Microsphaeropsin B as novel antibacterial agent, process for producing the same and pharmaceutical composition containing thereof

A compound of formula I,

• 11
• wherein
• R1 is O or OH;
• R5 is a group represented by formula II or III,
• 12
• R2 is O or OH;
• each of the dashed lines independently represents a single bond or nothing so that the two atoms attached to the two ends of the dashed line are connected by a single or double bond, wherein the dashed line attached to R1 represents a single bond when R1 is O or nothing when R1 is OH, and the dashed line attached to R2 represents a single bond when R2 is O or nothing when R2is OH;
• R3 is H, C1-C6 alkyl, —C(O)R11, —C(O)R12, —P(O)(OH)2, an amino acid residue, a dicarboxylic acid residue, —C(O)—C(O)R13 or —C(O)OR14;
• R4 is H, C1-C6 alkyl, —C(O)R41, —C(O)R42, —P(O)(OH)2, an amino acid residue, a dicarboxylic acid residue, —C(O)—C(O)R43 or —C(O)OR44;
• the amino acid residue is an amino acid having OH removed from a carboxyl group;
• the dicarboxylic acid residue is a dicarboxylic acid having OH removed from one of the carboxyl groups;
• R12 and R41 are each independently (C1-C20)alkyl, (C1-C20)alkyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, (C2-C20)alkenyl, (C2-C20)alkenyl substituted by one to three halogen atoms, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, benzyl, benzyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups, or a cyclic moiety which is a (C4-C8)cycloalkyl, phenyl, naphthyl or heterocyclic group, wherein the cyclic moiety is unsubstituted or substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups;
• R12 and R42 are each independently —N(R20)(R21), 1-imidazolyl or pyrrolyl;
• R20 and R21 are each independently H, (C1-C6)alkyl, (C1-C6)alkyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, (C2-C6)alkenyl, (C2-C6)alkenyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, benzyl, benzyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups, or a cyclic moiety which is a (C4-C8)cycloalkyl, phenyl, naphthyl or heterocyclic group, wherein the cyclic moiety is unsubstituted or substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups;
• R13 and R43 are each independently (C1-C6)alkyl or (C1-C6)alkyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups;
• and
• R14 and R44 are each independently (C1-C6)alkyl, (C1-C6)alkyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, (C2-C6)alkenyl, (C2-C6)alkenyl substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino or (C1-C6)alkyl-carbonyl groups, benzyl, benzyl substituted by one to three halogen atoms, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups, or a cyclic moiety which is a (C4-C8)cycloalkyl, phenyl, naphthyl or heterocyclic group, wherein the cyclic moiety is unsubstituted or substituted by one to three halogen, OH, SH, nitro, amino, mono-(C1-C6)alkyl-amino, di-(C1-C6)alkyl-amino, (C1-C6)alkyl-carbonyl, (C1-C6)alkyl or (C2-C6)alkenyl groups;
• wherein the heterocyclic group is a 5- or 6-membered ring containing one to three N, O and/or S ring atoms optionally fused with a benzene or 5- or 6-membered ring containing one to three N, O and/or S ring atoms;
• with the proviso that a compound of formula IV
• 13
• is excluded;
• or
• a pharmaceutically acceptable salt, solvate or hydrate thereof.