GB1420759A - Piperidine derivatives - Google Patents

Piperidine derivatives

Info

Publication number
GB1420759A
GB1420759A GB1721674A GB1721674A GB1420759A GB 1420759 A GB1420759 A GB 1420759A GB 1721674 A GB1721674 A GB 1721674A GB 1721674 A GB1721674 A GB 1721674A GB 1420759 A GB1420759 A GB 1420759A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
carbon atoms
prepared
methyl
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
GB1721674A
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.)
John Wyeth and Brother Ltd
Original Assignee
John Wyeth and Brother 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 John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd
Priority to GB1721674A priority Critical patent/GB1420759A/en
Publication of GB1420759A publication Critical patent/GB1420759A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Abstract

1420759 Piperidinoalkanoic acid amide; nitriles; esters JOHN WYETH & BRO Ltd 12 July 1973 [12 July 1972] 17216/74 Divided out of 1420758 Heading C2C Novel compounds of Formula I wherein R represents hydrogen or up to 5 nuclear methyl groups; A is an alkylene chain containing 2 or 3 carbon atoms which may contain a lower alkyl substituent; R<SP>1</SP> represents hydrogen and R<SP>2</SP> represents t-butyl, or R<SP>1</SP> and R<SP>2</SP> together with the nitrogen atom to which they are attached represent a piperidino group; with the proviso that when A is an alkylene chain of 2-3 carbon atoms, carrying a methyl substituent then R<SP>1</SP> and R<SP>2</SP> may also represent hydrogen, alkyl of I to 6 carbon atoms or aralkyl wherein the alkyl portion contains from 1 to 6 carbon atoms; and the pharmaceutically acceptable acid addition salts thereof, are prepared by one of the following methods: (a) a compound of Formula II: is reacted with a compound Halogen-A-CO: NR<SP>1</SP>R<SP>2</SP>; (b) a compound of Formula IV: wherein Z is OH, alkoxy or an anhydride residue is reacted with a compound R<SP>1</SP>NHR<SP>2</SP> or (c) by partial hydrolysis of the corresponding nitrile of Formula V: Nitriles of Formula V above are prepared from piperidine and the corresponding terminally unsaturated nitrile. Esters of Formula IV above are prepared from piperidine and a terminally halogen-substituted alkanoic acid ester. Methyl 4-bromo-3-methylbutanoate is prepared from ethyl α-carbethoxy-#-methylglutarate by partial hydrolysis and then treated to form the silver salt which is reacted with bromine to give methyl 4-bromo-3-methylbutanoate. Pharmaceutical compositions in conventional forms for oral administration having anti-ulcer activity comprise an above novel compound and a carrier or diluent excluding antacids.
GB1721674A 1972-07-12 1972-07-12 Piperidine derivatives Expired GB1420759A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1721674A GB1420759A (en) 1972-07-12 1972-07-12 Piperidine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1721674A GB1420759A (en) 1972-07-12 1972-07-12 Piperidine derivatives

Publications (1)

Publication Number Publication Date
GB1420759A true GB1420759A (en) 1976-01-14

Family

ID=10091274

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1721674A Expired GB1420759A (en) 1972-07-12 1972-07-12 Piperidine derivatives

Country Status (1)

Country Link
GB (1) GB1420759A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024356A1 (en) * 1979-08-21 1981-03-04 Merck & Co. Inc. Pharmaceutical composition for treating a condition exhibiting pain, fever, and inflammation comprising 2-(substituted piperidinomethyl) propane- and propene nitriles
US4721788A (en) * 1985-07-12 1988-01-26 Eisai Co., Ltd. 4-cyanopiperidine derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024356A1 (en) * 1979-08-21 1981-03-04 Merck & Co. Inc. Pharmaceutical composition for treating a condition exhibiting pain, fever, and inflammation comprising 2-(substituted piperidinomethyl) propane- and propene nitriles
US4721788A (en) * 1985-07-12 1988-01-26 Eisai Co., Ltd. 4-cyanopiperidine derivatives

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Legal Events

Date Code Title Description
PS Patent sealed
746 Register noted 'licences of right' (sect. 46/1977)
PCNP Patent ceased through non-payment of renewal fee