Patent EA-004304-B1 (EA)
Title: Novel ribose-substituted aromatic amides, method for the production and use thereof as medicaments
Inventor: DEMASSEY JACQUE
IPC: A61P31/16
Filed: 2000-04-18
Abstract: 1. Compounds of formula (I) wherein: R1 is alkyl, alkenyl or alkynyl, O-alkyl, O-alkenyl or O-alkynyl, linear, branched or cyclic, comprising up to 8 carbon atoms optionally substituted by one or several halo atoms, optionally interrupted O, S or N comprising up to 18 carbon atoms, linear, branched or cyclic, comprising up to 8 carbon atoms, aromatic or non-aromatic heterocyclic radical, mono- or polycyclic, optionally substituted radical, NH2, NHalc1 or NHalc2, wherein alc1 and alc2 are alkyl radical comprising up to 8 carbon atoms, R2 is a hydrogen or halogen atom; R3 is a hydrogen atom comprising up to 8 carbon atoms or a halogen atom; R4 is NHR' or NHOR'' radical, in which R' or R'' are identical or different and represent hydrogen, alkyl, alkenyl or alkynyl radical, linear, branched or cyclic, comprising up to 8 carbon atoms, aryl radical comprising up to 14 carbon atoms, optionally substituted R5 is a hydrogen atom or O-alkyl radical; R6 is alkyl radical or CH2-O-alkyl radical; R7 is a hydrogen atom or alkyl radical comprising up to 8 carbon atoms, or R6 and R7 form a cycle together with the carbon atom carrying them in addition to the addition salts thereof with bases. 2. The compounds of formula (I) according to claim 1, wherein R1 is an alkyl radical comprising up to 4 carbon atoms. 3. The compounds of formula (I) according to claim 2, wherein R1 is a radical: 4. The compounds of formula (I) according to claim 1, wherein R1 is a phenyl radical. 5. The compound of formula (I) according to any one of claims 1 to 4, wherein R2 is a hydrogen atom. 6. The compound of formula (I) according to any one of claims 1 to 5, wherein R3 is a methyl radical. 7. The compound of formula (I) according to any one of claims 1 to 6, wherein R3 is a OCH2 radical. 8. The compound of formula (I) according to any one of claims 1 to 7, wherein R6 and R7 are a methyl radical. 9. The compound of formula (I) according to any one of claims 1 to 7, wherein R6 and R7 are an ethyl radical. 10. The compound of formula (I) according to any one of claims 1 to 7, wherein R6 and R7 form with a hydrogen atom with which they are bound a cyclopentyl radical. 11. The compound of formula (I) according to any one of claims 1 to 7, wherein R4 is NH-O-CH2-C [triple bond] CH. 12. The compound of formula (I) according to claim 1 which is: [7R-(7alpha, 8beta, 9beta, 10alpha)]-8-hydroxy-7-[4-hydroxy-8-methyl-2-oxo-3-(benzoilamino)-2H-1-benzopyran-7-yl]-1omethoxy-6-oxapiro]4,5] decan-9-yl-(2-propynyloxy)-carbamate. 13. The compound of formula (I) according to claim 1 which is: [7R-(7alpha, 8beta, 9beta, 10alpha)]-7-[4-hydroxy-8-methyl-3](2-methyl-1-oxo-propyl)amino]-2-oxo-2H-1benzopylan-7-yl]-10-methoxy-6-oxapiro]4,5] decan-9-yl-(2-propynyloxy)-carbamate. 14. Use of the compounds according to claim 1 and addition salts thereof with pharmaceutically acceptable bases as a medicament. 15. Use of the compounds according to claim 12 or 13 and addition salts thereof with pharmaceutically acceptable bases as a medicament. 16. A pharmaceutical composition comprising at least one medicament as an active compound according to claim 14 or 15. 17. A method for producing compounds of formula (I) according to claim 1, characterized in that the compound of formula (II) reacts with compound of formula in which R1 is as defined above and Hal is a halogen atom obtaining the compound of formula (III): which reacts with compound of formula R4H obtaining the compound of formula (I): 18. The compound of formula (II) as defined in claim 17. 19. The compound of formula (III) as defined in claim 17. 20. A method for the production of compound of formula (I) as defined in claim 1, characterized in that the compound of formula (V), in which the substituents are as defined above and OM is a protected hydroxy radical, react with a compound of formula R1COHal, in which R1 is as defined above and Hal is a halo atom then is treated with an agent liberating the OH group and obtaining a compound of formula (I): 21. A compound of formula (V), is as defined in claim 20.