IP Library › Patent Application 18925841

Patent Application

App. No. 18/925,841

5-AZAINDAZOLE DERIVATIVES AS ADENOSINE RECEPTOR ANTAGONISTS

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Patent No.: US None
App. No.: 18/925,841

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Abstract

The present invention relates to novel 5-azaindazole derivatives of formula (I), as described and defined herein, and pharmaceutically acceptable salts, solvates and prodrug thereof, as well as pharmaceutical compositions comprising such compounds. The 5-azaindazole derivatives according to the invention have been found to be highly effective dual A 2A /A 2B adenosine receptor antagonists, and can thus be used as therapeutic agents, particularly in the treatment or prevention of hyperproliferative or infectious diseases or disorders.

Claims (441)

1 - 25 . (canceled)

26 . A method of treating or preventing cancer, a hyperproliferative disease or disorder, an immunoproliferative disease or disorder, or an infectious disease or disorder, comprising administering a compound of formula (I) or a pharmaceutically acceptable salt, solvate or prodrug thereof in an effective amount to a subject in need thereof or

a method for the in vitro use of a compound of formula (I) or a pharmaceutically acceptable salt, solvate or prodrug thereof as a dual adenosine A 2A and A 2B receptor antagonist, comprising administering said compound or a pharmaceutically acceptable salt, solvate or prodrug thereof to said adenosine A 2A and A 2B receptors,

wherein the compound of formula (I) is as follows

wherein:

R 1A and R 1B are mutually linked to form, together with the nitrogen atom that they are attached to, a heterocycloalkyl which is optionally substituted with one or more groups R 11 ;

or, alternatively, R 1A and R 1B are each independently selected from hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —CO(C 1-5 alkyl), carbocyclyl, and heterocyclyl, wherein said alkyl, said alkenyl, said alkynyl, and the alkyl moiety of said —CO(C 1-5 alkyl) are each optionally substituted with one or more groups R 12 , and further wherein said carbocyclyl and said heterocyclyl are each optionally substituted with one or more groups R 3 ;

each R 11 is independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —(C 0-3 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-O(C 1-5 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-SH, —(C 0-3 alkylene)-S(C 1-5 alkyl), —(C 0-3 alkylene)-NH 2 , —(C 0-3 alkylene)-NH(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-halogen, —(C 0-3 alkylene)-(C 1-5 haloalkyl), —(C 0-3 alkylene)-O—(C 1-5 haloalkyl), —(C 0-3 alkylene)-CF 3 , —(C 0-3 alkylene)-CN, —(C 0-3 alkylene)-NO2, —(C 0-3 alkylene)-CHO, —(C 0-3 alkylene)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-COOH, —(C 0-3 alkylene)-CO—O—(C 1-5 alkyl), —(C 0-3 alkylene)-O—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-CO—NH 2 , —(C 0-3 alkylene)-CO—NH(C 1-5 alkyl), —(C 0-3 alkylene)-CO—N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —NH 2 , —(C 0-3 alkylene)-SO 2 —NH(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-SO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-carbocyclyl, and —(C 0-3 alkylene)-heterocyclyl, wherein the carbocyclyl moiety of said —(C 0-3 alkylene)-carbocyclyl and the heterocyclyl moiety of said —(C 0-3 alkylene)-heterocyclyl are each optionally substituted with one or more groups independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —O—(C 1-5 haloalkyl), —CF 3 , —CN, —NO2, —CHO, —CO—(C 1-5 alkyl), —COOH, —CO—O—(C 1-5 alkyl), —O—CO—(C 1-5 alkyl), —CO—NH 2 , —CO—NH(C 1-5 alkyl), —CO—N(C 1-5 alkyl)(C 1-5 alkyl), —NH—CO—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —SO 2 —NH 2 , —SO 2 —NH(C 1-5 alkyl), —SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —NH—SO 2 —(C 1-5 alkyl), —N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —SO—(C 1-5 alkyl), —SO 2 —(C 1-5 alkyl), cycloalkyl, and heterocycloalkyl;

each R 12 is independently selected from —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —O—(C 1-5 haloalkyl), —CF 3 , —CN, —NO2, —CHO, —CO—(C 1-5 alkyl), —COOH, —CO—O—(C 1-5 alkyl), —O—CO—(C 1-5 alkyl), —CO—NH 2 , —CO—NH(C 1-5 alkyl), —CO—N(C 1-5 alkyl)(C 1-5 alkyl), —NH—CO—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —SO 2 —NH 2 , —SO 2 —NH(C 1-5 alkyl), —SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —NH—SO 2 —(C 1-5 alkyl), —N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —SO—(C 1-5 alkyl), —SO 2 —(C 1-5 alkyl), cycloalkyl, and heterocycloalkyl;

each R 13 is independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —(C 0-3 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-O(C 1-5 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-SH, —(C 0-3 alkylene)-S(C 1-5 alkyl), —(C 0-3 alkylene)-NH 2 , —(C 0-3 alkylene)-NH(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-halogen, —(C 0-3 alkylene)-(C 1-5 haloalkyl), —(C 0-3 alkylene)-O—(C 1-5 haloalkyl), —(C 0-3 alkylene)-CF 3 , —(C 0-3 alkylene)-CN, —(C 0-3 alkylene)-NO2, —(C 0-3 alkylene)-CHO, —(C 0-3 alkylene)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-COOH, —(C 0-3 alkylene)-CO—O—(C 1-5 alkyl), —(C 0-3 alkylene)-O—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-CO—NH 2 , —(C 0-3 alkylene)-CO—NH(C 1-5 alkyl), —(C 0-3 alkylene)-CO—N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —NH 2 , —(C 0-3 alkylene)-SO 2 —NH(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-SO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-cycloalkyl, and —(C 0-3 alkylene)-heterocycloalkyl;

R 2 and R 4 are each independently selected from hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —(C 0-3 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-O(C 1-5 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-SH, —(C 0-3 alkylene)-S(C 1-5 alkyl), —(C 0-3 alkylene)-NH 2 , —(C 0-3 alkylene)-NH(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-halogen, —(C 0-3 alkylene)-(C 1-5 haloalkyl), —(C 0-3 alkylene)-O—(C 1-5 haloalkyl), —(C 0-3 alkylene)-CF 3 , —(C 0-3 alkylene)-CN, —(C 0-3 alkylene)-NO2, —(C 0-3 alkylene)-CHO, —(C 0-3 alkylene)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-COOH, —(C 0-3 alkylene)-CO—O—(C 1-5 alkyl), —(C 0-3 alkylene)-O—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-CO—NH 2 , —(C 0-3 alkylene)-CO—NH(C 1-5 alkyl), —(C 0-3 alkylene)-CO—N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —NH 2 , —(C 0-3 alkylene)-SO 2 —NH(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-SO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-carbocyclyl, and —(C 0-3 alkylene)-heterocyclyl, wherein the carbocyclyl moiety of said —(C 0-3 alkylene)-carbocyclyl and the heterocyclyl moiety of said —(C 0-3 alkylene)-hetero-cyclyl are each optionally substituted with one or more groups independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —O—(C 1-5 haloalkyl), —CF 3 , —CN, —NO2, —CHO, —CO—(C 1-5 alkyl), —COOH, —CO—O—(C 1-5 alkyl), —O—CO—(C 1-5 alkyl), —CO—NH 2 , —CO—NH(C 1-5 alkyl), —CO—N(C 1-5 alkyl)(C 1-5 alkyl), —NH—CO—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —SO 2 —NH 2 , —SO 2 —NH(C 1-5 alkyl), —SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —NH—SO 2 —(C 1-5 alkyl), —N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —SO—(C 1-5 alkyl), —SO 2 —(C 1-5 alkyl), cycloalkyl, and heterocycloalkyl;

R 3 is selected from hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —(C 1-5 alkylene)-OH, —(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 1-5 alkylene)-O(C 1-5 alkylene)-OH, —(C 1-5 alkylene)-O(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 1-5 alkylene)-SH, —(C 1-5 alkylene)-S(C 1-5 alkyl), —(C 1-5 alkylene)-NH 2 , —(C 1-5 alkylene)-NH(C 1-5 alkyl), —(C 1-5 alkylene)-N(C 1-5 alkyl)(C 1-5 alkyl), —(C 1-5 alkylene)-halogen, C 1-5 haloalkyl, —(C 1-5 alkylene)-O—(C 1-5 haloalkyl), —(C 1-5 alkylene)-CF 3 , —(C 1-5 alkylene)-CN, —(C 1-5 alkylene)-NO2, —(C 1-5 alkylene)-Si(C 1-5 alkyl) 3 , —(C 1-5 alkylene)-O(C 1-5 alkylene)-Si(C 1-5 alkyl)3, —(C 1-5 alkylene)-CHO, —(C 1-5 alkylene)-CO—(C 1-5 alkyl), —(C 1-5 alkylene)-COOH, —(C 1-5 alkylene)-CO—O—(C 1-5 alkyl), —(C 1-5 alkylene)-O—CO—(C 1-5 alkyl), —(C 1-5 alkylene)-CO—NH 2 , —(C 1-5 alkylene)-CO—NH(C 1-5 alkyl), —(C 1-5 alkylene)-CO—N(C 1-5 alkyl)(C 1-5 alkyl), —(C 1-5 alkylene)-NH—CO—(C 1-5 alkyl), —(C 1-5 alkylene)-N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —(C 1-5 alkylene)-NH—CO—O—(C 1-5 alkyl), —(C 1-5 alkylene)-N(C 1-5 alkyl)-CO—O—(C 1-5 alkyl), —(C 1-5 alkylene)-O—CO—NH—(C 1-5 alkyl), —(C 1-5 alkylene)-O—CO—N(C 1-5 alkyl)-(C 1-5 alkyl), —(C 1-5 alkylene)-SO 2 —NH 2 , —(C 1-5 alkylene)-SO 2 —NH(C 1-5 alkyl), —(C 1-5 alkylene)-SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —(C 1-5 alkylene)-NH—SO 2 —(C 1-5 alkyl), —(C 1-5 alkylene)-N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —(C 1-5 alkylene)-SO—(C 1-5 alkyl), —(C 1-5 alkylene)-SO 2 —(C 1-5 alkyl), —(C 0-5 alkylene)-carbocyclyl, and —(C 0-5 alkylene)-heterocyclyl, wherein the carbocyclyl moiety of said —(C 0-5 alkylene)-carbocyclyl and the heterocyclyl moiety of said —(C 0-5 alkylene)-heterocyclyl are each optionally substituted with one or more groups independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —O—(C 1-5 haloalkyl), —CF 3 , —CN, —NO2, —CHO, —CO—(C 1-5 alkyl), —COOH, —CO—O—(C 1-5 alkyl), —O—CO—(C 1-5 alkyl), —CO—NH 2 , —CO—NH(C 1-5 alkyl), —CO—N(C 1-5 alkyl)(C 1-5 alkyl), —NH—CO—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —NH—CO—O—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—O—(C 1-5 alkyl), —O—CO—NH—(C 1-5 alkyl), —O—CO—N(C 1-5 alkyl)-(C 1-5 alkyl), —SO 2 —NH 2 , —SO 2 —NH(C 1-5 alkyl), —SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —NH—SO 2 —(C 1-5 alkyl), —N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —SO—(C 1-5 alkyl), —SO 2 —(C 1-5 alkyl), cycloalkyl, and heterocycloalkyl.

L is C 1-5 alkylene, wherein one or more —CH 2 — units comprised in said alkylene are each optionally replaced by a group independently selected from —N(R L )—, —N(R L )—CO—, —CO—N(R L )—, —CO—, —O—, —CO—O—, —O—CO—, —S—, —SO—, —SO2-, —SO 2 —N(R L )—, and —N(R L )—SO 2 —;

each R L is independently selected from hydrogen and C 1-5 alkyl;

ring A is aryl or monocyclic heteroaryl, wherein said aryl or said monocyclic heteroaryl is optionally substituted with one or more groups R A ; and

each R A is independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —(C 0-3 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-O(C 1-5 alkylene)-OH, —(C 0-3 alkylene)-O(C 1-5 alkylene)-O(C 1-5 alkyl), —(C 0-3 alkylene)-SH, —(C 0-3 alkylene)-S(C 1-5 alkyl), —(C 0-3 alkylene)-NH 2 , —(C 0-3 alkylene)-NH(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-halogen, —(C 0-3 alkylene)-(C 1-5 haloalkyl), —(C 0-3 alkylene)-O—(C 1-5 haloalkyl), —(C 0-3 alkylene)-CF 3 , —(C 0-3 alkylene)-CN, —(C 0-3 alkylene)-NO2, —(C 0-3 alkylene)-CHO, —(C 0-3 alkylene)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-COOH, —(C 0-3 alkylene)-CO—O—(C 1-5 alkyl), —(C 0-3 alkylene)-O—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-CO—NH 2 , —(C 0-3 alkylene)-CO—NH(C 1-5 alkyl), —(C 0-3 alkylene)-CO—N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—CO—(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —NH 2 , —(C 0-3 alkylene)-SO 2 —NH(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —(C 0-3 alkylene)-NH—SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-SO—(C 1-5 alkyl), —(C 0-3 alkylene)-SO 2 —(C 1-5 alkyl), —(C 0-3 alkylene)-carbocyclyl, and —(C 0-3 alkylene)-heterocyclyl, wherein the carbocyclyl moiety of said —(C 0-3 alkylene)-carbocyclyl and the heterocyclyl moiety of said —(C 0-3 alkylene)-hetero-cyclyl are each optionally substituted with one or more groups independently selected from C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —O—(C 1-5 haloalkyl), —CF 3 , —CN, —NO2, —CHO, —CO—(C 1-5 alkyl), —COOH, —CO—O—(C 1-5 alkyl), —O—CO—(C 1-5 alkyl), —CO—NH 2 , —CO—NH(C 1-5 alkyl), —CO—N(C 1-5 alkyl)(C 1-5 alkyl), —NH—CO—(C 1-5 alkyl), —N(C 1-5 alkyl)-CO—(C 1-5 alkyl), —SO 2 —NH 2 , —SO 2 —NH(C 1-5 alkyl), —SO 2 —N(C 1-5 alkyl)(C 1-5 alkyl), —NH—SO 2 —(C 1-5 alkyl), —N(C 1-5 alkyl)-SO 2 —(C 1-5 alkyl), —SO—(C 1-5 alkyl), —SO 2 —(C 1-5 alkyl), cycloalkyl, and heterocycloalkyl.

27 . The method according to claim 26 , which is for treating or preventing cancer.

28 . The method according to claim 27 , wherein the cancer is selected from the group consisting of acute granulocytic leukemia, acute lymphocytic leukemia, acute myeloid leukemia, adrenal cortex cancer, bladder cancer, brain cancer, breast cancer, cervical cancer, cervical hyperplasia, cervical cancer, chorio cancer, chronic granulocytic leukemia, chronic lymphocytic leukemia, chronic myeloid leukemia, colon cancer, endometrial cancer, esophageal cancer, essential thrombocytosis, genitourinary carcinoma, glioma, glioblastoma, hairy cell leukemia, head and neck carcinoma, Hodgkin's disease, Kaposi's sarcoma, lung carcinoma, lymphoma, malignant carcinoid carcinoma, malignant hypercalcemia, malignant melanoma, malignant pancreatic insulinoma, medullary thyroid carcinoma, melanoma, multiple myeloma, mycosis fungoides, neuroblastoma, non-Hodgkin's lymphoma, non-small cell lung cancer, osteogenic sarcoma, ovarian carcinoma, pancreatic carcinoma, polycythemia vera, primary brain carcinoma, primary macroglobulinemia, prostatic cancer, renal cell cancer, rhabdomyosarcoma, skin cancer, small-cell lung cancer, soft-tissue sarcoma, squamous cell cancer, stomach cancer, testicular cancer, thyroid cancer and Wilms' tumor.

29 . The method according to claim 26 , which is for treating or preventing a hyperproliferative disease or disorder, wherein said hyperproliferative disease or disorder is selected from the group consisting of age-related macular degeneration, Crohn's disease, cirrhosis, a chronic inflammatory-related disorder, proliferative diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, granulomatosis, immune hyperproliferation associated with organ or tissue transplantation, and an immunoproliferative disease or disorder.

30 . The method according to claim 26 , which is for treating or preventing an immunoproliferative disease or disorder, wherein the immunoproliferative disease or disorder is selected from the group consisting of inflammatory bowel disease, psoriasis, rheumatoid arthritis, systemic lupus erythematosus (SLE), vascular hyperproliferation secondary to retinal hypoxia, and vasculitis.

31 . The method according to claim 26 , which is for treating or preventing is an infectious disease or disorder, wherein said infectious disease or disorder is selected from the group consisting of:

(a) virally induced infectious diseases which are caused by retroviruses, hepadnaviruses, herpesviruses, flaviviridae and/or adenoviruses, wherein the retroviruses are selected from lentiviruses or oncoretroviruses, wherein the lentivirus is selected from the group consisting of HIV-1, HIV-2, FIV, BIV, SIVs, SHIV, CAEV, VMV and EIAV, wherein the oncoretrovirus is selected from the group consisting of HTLV-I, HTLV-II and BLV, wherein the hepadnavirus is selected from the group consisting of HBV, GSHV and WHV, wherein the herpesvirus is selected from the group consisting of HSV I, HSV II, EBV, VZV, HCMV and HHV 8, and wherein the flaviviridae are selected from the group consisting of HCV, West nile and Yellow Fever;

(b) bacterial infectious diseases which are caused by Gram-positive bacteria, wherein the Gram-positive bacteria are selected from the group consisting of methicillin-susceptible and methicillin-resistant staphylococci (including Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus haemolyticus, Staphylococcus hominis, Staphylococcus saprophyticus , and coagulase-negative staphylococci), glycopeptides-intermediate susceptible Staphylococcus aureus (GISA), penicillin-susceptible and penicillin-resistant streptococci (including Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae, Streptococcus avium, Streptococcus bovis, Streptococcus lactis, Streptococcus sanguis and Streptococci Group C (GCS), Streptococci Group G (GGS) and viridans streptococci), enterococci (including vancomycinsusceptible and vancomycin-resistant strains such as Enterococcus faecalis and Enterococcus faecium ), Clostridium difficile, Listeria monocytogenes, Corynebacterium jeikeium, Chlamydia spp (including C. pneumoniae ) and Mycobacterium tuberculosis;

(c) bacterial infectious diseases which are caused by Gram-negative bacteria, wherein the Gram-negative bacteria are selected from the group consisting of the genus Enterobacteriaceae , including Escherichia spp. (including Escherichia coli ), Klebsiella spp., Enterobacter spp., Citrobacter spp., Serratia spp., Proteus spp., Providencia spp., Salmonella spp., Shigella spp., the genus Pseudomonas (including P. aeruginosa ), Moraxella spp. (including M. catarrhalis ), Haemophilus spp. and Neisseria spp.; and

(d) infectious diseases induced by intracellular active parasites selected from the group consisting of the phylum Apicomplexa, Sarcomastigophora (including Trypanosoma, Plasmodia, Leishmania, Babesia or Theileria ), Cryptosporidia, Sacrocystida, Amoebia, Coccidia and Trichomonadia.

32 . The method according to claim 26 , wherein the subject to be treated is a human.

33 . The method according to claim 26 , which is for the in vitro use of the compound of formula (I) as a dual adenosine A 2A and A 2B receptor antagonist.

34 . The method according to claim 26 , wherein, in the compound of formula (I),

R 1A and R 1B are mutually linked to form, together with the nitrogen atom that they are attached to, a group which is selected from

wherein each one of the above-depicted groups is optionally substituted with one or more groups R 11 ;

R 3 is —CH 2 —CF 3 or —CH 2 —SO 2 —CH 3 ;

L is C 1-5 alkylene, wherein one or more —CH 2 — units in said alkylene are each optionally replaced by a group independently selected from —N(R L )—, —N(R L )—CO—, —CO—N(R L )—, —CO—, —O—, —CO—O—, —O—CO—, —S—, —SO—, —SO 2 —, —SO 2 —N(R L )—, and —N(R L )—SO 2 —;

each R L is independently selected from hydrogen and C 1-5 alkyl;

ring A is aryl or monocyclic heteroaryl, wherein said aryl or said monocyclic heteroaryl is optionally substituted with one or more groups R A ; and

or a pharmaceutically acceptable salt or solvate thereof.

35 . The method according to claim 26 , wherein, in the compound of formula (I),

R 2 and R 4 are each independently selected from hydrogen, C 1-5 alkyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —CF 3 , and —CN.

36 . The method according to claim 26 , wherein, in the compound of formula (I),

L is C 1-3 alkylene, wherein one —CH 2 — unit in said alkylene is optionally replaced by a group selected from —N(R L )—, —N(R L )—CO—, —CO—N(R L )—, and —CO—, and further wherein each R L is independently selected from hydrogen, methyl and ethyl.

37 . The method according to claim 26 , wherein, in the compound of formula (I),

L is —NH—;

and/or

ring A is phenyl or a 6-membered monocyclic heteroaryl, wherein said phenyl or said monocyclic heteroaryl is optionally substituted with one or more groups R A and/or

each R A is independently selected from C 1-5 alkyl, —OH, —O(C 1-5 alkyl), —O(C 1-5 alkylene)-OH, —O(C 1-5 alkylene)-O(C 1-5 alkyl), —SH, —S(C 1-5 alkyl), —NH 2 , —NH(C 1-5 alkyl), —N(C 1-5 alkyl)(C 1-5 alkyl), halogen, C 1-5 haloalkyl, —CF 3 , and —CN.

38 . A method of treating or preventing cancer, a hyperproliferative disease or disorder, an immunoproliferative disease or disorder, or an infectious disease or disorder, comprising administering a compound selected from compounds 1 to 127 or a pharmaceutically acceptable salt, solvate or prodrug thereof in an effective amount to a subject in need thereof or

a method for the in vitro use of a compound selected from compounds 1 to 127 or a pharmaceutically acceptable salt, solvate or prodrug thereof as a dual adenosine A 2A and A 2B receptor antagonist, comprising administering said compound or a pharmaceutically acceptable salt, solvate or prodrug thereof to said adenosine A 2A and A 2B receptors,

wherein the compounds 1 to 127 are as follows

[3-(2-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-anilino-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-

4-yl)methanone

[3-(2-methoxyanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

[3-(2-methylanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(N-methylanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(3-methoxyanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

3-[[6-(1,4-oxazepane-4-carbonyl)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-3-yl]amino]benzonitrile

3-[[6-(1,4-oxazepane-4-carbonyl)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-3-yl]amino]benzamide

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(4-methoxyanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

1,4-oxazepan-4-yl-[3-(3-pyridylamino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]methanone

4-[[6-(1,4-oxazepane-4-carbonyl)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-3-yl]amino]benzonitrile

4-[[6-(1,4-oxazepane-4-carbonyl)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-3-yl]amino]benzamide

[3-(3,5-difluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

[3-(3-fluoro-4-methylanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-(3,4-difluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

[3-(3-chloro-4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-

yl]-(1,4-oxazepan-4-yl)methanone

[3-(4-chloro-3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-

yl]-(1,4-oxazepan-4-yl)methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(8-

oxa-3-azabicyclo[3.2.1]octan-3-yl)methanone

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(8-

oxa-3-azabicyclo[3.2.1]octan-3-yl)methanone

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(4-

hydroxy-1-piperidyl)methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(4-

hydroxy-1-piperidyl)methanone

(4-hydroxy-1-piperidyl)-[3-(2-pyridylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(3-

endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(3-

endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

[3-(4-fluoroanilino)-1-(methylsulfonylmethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

[3-(3-fluoroanilino)-1-(methylsulfonylmethyl)pyrazolo[4,3-c]pyridin-6-yl]-

(1,4-oxazepan-4-yl)methanone

[3-anilino-1-(methylsulfonylmethyl)pyrazolo[4,3-c]pyridin-6-yl]-(3-endo-

hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

[3-(4-fluoroanilino)-1-(methylsulfonylmethyl)pyrazolo[4,3-c]pyridin-6-yl]-(3-

endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

[3-(3-fluoroanilino)-1-(methylsulfonylmethyl)pyrazolo[4,3-c]pyridin-6-yl]-(3-

endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(6-

hydroxy-1,4-oxazepan-4-yl)methanone

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(6-

hydroxy-1,4-oxazepan-4-yl)methanone

[3-(4-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(4-

hydroxy-4-methyl-1-piperidyl)methanone

[3-(3-fluoroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(4-

hydroxy-4-methyl-1-piperidyl)methanone

1,4-oxazepan-4-yl-[3-(pyrimidin-2-ylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-(3-chloroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(4-chloroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

[3-(2-chloroanilino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-

oxazepan-4-yl)methanone

(6,6-dideuterio-1,4-oxazepan-4-yl)-[3-(3-fluoroanilino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

(6,6-dideuterio-1,4-oxazepan-4-yl)-[3-(4-fluoroanilino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

1,4-oxazepan-4-yl-[3-(2-pyridylamino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]methanone

1,4-oxazepan-4-yl-[3-(4-pyridylamino)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]methanone

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(6-methoxy-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(4-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

8-oxa-3-azabicyclo[3.2.1]octan-3-yl-[3-(2-pyridylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(5-chloro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(6-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-methoxy-3-methyl-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(6-chloro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

(6-hydroxy-1,4-oxazepan-4-yl)-[3-(2-pyridylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

(4-hydroxy-4-methyl-1-piperidyl)-[3-(2-pyridylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(3-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(3-chloro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-3-methyl-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-4-methyl-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-6-methyl-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

(6,6-dideuterio-1,4-oxazepan-4-yl)-[3-(2-pyridylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

(6,6-dideuterio-1,4-oxazepan-4-yl)-[3-[(4-fluoro-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

1,4-oxazepan-4-yl-[3-(pyrazin-2-ylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

1,4-oxazepan-4-yl-[1-(2,2,2-trifluoroethyl)-3-[[4-(trifluoromethyl)-2-

pyridyl]amino]pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(4-methoxy-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(4-chloro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(6-chloro-5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(4-chloro-5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(3-chloro-5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(4-methyl-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(1,4-oxazepan-4-yl)methanone

1,4-oxazepan-4-yl-[3-(pyridazin-3-ylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(4-fluoro-3-methyl-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-chloro-4-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(3,5-difluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[1,4]Oxazepan-4-yl-[3-(pyrimidin-4-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-

pyrazolo[4,3-c]pyridin-6-yl]-methanone

(4-Hydroxy-piperidin-1-yl)-[3-(pyrazin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-

1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

[3-(5-Chloro-pyrazin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-hydroxy-piperidin-1-yl)-methanone

(4-Hydroxy-piperidin-1-yl)-[3-(pyrimidin-4-ylamino)-1-(2,2,2-trifluoro-ethyl)-

1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

[3-(5-Fluoro-pyridin-2-ylamino)-1-methanesulfonylmethyl-1H-pyrazolo[4,3-

c]pyridin-6-yl]-[1,4]oxazepan-4-yl-methanone

[3-(5-Chloro-pyridin-2-ylamino)-1-methanesulfonylmethyl-1H-pyrazolo[4,3-

c]pyridin-6-yl]-[1,4]oxazepan-4-yl-methanone

[3-(4-Chloro-pyridin-2-ylamino)-1-methanesulfonylmethyl-1H-pyrazolo[4,3-

c]pyridin-6-yl]-[1,4]oxazepan-4-yl-methanone

[3-[(5,6-difluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-4-methoxy-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-6-methoxy-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-(5-Methoxy-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-[1,4]oxazepan-4-yl-methanone

[1,4]Oxazepan-4-yl-[3-(thiazol-5-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-

pyrazolo[4,3-c]pyridin-6-yl]methanone

[1,4]Oxazepan-4-yl-[3-(thiazol-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-

pyrazolo[4,3-c]pyridin-6-yl]methanone

6-[6-([1,4]Oxazepane-4-carbonyl)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-3-ylamino]-1H-pyridin-2-one

3-[[6-(1,4-oxazepane-4-carbonyl)-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridin-3-yl]amino]-1H-pyridin-2-one

[3-[(5-fluoro-4-hydroxy-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(5-fluoro-3-hydroxy-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

[3-[(4-fluoro-3-hydroxy-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]-(1,4-oxazepan-4-yl)methanone

(6,6-dideuterio-1,4-oxazepan-4-yl)-[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(6-hydroxy-1,4-oxazepan-4-yl)methanone

[(6S)-6-fluoro-1,4-oxazepan-4-yl]-[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(4-hydroxypiperidin-1-yl)methanone

[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-hydroxy-4-methyl-piperidin-1-yl)-methanone

(4-Fluoro-piperidin-1-yl)-[3-(5-fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-

ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

[(3R)-3-hydroxy-piperidin-1-yl]-[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]methanone

[(3S)-3-hydroxy-piperidin-1-yl]-[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]methanone

[(3R)-3-fluoro-piperidin-1-yl]-[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]methanone

100

[(3S)-3-fluoro-piperidin-1-yl]-[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]methanone

101

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-[(3R)-3-(hydroxymethyl)-1-piperidyl]methanone

102

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-[(3S)-3-(hydroxymethyl)-1-piperidyl]methanone

103

(3,3-Difluoro-4-hydroxy-piperidin-1-yl)-[3-(5-fluoro-pyridin-2-ylamino)-1-

(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

104

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(3-hydroxy-3-methyl-piperidin-1-yl)methanone

105

Cis-[3-(5-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-

pyrazolo[4,3-c]pyridin-6-yl]-(3-hydroxy-4-methyl-piperidin-1-yl)-methanone

106

Cis-(3-Fluoro-4-hydroxy-piperidin-1-yl)-[3-(5-fluoro-pyridin-2-ylamino)-1-

(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

107

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

108

1-[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-

c]pyridine-6-carbonyl]pyridine-4-carboxylic acid

109

[3-[(4-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(6-hydroxy-1,4-oxazepan-4-yl)methanone

110

[(6S)-6-fluoro-1,4-oxazepan-4-yl]-[3-(4-fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

111

[3-[(4-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(4-hydroxypiperidin-1-yl)methanone

112

[3-(4-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-hydroxy-4-methyl-piperidin-1-yl)-methanone

113

[3-(4-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-ethyl-4-hydroxypiperidin-1-yl)-methanone

114

[3-(4-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-isopropyl-4-hydroxypiperidin-1-yl)-methanone

115

[3-(4-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-cyclopropyl-4-hydroxypiperidin-1-yl)-methanone

116

(4-Fluoro-piperidin-1-yl)-[3-(4-fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-

ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

117

[(3S)-3-hydroxy-piperidin-1-yl]-[3-(4-fluoro-pyridin-2-ylamino)-1-(2,2,2-

trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]methanone

118

[3-(4-Fluoro-pyridin-2-ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-

c]pyridin-6-yl]-(4-hydroxy-2,2-dimethyl-piperidin-1-yl)-methanone

119

(3,3-Difluoro-4-hydroxy-piperidin-1-yl)-[3-(4-fluoro-pyridin-2-ylamino)-1-

(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

120

[3-[(4-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

121

6,6-dideuterio-1,4-oxazepan-4-yl)-[3-(pyrazin-2ylamino)-1-(2,2,2-

trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone

122

[(6S)-6-fluoro-1,4-oxazepan-4-yl]-[3-(pyrazin-2ylamino)-1-(2,2,2-trifluoro-

ethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-methanone

123

[3-(pyrazin-2ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-

yl]-(4-hydroxy-4-methyl-piperidin-1-yl)-methanone

124

[3-(pyrazin-2ylamino)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[4,3-c]pyridin-6-

yl]-(4-fluoro-piperidin-1-yl)-methanone

125

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-[(2R)-2-(2-hydroxy-2-methyl-propyl)pyrrolidin-1-yl]methanone

126

[3-[(5-fluoro-2-pyridyl)amino]-1-(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-

6-yl]-[(2S)-2-(2-hydroxy-2-methyl-propyl)pyrrolidin-1-yl]methanone

127

(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-[3-(2-pyridylamino)-1-

(2,2,2-trifluoroethyl)pyrazolo[4,3-c]pyridin-6-yl]methanone.

39 . The method according to claim 38 , which is for treating or preventing cancer, wherein the cancer is selected from the group consisting of acute granulocytic leukemia, acute lymphocytic leukemia, acute myeloid leukemia, adrenal cortex cancer, bladder cancer, brain cancer, breast cancer, cervical cancer, cervical hyperplasia, cervical cancer, chorio cancer, chronic granulocytic leukemia, chronic lymphocytic leukemia, chronic myeloid leukemia, colon cancer, endometrial cancer, esophageal cancer, essential thrombocytosis, genitourinary carcinoma, glioma, glioblastoma, hairy cell leukemia, head and neck carcinoma, Hodgkin's disease, Kaposi's sarcoma, lung carcinoma, lymphoma, malignant carcinoid carcinoma, malignant hypercalcemia, malignant melanoma, malignant pancreatic insulinoma, medullary thyroid carcinoma, melanoma, multiple myeloma, mycosis fungoides, neuroblastoma, non-Hodgkin's lymphoma, non-small cell lung cancer, osteogenic sarcoma, ovarian carcinoma, pancreatic carcinoma, polycythemia vera, primary brain carcinoma, primary macroglobulinemia, prostatic cancer, renal cell cancer, rhabdomyosarcoma, skin cancer, small-cell lung cancer, soft-tissue sarcoma, squamous cell cancer, stomach cancer, testicular cancer, thyroid cancer and Wilms' tumor.

40 . The method according to claim 38 , which is for treating or preventing a hyperproliferative disease or disorder, wherein said hyperproliferative disease or disorder is selected from the group consisting of age-related macular degeneration, Crohn's disease, cirrhosis, a chronic inflammatory-related disorder, proliferative diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, granulomatosis, immune hyperproliferation associated with organ or tissue transplantation, and an immunoproliferative disease or disorder.

41 . The method according to claim 38 , which is for treating or preventing an immunoproliferative disease or disorder, wherein the immunoproliferative disease or disorder is selected from the group consisting of inflammatory bowel disease, psoriasis, rheumatoid arthritis, systemic lupus erythematosus (SLE), vascular hyperproliferation secondary to retinal hypoxia, and vasculitis.

42 . The method according to claim 38 , which is for treating or preventing is an infectious disease or disorder, wherein said infectious disease or disorder is selected from the group consisting of:

(a) virally induced infectious diseases which are caused by retroviruses, hepadnaviruses, herpesviruses, flaviviridae and/or adenoviruses, wherein the retroviruses are selected from lentiviruses or oncoretroviruses, wherein the lentivirus is selected from the group consisting of HIV-1, HIV-2, FIV, BIV, SIVs, SHIV, CAEV, VMV and EIAV, wherein the oncoretrovirus is selected from the group consisting of HTLV-I, HTLV-II and BLV, wherein the MERCK-5015 hepadnavirus is selected from the group consisting of HBV, GSHV and WHV, wherein the herpesvirus is selected from the group consisting of HSV I, HSV II, EBV, VZV, HCMV and HHV 8, and wherein the flaviviridae are selected from the group consisting of HCV, West nile and Yellow Fever;

43 . The method according to claim 38 , wherein the subject to be treated is a human.

44 . The method according to claim 38 , which is for the in vitro use of the compound of formula (I) as a dual adenosine A 2A and A 2B receptor antagonist.

Assignments (4)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2025

From: MERCK PATENT GMBH; MERCK HEALTHCARE KGAA

To: DOMAIN THERAPEUTICS

Reel/Frame 072033/0504 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2024

From: BLAYO, ANNE-LAURE; MANTEAU, BAPTISTE; AMALRIC, CAMILLE; MAYER, STANISLAS; SCHANN, STEPHAN; FER, MICKAEL

To: DOMAIN THERAPEUTICS SA

Reel/Frame 069554/0450 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2024

From: DOMAIN THERAPEUTICS SA

To: MERCK HEALTHCARE KGAA

Reel/Frame 069554/0688 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2024

From: MERCK HEALTHCARE KGAA

To: MERCK PATENT GMBH

Reel/Frame 069554/0761 →