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GB863243A - Improvements in or relating to acylphenothiazines - Google Patents

Improvements in or relating to acylphenothiazines

Info

Publication number
GB863243A
GB863243A GB30147/59A GB3014759A GB863243A GB 863243 A GB863243 A GB 863243A GB 30147/59 A GB30147/59 A GB 30147/59A GB 3014759 A GB3014759 A GB 3014759A GB 863243 A GB863243 A GB 863243A
Authority
GB
United Kingdom
Prior art keywords
carboxamide
piperidine
general formula
pyridine
propionylphenthiazine
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
GB30147/59A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB863243A publication Critical patent/GB863243A/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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0863243/IV (b)/1> and their pharmaceutically acceptable nontoxic acid addition and quaternary ammonium salts (wherein R is a C1-6 alkyl radical; Alk is a C2-6 alkylene radical; and R1 and R11 are alike or unlike and are each a hydrogen atom or a C1-8 alkyl or hydroxyalkyl radical); and the preparation thereof by condensing a compound of the general formula: <FORM:0863243/IV (b)/2> with at least one equivalent of a compound of the general formula: <FORM:0863243/IV (b)/3> (wherein one of the symbols X and Y is a hydrogen atom and the other a Halogen-Alk group) in the presence of at least an additional equivalent of base. 10- (3-Chloropropyl) - 2 - propionylphenthiazine is made from 2-propionylphenthiazine and 1-bromo-3-chloropropane. 10- (b -Chloroethyl)-2-[21-(21- methyl 11,31-dioxolanyl)]-phenthiazine is made from 2-[21-(21-methyl-11,31-dioxolanyl) ]-phenthiazine and 2-chloroethyl p-toluenesulphonate. Piperidine-4-carboxamide hydroacetate is formed from piperidine-4-carboxamide and acetic acid. Pyridine-2-carboxamide is prepared by reacting ethyl pyridine-2-carboxylate with concentrated ammonium hydroxide, and is catalytically hydrogenated to piperidine-2-carboxamide. Similarly made are pyridine-4-(N,N-diethyl) carboxamide and piperidine-4-(N,N-diethyl) carboxamide.
GB30147/59A 1958-09-04 1959-09-03 Improvements in or relating to acylphenothiazines Expired GB863243A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US863243XA 1958-09-04 1958-09-04

Publications (1)

Publication Number Publication Date
GB863243A true GB863243A (en) 1961-03-22

Family

ID=22197821

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30147/59A Expired GB863243A (en) 1958-09-04 1959-09-03 Improvements in or relating to acylphenothiazines

Country Status (1)

Country Link
GB (1) GB863243A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4021552A (en) * 1975-06-27 1977-05-03 A. H. Robins Company, Incorporated 10-[ω-(BENZOYLPIPERIDINYL)ALKYL]PHENOTHIAZINES
CN109053716A (en) * 2018-09-26 2018-12-21 暨明医药科技（苏州）有限公司 A kind of new process preparing metopimazine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4021552A (en) * 1975-06-27 1977-05-03 A. H. Robins Company, Incorporated 10-[ω-(BENZOYLPIPERIDINYL)ALKYL]PHENOTHIAZINES
CN109053716A (en) * 2018-09-26 2018-12-21 暨明医药科技（苏州）有限公司 A kind of new process preparing metopimazine

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