Synthesis of Delta 9,11 Steroids
AssigneeSanthera Pharmaceuticals (Schweiz) AG
InventorsGabriel Schäfer, Lauso Olivieri, Marco Martin
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Abstract
The present invention is directed to a process for the preparation of Δ9,11 steroids by deoxygenation of 9,11-epoxy steroids using HI. The disclosed process selectively forms Δ9,11 steroids such as Vamorolone and can also be used for steroid synthesis of Δ9,11 steroids in pharmaceutical purity.
Claims20
A method of making a Δ9,11 steroid from a 9,11 epoxy steroid, comprising treating the 9,11 epoxy steroid with hydroiodic acid (HI).
A process for preparing a Δ9,11 steroids of formula I,
- wherein the dotted line is a single or a double bond;
- R1 is H or OH;
- one of R2 or R3 is CH3 and the other is H or both are H;
- and X is H, halo, OR, wherein R is H or C(O)RI, and RI is CF3, C1-C6 alkyl, C5-C12 cycloalkyl, aryl, heteroaryl or C1-C6 alkoxy, or NRII, wherein NRII is a tertiary amine, wherein the tertiary amine is part of a linear or cyclic substructure,
- the process comprising treating an 9,11 epoxy steroid of formula II
- wherein the dotted line is a single or a double bond;
- R1 is H or OH;
- one of R2 or R3 is CH3 and the other is H or both are H;
- and X is H, halo, OR, wherein R is H or C(O)RI, and RI is CF3, C1-C6 alkyl, C5-C12 cycloalkyl, aryl, heteroaryl or C1-C6 alkoxy, or NRII, wherein NRII is a tertiary amine,
- with hydroiodic acid, HI, to form the Δ9,11 steroid of formula I.
A process of purifying Vamorolone comprising a step of re-crystallizing crude Vamorolone in isopropanol or in a mixture of water and isopropanol, thereby forming purified Vamorolone of 99.5 wt % purity or more.
Dependencies are inferred from the claim text.