A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof:

##STR00001##

where: X.sup.1 is a branched or unbranched C.sub.1-10 alkyl, (CH.sub.2).sub.sNH(CH.sub.2).sub.t, (CH.sub.2).sub.sO(CH.sub.2).sub.t, or (CH.sub.2).sub.sC(NH.sub.2)(CH.sub.2).sub.vNH(CH.sub.2).sub.t, where s, t and v are each, independently an integer from 1 to 5; A and B are each, independently, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups; C and D are each, independently, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl-C.sub.1-6alkyl, C.sub.3-7 heterocycloalkyl, C.sub.3-7 heterocycloalkyl-C.sub.1-6 alkyl, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups; each R.sup.g is, independently, halogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, hydroxyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, amino, C.sub.1-6alkylamino, or di-C.sub.1-6alkylamino; and n.sup.1 and p.sup.1 are each, independently, integers from 1 to 10.

The present invention relates generally to glutaminase inhibitors of Formula I, Formula II, or Formula III, as well as pharmaceutical compounds containing them and methods of their use.

The present invention relates generally to glutaminase inhibitors of Formula I, Formula II, or Formula III, as well as pharmaceutical compounds containing them and methods of their use.

A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: ##STR00001##
where:
X.sup.1 is a branched or unbranched C.sub.1-10 alkyl, (CH.sub.2).sub.sNH(CH.sub.2).sub.t, (CH.sub.2).sub.sO(CH.sub.2).sub.t, or (CH.sub.2).sub.sC(NH.sub.2)(CH.sub.2).sub.vNH(CH.sub.2).sub.t, where s, t and v are each, independently an integer from 1 to 5;
A and B are each, independently, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups;
C and D are each, independently, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl-C.sub.1-6alkyl, C.sub.3-7 heterocycloalkyl, C.sub.3-7 heterocycloalkyl-C.sub.1-6 alkyl, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups;
each R.sup.g is, independently, halogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, hydroxyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, amino, C.sub.1-6 alkylamino, or di-C.sub.1-6alkylamino; and
n.sup.1 and p.sup.1 are each, independently, integers from 1 to 10.

A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: ##STR00001##
where:
X.sup.1 is a branched or unbranched C.sub.1-10 alkyl, (CH.sub.2).sub.sNH(CH.sub.2).sub.t, (CH.sub.2).sub.sO(CH.sub.2).sub.t, or (CH.sub.2).sub.sC(NH.sub.2)(CH.sub.2).sub.vNH(CH.sub.2).sub.t, where s, t and v are each, independently an integer from 1 to 5;
A and B are each, independently, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups;
C and D are each, independently, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl-C.sub.1-6alkyl, C.sub.3-7 heterocycloalkyl, C.sub.3-7 heterocycloalkyl-C.sub.1-6 alkyl, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups;
each R.sup.g is, independently, halogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, hydroxyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, amino, C.sub.1-6 alkylamino, or di-C.sub.1-6alkylamino; and
n.sup.1 and p.sup.1 are each, independently, integers from 1 to 10.

An organic electroluminescent device of which emission life may be improved. The organic electroluminescent device includes an anode, an emission layer, and an anode-side hole transport layer provided between the anode and the emission layer and including an anode-side hole transport material. An electron accepting material is doped in the anode-side hole transport layer. An intermediate hole transport material layer is provided between the anode-side hole transport layer and the emission layer and includes an intermediate hole transport material, and an emission layer-side hole transport layer is provided between the intermediate hole transport material layer and the emission layer and adjacent to the emission layer. The emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1.

##STR00001##

An organic electroluminescent device of which emission life may be improved. The organic electroluminescent device includes an anode, an emission layer, and an anode-side hole transport layer provided between the anode and the emission layer and including an anode-side hole transport material. An electron accepting material is doped in the anode-side hole transport layer. An intermediate hole transport material layer is provided between the anode-side hole transport layer and the emission layer and includes an intermediate hole transport material, and an emission layer-side hole transport layer is provided between the intermediate hole transport material layer and the emission layer and adjacent to the emission layer. The emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1.

##STR00001##

An organic electroluminescent device of which emission life may be improved. The organic electroluminescent device includes an anode, an emission layer, and an anode-side hole transport layer provided between the anode and the emission layer and including an anode-side hole transport material. An electron accepting material is doped in the anode-side hole transport layer. An intermediate hole transport material layer is provided between the anode-side hole transport layer and the emission layer and includes an intermediate hole transport material, and an emission layer-side hole transport layer is provided between the intermediate hole transport material layer and the emission layer and adjacent to the emission layer. The emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1. ##STR00001##

An organic electroluminescent device of which emission life may be improved. The organic electroluminescent device includes an anode, an emission layer, and an anode-side hole transport layer provided between the anode and the emission layer and including an anode-side hole transport material. An electron accepting material is doped in the anode-side hole transport layer. An intermediate hole transport material layer is provided between the anode-side hole transport layer and the emission layer and includes an intermediate hole transport material, and an emission layer-side hole transport layer is provided between the intermediate hole transport material layer and the emission layer and adjacent to the emission layer. The emission layer-side hole transport layer includes an emission layer-side hole transport material represented by the following Formula 1. ##STR00001##

Provided herein are PLpro inhibitors and methods of treating and/or preventing an infection caused by a coronavirus by administration of one or more of said PLpro inhibitors to a subject in need thereof, as well as pharmaceutical formulations and kits for use in these methods.