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GB969813A - Improvements in or relating to 1,2,4-oxadiazole derivatives - Google Patents

Improvements in or relating to 1,2,4-oxadiazole derivatives

Info

Publication number
GB969813A
GB969813A GB2430562A GB2430562A GB969813A GB 969813 A GB969813 A GB 969813A GB 2430562 A GB2430562 A GB 2430562A GB 2430562 A GB2430562 A GB 2430562A GB 969813 A GB969813 A GB 969813A
Authority
GB
United Kingdom
Prior art keywords
alkyl
general formula
amidoxime
hcl
reacting
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
GB2430562A
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
Publication of GB969813A publication Critical patent/GB969813A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,2,4-Oxadiazoles of the general Formula I <FORM:0969813/C1/1> wherein R is acyl, optionally substituted by halogen, alkoxy, alkyl, sulphonamido, or an alkyl substituted or unsubstituted aralkyl including naphthyl, R1 is alkyl, R2 is alkyl, R1 and R1 being identical or different, or R1 and R2 together with the nitrogen atom forming a heterocyclic ring, are made by reacting an amidoxime of the general Formula II <FORM:0969813/C1/2> with acrylyl chloride, in the presence of an HCl capturing agent at ambient or below ambient temperature, and reacting the resulting O-acrylyl-amidoxime with an amine of the general Formula III <FORM:0969813/C1/3> at preferably 40-100 DEG C. The HCl capturing agents specified include alkali-metal carbonates and e.g. pyridine and it is advantageous to perform one or both stages of the reaction in an inert solvent e.g. benzene, chloroform, dioxan and acetone. The products may be converted to their salts, citrates and hydrochlorides being exemplified. Numerous examples are given. Reference has been directed by the Comptroller to Specification 924,608.
GB2430562A 1962-03-26 1962-06-25 Improvements in or relating to 1,2,4-oxadiazole derivatives Expired GB969813A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT580562 1962-03-26

Publications (1)

Publication Number Publication Date
GB969813A true GB969813A (en) 1964-09-16

Family

ID=11120525

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2430562A Expired GB969813A (en) 1962-03-26 1962-06-25 Improvements in or relating to 1,2,4-oxadiazole derivatives

Country Status (1)

Country Link
GB (1) GB969813A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2401263A2 (en) * 2009-02-25 2012-01-04 SK Biopharmaceuticals Co., Ltd. Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2401263A2 (en) * 2009-02-25 2012-01-04 SK Biopharmaceuticals Co., Ltd. Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same
CN102333764A (en) * 2009-02-25 2012-01-25 爱思开生物制药株式会社 Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same
EP2401263A4 (en) * 2009-02-25 2012-11-28 Sk Biopharmaceuticals Co Ltd Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same
US8828992B2 (en) 2009-02-25 2014-09-09 Sk Biopharmaceuticals Co., Ltd. Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same
AU2010218584B2 (en) * 2009-02-25 2015-12-03 Sk Biopharmaceuticals Co., Ltd. Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same
CN102333764B (en) * 2009-02-25 2016-01-06 爱思开生物制药株式会社 The pyrrole derivative replaced, containing the medicinal compositions of these derivatives and treat parkinsonian method with it
RU2578596C2 (en) * 2009-02-25 2016-03-27 Ск Байофармасьютикалз Ко., Лтд. Substituted azol derivatives, pharmaceutical composition containing these derivatives, and methods of treating parkinson's disease with using these derivatives

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