Prodrugs of tetrahydrocannabinol, compositions comprising prodrugs of tetrahydrocannabinol and methods of using the same

1. A compound having the formula:

Wherein OR 1 is selected from, a carbonate, a carbamate, an amino ester, and a phosphate.

2. The compound of claim 1 where in the amino ester is selected from the group consisting of an amino ester, a cyclic amino ester and an acylated amino ester.

3. The compound of claim 1 wherein the carbamate is selected from the group consisting of: an alkyl carbamate, an aminoalkyl carbamate, an acylated aminoalkyl carbamate, a cyclic aminoalkyl carbamate, an oxacarbamate, a pegylated carbamate, a hydroxylated carbamate, a branched hydroxylated carbamate, and a hydroxycarbonylalkyl carbamate.

4. The compound of claim 1 wherein the carbonate is selected from the group consisting of: an oxygenated carbonate, an oxacarbonate, a pegylated carbonate, a hydroxylated carbonate, a branched hydroxylated carbonate, an aminoalkyl carbonate, a cyclic aminoalkyl carbonate, an acylated aminoalkyl carbonate, and a hydroxycarbonylalkyl carbonate.

5. The compound from claim 1 selected from the group consisting of:

wherein X and Y is selected from a group consisting of: hydrogen, salt-forming cations including alkali metals, alkaline earth metals, and cations of pharmaceutically acceptable organic bases.

6. A pharmaceutical composition comprising:

(a) a compound as described in claim 1 ; and

(b) a pharmaceutically acceptable excipient.

7. A pharmaceutical composition comprising:

a) a compound selected from the group consisting of:

wherein X and Y is selected from a group consisting of: hydrogen, salt-forming cations including alkali metals, alkaline earth metals, and cations of pharmaceutically acceptable organic bases; and

(b) a pharmaceutical excipient.

8. A method of treating a medical condition in a mammal comprising the step of administering a compound as described in claim 1 , wherein the medical condition is selected from the group consisting of: anorexia, nausea, emesis, pain, wasting syndrome, HIV-wasting, chemotherapy induced nausea and vomiting, alcohol use disorders, anti-tumor, amyotrophic lateral sclerosis, glioblastoma multiforme, glioma, increased intraocular pressure, glaucoma, cannabis use disorders, Tourette's syndrome, dystonia, multiple sclerosis, inflammatory bowel disorders, arthritis, dermatitis, Rheumatoid arthritis, systemic lupus erythematosus, anti-inflammatory, anti-convulsant, anti-psychotic, anti-oxidant, neuroprotective, anti-cancer, immunomodulatory effects, peripheral neuropathic pain, neuropathic pain associated with post-herpetic neuralgia, diabetic neuropathy, shingles, burns, actinic keratosis, oral cavity sores and ulcers, post-episiotomy pain, psoriasis, pruritis, contact dermatitis, eczema, bullous dermatitis herpetiformis, exfoliative dermatitis, mycosis fungoides, pemphigus, severe erythema multiforme (e.g. Stevens-Johnson syndrome), seborrheic dermatitis, ankylosing spondylitis, psoriatic arthritis, Reiter's syndrome, gout, chondrocalcinosis, joint pain secondary to dysmenorrhea, fibromyalgia, musculoskeletal pain, neuropathic-postoperative complications, polymyositis, acute nonspecific tenosynovitis, bursitis, epicondylitis, post-traumatic osteoarthritis, synovitis, and juvenile rheumatoid arthritis.

9. The method of claim 8 wherein the compound is administered by a route selected from the group consisting of: transdermal, topical, oral, buccal, sublingual, intra venous, intra muscular, vaginal, rectal, ocular, nasal and follicular.

10. A method of treating a medical condition in a mammal comprising the steps of administering a compound selected from the group consisting of:

wherein X and Y is selected from a group consisting of: hydrogen, salt-forming cations including alkali metals, alkaline earth metals, and cations of pharmaceutically acceptable organic bases; and

wherein the medical condition is selected from the group consisting of: anorexia, nausea, emesis, pain, wasting syndrome, HIV-wasting, chemotherapy induced nausea and vomiting, alcohol use disorders, anti-tumor, amyotrophic lateral sclerosis, glioblastoma multiforme, glioma, increased intraocular pressure, glaucoma, cannabis use disorders, Tourette's syndrome, dystonia, multiple sclerosis, inflammatory bowel disorders, arthritis, dermatitis, Rheumatoid arthritis, systemic lupus erythematosus, anti-inflammatory, anti-convulsant, anti-psychotic, anti-oxidant, neuroprotective, anti-cancer, immunomodulatory effects, peripheral neuropathic pain, neuropathic pain associated with post-herpetic neuralgia, diabetic neuropathy, shingles, burns, actinic keratosis, oral cavity sores and ulcers, post-episiotomy pain, psoriasis, pruritis, contact dermatitis, eczema, bullous dermatitis herpetiformis, exfoliative dermatitis, mycosis fungoides, pemphigus, severe erythema multiforme (e.g., Stevens-Johnson syndrome), seborrheic dermatitis, ankylosing spondylitis, psoriatic arthritis, Reiter's syndrome, gout, chondrocalcinosis, joint pain secondary to dysmenorrhea, fibromyalgia, musculoskeletal pain, neuropathic-postoperative complications, polymyositis, acute nonspecific tenosynovitis, bursitis, epicondylitis, post-traumatic osteoarthritis, synovitis, and juvenile rheumatoid arthritis.

11. The method of claim 10 wherein the compound is administered by a route selected from the group consisting of: transdermal, topical, oral, buccal, sublingual, intra venous, intra muscular, vaginal, rectal, ocular, nasal and follicular.

12. A method of administering a compound to a mammal comprising the steps of:

(a) combining a compound of claim 1 with a pharmaceutical excipient to form a pharmaceutical composition;

(b) creating a dosage form suitable for administration to a mammal from the pharmaceutical composition; and

(c) administering the dosage form to a mammal.

13. The method of claim 12 wherein the pharmaceutical composition is administered by a route selected from the group consisting of: transdermal, topical, oral, buccal, sublingual, intra venous, intra muscular, vaginal, rectal, ocular, nasal and follicular.

14. A method of administering a compound to a mammal comprising the steps of:

(a) combining selected from the group consisting of:

wherein X and Y is selected from a group consisting of: hydrogen, salt-forming cations including alkali metals, alkaline earth metals, and cations of pharmaceutically acceptable organic bases; and

with a pharmaceutical excipient to form a pharmaceutical composition;

(b) creating a dosage form suitable for administration to a mammal from the pharmaceutical composition; and

(c) administering the dosage form to a mammal.

15. The method of claim 14 wherein the pharmaceutical composition is administered by a route selected from the group consisting of: transdermal, topical, oral, buccal, sublingual, intra venous, intra muscular, vaginal, rectal, ocular, nasal and follicular.

16. The compound of claim 1 which is:

17. The compound of claim 1 which is: