GB907848A - 5-aryl-2-amino-2-oxazolin-4-ones - Google Patents

5-aryl-2-amino-2-oxazolin-4-ones

Info

Publication number
GB907848A
GB907848A GB662561A GB662561A GB907848A GB 907848 A GB907848 A GB 907848A GB 662561 A GB662561 A GB 662561A GB 662561 A GB662561 A GB 662561A GB 907848 A GB907848 A GB 907848A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aryl
phenyl
general formula
hydrogen atoms
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
GB662561A
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 Holdings LLC
Original Assignee
American Cyanamid Co
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 Cyanamid Co filed Critical American Cyanamid Co
Priority to DE19611545562 priority Critical patent/DE1545562A1/en
Priority to DE19611420954 priority patent/DE1420954A1/en
Publication of GB907848A publication Critical patent/GB907848A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/46—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 5-aryl-2-amino-2-oxazolin-4-ones of the general formula: <FORM:0907848/IV (b)/1> and the non toxic acid addition salts and tautomers thereof, wherein X is a halogen atom and R1 and R2 are the same or different and are hydrogen atoms or C1-6 alkyl groups or X is a hydrogen atom and R1 and R2 are the same or different C1-6 alkyl groups and the preparation thereof (a) by condensing a 2-oxazolid-4-one of the formula <FORM:0907848/IV (b)/2> with an alkylating or aminating agent, wherein (i) when Y is NHR1, in which R1 is a hydrogen atom or a C1-6 alkyl group and X is aydrogen or halogen atom the alkylating agent is a C1-6 alkyl sulphate or sulphonate, the alkylation being carried out in the presence of a base; (ii) when Y is -NR3R4 or SR3 in which R3 and/or R4 are hydrogen atoms or alkyl or aryl groups then the aminating agent is R1R2NH; X, R1 and R2 being defined as in I or (b) by cyclizing a phenylacetic acid derivative of the general formula <FORM:0907848/IV (b)/3> wherein (i) K is -NH-C:Z-NR1R2 in which Z is O when Y is halogen or sulphonyloxy and Z is NH or S when Y is OH or (ii) K is NHCN and Y is OH, or (iii) K is NR3R4 or OR5 in which R3 and R4 are hydrogen atoms, alkyl or aryl groups and R5 is an alkyl or aryl group and Y is -O-C:NH-NR1R2. The starting materials for process (b) are prepared in situ from an appropriate reactive phenylacetic acid derivative and a urea, thiourea, guanidine, or cyanamide. Acyl ureas derived from urea or dialkylurea and 2-phenyl-2-haloacetyl halides, alkyl 2-phenyl-2-haloacetates, 2-phenyl-2-(p-toluenesulphonyloxy)-acetyl halides or their o-halophenyl analogues may be isolated. Ethyl o-fluoromandelate is prepared by esterification of the acid with ethanol in the presence of p-toluenesulphonic acid. Pharmaceutical compositions useful as central nervous system stimulants comprise the compounds of general formula I together with a pharmaceutical excipient and may be in the form of tablets, dragees, capsules, suppositories, liquids to be administered in drops, emulsions, suspensions, syrups, chocolate, candy and chewing gum. U.S.A. Specification 2,892,753 is referred to.
GB662561A 1960-06-10 1961-02-23 5-aryl-2-amino-2-oxazolin-4-ones Expired GB907848A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19611545562 DE1545562A1 (en) 1960-06-10 1961-03-06 Process for the preparation of nitrogen-containing compounds
DE19611420954 DE1420954A1 (en) 1960-06-10 1961-03-06 Process for the preparation of nitrogen-containing compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3511660A 1960-06-10 1960-06-10
US3511560A 1960-06-10 1960-06-10

Publications (1)

Publication Number Publication Date
GB907848A true GB907848A (en) 1962-10-10

Family

ID=26711766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB662561A Expired GB907848A (en) 1960-06-10 1961-02-23 5-aryl-2-amino-2-oxazolin-4-ones

Country Status (6)

Country Link
AT (1) AT256101B (en)
CH (4) CH401057A (en)
DK (2) DK105405C (en)
ES (1) ES265401A1 (en)
FR (1) FR1555453A (en)
GB (1) GB907848A (en)

Also Published As

Publication number Publication date
CH413840A (en) 1966-05-31
CH437293A (en) 1967-06-15
DK102861C (en) 1965-10-18
FR1555453A (en) 1969-01-31
ES265401A1 (en) 1961-09-01
AT256101B (en) 1967-08-10
CH401057A (en) 1965-10-31
CH421965A (en) 1966-10-15
DK105405C (en) 1966-09-26

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