2,4-diaminoquinazoline derivatives and medical uses thereof
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A methyl, pharmaceutical technology, applied in the field of medical use in the field of therapy, can solve the problem of complicated methods
Pending Publication Date: 2020-10-30
JANSSEN SCI IRELAND UC
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This can complicate the use of experimental animals as models of human innate immunity
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[0142] Table 1:
[0143]
[0144]
[0145] Compound preparation
[0146] 2-Amino-5-bromoquinazolin-4-ol. The title compound was prepared following a procedure similar to that described for 2-amino-6,7-difluoroquinazolin-4-ol. Rt: 1.16, m / z=240 / 242 [M+H], method: G.
[0147] (R)-2-((2-Amino-5-bromoquinazolin-4-yl)amino)hexan-1-ol. 2-Amino-5-bromoquinazolin-4-ol (2.4g, 8.68mmol), D-norleucinol (2.75g, 23.43mmol), DBU (3.9mL, 26.0mmol) and BOP (4.61g , 10.42 mmol) in anhydrous DMF (40 mL) was stirred at room temperature for 2 hours and concentrated to give the title product. Rt: 2.16, m / z=339 / 341 [M+H], method: D.
[0148] (R)-2-((2-Amino-5-cyclopropylquinazolin-4-yl)amino)hexan-1-ol (1). (R)-2-((2-Amino-5-bromoquinazolin-4-yl)amino)hexan-1-ol (200mg, 0.59mmol), cyclopropylboronic acid (151mg, 1.77mmol), and A mixture of potassium phosphate (375 mg, 1.77 mmol) in dioxane (10 mL) and water (0.1 mL) was purged with nitrogen for 10 min. Add PdCl 2 (dppf) (38mg, 0....
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Abstract
This application relates to quinazoline derivatives of formula (I), pharmaceutical compositions comprising the compounds of formula (I), and the use of the compounds of formula (I) in the treatment orprevention of a viral infection, of a virus-induced disease, of cancer or of an allergy. In formula (I), R<1> is a C<3-8> alkyl, optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, amino, nitrile, ester, amide, C<1-3> alkyl, or C<1-3> alkoxy, the carbon of R<1> bonded to the amine in the 4-position of the quinazoline is in (R)-configuration, R<2> ishydrogen, deuterium, fluorine, chlorine, methyl, methoxy, cyclopropyl, trifluoromethyl, or carboxylic amide, wherein each of methyl, methoxy and cyclopropyl is optionally substituted by one or more substituents independently selected from fluorine and nitrile, R<3> is hydrogen or deuterium, R<4> is hydrogen, deuterium, fluorine, methyl, carboxylic ester, carboxylic amide, nitrile, cyclopropyl, C<4-7> heterocycle, or 5-membered heteroaryl group, wherein each of methyl, cyclopropyl, C<4-7> heterocycle and 5-membered heteroaryl group is optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, or methyl, R<5> is hydrogen, deuterium, fluorine, chlorine, methyl, or methoxy, provided that at least one of R<2>, R<3>, R<4> and R<5> is not hydrogen.
Description
technical field [0001] The present application describes quinazoline derivatives, processes for their preparation, pharmaceutical compositions and medical use, more particularly in the therapeutic field. The means described in this application are suitable for modulating (more particularly agonizing) Toll-like receptors (TLRs), more particularly TLR8. The means described in this application are especially useful in the treatment or prevention of diseases or disorders (eg viral infections, immune or inflammatory disorders). Background technique [0002] Toll-like receptors are major transmembrane proteins characterized by a leucine-rich extracellular domain and a cytoplasmic extension containing a conserved region. The innate immune system can recognize pathogen-associated molecular patterns via these TLRs expressed on the cell surface of certain types of immune cells. Recognition of foreign pathogens activates cytokine production and upregulation of co-stimulatory molecule...
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