MY103817A - Chloroaniline derivatives - Google Patents

Abstract

THE INVENTION PROVIDES COMPOUNDS OF THE GENERAL FORMULA (1) (FORMULA 1) AND PHYSIOLOGICALLY ACCEPTABLE SALTS AND SOLVATES THEREOF, WHEREIN Q REPRESENTS CHLORINE ATOM OR A TRIFLUOROMETHYL GROUP; X REPRESENTS BOND OR A C2- 6 ALKYLENE, C2- 6 ALKENYLENE OR C2- 6 ALKYNYLENE CHAIN AND Y REPRESENTS A BOND, OR A C1- 6 ALKYLENE, C2- 6 ALKENYLENE OR C2- 6 ALKYNYLENE CHAIN WITH THE PROVISO THAT THE SUM TOTAL OR CORBON ATOMS IN THE CHAINS X AND Y IS NOT MORE THAN 10, AND THE CHAINS XCH2 AND CH2Y MAY EACH BE OPTIONALLY SUBSTITUTED BY ONE OR TWO C1- 3 ALKYL GROUPS, OR, WHEN ONE CARBON ATOM IS SUBSTITUTEDBY TWO ALKYL GROUPS, THESE MAY BE LINKED TO FORM AN ALKYLENE GROUP; R REPRESENTS A HYDROGEN ATOM OR A C1- 3 ALKYL GROUP; R1 AND R2 EACH REPRESENT A HYDROGEN ATOM OR A C1- 3 ALKYL GROUP, WITH THE PROVISO THAT THE SUM TOTAL OF CARBON ATOMS IN R1 AND R2 IS NOT MORE THAN 4; AND HET REPRESENTS BENZOHETEROARYL OR A MONOCYCLIC HETEROARYL GROUP WHEREIN THE HETEROARYL GROUP IS 5 OR 6 MEMBERED AND CONTAINS1, 2, OR 3 HETERO ATOMS ONE OF WHICH IS A NITROGEN ATOM AND THE OTHER (S) IS (ARE) NITROGEN, OXYGEN OR SULPHUR ATOM (S), AND THE GROUP HET MAY OPTIONALLY BE SUBSTITUTED BY ONE OR TWO GROUPS SELECTED FROM C1-4 ALKYL, C1- 4 ALKOXY, HYDROXY, HALOGEN, -NR3 R4 AND - COR8; WHERE R3 AND R4 EACH REPRESENT A HYDROGEN ATOM OR A C1- 4 ALKYL GROUP OR -NR3R4 FORMS A SATURATED HETEROCYCLIC AMINO GROUP WHICH HAS 5- 7 RING MEMBERS AND OPTIONALLY CONTAINS IN THE RING ONE OR MORE ATOMS SELECTED FROM -0- OR -S-OR A GROUP -NH- OR -N (CH3);- AND R8 REPRESENTS HYDROXY, C1- 4 ALKOXY OR - NR3R4 WITH THE PROVISO THAT(i) WHEN HET REPRESENTS A PYRIDYL GROUP SUBSTITUTED BY THE GROUP -NR3R4 OR -COR8 AND Q IS A CHLORINE ATOM, OR (ii) WHEN HET REPRESENTS A PYRIDYL GROUP OPTIONALLY SUBSTITUTED BY ONE OR TWO GROUPS SELECTED FROM HALOGEN, HYDROXY, C1- 3 ALKYL AND C1- 3 ALKOXY, AND Y REPRESENTS A BOND OR A C1- 4 ALKYLENE, C2- 4 ALKENYLENE OR C2- 4 ALKYNYLENE CHAIN, THEN IN BOTH CASES, R REPRESENTS A C1- 3 ALKYL GROUP AND/OR AT LEAST ONE OF THE CHAINS -XCH2- AND -CH2Y- IS SUBSTITUTED BY ONE OR TWO C1- 3 ALKYL GROUPS. THE COMPOUNDS HAVE A STIMULANT ACTION AT 2- ADRENORECEPTORS AND MAY BE USED IN THE TREATMENT OF DISEASES ASSOCIATED WITH REVERSIBLE AIRWAYS OBSTRUCTION SUCH AS ASTHMA AND CHRONIC BRONCHITIS.