Rearranged pentanols, a process for their production and their use as anti-inflammatory agents

A compound of formula I

• in which
• R1 means an optionally substituted phenyl radical,
• R2 means a monocyclic or bicyclic aromatic, partially aromatic or non-aromatic ring system, which optionally contains 1-3 nitrogen atoms, 1-2 oxygen atoms and/or 1-2 sulfur atoms and optionally is substituted in one or more places by a radical that is selected from the group carbonyl, halogen, hydroxy, (C1-C5)-alkyl, which optionally can be substituted by 1-3 hydroxy groups, 1-3 (C1-C5)alkoxy groups and/or 1-3 COOR6 groups,
• (C1-C5)alkoxy, (C1-C5)-alkylthio, (C1-C5)-perfluoroalkyl, cyano, nitro, or NR4R5,
• whereby R4 and R5, independently of one another, can be hydrogen, C1-C5-alkyl or (CO)—C1-C5-alkyl,
• COOR6,
• whereby R6 means hydrogen or a C1-C5-alkyl group,
• (CO)NR7R8,
• whereby R7 and R8, independently of one another, mean hydrogen or a C1-C5-alkyl group,
• or a (C1-C5-alkylene)-O—(CO)—(C1-C5)alkyl group,
• R3 means a C1-C3-alkyl group or a partially or completely fluorinated C1-C3-alkyl group,
• and the dotted line means a double bond between atoms a and b or a double bond between atoms b and c or only a single bond between atoms a and b as well as b and c, racemates,
• separately present stereoisomers or physiologically compatible salts thereof.

A process for the production of compounds of formula I,

• in which
• R1 means an optionally substituted phenyl radical,
• R2 means a monocyclic, or bicyclic, aromatic, partially aromatic, or non-aromatic ring system, which optionally contains 1-3 nitrogen atoms, 1-2 oxygen atoms and/or 1-2 sulfur atoms and optionally is substituted in one or more places by a radical that is selected from the group carbonyl, halogen, hydroxy, or (C1-C5)-alkyl, which optionally can be substituted by 1-3 hydroxy groups, 1-3 (C1-C5)alkoxy groups and/or 1-3 COOR6 groups,
• (C1-C5)alkoxy, (C1-C5)-alkylthio, (C1-C5)-perfluoroalkyl, cyano, nitro, or two substituents together form a group that is selected from the groups —O—(CH2)n—O—, —O—(CH2)n—CH2—, —O—CH═CH—, —(CH2)n+2—, —NH—(CH2)n+1—, —N(C1-C3-alkyl)-(CH2)n+1—, and —NH—N═CH—,
• whereby n=1 or 2, and the terminal oxygen atoms and/or carbon atoms and/or nitrogen atoms are linked to directly adjacent ring-carbon atoms,
• NR4R5,
• whereby R4 and R5, independently of one another, can be hydrogen, C1-C5-alkyl or (CO)—C1-C5-alkyl,
• COOR6,
• whereby R6 means hydrogen or a C1-C5-alkyl group,
• (CO)NR7R8,
• whereby R7 and R8, independently of one another, mean hydrogen or a C1-C5-alkyl group,
• or a (C1-C5-alkylene)-O—(CO)—(C1-C5)alkyl group,
• R3 means a C1-C3-alkyl group or a partially or completely fluorinated C1-C3-alkyl group,
• and the broken line means a double bond between atoms a and b or a double bond between atoms b and c or only a single bond between atoms a and b, as well as b and c, racemates, separately present stereoisomers, or physiologically compatible salts thereof,
• comprising reacting imines of formula II
• with Lewis acid in an organic solvent, to obtain compounds of formula I.

A method for the treatment of an inflammatory disease in a host in need thereof, comprising administering to said host an effective amount of a compound of formula I

• in which
• R1 means an optionally substituted phenyl radical,
• R2 means a monocyclic, or bicyclic, aromatic, partially aromatic, or non-aromatic ring system, which optionally contains 1-3 nitrogen atoms, 1-2 oxygen atoms and/or 1-2 sulfur atoms and optionally is substituted in one or more places by a radical that is selected from the group carbonyl, halogen, hydroxy, or (C1-C5)-alkyl, which optionally can be substituted by 1-3 hydroxy groups, 1-3 (C1-C5)alkoxy groups and/or 1-3 COOR6 groups,
• (C1-C5)alkoxy, (C1-C5)-alkylthio, (C1-C5)-perfluoroalkyl, cyano, nitro, or two substituents together form a group that is selected from the groups —O—(CH2)n—O—, —O—(CH2)n—CH2—, —O—CH═CH—, —(CH2)n+2—, —NH—(CH2)n+1—, —N(C1-C3-alkyl)-(CH2)n+1—, and —NH—N═CH—,
• whereby n=1 or 2, and the terminal oxygen atoms and/or carbon atoms and/or nitrogen atoms are linked to directly adjacent ring-carbon atoms,
• NR4R5,
• whereby R4 and R5, independently of one another, can be hydrogen, C1-C5-alkyl or (CO)—C1-C5-alkyl,
• COOR6,
• whereby R6 means hydrogen or a C1-C5-alkyl group,
• (CO)NR7R8,
• whereby R7 and R8, independently of one another, mean hydrogen or a C1-C5-alkyl group,
• or a (C1-C5-alkylene)-O—(CO)—(C1-C5)alkyl group,
• R3 means a C1-C3-alkyl group or a partially or completely fluorinated C1-C3-alkyl group,
• and the broken line means a double bond between atoms a and b or a double bond between atoms b and c or only a single bond between atoms a and b, as well as b and c, racemates,
• separately present stereoisomers, or physiologically compatible salts thereof.