Cannabinoid prodrug compounds

A pharmaceutical composition comprising a therapeutically effective amount of a compound represented by Formula I,

• wherein:
• X is
• wherein:
• R1 is selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl;
• R2 is H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl, wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• and R3 is
• wherein
• Ra in each instance is OH, NHC1-10alkyl or OC1-10alkyl, provided that Ra is a covalent bond when Ra is in a non-terminal position;
• and m is 1 to 9;
• Rb in each instance is independently H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl, wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• Rc in each instance is independently selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl, wherein Rb and Rc optionally link up to form a 5 to 7 membered ring;
• and m is an integer ranging from 1 to 9;

A compound represented by Formula I,

• wherein:
• X is
• wherein:
• R1 is selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl;
• R2 is H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl, wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• and R3 is selected from the group consisting of C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl, and
• wherein
• Ra in each instance is OH, NHC1-10alkyl or OC1-10alkyl, provided that Ra is a covalent bond when Ra is in a non-terminal position;
• and m is 1 to 9;
• Rb in each instance is independently H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl, wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• Rc in each instance is independently selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl, wherein Rb and Rc optionally link up to form a 5 to 7 membered ring;
• and m is an integer ranging from 1 to 9;
• wherein:
• R4 is selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl and
• wherein
• Ra in each instance is OH, NHC1-10alkyl or OC1-10alkyl, provided that Ra is a covalent bond when Ra is in a non-terminal position;
• and m is 1 to 9;
• Rb in each instance is independently H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl (e.g. phenyl), wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• Rc in each instance is independently selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl, wherein Rb and Rc optionally link up to form a 5 to 7 membered ring;
• and 0 is an integer ranging from 1 to 9;
• c) (A)n (Formula X-c), wherein A is an amino acid residue, wherein each A is independently represented by
• wherein:
• R5 is H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, imidazolyl, or aryl optionally substituted with C1-4 alkyl or OH;
• R6 and R7 in each instance are each independently s H, or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, or aryl;
• provided that R7 is a covalent bond to a carbonyl group if the amino acid residue is in a non-terminal position;
• and n is an integer ranging from 1 to 9;
• Optionally R5 and R6 link up to form a 5 to 7 membered ring;
• wherein:
• R8 is selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl;
• R9 is selected from the group consisting of C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl and
• wherein
• Ra in each instance is OH, NHC1-10alkyl or OC1-10alkyl, provided that Ra is a covalent bond when Ra is in a non-terminal position;
• and m is 1 to 9;
• Rb in each instance is independently H or C1-10 alkyl optionally substituted with OH, SH, SC1-4 alkyl, heteroaryl, CONH2, COOH, NH2, NHC(NH)NH2, or aryl (e.g. phenyl), wherein the heteroaryl and aryl is optionally substituted with CN, halogen, CF3, C1-4 alkyl or OH;
• Rc in each instance is independently selected from the group consisting of H, C1-10 alkyl, C1-4 alkyl-aryl, C1-4 alkyl-heteroaryl, wherein Rb and Rc optionally link up to form a 5 to 7 membered ring;
• and p is an integer ranging from 1 to 9;
• wherein R10 is a polyethylene or derivative thereof or a C1-10 alkyl wherein one or more carbons of the C1-10 alkyl is replaced O, S, NH or NH2;
• or
• f) R11, wherein R11 is an optionally substituted arylalkyl, a sugar, alkyl or a C1-10 alkyl wherein one or more carbons of the C1-10 alkyl is replaced O, S, NH or NH2.