WO1991008189A1 - Preparation pharmaceutique a base de polyhydroxy-1,4-naphtoquinones utilisee comme protecteur du myocarde sous ischemie et reperfusion - Google Patents
Preparation pharmaceutique a base de polyhydroxy-1,4-naphtoquinones utilisee comme protecteur du myocarde sous ischemie et reperfusion Download PDFInfo
- Publication number
- WO1991008189A1 WO1991008189A1 PCT/SU1990/000267 SU9000267W WO9108189A1 WO 1991008189 A1 WO1991008189 A1 WO 1991008189A1 SU 9000267 W SU9000267 W SU 9000267W WO 9108189 A1 WO9108189 A1 WO 9108189A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- compound
- polyhydroxy
- naphthoquinones
- hydroxy group
- Prior art date
Links
- 208000028867 ischemia Diseases 0.000 title claims abstract description 12
- 210000004165 myocardium Anatomy 0.000 title abstract description 5
- 230000010410 reperfusion Effects 0.000 title abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 230000001012 protector Effects 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- -1 glutathionyl Chemical group 0.000 claims abstract description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 206010011878 Deafness Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 abstract description 5
- GBVZULYIRHSBLP-UHFFFAOYSA-N 3-(1,3,4,6,7-pentahydroxy-5,8-dioxonaphthalen-2-yl)propanoic acid Chemical compound OC=1C(C2=C(C(=C(C(=C2C(C1O)=O)O)O)CCC(=O)O)O)=O GBVZULYIRHSBLP-UHFFFAOYSA-N 0.000 abstract 1
- XZBBWHXFJGWXGE-XUXIUFHCSA-N OC1=C2C(C(=C(C(C2=C(C(=C1O)C)O)=O)N[C@H](C(=O)O)CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)N[C@H](C(=O)O)CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)=O Chemical compound OC1=C2C(C(=C(C(C2=C(C(=C1O)C)O)=O)N[C@H](C(=O)O)CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)N[C@H](C(=O)O)CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)=O XZBBWHXFJGWXGE-XUXIUFHCSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 208000010125 myocardial infarction Diseases 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 210000005069 ears Anatomy 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 108010068370 Glutens Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 235000021312 gluten Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 4
- 239000000006 Nitroglycerin Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229960003711 glyceryl trinitrate Drugs 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000009931 harmful effect Effects 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000010309 melting process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- QCNHIJXDZKTWSA-UHFFFAOYSA-N 1,2,3,4-Tetramethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1OC QCNHIJXDZKTWSA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- KPYCVQASEGGKEG-UHFFFAOYSA-N 3-hydroxyoxolane-2,5-dione Chemical compound OC1CC(=O)OC1=O KPYCVQASEGGKEG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- TWJPKRPAWOEANM-UHFFFAOYSA-N C[ClH]C Chemical compound C[ClH]C TWJPKRPAWOEANM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- 241000700112 Chinchilla Species 0.000 description 1
- 206010011703 Cyanosis Diseases 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 241000531375 Dexamine Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 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
- 206010061216 Infarction Diseases 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 206010000891 acute myocardial infarction Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
- 229960003459 allopurinol Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 230000007654 ischemic lesion Effects 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 208000037891 myocardial injury Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 230000035806 respiratory chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- LMICSZURMWFXCZ-UHFFFAOYSA-N s-butanoyl butanethioate Chemical compound CCCC(=O)SC(=O)CCC LMICSZURMWFXCZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the biological activity of the claimed compounds has been studied on an experimental model of myocardial infarction in the population.
- the reaction is 39.5 g (0.28 mol) of dimethyl hydrochloride, 95.0 g (0.57 mol) of diacid anhydride, 338.0 g (2.5 mol.) Of aluminum and aluminum g ⁇ l ⁇ ida na ⁇ iya in usl ⁇ viya ⁇ , anal ⁇ gichny ⁇ ⁇ isannym in ⁇ ime ⁇ e I. P ⁇ luchayu ⁇ 68.2 g (92 wt. $) 5.8 digid ⁇ si -di ⁇ l ⁇ -2,3- ⁇ , 4-na ⁇ in ⁇ na. Melting plant ⁇ 94- ⁇ 96 ° ⁇ .
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Vascular Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Polyhydroxy-1,4-naphtoquinone de la formule générale (I), dans laquelle, lorsque R1=R2= un groupe hydroxy, R3= tret.butyle et R4= hydrogène, ou R3= un groupe hydroxy et R4=propyle ou 2-carboxyéthyle; lorsque R1=R2= un groupe 2-hydroxyéthyle, R3= un groupe hydroxy et R4= méthyle; lorsque R1=R2= glutathionyle, R3= un groupe hydroxy et R4= méthyle ou éthyle ou un groupe hydroxy. Les compositions de l'invention présentent une propriété de protection du myocarde sous ischémie et reperfusion. Les compositions les plus actives sont 2,3,5,6,8-pentahydroxy-7-(2-carboxyéthyle)-1,4-naphtoquinone et 5,6,8-trihydroxy-2,3-diglutathionyle-7-méthyle-1,4-naphtoquinone. Les polyhydroxy-1,4-naphtoquinones constituent les substances actives de la préparation pharmaceutique de l'invention.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU4765332/04 | 1989-12-06 | ||
| SU894765332A RU1822549C (ru) | 1989-12-06 | 1989-12-06 | Полигидрокси-1,4-нафтохиноны, обладающие свойством протектора миокарда при его ишемии и реперфузии |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1991008189A1 true WO1991008189A1 (fr) | 1991-06-13 |
Family
ID=21482727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/SU1990/000267 WO1991008189A1 (fr) | 1989-12-06 | 1990-12-06 | Preparation pharmaceutique a base de polyhydroxy-1,4-naphtoquinones utilisee comme protecteur du myocarde sous ischemie et reperfusion |
Country Status (2)
| Country | Link |
|---|---|
| RU (1) | RU1822549C (fr) |
| WO (1) | WO1991008189A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292737A (en) * | 1992-10-23 | 1994-03-08 | Sphinx Pharmaceuticals Corporation | N,N'-bis(sulfonamido)-2-amino-4-iminonaphthalen-1-ones and N,N'-bis(amido)-2-amino-4-iminonaphthalen-1-ones |
| RU2625740C1 (ru) * | 2016-10-10 | 2017-07-18 | Федеральное государственное бюджетное учреждение науки Тихоокеанский институт биоорганической химии им. Г.Б. Елякова Дальневосточного отделения Российской академии наук (ТИБОХ ДВО РАН) | Средство для лечения ишемии сосудов головного мозга |
| RU2651042C1 (ru) * | 2017-06-05 | 2018-04-18 | Федеральное государственное бюджетное учреждение науки Тихоокеанский институт биоорганической химии им. Г.Б. Елякова Дальневосточного отделения Российской академии наук (ТИБОХ ДВО РАН) | Лекарственная форма гистохрома для перорального введения и пролонгированного действия |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4436753A (en) * | 1979-12-30 | 1984-03-13 | Takeda Chemical Industries, Ltd. | Method for therapy of ischemic disease |
| GB2159056A (en) * | 1984-04-04 | 1985-11-27 | Alan Alaexander Torrance Sime | Biocidal compositions comprising polyhydroxynaphthoquinones |
-
1989
- 1989-12-06 RU SU894765332A patent/RU1822549C/ru active
-
1990
- 1990-12-06 WO PCT/SU1990/000267 patent/WO1991008189A1/fr unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4436753A (en) * | 1979-12-30 | 1984-03-13 | Takeda Chemical Industries, Ltd. | Method for therapy of ischemic disease |
| GB2159056A (en) * | 1984-04-04 | 1985-11-27 | Alan Alaexander Torrance Sime | Biocidal compositions comprising polyhydroxynaphthoquinones |
Non-Patent Citations (4)
| Title |
|---|
| HELVETICA CHIMICA ACTA, ENDENDA CURAT SOCIETAS CHIMICA HELVETICA, Volume 47, No. 7, 1964, VERLAG HELVETICA CHIMICA ACTA (Basel), E. HARDEGGER et al.: "Bicyclische Zwischenprodukte zur Synthese des Javanicins", pages 2017-2021. * |
| IZVESTIA AKADEMII NAUK SSSR, seria Kchimicheskaya, No. 2, 1988, Nauka (Moscow), L.V. BAGUSLAVSKAYA et al.: "O Kinetike Nizkotemperaturnogo Initsiirovannogo Okislenia Etilbenzola, Ingibirovannogo Poligidroksinaftokhinomai", page 283. * |
| IZVESTIA AKADEMII NAUK SSSR, seria Khimicheskaya, No. 7, 1985, Nauka (Moscow), L.V. BAGUSLAVSKAYA et al.: "Poligidroksinaftokhinonynovyi Klass Prirodnykh Antioksidantov", page 1471. * |
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Cited By (3)
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| US5292737A (en) * | 1992-10-23 | 1994-03-08 | Sphinx Pharmaceuticals Corporation | N,N'-bis(sulfonamido)-2-amino-4-iminonaphthalen-1-ones and N,N'-bis(amido)-2-amino-4-iminonaphthalen-1-ones |
| RU2625740C1 (ru) * | 2016-10-10 | 2017-07-18 | Федеральное государственное бюджетное учреждение науки Тихоокеанский институт биоорганической химии им. Г.Б. Елякова Дальневосточного отделения Российской академии наук (ТИБОХ ДВО РАН) | Средство для лечения ишемии сосудов головного мозга |
| RU2651042C1 (ru) * | 2017-06-05 | 2018-04-18 | Федеральное государственное бюджетное учреждение науки Тихоокеанский институт биоорганической химии им. Г.Б. Елякова Дальневосточного отделения Российской академии наук (ТИБОХ ДВО РАН) | Лекарственная форма гистохрома для перорального введения и пролонгированного действия |
Also Published As
| Publication number | Publication date |
|---|---|
| RU1822549C (ru) | 1996-08-20 |
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