AU596108B2 - 1,4-benzodioxane derivatives - Google Patents
1,4-benzodioxane derivatives Download PDFInfo
- Publication number
- AU596108B2 AU596108B2 AU60424/86A AU6042486A AU596108B2 AU 596108 B2 AU596108 B2 AU 596108B2 AU 60424/86 A AU60424/86 A AU 60424/86A AU 6042486 A AU6042486 A AU 6042486A AU 596108 B2 AU596108 B2 AU 596108B2
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- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
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- 239000008196 pharmacological composition Substances 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
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- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
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- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
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- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 1
- 229960000305 enflurane Drugs 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960000201 isosorbide dinitrate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- 150000007522 mineralic acids Chemical class 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 239000000377 silicon dioxide Substances 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
- 210000000115 thoracic cavity Anatomy 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 |
|---|---|---|---|
| JP60161096A JPS6222777A (ja) | 1985-07-23 | 1985-07-23 | １，４−ベンゾジオキサン誘導体 |
| JP60-161096 | 1985-07-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6042486A AU6042486A (en) | 1987-01-29 |
| AU596108B2 true AU596108B2 (en) | 1990-04-26 |
Family
ID=15728530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU60424/86A Ceased AU596108B2 (en) | 1985-07-23 | 1986-07-22 | 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 |
| CA1277321C (en) | 1990-12-04 |
| PH23359A (en) | 1989-07-14 |
| AU6042486A (en) | 1987-01-29 |
| JPH0535150B2 (en, 2012) | 1993-05-25 |
| DE3650347T2 (de) | 1996-01-25 |
| HUT44776A (en) | 1988-04-28 |
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