Novel compounds

Abstract

The invention provides compounds of formula in which R 1 , R 2 , R 3 and R 4 have the meanings defined in the specification; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.

1 . A method of treating cancer comprising administering a therapeutically effective amount of a pharmaceutical composition comprising a compound of formula (I): 
       
         
           
           
               
               
           
         
         or pharmaceutically acceptable salt thereof, to a cancer patient with hematopoietic tumors of lymphoid lineage wherein 
         R 1  represents a 5- or 6-membered heteroaromatic ring comprising at least one ring heteroatom selected from nitrogen, oxygen, and sulphur, the ring being optionally substituted with at least one substituent selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy (each of which may be optionally substituted by at least one substituent selected from halogen, amino, hydroxyl, and trifluoromethyl), halogen, nitro, cyano, —NR 5 R 6 , carboxyl, hydroxyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylamino, phenylcarbonyl, —S(O) m C 1 -C 6 alkyl, —C(O)NR 7 R 8 , —SO 2 NR 7a R 8a , and an unsaturated 5- to 6-membered ring which may comprise at least one ring heteroatom selected from nitrogen, oxygen, and sulphur, the ring itself being optionally substituted with at least one substituent selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy (each of which may be optionally substituted by at least one substituent selected from halogen, amino, hydroxyl, and trifluoromethyl), halogen, nitro, cyano, —NR 9 R 10 , carboxyl, hydroxyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylamino, phenylcarbonyl, —S(O) n C 1 -C 6 alkyl, —C(O)NR 11 R 12 , and —SO 2 NR 11a R 12a ; 
         m is 0, 1, or 2; 
         n is 0, 1, or 2; 
         R 2  represents a C 1 -C 4 alkyl group optionally substituted with at least one substituent selected from halogen, hydroxyl, and C 1 -C 3 alkoxy; 
         R 3  represents halogen; 
         R 4  represents a 5-membered heteroaromatic ring comprising at least one ring heteroatom selected from nitrogen, oxygen, and sulphur, the ring being optionally substituted with at least one substituent selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy (each of which may be optionally substituted by at least one substituent selected from halogen, amino, hydroxyl, and trifluoromethyl), halogen, nitro, cyano, —NR 13 R 14 , carboxyl, hydroxyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylcarbonylamino, phenylcarbonyl, —S(O) p C 1 -C 4 alkyl, —C(O)NR 15 R 16 , and —SO 2 NR 15a R 16a ; 
         p is 0, 1, or 2; 
         R 5  and R 6  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 5  and R 6  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 7  and R 8  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 7  and R 8  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 7a  and R 8a  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 7a  and R 8a  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 9  and R 10  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 9  and R 10  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 11  and R 12  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 11  and R 12  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 11a  and R 12a  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 11a  and R 12a  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 13  and R 14  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 13  and R 14  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; 
         R 15  and R 16  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 15  and R 16  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle; and 
         R 15a  and R 16a  each independently represent hydrogen, C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, or R 15a  and R 16a  together with the nitrogen atom to which they are attached form a 4- to 6-membered saturated heterocycle. 
       
     
     
         2 . The method of  claim 1 , wherein said patient has a cancer selected from acute lymphocytic leukaemia, B-cell lymphoma, and Burketts lymphoma. 
     
     
         3 . A compound 2,5-dichloro-4-(5-methyl-1H-pyrrazol-3-ylamino)pyrimidine.