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Rapid Access to a Broad Range of 6?-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

Light-emitting firefly luciferin analogues contain electron-donating groups in the 6?-position, but the scope of known 6?-substitution remains narrow. A two-step route to a broad range of 6?-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6?-functionality. This chemistry allowed direct access to “caged” amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.

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NOVEL COMPOUND USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES

A novel compound able to inhibit JAK is disclosed, this compound may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, inflammatory conditions, autoimmune diseases, proliferative diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformations, and/or diseases associated with hypersecretion of IL6.

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Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) ? Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

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Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects.

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PROTECTED MONOMER AND METHOD OF FINAL DEPROTECTION FOR RNA SYNTHESIS

A nucleoside monomer that is protected by a thionocarbamate protecting group is provided, as well as a method for making a polynucleotide that uses the same. Also provided is a polynucleotide synthesis method that employs a diamine to deprotect a protected polynucleotide.

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CATHEPSIN CYSTEINE PROTEASE INHIBITORS

This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

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Chemotherapeutically active nitro compounds. 4,5-Nitroimidazoles (Part II)

More than 170 1-methyl-5-nitroimidazoles substituted in the 2-position via an aminomethyl, thiomethyl, sulphinylmethyl or sulphonylmethyl group were synthesized and tested for their effect against various protozoa. In the NMRI mouse which had been i.p. infected with Trichomonas fetus 2 compounds showed an effect superior to that of tinidazole and 31 showed similarly good efficacy as that compound. In comparison with metronidazole 54 preparations proved to be distinctly more active, while 34 others lay in the range of efficacy of the standard compound. A large majority of the most active derivatives is substituted in the 2-position via a C-S bridge with heterocyclics, particularly with a pyridyl radical. An effect against Entamoeba histolytica in the intrahepatically infected golden hamster was observed much less often. Only 14 preparations developed a systemic effect comparable with that of metronidazole. In the NMRI mouse infected i.p. with Trypanosoma brucei or s.c. with T. cruzi parasitemia was clearly influenced by 11 compounds. With a few exceptions a trypanocidal effect against T. brucei occurred only at high doses. Only 3 compounds showed pronounced suppressive activity against blood forms of T. cruzi and only after prolonged treatment. The structure-activity relationship of the new 5-nitroimidazoles is discussed.

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PIPERIDINE DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS

The present application relates to compounds of formula (I) wherein the definitions are as described in claim 1. It has been found that the present compounds are high potential NK-3 receptor antagonists for the treatment of depression, pain, psychosis, Parkinson’s disease, schizophrenia, anxiety and attention deficit hyperactivity disorder (ADHD).

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FILGOTINIB: Tyrosine-protein kinase JAK1 inhibitor, treatment of rheumatoid arthritis, treatment of crohn’s disease

Rheumatoid arthritis (RA), a chronic autoimmune inflammatory disease, is associated with pain, progressive disability, systemic comorbidities and early death. Filgotinib (GLPG-0634), a new selective tyrosine-protein kinase (JAK1) inhibitor, is currently in phase II clinical trials for the treatment of RA and Crohn’s disease. In in vitro biochemical and cellular and human whole blood assays, filgotinib showed selective potency, inhibiting JAK1 in the nanomolar range. In models of RA and Crohn’s disease in vivo in rodents it showed antiinflammatory efficacy. In a proof-of-concept trial in 36 RA patients with insufficient response to methotrexate, at doses of 100 mg b.i.d. and 200 mg once daily 91.7% and 75% of patients reached ACR20 scores, respectively. The pooled values for ACR20, DAS28 and C-reactive protein (CRP) change versus placebo at week 4 reached statistical significance. Of note, typical side effects of non-selective JAK inhibitors, i.e., anemia and increases in LDL cholesterol, liver enzymes and creatinine, were not detected.

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TETRAHYDROQUINOXALINE UREA DERIVATIVES, PREPARATION THEREOF, AND THERAPEUTIC USE THEREOF

The invention relates to compounds of formula (I), where: A is a bond, an oxygen, or an ?CH2? group; Ar1 is a phenyl or heteroaryl group; Ar2 is a phenyl, heteroaryl, or heterocycloalkyl group; R1a,b,c and R2a,b,c are hydrogen or halogen, or an alkyl, cycloalkyl, or lkyl-cycloalkyl group optionally, substituted by one or more halogen atoms, or a ?OR5 (hydroxy or alkoxy), hydroxy-alkyl, alkoxy-alkyl, alkoxy-alkoxy, halogenoalkyl, ?O-halogenoalkyl, oxo, ?CO-alkyl, ?CO-alkyl-NR6R7, ?CO-halogenoalkyl, ?COOR5, alkyl-COOR5, ?O-alkyl-COOR5, ?SO2-alkyl, ?SO2-cycloalkyl, ?SO2-alkyl-cycloalkyl, ?SO2-alkyl-OR5, ?SO2-alkyl-COOR5, ?SO2-alkyl-NR6R7, ?SO2-halogenoalkyl, alkyl-SO2-alkyl, ?SO2?NR6R7, ?SO2-alkyl-O-alkyl-OR5, ?CONR6R7, -alkyl-CONR6R7, or -alkyl-NR6R7 group, or further R1a, R1b, and R1c are bonded to R2a, R2b, R2c, respectively, and to the carbon atom having same, and are -alkyl-O?; R3 is a hydrogen atom or an alkyl group; R4 is a hydrogen or halogen atom or a cyano, ?OR5, hydroxyalkyl, ?COOR5, ?NR6R7, ONR6R7, ?SO2-alkyl, SO2?NR6R7, ?NR6?COOR5, ?NR6?COR5, or ?CO?NR6-alkyl-OR5 group; R5, R6, and R7 are a hydrogen, or an alkyl or alkyl-phenyl group; and R8 is an alkyl, alkyl-Si(alkyl)3, ?SO2-alkyl-Si(alkyl)3, phenyl, alkoxy-imino group, or alkyl-cycloalkyl group optionally substituted by one or more halogen atoms or one or more hydroxyl or hydroxyl-alkyl groups; or R8 and R9, together with the carbon atoms to which they are bonded, form a cycloalkyl group optionally substituted by one or more halogen atoms or one or more carboxy groups; and R9 is a hydrogen atom or an alkyl group; with the proviso that, when R8 is an alkyl group, it is bonded onto the Ar2 silicon atom. The invention also relates to a method for preparing same and to the therapeutic use thereof.

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