GB772147A - Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines - Google Patents

Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines

Info

Publication number
GB772147A
GB772147A GB2337/55A GB233755A GB772147A GB 772147 A GB772147 A GB 772147A GB 2337/55 A GB2337/55 A GB 2337/55A GB 233755 A GB233755 A GB 233755A GB 772147 A GB772147 A GB 772147A
Authority
GB
United Kingdom
Prior art keywords
acyl
carbamyl
piperazine
benzoyl
unsymmetrically substituted
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
GB2337/55A
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
Priority to GB2337/55A priority Critical patent/GB772147A/en
Publication of GB772147A publication Critical patent/GB772147A/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
    • C07D295/20—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 1,4-unsymmetrically substituted piperazines having the general formula <FORM:0772147/IV(b)/1> wherein O=C-R is an acyl radical, R being an alkyl, aryl or halo-aryl radical, such as for example, benzoyl, dichlorobenzoyl, o-chlorobenzoyl, acetyl, propionyl or n-butyryl. Such compounds are obtained by treating 1-carbamyl - 4 - carbobenzoxy - piperazine with hydrogen and a reducing agent and then reacting the 1-carbamyl-piperazine thus produced with an acylating agent, i.e. an acyl halide or acyl anhydride. The reduction can be effected by the action of hydrogen and a palladiumcharcoal catalyst, preferably in a neutral or weakly acidic medium such as water, ethanol or acetic acid. In Example (1) 1-carbamylpiperazine (from the reduction of 1-carbamyl-4-carbobenzoxy-piperazine) is reacted with benzoyl chloride to give 1-benzoyl-4-carbamylpiperazine. In a generally similar manner are prepared 1 - acyl - 4 - carbamyl - piperazines in which the acyl groups are respectively (2) 2,6-dichlorobenzoyl; (3) acetyl; (4) propionyl; (5) o-chlorobenzoyl.
GB2337/55A 1955-01-26 1955-01-26 Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines Expired GB772147A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2337/55A GB772147A (en) 1955-01-26 1955-01-26 Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2337/55A GB772147A (en) 1955-01-26 1955-01-26 Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines

Publications (1)

Publication Number Publication Date
GB772147A true GB772147A (en) 1957-04-10

Family

ID=22136731

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2337/55A Expired GB772147A (en) 1955-01-26 1955-01-26 Improvements relating to the preparation of new 1,4-unsymmetrically substituted piperazines

Country Status (1)

Country Link
GB (1) GB772147A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0224176A1 (en) * 1985-11-29 1987-06-03 Bayer Ag Process for preparing oligomers and telechelics with carboxy-piperazine units, and oligomers and telechelics of poly(carboxypiperazine)
EP1536813A2 (en) * 2002-06-26 2005-06-08 EntreMed, Inc. Compositions and methods comprising protein activated receptor antagonists
US7867975B2 (en) 1995-10-23 2011-01-11 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0224176A1 (en) * 1985-11-29 1987-06-03 Bayer Ag Process for preparing oligomers and telechelics with carboxy-piperazine units, and oligomers and telechelics of poly(carboxypiperazine)
US4758652A (en) * 1985-11-29 1988-07-19 Bayer Ag Process for preparing oligomers and telechels having carboxy-piperazine units, and new oligomers and telechels of poly(carboxypiperazine)
US7867975B2 (en) 1995-10-23 2011-01-11 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions
EP1536813A2 (en) * 2002-06-26 2005-06-08 EntreMed, Inc. Compositions and methods comprising protein activated receptor antagonists
EP1536813A4 (en) * 2002-06-26 2005-11-09 Entremed Inc Compositions and methods comprising protein activated receptor antagonists

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