GB833474A - Piperazine derivatives - Google Patents

Piperazine derivatives

Info

Publication number
GB833474A
GB833474A GB38774/57A GB3877457A GB833474A GB 833474 A GB833474 A GB 833474A GB 38774/57 A GB38774/57 A GB 38774/57A GB 3877457 A GB3877457 A GB 3877457A GB 833474 A GB833474 A GB 833474A
Authority
GB
United Kingdom
Prior art keywords
piperazine
give
propyl
phenothiazyl
hydroxyethyl
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
GB38774/57A
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.)
Scherico Ltd
Original Assignee
Scherico Ltd
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 Scherico Ltd filed Critical Scherico Ltd
Publication of GB833474A publication Critical patent/GB833474A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0833474/IV (b)/1> and their pharmaceutically acceptable acid addition salts, and the preparation thereof by condensing a compound of the general formula <FORM:0833474/IV (b)/2> with a piperazine of the formula <FORM:0833474/IV (b)/3> wherein n is 1 or 2, R1 is a hydrogen atom or a lower alkyl group or the residue of a lower aliphatic carboxylic acid (the term "lower" indicating not more than 6 carbon atoms in the group so described) and of P and Q one is hydrogen and the other is a group CH2CH2CH2X or CH2CH2COX, X being a reactive electronegative atom or radical, such as a p halogen atom or an aryl sulphonic ester radical, and if necessary reducing CH2CH2CO to propylene. The reaction is preferably carried out in the presence of a basic condensing agent. In an example, 2-trifluoromethylphenothiazine is condensed with 1-chloro-3-bromopropane in the presence of sodium amide and liquid ammonia, to form 10-(3-chloropropyl)-2-trifluoromethylphenothiazine which is heated with 1-(2hydroxyethyl)-piperazine to give 1-(2-hydroxyethyl) - 4 - [3 - (2 - trifluoromethyl - 10 - phenothiazyl)-propyl]-piperazine. Similarly, but using 1 - (3 - hydroxypropyl) - piperazine the corresponding propyl analogue is obtained. In further examples the 1-(2-hydroxyethyl) derivative is reacted with phenyl chlorocarbonate to give the corresponding phenyl carbonate ester and this in turn with ammonia yields the carbamate of 1-(2-hydroxyethyl)-4-[3-(2trifluoromethyl - 10 - phenothiazyl) - propyl]piperazine; with dimethylcarbamyl chloride to give the dimethylcarbamate ester; with ethyl chlorocarbonate to give the ethyl carbonate ester (both with the 1-(2-hydroxy)ethyl) and 1-(3-hydroxypropyl) derivatives); and with acetic or propionic anhydrides to give the acetate or propionate esters. Condensing 10gives 1 - (2 - ethoxyethyl) - 4 - [3 - 2 - trifluoromethyl - 10 - phenothiazyl) - propyl] - piperazine. The dihydrochlorides and dimaleates of the esters above are also described.
GB38774/57A 1956-12-13 1957-12-13 Piperazine derivatives Expired GB833474A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US356775XA 1956-12-13 1956-12-13
CH349268T 1957-12-09

Publications (1)

Publication Number Publication Date
GB833474A true GB833474A (en) 1960-04-27

Family

ID=25737052

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38774/57A Expired GB833474A (en) 1956-12-13 1957-12-13 Piperazine derivatives

Country Status (4)

Country Link
CH (1) CH356775A (en)
DE (1) DE1168434B (en)
GB (1) GB833474A (en)
MY (1) MY6200102A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169962A (en) * 1963-02-28 1965-02-16 Olin Mathieson Benzhydryl ethers of 10-(hydroxyethylpiperazinopropyl) phenothiazines
US3282934A (en) * 1964-05-15 1966-11-01 Schering Corp Nitrogenous esters of hydroxylalkylamino phenothiazines
WO2013138101A2 (en) 2012-03-16 2013-09-19 Children's Medical Center Corporation Calmodulin inhibitors for the treatment of ribosomal disorders and ribosomapathies

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694705A (en) * 1954-11-16 Nx c c ox a a
GB666457A (en) * 1948-10-30 1952-02-13 Henri Morren Carbonyl chlorides and monocarboxyamides of piperazine and process for the preparation thereof
BE558008A (en) * 1956-06-21

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169962A (en) * 1963-02-28 1965-02-16 Olin Mathieson Benzhydryl ethers of 10-(hydroxyethylpiperazinopropyl) phenothiazines
US3282934A (en) * 1964-05-15 1966-11-01 Schering Corp Nitrogenous esters of hydroxylalkylamino phenothiazines
WO2013138101A2 (en) 2012-03-16 2013-09-19 Children's Medical Center Corporation Calmodulin inhibitors for the treatment of ribosomal disorders and ribosomapathies
EP3461482A1 (en) 2012-03-16 2019-04-03 Children's Medical Center Corporation Calcium channel blockers for the treatment of ribosomal disorders and ribosomapathies

Also Published As

Publication number Publication date
DE1168434B (en) 1964-04-23
MY6200102A (en) 1962-12-31
CH356775A (en) 1961-09-15

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