NZ575011A - Substituted imidazolone derivatives, preparation and uses - Google Patents

Info

Publication number

NZ575011A

NZ575011A NZ575011A NZ57501107A NZ575011A NZ 575011 A NZ575011 A NZ 575011A NZ 575011 A NZ575011 A NZ 575011A NZ 57501107 A NZ57501107 A NZ 57501107A NZ 575011 A NZ575011 A NZ 575011A

Authority

NZ

New Zealand

Prior art keywords

methyl

imidazol

butyl

oxy

carboxy

Prior art date

2006-07-24

Links

• Espacenet
• Global Dossier
• Discuss

• 238000002360 preparation method Methods 0.000 title claims description 26
• WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 title abstract description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 288
• 150000001875 compounds Chemical class 0.000 claims abstract description 260
• -1 3'-((1-carboxy-1,1-dimethylmethyl)oxy)biphenyl-4-yl Chemical group 0.000 claims abstract description 254
• 206010020772 Hypertension Diseases 0.000 claims abstract description 25
• 230000007170 pathology Effects 0.000 claims abstract description 17
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 13
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 11
• 230000002526 effect on cardiovascular system Effects 0.000 claims abstract description 10
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 7
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 7
• 208000008589 Obesity Diseases 0.000 claims abstract description 7
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 7
• 235000020824 obesity Nutrition 0.000 claims abstract description 7
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 6
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 6
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 5
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
• 230000000626 neurodegenerative effect Effects 0.000 claims abstract description 5
• 230000007423 decrease Effects 0.000 claims abstract description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 238000011282 treatment Methods 0.000 claims description 60
• 125000003118 aryl group Chemical group 0.000 claims description 57
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 37
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• 239000007787 solid Chemical group 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 125000003342 alkenyl group Chemical group 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000000304 alkynyl group Chemical group 0.000 claims description 28
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 150000002825 nitriles Chemical class 0.000 claims description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
• 125000004434 sulfur atom Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 9
• 150000003839 salts Chemical group 0.000 claims description 9
• 150000003536 tetrazoles Chemical class 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 230000001225 therapeutic effect Effects 0.000 claims description 7
• 239000004215 Carbon black (E152) Substances 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 229930195733 hydrocarbon Natural products 0.000 claims description 6
• 150000003573 thiols Chemical class 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 150000004677 hydrates Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 150000007970 thio esters Chemical class 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 4
• 239000000470 constituent Substances 0.000 claims description 4
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
• 150000002430 hydrocarbons Chemical class 0.000 claims description 4
• 239000012453 solvate Chemical group 0.000 claims description 4
• 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
• VZAKJEDGHNBXGU-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-dimethyl-5-oxoimidazol-1-yl)methyl]phenyl]phenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(C)(C)C(=O)N1CC1=CC=C(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C=C1 VZAKJEDGHNBXGU-UHFFFAOYSA-N 0.000 claims description 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
• 239000002537 cosmetic Substances 0.000 claims description 3
• NAYAKJIEBAOSTF-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]-4-fluorophenoxy]-3-methylbutanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C(=CC=C(OC(C(C)C)C(O)=O)C=2)F)C=C1 NAYAKJIEBAOSTF-UHFFFAOYSA-N 0.000 claims description 2
• FDUCJDKCXPJHSB-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]phenoxy]propanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C=C(OC(C)C(O)=O)C=CC=2)C=C1 FDUCJDKCXPJHSB-UHFFFAOYSA-N 0.000 claims description 2
• PSSACIZQBPYDSL-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-5-oxo-4-phenyl-4h-imidazol-1-yl)methyl]phenyl]phenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(C=2C=CC=CC=2)C(=O)N1CC(C=C1)=CC=C1C1=CC=CC(OC(C)(C)C(O)=O)=C1 PSSACIZQBPYDSL-UHFFFAOYSA-N 0.000 claims description 2
• HUAORTYKYMCFMJ-UHFFFAOYSA-N 2-[4-bromo-2-[4-[(2-butyl-5-oxo-4-phenyl-4h-imidazol-1-yl)methyl]phenyl]phenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(C=2C=CC=CC=2)C(=O)N1CC(C=C1)=CC=C1C1=CC(Br)=CC=C1OC(C)(C)C(O)=O HUAORTYKYMCFMJ-UHFFFAOYSA-N 0.000 claims description 2
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000003367 polycyclic group Chemical group 0.000 claims description 2
• 229910052711 selenium Inorganic materials 0.000 claims description 2
• IDPGORLEXVSQCU-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]phenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)C=C1 IDPGORLEXVSQCU-UHFFFAOYSA-N 0.000 claims 1
• NFGGISCBJMKFHO-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]phenoxy]-3-methylbutanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C=C(OC(C(C)C)C(O)=O)C=CC=2)C=C1 NFGGISCBJMKFHO-UHFFFAOYSA-N 0.000 claims 1
• XUNMBHZKXIOKMO-UHFFFAOYSA-N 4,4-diethyl-1h-imidazol-5-one Chemical compound CCC1(CC)N=CNC1=O XUNMBHZKXIOKMO-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 801
• 238000000034 method Methods 0.000 description 375
• 239000000047 product Substances 0.000 description 339
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 306
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 208
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 189
• 239000000741 silica gel Substances 0.000 description 189
• 229910002027 silica gel Inorganic materials 0.000 description 189
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 177
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 151
• 239000003480 eluent Substances 0.000 description 131
• 239000012230 colorless oil Substances 0.000 description 74
• 239000003921 oil Substances 0.000 description 69
• 235000019198 oils Nutrition 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 68
• 239000000243 solution Substances 0.000 description 66
• 230000002829 reductive effect Effects 0.000 description 61
• 239000003208 petroleum Substances 0.000 description 59
• 238000002329 infrared spectrum Methods 0.000 description 55
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 239000012044 organic layer Substances 0.000 description 46
• 238000005893 bromination reaction Methods 0.000 description 45
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
• 230000014509 gene expression Effects 0.000 description 38
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
• 230000031709 bromination Effects 0.000 description 34
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 26
• 239000012267 brine Substances 0.000 description 25
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• 210000001519 tissue Anatomy 0.000 description 25
• 229940125904 compound 1 Drugs 0.000 description 24
• 230000002440 hepatic effect Effects 0.000 description 24
• 238000006722 reduction reaction Methods 0.000 description 24
• 241000699666 Mus <mouse, genus> Species 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
• 229910052938 sodium sulfate Inorganic materials 0.000 description 22
• 235000011152 sodium sulphate Nutrition 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 238000010828 elution Methods 0.000 description 21
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
• 235000019341 magnesium sulphate Nutrition 0.000 description 21
• 230000009467 reduction Effects 0.000 description 21
• CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 19
• 239000002253 acid Substances 0.000 description 19
• 230000006870 function Effects 0.000 description 19
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
• 238000006069 Suzuki reaction reaction Methods 0.000 description 18
• 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 18
• 229910000027 potassium carbonate Inorganic materials 0.000 description 18
• 239000000843 powder Substances 0.000 description 18
• 101800000733 Angiotensin-2 Proteins 0.000 description 17
• 102400000345 Angiotensin-2 Human genes 0.000 description 17
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 17
• 229950006323 angiotensin ii Drugs 0.000 description 17
• 229940126086 compound 21 Drugs 0.000 description 17
• 230000000694 effects Effects 0.000 description 17
• 230000006698 induction Effects 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 238000006467 substitution reaction Methods 0.000 description 17
• 230000004872 arterial blood pressure Effects 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
• 108090000623 proteins and genes Proteins 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 14
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 13
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 13
• 238000010520 demethylation reaction Methods 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
• 241001465754 Metazoa Species 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 230000017858 demethylation Effects 0.000 description 11
• 238000011156 evaluation Methods 0.000 description 11
• 229910052736 halogen Inorganic materials 0.000 description 11
• 150000002367 halogens Chemical class 0.000 description 11
• 238000005259 measurement Methods 0.000 description 11
• 230000008569 process Effects 0.000 description 11
• 101710155857 C-C motif chemokine 2 Proteins 0.000 description 10
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
• 238000007327 hydrogenolysis reaction Methods 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 150000002632 lipids Chemical class 0.000 description 10
• 230000028327 secretion Effects 0.000 description 10
• 238000001149 thermolysis Methods 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 102000000018 Chemokine CCL2 Human genes 0.000 description 9
• 238000010934 O-alkylation reaction Methods 0.000 description 9
• 239000000556 agonist Substances 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 9
• 238000006460 hydrolysis reaction Methods 0.000 description 9
• 239000002207 metabolite Substances 0.000 description 9
• OPUJUITUYWGUEP-UHFFFAOYSA-N methyl 1-aminocyclopentane-1-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(N)CCCC1 OPUJUITUYWGUEP-UHFFFAOYSA-N 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 150000003626 triacylglycerols Chemical class 0.000 description 9
• 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 9
• 108010029485 Protein Isoforms Proteins 0.000 description 8
• 102000001708 Protein Isoforms Human genes 0.000 description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000000338 in vitro Methods 0.000 description 8
• 238000001727 in vivo Methods 0.000 description 8
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
• 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 8
• 238000000746 purification Methods 0.000 description 8
• 102000005962 receptors Human genes 0.000 description 8
• 108020003175 receptors Proteins 0.000 description 8
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 8
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
• VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 7
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 7
• 238000005804 alkylation reaction Methods 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 230000000055 hyoplipidemic effect Effects 0.000 description 7
• IZNSMYBVTREDJM-UHFFFAOYSA-N tert-butyl 2-[3-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 IZNSMYBVTREDJM-UHFFFAOYSA-N 0.000 description 7
• YCISNMVJZZPXBG-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(Br)=C1 YCISNMVJZZPXBG-UHFFFAOYSA-N 0.000 description 6
• JHFVSGIMLDFLIC-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C=C1Br JHFVSGIMLDFLIC-UHFFFAOYSA-N 0.000 description 6
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 6
• 101150059573 AGTR1 gene Proteins 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 6
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 6
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 6
• 241000700159 Rattus Species 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• DWSINROGTIDKRL-UHFFFAOYSA-N 1-(2-bromo-4-methoxyphenyl)-2-methylpropan-1-one Chemical compound COC1=CC=C(C(=O)C(C)C)C(Br)=C1 DWSINROGTIDKRL-UHFFFAOYSA-N 0.000 description 5
• LMFOTABZFINGGW-UHFFFAOYSA-N 1-(4-bromo-2-methoxyphenyl)-2-methylpropan-1-one Chemical compound COC1=CC(Br)=CC=C1C(=O)C(C)C LMFOTABZFINGGW-UHFFFAOYSA-N 0.000 description 5
• KYZHKXMHJFOQPM-UHFFFAOYSA-N 1-(4-bromo-2-methoxyphenyl)ethanone Chemical compound COC1=CC(Br)=CC=C1C(C)=O KYZHKXMHJFOQPM-UHFFFAOYSA-N 0.000 description 5
• GBOWQPRFJSAMCS-UHFFFAOYSA-N 2-butyl-4-phenyl-1,4-dihydroimidazol-5-one Chemical compound O=C1NC(CCCC)=NC1C1=CC=CC=C1 GBOWQPRFJSAMCS-UHFFFAOYSA-N 0.000 description 5
• 102000004539 Acyl-CoA Oxidase Human genes 0.000 description 5
• 108020001558 Acyl-CoA oxidase Proteins 0.000 description 5
• 102000015427 Angiotensins Human genes 0.000 description 5
• 108010064733 Angiotensins Proteins 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• 206010061218 Inflammation Diseases 0.000 description 5
• 230000003213 activating effect Effects 0.000 description 5
• 239000012190 activator Substances 0.000 description 5
• 239000012300 argon atmosphere Substances 0.000 description 5
• 235000019445 benzyl alcohol Nutrition 0.000 description 5
• 238000009835 boiling Methods 0.000 description 5
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 201000010063 epididymitis Diseases 0.000 description 5
• QVYBLBYCDLTUHZ-UHFFFAOYSA-N ethyl 2-[3-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 QVYBLBYCDLTUHZ-UHFFFAOYSA-N 0.000 description 5
• ZZIIPGFXBCCYPP-UHFFFAOYSA-N ethyl 2-[4-bromo-2-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Br)C=C1C1=CC=C(CBr)C=C1 ZZIIPGFXBCCYPP-UHFFFAOYSA-N 0.000 description 5
• RCXZZCSTQFSXPD-UHFFFAOYSA-N ethyl 2-[4-bromo-3-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Br)C(C=2C=CC(CBr)=CC=2)=C1 RCXZZCSTQFSXPD-UHFFFAOYSA-N 0.000 description 5
• XLVSXTNEASHWQT-UHFFFAOYSA-N ethyl pentanimidate;hydrochloride Chemical compound Cl.CCCCC(=N)OCC XLVSXTNEASHWQT-UHFFFAOYSA-N 0.000 description 5
• 230000004054 inflammatory process Effects 0.000 description 5
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 5
• YDMRDHQUQIVWBE-UHFFFAOYSA-N (2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1O YDMRDHQUQIVWBE-UHFFFAOYSA-N 0.000 description 4
• BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 4
• BHCGDEJUEYWMDO-UHFFFAOYSA-N 1-(4-bromo-2-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Br)C=C1OC BHCGDEJUEYWMDO-UHFFFAOYSA-N 0.000 description 4
• DVQWNQBEUKXONL-UHFFFAOYSA-N 1-iodo-2-methoxybenzene Chemical compound COC1=CC=CC=C1I DVQWNQBEUKXONL-UHFFFAOYSA-N 0.000 description 4
• NRRCYQZPZNDJER-UHFFFAOYSA-N 3-(4-methylphenyl)phenol Chemical compound C1=CC(C)=CC=C1C1=CC=CC(O)=C1 NRRCYQZPZNDJER-UHFFFAOYSA-N 0.000 description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
• 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 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• 102100027947 Carnitine O-palmitoyltransferase 1, muscle isoform Human genes 0.000 description 4
• 101710108984 Carnitine O-palmitoyltransferase 1, muscle isoform Proteins 0.000 description 4
• 102400001064 Fibrinogen beta chain Human genes 0.000 description 4
• 101710170765 Fibrinogen beta chain Proteins 0.000 description 4
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 4
• 102000004877 Insulin Human genes 0.000 description 4
• 108090001061 Insulin Proteins 0.000 description 4
• 102000004890 Interleukin-8 Human genes 0.000 description 4
• 108090001007 Interleukin-8 Proteins 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
• 229940126033 PPAR agonist Drugs 0.000 description 4
• 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 235000001014 amino acid Nutrition 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 239000002876 beta blocker Substances 0.000 description 4
• 229940097320 beta blocking agent Drugs 0.000 description 4
• 235000012000 cholesterol Nutrition 0.000 description 4
• 238000009833 condensation Methods 0.000 description 4
• 230000005494 condensation Effects 0.000 description 4
• 238000006482 condensation reaction Methods 0.000 description 4
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• YHLJHRIRIYQZBL-UHFFFAOYSA-N ethyl 2-[2-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1C1=CC=C(CBr)C=C1 YHLJHRIRIYQZBL-UHFFFAOYSA-N 0.000 description 4
• CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 4
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
• 229940125753 fibrate Drugs 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 229940125396 insulin Drugs 0.000 description 4
• XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 4
• 229940096397 interleukin-8 Drugs 0.000 description 4
• 238000001990 intravenous administration Methods 0.000 description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
• 230000004060 metabolic process Effects 0.000 description 4
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
• IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
• 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 4
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• 125000003831 tetrazolyl group Chemical group 0.000 description 4
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
• 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 3
• PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 3
• UHHXITPNGSCOBA-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CBr)=CC=C1Br UHHXITPNGSCOBA-UHFFFAOYSA-N 0.000 description 3
• ZKSAFWBHFTUHMZ-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-methoxybenzene Chemical compound COC1=CC(CBr)=CC=C1Br ZKSAFWBHFTUHMZ-UHFFFAOYSA-N 0.000 description 3
• PXAIZWVEYHNBLL-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(CBr)=CC=C1Br PXAIZWVEYHNBLL-UHFFFAOYSA-N 0.000 description 3
• YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 3
• ZZFKRTRYOSBWQY-UHFFFAOYSA-N 2-(4-methylphenyl)phenol Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1O ZZFKRTRYOSBWQY-UHFFFAOYSA-N 0.000 description 3
• ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 3
• UTSKAQLJCLJSDV-UHFFFAOYSA-N 2-butyl-4,4-dimethyl-1h-imidazol-5-one Chemical compound CCCCC1=NC(C)(C)C(=O)N1 UTSKAQLJCLJSDV-UHFFFAOYSA-N 0.000 description 3
• 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 3
• SCFCSDBZMDPIGY-UHFFFAOYSA-N 3-(4-methylphenoxy)phenol Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(O)=C1 SCFCSDBZMDPIGY-UHFFFAOYSA-N 0.000 description 3
• MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 3
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• 229940123413 Angiotensin II antagonist Drugs 0.000 description 3
• 108010056301 Apolipoprotein C-III Proteins 0.000 description 3
• 102100030970 Apolipoprotein C-III Human genes 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
• 235000019502 Orange oil Nutrition 0.000 description 3
• 101150014691 PPARA gene Proteins 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
• 241000700157 Rattus norvegicus Species 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 229940123464 Thiazolidinedione Drugs 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 3
• 230000004913 activation Effects 0.000 description 3
• 125000005907 alkyl ester group Chemical group 0.000 description 3
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 208000006673 asthma Diseases 0.000 description 3
• 229960002274 atenolol Drugs 0.000 description 3
• 150000001649 bromium compounds Chemical class 0.000 description 3
• 239000000480 calcium channel blocker Substances 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 239000002158 endotoxin Substances 0.000 description 3
• 125000004185 ester group Chemical group 0.000 description 3
• 238000006266 etherification reaction Methods 0.000 description 3
• XYJFWAAUVZXLFG-UHFFFAOYSA-N ethyl 2-[2-(2-bromoethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1CCBr XYJFWAAUVZXLFG-UHFFFAOYSA-N 0.000 description 3
• FNQDXPIXGFBCFG-UHFFFAOYSA-N ethyl 2-[3-(2-bromoethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(CCBr)=C1 FNQDXPIXGFBCFG-UHFFFAOYSA-N 0.000 description 3
• BSARASXZMNRHDV-UHFFFAOYSA-N ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(CCBr)C=C1 BSARASXZMNRHDV-UHFFFAOYSA-N 0.000 description 3
• KXFYOQJSKHZBQE-UHFFFAOYSA-N ethyl 2-[4-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1=CC=C(CBr)C=C1 KXFYOQJSKHZBQE-UHFFFAOYSA-N 0.000 description 3
• 229960002297 fenofibrate Drugs 0.000 description 3
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• 229910052731 fluorine Inorganic materials 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical class [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000000842 isoxazolyl group Chemical group 0.000 description 3
• 229960001632 labetalol Drugs 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 229920006008 lipopolysaccharide Polymers 0.000 description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
• GRJDNFSKEWOMIM-UHFFFAOYSA-N methyl 4-bromo-3-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C(CBr)=C1 GRJDNFSKEWOMIM-UHFFFAOYSA-N 0.000 description 3
• GMBKTXOUEBFCMP-UHFFFAOYSA-N methyl 5-[2-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=CC=C1C1=CC=C(CBr)C=C1 GMBKTXOUEBFCMP-UHFFFAOYSA-N 0.000 description 3
• XVFVAMCSKBGKQN-UHFFFAOYSA-N methyl 5-[4-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethylpentanoate Chemical compound C1=CC(OCCCC(C)(C)C(=O)OC)=CC=C1C1=CC=C(CBr)C=C1 XVFVAMCSKBGKQN-UHFFFAOYSA-N 0.000 description 3
• DDMBXXYJUWSHAV-UHFFFAOYSA-N methyl 5-iodo-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCI DDMBXXYJUWSHAV-UHFFFAOYSA-N 0.000 description 3
• BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 3
• 229960002237 metoprolol Drugs 0.000 description 3
• 210000001616 monocyte Anatomy 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 230000031990 negative regulation of inflammatory response Effects 0.000 description 3
• 239000010502 orange oil Substances 0.000 description 3
• 150000002905 orthoesters Chemical class 0.000 description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 230000010412 perfusion Effects 0.000 description 3
• 230000021715 photosynthesis, light harvesting Effects 0.000 description 3
• 229960003712 propranolol Drugs 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
• 150000001467 thiazolidinediones Chemical class 0.000 description 3
• 125000001544 thienyl group Chemical group 0.000 description 3
• 238000005732 thioetherification reaction Methods 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
• 229940124549 vasodilator Drugs 0.000 description 3
• 239000003071 vasodilator agent Substances 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• TWPKIBFRKXFXRJ-UHFFFAOYSA-N (1-bromo-2-phenylethyl)benzene Chemical class C=1C=CC=CC=1C(Br)CC1=CC=CC=C1 TWPKIBFRKXFXRJ-UHFFFAOYSA-N 0.000 description 2
• CEVCYBWRNWZIAA-UHFFFAOYSA-N (2-hydroxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1O CEVCYBWRNWZIAA-UHFFFAOYSA-N 0.000 description 2
• IANDXFCUVROAOX-UHFFFAOYSA-N (2-methoxyphenyl)-(4-methylphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(C)C=C1 IANDXFCUVROAOX-UHFFFAOYSA-N 0.000 description 2
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
• ZMGPTWDNUWDBSE-UHFFFAOYSA-N (3-hydroxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC(O)=C1 ZMGPTWDNUWDBSE-UHFFFAOYSA-N 0.000 description 2
• IFKWLKCPUIQXPU-UHFFFAOYSA-N (4-bromo-2-methylphenyl)methanol Chemical compound CC1=CC(Br)=CC=C1CO IFKWLKCPUIQXPU-UHFFFAOYSA-N 0.000 description 2
• KJLJDWXNJBJBLG-UHFFFAOYSA-N (4-bromo-3-ethylphenyl)methanol Chemical compound CCC1=CC(CO)=CC=C1Br KJLJDWXNJBJBLG-UHFFFAOYSA-N 0.000 description 2
• KXUYHKRDJBTPDF-UHFFFAOYSA-N (4-bromo-3-methoxyphenyl)methanol Chemical compound COC1=CC(CO)=CC=C1Br KXUYHKRDJBTPDF-UHFFFAOYSA-N 0.000 description 2
• GAANESYOLGFJFC-UHFFFAOYSA-N (4-bromo-3-nitrophenyl)methanol Chemical compound OCC1=CC=C(Br)C([N+]([O-])=O)=C1 GAANESYOLGFJFC-UHFFFAOYSA-N 0.000 description 2
• HMBOJWOOJNYKPD-UHFFFAOYSA-N (4-bromo-3-propylphenyl)methanol Chemical compound CCCC1=CC(CO)=CC=C1Br HMBOJWOOJNYKPD-UHFFFAOYSA-N 0.000 description 2
• HPJMSFQWRMTUHT-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(O)C=C1 HPJMSFQWRMTUHT-UHFFFAOYSA-N 0.000 description 2
• IHMWJDNMIIEDDN-UHFFFAOYSA-N (4-methoxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 IHMWJDNMIIEDDN-UHFFFAOYSA-N 0.000 description 2
• SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 2
• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
• KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
• BMWITEOIYWUGTD-UHFFFAOYSA-N 1-[1-(phenylmethoxymethyl)tetrazol-5-yl]propan-1-ol Chemical compound CCC(O)C1=NN=NN1COCC1=CC=CC=C1 BMWITEOIYWUGTD-UHFFFAOYSA-N 0.000 description 2
• NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 description 2
• XIFHUXKZQVRHEK-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-propylbenzene Chemical compound CCCC1=CC(CBr)=CC=C1Br XIFHUXKZQVRHEK-UHFFFAOYSA-N 0.000 description 2
• ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
• WGMHMVLZFAJNOT-UHFFFAOYSA-N 1-ethoxyethylideneazanium;chloride Chemical compound [Cl-].CCOC(C)=[NH2+] WGMHMVLZFAJNOT-UHFFFAOYSA-N 0.000 description 2
• RSHBAGGASAJQCH-UHFFFAOYSA-N 1-iodo-3-methoxybenzene Chemical compound COC1=CC=CC(I)=C1 RSHBAGGASAJQCH-UHFFFAOYSA-N 0.000 description 2
• PEOOXYNSXLWKJK-UHFFFAOYSA-N 1-methoxy-3-(4-methylphenoxy)benzene Chemical compound COC1=CC=CC(OC=2C=CC(C)=CC=2)=C1 PEOOXYNSXLWKJK-UHFFFAOYSA-N 0.000 description 2
• BHOACKQMLUQRAG-UHFFFAOYSA-N 1-methoxy-3-(4-methylphenyl)sulfanylbenzene Chemical compound COC1=CC=CC(SC=2C=CC(C)=CC=2)=C1 BHOACKQMLUQRAG-UHFFFAOYSA-N 0.000 description 2
• ILQBIDNUYXFZKH-UHFFFAOYSA-N 1-methoxy-4-(4-methylphenyl)sulfanylbenzene Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1 ILQBIDNUYXFZKH-UHFFFAOYSA-N 0.000 description 2
• RKMZJVBSOAVGQS-UHFFFAOYSA-N 1-methylsulfonylethanol Chemical compound CC(O)S(C)(=O)=O RKMZJVBSOAVGQS-UHFFFAOYSA-N 0.000 description 2
• 125000006023 1-pentenyl group Chemical group 0.000 description 2
• 125000006017 1-propenyl group Chemical group 0.000 description 2
• AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 2
• 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 2
• YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
• FKASAVXZZLJTNX-UHFFFAOYSA-N 2-(dimethylamino)acetic acid;hydrochloride Chemical compound [Cl-].C[NH+](C)CC(O)=O FKASAVXZZLJTNX-UHFFFAOYSA-N 0.000 description 2
• LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
• DMXHDKBRSAUKTR-UHFFFAOYSA-N 2-[3-(4-methylphenyl)phenoxy]acetonitrile Chemical compound C1=CC(C)=CC=C1C1=CC=CC(OCC#N)=C1 DMXHDKBRSAUKTR-UHFFFAOYSA-N 0.000 description 2
• ZJLCRIDNYBWJIF-UHFFFAOYSA-N 2-[3-[4-(bromomethyl)phenyl]phenoxy]acetonitrile Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC(OCC#N)=C1 ZJLCRIDNYBWJIF-UHFFFAOYSA-N 0.000 description 2
• PIPKSXJTPSSWRY-UHFFFAOYSA-N 2-bromo-1-ethyl-4-methoxybenzene Chemical compound CCC1=CC=C(OC)C=C1Br PIPKSXJTPSSWRY-UHFFFAOYSA-N 0.000 description 2
• VYALNMHJQCOGBC-UHFFFAOYSA-N 2-bromo-4-methoxy-1-(2-methylpropyl)benzene Chemical compound COC1=CC=C(CC(C)C)C(Br)=C1 VYALNMHJQCOGBC-UHFFFAOYSA-N 0.000 description 2
• CGOHDBLVDIXZPB-UHFFFAOYSA-N 2-bromo-4-methoxy-1-propylbenzene Chemical compound CCCC1=CC=C(OC)C=C1Br CGOHDBLVDIXZPB-UHFFFAOYSA-N 0.000 description 2
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
• LIDKBZBKWGILIY-UHFFFAOYSA-N 2-butyl-4,4-diethyl-1h-imidazol-5-one Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1 LIDKBZBKWGILIY-UHFFFAOYSA-N 0.000 description 2
• RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 2
• QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
• 125000006024 2-pentenyl group Chemical group 0.000 description 2
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• AMQIPHZFLIDOCB-UHFFFAOYSA-N 3-(2-hydroxyethyl)phenol Chemical compound OCCC1=CC=CC(O)=C1 AMQIPHZFLIDOCB-UHFFFAOYSA-N 0.000 description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
• SDGFJYRTWKBZFB-UHFFFAOYSA-N 4-(4-methylphenoxy)phenol Chemical compound C1=CC(C)=CC=C1OC1=CC=C(O)C=C1 SDGFJYRTWKBZFB-UHFFFAOYSA-N 0.000 description 2
• DDZACMDGXVXOOH-UHFFFAOYSA-N 4-(4-methylphenyl)phenol Chemical compound C1=CC(C)=CC=C1C1=CC=C(O)C=C1 DDZACMDGXVXOOH-UHFFFAOYSA-N 0.000 description 2
• LADOBJZJEARFJO-UHFFFAOYSA-N 4-(4-methylphenyl)sulfanylphenol Chemical compound C1=CC(C)=CC=C1SC1=CC=C(O)C=C1 LADOBJZJEARFJO-UHFFFAOYSA-N 0.000 description 2
• ZZTXSTDMMAAYCJ-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-ethylbenzene Chemical compound CCC1=CC(Br)=CC=C1CBr ZZTXSTDMMAAYCJ-UHFFFAOYSA-N 0.000 description 2
• RRBOULIORCZELO-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC(Br)=CC=C1CBr RRBOULIORCZELO-UHFFFAOYSA-N 0.000 description 2
• BIDHQMJRQFWEDT-UHFFFAOYSA-N 4-bromo-1-ethyl-2-methoxybenzene Chemical compound CCC1=CC=C(Br)C=C1OC BIDHQMJRQFWEDT-UHFFFAOYSA-N 0.000 description 2
• PWZSHFCSKSRQJF-UHFFFAOYSA-N 4-bromo-2-methoxy-1-propylbenzene Chemical compound CCCC1=CC=C(Br)C=C1OC PWZSHFCSKSRQJF-UHFFFAOYSA-N 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
• RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 2
• 101710095339 Apolipoprotein E Proteins 0.000 description 2
• 102100029470 Apolipoprotein E Human genes 0.000 description 2
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
• 229940127291 Calcium channel antagonist Drugs 0.000 description 2
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
• PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 2
• 102000053602 DNA Human genes 0.000 description 2
• 108020004414 DNA Proteins 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• 108010061435 Enalapril Proteins 0.000 description 2
• 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
• 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 2
• 108010023302 HDL Cholesterol Proteins 0.000 description 2
• 108010010234 HDL Lipoproteins Proteins 0.000 description 2
• 102000015779 HDL Lipoproteins Human genes 0.000 description 2
• 101500024730 Homo sapiens Angiotensin-2 Proteins 0.000 description 2
• 101001074035 Homo sapiens Zinc finger protein GLI2 Proteins 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• 108010028554 LDL Cholesterol Proteins 0.000 description 2
• 102000004895 Lipoproteins Human genes 0.000 description 2
• 108090001030 Lipoproteins Proteins 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• 108090000472 Phosphoenolpyruvate carboxykinase (ATP) Proteins 0.000 description 2
• 102100034792 Phosphoenolpyruvate carboxykinase [GTP], mitochondrial Human genes 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-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
• 102000040945 Transcription factor Human genes 0.000 description 2
• 108091023040 Transcription factor Proteins 0.000 description 2
• 108010069201 VLDL Cholesterol Proteins 0.000 description 2
• 102100035558 Zinc finger protein GLI2 Human genes 0.000 description 2
• JZNXJKZTUXTCPS-UHFFFAOYSA-N [4-bromo-3-(trifluoromethyl)phenyl]methanol Chemical compound OCC1=CC=C(Br)C(C(F)(F)F)=C1 JZNXJKZTUXTCPS-UHFFFAOYSA-N 0.000 description 2
• XSVFJXSRBWNCFA-UHFFFAOYSA-N [bromo(phenyl)methyl]sulfanylbenzene Chemical class C=1C=CC=CC=1C(Br)SC1=CC=CC=C1 XSVFJXSRBWNCFA-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 150000001263 acyl chlorides Chemical class 0.000 description 2
• 239000002170 aldosterone antagonist Substances 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 2
• 229960000528 amlodipine Drugs 0.000 description 2
• 235000019270 ammonium chloride Nutrition 0.000 description 2
• 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 description 2
• 230000003178 anti-diabetic effect Effects 0.000 description 2
• 230000003110 anti-inflammatory effect Effects 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 230000027455 binding Effects 0.000 description 2
• 239000004305 biphenyl Substances 0.000 description 2
• 235000010290 biphenyl Nutrition 0.000 description 2
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 150000004768 bromobenzenes Chemical class 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 2
• 229960000830 captopril Drugs 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 2
• 229940093530 coenzyme a Drugs 0.000 description 2
• 229940125797 compound 12 Drugs 0.000 description 2
• 229940126545 compound 53 Drugs 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 238000006900 dealkylation reaction Methods 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 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 2
• 229960004166 diltiazem Drugs 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• 239000002934 diuretic Substances 0.000 description 2
• 229940030606 diuretics Drugs 0.000 description 2
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
• 229960000873 enalapril Drugs 0.000 description 2
• GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 2
• FOGZQGMFFNTURS-UHFFFAOYSA-N ethyl 2-(2-bromophenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1Br FOGZQGMFFNTURS-UHFFFAOYSA-N 0.000 description 2
• JIGVVUZSRMJMNC-UHFFFAOYSA-N ethyl 2-(3-bromophenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(Br)=C1 JIGVVUZSRMJMNC-UHFFFAOYSA-N 0.000 description 2
• IOVDAUBZQSIHIQ-UHFFFAOYSA-N ethyl 2-(4-bromophenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Br)C=C1 IOVDAUBZQSIHIQ-UHFFFAOYSA-N 0.000 description 2
• QTNVLNSDIIWAML-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazole-5-carboxylate Chemical compound N=1N2C(C)=C(C(=O)OCC)SC2=NC=1C1=CC=C(OC)C=C1 QTNVLNSDIIWAML-UHFFFAOYSA-N 0.000 description 2
• NUCCDBNGXUBEKF-UHFFFAOYSA-N ethyl 2-[2-(2-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1CCO NUCCDBNGXUBEKF-UHFFFAOYSA-N 0.000 description 2
• VKIRPPLYGDSMOU-UHFFFAOYSA-N ethyl 2-[3-(2-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(CCO)=C1 VKIRPPLYGDSMOU-UHFFFAOYSA-N 0.000 description 2
• UIRMSQVVSPLTKD-UHFFFAOYSA-N ethyl 2-[3-[4-(bromomethyl)benzoyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C(=O)C=2C=CC(CBr)=CC=2)=C1 UIRMSQVVSPLTKD-UHFFFAOYSA-N 0.000 description 2
• MRJJGAVVMDBIIO-UHFFFAOYSA-N ethyl 2-[4-(2-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(CCO)C=C1 MRJJGAVVMDBIIO-UHFFFAOYSA-N 0.000 description 2
• MLHTUEDPNBKQFR-UHFFFAOYSA-N ethyl 2-[4-[4-(bromomethyl)benzoyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=C(CBr)C=C1 MLHTUEDPNBKQFR-UHFFFAOYSA-N 0.000 description 2
• IBZPDDVIOZFROP-UHFFFAOYSA-N ethyl 2-methyl-2-[2-(4-methylphenyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1C1=CC=C(C)C=C1 IBZPDDVIOZFROP-UHFFFAOYSA-N 0.000 description 2
• ASAVFWNHFYYLGW-UHFFFAOYSA-N ethyl 2-methyl-2-[3-(4-methylphenyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C=2C=CC(C)=CC=2)=C1 ASAVFWNHFYYLGW-UHFFFAOYSA-N 0.000 description 2
• UKMVUPAPYVHIQJ-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(4-methylbenzoyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=C(C)C=C1 UKMVUPAPYVHIQJ-UHFFFAOYSA-N 0.000 description 2
• KXHNVZYFVSLBNR-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(4-methylphenyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1=CC=C(C)C=C1 KXHNVZYFVSLBNR-UHFFFAOYSA-N 0.000 description 2
• IWGUPOMJPZNXGC-UHFFFAOYSA-N ethyl 2-phenylethanimidate;hydron;chloride Chemical compound Cl.CCOC(=N)CC1=CC=CC=C1 IWGUPOMJPZNXGC-UHFFFAOYSA-N 0.000 description 2
• XWCLYXOMBGMKCJ-UHFFFAOYSA-N ethyl 2-thiophen-3-ylethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC=1C=CSC=1 XWCLYXOMBGMKCJ-UHFFFAOYSA-N 0.000 description 2
• JFVSYMXTFJYMEZ-UHFFFAOYSA-N ethyl 3-methylbutanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC(C)C JFVSYMXTFJYMEZ-UHFFFAOYSA-N 0.000 description 2
• OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 2
• YGBFFMMKLWVKGU-UHFFFAOYSA-N ethyl butanimidate;hydrochloride Chemical compound [Cl-].CCCC(=[NH2+])OCC YGBFFMMKLWVKGU-UHFFFAOYSA-N 0.000 description 2
• ATZIPACKTBIFAX-UHFFFAOYSA-N ethyl propanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC ATZIPACKTBIFAX-UHFFFAOYSA-N 0.000 description 2
• 229960003580 felodipine Drugs 0.000 description 2
• 229960002390 flurbiprofen Drugs 0.000 description 2
• SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 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 2
• 229960003883 furosemide Drugs 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 238000011577 humanized mouse model Methods 0.000 description 2
• 229960002003 hydrochlorothiazide Drugs 0.000 description 2
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
• 150000002431 hydrogen Chemical class 0.000 description 2
• NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 2
• 229960004569 indapamide Drugs 0.000 description 2
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
• 230000002757 inflammatory effect Effects 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 230000037356 lipid metabolism Effects 0.000 description 2
• 238000004020 luminiscence type Methods 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 238000002483 medication Methods 0.000 description 2
• 208000030159 metabolic disease Diseases 0.000 description 2
• 239000003863 metallic catalyst Substances 0.000 description 2
• CBTYOUVDLXSENN-UHFFFAOYSA-N methyl 2,2-dimethyl-3-[3-(4-methylphenyl)phenoxy]propanoate Chemical compound COC(=O)C(C)(C)COC1=CC=CC(C=2C=CC(C)=CC=2)=C1 CBTYOUVDLXSENN-UHFFFAOYSA-N 0.000 description 2
• JKXYXUJLTQPERQ-UHFFFAOYSA-N methyl 2,2-dimethyl-5-[2-(4-methylphenyl)phenoxy]pentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=CC=C1C1=CC=C(C)C=C1 JKXYXUJLTQPERQ-UHFFFAOYSA-N 0.000 description 2
• PGMPMHMVLSHRJL-UHFFFAOYSA-N methyl 2,2-dimethyl-5-[3-(4-methylphenyl)phenoxy]pentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=CC(C=2C=CC(C)=CC=2)=C1 PGMPMHMVLSHRJL-UHFFFAOYSA-N 0.000 description 2
• UAPRQAQXVZCEHC-UHFFFAOYSA-N methyl 2,2-dimethyl-5-[4-(4-methylphenyl)phenoxy]pentanoate Chemical compound C1=CC(OCCCC(C)(C)C(=O)OC)=CC=C1C1=CC=C(C)C=C1 UAPRQAQXVZCEHC-UHFFFAOYSA-N 0.000 description 2
• CXTCDMCFOLSIEB-UHFFFAOYSA-N methyl 2,2-dimethyl-8-[2-(4-methylphenyl)phenoxy]octanoate Chemical compound COC(=O)C(C)(C)CCCCCCOC1=CC=CC=C1C1=CC=C(C)C=C1 CXTCDMCFOLSIEB-UHFFFAOYSA-N 0.000 description 2
• BIODDQGVQGOUQK-UHFFFAOYSA-N methyl 2-amino-2-ethylbutanoate;hydrochloride Chemical compound Cl.CCC(N)(CC)C(=O)OC BIODDQGVQGOUQK-UHFFFAOYSA-N 0.000 description 2
• DTHMTBUWTGVEFG-UHFFFAOYSA-N methyl 2-amino-2-phenylacetate;hydrochloride Chemical compound [Cl-].COC(=O)C([NH3+])C1=CC=CC=C1 DTHMTBUWTGVEFG-UHFFFAOYSA-N 0.000 description 2
• NQKSZCPKBRDNJE-UHFFFAOYSA-N methyl 3-[3-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)COC1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 NQKSZCPKBRDNJE-UHFFFAOYSA-N 0.000 description 2
• BQFYJRUXPFOBOX-UHFFFAOYSA-N methyl 4-bromo-3-ethylbenzoate Chemical compound CCC1=CC(C(=O)OC)=CC=C1Br BQFYJRUXPFOBOX-UHFFFAOYSA-N 0.000 description 2
• GFDMVAVUQPFMHB-UHFFFAOYSA-N methyl 4-bromo-3-propylbenzoate Chemical compound CCCC1=CC(C(=O)OC)=CC=C1Br GFDMVAVUQPFMHB-UHFFFAOYSA-N 0.000 description 2
• PYSJIVQKLFYGJH-UHFFFAOYSA-N methyl 8-[2-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethyloctanoate Chemical compound COC(=O)C(C)(C)CCCCCCOC1=CC=CC=C1C1=CC=C(CBr)C=C1 PYSJIVQKLFYGJH-UHFFFAOYSA-N 0.000 description 2
• KRPOBQXKLDMWMI-UHFFFAOYSA-N methyl 8-iodo-2,2-dimethyloctanoate Chemical compound COC(=O)C(C)(C)CCCCCCI KRPOBQXKLDMWMI-UHFFFAOYSA-N 0.000 description 2
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
• SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 2
• 108010038232 microsomal triglyceride transfer protein Proteins 0.000 description 2
• 229960003512 nicotinic acid Drugs 0.000 description 2
• 239000011664 nicotinic acid Substances 0.000 description 2
• 235000001968 nicotinic acid Nutrition 0.000 description 2
• 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 2
• 229960001597 nifedipine Drugs 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 150000002978 peroxides Chemical class 0.000 description 2
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
• PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 2
• 229930029653 phosphoenolpyruvate Natural products 0.000 description 2
• DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 2
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 229960001455 quinapril Drugs 0.000 description 2
• JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 2
• 230000002285 radioactive effect Effects 0.000 description 2
• 229960003401 ramipril Drugs 0.000 description 2
• 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 2
• FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 2
• PFGWGEPQIUAZME-NXSMLHPHSA-N saralasin Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)CNC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)C1=CC=C(O)C=C1 PFGWGEPQIUAZME-NXSMLHPHSA-N 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 235000019345 sodium thiosulphate Nutrition 0.000 description 2
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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
• UQHHGHGBROLOCF-UHFFFAOYSA-N tert-butyl 2-[3-[4-(bromomethyl)phenoxy]phenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(OC=2C=CC(CBr)=CC=2)=C1 UQHHGHGBROLOCF-UHFFFAOYSA-N 0.000 description 2
• LGJKNOWQSDWIDL-UHFFFAOYSA-N tert-butyl 2-[3-[4-(bromomethyl)phenyl]sulfanylphenoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=CC(SC=2C=CC(CBr)=CC=2)=C1 LGJKNOWQSDWIDL-UHFFFAOYSA-N 0.000 description 2
• UGWFDBJONUNYAX-UHFFFAOYSA-N tert-butyl 2-[4-[4-(bromomethyl)phenoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1OC1=CC=C(CBr)C=C1 UGWFDBJONUNYAX-UHFFFAOYSA-N 0.000 description 2
• PWIQSMLOWQJOPD-UHFFFAOYSA-N tert-butyl 2-[4-[4-(bromomethyl)phenyl]sulfanylphenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1SC1=CC=C(CBr)C=C1 PWIQSMLOWQJOPD-UHFFFAOYSA-N 0.000 description 2
• AFRFXFCIJIWWPH-UHFFFAOYSA-N tert-butyl 2-methyl-2-[3-(4-methylphenoxy)phenoxy]propanoate Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(OC(C)(C)C(=O)OC(C)(C)C)=C1 AFRFXFCIJIWWPH-UHFFFAOYSA-N 0.000 description 2
• KDPGCYCDLWGLFX-UHFFFAOYSA-N tert-butyl 2-methyl-2-[3-(4-methylphenyl)phenoxy]propanoate Chemical compound C1=CC(C)=CC=C1C1=CC=CC(OC(C)(C)C(=O)OC(C)(C)C)=C1 KDPGCYCDLWGLFX-UHFFFAOYSA-N 0.000 description 2
• XWEGABHSMLWREM-UHFFFAOYSA-N tert-butyl 2-methyl-2-[4-(4-methylphenoxy)phenoxy]propanoate Chemical compound C1=CC(C)=CC=C1OC1=CC=C(OC(C)(C)C(=O)OC(C)(C)C)C=C1 XWEGABHSMLWREM-UHFFFAOYSA-N 0.000 description 2
• 239000003451 thiazide diuretic agent Substances 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• 230000001052 transient effect Effects 0.000 description 2
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
• 210000003606 umbilical vein Anatomy 0.000 description 2
• 229960001722 verapamil Drugs 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
• CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical class CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 description 1
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
• ZXEIEKDGPVTZLD-NDEPHWFRSA-N (2s)-2-dodecylsulfanyl-n-(4-hydroxy-2,3,5-trimethylphenyl)-2-phenylacetamide Chemical compound O=C([C@@H](SCCCCCCCCCCCC)C=1C=CC=CC=1)NC1=CC(C)=C(O)C(C)=C1C ZXEIEKDGPVTZLD-NDEPHWFRSA-N 0.000 description 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
• WFWQWTPAPNEOFE-UHFFFAOYSA-N (3-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(O)=C1 WFWQWTPAPNEOFE-UHFFFAOYSA-N 0.000 description 1
• KZQIJMIURWFUIS-UHFFFAOYSA-N (3-methoxyphenyl)-(4-methylphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(C)=CC=2)=C1 KZQIJMIURWFUIS-UHFFFAOYSA-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
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
• FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
• HBEIHPSICGGZIF-UHFFFAOYSA-N (4-bromo-2-methoxyphenyl)methanol Chemical compound COC1=CC(Br)=CC=C1CO HBEIHPSICGGZIF-UHFFFAOYSA-N 0.000 description 1
• COIQUVGFTILYGA-UHFFFAOYSA-N (4-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(O)C=C1 COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 description 1
• SRKGZXIJDGWVAI-GVAVTCRGSA-M (e,3r)-7-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)C1=NC(C(C)(C)C)=CC(C=2C=CC(F)=CC=2)=C1\C=C\C(O)C[C@@H](O)CC([O-])=O SRKGZXIJDGWVAI-GVAVTCRGSA-M 0.000 description 1
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
• AAAXMNYUNVCMCJ-UHFFFAOYSA-N 1,3-diiodopropane Chemical compound ICCCI AAAXMNYUNVCMCJ-UHFFFAOYSA-N 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• QLIMAARBRDAYGQ-UHFFFAOYSA-N 1,6-diiodohexane Chemical compound ICCCCCCI QLIMAARBRDAYGQ-UHFFFAOYSA-N 0.000 description 1
• WAUNFWSVXRPCDQ-UHFFFAOYSA-N 1-(bromomethyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1CBr WAUNFWSVXRPCDQ-UHFFFAOYSA-N 0.000 description 1
• OZVKFLCLBGLQAN-UHFFFAOYSA-N 1-(phenylmethoxymethyl)tetrazole Chemical compound C=1C=CC=CC=1COCN1C=NN=N1 OZVKFLCLBGLQAN-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
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
• WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 description 1
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
• QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
• ZPCJPJQUVRIILS-UHFFFAOYSA-N 1-bromo-3-(bromomethyl)benzene Chemical compound BrCC1=CC=CC(Br)=C1 ZPCJPJQUVRIILS-UHFFFAOYSA-N 0.000 description 1
• ZVWCZRGXNBTXOB-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-ethylbenzene Chemical compound CCC1=CC(CBr)=CC=C1Br ZVWCZRGXNBTXOB-UHFFFAOYSA-N 0.000 description 1
• CWOKZNRRLJXSAA-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC(CBr)=CC=C1Br CWOKZNRRLJXSAA-UHFFFAOYSA-N 0.000 description 1
• AALQUOHYAMXZRQ-UHFFFAOYSA-N 1-methoxy-4-(4-methylphenoxy)benzene Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C)C=C1 AALQUOHYAMXZRQ-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
• JVNCFFFHVBWVBR-UHFFFAOYSA-N 2-(1-hydroxyethyl)phenol Chemical compound CC(O)C1=CC=CC=C1O JVNCFFFHVBWVBR-UHFFFAOYSA-N 0.000 description 1
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
• ODJXDERKANYVSL-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2C(=CC=CC=2)O)=C1 ODJXDERKANYVSL-UHFFFAOYSA-N 0.000 description 1
• ABFCOJLLBHXNOU-UHFFFAOYSA-N 2-(2-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=CC=C1O ABFCOJLLBHXNOU-UHFFFAOYSA-N 0.000 description 1
• RLMRVKKDBUFIHN-UHFFFAOYSA-N 2-(3-bromophenoxy)acetonitrile Chemical compound BrC1=CC=CC(OCC#N)=C1 RLMRVKKDBUFIHN-UHFFFAOYSA-N 0.000 description 1
• ZDQJMPZGBDACLX-UHFFFAOYSA-N 2-(3-bromophenoxy)butanenitrile Chemical compound CCC(C#N)OC1=CC=CC(Br)=C1 ZDQJMPZGBDACLX-UHFFFAOYSA-N 0.000 description 1
• ACNHMDZFOSJISH-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]-4-fluorophenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C(=CC=C(OC(C)(C)C(O)=O)C=2)F)C=C1 ACNHMDZFOSJISH-UHFFFAOYSA-N 0.000 description 1
• YUWJXIOPMCFSEO-UHFFFAOYSA-N 2-[3-[4-[(2-butyl-4,4-diethyl-5-oxoimidazol-1-yl)methyl]phenyl]phenoxy]butanoic acid Chemical compound CCCCC1=NC(CC)(CC)C(=O)N1CC1=CC=C(C=2C=C(OC(CC)C(O)=O)C=CC=2)C=C1 YUWJXIOPMCFSEO-UHFFFAOYSA-N 0.000 description 1
• OQDPVLVUJFGPGQ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]pyrimidine Chemical compound C=1C=C2OCOC2=CC=1CN(CC1)CCN1C1=NC=CC=N1 OQDPVLVUJFGPGQ-UHFFFAOYSA-N 0.000 description 1
• CBUOGMOTDGNEAW-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(CBr)C=C1 CBUOGMOTDGNEAW-UHFFFAOYSA-N 0.000 description 1
• DOMSQRZPCGHIHB-UHFFFAOYSA-N 2-[4-[4-[(2-butyl-5-oxo-4-phenyl-4h-imidazol-1-yl)methyl]benzoyl]phenoxy]-2-methylpropanoic acid Chemical compound CCCCC1=NC(C=2C=CC=CC=2)C(=O)N1CC(C=C1)=CC=C1C(=O)C1=CC=C(OC(C)(C)C(O)=O)C=C1 DOMSQRZPCGHIHB-UHFFFAOYSA-N 0.000 description 1
• AADGYGICLHMGSB-UHFFFAOYSA-N 2-[4-bromo-3-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Br)C(C=2C=CC(CBr)=CC=2)=C1 AADGYGICLHMGSB-UHFFFAOYSA-N 0.000 description 1
• FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 1
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
• KWOMLHIFHFWBSB-UHFFFAOYSA-N 2-azaniumyl-2-ethylbutanoate Chemical compound CCC(N)(CC)C(O)=O KWOMLHIFHFWBSB-UHFFFAOYSA-N 0.000 description 1
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
• MNNDREXLRLDWEY-UHFFFAOYSA-N 2-bromo-4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(Br)=C1 MNNDREXLRLDWEY-UHFFFAOYSA-N 0.000 description 1
• CGPTZCZFFUYDCB-UHFFFAOYSA-N 2-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(Br)=C1 CGPTZCZFFUYDCB-UHFFFAOYSA-N 0.000 description 1
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• GWZCLMWEJWPFFA-UHFFFAOYSA-N 2-thiophen-3-ylacetonitrile Chemical compound N#CCC=1C=CSC=1 GWZCLMWEJWPFFA-UHFFFAOYSA-N 0.000 description 1
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
• KWHAWSFIMHIJGD-UHFFFAOYSA-N 3-(4-methylphenyl)sulfanylphenol Chemical compound C1=CC(C)=CC=C1SC1=CC=CC(O)=C1 KWHAWSFIMHIJGD-UHFFFAOYSA-N 0.000 description 1
• IIGNZLVHOZEOPV-UHFFFAOYSA-N 3-Methoxybenzyl alcohol Chemical compound COC1=CC=CC(CO)=C1 IIGNZLVHOZEOPV-UHFFFAOYSA-N 0.000 description 1
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
• NGVMXYZQTRFAHF-UHFFFAOYSA-N 3-iodo-2,2-dimethylpropanoic acid Chemical compound ICC(C)(C)C(O)=O NGVMXYZQTRFAHF-UHFFFAOYSA-N 0.000 description 1
• RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 1
• 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
• MLRAJZNPKPVUDQ-UHFFFAOYSA-N 3-sulfanyl-1,2-dihydrotriazole Chemical compound SN1NNC=C1 MLRAJZNPKPVUDQ-UHFFFAOYSA-N 0.000 description 1
• DQFMPTUTAAIXAN-UHFFFAOYSA-N 4,4-dimethyl-1h-imidazol-5-one Chemical compound CC1(C)NC=NC1=O DQFMPTUTAAIXAN-UHFFFAOYSA-N 0.000 description 1
• OWYLAEYXIQKAOL-UHFFFAOYSA-N 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCC1 OWYLAEYXIQKAOL-UHFFFAOYSA-N 0.000 description 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
• ZGNKVLNPAFWDIC-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1CBr ZGNKVLNPAFWDIC-UHFFFAOYSA-N 0.000 description 1
• BXIMEAILBFUBCC-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-propylbenzene Chemical compound CCCC1=CC(Br)=CC=C1CBr BXIMEAILBFUBCC-UHFFFAOYSA-N 0.000 description 1
• ZOBCLWSQVDWKDY-UHFFFAOYSA-N 4-bromo-1-methoxy-2-(2-methylpropyl)benzene Chemical compound COC1=CC=C(Br)C=C1CC(C)C ZOBCLWSQVDWKDY-UHFFFAOYSA-N 0.000 description 1
• JXHWAPDBDXPBEQ-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1C(F)(F)F JXHWAPDBDXPBEQ-UHFFFAOYSA-N 0.000 description 1
• AHEFLXSBFQVHOM-UHFFFAOYSA-N 4-bromo-2-methoxy-1-(2-methylpropyl)benzene Chemical compound COC1=CC(Br)=CC=C1CC(C)C AHEFLXSBFQVHOM-UHFFFAOYSA-N 0.000 description 1
• ZIRHHEZLJGORGU-UHFFFAOYSA-N 4-bromo-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1[N+]([O-])=O ZIRHHEZLJGORGU-UHFFFAOYSA-N 0.000 description 1
• KWVXDZLVCISXIB-UHFFFAOYSA-N 4-bromo-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1Br KWVXDZLVCISXIB-UHFFFAOYSA-N 0.000 description 1
• GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-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
• RTTMZCCBDAJGRW-UHFFFAOYSA-N 5-(3-methoxyphenyl)-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound COC1=CC=CC(C=2NNC(=S)N=2)=C1 RTTMZCCBDAJGRW-UHFFFAOYSA-N 0.000 description 1
• USRWSSVQAGNWRI-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound C1=CC(OC)=CC=C1C1=NC(=S)NN1 USRWSSVQAGNWRI-UHFFFAOYSA-N 0.000 description 1
• ZDXUVDGTLMMLPW-UHFFFAOYSA-N 5-(bromomethyl)-2-(3-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazole Chemical compound COC1=CC=CC(C2=NN3C(C)=C(CBr)SC3=N2)=C1 ZDXUVDGTLMMLPW-UHFFFAOYSA-N 0.000 description 1
• UACLKICXWDLRHG-UHFFFAOYSA-N 5-(bromomethyl)-2-(4-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazole Chemical compound C1=CC(OC)=CC=C1C1=NN2C(C)=C(CBr)SC2=N1 UACLKICXWDLRHG-UHFFFAOYSA-N 0.000 description 1
• CZFLIHOPQXKRSH-UHFFFAOYSA-N 5-[3-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCOC1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 CZFLIHOPQXKRSH-UHFFFAOYSA-N 0.000 description 1
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
• KEBHWHNQGDAHAN-UHFFFAOYSA-N 5-iodo-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCI KEBHWHNQGDAHAN-UHFFFAOYSA-N 0.000 description 1
• QFZZUAINSDZUDG-UHFFFAOYSA-N 5h-[1,3]thiazolo[4,5-d]triazole Chemical compound N1=NC2=NCSC2=N1 QFZZUAINSDZUDG-UHFFFAOYSA-N 0.000 description 1
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
• ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 1
• 108050000824 Angiotensin II receptor Proteins 0.000 description 1
• 102000008873 Angiotensin II receptor Human genes 0.000 description 1
• 102400000344 Angiotensin-1 Human genes 0.000 description 1
• 101800000734 Angiotensin-1 Proteins 0.000 description 1
• 108010060219 Apolipoprotein E2 Proteins 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 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
• PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 description 1
• 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 1
• 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
• 239000004342 Benzoyl peroxide Substances 0.000 description 1
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
• 229940123208 Biguanide Drugs 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• 201000006474 Brain Ischemia Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
• 102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
• 239000002083 C09CA01 - Losartan Substances 0.000 description 1
• 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
• 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
• 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
• 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
• 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 206010008120 Cerebral ischaemia Diseases 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• 229940126639 Compound 33 Drugs 0.000 description 1
• 229940127007 Compound 39 Drugs 0.000 description 1
• 206010052895 Coronary artery insufficiency 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
• 230000004568 DNA-binding Effects 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 240000001879 Digitalis lutea Species 0.000 description 1
• WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
• LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
• 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 description 1
• HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=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](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)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(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
• 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 1
• 108010001515 Galectin 4 Proteins 0.000 description 1
• 102100039556 Galectin-4 Human genes 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
• 239000009429 Ginkgo biloba extract Substances 0.000 description 1
• 229940127552 Glucagon-like Peptide-1 (GLP-1) Agonists Drugs 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
• 206010019280 Heart failures Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 description 1
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 102000014150 Interferons Human genes 0.000 description 1
• 108010050904 Interferons Proteins 0.000 description 1
• 238000008214 LDL Cholesterol Methods 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 229940122048 Leucotriene receptor antagonist Drugs 0.000 description 1
• 229940127470 Lipase Inhibitors Drugs 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
• IRLWJILLXJGJTD-UHFFFAOYSA-N Muraglitazar Chemical compound C1=CC(OC)=CC=C1OC(=O)N(CC(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 IRLWJILLXJGJTD-UHFFFAOYSA-N 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 208000021642 Muscular disease Diseases 0.000 description 1
• 201000009623 Myopathy Diseases 0.000 description 1
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
• BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 1
• KBAFPSLPKGSANY-UHFFFAOYSA-N Naftidrofuryl Chemical compound C=1C=CC2=CC=CC=C2C=1CC(C(=O)OCCN(CC)CC)CC1CCCO1 KBAFPSLPKGSANY-UHFFFAOYSA-N 0.000 description 1
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
• 244000061176 Nicotiana tabacum Species 0.000 description 1
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
• SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 102000004316 Oxidoreductases Human genes 0.000 description 1
• 108090000854 Oxidoreductases Proteins 0.000 description 1
• RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
• BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
• 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 240000001987 Pyrus communis Species 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
• 229910006069 SO3H Inorganic materials 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• 108010083387 Saralasin Proteins 0.000 description 1
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
• 108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• 206010047139 Vasoconstriction Diseases 0.000 description 1
• 229930003427 Vitamin E Natural products 0.000 description 1
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
• PDGKPDALSDRSHF-UHFFFAOYSA-N [1,3]thiazolo[3,2-b][1,2,4]triazole Chemical compound N1=CN=C2SC=CN21 PDGKPDALSDRSHF-UHFFFAOYSA-N 0.000 description 1
• KXMUDHYKFRXYJN-UHFFFAOYSA-N [2-(3-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazol-5-yl]methanol Chemical compound COC1=CC=CC(C2=NN3C(C)=C(CO)SC3=N2)=C1 KXMUDHYKFRXYJN-UHFFFAOYSA-N 0.000 description 1
• XTUOEDUNJCUEFT-UHFFFAOYSA-N [2-(4-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazol-5-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=NN2C(C)=C(CO)SC2=N1 XTUOEDUNJCUEFT-UHFFFAOYSA-N 0.000 description 1
• GLYOPNLBKCBTMI-UHFFFAOYSA-N [2-chloro-2-(1-chloro-2-phenylethoxy)ethyl]benzene Chemical compound C=1C=CC=CC=1CC(Cl)OC(Cl)CC1=CC=CC=C1 GLYOPNLBKCBTMI-UHFFFAOYSA-N 0.000 description 1
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
• UEFAYWPDOUCERJ-UHFFFAOYSA-N [bromo(phenoxy)methyl]benzene Chemical class C=1C=CC=CC=1C(Br)OC1=CC=CC=C1 UEFAYWPDOUCERJ-UHFFFAOYSA-N 0.000 description 1
• GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• FPHLBGOJWPEVME-UHFFFAOYSA-N alminoprofen Chemical compound OC(=O)C(C)C1=CC=C(NCC(C)=C)C=C1 FPHLBGOJWPEVME-UHFFFAOYSA-N 0.000 description 1
• 229960004663 alminoprofen Drugs 0.000 description 1
• 239000002160 alpha blocker Substances 0.000 description 1
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
• 229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
• ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
• QZNJPJDUBTYMRS-UHFFFAOYSA-M amfenac sodium hydrate Chemical group O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 QZNJPJDUBTYMRS-UHFFFAOYSA-M 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229960005260 amiodarone Drugs 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• 238000000540 analysis of variance Methods 0.000 description 1
• 238000012443 analytical study Methods 0.000 description 1
• ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
• 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
• 229940127282 angiotensin receptor antagonist Drugs 0.000 description 1
• MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 230000002253 anti-ischaemic effect Effects 0.000 description 1
• 239000000883 anti-obesity agent Substances 0.000 description 1
• 239000000924 antiasthmatic agent Substances 0.000 description 1
• 239000003472 antidiabetic agent Substances 0.000 description 1
• 239000002220 antihypertensive agent Substances 0.000 description 1
• 229940030600 antihypertensive agent Drugs 0.000 description 1
• 229940124572 antihypotensive agent Drugs 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 229940125710 antiobesity agent Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 229940127218 antiplatelet drug Drugs 0.000 description 1
• 210000002376 aorta thoracic Anatomy 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 150000005840 aryl radicals Chemical class 0.000 description 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
• 230000003143 atherosclerotic effect Effects 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 229950010046 avasimibe Drugs 0.000 description 1
• UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000019400 benzoyl peroxide Nutrition 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 description 1
• 229960003665 bepridil Drugs 0.000 description 1
• 229960002537 betamethasone Drugs 0.000 description 1
• UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 239000003613 bile acid Substances 0.000 description 1
• 239000012455 biphasic mixture Substances 0.000 description 1
• LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• HSBHWEVOJUMLEY-UHFFFAOYSA-N boron;dimethyl sulfite Chemical compound [B].COS(=O)OC HSBHWEVOJUMLEY-UHFFFAOYSA-N 0.000 description 1
• 125000005620 boronic acid group Chemical class 0.000 description 1
• 229940124630 bronchodilator Drugs 0.000 description 1
• 239000000168 bronchodilator agent Substances 0.000 description 1
• 229960001415 buflomedil Drugs 0.000 description 1
• DONPXXYPNADLEN-UHFFFAOYSA-N butyl 2-[3-[4-(bromomethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound BrCC1=CC=C(C=C1)C1=CC(=CC=C1)OC(C(=O)OCCCC)(C)C DONPXXYPNADLEN-UHFFFAOYSA-N 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 229960000932 candesartan Drugs 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
• 239000002775 capsule Substances 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
• 230000003293 cardioprotective effect Effects 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 229960000590 celecoxib Drugs 0.000 description 1
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
• 230000021164 cell adhesion Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 206010008118 cerebral infarction Diseases 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 230000001906 cholesterol absorption Effects 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 229960003009 clopidogrel Drugs 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
• RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
• 239000005516 coenzyme A Substances 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 229940126543 compound 14 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 229940126208 compound 22 Drugs 0.000 description 1
• 229940125961 compound 24 Drugs 0.000 description 1
• 229940125851 compound 27 Drugs 0.000 description 1
• 229940127204 compound 29 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 229940125878 compound 36 Drugs 0.000 description 1
• 229940125807 compound 37 Drugs 0.000 description 1
• 229940127573 compound 38 Drugs 0.000 description 1
• 229940126540 compound 41 Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 229940127113 compound 57 Drugs 0.000 description 1
• 229940125900 compound 59 Drugs 0.000 description 1
• 229940126179 compound 72 Drugs 0.000 description 1
• 230000001143 conditioned effect Effects 0.000 description 1
• 230000021615 conjugation Effects 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 229940109248 cromoglycate Drugs 0.000 description 1
• IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 1
• 239000000824 cytostatic agent Substances 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• 239000002254 cytotoxic agent Substances 0.000 description 1
• 231100000599 cytotoxic agent Toxicity 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
• 230000003831 deregulation Effects 0.000 description 1
• 238000003795 desorption Methods 0.000 description 1
• 239000011903 deuterated solvents‎ Substances 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960001259 diclofenac Drugs 0.000 description 1
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
• 229960000648 digitoxin Drugs 0.000 description 1
• LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
• 229960005156 digoxin Drugs 0.000 description 1
• LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
• NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 description 1
• 229960002768 dipyridamole Drugs 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
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 229950005925 eflucimibe Drugs 0.000 description 1
• 210000002889 endothelial cell Anatomy 0.000 description 1
• 230000003511 endothelial effect Effects 0.000 description 1
• 230000008753 endothelial function Effects 0.000 description 1
• 229960000972 enoximone Drugs 0.000 description 1
• ZJKNESGOIKRXQY-UHFFFAOYSA-N enoximone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=C(C)NC(=O)N1 ZJKNESGOIKRXQY-UHFFFAOYSA-N 0.000 description 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• ADFASIQRQWKXSJ-UHFFFAOYSA-N ethyl 1-aminocyclopentane-1-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1(N)CCCC1 ADFASIQRQWKXSJ-UHFFFAOYSA-N 0.000 description 1
• ZKTSNAQZASWKOE-UHFFFAOYSA-N ethyl 2-(3-methoxyphenyl)-6-methyl-[1,3]thiazolo[3,2-b][1,2,4]triazole-5-carboxylate Chemical compound N=1N2C(C)=C(C(=O)OCC)SC2=NC=1C1=CC=CC(OC)=C1 ZKTSNAQZASWKOE-UHFFFAOYSA-N 0.000 description 1
• JUGUSUOWAHPNFU-UHFFFAOYSA-N ethyl 2-[2-[4-(bromomethyl)benzoyl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1C(=O)C1=CC=C(CBr)C=C1 JUGUSUOWAHPNFU-UHFFFAOYSA-N 0.000 description 1
• RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
• SXOKHVOVQBTWJS-UHFFFAOYSA-N ethyl 2-methyl-2-[2-(4-methylbenzoyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1C(=O)C1=CC=C(C)C=C1 SXOKHVOVQBTWJS-UHFFFAOYSA-N 0.000 description 1
• IOYJFGMGNOZRGR-UHFFFAOYSA-N ethyl 2-methyl-2-[3-(4-methylbenzoyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C(=O)C=2C=CC(C)=CC=2)=C1 IOYJFGMGNOZRGR-UHFFFAOYSA-N 0.000 description 1
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• YKSUEQRNXOAPPK-UHFFFAOYSA-N ethyl pentanimidate Chemical compound CCCCC(=N)OCC YKSUEQRNXOAPPK-UHFFFAOYSA-N 0.000 description 1
• XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 1
• 229960005293 etodolac Drugs 0.000 description 1
• 229960001519 exenatide Drugs 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 229960000815 ezetimibe Drugs 0.000 description 1
• OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 239000007897 gelcap Substances 0.000 description 1
• 229960003627 gemfibrozil Drugs 0.000 description 1
• 229910052732 germanium Inorganic materials 0.000 description 1
• GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
• 229940068052 ginkgo biloba extract Drugs 0.000 description 1
• 235000020686 ginkgo biloba extract Nutrition 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• 229960000346 gliclazide 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
• 229960004346 glimepiride Drugs 0.000 description 1
• 230000023611 glucuronidation Effects 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
• 230000012010 growth Effects 0.000 description 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 208000019622 heart disease Diseases 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 229960000890 hydrocortisone Drugs 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
• 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
• 239000005555 hypertensive agent Substances 0.000 description 1
• 230000001631 hypertensive effect Effects 0.000 description 1
• 230000001227 hypertriglyceridemic effect Effects 0.000 description 1
• 229960001680 ibuprofen Drugs 0.000 description 1
• 150000002463 imidates Chemical class 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 229960000905 indomethacin Drugs 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 238000003780 insertion Methods 0.000 description 1
• 230000037431 insertion Effects 0.000 description 1
• 229940047124 interferons Drugs 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229960002198 irbesartan Drugs 0.000 description 1
• YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
• QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
• 229960000201 isosorbide dinitrate Drugs 0.000 description 1
• MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
• 239000000644 isotonic solution Substances 0.000 description 1
• QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
• 229960000991 ketoprofen Drugs 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 239000002502 liposome Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 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
• 210000002540 macrophage Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229960001929 meloxicam Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 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
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical class COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
• GRKWHXNAHIMNJD-UHFFFAOYSA-N methoxysulfanyloxymethane Chemical class COSOC GRKWHXNAHIMNJD-UHFFFAOYSA-N 0.000 description 1
• AVKWDOWMCZXYAD-UHFFFAOYSA-N methyl 1-amino-2-methylcyclohexane-1-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(N)CCCCC1C AVKWDOWMCZXYAD-UHFFFAOYSA-N 0.000 description 1
• MTPXRXOMKRLUMU-UHFFFAOYSA-N methyl 1-aminocyclohexane-1-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(N)CCCCC1 MTPXRXOMKRLUMU-UHFFFAOYSA-N 0.000 description 1
• CMXCNXJZKXRQNL-UHFFFAOYSA-N methyl 3-iodo-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CI CMXCNXJZKXRQNL-UHFFFAOYSA-N 0.000 description 1
• GTZTYNPAPQKIIR-UHFFFAOYSA-N methyl 4-bromo-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C(C)=C1 GTZTYNPAPQKIIR-UHFFFAOYSA-N 0.000 description 1
• DVWLURWTHYVSJK-UHFFFAOYSA-N methyl 5-[3-[4-(bromomethyl)phenyl]phenoxy]-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 DVWLURWTHYVSJK-UHFFFAOYSA-N 0.000 description 1
• ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
• 229940095102 methyl benzoate Drugs 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 229960003574 milrinone Drugs 0.000 description 1
• PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
• 229960004027 molsidomine Drugs 0.000 description 1
• 229960005127 montelukast Drugs 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 229950001135 muraglitazar Drugs 0.000 description 1
• 229940105132 myristate Drugs 0.000 description 1
• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 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
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960004270 nabumetone Drugs 0.000 description 1
• 229960001132 naftidrofuryl Drugs 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229960002009 naproxen Drugs 0.000 description 1
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-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
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000002560 nitrile group Chemical group 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 102000006255 nuclear receptors Human genes 0.000 description 1
• 108020004017 nuclear receptors Proteins 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
• 229940012843 omega-3 fatty acid Drugs 0.000 description 1
• 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
• 239000006014 omega-3 oil Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 125000002734 organomagnesium group Chemical group 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
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 230000036542 oxidative stress Effects 0.000 description 1
• 229960001476 pentoxifylline Drugs 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
• 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 230000003285 pharmacodynamic effect Effects 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
• TYZYRCHEVXXLSJ-UHFFFAOYSA-N phenylmethoxymethoxymethoxymethylbenzene Chemical compound C=1C=CC=CC=1COCOCOCC1=CC=CC=C1 TYZYRCHEVXXLSJ-UHFFFAOYSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
• 229940068065 phytosterols Drugs 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229960004310 piribedil Drugs 0.000 description 1
• 229960002702 piroxicam Drugs 0.000 description 1
• QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
• 230000036470 plasma concentration Effects 0.000 description 1
• 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 229940068968 polysorbate 80 Drugs 0.000 description 1
• 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
• 229960005205 prednisolone Drugs 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 1
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
• 239000003755 preservative agent Substances 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
• 229940002612 prodrug Drugs 0.000 description 1
• 239000000651 prodrug Substances 0.000 description 1
• 239000000583 progesterone congener Substances 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
• 239000012264 purified product Substances 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000005412 pyrazyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000001172 regenerating effect Effects 0.000 description 1
• 239000003488 releasing hormone Substances 0.000 description 1
• 230000036454 renin-angiotensin system Effects 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 1
• 229960003015 rimonabant Drugs 0.000 description 1
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
• 229960000371 rofecoxib Drugs 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 229960004785 saralasin Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 230000007017 scission 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
• 230000000580 secretagogue effect Effects 0.000 description 1
• 230000000276 sedentary effect Effects 0.000 description 1
• 239000011669 selenium Substances 0.000 description 1
• 239000003352 sequestering agent Substances 0.000 description 1
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
• 229960004425 sibutramine Drugs 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
• 229940075620 somatostatin analogue Drugs 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
• 229960000894 sulindac Drugs 0.000 description 1
• MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 229960005187 telmisartan Drugs 0.000 description 1
• LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 description 1
• 229960002871 tenoxicam Drugs 0.000 description 1
• PDTIJONSXYTTGT-UHFFFAOYSA-N tert-butyl 2-methyl-2-[3-(4-methylphenoxy)phenyl]sulfanylpropanoate Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(SC(C)(C)C(=O)OC(C)(C)C)=C1 PDTIJONSXYTTGT-UHFFFAOYSA-N 0.000 description 1
• AWBIMXVCKGXIFE-UHFFFAOYSA-N tert-butyl 2-methyl-2-[3-(4-methylphenyl)sulfanylphenoxy]propanoate Chemical compound C1=CC(C)=CC=C1SC1=CC=CC(OC(C)(C)C(=O)OC(C)(C)C)=C1 AWBIMXVCKGXIFE-UHFFFAOYSA-N 0.000 description 1
• KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
• 229950004704 tesaglitazar Drugs 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 229960001312 tiaprofenic acid Drugs 0.000 description 1
• 229960005001 ticlopidine Drugs 0.000 description 1
• PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-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
• 230000002103 transcriptional effect Effects 0.000 description 1
• 238000010361 transduction Methods 0.000 description 1
• 230000026683 transduction Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 238000007473 univariate analysis Methods 0.000 description 1
• 229960004699 valsartan Drugs 0.000 description 1
• ACWBQPMHZXGDFX-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=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 210000005167 vascular cell Anatomy 0.000 description 1
• 230000025033 vasoconstriction Effects 0.000 description 1
• 239000005526 vasoconstrictor agent Substances 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
• 229960001254 vildagliptin Drugs 0.000 description 1
• 235000019165 vitamin E Nutrition 0.000 description 1
• 229940046009 vitamin E Drugs 0.000 description 1
• 239000011709 vitamin E Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1