FR2417498A1 - N-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoyl-benzamide levogyre, sa preparation et ses utilisations therapeutiques - Google Patents

N-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoyl-benzamide levogyre, sa preparation et ses utilisations therapeutiques

Info

Publication number
FR2417498A1
FR2417498A1 FR7903216A FR7903216A FR2417498A1 FR 2417498 A1 FR2417498 A1 FR 2417498A1 FR 7903216 A FR7903216 A FR 7903216A FR 7903216 A FR7903216 A FR 7903216A FR 2417498 A1 FR2417498 A1 FR 2417498A1
Authority
FR
France
Prior art keywords
ethyl
levorotatory
sulfamoyl
methoxy
pyrrolidinomethyl
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
FR7903216A
Other languages
English (en)
Other versions
FR2417498B1 (fr
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.)
Ravizza SpA
Original Assignee
Ravizza SpA
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 Ravizza SpA filed Critical Ravizza SpA
Publication of FR2417498A1 publication Critical patent/FR2417498A1/fr
Application granted granted Critical
Publication of FR2417498B1 publication Critical patent/FR2417498B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D207/10—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 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

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

Abstract

Ce composé présente les caractéristiques ci-après : p.f. = 186-188 degrés C ; Ø alpha õ D 20 degrés C = -68,5 degrés C (c = 1 % dans le diméthylformamide). On forme le N-(1-éthyl-2-pyrrolidinométhyl)-2-méthoxy-5-sulfamoyl-benzamide (de la formule ci-après) lévogyre en partant de la proline lévogyre qu'on acétyle, on réduit ensuite la N-acétyl-proline lévogyre à l'aide d'un hydrure métallique dans un solvant organique, ce qui donne le N-éthyl-2-pyrrolidinométhanol lévogyre qu'on convertit en le chlorure correspondant puis, par réaction avec l'ammoniac alcoolique, en N-éthyl-2-aminométhyl-pyrrolidine lévogyre, qu'on fait réagir avec du 2-méthoxy-5-sulfamoyl-benzoate d'éthyle. Le produit obtenu est un médicament à effet psychotrope, utile en neurologie et en psychiatrie, seul ou en association avec d'autres tranquillisants; le médicament, qui existait auparavant sous la forme racémique, est plus actif et moins toxique sous la forme lévogyre.
FR7903216A 1978-02-16 1979-02-08 N-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoyl-benzamide levogyre, sa preparation et ses utilisations therapeutiques Granted FR2417498A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT20295/78A IT1095415B (it) 1978-02-16 1978-02-16 Processo per la produzione di una benzamide otticamente attiva,benzamide otticamente attiva cosi'ottenuta e composizioni

Publications (2)

Publication Number Publication Date
FR2417498A1 true FR2417498A1 (fr) 1979-09-14
FR2417498B1 FR2417498B1 (fr) 1983-01-21

Family

ID=11165504

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7903216A Granted FR2417498A1 (fr) 1978-02-16 1979-02-08 N-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoyl-benzamide levogyre, sa preparation et ses utilisations therapeutiques

Country Status (15)

Country Link
JP (1) JPS54130562A (fr)
AT (1) AT373870B (fr)
CA (1) CA1097662A (fr)
CH (1) CH639951A5 (fr)
DE (1) DE2903891A1 (fr)
DK (1) DK152752C (fr)
EG (1) EG14440A (fr)
FR (1) FR2417498A1 (fr)
GB (1) GB2014990B (fr)
GR (1) GR78220B (fr)
IT (1) IT1095415B (fr)
MX (1) MX5632E (fr)
NL (1) NL190845C (fr)
SE (1) SE430888B (fr)
YU (1) YU41145B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1141095B (it) * 1980-11-27 1986-10-01 Ravizza Spa Processo di risoluzione della sulpiride racema
EP0088849A1 (fr) * 1982-03-11 1983-09-21 Choay S.A. Isomères lévogyres de composés benzènesulfonamides N-substitués, leur procédé de préparation et compositions pharmaceutiques les contenant
SE8602339D0 (sv) * 1986-05-22 1986-05-22 Astra Laekemedel Ab An efficient stereoconservative synthesis of 1-substituted (s)- and (r)-2-aminomethylpyrrolidines
DE4103451C2 (de) * 1991-02-02 1994-08-25 Hormosan Kwizda Gmbh Verwendungen des Wirkstoffes Sulpirid in seiner R- bzw. S-Form
WO2003055857A1 (fr) * 2001-12-28 2003-07-10 Farmaceutsko-Hemijska Industrija 'zdravlje' Procede relatif a la synthese de benzamides d'aminoalkyle heterocycliques
ITMI20051943A1 (it) * 2005-10-14 2007-04-15 Procos Spa Processo di risoluzione anantiomerica di 2-aminometil-pirrolidine 1-sostitute per ammidazione in presenza di lipasi
CL2012000874S1 (es) 2012-01-31 2013-03-22 Saverglass Botella de cuerpo paralelepipedico rectangular ahusado orientado de forma vertical, con su parte mas angosta situada en el extremo inferior, tiene todos su bordes curvos, en su extremo superior forma una superficie rectangular con sus lados convexos, la cual esta unida al cuello de botella mediante ligeras pendientes.
CN103772256B (zh) * 2012-10-24 2017-10-10 江苏天士力帝益药业有限公司 一种高纯度舒必利或其光学异构体的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU77917A1 (fr) * 1976-08-05 1977-11-14
JPS5365875A (en) * 1976-11-24 1978-06-12 Teijin Ltd Preparation of benzenesulfone amide derivs.
LU78681A1 (fr) * 1977-06-13 1978-07-11
FR2393794A2 (fr) * 1977-06-06 1979-01-05 Synthelabo Preparation de methoxy-2 benzamides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3891671A (en) * 1968-08-01 1975-06-24 Ile De France N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides
CH605793A5 (fr) * 1974-03-05 1978-10-13 Ile De France

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU77917A1 (fr) * 1976-08-05 1977-11-14
JPS5365875A (en) * 1976-11-24 1978-06-12 Teijin Ltd Preparation of benzenesulfone amide derivs.
FR2393794A2 (fr) * 1977-06-06 1979-01-05 Synthelabo Preparation de methoxy-2 benzamides
LU78681A1 (fr) * 1977-06-13 1978-07-11

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CA1978 *

Also Published As

Publication number Publication date
AT373870B (de) 1984-02-27
DE2903891A1 (de) 1979-08-23
CH639951A5 (de) 1983-12-15
GB2014990A (en) 1979-09-05
IT7820295A0 (it) 1978-02-16
MX5632E (es) 1983-11-15
FR2417498B1 (fr) 1983-01-21
ATA110179A (de) 1983-07-15
NL7901251A (nl) 1979-08-20
GB2014990B (en) 1982-06-09
DK66579A (da) 1979-08-17
YU41145B (en) 1986-12-31
DK152752C (da) 1988-09-26
DK152752B (da) 1988-05-09
SE430888B (sv) 1983-12-19
SE7901337L (sv) 1979-08-17
CA1097662A (fr) 1981-03-17
JPS54130562A (en) 1979-10-09
EG14440A (en) 1984-03-31
NL190845B (nl) 1994-04-18
GR78220B (fr) 1984-09-26
NL190845C (nl) 1994-09-16
DE2903891C2 (fr) 1992-02-06
IT1095415B (it) 1985-08-10
YU30879A (en) 1983-02-28

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