C07C43/215

SYNTHESIS OF CANNABIDIOL AND ANALOGS THEREOF, AND RELATED COMPOUNDS, FORMULATIONS, AND METHODS OF USE

Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((-)-trans-Δ.sup.9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

METHOD OF PREPARING SOLID-SUPPORTED PALLADIUM CATALYST

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

METHOD OF PREPARING SOLID-SUPPORTED PALLADIUM CATALYST

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

Jute stick-palladium nanoparticle dip catalysts useful for aqueous Suzuki-Miyaura and Mizoroki-Heck C—C bond formation

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

Jute stick-palladium nanoparticle dip catalysts useful for aqueous Suzuki-Miyaura and Mizoroki-Heck C—C bond formation

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

Inhibitors of SOX18 protein activity for treating angiogenesis-and/or lymphangiogenesis-related diseases

Disclosed are compounds of a formula provided herein that show efficacy in the inhibition of SOX18 protein activity, and in particular with respect to the ability of SOX18 to bind DNA and/or particular protein partners. Further, methods of treating angiogenesis- and/or lymphangiogenesis-related diseases, disorders or conditions, such as cancer metastasis and vascular cancers, are provided herein.

Inhibitors of SOX18 protein activity for treating angiogenesis-and/or lymphangiogenesis-related diseases

Disclosed are compounds of a formula provided herein that show efficacy in the inhibition of SOX18 protein activity, and in particular with respect to the ability of SOX18 to bind DNA and/or particular protein partners. Further, methods of treating angiogenesis- and/or lymphangiogenesis-related diseases, disorders or conditions, such as cancer metastasis and vascular cancers, are provided herein.

CATALYTIC CANNABINOID PROCESSES AND PRECURSORS
20220220089 · 2022-07-14 ·

The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.