Heat-Labile Prodrugs

A prodrug of a phenolic drug compound, the prodrug having the general structural formula:

• wherein
• DRUG-O— is a hydroxyl functional group attached to a carbon atom of an aromatic ring of the phenolic drug compound;
• R1 is selected from the group consisting of H, cycloalkyl groups having up to 10 carbon atoms, straight or branched chain alkyl, alkenyl or alkynyl groups of 1 to 10 carbon atoms, wherein the chains thereof (i) may be interrupted by at least one N, S, or O atom, or (ii) may be substituted by at least one group selected from the group consisting of COR2, COOR2 and CON(R2)2, hydrocarbyl aryl groups, aryl groups substituted by at least one group selected from the group consisting of COR2, COOR2, CON(R2)2, N(R2)2, OR2, halogen, SR2, NO2, and R2, mono- bi-cyclic saturated or unsaturated heterocyclic rings, each ring consisting of 3 to 7 members selected from the group consisting of carbon, nitrogen, oxygen and sulfur, CN, COR2, COOR2, CON(R2)2, and C(halogens)3;
• R2 is selected from the group consisting of cycloalkyl groups having up to 10 carbon atoms, straight or branched chain alkyl, alkenyl and alkynyl groups having 1 to 10 carbon atoms, straight or branched chain alkyl, alkenyl and alkynyl groups of 1 to 10 carbon atoms wherein the chains thereof may be interrupted by at least on N, S or O atom, hydrocarbyl arl groups, and in the case of —N(R2)2 taken with the other R2 group and N is mono- or bi-cyclic saturated or unsaturated heterocyclic ring, wherein each ring consists of 3 to 7 members selected from the group consisting of carbon, nitrogen, oxygen and sulfur;
• and
• (B) salts thereof.

A prodrug of a phenolic drug compound, the prodrug having the general structural formula:

• wherein
• DRUG-O— is a hydroxyl functional group attached to a carbon atom of an aromatic ring of the phenolic drug compound;
• R1, R2, R3, R4, R5, R6 and R7 are independently selected from the group consisting of H, cycloalkyl groups having up to 10 carbon atoms, straight or branched chain alkyl, alkenyl or alkynyl groups of 1 to 10 carbon atoms, wherein the chains thereof (i) may be interrupted by at least one N, S, or O atom, or (ii) may be substituted by at least one group selected from the group consisting of COR8, COOR8 and CON(R8)2, hydrocarbyl aryl groups, aryl groups substituted by at least one group selected from the group consisting of COR8, COOR8, CON(R8)2, N(R8)2, OR8, halogen, SR8, NO2, and R8, mono-bi-cyclic saturated or unsaturated heterocyclic rings, each ring consisting of 3 to 7 members selected from the group consisting of carbon, nitrogen, oxygen and sulfur, CN, COR8, COOR8, CON(R8)2, and C(halogens)3;
• R8 is selected from the group consisting of cycloalkyl groups having up to 10 carbon atoms, straight or branched chain alkyl, alkenyl and alkynyl groups having 1 to 10 carbon atoms, straight or branched chain alkyl, alkenyl and alkynyl groups of 1 to 10 carbon atoms wherein the chains thereof may be interrupted by at least on N, S or O atom, hydrocarbyl arl groups, and in the case of —N(R8)2 taken with the other R8 group and N is mono- or bi-cyclic saturated or unsaturated heterocyclic ring, wherein each ring consists of 3 to 7 members selected from the group consisting of carbon, nitrogen, oxygen and sulfur;
• and
• (B) salts thereof.

A prodrug of a phenolic drug compound, the prodrug having the general structural formula:

• wherein
• DRUG-X— is a carbon atom of an aromatic ring of the phenolic drug compound in the o- or p- position relative to a hydroxyl functional group attached to a different carbon atom of said aromatic ring;
• R1 selected from the group consisting of H, cycloalkyl groups having up to 10 carbon atoms, straight or branched chain alkyl groups of 1 to 10 carbon atoms;
• and
• (B) salts thereof.