Process

1. A process for preparation of a compound of Formula (IA) or a pharmaceutically acceptable salt thereof:

wherein:

R 1 represents an aryl or phenoxymethyl group, each of which is optionally substituted by one or more substituents selected from: halogen, C 1-6 alkoxy, C 1-6 alkyl, nitro, cyano, trifluoromethyl, —NR 8 R 9 and —NHSO 2 R 8 ;

R 2 represents hydrogen or C 1-6 alkyl;

R 3 represents hydrogen or C 1-6 alkyl;

X 1 and X 2 independently represent (a) hydrogen, (b) C 1-6 alkylCO, or (c) an aryl CO group optionally substituted by halogen or a C 1-6 alkyl group, with the proviso that when one is (b) or (c) the other is hydrogen (a);

R 4 represents a group (W):

wherein A represents an aryl, pyridine, thiophene or furan group; R 5 represents cyano, tetrazol-5-yl, —CO 2 H or —CO 2 R 8 ; R 6 and R 7 independently represent hydrogen, C 1-6 alkyl, —CO 2 H, —CO 2 R 8 , cyano, tetrazol-5-yl, halogen, trifluoromethyl or C 1-6 alkoxy, or when R 6 and R 7 are bonded to adjacent carbon atoms, R 6 and R 7 may, together with the carbon atoms to which they are bonded, form a fused 5- or 6- membered ring optionally having one or two nitrogen, oxygen or sulfur atoms; each R 12 independently represents substituents selected from: C 1-6 alkyl, halogen, trifluoromethyl and C 1-6 alkoxy, and n represents an integer from 0-4; and

R 8 and R 9 independently represent C 1-6 alkyl;

comprising hydrolysis of a compound of Formula (IB) or a pharmaceutically acceptable salt thereof:

wherein:

R 1 represents an aryl or phenoxymethyl group, each of which is optionally substituted by one or more substituents selected from: halogen, C 1-6 alkoxy, C 1-6 alkyl, nitro, cyano, trifluoromethyl, —NR 8 R 9 and —NHSO 2 R 8 ;

R 2 represents hydrogen or C 1-6 alkyl;

R 3 represents hydrogen or C 1-6 alkyl;

R 4 represents a group (W):

wherein A represents an aryl, pyridine, thiophene or furan group; R 5 represents cyano, tetrazol-5-yl or —CO 2 R 8 ; R 6 and R 7 independently represent hydrogen, C 1-6 alkyl, —CO 2 R 8 , cyano, tetrazol-5-yl, halogen, trifluoromethyl, or C 1-6 alkoxy, or when R 6 and R 7 are bonded to adjacent carbon atoms, R 6 and R 7 may, together with the carbon atoms to which they are bonded, form a fused 5- or 6- membered ring optionally having one or two nitrogen, oxygen or sulfur atoms; each R 12 independently represents substituents selected from: C 1-6 alkyl, halogen, trifluoromethyl and C 1-6 alkoxy, and n represents an integer from 0-4;

R 8 and R 9 independently represent C 1-6 alkyl; and

R 11 represents C 1-6 alkyl or aryl optionally substituted by C 1-6 alkyl or halogen.

2. The process of claim 1 wherein when the group R 4 in formula IB is substituted by —C 2 R 8 , the step of hydrolysing the ester group —C 2 R 8 to produce a compound of Formula (IA), wherein R 4 is substituted by a —CO 2 H group.

3. The process for preparation of a compound of Formula (IA) as claimed in claim 1 wherein the compound of Formula (IB) is prepared by reacting a compound of Formula (II)

with a compound of Formula (III)

4. The process as claimed in claim 1 wherein R 6 and R 7 represent hydrogen.

5. The process as claimed in claim 1 wherein n represents 0.

6. The process as claimed in claim 1 wherein R 1 represents an aryl group optionally substituted by one or more substituents selected from: halogen, C 1-6 alkoxy, C 1-6 alkyl and trifluoromethyl.

7. The process as claimed in claim 1 wherein R 1 represents phenyl substituted by a halogen group.

8. The process as claimed in claim 1 wherein R 2 represents hydrogen.

9. The process as claimed in claim 1 wherein R 3 represents hydrogen.

10. The process as claimed in claim 1 wherein X 1 and X 2 both represent hydrogen.

11. The process as claimed in claim 1 wherein R 11 represents methyl.

12. A process as claimed in claim 1 wherein the compound of Formula (IA) is selected from the group consisting of:

3′-[(2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino][1,1′-biphenyl]-3-carboxylic acid hydrochloride,

2-{3-[(2{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino]phenyl}-3-furoic acid,

3-{3-[(2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino]phenyl}isonicotinic acid,

3′-[((2R)-2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)amino]-1,1′-biphenyl-2-carboxylic acid, and

2-{3-[(2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino]phenyl}thiophene-3-carboxylic acid and pharmaceutically acceptable salts thereof.

13. A compound of Formula (IB):

wherein:

R 1 represents an aryl or phenoxymethyl group, each of which is optionally substituted by one or more substituents selected from: halogen, C 1-6 alkoxy, C 1-6 alkyl, nitro, cyano, trifluoromethyl, —NR 8 R 9 and —NHSO 2 R 8 ;

R 2 represents hydrogen or C 1-6 alkyl;

R 3 represents hydrogen or C 1-6 alkyl;

R 4 represents a group (W):

wherein A represents an aryl, pyridine, thiophene or furan group; R 5 represents cyano, tetrazol-5-yl or —C 2 R 8 ; R 6 and R 7 independently represent hydrogen, C 1-6 alkyl, —CO 2 R 8 , cyano, tetrazol-5-yl, halogen, trifluoromethyl or C 1-6 alkoxy, or when R 6 and R 7 are bonded to adjacent carbon atoms, R 6 and R 7 may, together with the carbon atoms to which they are bonded, form a fused 5- or 6- membered ring optionally having one or two nitrogen, oxygen or sulfur atoms; each R 12 independently represents substituents selected from: C 1-6 alkyl, halogen, trifluoromethyl and C 1.6 alkoxy, and n represents an integer from 0-4;

R 8 and R 9 independently represent C 1-6 alkyl; and

R 11 represents C 1-6 alkyl or aryl optionally substituted by C 1-6 alkyl or halogen.

14. A compound of Formula (III):

wherein:

R 2 represents hydrogen or C 1-6 alkyl;

R 3 represents hydrogen or C 1-6 alkyl;

R 4 represents a group (W):

wherein A represents an aryl, pyridine, thiophene or furan group; R 5 represents cyano, tetrazol-5-yl or —CO 2 R 8 ; R 6 and R 7 independently represent hydrogen, C 1-6 alkyl, —CO 2 R 8 , cyano, tetrazol-5-yl, halogen, trifluoromethyl or C 1-6 alkoxy, or when R 6 and R 7 are bonded to adjacent carbon atoms, R 6 and R 7 may, together with the carbon atoms to which they are bonded, form a fused 5- or 6- membered ring optionally having one or two nitrogen, oxygen or sulfur atoms; each R 12 independently represents substituents selected from: C 1-6 alkyl, halogen, trifluoromethyl and C 1-6 alkoxy, and n represents an integer from 0-4;

R 8 represents C 1-6 alkyl;

R 11 represents C 1-6 alkyl or aryl optionally substituted by C 1-6 alkyl or halogen.

15. The process according to claim 1 wherein:

R 1 is phenyl substituted by a chlorine atom located in the meta position;

R 2 is hydrogen;

R 3 is hydrogen;

X 1 and X 2 are both hydrogen;

R 4 is W;

A is located meta to the phenyl ring;

R 5 is —CO 2 H in the compound of Formula (IA) and —CO 2 CH 3 in the compound of Formula (IB);

R 6 and R 7 are both hydrogen;

R 11 represents methyl; and

n is 0.

16. The process according to claim 1 wherein:

the compound of Formula (IA) is:

or a salt thereof; and

the compound of Formula (IB) is:

17. The compound of Formula (IB) according to claim 13 wherein

R 1 is phenyl substituted by a chlorine atom located in the meta position;

R 2 is hydrogen;

R 3 is hydrogen;

R 4 is W;

A is located meta to the phenyl ring;

R 5 is —CO 2 CH 3 ;

R 6 and R 7 are both hydrogen;

R 11 represents methyl; and

n is 0.

18. The compound of Formula (IB) according to claim 13 , wherein said compound is:

19. The compound of Formula (III) according to claim 14 wherein

R 2 is hydrogen;

R 3 is hydrogen;

R 4 is W

R 5 is —CO 2 H;

R 6 and R 7 are both hydrogen;

R 11 represents methyl; and

n is 0.

20. The compound of Formula (III) according to claim 14 wherein said compound is: