# US 11,077,107 B2 · Triazolopyrazine > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,077,107 B2 - Document ID: US11077107B2 - Status: Granted - Kind: B2 - Application number: 16/389,062 - Filed: 2019-04-19 - Published: 2019-08-08 - Granted: 2021-08-03 - Earliest claimed: 2012-11-16 - Assignees: Boehringer Ingelheim International GmbH - Applicants: Boehringer Ingelheim International GmbH - Inventors: Harald Engelhardt; Davide Gianni; Christian Smethurst - Web page: https://patentgrep.com/patent/US11077107B2 ## CPC - A61K 31/4985: Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems - A61K 31/501: not condensed and containing further heterocyclic rings - A61K 31/52: Purines, e.g. adenine - A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61P 35/00: Antineoplastic agents - A61P 35/02: specific for leukemia - C07D 473/32: Nitrogen atom - C07D 487/04: Ortho-condensed systems - C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Disclosed are compounds of the formula (I) wherein the groups R1 to R3 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament. ## Claims ### Claim 1 A compound of the formula: ### Claim 2 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 3 (depends on 1) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 1. ### Claim 4 (depends on 3) The method according to claim 3, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 5 (depends on 2) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 2. ### Claim 6 (depends on 5) The method according to claim 5, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 7 A compound of the formula: ### Claim 8 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 9 (depends on 7) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 7. ### Claim 10 (depends on 9) The method according to claim 9, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 11 (depends on 8) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 8. ### Claim 12 (depends on 11) The method according to claim 11, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 13 A compound of the formula: ### Claim 14 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 15 (depends on 13) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 13. ### Claim 16 (depends on 15) The method according to claim 15, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 17 (depends on 14) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 14. ### Claim 18 (depends on 17) The method according to claim 17, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 19 A compound of the formula: ### Claim 20 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 21 (depends on 19) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 19. ### Claim 22 (depends on 21) The method according to claim 21, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 23 (depends on 20) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 20. ### Claim 24 (depends on 23) The method according to claim 23, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 25 A compound of the formula: ### Claim 26 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 27 (depends on 25) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 25. ### Claim 28 (depends on 27) The method according to claim 27, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 29 (depends on 26) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 26. ### Claim 30 (depends on 29) The method according to claim 29, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 31 A compound of the formula: ### Claim 32 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 33 (depends on 31) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 31. ### Claim 34 (depends on 33) The method according to claim 33, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 35 (depends on 32) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 32. ### Claim 36 (depends on 35) The method according to claim 35, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 37 A compound of the formula: ### Claim 38 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 39 (depends on 37) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 37. ### Claim 40 (depends on 39) The method according to claim 39, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 41 (depends on 38) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 38. ### Claim 42 (depends on 41) The method according to claim 41, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 43 A compound of the formula: ### Claim 44 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 45 (depends on 43) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 43. ### Claim 46 (depends on 45) The method according to claim 45, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 47 (depends on 44) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 44. ### Claim 48 (depends on 47) The method according to claim 47, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 49 A compound of the formula: ### Claim 50 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 51 (depends on 49) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 49. ### Claim 52 (depends on 51) The method according to claim 51, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 53 (depends on 50) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 50. ### Claim 54 (depends on 53) The method according to claim 53, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 55 A compound of the formula: ### Claim 56 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 57 (depends on 55) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 55. ### Claim 58 (depends on 57) The method according to claim 57, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 59 (depends on 56) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 56. ### Claim 60 (depends on 59) The method according to claim 59, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 61 A compound of the formula: ### Claim 62 A pharmaceutically acceptable salt of a compound of the formula: ### Claim 63 (depends on 61) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound according to claim 61. ### Claim 64 (depends on 63) The method according to claim 63, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer. ### Claim 65 (depends on 62) A method for inhibiting bromodomain protein 4 activity in a patient, comprising administering to the patient a therapeutically effective amount of a pharmaceutically acceptable salt according to claim 62. ### Claim 66 (depends on 65) The method according to claim 65, wherein the patient has a cancer selected from the group consisting of lung cancer, liver cancer, colon cancer, brain cancer, thyroid cancer, pancreatic cancer, breast cancer, ovarian cancer and prostate cancer.