Novel opiate compounds, methods of making and methods of use

A compound represented by formula (II):

• 19
• R1 is an alkyl group or aralkyl group;
• and
• R3, R4, R5, R6 are each, independently, hydrogen, an alkyl group, —OH, —NHK, —NHR, —N(R)2, halogen, —OR, —CF3, —CN, —NO2, or —NHC(O)R, wherein when any of R3, R4, R5, or R6 is N(R)2 the R groups may, together, form a cyclic alkyl group;
• each R is, independently, an alkyl group, an aryl group, or an alkaryl group;
• and
• R7 is hydrogen or an alkyl group,
• or a pharmaceutically acceptable salt thereof.

A compound represented by formula (III):

• 20
• where
• R1 is an alkyl group or an aralkyl group;
• R2 is hydrogen, an alkyl group, an aralkyl group, ═O, —NH2, —NHR, —N(R)2, —NHC(O)R, —NRC(O)R, —NHC(O)R5, or —NRC(O)R5;
• R3 and R4 may be hydrogen or methyl, with the proviso that when R3 is methyl then R4 is hydrogen and when R3 is hydrogen then R4 is methyl;
• each R is, independently, an alkyl group, an aryl group, or an alkaryl group;
• and
• R5 is
• 21
• each X is, independently, halogen, —OH, —OR, an alkyl group, an aryl group, —NH2, —NHR, —N(R)2, —CF3, —CN, —C(O)NH2, —C(O)NHR, or —C(O)N(R)2;
• each R is, independently, an alkyl group, an aryl group, or an alkaryl group;
• n is 0 or an integer from 1 to 5;
• and
• Ra is hydrogen or an alkyl group,
• or a pharmaceutically acceptable salt thereof.

A compound represented by formula (IV):

• 22
• where
• Ra and Rb are each, independently, hydrogen or an alkyl group, or Ra and Rb, together, form a cycloalkyl group;
• each X is, independently, an alkyl group;
• ◯ is a five- or six-membered aryl or heteroaryl group;
• each Z is, independently, an alkyl group, —OH, —OR, halogen, —CF3, —CN, —NH2, —NHR, or —N(R)2, wherein when Z is —N(R)2 the R groups may, together, form a cyclic alkyl group;
• each R is, independently, an alkyl group, an aryl group, or an alkaryl group;
• each W is an alkyl group;
• n is 0 or an integer from 1 to 4;
• y is 0 or an integer from 1 to 5;
• z is 0 or an integer from 0 to 8;
• and
• R5 is an alkyl group, alkenyl group, or aralkyl group,
• or a pharmaceutically acceptable salt thereof.