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1. WO2020109224 - FURTHER HETEROAROMATIC COMPOUNDS HAVING ACTIVITY AGAINST RSV

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

Claims

1. A compound of formula (I) wherein


including any stereochemically isomeric form thereof, wherein


X1 X2, and X3 are selected from Xj is N, X2 is CH, and X3 is CH;

or Xi is N, X2 is N, and X3 is CH,

or Xi is N, X2 is CH, and X3 is N,

or Xi is CH, X2 is CH, and X3 is CH, and

or Xx is CH, X2 is N, and X3 is CH,

wherein each CH is optionally substituted with halo or

C^alkyl;

Y1 and Y2 are each independently selected from CH, CF and N;

R1 is CH3 or CH2CH3;

R2 is hydrogen, halo or C| -4alkyl;

R12 is C^alkyl;

R13 and R14 are each independently selected from C^alkyl;

R15 is hydrogen or C| -4alkyl;

R3 is halo;

R4 is C| -6alkyl; C3_6cycloalkyl; di(C| -4alkyl)amino, pyrrolidinyl, Heteroaryl1; phenyl; phenyl substituted with 1, 2 or 3 substituents each individually selected from halo, hydroxy, cyano, C^alkyl, polyhaloC| -4alkyl, and C| -4alkyloxy;

R6 is a substituent selected from substituent (a), (b), (c), (d) or (e); wherein

(a) is -(CO)-OH, -(CO)-NR7R8, or -NR7R8;

(b) is Heteroaryl2;

(c) is C2-6alkenyl substituted with one or two substituents selected from C| -6alkyl, -(CO)-OH or -(CO)-NR8R9; or

(d) is -NR8-(CO)-Heterocycle wherein said Heterocycle is substituted with one, two or three substituents each independently selected from halo, hydroxy, C| -4alkyl of Ci_4alkyloxy; or

(e) is C3_6cycloalkyl or Heterocycle, wherein said C3_6cycloalkyl and Heterocycle is substituted with one, two or three substituents each independently selected from

C^alkyl;

C| -6alkyl substituted with one, two or three substituents each independently selected from halo, hydroxy, hydroxycarbonyl, and aminocarbonyl; hydroxy;

halo;

-(CO)-OH;

-(CO)-NR10R11;

-(C0)-NR8-S02-R9;

-NR8R9;

-NR8-(CO)-C i _4alkyl;

-NR8-(CO)-C3_6cycloalkyl;

-NR8-S02-R9;

-S02-NR10R11; or

-S02-NR8-(C0)-R9;

wherein

R7 is hydrogen, C | _4alky 1 , hydroxyC| -4alkyl or dihydroxyC| -4alkyl;

each R8 is independently selected from hydrogen, C| -4alkyl, or hydroxyC| -4alkyl;

R10 and R11 are each indepently selected from hydrogen; C| -4alkyl;

polyhaloC| -4alkyl; C3_6cycloalkyl; C3_6cycloalkyl substituted with C i _4alky 1 ; or C| -4alkyl substituted with hydroxy or cyano;

Heterocycle is azetidinyl, pyrrolodinyl, piperidinyl, or homopiperidinyl;

Heteroaryl1 is thienyl, pyridinyl or pyrimidinyl, wherein each Heteroaryl1 is optionally substituted with one or two substituents each independently selected from C| -4alkyl, halo, amino, and aminocarbonyl;

Heteroaryl2 is pyrrolyl, pyrazolyl or thiazolyl; wherein each Heteroaryl2 is optionally

substituted with one or two substituents each independently selected from C | _4al ky 1, halo, -(CO)-OR7 or -(CO)-NR8R9;

or a pharmaceutically acceptable acid addition salt thereof.

2. The compound as claimed in claim 1 wherein X | is N, X2 is CH, and X3 is CH.

3. The compound as claimed in claim 1 wherein X | is N, X2 is N, and X3 is CH.

4. The compound as claimed in claim 1 wherein X | is N, X2 is CH, and X3 is N.

5. The compound as claimed in claim 1 wherein A is a radical of formula (a-1) wherein R1 is CH3.

6. The compound as claimed in claim 1 wherein A is a radical of formula (a-2) wherein R1 is CH3.

7. The compound as claimed in claim 1 wherein A is a radical of formula (a-5) wherein R1 is CH3.

8. The compound as claimed in any one of claims 1 to 7 wherein R4 is C3_6cycloalkyl.

9. The compound as claimed in any one of claims 1 to 8 wherein R6 is C3_6cycloalkyl or

pyrrolidinyl, wherein said C3_6cycloalkyl or pyrrolidinyl are substituted with one or two substituents each independently selected from OH, -(CO)-OH or -(CO)-NR10R11.

10. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a

therapeutically active amount of a compound as claimed in any one of claims 1 to 9.

11. The pharmaceutical composition according to claim 10, which further comprises another antiviral agent.

12. The pharmaceutical composition according to claim 11, wherein the other antiviral agent is a RSV inhibiting compound.

13. A process for preparing a pharmaceutical composition as claimed in any one of claims 10 to 12 wherein a therapeutically active amount of a compound as claimed in any one of claims 1 to 9 is intimately mixed with a pharmaceutically acceptable carrier.

14. A compound as claimed in any one of claims 1 to 9 for use as a medicine.

15. A compound as claimed in any one of claims 1 to 9, or a pharmaceutical composition as claimed in any one of claims 10 to 12, for use in the treatment or prevention of a respiratory syncytial virus infection.