FR2378520A1 - N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics - Google Patents

N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics

Info

Publication number
FR2378520A1
FR2378520A1 FR7639034A FR7639034A FR2378520A1 FR 2378520 A1 FR2378520 A1 FR 2378520A1 FR 7639034 A FR7639034 A FR 7639034A FR 7639034 A FR7639034 A FR 7639034A FR 2378520 A1 FR2378520 A1 FR 2378520A1
Authority
FR
France
Prior art keywords
alkyl
benzamide
cpds
esp
pyrrolidinyl
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
FR7639034A
Other languages
French (fr)
Other versions
FR2378520B1 (en
Inventor
Jean-Pierre Kaplan
Henry Najer
Bernard Raizon
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
Application filed by Synthelabo SA filed Critical Synthelabo SA
Priority to FR7639034A priority Critical patent/FR2378520A1/en
Priority to NO774402A priority patent/NO774402L/en
Priority to GB53570/77A priority patent/GB1556566A/en
Priority to NZ186075A priority patent/NZ186075A/en
Priority to DK575877A priority patent/DK575877A/en
Priority to FI773911A priority patent/FI773911A/en
Priority to DE19772757406 priority patent/DE2757406A1/en
Priority to AU31921/77A priority patent/AU3192177A/en
Priority to IL53680A priority patent/IL53680A0/en
Priority to SE7714659A priority patent/SE7714659L/en
Priority to JP15630677A priority patent/JPS5382771A/en
Priority to ES465366A priority patent/ES465366A2/en
Priority to LU78773A priority patent/LU78773A1/en
Priority to NL7714301A priority patent/NL7714301A/en
Priority to GR55032A priority patent/GR66082B/el
Publication of FR2378520A1 publication Critical patent/FR2378520A1/en
Application granted granted Critical
Publication of FR2378520B1 publication Critical patent/FR2378520B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl 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
    • C07C45/45—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles

Landscapes

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

Abstract

N-(1-Benzyl-2-pyrrolidinyl-methyl)-2-methoxy-benzamides of formula (I) as the racemates or optical isomers and their acid addn. salts and intermediates (VI) are novel (where R1 is Cl, SO2R6 or -SO2NR7R8; R6 is 1-4C alkyl; R7 and R8 are independently H or 1-4C alkyl; R2 is H or 1-4C alkyl; R3 and R4 are independently halo, CF3, CF3O, CF3S, 1-4C alkyl or 1-4C alkoxy; R5 is H, halo, CF3, CF3O, CF3S, 1-4C alkoxy or 1-4C alkyl; and R is cyano, formyl, hydroxymethyl, aminomethyl, chloromethyl, carboxy, fluorocarbonyl, chlorocarbonyl, alkoxycarbonyl or carbamoyl. Cpds. (I) are psychotropic drugs which are administered as their methanesulphonates by oral, rectal or parenteral routes in daily doses of 5-300mg. They are used to treat psychosomatic disorders such as gastric-duodenal ulcers, migraine, vertigo, depressive and psychopathological conditions, esp. in old age. At higher dose levels they are used used for psychotic conditions because of their neuroleptic properties free of side-effects.
FR7639034A 1976-12-24 1976-12-24 N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics Granted FR2378520A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
FR7639034A FR2378520A1 (en) 1976-12-24 1976-12-24 N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics
NO774402A NO774402L (en) 1976-12-24 1977-12-21 R METHOD OF PREPARATION OF METHOXY BENZAMIDE DERIVATIVES
SE7714659A SE7714659L (en) 1976-12-24 1977-12-22 METHOXYBENZAMIDES
DK575877A DK575877A (en) 1976-12-24 1977-12-22 PROCEDURE FOR THE PREPARATION OF 2-METHOXYBENZAMIDES
FI773911A FI773911A (en) 1976-12-24 1977-12-22 METHOXIBENZAMIDE DERIVATIVES
DE19772757406 DE2757406A1 (en) 1976-12-24 1977-12-22 2-METHOXY-BENZAMIDE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM
AU31921/77A AU3192177A (en) 1976-12-24 1977-12-22 2-methoxybenzamides
IL53680A IL53680A0 (en) 1976-12-24 1977-12-22 Novel 2-methoxybenzamide derivatives their preparation and pharmaceutical compositions containing them
GB53570/77A GB1556566A (en) 1976-12-24 1977-12-22 2-methoxybenzamides
NZ186075A NZ186075A (en) 1976-12-24 1977-12-22 2-methoxybenzamide derivatives, and pharmaceutical compositions containing them
JP15630677A JPS5382771A (en) 1976-12-24 1977-12-23 Methoxybenzamide derivative
ES465366A ES465366A2 (en) 1976-12-24 1977-12-23 2-methoxybenzamides
LU78773A LU78773A1 (en) 1976-12-24 1977-12-23 METHOD FOR PREPARING METHOXY-2-BENZAMIDES
NL7714301A NL7714301A (en) 1976-12-24 1977-12-23 METHOD OF PREPARING A MEDICINAL PRODUCT, SUCH AS FORMED MEDICINAL PRODUCT.
GR55032A GR66082B (en) 1976-12-24 1977-12-27

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7639034A FR2378520A1 (en) 1976-12-24 1976-12-24 N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics

Publications (2)

Publication Number Publication Date
FR2378520A1 true FR2378520A1 (en) 1978-08-25
FR2378520B1 FR2378520B1 (en) 1979-05-11

Family

ID=9181520

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7639034A Granted FR2378520A1 (en) 1976-12-24 1976-12-24 N-1-enzyl-2-pyrrolidinyl-methyl 2-methoxy-benzamide derivs. - esp. the 5-sulphamoyl-benzamide cpds., are psychotropics and neuroleptics

Country Status (1)

Country Link
FR (1) FR2378520A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2305973A1 (en) * 1975-04-02 1976-10-29 Yamanouchi Pharma Co Ltd NEW DERIVATIVES OF BENZAMIDE

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2305973A1 (en) * 1975-04-02 1976-10-29 Yamanouchi Pharma Co Ltd NEW DERIVATIVES OF BENZAMIDE

Also Published As

Publication number Publication date
FR2378520B1 (en) 1979-05-11

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