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US 2019/0092807 A1Published application
Process and new intermediates for the preparation of 11-methylene steroids
AssigneeCrystal Pharma, S.A.U.
InventorsCelso Miguel SANDOVAL RODRÍGUEZ, Ignacio HERRÁIZ SIERRA, lvano MESSINA, Jesús Miguel IGLESIAS RETUERTO
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Abstract
The invention relates to a process for the preparation of 11-methylene steroids through selective olefination of the ketone at position 11. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as Etonogestrel and Desogestrel.
Claims22
A process for the preparation of a compound of formula (I), or a solvate thereof
- wherein
- X represents H or it forms together with the carbon atom to which it is bonded a ketone protecting group;
- Y together with the carbon atom to which it is bonded represents C═CH2 or C(OH)CH2Z, wherein Z is selected from H and SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- R6 is selected from H, C1-C6 alkyl and halogen;
- R10 is selected from H, C1-C6 alkyl and halogen, or is absent when there is a double bond between C1 and C10;
- R13 is selected from H and C1-C6 alkyl;
- R16 is selected from H, C1-C6 alkyl and halogen;
- is a single or double bond;
- which comprises reacting a compound of formula (II) or a solvate thereof
- wherein X, R6, R10, R13, R16, and can take the meanings defined above;
- with a compound of formula (III)
- wherein Z can take the meanings defined above and M is selected from Li, Mg Br, MgCI and Mgl.
9 more elements
A compound of formula (Ic), or a solvate thereof
- wherein
- X represents H or it forms together with the carbon atom to which it is bonded a ketone protecting group;
- Z is selected from H and SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- R6 is selected from H, C1-C6 alkyl and halogen;
- R10 is selected from H, C1-C6 alkyl and halogen, or is absent when there is a double bond between C1 and C10;
- R13 is selected from H and C1-C6 alkyl;
- R16 is selected from H, C1-C6 alkyl and halogen;
- and
- is a single or double bond.
6 more elements
A compound of formula (IVc), or a solvate thereof
- wherein
- X represents H or it forms together with the carbon atom to which it is bonded a ketone group or a ketone protecting group;
- Z is selected from H and SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- R1 is selected from H and SiR″3, wherein each R″ is independently selected from C1-C6 alkyl, C6-C10 aryl and halogen;
- R6 is selected from H, C1-C6 alkyl and halogen;
- R10 is selected from H, C1-C6 alkyl and halogen, or is absent when there is a double bond between C1 and C10;
- R13 is selected from H and C1-C6 alkyl;
- R16 is selected from H, C1-C6 alkyl and halogen;
- and
- is a single or double bond.
7 more elements
Dependencies are inferred from the claim text.