GB786384A - Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same - Google Patents

Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same

Info

Publication number
GB786384A
GB786384A GB21868/55A GB2186855A GB786384A GB 786384 A GB786384 A GB 786384A GB 21868/55 A GB21868/55 A GB 21868/55A GB 2186855 A GB2186855 A GB 2186855A GB 786384 A GB786384 A GB 786384A
Authority
GB
United Kingdom
Prior art keywords
phenothiazine
carboxylic acid
alk
bases
prepared
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
GB21868/55A
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.)
Wyeth Canada Inc
Original Assignee
Ayerst Mckenna and Harrison Inc
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 Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc
Publication of GB786384A publication Critical patent/GB786384A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
    • 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
    • A61K31/5415—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 ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom

Landscapes

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

Abstract

The invention comprises basic esters of the formula <FORM:0786384/IV (b)/1> where "Alk" represents a straight-chain or branched-chain alkylene group having 2 or 3 carbon atoms and R1 and R2 are straight or branched chain alkyl groups containing not more than 6 carbon atoms and acid addition salts and quaternary ammonium salts of such bases. The bases are obtained by reacting at elevated temperature a phenothiazine-10-carboxylic acid halide and a basically substituted alkoxyalkanol of the formula HO-Alk-O-Alk-NR1R2 Addition salts may be formed with hydrochloric, hydrobromic, sulphuric, maleic, oxalic, tartaric, citric, picric and picrolonic acids. As quaternizing agents are specified methyl and ethyl bromides, iodides and chlorides and di-methyl sulphate. In examples: (1) phenothiazine-10-carboxylic acid chloride and b -di-isopropylamino-ethoxyethanol are reacted to form b - diisopropylaminoethoxyethyl phenothiazine-10-carboxylate. The corresponding dimethyl and diethylamino derivatives are obtained similarly; (2) the first product of Example (1) is converted to the picrate; (3) the hydrochlorides of the three esters obtained in Example (1) are prepared and purified by reprecipitation with ether from their methanol solutions; (4), (5) and (6) the maleate, tartrate, oxalate and picrolonate of the diisopropyl derivative of Example (1) are prepared; (7) the bases prepared in Example (1) are quaternated by heating with excess methyl bromide.
GB21868/55A 1955-01-31 1955-07-28 Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same Expired GB786384A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US786384XA 1955-01-31 1955-01-31

Publications (1)

Publication Number Publication Date
GB786384A true GB786384A (en) 1957-11-20

Family

ID=22145330

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21868/55A Expired GB786384A (en) 1955-01-31 1955-07-28 Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same

Country Status (1)

Country Link
GB (1) GB786384A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3238199A (en) * 1961-02-27 1966-03-01 Hoffmann La Roche Phenothiazine compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3238199A (en) * 1961-02-27 1966-03-01 Hoffmann La Roche Phenothiazine compounds

Similar Documents

Publication Publication Date Title
GB828393A (en) New phenthiazine derivatives and processes for their preparation
GB786384A (en) Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same
GB714230A (en) Pyridine compounds and process for the manufacture thereof
GB872997A (en) Substituted ún-aminoalkoxy-acyl benzenes and processes for their manufacture
GB778936A (en) Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls
GB1080496A (en) Improvements in or relating to a new derivatives of 2,4,6-triiodo-3-hydroxy-benzene and process for preparing the same
GB781237A (en) Anthracene derivatives and their preparation
GB668659A (en) Improvements in and relating to basic derivatives of imino dibenzyl compounds
GB834370A (en) Phenothiazine derivatives
US2655503A (en) Quaternary salts of y-stilbazolines
GB738690A (en) Improvements in or relating to derivatives of piperazine and the manufacture thereof
GB845822A (en) Improvements in or relating to piperidine derivatives
GB729967A (en) Isonicotinic acid derivatives and process for the manufacture thereof
GB799573A (en) Improvements in or relating to method of preparing 2-halo-10-(1-substituted-3-pyrrolidylmethyl) phenothiazines and salts thereof, and the compounds resulting therefrom
GB843908A (en) Novel morphinan derivatives and the manufacture thereof
GB886269A (en) Improvements in or relating to photographic colour development
GB793010A (en) Substituted piperidine 4-carboxylic esters
GB899556A (en) Substituted isonicotinic acid amides and process for their manufacture
GB757650A (en) Improvements in or relating to substituted imidazolines and the preparation thereof
ES214693A1 (en) New derivatives of phenthiazine and their method of preparation
GB931788A (en) Improvements in or relating to benzhydryl esters
GB765047A (en) Heterocyclic nitrogen compounds and methods for obtaining the same
GB855862A (en) Basic esters of xanthylidene acetic acid
GB748358A (en) Improvements in or relating to pyrimidines
GB1056475A (en) Process for preparing 4-amino-pyrazolone derivatives