Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/50—Three nitrogen atoms

Definitions

• the invention relates to a method for extracting the salt.
• TAP has Chemical Abstracts registration number 51 324 -37-9
• DANP has Chemical Abstracts registration number 2 387-48-6.
• TAP For chemical reactions in aqueous or aqueous / alcoholic solution, the TAP must be available as a readily soluble dihydrochloride (C.B. Storm, J. Org «Chem. 36 (1971) 3925).
• TAP-di-HCl can be obtained by reacting TAP sulfate with aqueous barium chloride solution, the resulting solution, in addition to the foreign organic accompanying substances still contains excess barium ions, which is questionable from a physiological point of view.
• TAP The products made from TAP are mostly natural products or important pharmaceutical components such as guanine, xanthine, folic acid and biopterin.
• TAP sulfate dissolves only slightly in hot 2% sulfuric acid and one is forced to work with large volumes, moreover the TAP sulfate purified in this way still has to be added a second reaction stage with BaCl 2 can be converted to TAP-DiHCl.
• the object of the invention was therefore to use TAP-Di-HCl with small amounts in a technically simple and economical manner - i.e. less than 1 mol.% - to produce foreign organic substances directly from the reduction products of the DANP with a single cleaning process.
• reaction with hot hydrochloric acid alone can remove a considerable part of the organic impurities accompanying the TAP.
• foreign matter contents of less than 1 mol% can only be achieved with about 20% by weight in the reaction medium after the addition of isopropyl alcohol.
• a particular advantage of the process according to the invention is that it allows the direct separation of pure TAP-Di-HCl from the filtered reduction solution of the Raney nickel hydrogenation. Accordingly, without the loss of yield, the intermediate stage of the separation of TAP sulfate using H ⁇ SO. perform, the filtered alkaline reducing solution ⁇ g acidified to H 2 and evaporated. The resulting syrup-thick crystal slurry is then subjected to the cleaning procedure according to the invention, pure TAP-Di-HCl being obtained in about 90% yield, based on DANP.
• reaction media were prepared by introducing hydrochloric acid gas into water / alcohol mixtures.
• the composition of the reaction media in alcohol and hydrochloric acid is shown in the table below, the water content always making up the residual percentages to 100% by weight.
• the crude reduction product of the DANP was then suspended in the form of the impure TAP sulfate or the TAP mono-HCl in the reaction media prepared in this way.
• the suspensions contained about 0.2 to 0.25 grams of TAP salt per kilogram of reaction medium.
• the batches were optionally kept under mild positive pressure at about 80 ° C. for the duration of the stated time, then cooled to below 30 ° C. and the crystals of TAP-di-HCl were washed with isopropyl alcohol. After drying in vacuo at 40 ° C, the crystals were analyzed.
• TAP-MonoHCl 20 40 isopropanol 1 hour 80 ° C 99.2 mol% 99.6 mol%.
• TAP sulfate 10 20 isopropanol 1 hour 80 ° C 99 mol% 98.5 mol%
• the raw TAP sulfate used had a purity of 92% by weight elementary analysis and a purity of 103 mol% iodometric.
• the crude TAP-MonoHCl used had a purity of 89 mol% elemental analysis and a purity of 94 mol% iodometric.
• Example 2 18 grams of the crude TAP sulfate used in Example 1 was suspended in 310 grams of 20% hydrochloric acid. The mixture was heated to 100 ° C., and solution occurred. After * 20 minutes, the solution was cooled to 80 ° C., 200 grams of isopropanol were added and the mixture was stirred at 80 ° C. for a further 6 ⁇ minutes.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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• 1984
  • 1984-02-01 DE DE3403468A patent/DE3403468A1/de active Granted
• 1985
  • 1985-01-02 WO PCT/EP1985/000001 patent/WO1985003506A1/de not_active Ceased
  • 1985-01-02 EP EP85900657A patent/EP0169864A1/de not_active Withdrawn
  • 1985-01-02 US US06/789,310 patent/US4670561A/en not_active Expired - Fee Related

Non-Patent Citations (1)

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