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Last Updated: December 16, 2025

Claims for Patent: 8,324,225


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Summary for Patent: 8,324,225
Title:Pyrrolopyrimidine compounds and their uses
Abstract:The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases, particularly pyrrolopyrimidine compounds and derivatives are described which inhibit protein kinases. The organic compounds are useful in treating proliferative disease.
Inventor(s):Christopher Thomas Brain, Moo Je Sung, Gebhard Thoma
Assignee:Astex Therapeutics Ltd, Novartis Pharmaceuticals Corp
Application Number:US12/302,223
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent 8,324,225
Patent Claims: 1. A compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein: the dashed line indicates a double bond; A is N; R2 is hydrogen and R3 is selected from the group consisting of hydrogen, hydroxyl, C1-C3-alkyl, C3-C8-cycloalkyl, heterocyclyl, aryl, heteroaryl, substituted C1-C3-alkyl, substituted C3-C8-cycloalkyl, substituted heterocyclyl, substituted aryl and substituted heteroaryl; R4 is selected from the group consisting of hydrogen, branched C1-C5-alkyl, branched C1-C5-alkyl substituted by phenyl and C3-C6-cycloalkyl; X is CR11 and Y is CR12; R11 is hydrogen or C1-C3-alkyl and R12 is BC(O)NR13R14; wherein B is a bond, C1-C3-alkyl or branched C1-C3-alkyl; wherein R13 and R14 are each, independently, selected from the group consisting of hydrogen, C1-C3-alkyl, C3-C8-cycloalkyl, heterocyclyl, aryl, heteroaryl, substituted alkyl, substituted cycloalkyl, substituted heterocyclyl, substituted aryl, and substituted heteroaryl.

2. The compound of claim 1, wherein R4 is C(H)(CH2CH3)2, C(H)(CH2CH3)Ph, CH2CH3, cyclopropyl, cyclopentyl or cyclohexyl.

3. The compound of claim 1, wherein R3 is an aryl group, which is further independently substituted one or more times by halogen, C1-C4-alkoxy, R15-amine, R15-heterocycle, or R15-heteroaryl, wherein R15 is a bond, C(O), N(H)C(O), N(H)SO2, OC(O) or (CH2)1-4, wherein the (CH2)1-4 group may be interrupted by O, N(CH3) or N(H).

4. The compound of claim 3, wherein the aryl group is phenyl.

5. The compound of claim 1, wherein the phenyl group is R3 is phenyl which is further independently substituted one or more times with fluoro, methoxy, diethylamine, R15-piperazinyl, R15-morpholinyl, R15-piperidinyl, R15-triazolyl, R15-phenyl, R15-pyridinyl, R15-piperazinyl, R15-indazolyl, R15-pyrrolidinyl or R15-imidazolyl, wherein the piperazinyl, morpholinyl, piperidinyl, triazolyl, phenyl, pyridinyl, piperazinyl, indazolyl, pyrrolidinyl or imidazolyl groups may be further substituted with C1-C4-alkyl, C(O)C1-C4-alkyl, S(O)2C1-C4-alkyl, OH, C(O)(CH2)1-3CN or N(H)C(O)C1-C4-alkyl and wherein R15 is a bond, C(O), N(H)C(O), N(H)SO2, OC(O) or (CH2)1-4, wherein the (CH2)1-4 group may be interrupted by O, N(CH3) or N(H).

6. The compound of claim 1, wherein R3 is phenyl which is further substituted by N(H)C(O)aryl, C(O)N(H)C1-C4-alkyl, C(O)N(C1-C4-alkyl)2 or C(O)N(H)C3-C6-cycloalkyl.

7. The compound of claim 1, wherein the compound is selected from the group consisting of

8. A compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein: the dashed line indicates a double bond; A is N; R2 is hydrogen and R3 is selected from the group consisting of hydrogen, hydroxyl, C1-C3-alkyl, C3-C8-cycloalkyl, heterocyclyl, aryl, heteroaryl, substituted C1-C3-alkyl, substituted C3-C8-cycloalkyl, substituted heterocyclyl, substituted aryl and substituted heteroaryl; R4 is branched or linear C1-C5-alkyl, wherein the branched C1-C5-alkyl group may be interrupted by one or more heteroatoms, and/or substituted with one or more heteroatoms, halogens, C3-C8 cycloalkyl groups, substituted C3-C8 cycloalkyl groups, C3-C8 hetrocyclyl groups, aryl groups, heteroaryl groups, substituted aryl groups, or substituted heteroaryl groups; X is CR11 and Y is CR12; R11 is hydrogen or C1-C3-alkyl and R12 is BC(O)NR13R14; wherein B is a bond, C1-C3-alkyl or branched C1-C3-alkyl; wherein R13 and R14 are each, independently, selected from the group consisting of hydrogen, C1-C3-alkyl, C3-C8-cycloalkyl, heterocyclyl, aryl, heteroaryl, substituted alkyl, substituted cycloalkyl, substituted heterocyclyl, substituted aryl, and substituted heteroaryl.

9. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier or excipient.

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