GB782431A - New phenthiazine derivatives and their preparation - Google Patents

New phenthiazine derivatives and their preparation

Info

Publication number
GB782431A
GB782431A GB3336654A GB3336654A GB782431A GB 782431 A GB782431 A GB 782431A GB 3336654 A GB3336654 A GB 3336654A GB 3336654 A GB3336654 A GB 3336654A GB 782431 A GB782431 A GB 782431A
Authority
GB
United Kingdom
Prior art keywords
phenthiazinyl
diethylaminoethyl
ethyl
chloride
propyl
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
GB3336654A
Inventor
Robert Michel Jacob
Jacques Georges Robert
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Priority to GB3336654A priority Critical patent/GB782431A/en
Priority to US469573A priority patent/US2755219A/en
Publication of GB782431A publication Critical patent/GB782431A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0782431/IV (a)/1> wherein Y represents a hydrogen or halogen atom, Z represents a sulphur atom or an SO or SO2 group, A and B each represent a divalent straight or branched hydrocarbon chain containing 2 to 4 carbon atoms, X represents a halogen atom or another acid residue, and R1, R2, R3 and R4 are alike or different and each represents either an individual alkyl group containing not more than 4 carbon atoms or an alkylene group containing not more than 4 carbon atoms and forming a part of a heterocyclic ring containing the nitrogen atom to which it is attached whereby one of the following variants of the foregoing formula is obtained <FORM:0782431/IV (a)/2> is replaced by <FORM:0782431/IV (a)/3> where A1 is an hydrocarbon chain containing at least one carbon atom fewer than A and the dotted lines indicate chains of methylene groups; <FORM:0782431/IV (a)/4> is replaced by <FORM:0782431/IV (a)/5> where the dotted lines indicate chains of methylene groups; <FORM:0782431/IV (a)/6> or <FORM:0782431/IV (a)/7> are replaced by pyrrolidino, piperidino, or morpholino groups. Such compounds are obtained by reacting a phenthiazine derivative of the general formula <FORM:0782431/IV (a)/8> with an amine of the general formula <FORM:0782431/IV (a)/9> one of the symbols P and Q representing the atom or acid residue X and the other representing the group <FORM:0782431/IV (a)/100> In examples: (1) 10-(2-dimethylaminoethyle phenthiazine and dimethylaminochloroethan) are heated in anhydrous ethanol to form [2-(10-phenthiazinyl)ethyl] - 2 - dimethylaminoethyl)-dimethylammonium chloride. In a generally similar manner there are prepared (2) [2-(3-chloro - 10 - phenthiazinyl)ethyl] - (2 - diethylaminoethyl)dimethylammonium chloride; (3) [2 - (10 - phenthiazinyl)ethyl] - 2 - piperidinoethyl)dimethylammonium chloride; (4) [1-(10-phenthiazinyl) - 2 - propyl] - (2 - diethylaminoethyl)dimethylammonium chloride; (5) 1:4-dimethyl - 1 - [2 - (10 - phenthiazinyl)ethyl]-1 - piperazinium toluene - p - sulphonate; (6) [2 - (10 - phenthiazinyl)ethyl] - (2 - diethylaminoethyl)diethylammonium chloride; (7) [3 - (3 - chloro - 10 - phenthiazinyl)propyl] - (2-diethylaminoethyl)dimethylammonium chloride; (8) [3 - (10 - phenthiazinyl)propyl] - (2-diethylaminoethyl)pyrrolidinium chloride; (9) [1 - (9 - oxy - 10 - phenthiazinyl) - 2 - propyl]-(2 - diethylaminoethyl) dimethylammonium chloride; (10) [1-(10-phenthiazinyl)-2-propyl] (2 - piperidinoethyl)diethylammonium chloride; (11) [1 - (9:9 - dioxy - 10 - phenthiazinyl) - 2-propyl] - (2 - diethylaminoethyl)dimethyl ammonium chloride; (12) [2-(9:9-dioxy-10-phenthiazinyl)ethyl] - (2 - diethylaminoethyl) dimethylammonium chloride; (13) [2-(3-chloro-9:9 - dioxy - 10 - phenthiazinyl)ethyl] - (2-diethylaminoethyl) dimethylammonium chloride; (14) [3-(3-chloro-9:9-dioxy-10-phenthiazinyl)propyl] - (2 - diethylaminoethyl)dimethylammonium chloride; (15) [3-(9:9 dioxy - 10 - phenthiazinyl) - 2 - methylpropyl]-(2 - diethylaminoethyl) dimethylammonium chloride; (16) 1-methyl-1-(2-diethylaminoethyl) - 3 - (10 - phenthiazinylmethyl) piperidinium chloride. Specification 769,440 is referred to.ALSO:Phenthiazine derivatives of the formula <FORM:0782431/VI/1> where Y represents a hydrogen or halogen atom, Z represents a sulphur atom or an SO or SO2 group, A and B each represent a divalent straight or branched hydrocarbon chain containing 2 to 4 carbon atoms, X represent a halogen atom or another acid residue and R1, R2, R3, R4 are the alike or different and each represents either an individual alkyl group containing not more than 4 carbon atoms or an alkylene group containing not more than 4 carbon atoms and forming a part of a heterocyclic ring containing the nitrogen atom to which it is attached possess a synergistic effect with regard to ganghoplegic products, including the compounds of Specification 769,440. Mixtures specified are the [2-(10-phenthiazinyl) - ethyl] - (2 - diethylaminoethyl) - dimethylammonium salts or [2-(3-chloro - 10 - phenthiazinyl) - ethyl] - (2 - diethylaminoethyl) - dimethylammonium salts with 1 : 4 - dimethyl - 1 : 4 - di - [5 - (3 - chloro - 10-phenthiazinyl) - 3 : 3 - dimethyl - 3 - azanium-1-pentyl]-piperazinium salts.
GB3336654A 1954-11-17 1954-11-17 New phenthiazine derivatives and their preparation Expired GB782431A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3336654A GB782431A (en) 1954-11-17 1954-11-17 New phenthiazine derivatives and their preparation
US469573A US2755219A (en) 1954-11-17 1954-11-17 2-(3, 4-methylenedioxyphenoxy) tetrahydropyran as a synergist for pyrethrins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3336654A GB782431A (en) 1954-11-17 1954-11-17 New phenthiazine derivatives and their preparation

Publications (1)

Publication Number Publication Date
GB782431A true GB782431A (en) 1957-09-04

Family

ID=10351992

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3336654A Expired GB782431A (en) 1954-11-17 1954-11-17 New phenthiazine derivatives and their preparation

Country Status (1)

Country Link
GB (1) GB782431A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2972612A (en) * 1961-02-21 Phenthiazine compounds
US3040043A (en) * 1959-03-18 1962-06-19 Degussa 3-trifluoromethyl-10-[3'-(4"-(2"'-hydroxy ethyl)-homopiperazino)-propyl]-phenothiazine and 3-trifluoromethyl-10-[3'-(4"-(2"'-acetoxyethyl)-homopiperazino)-propyl]-phenothiazine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2972612A (en) * 1961-02-21 Phenthiazine compounds
US3040043A (en) * 1959-03-18 1962-06-19 Degussa 3-trifluoromethyl-10-[3'-(4"-(2"'-hydroxy ethyl)-homopiperazino)-propyl]-phenothiazine and 3-trifluoromethyl-10-[3'-(4"-(2"'-acetoxyethyl)-homopiperazino)-propyl]-phenothiazine

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