Cannabinol derivatives

A cannabinol derivative having the following formula:

• 22
• wherein,
• R1 is:
• a) H,
• b) a C1-4 alkyl group or ester thereof,
• c) COOH,
• d) OH,
• e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
• f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
• g)
• 23
• wherein n=1 to 8
• h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
• i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
• j) a lactone (e.g., COCOH);
• or
• k) CH(CH3)CO2H or —OCOCH3
• R2 is:
• a) H, OH, COOH, or a halogen
• b) C1-6 carboxy or alkoxy group, or
• c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen.
• R3 is:
• a) (W)m—Y—(Z)n, wherein
• W is a C5-12 straight or branched (preferably 1S′CH3, 2R′CH3 dimethyl) alkyl, alkenyl, alkynyl, group, or mixture thereof, optionally substituted with at least one halogen,
• Y is a bond, O, S, SO, SO2, CO, NH, N(C1-6 alkyl), or NCS,
• Z is:
• i) a C5-12 alkyl, alkenyl, alkynyl, group, or mixture thereof, optionally substituted with at least one halogen, optionally substituted with a terminal aromatic ring,
• ii) CN1-3, CO2H, or CO2C1-4 alkyl, CONH2, CONHC1-4 alkyl, or CON(C1-4 alkyl)2, wherein each C1-4 alkyl on the amide nitrogen can be the same or different, or
• iii) a phenyl or benzyl group, optionally substituted with halo, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, CN, CF3, CO2H, or CO2C1-4 alkyl, CONH2, CONHC1-4 alkyl, or CON(C1-4 alkyl)2, wherein each C1-4 alkyl on the amide nitrogen can be the same or different, and wherein
• m and n are the same or different, and each is either 0 or 1,
• b) a C5-12 alkyl or haloalkyl group, optionally substituted with a terminal aromatic ring, CN1-3, NCS, CO2H, or CO2C1-4 alkyl, CONH2, CONHC1-4alkyl, or CON(C1-4 alkyl)2, wherein each C1-4 alkyl on the amide nitrogen can be the same or different, or
• c) a C5-12 alkene or alkyne group, optionally substituted with a halogen, dithiolene, terminal aromatic ring, CN1-3, NCS, CO2H, or CO2C1-4 alkyl, CONH2, CONHC1-4 alkyl, or CON(C1-4 alkyl)2,wherein each C1-4 alkyl on the amide nitrogen can be the same or different;
• R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
• a) hydrogen,
• b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
• c) CN,
• d) CO2H,
• e) CO2—C1-4 alkyl,
• f) C(Y)(Z)—OH,
• g) C(Y)(Z)—O—C1-4 alkyl, and
• h) C1-6 alkyl-CO2—Y,
• wherein Y and Z are each independently H or C1-6 alkyl,
• R7 is:
• a) hydroxy or lactone,
• b) halo,
• c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
• d) CN,
• e) N3,
• f) CO2H,
• g) CO2—C1-4 alkyl,
• h) C(Y)(Z)—OH,
• i) C(Y)(Z)—O—C1-4 alkyl,
• j) C1-6 alkyl-CO2—Y, or
• k) ═O or ═S,
• wherein Y and Z are each independently H or C1-6 alkyl;
• Q is:
• a) O or S, or
• b) N—W, wherein W is:
• i) hydrogen,
• ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl
• iii) OC1-6 alkyl, or OC1-6 haloalkyl,
• iv) CN,
• v) C1-6 alkyl,
• vi) C(Y)(Z)C1-4 alkyl, or
• vii) C1-6 alkyl-CO2—Z,
• wherein Y and Z are each independently H or C1-6 alkyl.