Inhibitors of UDP-Galactopyranose Mutase

A method for inhibiting the growth of a microorganism which comprises contacting the microorganism or an environment containing the microorganism with an effective amount of one or more compounds formula II or salts thereof as defined herein, wherein

• formula II is
• and salts thereof,
• where:
• Y is —OR4, or —NH2;
• p is 1, 2 or 3;
• R4 is selected from the group consisting of an alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group, each of which groups are optionally substituted, and hydrogen;
• each R5 is independently hydrogen or an optionally substituted alkyl group having 1-3 carbon atoms;
• and
• R10 is an —NR6R7 group or hydrogen,
• where:
• R6 and R7 are independently selected from the group consisting of hydrogen, or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl groups;
• where substitution, if present, is substitution with one or more substituents selected from the group consisting of halogen, nitro, cyano, isocyano, thiocyano, isothiocyano, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, sulfonamide (—SO2—N(RF)2), azide, sulfonyl (—SO2—RF), —COORF, —CORF, —CON(RF)2, —N(RF)2, and C1-C6 haloalkyl groups, where RF is hydrogen or a C1-C6 alkyl group.

A method of treating an infection by a microorganism having UGM in an individual in need of such treatment by administering to the individual an effective amount of one or more compounds of formula II or salts thereof, wherein:

• formula II is
• and salts thereof,
• where:
• Y is —OR4, or —NH2;
• p is 1, 2 or 3;
• R4 is selected from the group consisting of an alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group, each of which groups are optionally substituted, and hydrogen;
• each R5 is independently hydrogen or an optionally substituted alkyl group having 1-3 carbon atoms;
• and
• R10 is an —NR6R7 group or hydrogen,
• where:
• R6 and R7 are independently selected from the group consisting of hydrogen, or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl groups;
• where optional substitution for formula I and II is substitution with one or more substituents selected from the group consisting of halogen, nitro, cyano, isocyano, thiocyano, isothiocyano, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, sulfonamide (—SO2—N(RF)2), azide, sulfonyl (—SO2—RF), —COORF, —CORF, —CON(RF)2, —N(RF)2, and C1-C6 haloalkyl groups, where RF is hydrogen or a Cl-C6 alkyl group.

A pharmaceutically acceptable composition which comprises one or more compounds of formulas I or II or salts thereof and a pharmaceutically acceptable carrier wherein formula II is

• and salts thereof,
• where:
• Y is —OR4, or —NH2;
• p is 1, 2 or 3;
• R4 is selected from the group consisting of an alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group, each of which groups are optionally substituted, and hydrogen;
• each R5 is independently hydrogen or an optionally substituted alkyl group having 1-3 carbon atoms;
• and
• R10 is an —NR6R7 group or hydrogen,
• where:
• R6 and R7 are independently selected from the group consisting of hydrogen, or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl groups;
• where optional substitution for formula I and II is substitution with one or more substituents selected from the group consisting of halogen, nitro, cyano, isocyano, thiocyano, isothiocyano, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, sulfonamide (—SO2—N(RF)2), azide, sulfonyl (—SO2—RF), —COORF, —CORF, —CON(RF)2, —N(RF)2, and C1-C6 haloalkyl groups, where RF is hydrogen or a C1-C6 alkyl group.

A compound of formula II or a salt thereof, wherein formula II is

• and salts thereof,
• where:
• Y is —OR4, or —NH2;
• p is 1, 2 or 3;
• R4 is selected from the group consisting of an alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl group, each of which groups are optionally substituted, and hydrogen;
• each R5 is independently hydrogen or an optionally substituted alkyl group having 1-3 carbon atoms;
• and
• R10 is an —NR6R7 group or hydrogen,
• where:
• R6 and R7 are independently selected from the group consisting of hydrogen, or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl groups;
• where optional substitution is substitution with one or more substituents selected from the group consisting of halogen, nitro, cyano, isocyano, thiocyano, isothiocyano, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, sulfonamide (—SO2—N(RF)2), azide, sulfonyl (—SO2—RF), —COORF, —CORF, —CON(RF)2, —N(RF)2, and C1-C6 haloalkyl groups, where RF is hydrogen or a C1-C6 alkyl group, with the exception that the compound is not compound 10, 14 or 15.