GB781528A - Substituted ethylene dipiperazines - Google Patents

Substituted ethylene dipiperazines

Info

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
Application number
GB23934/55A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB781528A publication Critical patent/GB781528A/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
    • C07D295/16—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.
GB23934/55A 1954-09-10 1955-08-19 Substituted ethylene dipiperazines Expired GB781528A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
GB1167563A (en) Novel 3-(2-Substituted Ethyl) Indoles and Processes for Their Manufacture
GB1120463A (en) Derivatives of 1,3-diazafluoranthene-1-oxide
ES269967A1 (en) Pyrazolones and processes for their preparation
GB809760A (en) Improvements in or relating to pharmacologically active piperazine derivatives and processes for preparing them
GB1159340A (en) Thion- and Thiol-Carbamate Derivatives
GB781528A (en) Substituted ethylene dipiperazines
GB1414207A (en) Benzo b thiophene derivatives their preparation and use as pharmaceuticals
GB851311A (en) Morpholine compounds and their production
GB1116736A (en) Improvements in or relating to 3-morpholinone and morpholine-3-thione derivatives
GB834290A (en) Substituted piperidines
GB1067421A (en) Derivatives of rifamycin b
GB688354A (en) Improvements relating to compounds of the benzhydryl ether type
GB901455A (en) C-substituted piperazinones and the manufacture thereof
GB959203A (en) Indole derivatives and salts thereof
ES347893A1 (en) Biologically active substituted-s-triazines
GB818724A (en) Hydantoin derivatives
GB807877A (en) New indole derivatives
US3201405A (en) Pharmacologically active derivatives of nu-methyl-isonipecotic acid
GB763406A (en) Novel 6-aminomethyl-5-hydroxy-indane derivatives and a process for the manufacture thereof
GB731956A (en) New pyrimidine compounds
GB890725A (en) Improvements in or relating to azetidine derivatives
GB1073770A (en) Pyridazone derivatives and process for their preparation
GB875151A (en) Improvements in antiozonants for rubber
GB807750A (en) Improvements in or relating to piperazine derivatives
GB771151A (en) Method for the preparation of aminoacyl-anilides