GB866681A - N-substituted piperidines - Google Patents
N-substituted piperidinesInfo
- 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
- United Kingdom
- Prior art keywords
- hydrogen atom
- group
- represent
- methyl
- tetramethylpiperidine
- 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
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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
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.
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 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)
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 |
US8673352B2 (en) | 2005-04-15 | 2014-03-18 | Mcneil-Ppc, Inc. | Modified release dosage form |
US8673190B2 (en) | 2001-09-28 | 2014-03-18 | Mcneil-Ppc, Inc. | Method for manufacturing dosage forms |
-
1958
- 1958-05-22 GB GB1655158A patent/GB866681A/en not_active Expired
Cited By (11)
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 |
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 |
US8545887B2 (en) | 2001-09-28 | 2013-10-01 | 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 |
WO2006115456A1 (en) * | 2005-04-26 | 2006-11-02 | Cambrex Karlskoga Ab | Synthesis of 1-aminopiperidine |
WO2010142810A1 (en) * | 2009-06-12 | 2010-12-16 | Centre National De La Recherche Scientifique (Cnrs) | Synthesis of hydrazines from hydroxylamine-o-sulphonic acid |
FR2946651A1 (en) * | 2009-06-12 | 2010-12-17 | Centre Nat Rech Scient | SYNTHESIS OF HYDRAZINES FROM HYDROXYLAMINE-O-SULFONIC ACID. |
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