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US 12,227,537 B2Granted
Intermediates for the preparation of 11-methylene steroids
AssigneeCrystal Pharma, S.A.U.
InventorsCelso Miguel Sandoval Rodríguez, Ignacio Herráiz Sierra, Ivano Messina, Jesús Miguel Iglesias Retuerto
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Abstract
Compounds having the formula or solvates of the compounds can be used as intermediates in the preparation of the synthetic steroids, Etonogestrel and Desogestrel, as well as other pharmaceutically active agents.
Claims4
A compound of formula (Ic):
- 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;
- said compound meeting one of the following conditions (a) to (c):
- (a) wherein Z is SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- (b) with the proviso that the compound of formula (Ic) does not represent:
- (c) which is selected from:
- a compound of formula (Ia-1):
- wherein:
- X 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;
- and
- is a single or double bond;
- and
- a compound of formula (Ib-1):
- wherein:
- Z is selected from H and SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl.
20 more elements
A compound of formula (IVc):
- 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;
- said compound meeting one of the following conditions (a) to (b):
- (a) wherein R1 is SiR″3, wherein each R″ is independently selected from C1-C6 alkyl, C6-C10 aryl and halogen;
- (b) which is selected from:
- a compound of formula (IVa-2):
- wherein
- Z is SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- X forms together with the carbon atom to which it is bonded a ketone group or a ketone protecting group;
- R1 is selected from H and SiR″3, wherein each R″ is independently selected from C1-C6 alkyl, C6-C10 aryl and halogen;
- and
- is a single or double bond;
- and
- a compound of formula (IVb-2):
- wherein
- Z is selected from H and SiR′3 wherein each R′ is independently selected from C1-C6 alkyl and C6-C10 aryl;
- and
- R1 is selected from H and SiR″3, wherein each R″ is independently selected from C1-C6 alkyl, C6-C10 aryl and halogen.
23 more elements
Dependencies are inferred from the claim text.