Non-psychotropic cannabinoids

A pharmaceutical composition comprising as an active ingredient is a compound of the general formula (I):

• having the (3S,4S) configuration and being essentially free of the (3R,4R) enantiomer, wherein A—B indicates an optional 1(2) or 6(1) double bond,
• R1 is
• A) R3 where R3 is selected from the group consisting of
• a) a linear or branched, saturated or unsaturated, carbon side chain comprising 1-8 carbon atoms interrupted by 1-3 heteroatoms;
• or
• b) a saturated or unsaturated cyclic moiety or an aromatic or heterocyclic moiety having from 5-20 atoms comprising one or two-ringed structures, wherein each ring comprises 3-8 carbons interrupted by 1-4 heteroatoms, said heteroatoms in each independently selected from the group consisting of N, O, and S;
• wherein each ring optionally is further substituted with one or more groups selected from
• i) C1-6 alkyl,
• ii) C1-6 alkoxy,
• iii) C1-6 alkylthio,
• iv) Halo,
• v) Carboxyl
• vi) —CO2—C1-4 alkyl
• vii) keto,
• viii) nitro,
• ix) a saturated or unsaturated cyclic moiety, or an aromatic or a heterocyclic moiety wherein each ring comprises 3-8 carbons interrupted by 0-4 heteroatoms, said heteroatoms in each independently selected from the group consisting of N, O, and S;
• wherein each ring optionally is further substituted with one or more groups selected from i)-viii) as defined above;
• B) an amine or an amide substituted with at least one substituent as defined in R3 above;
• C) a thiol, a sulfide, a sulfoxide, a sulfone, a thioester or a thioamide optionally substituted with one substituent as defined in R3 above;
• or
• D) an ether —OR3 wherein R3 is as defined above;
• G is (a) halogen, (b) C1-C5 alkyl, or (c) —OR wherein R is (a′) —R″, wherein R″ is hydrogen or C1-C5 alkyl optionally containing a terminal —OR′″ or —OC(O)R′″ moiety wherein R′″ is hydrogen or C1-C5 alkyl, or (b′) —C(O)R′″ wherein R′″ is as previously defined, and
• R2 is (a) C1-C12 alkyl, (b) —OR″″, in which R″″ is a straight chain or branched C2-C9 alkyl which may be substituted at the terminal carbon atom by a phenyl group, or (c) —(CH2)nOR′″ wherein n is an integer of 1 to 7 and R′″ is hydrogen or C1-C5 alkyl;
• together with a pharmaceutically acceptable diluent or carrier.

A method for treating or preventing injuries to the central nervous system by administering to a patient a therapeutically effective amount of a pharmaceutical composition comprising a compound of the formula (I):

• having the (3S,4S) configuration and being essentially free of the (3R,4R) enantiomer, wherein A—B indicates an optional 1(2) or 6(1) double bond,
• R1 is
• A) R3 where R3 is selected from the group consisting of
• a) a linear or branched, saturated or unsaturated, carbon side chain comprising 1-8 carbon atoms interrupted by 1-3 heteroatoms;
• or
• b) a saturated or unsaturated cyclic moiety or an aromatic or heterocyclic moiety having from 5-20 atoms comprising one or two-ringed structures, wherein each ring comprises 3-8 carbons interrupted by 1-4 heteroatoms, said heteroatoms in each independently selected from the group consisting of N, O, and S;
• wherein each ring optionally is further substituted with one or more groups selected from
• i) C1 alkyl,
• ii) C1-6 alkoxy,
• iii) C1-6 alkylthio,
• iv) Halo,
• v) Carboxyl
• vi) —CO2—C1-4 alkyl
• vii) keto,
• viii) nitro,
• ix) a saturated or unsaturated cyclic moiety, or an aromatic or a heterocyclic moiety wherein each ring comprises 3-8 carbons interrupted by 0-4 heteroatoms, said heteroatoms in each independently selected from the group consisting of N, O, and S;
• wherein each ring optionally is further substituted with one or more groups selected from i)-viii) as defined above;
• B) an amine or an amide substituted with at least one substituent as defined in R3 above;
• C) a thiol, a sulfide, a sulfoxide, a sulfone, a thioester or a thioamide optionally substituted with one substituent as defined in R3 above;
• or
• D) an ether —OR3 wherein R3 is as defined above;
• G is (a) halogen, (b) C1-C5 alkyl, or (c) —OR wherein R is (a′) —R″, wherein R″ is hydrogen or C1-C5 alkyl optionally containing a terminal —OR′″ or —OC(O)R′″ moiety wherein R′″ is hydrogen or C1-C5 alkyl, or (b′) —C(O)R′″ wherein R′″ is as previously defined, and
• R2 is (a) C1-C12 alkyl, (b) —OR″″, in which R″″ is a straight chain or branched C2-C9 alkyl which may be substituted at the terminal carbon atom by a phenyl group, or (c) —(CH2)nOR′″ wherein n is an integer of 1 to 7 and R′″ is hydrogen or C1-C5 alkyl.