FR2395261A2 - Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals - Google Patents

Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals

Info

Publication number
FR2395261A2
FR2395261A2 FR7719391A FR7719391A FR2395261A2 FR 2395261 A2 FR2395261 A2 FR 2395261A2 FR 7719391 A FR7719391 A FR 7719391A FR 7719391 A FR7719391 A FR 7719391A FR 2395261 A2 FR2395261 A2 FR 2395261A2
Authority
FR
France
Prior art keywords
pyrrolidine
methyl
intermediates
optically active
derivs
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
FR7719391A
Other languages
French (fr)
Other versions
FR2395261B2 (en
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 FR7719391A priority Critical patent/FR2395261A2/en
Priority to IL52645A priority patent/IL52645A/en
Priority to DE2735036A priority patent/DE2735036C2/en
Priority to GR54101A priority patent/GR63594B/en
Priority to NZ184832A priority patent/NZ184832A/en
Priority to NL7708571A priority patent/NL7708571A/en
Priority to DK350377A priority patent/DK350377A/en
Priority to SE7708902A priority patent/SE7708902L/en
Priority to PT66894A priority patent/PT66894B/en
Priority to LU77917A priority patent/LU77917A1/xx
Priority to IT26497/77A priority patent/IT1085696B/en
Priority to AU27641/77A priority patent/AU510454B2/en
Priority to GB32790/77A priority patent/GB1555890A/en
Priority to JP9404477A priority patent/JPS5325563A/en
Priority to CA284,104A priority patent/CA1083586A/en
Priority to IE1633/77A priority patent/IE45544B1/en
Priority to ES461342A priority patent/ES461342A1/en
Priority to CH959477A priority patent/CH624933A5/fr
Priority to FI772363A priority patent/FI772363A/fi
Priority to NO772745A priority patent/NO772745L/en
Priority to AT0577377A priority patent/AT364818B/en
Publication of FR2395261A2 publication Critical patent/FR2395261A2/en
Application granted granted Critical
Publication of FR2395261B2 publication Critical patent/FR2395261B2/fr
Priority to AT281580A priority patent/AT364819B/en
Priority to SE8009074A priority patent/SE8009074L/en
Priority to CH4181A priority patent/CH626341A5/en
Priority to NO812871A priority patent/NO812871L/en
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
    • C07D207/18—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
    • 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
    • C07D207/04—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

Abstract

Optically active pyrrolidines of formulae (Ia and (Ib) are new. In (I) R is CHR1; R1 = H or 1-4C alkyl. R2,R3 and R4 = H,M halo (esp. Cl or F), CF3, CF3O, CF3S, or 1-4C alkyl or alkoxy. A = 1-4C opt. branched alkylene. m = 2-5. They are prepd. e.g. from proline by esterification reaction with NH3; N-acylation then redn. of the CO gps. (Ia) and (Ib) are intermediates for the therapeutically active cpds. of formula (where X = Cl, SO2R5 or SO2NR6R7 R5 = 1-4C alkyl). In an example (S) (-)-1-cyclopropylmethyl-2-aminomethylpyrrolidine was prepd. in 4 stages from L-proline.
FR7719391A 1976-08-05 1977-06-24 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals Granted FR2395261A2 (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
FR7719391A FR2395261A2 (en) 1977-06-24 1977-06-24 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals
IL52645A IL52645A (en) 1976-08-05 1977-08-02 Optically active 1 substituted 2 aminomethyl pyrrolidines stereospecifics synthesis thereof and process for the preparation of optically active 2 methoxy n pyrrolidylmethyl benzamides
GR54101A GR63594B (en) 1976-08-05 1977-08-03 Method for pyrrolidines composition of specific stereoisomeusm arrangement
NZ184832A NZ184832A (en) 1976-08-05 1977-08-03 Optically active n-substituted pyrrolidines
NL7708571A NL7708571A (en) 1976-08-05 1977-08-03 METHOD FOR THE STEREOSPECIFIC PREPARATION OF OPTICALLY ACTIVE PYRROLIDINE COMPOUNDS.
DE2735036A DE2735036C2 (en) 1976-08-05 1977-08-03 Process for the production of optically active, N-substituted pyrrolidines
CH959477A CH624933A5 (en) 1976-08-05 1977-08-04
PT66894A PT66894B (en) 1976-08-05 1977-08-04 PROCESS FOR STEREOSPECIFIC SYNTHESIS OF N-SUBSTITUTED PYRROLIDINES
LU77917A LU77917A1 (en) 1976-08-05 1977-08-04
IT26497/77A IT1085696B (en) 1976-08-05 1977-08-04 STEREOSPECIFIC SUMMARY OF N-SUBSTITUTED PYROLIDINS
AU27641/77A AU510454B2 (en) 1976-08-05 1977-08-04 N-substituted pyrrolidines
GB32790/77A GB1555890A (en) 1976-08-05 1977-08-04 Optically active n substituted pyrrolidines
DK350377A DK350377A (en) 1976-08-05 1977-08-04 PROCEDURE FOR STEREOSPECIFIC PREPARATION OF OPTICALLY ACTIVE N-SUBSTITUTED PYRROLIDINES
CA284,104A CA1083586A (en) 1976-08-05 1977-08-04 Stereospecific synthesis of pyrrolidines
IE1633/77A IE45544B1 (en) 1976-08-05 1977-08-04 Aptically active n-substituted pyrrolidines
ES461342A ES461342A1 (en) 1976-08-05 1977-08-04 Optically active n substituted pyrrolidines
SE7708902A SE7708902L (en) 1976-08-05 1977-08-04 STEREOSPECIFIC SYNTHESIS OF N-SUBSTITUTED PYRROLIDINES
FI772363A FI772363A (en) 1976-08-05 1977-08-04
NO772745A NO772745L (en) 1976-08-05 1977-08-04 PROCEDURES FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES
JP9404477A JPS5325563A (en) 1976-08-05 1977-08-04 Stereospecific method of preparation of nnsubstituted pyrrolidines
AT0577377A AT364818B (en) 1976-08-05 1977-08-05 METHOD FOR THE STEREO-SPECIFIC SYNTHESIS OF OPTICALLY ACTIVE, N-SUBSTITUTED PYRROLIDINES
AT281580A AT364819B (en) 1976-08-05 1980-05-27 METHOD FOR THE STEREO-SPECIFIC SYNTHESIS OF OPTICALLY ACTIVE, N-SUBSTITUTED PYRROLIDINES
SE8009074A SE8009074L (en) 1976-08-05 1980-12-22 PROCEDURE FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES
CH4181A CH626341A5 (en) 1976-08-05 1981-01-06 Process for the stereospecific synthesis of N-substituted pyrrolidines and their use
NO812871A NO812871L (en) 1976-08-05 1981-08-25 PROCEDURE FOR PREPARATION OF N-SUBSTITUTED N-PYRROLIDINES

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7719391A FR2395261A2 (en) 1977-06-24 1977-06-24 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals

Publications (2)

Publication Number Publication Date
FR2395261A2 true FR2395261A2 (en) 1979-01-19
FR2395261B2 FR2395261B2 (en) 1980-03-07

Family

ID=9192521

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7719391A Granted FR2395261A2 (en) 1976-08-05 1977-06-24 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals

Country Status (1)

Country Link
FR (1) FR2395261A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2447911A1 (en) * 1979-02-05 1980-08-29 Synthelabo Neuroleptics used to treat psychoses and depression - are N-1-cycloalkyl-alkyl-2-pyrrolidinyl-methyl 2-methoxy 5-tri:fluoro:methyl-benzamide(s)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2294698A1 (en) * 1974-12-18 1976-07-16 Synthelabo NEW DERIVATIVES OF 2-METHOXY BENZAMIDES SUBSTITUTE, THEIR SALTS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2294698A1 (en) * 1974-12-18 1976-07-16 Synthelabo NEW DERIVATIVES OF 2-METHOXY BENZAMIDES SUBSTITUTE, THEIR SALTS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2447911A1 (en) * 1979-02-05 1980-08-29 Synthelabo Neuroleptics used to treat psychoses and depression - are N-1-cycloalkyl-alkyl-2-pyrrolidinyl-methyl 2-methoxy 5-tri:fluoro:methyl-benzamide(s)

Also Published As

Publication number Publication date
FR2395261B2 (en) 1980-03-07

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