CN103687843B - 醌基一氧化氮供体化合物 - Google Patents
醌基一氧化氮供体化合物 Download PDFInfo
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- CN103687843B CN103687843B CN201280030505.1A CN201280030505A CN103687843B CN 103687843 B CN103687843 B CN 103687843B CN 201280030505 A CN201280030505 A CN 201280030505A CN 103687843 B CN103687843 B CN 103687843B
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- compound
- nitrate
- dialkylene
- methyl
- solution
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 305
- 125000004151 quinonyl group Chemical group 0.000 title abstract description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229910002651 NO3 Inorganic materials 0.000 claims description 66
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 66
- -1 methoxyl group Chemical group 0.000 claims description 64
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- AGDYNDJUZRMYRG-UHFFFAOYSA-N hexyl nitrate Chemical compound CCCCCCO[N+]([O-])=O AGDYNDJUZRMYRG-UHFFFAOYSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- UEFBRXQBUTYIJI-UHFFFAOYSA-N decyl nitrate Chemical compound CCCCCCCCCCO[N+]([O-])=O UEFBRXQBUTYIJI-UHFFFAOYSA-N 0.000 claims description 12
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
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- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
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- QQHZPQUHCAKSOL-UHFFFAOYSA-N butyl nitrate Chemical compound CCCCO[N+]([O-])=O QQHZPQUHCAKSOL-UHFFFAOYSA-N 0.000 claims description 7
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- BZNKICRUKQQYIQ-UHFFFAOYSA-N 1-nitrooxypentan-2-yl nitrate Chemical compound CCCC(O[N+]([O-])=O)CO[N+]([O-])=O BZNKICRUKQQYIQ-UHFFFAOYSA-N 0.000 claims description 4
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- 206010030043 Ocular hypertension Diseases 0.000 claims description 2
- SZXWCBDQKUTCNH-UHFFFAOYSA-N 1-nitrooxydecan-2-yl nitrate Chemical compound CCCCCCCCC(O[N+]([O-])=O)CO[N+]([O-])=O SZXWCBDQKUTCNH-UHFFFAOYSA-N 0.000 claims 1
- 230000007170 pathology Effects 0.000 abstract description 5
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- 150000003839 salts Chemical class 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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- UIXPTCZPFCVOQF-UHFFFAOYSA-N ubiquinone-0 Chemical compound COC1=C(OC)C(=O)C(C)=CC1=O UIXPTCZPFCVOQF-UHFFFAOYSA-N 0.000 description 10
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 9
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- WSNODXPBBALQOF-VEJSHDCNSA-N tafluprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1 WSNODXPBBALQOF-VEJSHDCNSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
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- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- 235000012711 vitamin K3 Nutrition 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7024—Esters of saccharides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
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- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/53—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/02—Nitrates; Nitrites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Ophthalmology & Optometry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Neurology (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims (22)
Priority Applications (1)
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CN201410014214.4A CN103739499B (zh) | 2011-10-24 | 2012-10-23 | 醌基一氧化氮供体化合物 |
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EP11186301 | 2011-10-24 | ||
EP11186301.5 | 2011-10-24 | ||
PCT/EP2012/070953 WO2013060673A1 (en) | 2011-10-24 | 2012-10-23 | Quinone based nitric oxide donating compounds |
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CN201410014214.4A Division CN103739499B (zh) | 2011-10-24 | 2012-10-23 | 醌基一氧化氮供体化合物 |
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CN103687843A CN103687843A (zh) | 2014-03-26 |
CN103687843B true CN103687843B (zh) | 2016-11-16 |
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CN201410014214.4A Active CN103739499B (zh) | 2011-10-24 | 2012-10-23 | 醌基一氧化氮供体化合物 |
CN201280030505.1A Active CN103687843B (zh) | 2011-10-24 | 2012-10-23 | 醌基一氧化氮供体化合物 |
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CN201410014214.4A Active CN103739499B (zh) | 2011-10-24 | 2012-10-23 | 醌基一氧化氮供体化合物 |
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EP (2) | EP2707354B1 (zh) |
JP (1) | JP6158194B2 (zh) |
CN (2) | CN103739499B (zh) |
CA (1) | CA2839390C (zh) |
ES (1) | ES2542702T3 (zh) |
HK (1) | HK1197054A1 (zh) |
WO (1) | WO2013060673A1 (zh) |
Families Citing this family (7)
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CN104994845B (zh) * | 2012-10-23 | 2017-11-17 | 尼科斯科学爱尔兰公司 | 用于眼科应用的醌基一氧化氮供体化合物 |
WO2015155234A1 (en) | 2014-04-09 | 2015-10-15 | Nicox Science Ireland | Quinone based nitric oxide donating compounds |
CN105218377B (zh) * | 2015-09-14 | 2017-10-27 | 西安交通大学 | 一种羟基酪醇no供体衍生物及其制备方法和应用 |
WO2017106803A1 (en) * | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
CN108341775B (zh) * | 2017-01-25 | 2021-03-16 | 重庆常捷医药有限公司 | 一种瑞巴派特中间体的合成方法 |
US20190328774A1 (en) * | 2017-02-09 | 2019-10-31 | Noxsano Inc. | Electrochemical gasotransmitter generating compositions and methods of using same and dressings and treatment systems incorporating same |
CN109364050B (zh) * | 2018-10-19 | 2021-02-02 | 大连医科大学 | 艾地苯醌在制备治疗肺动脉高压药物中的应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050165094A1 (en) * | 1999-04-30 | 2005-07-28 | Teijin Limited | Chemical compounds containing a superoxide scavenger and an organic nitrate or nitrite moiety |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57167981A (en) * | 1981-04-08 | 1982-10-16 | Kowa Co | Benzopyran derivative |
GB8717068D0 (en) * | 1987-07-20 | 1987-08-26 | Fujisawa Pharmaceutical Co | Nitric ester derivative |
JP2628756B2 (ja) | 1988-09-15 | 1997-07-09 | シュバルツファルマ アクチェンゲゼルシャフト | 新規有機ニトレート及びそれらの製造方法 |
NL8802276A (nl) * | 1988-09-15 | 1990-04-02 | Cedona Pharm Bv | Geneesmiddel met relaxerende werking, dat als aktieve stof een nitraatester bevat. |
DE4011505C2 (de) | 1990-04-10 | 1995-01-12 | Sanol Arznei Schwarz Gmbh | Nitratoalkancarbonsäure-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
NL9001955A (nl) | 1990-09-05 | 1992-04-01 | Cedona Pharm Bv | Nieuwe thiazolidinederivaten. |
IT1244472B (it) * | 1990-12-14 | 1994-07-15 | Italfarmaco Spa | Benzossazinoni e benzotiazinoni ad attivita' cardiovascolare |
FR2680173A1 (fr) | 1991-08-07 | 1993-02-12 | Hoechst Lab | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires . |
ES2142773B1 (es) | 1998-10-07 | 2001-01-01 | Lacer Sa | Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia desminuida. |
WO2006015930A1 (en) * | 2004-08-10 | 2006-02-16 | Nicox S.A. | Phenol derivatives |
US20100210694A1 (en) * | 2007-10-19 | 2010-08-19 | Nicox S.A. | New no-donor aspirin derivatives |
US8062653B2 (en) * | 2009-02-18 | 2011-11-22 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
CN101597231B (zh) * | 2009-07-10 | 2012-07-04 | 中国人民解放军第四军医大学 | No供体药物及其合成方法 |
CA2788078A1 (en) * | 2010-01-26 | 2011-08-04 | Yissum Research Development Company Of The Hebrew University Of Jerusale M Ltd. | Compositions and methods for prevention and treatment of pulmonary hypertension |
-
2012
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- 2012-10-23 US US14/126,363 patent/US9061962B2/en active Active
- 2012-10-23 ES ES12788142.3T patent/ES2542702T3/es active Active
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2014
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Patent Citations (1)
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US20050165094A1 (en) * | 1999-04-30 | 2005-07-28 | Teijin Limited | Chemical compounds containing a superoxide scavenger and an organic nitrate or nitrite moiety |
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Nitrooxyquinones: synthesis, X-ray diffraction and;Fabiane C. de Abreu等;《Tetrahedron Letters》;20021104;第43卷(第45期);第8153–8157页 * |
Superoxide radical scavenging activity of idebenone in vitro studied by ESR spin trapping method and direct ESR measurement at liquid nitrogen temperature;Morio Murakami等;《Arch. Gerontol. Geriatr》;19901101;第11卷(第3期);第199-214页 * |
Also Published As
Publication number | Publication date |
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EP2722326A1 (en) | 2014-04-23 |
CN103739499B (zh) | 2016-09-07 |
CN103739499A (zh) | 2014-04-23 |
JP6158194B2 (ja) | 2017-07-05 |
CA2839390C (en) | 2015-09-15 |
EP2707354A1 (en) | 2014-03-19 |
CN103687843A (zh) | 2014-03-26 |
HK1197054A1 (zh) | 2015-01-02 |
ES2542702T3 (es) | 2015-08-10 |
WO2013060673A1 (en) | 2013-05-02 |
US20140342998A1 (en) | 2014-11-20 |
EP2707354B1 (en) | 2015-04-29 |
CA2839390A1 (en) | 2013-05-02 |
JP2014530843A (ja) | 2014-11-20 |
US9061962B2 (en) | 2015-06-23 |
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