GB960895A - New piperidine derivatives and processes for preparing the same - Google Patents

New piperidine derivatives and processes for preparing the same

Info

Publication number
GB960895A
GB960895A GB3409161A GB3409161A GB960895A GB 960895 A GB960895 A GB 960895A GB 3409161 A GB3409161 A GB 3409161A GB 3409161 A GB3409161 A GB 3409161A GB 960895 A GB960895 A GB 960895A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
lower alkyl
alcohol
compounds
phenyl
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
GB3409161A
Inventor
Robert Geoffrey Willi Spickett
Charon Robin Ganellin
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
Priority to GB3409161A priority Critical patent/GB960895A/en
Publication of GB960895A publication Critical patent/GB960895A/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
    • C07D211/40—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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom 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
    • C07D211/36—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
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4

Abstract

The invention comprises compounds of the general formula: <FORM:0960895/C1/1> and their pharmaceutically acceptable acid addition salts (wherein R1 is hydrogen or a lower alkyl group; R2 is hydrogen, a lower alkyl, a phenyl or a benzyl group optionally substituted by a halogen atom; R3 is hydrogen or a lower alkyl or lower acyl group; and R4 is hydrogen or halogen or a lower alkyl, lower alkoxy or trifluoromethyl group; provided that when R1 is hydrogen or methyl and R4 is halogen or trifluoromethyl, R2 and R3 are not both hydrogen) and pharmaceutical compositions containing them. The compounds may exist in optical and configurational isomers and such forms are included within the scope of the invention. The compounds may be prepared by reacting the sodium salt of the corresponding alcohol with either an alkyl halide (R3=alkyl) or with a lower acyl halide (R3=acyl); or a 4-piperidone with an appropriate lower alkyl phenyl or benzyl magnesium halide or lithium compound to form the alcohol (R2=lower alkyl, phenyl or benzyl, R3=hydrogen) which may then be alkylated or acylated; or by reducing the corresponding 4-piperidone with an appropriate reducing agent e.g. alkali metal boro- or aluminium hydride (R2 or R3=hydrogen), and separating the racemic mixture into a - and b - isomers; or reacting an isomer of the N-unsubstituted alcohol with acetic anhydride to give the corresponding a - or b -isomer of 1-acetyl-4-acetoxypiperidine and reducing this with lithium aluminium hydride to give the desired a - or b -alcohol (R1=ethyl). Pharmaceutical compositions comprise the compounds of the invention together with a pharmaceutical carrier therefor and may be formulated as tablets, pills, sachets, packaged or encapsulated powders suitable for oral administration or in the form of a sterile solution or suspension suitable for parenteral administration. They have both stimulant and depressant activity on the central nervous system and are useful for treating psychiatric conditions.
GB3409161A 1961-09-22 1961-09-22 New piperidine derivatives and processes for preparing the same Expired GB960895A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3409161A GB960895A (en) 1961-09-22 1961-09-22 New piperidine derivatives and processes for preparing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3409161A GB960895A (en) 1961-09-22 1961-09-22 New piperidine derivatives and processes for preparing the same

Publications (1)

Publication Number Publication Date
GB960895A true GB960895A (en) 1964-06-17

Family

ID=10361269

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3409161A Expired GB960895A (en) 1961-09-22 1961-09-22 New piperidine derivatives and processes for preparing the same

Country Status (1)

Country Link
GB (1) GB960895A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248876A (en) * 1977-01-08 1981-02-03 John Wyeth & Brother Ltd. Piperidine derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248876A (en) * 1977-01-08 1981-02-03 John Wyeth & Brother Ltd. Piperidine derivatives

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