GB864536A - ª‡-ethyl-phenylacetylurea - Google Patents

ª‡-ethyl-phenylacetylurea

Info

Publication number
GB864536A
GB864536A GB3462257A GB3462257A GB864536A GB 864536 A GB864536 A GB 864536A GB 3462257 A GB3462257 A GB 3462257A GB 3462257 A GB3462257 A GB 3462257A GB 864536 A GB864536 A GB 864536A
Authority
GB
United Kingdom
Prior art keywords
isomer
alpha
ethyl
acid
excitive
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
GB3462257A
Inventor
Philippe Gold-Aubert
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.)
Sapos S A Lab
Original Assignee
Sapos S A Lab
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 Sapos S A Lab filed Critical Sapos S A Lab
Priority to GB3462257A priority Critical patent/GB864536A/en
Priority to CH6560558A priority patent/CH374644A/en
Publication of GB864536A publication Critical patent/GB864536A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/50—Y being a hydrogen or an acyclic carbon atom
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • A61K31/515—Barbituric acids; Derivatives thereof, e.g. sodium pentobarbital
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients

Landscapes

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

Abstract

The invention comprises the optically active isomers of alpha-ethyl-phenylacetylurea; and a process for the preparation of alpha-ethylphenylacetylurea which comprises reacting alpha-ethyl-phenylacetyl chloride with urea in the presence of an acid-binding agent and in the absence of a solvent. The process p is preferably effected at 75 to 150 DEG C. in the presence of 1-phenyl-2, 3-dimethyl- 5-pyrazolone or an alkali metal bicarbonate. When the d- or l-isomer of the acid chloride is used the process leads to the optically active isomers of the invention, and this process may be combined with the preparation of the active acid chlorides by reaction of the corresponding optically active acids with thionyl or sulphuryl chloride. This process may in turn be combined with the preparation of the active acids by resolution of racemic alpha-ethyl-phenylacetic acid with an optically active base followed by fractional crystallization of the resulting salts and recovery of the optically active acids therefrom. The preferred active base is cinchoridine and the crystallization is preferably effected in fifty per cent. aqueous ethanol, the d-acid salt of this base being less soluble than the l-acid salt. The l-isomer is preferably further purified after liberation from the cinchoridine salt by isolation as the codeine salt, from which the acid is again liberated. Examples are given, and reference is also made to the use of common solvents in the process of the invention. It is stated that while both the d- and l-isomers of alpha-ethyl-phenylacetylurea have anti-epileptic activity, the d-isomer has an excitive action whereas the l-isomer has a sedative action (see Group VI).ALSO:A composition for the treatment of epilepsy and like conditions, having substantially no sedative, soporific or excitive properties, comprises d-alpha-ethyl-phenylacetylurea together with one or more drugs having a soporific and/or sedative action. Such a composition is prepared by mixing with the said d-isomer, which itself has excitive properties, just sufficient of a sedative and/or soporific drug substantially to neutralize the excitive properties of the d-isomer. Such drugs include barbiturates, phenacemide and anti-convulsant drugs such as diphenylhydantoin, and in particular l-alpha-ethylphenylacetylurea, which itself has sedative properties. The compositions of the invention do not include racemic alpha-ethyl-phenylacetylurea, which has excitive properties, or compositions containing it. Preferred compositions contain the d- and l-isomers in a ratio of 1 : 3 to 1 : 1.25 parts by weight, preferably 30 to 40 parts by weight of the d-isomer to 60 to 70 of the l-isomer. Reference is also made to the use of the individual d- and l-isomers in the treatment of epilepsy, when they may be combined with a suitable pharmaceutical carrier and made up as tablets, capsules, syrups or elixirs, which may contain flavouring agents, or injection solutions.
GB3462257A 1957-11-06 1957-11-06 ª‡-ethyl-phenylacetylurea Expired GB864536A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3462257A GB864536A (en) 1957-11-06 1957-11-06 ª‡-ethyl-phenylacetylurea
CH6560558A CH374644A (en) 1957-11-06 1958-10-30 Process for the preparation of optically active α-ethyl-phenylacetylurea

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3462257A GB864536A (en) 1957-11-06 1957-11-06 ª‡-ethyl-phenylacetylurea

Publications (1)

Publication Number Publication Date
GB864536A true GB864536A (en) 1961-04-06

Family

ID=10367945

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3462257A Expired GB864536A (en) 1957-11-06 1957-11-06 ª‡-ethyl-phenylacetylurea

Country Status (2)

Country Link
CH (1) CH374644A (en)
GB (1) GB864536A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004087161A1 (en) * 2003-04-04 2004-10-14 Novartis Ag Combinations comprising anti-epileptic drugs for the treatment of neurological disorders
US9763954B2 (en) 2007-01-15 2017-09-19 Bial—Portela & Ca, S.A. Therapeutical uses of eslicarbazepine
US10675287B2 (en) 2005-05-06 2020-06-09 Bial-Portela & Ca S.A. Methods of treatment of partial onset seizures using eslicarbazepine acetate

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004087161A1 (en) * 2003-04-04 2004-10-14 Novartis Ag Combinations comprising anti-epileptic drugs for the treatment of neurological disorders
AU2004226825B2 (en) * 2003-04-04 2007-08-16 Novartis Ag Combinations comprising anti-epileptic drugs for the treatment of neurological disorders
US10675287B2 (en) 2005-05-06 2020-06-09 Bial-Portela & Ca S.A. Methods of treatment of partial onset seizures using eslicarbazepine acetate
US10695354B2 (en) 2005-05-06 2020-06-30 Bial-Portela & Ca S.A. Methods of treatment of partial onset seizures using eslicarbazepine acetate
US10702536B2 (en) 2005-05-06 2020-07-07 Bial-Portela & Ca S.A. Methods of treatment of partial onset seizures using eslicarbazepine acetate
US11364247B2 (en) 2005-05-06 2022-06-21 Bial-Portela & Ca S.A. Methods of treatment of partial onset seizures using eslicarbazepine acetate
US9763954B2 (en) 2007-01-15 2017-09-19 Bial—Portela & Ca, S.A. Therapeutical uses of eslicarbazepine

Also Published As

Publication number Publication date
CH374644A (en) 1964-01-31

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