EP2 receptor agonists
A compound of formula (I): or a salt, solvate and chemically protected form thereof, wherein: R 5 is an optionally substituted C 5-20 aryl or C 4-20 alkyl group; A is selected from the group consisting of: wherein X and Y are selected from the group consisting of: O and CR 3 ; S and CR 3 ; NH and CR 3 ; NH and N; O and N; S and N; N and S; and N and O, and where the dotted lines indicate a double bond in the appropriate location, and where Q is either N or CH; R 3 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl-C 1-4 alkyl groups; R 4 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl-C 1-4 alkyl groups; R 6 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl-C 1-4 alkyl groups; D is selected from: B is selected from the group consisting of: where R N′ is selected from H and C 1-4 alkyl; where one of R P3 and R P4 is —C m alkylene-R 2 and the other of R P3 and R P4 is H, m and n can be 0 or 1, and m+n=1 or 2; and additionally when R P3 is —C m alkylene-R 2 , m can also be 2 or 3, and m+n=1, 2, 3 or 4, and when R 2 is tetrazol-5-yl, m+n may be 0; or where one of R P3 and R P4 is —O—CH 2 —R 2 , and the other of R P3 and R P4 is H, n is 0; R N is H or optionally substituted C 1-4 alkyl; R 2 is either: —CO 2 H (carboxy); —CONH 2 ; —CH 2 —OH; or tetrazol-5-yl.
1. A compound of formula (I):
or a salt, solvate and chemically protected form thereof, wherein:
R 5 is phenyl substituted by one or more C 5-6 aryl;
A is
wherein Q is CH;
R 3 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl—C 1-4 alkyl groups;
R 4 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl—C 1-4 alkyl groups;
R 6 is selected from H, F, Cl and optionally substituted C 1-4 alkyl, C 1-4 alkoxy, C 5-7 aryl and C 5-7 aryl—C 1-4 alkyl groups;
D is
B is
where one of R P3 and R P4 is —C m alkylene-R 2 and the other of R P3 and R P4 is H, m and n can be 0 or 1, and m+n =1 or 2; and additionally when R P3 is —C m alkylene—R 2 , m can also be 2 or 3, and m+n =1, 2, 3 or 4, and when R 2 is tetrazol-5-yl, m+n may be 0; or
where one of R P3 and R P4 is —O—CH 2 —R 2 , and the other of R P3 and R P4 is H, n is 0;
R N is H or optionally substituted C 1-4 alkyl;
R 2 is either:
(i) —CO 2 H (carboxy);
(ii) —CONH 2 ;
(iii) —CH 2 —OH (methoxy); or
(iv) tetrazol-5-yl.
2. A compound according to claim 1 , wherein either:
(i) R 3 , R 4 and R 6 are H; or
(ii) one of R 3 , R 4 and R 6 are Cl or F.
3. A compound according to claim 1 , wherein R N is H.
4. A compound according to claim 1 , wherein R 2 is carboxy or tetrazoly-5-yl.
5. A compound according to claim 4 , wherein R 2 is carboxy.
6. A compound according to claim 1 , wherein R P4 is H, and R P3 is —CH═CH—R 2 .
7. A compound according to claim 1 , wherein R P3 is —O—CH 2 —R 2 .
8. A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier or diluent.