GB842651A - Novel acetylene compounds and process of preparing same - Google Patents
Novel acetylene compounds and process of preparing sameInfo
- 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
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.
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)
| 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 |
-
1957
- 1957-04-01 GB GB1059557A patent/GB842651A/en not_active Expired
Cited By (4)
| 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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