Checkpoint kinase inhibitors: A patent review (2009-2010)

Expert Opinion on Therapeutic Patents

Volumn 21, Issue 8, 2011, Pages 1191-1210

  Lainchbury, Michael ^a   Collins, Ian ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

cancer; cell cycle; checkpoint; DNA damage; inhibitor; kinase; potentiation; sensitization

Indexed keywords

AZD 7732; AZD 7762; CCT 241533; CHECKPOINT KINASE 1; CHECKPOINT KINASE 2; CHECKPOINT KINASE INHIBITOR; ENZYME INHIBITOR; GNE 900; LY 2603618; LY 2606368; SCH 900776; UNCLASSIFIED DRUG; VRX 0466617;

CANCER CHEMOTHERAPY; CANCER RESEARCH; CELL CYCLE PROGRESSION; CELL DIVISION; DNA DAMAGE; DRUG RESEARCH; DRUG STRUCTURE; HUMAN; NEOPLASM; NONHUMAN; PATENT; REVIEW;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE CHECKPOINTS; CELL CYCLE PROTEINS; HUMANS; MODELS, MOLECULAR; PATENTS AS TOPIC; PROTEIN CONFORMATION; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; PROTEIN-SERINE-THREONINE KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960679233     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2011.586632     Document Type: Review

References (70)

1. Reinhardt HC, Yaffe MB. Kinases that control the cell cycle in response to DNA damage: Chk1, Chk2, and MK2. Curr Opin Cell Biol 2009;21:245-55
2. Dai Y, Grant S. New insights into checkpoint kinase 1 in the DNA damaging response signaling network. Clin Cancer Res 2010;16:376-83
3. Garrett MD, Collins I. Anticancer therapy with checkpoint kinase inhibitors; what, where and when? Trends Pharmcol Sci 2011;32:308-16
4. Cole KA, Huggins J, Laquaglia M, et al. RNAi screen of the protein kinome identifies checkpoint kinase 1 (CHK1) as a therapeutic target in neuroblastoma. Proc Natl Acad Sci USA 2011;108:3336-41
5. Cavelier C, Didier C, Prade N, et al. Constitutive activation of the DNA damage signalling pathway in acute myeloid leukaemia with complex karyotype: potential importance in checkpoint targeting therapy. Cancer Res 2009;69:8652-61
6. Pommier Y, Weinstein JN, Aladjem MI, et al. Chk2 molecular interaction map and rationale for Chk2 inhibitors. Clin Cancer Res 2005;12:2657-61
7. Antoni L, Sodha N, Collins I, Garrett MD. CHK2 kinase: cancer susceptibility and cancer therapy - two sides of the same coin? Nat Rev Cancer 2007;7:925-36 (Pubitemid 350165855)
8. Arienti KL, Brunmark A, Axe FU, et al. Checkpoint kinase inhibitors: SAR and radioprotective properties of a series of 2-arylbenzimidazoles. J Med Chem 2005;48:1873-85 (Pubitemid 40396318)
9. Jobson AG, Lountos GT, Lorenzi PL, et al. Cellular inhibition of checkpoint kinase 2 (Chk2) and potentiation of camptothecins and radiation by the novel Chk2 inhibitor PV1019 [7-nitro-1H-indole-2-carboxylic acid {4-[1-(guanidinohydrazone)-ethyl]- phenyl}-amide]. J Pharmacol Expt Ther 2009;331:816-26
10. McCabe N, Turner NC, Lord CJ, et al. Deficiency in the repair of DNA damage by homologous recombination and sensitivity to poly(ADP-ribose) polymerase inhibition. Cancer Res 2006;66:8109-15 (Pubitemid 44299177)
11. Anderson VE, Walton MI, Eve PD, et al. CCT241533 is a potent and selective inhibitor of CHK2 that potentiates the cytotoxicity of PARP inhibitors. Cancer Res 2011;71:463-72
12. Registry of USA federal and privately supported clinical trials. Available from: http://www.clinicaltrials.gov [Accessed 28 February 2011]
13. Ma CX, Janetka JW, Piwnica-Worms H. Death by releasing the breaks: CHK1 inhibitors as cancer therapeutics. Trends Mol Med 2011;17:88-96
14. Janetka JW, Ashwell S, Zabludoff, et al. Inhibitors of checkpoint kinases: from discovery to the clinic. Curr Opin Drug Discov Devel 2007;10:473-86 (Pubitemid 47093131)
15. Prudhomme M. Novel checkpoint 1 inhibitors. Recent Patents Anti Cancer Drug Discov 2006;1:55-68
16. Janetka JW, Ashwell S. Checkpoint kinase inhibitors: a review of the patent literature. Expert Opin Ther Patents 2009;19:165-97
17. Tao Z-F, Wang L, Stewart KD, et al. Structure-based design, synthesis, and biological evaluation of potent and selective macrocyclic checkpoint kinase 1 inhibitors. J Med Chem 2007;50:1514-27 (Pubitemid 46564373)
18. Foloppe N, Fisher LM, Howes R, et al. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg Med Chem 2006;14:4792-802
19. Cancer Research Technology Ltd. Pyrazin-2-yl-pyridin-2-yl-amine and pyrazin-2-yl-pyrimidin-4-yl-amine compounds and their use. WO2009044162; 2009
20. Cancer Research Technology Ltd. Morpholino-substituted bicycloheteroaryl compounds and their use as anti cancer agents. WO2008075007; 2008
21. Cancer Research Technology Ltd. Bicyclyl-aryl-amine compounds and their use. WO2009103966; 2009
22. Walton MI, Eve PD, Hayes A, et al. The preclinical pharmacology and therapeutic activity of the novel CHK1 inhibitor SAR-020106. Mol Cancer Ther 2010;9:89-100
23. Pfizer, Inc. Substituted 2-heterocyclylamino pyrazine compounds as CHK-1 inhibitors. WO2010016005; 2010
24. Eli Lilly and Co. Compounds useful for inhibiting CHK1. WO2010077758; 2010
25. Characterization and preclinical development of LY2606368, a second generation Chk1 inhibitor. Poster presentation 194 at the 22nd EORTC-NCI-AACR Symposium on Molecular Targets and Cancer Therapeutics. Abstract Available from: http://www.poster-submission.com/EORTC [Accessed 28 February 2011]
26. Array Biopharma, Inc. Pyrazolopyridines as kinase inhibitors. WO2009089359; 2009
27. Array Biopharma, Inc. Pyrrolopyridines as kinase inhibitors. WO2009089352; 2009
28. Matthews TP, Klair S, Burns S, et al. Identification of inhibitors of checkpoint kinase 1 through template screening. J Med Chem 2009;52:4810-19
29. Array Biopharma, Inc. Preparation of pyrrolopyridines as checkpoint kinase CHK1 and/or CHK2 inhibitors. WO2009140320; 2009
30. Smithkline Beecham Plc. Preparation of N-pyrrolopyridinyl carboxamides as Chk1 kinase inhibitors for treating various forms of cancer and hyperproliferative disorders. WO2003028724; 2003
31. Array BioPharma, Inc. Checkpoint kinase 1 inhibitors for potentiating the effect of DNA damaging agents in treatment of cancer. WO2010118390; 2010
32. Blasina A, Hallin J, Chen E, et al. Breaching the DNA damage checkpoint via PF-00477736, a novel small-molecule inhibitor of checkpoint kinase 1. Mol Cancer Ther 2008;7:2394-404
33. Targeting Checkpoint Kinase 1: a study in the application of preclinical data to inform clinical strategy. Presentation for the 2nd Annual Cancer Targets & Therapeutics Conference 10/21/2010. Available from: www.arraybiopharma. com/-documents/Publication/PubAttachment410.pdf [Accessed 28 February 2011]
34. Cancer Research Technology Ltd. Morpholino-bicyclo-heteroaryl compounds as CHK1 kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. WO2008075007; 2008
35. Malek S, Blackwood E, OBrien T, et al. GNE-900, an orally bioavailable selective CHK1 inhibitor, illustrates that optimal chemosensitization is schedule and tumor type dependent. Poster 492 at the 22nd EORTC-NCI-AACR Symposium on Molecular Targets and Cancer Therapeutics. Abstract Available from: http://www.poster-submission.com/EORTC [Accessed 28 February 2011]
36. Cancer Research Technology Ltd. Preparation of 9H-pyrimido[4,5-b] indole, 9H-pyrido[4¢,3¢:4,5]pyrrolo[2,3- d]pyridine and 9H-1,3,6,9- tetraazafluorene derivatives as CHK1 kinase inhibitors. WO2009004329; 2009
37. Genentech, Inc. Diazacarbazoles as checkpoint kinase 1 inhibitors and their preparation and use in the treatment of cancer. WO2009151589; 2009
38. Genentech, Inc. Diazacarbazoles as checkpoint kinase 1 inhibitors and their preparation and use in the treatment of cancer. WO2009151598; 2009
39. Schering Corp. 2-Aminothiazole-4- carboxylic acid amides as protein kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO2008054701; 2008
40. Schering Corp. 2-Aminothiazole-4- carboxylic amides as protein kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO2008054749; 2008
41. Schering Corp. Thiazole derivatives as protein kinase inhibitors. WO2009058728; 2009
42. Schering Corp. Preparation of heterocyclic ether and thioether derivatives and methods of use thereof. WO2009058729; 2009
43. Schering Corp. Diamido thiazole derivatives as protein kinase inhibitors. WO2009058730; 2009
44. Schering Corp. Heterocyclic urea and thiourea derivatives and methods of use thereof. WO2009/058739; 2009
45. AstraZeneca UK Ltd. Thiophene derivatives as CHK 1 inhibitors. WO2005066163; 2005
46. Valeant Pharmaceuticals International. 3-Hydroxyisothiazole-4- carboxamidine derivatives as CHK2 inhibitors. WO2008157802; 2008
47. Carlessi L, Buscemi G, Larson G, et al. Biochemical and cellular characterization of VRX0466617, a novel and selective inhibitor for the checkpoint kinase Chk2. Mol Cancer Ther 2007;6:935-44 (Pubitemid 46554563)
48. Vernalis R&D Ltd. Indolyl-pyridone derivatives having checkpoint kinase 1 inhibitory activity. WO2009093012; 2009
49. Vernalis R&D Ltd. Pyrazole-substituted benzimidazole derivatives for use in the treatment of cancer and autoimmune disorders. WO2006134318; 2006
50. Haung S, Garbaccio RM, Fraley ME, et al. Development of 6-substituted indolylquinolinones as potent Chek1 kinase inhibitors. Bioorg Med Chem Lett 2006;16:5907-12 (Pubitemid 44486723)
51. Genentech, Inc. Substituted pyrroles and methods of use. WO2009151599; 2009
52. Cancer Research Technology Ltd. 5-Amidothiazole derivatives and their use as checkpoint kinase inhibitors. WO2010007389; 2010
53. Labroli M, Paruch K, Dwyer MP, et al. Discovery of pyrazolo[1,5-a] pyrimidinebased CHK1 inhibitors: a template-based approach-part 2. Bioorg Med Chem Lett 2011;21:471-4
54. Schering Corp. 2-Fluoropyrazolo[1,5-A] pyrimidines as protein kinase inhibitors. 2009070567; 2009
55. Paruch K, Dwyer MP, Alvarez C, et al. Discovery of Dinaciclib (SCH 727965): a potent and selective inhibitor of cyclin-dependent kinases. ACS Med Chem Lett 2010;1:204-8
56. Daud A, Springett GM, Mendelson DS, et al. A Phase I dose-escalation study of SCH 900776, a selective inhibitor of checkpoint kinase 1 (CHK1), in combination with gemcitabine (Gem) in subjects with advanced solid tumors. J Clin Oncol (Meeting Abstracts) 2010;28(Suppl):3064
57. Guzi TJ, Paruch K, Dwyer MP, et al. Targeting the replication checkpoint using SCH900776, a potent and functionally selective CHK1 inhibitor identified via high content screening. Mol Cancer Ther 2011;10:591-602
58. Schering Corp. Imidazopyrazines as protein kinase inhibitors. WO2010088368; 2010
59. Schering Corp. Imidazopyrazines as protein kinase inhibitors. WO2007145921; 2007
60. Cancer Research Technology Ltd. Therapeutic oxy-phenyl-aryl compounds and their use. WO2009053694; 2009
61. Caldwell JJ, Welsh EJ, Matijssen C, et al. Structure-based design of potent and selective 2-(quinazolin-2-yl)phenol inhibitors of checkpoint kinase 2. J Med Chem 2011;54:580-90
62. Hong PC, Chen LJ, Tai TY, et al. Synthesis of selenophene derivatives as novel CHK1 inhibitors. Bioorg Med Chem Lett 2010;20:5065-8
63. DCB-USA LLC. Protein kinase inhibitors. WO2009085040; 2009
64. Merck & Co., Inc. Inhibitors of checkpoint kinases. WO2009102537; 2009
65. Converso A, Hartingh T, Garbaccio RM, et al. Development of thioquinazolinones, allosteric Chk1 kinase inhibitors. Bioorg Med Chem Lett 2009;19:1240-4
66. Vanderpool D, Johnson TO, Ping C, et al. Characterization of the CHK1 allosteric inhibitor binding site. Biochemistry 2009;48:9823-30
67. Taiho Pharmaceutical Co. Ltd. New pyrrolocarbazole dione compound, or salt thereof. JP2010105920; 2010
68. AstraZeneca UK Ltd. Combination of checkpoint kinase (CHK) and telangiectasia mutated (ATM) inhibitors for the treatment of cancer. WO2008146036; 2008
69. Schering Corp. Novel modulators of cell cycle checkpoints and their use in combination with checkpoint kinase inhibitors. WO2009061781; 2009
70. Sandhu SK, Yap TA, de Bono JS. Poly(ADP-ribose) polymerase inhibitors in cancer treatment: a clinical perspective. Eur J Cancer 2010;46:9-20