Pleuromutilin derivatives and their use as antimicrobials

1. A compound of formula (I) or formula (II);

wherein

X is oxygen or sulfur, and

Y is a residue of pipecolic acid or a residue of an amino acid.

2. A compound-selected from the group consisting of:

14-O-[(3-{[((R)-Piperidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((R)-2-Amino-3-methyl)-butyroylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((2R,4R)-4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-Amino-3-(3H-imidazol-4-yl)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[2-(2-Amino-acetylamino)-acetylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((R)-Pyrrolidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[2-Amino-acetylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-((S)-2-Amino-propionylamino)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((S)-2-Amino-3-methyl)-butyroylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{(2-[((R)-Pyrrolidine-2-carbonyl)-amino]-acetylamino)-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((2R,3S)-2-Amino-3-hydroxy)-butyroylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2,6-Diamino-hexanoylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-(1H-indol-3-yl)-propylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-phenyl-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-carbamoyl-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2,6-Diamino-hexanoylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2((S)-2-Amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((R)-2-Amino-3-hydroxy)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-Amino-propylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-4-carbamoyl-butyroylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((S)-1-(2-Amino-acetyl)-pyrrolidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-(3H-imidazol-4-yl)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((S)-Piperidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((S)-Pyrrolidine-2-carbonyl)-amino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-Amino-3-phenyl-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((S)-2-Amino-3-hydroxy)-propionylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((2S,3R)-2-Amino-3-hydroxy)-butyroylamino]-methyl}-phenylsulfanyl)-acetyl]-mutilin,

14-O-[(3-{[((R)-2-Amino-3-hydroxy)-propionylamino]-methyl}-phenoxy)-acetyl]-mutilin,

14-O-[(3-{[((R)-Pyrrolidine-2-carbonyl)-amino]-methyl}-phenoxy)-acetyl]-mutilin,

14-O-[(3-{[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-phenoxy)-acetyl]-mutilin,

14-O-[(3-{[(R)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-phenoxy)-acetyl]-mutilin,

14-O-[(3-{[((R)-Pyrrolidine-2-carbonyl)-amino]-methyl}-phenoxy)-acetyl]-19,20-dihydromutilin,

14-O-[(3-{[((R)-2-Amino-3-hydroxy)-propionylamino]-methyl}-phenoxy)-acetyl]-19,20-dihydromutilin, or

14-O-[(3-{[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-phenoxy)-acetyl]-19,20-dihydromutilin.

3. The compound of claim 1 , in the form of a salt.

4. The compound of claim 1 , wherein the compound is in a pharmaceutical composition.

5. A method of treatment of bacterial diseases, which comprises:

administering to a subject in need of such treatment an effective amount of a compound of claims 1 .

6. A method of manufacturing a composition for treatment of bacterial diseases, the method comprising:

obtaining a compound according to claim 1 ; and

including the compound in a medicament for the treatment of bacterial diseases.

7. The method of claim 5 , wherein the bacterial disease is a skin or soft tissue infection.

8. A pharmaceutical composition comprising:

a compound of claim 1 in association with at least one pharmaceutical excipient.

9. The pharmaceutical composition of claim 8 , further comprising another pharmaceutically active agent.

10. The compound of claim 2 , in the form of a salt.

11. A method of treatment of bacterial diseases, which method comprises:

administering to a subject in need of such treatment an effective amount of a compound of claim 2 .

12. The method of claim 11 , wherein the bacterial diseases is a skin or soft tissue infection.

13. A method of treatment of bacterial diseases, which method comprises:

administering to a subject in need of such treatment an effective amount of a compound of claim 3 .

14. The method of claim 13 , wherein the bacterial diseases is a skin or soft tissue infection.

15. A method of treatment of bacterial diseases, which method comprises:

administering to a subject in need of such treatment an effective amount of a compound of claim 4 .

16. The method of claim 15 , wherein the bacterial diseases is a skin or soft tissue infection.

17. A pharmaceutical composition comprising:

a compound of claim 2 in association with at least one pharmaceutical excipient.

18. A pharmaceutical composition comprising:

a compound of claim 3 in association with at least one pharmaceutical excipient.

19. A pharmaceutical composition comprising:

a compound of claim 4 in association with at least one pharmaceutical excipient.