Antitumor m-AMSA analog

Details Antitumor m-AMSA analog Antitumor m-AMSA analog

1984-06-18

1986-03-11

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546103, A61K 3147, C07D21910

Patent

active

045755531

ABSTRACT:
The compounds are of the class of 9-anilinoacridines, useful as antitumor agents and are analogs of m-AMSA. These compounds have the formula ##STR1## in which R.sup.1 is Br, Cl or CH.sub.3, and R.sup.2 is CH.sub.2 NHCH.sub.3, CH.sub.2 N(CHO)CH.sub.3 or CH.sub.2 NHCHO. Intermediate 3-substituted-9(10H)acridone-5-carboxylic acids are prepared by converting diphenylaminedicarboxylic acids via acyl chloride to dipiperidides, purifying the dipiperidides, treating said dipiperidides with phosphorous oxychloride in an inert organic solvent at a temperature in the range of about 70.degree. C. to 110.degree. C. to yield 9-acridine, subjecting said 9-acridine to mild acid hydroylsis to yield 9-acridone and thereafter hydroylzing said 9-acridones to the acid product.

REFERENCES:
J. Med. Chem. 19, 772, 1124, 1409 (1976).
Drugs of the Future 5, 277 (1980).
Denny, et al., J. Med. Chem. vol. 25, No. 3, pp. 267-315 (1982), pp. 276-278, 281, 284, 298 and 302-315 relied upon and supplied.

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