DE1212974B - Process for the preparation of 5,5-diphenyl-N-carboaethoxyhydantoin - Google Patents

Process for the preparation of 5,5-diphenyl-N-carboaethoxyhydantoin

Info

Publication number
DE1212974B
DE1212974B DED42440A DED0042440A DE1212974B DE 1212974 B DE1212974 B DE 1212974B DE D42440 A DED42440 A DE D42440A DE D0042440 A DED0042440 A DE D0042440A DE 1212974 B DE1212974 B DE 1212974B
Authority
DE
Germany
Prior art keywords
diphenyl
preparation
diphenylhydantoin
ethyl chloroformate
carboaethoxyhydantoin
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.)
Pending
Application number
DED42440A
Other languages
German (de)
Inventor
Hideji Takamatsu
Susumu Umemoto
Katsuro Fujimoto
Keiji Nakamura
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.)
Dainippon Pharmaceutical Co Ltd
Original Assignee
Dainippon Pharmaceutical Co 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 Dainippon Pharmaceutical Co Ltd filed Critical Dainippon Pharmaceutical Co Ltd
Publication of DE1212974B publication Critical patent/DE1212974B/en
Pending 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

Landscapes

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

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. CL:Int. CL:

C07dC07d

Deutsche Kl.: 12p-9German class: 12p-9

Nummer: 1 212 974Number: 1 212 974

Aktenzeichen: D 42440IV d/12 ρFile number: D 42440IV d / 12 ρ

Anmeldetag: 10. September 1963Filing date: September 10, 1963

Auslegetag: 24. März 1966Opening day: March 24, 1966

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 5,5-Diphenyl-N3-carboäthoxyhydantoin der FormelThe invention relates to a process for the preparation of 5,5-diphenyl-N 3 -carboethoxyhydantoin of the formula

CO — N — COOC2H5 CO - N - COOC 2 H 5

NH-CONH-CO

das dadurch gekennzeichnet ist, daß man in an sich bekannter Weise entweder 5,5-Diphenylhydantoin in Gegenwart von Alkali oder ein Alkalimetallsalz von 5,5-Diphenylhydantoin mit Äthylchlorformiat umsetzt.which is characterized in that either 5,5-diphenylhydantoin is used in a manner known per se in the presence of alkali or an alkali metal salt of 5,5-diphenylhydantoin with ethyl chloroformate implements.

Die Umsetzung kann in einem inerten Lösungsmittel, z. B. in Äther oder Benzol, durchgeführt werden. Das Äthylchlorformiat kann man in äquimolarer Menge oder im Überschuß verwenden. Im zuletzt angegebenen Falle kann das Äthylchlorformiat gleichzeitig als Reaktionsmedium dienen. Die Umsetzung kann bei Raumtemperatur erfolgen, vorzugsweise erhitzt man jedoch. Das Lösungsmittel und der Äthylchlorformiatüberschuß werden abdestilliert, und der Rückstand wird aus einem geeigneten Lösungsmittel umkristallisiert.The reaction can be carried out in an inert solvent, e.g. B. in ether or benzene carried out will. The ethyl chloroformate can be used in an equimolar amount or in excess. in the The last case mentioned, the ethyl chloroformate can also serve as the reaction medium. The reaction can take place at room temperature, but it is preferred to heat. The solvent and the ethyl chloroformate excess are distilled off, and the residue is removed from a suitable one Recrystallized solvent.

Das 5,5-Diphenyl-N3-carboäthoxyhydantoin zeigt bei oraler Verabreichung hervorragende krampflösende Wirkung und ist in dieser Hinsicht dem bekannten 5-Phenyl-5-tert.butylhydantoin überlegen. Die krampflösende Wirkung zeigt sich sowohl im Cardiazol- als auch im Elektroschock-Test mit Ratten. Sie hält 24 bis 48 Stunden an. Das Verfahrensprodukt eignet sich somit für die Behandlung von an Epilepsie leidenden Patienten, wie klinisch nachgewiesen wurde.The 5,5-diphenyl-N 3 -carboethoxyhydantoin shows an excellent antispasmodic effect when administered orally and is superior to the known 5-phenyl-5-tert-butylhydantoin in this respect. The anticonvulsant effect is evident in both the cardiazole and the electric shock test with rats. It lasts for 24 to 48 hours. The process product is thus suitable for the treatment of patients suffering from epilepsy, as has been clinically proven.

Das folgende Beispiel erläutert das erfindungsgemäße Verfahren.The following example explains the method according to the invention.

Beispielexample

21 g Äthylchlorformiat werden zu 27,6 g 5,5-Diphenylhydantoinnatrium gegeben. Anschließend wird 30 Minuten unter Rückfluß auf dem Wasserbad erhitzt. Nach dem Abdestillieren des Äthylchlorformiatüberschusses wird dem Rückstand Wasser zugesetzt und gekühlt. Man erhält rohe Kristalle. Die Kristalle werden aus Isopropanol umkristallisiert. Ausbeute 25,0 g 5,5-Diphenyl-N3-carboäthoxyhydantoin in Form weißer nadeiförmiger Kristalle; F.=139 bis 1400C.21 g of ethyl chloroformate are added to 27.6 g of 5,5-diphenylhydantoin sodium. It is then refluxed for 30 minutes on a water bath. After the excess ethyl chloroformate has been distilled off, water is added to the residue and the mixture is cooled. Crude crystals are obtained. The crystals are recrystallized from isopropanol. Yield 25.0 g of 5,5-diphenyl-N 3 -carboethoxyhydantoin in the form of white needle-shaped crystals; F. = 139 to 140 0 C.

Verfahren zur Herstellung von 5,5-Diphenyl-Ns-carboäthoxyhydantoinProcess for the preparation of 5,5-diphenyl-N s -carboethoxyhydantoin

Anmelder:Applicant:

Dainippon Pharmaceutical Co., Ltd., Osaka (Japan)Dainippon Pharmaceutical Co., Ltd., Osaka (Japan)

Vertreter:Representative:

Dr. W. Beil, A. Hoeppener und Dr. H. J. Wolff, Rechtsanwälte,Dr. W. Beil, A. Hoeppener and Dr. H. J. Wolff, lawyers,

Frankfurt/M.-Höchst, Adelonstr. 58Frankfurt / M.-Höchst, Adelonstr. 58

Als Erfinder benannt:Named as inventor:

Hideji Takamatsu, Amagasaki-shi, Hyogo-ken; Susumu Umemoto, Sakai-shi, Osaka-fu; Katsuro Fujimoto, Neyagawa-shi, Osaka-fu; Keiji Nakamura, Amagasaki-shi, Hyogo-ken (Japan)Hideji Takamatsu, Amagasaki-shi, Hyogo-ken; Susumu Umemoto, Sakai-shi, Osaka-fu; Katsuro Fujimoto, Neyagawa-shi, Osaka-fu; Keiji Nakamura, Amagasaki-shi, Hyogo-ken (Japan)

Beanspruchte Priorität:Claimed priority:

Japan vom 12. September 1962 (39 217)Japan September 12, 1962 (39 217)

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von 5,5-Diphenyl-N3-carboäthoxyhydantoin der FormelProcess for the preparation of 5,5-diphenyl-N 3 -carboethoxyhydantoin of the formula CO — N — COOC2H5CO - N - COOC2H5 / NH — CO/ NH - CO dadurch gekennzeichnet, daß man in an sich bekannter Weise entweder 5,5-Diphenylhydantoin in Gegenwart von Alkali oder ein Alkalimetallsalz von 5,5-Diphenylhydantoin mit Äthylchlorformiat umsetzt.characterized in that either 5,5-diphenylhydantoin is used in a manner known per se in the presence of alkali or an alkali metal salt of 5,5-diphenylhydantoin with ethyl chloroformate. In Betracht gezogene Druckschriften: Deutsche Auslegeschriften Nr. 1067822, 1041502; W. H ü c k e 1, Pharmazeutische Chemie und Arzneimittelsynthese, Bd. II (Stuttgart, 1954), S. 245,246.Considered publications: German Auslegeschriften Nos. 1067822, 1041502; W. Hück e 1, Pharmaceutical Chemistry and Drug Synthesis, Vol. II (Stuttgart, 1954), pp. 245,246.
DED42440A 1962-09-12 1963-09-10 Process for the preparation of 5,5-diphenyl-N-carboaethoxyhydantoin Pending DE1212974B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1212974X 1962-09-12

Publications (1)

Publication Number Publication Date
DE1212974B true DE1212974B (en) 1966-03-24

Family

ID=14807759

Family Applications (1)

Application Number Title Priority Date Filing Date
DED42440A Pending DE1212974B (en) 1962-09-12 1963-09-10 Process for the preparation of 5,5-diphenyl-N-carboaethoxyhydantoin

Country Status (1)

Country Link
DE (1) DE1212974B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755350A (en) * 1970-10-06 1973-08-28 Rhone Poulenc Sa Substituted 3-phenyl hydantoins useful as fungicides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1041502B (en) * 1957-04-05 1958-10-23 Riedel De Haeen Ag Process for the preparation of a new hydantoin compound
DE1067822B (en) * 1958-07-11 1959-10-29 Riedel De Haeen Ag Process for the production of new hydantoins

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1041502B (en) * 1957-04-05 1958-10-23 Riedel De Haeen Ag Process for the preparation of a new hydantoin compound
DE1067822B (en) * 1958-07-11 1959-10-29 Riedel De Haeen Ag Process for the production of new hydantoins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755350A (en) * 1970-10-06 1973-08-28 Rhone Poulenc Sa Substituted 3-phenyl hydantoins useful as fungicides

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