FR2418222A2 - Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy - Google Patents

Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy

Info

Publication number
FR2418222A2
FR2418222A2 FR7805578A FR7805578A FR2418222A2 FR 2418222 A2 FR2418222 A2 FR 2418222A2 FR 7805578 A FR7805578 A FR 7805578A FR 7805578 A FR7805578 A FR 7805578A FR 2418222 A2 FR2418222 A2 FR 2418222A2
Authority
FR
France
Prior art keywords
phenyl
hydroxy
amino
alpha
anticonvulsants
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.)
Granted
Application number
FR7805578A
Other languages
French (fr)
Other versions
FR2418222B2 (en
Inventor
Bernard Michel Raison
Jean-Pierre Kaplan
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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
Priority claimed from FR7524065A external-priority patent/FR2319338A1/en
Priority claimed from FR7621922A external-priority patent/FR2358887A2/en
Application filed by Synthelabo SA filed Critical Synthelabo SA
Priority to FR7805578A priority Critical patent/FR2418222A2/en
Priority to JP2247179A priority patent/JPS54125644A/en
Priority to PT69288A priority patent/PT69288A/en
Priority to NO790646A priority patent/NO790646L/en
Priority to NL7901474A priority patent/NL7901474A/en
Priority to ES478070A priority patent/ES478070A1/en
Priority to IL56737A priority patent/IL56737A/en
Priority to DE19792907379 priority patent/DE2907379A1/en
Priority to IT20543/79A priority patent/IT1113010B/en
Priority to DK82079A priority patent/DK82079A/en
Priority to NZ189769A priority patent/NZ189769A/en
Priority to ZA79906A priority patent/ZA79906B/en
Priority to SE7901706A priority patent/SE7901706L/en
Priority to CH188579A priority patent/CH637112A5/en
Priority to AU44602/79A priority patent/AU520618B2/en
Priority to GB7906963A priority patent/GB2021559B/en
Priority to CA000322406A priority patent/CA1119613A/en
Priority to GR58490A priority patent/GR66971B/el
Priority to BE0/193728A priority patent/BE874488A/en
Priority to LU80974A priority patent/LU80974A1/en
Priority to FI790656A priority patent/FI790656A/en
Priority to AT0149179A priority patent/AT365564B/en
Priority to IE556/79A priority patent/IE47930B1/en
Publication of FR2418222A2 publication Critical patent/FR2418222A2/en
Publication of FR2418222B2 publication Critical patent/FR2418222B2/fr
Application granted granted Critical
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

alpha-(2-Hydroxy-phenyl)-benzylidene-amino-alkanoic acid derivs. of formula (I) and intermediate diphenyl ketones (II) are new (where X1-4 independently=H, halo methyl, methoxy, nitro, CF3, tert-butyl or acetylamino; n is 1-10; R is hydroxy, -OM, -NH2, cycloalkylamino, phenyl-amino, benzylamino, alkylamino, dialkylamino or alkyl(benzyl)amino; M is an alkali metal and R1 is H or alkyl. (Alkyl gps. contain 1-4C atoms). The cpds. (I) where R1 is H when X1-3 independently are H, halo, methyl or methoxy and X4 is H, the cpd. (i) where R1 is H; X1, X3, X4 are H, X2 is 5-Cl n is 1 and R is OH and cpds. (II) where R1-3 are H, halo, methyl or methoxy when X4 is H are excluded from those claimed. (I) are anticonvulsants used to treat psychoses and neurological troubles such as epilepsy by oral or parenteral administration in daily doses of 100-1500mg. The activity of (I) as an antagonist to bicuculline induced mortality in mice show AD50 (active dose) of 20-80 mg/kg. In acute toxicity tests in mice the i.p. LD50 was 700-1000mg/kg.
FR7805578A 1975-08-01 1978-02-27 Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy Granted FR2418222A2 (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
FR7805578A FR2418222A2 (en) 1975-08-01 1978-02-27 Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy
IT20543/79A IT1113010B (en) 1978-02-27 1979-02-26 BENZYLIDENE DERIVATIVES
ZA79906A ZA79906B (en) 1978-02-27 1979-02-26 Benzylidine derivates
AU44602/79A AU520618B2 (en) 1978-02-27 1979-02-26 Benzylidene derivatives
NO790646A NO790646L (en) 1978-02-27 1979-02-26 PROCEDURE FOR THE PREPARATION OF BENZYLIDE DERIVATIVES
NL7901474A NL7901474A (en) 1978-02-27 1979-02-26 PROCESS FOR PREPARING A MEDICINAL PRODUCT ACTIVE WITH REGARD TO THE CENTRAL NERVOUS SYSTEM, THE MEDICINAL PRODUCT SO PREPARED AND PROCESS FOR PREPARING THE ACTIVE BENZYLIDE DERIVATIVE.
ES478070A ES478070A1 (en) 1978-02-27 1979-02-26 Benzylidene derivatives
IL56737A IL56737A (en) 1976-07-12 1979-02-26 Diphenylmethyleneaminoalkanoic acid derivatives,their preparation and pharmaceutical compositions containing them
DE19792907379 DE2907379A1 (en) 1978-02-27 1979-02-26 BENZYLIDENE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM
PT69288A PT69288A (en) 1978-02-27 1979-02-26 PROCESS FOR THE PREPARATION OF BENZYLIDENIC DERIVATIVES
DK82079A DK82079A (en) 1978-02-27 1979-02-26 PROCEDURE FOR THE PREPARATION OF BENZYLIDENE DERIVATIVES
NZ189769A NZ189769A (en) 1978-02-27 1979-02-26 Benzylidene derivatives and pharmaceutical compositions
JP2247179A JPS54125644A (en) 1978-02-27 1979-02-26 Benzylidene derivative and its manufacture
SE7901706A SE7901706L (en) 1978-02-27 1979-02-26 BENZYLIDE DERIVATIVES
CH188579A CH637112A5 (en) 1978-02-27 1979-02-26 BENZYLIDENIC DERIVATIVES.
GB7906963A GB2021559B (en) 1978-02-27 1979-02-27 Benzylidene derivatives
AT0149179A AT365564B (en) 1978-02-27 1979-02-27 METHOD FOR PRODUCING NEW ALPHA-PHENYLBENZYLIDENAMINOALKANIC ACID DERIVATIVES
CA000322406A CA1119613A (en) 1978-02-27 1979-02-27 Process for preparing benzylidene derivatives
GR58490A GR66971B (en) 1978-02-27 1979-02-27
BE0/193728A BE874488A (en) 1978-02-27 1979-02-27 BENZYLIDENIC DERIVATIVES
LU80974A LU80974A1 (en) 1978-02-27 1979-02-27 BENZYLIDENIC DERIVATIVES
FI790656A FI790656A (en) 1978-02-27 1979-02-27 BENZYL DENDERIVAT
IE556/79A IE47930B1 (en) 1978-02-27 1979-08-08 Benzylidene derivatives

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR7524065A FR2319338A1 (en) 1975-08-01 1975-08-01 NEW A-PHENYL BENZYLIDENIC DERIVATIVES OF AMINO ACIDS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
FR7621922A FR2358887A2 (en) 1976-07-19 1976-07-19 Anticonvulsant alkanamide cpds. - with alpha-phenyl-benzylidene-amino substit.
FR7805578A FR2418222A2 (en) 1975-08-01 1978-02-27 Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy

Publications (2)

Publication Number Publication Date
FR2418222A2 true FR2418222A2 (en) 1979-09-21
FR2418222B2 FR2418222B2 (en) 1982-09-17

Family

ID=27250502

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7805578A Granted FR2418222A2 (en) 1975-08-01 1978-02-27 Alpha-phenyl 2-hydroxy-benzylidene amino-alkanoic acid derivs. - and novel di:phenyl-ketone intermediates, useful as anticonvulsants for treating epilepsy

Country Status (1)

Country Link
FR (1) FR2418222A2 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2282870A1 (en) * 1974-05-01 1976-03-26 Lawson Alexander PHARMACEUTICAL PRODUCT AND PROCESS FOR ITS MANUFACTURING
FR2358887A2 (en) * 1976-07-19 1978-02-17 Synthelabo Anticonvulsant alkanamide cpds. - with alpha-phenyl-benzylidene-amino substit.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2282870A1 (en) * 1974-05-01 1976-03-26 Lawson Alexander PHARMACEUTICAL PRODUCT AND PROCESS FOR ITS MANUFACTURING
FR2358887A2 (en) * 1976-07-19 1978-02-17 Synthelabo Anticonvulsant alkanamide cpds. - with alpha-phenyl-benzylidene-amino substit.

Also Published As

Publication number Publication date
FR2418222B2 (en) 1982-09-17

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