GB1356374A - Mononitrate esters of 1,3 3,6-dianhydro-d-glucitol - Google Patents

Mononitrate esters of 1,3 3,6-dianhydro-d-glucitol

Info

Publication number
GB1356374A
GB1356374A GB1882172A GB1882172A GB1356374A GB 1356374 A GB1356374 A GB 1356374A GB 1882172 A GB1882172 A GB 1882172A GB 1882172 A GB1882172 A GB 1882172A GB 1356374 A GB1356374 A GB 1356374A
Authority
GB
United Kingdom
Prior art keywords
nitrate
dianhydro
glucitol
introduce
group
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
Application number
GB1882172A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
American Home Products Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Home Products Corp filed Critical American Home Products Corp
Publication of GB1356374A publication Critical patent/GB1356374A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

Abstract

1356374 1,4; 3,6 - Dianhydro - D - glucibols AMERICAN HOME PRODUCTS CORP 24 April 1972 [29 April 1971] 18821/72 Heading C2C Novel compounds (I) and (II) in which R is C 1-6 alkanoyl, C 1-6 alkyl (including cyclobutyl, cyclopentyl and cyclohexyl), benzoyl, benzyl, sulphanoyl or carbamoyl are prepared (1) by a process in which 1,4:3,6-dianhydro-D-glucitol, 2 or 5-nitrate is (a) acylated to introduce a C 1-6 alkanoyl or benzoyl group, (b) alkylated to introduce a C 1-6 alkyl or benzyl group, (c) reacted with a sulphamoyl halide preferably in pyridine to introduce a sulphamoyl group, or (d) reacted with phosgene and the product formed thereby treated with ammonia to introduce a carbamoyl group, or (2) by nitration of the corresponding 2 or 5 -O-R substituted 1,4:3,6-dianydro-D-glucitol. Acylation is carried out in the presence of a tertiary amine using an acid anhydride or halide. Alkylation is carried out with a halide in an alkanol in the presence of silver oxide. The introduction of a carbamoyl group is carried out in an inert solvent preferably dioxan. Compounds (I) and (II) are 1,4:3,6-dianhydro-D- glucitol - 5 or 2 - acetate - 2 or 5 - nitrate, - 5 or 2 - carbamate - 2 or 5 - nitrate, - 2 - ethyl - 5- nitrate and -5-nitrate-2-sulphamate. Compounds (I) and (II) lower systemic blood pressure and coronary resistance and form with a carrier a pharmaceutical composition which may be administered parenterally.
GB1882172A 1971-04-29 1972-04-24 Mononitrate esters of 1,3 3,6-dianhydro-d-glucitol Expired GB1356374A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US13880571A 1971-04-29 1971-04-29

Publications (1)

Publication Number Publication Date
GB1356374A true GB1356374A (en) 1974-06-12

Family

ID=22483733

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1882172A Expired GB1356374A (en) 1971-04-29 1972-04-24 Mononitrate esters of 1,3 3,6-dianhydro-d-glucitol

Country Status (10)

Country Link
AU (1) AU465217B2 (en)
CA (1) CA967164A (en)
CH (1) CH576475A5 (en)
DE (1) DE2221080C2 (en)
DK (1) DK138182B (en)
FR (1) FR2134698B1 (en)
GB (1) GB1356374A (en)
NL (1) NL7205786A (en)
SE (1) SE385895B (en)
ZA (1) ZA722868B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4559351A (en) * 1982-12-29 1985-12-17 Heinrich Mack Nachf. Dihydropyridine derivatives of 1,4:3,6-dianhydrohexitols
EP0167008A2 (en) * 1984-06-06 1986-01-08 Heinrich Mack Nachf. 1,4:3,6-Dianhydro-hexite derivatives, process for their preparation and their use as medicaments
ES2340353A1 (en) * 2008-07-22 2010-06-01 Lacer, S.A. New stereospecific method for the preparation of dioxa-bicyclooctane compounds

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065488A (en) * 1977-02-24 1977-12-27 American Home Products Corporation Process for preparing 1,4:3,6-dianhydro-D-glucitol 2-nitrate
DE3028340A1 (en) * 1980-07-25 1982-02-25 Fa. Dr. Willmar Schwabe, 7500 Karlsruhe AMINO-DESOXY-1.4; 3.6-DIANHYDRO-HEXIT-NITRATE
DE3028289C2 (en) * 1980-07-25 1986-11-27 Dr. Willmar Schwabe GmbH & Co, 7500 Karlsruhe 2-O- and 5-O-substituted 1.4; 3.6-dianhydro-hexitol-mononitrate, process for their preparation and pharmaceutical preparations containing these compounds
DE3028288A1 (en) * 1980-07-25 1982-02-25 Fa. Dr. Willmar Schwabe, 7500 Karlsruhe If necessary, N-SUBSTITUTED AMINODESOXY-1.4; 3.6-DIANHYDRO-HEXITE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE
DE3028272A1 (en) * 1980-07-25 1982-02-25 Fa. Dr. Willmar Schwabe, 7500 Karlsruhe ALKYLAMINO-DESOXY-1.4; 3.6-DIANHYDRO-HEXIT-NITRATE SUBSTITUTED BY PURINE BASES, METHOD FOR THEIR PRODUCTION AND PHARMACEUTICAL PREPARATION
DE3479800D1 (en) * 1983-11-25 1989-10-26 Toshin Chemical Co A method for the preparation of isosorbide-5-nitrate and sodium isosorbide-5-nitrate hydrate as a precursor thereof
DE4410997A1 (en) * 1994-03-30 1995-10-26 Isis Pharma Gmbh Pharmaceutical preparations and drugs for the prevention and treatment of endothelial dysfunctions
ES2142773B1 (en) 1998-10-07 2001-01-01 Lacer Sa ISOSORBIDA MONONITRATE DERIVATIVES AND THEIR EMPLOYMENT AS VASODILATATING AGENTS WITH DECREASED TOLERANCE.
ES2258365B1 (en) * 2003-10-03 2007-12-01 Lacer, S.A. DERIVATIVES OF DISULFIDE, SULFIDE, SULFOXIDE AND SULFONE OF CYCLING SUGARS AND THEIR USES.
DE102008050597A1 (en) 2008-10-09 2010-04-15 Actavis Deutschland Gmbh & Co. Kg Preparation, useful for treating and preventing idiopathic sudden sensorineural hearing loss, comprises pentaerythritol tetra-, pentaerythritol trinitrate, pentaerythritol dinitrate or pentaerythritol mononitrate, and an excipient
WO2010055138A1 (en) * 2008-11-14 2010-05-20 Lacer, S.A. New stereospecific method for the preparation of dioxa-bicyclooctane compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4559351A (en) * 1982-12-29 1985-12-17 Heinrich Mack Nachf. Dihydropyridine derivatives of 1,4:3,6-dianhydrohexitols
EP0167008A2 (en) * 1984-06-06 1986-01-08 Heinrich Mack Nachf. 1,4:3,6-Dianhydro-hexite derivatives, process for their preparation and their use as medicaments
EP0167008A3 (en) * 1984-06-06 1987-04-15 Heinrich Mack Nachf. 1,4:3,6-dianhydro-hexite derivatives, process for their preparation and their use as medicaments
ES2340353A1 (en) * 2008-07-22 2010-06-01 Lacer, S.A. New stereospecific method for the preparation of dioxa-bicyclooctane compounds
ES2340353B1 (en) * 2008-07-22 2011-05-23 Lacer, S.A. NEW STEREOSPECIFIC METHOD FOR THE PREPARATION OF DIOXA-BICYCLOOCTANE COMPOUNDS.

Also Published As

Publication number Publication date
DE2221080C2 (en) 1984-06-28
DK138182C (en) 1978-12-27
NL7205786A (en) 1972-10-31
FR2134698A1 (en) 1972-12-08
CH576475A5 (en) 1976-06-15
DK138182B (en) 1978-07-24
ZA722868B (en) 1973-12-19
FR2134698B1 (en) 1975-12-26
CA967164A (en) 1975-05-06
DE2221080A1 (en) 1972-11-09
AU4149672A (en) 1973-11-01
AU465217B2 (en) 1975-09-18
SE385895B (en) 1976-07-26

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee