GB933686A - New guanidine derivatives - Google Patents

New guanidine derivatives

Info

Publication number
GB933686A
GB933686A GB46107/61A GB4610761A GB933686A GB 933686 A GB933686 A GB 933686A GB 46107/61 A GB46107/61 A GB 46107/61A GB 4610761 A GB4610761 A GB 4610761A GB 933686 A GB933686 A GB 933686A
Authority
GB
United Kingdom
Prior art keywords
prepared
reducing
lithium aluminium
aluminium hydride
dimethylpyrrolidine
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
GB46107/61A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB933686A publication Critical patent/GB933686A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0933686/IV(a)/1> (wherein R1 and R2, which may be the same or different, are C1-4 alkyl radicals and R3 and R4, which may be the same or different, are hydrogen atoms or C1-4 alkyl radicals, with the proviso that at least one of R1, R2, R3 and R4 is a methyl radical), the pharmaceutically-acceptable, non-toxic, acid addition salts thereof, and their preparation by reacting an N-(2-aminoethyl)-pyrrolidine of the general formula <FORM:0933686/IV(a)/2> with an alkylisothiourea salt containing 1-4 carbon atoms in the alkyl radical, cyanamide, an alkali metal salt of cyanamide, guanidine or an acid addition salt of guanidine. N-(2-guanidinoethyl)-3,3-dimethylpyrrolidine and its monosulphate are also prepared from N-(2-aminoethyl)-3,3-dimethylpyrrolidine and 1-guanidino-3,4-dimethylpyrazole nitrate. The N-(2-aminoethyl)-pyrrolidine starting materials are prepared by condensing the parent pyrrolidine with glycollonitrile and reducing the resulting N-cyanomethyl derivative with lithium aluminium. 3,3,4,4-Tetramethylpyrrolidine is prepared by catalytic hydrogenation of tetramethylsuccinic acid dinitrile or by reduction of tetramethylsuccinimide with lithium aluminium hydride. 3,3-Dimethylpyrrolidine is prepared by catalytically reducing a ,a -dimethylsuccinimide to 3,3-dimethylpyrrolidone, and reducing the latter with lithium aluminium hydride. 3,3,4-Trimethylpyrrolidine is prepared by reducing 3,3,4-trimethylsuccinimide to 3,3,4-trimethylpyrrolidone, and reducing the latter, successively, with lithium aluminium hydride. 3-Methyl-3-ethylpyrrolidine is prepared by reducing a -methyl-a -ethylsuccinimide with lithium aluminium hydride. Specification 883,282 is referred to.
GB46107/61A 1960-12-24 1961-12-22 New guanidine derivatives Expired GB933686A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF32847A DE1174781B (en) 1960-12-24 1960-12-24 Process for the preparation of salts of 1- (guanidinoalkyl) pyrrolidines

Publications (1)

Publication Number Publication Date
GB933686A true GB933686A (en) 1963-08-08

Family

ID=7094822

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46107/61A Expired GB933686A (en) 1960-12-24 1961-12-22 New guanidine derivatives

Country Status (5)

Country Link
BE (1) BE611886A (en)
DE (1) DE1174781B (en)
FR (3) FR1506253A (en)
GB (1) GB933686A (en)
SE (1) SE303498B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105859604A (en) * 2016-04-14 2016-08-17 梯尔希（南京）药物研发有限公司 Preparation method of deuterated ethosuximide-d5

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3479346A (en) * 1961-08-08 1969-11-18 Sterling Drug Inc N-acyl-n- (and n,n-bis-) ((1-piperidyl)-lower-alkyl)amines
IE52663B1 (en) * 1980-04-02 1988-01-20 Warner Lambert Co Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids
US4350704A (en) * 1980-10-06 1982-09-21 Warner-Lambert Company Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR346879A (en) * 1903-10-10 1905-02-13 Alba Thompson Kingsley Hasp lock system

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105859604A (en) * 2016-04-14 2016-08-17 梯尔希（南京）药物研发有限公司 Preparation method of deuterated ethosuximide-d5

Also Published As

Publication number Publication date
FR1506253A (en) 1967-12-22
SE303498B (en) 1968-09-02
FR2124M (en) 1963-11-04
FR2123M (en) 1963-11-04
DE1174781B (en) 1964-07-30
BE611886A (en) 1962-06-22

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