Patent GB-450254-A (GB)
Title: Process for the manufacture of acridinium compounds
IPC: C07D219/12
Filed: 1935-01-11
Abstract: 10-Alkyl- or aralkylacridinium compounds substituted in the 9-position by an amino group containing a further basic radicle, are obtained (1) by replacing a reactive substituent in the 9-position with an aliphatic polyamine containing at least one primary or secondary amino group, (II) by first replacing the reactive substituent in 9-position by an amino alcohol or aminoalkylhalide group, and treating the product with a primary or secondary amine, the intermediately-formed hydroxyalkylamino compounds being esterified, if desired, prior to the reaction with amine, and (III) by ring-closing the amides of N-alkyl- or N-aralkyl-diarylamino-2-carboxylic acids substituted in the amide group by an aliphatic amine radicle.  The basic radicle attached to the 9-amino group may contain one or more nitrogen atoms and may be substituted by OH-groups or interrupted by nitrogen or sulphur atoms. The acridine nucleus may be substituted by halogen, alkyl or alkoxy groups, and nitro and amino group. Specifications 267,169, [Class 2 (iii)], and 363,392 are referred to.  According to examples (1) 9-chloro-10-methylacridinium chloride is treated with diethylaminoethylamine and converted to the quaternary hydrochloride; the methylene disalicyclic quaternary salt of the 9 - a  - diethylamino - d  - pentylamino - 10 methylacridinium compound may be obtained by the same method and precipitation from the hydrochloride; (2) 9 - chloro - 10 - benzylacridinium chloride (obtained by treating 10-benzylacridone with PCl5) is treated with a -diethylamino-d -amino-pentane, and converted to the quaternary citrate; (3) 6 : 9-dichloro-10-methylacridinium chloride, (obtained by treating 6 - chloro - 10 - methylacridone with PCl5) are treated with a  - diethylamino - d  - aminopentane, and converted to the methylenedisalicylic salt; (4) 2-methoxy-6 : 9-dichloro10-methylacridinium, (obtained by treating 2 - methoxy - 6 - chloro - 10 - methyl - acridone with PCl5) is treated with as-diethylaminoethylamine to give the corresponding 9-substituted derivative; 2-methoxy-6-chloro-9-(a -diethylamino - b  - hydroxy - g - propyl - amino)-10-methylacridinium chloride is obtained in a similar manner.  Samples have been furnished under Sect. 2 (5) of the 1 : 1<1>-methylene-di(2-hydroxy-3-naphthoic acid salt of 4-nitro-9(b -diethylaminoethylamino)-10-methylacridinium obtained by the method of process (III) and by precipitation from the citric salt; the salt of 4-nitro-9(w-diethylaminoethyl - g  - mercapto - propylamino-10-methyl-acridinium with the same methyleneoxynaphthoic acid is obtained in a similar manner from diethylaminoethyl-g -mercaptopropylamine, (prepared by treating bromopropylphthalimide with b  - mercaptoethyldiethylamine and hydrolysis of the phthalic residue); the dihydrochloride salt of 2-methoxy-9(g  - diethylamino - b  - hydroxypropylamino - ethylamino) acridinium-10-methylchloride prepared by method I from the triamine g -diethylamino - b  - hydroxy - propylamino - ethylamine, which may be obtained by treating 1 - amino - 3 - diethylamino - 2 - propanol (cf. Specification 275,622, [Class 2 (iii)]), with bromethylphthalimide, followed by saponification of the product.  The Specification as open to inspection under Sect. 91 refers to the use of basic radicles in which the aliphatic group may be interrupted also by oxygen.  This subject-matter does not appear in the Specification as accepted.