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GB823733A - Phenothiazine derivatives - Google Patents

Phenothiazine derivatives

Info

Publication number
GB823733A
GB823733A GB3751056A GB3751056A GB823733A GB 823733 A GB823733 A GB 823733A GB 3751056 A GB3751056 A GB 3751056A GB 3751056 A GB3751056 A GB 3751056A GB 823733 A GB823733 A GB 823733A
Authority
GB
United Kingdom
Prior art keywords
methyl
pyrrolidyl
pyrrolidines
pyrrolidine
phenthiazine
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
GB3751056A
Inventor
Frank Peter Doyle
Minoo Dossabhoy Mehta
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.)
Beecham Research Laboratories Ltd
Original Assignee
Beecham Research Laboratories 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 Beecham Research Laboratories Ltd filed Critical Beecham Research Laboratories Ltd
Priority to GB3751056A priority Critical patent/GB823733A/en
Publication of GB823733A publication Critical patent/GB823733A/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- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0823733/IV (b)/1> and their acid addition salts (wherein R is a hydrogen atom or an alkyl radical with not more than four carbon atoms, R1 is a hydrogen, bromine or chlorine atom, and n is 1 or 2), and the preparation thereof by condensing a phenthiazine derivative of the formula <FORM:0823733/IV (b)/2> (wherein M is a lithium, potassium or sodium atom) with a 2-haloalkyl pyrrolidine of the formula <FORM:0823733/IV (b)/3> (wherein X is a halogen atom). The condensation can be effected in a non-polar solvent, e.g. benzene or toluene. The compounds of the invention have pharmaceutical properties. In Example (1) the product of reacting phenthiazine with potassium amide in toluene is treated with 1-methyl-2-chloromethyl pyrrolidine to give 10-(11-methyl-21-pyrrolidyl) methylphenthiazine, from which the hydrochloride is made. Similarly prepared are 10-[2-(11-methyl-21-pyrrolidyl) ethyl] phenthiazine and its dihydrogen citrate; 10-(11-methyl-21-pyrrolidyl) methyl - 2 - chlorophenthiazine; 10-[2 - (11 - methyl - 21 - pyrrolidyl) ethyl] - 2-chlorophenthiazine and its dihydrogen citrate. 2-Haloalkyl pyrrolidines are made by treating 2-hydroxyalkyl pyrrolidines with a halogenating agent, e.g. thionyl chloride. Both optically active and racemic forms of the 2-hydroxyalkyl pyrrolidines may be used. 1 - Methyl - 2 - (2 - hydroxyethyl) pyrrolidine is made by reducing ethyl-1-methyl-2-pyrrolidyl acetate with lithium. Specifications 772,179 and 820,503 are referred to.
GB3751056A 1956-12-07 1956-12-07 Phenothiazine derivatives Expired GB823733A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3751056A GB823733A (en) 1956-12-07 1956-12-07 Phenothiazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3751056A GB823733A (en) 1956-12-07 1956-12-07 Phenothiazine derivatives

Publications (1)

Publication Number Publication Date
GB823733A true GB823733A (en) 1959-11-18

Family

ID=10396999

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3751056A Expired GB823733A (en) 1956-12-07 1956-12-07 Phenothiazine derivatives

Country Status (1)

Country Link
GB (1) GB823733A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3251836A (en) * 1961-09-26 1966-05-17 Szabo Hnos Kessler & Cia S R L Oxazolidone derivatives and their preparation
WO2008087421A2 (en) * 2007-01-17 2008-07-24 King's College London Male contraceptive

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3251836A (en) * 1961-09-26 1966-05-17 Szabo Hnos Kessler & Cia S R L Oxazolidone derivatives and their preparation
WO2008087421A2 (en) * 2007-01-17 2008-07-24 King's College London Male contraceptive
WO2008087421A3 (en) * 2007-01-17 2009-07-23 King S College London Male contraceptive
US8927579B2 (en) 2007-01-17 2015-01-06 Nnaemkea Ikechukwu Amobi Male contraceptive

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