GB856587A - Substituted piperidines - Google Patents

Substituted piperidines

Info

Publication number
GB856587A
GB856587A GB9664/57A GB966457A GB856587A GB 856587 A GB856587 A GB 856587A GB 9664/57 A GB9664/57 A GB 9664/57A GB 966457 A GB966457 A GB 966457A GB 856587 A GB856587 A GB 856587A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
alkyl
sulphur
phenyl
oxygen
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
GB9664/57A
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB856587A publication Critical patent/GB856587A/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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms 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
    • C07D211/06—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
    • C07D211/08—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
    • C07D211/34—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 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
    • C07D211/04—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0856587/IV(b)/1> (wherein Ar is phenyl or naphthyl which may bear substituents unreactive to lithuim or magnesium under the conditions of forming the corresponding aryl-lithuim or aryl magnesium halide, Z is H or a carboxylic acyl radical having from 2 to 7 carbon atoms, R is an alkyl radical having at most 6 carbon atoms, n is zero or an integer from 1 to 8, X is a divalent aliphatic hydrocarbon radical having 2 to 6 carbon atoms and having its free valencies on different carbon atoms, A is oxygen or sulphur or a direct link between X and Ar1, X being saturated when A is oxygen or p sulphur, and Ar1 is phenyl which may be substituted) and non-toxic acid-addition salts thereof; and their preparation by reacting an appropriate N-(X-A-Ar1)-4-piperidone with an appropriate aryl lithuim or aryl magnesium halide and hydrolysing the N-(X-A-Ar1)-4-Ar-4-(O-Li or O-Mg halide)- piperidine so-obtained or acylating this metal derivative or the free hydroxy compound to form compounds of the general formula I wherein Z is hydrogen or acyl respectively. The acylation is preferably conducted with an acylanhydride, suitable acylating groups being alkanoyl, alkenoyl, alkoxyalkanoyl, carboxy-alkanoyl, benzoyl and furoyl. Preferred substituents for the radicals Ar and Ar1 are alkyl or alkoxy groups containing at most 6 carbon atoms. Examples are given and a list of saltforming organic and inorganic acids is provided. N-(X-A-Ar1)-4-piperidones bearing no alkyl substituents in the piperidine ring are prepared by reacting Ar1-A-X-NH2 with at least 2 molar equivalents of an alkyl acrylate to yield an N:N-bis-(carbalkoxyethyl)-N-(X-A-Ar1)-amine, heating this with a strong basic condensing agent in an inert solvent to form an N-(X-A-Ar1)-3-carbalkoxy -4-piperidone, and hydrolysing and decarboxylating this by refluxing with aqueous acid. Replacement of the alkyl acrylate by other alkyl 2-alkkenoates results in the formation of products containing one of more alkyl substituents in the piperidine ring via the corresponding intermediates. Specification 501,135 is referred to.ALSO:Pharmaceutical compositions contain as essential active ingredient compounds of the formula: <FORM:0856587/VI/1> (wherein Ar is phenyl or naphthyl which may be substituted, Z is H or a carboxylic acyl radical having from 2 to 7 carbon atoms, R is an alkyl radical having at most 6 carbon atoms, n is zero or an integer from 1 to 8, X is a divalent aliphatic hydrocarbon radical having 2 to 6 carbon atoms and having its free valencies on different carbon atoms, A is oxygen or sulphur or a direct link between X and Ar1, X being saturated when A is oxygen or sulphur, and Ar1 is phenyl which may be substituted) or non-toxic acid-addition salts thereof. The compositions may be in liquid or solid form, such as aqueous or aqueous-ethanolic solutions or tablets, powders or capsules, Specification 501,135 is referred to.
GB9664/57A 1956-04-02 1957-03-25 Substituted piperidines Expired GB856587A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US856587XA 1956-04-02 1956-04-02

Publications (1)

Publication Number Publication Date
GB856587A true GB856587A (en) 1960-12-21

Family

ID=22193104

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9664/57A Expired GB856587A (en) 1956-04-02 1957-03-25 Substituted piperidines

Country Status (1)

Country Link
GB (1) GB856587A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027037A1 (en) * 1968-12-24 1970-09-25 Hoffmann La Roche
FR2156470A2 (en) * 1971-10-21 1973-06-01 Synthelabo 1-(3,3-diphenyl-1-propyl)-4-aryl-piperidines - as analgesics spasmolytic and anti-tussive agents
JPS4985074A (en) * 1972-12-22 1974-08-15
JPS5544068B1 (en) * 1971-04-15 1980-11-10

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027037A1 (en) * 1968-12-24 1970-09-25 Hoffmann La Roche
JPS5544068B1 (en) * 1971-04-15 1980-11-10
FR2156470A2 (en) * 1971-10-21 1973-06-01 Synthelabo 1-(3,3-diphenyl-1-propyl)-4-aryl-piperidines - as analgesics spasmolytic and anti-tussive agents
JPS4985074A (en) * 1972-12-22 1974-08-15

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