-03-15 | Us Vitamin Pharm Corp | 3-(o-substituted phenyl) oxazolidinediones and process therefor |
| GB1081471A (en) | 1963-09-13 | 1967-08-31 | Stauffer Chemical Co | Glycol amide derivatives and use thereof in controlling weed growth |
| US3244398A (en) * | 1963-10-28 | 1966-04-05 | Scaramucci Domer | Composite seat ball valve |
| AT307640B (de) | 1970-06-18 | 1973-05-25 | Richter Gedeon Vegyeszet | Verfahren zur Herstellung von neuen 17-Aza-steroiden und deren Salzen |
| BE792364A (fr) | 1971-12-06 | 1973-06-06 | Basf Ag | Derives de substitution du sulfonylglycolanilide |
| DE2349256C2 (de) | 1973-10-01 | 1985-08-01 | Basf Ag, 6700 Ludwigshafen | 0-Alkylsulfonyl-glykolsäureanilide und diese enthaltende Herbizide |
| DE2828222A1 (de) | 1978-06-28 | 1980-01-10 | Bayer Ag | Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide |
| US4735959A (en) * | 1981-01-10 | 1988-04-05 | Dr. Karl Thomae Gmbh | Carboxylic acid amides and pharmaceutical compositions containing them |
| US5216167A (en) * | 1983-12-30 | 1993-06-01 | Dr. Karl Thomae Gmbh | Phenylacetic acid benzylamides |
| US5312924A (en) * | 1983-12-30 | 1994-05-17 | Dr. Karl Thomae Gmbh | Phenylacetic acid benzylamides |
| US5210208A (en) * | 1990-09-24 | 1993-05-11 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Disubstituted aryl compounds exhibiting selective leukotriene b4 antagonist activity |
| US5958792A (en) | 1995-06-07 | 1999-09-28 | Chiron Corporation | Combinatorial libraries of substrate-bound cyclic organic compounds |
| US6410585B1 (en) * | 1997-08-28 | 2002-06-25 | Scott D. Larsen | Inhibitors of protein tyrosine phosphatase |
| US6353023B1 (en) | 1997-08-28 | 2002-03-05 | Pharmacia & Upjohn Company | Inhibitors of protein tyrosine phosphatase |
| EP1030853A1 (de) | 1997-11-12 | 2000-08-30 | Ariad Pharmaceuticals, Inc. | Neue inhibitoren von signal-transduction, sie enthaltende zusammensetzungen |
| SE9801992D0 (sv) * | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| PL351898A1 (en) | 1999-04-06 | 2003-06-30 | Sankyo Co | O-substituted derivatives of carboxylic acids |
| WO2000061582A1 (fr) | 1999-04-08 | 2000-10-19 | Sankyo Company, Limited | Derives imidazole condenses substitues |
| AU4139600A (en) | 1999-04-14 | 2000-11-14 | University Of British Columbia, The | 1,3-dipolar cycloadditions to polypyrrolic macrocycles |
| AU3958200A (en) | 1999-04-20 | 2000-11-02 | Novo Nordisk A/S | New compounds, their preparation and use |
| YU72201A (sh) | 1999-04-28 | 2005-07-19 | Aventis Pharma Deutschland Gmbh. | Derivati di-aril kiseline kao ppar receptorski ligandi |
| JP4618845B2 (ja) | 1999-06-09 | 2011-01-26 | 杏林製薬株式会社 | ヒトペルオキシゾーム増殖薬活性化受容体（ＰＰＡＲ）αアゴニストとしての置換フェニルプロピオン酸誘導体 |
| TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| JP2001261612A (ja) | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | カテコールプロピオン酸誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
| AU2002222550A1 (en) * | 2000-11-29 | 2002-06-11 | Kyorin Pharmaceutical Co. Ltd. | Substituted carboxylic acid derivatives |
| WO2002044127A1 (fr) * | 2000-11-29 | 2002-06-06 | Kyorin Pharmaceutical Co., Ltd. | Dérivés d'acide carboxylique substitué |
| EP1360172A1 (de) | 2001-02-15 | 2003-11-12 | Pfizer Products Inc. | Ppar agonisten |
| WO2002083616A1 (fr) | 2001-04-10 | 2002-10-24 | Sankyo Company, Limited | DERIVE D'ACIDE GRAS φomega;-ARYLE α-SUBSTITUE |
| SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0229931D0 (en) | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| GB0314079D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| EP1517882A1 (de) * | 2002-06-19 | 2005-03-30 | Eli Lilly And Company | Amidlinker-modulatoren des peroxisom-proliferator-aktivierten rezeptors |
| GB0314134D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314129D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314136D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
-
2001
- 2001-12-19 SE SE0104334A patent/SE0104334D0/xx unknown
-
2002
- 2002-12-18 AU AU2002366315A patent/AU2002366315A1/en not_active Abandoned
- 2002-12-18 PT PT02788145T patent/PT1458672E/pt unknown
- 2002-12-18 UA UA20040604245A patent/UA77987C2/uk unknown
- 2002-12-18 UA UA20040604246A patent/UA77460C2/uk unknown
- 2002-12-18 BR BR0214988-5A patent/BR0214988A/pt not_active IP Right Cessation
- 2002-12-18 CA CA002469302A patent/CA2469302A1/en not_active Abandoned
- 2002-12-18 DK DK02804964T patent/DK1458673T3/da active
- 2002-12-18 IL IL16233002A patent/IL162330A0/xx unknown
- 2002-12-18 DK DK02788145T patent/DK1458672T3/da active
- 2002-12-18 HU HU0402133A patent/HUP0402133A3/hu unknown
- 2002-12-18 MX MXPA04006004A patent/MXPA04006004A/es active IP Right Grant
- 2002-12-18 CN CNA028281551A patent/CN1620423A/zh active Pending
- 2002-12-18 PT PT02804964T patent/PT1458673E/pt unknown
- 2002-12-18 PL PL02370672A patent/PL370672A1/xx not_active Application Discontinuation
- 2002-12-18 KR KR10-2004-7009517A patent/KR20040074094A/ko not_active Application Discontinuation
- 2002-12-18 EP EP02788145A patent/EP1458672B1/de not_active Expired - Lifetime
- 2002-12-18 SI SI200230570T patent/SI1458672T1/sl unknown
- 2002-12-18 AU AU2002352427A patent/AU2002352427A1/en not_active Abandoned
- 2002-12-18 US US10/499,378 patent/US7256307B2/en not_active Expired - Fee Related
- 2002-12-18 SI SI200230424T patent/SI1458673T1/sl unknown
- 2002-12-18 NZ NZ533276A patent/NZ533276A/en unknown
- 2002-12-18 RU RU2004116918/04A patent/RU2300517C2/ru not_active IP Right Cessation
- 2002-12-18 DE DE60214594T patent/DE60214594T2/de not_active Expired - Lifetime
- 2002-12-18 CN CNB2006100071731A patent/CN100406427C/zh not_active Expired - Fee Related
- 2002-12-18 NZ NZ533274A patent/NZ533274A/en unknown
- 2002-12-18 ES ES02804964T patent/ES2271381T3/es not_active Expired - Lifetime
- 2002-12-18 IL IL16233102A patent/IL162331A0/xx unknown
- 2002-12-18 MX MXPA04006003A patent/MXPA04006003A/es active IP Right Grant
- 2002-12-18 TW TW091136519A patent/TWI255807B/zh not_active IP Right Cessation
- 2002-12-18 EP EP02804964A patent/EP1458673B1/de not_active Expired - Lifetime
- 2002-12-18 AT AT02804964T patent/ATE338743T1/de not_active IP Right Cessation
- 2002-12-18 RU RU2004116917/04A patent/RU2303031C2/ru not_active IP Right Cessation
- 2002-12-18 CN CNB028281233A patent/CN1293044C/zh not_active Expired - Fee Related
- 2002-12-18 JP JP2003552709A patent/JP3784804B2/ja not_active Expired - Fee Related
- 2002-12-18 TW TW091136518A patent/TWI253444B/zh not_active IP Right Cessation
- 2002-12-18 AT AT02788145T patent/ATE363466T1/de not_active IP Right Cessation
- 2002-12-18 KR KR10-2004-7009501A patent/KR20040074092A/ko not_active Application Discontinuation
- 2002-12-18 US US10/499,261 patent/US7514471B2/en not_active Expired - Fee Related
- 2002-12-18 DE DE60220441T patent/DE60220441T2/de not_active Expired - Fee Related
- 2002-12-18 JP JP2003552710A patent/JP3820249B2/ja not_active Expired - Lifetime
- 2002-12-18 ES ES02788145T patent/ES2286310T3/es not_active Expired - Lifetime
- 2002-12-18 WO PCT/GB2002/005738 patent/WO2003051821A1/en active IP Right Grant
- 2002-12-18 BR BR0214986-9A patent/BR0214986A/pt not_active IP Right Cessation
- 2002-12-18 HU HU0402022A patent/HUP0402022A3/hu unknown
- 2002-12-18 CA CA002470491A patent/CA2470491A1/en not_active Abandoned
- 2002-12-18 PL PL02370673A patent/PL370673A1/xx not_active Application Discontinuation
- 2002-12-18 WO PCT/GB2002/005744 patent/WO2003051822A1/en active IP Right Grant
- 2002-12-18 MY MYPI20024740A patent/MY132565A/en unknown
- 2002-12-19 AR ARP020105002A patent/AR038045A1/es unknown
- 2002-12-19 AR ARP020105004A patent/AR038047A1/es not_active Application Discontinuation
-
2004
- 2004-06-03 IL IL162330A patent/IL162330A/en not_active IP Right Cessation
- 2004-06-11 ZA ZA200404657A patent/ZA200404657B/en unknown
- 2004-06-11 ZA ZA200404658A patent/ZA200404658B/en unknown
- 2004-06-14 IS IS7309A patent/IS7309A/is unknown
- 2004-06-15 IS IS7313A patent/IS7313A/is unknown
- 2004-07-15 NO NO20043023A patent/NO20043023L/no not_active Application Discontinuation
- 2004-07-16 NO NO20043164A patent/NO20043164L/no not_active Application Discontinuation
-
2005
- 2005-02-01 HK HK05100831A patent/HK1068604A1/xx not_active IP Right Cessation
- 2005-02-16 HK HK05101304A patent/HK1068870A1/xx not_active IP Right Cessation
- 2005-08-16 JP JP2005235794A patent/JP2005336209A/ja active Pending
-
2006
- 2006-04-27 JP JP2006123399A patent/JP2006298924A/ja active Pending
- 2006-12-05 CY CY20061101743T patent/CY1106276T1/el unknown
-
2007
- 2007-08-01 CY CY20071101028T patent/CY1106784T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA77987C2 (en) | Substituted derivatives of phenylpropionic acid as agonists of peroxisome proliferators activated alpha receptor, method for synthesis, pharmaceutical composition, intermediate (variants) | |
| JP3786945B2 (ja) | 治療薬剤 | |
| UA81807C2 (uk) | Фармацевтично корисні солі похідних карбонової кислоти | |
| UA77574C2 (en) | Method for metal strip heat treatment | |
| JP2006182782A (ja) | インスリン抵抗性の処置のためのオルト置換安息香酸誘導体 | |
| JP3810770B2 (ja) | ＰＰＡＲαの選択的アンタゴニストとしての３−フェニル−２−アリールアルキルチオプロピオン酸誘導体 | |
| UA81810C2 (uk) | Похідні 2-етокси-3-фенілпропіонової кислоти для лікування ліпідних розладів |