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Medicinal acidic cannabinoids




Title: Medicinal acidic cannabinoids.
Abstract: The invention relates to an acidic cannabinoid for medical use and to a cannabis extract comprising an acidic cannabinoid. The extract may comprise one or more compounds selected from the group consisting of cannabidiolic acid (CBD-A), cannabidiol (CBD), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabinolic acid (CBN-A) and cannabinol. The invention further relates to a method for preparing a preparation comprising extracting an acidic cannabinoid from cannabis. ...


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USPTO Applicaton #: #20110021617
Inventors: Henricus Adriaan A. J. Korthout, Kitty Catharina M. Verhoeckx, Rentje Frederik Witkamp, Robert Paul Doornbos, Mei Wang


The Patent Description & Claims data below is from USPTO Patent Application 20110021617, Medicinal acidic cannabinoids.

RELATED APPLICATION(S)

This application is a continuation of Ser. No. 11/461,818 and filed Aug. 2, 2006 which is a continuation of PCT application no. PCT/NL2005/000075, designating the United States and filed Feb. 2, 2005; which claims the benefit of the filing date of European application no. EP 04075300.6, filed Feb. 2, 2004; all of which are hereby incorporated herein by reference in their entirety.

FIELD OF THE INVENTION

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The invention relates to an acidic cannabinoid for medical use and to a cannabis extract comprising an acidic cannabinoid.

BACKGROUND

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OF THE INVENTION

Δ9-Tetrahydrocannabinol (THC) is naturally found in cannabis. THC has been reported to have use as an analgesic, for instance for patients suffering from rheumatoid arthritis. A side effect of THC is its psychoactive activity. Further, conventionally THC is administered by smoking, which may be detrimental to general health, in particular to the lungs and the coronary system.

WO 89/01332 describes an acidic metabolite of THC, wherein the methyl group at the 9-position, a major metabolite formed in humans and other mammals, is substituted by a carboxyl group. This metabolite is reported to be non-psychoactive. Its use as a therapeutic agent for such purposes as the treatment of chronic pain and tissue inflammation often associated with illnesses such as rheumatoid arthritis is suggested. The Examples show a mouse hot plate test for analgesia, which indicates that, in mice, the metabolite shows about the same analgesic activity as THC and a somewhat lower activity than Naproxen. The Examples further indicate that the metabolite does not induce the formation of gastric lesions in an animal test under conditions wherein aspirin does.

In a review by Bhargava (Gen. Pharmac. (1978) 9(4):195-213), potential uses of cannabinoids are mentioned in rather general terms. Bhargava mentions that several cannabinoids have been pharmacologically tested, without disclosing in any detail, a specific medical activity for carboxylated THCs (THC acids), such as Δ9-tetrahydrocannabinolic acid or the like. In addition, reference is made to the analgesic activity of THC and several other cannabinoids compared to morphine. THC is reported to perform equi-analgesic with morphine, but other tested cannabinoids are reported to be much less potent or even inactive.

Williamson and Evans (Drugs 2000, Dec. 60(6):1303-1314 discuss in general terms a potential clinical use of cannabis. The specific use of THC acids, such as Δ9-tetrahydrocannabinolic acid or the like, as the active pharmaceutical ingredient, is not disclosed.

GB-A 2 384 707 relates to the use of a cannabinoid acid, in particular cannabidiol (CBD) and cannabidiol acid (CBDA) for use as an active pharmaceutical substance in the treatment of nausea, vomiting, emisis and motion sickness. The compounds may be obtained by extraction from cannabis. As a result of the extraction, relatively small amounts of THC-acids may be present in the extract, but the use of a THC-acid as an active pharmaceutical substance is not mentioned.

SUMMARY

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There remains a continuing desire for alternative therapeutics. It is therefore an object of the invention to provide such a therapeutic.

Surprisingly, it has now been found that a specific precursor of THC has properties which are of interest to medical use, such as analgesic and/or anti-inflammatory properties. Accordingly, the present invention relates to an acidic THC precursor for medical use.

More in particular, the present invention relates to an acidic cannabinoid represented by formula Ia or Ib for use as a medicament

In these formulae X, Z and A each represent a different group selected from the groups —OH, hydrogen and a first alkyl; accordingly, each of these four groups are present in the compound. The first alkyl is preferably a C1-C10 linear or branched alkyl, more preferably a C4-C7 linear or branched alkyl, even more preferably n-pentyl. The first alkyl is preferably Z.

D represents —OH or alkyl, preferably a C1-C3 linear or branched alkyl, in particular a methyl.

R represents a hydrogen, a CnH2n—OH, a CnH2n—COOH or a second alkyl; The n in these groups is an integer, preferably 0, 1 or 2. R is preferably a C1-C3 linear or branched alkyl, more preferably —CH3.

BRIEF DESCRIPTION OF THE DRAWINGS

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FIG. 1 shows a cannabinoid biosynthetic pathway.

FIGS. 2A and 2B show the effect of treatment with a cannabis extract comprising THC-A on the release of TNF-α in an ELISA assay.

FIGS. 3A and 3B show respectively the inhibitory effect on TNF-α release and the stimulatory effect on interleukin-10 release of an unheated cannabis extract comprising THC-A

FIG. 4 shows the effect of treatment with (an extract comprising) THC-A in mice suffering from autoimmune encephalomyelitis.

DETAILED DESCRIPTION

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OF THE INVENTION

Within the context of the invention, the term “acidic” is used to describe a compound having a carboxyl group, unless specified otherwise. In general, an acidic precursor of THC is transformable into THC by decarboxylation, optionally in combination with one or more other reactions, such as a cyclisation of a precursor having two of the rings forming the core of the THC to form the third ring, (de)alkylation, (de)hydroxylation and the like. Besides the compounds of formula Ia and of Ib, examples of acidic THC precursors are cannabidiolic acid (CBDA), cannabichromenic acid (CBCA), cannabinorolic acid (CBNRA), cannabigerolic acid (CBGA), cannabinolic acid (CBNA) and functional and structural analogues thereof. A number of these compounds are shown in the pathway displayed in FIG. 1.

A compound according to the present invention has been found to have analgesic and/or anti-inflammatory activity. This is surprising, as this finding is contrary from what may be concluded from a standard receptor binding test wherein the dissociation constants (Kd) were determined for binding of the compounds to the cannabinoid receptors CB1 and CB2 and compared with the binding of THC (See Examples).

In particular, an acidic compound according to the invention may be used for relieving pain and/or for suppression of an inflammatory response, preferably for modulating the release of one or more inflammatory mediators, in particular cytokine(s), in an animal, preferably in a human.




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stats Patent Info
Application #
US 20110021617 A1
Publish Date
01/27/2011
Document #
File Date
12/31/1969
USPTO Class
Other USPTO Classes
International Class
/
Drawings
0


Cannabidiol Cannabigerol Cannabinoid Cannabis

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Nederlandse Organisatie Voor Toegepast- Natuurwetenschappelijk Onderzoek Tno


Browse recent Nederlandse Organisatie Voor Toegepast- Natuurwetenschappelijk Onderzoek Tno patents



Drug, Bio-affecting And Body Treating Compositions   Designated Organic Active Ingredient Containing (doai)   Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai   Oxygen Containing Hetero Ring   The Hetero Ring Is Six-membered   Polycyclo Ring System Having The Hetero Ring As One Of The Cyclos   Tricyclo Ring System Having The Hetero Ring As One Of The Cyclos  

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20110127|20110021617|medicinal acidic cannabinoids|The invention relates to an acidic cannabinoid for medical use and to a cannabis extract comprising an acidic cannabinoid. The extract may comprise one or more compounds selected from the group consisting of cannabidiolic acid (CBD-A), cannabidiol (CBD), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabinolic acid (CBN-A) and cannabinol. The invention |Nederlandse-Organisatie-Voor-Toegepast-Natuurwetenschappelijk-Onderzoek-Tno