2,6-Bis(1-piperidinoalkylideneamino)anthraquinones and method of treating cecal and hepatic amebic infections therewith

Information

  • Patent Grant
  • 4118498
  • Patent Number
    4,118,498
  • Date Filed
    Tuesday, November 15, 1977
    46 years ago
  • Date Issued
    Tuesday, October 3, 1978
    45 years ago
Abstract
Novel 2,6-bis(1-piperidinoalkylideneamino)anthraquinones that are effective against cecal and hepatic amebic infestations in warm-blooded animals are disclosed.
Description
Claims
  • 1. A compound of the formula: ##STR6## wherein R.sub.1 is selected from the group consistng of hydrogen and lower alkyl (C.sub.1 -C.sub.2) and R.sub.2 is selected from the group consisting of hydrogen and lower alkyl (C.sub.1 -C.sub.2) and pharmaceutically acceptable salts thereof.
  • 2. The compound according to claim 1, 2,6-bis(piperidinomethyleneamino)anthraquinone.
  • 3. The compound according to claim 1, 2,6-bis[(1-piperidinopropylidene)amino]anthraquinone.
  • 4. The compound according to claim 1, 2,6-bis[(1-piperidinoethylidene)amino]anthraquinone.
  • 5. The compound according to claim 1, 2,6-bis[1-(4-methyl-piperidinoethylidene)amino]anthraquinone.
  • 6. A method of treating cecal and hepatic amebic infections in warm-blooded animals which comprises administering to said animals an amount effective against said infections of a compound of the formula: ##STR7## wherein R.sub.1 is selected from the group consisting of hydrogen and lower alkyl (C.sub.1 -C.sub.2) and R.sub.2 is selected from the group consisting of hydrogen and lower alkyl (C.sub.1 -C.sub.2) and pharmaceutically acceptable salts thereof.
  • 7. The method according to claim 6 wherein the compound is 2,6-bis(piperidinomethyleneamino)anthraquinone.
  • 8. The method according to claim 6 wherein the compound is 2,6-bis(1-piperidinopropylidene)amino anthraquinone.
  • 9. The method according to claim 6 wherein the compound is 2,6-bis[(1-piperidinoethylidene)amino]anthraquinone.
  • 10. The method according to claim 6, wherein the compound is 2,6-bis[1-(4-methyl-piperidinoethylidene)amino]anthraquinone.
CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation of application Ser. No. 772,038, filed Feb. 25, 1977, now abandoned, which is a continuation-in-part of application Ser. No. 699,816, filed June 24, 1976, now abandoned, which is a division of application Ser. No. 606,805, filed Aug. 22, 1975, now abandoned. U.S. Pat. No. 3,184,482 discloses a compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or lower alkyl and R.sub.3, R.sub.4, and R.sub.5 are hydrogen, hydroxy or ##STR2## Utility is described as antibacterial antiviral, antiprotozoal and anthelmintic. U.S. Pat. No. 3,654,319, Neeff, make a gratuitous disclosure of a compound of the formula: ##STR3## but the compound is neither claimed nor exemplified. Neeff does exemplify 1,4- and 1,5-diaminoanthraquinones of the following formulae: ##STR4## but Applicants have prepared these compounds and have found them to be inactive for the claimed utility. This invention is concerned with novel compounds of the formula: ##STR5## wherein R.sub.1 is selected from the group consisting of hydrogen and lower alkyl (C.sub.1 -C.sub.4) and R.sub.2 is selected from the group consisting of hydrogen and lower alkyl (C.sub.1 -C.sub.2) and pharmaceutically acceptable salts thereof. This invention is also concerned with the method of treating cecal and hepatic amebic infections in warm-blooded animals with the disclosed compounds.

US Referenced Citations (2)
Number Name Date Kind
3184482 Steiger May 1965
3974186 Fleming et al. Aug 1976
Foreign Referenced Citations (1)
Number Date Country
2,521,357 Nov 1976 DEX
Divisions (1)
Number Date Country
Parent 606805 Aug 1975
Continuations (1)
Number Date Country
Parent 772038 Feb 1977
Continuation in Parts (1)
Number Date Country
Parent 699816 Jun 1976