GB722627A - Improvements relating to new 1-substituted-4-aminopiperazine derivatives and the preparation thereof - Google Patents

Improvements relating to new 1-substituted-4-aminopiperazine derivatives and the preparation thereof

Info

Publication number
GB722627A
GB722627A GB15339/52A GB1533952A GB722627A GB 722627 A GB722627 A GB 722627A GB 15339/52 A GB15339/52 A GB 15339/52A GB 1533952 A GB1533952 A GB 1533952A GB 722627 A GB722627 A GB 722627A
Authority
GB
United Kingdom
Prior art keywords
piperazyl
urea
ethyl
phenyl
thiourea
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
GB15339/52A
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 GB722627A publication Critical patent/GB722627A/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
    • C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises piperazine derivatives of the formula <FORM:0722627/IV (b)/1> where R is an alkyl, aralkyl, monocyclic aryl, carbalkoxy, dialkylcarbamyl or heterocyclic radical (the latter attached by a -c\s9N-group), Y1 and Y2 are hydrogen or methyl, and Z is carbalkoxy, R1-CO-, R1-SO2-, R2-NH-CO-, (R3)2N-CO- or R4-NH-CS-, R1 being alkyl, aryl or aralkyl, R2 cycloalkyl or aryl, R3 alkyl and R4 aryl, alkyl or alkenyl. These are prepared by treating the corresponding N-aminopiperazines with the appropriate acyl halides, sulphonyl halides, haloformic esters, carbamyl halides, isocyanates or isothiocyanates; the reaction may be carried out at 0-100 DEG C. in an inert solvent. When R is alkyl or aralkyl the products may be converted, into salts. Examples show the preparation of ethyl N-(4-carbethoxy-1-piperazyl)-carbamate, 1 - carbethoxy - 4 - acetyl - amino - piperazine, 1 - carbethoxy - 4 - phenylacetylamino - piper - azine, 1 - phenyl - 3 - (4 - carbethoxy - 1 - piperazyl) - urea, 1 - cyclohexyl - 3 - (4 - carbethoxy - 1 - piperazyl) - urea, 1 - phenyl - 3 - (4 - carbethoxy - 1 - piperazyl) - thiourea, 1 - allyl - 3 - (4 - carbethoxy - 1 - piperazyl) - thiourea, ethyl N - (4 - diethylcarbamyl - 1 - piperazyl) - carbamate, 1 - diethylcarbamyl - 4 - acetylaminopiperazine, 1 - diethylcarbamyl - 4 - benzoylaminopiperazine, 1 - phenyl - 3 -(4 - di - ethylcarbamyl - 1 - piperazyl) - urea, 1 - cyclo - hexyl - 3 - (4 - diethylcarbamyl - 1 - piperazyl) - urea, 1 - ethyl - 3 - (4 - diethylcarbamyl - 1 - piperazyl) - thiourea, N - (4 - diethylcarbamyl-1 - piperazyl) - 4 - chlorobenzenesulphonamide, ethyl N - (4 - methyl - 1 - piperazyl) - carbamate, 1 - cyclohexyl - 3 - (4 - methyl - 1 - piperazyl) - urea, 1 - ethyl - 3 - (4 - methyl - 1 - piperazyl) - thiourea, ethyl N - (4 - benzyl - 1 - piperazyl) - carbamate, 1 - benzyl - 4 - acetylaminopiper - azine, 1 - benzyl - 4 - phenylacetylamino - piperazine, 1 - benzyl - 4 - benzoylamino - piperazine, 1 - phenyl - 3 - (4 - benzyl - 1 - piperazyl) - urea, 1 - phenyl - 3 - (4 - benzyl - 1 - piperazyl) - thiourea, ethyl N - [4 - (p - chloro - phenyl) - 1 - piperazyl] - carbamate, 1 - (p - chlorophenyl) - 4 - acetylaminopiperazine, 1 - phenyl - 3 - [4 - (p - chlorophenyl) - 1 - piperazyl]-urea, 1 - (o - chlorophenyl) - 3 - [4 - (p - chloro - phenyl) - 1 - piperazyl] - urea, 1 : 1 - diethyl - 3 - [4 - (p - chlorophenyl) - 1 - piperazyl] - urea, 1 - allyl - 3 - [4 - (p - chlorophenyl) - 1 - piperazyl] - thiourea, ethyl N - [4 - (2 - pyridyl) - 1 - piper - azyl] - carbamate, 1 - (2 - pyridyl) - 4 - acetyl - aminopiperazine, 1 - phenyl - 3 - [4 - (2 - pyridyl) - 1 - piperazyl] - urea, 1 - allyl - 3 - [4 - (2 - pyridyl) - 1 - piperazyl] - thiourea, N - [4 - (2 - pyridyl) - 1 - piperazyl] - 4 - chloro - benzenesulphonamide, ethyl N - [4 - (2 - pyrimidyl) - 1 - piperazyl] - carbamate, 1 - (2 - pyrimidyl) - 4 - acetylaminopiperazine, 1 - cyclohexyl - 3 - [4 - (2 - pyrimidyl) - 1 - piper - azyl] - urea and 1 - ethyl - 3 - [4 - (2 - pyrimidyl)-1-piperazyl]-thiourea.
GB15339/52A 1951-06-22 1952-06-18 Improvements relating to new 1-substituted-4-aminopiperazine derivatives and the preparation thereof Expired GB722627A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US722627X 1951-06-22

Publications (1)

Publication Number Publication Date
GB722627A true GB722627A (en) 1955-01-26

Family

ID=22106529

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15339/52A Expired GB722627A (en) 1951-06-22 1952-06-18 Improvements relating to new 1-substituted-4-aminopiperazine derivatives and the preparation thereof

Country Status (1)

Country Link
GB (1) GB722627A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287454A (en) * 1964-11-04 1966-11-22 Searle & Co 1-substituted 4-isonicotinoylamino-piperazines
EP0436734A1 (en) * 1989-08-02 1991-07-17 Fujisawa Pharmaceutical Co., Ltd. New aminopiperazine derivatives
US5250528A (en) * 1989-08-02 1993-10-05 Fujisawa Pharmaceutical Co., Ltd. New aminopiperazine derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287454A (en) * 1964-11-04 1966-11-22 Searle & Co 1-substituted 4-isonicotinoylamino-piperazines
EP0436734A1 (en) * 1989-08-02 1991-07-17 Fujisawa Pharmaceutical Co., Ltd. New aminopiperazine derivatives
EP0436734A4 (en) * 1989-08-02 1992-01-02 Fujisawa Pharmaceutical Co., Ltd. New aminopiperazine derivatives
US5250528A (en) * 1989-08-02 1993-10-05 Fujisawa Pharmaceutical Co., Ltd. New aminopiperazine derivatives

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