Process for Making Biologically Active Compounds and Intermediates Thereof
AssigneeMAKScientific, LLC
InventorsAlexandros Makriyannis, Kiran Vemuri
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Abstract
A process of manufacturing biologically active compounds, their analogs, pharmaceutically acceptable salts, solvates, polymorphs, isotopic variants, and intermediates thereof. Notably, the compounds of the formula IA, 1B, 1C. 1D. 1E, 1F and IG for which novel processes have been disclosed, selectively act on the cannabinoid receptors, and with high affinity. The processes for the preparation of the compounds enable the syntheses of cannabinoid modulators on a large-scale that are eco-friendly and economically viable. Additionally, the processes disclosed enable the synthesis of cannabinoid modulators with high purity and in high yield for their use in making drug substance and drug products.
Claims9
A process for preparing a compound represented by Formula IA, its solvates, polymorphs and isotopic variations thereof:
- comprising:
- reacting a compound represented by Formula II:
- with a compound represented by Formula III:
- to provide a compound represented by Formula VII:
- and
- reacting the compound of Formula VII with an alkyne to provide a compound represented by formula I:
- or
- reacting a reacting a compound represented by Formula II:
- with a compound represented by Formula III:
- to provide a compound represented by Formula VII:
- and
- reacting the compound of Formula VII with an alkyne to provide a compound represented by Formula I:
- or
- reacting a compound represented by Formula II:
- with a compound represented by Formula III:
- to provide a compound represented by Formula VII:
- and
- reacting the compound of Formula VII with an alkyne to provide a compound represented by Formula I:
- or
- reacting a compound represented by Formula II:
- with a compound represented by Formula III:
- to provide a compound represented by Formula I:
- or
- reacting a compound represented by Formula II:
- with a compound represented by Formula III:
- to provide a compound represented by Formula I:
- and
- reacting the compound of Formula I with an alkali metal hydroxide to provide a compound represented by Formula V:
- reacting the compound of Formula V with a substituted hydrazine to provide a compound represented by the Formula IA;
- or
- reacting the compound of Formula I with a substituted hydrazine to provide a compound represented by Formula VI:
- and
- reacting the compound of Formula VI with a divinyl derivative to provide a compound represented by the Formula IA.
A process for preparing a compound represented by Formula ID, its solvates, polymorphs and isotopic variations thereof
- comprising:
- reacting a compound represented by Formula III:
- with substituted hydrazide to provide a compound represented by Formula IV:
- reacting the compound of Formula IV with a compound represented by Formula II:
- to provide a compound represented by the Formula ID.
Dependencies are inferred from the claim text.