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US 6,747,035 B2Granted
1-alkyl or 1-cycloalkyltriazolo[4,3-a]quinazolin-5-ones as phosphodiesterase inhibitors
AssigneeWarner-Lambert Company
InventorsBernard Guadillière, Remi Lavalette
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of formula (I), in which R1, R2 and R3 are as defined in the description, their use as medicaments, the process for their preparation and their use for the treatment of pathologies in which therapy by a PDE4 inhibitor is relevant.
Claims8
A compound of formula (I),
- in which
- R1 is:
- hydroxyl, halogen, nitro, mercapto, cyano or carboxyl,
- lower alkyl or lower alkoxy, these groups being optionally substituted with 1,2 or 3 halogen atoms, or
- —NR4R5 in which R4 and R5 are the same or different and are:
- H,
- lower alkyl, optionally substituted with 1,2 or 3 halogen, hydroxyl, cyano and lower alkoxy, or
- C(═O)R6 in which R6 is selected from:
- lower alkyl optionally substituted with OR7, or SR7 and
- —X1-cycloalkyl optionally substituted with OR7, SR7, NR7R8 or with a linear or branched C1-C4 alkyl,
- in which R7 and R8 are the same or different and are hydrogen or lower alkyl and X1 is a single bond or a linear or branched C1-C4 alkylene;
- R2 is:
- lower alkyl optionally substituted with OR9, SR9, or
- —X2-cycloalkyl optionally substituted with OR9, SR9, NR9R10 or with a linear or branched C1-C4 alkyl,
- in which R9 and R10 are the same or different and are hydrogen or lower alkyl and X2 is a single bond or a linear or branched C1-C4 alkylene;
- and
- R3 is:
- in which:
- n is an integer from 1 to 4,
- Ar is an aromatic ring comprising 5 or 6 atoms comprising zero to three O, S or N, and
- Y1, Y2 and Y3, which may be identical or different, are:
- hydrogen, hydroxyl, halogen, mercapto, nitro, C(=O)R11, C(=O)OR11, C(═O)NR12R13, NR12R13 or —(CH2)SCN in which s is an integer from 0 to 2;
- R11, R12 and R13 are each independently hydrogen or lower alkyl,
- lower alkyl or lower alkoxy, each optionally substituted with 1, 2 or 3 halogen atoms, or
- —S(O)mR14 in which m is 0 or 1 and R14 is lower alkyl, an isomer thereof or a pharmaceutically acceptable salt thereof.
22 more elements
4-Benzyl-1-cyclopentyl-7-(cyclopentylformamido)-4H[1,2,4]triazolo[4,3-a]quinazolin-5-one,
- 7-acetamido-4-benzyl-1-cyclopentyl-4H-[1,2,4] triazolo[4,3-a]quinazolin-5-one, 4-benzyl-7-(cyclopentylformamido)-1-methyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one, 7-acetamido4-benzyl-1-methyl-4H-[1,2,4]triazolol[4,3-a]quinazolin-5-one, 4-benzyl-1-cyclopentyl-7-(N-methylacetamido)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one,
- 4-benzyl-1cyclopentyl-7-(cyclopentyl-N-methylformamido)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one,
- 4-benzyl-1-cyclopentyl-7-methylamino-4H-[1, 2,4]triazolo[4,3-a]quinazolin-5-one, 4-(4-cyanobenzyl)-1cyclopentyl-7(N-methylamino)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one,
- 4-(4-cyanobenzyl)-1-cyclopentyl-7-(N-methylamino)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one,
- 4-benzyl-7-bromo-1-cyclopentyl-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one, or 4-benzyl-7-bromo-1-methyl4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one.
2 more elements
Dependencies are inferred from the claim text.