CA1277321C - Nitrataolkyl 1,4-benzodioxane derivatives - Google Patents
Nitrataolkyl 1,4-benzodioxane derivativesInfo
- Publication number
- CA1277321C CA1277321C CA000514414A CA514414A CA1277321C CA 1277321 C CA1277321 C CA 1277321C CA 000514414 A CA000514414 A CA 000514414A CA 514414 A CA514414 A CA 514414A CA 1277321 C CA1277321 C CA 1277321C
- Authority
- CA
- Canada
- Prior art keywords
- integer
- group
- acceptable salt
- formula
- represented
- 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.)
- Expired - Fee Related
Links
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000002252 acyl group Chemical group 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 206010019280 Heart failures Diseases 0.000 claims abstract description 7
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
- 230000003449 preventive effect Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 6
- ILSCSWSCKLXHMV-UHFFFAOYSA-N (5-hydroxy-6-nitro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl nitrate Chemical compound O1C(CO[N+]([O-])=O)COC2=CC=C([N+]([O-])=O)C(O)=C21 ILSCSWSCKLXHMV-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000029865 regulation of blood pressure Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000000304 vasodilatating effect Effects 0.000 description 3
- DRMOSUOUZKVUBE-UHFFFAOYSA-N 3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-ol Chemical compound C1=CC(O)=C2OC(CO)COC2=C1 DRMOSUOUZKVUBE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 206010061216 Infarction Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
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- 229940041616 menthol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- 229960002460 nitroprusside Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP161.096/85 | 1985-07-23 | ||
| JP60161096A JPS6222777A (ja) | 1985-07-23 | 1985-07-23 | １，４−ベンゾジオキサン誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1277321C true CA1277321C (en) | 1990-12-04 |
Family
ID=15728530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000514414A Expired - Fee Related CA1277321C (en) | 1985-07-23 | 1986-07-22 | Nitrataolkyl 1,4-benzodioxane derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4794118A (en, 2012) |
| EP (2) | EP0307970A1 (en, 2012) |
| JP (1) | JPS6222777A (en, 2012) |
| KR (1) | KR870001189A (en, 2012) |
| AT (1) | ATE124692T1 (en, 2012) |
| AU (1) | AU596108B2 (en, 2012) |
| CA (1) | CA1277321C (en, 2012) |
| DE (1) | DE3650347T2 (en, 2012) |
| DK (1) | DK347486A (en, 2012) |
| ES (2) | ES2004491A6 (en, 2012) |
| HU (1) | HU203230B (en, 2012) |
| NZ (1) | NZ216930A (en, 2012) |
| PH (1) | PH23359A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63179868A (ja) * | 1987-01-21 | 1988-07-23 | Eisai Co Ltd | １，４−ベンゾジオキサン誘導体及びその製法 |
| US5158956A (en) * | 1990-05-04 | 1992-10-27 | Eli Lilly And Company | Method of inhibiting gastric acid secretion with benzodioxanes |
| CA2438641A1 (en) | 2001-02-15 | 2002-08-22 | King Pharmaceuticals, Inc. | Stabilized pharmaceutical and thyroid hormone compositions and method of preparation |
| US7101569B2 (en) | 2001-08-14 | 2006-09-05 | Franz G Andrew | Methods of administering levothyroxine pharmaceutical compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3101345A (en) * | 1960-04-29 | 1963-08-20 | Thomae Gmbh Dr K | 2-hydroxymethyl-8-hydroxy-1,4-benzodioxane |
| US3166573A (en) * | 1963-11-08 | 1965-01-19 | Colgate Palmolive Co | 2-(nitratoalkyl)-1, 4-benzodioxanes |
-
1985
- 1985-07-23 JP JP60161096A patent/JPS6222777A/ja active Granted
-
1986
- 1986-07-18 US US06/887,720 patent/US4794118A/en not_active Expired - Fee Related
- 1986-07-21 HU HU862980A patent/HU203230B/hu not_active IP Right Cessation
- 1986-07-22 EP EP88116669A patent/EP0307970A1/en not_active Ceased
- 1986-07-22 ES ES8600473A patent/ES2004491A6/es not_active Expired
- 1986-07-22 CA CA000514414A patent/CA1277321C/en not_active Expired - Fee Related
- 1986-07-22 AU AU60424/86A patent/AU596108B2/en not_active Ceased
- 1986-07-22 KR KR1019860005935A patent/KR870001189A/ko not_active Withdrawn
- 1986-07-22 NZ NZ216930A patent/NZ216930A/xx unknown
- 1986-07-22 PH PH34049A patent/PH23359A/en unknown
- 1986-07-22 EP EP86110080A patent/EP0210581B1/en not_active Expired - Lifetime
- 1986-07-22 DK DK347486A patent/DK347486A/da not_active Application Discontinuation
- 1986-07-22 DE DE3650347T patent/DE3650347T2/de not_active Expired - Fee Related
- 1986-07-22 AT AT86110080T patent/ATE124692T1/de not_active IP Right Cessation
-
1988
- 1988-02-01 ES ES8800276A patent/ES2006545A6/es not_active Expired
- 1988-10-04 US US07/253,023 patent/US4959376A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6222777A (ja) | 1987-01-30 |
| DK347486A (da) | 1987-01-24 |
| ES2004491A6 (es) | 1989-01-16 |
| US4794118A (en) | 1988-12-27 |
| HU203230B (en) | 1991-06-28 |
| ATE124692T1 (de) | 1995-07-15 |
| DK347486D0 (da) | 1986-07-22 |
| US4959376A (en) | 1990-09-25 |
| KR870001189A (ko) | 1987-03-12 |
| DE3650347D1 (de) | 1995-08-10 |
| EP0210581A1 (en) | 1987-02-04 |
| EP0307970A1 (en) | 1989-03-22 |
| EP0210581B1 (en) | 1995-07-05 |
| NZ216930A (en) | 1989-08-29 |
| ES2006545A6 (es) | 1989-05-01 |
| PH23359A (en) | 1989-07-14 |
| AU6042486A (en) | 1987-01-29 |
| JPH0535150B2 (en, 2012) | 1993-05-25 |
| DE3650347T2 (de) | 1996-01-25 |
| AU596108B2 (en) | 1990-04-26 |
| HUT44776A (en) | 1988-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |