GB800632A - New derivatives of phenthiazine and processes for their production - Google Patents

New derivatives of phenthiazine and processes for their production

Info

Publication number
GB800632A
GB800632A GB3245954A GB3245954A GB800632A GB 800632 A GB800632 A GB 800632A GB 3245954 A GB3245954 A GB 3245954A GB 3245954 A GB3245954 A GB 3245954A GB 800632 A GB800632 A GB 800632A
Authority
GB
United Kingdom
Prior art keywords
phenthiazine
propyl
group
bispiperidino
groups
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
GB3245954A
Inventor
Raymond Jacques Horclois
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 GB3245954A priority Critical patent/GB800632A/en
Publication of GB800632A publication Critical patent/GB800632A/en
Expired legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention comprises phenthiazine derivatives of the general formula: <FORM:0800632/IV (b)/1> and their salts, including quaternary ammonium derivatives (wherein Y represents a sulphur atom or an SO or SO2 group, X represents one or more hydrogen or halogen atoms or acyl groups containing not more than four carbon atoms, which may be present in one or both carbocyclic nuclei, A represents the trivalent hydrocarbon group: <FORM:0800632/IV (b)/2> in which A1 represents a single bond or a divalent hydrocarbon group containing not more than three carbon atoms and in which the three valencies are each attached to a nitrogen atom, and the groups R are the same or different and, when individual atoms or groups, represent either hydrogen atoms or lower alkyl groups (i.e. containing not more than four carbon atoms), or, when pairs are linked together, form with the adjacent nitrogen atom a heterocyclic ring such as a pyrrolidino, piperidino or morpholino group) excluding those compounds in which simultaneously Y represents a sulphur atom, A represents a trivalent aliphatic chain of three carbon atoms and the R groups are alike and represent either methyl or ethyl groups. Such compounds are obtained by the interaction of a phenthiazine compound of the formula: <FORM:0800632/IV (b)/3> with a halogenodiamine of the formula: <FORM:0800632/IV (b)/4> or an acid addition salt thereof (wherein Hal represents a halogen atom and A1 either represents the group A as defined above or a group convertible by reduction into the group A) and, where A1 is other than A, reduction of the group A1 into the trivalent hydrocarbon group A. Alternatively, products of the first formula above in which Y represents an SO or SO2 group are obtained by oxidation of the corresponding phenthiazine compound in which Y represents a sulphur atom. The first reaction is preferably effected in e.g. toluene or xylene solution in the presence of a condensing agent such as an alkali metal, or the metal alkyl, metal aryl or the hydride, amide, hydroxide or alcoholate. As a result of isomerization during the reaction, a mixture of isomers is obtained having at the 10 position the groups: <FORM:0800632/IV (b)/5> and <FORM:0800632/IV (b)/6> respectively. The mixed isomers can be used therapeutically, or they can be separated by fractional crystallization of their dihydrochlorides from alcohol. Hydrohalides, 8-chloro-theophyllinates and methiodides of the products are mentioned. In Example (1) phenthiazine and 1 - dimethylamino - 2 - dimethylaminomethyl-3-chlorobutane are reacted in xylene in the presence of sodamide to give 10-[1-bis-(dimethylaminomethyl) - 2 - propyl] - phenthiazine (and its dihydrochloride). Similarly prepared are (2) 10 - [1 - bis - (diethylaminomethyl) - 2 - propyl] phenthiazine; (5) 10-(2 : 3-bispiperidino-1-propyl) phenthiazine; 3-chloro-10-(2 : 3-bispiperidino - 1 - propyl) phenthiazine, and 3-acetyl - 10 - (2 : 3 - bispiperidino - 1 - propyl)-phenthiazine (as its acid ditartrate).; (6) 9 : 9-dioxy - 10 - [2 : 3 - bis - (dimethylamino) 1-propyl]-phenthiazine. In further examples: (3) 10 - [2 : 3 - bis - (dimethylamino) - 1 - propyl]-phenthiazine in acetic acid is treated with sulphuric acid and hydrogen peroxide at 10 DEG to 20 DEG C. to give 9-oxy-10-[2 : 3-bis-(dimethylamino)-1-propyl] phenthiazine which is then converted (Example (4)) to its ethiodide. 3-Chloro - 9 - oxy - 10 - (2 : 3 - bispiperidino - 1-propyl) phenthiazine is prepared similarly. In preparing starting materials piperidine and epichlorhydrin are reacted at 60 DEG C. to give 1 : 3-bispiperidino - 2 - propanol which on treatment in chloroform with hydrogen chloride and thionyl chloride gives 1 : 3-bispiperidino-2-chloropropane dihydrochloride. Specification 800,635 is referred to.
GB3245954A 1954-11-09 1954-11-09 New derivatives of phenthiazine and processes for their production Expired GB800632A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3245954A GB800632A (en) 1954-11-09 1954-11-09 New derivatives of phenthiazine and processes for their production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3245954A GB800632A (en) 1954-11-09 1954-11-09 New derivatives of phenthiazine and processes for their production

Publications (1)

Publication Number Publication Date
GB800632A true GB800632A (en) 1958-08-27

Family

ID=10338919

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3245954A Expired GB800632A (en) 1954-11-09 1954-11-09 New derivatives of phenthiazine and processes for their production

Country Status (1)

Country Link
GB (1) GB800632A (en)

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