Antiviral indoles

1. A compound of the formula (I):

wherein

Ar is a moiety containing at least one aromatic ring and possesses 5-, 6-, 9- or 10-ring atoms optionally containing 1, 2 or 3 heteroatoms independently selected from N, O and S, which ring is optionally substituted by groups Q 1 and Q 2 ;

Q 1 is halogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, aryl, heteroaryl, CONR a R b , (CH 2 ) 0-3 NR a R b , O(CH 2 ) 1-3 NR a R b , O(CH 2 ) 0-3 CONR a R b , O(CH 2 ) 0-3 aryl, O(CH 2 ) 0-3 heteroaryl, O(CR e R f )aryl, O(CR e R f )heteroaryl or OCHR c R d ;

R a and R b are each independently selected from hydrogen, C 1-4 alkyl and C(O)C 1-4 alkyl;

or R a , R b and the nitrogen atom to which they are attached form a heteroaliphatic ring of 4 to 7 ring atoms, where said ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

R c and R d are each independently selected from hydrogen and C 1-4 alkoxy;

or R c and R d are linked by a heteroatom selected from N, O and S to form a heteroaliphatic ring of 4 to 7 ring atoms, where said ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

and wherein said C 1-4 alkyl, C 1-4 alkoxy and aryl groups are optionally substituted by halogen or hydroxy;

R e is hydrogen or C 1-6 alkyl;

R f is C 1-6 alkyl;

Q 2 is halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy, where said C 1-4 alkyl and C 1-4 alkoxy groups are optionally substituted by halogen or hydroxy;

or Q 1 and Q 2 may be linked by a bond or a heteroatom selected from N, O and S to form a ring of 4 to 7 atoms, where said ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

A is C 3-6 alkyl or C 2-6 alkenyl,

or A is a non-aromatic ring of 3 to 8 ring atoms where said ring may contain a double bond and/or may contain a O, S, SO, SO 2 or NH moiety,

or A is a non-aromatic bicyclic moiety of 4 to 8 ring atoms,

and A is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

D is N or CR g ;

R g is hydrogen, fluorine, chlorine, C 1-4 alkyl, C 2-4 alkenyl or C 1-4 alkoxy, where said C 1-4 alkyl, C 2-4 alkenyl and C 1-4 alkoxy groups are optionally substituted by hydroxy or fluorine;

W is a bond, C═O, O, S(O) 0-2 or —(CR 10 R 11 )—(CR 12 R 13 ) 0-1 —;

Y is a bond, C═O, O, —CR 14 R 15 — or NR 14 ;

Z is a bond, C═O, O, S(O) 0-2 , —(CR 10 R 11 )—(CR 12 R 13 ) 0-1 — or NR 10 ;

and none, one or two of W, Y and Z are a bond;

X is —CR 14a — or N;

R 10 , R 11 , R 12 , R 13 , R 14 , R 14a and R 15 are each independently selected from hydrogen, hydroxy, C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkoxy, C(O)C 1-6 alkyl, Het, (CH 2 ) 0-3 NR 16 R 17 , C(O)(CH 2 ) 0-3 NR 16 R 17 , NHC(O)(CH 2 ) 0-3 NR 16 R 17 , O(CH 2 ) 1-3 NR 16 R 17 , S(O) 0-2 (CH 2 ) 0-3 R 16 R 17 and C(O)(CH 2 ) 0-3 OR 16 ;

or one of R 10 , R 14 and R 14a is linked to R 22 or R 23 to form a ring of 4 to 10 atoms, where said ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

Het is a heteroaliphatic ring of 4 to 7 ring atoms, which ring may contain 1, 2 or 3 heteroatoms selected from N, O or S or a group S(O), S(O) 2 , NH or NC 1-4 alkyl;

R 16 and R 17 are independently selected from hydrogen, C 1-6 alkyl and (CH 2 ) 0-4 NR 18 R 19 ;

or R 16 , R 17 and the nitrogen atom to which they are attached form a heteroaliphatic ring of 4 to 7 ring atoms, which ring may optionally contain 1 or 2 more heteroatoms selected from O or S or a group S(O), S(O) 2 , NH or NC 1-4 alkyl, and which ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

R 18 and R 19 are independently selected from hydrogen and C 1-6 alkyl;

or R 18 , R 19 and the nitrogen atom to which they are attached form a heteroaliphatic ring of 4 to 7 ring atoms, which ring may optionally contain 1 or 2 more heteroatoms selected from O or S or a group S(O), S(O) 2 , NH or NC 1-4 alkyl, and which ring is optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy;

R 1 is hydrogen or C 1-6 alkyl;

B is —CR 20 R 21 —, —C(═O)—, —SO— or —SO 2 —;

R 20 and R 21 are independently selected from hydrogen and C 1-6 alkyl;

or R 20 and R 21 , together with the carbon atom to which they are joined, form a C 3-6 cycloalkyl group;

M is C 4-8 alkylene or C 4-8 alkenylene, optionally substituted by R 22 , where 1, 2 or 3 of the carbon atoms in the C 4-8 alkylene or C 4-8 alkenylene groups is optionally replaced by O, NR 23 , S, SO, SO 2 , piperidinyl, piperazinyl or pyrrolidinyl,

where R 23 is hydrogen or C 1-6 alkyl, or R 23 is linked to one of R 10 , R 14 and R 14a to form a ring of 4 to 10 atoms as hereinbefore described;

where R 22 is halo, C 1-4 alkyl, (CH 2 ) 0-3 C 3-8 cycloalkyl, (CH 2 ) 0-3 aryl, (CH 2 ) 0-3 heteroaryl, (CH 2 ) 0-3 Het or oxo,

or R 22 is linked to one of R 10 , R 14 and R 14a to form a ring of 4 to 10 atoms as hereinbefore described;

or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 in which Ar is phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl or 3-furanyl, optionally substituted by groups Q 1 and Q 2 as defined in claim 1 .

3. A compound according to claim 2 in which Q 1 is methoxy and Q 2 is absent.

4. A compound according to claim 1 in which A is cyclopentyl or cyclohexyl optionally substituted by halogen, hydroxy, C 1-4 alkyl or C 1-4 alkoxy.

5. A compound according to claim 1 in which D is CR g where R g is hydrogen or C 1-4 alkyl.

6. A compound according to claim 1 in which W is —CH 2 — or —CH 2 CH 2 —.

7. A compound according to claim 1 in which W is Z is a bond, O, —CH 2 — or —CH 2 CH 2 —.

8. A compound according to claim 1 in which Y is —CH 2 —, NH, N(C 1-4 alkyl), N(CH 2 ) 2 N(C 1-4 alkyl) 2 or NC(O)CH 2 N(C 1-4 alkyl) 2 .

9. A compound according to claim 1 in which X is —CH— or —C(C 1-6 alkyl)-.

10. A compound according to claim 1 in which R 1 is hydrogen or methyl.

11. A compound according to claim 1 in which B is —CH 2 — or —SO 2 —.

12. A compound according to claim 1 in which M is selected from:

13. A compound according to claim 1 of the formula (Ia):

or a pharmaceutically acceptable salt thereof, wherein W, X, Y, Z and M are as defined in relation to formula (I).

14. A compound according to claim 1 selected from:

(7R)-14-cyclohexyl-21,24-dimethyl-7,8-dihydro-6H-7,11-(epiminoethanoiminopropanothio iminomethano)indolo[1,2-e][1,5]benzoxazocin-15-one 17,17-dioxide,

(7R)-14-cyclohexyl-24-methyl-7,8-dihydro-6H-7,11-(epiminoethanoiminopropanothioimino methano)indolo[1,2-e][1,5]benzoxazocin-15-one 17,17-dioxide,

(7 R)-14-cyclohexyl-25-methyl-7,8-dihydro-6H-7,11-(epiminoethanoiminobutanothioimino methano)indolo[1,2-e][1,5]benzoxazocine-15,21-dione 17,17-dioxide,

(7R)-14-[(1R,2S) or (1S,2R)-2-fluorocyclohexyl]-21,24-dimethyl-7,8-dihydro-6H-7,11-(epiminoethanoiminopropanothioiminomethano)indolo[1,2-e][1,5]benzoxazocin-15-one 17,17-dioxide,

and pharmaceutically acceptable salts thereof.

15. A pharmaceutical composition comprising an effective amount of a compound of the formula (I), or a pharmaceutically acceptable salt thereof, according to claim 1 and a pharmaceutically acceptable carrier.