DERIVATIVES OF 5-FLUORO-N- (PIRIDIN-2-IL) PIRIDIN-2-AMINA CONTAINING A SULFOXIMINE GROUP

Argentina Patent

APP PUB NO AR-093505-A1
SERIAL NO

P130104211

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Abstract

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5-Fluoro-N- (pyridin-2-yl) -pyridin-2-amine derivatives containing a sulfoximin group and having the general formula (1), as described and defined herein. Methods to prepare them. Its use in the treatment and / or prophylaxis of various disorders, particularly hyperproliferative disorders, infectious diseases induced by viruses and / or cardiovascular diseases. Intermediate compounds useful for preparing the compounds of the general formula (1). Claim 1: A compound of the general formula (1) wherein R¹ represents a group selected from C alquilo alkyl, C ciclo cycloalkyl, heterocyclyl, phenyl, heteroaryl, phenyl-C₁₋₃ alkyl or heteroaryl-C₁₋₃ alkyl, wherein said group is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of hydroxy, cyano, halogen, halo C₁₋₃ alkyl, C alkoxy, C₁₋₃ fluoroalkoxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N-acetylamino, cyclic amines, -OP (O) (OH) ₂, -C (O) OH, -C (O) NH₂; R² represents a group selected from the group of formulas (2); R³, R⁴ independently represent each other, a group selected from a hydrogen atom, fluorine atom, chlorine atom, bromine atom, cyano, C₁₋₃ alkyl, C₁₋₃ alkoxy, halo-C₁₋₃ alkyl , C₁₋₃ fluoroalkoxy; R⁵ represents a group selected from a hydrogen atom, cyano, -C (O) R⁹, -C (O) OR⁹, -S (O) ₂R⁹, -C (O) NR¹⁰R¹¹, -P (O) (OR¹²) ₂ , -CH₂OP (OR¹²) ₂, C₁₋₆ alkyl, C₃₋₇ cycloalkyl, heterocyclyl, phenyl, heteroaryl, wherein said C₁₋₆ alkyl group, C₃₋₇ cycloalkyl, heterocyclyl, phenyl or heteroaryl is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, cyano, C₁₋₃ alkyl, C₁₋₃ alkoxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N-acetylamino, cyclic amines, halo-alkyl C₁₋₃, Coro fluoroalkoxy; R⁶, R⁷ independently represent each other, a group selected from a hydrogen atom, fluorine atom, chlorine atom, C₁₋₃ alkyl, C₁₋₃ alkoxy, halo C₁₋₃ alkyl, C₁₋ fluoroalkoxy ₃; R⁸ represents a group selected from a) a C₁₋₆ alkyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N- methyl-N-acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo C₁₋₃ alkyl, Coro fluoroalkoxy, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, C₃₋₇ cycloalkyl, heterocyclyl, phenyl, heteroaryl, wherein said C₃₋₇ cycloalkyl, heterocyclyl, phenyl or heteroaryl group is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, C₁₋₃ alkyl, C₁₋ alkoxy ₃, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N-acetylamino cyclic amines, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy; b) a C₃₋₇ cycloalkyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl -N-acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo C₁₋₃ alkyl, Coro fluoroalkoxy, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl; c) a heterocyclyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl -N- acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo C₁₋₃ alkyl, Coro fluoroalkoxy, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl; d) a phenyl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N- acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy, C₁₋₃ alkoxy; e) a heteroaryl group, which is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N- acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy, C₁₋₃ alkoxy; f) a phenyl-C₁₋₃ alkyl group, where the phenyl group thereof is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N acetylamino, cyclic amines, cyano, C₁₋₃ alkyl, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy, C₁₋₃ alkoxy; g) a heteroaryl-cyc3alkyl group wherein the heteroaryl group thereof is optionally substituted with one or two or three substituents, identically or differently, selected from the group consisting of halogen, hydroxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N-acetylamino cyclic amines, cyano, C₁₋₃ alkyl, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy, C₁₋₃ alkoxy; h) a C₃₋₆-C₁₋₃ cycloalkyl group where the C₃₋₆ cycloalkyl group thereof is optionally substituted with one or two or three Substituents identically or differently, selected from halogen, C₁₋₃ alkyl, C₁₋ alkoxy ₃, halo-C₁₋₃ -alkyl fluoro-C₁₋₃-alkoxy; i) a heterocyclyl-C₁₋₃ alkyl group, wherein the heterocyclyl group thereof is optionally substituted with one or two or three substituents, identically or differently, selected from halogen, C₁₋₃ alkyl, C₁₋₃ alkoxy, halo- C₁₋₃ alkyl, Coro fluoro-alkoxy; R⁹ represents a group selected from C₁₋₆ alkyl, halo-C₁₋₃ alkyl C₃₋₇ cycloalkyl, heterocyclyl, phenyl, benzyl or heteroaryl, wherein said group is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, C₁₋₃ alkyl, C₁₋₃ alkoxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl-N-acetylamino, cyclic amines, halo C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy; R¹⁰, R¹¹ independently represent each other, a group selected from hydrogen, C₁₋₆ alkyl, C₃₋₇ cycloalkyl, heterocyclyl, phenyl, benzyl or heteroaryl, wherein said C₁₋₆ alkyl group, C₃₋₇ cycloalkyl, heterocyclyl, phenyl, benzyl or heteroaryl is optionally substituted with one, two or three substituents, identically or differently, selected from halogen, hydroxy, C₁₋₃ alkyl, C₁₋₃ alkoxy, -NH₂, alkylamino, dialkylamino, acetylamino, N-methyl -N-acetylamino, cyclic amines, halo-C₁₋₃ alkyl, fluoro-C₁₋₃ alkoxy, or R¹⁰ and R¹¹, together with the nitrogen atom to which they are attached, form a cyclic amine; R² represents a group selected from hydrogen, C₁₋₄ alkyl or benzyl; and the enantiomers, diasteromers, salts, solvates or solvate salts thereof.

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Patent Owner(s)

Patent OwnerAddress
BAYER PHARMA AGDELEVERKUSEN GERMANY LEVERKUSEN NORTH RHINE-WESTPHALIA

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Inventor(s)

Inventor Name Address
GERHARD DR SIEMEISTER DE
PHILIP DR LIENAU DE
DIRK DR KOSEMUND DE
ULRICH DR LCKING DE
NIELS DR BHNKE DE
ARNE DR SCHOLZ DE
ULF DR BMER DE
ROLF DR BOHLMANN DE

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