Patent EA-004858-B1 (EA)
Title: Novel tetrahydropyridines, preparation method and pharmaceutical compositions containing same
Inventor: BARONI MARCO
IPC: A61K31/444
Filed: 2000-12-29
Abstract: 1. A compound of formula (I): in which R1 represents a hydrogen or halogen atom, or a group CF3; R2 and R3 represent, independently, a hydrogen atom or a methyl group; n and n' each represent, independently, 0 or 1; * represents the positions of attachment; A represents N or CH; X represents a sulfur or oxygen atom; R4 and R5 represent, independently, a hydrogen atom or a (C1-C6) alkyl group; and their salts or solvates. 2. The compound as claimed in claim 1, in which n is zero. 3. The compound as claimed in claim 1, in which R1 is in position 3 of the benzene. 4. The compound as claimed in claim 1, in which R2 and R3 are each a hydrogen atom. 5. The compound as claimed in claim 1, in which R1 is a group CF3. 6. The compound as claimed in claim 1, in which R4 and R5 are each a methyl group. 7. A method for preparing a compound of claim 1 wherein (a) the compound of formula (II): in which A and R1 are defined as in claim 1, is reacted with a functional derivative of the acid of formula (III): in which R2, R3, R4 R5, n and X are as defined in claim 1, (b) the carbonyl group of the compound of formula (IV): is reduced, (c) the intermediate piperidinol of formula (V): is dehydrated, (d) the compound of formula (I) thus obtained is isolated and, optionally, it is transformed into one of its salts or solvates, or its N-oxide. 8. A method for preparing a compound of claim 1 wherein a tetrahydropyridine of formula (VI): in which A and R1 are as defined in claim 1, is condensed with a compound of formula (VII): in which R2, R3, R4, R5, n and X are as defined above and Q is a leaving group, the compound of formula (I) thus obtained is isolated and is optionally transformed into one of its salts or solvates, or into its N-oxide. 9. A pharmaceutical composition containing, as active principle, a compound of formula (I) as claimed in claim 1, or one of its pharmaceutically acceptable salts or solvates. 10. The composition as claimed in claim 9 wherein it contains from 0.01 to 50 mg of active principle. 11. Use the composition of formula (I) as claimed in claim 1 or one of its pharmaceutically acceptable salts or solvates for preparing medicaments in the treatment of diseases related to immune and inflammatory disorders, atherosclerosis, autoimmune diseases, diseases which lead to the demyelinization of neurons, asthma, rheumatoid arthritis, fibrotic diseases, idiopathic pulmonary fibrosis, cystic fibrosis, glumerulonephritis, rheumatoid spondylitis, osteoarthritis, gout, bone and cartilage resorption, osteoporosis, Paget's disease, multiple myeloma, uveoretinitis, septic shock, septicemia, endotoxic shock, graft-versus-host reaction, graft rejection, adult respiratory distress syndrome, silicosis, asbestosis, pulmonary sarcoidosis, Crohn's disease, ulcerative colitis, amyotrophic lateral sclerosis, Alzheimer's disease, Parkinson's disease, lupus erythematosus disseminatus, hemodynamic shock, ischemic pathological conditions, postischemic reperfusion injuries, malaria, mycobacterial infections, meningitis, leprosy, viral infections, AIDS-related opportunistic infections, tuberculosis, psoriasis, atopic and contact dermatosis, diabetes, cachexia, cancer and radiation-mediated damage.