US 5,322,858 AGranted

N,N'-substituted imidodicarbonimidic diamides derived from hydroxylamines

AssigneeJacobus Pharmaceutical Company, Inc.

InventorsCraig Canfield, David P. Jacobus, Neil J. Lewis

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Abstract

There are provided compounds of the formula ##STR1## wherein R.sup.1 is a substituted or unsubstituted divalent aliphatic group of 1 to 16 carbon atoms; wherein the substituents are mono or poly and are selected from the group consisting of lower alkyl, aryl and arlkyl, R.sup.3 is selected from the group consisting of same group of values as R.sup.5, R.sup.5 is selected from the group consisting of substituted and unsubstituted alkyl of 1-10 carbon atoms, aryl, cycloalkyl and heterocycloalkyl of 3-8 carbon atoms, wherein the substituents are mono or poly and are selected from the group consisting of lower alkyl, cycloalkyl of 3-8 carbon atoms, lower alkenyl, lower alkynyl, nitro, lower alkoxy, lower alkoxycarbonyl, phenyl loweralkyl, phenyl, mono and polyhalophenyl, phenoxy, mono and polyhalophenoxy, R.sup.6 and R.sup.7 may be the same or different and are hydrogen, alkanoyl or alkoxyalkanoyl, R.sup.7 may also have the same value as R.sup.5, Y is oxygen or sulfur, m is 0 or 1, q is 0 or 1, wherein the prefix alk designates moieties which are straight chain or branched chain, and the term lower designates 1-6 carbon atoms and the unmodified term alk signifies 1-24 carbon atoms, the respective tautomers thereof, the pharmaceutically acceptable salts and addition salts thereof and the hydrates of said salts and addition salts. There are further provided methods of protecting subjects liable thereto from infections caused by an organism of the group Plasmodium sp., Mycobacterium sp. and Pneumocystis carinii by administering to a subject liable to such infection, a prophylactically effective amount of a compound of the foregoing formula. These compounds will also reduce the level of infection where said subjects have already been infected.

A compound of the formula ##STR7## wherein:

R.sup.1 is substituted or unsubstituted divalent aliphatic group of 1 to 16 carbon atoms;
wherein the substituents are mono or poly and are selected from the group consisting of lower alkyl, aryl and aralkyl,
R.sup.3 is selected from the group consisting of same group of values as R.sup.5 other than carbocycloaryl, and when further bonded to the nitrogen to which it is attached, a saturated heterocycle of 4-8 carbon atoms,
R.sup.5 is selected from the group consisting of substituted and unsubstituted alkyl of 1-10 carbon atoms, cycloalkyl, heterocycloalkyl of 3-8 carbon atoms, mono and polycarbocycloaryl of 4-7 atoms per ring, wherein the substituents are;
mono or poly and are selected from the group consisting of lower alkyl, halo lower alkyl, cycloalkyl of 3-8 carbon atoms, lower alkenyl, lower alkynyl, nitro, lower alkoxy, lower alkoxy-carbonyl, phenyl loweralkyl, phenyl, mono and polyhalophenyl, phenoxy, mono and polyhalophenoxy;
and halo provided however, that such halo substitution is in a mono and polycarbocycloaryl of 4-7 atoms per ring,
R.sup.6 and R.sup.7 which may be the same or different are hydrogen, alkanoyl or alkoxy alkanoyl, and when further bonded to the nitrogen to which either is attached, a saturated heterocycle of 4-8 carbon atoms, and
R.sup.7 may also be selected from the group consisting of same group of values as R.sup.5, and when further bonded to the nitrogen to which it is attached, a saturated or unsaturated heterocycle of 4-8 carbon atoms,
Y is oxygen or sulfur,
q is 0 or 1,
m is 1 or 0, having the latter value where R.sup.3 is a moiety having two bonds attached to N.sup.5,
provided that unless otherwise stated the prefix alk designates moieties which are straight chain or branched chain of 1-24 carbon atoms, and when further prefixed by the term lower, designates 1-6 carbon atoms,
the respective tautomers thereof, the pharmaceutically acceptable salts and addition salts thereof and the hydrates of said salts and addition salts and mono and diacyl derivatives thereof.

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Abstract

Claims32