GB866681A - N-substituted piperidines - Google Patents

N-substituted piperidines

Info

Publication number
GB866681A
GB866681A GB1655158A GB1655158A GB866681A GB 866681 A GB866681 A GB 866681A GB 1655158 A GB1655158 A GB 1655158A GB 1655158 A GB1655158 A GB 1655158A GB 866681 A GB866681 A GB 866681A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
hydrogen
atom
group
represents
represent
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
GB1655158A
Inventor
Leslie Bretherick
William Robert Wragg
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.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/22Heterocyclic 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 hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28Nitrogen atoms
    • C07D295/30Nitrogen atoms non-acylated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/98Nitrogen atom

Abstract

The invention comprises compounds of the general formula: <FORM:0866681/IV (b)/1> and their acid addition salts wherein R1 represents a hydrogen atom or a methyl or ethyl group, and R11 represents a hydrogen atom or R1 and R11 together represent a methylene, ethylidene or allylidene group, R2 represents a hydrogen atom or a methyl group, R41 represents a hydrogen atom or a C1-3 alkyl group and R3 and R4 each represent a hydrogen atom or together represent a single bond and the preparation thereof, wherein R1 and R11 represent hydrogen atoms, by reducing a compound of the general formula: <FORM:0866681/IV (b)/2> or by reacting a compound of the general formula: <FORM:0866681/IV (b)/3> with hydroxylamine-O-sulphonic acid; wherein R1 and R1 together represent a methylene, ethylidene or allylidene group, by reacting a compound of (I) wherein R1 and R11 both represent hydrogen atoms with an aldehyde R5CHO wherein R5 represents a hydrogen atom or a methyl or a vinyl group, or a derivative thereof such as an acetal, thioacetal, diacyl derivative or a bisulphite addition compound; and wherein R1 represents a methyl or ethyl group and R11 represents a hydrogen atom, by alkylating a compound (I) where in R1 and R11 are hydrogen atoms or by reducing a compound of the general formula: <FORM:0866681/IV (b)/4> The first Provisional Specification relates to compounds (I) wherein R1 and R11 additionally both represent lower alkyl groups and to quaternary ammonium salts of the bases in general. 1-Nitroso-2,2,6,6- tetramethyl-1,2,5,6- tetrahydropyridine is prepared from sodium nitrite and 2,2,6,6-tetramethyl-1,2,5,6-tetrahydropyridine. Similarly are prepared 1-nitroso-2,2,6-trimethylpiperidine and 1-nitroso-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyridine. 2,2,4,5,6- Pentamethyl-1,2,5,6- tetrahydropyridine hydriodide is prepared by reacting methyl magnesium iodide with 2,2,6,6-tetramethylpiperid-4-one and heating the hydriodide of the 2,2,4,6,6-pentamethylpiperidin-4-ol so formed. 1-Formylamino-2,2,6,6- tetramethylpiperidine is prepared from formic acid and 1-amino-2,2, 6,6-tetramethylpiperidine.ALSO:Pharmaceutical compositions comprise a pharmaceutical carrier together with compounds of the general formula <FORM:0866681/VI/1> or their acid addition salts wherein R1 represents a hydrogen atom, a methyl or an ethyl group and R11 represents a hydrogen atom or R1 and R11 together represent a methylene, ethylidene or allylidene group, R2 represents a hydrogen atom or a methyl group, R14 represents a hydrogen atom or a C1-3 alkyl group and R3 and R4 represent a hydrogen atom or together represent a single bond. Acid addition salts include hydrohalides, phosphates, nitrates, sulphates, maleates, fumarates, citrates, tartrates, methanesulphonates and ethane disulphonates. Compositions are suitable for oral or parenteral administration and are in the form of tablets, pills, dispersable powders, granules, emulsions, suspensions, syrups and elixirs. Examples are given of tablets containing 1 - amino - 2,2,6,6 - tetramethylpiperidine hydrogen tartrate and 1-methyleneamino-2,2,6,6 - tetramethylpiperidine hydrogen tartrate and injectable aqueous solutions containing 1 - amino - 2,2,6,6 - tetramethylpiperidine and 1 - methylamino - 2,2,6,6 - tetramethylpiperidine hydrochlorides.
GB1655158A 1958-05-22 1958-05-22 N-substituted piperidines Expired GB866681A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1655158A GB866681A (en) 1958-05-22 1958-05-22 N-substituted piperidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1655158A GB866681A (en) 1958-05-22 1958-05-22 N-substituted piperidines

Publications (1)

Publication Number Publication Date
GB866681A true true GB866681A (en) 1961-04-26

Family

ID=10079357

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1655158A Expired GB866681A (en) 1958-05-22 1958-05-22 N-substituted piperidines

Country Status (1)

Country Link
GB (1) GB866681A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003028703A2 (en) * 2001-09-28 2003-04-10 Mcneil-Ppc, Inc. Immediate release tablet
WO2006115456A1 (en) * 2005-04-26 2006-11-02 Cambrex Karlskoga Ab Synthesis of 1-aminopiperidine
US7838026B2 (en) 2001-09-28 2010-11-23 Mcneil-Ppc, Inc. Burst-release polymer composition and dosage forms comprising the same
WO2010142810A1 (en) * 2009-06-12 2010-12-16 Centre National De La Recherche Scientifique (Cnrs) Synthesis of hydrazines from hydroxylamine-o-sulphonic acid
US7968120B2 (en) 2001-09-28 2011-06-28 Mcneil-Ppc, Inc. Modified release dosage forms
US8673190B2 (en) 2001-09-28 2014-03-18 Mcneil-Ppc, Inc. Method for manufacturing dosage forms
US8673352B2 (en) 2005-04-15 2014-03-18 Mcneil-Ppc, Inc. Modified release dosage form

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003028703A2 (en) * 2001-09-28 2003-04-10 Mcneil-Ppc, Inc. Immediate release tablet
WO2003028703A3 (en) * 2001-09-28 2003-07-10 Mcneil Ppc Inc Immediate release tablet
US8545887B2 (en) 2001-09-28 2013-10-01 Mcneil-Ppc, Inc. Modified release dosage forms
US7838026B2 (en) 2001-09-28 2010-11-23 Mcneil-Ppc, Inc. Burst-release polymer composition and dosage forms comprising the same
US7968120B2 (en) 2001-09-28 2011-06-28 Mcneil-Ppc, Inc. Modified release dosage forms
US7972624B2 (en) 2001-09-28 2011-07-05 Shun-Por Li Method of manufacturing modified release dosage forms
US8673190B2 (en) 2001-09-28 2014-03-18 Mcneil-Ppc, Inc. Method for manufacturing dosage forms
US8673352B2 (en) 2005-04-15 2014-03-18 Mcneil-Ppc, Inc. Modified release dosage form
WO2006115456A1 (en) * 2005-04-26 2006-11-02 Cambrex Karlskoga Ab Synthesis of 1-aminopiperidine
FR2946651A1 (en) * 2009-06-12 2010-12-17 Centre Nat Rech Scient Synthesis of hydrazines from sulfonic hydroxylamine-o-.
WO2010142810A1 (en) * 2009-06-12 2010-12-16 Centre National De La Recherche Scientifique (Cnrs) Synthesis of hydrazines from hydroxylamine-o-sulphonic acid

Similar Documents

Publication Publication Date Title
US3389144A (en) 5-pyridyl-2, 3, 4, 5-tetrahydrobenzothiepin-5-ols
US3399192A (en) 1-oxa-2-oxo 3, 8-diaza spiro (4, 5) decanes
US3452040A (en) 5,5-disubstituted hydantoins
Isbell et al. Mutarotation, Hydrolysis, and Rearrangement Reactions of Glycosylamines1
Lown et al. Acetylenic esters. II. Further addition reactions with sulfur-and nitrogen-containing compounds
US3161653A (en) 2-[(2&#39;-methyl-benzo-thienyl-3&#39;)-methyl]-delta2-imidazoline and its pharmaceutically aceptable acid addition salts
US3852279A (en) 7-substituted -3,3a,4,5,6,7-hexahydro-3-substituted-2h- pyrazolo (4,3-c)pyridines
US3883651A (en) Pharmaceutical compositions containing a 2-(aminoalkylamino)-4-amino-thieno{8 3,2-d{9 pyrimidine and method of use
US3354178A (en) Nu-(4-amino-2-butynyl)-nu-alkylcarboxamides
US4141883A (en) Stabilization of synthetic polymers by penta-or-hexa-substituted 4-piperidinol derivatives
US3282947A (en) Unsymmetrically substituted 3, 9-diazaspiro(5, 5)undecane compounds
US3491093A (en) Derivatives of 5 aminomethyl-4,5,6,7-tetrahydro-4-oxoindoles
US4797406A (en) Amides and esters containing bridged piperidines and use as serotonin M antagonists
US4466972A (en) Benzoxadiazoles and benzothiadiazoles, their preparation and pharmaceutical compositions containing them
US2928829A (en) Alkyleneimino-lower alkyl-guanidines
US3341538A (en) Certain 2, 6-methano-3-benzazocines
US3050525A (en) Certain derivatives of s-triazolo [4, 3-a]-pyridine
US3476762A (en) 4&#39; - dimethylamino - 4 - (4 - hydroxy-4-phenyl piperidino)butyrophenones and 4 - (4-phenyl-4-hydroxy - piperidino)-1,1-ethylenedioxy - 1 - (4 - dimethylaminophenyl)butanes
WO1991013071A1 (en) Novel trisubstituted pyrrols, process for their production and medicaments containing these compounds
EP0244018A1 (en) Amino-thiazole and oxazole derivatives
US3804898A (en) Novel benzcyclobutene derivatives
US3822258A (en) 4-hydroxy-3-(3-isoxazolylcarbamoyl)-2h-1,2-benzothiazine 1,1-dioxides and process for their production
US3514462A (en) 1 and 2 ethoxy 3,4,5,10 - tetrahydroazepino(3,4-b) and (2,3-b)indoles and corresponding amino derivatives thereof
US3869463A (en) N-phenyl derivatives of alkanoylamido piperidines
US3905970A (en) 1,4-Dihydropyridine carboxylic acid esters