University of Ottawa

Owen-Barry Pharmaceuticals Inc.

Nectar Health Sciences Inc.

Other

Her Majesty the Queen in Right of Canada, as Represented by the Minister

Tony Durst

Michael Poulter

John Thor Arnason

Zulfiquar Merali

Hooman Shadnia

James S Wright

Muhammad Asim

Jay Van Der Vlugt

Amanda Saikaley

Luis J Poveda Alvarez

E Pablo Sanchez-Vindas

Stanley J Alkemade

Iqubal Velji

John Douglas Baker

Jose Miguel Wade

James C Freed

Margaret B Glinski-Oomen

Christine Pratt

Brian Foster

Ana Francis Carballo

Christian Cayer

Martha Mullally

The present application relates to compounds and methods for reducing the severity of convulsant activity or epileptic seizures, or for the treatment of chronic or acute pain.

Anticonvulsant compounds

Disclosed are methods for separating, recovering, and purifying cannabidiolic acid (CBDA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in C5-C7 hydrocarbon solvents, adding thereto a selected amine to thereby precipitate a CBDA-amine salt therefrom, dissolving the recovered CBDA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallizing a purified CBDA-amine salt therefrom. The recrystallized CBDA-amine salt may be decarboxylated to form a mixture of cannabidiol (CBD) and amine. The CBD amine mixture may be acidified to separate the amine from CBD. The recovered CBD may be concentrated to produce a highly purified CBD. Also disclosed are CBDA-amine salts produced with certain amines selected from groups of secondary amines, tertiary amines, diamines, amino alcohols, amino ethers, and highly basic amines.

Methods for extraction, processing, and purification of a selected family of target compounds from cannabis

Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of &#x394;9-tetrahydrocannabinol (&#x394;9-THC) and amine. The &#x394;9-THC amine mixture may be acidified to separate the amine from &#x394;9-THC. The recovered &#x394;9-THC may be concentrated to produce a highly purified &#x394;9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.

The present application relates to compounds and methods for reducing the severity of convulsant activity, or epileptic seizures.

The disclosure provides compositions containing preparations from plants of the family Marcgraviaceae and from plants of the family Platanaceae. The disclosure also provides methods and uses of plant preparations for treating anxiety, stress and glucocorticoid related disorders.

Plant compositions and methods and uses thereof for treating elevated glucocorticoid related disorders, and anxiety

Derivatives of dillapiol, sesamol and related monolignans having the following general formula:  These compounds have synergistic properties, inhibit cytochrome P450 enzymes such as human CYP3A4, and can be used as pesticide synergists or pharmaco-enhancers. Accordingly, methods for increasing the efficacy and/or bioavailability of a pharmaceutically active agent and for increasing the potency of a pesticide are described, as are synergistic pesticidal and pharmaceutical compositions.

Derivatives of dillapiol and related monolignans and use thereof

The presently disclosed and claimed inventive concept(s) provides new estrogenic compounds of the general formula and pharmaceutical compositions containing them. The compounds of the presently disclosed and claimed inventive concept(s) are useful, for example, in hormone replacement therapies (HRT/ERT), and as contraceptives, and estrogenic hormone therapies. Also provided is a process for synthesizing the compounds of the presently disclosed and claimed inventive concept(s).

Estrogenic compounds, process for their production and pharmaceutical uses thereof

Pharmaceutical compositions for preventing or treating anxiety, comprising betulinic acid or derivatives thereof are provided. Methods for preventing or treating anxiety with betulinic acid or derivatives thereof are also provided. The invention further provides betulinic-acid containing preparations of plants of the family Marcgraviaceae having anxiolytic activity and methods for making such extracts and using them to prevent or treat anxiety in a subject.

Anxiolytic marcgraviaceae compositions containing betulinic acid, betulinic acid derivatives, and methods

The present invention provides new estrogenic compounds of the general formula 

The present invention provides new estrogenic compounds of the general formula in which the substituents have the meanings that are explained in more detail in the description, and pharmaceutical compositions containing them. The compounds of the invention are useful, for example, in hormone replacement therapies (HRT/ERT) and as contraceptives and estrogenic hormone therapies. Also provided is a process for synthesizing the compounds of the invention.

Anxiolytic Marcgraviaceae compositions containing betulinic acid, betulinic acid derivatives, and methods

One aspect of this invention relates to 2-substituted podophyllotoxin corresponding to the formula: ##STR1## where R.sub.1 is the residue of an electrophile reactant with the precursor enolate, e.g., halogen, i.e., Br, Cl, F and I, lower alkyl (preferably methyl), hydroxyl, --SR.sub.5 where R.sub.5 is lower alkyl, aralkyl or aryl and COOR.sub.6 where R.sub.6 is hydrogen or lower alkyl. Another aspect of this invention relates to 2-substituted etopsides and related compounds corresponding to the formula: ##STR2## where R.sub.1 is as defined above, and where R.sub.2 is: ##STR3## where AcO is acetyl; or ##STR4## where R.sub.3 is hydrogen and R.sub.4 is alkyl, alkenyl, cycloalkyl, 2-furyl, 2-thienyl, aryl, aralkyl, or alkenyl wherein the aromatic ring (preferably phenyl) may be optionally substituted by one or more hydroxyl, alkyl, alkoxy, nitro or halogen; or where each of R.sub.3 and R.sub.4 is alkyl or where each of R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached signify a saturated cycloaliphatic ring having 5 or 6 carbon atoms; each alkyl, alkenyl or alkoxy above having no more than 10 carbon atoms and each aryl containing no more than 16 carbon atoms excluding substituent on the ring which are defined above. Yet another aspect of this invention relates to novel intermediate compounds. In addition, a further aspect of this invention relates to various methods for preparing the above compounds.

Growing community of inventors

Ottawa, Canada

Tony Durst