GB993748A - 4-azaphenthiazine derivatives - Google Patents

4-azaphenthiazine derivatives

Info

Publication number
GB993748A
GB993748A GB2487262A GB2487262A GB993748A GB 993748 A GB993748 A GB 993748A GB 2487262 A GB2487262 A GB 2487262A GB 2487262 A GB2487262 A GB 2487262A GB 993748 A GB993748 A GB 993748A
Authority
GB
United Kingdom
Prior art keywords
compound
group
formula
reacting
acid
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
GB2487262A
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Deutsche Gold und Silber Scheideanstalt
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
Priority claimed from DED36533A external-priority patent/DE1159464B/en
Priority claimed from DED38638A external-priority patent/DE1166206B/en
Application filed by Degussa GmbH, Deutsche Gold und Silber Scheideanstalt filed Critical Degussa GmbH
Publication of GB993748A publication Critical patent/GB993748A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0993748/C2/1> wherein the benzene ring of the 4-azaphenthiazine residue may be substituted by a chlorine atom, Alk represent a straight or branched alkylene residue of 2-4 carbon atoms, and X represents the group-NR1R2 in which R1 and R2 are like or different and represent hydrogen atoms or C1-4 alkyl groups or are joined to form a heterocyclic ring or X represents the group OR in which R is a hydrogen atom or a C1-4 alkyl group, their acid addition and quaternary ammonium salts and the preparation thereof, wherein X is the group -NR1R2 by (a) heating an appropriate 10-unsubstituted 4-azaphenthiazine with a compound of the formula <FORM:0993748/C2/2> in the presence of a condensation agent splitting off hydrogen halide and in an inert solvent; or (b) heating an appropriate 10-unsubstituted azophenthiazine with a compound of the general formula <FORM:0993748/C2/3> under the conditions of (a) and reacting the carboxylic ester group with an appropriate amine; or (c) heating an appropriate 10-unsubstituted 4-azaphenthiazine with a compound of the formula <FORM:0993748/C2/4> under the conditions of (a) and converting the nitrile into a carboxylic acid amide group; or (d) heating a compound of the formula <FORM:0993748/C2/5> wherein the benzene ring may be substituted by a chlorine atom and in which R represents a C1-4-alkyl group and Y represents an anion, with a compound of the formula <FORM:0993748/C2/6> at from 100-200 DEG C.; or (e) reacting a compound of the formula <FORM:0993748/C2/7> wherein the benzene ring may be substituted by a chlorine atom and Alk1 represents an alkylene group having one CH2 group less than the Alk group, or an acetate of such an aldehyde, with a piperidine carboxylic acid amide as in (d) in the presence of formic acid; or (f) reacting a compound of the formula <FORM:0993748/C2/8> wherein the benzene ring may be substituted by a chlorine atom, is reacted with a piperidine carboxylic acid amide, as in (d), with simultaneous catalytic hydrogenation in the presence of a noble metal catalyst in an alkali solution; or (g) reacting an appropriate 10-unsubstituted-4-azaphenthiazine with a piperidine carboxylic acid amide, as in (d), and a compound Cl-Alk-Br in the presence of a condensation agent splitting off hydrogen halide, optionally in the presence of an inert solvent or when X represents OR reacting an appropriate 10-unsubstituted 4-aza-phenthiazine with a compound of the formula <FORM:0993748/C2/9> in the presence of an inert solvent and in the presence of a condensation agent splitting off hydrogen halide. 1 - (3 - Bromopropyl) - nipecotinic acid diethyl amide is prepared by reacting nicotinic acid diethylamide with 3-chloro-1-propanol, hydrogenating the quaternary 3-hydroxypropyl-N-nicotinic acid diethylamide hydrobromide to 1 - (3 - hydroxypropyl) - nipecotinic acid diethylamide and reacting this with hydrobromic acid. 1 - (3 - Chloropropyl) - isonipecotinic acid dimethylamide, diethylamide and piperidide were prepared similarly through 1-(3-hydroxy-propyl)-isonipecotinic acid dimethylamide, diethylamide and piperidide and 1-(3-chloropropyl)-isonipecotinic acid ethyl ester through 1-3-hydroxypropyl)-isonipecotinic acid ethyl ester.
GB2487262A 1961-07-12 1962-06-28 4-azaphenthiazine derivatives Expired GB993748A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DED36533A DE1159464B (en) 1961-07-12 1961-07-12 Process for the preparation of 4-aza-phenthiazines substituted in the 10-position
DED38638A DE1166206B (en) 1962-04-11 1962-04-11 Process for the preparation of 4-azaphenthiazine derivatives

Publications (1)

Publication Number Publication Date
GB993748A true GB993748A (en) 1965-06-02

Family

ID=25971297

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2487262A Expired GB993748A (en) 1961-07-12 1962-06-28 4-azaphenthiazine derivatives

Country Status (2)

Country Link
CH (1) CH421111A (en)
GB (1) GB993748A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996031469A1 (en) * 1995-04-07 1996-10-10 Novo Nordisk A/S N-substituted azaheterocyclic carboxylic acids and esters thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996031469A1 (en) * 1995-04-07 1996-10-10 Novo Nordisk A/S N-substituted azaheterocyclic carboxylic acids and esters thereof

Also Published As

Publication number Publication date
CH421111A (en) 1966-09-30

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