NO832700L - Fremgangsmaate for fremstilling av en pyridylalkylnitratforbindelse. - Google Patents
Fremgangsmaate for fremstilling av en pyridylalkylnitratforbindelse.Info
- Publication number
- NO832700L NO832700L NO832700A NO832700A NO832700L NO 832700 L NO832700 L NO 832700L NO 832700 A NO832700 A NO 832700A NO 832700 A NO832700 A NO 832700A NO 832700 L NO832700 L NO 832700L
- Authority
- NO
- Norway
- Prior art keywords
- nitroxymethyl
- lower alkyl
- hydrogen
- produced
- halogen
- Prior art date
Links
- -1 NITRATE COMPOUND Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 19
- 229910002651 NO3 Inorganic materials 0.000 title claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 5
- KLKMRHCMLLGCSZ-UHFFFAOYSA-N (6-chloropyridin-2-yl)methyl nitrate Chemical compound [O-][N+](=O)OCC1=CC=CC(Cl)=N1 KLKMRHCMLLGCSZ-UHFFFAOYSA-N 0.000 claims description 3
- HKLBNRHIHKYZTB-UHFFFAOYSA-N 3-pyridin-4-ylpropyl nitrate Chemical compound [O-][N+](=O)OCCCC1=CC=NC=C1 HKLBNRHIHKYZTB-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- QEBGRZOEFXKNIZ-UHFFFAOYSA-N [4-chloro-6-(nitrooxymethyl)pyridin-2-yl]methyl nitrate Chemical compound [O-][N+](=O)OCC1=CC(Cl)=CC(CO[N+]([O-])=O)=N1 QEBGRZOEFXKNIZ-UHFFFAOYSA-N 0.000 claims description 3
- IBYVZIVEQGSCBX-UHFFFAOYSA-N [6-(nitrooxymethyl)pyridin-2-yl]methyl nitrate Chemical compound [O-][N+](=O)OCC1=CC=CC(CO[N+]([O-])=O)=N1 IBYVZIVEQGSCBX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GQLQYSTXJVGYFH-UHFFFAOYSA-N (3-nitrooxy-2-pyridin-2-ylpropyl) nitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)C1=CC=CC=N1 GQLQYSTXJVGYFH-UHFFFAOYSA-N 0.000 claims 1
- PCCCBXSNMNEXFD-UHFFFAOYSA-N (6-methylpyridin-2-yl)methyl nitrate Chemical compound CC1=CC=CC(CO[N+]([O-])=O)=N1 PCCCBXSNMNEXFD-UHFFFAOYSA-N 0.000 claims 1
- SLPBIRAFWRSHME-UHFFFAOYSA-N 2-pyridin-2-ylethyl nitrate Chemical compound [O-][N+](=O)OCCC1=CC=CC=N1 SLPBIRAFWRSHME-UHFFFAOYSA-N 0.000 claims 1
- AWWPAOSCTMXHNS-UHFFFAOYSA-N pyridin-2-ylmethyl nitrate Chemical compound [O-][N+](=O)OCC1=CC=CC=N1 AWWPAOSCTMXHNS-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
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- UOMMGMRPOFXGTJ-UHFFFAOYSA-N (3-nitrooxy-2-pyridin-2-ylpropyl) nitrate;hydrochloride Chemical compound Cl.[O-][N+](=O)OCC(CO[N+]([O-])=O)C1=CC=CC=N1 UOMMGMRPOFXGTJ-UHFFFAOYSA-N 0.000 description 1
- OETZAKJXBYDYBR-UHFFFAOYSA-N (6-methylpyridin-2-yl)methyl nitrate;hydrochloride Chemical compound Cl.CC1=CC=CC(CO[N+]([O-])=O)=N1 OETZAKJXBYDYBR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8221592 | 1982-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO832700L true NO832700L (no) | 1984-02-06 |
Family
ID=10531922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO832700A NO832700L (no) | 1982-07-26 | 1983-07-25 | Fremgangsmaate for fremstilling av en pyridylalkylnitratforbindelse. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4540701A (cs) |
| EP (1) | EP0100081B1 (cs) |
| JP (1) | JPS5951263A (cs) |
| KR (1) | KR900005470B1 (cs) |
| AT (1) | ATE40948T1 (cs) |
| AU (1) | AU565791B2 (cs) |
| CA (1) | CA1216850A (cs) |
| DE (1) | DE3379255D1 (cs) |
| DK (1) | DK311683A (cs) |
| ES (1) | ES8502088A1 (cs) |
| FI (1) | FI832490L (cs) |
| GR (1) | GR78629B (cs) |
| HU (1) | HU190497B (cs) |
| NO (1) | NO832700L (cs) |
| PH (1) | PH18083A (cs) |
| SU (1) | SU1189337A3 (cs) |
| ZA (1) | ZA835048B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6081166A (ja) * | 1983-10-11 | 1985-05-09 | Fujisawa Pharmaceut Co Ltd | ２−ニトロオキシメチル−６−クロロピリジンのβ−シクロデキストリン包接化合物およびその製造法 |
| JPS6215A (ja) * | 1985-02-26 | 1987-01-06 | Fujisawa Pharmaceut Co Ltd | ２−ニトロオキシメチル−６−クロロピリジンまたはそのβ−シクロデキストリン包接化合物含有持続性製剤 |
| ZA885069B (en) * | 1987-07-24 | 1989-03-29 | Fujisawa Pharmaceutical Co | Sustained-release percutaneous preparations |
| JPH02167279A (ja) * | 1988-09-30 | 1990-06-27 | Taisho Pharmaceut Co Ltd | アポビンカミン酸誘導体 |
| US5047543A (en) * | 1988-11-24 | 1991-09-10 | Taisho Pharmaceutical Co., Ltd. | 1,4-dihydropyridine derivatives |
| CN106318877A (zh) * | 2016-08-29 | 2017-01-11 | 刘翔 | 一种从茯砖茶中分离、纯化冠突散囊菌及其液态培养方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275642A (en) * | 1962-04-26 | 1966-09-27 | Bard Pharmaceutical Inc | 3-pyridine carbinol nitrate and its preparation |
| US3689494A (en) * | 1971-03-31 | 1972-09-05 | William R J Simpson | N-pyridinealkyl-alkanolamine nitrates |
-
1983
- 1983-07-05 DK DK311683A patent/DK311683A/da not_active Application Discontinuation
- 1983-07-07 AU AU16635/83A patent/AU565791B2/en not_active Ceased
- 1983-07-07 FI FI832490A patent/FI832490L/fi not_active Application Discontinuation
- 1983-07-11 ZA ZA835048A patent/ZA835048B/xx unknown
- 1983-07-11 GR GR71903A patent/GR78629B/el unknown
- 1983-07-19 JP JP58132645A patent/JPS5951263A/ja active Granted
- 1983-07-20 PH PH29255A patent/PH18083A/en unknown
- 1983-07-20 US US06/515,653 patent/US4540701A/en not_active Expired - Fee Related
- 1983-07-22 ES ES524375A patent/ES8502088A1/es not_active Expired
- 1983-07-23 EP EP83107232A patent/EP0100081B1/en not_active Expired
- 1983-07-23 AT AT83107232T patent/ATE40948T1/de not_active IP Right Cessation
- 1983-07-23 DE DE8383107232T patent/DE3379255D1/de not_active Expired
- 1983-07-25 HU HU832615A patent/HU190497B/hu unknown
- 1983-07-25 NO NO832700A patent/NO832700L/no unknown
- 1983-07-25 SU SU833625197A patent/SU1189337A3/ru active
- 1983-07-26 CA CA000433162A patent/CA1216850A/en not_active Expired
- 1983-07-26 KR KR1019830003459A patent/KR900005470B1/ko active IP Right Grant
-
1985
- 1985-05-08 US US06/731,893 patent/US4613608A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA835048B (en) | 1984-03-28 |
| GR78629B (cs) | 1984-09-27 |
| US4613608A (en) | 1986-09-23 |
| KR840005426A (ko) | 1984-11-12 |
| CA1216850A (en) | 1987-01-20 |
| DE3379255D1 (en) | 1989-04-06 |
| SU1189337A3 (ru) | 1985-10-30 |
| DK311683D0 (da) | 1983-07-05 |
| ES524375A0 (es) | 1984-12-16 |
| FI832490L (fi) | 1984-01-27 |
| ES8502088A1 (es) | 1984-12-16 |
| JPS6350343B2 (cs) | 1988-10-07 |
| PH18083A (en) | 1985-03-18 |
| EP0100081A3 (en) | 1985-05-02 |
| DK311683A (da) | 1984-01-27 |
| EP0100081B1 (en) | 1989-03-01 |
| ATE40948T1 (de) | 1989-03-15 |
| HU190497B (en) | 1986-09-29 |
| KR900005470B1 (ko) | 1990-07-30 |
| EP0100081A2 (en) | 1984-02-08 |
| FI832490A0 (fi) | 1983-07-07 |
| JPS5951263A (ja) | 1984-03-24 |
| AU565791B2 (en) | 1987-10-01 |
| US4540701A (en) | 1985-09-10 |
| AU1663583A (en) | 1984-02-02 |
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