[go: up one dir, main page]

GB805885A - 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof - Google Patents

3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof

Info

Publication number
GB805885A
GB805885A GB19970/56A GB1997056A GB805885A GB 805885 A GB805885 A GB 805885A GB 19970/56 A GB19970/56 A GB 19970/56A GB 1997056 A GB1997056 A GB 1997056A GB 805885 A GB805885 A GB 805885A
Authority
GB
United Kingdom
Prior art keywords
tropane
phenyl
ethane
ethanol
hydrochloride
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
GB19970/56A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB805885A publication Critical patent/GB805885A/en
Expired legal-status Critical Current

Links

Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of the tropane series of the general formula <FORM:0805885/IV (b)/1> (wherein R represents a straight or branched chain alkyl radical of 1-4 carbon atoms, n is from 0 to 3, and R2 and R3 each represent alkyl of 1-6 carbon atoms, cycloalkyl of 5 or 6 carbon atoms, cycloalkyl-alkyl of 6-10 carbon atoms, 2-pyridyl, or phenyl which may be substituted by an alkyl or alkoxy group of 1-4 carbon atoms) and their acid addition and quaternary ammonium salts, and the preparation thereof from tertiary alcohols of the general formula <FORM:0805885/IV (b)/2> by (a) reduction with phosphorus and hydriodic acid, or (b) dehydration by the process of Specification 805,884, followed by hydrogenation of the resulting products. In examples: (1) 3-benzhydrylidenetropane is hydrogenated in ethanol in the presence of "Raney" nickel (the word "Raney" is a Registered Trade Mark) to produce 3-benzhydryltropane, which is converted to its hydrochloride, methobromide and etho-ethylsulphate; similarly prepared are (2) 1 : 1-diphenyl-2-(3-tropane) ethane (and its hydrochloride, methobromide, metho-p-toluene-sulphonate and maleate) from 1 : 1-diphenyl-2-(3 - tropane) - ethylene, (4) 1-ethyl-1-phenyl-2-(3-tropane)-ethane (and its hydrochloride) from the dehydration product of 1-ethyl-1-phenyl-2-(3 - tropane) - ethanol, (6) 1 - cyclohexyl - 1 - phenyl - 2 - (3 - tropane) - ethane (and its hydrochloride, citrate and butyliodide) from the dehydration product of 1-cyclohexyl-1-phenyl - 2 - (3 - tropane) - ethanol, (7) 1 - p - anisyl - 1 - phenyl - 2 - (3 - N - isopropylnortropane)-ethane (and its methobromide) from 1 - p - anisyl - 1 - phenyl - 2 - (3 - N - isopropylnortropane) - ethylene, (8) 1 : 1 - diphenyl - 3 - (3 - tropane) - propane (and its citrate and methobromide) from 1 : 1-diphenyl-3-(3-tropane)-1-propene, (10) 3-isopropyltropane from the product obtained by refluxing dimethyl - 3 - tropanecarbinol with acetic and hydrochloric acids and treating the resulting hydrochloride with sodium carbonate in ether, (11) 2 - n - hexyl - 1 - (3 - N - isopropylnortropane)-octane from the product obtained by similarly neutralizing the hydrochloride of the dehydration product of 1 : 1-di-n-hexyl-2-(3-N - isopropylnortropane) - ethanol, and (12) 1 - cyclopentyl - 1 - phenyl - 4 - (3 - tropane)-butane from the dehydration product of 1-cyclopentyl - 4 - (3 - tropane) - butanol. In further examples: (3) 1-phenyl-1-(2-pyridyl)-2-(3-tropane)-ethylene is refluxed with cyclohexene and palladium-on-charcoal catalyst to form 1 - phenyl - 1 - (2 - pyridyl) - 2 - (3 - tropane)-ethane, which is converted to its dipicrate and tartrate; (5) 1-(2-cyclohexylethyl)-1-phenyl - 2 - (3 - tropane) - ethanol is refluxed with hydriodic acid and red phosphorus in acetic acid to produce 1-(2-cyclohexylethyl)-1-phenyl - 2 - (3 - tropane) - ethane hydriodide, which is converted to the free base and the latter to its hydrochloride; (9) 1-(2-pyridyl)-1-p-tolyl-4-(3-tropane)-1-butene is reduced as in (3) to 1 - (2 - pyridyl) - 1 - p - tolyl - 4 - (3 - tropane)-butane. Additional salt-forming and and quaternizing agents are listed as in Specifications 805,883 and 805,884. The products are useful as therapeutic agents acting on the parasympathetic and central nervous systems. Ethyl b -(3-tropane)-propionate (from which the starting material of Example (8) is obtained by successive application of the processes of Specifications 805,883 and 805,884) is prepared by acid hydrolysis of the corresponding nitrile (obtained by the action of potassium cyanide on 1 - chloro - 2 - (3 - tropane) - ethane in aqueous alcohol in the presence of sodium iodide), followed by esterification with ethanol in the presence of conc. H2SO4. 1-Chloro-2-(3-tropane)-ethane is prepared by refluxing 2-(3-tropane)-ethanol with thionyl chloride in chloroform and treating the resulting hydrochloride with potassium carbonate. 2-(3-Tropane)-ethanol is prepared by reducing ethyl 3-tropaneacetate with lithium aluminium hydride in ether.
GB19970/56A 1955-07-01 1956-06-27 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof Expired GB805885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US805885XA 1955-07-01 1955-07-01

Publications (1)

Publication Number Publication Date
GB805885A true GB805885A (en) 1958-12-17

Family

ID=22158331

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19970/56A Expired GB805885A (en) 1955-07-01 1956-06-27 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof

Country Status (1)

Country Link
GB (1) GB805885A (en)

Similar Documents

Publication Publication Date Title
GB909357A (en) Naphthalene derivatives
GB805885A (en) 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof
GB800969A (en) Novel 2-hydroxy-benzo [ª‡] quinolizines, acid addition salts thereof and a process for the manufacture of same
GB501135A (en) Manufacture of piperidine compounds
US2538793A (en) Alkamine esters of cyclopentylalkylacetic acids
GB788126A (en) Quaternary salts of piperidyl esters
Blicke et al. Synthetic mydriatics. III
US2881165A (en) alpha-alpha-diphenyl-gamma-hexamethyleneiminobutyramide
US3145211A (en) Tropyl esters of alpha-cycloalkylalkanoic acids
GB752331A (en) Improvements in or relating to n, n-disubstituted piperazines and process of preparing the same
GB807835A (en) New tertiary amines and their salts and process for their preparation
Blicke et al. Antispasmodics. XVII. β-Diethylaminoethyl esters of substituted acetic and glycidic acids
DE1493961C3 (en) l-Hydroxy-2-alkylamino-l-phenyläthanderivate their acid addition salts, process for their production and pharmaceutical preparations
GB894049A (en) Method of preparing 10-(1-substituted-3-pyrrolidylmethyl) phenothiazines
Blicke et al. Antispasmodics. XX. Basic 1, 3-Dioxolanes and 1, 3-Dioxanes
Jordan et al. The Stereoisomeric α, β-Dimorpholinyl-Benzylacetophenones
US3558631A (en) Benzhydryloxycyclopropyl heterocyclic amines
GB1440380A (en) Pyrrolidine derivatives
GB765853A (en) Improvements in or relating to substituted piperidines
US2863910A (en) Basic esters of substituted beta-benzoylacrylic acids
GB921979A (en) Substituted 2:3-diphenyl-propylamines and process for their manufacture
AT265278B (en) Process for the production of new, substituted piperazines and their acid addition salts
GB552076A (en) Process for the manufacture of ª‡-(4-methyl-phenyl)-ª‰-methyl-amino-propan
NO145098B (en) ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE ISOINDOLIN DERIVATIVES
Weilmuenster et al. THE PREPARATION OF CERTAIN QUATERNARY THENYL AMMONIUM HALIDES1