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1. (WO2019033164) SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP
Latest bibliographic data on file with the International BureauSubmit observation

Pub. No.: WO/2019/033164 International Application No.: PCT/AU2018/050866
Publication Date: 21.02.2019 International Filing Date: 16.08.2018
IPC:
C07C 51/09 (2006.01) ,C07D 311/80 (2006.01) ,C07D 311/94 (2006.01) ,C07D 311/74 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
51
Preparation of carboxylic acids or their salts, halides, or anhydrides
09
from carboxylic acid esters or lactones
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
311
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
02
ortho- or peri-condensed with carbocyclic rings or ring systems
78
Ring systems having three or more relevant rings
80
Dibenzopyrans; Hydrogenated dibenzopyrans
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
311
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
02
ortho- or peri-condensed with carbocyclic rings or ring systems
94
condensed with rings other than six-membered or with ring systems containing such rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
311
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
02
ortho- or peri-condensed with carbocyclic rings or ring systems
74
Benzo [b] pyrans, hydrogenated in the carbocyclic ring
Applicants:
THE UNIVERSITY OF SYDNEY [AU/AU]; Parramatta Road The University of Sydney, New South Wales 2006, AU
Inventors:
REEKIE, Tristan; AU
SCOTT, Michael; AU
KASSIOU, Michael; AU
Agent:
FPA PATENT ATTORNEYS PTY LTD; Level 43 101 Collins Street Melbourne, Victoria 3000, AU
Priority Data:
201790328816.08.2017AU
Title (EN) SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP
(FR) SYNTHÈSE DE PHYTOCANNABINOÏDES COMPRENANT UNE ÉTAPE DE DÉMÉTHYLATION
Abstract:
(EN) A method for demethylating a methylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes: heating a reaction mixture comprising the methylated phytocannabinoid compounds and a polar aprotic solvent in the presence of a dissolved inorganic alkaline salt for a time sufficient to demethylate at least a portion of the methylated phytocannabinoid compounds and form the phytocannabinoid compound.
(FR) L'invention concerne un procédé permettant la déméthylation d'un composé phytocannabinoïde méthylé de formule I pour former un composé phytocannabinoïde de formule II : formule I formule II, dans lesquelles : R1 est choisi dans le groupe consistant en : les groupes alkyle en C1-C5 substitués ou non substitués ; R2 est choisi dans le groupe consistant en : OH ou O, et R3 est choisi dans le groupe consistant en : un cyclohexène substitué ou non substitué, un alcène en C2-C8 substitué ou non substitué, ou un dialcène en C2-C8 substitué ou non substitué ; ou R2 est O, et R2 et R3 forment ensemble une structure cyclique dans laquelle R2 est un atome nucléaire interne ; le procédé comprenant : le chauffage d'un mélange réactionnel comprenant les composés phytocannabinoïdes méthylés et un solvant aprotique polaire en présence d'un sel d'un métal alcalin inorganique dissous pendant un temps suffisant pour déméthyler au moins une partie des composés phytocannabinoïdes méthylés et former le composé phytocannabinoïde.
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Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)