ES259622A1 - Improvements in or relating to basic esters of etherified benzilic acids - Google Patents

Improvements in or relating to basic esters of etherified benzilic acids

Info

Publication number
ES259622A1
ES259622A1 ES0259622A ES259622A ES259622A1 ES 259622 A1 ES259622 A1 ES 259622A1 ES 0259622 A ES0259622 A ES 0259622A ES 259622 A ES259622 A ES 259622A ES 259622 A1 ES259622 A1 ES 259622A1
Authority
ES
Spain
Prior art keywords
prepared
general formula
piperidines
ethyl
specifications
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
ES0259622A
Other languages
Spanish (es)
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.)
Beecham Research Laboratories Ltd
Original Assignee
Beecham Research 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 Beecham Research Laboratories Ltd filed Critical Beecham Research Laboratories Ltd
Publication of ES259622A1 publication Critical patent/ES259622A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Abstract

The invention comprises compounds of the general formula <FORM:0886437/IV (b)/1> wherein X is the group <FORM:0886437/IV (b)/2> where R and R1 are the same or different C1-4 alkyl groups and n is zero or one and their acid addition salts and the preparation thereof by reacting an ester of the general formula <FORM:0886437/IV (b)/3> wherein R2 is a C1-4 alkyl group, with an alcohol of the general formula HO(CH2)nX in the presence of a strong base as an esterification catalyst. 1-Ethyl-4-hydroxypiperidine and its picrate is prepared by reduction of 1-ethyl-4-piperidone, (characterised by the preparation of its 2 : 4-dinitrophenylhydrazone). 1-Methyl-2-, -3-, and -4-hydroxymethyl-piperidines are prepared by methylation of the corresponding 1-unsubstituted piperidines in turn prepared by reduction of the ethyl esters of the corresponding carboxylic acids. 1-Methyl-2- and -3-hydroxymethyl piperidines are characterised by the preparation of their methiodides and acetate methiodides and 1-methyl-4-hydroxymethylpiperidine by its hydrochloride. 1-Ethyl-2-, and -3- and -4-hydroxypiperidines characterised by the formation of their benzoate hydrochlorides and D-tartrates, are prepared by reduction of the corresponding 1-acetyl-ethoxycarbonylpiperidines in turn prepared by acetylation of the ethoxycarbonyl piperidines. Specifications 799,030, 820,503, 861,377, 886,436 and U.S.A. Specifications 2,657,211 and 2,830,997 are referred to.ALSO:Pharmaceutical compositions having antitussive properties comprise compounds of the general formula <FORM:0886437/VI/1> where X is the group <FORM:0886437/VI/2> , <FORM:0886437/VI/3> , <FORM:0886437/VI/4> or <FORM:0886437/VI/5> , where R and R1 are the same or different and are C1-4 alkyl groups and n is zero or one, or their acid addition salts, and a pharmaceutical carrier. The compositions may be in the form of a linctus. Specified salts are hydrohalides, sulphates, citrates and tartrates. Specifications 799,030, 820,503, 861,377 and 886,436 are referred to.
ES0259622A 1959-07-15 1960-07-13 Improvements in or relating to basic esters of etherified benzilic acids Expired ES259622A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2433659A GB886437A (en) 1959-07-15 1959-07-15 Improvements in or relating to basic esters of etherified benzilic acids

Publications (1)

Publication Number Publication Date
ES259622A1 true ES259622A1 (en) 1961-02-01

Family

ID=10210110

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0259622A Expired ES259622A1 (en) 1959-07-15 1960-07-13 Improvements in or relating to basic esters of etherified benzilic acids

Country Status (3)

Country Link
CH (1) CH394198A (en)
ES (1) ES259622A1 (en)
GB (1) GB886437A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT287711B (en) * 1968-06-25 1971-02-10 Boehringer Sohn Ingelheim Process for the preparation of new 1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl-carboxylic acid esters and their acid addition salts and quaternary ammonium compounds
FR2481702A1 (en) * 1980-04-30 1981-11-06 Anvar CYCLIC AMINOUS SUBSTITUTED PHENOXYACETATES, PROCESS FOR OBTAINING THE SAME, APPLICATIONS AS MEDICAMENTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

Also Published As

Publication number Publication date
GB886437A (en) 1962-01-10
CH394198A (en) 1965-06-30

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