GB984119A - Substituted piperidines and methods for their preparation - Google Patents

Substituted piperidines and methods for their preparation

Info

Publication number
GB984119A
GB984119A GB2224061A GB2224061A GB984119A GB 984119 A GB984119 A GB 984119A GB 2224061 A GB2224061 A GB 2224061A GB 2224061 A GB2224061 A GB 2224061A GB 984119 A GB984119 A GB 984119A
Authority
GB
United Kingdom
Prior art keywords
formula
general formula
group
compounds
reacting
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
GB2224061A
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.)
Aspro Nicholas Ltd
Original Assignee
Aspro Nicholas 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
Priority claimed from AU61676/60A external-priority patent/AU248763B2/en
Application filed by Aspro Nicholas Ltd filed Critical Aspro Nicholas Ltd
Publication of GB984119A publication Critical patent/GB984119A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—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 two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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 general formula <FORM:0984119/C2/1> and their acid addition and quaternary ammonium salts, wherein R1 is hydrogen, methyl, ethyl or n-rpopyl; R2 is a straight or branched C2- 9 alkyl group; R1 and R2 may together form a ring provided by the group (CH2)4, (CH2)5 or (CH2)6; R3 is propyl; R4 and R5 and R6 are hydrogen, C1- 4 alkoxy or hydroxy or an ester thereof having 1-4 carbon atoms; R4 and R5 or R5 and R6 may together form a methylene dioxy or ethylene dioxy group; and n is an integer from 1 to 3, the preparation thereof by reacting an appropriate phenyl alkyl amine of the general formula <FORM:0984119/C2/2> either with an appropriate glutaric anhydride, acid, or ester thereof followed by reduction of the resulting glutarimide with lithium aluminium hydride or other such suitable reducing agent or with a substituted alkane of the formula <FORM:0984119/C2/3> wherein X represents halogen or hydroxyl or by reacting a piperidine of the formula <FORM:0984119/C2/4> with a phenyl alkyl halide of the formula <FORM:0984119/C2/5> or with a carboxylic acid of the general formula <FORM:0984119/C2/6> followed by reduction of the resulting glutarimide with lithium aluminium hydride or other suitable reducing agent; and pharmaceutical compositions containing the above compounds. Pharmaceutical compositions, having antihypertensive action, comprise the compounds of the invention and in association with a pharmaceutical carrier. The composition may be in the form of tablets, solutions for injection, encapsulated powders, or liquid compositions.
GB2224061A 1960-06-20 1961-06-20 Substituted piperidines and methods for their preparation Expired GB984119A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AU61676/60A AU248763B2 (en) 1960-06-20 Substituted piperidines and methods for their preparation

Publications (1)

Publication Number Publication Date
GB984119A true GB984119A (en) 1965-02-24

Family

ID=3746638

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2224061A Expired GB984119A (en) 1960-06-20 1961-06-20 Substituted piperidines and methods for their preparation

Country Status (1)

Country Link
GB (1) GB984119A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965105A (en) * 1975-01-20 1976-06-22 Sterling Drug Inc. Phenyl-lower-alkylamines
EP0007479A1 (en) * 1978-07-08 1980-02-06 BASF Aktiengesellschaft N-Arylpropyl-substituted cyclic amines, fungicides containing these compounds, and process for the preparation thereof
US4593037A (en) * 1984-07-26 1986-06-03 Pfizer Inc. 1,3-disubstituted piperidine compounds as neuroleptic agents
US4623728A (en) 1984-07-26 1986-11-18 Pfizer Inc. Intermediates for 1,3-disubstituted piperidine compounds as neuroleptic agents
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives
EP0529688A2 (en) * 1988-08-31 1993-03-03 Daiichi Pharmaceutical Co., Ltd. Azaspiro n,m alkanes and diazaspiro n,m -alkanes
US5286723A (en) * 1988-08-31 1994-02-15 Daiichi Seiyaku Co., Ltd. Spiro compound

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3965105A (en) * 1975-01-20 1976-06-22 Sterling Drug Inc. Phenyl-lower-alkylamines
EP0007479A1 (en) * 1978-07-08 1980-02-06 BASF Aktiengesellschaft N-Arylpropyl-substituted cyclic amines, fungicides containing these compounds, and process for the preparation thereof
US4593037A (en) * 1984-07-26 1986-06-03 Pfizer Inc. 1,3-disubstituted piperidine compounds as neuroleptic agents
US4623728A (en) 1984-07-26 1986-11-18 Pfizer Inc. Intermediates for 1,3-disubstituted piperidine compounds as neuroleptic agents
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives
EP0339878A3 (en) * 1988-04-25 1990-12-05 Eli Lilly And Company Propanamine derivatives
EP0529688A2 (en) * 1988-08-31 1993-03-03 Daiichi Pharmaceutical Co., Ltd. Azaspiro n,m alkanes and diazaspiro n,m -alkanes
EP0529688A3 (en) * 1988-08-31 1993-03-10 Daiichi Pharmaceutical Co., Ltd. Azaspiro n,m alkanes and diazaspiro n,m -alkanes
US5286723A (en) * 1988-08-31 1994-02-15 Daiichi Seiyaku Co., Ltd. Spiro compound
US5508428A (en) * 1988-08-31 1996-04-16 Daiichi Phamaceutical Co., Ltd. Spiro compound

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