Granted Patent B2

US 12,227,537 · App. 17/319,545 · Granted Feb 18, 2025

Inventors: Celso Miguel Sandoval Rodríguez (Boecillo-Valladolid, ES); Ignacio Herráiz Sierra (Boecillo-Valladolid, ES); Ivano Messina (Boecillo-Valladolid, ES); Jesús Miguel Iglesias Retuerto (Boecillo-Valladolid, ES)

Assignee: CRYSTAL PHARMA, S.A.U.

C07J11/00C07J1/0059C07J1/0096C07J21/008C07J33/007C07J43/003C07J51/00C07J1/007C07J1/0077C07J1/0085

Abstract

Claims (48)

1. 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 C 1 -C 6 alkyl and C 6 -C 10 aryl;

R 6 is selected from H, C 1 -C 6 alkyl and halogen;

R 10 is selected from H, C 1 -C 6 alkyl and halogen, or is absent when there is a double bond between C 1 and C 10 ;

R 13 is selected from H and C 1 -C 6 alkyl;

R 16 is selected from H, C 1 -C 6 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 C 1 -C 6 alkyl and C 6 -C 10 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 C 1 -C 6 alkyl and C 6 -C 10 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 C 1 -C 6 alkyl and C 6 -C 10 aryl.

2. 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 C 1 -C 6 alkyl and C 6 -C 10 aryl;

R 1 is selected from H and SiR″ 3 , wherein each R″ is independently selected from C 1 -C 6 alkyl, C 6 -C 10 aryl and halogen;

R 6 is selected from H, C 1 -C 6 alkyl and halogen;

R 10 is selected from H, C 1 -C 6 alkyl and halogen, or is absent when there is a double bond between C 1 , and C 10 ;

R 13 is selected from H and C 1 -C 6 alkyl;

R 16 is selected from H, C 1 -C 6 alkyl and halogen; and

is a single or double bond;

said compound meeting one of the following conditions (a) to (b):

(a) wherein R 1 is SiR″ 3 , wherein each R″ is independently selected from C 1 -C 6 alkyl, C 6 -C 10 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 C 1 -C 6 alkyl and C 6 -C 10 aryl;

X forms together with the carbon atom to which it is bonded a ketone group or a ketone protecting group;

R 1 is selected from H and SiR″ 3 , wherein each R″ is independently selected from C 1 -C 6 alkyl, C 6 -C 10 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 C 1 -C 6 alkyl and C 6 -C 10 aryl; and

R 1 is selected from H and SiR″ 3 , wherein each R″ is independently selected from C 1 -C 6 alkyl, C 6 -C 10 aryl and halogen.

3. The compound according to claim 1 , which is selected from the group consisting of:

4. The compound according to claim 2 , which is selected from the group consisting of:

Assignments (4)

Priority Claims (1)

Continuity (2)

References Cited (25)