Pyrrolopyrazine kinase inhibitors

US 20090215750A1
Filed: 02/20/2009
Published: 08/27/2009
Est. Priority Date: 02/25/2008
Status: Active Grant

First Claim

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1. A compound of Formula I R is R¹, R², R³, or R⁴;

R¹is lower alkyl, lower alkoxy, phenyl, benzyl, heteroaryl, cycloalkyl, heterocycloalkyl, or cycloalkylalkyl, optionally substituted with one or more R^1a;

R^1ais R^1bor R^1c;

R^1bis halogen, oxo, hydroxy, or —

CN;

R^1cis —

C(═

O)O(R^1f), —

C(═

O)CH₂(R^1e), —

S(R^1f), —

S(O)₂(R^1f), or —

S(═

O) (R^1f), lower alkyl, lower alkoxy, amino, amido, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkyloxy, or heterocycloalkyloxy optionally substituted with one or more R^1d;

R^1dis H, halogen, hydroxy, lower alkyl, lower alkoxy, or lower haloalkyl;

R^1eis H, lower alkyl, lower alkoxy, —

CN, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, or heterocycloalkyl;

R^1fis H, lower alkyl, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, or heterocycloalkyl;

R²is N(R^2a)₂;

each R^2ais independently H or R^2b;

each R^2bis independently lower alkyl, phenyl, heteroaryl, cycloalkyl, heterocycloalkyl, or heterocycloalkyl alkylene, optionally substituted with one or more R^2c;

R^2cis R^2dor R^2e;

R^2dis halogen, oxo, or hydroxy;

R^2eis —

N(R^2g)₂, —

C(═

O)(R^2g), —

C(═

O)O(R^2g), —

C(═

O)N(R^2g)₂, —

N(R^2g)C(═

O)(R^2g), —

S(═

O)₂(R²), —

S(O)₂N(R^2g)₂, lower alkyl, lower alkoxy, lower haloalkyl, phenyl, heteroaryl, heteroaryloxy, cycloalkyl, or heterocycloalkyl, optionally substituted with one or more R^2f;

each R^2fis independently H, halogen, lower alkyl, lower alkoxy, lower haloalkyl;

each R^2gis independently H, lower alkyl, lower alkoxy, lower haloalkyl, or phenyl;

R³is —

C(═

O)R^1a;

R^3ais lower alkyl, lower alkoxy, phenyl, or N(R^3b)₂;

each R^3bis independently H or lower alkyl;

R⁴is —

O(R^4a);

R^4ais H or R^4b;

R^4bis lower alkyl, phenyl, benzyl, lower haloalkyl, cycloalkyl, heterocycloalkyl, heteroaryl, optionally substituted with one or more R^4c;

R^4cis halogen, hydroxy, lower alkyl, lower haloalkyl, or lower alkoxy;

Q²is cycloalkyl, cycloalkenyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q^2a;

Q^2ais Q^2bor Q^2c;

Q^2bis halogen, oxo, hydroxy, —

N, —

SCH₃, —

S(O)₂CH₃, or —

S(═

O)CH₃;

Q^2cis Q^2dor Q^2e;

or two Q^2acome together to form a bicyclic ring system, optionally substituted with one or more Q^2bor Q^2c;

Q^2dis —

O(Q^2e, —

S(═

O)₂(Q^2e), —

C(═

O)N(Q^2e)₂, —

S(O)₂(Q^2e, —

C(═

O)(Q^2e), C(═

O)O(Q^2e, —

N(Q^2e)₂;

—

N(Q^2e)C(═

O)(Q^2s), —

N(Q^2e)C(═

O)O(Q^2e), or —

N(Q^2e)C(═

O)N(Q^2e)₂;

each Q^2eis independently H or Q^2e′;

each Q^2eis independently lower alkyl, phenyl, benzyl, lower haloalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q^2f;

Q^2fis Q^2gor Q^2h;

Q^2gis halogen, hydroxy, cyano, oxo, or —

C(═

O)(Q^2h);

Q^2his lower alkyl, lower haloalkyl, lower alkoxy, amino, phenyl, benzyl, cycloalkyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q²ⁱ; and

Q²ⁱis halogen, hydroxy, cyano, lower alkyl, lower haloalkyl, or lower alkoxy;

or a pharmaceutically acceptable salt thereof.

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Abstract

The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I,

wherein the variables Q and R are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

Citations

54 Claims

1. A compound of Formula I R is R¹, R², R³, or R⁴;
- R¹is lower alkyl, lower alkoxy, phenyl, benzyl, heteroaryl, cycloalkyl, heterocycloalkyl, or cycloalkylalkyl, optionally substituted with one or more R^1a;
  
  R^1ais R^1bor R^1c;
  
  R^1bis halogen, oxo, hydroxy, or —
  
  CN;
  
  R^1cis —
  
  C(═
  
  O)O(R^1f), —
  
  C(═
  
  O)CH₂(R^1e), —
  
  S(R^1f), —
  
  S(O)₂(R^1f), or —
  
  S(═
  
  O) (R^1f), lower alkyl, lower alkoxy, amino, amido, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkyloxy, or heterocycloalkyloxy optionally substituted with one or more R^1d;
  
  R^1dis H, halogen, hydroxy, lower alkyl, lower alkoxy, or lower haloalkyl;
  
  R^1eis H, lower alkyl, lower alkoxy, —
  
  CN, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, or heterocycloalkyl;
  
  R^1fis H, lower alkyl, lower haloalkyl, phenyl, heteroaryl, cycloalkyl, or heterocycloalkyl;
  
  R²is N(R^2a)₂;
  
  each R^2ais independently H or R^2b;
  
  each R^2bis independently lower alkyl, phenyl, heteroaryl, cycloalkyl, heterocycloalkyl, or heterocycloalkyl alkylene, optionally substituted with one or more R^2c;
  
  R^2cis R^2dor R^2e;
  
  R^2dis halogen, oxo, or hydroxy;
  
  R^2eis —
  
  N(R^2g)₂, —
  
  C(═
  
  O)(R^2g), —
  
  C(═
  
  O)O(R^2g), —
  
  C(═
  
  O)N(R^2g)₂, —
  
  N(R^2g)C(═
  
  O)(R^2g), —
  
  S(═
  
  O)₂(R²), —
  
  S(O)₂N(R^2g)₂, lower alkyl, lower alkoxy, lower haloalkyl, phenyl, heteroaryl, heteroaryloxy, cycloalkyl, or heterocycloalkyl, optionally substituted with one or more R^2f;
  
  each R^2fis independently H, halogen, lower alkyl, lower alkoxy, lower haloalkyl;
  
  each R^2gis independently H, lower alkyl, lower alkoxy, lower haloalkyl, or phenyl;
  
  R³is —
  
  C(═
  
  O)R^1a;
  
  R^3ais lower alkyl, lower alkoxy, phenyl, or N(R^3b)₂;
  
  each R^3bis independently H or lower alkyl;
  
  R⁴is —
  
  O(R^4a);
  
  R^4ais H or R^4b;
  
  R^4bis lower alkyl, phenyl, benzyl, lower haloalkyl, cycloalkyl, heterocycloalkyl, heteroaryl, optionally substituted with one or more R^4c;
  
  R^4cis halogen, hydroxy, lower alkyl, lower haloalkyl, or lower alkoxy;
  
  Q²is cycloalkyl, cycloalkenyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q^2a;
  
  Q^2ais Q^2bor Q^2c;
  
  Q^2bis halogen, oxo, hydroxy, —
  
  N, —
  
  SCH₃, —
  
  S(O)₂CH₃, or —
  
  S(═
  
  O)CH₃;
  
  Q^2cis Q^2dor Q^2e;
  
  or two Q^2acome together to form a bicyclic ring system, optionally substituted with one or more Q^2bor Q^2c;
  
  Q^2dis —
  
  O(Q^2e, —
  
  S(═
  
  O)₂(Q^2e), —
  
  C(═
  
  O)N(Q^2e)₂, —
  
  S(O)₂(Q^2e, —
  
  C(═
  
  O)(Q^2e), C(═
  
  O)O(Q^2e, —
  
  N(Q^2e)₂;
  
  —
  
  N(Q^2e)C(═
  
  O)(Q^2s), —
  
  N(Q^2e)C(═
  
  O)O(Q^2e), or —
  
  N(Q^2e)C(═
  
  O)N(Q^2e)₂;
  
  each Q^2eis independently H or Q^2e′;
  
  each Q^2eis independently lower alkyl, phenyl, benzyl, lower haloalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q^2f;
  
  Q^2fis Q^2gor Q^2h;
  
  Q^2gis halogen, hydroxy, cyano, oxo, or —
  
  C(═
  
  O)(Q^2h);
  
  Q^2his lower alkyl, lower haloalkyl, lower alkoxy, amino, phenyl, benzyl, cycloalkyl, heterocycloalkyl, or heteroaryl, optionally substituted with one or more Q²ⁱ; and
  
  Q²ⁱis halogen, hydroxy, cyano, lower alkyl, lower haloalkyl, or lower alkoxy;
  
  or a pharmaceutically acceptable salt thereof.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54)
- - 2. The compound of claim 1, wherein R is R¹.
  - 3. The compound of claim 2, wherein R¹is lower alkyl.
  - 4. The compound of claim 3, wherein R¹is tert-butyl.
  - 5. The compound of claim 3, wherein R¹is —
    - CHC(CH₃)₃.
  - 6. The compound of claim 3, wherein R¹is iso-butyl.
  - 7. The compound of claim 3, wherein R¹is iso-propyl.
  - 8. The compound of claim 2, wherein R¹is cycloalkyl.
  - 9. The compound of claim 2, wherein R¹is heterocycloalkyl.
  - 10. The compound of claim 2, wherein R¹is benzyl.
  - 11. The compound of claim 2, wherein R¹is phenyl.
  - 12. The compound of claim 1, wherein R is R²and R²is NH(R^2a).
  - 13. The compound of claim 12, wherein R^2ais R^2b.
  - 14. The compound of claim 13, wherein R^2bis lower alkyl.
  - 15. The compound of claim 14, wherein R^2bis iso-propyl.
  - 16. The compound of claim 13, wherein R^2bis heterocycloalkyl.
  - 17. The compound of claim 13, wherein R^2bis cycloalkyl.
  - 18. The compound of claim 13, wherein R^2bis heterocycloalkyl alkylene.
  - 19. The compound of claim 18, wherein R^2bis pyrrolidinyl alkylene.
  - 20. The compound of claim 18, wherein R^2bpyrrolidinyl methylene.
  - 21. The compound of claim 1, wherein Q is Q².
  - 22. The compound of claim 21, wherein Q²is heterocycloalkyl, optionally substituted with one or more Q^2a.
  - 23. The compound of claim 22, wherein Q²is pyrrolidine.
  - 24. The compound of claim 22, wherein Q²is piperidine.
  - 25. The compound of claim 22, wherein Q²is heteroaryl, optionally substituted with one or more Q^2a.
  - 26. The compound of claim 25, wherein Q²is pyridine.
  - 27. The compound of claim 26, wherein Q^2ais Q^2cand Q^2Cis heterocycloalkyl.
  - 28. The compound of claim 27, wherein Q^2cis piperazine.
  - 29. The compound of claim 27, wherein Q^2cis pyrrolidine.
  - 30. The compound of claim 27, wherein Q^2cis piperidine.
  - 31. The compound of claim 21, wherein Q²is cycloalkyl.
  - 32. The compound of claim 21, wherein Q²is heteroaryl.
  - 34. A method for treating an inflammatory or autoimmune condition comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 35. The method of claim 34, further comprising administering an additional therapeutic agent selected from a chemotherapeutic or anti-proliferative agent, an anti-inflammatory agent, an immunomodulatory or immunosuppressive agent, a neurotrophic factor, an agent for treating cardiovascular disease, an agent for treating diabetes, or an agent for treating immunodeficiency disorders.
  - 36. A method for treating an inflammatory condition comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 37. A method for inhibiting T-cell proliferative disorder comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 38. A method for inhibiting T-cell proliferative disorder comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 39. The method of claim 38, wherein the proliferative disorder is cancer.
  - 40. A method for treating a B-cell proliferative disorder comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 41. A method for treating an immune disorder including lupus, multiple sclerosis, rheumatoid arthritis, psoriasis, Type I diabetes, complications from organ transplants, xeno transplantation, diabetes, cancer, asthma, atopic dermatitis, autoimmune thyroid disorders, ulcerative colitis, Crohn'"'"'s disease, Alzheimer'"'"'s disease, and Leukemia, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.
  - 42. A method for preventing or treating all forms of organ rejection, including acute allograft or xenograft rejection and chronic allograft or xenograft rejection, of vascularized or non-vascularized transplants, comprising administering to a patient in need thereof the compound of claim 1.
  - 43. A method for inhibiting JAK3 activity comprising administering the compound of claim 1, wherein the compound exhibits an IC₅₀of 50 micromolar or less in an in vitro biochemical assay of JAK3 activity.
  - 44. The method of claim 43 wherein the compound exhibits an IC₅₀of 100 nanomolar or less in an in vitro biochemical assay of JAK3 activity.
  - 45. The method of claim 44 wherein the compound exhibits an IC₅₀of 10 nanomolar or less in an in vitro biochemical assay of JAK3 activity.
  - 46. A method for inhibiting SYK activity comprising administering the compound of claim 1, wherein the compound exhibits an IC₅₀of 50 micromolar or less in an in vitro biochemical assay of SYK activity.
  - 47. The method of claim 46 wherein the compound exhibits an IC₅₀of 100 nanomolar or less in an in vitro biochemical assay of SYK activity.
  - 48. The method of claim 47 wherein the compound exhibits an IC₅₀of 10 nanomolar or less in an in vitro biochemical assay of SYK activity.
  - 49. A method for treating an inflammatory condition comprising co-administering to a patient in need thereof a therapeutically effective amount of an anti-inflammatory compound in combination with the compound of claim 1.
  - 50. A method for treating an immune disorder comprising co-administering to a patient in need thereof a therapeutically effective amount of an immunosuppressant compound in combination with the compound of claim 1.
  - 51. A pharmaceutical composition comprising the compound of claim 1, admixed with at least one pharmaceutically acceptable carrier, excipient or diluent.
  - 52. The pharmaceutical composition of claim 51, further comprising an additional therapeutic agent selected from a chemotherapeutic or anti-proliferative agent, an anti-inflammatory agent, an immunomodulatory or immunosuppressive agent, a neurotrophic factor, an agent for treating cardiovascular disease, an agent for treating diabetes, and an agent for treating immunodeficiency disorders.
  - 53. Use of the compound of claim 1 in the manufacture of a medicament for the treatment of an inflammatory disorder.
  - 54. Use of the compound of claim 1 in the manufacture of a medicament for the treatment of an autoimmune disorder.

33. A compound selected from the group consisting of:
- 1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-[2-(1H-Indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2-Cyclohex-1-enyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide;
  
  2-Cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide;
  
  1-{2-[2-(4-Acetyl-piperazin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(5-Methoxy-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  [1-(7-Isopropylcarbamoyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-piperidin-3-yl]-methyl-carbamic acid tert-butyl ester;
  
  2-(3-Methylamino-piperidin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide;
  
  compound with trifluoro-acetic acid;
  
  2,2-Dimethyl-1-(2-pyrrolidin-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  1-[7-(2,2-Dimethyl-propionyl)-2′
  
  -pyrrolidin-1-yl-5H-[2,5′
  
  ]bi[pyrrolo[2,3-b]pyrazinyl]-7′
  
  -yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-[2-(1-Cyclopentyl-1H-[1,2,3]triazol-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(3,4,5,6-tetrahydro-2H-[1,2′
  
  ]bipyridinyl-4′
  
  -yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-{2-[2-(3-Dimethylamino-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2-thiomorpholin-4-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-{2-[2-(2-methyl-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  1-[2-(1,3-Dihydro-isoindol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-[2-(2,3-Dihydro-indol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-3,4-dihydro-2H-isoquinolin-1-one;
  
  1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-3,4-dihydro-1H-quinolin-2-one;
  
  2-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydro-isoindol-1-one;
  
  1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-piperidin-2-one;
  
  1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrrolidin-2-one;
  
  1-[2-(1H-Indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(6-pyrrolidin-1-yl-pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(4-pyrrolidin-1-yl-pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-(2-pyridin-2-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  [1-(7-Isopropylcarbamoyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-piperidin-3-yl]-methyl-carbamic acid tert-butyl ester;
  
  2-(3-Methylamino-piperidin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid;
  
  isopropylamide;
  
  compound with trifluoro-acetic acid;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-3-carboxylic acid (tetrahydro-pyran-4-yl)-amide;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyclopentylamide;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (tetrahydro-pyran-4-yl)-amide;
  
  1-(2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-3-carboxylic acid;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-3-carboxylic acid (2-dimethylamino-ethyl)-amide;
  
  1-{2-[2-(3-Methoxy-phenyl)-cyclopent-1-enyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  6-{2-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-cyclopent-1-enyl}-pyridine-2-carboxylic acid ethyl ester;
  
  2,2-Dimethyl-1-[2-(2-phenyl-cyclopent-1-enyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  5-{2-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-cyclopent-1-enyl}-1H-indole-2-carboxylic acid ethyl ester;
  
  4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyanomethyl-methyl-amide;
  
  (1-Methyl-cyclohexyl)-{2-[5-(morpholine-4-carbonyl)-thiophen-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone;
  
  1-(2-Furan-3-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (1-ethyl-propyl)-amide;
  
  {2-[5-(4-Hydroxy-4-methyl-piperidine-1-carbonyl)-thiophen-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  2,2-Dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(3,4,5,6-tetrahydro-2H-[1,2′
  
  ]bipyridinyl-4′
  
  -yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-{2-[2-(3-Dimethylamino-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2-thiomorpholin-4-yl-pyridin-4-yl)-H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-{2-[2-(2-methyl-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  1-{2-[2-(3-Hydroxy-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[2-(3,3-Difluoro-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(2-Azepan-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-{2-[2-((S)-3-Fluoro-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[2-((R)-3-Fluoro-pyrrolidin-1-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[2-(1,1-Dioxo-1λ
  
  ⁶-thiomorpholin-4-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(2-Chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one 2,2-Dimethyl-1-{2-[2-(1-oxo-1λ
  
  ⁴-thiomorpholin-4-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  1-[2-(2-Cyclopent-1-enyl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  (1-Methyl-cyclohexyl)-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone;
  
  1-[2-(4-Hydroxy-3,4,5,6-tetrahydro-2H-[1,2′
  
  ]bipyridinyl-4′
  
  -yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  5-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (1-ethyl-propyl)-amide;
  
  {2-[5-(3,3-Difluoro-azetidine-1-carbonyl)-thiophen-2-yl]-H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  {2-[5-(4-Hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  (1-Methyl-cyclohexyl)-{2-[2-(1-oxo-1λ
  
  ⁴-thiomorpholin-4-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone;
  
  {2-[5-(Azetidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  {2-[5-(3-Hydroxy-azetidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  1-{2-[2-((1S,5R,6R)-6-Hydroxymethyl-3-aza-bicyclo[3.1.0]hex-3-yl)-pyridin-4-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  (1-Methyl-cyclohexyl)-{2-[5-(morpholine-4-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone;
  
  5-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid diethylamide;
  
  5-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyclopentyl-methyl-amide;
  
  {2-[5-(4-Hydroxy-4-methyl-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  5-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid bis-(2-hydroxy-ethyl)-amide;
  
  5-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (2-hydroxy-ethyl)-methyl-amide;
  
  {2-[5-(3-Hydroxy-pyrrolidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyanomethyl-methyl-amide;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid bis-(2-hydroxy-ethyl)-amide;
  
  1-{2-[5-(4-Hydroxy-4-methyl-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[5-(Azetidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-{2-[5-(pyrrolidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  2,2-Dimethyl-1-{2-[5-(piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  3-Dimethylamino-1-{5-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carbonyl}-azetidine-3-carbonitrile;
  
  1-{2-[5-(4-Hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[4-(Azetidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-{2-[4-(pyrrolidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  2,2-Dimethyl-1-{2-[4-(piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  (1-Methyl-cyclohexyl)-{2-[5-(4-methyl-piperazine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-methanone;
  
  {2-[5-(4-Dimethylamino-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  1-(2-Cyclopent-1-enyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-(2-pyrrolidin-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  1-[7-(2,2-Dimethyl-propionyl)-2′
  
  -pyrrolidin-1-yl-5H-[2,5′
  
  ]bi[pyrrolo[2,3-b]pyrazinyl]-7′
  
  -yl]-2,2-dimethyl-propan-1-one;
  
  N-{1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrrolidin-3-yl}-acetamide;
  
  2,2-Dimethyl-1-[2-(2-methyl-pyrrolidin-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-[2-(4-Acetyl-piperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-(2-morpholin-4-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  1-[2-(5-Fluoro-indol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-[2-(5-Methoxy-indol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-(2-Indol-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  1-(2-Indazol-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  1-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1,3,4,9-tetrahydro-β
  
  -carbolin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2-{1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-3-yl}-acetamide;
  
  2,2-Dimethyl-1-[2-(1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(3-phenyl-pyrrolidin-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-(2-Imidazol-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2-methyl-imidazol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2-methyl-4,5-dihydro-imidazol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-[2-(2-Ethyl-imidazol-1-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-(2-thiophen-2-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrrol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-(2-thiophen-3-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-(2-oxazol-5-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrazole-1-carboxylic acid tert-butyl ester;
  
  2,2-Dimethyl-1-(2-pyrazol-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-[2-(2H-pyrazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-(2-pyrrol-1-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-(2-thiazol-5-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indole-5-carbonitrile;
  
  1-[2-(5-Fluoro-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  [2-(1H-Indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone;
  
  1-{2-[1-(2-Hydroxy-1-hydroxymethyl-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(1H-Indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-(2-Benzo[b]thiophen-2-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(5-phenyl-thiophen-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1-methyl-1H-indol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-[2-(1H-Indol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-[2-(1H-Indol-3-yl)-5-methyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(5-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-{2-[1-(2-Hydroxy-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(6-Fluoro-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-{2-[1-(2-Methanesulfonyl-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-[2-(5-Methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-[2-(1-Ethyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(5-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-{2-[1-[2-(4-methyl-piperazin-1-yl)-ethyl]-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  2,2-Dimethyl-1-{2-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  1-{2-[1-(3-Hydroxy-2-hydroxymethyl-propyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  1-{2-[1-(3-Hydroxy-2-hydroxymethyl-propyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(6-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  1-[2-(6-Methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-{2-[1-(2-Amino-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(6-morpholin-4-yl-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  (1-Methyl-cyclohexyl)-[2-(6-morpholin-4-yl-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone;
  
  1-[2-(1H-Indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  1-(2-Imidazo[1,2-a]pyridin-3-yl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrrolo[3,2-c]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1H-pyrrolo[2,3-c]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-[2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one;
  
  2,2-Dimethyl-1-{2-[1-(2-oxo-2-piperazin-1-yl-ethyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one;
  
  1-(2-{1-[2-(4-Amino-piperidin-1-yl)-2-oxo-ethyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one;
  
  (1-Methyl-cyclohexyl)-[2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone;
  
  2,2-Dimethyl-1-(2-{1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one;
  
  (1-Methyl-cyclopentyl)-[2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone;
  
  1-[2-(5-Methoxy-pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one;
  
  4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (1-ethyl-propyl)-amide;
  
  {2-[5-(4-Hydroxy-4-methyl-piperidine-1-carbonyl)-thiophen-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  5-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (2-hydroxy-ethyl)-methyl-amide;
  
  2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-hydroxy-1,2-dimethyl-propyl)-amide;
  
  4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid;
  
  4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (2-amino-2-methyl-propyl)-amide;
  
  {2-[5-(4-Dimethylamino-piperidine-1-carbonyl)-thiophen-3-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone;
  
  2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-2,2-dimethyl-propyl)-amide;
  
  2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide;
  
  2-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrrole-1-carboxylic acid tert-butyl ester; and
  
  2-Thiophen-2-yl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-2,2-dimethyl-propyl)-amide.

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Current Assignee
Roche Palo Alto LLC (Roche Holding AG)
Original Assignee
Roche Palo Alto LLC (Roche Holding AG)
Inventors
Yang, Hanbiao, Owens, Timothy D., Kondru, Rama K., Lou, Yan, Smith, David Bernard, Elworthy, Todd Richard, Hendricks, Robert Than, Soth, Michael, Hermann, Johannes Cornelius, Yee, Calvin Wesley, Bamberg, Joe Timothy, Lemoine, Remy, Park, Jaehyeon, DuBois, Daisy Joe, Bartlett, Mark

Granted Patent

US 7,939,531 B2
Time in Patent Office

Days
Field of Search
US Class Current

514/217.50
CPC Class Codes

A61P 1/04   for ulcers, gastritis or re...

A61P 11/06   Antiasthmatics

A61P 17/00   Drugs for dermatological di...

A61P 17/02   for treating wounds, ulcers...

A61P 17/06   Antipsoriatics

A61P 19/02   for joint disorders, e.g. a...

A61P 25/00   Drugs for disorders of the ...

A61P 25/28   for treating neurodegenerat...

A61P 29/00   Non-central analgesic, anti...

A61P 3/10   for hyperglycaemia, e.g. an...

A61P 35/00   Antineoplastic agents

A61P 35/02   specific for leukemia

A61P 37/00   Drugs for immunological or ...

A61P 37/02   Immunomodulators

A61P 37/06   Immunosuppressants, e.g. dr...

A61P 37/08   Antiallergic agents antiast...

A61P 43/00   Drugs for specific purposes...

A61P 5/14   of the thyroid hormones, e....

C07D 487/04   Ortho-condensed systems

C07D 519/00   Heterocyclic compounds cont...

Pyrrolopyrazine kinase inhibitors

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Pyrrolopyrazine kinase inhibitors

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