GB781528A - Substituted ethylene dipiperazines - Google Patents
Substituted ethylene dipiperazinesInfo
- Publication number
- GB781528A GB781528A GB23934/55A GB2393455A GB781528A GB 781528 A GB781528 A GB 781528A GB 23934/55 A GB23934/55 A GB 23934/55A GB 2393455 A GB2393455 A GB 2393455A GB 781528 A GB781528 A GB 781528A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- carbethoxypiperazine
- dicarbethoxy
- reacted
- ethyl
- 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
- C07D295/16—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
- C07D295/16—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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- 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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0781528/IV (a)/1> and hydrochlorides and quaternary salts thereof, wherein X is a lower alkyl, lower alkylamino di-(lower alkyl) amino or lower alkoxy group, R1 is a lower alkyl, aryl, p-chlorophenyl, p-acetamidophenyl, p-lower alkoxyphenyl, hydroxy lower alkyl, or aralkyl radical, and R2 is hydrogen or a lower alkyl radical, the word "lower" being used to signify groups containing from 1 to 6 carbon atoms. The compounds are made by treating a corresponding dihaloethane derivative with a 1-substituted piperazine wherein the substituent is the group X-CO-, in the presence of a base such as an alkali metal carbonate, bicarbonate or hydroxide and preferably in the presence of an inert organic solvent such as methanol, ethanol, propanol, benzene, toluene, chlorobenzene or dioxane or an aqueous alcoholic mixture. The products may be converted into their acid addition and quaternary salts by standard methods. In examples: (1) 1 : 2-dibromopropane is reacted with 1-carbethoxypiperazine to give a -methyl-4 : 41-dicarbethoxy-1 : 11-ethylene diperazine; (2) 2 : 3-dibromobutane is reacted with 1-carbethoxypiperazine to give a : b - dimethyl - 4 : 41 - dicarbethoxy-1 : 11-ethylenedipiperazine; (3) 1 : 2-dibromobutane is reacted with 1-carbethoxypiperazine to give a - ethyl - 4 : 41 - dicarbethoxy - 1 : 11 ethylenedipiperazine; (4) 1 : 2 - dibromoethylbenzene is reacted with 1-carbethoxypiperazine to give a - phenyl - 4 : 41 - dicarbethoxy - 1 : 11 ethylenedipiperazine; (5) the product of (4) is converted into its hydrochloride; (6) the product of (1) is converted into the methiodide, and (7) the product of (2) is converted into its hydrochloride. Other specified products ininclude 4 : 41-bis-(acetyl, propionyl, butyryl, diethylcarbamyl, dipropylcarbamyl, carbopropoxy, carbobutoxy and carbethoxy)-a : b -dipiperazyl derivatives of a -methyl, a : a -dimethyl, a -ethyl, a -methyl-b -ethyl, a -ethyl-b -propyl, a : b -diethyl, a -p-methoxyphenyl, a -p-ethoxyphenyl, a - p - acetamidophenyl, a -hydroxymethyl, a -hydroxypropyl, a -benzyl and a -phenyl, ethanes.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US781528XA | 1954-09-10 | 1954-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB781528A true GB781528A (en) | 1957-08-21 |
Family
ID=22142257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23934/55A Expired GB781528A (en) | 1954-09-10 | 1955-08-19 | Substituted ethylene dipiperazines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB781528A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4761476A (en) * | 1985-06-28 | 1988-08-02 | The Dow Chemical Company | Compounds formed by the reaction of piperazine, and derivatives thereof, with glyoxal, and derivatives thereof |
US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
-
1955
- 1955-08-19 GB GB23934/55A patent/GB781528A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4761476A (en) * | 1985-06-28 | 1988-08-02 | The Dow Chemical Company | Compounds formed by the reaction of piperazine, and derivatives thereof, with glyoxal, and derivatives thereof |
US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
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