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GB1367598A - Derivatives of delta 1-pyrroline their method of preparation and their applications - Google Patents

Derivatives of delta 1-pyrroline their method of preparation and their applications

Info

Publication number
GB1367598A
GB1367598A GB2110173A GB2110173A GB1367598A GB 1367598 A GB1367598 A GB 1367598A GB 2110173 A GB2110173 A GB 2110173A GB 2110173 A GB2110173 A GB 2110173A GB 1367598 A GB1367598 A GB 1367598A
Authority
GB
United Kingdom
Prior art keywords
prepared
phenyl
radical
atom
formula
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
GB2110173A
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.)
Laboratoires Jacques Logeais SA
Original Assignee
Laboratoires Jacques Logeais 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 Laboratoires Jacques Logeais SA filed Critical Laboratoires Jacques Logeais SA
Publication of GB1367598A publication Critical patent/GB1367598A/en
Expired 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

Landscapes

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

Abstract

1367598 4-Phenyl-5-methyl-Al-pyrroline amines LABORATOIRES JACQUES LOGEAS 3 May 1973 [3 May 1972] 21101/73 Heading C2C Novel compounds of formula in which R 1 taken separately represents a hydrogen atom, an alkyl, phenylalkyl, phenyl radical, a dialkylaminoalkyl radical or an R 4 being an alkyl radical and R 2 taken separately represents a hydrogen atom, or R 1 and R 2 taken together form with the nitrogen atom on which they are fixed a heterocyclic nucleus having from 5 to 7 ring atoms which may comprise, as a second hetero atom, an oxygen atom or a nitrogen atom, which may itself carry an alkyl radical. R 3 is in position 3 and/or 4 on the phenyl nucleus and represents hydrogen, a halogen atom, an alkyl or alkoxy radical, and n is equal to 0, 1 or 2, and their salts of addition with acids are prepared by reacting an amine R 1 R 2 NH with a pyrroline of formula Intermediates of Formula III are prepared by reacting a triethyloxonium tetrafluoroborate (C 2 H 5 ) 3 O + BF 4 <SP>-</SP> with a pyrrolidinone-2 of formula the cis isomer of which may be prepared by hydrogenation of the 5-methyl-4-phenyl-4-pyrrolin-2-one prepared by action of ammonia on 3- levulinic acid; the trans isomer may be prepared by decarboxylation of 3-carboxy-5-methyl-4- phenyl-pyrrolidin-2-one obtained by reacting ethyl malonate sodium derivative with 2-nitro- 1-phenyl-propene (prepared from benzaldehyde, nitroethane and burylamine) followed by hydrogenation and action of KOH. Pharmaceutical compositions in conventional forms for oral and parenteral administration and having antidepressant, sedative and cardiovascular activity comprise an above novel compound or salt and a therapeutically acceptable vehicle.
GB2110173A 1972-05-03 1973-05-03 Derivatives of delta 1-pyrroline their method of preparation and their applications Expired GB1367598A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7215636A FR2186236B1 (en) 1972-05-03 1972-05-03

Publications (1)

Publication Number Publication Date
GB1367598A true GB1367598A (en) 1974-09-18

Family

ID=9097884

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2110173A Expired GB1367598A (en) 1972-05-03 1973-05-03 Derivatives of delta 1-pyrroline their method of preparation and their applications

Country Status (7)

Country Link
JP (1) JPS4947366A (en)
BE (1) BE798779A (en)
CH (1) CH566981A5 (en)
DE (1) DE2321950A1 (en)
ES (1) ES414289A1 (en)
FR (1) FR2186236B1 (en)
GB (1) GB1367598A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2143234A (en) * 1983-07-06 1985-02-06 Shinogi Seiyaku Kabushiki Kais (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives
US4699918A (en) * 1983-01-28 1987-10-13 Laboratoires Jacques Logeais 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same
US5854234A (en) * 1993-10-21 1998-12-29 G. D. Searle & Co. Amidino dervatives useful as nitric oxide synthase inhibitors
US5883251A (en) * 1995-04-20 1999-03-16 G. D. Searle & Co. Azepine derivatives useful as nitric oxide synthase inhibitors
US5945408A (en) * 1996-03-06 1999-08-31 G.D. Searle & Co. Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors
US5958958A (en) * 1997-07-22 1999-09-28 G.D. Searle & Co. 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors
US6344473B1 (en) 2000-08-07 2002-02-05 G.D. Searle & Co. Imidazoles useful as nitric oxide synthase inhibitors
US6489323B1 (en) 1998-06-10 2002-12-03 G.D. Searle & Co. Heterobicyclic and tricyclic nitric oxide synthase inhibitors

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50140080A (en) * 1974-04-25 1975-11-10
DE3149776C2 (en) * 1981-12-16 1985-11-14 Daimler-Benz Ag, 7000 Stuttgart Valve guide arrangement for a poppet valve controlling the connection of a main exhaust line of an internal combustion engine with a secondary exhaust line
JPS6222757A (en) * 1985-07-22 1987-01-30 Daicel Chem Ind Ltd Substituted anilino-2-pyrroline derivative
EP0561961A1 (en) * 1990-12-13 1993-09-29 E.I. Du Pont De Nemours And Company Novel heterocyclic amidines and guanidines as plant fungicides
SE520050C2 (en) 2000-03-30 2003-05-13 Bertil Johansson Composite projectile and cartridge containing such projectile
LV14346B (en) * 2009-11-05 2011-07-20 Grindeks, A/S 4r,5s-enantiomer of 2-(5-methil-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3632604A (en) * 1970-04-09 1972-01-04 Sandoz Ag 2-substituted-4-phenyl and substituted phenyl-1-pyrrolines

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4699918A (en) * 1983-01-28 1987-10-13 Laboratoires Jacques Logeais 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same
GB2143234A (en) * 1983-07-06 1985-02-06 Shinogi Seiyaku Kabushiki Kais (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives
US6046211A (en) * 1993-10-21 2000-04-04 G.D. Searle & Co. Amidino derivatives useful as nitric oxide synthase inhibitors
US5854234A (en) * 1993-10-21 1998-12-29 G. D. Searle & Co. Amidino dervatives useful as nitric oxide synthase inhibitors
US6448286B1 (en) 1993-10-21 2002-09-10 G.D. Searle & Co. Imino pyrrolidine derivatives useful as nitric oxide synthase inhibitors
US6071906A (en) * 1993-10-21 2000-06-06 G. D. Searle & Co. Imidino piperidine derivatives useful as nitric oxide synthase inhibitors
US5883251A (en) * 1995-04-20 1999-03-16 G. D. Searle & Co. Azepine derivatives useful as nitric oxide synthase inhibitors
US6043261A (en) * 1995-04-20 2000-03-28 G. D. Searle & Co. Pyrrolodino imidines useful as nitric oxide synthase inhibitors
US5945408A (en) * 1996-03-06 1999-08-31 G.D. Searle & Co. Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors
US5981556A (en) * 1997-07-22 1999-11-09 G.D. Searle & Co. 1,3-diazolino and 1,3-diazolidino heterocycles as useful nitric oxide synthase inhibitors
US5958958A (en) * 1997-07-22 1999-09-28 G.D. Searle & Co. 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors
US6136829A (en) * 1997-07-22 2000-10-24 G.D. Searle & Co. Oxathiadiazole derivatives usful as iNOS inhibitors
US6489323B1 (en) 1998-06-10 2002-12-03 G.D. Searle & Co. Heterobicyclic and tricyclic nitric oxide synthase inhibitors
US6344473B1 (en) 2000-08-07 2002-02-05 G.D. Searle & Co. Imidazoles useful as nitric oxide synthase inhibitors

Also Published As

Publication number Publication date
JPS4947366A (en) 1974-05-08
DE2321950A1 (en) 1973-11-15
FR2186236A1 (en) 1974-01-11
ES414289A1 (en) 1976-01-16
CH566981A5 (en) 1975-09-30
FR2186236B1 (en) 1975-08-01
BE798779A (en) 1973-08-16

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Legal Events

Date Code Title Description
PS Patent sealed
435 Patent endorsed 'licences of right' on the date specified (sect. 35/1949)
PCNP Patent ceased through non-payment of renewal fee