GB785248A - New therapeutically active derivatives of barbituric acid - Google Patents

New therapeutically active derivatives of barbituric acid

Info

Publication number
GB785248A
GB785248A GB24569/55A GB2456955A GB785248A GB 785248 A GB785248 A GB 785248A GB 24569/55 A GB24569/55 A GB 24569/55A GB 2456955 A GB2456955 A GB 2456955A GB 785248 A GB785248 A GB 785248A
Authority
GB
United Kingdom
Prior art keywords
bicyclo
octenyl
acid
methyl
cyanoacetic
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
GB24569/55A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB24569/55A priority Critical patent/GB785248A/en
Priority to CH3660956A priority patent/CH367175A/en
Publication of GB785248A publication Critical patent/GB785248A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters

Landscapes

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

Abstract

The invention comprises barbituric acids of the general formula <FORM:0785248/IV (a)/1> in which X stands for a saturated or unsaturated alkyl group, with 1 to 3 carbon atoms or 2 or 3 carbon atoms, respectively, Y stands for hydrogen or a methyl group and A denotes an oxygen or sulphur atom and salts of such acids. The acids are obtained by condensation of a functional derivative of bicyclo-octenyl cyanoacetic or malonic acid such as for example an ester, amide, nitrile or chloride and urea or a derivative or related compound such as guanidine, thiourea, dicyandiamide or isourea ethers, or the saturated or unsaturated alkyl derivatives of such compounds. The alkyl groups on the C5-atom may be present in the cyanoacetic or malonic acid or may be introduced subsequently into the barbiturates. In examples: (1) bicyclo-1,2,3-octan-2-one and cyanoacetic acid ethyl ester are reacted in the presence of ammonium acetate and acetic acid to give the bicyclo-octenyl cyanoacetic acid ethyl ester. This, reacted with methyl iodide in the presence of sodium gives (bicyclo-octenyl)-methyl-cyanoacetic acid ethyl ester which is reacted with urea to form 5-(bicyclo-octenyl)-5-methyl-barbituric acid. The acid is converted into its sodium and diethylaminoethanol salts; (2) 5-(bicyclo-octenyl)-5-ethyl-barbituric is prepared similarly; (3) (bicyclo-octenyl)-allyl-cyanoacetic acid ethyl ester and dicyandiamide are reacted in the presence of sodium to form (bicyclo-octenyl)-allyl cyaniminobarbituric acid which is saponified with sulphuric acid to 5-(bicyclo-octenyl)-5-allyl-barbituric acid; (4) 5-(bicyclo - octenyl) - 5 - methyl - barbituric acid is prepared similarly and then methylated with methyl sulphate in the 1-position also; (5), (6) and (8) 5-(bicyclo-octenyl)-5-methyl-(allyl- and ethyl-) thiobarbituric acids respectively are obtained in analogous manner from thiourea; (7) (bicyclo - octenyl) - ethyl - cyanoacetic acid ethyl ester and N-methyl-acetyl-urea are reacted in the presence of sodium to form 5-(bicyclo - octenyl) - 5 - ethyl - 1 - methyl-barbituric acid.
GB24569/55A 1955-08-26 1955-08-26 New therapeutically active derivatives of barbituric acid Expired GB785248A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB24569/55A GB785248A (en) 1955-08-26 1955-08-26 New therapeutically active derivatives of barbituric acid
CH3660956A CH367175A (en) 1955-08-26 1956-08-17 Process for the production of new 5,5-disubstituted barbituric acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB24569/55A GB785248A (en) 1955-08-26 1955-08-26 New therapeutically active derivatives of barbituric acid

Publications (1)

Publication Number Publication Date
GB785248A true GB785248A (en) 1957-10-23

Family

ID=10213708

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24569/55A Expired GB785248A (en) 1955-08-26 1955-08-26 New therapeutically active derivatives of barbituric acid

Country Status (2)

Country Link
CH (1) CH367175A (en)
GB (1) GB785248A (en)

Also Published As

Publication number Publication date
CH367175A (en) 1963-02-15

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