NOVEL IMIDAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS, PARTICULARLY DUAL-SPECIFICITY TYROSINE PHOSPHORYLATION-REGULATED KINASE 1A (DYRK1A), CDC2-LIKE KINASE 1 (CLK1) AND / OR CDC2-LIKE KINASE 4 (CLK4)

Abstract

The present invention relates to a compound of formula (I) SNN HN OR NH 1 (I) R2 wherein R1 represents an alkyl group (C1-C6), a spiro bicyclic ring (C5-C11), a fused phenyl group, a substituted phenyl, an R'-L- group, wherein L is either a single bond or an alkandiyl group (C1-C3), and R' represents a cycloalkyl group (C3-C8), a bridged cycloalkyl group (C6-C10), a heterocycloalkyl group (C3-C8), or a heteroaryl group (C3-C8), or an R'-L- group wherein L is an alkandiyl group (C1-C3), and R' is an optionally substituted phenyl group, and wherein R2 represents a hydrogen atom or an alkyl group (C1-C3) or any of its pharmaceutically acceptable salts. The present invention further relates to a composition comprising a compound of formula (I) and a process for manufacturing such a compound, as well as its synthesis intermediates.It also refers to such a compound for use as a drug, particularly in the treatment and / or prevention of cognitive deficits associated with Down syndrome; Alzheimer's disease; dementia; tauopathies; Parkinson's disease; CDKL5 deficiency disorder; Phelan-McDermid syndrome; autism; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis; Duchenne muscular dystrophy; various cancers; neuroinflammation, anemia, and viral and single-cell infections, and for regulating body temperature.

Description

NEW IMIDAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS, IN PARTICULAR DUAL-SPECIFICITY TYROSINE PHOSPHORYLATION-REGULATED KINASE 1A (DYRK1A), CHOLESTEROL-DEPENDENT CYTOLYSIN-LIKE KINASE 1 (CLK1) AND / OR CHOLESTEROL-DEPENDENT CYTOLYSIN-LIKE KINASE 4 (CLK4) Field of Invention The present invention relates to leucettinibs, a novel class of compounds useful as pharmacological agents. These novel compounds are particularly useful as kinase inhibitors, and even more particularly as inhibitors of DYRK1A and / or CLK1 and / or CLK4. They are effective in treating and / or preventing cognitive deficits associated with Down syndrome; Alzheimer's disease and related diseases; dementia; tauopathies; Parkinson's disease; other neurodegenerative diseases; CDKL5 deficiency disorder; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis; Duchenne muscular dystrophy; various cancers and leukemias; viral infections; and in regulating body temperature. Some of these compounds are additional inhibitors of other kinases, specifically other DYRKs (DYRK1B, 2, 3, 4) and the closely related cdc2-like kinases (CLK2, 3, 4). Such compounds fronr Ln / zznz / E / YiAi Ref 338579 may also be effective in treating and / or preventing Phelan-McDermid syndrome; autism; viral infections, cancers, neuroinflammation, anemia and infections caused by single-celled parasites. It also refers to pharmaceutical compositions containing such new compounds and the chemical synthesis processes for obtaining them. Background of the Invention The DYRK and CLK kinase families belong to the CMGC kinase group, which also includes mitogen-activated protein kinases (MAPKs), cyclin-dependent kinases (CDKs), and glycogen synthase kinase-3 (GSK-3). They phosphorylate many substrates involved in signaling pathways. DYRK and CLK play key roles in mRNA splicing, chromatin transcription, DNA damage repair, cell survival, cell cycle regulation, differentiation, homocysteine / methionine / folate regulation, endocytosis, neuronal development and function, and synaptic plasticity. DYRK1A and Down syndrome (DS) The gene encoding DYRK1A is located on chromosome 21, specifically in the critical region of Down syndrome (DSCR), whose triploidy is responsible for most of the deficits associated with DS. There is considerable genetic and pharmacological evidence showing that a mere 1.5-fold overexpression of DYRK1A is responsible for most of the cognitive deficits, especially memory and learning deficits, observed in patients with Down syndrome (Rueda N et al., 2020. Translational validity and implications of pharmacotherapies in preclinical models of Down syndrome. Prog Brain Res 251, 245). Pharmacological or genetic normalization of DYRK1A levels restores cognitive functions (Nguyen TL et al., 2017. Dualspecificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) inhibitors: a survey of recent patent literature. Expert Opin. Ther. Pat. 27, 1183-1199; Nguyen TL et al., 2018. Correction of cognitive deficits in mouse models of Down syndrome by pharmacological inhibition of DYRK1A. Dis. Model Mech. 11, dmm035634). DYRK1A and Alzheimer's disease (AD), Tauopathies There is growing evidence for a role of DYRK1A in the onset of AD. DYRK1A phosphorylates key substrates implicated in AD and dementia: tau, septin 4, amyloid precursor protein (APP), presenilin 1, neprilysin, and fronr Ln / zznz / E / YiAi Muncl8-1, α-synuclein, RCAN1, β-tubulin. There is evidence of abnormal expression and post-translational modifications of DYRK1A in AD. By modulating alternative splicing of exon 10, DYRK1A favors the production of the 3R-Tau splice isoform (characteristic of DS / AD / tauopathy) over the normal 4R-Tau isoform. Inhibition of DYRK1A promotes autophagy, which could counteract the autophagy deficit observed in AD. DYRK1A and Parkinson's disease (PD) and Pick's disease GWAS studies have revealed that DYRK1A is a risk factor for Parkinson's disease (Nalls MA et al., 2019. Identification of novel risk loci, causal insights, and heritable risk for Parkinson's disease: a meta-analysis of genome-wide association studies. Lancet Neurol 18, 1091). DYRK1A phosphorylates key factors for PD such as parkin, septin 4, and α-synuclein. Upregulation of specific microRNAs for DYRK1A expression is a PD target (Chiu CC et al., 2019. Upregulated expression of microRNA-204-5p leads to the death of dopaminergic cells by targeting DYRK1A-mediated apoptotic signaling cascade. Front Cell Neurosci 13, 399). There is further evidence that DYRK1A expression is increased in PD. DYRK1A is overexpressed in Pick's disease. front Ln / zznz / E / YiAi DYRK1A and other diseases (viral infections, type 1 and type 2 diabetes, cancers) DYRK1A and DYRK1B are used during placental replication of HCMV. Inhibition of DYRK prevents the replication of several viruses, including herpes simplex virus, cytomegalovirus, and HIV-1. DYRK1A inhibitors stimulate the proliferation of insulin-producing pancreatic β cells, a promising approach for type 1 and type 2 diabetes (Ackeifi C et al., 2020. Pharmacologic and genetic approaches define human pancreatic β cell mitogenic targets of DYRK1A inhibitors. JCI Insight 5, el32594; Kumar K et al., 2021. DYRK1A inhibitors as potential therapeutics for β-cell regeneration for diabetes. J Med Chem. 2021 Mar 8. doi: 10.1021 / acs.jmedchem.0c02050. Epub ahead of print. PMID: 33682417). Extensive literature links DYRK1A to cancer. Prominent examples include megakaryoblastic leukemia, acute lymphoblastic leukemia, pancreatic cancer, and brain tumors (glioblastoma). Therefore, abnormalities in DYRK1A dosage are associated with the cognitive impairments observed in Down syndrome and Alzheimer's disease. DYRK1A is a risk factor for Parkinson's disease. Inhibition of DYRK1A also triggers the proliferation of insulin-producing pancreatic β cells. Thus, DYRK1A inhibitors may find applications in preventing and / or treating Down syndrome, Alzheimer's disease and other tauopathies, dementia, Parkinson's disease, Niemann-Pick type C disease, CDKL5 deficiency disorder, type 1 and type 2 diabetes, viral infections, various cancers (leukemia, pancreatic cancer, glioblastoma), osteoarthritis, infections caused by single-celled parasites, and in regulating body temperature. Other DYRKs and human diseases DYRK1B is involved in the replication of several viruses, including hepatitis C virus, Chikungunya virus, dengue virus, SARS coronavirus, cytomegalovirus, and human papillomavirus. Like DYRK1A, inhibition of DYRK1B leads to the proliferation of insulin-producing pancreatic β cells. DYRK1B is also involved in neuroinflammation. Targeting DYRK1B provides a new rationale for treating various cancers, such as liposarcoma and breast cancer. DYRK2, in association with GSK-33, regulates neuronal morphogenesis. DYRK2 is involved in several ways in cancer development. DYRK3 promotes hepatocellular carcinoma. DYRK3 couples the condensation / dissolution of stress granules to mTORCl signaling. DYRK3 regulates the phase transition of non-membrane organelles in mitosis. DYRK3 and fronr Ln / zznz / E / YiAi DYRK4 are involved in regulating cytoskeleton organization and growth processes in neurons. DYRK1A decreases axon growth, DYRK3 and DYRK4 increase dendritic branching, and DYRK2 decreases the growth and branching of axons and dendrites. CLK and human diseases It is observed that CLK is a confusing abbreviation as it has the following meanings: (a) monooxygenase CLK1 (human homolog COQ7); (b) Collectin-Kl (CL-K1 or CL-11), a multifunctional Ca(2+) dependent lectin; (c) MAPK gene of the maize pathogen Curvularia Innata, Clkl; (d) mitochondrial membrane-bound enzyme Clock-1 (CLK-1); (e) Colletotrichum lindemuthianum kinase 1 (clkl). CLKs play essential roles in alternative splicing. CLKs act as a body temperature sensor that globally controls alternative splicing and gene expression. In fact, CLK activity responds strongly to physiological temperature changes, which is conferred by structural rearrangements within the kinase activation segment (Haltenhof T et al., 2020. Conserved kinase-based body temperature sensor globally controls alternative splicing and gene expression. Mol Cell 78, 57). CLK1 and human diseases CLK1 triggers periodic alternative splicing during the cell division cycle. CLK1 regulates the splicing of influenza A virus mRNA, and its inhibition prevents viral replication. CLK1 and CLK2 also regulate HIV-1 gene expression. CLK1 is an inducer of autophagy. Inhibition of CLK1 can prevent chemoresistance in glioma, and CLK1 inhibition by TG693 allows for the omission of the mutated exon 31 of the dystrophin gene in Duchenne muscular dystrophy. Other CLK and human diseases CLK2 inhibition has been proposed as a way to improve neuronal function and combat intellectual disability and autism in Phelan-McDermid syndrome (PMDS). Dual inhibition of CLK2 and DYRK1A by lorecivivint is a potential disease-modifying procedure for knee osteoarthritis. CLK2 inhibition compromises MYC-driven breast tumors, triple-negative breast cancer, and glioblastoma. CLK2 inhibition improves autistic features in Phelan-McDermid syndrome (PMDS). Alternative splicing of Tau exon 10 is regulated by CLK2 and other CLKs, leading to changes in the 3R / 4R isoform ratio and neurodegeneration in sporadic Alzheimer's disease. Inhibition of CLK2, CLK3, and CLK4 blocks HIV-1 production.By regulating the fronr Ln / zznz / E / YiAi alternative splicing, CLKs modulate the balance between pro-apoptotic and anti-apoptotic regulators, and therefore CLK inhibition may find applications in the treatment of numerous cancers. CLK3 contributes to hepatocellular carcinoma and prostate cancer. Table 1 below summarizes the involvement of DYRK and CLK kinases in various diseases Table 1 fronr Ln / zznz / E / YiAi Kinase target DYRK1A disease Down syndrome (DS) DYRK1A Alzheimer's disease (AD) and other tauopathies DYRK1A Parkinson's disease DYRK1A Pick's disease DYRK1A CDKL5 deficiency disorder DYRK1A Type 1 and type 2 diabetes DYRK1A Folate and methionine metabolism abnormalities DYRK1A Glioblastoma DYRK1A Squamous cell carcinoma of the head and neck DYRK1A Pancreatic ductal adenocarcinoma DYRK1A Megakaryoblastic leukemia DYRK1A Acute lymphoblastic leukemia (ALL) DYRK1A Osteoarthritis of the knee DYRK1A Human immunodeficiency virus type 1 Kinase target Disease (HIV-1) DYRK1A, DYRK1B Human cytomegalovirus (HCMV) DYRK1B Hepatitis C virus, Chikungunya virus, dengue virus and severe acute respiratory syndrome coronavirus, cytomegalovirus, human papillomavirus DYRK1B Type 1 and type 2 diabetes DYRK1B Neuroinflammation DYRK1B Liposarcoma, breast cancer, Hedgehog / GLI-dependent cancer DYRK2 Triple-negative breast cancer (TNBC) and multiple myeloma (MM) DYRK2 Glioblastoma DYRK3 Hepatocellular carcinoma DYRK3 Influenza virus replication DYRK3 Anemia DYRK Glioblastoma DYRK Herpes simplex, cytomegalovirus, varicella-zoster virus LmDYRK1 Leishmaniasis TbDYRK Trypanosoma brucellosis CLK1 Glioblastoma CLK1 Duchenne muscular dystrophy CLK1 Influenza A CLK2 HIV-1 Kinase target CLK1 / CLK2 Disease Triple-negative breast cancer CLK2 Autism, Phelan-McDermid syndrome (PMDS) CLK2 Knee osteoarthritis CLK2 Breast cancer, Triple-negative breast cancer, Glioblastoma CLK2 Alzheimer's disease (alternative splicing of Tau exon 10) CLK3 Hepatocellular carcinoma, Prostate cancer CLK Body temperature CLK Prostate cancer, Gastrointestinal cancer PfCLKs Malaria DYRK / CLK Glioblastoma and many other cancer types front Ln / zznz / E / YiAi DYRK and CLK inhibitors Several DYRK1A inhibitors have been reported in recent years. Most DYRK1A inhibitors also inhibit DYRK1B, 2, 3, and 4, as well as the closely related CLK1, 2, 3, and 4, with several possible inhibition profiles. Some imidazolone derivatives, referred to as Leucettins in the following text, are described in document W02009 / 050352 as kinase inhibitors and, more specifically, as DYRK1A kinase inhibitors. There is still a need to identify new compounds to treat and / or prevent the diseases mentioned above, and in particular through the inhibition, and in particular the selective inhibition, of DYRK1A, other DYRKs and related CLK kinases. Brief Description of the Invention Compounds as defined in formula (I) hereafter have now been found to be useful in the treatment and / or prevention of a selected disease from cognitive deficits associated with Down syndrome; Alzheimer's disease and related diseases; dementia; tauopathies; Parkinson's disease; other neurodegenerative diseases; CDKL5 Deficiency Disorder; Phelan-McDermid syndrome; autism; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis; various cancers and leukemias; neuroinflammation, anemia, infections caused by single-celled parasites, viral infections, and for regulating body temperature. The present invention therefore relates to a compound of formula (I), as defined below. The present invention further relates to a compound of formula (I) as defined below for use as a medicament. The present invention further relates to a compound of formula (I) as defined below for use in the treatment and / or prevention of a selected disease from cognitive deficits associated with Down syndrome; Alzheimer's disease and related diseases; dementia; tauopathies; Parkinson's disease; other neurodegenerative diseases; CDKL5 Deficiency Disorder; Phelan-McDermid syndrome; autism; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis; various cancers and leukemias, neuroinflammation, anemia, infections caused by single-celled parasites, viral infections, and for regulating body temperature. The present invention also relates to a pharmaceutical composition comprising it and processes for manufacturing it. The present invention finally relates to synthetic intermediates of formula (II) as defined below. DEFINITIONS As used herein, the term patient refers to an animal, such as an animal valued for breeding, companionship or preservation purposes, or preferably a human being or a human child, who suffers or has the potential to suffer from one or more of the diseases and conditions described herein. In particular, as used in the present application, the term patient refers to a mammal such as a rodent, cat, dog, primate or human, preferably such subject is a human and also extends to birds. Identifying patients requiring treatment for the diseases and conditions described herein is within the capabilities and knowledge of a skilled practitioner. A veterinarian or physician skilled in the technique can readily identify, through clinical trials, physical examinations, medical / family history, or biological and diagnostic tests, those patients who require such treatment. In the context of the invention, the term treat or treatment, as used herein, means to prevent, reverse, alleviate, inhibit the progression of, or prevent the disease and its cognitive, motor, or metabolic changes resulting from high DYRK1A kinase and / or CLK1 expression and activity, and optionally associated with abnormalities in other DYRKs (DYRK1B, 2, 3, 4) and other closely related cdc2-like kinases (CLK 2, 3, 4), and more particularly in conjunction with the diseases described later in the section PATHOLOGIES. Therefore, the term treat or treatment encompasses within the framework of the present invention the improvement of the medical conditions of patients suffering from the diseases described below in the section PATHOLOGIES, related to the high expression and activity of any of the DYRK1A and CLK1 kinases, and optionally associated with abnormalities in other DYRK (DYRK1B, 2, 3, 4) and the closely related cdc2-like kinases (CLK 2, 3, 4). As used herein, an effective amount refers to an amount of a compound of the present invention that is effective in preventing, reducing, eliminating, treating, or controlling the symptoms of the diseases and conditions described herein. The term "control" is intended to refer to all processes in which there may be a slowing, interruption, suppression, or stopping of the progression of the diseases and conditions described herein, but does not necessarily indicate a total elimination of all symptoms of diseases and conditions, and is intended to include prophylactic treatment. The term effective amount includes effective amount of prophylaxis as well as effective amount of treatment. The term prevent, as used herein, means to reduce the risk of occurrence or slow down the occurrence of a given phenomenon, specifically in the present invention, a disease resulting from abnormal activity of the DYRKs / CLKs kinase, in particular the DYRK1A kinase activity. As used herein, prevention also encompasses reducing the likelihood of it occurring or reducing the likelihood of it recurring. The term effective amount for prophylaxis refers to a concentration of compound of this invention that is effective in inhibiting, preventing, and decreasing the likelihood of any of the diseases described above. Similarly, the term effective treatment amount refers to a concentration of compound that is effective in treating the diseases described above, for example, leading to a reduction or normalization of DYRK1A and / or CLK1 kinase activity and, optionally, in addition to DYRKs / CLKs kinase activity, generally after examination when administered after the disease has occurred. As used herein, the term pharmaceutically acceptable refers to those compounds, materials, excipients, compositions, or dosage forms that, to the best of medical judgment, are suitable to come into contact with the tissues of humans and animals without excessive toxicity, irritation, allergic response, or other complications of the problem consistent with a reasonable risk / benefit ratio. front Ln / zznz / E / YiAi Detailed Description of the Invention The inventors have surprisingly found that the compounds of formula (I) as described herein inhibit DYRK1A, other DYRKs (DYRK1B, DYRK2, DYRK3, DYRK4), and CLKs (CLK1, CLK2, CLK3, CLK4). This assertion is based on data as illustrated in the following examples and further detailed herein. According to a first aspect, a subject matter of the present invention relates to a compound of formula (I) R1-NH (I) fronr Ln / zznz / E / YiAi where R1 represents: (i) . an alkyl group (C1-C4) substituted by one or two groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkoxy group (C1-C4) and a benzyloxy group, such benzyloxy is optionally substituted in its phenyl group by one to three halogen atoms, (ii) . a spirobicyclic ring (C5-C11), (iii) . a fused phenyl group, selected from phenyl groups fused to a cycloalkyl (C5Ce) or heterocycloalkyl (Cs-Cg) ring, wherein the cycloalkyl (Cs-Ce) and heterocycloalkyl (Cs-Ce) ring optionally comprises an unsaturation and is optionally substituted by an alkyl (C1-C4) group, a hydroxy group, a halogen atom, an alkoxy (C1-C3) group or a -CORa group, (iv).a phenyl group, substituted by one or two groups selected from an alkyl (C1-C3) group, a fluoroalkyl (C1-C3) group, a fluoroalkoxy (C1-C4) group, a halogen atom, and a heterocycloalkyl (C4-C7) group, such heterocycloalkyl (C4-C7) group being the same optionally substituted by an alkyl (C1-C4) group or (v). an R'-L- group, wherein L is either a single bond or an alkandiyl (C1-C3) group, optionally substituted by a group selected from a hydroxy group and an alkoxy (C1-C3) group, and. R' represents: (v.1) a cycloalkyl (Cs-Cg) group, optionally substituted by one, two, or three groups selected from a (C1-C4) alkyl group, a hydroxy group, a halogen atom, and a (C1-C3) alkoxy group, (v.2) a bridged cycloalkyl (Cg-Cio) group, optionally substituted by one to three groups selected from a (C1-C4) alkyl group, a (C1-C4) alkoxy group, a halogen atom, a hydroxy group, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, an -SO2Rd group, an -N(Re)2 group, and a -COORa group, (v.3) a (C3-C8) heterocycloalkyl group, optionally replaced by one to three groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkyl (C1-C4) group and an oxo group, (v.4) a heteroaryl (C3-C8) group, optionally substituted by one to three groups selected from a halogen atom, an alkyl (C1-C4) group, an alkoxy (C1-C4) group and a β-methylpiperazinyl group, or (v.5) a bridged heterocycloalkyl (Cg-C1o) group, or (vi) an R'-L- group where L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from a -NRbRc group, an alkoxy (C1-C4) group, a hydroxy group, a -COORay group and a halogen atom, and. R' is a phenyl group, optionally substituted by one to three groups selected from the group consisting of an alkyl group (C1-C6), a fluoroalkyl group (C1-C4) and a fluoroalkoxy group (C1-C4), a halogen atom and a hydroxy group, Ra represents an alkyl group (C1-C4) or a hydrogen atom, Rby Rc independently represent an alkyl group (Ci-Cg) or a hydrogen atom, Rd represents an alkyl group (C1-C4) or a cyclopropyl group, fronr Ln / zznz / E / YiAi Represents an alkyl group (C1-C3) , and fronr Ln / zznz / E / YiAi r2 represents a hydrogen atom or an alkyl group (C1-C3) , or any of its pharmaceutically acceptable salts. The inventors have surprisingly discovered that compounds having the following scaffolds of formula (A) to (F) show greatly reduced kinase inhibitory activities at DYRK1A and other related kinases compared to their benzothiazole homologs (compounds according to the invention): IC50 values ​​are reduced by factors of 10 to 1000 times, and some compounds were completely inactive at the highest dose tested (10 pM). These greatly reduced kinase-inhibiting activities have been verified, for example, by individual comparison of a compound of formula (I) and a compound having a scaffold of formula (A) to (F), wherein in both, R2 is a hydrogen atom and R1 is selected from the group consisting of cyclohexyl, cycloheptyl, cyclooethyl, 2-methoxy-l-phenylethyl. According to a particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, where R1 represents: (i) . an alkyl group (C2-Cg) substituted by one or two groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkoxy group (C1-C4) and a benzyloxy group, such benzyloxy is optionally substituted in its phenyl group by one to three halogen atoms, (ii) . a spirocyclic ring (C7-C9), (iii) . a fused phenyl group, selected from phenyl groups fused with a cyclopentyl or a heterocyclopentyl, wherein the cyclopentyl and heterocyclopentyl group optionally comprises an unsaturation and is optionally substituted by an alkyl group (C1-C4), a hydroxy group, a halogen atom, an alkoxy group (C1-C3) or a -CORa group, (iv) .a phenyl group, substituted by one or two groups selected from an alkyl group (C1-C8), a fluoroalkyl group (C1-C3), a fluoroalkoxy group (C1-C4), a halogen atom, and a heterocycloalkyl group (C4-C7), such heterocycloalkyl group (C4-C7) is the same optionally substituted by an alkyl group (C1-C4), or (v) an R'-L- group wherein • L is either a single bond or an alkandiyl group (C1-C3), optionally substituted by a group selected from a hydroxy group and an alkoxy group (C1-C3), and • R' represents: (v1) a (C3-C8) cycloalkyl group, optionally substituted by one, two, or three groups selected from a (C1-C4) alkyl group, a hydroxy group, a fluorine atom, and a (C1-C3) alkoxy group, (v2) a bridged (C7-C10) cycloalkyl group, optionally substituted by one to three groups selected from a (C1-C4) alkyl group, a (C1-C4) alkoxy group, a hydroxy group, a halogen atom, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, a -SO2-Rd group, an -N(Re)2 group, and a -COORa group, (v3) a (C4-C7) heterocycloalkyl group, optionally substituted by one to three groups selected from a group -COORa, a hydroxy group, a halogen atom, an alkyl (C1-C4) group and an oxo group, (v.4) a heteroaryl group, optionally substituted by one to three groups selected from a halogen atom, an alkyl (C1-C4) group, an alkoxy (C1-C4) group, a JV-methylpiperazinyl group, or fronr Ln / zznz / E / YiAi (v.5) a bridged heterocycloalkyl (Ce-Cio) group, or (vi) an R'-L- group wherein • L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from a -NRbRc group, a (C1-C3) alkoxy group, a hydroxy group, a -COORay group, and a halogen atom, and • R' is a phenyl group, optionally substituted by one to three groups selected from the group consisting of an alkyl (Ci-Ce) group, a fluoroalkyl (C1-C4) group, a fluoroalkoxy (C1-C4) group, a hydroxy group, and a halogen atom. Ra represents an alkyl group (C1-C4) or a hydrogen atom, Rby Rc independently represent an alkyl group (Ci-C6) or a hydrogen atom, Rd represents an alkyl group (C1-C4) or a cyclopropyl group, It represents an alkyl group (C1-C3), and R2 represents a hydrogen atom or an alkyl group (C1-C3), or any of its pharmaceutically acceptable salts. According to another particular embodiment, the present invention relates to a compound of formula (I) fronr Ln / zznz / E / YiAi as defined above herein, where R1 represents: (i) . an alkyl group (C2-Cg) substituted by one or two groups selected from a -COOCH3 group, a hydroxy group, a fluorine atom, a methoxy group, an ethoxy group, a tert-butoxy group, a cyclopropoxy group and a benzyloxy group, such benzyloxy being optionally substituted in its phenyl group by a fluorine atom, (ii) . a spirobicyclic ring (C7-Cg), in particular a spiro[3.3]heptyl, a spiro[2.5]octanyl or a 7-azaspiro[3.5]nonyl, (iii) . a fused phenyl group, selected from phenyl groups fused to a cyclopentyl or a heterocyclopentyl, wherein the cyclopentyl and heterocyclopentyl group optionally comprises an unsaturation and is optionally substituted by a methyl group, a hydroxy group, a methoxy group and a -COCH3 group, (iv) .a phenyl group, substituted by one or two groups selected from a methyl group, a hexyl group, a trifluoromethyl group, a difluoromethoxy group, a halogen atom, in particular a fluorine atom, a morpholino group and a 2V-methylpiperazinyl group, or (v) an R'-L- group where L is either a single bond or an alkandiyl (C1-C3) group, optionally substituted by a group chosen from a hydroxy group and an alkoxy (C1-C3) group, and R' is selected from the group consisting of: (vl) . a cycloalkyl group (C3-C8) in particular a cyclopropyl, a cyclobutyl, a cyclopentyl, a cyclohexyl, a cycloheptyl or a cyclooctyl, optionally replaced by one, two, or three selected groups starting from a methyl group, an isopropyl, a hydroxy group and a methoxy group, (v.2) . un grupo cicloalquilo (C7-C10) puenteado, en particular un adamantilo o un biciclo[3.1.1]heptilo, opcionalmente sustituido por uno a tres grupos seleccionados a partir de un grupo metilo, un grupo metoxi, un grupo hidroxi, un átomo de fúor, un grupo -OC(O)-CH3, un grupo OC (O)-C (CH3) 3, un grupo -OC (O) -NH-C (CH3) 3, un grupo -NHC(O)-CH3, un grupo -NH-C (O) -C3H4, un grupo -S(O)2-CH3, un grupo -S(O)2-C3H4, un grupo -N (CH3)2y un grupo -C (O)-O-CH3, (v.3).a heterocycloalkyl group (Cg-Cg), in particular a tetrahydropyranyl, a piperidinyl, an oxethanyl, a tetrahydrofuranyl or an oxepanil, a tetrahydrothiopyranyl, a pyrrolidinyl, a dioxepanil or a piperidinyl, optionally substituted by one, two or three group(s) selected from a -COORf group, a hydroxy group, a methyl group, and an oxo group, wherein Rf represents either an ethyl or isopropyl group, fronr Ln / zznz / E / YiAi (v.4). a heteroaryl group, in particular a pyrimidinyl, a pyridinyl, a thiazolyl, an imidazolyl, a pyrazolyl, a thiadiazolyl, a pyridazinyl, a pyrazinyl, a furyl, optionally substituted by one to three groups selected from a methyl group, a methoxy group and a 7V-methylpiperazinyl group, or (v.5). a bridged (C7-C10) cycloalkyl group, in particular a quinuclidin-3-yl, or (vi).an R'-L- group where L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from the group consisting of an NRbRc group, an alkoxy (C1-C4) group, a hydroxy group, a COORay group, and a halogen atom, in particular a fluorine atom, and. R' is a phenyl group, optionally substituted by one or two groups selected from the group consisting of a methyl group, a trifluoromethyl group and a trifluoromethoxy group, Ra represents an alkyl group (C1-C3), Rby Rcson are independently selected from a methyl group or a hydrogen atom, and R2 represents a hydrogen atom or an alkyl group (C1-C3), or any of its pharmaceutically acceptable salts. front Ln / zznz / E / YiAi According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above herein, wherein R1 is an R'-L- group, and L is selected from a group consisting of a -CH2- group, a CH(CH3)- group, a -CH(CH2OH)-CH2- group, a -CH(CH2OH)- group, a -CH(CH2OCH3)- group, a -CH(OH)-CH2- group, a -CH2CH(CH2OCH3)- group, a -CH(OCH3)-CH2- group, a -CH2CH(COOCH3)- group, a -CH(CH2F)- group, a -CH(CH2NH2)- group, a -CH(CH2NHCH3)- group, a -CH(CH2N(CH3)2)- group, a -CH2CH(CH2OH)- group, a -CH(OCH3)-CH2- group, a group -CH2-CH (OCH3) -, a -CH2-CH (OH)-CH2- group, a -CH2-CH (OCH3)-CH2 group, a — (CH2)3— group, a -(CH2)2- group and a -CH (CH2OC (CH3) 3) group or any of its pharmaceutically acceptable salts. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, wherein R1 is an R'-L- group, wherein: (v.1) When R' is a (C3-C8) cycloalkyl group, L is selected from the group consisting of a single bond, a -CH2- group, a -CH(CH3)- group, a -CH(CH2OH)-CH2- group, a -CH(CH2OH)- group, a -CH(CH2OCH3)- group, and a -CH(OH)-CH2- group and a -CH(OCH3)-CH2- group, (v.2) When R' is a bridged (C7-C10) cycloalkyl group, L is a single bond, a -CH2- group or a -CH(CH3)- group, (v.3) When R' is a (Cs-Cg) heterocycloalkyl group including spiro (Cs-Cg) heterocycloalkyls, L is a single bond or a -CH2- group, (v.4)When R' is a phenyl, L is selected from the group consisting of a single bond, a -CH2- group, a -CH2-CH(COOCH3)- group, a -CH(CH2F)- group, a -CH(CH2NH2) group, a -CH(CH2NHCH3)- group, a CH(CH2N(CH3)2) group, a -CH2-CH(CH2OH)- group, a CH(CH2OH)- group, a -CH(CH2OCH3)- group, a -CH(OH)-CH2- group, a -CH2-CH(CH2OCH3)- group, a -CH2-CH(OH)-CH2- group, and a CH2-CH(OCH3)-CH2 group, (v.5). When R' is a heteroaryl group, L is selected from the group comprising a single bond, a -CH2- group, a -(CH2)3- group and a -(CH2)2 group. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above herein, wherein R1 represents: an adamantyl group, optionally substituted by one to three groups, and in particular substituted by a group, selected from a methyl group, a methoxy group, a hydroxy group, a fluorine atom, a -0 group C(0)-CH3a group -0-C (0)-C (CH3) 3, a group -0-C(0)-NH29 C(CH3)3, a -NH-C (O)-CH3 group, a -NH-C (O) -C3H4 group, a -S (O) 2_CH3 group, a -S(O)2_C3H4 group, a -N(CH3)2 group and a -C (O)-O-CH3 group, the adamantyl group is preferably unsubstituted; or a group RO-CH2(R' ) -, where: or R is an alkyl group (C4-C4), preferably a methyl or ethyl group, or R' is an alkyl group (C4-C4), in particular an alkyl group (C3-C4), and preferably an isopropylmethyl group, or R' is a phenyl group, optionally substituted by one to three groups and in particular substituted by a group, selected from the group consisting of an alkyl group (Ci-Cg), a fluoroalkyl group (C4-C4), a fluoroalkoxy group (C4-C4), a halogen atom and a hydroxy group, the phenyl group being preferably unsubstituted. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, where R1 represents: an alkyl group (C1-C3) substituted by one or two groups selected from a -COORa group, a hydroxy group, a fluorine atom, an alkoxy group (C4-C4), and a benzyloxy group, such benzyloxy group being optionally substituted at its phenyl group by a halogen atom, a spiro bicyclic ring (C5-C5), or an R'-L- group, wherein L is either a single bond or an alkoxy group (C1-C3), optionally substituted by a group chosen from a hydroxy group and an alkoxy group (C1-C3), and R' is selected from the group consisting of: a cycloalkyl (C3-C8) group, optionally substituted by one, two, or three groups selected from a halogen atom, a (C1-C4) alkyl group, a hydroxy group, and a (C1-C3) alkoxy group, and a bridging cycloalkyl (Cg-Cio) group, optionally substituted by one to three groups selected from a (C1-C4) alkyl group, a (C1-C4) alkoxy group, a halogen atom, a hydroxy group, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, an -SO2Rd group, an -N(Re>2) group, and a -COORa group, Ra represents an alkyl group (C1-C4), Rd represents an alkyl group (C1-C4) or a cyclopropyl group and Re represents an alkyl group (C1-C3), and wherein R2 represents a hydrogen atom or an alkyl group (C1-C3), or any of its pharmaceutically acceptable salts. front Ln / zznz / E / YiAi This subgroup of compounds is grouped under the Al compound type within the following Table 1. Still in accordance with such embodiment, R1 may more particularly represent a cyclopropylmethyl, a cyclopropyl, a cyclobutyl, a cyclopentyl, a cyclohexylmethyl, a cyclohexyl, a cycloheptylmethyl, a cycloheptyl, a cyclooctyl, a 3-hydroxy-2,2-dimethylpropyl, a 2-benzyloxyethyl, a 2-methylcyclohexyl, a 1-cyclohexylethyl, a 1-adamantylmethyl, a 1-(1-adamantyl)ethyl, a 1-adamantyl, a 2-adamantyl, a 3,5-dimethyl-l-adamantyl, a 5-hydroxy-2-adamantyl, a 3-hydroxy-l-adamantyl, a 3-methoxy-l-adamantyl, a 2,6,6-trimethylnorpinan-3-yl, a 6,6-dimethylnorpinan-2-yl, a spiro[2,5]octan-2-yl, a spiro[3.3]heptan-2-yl, a 1,7,7trimethylnorbornan-2-yl, norbornan-2-yl, a 2-isopropyl-5methyl-cyclohexyl, a 1-(cyclohexylmethyl)-2-hydroxyethyl, 1(cyclopentylmethyl)-2-hydroxyethyl, 1- (cyclobutylmethyl)-2hydroxyethyl, 1-(cyclopropylmethyl1)-2-hydroxyethyl, 1(hydroxymethyl)-3-methyl-butyl, 1-(methoxymethyl)-3-methylbutyl, 1-(hydroxymethyl)propyl, 1-(fluoromethyl)-3-methylbutyl,l-cyclohexyl-2-hydroxy-ethyl, a 1-cyclohexyl-2-methoxy-ethyl, a 2-cyclohexyl-2-hydroxy-ethyl, 2-cyclohexyl2-methoxyethyl, 2-hydroxycyclopentyl, 2-methoxycyclopentyl, 2-hydroxycyclohexyl, 3-hydroxycyclohexyl, 4hydroxycyclohexyl, 2-methoxycyclohexyl, 4-methoxycyclohexyl, fronr Ln / zznz / E / YiAi a 2-hydroxycycloheptyl, a 3-hydroxycycloheptyl, a 2methoxycycloheptyl, a -CH (COOCH3)-CH (CH3)2, a -CH (COOCH3)CH3, a -CH (COOCH3)-CH2-CH (CH3)2, a -CH (COOCH3)-CHOH-CH3, a 3,3-difluorocyclopentyl, a 4,4-difluorocyclohexyl, a 3,3-difluorocyclohexyl, a 2,2-difluorocyclohexyl, a 3,3-difluorocycloheptyl, a 3-acetoxy-1-adamantyl, a 3pivaloyloxy-1-adamantyl, a 3-methoxycyclohexyl, a 4-hydroxycycloheptyl, a 3-methoxycycloheptyl, a 3methoxycycloheptyl, a 4-methoxycycloheptyl, a 3noradamantyl, 3-tert-butylcarbamoyloxy-1-adamantyl, 3fluoro-1-adamantyl, 1-(tert-butoxymethyl)-3-methyl-butyl, 3acetamido-1-adamantyl, 3-(cyclopropanecarbonylamino)-1adamantyl,a 3-(methansulfonamido)-1-adamantyl, a 3-(cyclopropylsulfonylamino)-1-adamantyl, a 3-(dimethylamino)-1-adamantyl, a 2-methoxycarbonyl-2-adamantyl, a 3,5-dihydroxy-l-adamantyl, a 3,5,7-trifluoro-l-adamantyl, a 1-(ethoxymethyl)-3-methylbutyl, a 1-(benzyloxymethyl)-3-methylbutyl, a 1-[(4-fluorophenyl)methoxymethyl]-3-methylbutyl or a 1-(cyclopropoxymethyl)-3-methylbutyl. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, where R1 represents: a fused phenyl group, selected from phenyl groups fused to a cycloalkyl (Cs-Cg) or heterocycloalkyl (C5-Cg) group, wherein the cycloalkyl (C5-Cg) and heterocycloalkyl (C5-Cg) group optionally comprises an unsaturation and is optionally substituted by an alkyl (C1-C4) group, a hydroxy group, a halogen atom, an alkoxy (C1-C3) group, and a -CORa group; a phenyl group, substituted by one or two groups selected from an alkyl (Ci-Cg) group, a fluoroalkyl (C1-C3) group, a fluoroalkoxy (C1-C4) group, a halogen atom, and a heterocycloalkyl (C4-C7) group; such heterocycloalkyl (C4-C7) group is the same optionally substituted by a group alkyl (C1-C4) , or an R'-L- group, wherein L is an alkandiyl (C1-C3) group, optionally substituted by a group chosen from a hydroxy group, an alkoxy (C1-C4) group, an -NRbRc group, a -COORay group, or a halogen atom, and R' is a phenyl group,optionally substituted by one to three groups selected from the group consisting of an alkyl (C1-C4) group, a fluoroalkyl (C1-C4) group and a fluoroalkoxy (C1-C4) group, a halogen atom and a hydroxy group, wherein Ra is an alkyl (C1-C4) or a hydrogen atom and R and Rc are independently selected from alkyl (C1-C4) and a hydrogen atom, and wherein R2 represents a hydrogen atom or a fluoroalkyl (C1-C3) group, or any pharmaceutically acceptable salt thereof. This subgroup of compounds is grouped under compound types A2 and A5 within the following Table 1. Still in accordance with such embodiment, R1 may more particularly represent a benzyl, an indan-2-yl, a (3,4-dimethylphenyl)methyl, a (2,4-dimethylphenyl)methyl, a [2-(trifluoromethyl)phenyl]methyl, a [2-(trifluoromethoxy)phenyl]methyl, a 2-hydroxyindan-l-yl, a 2-methoxyindan-l-yl, a -CH(COOCH3)-CIb-Ph, a -CH(CH2F)Ph, a 2-amino-l-phenylethyl, a 2-(methylamino)-1-phenylethyl, a 2-(dimethylamino)-1-phenylethyl, an l-benzyl-2-hydroxyethyl, an l-benzyl-2-methoxyethyl, a 2-hydroxy-l-phenylethyl, a 2-methoxy-l-phenylethyl, a 2-hydroxy-2-phenylethyl, a 2-methoxy-2-phenyl-ethyl, a 2-hydroxy-3-phenyl-propyl, a 2-methoxy-3-phenyl-propyl, a 3-fluoro-4-methyl-phenyl, a 4-fluorophenyl, a 4-n-hexylphenyl, a 4-(4-methylpiperazin-lyl)phenyl, a 3-(difluoromethoxy)phenyl, a 1-acetylindolin-6yl, a 3-(trifluoromethyl)phenyl, an indan-5-yl, a 4-morpholinophenyl, a 1-methyllindazol-7-yl or a 2-tert-butoxy1-phenyl-ethyl. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined in this document above in fronr Ln / zznz / E / YiAi where R2 represents a hydrogen atom or a methyl group. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, wherein R1 represents an R'-L- group, wherein: R' is a heteroaryl group (Cs-Cs), optionally substituted by one to three groups selected from a halogen atom, an alkyl group (C1-C4), an alkoxy group (C1-C4), and an N-methylpiperazinyl group, and L is an alkandiyl (C1-C3) or single bond, and where R2 represents a hydrogen atom, or any pharmaceutically acceptable salt thereof. This subgroup of compounds is grouped under compound type A3 and A6 within the following Table 1. Still in accordance with such modality, R1 may more particularly represent a (5-methylpyrazin-2-yl)methyl, a 2-pyridylmethyl, a 3-pyridylmethyl, a 4-pyridylmethyl, a (5-methyl-2-furyl)methyl, a (4-methylthiazol-2-yl)methyl, a 3-imidazol-l-ylpropyl, a 2-(,2-pyridyl)ethyl, a 1,3-benzothiazol-2-ylmethyl, a 2-pyrimidinyl, a 2-pyridyl, a l-methylpyrazol-3-yl, a 2-methoxy-6-methyl-3-pyridyl, a pyrimidin-5-yl, a 3-pyridyl, a 1,3,4-thiadiazol-2-yl, a 5-(4-methylpiperazin-l-yl)-2-pyridyl, 6-(4-methylpiperazin-l-yl)-3-pyridyl, a 2-(4-methylpiperazin-l-yl)pyrimidin-5-yl, a 5-(4-methylpiperazin-l-yl)pyrimidin-2-yl, a 5-(4-methylpiperazin-l-yl)pyrazin-2-yl or a 6-(4-methylpiperazin-l-yl)pyridazin-3-yl. According to another particular embodiment, the present invention relates to a compound of formula (I) as defined above in this document, wherein R1 represents an R'-L- group, wherein: R' is a (C3-C5) heterocycloalkyl group, optionally substituted by one to three groups selected from a hydroxyl group, a (C1-C4) alkyl group, an oxo group, and a -COORa group, where Ra4s is defined herein above, and L is a methylene or single bond, and where R2 represents a hydrogen atom, or any pharmaceutically acceptable salt thereof. This subgroup of compounds is grouped under compound type Ά4 and A7 within the following Table 1. Still in accordance with such modality, R1 may more particularly represent a (l-methyl-4-piperidyl)methyl, a tetrahydropyran-4-yl-methyl, a 1-tert-butyloxycarbonylpiperidin-4-yl-methyl, a 7-methyl-7azaspiro[3.5]nonan-2-yl, a tetrahydropyran-4-yl, a 1-tert-butyloxycarbonylpiperidin-4-yl, an ethyloxycarbonylpiperidin-4-yl, an l-methyl-4-piperidyl, an l-methyl-3-piperidyl, an oxetan-3-yl, tetrahydrofuran-3-yl, a tetrahydropyran-3-yl, a 6,6-dimethyltetrahydropyran-3-yl, a 4-hydroxytetrahydropyran-3-yl, an oxepan-3-yl, a 2-oxo-piperidin-3-yl, a 2-oxo-piperidin-5-yl, a quinuclidin-3-yl, a tetrahydrothiopyran3-yl, a 1,4dioxepan-6-yl, a 2-oxo-pyrrolidin-3-yl, a l-methyl-2-οχοpyrrolidin-3-yl, a 4, 4-dimethyl-2-oxo-pyrrolidin-3-yl, a l-methyl-2-oxo-piperidin-3-yl, a 3-methyl-2-oxo-pyrrolidin-3-yl or a 1,3-dimethyl-2-oxo-pyrrolidin-3-yl. In the context of the present invention, the term: - Halogen is understood to mean chlorine, fluorine, bromine, or iodine, and in particular denotes chlorine, fluorine, or bromine. Alkyl (Ci-Cx), as used herein, refers respectively to a normal, secondary, or tertiary monovalent saturated hydrocarbon radical Ci-Cx, e.g., alkyl (Ci-C6). Examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, terebutyl, pentyl, isopentyl, hexyl, and isohexyl groups, and the like. - alkandiyl (C1-C3), as used herein, refers to a divalent, branched or linear saturated hydrocarbon radical comprising 1 to 3 carbon atoms, and more particularly a methylene, ethylene or propylene, such as linear propylene or isopropylene, such alkandiyl can be substituted as is evident from the following description. - Cycloalkyl (C3-C8), as used herein, refers to a cyclic saturated hydrocarbon, of 3 to 8 carbon atoms, saturated or partially unsaturated and unsubstituted or substituted. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. The term "C3-C8 heterocycloalkyl group," as used herein, refers to a cycloalkyl (C3-C8) group in which one or two of the carbon atoms are replaced by a heteroatom such as oxygen, nitrogen, or sulfur, and more particularly by an oxygen or nitrogen atom. Such a heterocycloalkyl group may be saturated or partially saturated and unsubstituted or substituted. Examples include, but are not limited to, morpholinyl, piperazinyl, piperidinyl, pyrrolidinyl, aziridinyl, oxanyl, oxethanyl, tetrahydropyranyl, morpholinyl, tetrahydrofuranyl, oxepanyl, diazepanyl, dioxanyl, and tetrahydrothiopyranyl, and more particularly piperidinyl and piperazinyl, and even more particularly piperazinyl. The term alkoxy (Ci-CX), as used herein, refers to an -O-alkyl (C3-Cx) or -O-cycloalkyl (C3-Cx) group, where alkyl and cycloalkyl are as defined above, e.g., alkoxy (Ci-C8). Examples include, but are not limited to, methoxy, ethoxy, 1-propoxy, 2-propoxy, cyclopropoxy, butoxy, tert-butoxy, and pentoxy. A spiro bicyclic (C5-C11) ring refers to two rings connected through a single common defining atom. Such a spiro bicyclic alkyl generally comprises 5 to 11 carbon atoms, forming a spiro bicyclic (C5-C11) alkyl group. In one particular embodiment, one or more carbon atoms of the rings are replaced by heteroatoms such as oxygen, nitrogen, or sulfur, and more particularly by a nitrogen atom, forming a heteroalkyl spiro bicyclic (C5-C11) group. Such a spiro bicyclic ring may be substituted or unsubstituted, particularly by at least one alkyl (C3C3) group such as methyl. Examples include, but are not limited to, spiro[3,3]heptanyl, spiro[2,5]octanyl, and 7azaspiro[3,5]nonanyl. - A bridged cycloalkyl (C6-C10) group, as used herein, refers to a bi- or tricyclic compound where the rings are cycloalkyl, the rings share three or more atoms, and the bridge contains at least one atom, for example, 1, 2, or 3 atoms. Such bridged cycloalkyl groups may be substituted with one or more C1-C3 alkyl groups. Examples include, but are not limited to, adamantyl, 2,6,6-trimethylbicyclo[3.1.1]heptyl, 6,6-dimethylbicyclo[3.1.1]heptyl, bicyclo[3.1.1]heptyl, and 1,6,6-trimethylbicyclo[3.1.1]heptyl. A bridged heterocycloalkyl (C6-C10) group, as used herein, refers to a bridged cycloalkyl (C6-C10) group as defined above, wherein one or more carbon atoms of the rings are replaced by heteroatoms such as oxygen, nitrogen, or sulfur, and more particularly by a nitrogen atom. Examples include, but are not limited to, quinuclidin-3-yl. A fused phenyl group refers to a bicyclic radical containing a phenyl portion and which may be substituted. Such a fused phenyl group can be fused to a cycloalkyl or heterocycloalkyl group and attached to the rest of the molecule by its phenyl portion or by the cycloalkyl or heterocycloalkyl group. Examples include, but are not limited to, indanyl, acetylindolinyl, methylindazolyl, hydroxyindanyl, benzothiazolyl, indolyl, indazolyl, methoxyindanyl, and similar groups. - A heteroaryl group (C5-Cn), as used herein, refers to a monocyclic aromatic group or a bicyclic aromatic group in which at least one of the rings is aromatic and in which one to three carbon atoms of the ring are replaced by a heteroatom, such as nitrogen, oxygen, or sulfur. Examples of heteroaryl groups include, but do not include: be limited oxazole, isoxazole pyridine, pyrimidine fronr Ln / zznz / E / YiAi pyridazine, triazine, pyrazine, oxadiazole, furan, pyrazole, thiazole, isothiazole, thiadiazole, imidazole, triazole and the like. Within the framework of the present invention, heteroaryl is advantageously pyridine, imidazole, pyrazine, furan, thiazole, pyrazole, thiadiazole, pyridazine and pyrimidine. - an aromatic ring means, according to Hückel's rule, that a molecule has 4n + 2π electrons. - A fluoroalkyl group (Ch-Cx), as used herein, refers to an alkyl (Ci~Cx) as defined above herein in which one or more fluorine atoms have been replaced by hydrogen. In one embodiment, all the hydrogen atoms are replaced by fluorine atoms, forming perfluoroalkyl groups, such as trifluoromethyl. - A fluoroalkoxy (Ci-Cx), as used herein, refers to an alkoxy (Ci~Cx) as defined above herein in which one or more fluorine atoms have been replaced by hydrogen, such as trifluoromethoxy. In one embodiment, all the hydrogen atoms are replaced by fluorine atoms, forming perfluoroalkoxy groups, such as trifluoromethoxy. In the context of the present invention, the terms aromatic ring and heteroaryl include all positional isomers. front Ln / zznz / E / YiAi The nomenclature of the following compounds (1) to (216) was generated in accordance with the principles of the International Union of Pure and Applied Chemistry, using Accelrys Draw 4.1 SP1. To avoid confusion, the symbol (+) was added to designate a racemic mixture; the prefixes cisz / and trans were also used to assign the relative stereochemistry of two adjacent chiral centers. According to a preferred embodiment of the present invention, the compound of formula (I) is selected from: (1) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- (cyclopropylmethylamino)-lH-imidazole-5-one, (2). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2(cyclopropylamino)-lH-imidazole-5-one, (3). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2(cyclobutylamino)-lH-imidazole-5-one, (4). (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2(cyclopentylamino)-lH-imidazole-5-one, (5). (4Z)-4-(l,3-Benzothiazol-6-ylmethylene)-2(cyclohexylmethylamino)-lH-imidazole-5-one, (6). (42)-4-(1,3-Benzothiazol-6-íImethylene)-2(cyclohexylamino)-lH-imidazole-5-one, (7). (4Z)-4-(l,3-Benzothiazol-6-ylmethylene)-2(cycloheptlymethylamino)-lH-imidazole-5-one, (8). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- fronr Ln / zznz / E / YiAi (cycloheptylamino)-lH-imidazole-5-one, (9). (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclooctylamino)-lH-imidazole-5-one, (10). (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(3-hidroxi-2,2-dimetil-propil)amino]-lH-imidazol-5-ona, (11) . (4Z)-4-(l,3-Benzotiazol-6-ilmetilen)-2- (2-benciloxietilamino)-lH-imidazol-5-ona, (12) . ( + )-(4Z)-4-(1,3-Benzotiazol-6-ilmetilen)- 2-[[cis-2-metilciclohexil]amino]-lH-imidazol-5-ona, (13) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [ [ (IR) -1-ciclohexiletil] amino] -1 Jí-imidazol-5-ona, (14) . (4Z)-2 -(1-Adamantilmetilamino)-4 -(1,3- benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (15) . (+)-(4Z)-2-[1-(1-Adamantil)etilamino]-4- (1,3-benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (16) . (4Z)-2-(1-Adamantilamino)-4-(1,3- benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (17) . (4Z)-2-(2-Adamantilamino)-4-(1,3- benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (18) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[3,5-dimetil-l-adamantil]amino]-lH-imidazol-5-ona, (19) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(trans-5-hidroxi-2-adamantil)amino]-lH-imidazol-5-ona, (20) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(3-hidroxi-l-adamantil)amino]-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi (21) . (4Ζ) -4-(1,3-Benzotiazol-6-ilmetilen) -2- [(3-metoxi-l-adamantil)amino]-lH-imidazol-5-ona, (22) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(IR,2R,3R,5S)-2,6,6-trimetilnorpinan-3-il]amino]-1Himidazol-5-ona, (23) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(1S,2S,3S,5R)-2,6,6-trimetilnorpinan-3-il]amino]-1Himidazol-5-ona, (24) . (4Z)-4-(l,3-Benzotiazol-6-ilmetilen)-2- [[(lR,2R,5R)-6,6-dimetilnorpinan-2-il]metilamíno]-1Himidazol-5-ona, (25) . (±)-(4Z)-4-(1,3-Benzotiazol-6-ilmetilen)- 2-(espiro[2.5]octan-2-ilamino)-lH-imidazol-5-ona, (26) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (espiro[3.3]heptan-2-ilamino)-lH-imidazol-5-ona, (27) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(2R)-1,1,7-trimethylnorbornan-2-yl]amino]-1H-imidazol-5-one, (28) . ( + )-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-(norbornan-2-ylamino)-1n-imidazol-5-one, (29) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl]amino]-1Himidazol-5-one, (30) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(ciclohexylmetil)-2-hydroxy-etil]amino]-1H-imidazole fronr Ln / zznz / E / YiAi 5-ona (31) . (4Ζ)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(cyclopentylmethyl)-2-hydroxy-ethyl]amino]-1Himidazol-5-one, (32) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(ciclobutilmethyl)-2-hydroxy-ethyl]amino]-1H-imidazol-5-one, (33) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ (IR)-1-(ciclopropylmethyl)-2-hydroxy-ethyl]amino]-1Himidazol-5-one, (34) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(hidroxymetil)-3-methyl-butyl]amino]-lH-imidazol-5ona, (35) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(metoximetil)-3-methyl-butyl]amino]-lH-imidazol-5ona, (36) . (4Z) -4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S)-1-(hidroxymetil)-3-methyl-butyl]amino]-lH-imidazol-5ona, (37) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S)-1-(metoximetil)-3-methyl-butyl]amino]-lH-imidazol-5ona, (38) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(hydroxymethyl)propyl]amino]-lH-imidazol-5-ona, (39) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S)-1-(hidroximetil)propyl]amino]-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi 6(40) (±)-(42)-4-(1,3-Benzotiazol-6-ylmethylene)- 2- [ [1- (fluoromethyl) -3-methyl-butyl] amino] -1H-imidazol-5-one, (41) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2- [ (1-cyclohexyl-2-hydroxy-ethyl) amino] -1H-imidazol-5-one, (42) . ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2- [(1-cyclohexyl-2-methoxy-ethyl)amino]-1H-imidazol-5-one, (43) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2- [(2-cyclohexyl-2-hydroxy-ethyl)amino]-1H-imidazol-5-one, (44) . ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[(2-cyclohexyl-2-methoxy-ethyl)amino]-1H-imidazol-5-one, (45) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[cis-2-hydroxycyclopenty1]amino]-1H-imidazol-5-one, (46). (+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-2-hydroxycyclopenty1]amino]-1H-imidazol-5-one, (47) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[cis-2-methoxycyclopenty1]amino]-1H-imidazol-5-one, (48) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-2-methoxycyclopentyl]amino]-1H-imidazol-5-one, (49) .(±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[cis-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (50). (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (51). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,2S)-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (52). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2fronr Ln / zznz / E / YiAi. [[(1S,2R)-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (53) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1R,2R}-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (54) .(4Z}-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S,25}-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (55) .(±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-3-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (56) . ( + )-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-3-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (57) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(trans-4-Hydroxycyclohexyl)amino]-1H-imidazol-5-one, (58) . (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, (59) . ( + )-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, (60) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(trans-4-methoxycyclohexyl)amino]-1H-imidazol-5-one, (61) . (+)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (62) . (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (63) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1R,2R)-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (64) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S,25}-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, fronr Ln / zznz / E / YiAi (65) .(±)-(4Ζ)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-3-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (66) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-3-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (67) . ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-2-methoxycycloheptyl]amino]-1H-imidazol-5-one, (68) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-2-metoxicyclohepti1]amino]-lH-imidazol-5-ona, (69) . (25) -2-[[(42)-4-(1,3-benzotiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]-3-methyl-butanoate de methylo, (70) . (25) -2-[[(42)-4-(1,3-benzotiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]propanoate de methylo, (71) . (25)-2-[[(42)-4-(1,3-benzotiazol-6-ilmethylene)-5-oxo-lH-imidazol-2-il]amino]-4-methyl-pentanoate de methylo, (72) . (2R)-2-[[(42)-4-(1,3-benzotiazol-6-ilmethylene)-5-oxo-lH-imidazol-2-il]amino]-4-methyl-pentanoate de methylo, (73) . (25) -2-[[(42)-4-(1,3-benzotiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]-3-hydroxy-butanoate de methylo, (74) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (bencilamino)-lH-imidazol-5-ona, (75) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- fronr Ln / zznz / E / YiAi (indan-2-ilamino)-lH-imidazol-5-ona, (76) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(3,4-Dimethylphenyl)methylamino]-lH-imidazol-5-ona, (77) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(2,4-Dimethylphenyl)methylamino]-1H-imidazol-5-one, (78) . (42) -4-(1,3-Benzothiazol-6-ylmethylene)-2- [[2-(trifluoromethyl)phenyl]methylamino]-1H-imidazol-5-one, (79) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[2-(trifluoromethoxy)phenyl]methylamino]-1H-imidazol-5-one, (80) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-2-hydroxyindan-1-yl]amino]-1H-imidazol-5-one, (81) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-2-hydroxyindan-1-yl]amino]-1H-imidazol-5-one, (82) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1R,2R)-2-hydroxyindan-1-yl]amino]-1H-imidazol-5-one, (83). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S,23}-2-hydroxyindan-1-yl]amino]-1H-imidazol-5-one, (84) . ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-2-methoxyindan-1-yl]amino]-1H-imidazol-5-one, (85). (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-2-metoxiindan-l-il]amino]-lH-imidazol-5-ona, (86) . (2S) -2-[[(42)-4-(1,3-benzotiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]-3-phenyl-propanoate de methylo, (87) . fronr Ln / zznz / E / YiAi {2R}-2-[[(42)-4-(1,3-benzotiazol-6ylmethylene)-5-oxo-lH-imidazol-2-il]amino]-3-phenyl-propanoate de methylo, (88) . (±)-(42)-4-(1,3-Benzotiazol-6-ylmethylene)- 2-[(2-fluoro-l-phenyl-ethyl)amino]-lH-imidazol-5-ona, (89) . Dichlorhidrato de (!) -(42)-2-[(2-Amino-l- phenyl-ethyl)amino]-4-(1,3-benzotiazol-6-ylmethylene)-1Himidazol-5-ona, (90) . Dichlorhydrate of (±)-(4Z)-4-(1,3- Benzotiazol-6-ylmethylene)-2-[[2-(methylamino)-1-phenylethyl]amino]-lH-imidazol-5-ona, (91) . (±)-(42)-4-(1,3-Benzotiazol-6-ylmethylene)- 2-[[2-(dimethylamino)-1-phenyl-ethyl]amino]-1′-imidazol-5-ona, (92) . (+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(l-bencil-2-hydroxy-ethyl)amino]-lH-imidazol-5-ona, (93) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ (IR) -l-benzyl-2-hydroxy-ethyl] amino] -lJí-imidazol-5-one, (94) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(l-benzyl-2-methoxy-ethyl)amino]-lH-imidazol-5-one, (95) . (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(2-hydroxy-l-phenyl-ethyl)amino]-lH-imidazol-5-one, (96) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-2-hydroxy-l-phenyl-ethyl]amino]-lH-imidazol-5-one, (97) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1S)-2-hydroxy-l-phenyl-ethyl]amino]-lH-imidazol-5-one, (98) . fronr Ln / zznz / E / YiAi (±)- (42)-4-(1,3-Benzothiazol-6-ylmethylene)51 2-[(2-metoxi-l-phenyl-ethyl)amino]-lH-imidazol-5-ona, (99). (±)-(42)-4-(1,3-Benzotiazol-6-ylmethylene)2-[(2-hidroxy-2-phenyl-ethyl)amino]-lH-imidazol-5-ona, (100). (+)-(42)-4-(1,3-Benzotiazol-6-ylmethylene)2-[(2-metoxi-2-phenyl-ethyl)amino]-lH-imidazol-5-ona, (101). (±)-(42)-4-(l,3-Benzotiazol-6-ylmethylene)2-[(2-hidroxy-3-phenyl-propyl)amino]-lH-imidazol-5-ona, (102). (+)-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2- [ (2-metoxi-3-fenil-propil) amino] -llí-imidazol-5-ona, (103). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2[(5-metilpirazin-2-il)metilamino]-lH-imidazol-5-ona, (104). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2(2-piridilmetilamino)-1H-imidazol-5-ona, (105). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2(3-piridilmetilamino)-1H- imidazol-5-ona, (106). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2(4-pyridiImethylamino)-1H-imidazol-5-ona, (107). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[(5-methyl-2-furyl)methylamino]-lH-imidazol-5-ona, (108).(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[(4-metiltiazol-2-yl)methylamino]-1H-imidazol-5-ona, (109). (42)-4-(1,3-Benzotiazol-6-ylmethylene)-2(3-imidazol-l-ylpropylamino)-1H-imidazol-5-ona, (110). (42)-4-(1,3-Benzotiazol-6-ylmethylene)-2[2-(2-pyridyl)ethylamino]-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi (111) . (4Ζ)-2-(1,3-Benzothiazol-2-ylmethylamino)-. 4-(1,3-benzothiazol-6-ylmethylene)-lH-imidazol-5-ona, (112) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ (l-metil-4-piperidil) me til ami no] -lH-imidazol-5-ona, (113) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (tetrahidropiran-4-ilmetilamino)-lH-imidazol-5-ona, (114) . 4-[ [ [ (4Z)-4-(1,3-benzotiazol-6- ilmetilen)-5-oxo-lH-imidazol-2-il]amino]metil]piperidin-1carboxilato de tero-butilo, (115) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(7-metil-7-azaespiro[3.5]nonan-2-il)amino]-lfí-imidazol-5ona, (116) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (3-fluoro-4-metil-anilino)-lH-imidazol-5-ona, (117) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (4-fluoroanilino)-lH-imidazol-5-ona, (118) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (4-hexilanilino)-lH-imidazol-5-ona, (119) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [4-(4-metilpiperazin-l-il)anilino]-lH-imidazol-5-ona, (120) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [3-(difluorometoxi)anilino]-lH-imidazol-5-ona, (121) . (4Z) -2-[(1-Acetilindolin-6-il)amino]-4- (1,3-benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (122) . fronr Ln / zznz / E / YiAi (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-253 [3- (trifluorometil)anilino]-lH-imidazol-5-ona, (123) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (indan-5-ilamino)-lH-imidazol-5-ona, (124) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (4-morfolinoanilino)-lH-imidazol-5-ona, (125) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(l-metilindazol-7-il)amino]-lH-imidazol-5-ona, (126) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (pirimidin-2-ilamino)-lH-imidazol-5-ona, (127) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (2-piridilamino)-lH-imidazol-5-ona, (128) . (4Z) -4-(1,3-Benzotiazol-6-ilmetilen)-2- [ (l-metilpirazol-3-il)amino]-lH-imidazol-5-ona, (129) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(2-metoxi-6-metil-3-pyridil)amino]-lH-imidazol-5-ona, (130) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (pyrimidin-5-ilamino)-lH-imidazol-5-ona, (131) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (3-piridilamíno)-lH-imidazol-5-ona, (132) . (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (1,3,4-tiadiazol-2-ilamino)-lH-imidazol-5-ona, (133) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[5-(4-methylpiperazin-l-yl)-2-pyridyl]amino]-lH-imidazol-5ona, (134) . fronr Ln / zznz / E / YiAi (42)-4-(1,3-Benzotiazol-6-ilmetilen)-254 [[6-(4-methylpiperazin-l-yl)-3-pyridyl]amino]-lH-imidazol-5ona, (135) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[2-(4-methylpiperazin-l-il)pyrimidin-5-il]amino]-1H-imidazol5-ona, (136) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[5-(4-methylpiperazin-l-il)pyrimidin-2-il]amino]-lfl-imidazol5-ona, (137) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[5-(4-methylpiperazin-l-yl)pyrazin-2-yl]amino]-lH-imidazol-5one, (138) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[6-(4-methylpiperazin-l-yl)pyridazin-3-yl]amino]-1H-imidazol5-ona, (139) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(tetrahidropyran-4-ylamino)-1 H-imidazol-5-ona, (140) . 4 -[[(4Z)- 4-(1,3-benzothiazol-6-ylmethylene)- 5-oxo-1H-imidazol-2-yl]amino]piperidin-1-carboxylate of terebutyl, (141) . 4-[[(4Z)-4-(1,3-benzothiazol-6-ylmethylene)- 5-oxo-1H-imidazol-2-yl]amino]piperidin-1-carboxylate de ethyl, (142) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- [(l-methyl-4-piperidyl)amino]-1H-imidazol-5-ona, (143) . fronr Ln / zznz / E / YiAi (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)55 2-[(l-methyl-3-piperidil)amino]-lH-imidazol-5-ona, (144). (42)-4-(l,3-Benzotiazol-6-ilmetilen)-2(oxetan-3-ilamino)-lH-imidazol-5-ona, (145). (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3R)-tetrahydrofuran-3-il]amino]-lH-imidazol-5-ona, (146). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3S)-tetrahydrofuran-3-il]amino]-1 Jí-imidazol-5-ona, (147). (4Z)-4-(1,3-Benzotiazol-6-ilmetilene)-2[ [ (3R)-tetrahydropiran-3-il ] amino ]-1 Jí-imidazol-5-ona, (148). (42)-4-(1,3-Benzotiazol-6-ilmetilene)-2[[(3S)-tetrahydropiran-3-il]amino]-lfí-imidazol-5-ona, (149). (1)-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(6,6-dimetiltetrahydropiran-3-il)amino]-lH-imidazol-5-ona, (149A). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3R) / (3S)-6,6-dimethyltetrahidropiran-3-il]amino]-1Himidazol-5-ona, (149B). (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3R) / (3S)-6,6-dimethyltetrahidropiran-3-il]amino]-1Himidazol-5-ona, (150).(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(3R,4R)-4-hydroxytetrahydropyran-3-yl]amino]-1H-imidazol-5-one, (151) . (+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-. 2-(oxepan-3-ilamino)-lH-imidazol-5-ona, (152) . (±)-3- [ [ (42)-4-(1,3-Benzotiazol-6 fronr Ln / zznz / E / YiAi ilmetilen)-5-oxo-lH-imidazol-2-il]amino]piperidin-2-ona, (153) . (3S)-3-[[(4Z)-4-(1,3-Benzotiazol-6- ilmetilen)-5-oxo-lH-imidazol-2-il]amino]piperidin-2-ona, (154) . (5S) -5- [ [ (42) -4-(1,3-Benzotiazol-6- ilmetilen)-5-oxo-lH-imidazol-2-il]amino]piperidin-2-ona, (155). (±)-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2 - [ (3, 3-dif luorociclopent il) amino ] -1 Jí-imidazol-5-ona, (156) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[(4,4-difluorociclohexil)amino]-lH-imidazol-5-ona, (157). ( + )-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(3,3-difluorociclohexil)amino]-lH-imidazol-5-ona, (158). ( + )-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(2,2-difluorociclohexil)amino]-lH-imidazol-5-ona, (159). (+)-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(3,3-difluorocicloheptil)amino]-lH-imidazol-5-ona, (160). (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR)-1-(fluorometil)-3-metil-butil]amino]-lH-imidazol-5ona, (161).(42)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(1S)-1-(fluorometil)-3-metil-butil]amino]-lH-imidazol-5ona, (162). Acetato de [3-[[(4Z)-4-(1,3-Benzotiazol6-ilmetilen)-5-oxo-lH-imidazol-2-il]amino]-1-adamantilo], (163). 2,2-dimetilpropanoato de [3-[[(42)-4(1,3-Benzotiazol-6-ilmetilen)-5-oxo-lH-imidazol-2-il]amino]fronr Ln / zznz / E / YiAi. 1-adamantilo], (164). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,2R}-2-methoxycyclopentyl]amino]-1H-imidazol-5-one, (165). (4Z}-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(1S,25}-2-methoxycyclopentyl]amino]-1H-imidazol-5-one, (166). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[ [ (IR,2R)-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, (167). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(1S,25}-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, (168). (1)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[cis-3-methoxycyclohexyl]amino]-1H-imidazol-5-one, (169). (1)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-3-methoxycyclohexyl]amino]-1H-imidazol-5-one, (169A). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,3R) / (1S,35}-3-methoxycyclohexyl]amino]-1H-imidazol-5-one, (169B). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,3R) / (1S,3S)-3-methoxycyclohexyl]amino]-1H-imidazol-5-one, (170). (1)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-4-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (171). (1)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-4-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (171A). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,4R) / (1S,4S)-4-hydroxycycloheptyl]amino]-1H-imidazol-5-one, fronr Ln / zznz / E / YiAi (171Β) . (4Ζ)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(1R,4R) / (15,45)-4-hydroxycycloheptyl]amino]-1H-imidazol-5one, (172) . ( + )-(4S)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-3-methoxycycloheptyl]amino]-1H-imidazol-5-one, (173) . (±)-(45)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-3-methoxycycloheptyl]amino]-1H-imidazol-5-one, (174) . (+)-(45)-4-(1,3-Benzothiazol-6-ylmethylene)- - [[cis-4-methoxycyclohepti 1]amino]-1H-imidazol-5-one, (175). (±)-(4S)-4-(1,3-Benzothiazol-6-ylmethylene)2-[[trans-4-methoxycycloheptyl]amino]-1H-imidazol-5-one, (176) . (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-2-methoxy-l-phenyl-ethyl]amino]-lH-imidazol-5-one, (177) . (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(15)-2-methoxy-l-phenyl-ethyl]amino]-lH-imidazol-5-one, (178). (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(2R)-2-hydroxy-2-phenyl-ethyl]amino]-lH-imidazol-5-one, (179). (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(25)-2-hydroxy-2-phenyl-ethyl]amino]-lH-imidazol-5-one, (180) . Dichlorohydrate of (4Z)-2-[[(IR)-2-Amino-l- phenyl-ethyl]amino]-4-(1,3-benzothiazol-6-ylmethylene)-1Chimidazol-5-one, (181) . Dichlorohydrate of (45)-2-[[(15)-2-Amino-lphenyl-ethyl]amino]-4-(1,3-benzothiazol-6-ylmethylene)-1H fronr Ln / zznz / E / YiAi imidazol-5-ona (182) . (42) -4-(1,3-Benzothiazol-6-ylmethylene) -2- [[(3R)-quinuclidin-3-il]amino]-lH-imidazol-5-ona, (183). (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3S)-quinuclidin-3-il]amino]-lH-imidazol-5-ona, (184). ( + )-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2- (tetrahidrotiopiran3-ilamino)-lH-imidazol-5-ona, (185). (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)2-(1,4-dioxepan-6-ilamino)-lH-imidazol-5-ona, (186). ( + )-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(2-oxopirrolidin-3-il)amino]-lH-imidazol-5-ona, (187). (±)-(4Z)- 4-(1,3-Benzotiazol-6-ilmetilen)2-[(l-metil-2-oxo-pirrolidin-3-il)amino]-lH-imidazol-5-ona, (188). ( + )-(42)-4-(1,3-Benzotiazol-6-ilmetilen)2-[(4,4-dimetil-2-oxo-pirrolidin-3-il)amino]-lH-imidazol-5ona, (189). (3R) -3- [ [ (42) -4-(l,3-Benzotiazol-6ilmetilen)-5-oxo-lH-imidazol-2-il]amino]piperidin-2-ona, (190). (±)—3—[[(42)-4-(1,3-Benzotiazol-6ilmetilen)-5-oxo-lH-imidazol-2-il]amino]-l-metil-piperidin-2ona, (191). (±)-(4Z)- 4-(1,3-Benzotiazol-6-ilmetilen)2- [ (3-metil-2-oxo-pirrolidin-3-il) amino] -1 JJ-imidazol-5-ona, (192).(+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)2-[(1,3-dimethyl-2-oxo-pyrrolidin-3-yl)amino]-lH-imidazol-5 fronr Ln / zznz / E / YiAi ona, (192Α). (43)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(3R) / (33)-1,3-dimethyl-2-oxo-pyrrolidin-3-yl]amino]-1Himidazol-5-one, (192B) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(3R) / (3S)-1,3-dimethyl-2-oxo-pyrrolidin-3-yl]amino]-1Chimidazol-5-one, (193) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-. [[(33,43)-4-hydroxytetrahydropyran-3-yl]amino]-lH-imidazol-5one, (194) . (43)-2-(3-Noradamantilamino)-4-(1,3- benzothiazol-6-ylmethylene) -1 Jí-imidazol-5-one, (195) . 7V-terc-but ylcarbamate of [3-[[(43)-4- (1,3-Benzothiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]1-adamantyl], (196) . (43)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ (3-fluoro-l-adamantyl)amino]-lH-imidazol-5-one, (197) . (43)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(tert-butoxymethyl)-3-methyl-butyl]amino]-lH-imidazol5-one, (198) . (43)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-2-terc-butoxy-l-phenyl-ethyl]amino]-lH-imidazol-5-ona, (199) . N-[3-[[(43)-4-(1,3-Benzothiazol-6-ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]-1adamantyl]acetamida, (200). fronr Ln / zznz / E / YiAi N-[3-[[(43)-4-(1,3-Benzothiazol-6-ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-1adamantyl]cyclopropanecarboxamida, (201) . N-[3-[[(4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-1adamantyl]methanesulfonamida, (202) . N-[3-[[(4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-1adamantyl]cyclopropanesulfonamida, (203) . (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[3-(dimethylamino)-1-adamantyl]amino]-1H-imidazol-5-ona, (204) . 2-[[(4Z)-4-(1,3-benzothiazol-6-ylmethylene)- 5-oxo-1H-imidazol-2-yl]amino]adamantan-2-carboxylate de methyl, (205) . (4Z)-2-(Cyclohexylamine)-4-[(2-methyl-1,3-benzothiazol-6-yl) mothylene]-1 Jí-imidazol-5-ona, (206) . (4 Z)-2-(Cycloheptylamino)-4-[(2-methyl- 1,3-be nzotiazol-6-yl)methylene]-lH-imidazol-5-ona, (207) . (4Z)-2-[[(IR)-1-(Methoximetil)-3-methyl-butyl]amino]-4-[(2-metil-l,3-benzotiazol-6-yl)methylene]-1Himidazol-5-ona, (208) . (4Z)-2-[[(IR)-2-Metoxi-l-phenyl-ethyl]amino]-4-[(2-metil-l,3-benzotiazol-6-yl)methylene]-1Himidazol-5-ona, (209) . (4Z)-2-(1-Adamantylamino)-4-[(2-methyl- 1,3-be nzotiazol-6-il)metilen]-lH-imidazol-5-ona, y fronr Ln / zznz / E / YiAi (210) . (42) -2-[(3-Hidroxi-l-adamantil)amino]-4- [(2-methyl-l,3-benzotiazol-6-yl)methylene]-lH-imidazol-5-ona, (211) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(3,5-dihidroxy-l-adamantil)amino]-lH-imidazol-5-ona, (212) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(3,5,7-trifluoro-l-adamantil)amino]-lH-imidazol-5-ona, (213) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(etoximetil)-3-methyl-butyl]amino]-lH-imidazol-5-ona, (214) . (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(benzyloxymethyl)-3-methyl-butyl]amino]-lH-imidazole-5one, (215). (42)-4-(l,3-Benzothiazol-6-ylmethylene)-2[[(IR)-1-[(4-fluorophenyl)methoxymethyl]-3-methyl-butyl]amino]lH-imidazole-5-one, (216). (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ (IR)-1- (cyclopropoxymethyl)-3-methyl-butyl]amino]-1-Himidazol-5-one, or any of its pharmaceutically acceptable salts. According to an even more preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (4), (5), (6), (7), (8), (9), (12), (13), (14), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), (27), (28), (30), (31), (32), (34), (35), (36), (38), (40), fronr Ln / zznz / E / YiAi (41) , (42) , (43) , (44) , (46) , (48) , (49) , (50) , (51) , (53) , (55) , (56) , (57) , (59) , (60) , (61) , (62) , (63) , (64) , (65) , (66) , (67) , (68) , (69) , (70) , (71) , (72) , (73) , (74) , (77) , (78) , (80) , (81) , (83) , (85) , (86) , (89) , (90) , (92) , (93) , (94), (95), (96), (97), (98), (99), (104), (106), (108), (117), (119), (125), (127), (128), (135), (146), (147), (148), (149), (149Α), (149Β), (150), (151), (154), (155), (157), (158), (159), (160), (161), (162), (164), (165), (167), (168), (169), (169Α), (169Β), (170), (171), (171Α), (171Β), (172), (173), (174), (175), (176), (178), (179), (180), (181), (182), (184), (185), (191), (192), (192A), (194), (195), (196), (197), (198), (199), (200), (201), (203), (204), (208), (209), (210) and their pharmaceutically acceptable salts. According to an even more preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (6), (7), (8), (9), (12), (14), (16), (17), (19), (20) , (21) , (22) , (24) , (25) , (27) , (28) , (31) , (32) , (34) , (35) , (36) , (38) , (40) , (41) , (43) , (44) , (46) , (48) , (49) , (51) , (53) , (55) , (56) , (57) , (59) , (61) , (62) , (63) , (64) , (65) , (66) , (67) , (68) , (69) , (74) , (77) , (78) , (81) , (83) , (85) , (86) , (89) , (90) , (92) , (93) , (95) , (96) , (97) , (98) , (99), (108), (119), (125), (146), (148), (149), (149A), (149B), (150), (151), (155), (157), (158), (159), (160), (161), (162), (164), (165), (167), (168), (169), (169Α), (169Β), (170), (171), (171Α), (171Β), (172), (173), (174), (175), (176), (178), (179), (180), (181), (182), (184), (185), (191), (192), (192Α), (194), (195), (196) (197), (198), (199), (200), (201), (203), (204), (208), and their pharmaceutically acceptable salts. According to an even more preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (9), (16), (17), (19), (20), (21), (22), (25), (27), (34), (35), (40), (48), (61), (65), (66), (78), (81), (83), (89), (95), (96), (97), (99), (158), (159), (160), (162), (169), (172), (173), (175), (176), (184), (194), (195), (196), (199), (200), (201), (203), (210) and their pharmaceutically acceptable salts. According to an alternative embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (1), (3), (4), (5), (6), (7), (8), (9), (10), (12), (13), (14), (16), fronr Ln / zznz / E / YiAi (17) , (19) , (20) , (21) , (22) , (23) , (24) , (25) , (26) , (27) (28) , (30) , (31) , (32) , (33) , (34) , (35) , (36) , (37) , (38) (39) , (40) , (41) , (42) , (43) , (44) , (45) , (46) , (47) , (48) (49) , (50) , (51) , (53) , (55) , (56) , (57) , (58) , (59) , (60) (61) , (62) , (63) , (64) , (65) , (66) , (67) , (68) , (69) , (70) (71) , (72) , (73) , (74) , (75) , (76) , (77) , (78) , (79) , (80) (81), (82), (83), (85), (86), (88), (89), (90), (92), (93), (94), (95), (96), (97), (98), (99), (100), (101), (102), (103), (104), (105), (106), (197), (198). (110), (111), (113), (117), (119), (120), (121), (126), (127), (128), (129), (130), (131), (132), (135), (137), (139), (141), (144), (14), (4), (4), (4), (4), (4), (149), (149Α), (149Β), (150), (151), (154), (155), (156), (157), (158), (159), (160), (161), (162), (163), (164), (165), (166), (166), (16), (19), (196), (19Α), (169Β), (170), (171), (171Α), (171Β), (172), (173), (174), (175), (176), (178), (179), (180), (181), (182), (183), (184), (185), (192), (192), (192). (192Β), (194), (195), (196), (197), (198), (199), (200), (201), (203), (208), (209), (210), and their pharmaceutically acceptable salts. fronr Ln / zznz / E / YiAi According to a preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (1),(4), (5), (6), (7), (8), (9), (10), (12), (13), (14), (16), (17), (19), (20), (21), (22), (23), (24), (25), (26), (27),(28), (30), (31), (32), (33), (34), (35), (36), (38), (40),(41), (43), (44), (46), (48), (49), (51), (53), (55), (56),(57), (59), (61), (62), (63), (64), (65), (66), (67), (68),(69), (70), (71), (73), (74), (76), (77), (78), (79), (80),(81), (82), (83), (85), (86), (88), (89), (90), (92), (93),(94), (95), (96), (97), (98), (99), (100), (101), (102), (104), (105), (106), (108), (109), (113), (117), (119), (127), (128), (130), (131), (135), (139), (141), (146), (147), (148), (149), (149Α), (149Β), (150), (151), (155), (156), (157), (158), (159), (160), (161), (162), (163), (164), (165), (166), (167), (168), (169), (169Α), (169Β), (170), (171), (171Α), (171Β), (172), (173), (174), (175), (176), (178), (179), (180),(181), (182), (183), (184), (185), (191), (192), (192A), (192B), (194), (195), (196), (198), (199), (200), (201), (203), (210), and their pharmaceutically acceptable salts. According to an even more preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (9), (16), (19), (20), (21), (35), (48), (61), (73), (78), (81), (95), (96), (155), (159), (160), (161), (169), (169A), (171A), (176), (184), (196), (199), (200), (201), (203), (210), and their pharmaceutically acceptable salts. According to a further embodiment of the present invention, the compound of formula (I) is selected from the group consisting of compounds (7), (8), (9), (10), (12), (16), (17), (19), (20), (21), (23), (25), (26), (28), (32), (33), (34), (35), (40), (41), (43), (44), (46), (48), (55), (56), (57), (59), (61), (62), (63), (65), (66), (67), (68), (69), (70), (73), (77), (78), (81), (83), (88), (89), (90), (95), (96), (97), (98), (99), (100), (101), (102), (104), (105), (106), (117), (119), (127), (131), (139), (148), (149), (149Β), (151), (155), (156), (157), (158), (159, (160), (161), (164), (165), (167), (169), (169Α), (169Β), (170), (171), (171Α), (171Β), (172), (173), (176), (178), (179), (180), (181), (184), (185), (191), (192), (192Α), (194), (196), (198), (199), (200), (201), (203), (210) and their pharmaceutically acceptable salts. front Ln / zznz / E / YiAi The groups of compounds defined by the list of compounds identified in Example 4 below through Tables 4A to Table 4F and specifically identified as more potent kinase inhibitors, as well as multi-target kinase inhibitors, are also part of the present invention. In accordance with another aspect, an object of the present invention relates to a compound of formula (I) as defined above or any of its pharmaceutically acceptable salts, or at least any of the compounds (1) to (216) or any of their pharmaceutically acceptable salts, for use as a medicament. Pharmaceutically acceptable same salt refers to salts that are formed from acid addition salts formed with inorganic acids (e.g., hydrochloric acid, hydrobromic acid), as well as salts formed with organic acids such as acetic acid, tartaric acid, and succinic acid. front Ln / zznz / E / YiAi Suitable physiologically acceptable acid addition salts of compounds of formula (I) include hydrobromide, tartrate, hydrochloride, succinate, and acetate. The compounds of formula (I) and any of the compounds (1) to (216) or any of their pharmaceutically acceptable salts can form solvates or hydrates and the invention includes all these solvates and hydrates. The terms hydrates and solvates simply mean that the compounds (I) according to the invention can be in the form of a hydrate or solvate, i.e., combined or associated with one or more molecules of water or solvent. This is merely a chemical characteristic of such compounds, which can be applied to all organic compounds of this type. Compounds of formula (I) may comprise one or more asymmetric carbon atoms. They may thus exist as enantiomers or diastereomers. These enantiomers, diastereomers, and mixtures thereof, including racemic mixtures, are included within the scope of the present invention. The compounds of the present invention can be prepared by conventional organic synthesis methods practiced by those skilled in the art. The general reaction sequences described below represent a useful general method for preparing the compounds of the present invention and are not intended to limit its scope or utility. List of abbreviations: front Ln / zznz / E / YiAi Abbreviation / Acronym Name Ac Acetyl ACN Acetonitrile Alk Alkyl ATP Adenosine Triphosphate Br s Broad Singlet C Molar Concentration Comp. NO. Compound Number D Doublet DCM Methylene Chloride Dd Doublet of Doublets DI PEA N,N-Diisopropylethylamine DMF Dimethylformamide DMSO Dimethyl Sulfoxide DTT Dithiothreitol Eq. Equivalent ESI Electrospray Ionization 70 Abbreviation / Acronym Name Et Ethyl FC Flash Chromatography GP General Protocol GST Glutathione S-transferase Hal Halogen HEPES 4-(2-Hydroxyethyl)-1-piperazine ethanosulfate His-Labeling Polyhistidine Labeling HPLC High-Performance Liquid Chromatography IC50 Half of the maximum inhibitory concentration m Multiplet M Molarity Me Methyl MS Mass Spectroscopy PM Molecular Weight NMR Nuclear Magnetic Resonance N / A Not Applicable nt Not Tested Piv Pivaloyl Rae Racemic ta Room Temperature fronr ίη / ζζηζ / Ε / γίΛΐ Abbreviation / Acronym Name S Singlet SFC Supercritical Fluid Chromatography SDS PAGE Sodium-T-polyacrylamide dodecyl sulfate electrophoresis Triplet TEA Triethylamine TEA Trifluoroacetic acid THE Tetrahydrofuran TLC Thin Layer Chromatography T °C Temperature in degrees Celsius PTLC Preparative Thin Layer Chromatography UV Ultraviolet v / v Volume per volume w / v Weight per volume δH Chemical displacement of hydrogen pw Microwave irradiation Compounds of general formula (I) can be prepared according to the following reaction scheme 1. fronr Ln / zznz / E / YiAi fronr Ln / zznz / E / YiAi Reaction scheme 1: Synthetic route: The synthesis of compounds according to the invention is based on a functionalization of a compound of formula (II) by an amine of formula R1NH2 where R1 is as defined above, following the general protocol (GP3), described below. In accordance with GP3, the compound of formula (II) can be placed in an aprotic solvent such as THF or dioxane, or a mixture of both. The amine of formula RXNH2 can be added, for example, in a molar ratio of 2 to 6, particularly 4, with respect to the compound of formula (II). The reaction mixture can be placed in a sealed tube and heated, for example, by a heating block or microwave. Once the reaction is complete, the mixture can be returned to room temperature. In a mode called GP3-A, the reaction mixture can be stirred at a temperature that varies between -10 °C and 10 °C, for example at 0 °C, for a time ranging from 30 minutes to 2 hours, for example for 1 hour. Depending on the state of the product obtained (solid, precipitate), purification methods well known to the skilled worker can be carried out, for example filtration, washing, grinding, vacuum drying, flash chromatography, precipitation and reflux. In a modality designated GP3-B, where the product does not precipitate, the reaction mixture can be concentrated, particularly in vacuo, and purified, particularly by ultrafast chromatography. A second purification step can be performed, specifically selected from reprecipitation, trituration, and recrystallization. In another modality, designated GP3-C, where the product does not precipitate, the reaction mixture can be concentrated, particularly in vacuo, and the resulting crude can be purified by trituration in a polar protic solvent such as ethanol. This trituration can be carried out at a temperature between 20 and 100°C, particularly at room temperature. A second purification step can be performed, specifically selected from reprecipitation, trituration, and recrystallization. A compound of formula (II) as defined above can be obtained by S-alkylation of a compound of formula (III) wherein R2 is as defined above and Alk is an alkyl (C1-C5). In accordance with the GP2 general protocol, a compound of formula (III) can be placed in a polar aprotic solvent such as dimethylformamide (DMF). An alkyl halide of formula Alk-Hal, where Hal is a halide such as iodine or bromine, can then be added dropwise, for example, in a molar ratio ranging from 0.75 to 1.50, particularly 1.05, with respect to the compound of formula (III), in the presence of an inorganic base such as K₂CO₃, for example, in a molar ratio ranging from 0.7 to 1.5, particularly 1, with respect to the compound of formula (III). The reaction mixture can be stirred during the addition of the alkyl halide. In one particular mode, the resulting mixture can be stirred, for example, for 8 to 16 hours, particularly for 12 hours at room temperature. In another modality, the resulting mixture can be stirred, for example, for 2 to 8 hours, particularly for 6 hours, at a temperature ranging from -10 °C to 10 °C, particularly at 0 °C. A compound of formula (III) as defined above can be obtained from a compound of formula (IV) where R2 is as defined above, following the general protocol GP1. front Ln / zznz / E / YiAi In accordance with GP1, the compound of formula (IV) can be placed in a protic solvent such as ethanol in the presence of 2-thiohydantoin, for example in a molar ratio ranging from 0.85 to 1.15, in particular from 1, with respect to the compound of formula (IV), in the presence of an organic base such as piperidine in a molar ratio ranging from 0.85 to 1.15, in particular from 1, always with respect to the compound of formula (II), in the presence of an organic acid such as acetic acid for example in a molar ratio ranging from 0.85 to 1.15, in particular from 1, always with respect to the compound of formula (IV). The reaction mixture can be placed in a sealed tube, shaken, and heated to a temperature ranging, for example, from 60 °C to 130 °C, particularly from 80 °C, for a duration ranging from 10 to 100 minutes, particularly from 15 to 90 minutes. The reaction mixture can be irradiated, for example, with microwaves. Accordingly, the present invention further relates to the synthesis process for manufacturing novel compounds of formula (I) as defined above, comprising at least one step of substituting a compound of formula (II) with a primary amine. The present invention relates to a synthesis process for manufacturing a compound of formula (I) as defined above or any of its pharmaceutically acceptable salts or any of compounds (1) to (216) as defined above or any of their pharmaceutically acceptable salts, comprising at least one step of coupling a compound of formula (II) below. front Ln / zznz / E / YiAi Alk-S where Alk is an alkyl (C1-C5) , with an amine of formula H1NH2 where R1 and R2 are as defined above. The present invention further relates to a synthetic intermediate of formula (II) below where Alk is an alkyl (C1-C5), in particular Alk is selected from the group consisting of an ethyl and a methyl and R2 is as defined above. The chemical structures, analytical and spectroscopic data of some compounds of formula (I) of the invention are illustrated respectively in the following Table 2 and Table 3. The reactions were performed using oven-dried glassware under an inert argon atmosphere. Unless otherwise noted, all reagent-grade chemicals and solvents were obtained from commercial suppliers and used as received. The reactions were monitored by thin-layer chromatography on aluminum plates pre-coated with silica gel 60 F254 (0.25 mm). Visualization was performed under ultraviolet light at 254 or 312 nm, or with appropriate TLC stains including, but not limited to: phosphomolybdic acid, KMnO4, ninhydrin, CAM, vanillin, and anisaldehyde. Microwave experiments were performed in an Anton Paar Monowave 400® microwave reactor. The experiments were conducted in a single-mode cavity with a power supply of 0 to 850 W, enabling pressurized reactions (0 to 30 bar) in sealed glass vials (4 to 30 ml) fitted with snap-on caps and silicone septa. The temperature (0 to 300 °C) was monitored by a non-contact infrared sensor and calibrated with a ruby ​​thermometer. Temperature, pressure, and power profiles were edited and monitored via a touchscreen control panel. The times reported in the various protocols are the measured times when the mixtures reached the programmed temperature after a 3-minute ramp-up period. Chromatographic purifications of the compounds were achieved in an automated Interchim Puriflash XS420 equipped with 30 μιη spherical silica prepacked columns filled with fronr Ln / zznz / E / YiAi as the stationary phase. Some compounds of the invention are described with their structure in Table 2 below, which is merely illustrative and does not limit the scope of the present invention Table 2: Structure of compounds (1) to (216) . The formulas and molecular weights were generated using Perkin Elmer's Chemdraw® version 17.1.0.105. Comp NO. Rl-NH- R1-nh y=N HN o í Γ x)-r2 Formula PM Stereochemistry R2 Class 1 / “~NH<J y H Al C15H14N4OS 298.36 N / A 2 C^NH y H Al C14H12N4OS 284.34 N / A 3 \ > -NH and H Al C15H14N4OS 298.36 N / A 4 L ZNH and H Al Ci6Hi6N4OS 312.39 N / A 5 Z*NH cP H Al C18H20N4OS 340.45 N / A 6 \ / “NH and H Al Ci7H18N4OS 326.42 N / A 7 Z“~NH í) H Al C19H22N4OS 354.47 N / A 8 t Xnh and H Al C18H20N4OS 340.45 N / A R1-nh hn L Γ jT Ar2 or Comp NO. Rl-NH- R2 Clase Fórmula PM Estereoquímica 9 ( \nh H Al Ci9H22N4OS 354.47 N / AO > 10 z~NH / -< y H Al C16H18N4O2S 330.41 N / A HO / z~NH 11 > H Al C20H18N4O2S 378.45 N / A 12 Π·.,ΝΗ H Al C18H20N4OS 340.45 trans - rae 13 H Al Ci9H22N4OS 354.47 (IR) / '”NH Z > 14 H Al C22H24N4OS 392.17 N / A 15 _ 1—NH Υ2Λ H Al C23H26N4OS 406.55 rae 16 ¿L / nh H Al C2iH22N4OS 378.49 N / A 17<sA--Nh η Al C21H22N4OS 378.49 N / A V > 18 4Lp\HH Al C23H26N4OS 4 0 6.55 N / A / -y-7 > 19 ^Nnh H Al C21H22N4O2S 3 94.4 9 trans HO'V > HO 20 <r~VNH H Al C21H22N4O2S 394.49 N / A R1-nh hn L Γ jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry ^0 21 <ίΎ.ΝΗ H Al C22H24N4O2S 408.52 N / A 22 c(«U-Zffl3 αΟ··'νη H Al C21H24N4OS 380, 24R, 5S) H3C(¿Mr)> 23 (S) u zd 7Γ 3 Χ)Λ-Νη η Al C21H24N4OS 380.51 (13, 2S,3S,5R) HaC V_ / (S) x («) > H. H 24 ΛΠ81 > H Al C24 2428, IR. 2R,5R) H'm 25 _D>—nh H Al C19H20N4OS 352.46 rae 26 H Al C18H18N4OS 338.43 N / A y \λ h 27 h Al C2iH24N4OS 380.51 (2A) y\ >*H·T H·V 'T C18H18N4OS 380.51 rao V > (S) / 29 H Al C21H26N4OS 382.53 (1R,2S,5R) \ / 'NH ( / ?)}—<( / ?) HO^ 30 H Al C20H24N4O2S 384.50 (IRv) Al C20H24N4O2S 384.50 rv— Al\NH 382.53 C19H22N4O2S 370.47 (IR) HO^ 32 H Al C18H20N4O2S 356.44 (IR) fronr ίη / ζζηζ / Ε / γίΛΐ R1-nh hnL Γ jT r2 o Comp NO. Rl-NH- R2 Clase Fórmula PM Estereoquímica 33 HO—y £J7'NH H Al C17H18N4O2S 342.42 (IR) 34 HO—v \ίτ,,Ν£ h ai C17H20N4O2S 344.43 (ia) 35 \\μ^·'·ΝΗ H Al C18H22N4O2S 344.43 (IR) HO—< 36 VT'T H Al C17H20N4O2S 344.43 (13) / \ 0—< 37 \(s))-nh H Al C18H22N4O2S 344.43 (13) / 38 HO—\ '«¡ / •NH H Al Ci5Hi6N4O2S 316.38 (IR) fronr ίη / ζζηζ / Ε / γίΛΐ 39 HO—\ ιψΉΗ h Al Ci5Hi6N4O2S 316.38 (13) F—\ 40 H Al C17H19FN4OS 346.42 rae HO—í 41 ,—y. H Al C19H22N4O2S 3 7 0.47 rae °^V 42 H Al C20H24N4O2S 384.50 rae / —\ / 0H 43 W\_NH H Al C19H22N4O2S 384.50 rae y X° 44 OA η Al C20H24N4O2S 384.50 rao — ^~NH R1-nh hn L jC jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry OH 45 ΓΛ.„νη H Al C16H16N4O2S 328.39 cis - rae > OH 46 r\„,NH H Al C16H16N4O2S 328.39 trans - rae y p H\ Al C17H18N4O2S 342.42 cis - rae ky-'N^ Xo 48 rX H Al C17H18N4O2S 342.42 trans - rae L / 'NH y VOH 49 ΛΛ,„νη H Al C17H18N4O2S 342.42 y - rae y Ó)„,NH H Al C17H18N4O2S 342.42 trans - rae y (%ΡΗ 51 0„,NH H Al C17H18N4O2S 342.42 (1R,2S) (rlPH 52 (μΝΗ H Al C17H18N4O2S 342.42S) (1R,2S) ^>y <y°H 53 H Al C17H18N4O2S 342.42 (1R,2R) (%PH 54 H Al C17H18N4O2S 342.42 (1S, 2S) HO 55 ΛΆ NH H Al C17H18N4O2S 342.42 cis - rae HO 56 Λλ.„νη H Al C17H18N4O2S 342.42 trans - rae R1-nh hn L jC jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry 57 H° VZNH H Al Ci7Hi8N4O2S 342.42 trans p 58 / ~~\ H Al C18H20N4O2S 356.44 cis - rae \ / 'NH >* \ 0 59 Al Ci7Hi8N4O2S\H 356.44 trans - rae \ / NH 60 MeO«— / \ \?'nh H Al Ci8H2oN402S 356.44 trans VOH 61 θ,,,ΝΗ H Al C18H20N4O2S 356.44 cis - rae OH 62 Q. 356.44 trans - rae WLPH 63 H Al Ci8H2oN402S 356.44 (1R,2R) as),PH 64 (>^NH H Al Ci8H20N4O2S 356.44 (1S, 2S) HO 65 K~\ h H Al C18H2424OHON ci8H24O2S 66 NH H Al C18H20N4O2S 356.44 trans - rae \ p 67 H Al C19H22N4O2S 370.47 cis - rae k_ / N£, 68 H Al CigH22N4O2S 370.47 trans - rae ί / 'NH fronr ίη / ζζηζ / Ε / γίΛΐ R1-nh hn L Γ jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry MeOOC (S) 69 >~NH h Al C17H18N4O3S 358.42 (2S) MeOOC 70 / ^NH h Al C15H14N4O3S 330.36 (2S) MeOOC (S\) 7 h ) Al C17H18N4O3S C18H20N4O3S 372.44 (2S) / > MeOOC ( / ?) 72 \ >'NH H Al C18H20N4O3S 372.44 (2R) / > MeOOC <s>73 H Al C16H16N4O4S 360.39 (2S) OH / ~NH 74 / =Ά > Η A2 C18H14N4OS 334.40 N / A 75 CjTVnh Η A2 C20H16N4OS 360.44 N / A 7 Y^N6 A2 -θ C20H18N4OS 362.45 N / A \ / ~NH 77 θ Η A2 C20H18N4OS 362.45 N / A F3C. r-NH 78 / ==< > Η A2 C19H13F3N4OS 402.40 N / A w F3C0> y^NH 79 / =< > Η A2 Ci9H13F3N4O2S 418.39 N / A w PH 80 £3·Νη η A2 C19H13F3N4OS 402.40 6.43 cis - rae fronr ίη / ζζηζ / Ε / γίΛΐ R1-nh hn L jC jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry OH 81 ΓΛ·νη Η A2 C20H16N4O2S 37 6.43 trans - rae 0 > OH W 82 Η A2 C20H16N4O2S 376.43 (1ROH,20A) (S) ? 83 ΓΎ,νη Η A2 C20H16N4O2S 376.43 (13,23) c* > 84 ΓΛ·.1Νη Η A2 C21H18N4O2S 390.46 cis - rae σ * \ 0 8 Η A2 C20H16N4O2S 376.43 3 90.4 6 trans - rae a MeOOC 86 AbNH Η A2 C21H18N4O3S 4 0 6.46 (2 3) fronr ίη / ζζηζ / Ε / γίΛΐ 87 MeOOC... A2 C21H18N4O3S 406.46 (2.R) O- T^NH 7 > H f~a 88 ^•NH H A2 C19H15FN4OS 366.41 rae ti h2n-^ •2HCI 89 d \-NH H A21949HOS 236363N. \ HN—x •2HCI 90 d ^•NH > H A2 C20H21CI2N5OS 450.38 rae \ zn~A 91 ó ^NH > H A2 C21H21N5OS 391.49 rae R1-nh hn L jC jT Ar2 o Comp NO. Rl-NH- R2 Class PM Formula Stereochemistry HO—v 92 #~V / ~NH Η A2 C20H18N4O2S 378.45 rae \= / ~^ > 93 h°-\(R) / 'NH Η A2 C20H18N4O2S 378.94 A2 / \ \ IR. ΖΓ-Λ VNH Η A2 C21H20N4O2S 392.48 rae CJ-^y ΗΟ-λ 95 Η A2 C19H16N4O2S 364.42 rae w ΗΟ-λ λ( / ?) 96 / =Η, Η A^2S C19H16N4O2S 364.42 (IR) w HO—-v Λ($) 97 Η A2 Ci9Hi6N4O2S 364.42 (1S) w \ o-\ 98 Η A2 C20H18N4O2S 378.45 rae O 93 y_H= A2 C19H16N4O2S 364.42 rae y 100 λα)3 V / A Η A2 C20H18N4O2S 378.45 rae '—NH y OH 101 / =Λ~νΝΗ Η A2 C20H18N4O2S 378\24 rae 100 . ^ / A-nh h a2 C21H20N4O2S 392.48 rae wy Z-NH 103 N=ZV* Η A3 Ci7Hi4N6OS 350.41 N / A / -N R1-nh hn L jC jT r2 o S* Rl-NH- NO. R2 Class PM Formula Stereochemistry fronr in / zzh / E / yLi / —NH 104 / N=\ > V / H A3 C17H13N5OS 335.39 N / A / —NH 105 o > H A3 C17H13N5OS 335.39 N / A Z~~ NH 106 Z=\ > H A3 C17H13N5OS 335.39 N / A 107 Z—NH ZA > H A3 C17H14N4O2S 338.39 N / AZ~NH 108 ζρN H A3 C16H13N5OS2 355.43 N / A / —NH 109 [j-ti H A3 Ci7Hi6N6OS 352.42 N / A 110 H A3 CisHisNsOS 34 9.41 N / A r~ NH 111 H A3 Ci9H13N5OS2 391.47 N / A 112 H A4 C18H21N5OS 355.46 N / AN— / / z-NH 113 ζ~\ H A4 C17H18N4O2S 342.42 N / AO— / Z—NH . z~\ y 114 VZ H A4 C22H27N5O3S 441.55 N / A 115 H A4 C20H23N5OS 381.50 N / A Comp NO. R1-nh hn 0 jC jT r2 o Rl-NH- R2 Clase Fórmula PM Estereoquímica 116 F ~Z~VNH Η A5 C18H13FN4OS 352.39 N / A 117 f~C3~nh η A5 C17H11FN4OS 338.37 N / A 118 zZ~V Η A5 C23H24N4OS 404.53 N / A 119 'O<VNH Η A5 C22H22N6OS 418.52 N / A 120 F2HCO ?~VNH η A5 C18H12F2N4O2S 386.37 N / A 121 > Η A5 C21H17N5O2S 403.47 N / A 122 F3C ?~VNH Η A5 C18H11F3N4OS 388.37 N / A 123 γΥΛ-νη Η A5 C20H16N4OS 3 60.4 4 N / A 124 ΟΟνΌ~νη η A5 C21H19N5O2S 4 05.48 N / A 125 >=f > Η A5 C19H14N6OS 374.42 N / A 126 z—μ <'>~ΝΗ Η A6 Ci5Hi0N6OS 322.35 N / A ny 127 ^~N- V>~nh Η A6 CieHnNsOS 321.36 N / A fronr ίη / ζζηζ / Ε / γίΛΐ Comp NO. R1-nh hn L jC jT r2 o Rl-NH- R2 Clase Fórmula PM Estereoquímica 128 L>-nh H A6 Ci5Hi2N6OS 324.37 N / A 129 \ 0 H A6 C18H15N5O2S 365.41 N / A \ Z~NH 130 N-, <7 / ~~nh H A6 CisHioNgOS 322.35 N / AN=7 y 131 N-λ O-nh η A6 CieHnNsOS 321.36 N / A > 132 r*s\ ,l'i-NH H A6 Ci3H8N6OS2 328.37 N / AN y 133 ~NOnO~ne η A6 C21H21N7OS 419.51 N / A \=N y 134 ~nQn- / ANh H A6 C2iH2iN7OS 419.51 N / A n= / 135 Vnh η A6 C2oH20N8OS 420.50 N / A n-7 y 136 —N7 X-Λλ >-nh η A6 C20H20N8OS 420.50 N / A \=ny 137 _ / \ N—LN\__ / n~X / —nh η A6 C20H20N8OS 420.50 N / A y 138 / N~N V_yN~O-NH H A6 C20H20N8OS 420.50 N / A 139 oGYN h A 7 Ci6Hi6N4O2S 328.39 N / A fronr in / zzh / E / yLi R1-nh hnL jC jT r2 o Comp NO. Rl-NH- R2 Clase Fórmula PM Estereoquímica 140 —r~o t___ ' λ-i / L-NM H A7 C21H25N5O3S 427.52 N / A 0 > J—v ¿_ 141 „^N> / —nh H A7 C19H21N5O3S 399.47 N / A 0 y 142 ~nJ-nh H A7 C17H19N5OS 341.43 N / A 143 (_ / -nh η A7 C17H19N5OS 341.43 rae zN > 144 °0^NH η A7 C14H12N4O2S 300.34 N / A fronr in / zzh / E / yLi 145 0^ <( / ?) >'NH H A7 C15H14N4O2S 314.36 (3R) 146 0-^ \(S) >*NH H A7 C15H14N4O2S 314.36 (3S) 147 O— \(R) / '•'NH > H A7 C16H16N4O2S 328.39 (3A) 148 O— \(S) / -•NH H A7 C16H16N4O2S 328.39 (33) 149 \ / °· X-NH H A7 C18H20N4O2S 356.44 rae 14 9A \ P—\ zA / '"NH (RorS) * H A7 C18H2oN402S 356.44 Enantiómero A (3R) 0 (33) 14 9B \ / °~λ ✓A X-NH (R or S) H A7 C18H20N4O2S 356.44 Enantiómero B (3R) 0 (33) R1-nh hn L jC jT r2 o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry 150 <« / H Π.„„μ Η A 7 Ci6Hi6N4O3S 344.39 (3R,4R) o- / *™ z°> 151 i / —nh Η A 7 C17H18N4O3S 423S rae >2424. 152 UN—y (( Λνη Η A7 C16H15N5O2S 341.39 rae 153 0 ΓΎνη h a7 CieHisNsOzS 341.39 (33) Us / y, ΗΝ-λ 154 0NH=K= Η A7 C16H15N5O2S 341.39 (53) '— / (Si F 155 FÍ3-nh h a1 Ci6Hi4F2N4OS 348.37 rae > --- 156 A 7-nh η Al C17H16F2N4OS 362.40 N / A NH 157 Hλ Al Ci7Hi6F2N4OS 362.40 rae F 158 ¿y_FNH H Al C17H16F2N4OS 3 62.4 0 rae FF 159 h Al Ci8Hi8F2N4OS 376.43 rae 160 \>-N£ H Al C17Hi6F2N4OS 416.46. F~\(S) \ / -NH H Al C17H19FN4OS 346.42 (13) fronr ίη / ζζηζ / Ε / γίΛΐ Comp NO. R1-nh hnE Γ jT r2 o Rl-NH- R2 Class Formula PM Stereochemistry 162 AcO H Al C23H24N4O3S 436.53 N / A 163 PivO NH H Al C26H30N4O3S 478.61 N / AA? > 164 (R) / 3171® ΓΑ,,,νη η Al C17H18N4O2S 342.42 (1A,2R) 165 OMe (S)? rVNH H Al C17H18N4O2S 342.42 (1S, 2S) 166 \ IR),0 / Λ H Al Ci8H2oN402S 356.44 (1A,2A) 167 \ (S),PH Al C18H20N4O2S 356.44 (18S) Me Αλ NH H Al Ci8H2oN402S 356.44 cis-rac 169 MeO Αλ nh H Al C18H20N4O2S 356.44 trans-rac Meo Enantiomer A 169A (kNH H Al Ci8H20N4O2S 356.4O2S 356.4R) (R,R)or(S,S) (1S, 3S) 169B Meo Enantiomer B (Α,.νη H Al Ci8H20N4O2S 356.44 (1A, 3R) 0 > (R,R) or (S,S) (13,33) 170 ^2^nh Al 356.44 cis-rac fronr ίη / ζζηζ / Ε / γίΛΐ R1-nh hn L jC jT r2 or Comp NO. Rl-NH- R2 Clase Fórmula PM Estereoquímica H0S / ^\ 171 T )·..ΝΗ H Al C18H20N4O2S 356.44 trans-rac Enantiómero A 171A i__ / ••NH H Al C18H20N4O2S 356.44 (IR, 4R) 0 (R,R)or(S,S) (1S, 4S) Enantiómer B 171B <óy*'NH H Al C18H20N4O2S 356.44 (IR,4R) 0 (R,R) or (S,S) (1S, 4S) MeO 172 H Al C19H22N4O2S 370.47 cis-rac l / 'NH y MeO 173 H Al C19H22N4O2S 370.47 trans-rac MeO,, 174 ζ y,NH H Al C19H22N4O2S 370.47 cis-rac 175 T y..NH H Al C19H22N4O2S 370.47 trans-rac y \ °~\<») 176 Η A2 C20H18N4O2S 378.45 (IR) \ 177 ^_Λνχη Η A2 C20H18N4O2S 378.45 (1S) w 178 \= / \Ü2nh η A2 C19H16N4O2S 364.42 (2R) y 179 \= / \2nh η A2 C19H16N4O2S 364.42 (2S) y Comp NO. R1-nh hnL Γ jT r2 o Rl-NH- R2 Clase Fórmula PM Estereoquímica 180 UM 2HCI H2N—.(R| Η A2 C19H19C12N5OS 436.36 (IR) O 181 H2N-vs7hci Η A2 C19H19CI2N5OS 436.36 (1S) O 182 HA 7 C18H19N5OS 353.44 (3R) H > 183 1 <S| Η A7 C18H19N5OS 353.4 4 (3S) V 184 S—. < >-nh η A7 C16H16N4OS2 344.45 rae 185 C Ύ-νη Η A7 C16H16N4O3S 344.39 N / A S- / > 186 0 HL >-NH H A7 C19H13N5O2S 327.36 rae 187 p W-NH h a7 C16H15N5O2S 341.39 rao 188 HL z—nh HA 7 C17H17N5O2S 355.42 rae 189 .0 HN~r ( ),,NH HA 7 C16H15N5O2S 341.39 (3A) 190 < >-nh H A7 C17H17N5O2S 355.42 rae W > 191 O hnXj¿nh η A7 C16H15N5O2S 341.39 rae fronr ίη / ζζηζ / Ε / γίΛΐ Comp NO. R1-nh hn L jC jT r2 o Rl-NH- R2 Clase Fórmula PM Estereoquímica 192 0 ->Λ^N£ η A 7 C17H17N5O2S 355.42 rae 192A V / Enantiómero A viT-nh Η A7 C17H17N5O2S 355.42 (F? (3R) 0 (3S) 192B V / Enantiómero B - / 7-™ η A7 C17H17N5O2S 355.42 (3R) 0 (3S) 193 (SU°H Η A7 CisHielúOsS 344.39 (3S, 4S) O- / W 194 H Al C20H20N4OS 364.47 N / A 195 0 \ / 0 HUH Al C26H31N5O3S 4 93.63 N / AV 196 ^Q-NH H Al C21H21FN4OS 396.48 N / A 197 h a1 C21H28N4O2S 400.54 (1A) \ W / ''ΝΠ 198 Η A2 C23H24N4O2S 420.53 (IB) 0 199 O HN H Al C23H25N5O2S 435.55 N / A > O 200 hn'^FH Al C25H27N5O2S 461.58 N / A fronr ίη / ζζηζ / Ε / γίΛΐ Comp NO. R1-nh hn 0 jC jT r2 o Rl-NH- R2 Class Formula PM Stereochemistry 201 p ^?'NH °J-\ H Al C22H25N5O3S2 471.59 N / A Ζ^Γ> 202 ,?~NH 0 H Al C24H27N5O3S2 497.63 N / A \\ J~NH 203 N7 H Al C23H27N5OS 421.56 N / A \\ / bNH ¿2^ V 204 / —v COOMe H Al C23H24N4O3S 436.53 N / A 205 O~nh Me Al C18H20N4OS 340.45 N / A 206 í Ύ-νη Me Al Ci9H22N4OS 354.47 N / A >· 207 \ \^··.νη Me Al Ci9H24N4O2S 372.49 (IR) 208 \ J7'nxH Μθ A2 C2iH20N4O2S 392.48 (IR) 0 209 Me Al C22H24N4OS 3 92.52 N / A 210 HO (ΓΆ 1Μ Me Al C22H24N4O2S 408.52 N / A 2^ / > 211 η Al C2iH22N4O3S 410.49 N / A HO fronr ίη / ζζηζ / Ε / γίΛΐ R1-nh fronr Ln / zznz / E / YiAi o Comp NO. Rl-NH- R2 Class Formula PM Stereochemistry 212 FFH Al C21H19F3N4OS 432.47 N / A 213 F > H Al C19H24N4O2S 372.49 (IR) 214 οΛ F and H Al C24H26N4O2S 434.56 (IR) F- / V 215 °AF > H Al C24H25FN4O2S 452.55 (IR) 216 5, F > H Al C20H24N4O2 s 384.50 (IR) . The following Table 3 describes the analytical and spectroscopic data of the compounds entered in Table 2. NXR (400 or 500 MHz) and 13C NMR (101 MHz) spectra were recorded using a Bruker ULTRASHIELD 500 or 400 spectrometer. Spectral processing and analysis were performed using MestReNova. Data are presented in the following order: chemical shifts in ppm, referring to the internal solvent signal, multiplicity, number of protons, and coupling constant J in Hertz. Reversed-phase HPLC / MS analyses were performed using a Waters Alliance 2795 HPLC system equipped with an autosampler, an online membrane degasser, a column oven (T = 45 °C), a UV detector, and a ZQ quadrupole mass spectrometer operating in ionization, electrospray mode. Compounds (0.1 to 0.3 mg) were solubilized in a minimal amount of DMSO, topped up with acetonitrile (Vtotal = 1 mL). Standard analytical parameters: flow rate: 1 mL / min, Viny = 5 pL. - Acidic conditions: Waters XSelect CSH C18 column (3.5 pm, 2.1 x 50 mm). Gradient: (¾ O + 0.04% v / v HCOOH (10mM)) / ACN from 95 / 5 to 0 / 100 in 18.5 min. - Alkaline conditions: Waters Xbridge C18 column (3.5 pm, 2.1 x 50 mm). Gradient: (H2O + 0.06 % v / v NH3(aq)(10 mM)) / ACN from 95 / 5 to 0 / 100 in 18.5 min. The enantiomers of the racemic products (149), (169), (171), and (192) were separated by Reach Separations (Bio City, Pennyfoot St., Nottingham, NG1 IGF, UK. www.reachseparations.com) using preparative chiral SFC. Briefly: the racemic products were solubilized in MeOH and purified by preparative SFC (conditions in Table 3). The pooled fractions containing the first eluted enantiomer were evaporated to near dryness using a rotary evaporator, transferred to final containers with DCM, which was removed in a Biotage VIO at 35 °C before being stored in a vacuum oven at 35 °C and 5 mbar to constant weight to obtain the pure enantiomer. The fractions containing the second eluted enantiomer were combined, concentrated, and repurified as described above. The optical purity of each enantiomer was controlled with respect to the racemate by analytical chiral SFC (conditions in Table 3).The chemical purity of each enantiomer was controlled by UHPLC analysis in an Acquity BEH C18 (1.7 pm, 50 x 2.1 mm) (60 °C, 1 mL / min, iny. vol. = 1 pL), gradient: (H3O + 0.1% v / v TFA) / ACN from 98 / 2 to 0 / 100 in 2.02 min. fronr Ln / zznz / E / YiAi 100 Tabla 3. Analytical and spectroscopic characterization of the compounds fronr Ln / zznz / E / YiAi fronr in / zzh / E / yΛΐ (tí M 3 <0 M CN fronr Ln / zznz / E / YiAi (tí M 3 <0 M 103 fronr in / zzh / E / yLi LO 104 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 106 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi LO 109 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 111 fronr in / zzh / E / yLi LO 112 fronr in / zzh / E / yLi LO 113 fronr in / zzh / E / yLi LO 114 fronr in / zzh / E / yLi 115 fronr Ln / zznz / E / YiAi LO 116 fronr in / zzh / E / yLi LO 117 fronr in / zzh / E / yLi LO 118 fronr in / zzh / E / yLi LO 119 fronr in / zzh / E / yLi LO 120 fronr in / zzh / E / yLi LO 121 fronr in / zzh / E / yLi LO 122 [M+H]+381. LO 123 fronr in / zzh / E / yLi LO 124 fronr in / zzh / E / yLi LO 125 fronr in / zzh / E / yLi LO 126 fronr in / zzh / E / yLi LO 127 fronr in / zzh / E / yLi LO 128 fronr in / zzh / E / yLi LO 129 fronr Ln / zznz / E / YiAi LO 130 fronr in / zzh / E / yLi LO 131 fronr in / zzh / E / yLi LO 132 front in / zz / E / yLi Comp Estructura Fórmula PM HPLC Descripción NO. Sólido amarillo. RMN (400 MHz, DMSO-de, 323K) de tautomero mayor δH 10.37 (br s, 5 1H, NH, D2O intercambiado), 9.33 (s, 1H) , 8.98 - 8.72 (m, 1H), 8.34 - 8.12 (m, 1H) , 8.02 (d, J = 8.5 Hz, 1H) , 7.23 (br s, 1H, NH, D2O intercambiado) , 33 >= C17H18N4O2S 342.2 >98% yAsAsA- / 6.41 (s, 1H) , 4.77 (br s, 1H, OH, D2O intercambiado), 4.11 - q 3.87 (m, 1H) , 3.70 - 3.44 (m, 2H), 1.69 - 1.51 (m, 1H), 1.51 -1.40 (m, 1H), 0.87-0.71 (m, 1H), 0.52 - 0.37 (m, 2H), 0.25 - 0.03 (m, 2H). MS (ESI + ) : [M+H] + 343.1 . 133 fronr in / zzh / E / yLi LO 134 fronr in / zzh / E / yLi LO 135 fronr in / zzh / E / yLi LO 136 fronr in / zzh / E / yLi LO 137 fronr in / zzh / E / yLi LO 139 fronr in / zzh / E / yLi 140 fronr in / zzh / E / yLi LO 141 fronr in / zzh / E / yLi LO 142 fronr in / zzh / E / yLi LO fronr in / zzh / E / yΛi fronr in / zzh / E / yΛi (tí M 3 <0 M (i E O ir LO 145 fronr Ln / zznz / E / YiAi LO 146 front in / zz / E / yLi <0 M 147 fronr in / zzh / E / yLi LO 148 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi (tí M 3 <0 M The r LO 150 fronr in / zzh / E / yLi LO 151 fronr in / zzh / E / yLi LO 152 fronr in / zzh / E / yLi LO 153 fronr in / zzh / E / yLi LO 154 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi LO 157 fronr in / zzh / E / yLi LO fronr in / zzhiz / E / yLi (tí M 3 <0 M oO © C) » 159 fronr Ln / zznz / E / YiAi LO 160 fronr in / zzh / E / yLi LO 161 fronr in / zzh / E / yLi LO 162 fronr in / zzh / E / yLi LO 163 fronr in / zzh / E / yLi LO 164 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 166 fronr in / zzh / E / yLi LO 167 fronr in / zzh / E / yLi LO 168 fronr in / zzh / E / yLi LO 169 fronr in / zzh / E / yLi LO 170 fronr in / zzh / E / yLi LO 171 fronr Ln / zznz / E / YiAi LO 172 fronr in / zzh / E / yLi LO 173 fronr in / zzh / E / yLi LO 174 fronr in / zzh / E / yLi LO 175 fronr in / zzh / E / yLi LO 176 fronr in / zzh / E / yLi LO 177 fronr in / zzh / E / yLi LO 178 fronr in / zzh / E / yLi LO 179 fronr in / zzh / E / yLi LO 180 fronr in / zzh / E / yLi LO 181 fronr in / zzh / E / yLi LO 182 fronr in / zzh / E / yLi LO 183 fronr in / zzh / E / yLi LO 184 fronr in / zzh / E / yLi LO 185 fronr in / zzh / E / yLi LO 186 fronr in / zzh / E / yLi LO 187 fronr Ln / zznz / E / YiAi LO 188 fronr in / zzh / E / yLi LO 189 fronr in / zzh / E / yLi LO 190 fronr in / zzh / E / yLi LO 191 (400 F O ω P £ o Ο re! co LO co p £ <0 O Ο re! -rH 1 <o CN O 0 £ co CO + ω S Descripción Sólido amarillo. RMN g Ό 1 o ω S Q N S LO LO P O o g o p o g Ό 0 res -O Ό g res O P Φ 4-> c HOQX co co 1 si X ω co en Oh x co 1 en co X í¡ NK co II £ ng res OP Φ -P c -HOQ aan? ω X CN 1 CN ω kO X! XOX LO 1 00 LO en 1 00 O O re! O g re! OP Φ +JC OR X CN σ> 1 CO LO X ω XX CN OJ 1 CN Oh + X + X HPLC o\o CO σ> Λ LO PM co co ni ω HJ 1 O £ Fór £ ω Estructura w J Λ i Comp NO. LO CN p> fronr in / zzh / E / yLi 192 fronr in / zzh / E / yLi LO 193 fronr in / zzh / E / yLi LO 194 fronr in / zzh / E / yLi LO 195 fronr in / zzh / E / yLi LO 196 fronr in / zzh / E / yLi LO 197 fronr in / zzh / E / yLi LO 198 fronr in / zzh / E / yLi LO 199 fronr in / zzh / E / yLi LO 200 fronr in / zzh / E / yLi LO 201 fronr in / zzh / E / yLi 202 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 204 fronr in / zzh / E / yLi LO 205 front in / zz / E / yLi <0 M oO © C) » fronr in / zzh / E / yLi fronr in / zzh / E / yLi 208 fronr in / zzh / E / yLi LO 209 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi LO 211 fronr in / zzh / E / yLi LO 212 fronr in / zzh / E / yLi LO 213 fronr in / zzh / E / yLi LO 214 fronr in / zzh / E / yLi LO 215 fronr in / zzh / E / yLi LO 216 fronr in / zzh / E / yLi LO 217 fronr in / zzh / E / yLi LO 218 fronr in / zzh / E / yLi LO 219 fronr in / zzh / E / yLi LO 220 fronr in / zzh / E / yLi LO 221 fronr in / zzh / E / yLi LO 222 fronr in / zzh / E / yLi 223 fronr in / zzh / E / yLi LO 224 fronr in / zzh / E / yLi LO 225 fronr in / zzh / E / yLi 226 fronr in / zzh / E / yLi LO 227 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 229 fronr in / zzh / E / yLi LO 230 fronr in / zzh / E / yLi LO 231 fronr in / zzh / E / yLi LO 232 fronr Ln / zznz / E / YiAi LO 233 fronr in / zzh / E / yLi 234 fronr in / zzh / E / yLi LO 235 fronr in / zzh / E / yLi LO 236 fronr in / zzh / E / yLi LO 237 fronr in / zzh / E / yLi LO 238 fronr in / zzh / E / yLi LO 239 fronr in / zzh / E / yLi LO 240 fronr in / zzh / E / yLi LO 241 fronr in / zzh / E / yLi LO 242 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi fronr in / zzh / E / yLi 245 fronr in / zzh / E / yLi 246 fronr in / zzh / E / yLi LO 247 fronr in / zzh / E / yLi LO 248 fronr in / zzh / E / yLi LO 249 fronr in / zzh / E / yLi LO 250 fronr in / zzh / E / yLi LO 251 fronr Ln / zznz / E / YiAi LO 252 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 254 fronr in / zzh / E / yLi LO 255 fronr in / zzh / E / yLi LO 256 fronr in / zzh / E / yLi LO 257 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi LO 259 fronr in / zzh / E / yLi 260 fronr in / zzh / E / yLi LO 261 fronr in / zzh / E / yLi LO 262 fronr in / zzh / E / yLi LO 263 fronr in / zzh / E / yLi LO 264 fronr in / zzh / E / yLi LO 265 fronr in / zzh / E / yLi LO 266 fronr in / zzh / E / yLi LO 267 fronr in / zzh / E / yLi LO 268 fronr in / zzh / E / yLi 269 fronr in / zzh / E / yLi 270 fronr Ln / zznz / E / YiAi LO 272 fronr in / zzh / E / yLi LO 273 fronr in / zzh / E / yLi LO 274 fronr in / zzh / E / yLi LO 275 fronr in / zzh / E / yLi LO 276 fronr in / zzh / E / yLi LO 277 fronr in / zzh / E / yLi LO 278 fronr in / zzh / E / yLi LO 279 fronr in / zzh / E / yLi LO 280 fronr in / zzh / E / yLi LO 281 fronr in / zzh / E / yLi LO 282 fronr in / zzh / E / yLi LO 283 fronr in / zzh / E / yLi LO 284 fronr in / zzh / E / yLi LO 285 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 287 fronr in / zzh / E / yLi LO 288 fronr in / zzh / E / yLi LO 289 fronr Ln / zznz / E / YiAi LO 290 fronr in / zzh / E / yLi LO 291 fronr in / zzh / E / yLi LO 292 fronr in / zzh / E / yLi LO 293 Description Sólido amarillo. RMN (400<D Ό CN Ό 1 o ω S Q N S ω íq £ KD P O O 6 o íq Φ E Ό 0 re! +J o Ό re! Λ2 E re! o P Φ 4->C -HOQXX oh co co X! O LO en Oh LO co x NX CO II s kO C\) co íq Π — — o Ό re! the . £¡ EO o - íq ω | 1 1-1 c -HQ kO CO HX II 'OX Ό ω o QZK ω íq £ co π w co V1 co O Ο rtj JO E res o !q Φ -PC •H 1 LO co CN X CN £ LO O] co 1 kO 00 II Ό 3 co cq K £ CM ω kO XNXC\1 CO CX] C\1 + X + £ + ω s ω s K CO HPLC oP CO siΊ A PM Oh co co muía ω O LT) s iD Fór £ o Estructura 1 1 vo A 1 ' 1 Comp NO. LO s fronr in / zzh / E / yLi 294 fronr in / zzh / E / yLi 295 fronr in / zzh / E / yLi LO 296 fronr in / zzh / E / yLi LO 297 fronr in / zzh / E / yLi LO 298 fronr in / zzh / E / yLi LO 299 fronr in / zzh / E / yLi LO 300 .83 (m, 4H), 1.67-1.53 ​​(m <0 M <Oh yeah 301 fronr in / zzh / E / yLi LO 302 fronr in / zzh / E / yLi LO 303 fronr in / zzh / E / yLi LO 304 fronr in / zzh / E / yLi LO fronr in / zzh / E / yLi 306 fronr in / zzh / E / yLi LO 307 fronr in / zzh / E / yLi 308 .00 (m, 4H) , 1.91 - 1.58 (m fronr in / zzh / E / yLi LO 310 fronr in / zzh / E / yLi LO 311 fronr in / zzh / E / yLi LO 312 front in / zz / E / yLi c¡ MN íR (400 <D Ό ω íq £ O Ό re! Λ2 E res O íq 1 kO CO X! μ £ CO CO 1 o Ό re! -H n E re) o íq Φ r- -O 1 kO CN LO X e' ω 04 CO 1 LO X! CO II £ CO 04 CN Oh + Ό H O & H 0 tn <u q arillo. rl ό 1 o ω lo s3 6 φ 4->C -HOQ LO LO si X -OC -HOQNK CO II Os] NX! kO 00 04 X CM ω Oh kO Oh 00 X II £ X co ω + £ ll ω olido am SQN o íq Φ E Ό re) CO 1 £ Oh Oh § s CO II £ NX LO XN £ 00 LO LO XN w ω s Comp Estructura Fórmula PM HPLC NO. ω S -O CO ω o\° CO Oh Λ CO 04 Oh CO ω O £ £ O 00 o CN II X LO 00 LO 313 fronr in / zzh / E / yLi LO 314 fronr in / zzh / E / yLi LO 315 fronr in / zzh / E / yLi LO 316 fronr in / zzh / E / yLi LO 317 fronr in / zzh / E / yLi LO 318 fronr in / zzh / E / yLi LO 319 fronr in / zzh / E / yLi LO 320 fronr in / zzh / E / yLi LO 321 PATHOLOGIES Compounds of formula (I) may be useful in the treatment and / or prevention of a selected disease from the cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; and other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick type C disease); CDKL5 deficiency disorder; McDermid syndrome; autism; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis, particularly knee osteoarthritis; Duchenne muscular dystrophy;various types of cancer, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia, acute lymphoblastic leukemia, squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, breast cancer, such as triple-negative breast cancer (TNBC), tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), fronr Ln / zznz / E / YiAi; 322 Influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus, herpes simplex virus (HSV), hepatitis C virus, chikungunya virus, dengue virus, influenza virus and severe acute respiratory syndrome coronavirus (SARS), cytomegalovirus and human papillomavirus; neuroinflammation; anemia; infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and livestock diseases caused by single-celled pathogens and to regulate body temperature. According to a particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of a selected disease from the cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick type C disease); CDKL5 deficiency disorder; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis, particularly knee osteoarthritis; Duchenne muscular dystrophy; various types of cancer, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia, and frontal lobe leukemia. 323 acute lymphoblastic leukemia, squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, and breast cancer, such as triple-negative breast cancer (TNBC), and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus, and herpes simplex virus (HSV), and to regulate body temperature. Such diseases are most particularly associated with abnormalities in the dosage of DYRK1A and / or CLK1. Still in accordance with this particular modality, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of a selected disease from Down syndrome, Alzheimer's disease, dementia, tauopathies, Parkinson's disease, Niemann-Pick type C disease, CDKL5 deficiency disorder and Phelan-McDermid syndrome and their associated cognitive and motor conditions, more particularly due to the high expression and activity of DYRK1A. Still in accordance with this particular modality, the compounds of formula (I) of the present fronr Ln / zznz / E / YiAi The invention, number 324, may be useful in the treatment and / or prevention of a selected disease from Down syndrome, Alzheimer's disease and related tauopathies, Parkinson's disease, cognitive / motor disorders associated with it, or one or more symptoms of such diseases. A typical symptom of this type of disease is a decline in learning, memory, and social interaction. Still in accordance with this particular modality, the compounds of formula (I) of the present invention may be useful to combat the cognitive impairment associated with Down syndrome (Trisomy 21), in learning and memory, particularly associated with cognitive or neurodegenerative disorders as mentioned above. Still in accordance with this particular modality, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of type 1 and type 2 diabetes. The compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of type 1 and type 2 diabetes either by direct treatment of the diabetic patient or by treatment of pancreatic islets or β cells before transplantation in diabetic patients. 325 Still in accordance with this particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of viral infections, particularly those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpesvirus, rhesus macaque cytomegalovirus, varicella-zoster virus, and herpes simplex virus (HSV), and in particular by herpes, coronavirus, cytomegalovirus, and influenza. These infections may be associated with high expression and activity of DYRK1A and / or CLK1 and, optionally, additionally with dual inhibitors of CLKs / DYRKs. Acute respiratory illness has recently been caused by a novel coronavirus (SARS-CoV-2, formerly known as 2019-nCoV), also referred to herein as coronavirus 2019 (COVID-19), which belongs to the Coronaviridae family. Compounds of formula (I) according to the present invention can also treat such infection caused by the SARS-CoV-2 virus. Still in accordance with this particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of cancers, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia. 326 and acute lymphoblastic leukemia, head and neck squamous cell carcinoma, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, and breast cancer, such as triple-negative breast cancer (TNBC). These cancers may be associated with high expression and activity of DYRK1A and / or CLK1, and optionally additionally with dual CLK / DYRK inhibitors. Still in accordance with this particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of osteoarthritis. Osteoarthritis may be associated with high expression and activity of DYRK1A and / or CLK2. Still in accordance with this particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of infections caused by unicellular parasites, such as malaria, leishmaniasis, Chagas disease, and sleeping sickness (Trypanosoma sp.), and livestock diseases due to unicellular pathogens. Such parasitic infections may be associated with the expression and activity of DYRKs / CLKs. Still in accordance with this particular embodiment, the compounds of formula (I) of the present invention may be useful in regulating body temperature. Such regulation of body temperature fronr Ln / zznz / E / YiAi 327 body may be associated with the expression and activity of CLK. According to another particular embodiment, the compounds of formula (I) of the present invention may be useful in the treatment and / or prevention of a selected disease from Phelan-McDermid syndrome; autism; other viral infections, such as those caused by hepatitis C virus, Chikungunya virus, dengue virus, influenza virus and severe acute respiratory syndrome coronavirus (SARS), cytomegalovirus and human papillomavirus; other types of cancer, such as tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, neuroinflammation, anemia, infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and livestock diseases due to single-celled pathogens.Such diseases are most particularly associated with abnormalities in other DYRKs (DYR1B, 2, 3, 4) and additional closely related cdc2-like kinases (CLK) (CLK 2, 3, 4). The following examples are provided as illustrations and in no way limit the scope of this invention. 328 The following examples illustrate in detail the preparation of some compounds according to the invention. The structures of the products obtained have been confirmed by NMR analysis and mass spectrometry. Example 1: General Protocol 1 - Synthesis of (5Z)5-heteroaryl-2-thioxo-imidazolidin-4-ones O (1 eq) Piperidine (1 eq) AcOH (1 eq) EtOH (c = 0.3 NI) pw (Antón Paar), T °C, time In the reaction scheme above, R2 represents a hydrogen atom or an alkyl group (C1-C3), in particular R2 represents a hydrogen atom or a methyl group. GP1: A stirred solution of 2-thiohydantoin (1 eq), the appropriate heteroarylcarbaldehyde (1 eq), piperidine (1 eq), and AcOH (1 eq) in EtOH (c = 0.3 M) was heated in a sealed tube in a microwave oven (Anton Paar) for the appropriate time at the specified temperature. Upon completion (followed by consumption of the aldehyde in TLC), the reaction medium was cooled and added dropwise over water. The precipitated solid was stirred for 30 min, filtered through a fritted glass funnel, thoroughly dried, and could be used in the next step without further purification. 329 If necessary, a final crushing in EtOH can help remove trace impurities without a significant loss of yield. Example 1.1: Synthesis of (5Z)-5-(1,3-benzothiazol-6-ylmethylene)-2-thioxo-imidazolidin-4-one (1.1) front Ln / zznz / E / YiAi Compound (1.1) was synthesized according to GP1: the reaction was carried out on a scale of 4.2 mmol of 2-thiohydantoin, benzothiazo-6-carbaldehyde, AcOH, and piperidine. Reaction temperature: 110 °C, time: 90 min. The yellow solid was ground in EtOH after filtration. Yellow solid, 89% (978 mg). 1H NMR (400 MHz, DMSO-dg) δΗ 12.44 (br s, 1H, NH, exchanged D2O), 12.25 (br s, 1H, NH, exchanged D2O), 9.47 (s, 1H), 8.61 (d, J = 1.8 Hz, 1H), 8.09 (d, J = 8.5 Hz, 1H), 7.84 (dd, J = 8.6, 1.8 Hz, 1H), 6.64 (s, 1H). 13C NMR (101 MHz, DMSO-d6) oc179.3, 165.7, 158.0, 153.1, 134.4, 129.8, 128.9, 128.1, 123.7, 123.1, 110.9. MS (ESI+): [M+H]+262.1. Example 1.2: Synthesis of (5Z)-5-[(2-methyl-1,3-benzothiazol-6-yl)methylene]-2-thioxo-imidazolidin-4-one (1.2) or (1.2) 330 Compound (1.2) was synthesized in accordance with GP1: The reaction was carried out on a scale of 7.34 mmol of 2-thiohydantoin, 2-methyl-1,3-benzothiazo-6-carbaldehyde, AcOH, and piperidine. Reaction temperature: 110 °C, time: 90 min. The yellow solid was ground in EtOH after filtration. Yellow solid, 94% (1.898 g). 2H NMR (400 MHz, DMSO-dg) δΗ 12.42 (br s, 1H, NH, exchanged D2O), 12.21 (br s, 1H, NH, exchanged D2O), 8.48 (s, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 6.60 (s, 1H), 2.82 (s, 3H). 13C NMR (101 MHz, DMSO-d6) 5C179.2, 169.1, 165.7, 153.1, 136.0, 129.0, 128.8, 127.7, 123.0, 122.0, 111.1, 20.0. MS (ESI+) : [M+H]+275.9 . Example 2: General Protocol 2 - S-Alkylation of (5Z)-5-heteroaryl-2-thioxo-imidazolidin-4-ones (III) (1 eq) Alk-Hal K2CO3(1 eq) Alk-S DMF (c = 0.3 M) 0 °C or rt, 6-12h (1.05 eq) from Ln / zznz / E / YiAi In the reaction scheme above, Hal represents a halogen atom, in particular selected from an iodine and a bromine atom, Alk is an alkyl (C1-C5) and R2 represents a hydrogen atom or an alkyl (C1-C3) group, in particular R2 represents a hydrogen atom or a methyl group. GP2: The appropriate alkyl iodide (1.05 eq) is 331 Added dropwise to a stirred solution of (5Z)-5heteroaryl-2-thioxo-imidazolidin-4-one (1 eq) and K2CO3 (1 eq) in DMF (c = 0.3 M) at the appropriate temperature. The resulting mixture was stirred at the indicated temperature for the appropriate time. At the end of the reaction (TLC), the mixture was poured into water. The precipitated solid was stirred for 30 min and filtered through a fritted glass funnel, thoroughly dried, and could be used in the next stage without further purification. Trace impurities resulting from the double alkylation can be removed by FC: elution: cyclohexane / AcOEt 7 / 3 to 3 / 7 or grinding. Example 2.1: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-ethylsulfanyl-1H-imidazol-5-one (2.1) EtS fronr Ln / zznz / E / YiAi (2.1) Compound (2.1) was synthesized in accordance with GP2: The reaction was carried out with (5L)-5-(1,3-benzothiazol6-ylmethylene)-2-thioxo-imidazolidin-4-one (7.69 mmol) and EtI, at room temperature, for 12h. Yellow solid, 89% (978 mg). 3Η NMR (400 MHz, DMSO-d6) δΗ 11.85 (br s, 1H, NH, D2O exchanged), 9.46 (s, 1H), 8.90 (s, 1H), 8.45 (d, J = 8.6 Hz, 1H), 8.12 (d, J= 8.6 Hz, 1H) , 6.88 (s, 1H), 3.70 - 3.17 (m, 2H), 1.44 (t, J = 7.3 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) 5C170.5, 165.0, 157.8, 153.2, 139.5, 134.1, 132.0, 129.2, 332 125.4, 123.0, 119.9, 24.4, 14.5. MS (ESI+) : [M+H]+289.9. Example 2.2: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-methylsulfanyl-1H-imidazol-5-one (2.2) MeS fronr Ln / zznz / E / YiAi Compound (2.2) was synthesized according to GP2: 1a reaction was carried out with (5Z)-5-(1,3-benzothiazol-6-ylmethylene)-2-thioxo-imidazolidin-4-one (3.83 mmol) and Mel, at 0 °C, for 6 h. The yellow solid was ground in DCM after filtration. Yellow solid, 83% (879 mg). NMR (400 MHz, DMSO-dg) δΗ11.89 (br s, 1H, NH, exchanged D2O), 9.46 (s, 1H), 8.92 (d, J= 1.6 Hz, 1H), 8.45 (d, J= 8.6 Hz, 1H), 8.12 (d, J= 8.6 Hz, 1H), 6.88 (s, 1H), 2.72 (s, 3H). NMR13C (101 MHz, DMSO-de) δ 171.1, 166.1, 158.3, 153.7, 140.0, 134.6, 132.4, 129.8, 125.9, 123.5, 120.4, 12.8. MS (ESI+) : [M+H]+ 275.9. Example 2.3: Synthesis of (4Z)-2-ethylsulfanyl-4-[(2-methyl-1,3-benzothiazol-6-yl)methylene]-1H-imidazol-5-one (2.3) EtS Compound (2.3) was synthesized in accordance with GP2: 1a reaction was carried out with (5Z)-5-[(2-methyl-1, 3-benzothiazol-6-yl)methylene]-2-thioxo-imidazolidin-4-one (1.45 333 mmol) and EtI, at room temperature, for 12h. Yellow solid, 84% (368 mg). RMNXH (400 MHz, DMSO-dg) δΗ11.82 (br s, 1H, NH, D2O exchanged), 8.75 (s, 1H), 8.39 (d, J = 8.5 Hz, 1H), 7.94 (d, J = 8.6 Hz, 1H), 6.85 (s, 1H), 3.43 - 3.21 (m, 2H), 2.82 (s, 3H), 1.44 (t, J= 7.3 Hz, 3H). NMR13C (101 MHz, DMSO-de) 5C170.5, 169.0, 164.6, 153.3, 139.2, 135.7, 131.2, 129.1, 124.8, 122.0, 120.1, 24.3, 19.9, 14.5. MS (ESI+) : [M+H]+303.9. Example 2.4: Synthesis of (4Z)-4-[(2-methyl-l,3fronr Ln / zznz / E / YiAi benzothiazol-6-yl)methylene]-2-methylsulfanyl-lH-imidazole-5-one (2.4) Month (2.4) Compound (2.4) was synthesized in accordance with GP2: The first reaction was carried out with (5Z)-5-[(2-methyl-1,3-benzothiazol-6-yl)methylene]-2-thioxo-imidazolidin-4-one (3.63 mmol) and Mel, at room temperature, for 6 h. The yellow solid was ground in DCM after filtration. Yellow solid, 92% (962 mg). RMNXH (400 MHz, DMSO-dg) δΗ 11.86 (br s, 1H, NH, D2O exchanged), 8.77 (s, 1H), 8.39 (d, J = 8.6 Hz, 1H), 7.94 (d, J = 8.6 Hz, 1H), 6.85 (s, 1H), 2.82 (s, 3H) , 2.71 (s, 3H) . 13C NMR (101 MHz, DMSO-d6) oc170.6, 169.0, 165.3, 153.3, 139.2, 135.7, 131.2, 129.3, 124.9, 121.9, 120.2, 19.9, 12.3. MS (ESI+): [M+H]+ 290.1. 334 Example 3: General Protocol 3 - Addition of aliphatic and aromatic amines to (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-alkylsulfanyl-1H-imidazol-5-ones fronr Ln / zznz / E / YiAi R1'NH N Sealed tube V— R2+ r1nh2------------► g solvent (c = 0.3 M) T °C, time (x eq) above reaction scheme, Alk is an alkyl (C1-C5) and R2 represents a hydrogen atom or an alkyl group (C1-C3), in particular R2 represents a hydrogen atom or a methyl group. The appropriate amine (a) (x eq) was added to a stirred suspension of (4Z)-4-heteroaryl-2-alkylsulfanyl-1-himidazol-5-one (b) (1 eq) in the appropriate solvent mixture (c = 0.3 M) in a sealed tube (heating block or pw). The mixture was thoroughly purged with vacuum / argon cycles and heated (pw or heating block) to the appropriate temperature for the specified time. At completion (followed by consumption of the isothiourea in TLC), the mixture was brought back to room temperature. GP3-A: Direct precipitation of the desired product: The reaction medium was stirred for 1 hour at 0 °C. The precipitated solid was filtered through a fritted glass funnel. High purity can be achieved after filtration by washing, reprecipitation, grinding, or 335 recrystallization. - GP3-B: The product did not precipitate: The reaction mixture was concentrated in a vacuum, adsorbed onto silica, and purified by FC. High purity can be achieved after filtration by reprecipitation, trituration, or recrystallization. - GP3-C: the product did not precipitate: the reaction mixture was concentrated under vacuum. The resulting crude was crushed in EtOH (at room temperature or under reflux), and filtered through a fritted glass funnel. High purity can be achieved after filtration by purification, reprecipitation, crushing, or recrystallization. (a) When amine hydrochlorides were used, they were quenched in situ with TEA or DIPEA. (b) May require activation with AcOH, depending on the amine. Selected examples from subgroup A1: Example 3.1: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-(cyclohexylamino)-1H - imidazol-5-one (6) The reaction was carried out according to GP3-A, in THE (0.3 M), on a 2.73 mmol (2.1) scale, with 4 eq of cyclohexylamine at 110 °C (sealed tube, heating block), for 12 h. The product precipitated directly in the reaction medium: it was isolated after filtration, washing with cold THF and then with pentane. Isolate yield: 34%. front Ln / zznz / E / YiAi 336 Example 3.2: Synthesis of (42)-4-(1,3-benzothiazol-6-ylmethylene)-2-(cycloheptylmethylamino)-1H-imidazol-5-one (7) The reaction was carried out according to GP3B, in THF (0.3 M), on a scale of 1.01 mmol of (2.1), with 4 eq of cycloheptylmethylamine at 110 °C (sealed tube, heating block), for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 23% . Example 3.3: Synthesis of (42) -4-(1,3-benzothiazol-6-ylmethylene)-2-(cycloheptylamino)-1H-imidazol-5-one (8) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a scale of 4.84 mmol of (2.1), with 4 eq of cycloheptylamine at 110 °C (sealed tube, heating block), for 12 h. The product precipitated directly in the reaction medium: it was isolated after filtration, washed with cold THF, then with pentane. Isolate yield: 49%. Example 3.4: Synthesis of (42)-4-(1,3-benzothiazol-6-ylmethylene)-2-(cyclooctylamino)-lyf-imidazol-5-one (9) The reaction was carried out in accordance with GP3- A, in THF (0.3 M), on a scale of 2.73 mmol of (2.1) and 4 eq of cyclooctylamine at 110 °C (sealed tube, heating block), for 12 h. The product that precipitated directly into the reaction medium was isolated after filtration, fronr Ln / zznz / E / YiAi 337 washed with cold THF, then pentane. Isolated yield: 58%. Example 3.5: Synthesis of (4Z)-2-(1-adamantylamino)4-(1,3-benzothiazol-6-ylmethylene)-1H-imidazol-5-one (16) The reaction was carried out in accordance with GP3- B, in THF (0.3 M), on a scale of 2.54 mmol of (2.2), with 3 eq of 1-adamantylamine and 15 eq of AcOH, at 160 °C (sealed tube, heating block), for 24 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required two excessive triturations with EtOH under reflux. Isolated yield: 61%. Example 3.6: Synthesis of (4Z)-2-(2-adamantylamino)4-(1,3-benzothiazol-6-ylmethylene)-1H-imidazol-5-one (17) The reaction was carried out in accordance with GP3- B, in THF (0.3 M), on a 746 pmol scale of (2.2), with 4 eq of 2-adamantylamine and 15 eq of AcOH, at 170 °C (sealed tube, heating block), for 12 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in EtOH at 0 °C. Isolated yield: 44%. Example 3.7: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[(trans-5-hydroxy-2-adamantyl)amino]-1-Himidazol-5-one (19) The reaction was carried out in accordance with GP3- B, in THF (0.3 M), on a 746 pmol scale from (2.2), with 4 eq of trans-4-aminoadamantan-l-ol and 15 eq of AcOH, at 170 °C fronr Ln / zznz / E / YiAi 338 (sealed tube, heating block), for 12h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in EtOH at 0 °C. Isolated yield: 27%. Example 3.8: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[(3-hydroxy-l-adamantyl)amino]-lH-imidazol-5-one (20) The reaction was carried out according to GP3B, in THE (0.3 M) , on a scale of 746 pmol of (2.2), with 4 eq of 3-amino-l-adamantanol and 15 eq of AcOH, at 160 °C (sealed tube, heating block), for 12 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in EtOH at 0 °C. Isolated yield: 59%. Example 3.9: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(1R,2R,3R,5S)-2,6,6-trimethylnorpinan-3-yl]amino]-1H-imidazol-5-one (22) The reaction was carried out according to GP3B, in 0.3 M THE, on a scale of 746 pmol of (2.1), with 4 eq of (IR,2R,3R,55)-3-pinanamine, at 120 °C (sealed tube, heating block), for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 60%. Example 3.10: Synthesis of (±)-(4Z)-4-(1,3fronr Ln / zznz / E / YiAi 339 benzothiazol-6-ylmethylene)-2-(spiro[2.5]octan-2-ylamino)-1Himidazol-5-one (25) The reaction was carried out according to GP3B, in THF (0.3 M), on a scale of 773 pmol of (2.1), with 2 eq of (+)-spiro[2.5]octan-2-amine hydrochloride and 2 eq of TEA, at 110 °C (sealed tube, heating block), for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 61%. Example 3.11: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(2R)-1,7,7-trimethylnorbornan-2-yl]amino]-1-Himidazol-5-one (27) The reaction was carried out according to GP3B, in THF (0.3 M) on a 746 pmol scale of (2.1), with 3 eq of (R)-(+)-bornylamine, at 150 °C (sealed tube, heating block), for 8 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 34%. Example 3.12: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(IR)-1-(hydroxymethyl)-3-methylbutyl]amino]1H-imidazol-5-one (34) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 746 pmol of (2.1), with 4 eq of D-leucinol, at 110 °C (sealed tube, front block Ln / zznz / E / YiAi 340 warming), for 12h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 39%. Example 3.13: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene) -2- [ [ (1.R) -1- (methoxymethyl) -3-methyl-butyl] amino] lH-imidazole-5-one (35) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 2.91 mmol of (2.2), with 2.5 eq of (2R)-l-methoxy-4-methylpentan-2-amine, at 120 °C (sealed tube, heating block), for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 74%. Example 3.14: Synthesis of (4Z)-4-(1,3-Benzothiazol6-ylmethylene)-2-[[(1S)-1-(hydroxymethyl)-3-methylbutyl]amino]1H-imidazol-5-one (36) The reaction was carried out according to GP3B, in THF (0.3 M) on a 746 pmol scale of (2.1), with 4 eq of L-leucinol, at 110 °C (sealed tube, heating block), for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: front Ln / zznz / E / YiAi 39%. 341 Example 3.15: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[1-(fluoromethyl)-3-methylbutyl]amino]-1-Himidazol-5-one (40) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 908 pmol of (2.2), with 1.2 eq of (±)-1-fluoro-4-methylpentan-2-amine, at 150 °C (sealed tube, heating block), for 96 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7) after PTLC. Isolated yield: 8%. Example 3.16: Synthesis of (±)-(4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[trans-2-methoxycyclopentyl]amino]-1H-imidazol-5-one (48) The reaction was carried out in accordance with GP3B, in THF (0.3 M) at a 272 pmol scale of (2.2), with 3 eq of (±)-trans-2-methoxycyclopentanamine hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block), for 7 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in refluxing EtOH. Isolated yield: 81%. Example 3.17: Synthesis of (±)-(4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[cis-3-hydroxycyclohexyl]amino]lH-imidazol-5-one (55) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 272 pmol of (2.2), with 3 eq of (±)-cis-3-aminocyclohexanol hydrochloride and 4 eq of fronr Ln / zznz / E / YiAi 342 DIPEA, at 120 °C (sealed tube, heating block) for 24h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 82%. Example 3.18: Synthesis of ( + )-(42)-4-(1,3benzothiazol-6-ylmethylene)-2-[[trans-3-hydroxycyclohexyl]amino]-1H-imidazol-5-one (56) The reaction was carried out in accordance with GP3B, in THF (0.3 M) at a 272 pmol scale of (2.2), with 3 eq of (+)-trans-3-aminocyclohexanol hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block) for 24 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7) after PTLC. Isolated yield: 82%. Example 3.19: Synthesis of (±) - (42)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[trans-2-methoxycyclohexyl]amino]1H-imidazol-5-one (59) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a 272 pmol scale of (2.2), with 3 eq of (+)-trans-2-methoxycyclohexanamine hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block) for 28 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 82%. Example 3.20: Synthesis of ( + )-(42)-4-(1,3benzothiazol-6-ylmethylene)-2-[[cis-2-hydroxycycloheptyl]amino]lH-imidazol-5-one (61) fronr Ln / zznz / E / YiAi The reaction was carried out in accordance with GP3 343 B, in THF (0.3 M) on a 272 μιηοΐ scale of (2.2), with 3 eq of (±)-cis-2-aminocycloheptanol hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block), for 28 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product requires trituration in refluxing EtOH. Isolated yield: 56%. Example 3.21: Synthesis of (±) - (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[trans-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one (62) The reaction was carried out according to GP3B, in THF (0.3 M) at a 272 pmol scale of (2.2), with 3 eq of (±)-trans-2-aminocycloheptanol, at 120 °C (sealed tube, heating block), for 6 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in refluxing EtOH. Isolated yield: 31%. Example 3.22: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[[(1K,21?)-2-hydroxycycloheptyl]amino]-1Himidazol-5-one (63) The reaction was carried out according to GP3B, in THF (0.3 M) on a 746 pmol scale of (2.1), with 3 eq of (IR,2R)-2-aminocycloheptanol, at 110 °C (sealed tube, heating block) for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: front Ln / zznz / E / YiAi 49%. 344 Example 3.23: Synthesis of (±) - (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[cis-3-hydroxycycloheptyl]amino]lH-imidazol-5-one (65) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 218 pmol of (2.2), with 3 eq of (±)-cis-3-aminocycloheptanol hydrochloride and 4 eq of DIPEA, at 150 °C (sealed tube, pw) for 6 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 46%. Example 3.24: Synthesis of (±)-(4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[trans-3-hydroxycycloheptyl]amino]-1H-imidazol-5-one (66) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a scale of 272 pmol of (2.2), with 3 eq of (±)-trans-3-aminocycloheptanol hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block) for 31 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7) after PTLC. Isolated yield: 67%. Example 3.25: Synthesis of (±)-(4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[trans-2-methoxycycloheptyl]amino]-1H-imidazol-5-one (68) The reaction was carried out in accordance with GP3B, in THF (0.3 M) on a 272 pmol scale of (2.2), with 3 eq of (±)-trans-2-methoxycycloheptanamine, at 120 °C (sealed tube, heating block) for 24 h. Purification by fronr Ln / zznz / E / YiAi 345 FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 79%. Selected examples from subgroup A2: Example 3.26: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-(benzylamino)-1H-imidazol-5-one (74) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a scale of 1.38 mmol of (2.1), with 4 eq of benzylamine at 110 °C (sealed tube, heating block) for 12 h. The product precipitated directly in the reaction medium: it was isolated after filtration, washed with cold THF, then with pentane. Isolate yield: 80%. Example 3.27: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[[2-(trifluoromethyl)phenyl]methylamino]-1-Himidazol-5-one (78) The reaction was carried out in accordance with GP3- A, in THF (0.3 M) , on a scale of 272 pmol of (2.2), with 3 eq of [2-(trifluoromethyl)phenyl]methanamine at 120 °C (sealed tube, heating block) for 24h. The product precipitated directly into the reaction medium: it was isolated after filtration and washed with cold THF. The final product requires grinding in refluxed EtOH. Isolated yield: 72%. Example 3.28: Synthesis of (±)-(4Z)-4-(1,3benzothiazol-6-ylmethylene)-2-[[trans-2-hydroxyindan-1fronr Ln / zznz / E / YiAi 346 yl]amino]-lH-imidazole-5-one (81) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a scale of 272 pmol of (2.2), with 3 eq of (±)-trans-l-aminoindan-2-ol at 120 °C (sealed tube, heating block) for 30 h. The product precipitated directly in the reaction medium: it was isolated after filtration and washed with cold THF. The final product required trituration in EtOH at a specific temperature. Isolated yield: 56%. Example 3.29: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(1S,2S)-2-hydroxyindan-l-yl]amino]-1-Himidazol-5-one (83) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a scale of 272 pmol of (2.2), with 3 eq of (1S,2S)-l-aminoindan-2-ol at 120 °C (sealed tube, heating block) for 40 h. The product precipitated directly in the reaction medium: it was isolated after filtration and washed with cold THF. The final product required trituration in EtOH. Isolated yield: 62%. Example 3.30: Synthesis of (±) (4Z)-2-[(2-amino-l-phenyl-ethyl)amino]-4-(1,3-benzothiazol-6ylmethylene)-lH-imidazole-5-one dihydrochloride (89) The reaction was carried out in accordance with GP3- B, in THF (0.3 M) , on a scale of 363 pmol (2.2), with 3 eq of (±)-tere-butyl N-(2-amino-2-phenylethyl)carbamate at 120 (sealed tube heating block) by 48h. front Ln / zznz / E / YiAi 347 Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7) followed by deprotection with HC1 (4M in dioxane). Isolated yield: 63%. Example 3.31: Synthesis of ( + )-(42)-4-(1,3benzothiazol-6-ylmethylene)-2-[(2-hydroxy-l-phenylethyl)amino]lH-imidazol-5-one (95) The reaction was carried out according to GP3B, in THF (0.3 M), on a scale of 272 pmol of (2.2), with 3 eq of (+)-2-phenylglycinol at 150 °C (sealed tube, heating block) for 8 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in refluxing EtOH. Isolated yield: 37%. Example 3.32: Synthesis of (±) - (42)-4-(1,3-benzothiazol-6-ylmethylene)-2-[(2-methoxy-l-phenylethyl)amino]-1-Himidazol-5-one (98) The reaction was carried out according to GP3B, in THF (0.3 M), on a scale of 272 pmol of (2.2), with 3 eq of (+)-2-methoxy-l-phenylethanamine at 120 °C (sealed tube, heating block) for 48 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in refluxing EtOH. Isolated yield: 41%. Example 3.33: Synthesis of ( + )-(42)-4-(1,3benzothiazol-6-ylmethylene)-2-[(2-hydroxy-l-phenyl-ethyl)amino]lH-imidazole-5-one (99) fronr Ln / zznz / E / YiAi The reaction was carried out in accordance with GP3 348 B, in THF (0.3 M), on a 272 pmol scale of (2.2), with 3 eq of (±)-2-amino-l-phenylethanol hydrochloride and 4 eq of DIPEA, at 120 °C (sealed tube, heating block) for 2.5 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product requires trituration in refluxing EtOH. Isolated yield: 41%. Example 3.34: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(1K)-2-methoxy-l-phenylethyl]amino]-1-Himidazol-5-one (176) The reaction was carried out according to GP3A in 0.3 M THF, on a scale of 12.71 mmol of (2.2), with 3 eq of (IR)-2-methoxy-l-phenylethanamine at 140 °C (sealed tube, heating block) for 24 h. The product precipitated directly into the reaction medium; it was isolated after filtration and washed with cold THF. The final product requires trituration in refluxing EtOH. Isolate yield: 51%. Selected examples from subgroup A3: Example 3.35: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-[(5-methylpyrazin-2-yl)methylamino]-IH-imidazol-5-one (103) The reaction was carried out in accordance with GP3B, in THF (0.3 M), on a scale of 182 pmol of (2.2), with 3 eq of (5-methylpyrazin-2-yl)methanamine, at 80 °C (sealed tube, heating block) for 16 h. Purification by FC fronr Ln / zznz / E / YiAi 349 (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 47%. Example 3.36: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[(4-methylthiazol-2-yl)methylamino]-1H-imidazol5-one (108) The reaction was carried out according to GP3B, in THF (0.3 M), on a scale of 182 pmol of (2.2), with 3 eq of (4-methylthiazol-2-yl)methanamine, at 120 °C (sealed tube, heating block) for 24 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required trituration in refluxing EtOH. Isolated yield: 40%. Selected examples from subgroup A4: Example 3.37: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-(tetrahydropyran-4-ylmethylamino)-1H-imidazol5-one (113) The reaction was carried out in accordance with GP3-B, in THF (0.3 M), on a scale of 182 pmol of (2.2), with 3 eq of tetrahydropyran-4-ylmethanamine, at 120 °C (sealed tube, heating block) for 2 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 51%. Selected examples from subgroup A5: Example 3.38: Synthesis of (4Z) -4-(1,3-benzothiazol6-ylmethylene)-2-[4-(4-methylpiperazin-l-yl)anilino]-1Himidazol-5-one (119) fronr Ln / zznz / E / YiAi The reaction was carried out in accordance with GP3 350 A, in THF (0.3 M), on a scale of 182 pmol of (2.1), with 5 eq of 4-(4-methylpiperazin-l-yl)aniline, at 150 °C (sealed tube, pw) for 3 h. The product precipitated directly in the reaction medium and was isolated after filtration. The final product required two excessive triturations with EtOH under reflux. Isolate yield: 65%. Example 3.39: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[(l-methylindazol-7-yl)amino]-lH-imidazol-5-one (125) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a scale of 182 pmol of (2.2), with 5 eq of l-methylindazol-7-amine and 15 eq AcOH, at 130 °C (sealed tube, heating block) for 5 h. The product precipitated directly into the reaction medium and was isolated after filtration. The final product required trituration in EtOH. Isolated yield: 52%. Selected examples from subgroup A6: Example 3.40: Synthesis of (4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-(2-pyridylamino)-1H-imidazol-5-one (127) The reaction was carried out in accordance with GP3A, in THF (0.3 M), on a 1.05 mmol scale of (2.2), with 5 eq of pyridine-2-amine and 15 eq of AcOH, at 150 °C (sealed tube, pw) for 2 h. The product precipitated directly into the reaction medium and was isolated after filtration. The final product requires trituration in refluxing EtOH. Yield fronr Ln / zznz / E / YiAi 351 isolated: 41%. Example 3.41: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[(l-methylpyrazol-3-yl)amino]-lH-imidazol-5-one (128) The reaction was carried out in accordance with GP3- A, in THF (0.3 M), on a scale of 182 pmol of (2.2), with 5 eq of l-methylpyrazol-3-amine, at 150 °C (sealed tube, pw) for 3 h. The product precipitated directly in the reaction medium: it was isolated after filtration. The final product required trituration in EtOH at ta Isolated yield: 71%. Selected examples from subgroup A7: Example 3.42: Synthesis of (4Z)-4-(1,3-benzothiazol6-ylmethylene)-2-[[(3S)-tetrahydrofuran-3-yl]amino]-1-Himidazol-5-one (146) The reaction was carried out in accordance with GP3- B, in THF (0.3 M), on a 746 pmol scale of (2.2), with 3 eq of (3S)-tetrahydrofuran-3-amine, at 120 °C (sealed tube, heating block) for 12 h. The product precipitated directly into the reaction medium: it was isolated after filtration. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required DCM / pentane precipitation at 0 °C. Isolated yield: 51%. Example 3.43: Synthesis of (4Z)-4-(1,3-benzothiazolfronr Ln / zznz / E / YiAi 352 6-ylmethylene)-2-[[(3K)-tetrahydropyran-3-yl]amino]-1Himidazol-5-one (147) The reaction was carried out according to GP3B, in 0.3 M THF, on a scale of 1.04 mmol of (2.1), with 4 eq of (3R)-tetrahydropyran-3-amine hydrochloride and 6 eq of TEA, at 110 °C (sealed tube, heating block) for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 60%. Example 3.44: Synthesis of (42)-4-(1,3-benzothiazol6-ylmethylene)-2-[[(3S)-tetrahydropyran-3-yl]amino]-1-Himidazol-5-one (148) The reaction was carried out according to GP3B, in 0.3 M THF, on a 746 pmol scale of (2.2), with 3 eq of (3S)-tetrahydropyran-3-amine hydrochloride and 4 eq of DIPEA, at 130 °C (sealed tube, heating block) for 12 h. Purification was performed by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 62%. Example 3.45: Synthesis of (42)-4-(1,3-benzothiazol-6-ylmethylene)-2-[[(3R,4R)-4-hydroxytetrahydropyran-3-yl]amino]-1H-imidazol-5-one (150) The reaction was carried out in accordance with GP3B, in THF (0.3 M), on a 746 pmol scale of (2.2), with 3 eq of (3R,4R)-3-aminotetrahydropyran-4-ol, at 130 °C (tube fronr Ln / zznz / E / YiAi 353 sealed, heating block) for 12h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). The final product required precipitation of DCM / pentane at 0 °C. Isolated yield: 35%. Example 3.46: Synthesis of (±)-(4Z)-4-(1,3-benzothiazol-6-ylmethylene)-2-(oxepan-3-ylamino)-1H-imidazol-5-one (151) The reaction was carried out in accordance with GP3-B, in THF (0.3 M), on a scale of 272 pmol of (2.2), with 1.2 eq of (+)-oxepan-3-amine, at 130 °C (sealed tube, heating block) for 12 h. Purification by FC (elution: DCM / MeOH: 99 / 1 to 93 / 7). Isolated yield: 33%. Example 4: Biological activity MATERIALS AND METHODS PROTEIN KINASE ASSAYS 1. Generalities The tests were carried out by ProQinase GmbH (Engesserstr. 4, D-79108 Freiburg, Germany. www.proqinase.com) (Now Reaction Biology; https: / / www.reactionbiology.com / ). The IC50 profile of all compounds was determined using 12 protein kinases (CDK5 / p25, CK1s, CLK1, 2, 3, 4, DYRK1A, IB, 2, 3, 4, 63K3β). IC50 values ​​were measured by analyzing 10 concentrations (10 μM to 30 nM) of each compound in singlicate. front Ln / zznz / E / YiAi 354 2. Test compounds The compounds were provided as 1 μM base solutions in 100% DMSO. Prior to testing, the 1 μM base solutions underwent serial semi-logarithmic dilution using 100% DMSO as the solvent. This resulted in 10 distinct concentrations, with an endpoint dilution of 3 x 10⁻⁵ nM / 100% DMSO, using 100% DMSO as controls. In the process, 90 pL of H₂O was added to each well of each compound dilution plate. To minimize potential precipitation, H₂O was added to each plate only a few minutes before the compound solutions were transferred to the assay plates. The plate was thoroughly shaken, resulting in a 10% compound / DMSO dilution plate. For the assays (see below), 5 μL of solution were transferred from each well of the compound / 10% DMSO dilution plates to the assay plates. The final assay volume was 50 pL. All compounds were tested at 10 final assay concentrations in the range of 10 μM to 30 nM. The final DMSO concentration in the reaction cocktails was 1% in all cases. 3. Recombinant Protein Kinases All protein kinases provided by ProQinase were expressed in insect Sf9 cells or in E. coli as recombinant GST fusion proteins or fronr Ln / zznz / E / YiAi labeled proteins 355 with His, either as full-length fragments or enzymatically active. All kinases were produced from human cDNA and purified by affinity chromatography with GSH or immobilized metal. Affinity tags were removed from several kinases during purification. Protein kinase purity was examined by SDS-PAGE / Coomassie staining, and identity was confirmed by mass spectrometry. 4. Protein Kinase Assay A radiometric protein kinase assay (33PanQinase® Activity Assay) was used to measure the kinase activity of the 12 protein kinases. All kinase assays were performed in 96-well FlashPlates™ from PerkinElmer (Boston, MA, USA) in a reaction volume of 50 pl. The reaction cocktail was pipetted in four steps in the following order: • 25 pL of assay buffer (standard buffer / [γ-33P] -ATP), • 10 pL of ATP solution (in H2O), • 5 pL of test compound (in 10% DMSO), • 10 pL of enzyme / substrate mixture. The assay for all protein kinases contains HEPES-NaOH 7.0 mM pH 7.5, MgCl2 3 mM, MnCl2 3 mM, Na orthovanadate 3 pM, DTT 1.2 mM, PEG20000 50 pg / ml, ATP (variable concentrations, corresponding to the apparent ATP-Km of the respective kinase), [γ-33P]-ATP (approx. 6.5 x 10-05 cpm per well), fronr Ln / zznz / E / YiAi 356 protein kinase (variable amounts) and substrate (variable amounts) were added. The reaction cocktails were incubated at 30°C for 60 minutes. The reaction was stopped with 50 pL of 2% (v / v) H3PO4, the plates were aspirated, and washed twice with 200 pL of 0.9% (w / v) NaCl. The incorporation of 33Pi was determined using a microplate scintillation counter (Microbeta, Wallac). IC50 values ​​for all compounds were calculated from the dose-response curves. 5. Quality controls As a parameter for assay quality, the Z' factor (Zhang et al., J. Biomol. Screen. 2: 67-73, 1999) was used for the high and low controls of each assay plate (n = 8). The ProQinase criterion for repeating an assay plate is a Z' factor below 0.4 (Iversen et al., J. Biomol. Screen. 3: 247-252, 2006). Its activity has been classified according to two criteria: kinase inhibition potency and kinase selectivity. The classification of kinase inhibition potency was performed according to the following IC50 value intervals: Some compounds have an IC50 activity that varies above 0.050 pM. These compounds correspond to the previously mentioned class E. Some compounds have an IC50 activity that varies from 0.025 to 0.050 pM. These fronr Ln / zznz / E / YiAi 357 compounds correspond to the aforementioned Class D. Some compounds of the invention have an IC50 activity ranging from 0.010 to 0.025 μM. These compounds correspond to the aforementioned Class C. In addition, some particular compounds have an IC50 activity ranging from 0.005 to 0.010 μM. These compounds correspond to the aforementioned Class B. Compounds of the invention with an IC50 activity of less than 0.005 μM are preferred. These compounds correspond to the aforementioned Class A. This classification was applied to CLK1 and DYRK1A. The letters A through E were used to describe the activity / efficacy of the compounds of the invention in Tables 4, 4A, and 4B below. The kinase selectivity classification was based on a comparison of the IC50 values ​​of DYRK1A with those of CLK1 or DYRK1B. The classification was made according to the following ranges of values: I: IC50 ratio of CLK1 or DYRK1B to IC50 of DYRK1A > 10 times (most compounds selective for DYRK1A); II: ratio between 2 and 10 times; III: ratio between 0.5 and 2 times; IV: ratio between 0.1 and 0.5 times; V: ratio > 0.1 times (most compounds selective for CLK1 or DYRK1B). These numbers I to V were used to quote the relative selectivity of the compounds of the invention in the following tables. front Ln / zznz / E / YiAi 358 front Ln / zznz / E / YiAi CN 3 '(D φ — O +JW Ό IT 359 Class of Class of Class of Class of University Entrance Exam Class Selectivity Ccnp Selectivity Power Power DYRK1A Power Power DYRK1A front Ln / zznz / E / YiAi 360 Class of Class of Class of Class of University Entrance Exam Class Selectivity Ccnp Selectivity Power Power DYRK1A Power Power DYRK1A fronr ίη / ζζηζ / Ε / γίΛΐ 361 Class of Class of Class of Class of University Entrance Exam Class Selectivity Ccnp Selectivity Power Power DYRK1A Power Power DYRK1A fronr ίη / ζζηζ / Ε / γίΛΐ 362 Class of Class of Class of Class of University Entrance Exam Class Selectivity Ccnp Selectivity Power Power DYRK1A Power Power DYRK1A fronr ίη / ζζηζ / Ε / γίΛΐ 363 Class of Class of Class of Class of University Entrance Exam Class Selectivity Ccnp Selectivity Power Power DYRK1A Power Power DYRK1A fronr ίη / ζζηζ / Ε / γίΛΐ 365 Table 4A. More potent CLK1 inhibitors (IC50 < nM). Kinase inhibition potency classes: IC50 values: A < 0.005 μM; B < 0.010 μM; C < 0.025 μM; D < 0.050 μM; E > 0.050 μM. Kinase selectivity classes based on DYRK1A: class I (selectivity >10-fold), class II (selectivity 2–10-fold), class III (selectivity 0.5–2-fold = equipotency). Some compounds show better selectivity for CLK1 or DYRK1B compared to DYRK1A. These compounds correspond to the previously reported class IV (selectivity 2–10-fold) or class V (selectivity >10-fold). Comp. Clase de Clase de Power Clase de Selectividad NO. Power CLK1 DYRK1A DYRK1A contra CLK1 19 AA II 73 BE IV 78 BB III 20 BA 1 21 BA II 61 BA II 95 BA II 16 BA II 35 BA II 48 BA III 81 BA II 96 BA II 9 BB III 155 BC III 159 BA II 160 BA II 366 161 BD IV 169 BB III 169A BC III 171A BC III 176 BA III 184 BA II 196 BAI 199 BA II 200 BA II 201 BA II 202 BA II 203 BA II 210 BA II fronr Ln / zznz / E / YiAi The most powerful CLK2 inhibitors, with an IC50 lower or equal to 10 nM are the computers (9) , (16) , (20) , (21), (22), (24), (25), (81), (83), (89), (95), (96), (159), (181), (194), (196), (199), (200), (201), (202) and (203). The most powerful CLK3 inhibitors, with an IC50 lower than or equal to 100 nM are the compounds (48), (89) (90), (159), (164), (165), (169), (169B), (178) and (181). The most potent CLK4 inhibitors, with an IC50 less than or equal to 10 nM, are compounds (7), (8), (9), (10), (12) , (16) , (17) , (19) , (20) , (21) , (23) , (25) , (26) , (28) , (32) , (33) , (34) , (35) , (40) , (41) , (43) , (44) , (46) , (48) , (51) , (55) , (56) , (57) , (59) , (61) , (62) , (63) , (65) , (66) , (67) , (68) , (69) , (70) , (73) , (77) , (78) , (81) , (83) , (88), (89), (90), (95), (96), (97), (98), (99), (100), (101), 367 (102), (104), (105), (106), (117), (119), (127), (131), (139), (148), (149), (149B), (151), (155), (156), (157), (158), (159), (160), (161), (164), (165), (167), (169), (169Α), (169Β), (170), (171), (171A), (171B) , (172), (173), (176), (178) , (179) , (180) , (181), (184), (185), (191), (192), (192Α), (194) , (196) , (198) , (199), (200), (201), (202), (203) and (210) . Table 4Β. More potent DYRK1A inhibition (IC50 < 10 ηΜ) . China inhibition effectiveness classes and China selection classes as described in Table 4A. fronr ίη / ζζηζ / Ε / γίΛΐ Comp NO. Power Clamp CLK1 Power Clamp DYRK1A Selective Clase DYRK1A against CLK1 Selective Clase DYRK1A against DYRK1B 20 BAI II 16 BA II III 19 AA II II 27 CA II II 21 BA II II 22 CAI II 81 BA II III 61 BA II II 35 BA II II 95 BA II II 96 BA II II 65 CA II II 66 CA II II 34 CA II III 25 CA II II 368 Comp NO. CLK1 Power Class DYRK1A Potency Class DYRK1A versus CLK1 Selectivity Class DYRK1A versus DYRK1B 48 BA III II 159 BA II II 160 BA II 4 4 BA II II 176 BA III II 184 BA II 176 BA III II 184 BA II II II 200 BA II II 201 BA II II 202 BA II III 203 BA II II 210 BA II II 83 CB II IV 40 CB II II 9 BB III III 89 CB II II 17 CB II II 9 9 BB III II 97 CB II II IBB 916 CB III1 CB II I 173 CB III I 195 CB III III 162 DB II III 175 DB II I 369 The most potent DYRK1B inhibitors, with an IC50 less than or equal to 10 nM are compounds (20), (16), (83), (81), (34), (95), (21), (22), (27), (35), (61), (9), (96), (1979), (1519), (160), (196), (199), (200), (201), (202), (203) and (210) . The most potent DYRK2 inhibitors, with an IC50 less than or equal to 100 nM, are compounds (16), (20), (21), (48), (89), (90), (99), (119), (158), (159), (169), (179), (194), (196), (199), (200), (201), (203) and (210). The most potent DYRK3 inhibitors, with an IC50 less than or equal to 100 nM, are compounds (16), (20), (21), (89), (90), (119), (162), (159), (181), (194), (196), (199), (200), (201) and (203). The most potent DYRK4 inhibitors, with an IC5o less than or equal to 100 nM, are compounds (20) and (48), fronr Ln / zznz / E / YiAi (164), (194) and (196). 370 Table 4C. Most selective DYRK1A inhibitors compared to CLK1. Kinase Selectivity Classes as described in Table 4A. Comp NO. Selectivity Class DYRK1A vs CLK1 Comp NO. Selectivity Class DYRK1A vs CLK1 20 I 66 II 22 I 83 II 194 I 18 II 196 I 29 II 204 I 125 II 16 II 36 II 17 II 159 II 21 II 160 II 61 II 162 II 27 II 172 II 35 II 174 II 95 II 175 II 96 II 184 II 97 II 192B II 9 II 199 II 19 II 200 II 81 II 201 II 148 II 202 II II 203 II 34 II 205 II 40 II 209 II 25 II 210 II 371 Table 4D. Most selective CLK1 inhibitors compared to DYRK1A. Kinase Selectivity Classes as described in Table 4A. front Ln / zznz / E / YiAi Comp. NO. Selectivity Class DYRK1A vs CLK1 79 V 115 V 123 V 82 V 10 V 33 V 102 V 26 V 105 V 372 Table 4E. Most selective inhibitors of DYRK1A compared to DYRK1B. Kinase Selectivity Classes fronr Ln / zznz / E / YiAi as described in Table 4A. Comp. NO. Clase de Selectividad DYRK1A against DYRK1B Comp. NO. Clase de Selectividad DYRK1A versus DYRK1B 28 I 153 II 120 I 13 II 116 I 152 II 42 I 77 II 148 I 15 II 168 I 136 II 169 I 48 II 170 I 85 II 171 I 49 II 172 I 62 II 173 I 59 II 174 I 90 II 175 I 43 II 178 I 99 II 185 I 63 II 190 I 80 II 191 I 98 II 76 II 86 II 111 II 45 II 75 II 12 II 122 II 56 II 46 II 149 II 71 II 50 II 67 II 150 II 129 II 121 II 144 II 55 II 141 II 146 II 37 II 44 II fronr ίη / ζζηζ / Ε / γίΛΐ Comp. Clase de Selectividad Comp. Class of Selectivity NO. DYRK1A versus DYRK1B NO. DYRK1A versus DYRK1B 93 II 22 II 51 II 149A II 52 II 158 II 53 II 159 II 54 II 160 II 57 II 163 II 78 II 164 II 64 II 166 II 60 II 167 II 154 II 169A II 14 II 169B II 87 II 176 II 84 II 177 II 17 II 181 II 61 II 182 II 27 II 183 II 35 II 184 II 95 II 186 II 96 II 187 II 97 II 188 II 89 II 189 II 19 II 192 II 65 II 192A II 40 II 192B II 25 II 197 II 66 II 198 II 29 II 199 II 36 II 200 II 20 II 205 II 21 II 207 II 374 fronr ίη / ζζηζ / Ε / γίΛΐ Comp. Selectivity Class NO. DYRK1A versus DYRK1B 208 II 209 II 210 II 375 Table 4F. Most selective DYRK1B inhibitors compared to DYRK1A. Kinase Selectivity Classes as described in Table 4A. front Ln / zznz / E / YiAi Comp NO. Selectivity Class DYRK1A vs DYRK1B 26 V 115 IV 123 IV 82 IV 10 IV 33 IV 88 IV 23 IV 100 IV 135 IV 83 IV RESULTS Most of the compounds of the present invention exhibit an IC50 activity of less than 2 pM on CLK or DYRK. All compounds were inhibitors of DYRK1A and CLK1 (Table 4). The compounds were preferentially inhibitors of CLK1 (Table 4A), CLK4, DYRK1A (Table 4B) and DYRK1B. Some are more selective for DYRK1A versus CLK1 (Table 4C), DYRK1A versus DYRK1B (Table 4E), DYRK1B versus DYRK1A (Table 4F), or CLK1 versus DYRK1A (Table 4D). Some compounds show better selectivity for DYRK1A. 376 compared to CLK1 or DYRK1B. These compounds correspond to Class I (selectivity >10 times greater) or Class II (selectivity 2 to 10 times greater) mentioned above. Some compounds are equipotent. These compounds correspond to Class III (selectivity 0.5 to 2 times greater) mentioned above. Some compounds show better selectivity for CLK1 or DYRK1B compared to DYRK1A. These compounds correspond to Class IV (selectivity 2 to 10 times greater) or Class V (selectivity >10 times greater) mentioned above. CONCLUSION Based on the above results, it can be concluded that the compounds of formula (I) are suitable chemical compounds in the prevention and / or treatment of cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick type C disease); CDKL5 deficiency disorder; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis, particularly knee osteoarthritis; Duchenne muscular dystrophy; various types of cancer, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia and acute lymphoblastic leukemia, and the front Ln / zznz / E / YiAi 377 squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer and breast cancer, such as triple-negative breast cancer (TNBC), malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and diseases of livestock caused by single-celled pathogens, viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus and herpes simplex virus (HSV) and in the regulation of body temperature. It can also be concluded that some compounds of formula (I) are also suitable for treating and / or preventing Phelan-McDermid syndrome; autism; other viral infections, such as those caused by hepatitis C virus, Chikungunya virus, dengue virus, influenza virus and severe acute respiratory syndrome coronavirus (SARS), cytomegalovirus and human papillomavirus; other types of cancer, such as tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, neuroinflammation, anemia, infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and borderline soft tissue disease. 378 sleep (Trypanosoma sp.) and livestock diseases due to unicellular pathogens. Leucettinibs exhibit significantly increased efficacy (ICsq values ​​dropping to submicromolar and single-digit micromolar levels) compared to reference compounds. They also show a broad selectivity range for DYRK1A or CLK1. Some products that are equipotent to CLK and DYRK may also find applications as dual-specificity inhibitors. The present invention further relates to a pharmaceutical composition comprising at least one compound of formula (I) as defined above or any of its pharmaceutically acceptable salts or at least any of the compounds (1) to (216) as defined above or any of their pharmaceutically acceptable salts and also at least one pharmaceutically acceptable excipient. The pharmaceutical compositions of the invention may contain one or more compounds of the invention in any form described herein. Another object of the present invention consists of the use of at least one compound of formula (I) as defined above, and compounds (1) to (216) as defined above, or one of their pharmaceutically acceptable salts according to the present invention for the preparation of a drug for the prevention and / or treatment of Ln / zznz / E / YiAi 379 of a selected disease of cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; and other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick disease type C); CDKL5 deficiency disorder; McDermid syndrome; autism; type 1 and type 2 diabetes; regulation of folate and methionine metabolism; osteoarthritis, particularly knee osteoarthritis; Duchenne muscular dystrophy;various cancers, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia, squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, breast cancer, such as triple-negative breast cancer (TNBC), tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus, herpes simplex virus (HSV), hepatitis C virus, chikungunya virus, dengue virus, influenza virus, and acute respiratory syndrome coronavirus. Ln / zznz / E / YiAi; 380 severe (SARS), cytomegalovirus and human papillomavirus; neuroinflammation; anemia; infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and livestock diseases caused by single-celled pathogens, and to regulate body temperature. A further objective of the present invention is the use of at least one compound of formula (I) as defined above, and compounds (1) to (216) as defined above, or one of their pharmaceutically acceptable salts according to the present invention, for the preparation of a drug for the prevention and / or treatment of a selected disease of cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick type C disease); CDKL5 deficiency disorder; type 1 and type 2 diabetes; regulation of folate and methionine metabolism; osteoarthritis, particularly osteoarthritis of the knee; Duchenne muscular dystrophy;various types of cancer, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia, squamous cell carcinoma of the head and neck, pancreatic cancer, including the front Ln / zznz / E / YiAi; 381 pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer and breast cancer, such as triple-negative breast cancer (TNBC), infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and livestock diseases due to single-celled pathogens and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus and herpes simplex virus (HSV), and to regulate body temperature. Yet another objective of the present invention is the use of at least one compound of formula (I), as defined above, and compounds (1) to (216) as defined above, or one of their pharmaceutically acceptable salts according to the present invention, to prepare a medicament for combating a selected disease of type 1 and type 2 diabetes, viral infections, in particular as mentioned above, osteoarthritis, cancers, in particular as mentioned above, infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease, and sleeping sickness (Trypanosoma sp.), and diseases of livestock due to single-celled pathogens, and for regulating body temperature. front Ln / zznz / E / YiAi 382 Depending on the specific modality, the treatment is either continuous or discontinuous. Continuous treatment means long-term treatment that can be implemented with various administration frequencies, such as once a day, every three days, once a week, once every two weeks, or once a month, or via transdermal patch. According to one modality, the compound of formula (I), or any of its pharmaceutically acceptable salts, is administered at a dose ranging from 0.1 to 1000 mg, in particular from 1 to 500 mg, or for example ranging from 5 to 100 mg. Another objective of the invention relates to a therapeutic method for the treatment and / or prevention of selected cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; and other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick type C disease); CDKL5 deficiency disorder; McDermid syndrome; autism; type 1 and type 2 diabetes; regulation of folate and methionine metabolism; osteoarthritis, particularly knee osteoarthritis; Duchenne muscular dystrophy; various cancers, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia, and frontal carcinoma. 383 squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, breast cancer, such as triple-negative breast cancer (TNBC), tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMVj), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus, herpes simplex virus (HSV), hepatitis C virus, chikungunya virus, dengue virus, influenza virus, and severe acute respiratory syndrome coronavirus (SARS), cytomegalovirus, and human papillomavirus; neuroinflammation; anemia; infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease and sleeping sickness (Trypanosoma sp.), and diseases of livestock caused by single-celled pathogens, and for the regulation of body temperature, in a patient who needs it, comprising at least one step of administering a therapeutically effective amount of a compound of formula (I) or of compounds (1) to (216), as defined above or one of their acceptable salts. In one specific embodiment, the invention provides for the use of a compound of formula (I) of fronr Ln / zznz / E / YiAi 384 in accordance with the invention or a pharmaceutically acceptable salt thereof or a pharmaceutically active derivative thereof or a method in accordance with the invention wherein the compound of formula (I) is to be administered in combination with a co-agent useful in any of the above-mentioned diseases. The compounds can be administered via any route of administration such as intramuscular, intravenous, intranasal or oral, transdermal patch, etc. The inventive composition may further include one or more additives such as diluents, excipients, stabilizers, and preservatives. Such additives are well known to those skilled in the art and are notably described in Ullmann's Encyclopedia of Industrial Chemistry, 6th Ed. (various editors, 1989-1998, Marcel Dekker) and in Pharmaceutical Dosage Forms and Drug Delivery Systems (Ansel et al., 1994, Williams & Wilkins). The aforementioned excipients are selected according to the desired dosage form and mode of administration. The compositions of this invention can be administered in any manner, including, but not limited to, orally, parenterally, sublingually, transdermally, vaginally, rectally, transmucosally, topically, orally. 385 Intranasal, by inhalation, by oral or intranasal administration, or combinations thereof. Parenteral administration includes, but is not limited to, intravenous, intra-arterial, intraperitoneal, subcutaneous, intramuscular, intrathecal, and intra-articular administration. The compositions of this invention can also be administered in implant form, allowing for slow release of the compositions as well as slow, controlled intravenous infusion. For example, a compound of formula (I) may be present in any pharmaceutical form that is suitable for enteral or parenteral administration, in association with appropriate excipients, for example, in the form of plain or coated tablets, hard gelatin, soft-coated capsules and other capsules, suppositories or drinkable solutions, such as suspensions, syrups or injectable solutions or suspensions. In one particular embodiment, a compound of formula (I) according to the invention is administered orally. In particular, the oral route of administration is preferred in the aspect of prophylaxis or treatment of the invention. It is noted that with regard to this date the best method for putting the aforementioned invention into practice is the one that is clear from the description of the present invention. < / s>

Claims

1. A compound of formula (I) R1-nh (i) characterized in that R1 represents: (i) an alkyl group (C1-C4) substituted by one or two groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkoxy group (C1-C4) and a benzyloxy group, such benzyloxy being optionally substituted in its phenyl group by one to three halogen atoms, (ii) a spirobicyclic ring (C5-Cn), (iii) a fused phenyl group, selected from phenyl groups fused to a cycloalkyl (Cs-Ce) or heterocycloalkyl (C5-C6) ring, wherein the cycloalkyl (C5-Ce) and heterocycloalkyl (C5-Cg) ring optionally comprises an unsaturation and is optionally substituted by an alkyl (C1-C4) group, a hydroxy group, a halogen atom, an alkoxy (C1-C3) group or a -CORa group, (iv).a phenyl group, substituted by one or two groups selected from an alkyl (Ci-Cs), a fluoroalkyl (C1-C3) group, a fluoroalkoxy (C1-C4) group, a halogen atom, and a heterocycloalkyl (C4-C7) group, such heterocycloalkyl (C4-C7) group being the same optionally substituted by an alkyl (C1-C4) group or (v). an R'-L- group, wherein L is either a single bond or an alkoxy (C1-C3) group, optionally substituted by a group selected from a hydroxy group and an alkoxy (C1-C3) group, and R' represents: (vl) a cycloalkyl (Cg-Cg) group, optionally substituted by one, two, or three groups selected from an alkyl (C1-C4) group, a hydroxy group, a halogen atom and an alkoxy (C1-C3) group, (v.(2) a bridged cycloalkyl (Cg-Cio) group, optionally substituted by one to three groups selected from an alkyl (C1-C4) group, an alkoxy (C1-C4) group, a halogen atom, a hydroxy group, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, an -SO2-Rd group, an -N(Re)2 group and a -COORa group, (v.3) a heterocycloalkyl (Cg-Cg) group, optionally substituted by one to three groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkyl (C1-C4) group and an oxo group, (v.4) a heteroaryl (C3-C3) group, optionally substituted by one to three groups selected from a halogen atom, an alkyl group (C1-C4), a fronr Ln / zznz / E / YiAi 388 alkoxy group (C1-C4) and an N-methylpiperazinyl group, or (v.5) a bridged heterocycloalkyl group (Cg-Cio), or (vi).an R'-L- group where L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from a -NRbRc group, an alkoxy (CqC4) group, a hydroxy group, a -COORa group and a halogen atom, and R' is a phenyl group, optionally substituted by one to three groups selected from the group consisting of an alkyl (Cq-Cg) group, a fluoroalkyl (C1-C4) group and a fluoroalkoxy (C1-C4) group, a halogen atom and a hydroxy group, Ra represents an alkyl (C1-C4) group or a hydrogen atom, Rb and Rc independently represent an alkyl (Cq-C6) group or a hydrogen atom, Rd represents an alkyl (C1-C4) group or a cyclopropyl group, Re represents an alkyl (C1-C3) group, and R2 represents an atom of hydrogen or an alkyl group (C1-C3), or any of its pharmaceutically acceptable salts.

2. A compound of formula (I) according to claim 1, characterized in that R1 represents: (i) . an alkyl group (C2-Cg) substituted by one or two groups selected from a -COORa group, a hydroxy group, a halogen atom, an alkoxy group (C1-C4) and a benzyloxy group, such benzyloxy is optionally substituted at its phenyl group by one to three halogen atoms, (ii) . a spirocyclic ring (C7-C9), (iii) . a fused phenyl group, selected from phenyl groups fused to a cyclopentyl or a heterocyclopentyl, wherein the cyclopentyl and heterocyclopentyl group optionally comprises an unsaturation and is optionally substituted by an alkyl (C4-C4) group, a hydroxy group, a halogen atom, an alkoxy (C1-C3) group or a -CORa group, (iv).a phenyl group, substituted by one or two groups selected from an alkyl group (C1-C3), a fluoroalkyl group (C1-C4), a halogen atom, and a heterocycloalkyl group (C4-C7), such heterocycloalkyl group (C4-C7) is the same optionally substituted by an alkyl group (C1-C4), or (v). an R'-L- group where • L is either a single bond or an alkandiyl (C1-C3) group, optionally substituted by a group selected from a hydroxy group and an alkoxy (C1-C3) group, and fronr Ln / zznz / E / YiAi 390 • R' represents: (vl) a cycloalkyl (Cs-Cs) group, optionally substituted by one, two, or three groups selected from an alkyl (C1-C4) group, a hydroxy group, a fluorine atom and an alkoxy (C1-C3) group, (v .(2) a bridged (C7-C10) cycloalkyl group, optionally substituted by one to three groups selected from a (C1-C4) alkyl group, a (C1-C4) alkoxy group, a hydroxy group, a halogen atom, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, an -SO2-Rd group, an -N(Re)2 group and a -COORa group, (v.3) a (C4-C7) heterocycloalkyl group, optionally substituted by one to three groups selected from a -COORa group, a hydroxy group, a halogen atom, a (C1-C4) alkyl group and an oxo group, (v.4) a heteroaryl group, optionally substituted by one to three groups selected from a halogen atom, a (C1-C4) alkyl group , an alkoxy (C1-C4), an N-methylpiperazinyl group, or (v.5) a bridged heterocycloalkyl (Ce-Cio) group, or (vi) .an R'-L- group wherein • L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from a -NRbRc group, an alkoxy (C1-C4) group, a hydroxy group, a -COORa group and a halogen atom, and • R' is a phenyl group, optionally substituted by one to three groups selected from the group consisting of an alkyl (C1-C6) group, a fluoroalkyl (C4-C4) group and a fluoroalkoxy (C1-C4) group, a hydroxy group and a halogen atom, Ra represents an alkyl (C1-C4) group or a hydrogen atom, Rb and Rc independently represent an alkyl (C1-C4) group or a hydrogen atom, Rd represents an alkyl (C4-C4) group or a hydrogen atom cyclopropyl, Re represents a (C1-C3) alkyl group, and R2 represents a hydrogen atom or a (C1-C3) alkyl group, or any of its pharmaceutically acceptable salts.

3. A compound of formula (I) according to any one of claim 1 or 2, characterized in that R1 represents: (i) . an alkyl group (C2-Cg) substituted by one or two groups selected from a -COOCH3 group, a hydroxy group, a fluorine atom, a methoxy group, an ethoxy group, a tert-butoxy group, a cyclopropoxy group and a benzyloxy group, such benzyloxy being optionally substituted at its phenyl group by a fluorine atom, (ii) . a spirobicyclic ring (Cv-Cg), in particular a spiro[3.3]heptyl, a spiro[2.5]octanyl or a 7-azaspiro[3.5]nonyl, (iii) . a fused phenyl group, selected from phenyl groups fused to a cyclopentyl or a heterocyclopentyl, wherein the cyclopentyl and heterocyclopentyl group optionally comprises an unsaturation and is optionally substituted by a methyl, a hydroxy group, a methoxy group and a -COCH3 group, (iv) .a phenyl group, substituted by one or two groups selected from a methyl group, a hexyl group, a trifluoromethyl group, a difluoromethoxy group, a halogen atom, in particular a fluorine atom, a morpholino group and an N-methylpiperazinyl group, or (v) an R'-L- group where L is either a single bond or an alkandiyl (C1-C3) group, optionally substituted by a group chosen from a hydroxy group and an alkoxy (C1-C3) group, and R' is selected from the group consisting of: (vl) a cycloalkyl (C3-C8) group, in particular a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, optionally substituted by one, two, or three groups selected from a methyl, isopropyl, hydroxy and methoxy group, (v.2) . a bridged cycloalkyl (C7-C10) group, in particular an adamantyl or a bicyclo[3.1.1]heptyl, optionally substituted by one to three groups selected from a methyl group, a methoxy group, a hydroxy group, a fluorine atom, a -OC(O)-CH3 group, an OC (O) -C (CH3) 3 group, a -OC (O)-NH-C (CH3) 3 group, a -NHC(O)-CH3 group, a -NH-C (O)-C3H4 group, a -S(O)2-CH3, a group — S(O)2—C3H4, a group -N(CH3)2 and a group -C(O)-O-CH3, (v.3). a heterocycloalkyl group (Cg-Cg), in particular a tetrahydropyranyl, a piperidinyl, an oxethanyl, a tetrahydrofuranyl, an oxepanyl, a tetrahydrothiopyranyl, a pyrrolidinyl, a dioxepanyl or a piperidinyl, optionally substituted by one, two or three group(s) selected from a -COORf, a hydroxy group, a methyl group and an oxo group, wherein Rf represents either an ethyl or isopropyl group, (v.4).a heteroaryl group, in particular a pyrimidinyl, a pyridinyl, a thiazolyl, an imidazolyl, a pyrazolyl, a thiadiazolyl, a pyridazinyl, a pyrazinyl, a furyl, optionally substituted by one to three groups selected from a methyl group, a methoxy group and an N-methylpiperazinyl group, o (v.5) . a bridged (C7-C10) cycloalkyl group, fronr Ln / zznz / E / YiAi 394 in particular a quinuclidin-3-yl, o (vi) .an R'-L- group where L is an alkandiyl (C1-C3) group, optionally substituted by a group selected from the group consisting of an NRbRc group, an alkoxy (C1-C4) group, a hydroxy group, a COORa group and a halogen atom, in particular a fluorine atom, and R' is a phenyl group, optionally substituted by one or two groups selected from the group consisting of a methyl group, a trifluoromethyl group and a trifluoromethoxy group, Ra represents an alkyl (C1-C3) group, Rb and Rc are independently selected from a methyl group or a hydrogen atom, and R2 represents a hydrogen atom or an alkyl (C1-C3) group, or any of their pharmaceutically acceptable salts.

4. A compound of formula (I) according to any of the preceding claims, characterized in that L is selected from a group consisting of a -CH2- group, a -CH(CH3)- group, a CH(CH2OH)-CH2- group, a -CH(CH2OH)- group, a -CH(CH2OCH3)- group, a CH(OH)-CH2- group, a -CH2-CH(CH2OCH3)- group, a -CH(OCH3)CH2- group, a -CH2-CH(COOCH3)- group, a -CH(CH2F)- group, a -CH(CH2NH2)- group, a -CH(CH2NHCH3)- group, a -CH(CH2N(CH3)2)- group, a -CH2-CH(CH2OH)- group, a -CH(OCH3)-CH2- group, a group -CH2CH(OCH3)-, a -CH2-CH (OH)-CH2- group, a -CH2-CH (OCH3) CH2 group, a -(CH2)3- group, a -(CH2)2- group and a CH (CH2OC (CH3) 3) group, or any of its pharmaceutically acceptable salts.

5. A compound of formula (I) according to any of the preceding claims, characterized in that: (v.1) when R' is a (C3-Cg) cycloalkyl group, L is selected from the group consisting of a single bond, a -CH2- group, a -CH(CH3)- group, a -CH(CH2OH)-CH2- group, a -CH(CH2OH)- group, a -CH(CH2OCH3)- group, and a -CH(OH)-CH2- group and a -CH(OCH3)-CH2- group, (v.2) when R' is a bridged (C7-C10) cycloalkyl group, L is a single bond, a -CH2- group or a -CH(CH3)- group, (v.3). when R' is a heterocycloalkyl (C5-Cg) group including spiro (C3-Cg) heterocycloalkyls, L is a single bond or a -CH2- group, (v.4) .When R' is a phenyl, L is selected from the group consisting of a single bond, a —CH2— group, a -CH2-CH (COOCH3) - group, a -CH(CH2F)- group, a -CH (CH2NH2)- group, a -CH (CH2NHCH3)- group, a CH(CH2N(CH3)2) group, a -CH2-CH(CH2OH) group, a front group, a -CH(CH2OH)- group, a -CH (CH2OCH3) - group, a -CH(OH)-CH2- group, a -CH2-CH (CH2OCH3) - group, a -CH2-CH (OH)-CH2- group, and a CH2-CH (OCH3) —ch2 group, (v.5). When R' is a heteroaryl group, L is selected from the group comprising a single bond, a -CH2- group, a -(CH2)3- group and a -(CH2)2 group, Y (v.6). When R' is a bridged (Ct-Cío) heterocycloalkyl group, L is a single bond.

6. A compound of formula (I) according to any of the preceding claims, characterized in that R1 represents: an adamantyl group, optionally substituted by one to three groups, and in particular substituted by a group, selected from a methyl group, a methoxy group, a hydroxy group, a fluorine atom, an -OC(O)-CH3 group, an -OC(O)-C(CH3)3 group, an -OC(O)-NHC(CH3)3 group, an -NH-C(O)-CH3 group, an -NH-C(O)-C3H4 group, an -S(O)2-CH3 group, an -S(O)2-C3H4 group, an -N(CH3)2 group, and a -C(O)-O-CH3 group, the adamantyl group being preferably unsubstituted;or a group RO-CH2(R')-, wherein: o R is an alkyl group (C1-C4) , preferably a methyl or ethyl group, o R' is an alkyl group (C1-C4) , in particular an alkyl group (C3-C4) , and preferably an isopropylmethyl group, o R' is a phenyl group, optionally substituted by one to three groups and in particular substituted by a group, selected from the group consisting of an alkyl group (C1-C4) , a fluoroalkyl group (C1-C4) , a fluoroalkoxy group (C1-C4) , a halogen atom and a hydroxy group, the phenyl group being preferably unsubstituted.

7. A compound of formula (I) according to claim 1, characterized in that R1 represents: an alkyl group (C1-C4) substituted by one or two groups selected from a -COORa group, a hydroxy group, a fluorine atom, an alkoxy group (C1-C4), and a benzyloxy group, such benzyloxy being optionally substituted at its phenyl group by a halogen atom, a spirobicyclic ring (C5-C11), or an R'-L- group, wherein L is either a single bond or an alkandiyl group (C1-C3), optionally substituted by a group selected from a hydroxy group and an alkoxy group (C1-C3), and R' is selected from the group consisting of: a cycloalkyl group (C3-C4), optionally substituted by one, two, or three groups selected from Ln / zznz / E / YiAi 398 of a halogen atom, an alkyl group (C1-C4), a hydroxy group and an alkoxy group (C1-C3), and a bridged cycloalkyl group (Cg-Cio),optionally substituted by one to three groups selected from a (C1-C4) alkyl group, a (C1-C4) alkoxy group, a halogen atom, a hydroxy group, an -OC(O)-Rd group, an -OC(O)-NHRd group, an -NH-C(O)-Rd group, an -SO2-Rd group, an -N(Re)2 group and a -COORa group, Ra represents a (C1-C4) alkyl group, Rd represents a (C1-C4) alkyl group or a cyclopropyl group and Re represents a (C1-C3) alkyl group, and wherein R2 represents a hydrogen atom or a (C1-C3) alkyl group, or any of its pharmaceutically acceptable salts.

8. A compound of formula (I) according to claim 1, characterized in that R1 represents: a fused phenyl group, selected from phenyl groups fused to a cycloalkyl (C5-Cg) or heterocycloalkyl (Cs-Cg) group, wherein the cycloalkyl (C5-C6) and heterocycloalkyl (Cs-Cg) group optionally comprises an unsaturation and is optionally substituted by an alkyl (C1-C4) group, a hydroxy group, a halogen atom, an alkoxy (C1-C3) group, and a -CORa group; a phenyl group, substituted by one or two groups selected from an alkyl (C1-Cg) group, a fluoroalkyl (C1-C3) group, a fluoroalkoxy (C1-C4) group, a halogen atom, and a heterocycloalkyl group. (C4-C7) such heterocycloalkyl (C4-C7) group is the same optionally substituted by an alkyl (C1-C4) group, or an R'-L- group, wherein or L is an alkandiyl (C1-C3) group, optionally substituted by a group chosen from a hydroxy group, an alkoxy (C1-C4) group,a -NRbRc group, a -COORa group and a halogen atom, and R' is a phenyl group, optionally substituted by one to three groups selected from the group consisting of an alkyl (Ci-Ce) group, a fluoroalkyl (C1-C4) group and a fluoroalkoxy (C1-C4) group, a halogen atom and a hydroxy group, wherein Ra is an alkyl (C1-C4) or a hydrogen atom and Rb and Rc are independently selected from alkyl (Ci-Cg) and a hydrogen atom, and wherein R2 represents a hydrogen atom or an alkyl (C1-C3) group, or any pharmaceutically acceptable salt thereof.

9. A compound of formula (I) according to any of the preceding claims, characterized in that R2 represents a hydrogen atom or a methyl group. fronr Ln / zznz / E / YiAi 400 10. A compound of formula (I) according to claim 1, characterized in that R1 represents an R'-L- group wherein R' is a (C3-C8) heteroaryl group, optionally substituted by one to three groups selected from a halogen atom, an (C1-C4) alkyl group, an (C1-C4) alkoxy group, and an N-methylpiperazinyl group, and L is an (C1-C3) alkandiyl or a single bond, and wherein R2 represents a hydrogen atom, or any pharmaceutically acceptable salt thereof.

11. A compound of formula (I) according to claim 1, characterized in that R1 represents an R'-L- group wherein R' is a (C3-C5) heterocycloalkyl group, optionally substituted by one to three groups selected from a hydroxy group, a (C1-C4) alkyl group, an oxo group, and a -COORa group, wherein Ra is as defined in claim 1, and L is a methylene or single bond, and wherein R2 represents a hydrogen atom, or any pharmaceutically acceptable salt thereof.

12. A compound of formula (I) according to any one of claims 1 to 5, characterized in that it is selected from: (1) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclopropylmethylamino)-1H-imidazol-5-one, (2) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclopropylamino)-1H-imidazol-5-one, (3) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclobutylamino)-1H-imidazol-5-one, (4) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclopentylamino)-1H-imidazol-5-one, (5) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- (cyclohexylmethylamino)-lH-imidazole-5-one, (6) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- (cyclohexylamine)-lH-imidazole-5-one, (7) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- (cycloheptylmethylamino)-lH-imidazole-5-one, (8) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- (cycloheptylamino)-lH-imidazole-5-one, (9) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(cyclooctylamino)-lH-imidazole-5-one, (10) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[ (3-hydroxy-2,2-dimethyl-propyl)amino]-lH-imidazole-5-one,(11) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2-(2- benciloxietilamino)-1H- imidazol-5-ona, (12) (±)-(45)-4-(1,3-Benzotiazol-6-ilmetilen)-2- fronr Ln / zznz / E / YiAi 402 [[cis-2-metilciclohexil]amino]-lH-imidazol-5-ona, (13) (43)-4-(1,3-Benzotiazol-6-ilmetilen) - 2 - [ [ (IR) - 1-ciclohexiletil]amino]-lH-imidazol-5-ona, (14) (42)-2-(1-Adamantilmetilamino)-4-(1,3- benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (15) (±)-(42)-2-[l-(1-Adamantil)etilamino]-4-(1,3- benzotiazol-6-ilmetilen)-lH-imidazol-5-ona, (16) (42)-2-(1-Adamantilamino)-4- (1,3-benzotiazol6-ilmetilen)-lH-imidazol-5-ona, (17) (42)-2-(2-Adamantilamino)-4-(1,3-benzotiazol- 6-ilmetilen)-lH-imidazol-5-ona, (18) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2 -[ [3,5- dimetil-l-adamantil]amino]-lH-imidazol-5-ona, (19) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(trans-5-hidroxi-2-adamantil)amino]-lH-imidazol-5-ona, (20) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2-[(3- hidroxi-l-adamantil)amino]-lH-imidazol-5-ona, (21) (42)-4-(1,3-Benzotiazol-6-ylmethylene)-2-[(3-metoxi-l-adamantil)amino]-lH-imidazol-5-ona, (22) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR,2R,3R,5S)-2,6,6-trimethylnorpinan-3-il]amino]-1Himidazol-5-ona, (23) (42)-4-(1,3-Benzotiazol-6-ilmethylene)-2-[[(1S,2S,3S,5R)-2,6,6-trimethylnorpinan-3-il]amino]-1H fronr Ln / zznz / E / YiAi imidazol-5-ona 403 (24) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(lR,2R,5R)-6,6-dimetilnorpinan-2-il]metilamino]-1Himidazol-5-ona, (25) (±)-(42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (espiro[2.5]octan-2-ilamino)-lH-imidazol-5-ona, (26) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (espiro[3.3]heptan-2-ilamino)-lH-imidazol-5-ona, (27) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2-[[(2R)- 1.7.7-trimethylnorbornan-2-il]amino]-lH-imidazol-5-ona, (28) (+)-(42)-4-(1,3-Benzotiazol-6-ilmethylene)-2-(norbornan-2-ilamino)-lH-imidazol-5-ona, (29) (42)-4-(1,3-Benzothiazol-6-ilmethylene)-2- [[(IR,2S,5R)-2-isopropyl-5-methyl-cyclohexyl]amino]-1Himidazol-5-ona, (30) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR)- 1-(cyclohexylmethyl)-2-hydroxy-ethyl]amino]-1H-imidazol-5-one, (31) (42)-4-(1,3-Benzothiazol-6-ylmethylene)—2 — [[(IR) — 1-(cyclopentylmethyl)-2-hydroxy-ethyl]amino]-1H-imidazol-5-one, (32) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR)- 1-(cyclobutylmethyl)-2-hydroxy-ethyl]amino]-1H-imidazol-5-one, (33) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR)- 1-(cyclopropylmethyl)-2-hydroxy-ethyl]amino]-1H-imidazol-5-one, (34) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR)1-(hydroxymethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one, fronr Ln / zznz / E / YiAi (35) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR)-404 1-(Methoxymethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one, (36) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(1S)-1-(hydroxymethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one, (37) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(1S)-1-(hydroxymethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one. 1-(Methoxymethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one, (38) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[ [ (IR)-1-(hydroxymethyl)propyl]amino]-1H-imidazol-5-one,(39) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(1S)- 1-(hydroxymethyl)propyl]amino]-1H-imidazol-5-one, (40) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[1-(fluoromethyl)-3-methyl-butyl]amino]-1H-imidazol-5-one, (41) (+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(1-cyclohexyl-2-hydroxy-ethyl)amino]-1H-imidazol-5-one, (42) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(1-cyclohexyl-2-methoxy-ethyl)amino]-1H-imidazol-5-one, (43) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ (2-cyclohexyl-2-hydroxy-ethyl)amino]-1H-imidazol-5-one, (44) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[(2-cyclohexyl-2-methoxy-ethyl)amino]-1H-imidazol-5-one, (45) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[cis-2-hydroxycyclopentyl]amino]-1H-imidazol-5-one, (46) (!) -(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-2-hydroxycyclopentyl]amino]-1H-imidazol-5-one, (47) (±) -(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-fronr Ln / zznz / E / YiAi 405 [[cis-2-methoxycyclopentyl]amino]-1H-imidazol-5-one, (48) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[trans-2-methoxycyclopentyl]amino]-1H-imidazol-5-one, (49) ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[cis-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (50) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ trans-2-hydroxycyclohexyl ]amino] -1H-imidazol-5-one, (51) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2 - [ [ (IR, 2S) -2-hydroxycyclohexyl ]amino] -1H-imidazol-5-one, (52) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(1S,2R)-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (53) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(1R,2R)-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (54) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(12,2S)-2-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (55) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[cis-3-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (56) (+)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-3-hydroxycyclohexyl]amino]-1H-imidazol-5-one, (57) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(trans-4-hydroxycyclohexyl)amino]-1H-imidazol-5-one, (58) (±) -(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[cis-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, (59) (±) -(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-2-methoxycyclohexyl]amino]-1H-imidazol-5-one, from Ln / zznz / E / YiAi 406 (60) (42)-4-(1,3-Benzothiazol-6-ylmethylene) -2- [ (trans-4-methoxycyclohexyl)amino]-1H-imidazol-5-one, (61) (±) -(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[cis-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (62) (+)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (63) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ (IR, 2R)-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (64) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2 - [[(1S,2S)-2-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (65) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[cis-3-hydroxycycloheptyl]amino]-1H-imidazol-5-one, (66) (+)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-3-hidroxycycloheptyl]amino]-lH-imidazol-5-ona, (67) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[cis-2-methoxycycloheptyl]amino]-lH-imidazol-5-ona, (68) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[trans-2-methoxycycloheptyl]amino]-lH-imidazol-5-ona, (69) (2S)-2-[[(4Z)-4-(1,3-benzothiazol-6-ylmethylene)- 5-oxo-1H-imidazol-2-yl]amino]-3-methyl-butanoato de methylo, (70) (2S)-2-[[(4Z)-4-(1,3-benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]propanoato de methylo, (71) (2S)-2-[[(4Z)-4-(1,3-benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-4-methyl-pentanoato de methylo, fronr Ln / zznz / E / YiAi 407 (72) (2R)-2-[[(4Ζ)-4-(1,3-benzothiazol-6- (73) (2S)-2-[[(4 2)-4-(1,3-benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-3-hydroxy-butanoato de methylo, (74) (42)-4-(1,3-Benzothiazol-6-ylmethylen)-2(bencylamino)-1H-imidazol-5-one, (75) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-(indan2-ylamino)-lH-imidazol-5-one, (76) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ (3,4 — dimethylphenyl)methylamino]-lH-ylmethylene, (77) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2 -[ (2,4 — dimethylphenyl)methylamino]-lH-imidazol-5-one, (78) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[2(trifluoromethyl)phenyl]methylamino]-lH-imidazol-5-one, (79) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2 - [ [ 2(trifluoromethoxy)phenyl]methylamino]-lH-imidazole-5-one, (80) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[cis-2-hydroxyindan-l-yl]amino]-lH-imidazole-5-one, (81) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[trans-2-hydroxyindan-1-i1]amino]-lH-imidazol-5-one, (82) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[(IR,2R)-2-hydroxyindan-l-yl]amino]-lH-imidazol-5-one, (83) (42) -4-(1,3-Benzothiazol-6-ylmethylene)-2-2-Fronzo / L / Y [[(1S,2S)-2-hydroxyindan-l-yl]amino]-lH-imidazole-5-one, (84) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[cis-2-methoxyindan-l-yl]amino]-l-H-imidazole,(85) ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylen)-2[[trans-2-methoxyindan-1-yl]amino]-1H-imidazol-5-one, (86) (2S)-2-[[(4 2)-4-(1,3-benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-3-phenyl-methylpropanoate, (87) (2R)-2-[[(42)- 4-(1, 3-benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-3-phenyl-methylpropanoate, (88) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[(2-fluoro-l-phenyl-ethyl)amino]-1H-imidazol-5-ona, (89) Dichlorohydrate de (+)-(42)-2-[(2-Amino-l-phenylethyl)amino]-4-(1,3-benzothiazol-6-ylmethylene)-lH-imidazol-5ona, (90) Dichlorohydrate of (±) -(42)-4-(1,3-Benzothiazol6-ylmethylene)-2-[[2-(methylamino)-1-phenyl-ethyl]amino]-1Himidazol-5-ona, (91) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[[2-(dimethylamino)-1-phenyl-ethyl]amino]-1H-imidazol-5-ona, (92) (±)-(42)-4-(1,3-Benzothiazol-6-ylmethylene)-2[(l-bencyl-2-hidroxy-ethyl)amino]-lH-imidazol-5-ona, (93) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2 - [ [ (IR) l-bencyl-2-hidroxy-ethyl]amino]-lH-imidazol-5-ona,fronr Ln / zznz / E / YiAi 409 (94) ( + ) -(4Ζ)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(l-benzyl-2-methoxy-ethyl)amino]-lH-imidazol-5-one, (95) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(2-hydroxy-l-phenyl-ethyl)amino]-lH-imidazole-5-one, (96) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[[(IR) 2-hydroxy-l-phenyl-ethyl]amino]-lH-imidazole-5-one, (97) (4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-[ [ (15) - 2-hydroxy-l-phenyl-ethyl]amino]-lH-imidazole-one, (98) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(2-methoxy-l-phenyl-ethyl)amino]-lH-imidazole-5-one, (99) (±)-(4Z)-4-(1,3-Benzothiazol-6-ylmethylene)-2-2- [(2-hydroxy-2-phenyl-ethyl)amino]-lH-imidazol-5-one, (100) ( + )-(4Z)- 4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(2-methoxy-2-phenyl-ethyl)amino]-lH-imidazol-5-one, (101) (±)-(4Z)-4-(l,3-Benzothiazol-6-ylmethylene)- 2-[(2-hydroxy-3-phenyl-propyl)amino]-lH-imidazol-5-one, (102) ( + )-(4Z)- 4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(2-methoxy-3-phenyl-propyl)amino]-lH-imidazol-5-one, (103) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(5-metilpirazin-2-il)metilamino]-lH-imidazol-5-ona, (104) (4 Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (2-piridilmetilamino)-lH-imidazol-5-ona, (105) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (3-piridilmetilamino)-lH-imidazol-5-ona, (106) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- fronr Ln / zznz / E / YiAi 410 (4-piridilmetilamino) -lH-imidazol-5-ona, (107) (45)-4-(1,3-Benzotiazol-6-ylmethylene)-2-[(5-metil-2-furyl)methylamino]-lH-imidazol-5-ona, (108) (45)-4-(1,3-Benzotiazol-6-ylmethylene)-2-[(4-metiltiazol-2-yl)methylamino]-lH-imidazol-5-ona, (109) (45)-4-(1,3-Benzotiazol-6-ylmethylene)-2-(3-imidazol-l-ylpropylamino)-lH-imidazol-5-ona, (110) (45)-4-(1,3-Benzotiazol-6-ylmethylene)-2-[2-(2-pyridyl)ethylamino]-lH-imidazol-5-ona, (111) (45)-2-(1,3-Benzotiazol-2-ylmethylamino)-4-(1,3-benzotiazol-6-ylmethylene)-lH-imidazol-5-ona, (112) (45)-4-(1,3-Benzotiazol-6-ylmethylene)-2-[(l-methyl-4-piperidil)methylamíno]-lH-imidazol-5-ona, (113) (45)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (tetrahidropiran-4-ilmetilamino)-lH-imidazol-5-ona, (114) 4 -[[[ (4Z)-4-(l,3-benzotiazol-6- ilmetilen)-5-oxo-lH-imidazol-2-il]amino]metil]piperidin-lcarboxilato de tero-butilo, (115) (45)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [ (7-metil-7-azaespiro[3.5]nonan-2-il)amino]-lH-imidazol-5ona, (116) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- (3-fluoro-4-metil-anilino)-lH-imidazol-5-ona, (117) (45) -4-(1,3-Benzotiazol-6-ilmetilen)-2- (4-fluoroanilino)-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi 411 (118) (4 Ζ) -4- (1,3-Benzotiazol-6-ilmetilen) -2- (4-hexilanilino)-lH-imidazol-5-ona, (119) (4Z) -4 - (1,3-Benzotiazol-6-ilmetilen)-2- [4-(4-metilpiperazin-l-il)anilino]-lH-imidazol-5-ona, (120) (4Z)-4-(1,3-Benzotiazol-6-ilmethylene)-2-[3-(difluorometoxi)anilino]-lH-imidazol-5-ona, (121) (4 Z)-2 -[(1-Acetilindo1in-6-il)amino]-4-(1,3-benzotiazol-6-ilmethylene)-lH-imidazol-5-ona, (122) (4 Z)-4 -(1,3-Benzothiazol-6-ylmethylene)-2- [3-(trifluoromethyl)anilino]-lH-imidazol-5-ona,(123) (4 Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (indan-5-ilamino)-lH-imidazol-5-ona, (124) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- (4-morfolinoanilino) -lJí-imidazol-5-ona, (125) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(l-metilindazol-7-il)amino]-lH-imidazol-5-ona, (126) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- (pyrimidin-2-ilamino)-lH-imidazol-5-ona, (127) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- (2-piridilamino)-lH-imidazol-5-ona, (128) (4 Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(l-metilpirazol-3-il)amino]-lH-imidazol-5-ona, (129) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [(2-metoxi-6-metil-3-pyridil)amino]-lH-imidazol-5-ona, (130) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2 fronr Ln / zznz / E / YiAi 412 (pyrimidin-5-ilamino) -lH-imidazol-5-ona, (131) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- (3-pyridlamino)-lH-imidazol-5-ona, (132) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- (1,3,4-tiadiazol-2-ilamino)-lH-imidazol-5-ona, (133) (4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- [[5-(4-methylpiperazin-l-yl)-2-pyridyl]amino]-lH-imidazol-5-one, (134) (4 Z)-4 -(1,3-Benzothiazol-6-ylmethylen)-2- [[6 —(4-methylpiperazin-l-yl)-3-pyridyl]amino]-lH-imidazol-5-one, (135) (4 Z)-4 -(1,3-Benzothiazol-6-ylmethylen)-2- [ [2-(4-methylpiperazin-l-yl)pyrimidin-5-yl]amino]-1H-imidazol5-one, (136) (4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- [[5-(4-methylpiperazin-l-yl)pyrimidin-2-yl]amino]-1H-imidazol5-one, (137) (4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- [[5-(4-methylpiperazin-l-yl)pyrazin-2-yl]amino]-1H-imidazol-5-one, (138) (4 Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- [[6-(4-methylpiperazin-l-yl)pyridazin-3-yl]amino]-1H-imidazol5-one, (139) (4Z)-4-(1,3-Benzothiazol-6-ylmethylen)-2- (tetrahydropyran-4-ylamino)-1H-imidazol-5-one, fronr Ln / zznz / E / YiAi 413 (140) 4-[[(4 Ζ) —4-(1,3-benzothiazol-6-ylmethylene)- 5-oxo-lH-imidazol-2-yl]amino]piperidin-l-carboxylate of terobutyl, (141) 4-[[(4 Z)-4-(1,3-benzotiazol-6-ilmetilen)- 5-oxo-lH-imidazol-2-il]amino]piperidin-l-carboxilato de etilo, (142) (4 Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [ (l-metil-4-piperidil)amino]-lH-imidazol-5-ona, (143) ( + )-(4Z)- 4-(1,3-Benzotiazol-6-ilmetilen)- 2-[(l-metil-3-piperidil)amino]-lH-imidazol-5-ona, (144) (4Z) -4-(1,3-Benzotiazol-6-ilmetilen)-2- (oxetan-3-ilamino)-lH-imidazol-5-ona, (145) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- [ [ (3R) -tetrahidrofuran-3-il] amino] -lJí-imidazol-5-ona, (146) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(3S)-tetrahidrofuran-3-il]amino]-lH-imidazol-5-ona, (147) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- [[(3R)-tetrahidropiran-3-il]amino]-lH-imidazol-5-ona, (148) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(3S)-tetrahidropiran-3-il]amino]-lH-imidazol-5-ona, (149) (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)- 2-[(6,6-dimetiltetrahidropiran-3-il)amino]-lH-imidazol-5-ona, (149A). (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(3R) / (3S)-6,6-dimethyltetrahydropyran-3-yl]amino]-1H fronr Ln / zznz / E / YiAi imidazole-5-one 414 (149Β). (4Ζ)-4-(1,3-Benzothiazole-6-ylmethylene)-2[[(3R) / (33)-6,6-dimethyltetrahydropyran-3-yl]amino]-1Himidazole-5-one, (150) (43)-4-(1,3-Benzothiazolene-6-ylmethylene)-2- [[(3R,4R)-4-hydroxytetrahydropyran-3-yl]amino]-lH-imidazole-5one, (151) (+)-(43)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-(oxepan-3-ylamino)-lB-imide, [+)-5-5-one, (+) (43)-4-(1,3-Benzothiazol-6- ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]piperidin-2-one, (153) (33)-3-[[(4Z)-4 - (1,3-Benzothiazol-6- ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]piperidin-2-one, (154) (53)-5-[[(43)-4-(1,3-Benzothiazol-6- ylmethylene)-5-oxo-lH-imidazol-2-yl]amino-pyridine-2-one, (155) (±)-(43)-4-(l,3-Benzothiazol-6-ylmethylene)- 2- [ (3, 3-difluorocyclopentyl) amino] -llí-imidazol-5-one, (156) (43)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(4,4-difluorocyclohexyl)amino]-lH-imidazol-5-one, (157) (±)-(43)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(3,3-difluorociclohexil)amino]-lH-imidazol-5-ona, (158) (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)- 2-[(2,2-difluorociclohexil)amino]-lH-imidazol-5-ona, (159) ( + )-(4Z)- 4-(1,3-Benzotiazol-6-ilmetilen)- 2-[(3,3-difluorocicloheptil)amino]-lH-imidazol-5-ona, (160) (4Z) -4-(1,3-Benzotiazol-6-ilmetilen)-2- fronr Ln / zznz / E / YiAi 415 [[(IR)-1-(fluorometil)-3-metil-butil]amino]-lH-imidazol-5ona, (161) (4Z) -4 - (1,3-Benzotiazol-6-ilmetilen)-2- [[(1S)-1-(fluorometil)-3-metil-butil]amino]-1H-imidazol-5ona, (162) Acetato de [3-[[(4Z)-4-(1,3-Benzotiazol6-ilmetilen)-5-oxo-lH-imidazol-2-il]amino]-1-adamantilo], (163) 2,2-dimetilpropanoato de [3-[[(4Z)-4- (1,3-Benzotiazol-6-ilmetilen)-5-oxo-lH-imidazol-2-il]amino]1-adamantilo], (164) (4 Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [[(IR,2R)-2-metoxiciclopentil]amino]-lH-imidazol-5-ona, (165) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2- [[(1S,2S)-2-metoxiciclopentil]amino]-lH-imidazol-5-ona, (166) (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR,2R)-2-metoxiciclohexil]amino]-lH-imidazol-5-ona, (167) (4 Z)-4 -(1,3-Benzotiazol-6-ilmetilen)-2[[(1S,2S)-2-metoxiciclohexil]amino]-lH-imidazol-5-ona, (168) (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)- 2-[[cis-3-metoxicic1ohexi1]amino]-lH-imidazol-5-ona, (169) (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)- 2-[[trans-3-metoxiciclohexil]amino]-lH-imidazol-5-ona, (169A) . (4Z)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR,3R) / (1S,3S)-3-metoxiciclohexil]amino]-lH-imidazol-5 fronr Ln / zznz / E / YiAi ona 416 (169Β) . (45)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR,3R) / (15,35)-3-metoxiciclohexil]amino]-lfí-imidazol-5ona, (170) (+)-(45)-4-(1,3-Benzotiazol-6-ilmetilen)- 2-[[cis-4-hidroxicicloheptil]amino]-lH-imidazol-5-ona, (171) (±)-(4Z)-4-(l,3-Benzotiazol-6-ilmetilen)- 2-[[trans-4-hidroxicicloheptil]amino]-lH-imidazol-5-ona, (171A) . (4Z) -4-(1,3-Benzotiazol-6-ilmetilen)-2[ [ (IR, 4R) / (15, 45) -4-hidroxicicloheptil] amino] -lH-imidazol-5ona, (171B) . (45)-4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR,4R) / (15,45)-4-hydroxycicloheptil]amino]-lH-imidazol-5one, (172) (+)-(45)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[cis-3-methoxycicloheptil]amino]-lH-imidazol-5-one, (173) (±)-(45)-4-(1,3-Benzothiazol-6-ylmethylene)- 2-[[trans-3-methoxyciclohepti1]amino]-lH-imidazol-5-one, (174) (+)-(45)-4-(1,3-Benzothiazol-6-ylmethylene)- 2 - [ [ cis-4-methoxyciclohepti 1 ] amino]-llí-imidazol-5-one, (175) (±)-(45)-4-(l,3-benzothiazol-6-ylmethylene)- 2-[[trans-4-methoxyciclohepti1]amino]-lH-imidazol-5-ona, (176) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [ [ (IR) -2-methoxy-l-fenil-ethyl] amino] -l / í-imidazol-5-ona, (177) (45)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(15)-2-methoxy-l-fenil-etil]amino]-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi 417 (178) (4 Z) -4-(1,3-Benzothiazol-6-ylmethylene) -2- [[(2R)-2-hydroxy-2-fenil-etil]amino]-lH-imidazol-5-ona, (179) (4Z) -4 (1,3-Benzothiazol-6-ylmethylene)-2- [[(2S)-2-hidroxi-2-fenil-etil]amino]-lH-imidazol-5-ona, (180) Dichlorhidrato de (4Z)-2-[ [ (IR)-2-Amino-lfenil-etil]amino]-4-(1,3-benzothiazol-6-ylmethylene)-1Chimidazol-5-one, (181) Dichlorohydrate of (4Z)-2-[ [ (1S)-2-Amino-lphenyl-ethyl]amino]-4-(1,3-benzothiazol-6-ylmethylene)-1Chimidazol-6-ylmethylene (4) —4—2 (1,3-Benzothiazol-6-ylmethylene)-2- [[(3R)-quinuclidin-3-yl]amino]-lH-imidazol-5-one, (183) (4 Z)-4 -(1,3-Benzothiazol-6-ylmethylene)-2- [[(3S)-quinuclidin-3-yl]amino]-lH-imidazol-5-one, (184) (±)-(4Z)-4-(l,3-Benzothiazol-6-ylmethylene)- 2-(tetrahydrothiopyran3-ylamino)-lH-imidazol-5-one, (185) (±)-(4Z)-4-(l,3-Benzothiazol-6-ylmethylene)- 2-(1,4-dioxepan-6-ylamino)-lH-imidazol-5-one, (186) (±)-(4Z)-4-(l,3-Benzothiazol-6-ylmethylene)- 2-[(2-oxopyrrolidin-3-yl)amino]-lH-imidazol-5-one, (187) (±)-(4Z)-4-(l,3-Benzothiazol-6-ylmethylene)- 2-[(l-methyl-2-oxo-pyrrolidin-3-yl)amino]-l-H-imidazole, (+18) )-(4Z)- 4-(1,3-Benzothiazol-6-ylmethylene)- 2-[(4,4-dimethyl-2-oxo-pyrrolidin-3-yl)amino]-lH-imidazole-5 fronr Ln / zznz / E / YiAi has been 418 (189) (R) (3) (3-4-Ζ) -4-(1,3-Benzothiazol-6- ylmethylene)-5-oxo-lH-imidazol-2-yl]amino]piperidin-2-one,(190) (±) -3- [ [ (42) -4-(1,3-Benzothiazol-6- ylmethylen)-5-oxo-1H-imidazol-2-yl]amino]-1-methyl-piperidin-2ona, (191) (±)-(42)- 4-(1,3-Benzothiazol-6-ylmethylen)- 2- [ (3-methyl-2-oxo-pyrrolidin-3-yl) amino] -1 Jí-imidazol-5-ona, (192) ( + )-(42)-4-(1,3-Benzothiazol-6-ylmethylen)2-[(1,3-dimethyl-2-oxo-pyrrolidin-3-yl)amino]-1H-imidazol-5ona, (192A) . (42) -4-(1,3-Benzothiazol-6-ylmethylene)-2[[(3R) / (3S)-1,3-dimethyl-2-oxo-pyrrolidin-3-yl]amino]-1Himidazol-5-ona, (192B) . (42)-4-(1,3-Benzotlazol-6-ylmethylene)-2[[(3R) / (3S)-1,3-dimethyl-2-oxo-pyrrolidin-3-yl]amino]-1Himidazol-5-ona, (193) (42)-4-(1,3-Benzotlazol-6-ylmethylene)-2- [[(3S,4S)-4-hidroxitetrahidropyran-3-yl]amino]-lH-imidazol-5ona, (194) (42)-2-(3-Noradamantilamino)-4-(1,3-benzothiazol-6-ylmethylene)-lH-imidazol-5-ona, (195) W-terc-butylcarbamate de [3-[[(42)-4- (1,3-Benzothiazol-6-ylmethylene)-5-oxo-1H-imidazol-2-yl]amino]1-adamantyl], (196) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- fronr Ln / zznz / E / YiAi 419 [(3-fluoro-l-adamantil)amino]-lH-imidazol-5-ona, (197) (4 2) -4-(1,3-Benzotiazol-6-ilmetilen)-2[[(IR)-1-(terc-butoximetil)-3-metil-butil]amino]-lH-imidazol5-ona, (198) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2- [ [ (IR) -2-terc-butoxi-l-fenil-etil] amino] -1 Jí-imidazol-5-ona, (199) 7\7-[3-[[(4Z)-4-(l, 3-Benzotiazol-6ylmethylene)-5-oxo-lH-imidazol-2-il]amino]-1adamantil]acetamida, (200) W-[3-[[ (42)-4-(1,3-Benzotiazol-6-ilmethylene)-5-oxo-lH-imidazol-2-il]amino]-1adamantil]cyclopropancarboxamida, (201) N-[3-[[(42) Z)-4-(1,3-Benzotiazol-6-ylmethyl)-5-oxo-lH-imidazol-2-il]amino]-1adamantil]metansulfonamida, (202) N-[3-[[(42)-4-(1,3-Benzotiazol-6- ilmetilen)-5-oxo-lH-imidazol-2-il]amino]-1adamantil]cyclopropansulfonamida, (203) (42)-4-(1,3-Benzotiazol-6-ilmetilen)-2-[[3-(dimethylamino)-1-adamantil]amino]-lH-imidazol-5-ona, (204) 2-[[(4Z)-4-(1,3-benzotiazol-6-ylmethylene)5-oxo-lH-imidazol-2-yl]amino]adamantan-2-carboxylato de methyl,(205) (42)-2-(Ciclohexilamino)-4-[(2-meti1-1,3- benzotiazol-6-il)metilen]-lH-imidazol-5-ona, fronr Ln / zznz / E / YiAi 420 (206) (42)-2-(Cicloheptilamino)-4-[(2-metil- 1,3-be nzotiazol-6-il)metilen]-lfí-imidazol-5-ona, (207) (42)-2-[[(IR)-1-(Metoximetil)-3-metil- butil] amino]-4-[(2-metil-l,3-benzotiazol-6-il)metilen]-1Himidazol-5-ona, (208) (42)-2-[[(IR)-2-Metoxi-l-phenyl-ethyl]amino]-4-[(2-metil-l,3-benzotiazol-6-yl)methylene]-lHimidazol-5-ona, (209) (42)-2-(1-Adamantylamino)-4-[(2-metil- 1,3-be nzotiazol-6-yl)methylene]-lH-imidazol-5-ona, y (210) (42)-2-[(3-Hydroxy-l-adamantil)amino]-4-[(2-metil-l,3-benzotiazol-6-yl)methylene]-lH-imidazol-5-ona, (211) (42)-4-(1,3-Benzotiazol-6-ylmethylene)-2- [(3,5-dihidroxy-l-adamantil)amino]-lH-imidazol-5-ona, (212) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [(3,5.7-trifluoro-l-adamantil)amino]-lH-imidazol-5-ona, (213) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(etoximetil)-3-methyl-butyl]amino]-lH-imidazol-5-ona, (214) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-(benzyloxymethyl)-3-methyl-butyl]amino]-lH-imidazole-5one, (215) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- [[(IR)-1-[(4-fluorophenyl)methoxymethyl]-3-methyl-butyl]amino]lH-imidazole-5-one, (216) (42)-4-(1,3-Benzothiazol-6-ylmethylene)-2- fronr Ln / zznz / E / YiAi 421 [[(IR)-1-(cyclopropoxymethyl)-3-methyl-butyl]amino]-1Himidazol-5-one, or any of its pharmaceutically acceptable salts., 13. A pharmaceutical composition, characterized in that it comprises at least one compound according to any one of claims 1 to 11, or any of its pharmaceutically acceptable salts or according to claim 12.

14. A synthesis process for manufacturing a compound of formula (I), according to any of claims 1 to 11 or any of its pharmaceutically acceptable salts or according to claim 12 or any of its pharmaceutically acceptable salts, characterized in that it comprises at least one step of coupling a compound of formula (II) below Alk-S fronr Ln / zznz / E / YiAi wherein Alk is a (C1-C5) alkyl, with an amine of formula R1NH2 wherein R1 and R2 are as defined according to any of claims 1 to 11.

15. A synthetic intermediate of formula (II) below 422 Alk-S fronr Ln / zznz / E / YiAi characterized in that Alk is an alkyl (C1-C5) , in particular Alk is selected from the group consisting of an ethyl and a methyl and R2 is in accordance with any of claims 1 to 11.

16. A compound of formula (I) according to any one of claims 1 to 11 or any of its pharmaceutically acceptable salts, or at least any one of the compounds (1) to (216) according to claim 12 or any of its pharmaceutically acceptable salts, for use as a medicament.

17. A compound of formula (I) according to any one of claims 1 to 11 or any pharmaceutically acceptable salts thereof, or at least any one of compounds (1) to (216), according to claim 12 or any pharmaceutically acceptable salts thereof, for use in the treatment and / or prevention of a selected disease of cognitive deficits associated with Down syndrome (Trisomy 21); Alzheimer's disease and related diseases; dementia; tauopathies; and other neurodegenerative diseases (Parkinson's disease; Pick's disease, including Niemann-Pick disease type C); CDKL5 deficiency disorder; McDermid syndrome; autism; type 1 and type 2 diabetes; abnormal folate and methionine metabolism; osteoarthritis, in particular osteoarthritis of the knee; Duchenne muscular dystrophy;Various types of cancer, such as brain cancer, including glioblastoma, leukemia, including megakaryoblastic leukemia and acute lymphoblastic leukemia, squamous cell carcinoma of the head and neck, pancreatic cancer, including pancreatic ductal adenocarcinoma, prostate cancer, gastrointestinal cancer, breast cancer, such as triple-negative breast cancer (TNBC), tissue cancer, including liposarcoma, Hedgehog / GLI-dependent cancer, liver cancer, including hepatocellular carcinoma, and viral infections, such as those caused by human immunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV), influenza A, herpes virus, rhesus macaque cytomegalovirus, varicella-zoster virus, herpes simplex virus (HSV), hepatitis C virus, chikungunya virus, dengue virus, influenza virus, and severe acute respiratory syndrome coronavirus (SARS), cytomegalovirus and human papillomavirus;neuroinflammation; anemia; infections caused by single-celled parasites, such as malaria, leishmaniasis, Chagas disease, and sleeping sickness (Trypanosoma sp.), and livestock diseases caused by single-celled pathogens; and to regulate body temperature. fronr Ln / zznz / E / YiAi 424; 18. A compound of formula (I) for use according to any one of claims 1 to 11, or any of its pharmaceutically acceptable salts, or at least any one of the compounds (1) to (216) according to claim 12 or any of its pharmaceutically acceptable salts, for use in the treatment and / or prevention of a selected disease from Down syndrome, Alzheimer's disease, dementia, tauopathies, Parkinson's disease, Niemann-Pick disease type C, CDKL5 deficiency disorder and Phelan-McDermid syndrome and their associated cognitive and motor conditions and type 1 and type 2 diabetes.