GB762711A - New phenthiazine derivatives and process for their preparation - Google Patents
New phenthiazine derivatives and process for their preparationInfo
- Publication number
- GB762711A GB762711A GB2164554A GB2164554A GB762711A GB 762711 A GB762711 A GB 762711A GB 2164554 A GB2164554 A GB 2164554A GB 2164554 A GB2164554 A GB 2164554A GB 762711 A GB762711 A GB 762711A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenthiazine
- chloroethyl
- aminopropyl
- compounds
- ethyl
- 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
-
- 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
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises phenthiazine derivatives of the formula <FORM:0762711/IV(b)/1> and their salts, including quaternary ammonium derivatives, wherein X represents a hydrogen or halogen atom or a methyl, methoxy, aryl or aryloxy group, R represents a hydrogen atom or a methyl, methoxy, ethyl, b -chloroethyl or benzyl group and A represents a saturated divalent straight or branched aliphatic radical containing 2 or 3 carbon atoms. Such compounds are obtained by reacting the corresponding mono- or di-N-(b -hydroxyethyl) derivative with any known reagent for replacing a hydroxy group in an aliphatic chain by a chlorine atom. Thionyl chloride, phosphorus oxychloride and phosphorus chlorides are specified. Salts, quaternary compounds and addition compounds, e.g. with 8-chloro-theophyllinates are mentioned. In Example (1) 10 - [2 - (N - b - chloroethyl - N - ethyl) - aminoethyl]-phenthiazine hydrochloride is prepared by reacting thionyl chloride with 10-[2-(N-b -hydroxyethyl - N - ethyl) aminoethyl] - phenthiazine, which is itself obtained by treating 10-(2-chlorethyl) - phenthiazine with N - ethylmonoethanolamine and copper powder. Further examples describe similar compounds having in some cases a 3-chlorine substituent and in the 10-position groups selected from 3-(N-b -chlorethyl-N-ethyl) aminopropyl, 2-(N-b -chloroethyl-N - ethyl) aminopropyl, 3 - (di - N - b - chloroethyl) aminopropyl, 2-(N-b -chloroethyl) aminopropyl, 3 - (N - b - chloroethyl) aminopropyl, 2 - (N - b - chloroethyl - N - methyl) aminopropyl, 3 - (N - b - chloroethyl - N - benzyl) aminopropyl and 2-(N-b -chloroethyl-N-benzyl) aminoethyl groups. The preparation of the N-hydroxyalkyl compounds used as starting materials by reaction of the appropriate N-chloralkylphenthiazine with a substituted ethanolamine is described. Compounds with methyl, methoxy, phenyl and phenoxy groups in the 3 position are also referred to. Other starting materials. 10-(2-Hydroxypropyl)-phenthiazine is obtained by the hydrochloric acid hydrolysis of 10-(2-tetrahydropyranyloxypropyl) phenthiazine, itself obtained by the action of 2-(2-tetrahydropyranyloxy)-1-chloropropane on phenthiazine in the presence of sodamide. 3 - Chloro - 10 - (3 - hydroxypropyl)-phenthiazine is obtained from 3-chlorophenthiazine and 3-(2-tetrahydropyranyloxy)-1-chloropropane. 3 - Chloro - 10 - (2 - hydroxypropyl)-phentiazine is obtained by the acid hydrolysis of 3-chloro-10-(2-tetrahydropyranyloxypropyl-phenthiazine, itself obtained by the reaction of 2 - (2 - tetrahydropyranyloxy) - 1 - chloropropane on phenthiazine in the presence of sodamide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2164554A GB762711A (en) | 1954-07-23 | 1954-07-23 | New phenthiazine derivatives and process for their preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2164554A GB762711A (en) | 1954-07-23 | 1954-07-23 | New phenthiazine derivatives and process for their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB762711A true GB762711A (en) | 1956-12-05 |
Family
ID=10166409
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2164554A Expired GB762711A (en) | 1954-07-23 | 1954-07-23 | New phenthiazine derivatives and process for their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB762711A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2500039A1 (en) * | 2007-03-12 | 2012-09-19 | Nektar Therapeutics | Oligomer-antihistamine conjugates |
-
1954
- 1954-07-23 GB GB2164554A patent/GB762711A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2500039A1 (en) * | 2007-03-12 | 2012-09-19 | Nektar Therapeutics | Oligomer-antihistamine conjugates |
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