CA2871601C - Broncholytic drug on the basis of prostaglandin - Google Patents
Broncholytic drug on the basis of prostaglandin Download PDFInfo
- Publication number
- CA2871601C CA2871601C CA2871601A CA2871601A CA2871601C CA 2871601 C CA2871601 C CA 2871601C CA 2871601 A CA2871601 A CA 2871601A CA 2871601 A CA2871601 A CA 2871601A CA 2871601 C CA2871601 C CA 2871601C
- Authority
- CA
- Canada
- Prior art keywords
- drug
- nitroproston
- keto
- dihydroxy
- prostadienoic acid
- Prior art date
- 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.)
- Active
Links
- 239000003814 drug Substances 0.000 title claims abstract description 27
- 229940079593 drug Drugs 0.000 title claims abstract description 24
- 229940124630 bronchodilator Drugs 0.000 title abstract description 6
- 230000001813 broncholytic effect Effects 0.000 title abstract description 5
- 150000003180 prostaglandins Chemical class 0.000 title abstract description 5
- 208000006673 asthma Diseases 0.000 claims abstract description 14
- 230000000414 obstructive effect Effects 0.000 claims abstract description 9
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 8
- 206010006451 bronchitis Diseases 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims abstract description 4
- 230000000916 dilatatory effect Effects 0.000 claims description 5
- 208000023504 respiratory system disease Diseases 0.000 claims description 5
- 210000002345 respiratory system Anatomy 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- SGMBTYBNUOWYOV-CXZSOYKBSA-N nitroproston Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC(CO[N+]([O-])=O)CO[N+]([O-])=O SGMBTYBNUOWYOV-CXZSOYKBSA-N 0.000 abstract description 30
- 230000000694 effects Effects 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 6
- 229960002986 dinoprostone Drugs 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 206010006482 Bronchospasm Diseases 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000644 isotonic solution Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 210000000621 bronchi Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- LSLYOANBFKQKPT-UHFFFAOYSA-N fenoterol Chemical compound C=1C(O)=CC(O)=CC=1C(O)CNC(C)CC1=CC=C(O)C=C1 LSLYOANBFKQKPT-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940125389 long-acting beta agonist Drugs 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 206010005746 Blood pressure fluctuation Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 102000008866 Prostaglandin E receptors Human genes 0.000 description 1
- 108010088540 Prostaglandin E receptors Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- WXAXNYYAYJKARR-UHFFFAOYSA-N benzene;2-(1,4-dioxan-2-yl)acetic acid Chemical compound C1=CC=CC=C1.OC(=O)CC1COCCO1 WXAXNYYAYJKARR-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003153 cholinolytic effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940041682 inhalant solution Drugs 0.000 description 1
- 229940125369 inhaled corticosteroids Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000017953 prostanoid receptors Human genes 0.000 description 1
- 108050007059 prostanoid receptors Proteins 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004202 respiratory function Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2012116226 | 2012-04-24 | ||
| RU2012116226/15A RU2500397C1 (ru) | 2012-04-24 | 2012-04-24 | Бронхолитическое средство на основе простагландина |
| PCT/RU2013/000163 WO2013162416A1 (ru) | 2012-04-24 | 2013-03-01 | Бронхолитическое средство на основе простагландина |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2871601A1 CA2871601A1 (en) | 2013-10-31 |
| CA2871601C true CA2871601C (en) | 2020-02-18 |
Family
ID=49446371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2871601A Active CA2871601C (en) | 2012-04-24 | 2013-03-01 | Broncholytic drug on the basis of prostaglandin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9408820B2 (enExample) |
| EP (1) | EP2842554B1 (enExample) |
| JP (1) | JP6126204B2 (enExample) |
| CN (1) | CN104470510A (enExample) |
| AU (1) | AU2013253042B2 (enExample) |
| BR (1) | BR112014026610A2 (enExample) |
| CA (1) | CA2871601C (enExample) |
| EA (1) | EA027724B1 (enExample) |
| RU (1) | RU2500397C1 (enExample) |
| WO (1) | WO2013162416A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170326094A1 (en) * | 2014-12-09 | 2017-11-16 | Nestec S.A. | Uses of bioactive lipids |
| RU2662099C1 (ru) * | 2017-10-16 | 2018-07-23 | Общество с ограниченной ответственностью "Гурус БиоФарм" | Фармацевтические композиции для ингаляций, содержащие нитропростон |
| RU2695068C1 (ru) * | 2018-06-26 | 2019-07-19 | Общество с ограниченной ответственностью "Гурус БиоФарм" | Средство для лечения хронических облитерирующих заболеваний периферических сосудов на основе простагландина |
| CN117924133A (zh) * | 2022-10-17 | 2024-04-26 | 广州楷石医药有限公司 | 一种前列地尔偶联一氧化氮供体药物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2067094C1 (ru) * | 1993-09-27 | 1996-09-27 | Владимир Виленович Безуглов | 1,3-динитроглицериновые эфиры полиненасыщенных жирных кислот, гидроксипроизводных полиненасыщенных жирных кислот и простагландинов и способы их получения |
| US5625083A (en) * | 1995-06-02 | 1997-04-29 | Bezuglov; Vladimir V. | Dinitroglycerol esters of unsaturated fatty acids and prostaglandins |
-
2012
- 2012-04-24 RU RU2012116226/15A patent/RU2500397C1/ru active
-
2013
- 2013-03-01 EP EP13781656.7A patent/EP2842554B1/en not_active Not-in-force
- 2013-03-01 WO PCT/RU2013/000163 patent/WO2013162416A1/ru not_active Ceased
- 2013-03-01 JP JP2015508895A patent/JP6126204B2/ja not_active Expired - Fee Related
- 2013-03-01 BR BR112014026610A patent/BR112014026610A2/pt not_active Application Discontinuation
- 2013-03-01 EA EA201401178A patent/EA027724B1/ru not_active IP Right Cessation
- 2013-03-01 CA CA2871601A patent/CA2871601C/en active Active
- 2013-03-01 AU AU2013253042A patent/AU2013253042B2/en not_active Ceased
- 2013-03-01 CN CN201380022111.6A patent/CN104470510A/zh active Pending
- 2013-03-01 US US14/397,092 patent/US9408820B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP6126204B2 (ja) | 2017-05-10 |
| EP2842554A1 (en) | 2015-03-04 |
| CA2871601A1 (en) | 2013-10-31 |
| US9408820B2 (en) | 2016-08-09 |
| RU2500397C1 (ru) | 2013-12-10 |
| BR112014026610A2 (pt) | 2017-07-18 |
| EA201401178A1 (ru) | 2015-10-30 |
| AU2013253042A1 (en) | 2014-12-11 |
| EP2842554B1 (en) | 2018-10-24 |
| EP2842554A4 (en) | 2016-01-06 |
| EA027724B1 (ru) | 2017-08-31 |
| US20150141505A1 (en) | 2015-05-21 |
| JP2016506359A (ja) | 2016-03-03 |
| CN104470510A (zh) | 2015-03-25 |
| AU2013253042B2 (en) | 2017-08-31 |
| WO2013162416A1 (ru) | 2013-10-31 |
| RU2012116226A (ru) | 2013-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20170223 |