JP2004528337A5 - - Google Patents

Info

Publication number

JP2004528337A5

JP2004528337A5 JP2002584860A JP2002584860A JP2004528337A5 JP 2004528337 A5 JP2004528337 A5 JP 2004528337A5 JP 2002584860 A JP2002584860 A JP 2002584860A JP 2002584860 A JP2002584860 A JP 2002584860A JP 2004528337 A5 JP2004528337 A5 JP 2004528337A5

Authority

JP

Japan

Prior art keywords

group

nitric oxide

acid

nitrosated

nebivolol

Prior art date

2002-05-01

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

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• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 535
• 150000001875 compounds Chemical class 0.000 description 212
• -1 hydrazine compound Chemical class 0.000 description 181
• KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 description 164
• 229960000619 nebivolol Drugs 0.000 description 102
• 239000003814 drug Substances 0.000 description 94
• 239000000203 mixture Substances 0.000 description 85
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
• 238000000034 method Methods 0.000 description 67
• 239000002253 acid Substances 0.000 description 65
• 125000000217 alkyl group Chemical group 0.000 description 65
• 150000002148 esters Chemical class 0.000 description 62
• 125000003118 aryl group Chemical group 0.000 description 60
• 208000024172 Cardiovascular disease Diseases 0.000 description 58
• 229940124597 therapeutic agent Drugs 0.000 description 55
• 150000003839 salts Chemical class 0.000 description 44
• 239000003963 antioxidant agent Substances 0.000 description 43
• 239000001257 hydrogen Substances 0.000 description 42
• 229910052739 hydrogen Inorganic materials 0.000 description 42
• 235000006708 antioxidants Nutrition 0.000 description 40
• 239000011159 matrix material Substances 0.000 description 36
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 34
• 239000002840 nitric oxide donor Substances 0.000 description 34
• 150000001412 amines Chemical class 0.000 description 33
• 125000003396 thiol group Chemical group [H]S* 0.000 description 33
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
• 102000008299 Nitric Oxide Synthase Human genes 0.000 description 32
• 108010021487 Nitric Oxide Synthase Proteins 0.000 description 32
• 239000003795 chemical substances by application Substances 0.000 description 32
• 239000000066 endothelium dependent relaxing factor Substances 0.000 description 32
• 125000000623 heterocyclic group Chemical group 0.000 description 31
• 239000000758 substrate Substances 0.000 description 28
• 238000001727 in vivo Methods 0.000 description 27
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
• 238000004519 manufacturing process Methods 0.000 description 26
• 239000002904 solvent Substances 0.000 description 26
• 206010020772 Hypertension Diseases 0.000 description 25
• 230000003078 antioxidant effect Effects 0.000 description 25
• 230000015572 biosynthetic process Effects 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 25
• 125000000753 cycloalkyl group Chemical group 0.000 description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
• 125000006239 protecting group Chemical group 0.000 description 25
• 238000012546 transfer Methods 0.000 description 25
• 230000002792 vascular Effects 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000002585 base Substances 0.000 description 24
• 239000002552 dosage form Substances 0.000 description 23
• 239000000126 substance Substances 0.000 description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
• 239000003054 catalyst Substances 0.000 description 21
• 238000011282 treatment Methods 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 150000002431 hydrogen Chemical class 0.000 description 20
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 18
• 229930195733 hydrocarbon Natural products 0.000 description 18
• 230000001965 increasing effect Effects 0.000 description 18
• 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 18
• 239000012730 sustained-release form Substances 0.000 description 18
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 17
• 238000013268 sustained release Methods 0.000 description 17
• 210000001519 tissue Anatomy 0.000 description 17
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 16
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• 229910002651 NO3 Inorganic materials 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 125000003545 alkoxy group Chemical group 0.000 description 16
• 150000008064 anhydrides Chemical class 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 16
• 239000012024 dehydrating agents‎ Substances 0.000 description 16
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 16
• YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 238000010511 deprotection reaction Methods 0.000 description 15
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 14
• 102000004190 Enzymes Human genes 0.000 description 14
• 108090000790 Enzymes Proteins 0.000 description 14
• 229920002675 Polyoxyl Polymers 0.000 description 14
• 238000009833 condensation Methods 0.000 description 14
• 230000005494 condensation Effects 0.000 description 14
• 230000007812 deficiency Effects 0.000 description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
• 229940088598 enzyme Drugs 0.000 description 14
• 150000002430 hydrocarbons Chemical class 0.000 description 14
• 229960000201 isosorbide dinitrate Drugs 0.000 description 14
• 108090000765 processed proteins & peptides Proteins 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• 210000004509 vascular smooth muscle cell Anatomy 0.000 description 14
• 239000004215 Carbon black (E152) Substances 0.000 description 13
• 201000010099 disease Diseases 0.000 description 13
• RPTUSVTUFVMDQK-UHFFFAOYSA-N hydrallazine Natural products C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 13
• 229960003827 isosorbide mononitrate Drugs 0.000 description 13
• 241000894007 species Species 0.000 description 13
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
• GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 12
• 125000003158 alcohol group Chemical group 0.000 description 12
• 235000001014 amino acid Nutrition 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 102000004196 processed proteins & peptides Human genes 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 108090000623 proteins and genes Proteins 0.000 description 12
• 239000003642 reactive oxygen metabolite Substances 0.000 description 12
• 150000003568 thioethers Chemical class 0.000 description 12
• 208000019553 vascular disease Diseases 0.000 description 12
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 11
• 125000003282 alkyl amino group Chemical group 0.000 description 11
• 150000001413 amino acids Chemical class 0.000 description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
• 210000004204 blood vessel Anatomy 0.000 description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
• 239000000306 component Substances 0.000 description 11
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 11
• 229920001184 polypeptide Polymers 0.000 description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• 239000008280 blood Substances 0.000 description 10
• 210000004369 blood Anatomy 0.000 description 10
• 150000003857 carboxamides Chemical class 0.000 description 10
• 239000002207 metabolite Substances 0.000 description 10
• 229910052760 oxygen Inorganic materials 0.000 description 10
• 239000001301 oxygen Substances 0.000 description 10
• 230000000144 pharmacologic effect Effects 0.000 description 10
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• 230000001225 therapeutic effect Effects 0.000 description 10
• 239000005541 ACE inhibitor Substances 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 239000011248 coating agent Substances 0.000 description 9
• 238000000576 coating method Methods 0.000 description 9
• 125000004663 dialkyl amino group Chemical group 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 239000003937 drug carrier Substances 0.000 description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
• 239000011859 microparticle Substances 0.000 description 9
• YAYBWZFZDMHVDH-UHFFFAOYSA-N n-amino-n-hydroxynitrous amide Chemical class NN(O)N=O YAYBWZFZDMHVDH-UHFFFAOYSA-N 0.000 description 9
• 235000018102 proteins Nutrition 0.000 description 9
• 102000004169 proteins and genes Human genes 0.000 description 9
• 230000004044 response Effects 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• 239000011593 sulfur Substances 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• XWOYCQCJZYOINY-UHFFFAOYSA-N 2-(oxan-2-ylsulfanyl)oxane Chemical compound O1CCCCC1SC1OCCCC1 XWOYCQCJZYOINY-UHFFFAOYSA-N 0.000 description 8
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
• 201000001320 Atherosclerosis Diseases 0.000 description 8
• 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 8
• KEJOCWOXCDWNID-UHFFFAOYSA-N Nitrilooxonium Chemical compound [O+]#N KEJOCWOXCDWNID-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 208000003782 Raynaud disease Diseases 0.000 description 8
• 208000012322 Raynaud phenomenon Diseases 0.000 description 8
• 125000002877 alkyl aryl group Chemical group 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 239000005557 antagonist Substances 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 125000001769 aryl amino group Chemical group 0.000 description 8
• 239000002876 beta blocker Substances 0.000 description 8
• 230000017531 blood circulation Effects 0.000 description 8
• 150000001733 carboxylic acid esters Chemical class 0.000 description 8
• 150000001767 cationic compounds Chemical class 0.000 description 8
• PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 8
• AVTGHGVUVGIZRD-UHFFFAOYSA-N dinitroso sulfite Chemical compound O=NOS(=O)ON=O AVTGHGVUVGIZRD-UHFFFAOYSA-N 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 125000004438 haloalkoxy group Chemical group 0.000 description 8
• 229960002474 hydralazine Drugs 0.000 description 8
• 229910001411 inorganic cation Inorganic materials 0.000 description 8
• 239000002105 nanoparticle Substances 0.000 description 8
• 150000002892 organic cations Chemical class 0.000 description 8
• 239000007800 oxidant agent Substances 0.000 description 8
• 230000001590 oxidative effect Effects 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 208000037803 restenosis Diseases 0.000 description 8
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
• 230000035882 stress Effects 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 150000007970 thio esters Chemical class 0.000 description 8
• 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 8
• 210000005166 vasculature Anatomy 0.000 description 8
• NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 7
• 229940127291 Calcium channel antagonist Drugs 0.000 description 7
• 229940123237 Taxane Drugs 0.000 description 7
• 125000004947 alkyl aryl amino group Chemical group 0.000 description 7
• 125000005431 alkyl carboxamide group Chemical group 0.000 description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
• 125000000747 amidyl group Chemical group [H][N-]* 0.000 description 7
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 7
• 239000010836 blood and blood product Substances 0.000 description 7
• 239000012503 blood component Substances 0.000 description 7
• 229940125691 blood product Drugs 0.000 description 7
• 239000000480 calcium channel blocker Substances 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 125000004986 diarylamino group Chemical group 0.000 description 7
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 230000007246 mechanism Effects 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• 150000002832 nitroso derivatives Chemical class 0.000 description 7
• 230000002265 prevention Effects 0.000 description 7
• 150000003254 radicals Chemical class 0.000 description 7
• 239000002461 renin inhibitor Substances 0.000 description 7
• 229940086526 renin-inhibitors Drugs 0.000 description 7
• FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 7
• GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
• 108050009340 Endothelin Proteins 0.000 description 6
• 102000002045 Endothelin Human genes 0.000 description 6
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 6
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• 102100035792 Kininogen-1 Human genes 0.000 description 6
• ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 6
• 229930064664 L-arginine Natural products 0.000 description 6
• 235000014852 L-arginine Nutrition 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 125000001931 aliphatic group Chemical group 0.000 description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
• 125000004103 aminoalkyl group Chemical group 0.000 description 6
• 125000005001 aminoaryl group Chemical group 0.000 description 6
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 6
• 125000003710 aryl alkyl group Chemical group 0.000 description 6
• 125000005129 aryl carbonyl group Chemical group 0.000 description 6
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 6
• 230000004087 circulation Effects 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 238000007796 conventional method Methods 0.000 description 6
• 230000002526 effect on cardiovascular system Effects 0.000 description 6
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 6
• 210000002744 extracellular matrix Anatomy 0.000 description 6
• RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 150000002823 nitrates Chemical class 0.000 description 6
• JYTMDRMFLPOETK-UHFFFAOYSA-N nitrous acid thionyl dichloride Chemical compound ON=O.ClS(Cl)=O JYTMDRMFLPOETK-UHFFFAOYSA-N 0.000 description 6
• ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 6
• 125000004043 oxo group Chemical group O=* 0.000 description 6
• 229920000642 polymer Polymers 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
• 229940124530 sulfonamide Drugs 0.000 description 6
• 150000003456 sulfonamides Chemical class 0.000 description 6
• URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 6
• 101800004538 Bradykinin Proteins 0.000 description 5
• 102000014914 Carrier Proteins Human genes 0.000 description 5
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