Substituted furochromene compounds of antiinflammatory action

A processes for the preparating a compound of formula (I)

• wherein
• A and B taken together with the carbon atoms to which they are attached, each independently represent an aromatic moiety or a heteroaromatic moiety, which is:
• (c) unsubstituted or substituted by one or more substituents which are each independently selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halo-C1-C4-alkyl, hydroxy, C1-C4-alkoxy, trifluoromethoxy, C1-C4-alkanoyl, amino, amino-C1-C4-alkyl, N—(C1-C4-alkyl)amino, N,N-di(C1-C4-alkyl)amino, sulfanyl, C1-C4-alkylsulfanyl, sulfo, C1-C4-alkylsulfo, sulfino, C1-C4-alkylsulfino, carboxy, C1-C4-alkoxycarbonyl, cyano, and nitro;
• and/or
• (d) fused with an unsubstituted or substituted heteroaromatic moiety or heterocycle, and
• stereoisomers, tautomers, pharmaceutically acceptable salts and solvates thereof, comprising reacting a compound of the formula (II) or a salt thereof
• with glyoxal of the formula (III)
• in an aqueous-organic medium at a reaction temperature of from about room temperature to about 90° C.

A pharmaceutical composition comprising a compound of the formula (I)

• wherein
• A and B taken together with the carbon atoms to which they are attached, each independently represent an aromatic moiety or a heteroaromatic moiety, which is:
• (e) unsubstituted or substituted by one or more substituents which are each independently selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halo-C1-C4-alkyl, hydroxy, C1-C4-alkoxy, trifluoromethoxy, C1-C4-alkanoyl, amino, amino-C1-C4-alkyl, N—(C1-C4-alkyl)amino, N,N-di(C1-C4-alkyl)amino, sulfanyl, C1-C4-alkylsulfanyl, sulfo, C1-C4-alkylsulfo, sulfino, C1-C4-alkylsulfino, carboxy, C1-C4-alkoxycarbonyl, cyano, and nitro;
• and/or
• (f) fused with an unsubstituted or substituted heteroaromatic moiety or heterocycle, and
• stereoisomers, tautomers, pharmaceutically acceptable salts and solvates thereof and a pharmaceutically acceptable diluent or carrier.

A method of treating or preventing an inflammatory disease or condition associated with an undesirable inflammatory immune response, which comprises administering to a subject an amount of a compound of formula (I)

• wherein
• A and B taken together with the carbon atoms to which they are attached, each independently represent an aromatic moiety or a heteroaromatic moiety, which is:
• (a) unsubstituted or substituted by one or more substituents which are each independently selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halo-C1-C4-alkyl, hydroxy, C1-C4-alkoxy, trifluoromethoxy, C1-C4-alkanoyl, amino, amino-C1-C4-alkyl, N—(C1-C4-alkyl)amino, N,N-di(C1-C4-alkyl)amino, sulfanyl, C1-C4-alkylsulfanyl, sulfo, C1-C4-alkylsulfo, sulfino, C1-C4-alkylsulfino, carboxy, C1-C4-alkoxycarbonyl, cyano, and nitro;
• and/or
• (b) fused with an unsubstituted or substituted heteroaromatic moiety or heterocycle, and
• stereoisomers, tautomers, pharmaceutically acceptable salts and solvates thereof, effective to reduce or inhibit said inflammatory response.

A method of inhibiting granulocyte degranulation, comprising exposing mammalian granulocytes to an amount of a compound of formula (I)

• wherein
• A and B taken together with the carbon atoms to which they are attached, each independently represent an aromatic moiety or a heteroaromatic moiety, which is:
• (a) unsubstituted or substituted by one or more substituents which are each independently selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halo-C1-C4-alkyl, hydroxy, C1-C4-alkoxy, trifluoromethoxy, C1-C4-alkanoyl, amino, amino-C1-C4-alkyl, N—(C1-C4-alkyl) amino, N,N-di(C1-C4-alkyl) amino, sulfanyl, C1-C4-alkylsulfanyl, sulfo, C1-C4-alkylsulfo, sulfino, C1-C4-alkylsulfino, carboxy, C1-C4-alkoxycarbonyl, cyano, and nitro;
• and/or
• (b) fused with an unsubstituted or substituted hetero aromatic moiety or heterocycle, and
• stereoisomers, tautomers, pharmaceutically acceptable salts and solvates thereof, effective to inhibit granulocyte degranulation.

A method of reducing hyperreactivity of a respiratory airway, comprising exposing the respiratory airway of a mammal to an amount of a compound of formula (I)

• wherein
• A and B taken together with the carbon atoms to which they are attached, each independently represent an aromatic moiety or a heteroaromatic moiety, which is:
• (a) unsubstituted or substituted by one or more substituents which are each independently selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halo-C1-C4-alkyl, hydroxy, C1-C4-alkoxy, trifluoromethoxy, C1-C4-alkanoyl, amino, amino-C1-C4-alkyl, N—(C1-C4-alkyl)amino, N,N-di(C1-C4-alkyl)amino, sulfanyl, C1-C4-alkylsulfanyl, sulfo, C1-C4-alkylsulfo, sulfino, C1-C4-alkylsulfino, carboxy, C1-C4-alkoxycarbonyl, cyano, and nitro;
• and/or
• (b) fused with an unsubstituted or substituted heteroaromatic moiety or heterocycle, and
• stereoisomers, tautomers, pharmaceutically acceptable salts and solvates thereof, effective to decrease the hyperreactivity of the respiratory airway.