GB932487A - Piperidine derivatives - Google Patents

Piperidine derivatives

Info

Publication number
GB932487A
GB932487A GB2639161A GB2639161A GB932487A GB 932487 A GB932487 A GB 932487A GB 2639161 A GB2639161 A GB 2639161A GB 2639161 A GB2639161 A GB 2639161A GB 932487 A GB932487 A GB 932487A
Authority
GB
United Kingdom
Prior art keywords
compounds
hydrogen atom
formula
pyridine
hydrazide
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
GB2639161A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB932487A publication Critical patent/GB932487A/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
    • C07D211/04—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of the formula:-<FORM:0932487/IV(a)/1> (wherein R1 is a phenyl, benzyl, trifluoromethylphenyl, fluorophenyl or chlorophenyl radical, R2 is a hydrogen atom or a lower alkyl or lower hydroxyalkyl radical, and R3 is a hydrogen atom or an amino, lower alkyl, lower monodi- and tri-hydroxyalkyl radical) and their non-toxic acid salts, e.g. hydrochloride, hydrobromide, tartrate, maleate, methobromide, ethochloride and ethobromide. The compounds are prepared by treating an alkoxycarbonyl pyridine with a primary or secondary amine or hydrazine, catalytically hydrogenating the pyridine carboxamide or hydrazide obtained and alkylating the resulting piperidine carboxamide or hydrazide by reaction with a primary alkyl halide of the formula <FORM:0932487/IV(a)/2> itself prepared by condensation of an o -haloalkyl phenyl ketone with an aralkyl Grignard reagent R1MgX. The invention is illustrated by 22 detailed examples. The compounds display anti-inflammatory activity and other pharmacological properties.
GB2639161A 1960-07-25 1961-07-20 Piperidine derivatives Expired GB932487A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4489160A 1960-07-25 1960-07-25

Publications (1)

Publication Number Publication Date
GB932487A true GB932487A (en) 1963-07-31

Family

ID=21934891

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2639161A Expired GB932487A (en) 1960-07-25 1961-07-20 Piperidine derivatives

Country Status (1)

Country Link
GB (1) GB932487A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055997A2 (en) * 1979-03-07 1982-07-14 Imperial Chemical Industries Plc Oxirane and halohydrin compounds
EP0213080A3 (en) * 1985-08-27 1987-10-21 Ciba-Geigy Ag Hydrogenated pyridine derivatives
US4904673A (en) * 1988-01-14 1990-02-27 Dr. Karl Thomae, Gmbh Agent for treating bradycardia and bradyarrhythmia
US4957928A (en) * 1986-06-26 1990-09-18 Ciba-Geigy Corporation Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds
WO2005021505A1 (en) * 2003-09-03 2005-03-10 Galapagos Nv The claimed invention relates to novel 4-piperidinecarboxamide and the use thereof for the preparation of medicaments against 5-ht2a receptor-related disorders
US7867992B2 (en) 2004-07-21 2011-01-11 Aicuris Gmbh & Co. Kg Substituted quinolones
US7977349B2 (en) 2006-02-09 2011-07-12 Aicuris Gmbh & Co. Kg Substituted quinolones III

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0055997A2 (en) * 1979-03-07 1982-07-14 Imperial Chemical Industries Plc Oxirane and halohydrin compounds
EP0055997A3 (en) * 1979-03-07 1982-08-04 Imperial Chemical Industries Plc Oxirane and halohydrin compounds
EP0213080A3 (en) * 1985-08-27 1987-10-21 Ciba-Geigy Ag Hydrogenated pyridine derivatives
US4833169A (en) * 1985-08-27 1989-05-23 Ciba-Geigy Corporation Hydropyridine derivatives
US4939160A (en) * 1985-08-27 1990-07-03 Ciba-Geigy Corporation Hydropyridine derivatives
US4957928A (en) * 1986-06-26 1990-09-18 Ciba-Geigy Corporation Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds
US5112855A (en) * 1986-06-26 1992-05-12 Ciba-Geigy Corporation Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds and compositions
US4904673A (en) * 1988-01-14 1990-02-27 Dr. Karl Thomae, Gmbh Agent for treating bradycardia and bradyarrhythmia
WO2005021505A1 (en) * 2003-09-03 2005-03-10 Galapagos Nv The claimed invention relates to novel 4-piperidinecarboxamide and the use thereof for the preparation of medicaments against 5-ht2a receptor-related disorders
US7867992B2 (en) 2004-07-21 2011-01-11 Aicuris Gmbh & Co. Kg Substituted quinolones
US7977349B2 (en) 2006-02-09 2011-07-12 Aicuris Gmbh & Co. Kg Substituted quinolones III

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