BRPI0609207A2 - derivados de Ácido pirimidincarboxÍlico e seu uso - Google Patents

Info

Publication number

BRPI0609207A2

BRPI0609207A2 BRPI0609207-1A BRPI0609207A BRPI0609207A2 BR PI0609207 A2 BRPI0609207 A2 BR PI0609207A2 BR PI0609207 A BRPI0609207 A BR PI0609207A BR PI0609207 A2 BRPI0609207 A2 BR PI0609207A2

Authority

BR

Brazil

Prior art keywords

formula

alkyl

alkoxy

see original

original document

Prior art date

2005-03-12

Links

• Espacenet
• Global Dossier
• Discuss

• ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 115
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 230000008569 process Effects 0.000 claims abstract description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 201000010099 disease Diseases 0.000 claims abstract description 16
• 239000003814 drug Substances 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 8
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 238000011321 prophylaxis Methods 0.000 claims abstract description 8
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 6
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 6
• 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 6
• 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 223
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 40
• -1 zinc organic compounds Chemical class 0.000 claims description 38
• 239000012453 solvate Substances 0.000 claims description 35
• 239000011737 fluorine Substances 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 30
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical group 0.000 claims description 28
• 239000002904 solvent Substances 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
• 239000003112 inhibitor Substances 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 21
• 239000000460 chlorine Chemical group 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
• 229910052801 chlorine Chemical group 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000013543 active substance Substances 0.000 claims description 12
• 239000012442 inert solvent Substances 0.000 claims description 12
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 10
• 239000005557 antagonist Substances 0.000 claims description 10
• 230000015572 biosynthetic process Effects 0.000 claims description 10
• 239000000556 agonist Substances 0.000 claims description 9
• 238000003786 synthesis reaction Methods 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 150000007513 acids Chemical class 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 6
• 239000003146 anticoagulant agent Substances 0.000 claims description 6
• 150000001735 carboxylic acids Chemical class 0.000 claims description 6
• 102000004877 Insulin Human genes 0.000 claims description 5
• 108090001061 Insulin Proteins 0.000 claims description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 239000003963 antioxidant agent Substances 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 229940125753 fibrate Drugs 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 102000005962 receptors Human genes 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 239000005541 ACE inhibitor Substances 0.000 claims description 4
• 102000015427 Angiotensins Human genes 0.000 claims description 4
• 108010064733 Angiotensins Proteins 0.000 claims description 4
• 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
• 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
• 230000003178 anti-diabetic effect Effects 0.000 claims description 4
• 239000002876 beta blocker Substances 0.000 claims description 4
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 4
• 239000002934 diuretic Substances 0.000 claims description 4
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
• 229940125396 insulin Drugs 0.000 claims description 4
• 229960003512 nicotinic acid Drugs 0.000 claims description 4
• 239000011664 nicotinic acid Substances 0.000 claims description 4
• 235000001968 nicotinic acid Nutrition 0.000 claims description 4
• 210000001685 thyroid gland Anatomy 0.000 claims description 4
• 239000005495 thyroid hormone Substances 0.000 claims description 4
• 229940036555 thyroid hormone Drugs 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 3
• 229940127470 Lipase Inhibitors Drugs 0.000 claims description 3
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 3
• 150000001409 amidines Chemical class 0.000 claims description 3
• 239000003705 antithrombocytic agent Substances 0.000 claims description 3
• 230000001906 cholesterol absorption Effects 0.000 claims description 3
• 229940030606 diuretics Drugs 0.000 claims description 3
• PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 3
• BMUIXCLLFWRJOQ-UHFFFAOYSA-N ethyl 4-(2,3-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC(C)=C1C BMUIXCLLFWRJOQ-UHFFFAOYSA-N 0.000 claims description 3
• LWRSBFSYHAOCQM-UHFFFAOYSA-N ethyl 4-(2-methylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical class CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1C LWRSBFSYHAOCQM-UHFFFAOYSA-N 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 3
• 229920000642 polymer Polymers 0.000 claims description 3
• 229940031439 squalene Drugs 0.000 claims description 3
• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 3
• KCJKKFMNAXDVEL-UHFFFAOYSA-N 2-phenyl-4-(2,4,5-trichlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=C(Cl)C=C1Cl KCJKKFMNAXDVEL-UHFFFAOYSA-N 0.000 claims description 2
• WDZBQJRINYWGMV-UHFFFAOYSA-N 4-(2-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O WDZBQJRINYWGMV-UHFFFAOYSA-N 0.000 claims description 2
• 108010016731 PPAR gamma Proteins 0.000 claims description 2
• 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 claims description 2
• 229940127219 anticoagulant drug Drugs 0.000 claims description 2
• 239000003054 catalyst Substances 0.000 claims description 2
• 229910052763 palladium Inorganic materials 0.000 claims description 2
• 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 claims description 2
• 229910052725 zinc Inorganic materials 0.000 claims description 2
• 239000011701 zinc Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 14
• 150000003973 alkyl amines Chemical class 0.000 claims 2
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical group [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims 2
• 102100033868 Cannabinoid receptor 1 Human genes 0.000 claims 1
• 101710187010 Cannabinoid receptor 1 Proteins 0.000 claims 1
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 66
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 102
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 66
• 238000005160 1H NMR spectroscopy Methods 0.000 description 63
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 49
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 37
• 239000000203 mixture Substances 0.000 description 36
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 238000004128 high performance liquid chromatography Methods 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 239000003480 eluent Substances 0.000 description 23
• 238000007429 general method Methods 0.000 description 23
• 239000000243 solution Substances 0.000 description 23
• 229910000027 potassium carbonate Inorganic materials 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 17
• 235000019253 formic acid Nutrition 0.000 description 17
• OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 238000012360 testing method Methods 0.000 description 11
• 238000000825 ultraviolet detection Methods 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 150000003254 radicals Chemical class 0.000 description 10
• 235000011121 sodium hydroxide Nutrition 0.000 description 10
• 150000003626 triacylglycerols Chemical class 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 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 9
• 239000002585 base Substances 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000000018 receptor agonist Substances 0.000 description 7
• 229940044601 receptor agonist Drugs 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 210000004369 blood Anatomy 0.000 description 6
• 239000008280 blood Substances 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 102000023984 PPAR alpha Human genes 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 5
• 230000000144 pharmacologic effect Effects 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 108010028554 LDL Cholesterol Proteins 0.000 description 4
• 238000008214 LDL Cholesterol Methods 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• 235000006708 antioxidants Nutrition 0.000 description 4
• 230000000923 atherogenic effect Effects 0.000 description 4
• 230000027455 binding Effects 0.000 description 4
• 230000036772 blood pressure Effects 0.000 description 4
• 238000010494 dissociation reaction Methods 0.000 description 4
• 230000005593 dissociations Effects 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 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
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 210000002966 serum Anatomy 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 3
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 229940123208 Biguanide Drugs 0.000 description 3
• 229940122820 Cannabinoid receptor antagonist Drugs 0.000 description 3
• MZPMUWYUEZURIN-UHFFFAOYSA-N ClC1=C(C[Zn])C=CC=C1.[Br] Chemical compound ClC1=C(C[Zn])C=CC=C1.[Br] MZPMUWYUEZURIN-UHFFFAOYSA-N 0.000 description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
• 108010049003 Fibrinogen Proteins 0.000 description 3
• 102000008946 Fibrinogen Human genes 0.000 description 3
• 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 3
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
• 108010007622 LDL Lipoproteins Proteins 0.000 description 3
• 102000007330 LDL Lipoproteins Human genes 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 3
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• 235000019270 ammonium chloride Nutrition 0.000 description 3
• 229960004676 antithrombotic agent Drugs 0.000 description 3
• 239000003536 cannabinoid receptor antagonist Substances 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 235000012000 cholesterol Nutrition 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000001514 detection method Methods 0.000 description 3
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 229940012952 fibrinogen Drugs 0.000 description 3
• 239000008103 glucose Substances 0.000 description 3
• 239000003316 glycosidase inhibitor Substances 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 150000002430 hydrocarbons Chemical class 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 210000004185 liver Anatomy 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 239000003614 peroxisome proliferator Substances 0.000 description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
• 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 239000003643 water by type Substances 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 2
• OFJRNBWSFXEHSA-UHFFFAOYSA-N 2-(3-amino-1,2-benzoxazol-5-yl)-n-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CN(C)CC1=NC=CN1C(C=C1F)=CC=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=CC=C(ON=C2N)C2=C1 OFJRNBWSFXEHSA-UHFFFAOYSA-N 0.000 description 2
• JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 2
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
• UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical class ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
• VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• LHEZBZQXLZNMOA-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O LHEZBZQXLZNMOA-UHFFFAOYSA-N 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 201000004624 Dermatitis Diseases 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 102100039556 Galectin-4 Human genes 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
• 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 2
• 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 2
• 102100021711 Ileal sodium/bile acid cotransporter Human genes 0.000 description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
• 108060001084 Luciferase Proteins 0.000 description 2
• 239000005089 Luciferase Substances 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• 108700010041 Nicotinic acid receptor Proteins 0.000 description 2
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
• 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 2
• 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
• 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• 229920001304 Solutol HS 15 Polymers 0.000 description 2
• AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 239000003472 antidiabetic agent Substances 0.000 description 2
• 238000003556 assay Methods 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 150000004283 biguanides Chemical class 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
• 229950005499 carbon tetrachloride Drugs 0.000 description 2
• 150000001733 carboxylic acid esters Chemical class 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 229960001701 chloroform Drugs 0.000 description 2
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 230000006806 disease prevention Effects 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 238000010931 ester hydrolysis Methods 0.000 description 2
• 239000012894 fetal calf serum Substances 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 150000008282 halocarbons Chemical class 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 150000004677 hydrates Chemical class 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 208000006575 hypertriglyceridemia Diseases 0.000 description 2
• 230000002218 hypoglycaemic effect Effects 0.000 description 2
• 239000007943 implant Substances 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 208000017169 kidney disease Diseases 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 102000005861 leptin receptors Human genes 0.000 description 2
• 108010019813 leptin receptors Proteins 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• 239000002609 medium Substances 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• 235000013336 milk Nutrition 0.000 description 2
• 239000008267 milk Substances 0.000 description 2
• 210000004080 milk Anatomy 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 102000006255 nuclear receptors Human genes 0.000 description 2
• 108020004017 nuclear receptors Proteins 0.000 description 2
• 229940100688 oral solution Drugs 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 229940049954 penicillin Drugs 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 150000002989 phenols Chemical class 0.000 description 2
• 229960005095 pioglitazone Drugs 0.000 description 2
• 125000004193 piperazinyl group Chemical group 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• 229950008882 polysorbate Drugs 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
• 238000003825 pressing Methods 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 239000002516 radical scavenger Substances 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 210000002784 stomach Anatomy 0.000 description 2
• 229960005322 streptomycin Drugs 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 229910052717 sulfur Inorganic materials 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
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 150000001467 thiazolidinediones Chemical class 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
• CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
• NXWGWUVGUSFQJC-GFCCVEGCSA-N (2r)-1-[(2-methyl-1h-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-GFCCVEGCSA-N 0.000 description 1
• DMYZJLOWGSRVKP-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)NC1=CC=C(Cl)C=C1 DMYZJLOWGSRVKP-RTBURBONSA-N 0.000 description 1
• LJCBAPRMNYSDOP-LVCYMWGESA-N (2s)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3s)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid;hydron;chloride;pentahydrate Chemical compound O.O.O.O.O.Cl.C1N(C(=N)C)CC[C@@H]1OC1=CC=C([C@H](CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(O)=O)C=C1 LJCBAPRMNYSDOP-LVCYMWGESA-N 0.000 description 1
• 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 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
• METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
• KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 description 1
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
• 125000004161 1,4-diazepinyl group Chemical group 0.000 description 1
• PURSZYWBIQIANP-UHFFFAOYSA-N 1-(bromomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CBr PURSZYWBIQIANP-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
• ZUCFGSAENWHFPO-UHFFFAOYSA-N 1-[4-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-[3-(3-hydroxypropoxy)phenyl]-2-oxo-1,8-naphthyridin-3-yl]urea;hydrate;hydrochloride Chemical compound O.Cl.CC(C)C=1C=C(N)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C1=CC=CC(OCCCO)=C1 ZUCFGSAENWHFPO-UHFFFAOYSA-N 0.000 description 1
• PMGZJNCIQHGNLT-UHFFFAOYSA-N 1-[bis(2,2-dimethylpropanoyloxymethoxy)phosphoryl]-4-(3-phenoxyphenyl)butane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C(S(O)(=O)=O)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PMGZJNCIQHGNLT-UHFFFAOYSA-N 0.000 description 1
• GUSVHVVOABZHAH-OPZWKQDFSA-N 1aw8p77hkj Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GUSVHVVOABZHAH-OPZWKQDFSA-N 0.000 description 1
• BLJBBKAZKREJGI-UHFFFAOYSA-N 2,3-dichlorooxirane Chemical class ClC1OC1Cl BLJBBKAZKREJGI-UHFFFAOYSA-N 0.000 description 1
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
• UTYTWAQOXSZJIM-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)-4-(2-chlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(C=2N=C(OC=3C(=CC=CC=3)Cl)C(C(O)=O)=CN=2)=C1 UTYTWAQOXSZJIM-UHFFFAOYSA-N 0.000 description 1
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
• CMLUGNQVANVZHY-POURPWNDSA-N 2-[1-[2-[(3r,5s)-1-(3-acetyloxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)COC(C)=O)C(=O)[C@@H](CC(=O)N3CCC(CC(O)=O)CC3)O2)=C1OC CMLUGNQVANVZHY-POURPWNDSA-N 0.000 description 1
• FZWCOQHVCJQFSQ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-4-(2,5-dichlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N=C1OC1=CC(Cl)=CC=C1Cl FZWCOQHVCJQFSQ-UHFFFAOYSA-N 0.000 description 1
• UDMJFEZKKVOXKU-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-4-(2-chlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N=C1OC1=CC=CC=C1Cl UDMJFEZKKVOXKU-UHFFFAOYSA-N 0.000 description 1
• SUIZARUATMVYRT-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)phenol Chemical compound OC1=CC(C(F)(F)F)=CC=C1Cl SUIZARUATMVYRT-UHFFFAOYSA-N 0.000 description 1
• VCDJPGDATCBGMF-UHFFFAOYSA-N 2-fluorobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC=C1F VCDJPGDATCBGMF-UHFFFAOYSA-N 0.000 description 1
• GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 1
• SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 1
• CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
• YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 description 1
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
• LKVQFNAKRYHEAT-UHFFFAOYSA-N 3,4,5-trifluorobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC(F)=C(F)C(F)=C1 LKVQFNAKRYHEAT-UHFFFAOYSA-N 0.000 description 1
• WIFHYQZBCRLTBT-UHFFFAOYSA-N 3,4-difluorobenzenecarboximidamide;hydron;chloride Chemical compound Cl.NC(=N)C1=CC=C(F)C(F)=C1 WIFHYQZBCRLTBT-UHFFFAOYSA-N 0.000 description 1
• DPDIFHFFPSBNLT-UHFFFAOYSA-N 3,4-dimethylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CC1=CC=C(C(N)=N)C=C1C DPDIFHFFPSBNLT-UHFFFAOYSA-N 0.000 description 1
• NLZGCTAVRJBVFN-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzenecarboximidamide Chemical compound NC(=N)C1=CC=C(C(F)(F)F)C(F)=C1 NLZGCTAVRJBVFN-UHFFFAOYSA-N 0.000 description 1
• UXNPMDKLHYMKBZ-UHFFFAOYSA-N 3-hydroxy-4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1O UXNPMDKLHYMKBZ-UHFFFAOYSA-N 0.000 description 1
• AGURKSYKTJQPNA-UHFFFAOYSA-N 4,6-ditert-butyl-2,2-dipentyl-3h-1-benzofuran-5-ol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C2=C1OC(CCCCC)(CCCCC)C2 AGURKSYKTJQPNA-UHFFFAOYSA-N 0.000 description 1
• OOIWZCIYNAWTKJ-UHFFFAOYSA-N 4-(2,3-dichlorophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC(Cl)=C1Cl OOIWZCIYNAWTKJ-UHFFFAOYSA-N 0.000 description 1
• CEXYFIOWJQXJCK-UHFFFAOYSA-N 4-(2,4-dichloro-3,5-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=C(Cl)C(C)=CC(OC=2C(=CN=C(N=2)C=2C=CC=CC=2)C(O)=O)=C1Cl CEXYFIOWJQXJCK-UHFFFAOYSA-N 0.000 description 1
• VMMMZKHSCYVBDX-UHFFFAOYSA-N 4-(2,4-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC(C)=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O VMMMZKHSCYVBDX-UHFFFAOYSA-N 0.000 description 1
• ARLIUSBWSBBZAO-UHFFFAOYSA-N 4-(2,5-dichlorophenoxy)-2-(3-fluoro-4-methylphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(F)C(C)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=C(Cl)C=2)Cl)=N1 ARLIUSBWSBBZAO-UHFFFAOYSA-N 0.000 description 1
• MJDHNKWKAUHBNL-UHFFFAOYSA-N 4-(2,5-dichlorophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=CC=C1Cl MJDHNKWKAUHBNL-UHFFFAOYSA-N 0.000 description 1
• ZORFSJKGOCFHBR-UHFFFAOYSA-N 4-(2,5-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=C(C)C(OC=2C(=CN=C(N=2)C=2C=CC=CC=2)C(O)=O)=C1 ZORFSJKGOCFHBR-UHFFFAOYSA-N 0.000 description 1
• MGDQSOJZANHDQI-UHFFFAOYSA-N 4-(2-bromophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1Br MGDQSOJZANHDQI-UHFFFAOYSA-N 0.000 description 1
• DKGKYAGUCOQKAY-UHFFFAOYSA-N 4-(2-chloro-4-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O DKGKYAGUCOQKAY-UHFFFAOYSA-N 0.000 description 1
• DVIKIUXSTAWLBR-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(2-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C(=CC=CC=2)F)N=C1OC1=CC=CC=C1Cl DVIKIUXSTAWLBR-UHFFFAOYSA-N 0.000 description 1
• ORBKHCZNWCJDMU-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(3,4,5-trifluorophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(F)C(F)=C(F)C=2)N=C1OC1=CC=CC=C1Cl ORBKHCZNWCJDMU-UHFFFAOYSA-N 0.000 description 1
• KEIDAINLIAVULD-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(3,4-difluorophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(F)C(F)=CC=2)N=C1OC1=CC=CC=C1Cl KEIDAINLIAVULD-UHFFFAOYSA-N 0.000 description 1
• SGCSRODTNHPOFV-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(3,4-dimethylphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=CC=2)Cl)=N1 SGCSRODTNHPOFV-UHFFFAOYSA-N 0.000 description 1
• JAXSSPXYYHWOPI-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(3-fluoro-4-methylphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(F)C(C)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=CC=2)Cl)=N1 JAXSSPXYYHWOPI-UHFFFAOYSA-N 0.000 description 1
• FSESUBCNSPCGFM-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(3-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(F)C=CC=2)N=C1OC1=CC=CC=C1Cl FSESUBCNSPCGFM-UHFFFAOYSA-N 0.000 description 1
• MALRBCIDKYOKMC-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(4-fluoro-3-methoxyphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(F)C(OC)=CC(C=2N=C(OC=3C(=CC=CC=3)Cl)C(C(O)=O)=CN=2)=C1 MALRBCIDKYOKMC-UHFFFAOYSA-N 0.000 description 1
• FHVNCVAREODGAV-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(4-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC(F)=CC=2)N=C1OC1=CC=CC=C1Cl FHVNCVAREODGAV-UHFFFAOYSA-N 0.000 description 1
• IAPQGLIWZHXMOM-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(4-methoxyphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=CC=2)Cl)=N1 IAPQGLIWZHXMOM-UHFFFAOYSA-N 0.000 description 1
• AEZZGQKHVICHJA-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(4-methyl-3-nitrophenyl)pyrimidine-5-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=CC=2)Cl)=N1 AEZZGQKHVICHJA-UHFFFAOYSA-N 0.000 description 1
• VNFZDSHOGGJIML-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-(4-methylphenyl)pyrimidine-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC=C(C(O)=O)C(OC=2C(=CC=CC=2)Cl)=N1 VNFZDSHOGGJIML-UHFFFAOYSA-N 0.000 description 1
• DIEGAGJUPJAEKW-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=C(F)C(=CC=2)C(F)(F)F)N=C1OC1=CC=CC=C1Cl DIEGAGJUPJAEKW-UHFFFAOYSA-N 0.000 description 1
• OUWLOUPCMRYBOD-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1Cl OUWLOUPCMRYBOD-UHFFFAOYSA-N 0.000 description 1
• HZECXPTVKQVWHB-UHFFFAOYSA-N 4-(2-cyanophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1C#N HZECXPTVKQVWHB-UHFFFAOYSA-N 0.000 description 1
• LVAGVIMFCGRRQP-UHFFFAOYSA-N 4-(2-fluorophenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1F LVAGVIMFCGRRQP-UHFFFAOYSA-N 0.000 description 1
• WCNVGPPMZKOEHB-UHFFFAOYSA-N 4-(5-chloro-2-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=C(Cl)C=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O WCNVGPPMZKOEHB-UHFFFAOYSA-N 0.000 description 1
• XPBOQIROMVVETC-UHFFFAOYSA-N 4-(5-cyano-2-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=C(C#N)C=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O XPBOQIROMVVETC-UHFFFAOYSA-N 0.000 description 1
• NOBZETMXGVAWIM-UHFFFAOYSA-N 4-[(2-carbamimidoyl-3,4-dihydro-1h-isoquinolin-7-yl)oxymethyl]-1-pyridin-4-ylpiperidine-4-carboxylic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=C2CN(C(=N)N)CCC2=CC=C1OCC(CC1)(C(O)=O)CCN1C1=CC=NC=C1 NOBZETMXGVAWIM-UHFFFAOYSA-N 0.000 description 1
• PFLAORIGDZBNEH-UHFFFAOYSA-N 4-[(2-chlorophenyl)methyl]-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1CC1=CC=CC=C1Cl PFLAORIGDZBNEH-UHFFFAOYSA-N 0.000 description 1
• VRICOVYXHPULSM-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenoxy]-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(C(F)(F)F)=CC=C1Cl VRICOVYXHPULSM-UHFFFAOYSA-N 0.000 description 1
• ZOAZKNCJPDBJMZ-UHFFFAOYSA-N 4-chloro-3-methylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CC1=CC(C(N)=N)=CC=C1Cl ZOAZKNCJPDBJMZ-UHFFFAOYSA-N 0.000 description 1
• KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 description 1
• QYWLIQSKUKCVPL-UHFFFAOYSA-N 4-fluoro-3-methoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.COC1=CC(C(N)=N)=CC=C1F QYWLIQSKUKCVPL-UHFFFAOYSA-N 0.000 description 1
• BXPBQGOKPVBXOE-UHFFFAOYSA-N 4-phenoxy-2-phenylpyrimidine-5-carboxylic acid Chemical class OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1 BXPBQGOKPVBXOE-UHFFFAOYSA-N 0.000 description 1
• KKFPXGXMSBBNJI-UHFFFAOYSA-N 5-chloro-2-methylphenol Chemical compound CC1=CC=C(Cl)C=C1O KKFPXGXMSBBNJI-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 102000004146 ATP citrate synthases Human genes 0.000 description 1
• 108090000662 ATP citrate synthases Proteins 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
• 208000002874 Acne Vulgaris Diseases 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
• 206010002091 Anaesthesia Diseases 0.000 description 1
• 206010002383 Angina Pectoris Diseases 0.000 description 1
• 102000005666 Apolipoprotein A-I Human genes 0.000 description 1
• 108010059886 Apolipoprotein A-I Proteins 0.000 description 1
• 102000007592 Apolipoproteins Human genes 0.000 description 1
• 108010071619 Apolipoproteins Proteins 0.000 description 1
• 102000006410 Apoproteins Human genes 0.000 description 1
• 108010083590 Apoproteins Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 206010003178 Arterial thrombosis Diseases 0.000 description 1
• 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 description 1
• 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 description 1
• 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 1
• 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
• 108010073466 Bombesin Receptors Proteins 0.000 description 1
• 239000002083 C09CA01 - Losartan Substances 0.000 description 1
• 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
• 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
• 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
• 229940124638 COX inhibitor Drugs 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 description 1
• 108091006146 Channels Proteins 0.000 description 1
• 229940122444 Chemokine receptor antagonist Drugs 0.000 description 1
• 244000138502 Chenopodium bonus henricus Species 0.000 description 1
• 235000008645 Chenopodium bonus henricus Nutrition 0.000 description 1
• 208000010445 Chilblains Diseases 0.000 description 1
• 206010008528 Chillblains Diseases 0.000 description 1
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
• 229920002911 Colestipol Polymers 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 208000031288 Combined hyperlipidaemia Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 241000699802 Cricetulus griseus Species 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
• 230000004568 DNA-binding Effects 0.000 description 1
• 206010012289 Dementia Diseases 0.000 description 1
• 208000020401 Depressive disease Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• YARKMNAWFIMDKV-UHFFFAOYSA-N Epanolol Chemical compound C=1C=CC=C(C#N)C=1OCC(O)CNCCNC(=O)CC1=CC=C(O)C=C1 YARKMNAWFIMDKV-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 229940123583 Factor Xa inhibitor Drugs 0.000 description 1
• 108090000331 Firefly luciferases Proteins 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• 102000051325 Glucagon Human genes 0.000 description 1
• 108060003199 Glucagon Proteins 0.000 description 1
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 1
• FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound 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
• 208000002705 Glucose Intolerance Diseases 0.000 description 1
• 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
• 229940122069 Glycosidase inhibitor Drugs 0.000 description 1
• 201000005569 Gout Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 108010002059 Histamine Receptors Proteins 0.000 description 1
• 102000000543 Histamine Receptors Human genes 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101100109133 Homo sapiens APOA1 gene Proteins 0.000 description 1
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 description 1
• 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
• 241000701024 Human betaherpesvirus 5 Species 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010021024 Hypolipidaemia Diseases 0.000 description 1
• 101710156096 Ileal sodium/bile acid cotransporter Proteins 0.000 description 1
• 206010021639 Incontinence Diseases 0.000 description 1
• 206010022489 Insulin Resistance Diseases 0.000 description 1
• 229940122355 Insulin sensitizer Drugs 0.000 description 1
• 102100025306 Integrin alpha-IIb Human genes 0.000 description 1
• 101710149643 Integrin alpha-IIb Proteins 0.000 description 1
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• 102000000853 LDL receptors Human genes 0.000 description 1
• 108010001831 LDL receptors Proteins 0.000 description 1
• 102000003680 Leukotriene B4 receptors Human genes 0.000 description 1
• 108090000093 Leukotriene B4 receptors Proteins 0.000 description 1
• 229940086609 Lipase inhibitor Drugs 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 235000019759 Maize starch Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 208000001145 Metabolic Syndrome Diseases 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 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
• ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-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
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 208000010428 Muscle Weakness Diseases 0.000 description 1
• 206010028372 Muscular weakness Diseases 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• 238000011785 NMRI mouse Methods 0.000 description 1
• 201000009053 Neurodermatitis Diseases 0.000 description 1
• 101100297828 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chol-2 gene Proteins 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• 108091028043 Nucleic acid sequence Proteins 0.000 description 1
• 206010030113 Oedema Diseases 0.000 description 1
• 102000002512 Orexin Human genes 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 102000000536 PPAR gamma Human genes 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
• 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 description 1
• 241000254064 Photinus pyralis Species 0.000 description 1
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 229940127343 Potassium Channel Agonists Drugs 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
• 201000004681 Psoriasis Diseases 0.000 description 1
• 241000700157 Rattus norvegicus Species 0.000 description 1
• 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
• QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy 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
• 108091006614 SLC10A2 Proteins 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 238000000692 Student's t-test Methods 0.000 description 1
• RKSMVPNZHBRNNS-UHFFFAOYSA-N Succinobucol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SC(C)(C)SC=2C=C(C(OC(=O)CCC(O)=O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 RKSMVPNZHBRNNS-UHFFFAOYSA-N 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 1
• 229940123464 Thiazolidinedione Drugs 0.000 description 1
• 108090000190 Thrombin Proteins 0.000 description 1
• 229940122388 Thrombin inhibitor Drugs 0.000 description 1
• 102000006601 Thymidine Kinase Human genes 0.000 description 1
• 108020004440 Thymidine kinase Proteins 0.000 description 1
• JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 206010047249 Venous thrombosis Diseases 0.000 description 1
• 208000000260 Warts Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 229960000446 abciximab Drugs 0.000 description 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
• 206010000210 abortion Diseases 0.000 description 1
• 231100000176 abortion Toxicity 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 238000010306 acid treatment Methods 0.000 description 1
• 229950000146 acifran Drugs 0.000 description 1
• DFDGRKNOFOJBAJ-UHFFFAOYSA-N acifran Chemical compound C=1C=CC=CC=1C1(C)OC(C(O)=O)=CC1=O DFDGRKNOFOJBAJ-UHFFFAOYSA-N 0.000 description 1
• 229960003526 acipimox Drugs 0.000 description 1
• 206010000496 acne Diseases 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• IPGLIOFIFLXLKR-AXYNENQYSA-N adaprolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CC(=O)OCCC1(C2)C[C@@H](C3)C[C@H]2C[C@@H]3C1 IPGLIOFIFLXLKR-AXYNENQYSA-N 0.000 description 1
• 229950000221 adaprolol Drugs 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 229940083712 aldosterone antagonist Drugs 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Chemical class OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229960002213 alprenolol Drugs 0.000 description 1
• PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
• 229960000528 amlodipine Drugs 0.000 description 1
• ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000037005 anaesthesia Effects 0.000 description 1
• 229940035676 analgesics Drugs 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 210000004102 animal cell Anatomy 0.000 description 1
• 230000000578 anorexic effect Effects 0.000 description 1
• 239000000730 antalgic agent Substances 0.000 description 1
• 230000001741 anti-phlogistic effect Effects 0.000 description 1
• 230000002785 anti-thrombosis Effects 0.000 description 1
• 229940127090 anticoagulant agent Drugs 0.000 description 1
• 239000000935 antidepressant agent Substances 0.000 description 1
• 229940005513 antidepressants Drugs 0.000 description 1
• 229940125708 antidiabetic agent Drugs 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 239000003698 antivitamin K Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 229960002274 atenolol Drugs 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
• 229910001863 barium hydroxide Inorganic materials 0.000 description 1
• LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229960004324 betaxolol Drugs 0.000 description 1
• CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229960002781 bisoprolol Drugs 0.000 description 1
• VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
• OIRCOABEOLEUMC-GEJPAHFPSA-N bivalirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 OIRCOABEOLEUMC-GEJPAHFPSA-N 0.000 description 1
• 229960001500 bivalirudin Drugs 0.000 description 1
• 108010055460 bivalirudin Proteins 0.000 description 1
• 230000017531 blood circulation Effects 0.000 description 1
• 210000001772 blood platelet Anatomy 0.000 description 1
• 229960000330 bupranolol Drugs 0.000 description 1
• HQIRNZOQPUAHHV-UHFFFAOYSA-N bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 239000000480 calcium channel blocker Substances 0.000 description 1
• ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical class [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 1
• SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
• 229960000932 candesartan 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
• 229960000830 captopril Drugs 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 235000014633 carbohydrates Nutrition 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 238000012754 cardiac puncture Methods 0.000 description 1
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
• 229960001222 carteolol Drugs 0.000 description 1
• LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 1
• 229960004195 carvedilol Drugs 0.000 description 1
• NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
• 229960002320 celiprolol Drugs 0.000 description 1
• 238000000423 cell based assay Methods 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 208000015114 central nervous system 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
• NPNSVNGQJGRSNR-UHFFFAOYSA-N chembl73193 Chemical compound N=1C(OC=2C(=CC=C(C=2)C(N)=N)O)=C(F)C(N(CC(O)=O)C)=C(F)C=1OC(C=1)=CC=CC=1C1=NCCN1C NPNSVNGQJGRSNR-UHFFFAOYSA-N 0.000 description 1
• 238000000451 chemical ionisation Methods 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000002559 chemokine receptor antagonist Substances 0.000 description 1
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
• 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 1
• 208000019425 cirrhosis of liver Diseases 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 229960002896 clonidine Drugs 0.000 description 1
• 238000010367 cloning Methods 0.000 description 1
• GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
• 229960003009 clopidogrel Drugs 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
• 229960004126 codeine Drugs 0.000 description 1
• GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 1
• 229960002604 colestipol Drugs 0.000 description 1
• 238000004590 computer program Methods 0.000 description 1
• 229960000956 coumarin Drugs 0.000 description 1
• 235000001671 coumarin Nutrition 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• IJNIQYINMSGIPS-UHFFFAOYSA-N darexaban Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC(O)=C1NC(=O)C1=CC=C(N2CCN(C)CCC2)C=C1 IJNIQYINMSGIPS-UHFFFAOYSA-N 0.000 description 1
• 229960002887 deanol Drugs 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 230000003247 decreasing effect Effects 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
• 229960005227 delapril Drugs 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 229960001767 dextrothyroxine Drugs 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• FPUQGCOBYOXAED-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FPUQGCOBYOXAED-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 229960002877 dihydralazine Drugs 0.000 description 1
• VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 1
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
• 229960004166 diltiazem Drugs 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 230000003467 diminishing effect Effects 0.000 description 1
• IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
• 229960002768 dipyridamole Drugs 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000001882 diuretic effect Effects 0.000 description 1
• GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 239000003651 drinking water Substances 0.000 description 1
• 235000020188 drinking water Nutrition 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 229960000622 edoxaban Drugs 0.000 description 1
• PSMMNJNZVZZNOI-SJILXJHISA-N edoxaban tosylate hydrate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1.N([C@H]1CC[C@@H](C[C@H]1NC(=O)C=1SC=2CN(C)CCC=2N=1)C(=O)N(C)C)C(=O)C(=O)NC1=CC=C(Cl)C=N1 PSMMNJNZVZZNOI-SJILXJHISA-N 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• XFLQIRAKKLNXRQ-UUWRZZSWSA-N elobixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)NCC(O)=O)C=3C=CC=CC=3)C=C2S(=O)(=O)CC(CCCC)(CCCC)CN1C1=CC=CC=C1 XFLQIRAKKLNXRQ-UUWRZZSWSA-N 0.000 description 1
• 229950006127 embusartan Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 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 1
• 229960000873 enalapril Drugs 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• 229960002711 epanolol Drugs 0.000 description 1
• 206010015037 epilepsy Diseases 0.000 description 1
• 229960003745 esmolol Drugs 0.000 description 1
• AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical compound COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical class CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• NWGUSKXVQHPSTL-UHFFFAOYSA-N ethyl 2-(3,4-difluorophenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(F)C(F)=C1 NWGUSKXVQHPSTL-UHFFFAOYSA-N 0.000 description 1
• FSBVKDDTBMJFTF-UHFFFAOYSA-N ethyl 2-(3,4-dimethylphenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(C)C(C)=C1 FSBVKDDTBMJFTF-UHFFFAOYSA-N 0.000 description 1
• JMKDZJFOSRWVNH-UHFFFAOYSA-N ethyl 2-(3-fluoro-4-methylphenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(C)C(F)=C1 JMKDZJFOSRWVNH-UHFFFAOYSA-N 0.000 description 1
• FACMLVAQNLLNPL-UHFFFAOYSA-N ethyl 2-(4-chloro-3-methylphenyl)-4-(2-chlorophenoxy)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(C)C(Cl)=CC=2)N=C1OC1=CC=CC=C1Cl FACMLVAQNLLNPL-UHFFFAOYSA-N 0.000 description 1
• WYCVRECEUGMSMT-UHFFFAOYSA-N ethyl 2-(4-chloro-3-methylphenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(Cl)C(C)=C1 WYCVRECEUGMSMT-UHFFFAOYSA-N 0.000 description 1
• HXCVYKLNNWVKKA-UHFFFAOYSA-N ethyl 2-(4-methyl-3-nitrophenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(C)C([N+]([O-])=O)=C1 HXCVYKLNNWVKKA-UHFFFAOYSA-N 0.000 description 1
• MZPNBNHCQDXZBK-UHFFFAOYSA-N ethyl 2-[3,5-bis(trifluoromethyl)phenyl]-4-(2-chlorophenoxy)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N=C1OC1=CC=CC=C1Cl MZPNBNHCQDXZBK-UHFFFAOYSA-N 0.000 description 1
• SGAZJHBVFUCANY-UHFFFAOYSA-N ethyl 2-[3,5-bis(trifluoromethyl)phenyl]-4-chloropyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SGAZJHBVFUCANY-UHFFFAOYSA-N 0.000 description 1
• CAXSNXDYDLFJJE-UHFFFAOYSA-N ethyl 2-[3,5-bis(trifluoromethyl)phenyl]-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CAXSNXDYDLFJJE-UHFFFAOYSA-N 0.000 description 1
• QTEBDGVFYWXBAQ-UHFFFAOYSA-N ethyl 2-[3-fluoro-4-(trifluoromethyl)phenyl]-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=C(C(F)(F)F)C(F)=C1 QTEBDGVFYWXBAQ-UHFFFAOYSA-N 0.000 description 1
• NLJDAATYJCNAGQ-UHFFFAOYSA-N ethyl 4-(2,5-dichlorophenoxy)-2-(3-fluoro-4-methylphenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(F)C(C)=CC=2)N=C1OC1=CC(Cl)=CC=C1Cl NLJDAATYJCNAGQ-UHFFFAOYSA-N 0.000 description 1
• ZWKCKPPWFGDSRO-UHFFFAOYSA-N ethyl 4-(2,5-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(C)=CC=C1C ZWKCKPPWFGDSRO-UHFFFAOYSA-N 0.000 description 1
• KLGDRCBRARPONF-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-(3,4,5-trifluorophenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(F)C(F)=C(F)C=2)N=C1OC1=CC=CC=C1Cl KLGDRCBRARPONF-UHFFFAOYSA-N 0.000 description 1
• UAKKTEOAEVANIY-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-(3,4-difluorophenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(F)C(F)=CC=2)N=C1OC1=CC=CC=C1Cl UAKKTEOAEVANIY-UHFFFAOYSA-N 0.000 description 1
• NFQNXVXXEQPYLS-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-(3-fluoro-4-methylphenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(F)C(C)=CC=2)N=C1OC1=CC=CC=C1Cl NFQNXVXXEQPYLS-UHFFFAOYSA-N 0.000 description 1
• FCISLJXHELNYAL-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-(4-fluoro-3-methoxyphenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(OC)C(F)=CC=2)N=C1OC1=CC=CC=C1Cl FCISLJXHELNYAL-UHFFFAOYSA-N 0.000 description 1
• KWOTWKIWMVUHCP-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-(4-methyl-3-nitrophenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(C(C)=CC=2)[N+]([O-])=O)N=C1OC1=CC=CC=C1Cl KWOTWKIWMVUHCP-UHFFFAOYSA-N 0.000 description 1
• MXACWVAHNQLWPO-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=C(F)C(=CC=2)C(F)(F)F)N=C1OC1=CC=CC=C1Cl MXACWVAHNQLWPO-UHFFFAOYSA-N 0.000 description 1
• OYLKLPZWPMOCQU-UHFFFAOYSA-N ethyl 4-(2-chlorophenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1Cl OYLKLPZWPMOCQU-UHFFFAOYSA-N 0.000 description 1
• RTRSQDWGYKVGSM-UHFFFAOYSA-N ethyl 4-(2-cyanophenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC=C1C#N RTRSQDWGYKVGSM-UHFFFAOYSA-N 0.000 description 1
• KNSICBQVIAYZMF-UHFFFAOYSA-N ethyl 4-(5-chloro-2-methylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=CC=C1C KNSICBQVIAYZMF-UHFFFAOYSA-N 0.000 description 1
• LRBUIFJIEXMLIH-UHFFFAOYSA-N ethyl 4-(5-cyano-2-methylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(C#N)=CC=C1C LRBUIFJIEXMLIH-UHFFFAOYSA-N 0.000 description 1
• MEUQVGZOWSTIQY-UHFFFAOYSA-N ethyl 4-[(2-chlorophenyl)methyl]-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1CC1=CC=CC=C1Cl MEUQVGZOWSTIQY-UHFFFAOYSA-N 0.000 description 1
• OUOCOLQMRRARFG-UHFFFAOYSA-N ethyl 4-[2-chloro-5-(trifluoromethyl)phenoxy]-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(C(F)(F)F)=CC=C1Cl OUOCOLQMRRARFG-UHFFFAOYSA-N 0.000 description 1
• UGSIEVCGPHQLIS-UHFFFAOYSA-N ethyl 4-chloro-2-(2-fluorophenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=CC=C1F UGSIEVCGPHQLIS-UHFFFAOYSA-N 0.000 description 1
• NCMMALNDFUCMSP-UHFFFAOYSA-N ethyl 4-chloro-2-(3,4,5-trifluorophenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC(F)=C(F)C(F)=C1 NCMMALNDFUCMSP-UHFFFAOYSA-N 0.000 description 1
• HQVZGMUWGBQXOX-UHFFFAOYSA-N ethyl 4-chloro-2-(3,4-difluorophenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(F)C(F)=C1 HQVZGMUWGBQXOX-UHFFFAOYSA-N 0.000 description 1
• IBTCIEPAVPYRDS-UHFFFAOYSA-N ethyl 4-chloro-2-(3,4-dimethylphenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(C)C(C)=C1 IBTCIEPAVPYRDS-UHFFFAOYSA-N 0.000 description 1
• GAQQPJUCPLBJBN-UHFFFAOYSA-N ethyl 4-chloro-2-(3-fluoro-4-methylphenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(C)C(F)=C1 GAQQPJUCPLBJBN-UHFFFAOYSA-N 0.000 description 1
• YLEAEJCFPLNSJR-UHFFFAOYSA-N ethyl 4-chloro-2-(4-chloro-3-methylphenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(Cl)C(C)=C1 YLEAEJCFPLNSJR-UHFFFAOYSA-N 0.000 description 1
• PWFBTWCNQPXUSO-UHFFFAOYSA-N ethyl 4-chloro-2-(4-fluoro-3-methoxyphenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(F)C(OC)=C1 PWFBTWCNQPXUSO-UHFFFAOYSA-N 0.000 description 1
• QJKASPRCQZGANG-UHFFFAOYSA-N ethyl 4-chloro-2-(4-methyl-3-nitrophenyl)pyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=C(C)C([N+]([O-])=O)=C1 QJKASPRCQZGANG-UHFFFAOYSA-N 0.000 description 1
• VXWYTPARKVGWFX-UHFFFAOYSA-N ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CN=C1C1=CC=CC=C1 VXWYTPARKVGWFX-UHFFFAOYSA-N 0.000 description 1
• VJAJUZZHCRUIGU-UHFFFAOYSA-N ethyl 6-oxo-2-(3,4,5-trifluorophenyl)-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC(F)=C(F)C(F)=C1 VJAJUZZHCRUIGU-UHFFFAOYSA-N 0.000 description 1
• JSIHCFJCICVJHJ-UHFFFAOYSA-N ethyl 6-oxo-2-phenyl-1h-pyrimidine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1 JSIHCFJCICVJHJ-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• YCWDQAKDVQNVAR-UHFFFAOYSA-N ethyl pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=CN=C1 YCWDQAKDVQNVAR-UHFFFAOYSA-N 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000004129 fatty acid metabolism Effects 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 229950010034 fidexaban Drugs 0.000 description 1
• 239000010408 film Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• KANJSNBRCNMZMV-ABRZTLGGSA-N fondaparinux Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](OC)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O4)NS(O)(=O)=O)[C@H](O3)C(O)=O)O)[C@@H](COS(O)(=O)=O)O2)NS(O)(=O)=O)[C@H](C(O)=O)O1 KANJSNBRCNMZMV-ABRZTLGGSA-N 0.000 description 1
• 229960001318 fondaparinux Drugs 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 229960002490 fosinopril Drugs 0.000 description 1
• 239000001530 fumaric acid Chemical class 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
• 229960003883 furosemide Drugs 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 238000003304 gavage Methods 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000002523 gelfiltration Methods 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• 229960000346 gliclazide Drugs 0.000 description 1
• 229960004346 glimepiride Drugs 0.000 description 1
• 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 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
• MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
• 229960004666 glucagon Drugs 0.000 description 1
• 230000004110 gluconeogenesis Effects 0.000 description 1
• 239000003292 glue Substances 0.000 description 1
• 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 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 230000004116 glycogenolysis Effects 0.000 description 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 239000010931 gold Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000002140 halogenating effect Effects 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 229960002897 heparin Drugs 0.000 description 1
• 229920000669 heparin Polymers 0.000 description 1
• 102000054223 human PPARA Human genes 0.000 description 1
• 229940106780 human fibrinogen Drugs 0.000 description 1
• 229960002474 hydralazine Drugs 0.000 description 1
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
• 201000001421 hyperglycemia Diseases 0.000 description 1
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
• 201000008980 hyperinsulinism Diseases 0.000 description 1
• 208000029498 hypoalphalipoproteinemia Diseases 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 239000000411 inducer Substances 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000001023 inorganic pigment Substances 0.000 description 1
• 239000004026 insulin derivative Substances 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
• 235000013980 iron oxide Nutrition 0.000 description 1
• VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 206010023332 keratitis Diseases 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 229960001632 labetalol Drugs 0.000 description 1
• 239000004310 lactic acid Chemical class 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• WMDSZGFJQKSLLH-RBBKRZOGSA-N landiolol Chemical compound O1C(C)(C)OC[C@H]1COC(=O)CCC(C=C1)=CC=C1OC[C@@H](O)CNCCNC(=O)N1CCOCC1 WMDSZGFJQKSLLH-RBBKRZOGSA-N 0.000 description 1
• 229950005241 landiolol Drugs 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 108020001756 ligand binding domains Proteins 0.000 description 1
• 230000037356 lipid metabolism Effects 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 206010024627 liposarcoma Diseases 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 239000006193 liquid solution Substances 0.000 description 1
• 229910052808 lithium carbonate Inorganic materials 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
• 239000006210 lotion Substances 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
• 239000003055 low molecular weight heparin Chemical class 0.000 description 1
• 229940127215 low-molecular weight heparin Drugs 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 239000002697 lyase inhibitor Substances 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 239000001630 malic acid Chemical class 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• DKWNMCUOEDMMIN-PKOBYXMFSA-N melagatran Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)[C@H]1N(C(=O)[C@H](NCC(O)=O)C2CCCCC2)CC1 DKWNMCUOEDMMIN-PKOBYXMFSA-N 0.000 description 1
• 229960002137 melagatran Drugs 0.000 description 1
• 229960003134 mepindolol Drugs 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 229940041669 mercury Drugs 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
• 229960003105 metformin Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• LYVGOAYMIAQLHI-UHFFFAOYSA-N methyl 2-butyl-1-[[2-fluoro-4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-6-oxopyridine-4-carboxylate Chemical compound CCCCC1=CC(C(=O)OC)=CC(=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1F LYVGOAYMIAQLHI-UHFFFAOYSA-N 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 229960002704 metipranolol Drugs 0.000 description 1
• BLWNYSZZZWQCKO-UHFFFAOYSA-N metipranolol hydrochloride Chemical compound [Cl-].CC(C)[NH2+]CC(O)COC1=CC(C)=C(OC(C)=O)C(C)=C1C BLWNYSZZZWQCKO-UHFFFAOYSA-N 0.000 description 1
• 229960002237 metoprolol Drugs 0.000 description 1
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000002394 mineralocorticoid antagonist Substances 0.000 description 1
• 229960003632 minoxidil Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 210000000214 mouth Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 230000002911 mydriatic effect Effects 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 210000004165 myocardium Anatomy 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960004255 nadolol Drugs 0.000 description 1
• VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
• YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-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
• 229920005615 natural polymer Polymers 0.000 description 1
• 229960000619 nebivolol Drugs 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
• NPORIZAYKBQYLF-LREBCSMRSA-N nicotinyl alcohol tartrate Chemical compound OCC1=CC=CN=C1.OC(=O)[C@H](O)[C@@H](O)C(O)=O NPORIZAYKBQYLF-LREBCSMRSA-N 0.000 description 1
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
• 229960001597 nifedipine Drugs 0.000 description 1
• MVPQUSQUURLQKF-MCPDASDXSA-E nonasodium;(2s,3s,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3s,4s,5r,6r)-2-carboxylato-4,5-dimethoxy-6-[(2r,3r,4s,5r,6s)-6-methoxy-4,5-disulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-disulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]oxy-4,5-di Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)O[C@@H]1[C@@H](OS([O-])(=O)=O)[C@@H](OC)O[C@H](COS([O-])(=O)=O)[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@@H]2[C@@H]([C@@H](OS([O-])(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](OC)[C@H](O[C@@H]4[C@@H]([C@@H](OC)[C@H](OC)[C@@H](COS([O-])(=O)=O)O4)OC)[C@H](O3)C([O-])=O)OC)[C@@H](COS([O-])(=O)=O)O2)OS([O-])(=O)=O)[C@H](C([O-])=O)O1 MVPQUSQUURLQKF-MCPDASDXSA-E 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229940100692 oral suspension Drugs 0.000 description 1
• 108060005714 orexin Proteins 0.000 description 1
• 239000003960 organic solvent Substances 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
• 210000001672 ovary Anatomy 0.000 description 1
• JPILDORBIJCDHE-UHFFFAOYSA-N oxadiazolidin-4-one Chemical class O=C1CONN1 JPILDORBIJCDHE-UHFFFAOYSA-N 0.000 description 1
• 229960004570 oxprenolol Drugs 0.000 description 1
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• VWMZIGBYZQUQOA-QEEMJVPDSA-N pamaqueside Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC(=O)[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VWMZIGBYZQUQOA-QEEMJVPDSA-N 0.000 description 1
• 229950005482 pamaqueside Drugs 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 208000024691 pancreas disease Diseases 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 229960002035 penbutolol Drugs 0.000 description 1
• KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
• 229960002582 perindopril Drugs 0.000 description 1
• 208000033808 peripheral neuropathy Diseases 0.000 description 1
• 239000008194 pharmaceutical composition Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
• 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 229960002508 pindolol Drugs 0.000 description 1
• PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 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
• 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
• 238000001121 post-column derivatisation Methods 0.000 description 1
• 230000000291 postprandial effect Effects 0.000 description 1
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
• 230000035935 pregnancy Effects 0.000 description 1
• 230000009862 primary prevention Effects 0.000 description 1
• FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
• 229960003912 probucol Drugs 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 230000005180 public health Effects 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class 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
• 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 1
• 229960003401 ramipril Drugs 0.000 description 1
• 229950010535 razaxaban Drugs 0.000 description 1
• 108091006084 receptor activators Proteins 0.000 description 1
• 239000002464 receptor antagonist Substances 0.000 description 1
• 229940044551 receptor antagonist Drugs 0.000 description 1
• 239000003087 receptor blocking agent Substances 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 210000005000 reproductive tract Anatomy 0.000 description 1
• 229960003147 reserpine Drugs 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 238000004007 reversed phase HPLC Methods 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229960001148 rivaroxaban Drugs 0.000 description 1
• KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 description 1
• MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 229960000672 rosuvastatin Drugs 0.000 description 1
• 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 description 1
• 239000000523 sample Substances 0.000 description 1
• 238000005488 sandblasting Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 230000037390 scarring Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000009863 secondary prevention Effects 0.000 description 1
• 230000028327 secretion Effects 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
• 201000000849 skin cancer Diseases 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 201000010153 skin papilloma Diseases 0.000 description 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 229960002370 sotalol Drugs 0.000 description 1
• ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 238000010972 statistical evaluation Methods 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000008961 swelling Effects 0.000 description 1
• 229920001059 synthetic polymer Polymers 0.000 description 1
• 238000012353 t test Methods 0.000 description 1
• 239000011975 tartaric acid Chemical class 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229960005187 telmisartan Drugs 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 229960004072 thrombin Drugs 0.000 description 1
• 239000003868 thrombin inhibitor Substances 0.000 description 1
• 208000021510 thyroid gland disease Diseases 0.000 description 1
• PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
• 229960005001 ticlopidine Drugs 0.000 description 1
• 229960004605 timolol Drugs 0.000 description 1
• 229950004437 tiqueside Drugs 0.000 description 1
• COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 description 1
• 229960003425 tirofiban Drugs 0.000 description 1
• 229960005371 tolbutamide Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
• 229950004514 torcetrapib Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 230000001131 transforming effect Effects 0.000 description 1
• 230000009261 transgenic effect Effects 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• 238000001291 vacuum drying Methods 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
• 229960001722 verapamil Drugs 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 229940019333 vitamin k antagonists Drugs 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1
• 239000000230 xanthan gum Substances 0.000 description 1
• 229920001285 xanthan gum Polymers 0.000 description 1
• 235000010493 xanthan gum Nutrition 0.000 description 1
• 229940082509 xanthan gum Drugs 0.000 description 1
• ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
• 229960001522 ximelagatran Drugs 0.000 description 1
• 150000003752 zinc compounds Chemical class 0.000 description 1