4-phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives

C - Chemistry – Metallurgy – 07 – D

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C07D 239/42 (2006.01) A61K 31/505 (2006.01) A61K 31/506 (2006.01) A61P 9/10 (2006.01) A61P 19/10 (2006.01) C07D 239/34 (2006.01) C07D 239/36 (2006.01) C07D 239/38 (2006.01) C07D 401/04 (2006.01) C07D 401/12 (2006.01) C07D 403/04 (2006.01) C07D 403/12 (2006.01)

Patent

CA 2621040

The invention relates to 4-phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives having Formula (I) wherein R represents 1-3 optional substituents independently selected from (C1-4)- alkyl (optionally substituted with one or more halogens), (C1-4)alkyloxy (optionally substituted with one or more halogens) and halogen; X is NR1, O or S; R1 is H or (C1-4)alkyl; Y is (C1- 4)alkyl, benzyl or (C2-6)alkyl, substituted with a group selected from OH, (C1- 4)alkyloxy, NR2R3, a 4-8 membered saturated heterocyclic ring comprising 1 or 2 heteroatoms selected from O, S and NR4, and a 5 or 6-membered aromatic heterocyclic group comprising 1-4 N atoms; or R1 and Y form together with the nitrogen to which they are bonded a 5-8 membered saturated heterocyclic ring, optionally comprising a further heteroatom selected from O, S, NR4 and NO; the ring being optionally substituted with NR2R3 or with 1 to 4 (C1-3)alkyl groups; R2 and R3 are independently H or (C1-4)alkyl; or R2 and R3 form together with the nitrogen to which they are bonded a 4-8 membered saturated heterocyclic ring, optionally comprising a further heteroatom selected from O, S and NR4; R4 is H, (C1-6)alkyl,(C3-6) cycloalkyl, (C3-6)cycloalkyl(C1- 4)alkyl, (C1-4)alkyloxy-(C1-4)alkyl, benzyl, amido- (C1-4)alkyl, (C1- 6)alkyloxycarbonyl(C1-4)alkyl or carboxy(C1-4)alkyl; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of these 4-phenyl-6-substituted-pyrimidine-2- carbonitrile derivatives for the preparation of a medicament for the treatment of cathepsin K and cathepsin S related disorders, e.g. osteoporosis, atherosclerosis, inflammation and immune disorders such as rheumatoid arthritis and chronic pain.

La présente invention concerne des dérivés de 4-phényl-6-substitué-pyrimidine-2-carbonitrile de formule (I) dans laquelle R représente de 1 à 3 substituants facultatifs indépendamment choisis parmi un (C1-4)-alkyle (portant facultativement une substitution par un ou plusieurs halogènes), un (C1-4)alkyloxy (portant facultativement une substitution par un ou plusieurs halogènes) et un halogène ; X est NR1, O ou S ; R1 est H ou un (C1-4)alkyle ; Y est un (C1-4)alkyle, un benzyle ou un (C2-6)alkyle, portant une substitution par un groupe choisi parmi OH, un (C1-4)alkyloxy, NR2R3, un noyau hétérocyclique saturé de 4 à 8 chaînons comprenant 1 ou 2 hétéroatomes choisis parmi O, S et NR4, et un groupe hétérocyclique aromatique de 5 ou 6 chaînons comprenant de 1 à 4 atomes N ; ou R1 et Y forment avec l'azote auquel ils sont liés un noyau hétérocyclique saturé de 5 à 8 chaînons, comprenant facultativement un hétéroatome supplémentaire choisi parmi O, S, NR4 et NO ; le noyau portant facultativement une substitution par NR2R3 ou par 1 à 4 groupes (C1-3)alkyle ; R2 et R3 sont indépendamment H ou un (C1-4)alkyle ; ou R2 et R3 forment avec l'azote auquel ils sont liés un noyau hétérocyclique saturé de 4 à 8 chaînons, comprenant facultativement un hétéroatome supplémentaire choisi parmi O, S et NR4 ; R4 est H, un (C1-6)alkyle, un (C3-6)cycloalkyle, un (C3-6)cycloalkyl(C1-4)alkyle, un (C1-4)alkyloxy-(C1-4)alkyle, un benzyle, un amido-(C1-4)alkyle, un (C1-6)alkyloxycarbonyl(C1-4)alkyle ou un carboxy(C1-4)alkyle ; ou un de leurs sels pharmaceutiquement acceptable. L'invention concerne également des compositions pharmaceutiques comprenant lesdits dérivés, ainsi que l'utilisation de ces dérivés de 4-phényl-6-substitué-pyrimidine-2-carbonitrile pour la préparation d'un médicament destiné au traitement de troubles liés à la cathepsine K et à la cathepsine S tels que l'ostéoporose, l'athérosclérose, l'inflammation, des troubles immunitaires tels que la polyarthrite rhumatoïde et la douleur chronique.

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