GB821012A - New phenthiazine derivatives and processes for their preparation - Google Patents
New phenthiazine derivatives and processes for their preparationInfo
- Publication number
- GB821012A GB821012A GB333/58A GB33358A GB821012A GB 821012 A GB821012 A GB 821012A GB 333/58 A GB333/58 A GB 333/58A GB 33358 A GB33358 A GB 33358A GB 821012 A GB821012 A GB 821012A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazine
- phenthiazinyl
- propyl
- chloro
- formula
- 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
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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0821012/IV (a)/1> and their acid addition and quaternary ammonium salts (wherein A is a straight or branched chain divalent saturated aliphatic hydrocarbon group with 2 to 4 carbon atoms, Y is a sulphur atom or an SO or SO2 group, X is a hydrogen or halogen atom or a lower alkyl or alkoxy group or a cyano, methylthio or dimethylsulphamoyl group, R1 and R2 are the same or different and either each is a hydrogen atom or a lower alkyl, benzyl or cyclo-hexyl group, or R1 and R2 together with the adjacent nitrogen atom collectively represent a pyrrolidino, piperidino or morpholino group, and n is 1 or 2), and the preparation thereof by: (a) reacting a phenthiazine of the formula <FORM:0821012/IV (a)/2> with a piperazine derivative of the formula <FORM:0821012/IV (a)/3> (wherein Z is the acid residue of a reactive ester), (b) reacting a phenthiazine of the formula <FORM:0821012/IV (a)/4> with a piperazine derivative of the formula <FORM:0821012/IV (a)/5> (c) reacting a phenthiazine of the formula <FORM:0821012/IV (a)/6> with a reactive ester of the formula <FORM:0821012/IV (a)/7> (d) reacting a phenthiazine of the formula <FORM:0821012/IV (a)/8> (wherein -COZ1 is a functionally converted carboxyl group such as an acid halide, azide or ester group) with an amine of the formula <FORM:0821012/IV (a)/9> (e) decarboxylating a phenthiazine-10-carboxylate of the formula <FORM:0821012/IV (a)/100> by heating, preferably to a temperature above 100 DEG C., until evolution of carbon dioxide ceases. The phenthiazine derivatives in which Y is an SO or SO2 group may also be made by oxidizing the corresponding phenthiazines in which Y is a sulphur atom or SO group. The word "lower" means that the group in question contains not more than four carbon atoms. Other methods for preparing the compounds of the invention are described. Suitable acid addition salts are the hydrohalides, nitrates, phosphates, sulphates, citrates, fumarates, maleates, oxalates, tartrates, methane sulphonates and ethanedisulphonates. Quaternary ammonium salts may be made from organic halides (e.g. methyl or ethyl bromide, chloride or iodide, or allyl or benzyl bromide or chloride) or other reactive esters (e.g. toluene-p-sulphonates). The compounds of the invention have therapeutic properties. The following compounds are made in the examples: 1-[3-(3-chloro - 10 - phenthiazinyl)propyl] - 4 - dimethyl-carbamoylmethyl-piperazine and its hydrochloride, 1 - [3 - (3 - chloro - 10 - phenthiazinyl)-propyl] - 4 - carbamoylmethyl - piperazine, 1-[3 - (3 - chloro - 10 - phenthiazinyl)propyl] - 4 - carbamoylethyl - piperazine, 1 - [3 - (3 - chloro - 10 - phenthiazinyl)propyl] - 4 - dimethylcarbamoylethyl - piperazine and its dimaleate, 1 - [3 - (3 - chloro - 10 - phenthiazinyl)propyl]-4-diethylcarbamoylmethyl - piperazine and its dihydrochloride, 1 - [3 - (3 - chloro - 10 - phethiazinyl)propyl]-4-morpholinocarbonylmethyl-piperazine, 1 - [3 - (3 - chloro - 10 - phenthiazinyl)-propyl] - 4 - piperidinocarbonylmethyl-piperazine and its dihydrochloride, 1-[3-(3-chloro-10-phenthiazinyl)propyl] - 4 - 11 - pyrrolidinylcarbonylmethyl-piperazine and its dihydrochloride and dimethiodide, 1 - [3 - (3 - methoxy - 10 - phenthiazinyl)propyl] - 4 - dimethylcarbamoylmethyl-piperazine and its hydrochloride, 1-[1-(3 - chloro - 10 - phenthiazinyl) - 2 - propyl] - 4 - dimethylcarbamoylmethyl - piperazine and its hydrochloride, 1 - [2 - (10 - phenthiazinyl)ethyl]-4 - dimethylcarbamoylmethyl - piperazine and its dihydrochloride, 1 - [3 - (3 - dimethylsulphamoyl - 10 - phenthiazinyl)propyl] - 4 - dimethyl-carbamoylmethyl-piperazine and its dimethanesulphonate, 1-[3-(3 - chloro - 10 - phenthiazinyl)-propyl]-4- methylcarbamoylmethyl - piperazine and its dihydrochloride, 1-[3-(3-chloro-10-phenthiazinyl)propyl] - 4 - cyclohexylcarbamoylmethyl - piperazine, 1 - [3 - (3 - chloro - 10 - phentiazinyl)propyl] - 4 - benzylcarbamoylmethyl - piperazine, 1 - [3 - (3 - cyano - 10 - phenthiazinyl)propyl] - 4 - 11 - pyrrolidinylcarbonylmethyl-piperazine and its dimaleate, 1-[3 - (3 - methylthio - 10 - phenthiazinyl)propyl] 4 - 11 - pyrrolidinylcarbonylmethyl - piperazine and its dimaleate, 1-[3-(3-chloro-9-oxy-10-phenthiazinyl)propyl] - 4 - carbamoylethyl - piperazine, 1 - [3 - (3 - chloro - 9:9 - dioxy - 10 - phenthiazinyl)propyl] - 4 - 11 - pyrrolidinylcarbonylmethyl-piperazine. 1-Dimethyl carbamoylmethyl-piperazine is made from anhydrous piperazine and N-dimethylchloracetamide; 1 - chloro - propan - 3 - ol is reacted with 1-dimethylcarbamoylmethyl-piperazine to give 1-(3-hydroxypropyl)-4-dimethylcarbamoylmethyl-piperazine, which with thionyl chloride gives 1-(3-chloropropyl)-4-dimethylcarbamoylmethyl-piperazine; 1 - [3 - (3 - chloro - 10 - phenthiazinyl)carbonyloxypropyl] - 4 - dimethylcarbamoylmethyl-piperazine (the dimethyl sulphonate of which is also made) is prepared by reacting 3 - chlorophenthiazinyl - 10 - carbonyl chloride with 1 - (3 - hydroxypropyl) - 4 - dimethylcarbamoylmethyl - piperazine; 1-[3-(3-chloro - 10 - phenthiazinyl)propyl] - 4 - methoxy - carbonylmethyl-piperazine is made from 1-[3-(3-chloro - 10 - phenthiazinyl)propyl] - piperazine and methyl bromoacetate; 1-11-pyrrolidinylcarbonylmethyl-piperazine is made from anhydrous piperazine and chloracetopyrrolidide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR821012X | 1957-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB821012A true GB821012A (en) | 1959-09-30 |
Family
ID=9274852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB333/58A Expired GB821012A (en) | 1957-01-15 | 1958-01-03 | New phenthiazine derivatives and processes for their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB821012A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3112310A (en) * | 1962-01-15 | 1963-11-26 | Searle & Co | 10-alkylaminoalkylphenothiazine-2-carboxamides |
JP2002536442A (en) * | 1999-02-10 | 2002-10-29 | サノフィ−サンテラボ | (1-Phenacyl-3-phenyl-3-piperidylethyl) piperidine derivative, method for producing the same, and pharmaceutical composition containing the same |
-
1958
- 1958-01-03 GB GB333/58A patent/GB821012A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3112310A (en) * | 1962-01-15 | 1963-11-26 | Searle & Co | 10-alkylaminoalkylphenothiazine-2-carboxamides |
JP2002536442A (en) * | 1999-02-10 | 2002-10-29 | サノフィ−サンテラボ | (1-Phenacyl-3-phenyl-3-piperidylethyl) piperidine derivative, method for producing the same, and pharmaceutical composition containing the same |
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