GB959407A - Process for the production of 1,6-dibromo-1,6-didesoxy-d-mannitol - Google Patents

Process for the production of 1,6-dibromo-1,6-didesoxy-d-mannitol

Info

Publication number
GB959407A
GB959407A GB3319461A GB3319461A GB959407A GB 959407 A GB959407 A GB 959407A GB 3319461 A GB3319461 A GB 3319461A GB 3319461 A GB3319461 A GB 3319461A GB 959407 A GB959407 A GB 959407A
Authority
GB
United Kingdom
Prior art keywords
mannitol
hydrogen bromide
hours
dibromo
reacted
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
GB3319461A
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB959407A publication Critical patent/GB959407A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

In a process for preparing 1, 6-dibromo-1, 6-didesoxy -D- mannitol either (a) D-mannitol is reacted with aqueous hydrogen bromide containing more than 47% of hydrogen bromide in a closed reaction system at 50 to 95 DEG C. for a maximum of 0.5 to 12 hours, or (b) 1, 4-3, 6-dianhydro -D- mannitol or an acetal thereof is reacted with aqueous hydrogen bromide containing more than 30% hydrogen bromide, or (c) 1, 2-5, 6-dianhydro -D- mannitol or an acetal thereof is reacted with aqueous hydrogen bromide Preferably reaction (a) is carried out at 60 DEG C. for 7-9 hours or at 80 DEG C. for 0.5 to 2 hours; (b) at 90-125 DEG C. under atmospheric pressure for 0.5-2 hours, and moreover saturating the starting material with hydrogen bromide at 0 DEG C. and autoclaving the mixture for 2-5 hours at 70-90 DEG C.; and (c) by reacting the starting material with an excess of hydrogen bromide in the presence of a water soluble organic solvent. The dibromo mannitol may be recrystallized in high yield by dissolving it in a solvent such as methanol and precipitating it by the addition of a chlorinated hydrocarbon. 1, 2, 6-Tribromo-1, 2, 6-tridesoxy -D- mannitol is formed as a by-product in the above reaction, the amount formed depending on the conditions of the reaction. The dibromo- and tribromo-mannitols are separated by fractional crystallisation.ALSO:A pharmaceutical composition comprises 1,6 - dibromo - 1,6 - didesoxy - D - mannitol in admixture with a pharmaceutical carrier or excipient. The compositions may be in the form of a tablet, dragee, capsule, solution or an injection solution and are useful in the treatment of myeloid leukaemia.
GB3319461A 1960-09-15 1961-09-15 Process for the production of 1,6-dibromo-1,6-didesoxy-d-mannitol Expired GB959407A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUGO000760 1960-09-15
HUCI000381 1961-09-06

Publications (1)

Publication Number Publication Date
GB959407A true GB959407A (en) 1964-06-03

Family

ID=26318369

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3319461A Expired GB959407A (en) 1960-09-15 1961-09-15 Process for the production of 1,6-dibromo-1,6-didesoxy-d-mannitol

Country Status (3)

Country Link
AT (1) AT245580B (en)
DK (1) DK113988B (en)
GB (1) GB959407A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993781A (en) * 1965-01-13 1976-11-23 Chinoin Gyogyszer-Es Vegyeszeti Termekek Gyara Rt 1,6-Dibromo-1,6-dideoxy-dulcitol and pharmaceutical compositions containing same
US4078137A (en) * 1975-05-16 1978-03-07 Hommel Aktiengesellschaft Process for manufacturing a flavone derivative
US4228150A (en) * 1979-04-23 1980-10-14 Iowa State University Research Foundation, Inc. Method of inhibiting dextransucrase and oral compositions for use therein
US4335100A (en) * 1979-04-23 1982-06-15 Iowa State University Research Foundation, Inc. Method of inhibiting dextransucrase and oral compositions for use therein

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993781A (en) * 1965-01-13 1976-11-23 Chinoin Gyogyszer-Es Vegyeszeti Termekek Gyara Rt 1,6-Dibromo-1,6-dideoxy-dulcitol and pharmaceutical compositions containing same
US4078137A (en) * 1975-05-16 1978-03-07 Hommel Aktiengesellschaft Process for manufacturing a flavone derivative
US4228150A (en) * 1979-04-23 1980-10-14 Iowa State University Research Foundation, Inc. Method of inhibiting dextransucrase and oral compositions for use therein
US4335100A (en) * 1979-04-23 1982-06-15 Iowa State University Research Foundation, Inc. Method of inhibiting dextransucrase and oral compositions for use therein

Also Published As

Publication number Publication date
AT245580B (en) 1966-03-10
DK113988B (en) 1969-05-19

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