Lincomycin Derivatives and Antimicrobial Agents Comprising the Same as Active Ingredient

A compound of formula (I) or its pharmacologically acceptable salt or solvate:

• wherein
• A represents
• aryl optionally substituted by a group selected from the group consisting of benzyl and C1-6 alky;
• or
• a monocyclic or bicyclic heterocyclic group in which each ring is a four- to seven-membered ring and which is optionally substituted by a group selected from the group consisting of C1-6 alkyl and halogenated C1-6 alkyl,
• wherein the heterocyclic group contains one to four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms,
• R1 represents
• a halide;
• cyano;
• nitro;
• substituted C1-6 alkyl
• wherein the C1-6 alkyl group is substituted by one or more groups selected from the group consisting of hydroxy, halides, carbamoyl, C1-6 alkyloxycarbonyl, cyano, di-C1-6 alkylcarbamoyl, C1-6 alkyloxy, heterocyclic carbonyl, and heterocyclic groups, and the heterocyclic carbonyl and heterocyclic groups are optionally substituted by one or more groups selected from the group consisting of halides, nitro, C1-6 alkyl, C1-6 alkylamino, amino, cyano, di-C1-6 alkylamino, C1-6 alkyloxy, hydroxy, acylamino, oxo, carbamoyl, di-C1-6 alkylaminocarbonyl, and C1-6 alkylaminocarbonyl;
• optionally substituted amino
• wherein the amino group is optionally substituted by one or more groups selected from the group consisting of C1-6 alkyl, C2-6 alkenyl, C1-6 acyl, optionally substituted heterocyclic groups, and optionally substituted aryl, the heterocyclic group, which can substitute the amino group, is optionally substituted by one or more groups selected from the group consisting of halides, nitro, cyano, di-C1-6 alkylamino, C1-6 alkyloxy, hydroxy, acylamino, C1-6 alkyl, C1-6 alkylamino, amino, oxo, carbamoyl, di-C1-6 alkylaminocarbonyl, and C1-6 alkylaminocarbony, and the aryl group is optionally substituted by one or more groups selected from the group consisting of halides, nitro, amino, C1-6 alkyl, cyano, C1-6 alkylthio, halogenated C1-6 alkylthio, C1-6 alkylsulfonyl, C1-6 alkyloxy, hydroxy C1-6 alkylamino, C1-6 alkylamino, di-C1-6 alkylamino, C1-6 alkylsulfinyl, C1-6 alkyloxycarbonyl, carbamoyl, and di-C1-6 alkylaminocarbonyl;
• N-amino-C1-6 alkylcarbonyl-N—C1-6 alkylamino;
• N—C1-6 alkyloxycarbonyl-C1-6 alkyl-N—C1-6 alkylamino;
• N—C1-6 alkyloxy substituted C1-6 alkylcarbonyl-N—C1-6 alkylamino;
• C1-6 alkylcarbonylamino optionally substituted by one or more groups selected from the group consisting of amino and hydroxy;
• C1-6 alkylamino-C1-6 alkylcarbonylamino;
• (di-C1-6 alkylamino)-C1-6 alkylcarbonylamino;
• C1-6 alkyloxy-C1-6 alkylcarbonylamino;
• N—C2-6 alkenylcarbonylamino;
• C1-6 alkyloxycarbonylamino;
• heterocyclic carbonylamino optionally substituted by one or more C1-6 alkyl;
• C1-6 alkylsulfonylamino;
• (S)-2-amino-3-succinamide;
• carbamoyl;
• N—C1-6 alkyl substituted carbamoyl;
• N—C1-6 alkyl-N—C1-6 alkyloxy substituted carbamoyl;
• N,N-di-C1-6 alkyl substituted carbamoyl;
• N—C3-6 cycloalkyl substituted carbamoyl;
• N-adamantyl substituted carbamoyl;
• N-amino substituted carbamoyl;
• N-heterocyclic C1-6 alkyl substituted carbamoyl;
• N-(hydroxy-C1-6 alkyl) substituted carbamoyl;
• N-(dihydroxy-C1-6 alkyl) substituted carbamoyl;
• N-(di-C1-6 alkyloxy-C1-6 alkyl) substituted carbamoyl;
• N,N-di(hydroxy-C1-6 alkyl) substituted carbamoyl;
• N,N-di(C1-6 alkyloxy-C1-6 alkyl) substituted carbamoyl;
• carboxyl;
• C1-6 alkylcarbonyl;
• heterocyclic-C1-6 alkylcarbonyl;
• C1-6 alkyloxycarbonyl;
• heterocyclic aminocarbonyl;
• optionally substituted arylcarbonyl
• wherein the arylcarbonyl group is optionally substituted by one or more groups selected from the group consisting of halides, nitro, amino, C1-6 alkyl, cyano, C1-6 alkylthio, C1-6 alkylsulfonyl, C1-6 alkyloxy, hydroxy C1-6 alkylamino, C1-6 alkylamino, di-C1-6 alkylamino, C1-6 alkylsulfinyl, C1-6 alkyloxycarbonyl, carbamoyl, and di-C1-6 alkylaminocarbonyl;
• optionally substituted 4- to 7-membered heterocyclic carbonyl
• wherein the heterocyclic carbonyl group is optionally substituted by one or more groups selected from the group consisting of C1-6 alkyl, hydroxy C1-6 alkyl, cyano, di-C1-6 alkylamino, C1-6 alkyloxy, C2-6 alkenyloxy-C1-6 alkyl, hydroxy, C1-6 alkylcarbonylamino, C1-6 alkylthio-C1-6 alkyl, amino-C1-6 alkyl, C1-6 alkyloxy-C1-6 alkyl, oxo, C1-6 alkylamino, carbamoyl, di-C1-6 alkylaminocarbonyl, C1-6 alkylaminocarbonyl, C1-6 alkylamino-C1-6 alkyl, di-C1-6 alkylamino-C1-6 alkyl, C1-6 alkylsulfonyl-C1-6 alkyl, cyano, halides, amino, acylamino C1-6 alkyl, and acylamino;
• C1-6 alkylthio substituted by amino or carbamoyl;
• pyridylthio;
• C1-6 alkylsulfonyl;
• arylsulfonyl;
• heterocyclic sulfonyl;
• pyridyloxy;
• optionally substituted aryl
• wherein the aryl group is optionally substituted by one or more groups, which may be the same or different, selected from the group consisting of a fluorine atom, a chlorine atom, nitro, amino, C1-6 alkyl, cyano, C1-6 alkyloxy, halogenated C1-6 alkyloxy, hydroxy C1-6 alkyl, hydroxy C1-6 alkylamino, C1-6 alkylamino, di-C1-6 alkylamino, C1-6 alkylthiocarbamoyl, C1-6 alkylcarbonylamino, C1-6 alkylsulfonylamino, formylamino, C1-6 alkyloxycarbonyl, and azetidinyl;
• an optionally substituted four- to seven-membered monocyclic heterocyclic group
• wherein the heterocyclic group is optionally substituted by one or more groups selected from the group consisting of halides, nitro, cyano, di-C1-6 alkylamino, C1-6 alkyloxy, hydroxy, acylamino, C1-6 alkyl, C1-6 alkylamino, amino, oxo, carbamoyl, di-C1-6 alkylaminocarbonyl, C1-6 alkylaminocarbonyl, C1-6 alkyloxy-C1-6 alkyl, and N-oxide;
• or
• a bicyclic heterocyclic group in which each ring is a four- to seven-membered ring,
• when n is 2, individual R1s may be the same or different,
• R2 represents
• a hydrogen atom;
• optionally substituted C1-6 alkyl;
• optionally substituted C2-6 alkenyl;
• optionally substituted acyl;
• or
• optionally substituted C1-6 alkyloxycarbonyl
• wherein the C1-6 alkyl, C2-6 alkenyl, acyl, and C1-6 alkyloxycarbonyl groups are optionally substituted by one or more groups selected from the group consisting of heterocyclic rings optionally substituted by C1-6 alkyl;
• amino;
• hydroxy;
• and cyano,
• R3 represents
• optionally substituted C1-6 alkyl
• wherein the C1-6 alkyl group is optionally substituted by one or more groups selected from the group consisting of halides, nitro, hydroxy, amino, C1-6 alkyloxycarbonyl, carbamoyl, cyano, C1-6 alkyloxy, oxo, heterocyclic ring, carbamoyl, azide, C1-6 alkylaminocarbonyl, di-C1-6 alkylaminocarbonyl, and optionally substituted aryl;
• or
• C2-6 alkenyl,
• R4, R5, and R6, which may be the same or different, represent
• a hydrogen atom;
• optionally substituted C1-6 alkyl;
• or
• optionally substituted acyl
• wherein the C1-6 alkyl group and hydrogen atoms on the acyl group are optionally substituted by one or more groups selected from the group consisting of halides;
• nitro;
• hydroxy;
• amino;
• C1-6 alkyloxycarbonyl;
• carbamoyl;
• cyano;
• nitro halide;
• C1-6 alkyloxy;
• oxo;
• heterocyclic rings;
• carbamoyl;
• azide;
• C1-6 alkylaminocarbonyl;
• di-C1-6 alkylaminocarbonyl;
• and aryl optionally substituted by a halide, hydroxy or C1-4 alkyl,
• R7 represents C1-6 alkyl optionally substituted by one or more groups selected from the group consisting of halides and hydroxy,
• m is 1 to 3, and
• n is 1 or 2.