GB952736A - Quaternary ammonium compounds and their preparation - Google Patents
Quaternary ammonium compounds and their preparationInfo
- Publication number
- GB952736A GB952736A GB2059859A GB2059859A GB952736A GB 952736 A GB952736 A GB 952736A GB 2059859 A GB2059859 A GB 2059859A GB 2059859 A GB2059859 A GB 2059859A GB 952736 A GB952736 A GB 952736A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydrogen
- ethyl
- methyl
- prepared
- 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
- C07D295/04—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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a quaternary ammonium compound containing a cation of the formula: <FORM:0952736/C2/1> (wherein Q is an acetyl, phenacetyl, propionyl, butyryl, methoxycarbonyl, isopropoxycarbonyl, acetamido or propionamido group when E is an ethylene group, L and M are halogen atoms or methyl, ethyl or methoxy groups, or one of them may be hydrogen, and Z is hydrogen; or Q is an ethoxycarbonyl group when E is an ethylene group, L and M are hydrogen or halogen atoms or methyl, ethyl or methoxy groups, and Z is a hydrogen atom; or Q is a benzoyl group which may be mono-halogen, -C1-4 alkyl, -C1-4 alkoxy, -nitro or -amino substituted when E is ethylene, trimethylene or 1- or 2-methyl-ethylene, L and M are hydrogen or halogen atoms or methyl, ethyl or methoxy groups, and Z is hydrogen or hydroxy; and R7 is methyl, ethyl or 2-hydroxyethyl); and the preparation thereof by reacting a tertiary amine (which may be formed in situ) with a reactive derivative of the group it is desired to introduce. The amino-benzoyl compounds are prepared by reduction of the nitro-benzoyl compounds. Amions may be exchanged by metathesis. Reactive esters referred to are halides and hydrocarbon sulphonates. The compounds may also be prepared by quaternization through intramolecular rearrangement of a tertiary phenoxyalkylamine R7R10N(CH2)4 X wherein R10 is the required phenoxyalkyl group and X is a reactive group, either by heating the base alone or in a solvent. Examples are given. 1 - (4 - Benzoyl -2, 6- dimethylphenoxy) -2- pyrrolidinoethane is prepared from 1-(4-benzoyl-2, 6-dimethylphenoxy) - 2 - bromoethane and pyrrolidine. 1-(4-butyryl -2, 6-dimethylphenoxy) -2- pyrrolidinoethane is prepared by reacting 4-hydroxy -3, 5-dimethyl-butyrophenone with ethylene dibromide to give 1-bromo-2(4-butyryl -2, 6-dimethylphonexy)-ethane and reacting this with pyrrolidine. By similar methods are prepared 1 - (2, 6 - dimethyl -4- propionylphenoxy) -2- pyrrolidinoethane and 1- (2-bromo -4- ethoxycarbonylphenoxy) -2- pyrrolidionoethane The compounds of the invention, which are stated to depress the peripheral sympathetic, nervous system, may be formulated as pharmaceutical preparations with suitable carrirs. These may take any of the forms described in Specification 919,126. Tablets and injection solutions containing N-[2-(2-bromo -4- ethoxycarbonylphenoxy)-ethyl] -N- ethylpyrrolidinium iodide are described. The Provisional Specification describes compounds containing a cation as decrbied in the first Provisional Specification of the parent Specification except that R1 and R2 form, with the nitrogen atom, a pyrrolidine ring. Additional methods of preparation are also described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2059859A GB952736A (en) | 1959-06-16 | 1959-06-16 | Quaternary ammonium compounds and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2059859A GB952736A (en) | 1959-06-16 | 1959-06-16 | Quaternary ammonium compounds and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB952736A true GB952736A (en) | 1964-03-18 |
Family
ID=10148581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2059859A Expired GB952736A (en) | 1959-06-16 | 1959-06-16 | Quaternary ammonium compounds and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB952736A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017209A1 (en) * | 1979-04-04 | 1980-10-15 | BASF Aktiengesellschaft | Substituted alkylammonium salts, their preparation and use in plant growth regulation |
| EP2850113B1 (en) * | 2012-05-16 | 2017-08-09 | Coloplast A/S | Novel polymeric photoinitiators and photoinitiator monomers |
-
1959
- 1959-06-16 GB GB2059859A patent/GB952736A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017209A1 (en) * | 1979-04-04 | 1980-10-15 | BASF Aktiengesellschaft | Substituted alkylammonium salts, their preparation and use in plant growth regulation |
| US4350518A (en) | 1979-04-04 | 1982-09-21 | Basf Aktiengesellschaft | Plant growth regulating substituted alkylammonium salts |
| EP2850113B1 (en) * | 2012-05-16 | 2017-08-09 | Coloplast A/S | Novel polymeric photoinitiators and photoinitiator monomers |
| US10040893B2 (en) | 2012-05-16 | 2018-08-07 | Coloplast A/S | Polymeric photoinitiators and photoinitiator monomers |
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