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GB997037A - New hydrantoin derivatives - Google Patents

New hydrantoin derivatives

Info

Publication number
GB997037A
GB997037A GB1036262A GB1036262A GB997037A GB 997037 A GB997037 A GB 997037A GB 1036262 A GB1036262 A GB 1036262A GB 1036262 A GB1036262 A GB 1036262A GB 997037 A GB997037 A GB 997037A
Authority
GB
United Kingdom
Prior art keywords
formula
heating
strong acid
aqueous medium
bromophenylisocyanate
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
GB1036262A
Inventor
Wilson Shaw Waring
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1036262A priority Critical patent/GB997037A/en
Publication of GB997037A publication Critical patent/GB997037A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0997037/C2/1> (wherein R1 stands for an o-substituted phenyl radical which may optionally bear one or more additional substituents in the remaining positions of the phenyl radical, the substituent(s) being selected from halogen atoms and methyl, trifluoromethyl, methoxy, phenyl, halophenyl and nitro groups, and R2 stands for a hydrogen atom or a C1-4 alkyl group), pharmaceutical preparations containing them, and their preparation by (a) reacting an aminonitrile of the formula <FORM:0997037/C2/2> with R1NCO and heating the product with a strong acid in an aqueous medium, (b) heating a ureido derivative of the formula <FORM:0997037/C2/3> with a strong acid in an aqueous medium or (c) heating an iminohydantoin of the formula <FORM:0997037/C2/4> with a strong acid in an aqueous medium. The following intermediates are prepared from the starting materials indicated in parentheses: 2 - (p - bromophenyl) 5 bromophenylisocyanate (2 - (p - bromophenyl) - 5 - bromoaniline); 2 - (p - chlorophenyl) - 5 - chlorophenylisocyanate (2 - (p - chlorophenyl) - 5 - chloroaniline); 2 - (p - fiuorophenyl) - 5 - fluorophenylisocyanate (2 - (p - fluorophenyl) - 5 - fluoroaniline hydrochloride); o - iodophenylisocyanate (o - iodoaniline); o - bromophenylisocyanate (o - bromoaniline) 4 - chloro - 2 - trifluoromethylphenylisocyanate (4 - chloro - 2 - trifluoromethylaniline). The compounds of the invention are anticonvulsants useful in the treatment of epilepsy, and may be administered orally in the form of pharmaceutical preparations (e.g. tablets, capsules, aqueous or oily solutions or suspensions, dispersible powders or granules, syrups or elixirs) containing them together with a diluent or carrier.
GB1036262A 1962-03-19 1962-03-19 New hydrantoin derivatives Expired GB997037A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1036262A GB997037A (en) 1962-03-19 1962-03-19 New hydrantoin derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1036262A GB997037A (en) 1962-03-19 1962-03-19 New hydrantoin derivatives

Publications (1)

Publication Number Publication Date
GB997037A true GB997037A (en) 1965-06-30

Family

ID=9966447

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1036262A Expired GB997037A (en) 1962-03-19 1962-03-19 New hydrantoin derivatives

Country Status (1)

Country Link
GB (1) GB997037A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2649925A1 (en) * 1975-10-29 1977-05-12 Roussel Uclaf NEW IMIDAZOLIDINS, PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL COMPOSITIONS THEREOF
EP0017976A2 (en) * 1979-04-24 1980-10-29 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for preparing imidazole derivatives
US4234736A (en) 1977-10-28 1980-11-18 Hoffmann-La Roche Inc. Antiandrogenic and schistosomicidal imidazolidine derivatives
EP0091596A2 (en) * 1982-04-08 1983-10-19 Shell Internationale Researchmaatschappij B.V. Hydantoins, their preparation and application
WO1995018794A1 (en) * 1994-01-05 1995-07-13 Roussel Uclaf Novel optionally substituted phenylimidazolidines, intermediates and process for their preparation, their use as drugs and pharmaceutical compositions containing them
FR2715402A1 (en) * 1994-01-05 1995-07-28 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
FR2724169A1 (en) * 1994-09-06 1996-03-08 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
WO1997006149A1 (en) * 1995-08-10 1997-02-20 Arzneimittelwerk Dresden Gmbh Novel imidazoline-2,4-diones with an ortho-substituted ar(alk)yl radical in position 1, having an anti-convulsive effect, and process for their production
EP0816342A2 (en) * 1996-06-24 1998-01-07 Sumitomo Chemical Company, Limited Process for producing 1-substituted-hydantoins
WO1998004525A1 (en) * 1996-07-27 1998-02-05 Agrevo Uk Limited Fungicidal n-aryl five-membered cyclic imides

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2649925A1 (en) * 1975-10-29 1977-05-12 Roussel Uclaf NEW IMIDAZOLIDINS, PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL COMPOSITIONS THEREOF
US4234736A (en) 1977-10-28 1980-11-18 Hoffmann-La Roche Inc. Antiandrogenic and schistosomicidal imidazolidine derivatives
EP0017976A2 (en) * 1979-04-24 1980-10-29 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for preparing imidazole derivatives
EP0017976A3 (en) * 1979-04-24 1981-04-01 F. Hoffmann-La Roche & Co. Aktiengesellschaft Process for preparing imidazole derivatives and the starting materials used in this process
EP0091596A2 (en) * 1982-04-08 1983-10-19 Shell Internationale Researchmaatschappij B.V. Hydantoins, their preparation and application
EP0091596A3 (en) * 1982-04-08 1985-04-10 Celamerck Gmbh & Co. Kg Hydantoins, their preparation and application
WO1995018794A1 (en) * 1994-01-05 1995-07-13 Roussel Uclaf Novel optionally substituted phenylimidazolidines, intermediates and process for their preparation, their use as drugs and pharmaceutical compositions containing them
FR2715402A1 (en) * 1994-01-05 1995-07-28 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
FR2724169A1 (en) * 1994-09-06 1996-03-08 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
WO1997006149A1 (en) * 1995-08-10 1997-02-20 Arzneimittelwerk Dresden Gmbh Novel imidazoline-2,4-diones with an ortho-substituted ar(alk)yl radical in position 1, having an anti-convulsive effect, and process for their production
EP0816342A2 (en) * 1996-06-24 1998-01-07 Sumitomo Chemical Company, Limited Process for producing 1-substituted-hydantoins
EP0816342A3 (en) * 1996-06-24 1998-01-28 Sumitomo Chemical Company, Limited Process for producing 1-substituted-hydantoins
WO1998004525A1 (en) * 1996-07-27 1998-02-05 Agrevo Uk Limited Fungicidal n-aryl five-membered cyclic imides

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