GB842651A - Novel acetylene compounds and process of preparing same - Google Patents

Novel acetylene compounds and process of preparing same

Info

Publication number
GB842651A
GB842651A GB1059557A GB1059557A GB842651A GB 842651 A GB842651 A GB 842651A GB 1059557 A GB1059557 A GB 1059557A GB 1059557 A GB1059557 A GB 1059557A GB 842651 A GB842651 A GB 842651A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
represent
heterocyclic group
salts
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
GB1059557A
Inventor
John H Biel
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.)
LAKESIDE LAB Inc
Original Assignee
LAKESIDE LAB 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 LAKESIDE LAB Inc filed Critical LAKESIDE LAB Inc
Priority to GB1059557A priority Critical patent/GB842651A/en
Priority to DEL27432A priority patent/DE1083254B/en
Publication of GB842651A publication Critical patent/GB842651A/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
    • C07D295/02—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

Landscapes

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

Abstract

The invention comprises compounds of the formula: <FORM:0842651/IV(b)/1> wherein m and n represent the same or a different integer greater than 1 and the sum of which is at least 4; R1, R2, R3 and R4 represent the same or a different alkyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl or heterocyclic group or a group wherein R1 and R2, and R3 and R4, ar joined so that the nitrogen is part of a heterocyclic group (e.g. pyrrolidino-, piperidino- or morpholino-); and acid addition salts and quaternary ammonium salts thereof. The compounds are prepared (1) by reaching at an elevated temperature a compound to the formula: <FORM:0842651/IV(b)/2> (where X is halogen) with a compound of the formula: <FORM:0842651/IV(b)/3> (where Y is a reactive metal); and (2) by reacting a compound of the formula: <FORM:0842651/IV(b)/4> with a compound of the formula: <FORM:0842651/IV(b)/5> (where X is halogen) to produce compound of the formula: <FORM:0842651/IV(b)/6> and reacting the latter in the form of a reactive metal salt at an elevated temperature with a compound of the formula: <FORM:0842651/IV(b)/7> (where X is halogen). Acid addition salts may be obtained by subsequent treatment with, e.g., hydrohalic, sulphuric, formic or citric acids. Quaternary salts are obtained by subsequent treatment with alkyl and aralkyl esters of mineral and organic acids, e.g. methyl chloride, ethyl bromide and methyl sulphate. The compounds are used for lowering blood pressure. They may be reduced to the corresponding olefin derivatives and the latter may be either polymerized or hydrolyzed to the corresponding ketones and then reduced with sodium borohydride to give the corresponding alcohols. Reactive metal salts of the formula: <FORM:0842651/IV(b)/8> (where Y is a reactive metal, e.g. Li, Na or K) are prepared by reacting aminoalkynes of the formula: <FORM:0842651/IV(b)/9> with an alkali metal amide or hydride. Specification 750,346 is referred to.ALSO:A pharmaceutical composition comprises as the active ingredient a bis-aminoacetylene of the formula: wherein m and n represent the same or a different integer greater than 1 and the sum of which is at least 4; R1, R2, R3 and R4 represent the same or a different alkyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl or heterocyclic group or a group wherein R1 and R2, and R3 and R4, are joined so that the nitrogen is part of a heterocyclic group, or aid addition or graternary ammonium salts thereof, together with a suitable pharmaceutical carrier. The composition may be in the form of solutions, isotaric solutions, suspensions, powders, tablets or capsules. Specification 750,346 is referred to.
GB1059557A 1957-04-01 1957-04-01 Novel acetylene compounds and process of preparing same Expired GB842651A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB1059557A GB842651A (en) 1957-04-01 1957-04-01 Novel acetylene compounds and process of preparing same
DEL27432A DE1083254B (en) 1957-04-01 1957-04-17 Process for the preparation of blood pressure lowering N-disubstituted diaminoalkynes, their acid addition salts or quaternary ammonium salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1059557A GB842651A (en) 1957-04-01 1957-04-01 Novel acetylene compounds and process of preparing same

Publications (1)

Publication Number Publication Date
GB842651A true GB842651A (en) 1960-07-27

Family

ID=9970733

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1059557A Expired GB842651A (en) 1957-04-01 1957-04-01 Novel acetylene compounds and process of preparing same

Country Status (1)

Country Link
GB (1) GB842651A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1172925B (en) * 1957-02-16 1964-06-25 Basf Ag Anti-corrosive agents
US3201467A (en) * 1962-05-07 1965-08-17 Dow Chemical Co Propargylabietylamines
WO1992015551A1 (en) * 1991-03-01 1992-09-17 University Of Saskatchewan Aliphatic propargylamines as selective mao-b inhibitors and as neuroprotective agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1172925B (en) * 1957-02-16 1964-06-25 Basf Ag Anti-corrosive agents
US3201467A (en) * 1962-05-07 1965-08-17 Dow Chemical Co Propargylabietylamines
WO1992015551A1 (en) * 1991-03-01 1992-09-17 University Of Saskatchewan Aliphatic propargylamines as selective mao-b inhibitors and as neuroprotective agents
US5508311A (en) * 1991-03-01 1996-04-16 University Of Saskatchewan Aliphatic propargylamines as selective MAO-B inhibitors and as neuroprotective agents

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