Aminoheterocyclic derivatives as antithrombotic or anticoagulant

A compound of the formula I wherein:

• each of G.sup.1 and G.sup.3 is CH and G.sup.2 is N, or each of G.sup.1 and G.sup.2 is CH and G.sup.3 is N;
• m is 1 or 2;
• each R.sup.1 is independently selected from hydrogen, amino, halogeno, cyano, (1-4C)alkyl and (1-4C)alkoxy;
• M.sup.1 is a group of the formula
• NR.sup.2 -L.sup.1 -T.sup.1 R.sup.3
• in which R.sup.2 and R.sup.3 together form a (1-4C)alkylene group,
• L.sup.1 is (1-4C)alkylene, and
• T.sup.1 is CH or N,
• and wherein 1 or 2 methylene groups within L.sup.1 and the rings formed when R.sup.2 and R.sup.3 are linked optionally bears a (1-4C)alkyl substituent;
• A is a direct link to the carbonyl group, or A is (1-4C)alkylene;
• M.sup.2 is a group of the formula
• (T.sup.2 R.sup.4).sub.r -L.sup.2 -T.sup.3 R.sup.5
• in which r is 0 or 1,
• T.sup.2 is N,
• T.sup.3 is N,
• R.sup.4 is hydrogen or (1-4C)alkyl,
• R.sup.5 is hydrogen or (1-4C)alkyl,
• or R.sup.4 and R.sup.5 together form a (1-4C)alkylene, methylenecarbonyl or carbonylmethylene group, or R.sup.4 is a (2-3C)alkylene group which is linked to a methylene group within L.sup.2 forming a 5- or 6-membered ring involving R.sup.4 and T.sup.2, or R.sup.5 is a (2-3C)alkylene group which is linked to a methylene group within L.sup.2 forming a 5- or 6-membered ring involving R.sup.5 and T.sup.3,
• L.sup.2 is (1-4C)alkylene or (1-3C)alkylene-carbonyl, and, when r is 1, L.sup.2 may also be carbonyl-(1 -3C)alkylene,
• and wherein 1 or 2 methylene groups within L.sup.2 and the rings formed when R.sup.4 and R.sup.5,
• R.sup.4 and L.sup.2 or R.sup.5 and L.sup.2 are linked optionally bears a substituent selected from the group consisting of oxo, carboxy, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, pyrrolidin- 1 -ylcarbonyl, piperidinocarbonyl, morpholinocarbonyl, piperazin-1-ylcarbonyl, 4-(1-4C)alkylpiperazin-1-ylcarbonyl, N-phenylcarbamoyl, N-(1-4C)alkyl-N-phenylcarbamoyl, N-[phenyl-(1-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[phenyl-(1-3C)alkyl]carbamoyl, N-[hydroxy-(2-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[hydroxy(2-3C)alkyl]carbamoyl, N-[(1-4C)alkoxy-(2-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[(1-4C)alkoxy-(2-3C)alkyl]carbamoyl, N-[carboxy-(1-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[carboxy-(1 -3C)alkyl]carbamoyl, N-[carboxy-(1-3C)alkyl]-N-[hydroxy-(2-3C)alkyl]carbamoyl, N-[carboxy-(1-3C)alkyl]-N-[(1-4C)alkoxy-(2-3C)alkyl]carbamoyl, N-[(1-4C)alkoxycarbonyl-(1-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[(1-4C)alkoxycarbonyl-(1-3C)alkyl]carbamoyl, N-[(1-4C)alkoxycarbonyl-(1-3C)alkyl]-N-[hydroxy-(2-3C)alkyl]carbamoyl, N-[(1-4C)alkoxycarbonyl-(1-3C)alkyl]-N-[( 1-4C)alkoxy-(2-3C)alkyl]carbamoyl, (1-4C)alkyl, carboxy-(1-4C)alkyl, (1-4C)alkoxycarbonyl-(1-4C)alkyl, carbamoyl-(1-4C)alkyl, N-(1-4C)alkylcarbamoyl-(1-4C)alkyl, N,N-di-(1-4C)alkylcarbamoyl-(1-4C)alkyl, pyrrolidin-1-ylcarbonyl-(1-4C)alkyl, piperidinocarbonyl-(1-4C)alkyl, morpholinocarbonyl-(1-4C)alkyl, piperazin-1-ylcarbonyl-(1-4C)alkyl, 4-(1-4C)alkylpiperazin-1-ylcarbonyl-(1-4C)alkyl, N-phenylcarbamoyl-(1-4C)alkyl, N-[phenyl-(1-3C)alkyl]carbamoyl-(1-4C)alkyl, hydroxy-(1-4C)alkyl, (1-4C)alkoxy-(1-4C)alkyl and phenyl-(1-4C)alkyl,
• and wherein any heterocyclic group in said substituent optionally bears 1 or 2 substituents selected from the group consisting of (1-4C)alkyl, (1-4C)alkoxy, carboxy, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl and N,N-di-(1-4C)alkylcarbamoyl,
• and wherein any phenyl or phenylene group in M.sup.2 optionally bears 1 or 2 substituents selected from the group consisting of halogeno, trifluoromethyl, (1-4C)alkyl and (1-4C)alkoxy;
• M.sup.3 is a direct link to X, or M.sup.3 is a group of the formula
• L.sup.3 -(NR.sup.6).sub.s
• in which s is 0 or 1,
• R.sup.6 is hydrogen or (1-4C)alkyl, or R.sup.5 and R.sup.6 together form a (1-4C)alkylene, methylenecarbonyl or carbonylmethylene group, or R.sup.6 is a (2-3C)alkylene group which is linked to a methylene group within L.sup.3 forming a 5- or 6-membered ring involving NR.sup.6,
• L.sup.3 is (1-4C)alkylene or carbonyl-(1-3C)alkylene, and, when s is 1, L.sup.3 may also be (1-3C)alkylene-carbonyl,
• and wherein 1 or 2 methylene groups within L.sup.3 and the rings formed when R.sup.5 and R.sup.6 or R.sup.6 and L.sup.3 are linked optionally bears a substituent selected from the group consisting of oxo, carboxy, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, pyrrolidin-1-ylcarbonyl, piperidinocarbonyl, morpholinocarbonyl, piperazin-1-ylcarbonyl, 4-(1-4C)alkylpiperazin-1-ylcarbonyl, N-phenylcarbamoyl, N-(1-4C)alkyl-N-phenylcarbamoyl, N-[phenyl-(1-3C)alkyl]carbamoyl, N-(1-4C)alkyl-N-[phenyl-(1-3C)alkyl]carbamoyl, (1-4C)alkyl, carboxy-(1-4C)alkyl, (1-4C)alkoxycarbonyl-(1-4C)alkyl, carbamoyl-(1-4C)alkyl, N-(1-4C)alkylcarbamoyl-(1-4C)alkyl, N,N-di-(1-4C)alkylcarbamoyl-(1-4C)alkyl, pyrrolidin-1-ylcarbonyl-(1-4C)alkyl, piperidinocarbonyl-(1-4C)alkyl, morpholinocarbonyl-(1-4C)alkyl, piperazin-1-ylcarbonyl-(1-4C)alkyl, 4-(1-4C)alkylpiperazin-1-ylcarbonyl-(1-4C)alkyl, N-phenylcarbamoyl-(1-4C)alkyl, N-[phenyl-(1-3C)alkyl]carbamoyl-(1-4C)alkyl, hydroxy-(1-4C)alkyl, (1-4C)alkoxy-(1-4C)alkyl and phenyl-(1-4C)alkyl,
• and wherein any heterocyclic group in said substituent optionally bears 1 or 2 substituents selected from the group consisting of (1-4C)alkyl, (1-4C)alkoxy, carboxy, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl and N,N-di-( 1-4C)alkylcarbamoyl,
• and wherein any phenyl or phenylene group in M.sup.3 optionally bears 1 or 2 substituents selected from the group consisting of halogeno, trifluoromethyl, (1-4C)alkyl and (1-4C)alkoxy;
• X is oxy, thio, sulphinyl, sulphonyl, sulphonylamino, methylene, (1-4C)alkylmethylene or di-(1-4C)alkylmethylene, or, when T.sup.3 is CH and M.sup.3 is a direct link to X, X may also be aminosulphonyl or oxycarbonyl;
• and
• Q is phenyl, naphthyl, phenyl-(1-4C)alkyl, phenyl-(2-4C)alkenyl, phenyl-(2-4C)alkynyl, (5-7C)cycloalkyl or a heterocyclic moiety containing up to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, and Q optionally bears 1, 2 or 3 substituents selected from the group consisting of hydroxy, amino, halogeno, cyano, trifluoromethyl, nitro, carboxy, carbamoyl, formyl, formimidoyl, formohydroximoyl, (1-4C)alkoxycarbonyl, (1-4C)alkyl, (1-4C)alkoxy, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, (1-4C)alkylamino, di-(1-4C)alkylamino, (2-4C)alkanoylamino, (2-4C)alkanoyl, (2-4C)alkanoimidoyl, (2-4C)alkanohydroximoyl, phenyl, heteroaryl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, heteroaryloxy, heteroarylthio, heteroarylsulphinyl, heteroarylsulphonyl, benzyl and benzoyl,
• and wherein said heteroaryl substituent or the heteroaryl group in a heteroaryl-containing substituent comprises a 5- or 6-membered monocyclic heteroaryl ring containing up to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur,
• and wherein said phenyl, heteroaryl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, heteroaryloxy, heteroarylthio, heteroarylsulphinyl, heteroarylsulphonyl, benzyl or benzoyl substituent optionally bears 1, 2, 3 or 4 substituents selected from the group consisting of halogeno, trifluoromethyl, cyano, trifluoromethoxy, nitro, (1-4C)alkyl, (1-4C)alkoxy, hydroxy, amino, carboxy, carbamoyl, (1-4C)alkoxycarbonyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, (1-4C)alkylamino, di-(1-4C)alkylamino, (2-4C)alkanoylamino and tetrazolyl;
• or a pharmaceutically-acceptable salt thereof.