10a-azalide compound having 4-membered ring structure
View Patent ↗A 10 a -azalide compound having a 4-membered ring structure crosslinked at the 10 a - and 12-positions, which is represented by the formula (I), and is effective on even Haemophilus influenzae , or erythromycin resistant bacteria (e.g., resistant pneunococci and streptococci).
1. A 10a-azalide compound represented by the formula (I):
wherein, in the formula, R 2 and R 3 combine together to represent an oxo group, or one of them is a hydrogen atom, and the other is:
a hydroxyl group,
a protected hydroxyl group,
a group represented by the formula —X 031 —R 031 , or a group represented by the formula (II):
wherein X 031 is:
a group represented by the formula —O—,
a group represented by the formula —OCO—, or
a group represented by the formula —OCON(R 20 )—,
R 031 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A,
the group A is a group consisting of a hydroxyl group, a halogen atom, an amino group, a carboxyl group, a cyano group, a C 1-6 alkyl group (this C 1-6 alkyl group may be substituted with amino group, or a C 1-6 alkylamino group), a C 1-6 alkylamino group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 2-7 alkoxycarbonyl group, nitro group, a saturated heterocyclic group, a C 7-12 aralkyloxy group, and a C 1-11 acyl group,
one of R 32 and R 33 is a hydrogen atom, and the other is:
a hydrogen atom,
a hydroxyl group,
a protected hydroxyl group,
an amino group,
a protected amino group,
a group represented by the formula —X 331 —R 331 ,
a group represented by the formula —X 331 —A 331 —X 332 —R 331 ,
a group represented by the formula —X 331 —A 331 —X 332 —A 332 —X 333 —R 331 , or
a group represented by the formula —X 331 —A 331 —X 332 —A 332 —X 333 —A 333 —X 334 —R 331 ,
wherein X 331 is:
a group represented by the formula —O—,
a group represented by the formula —OCO—,
a group represented by the formula —OCON(R 20 )—,
a group represented by the formula —N(R 20 )—,
a group represented by the formula —N(R 20 )CO—, or
a group represented by the formula —OCSN(R 20 )—, and
R 331 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A, or
one of R 32 and R 33 is a hydroxyl group, and the other is:
a group represented by the formula —X 335 —R 332 ,
a group represented by the formula —X 335 —A 334 —X 336 —R 332 , or
a group represented by the formula —X 335 —A 334 —X 336 —A 335 —X 337 —R 332 ,
wherein X 335 is:
a single bond,
a group represented by the formula —CH 2 N(R 20 )—,
a group represented by the formula —CH 2 N(R 20 )CO—,
a group represented by the formula —CH 2 N(R 20 )CO 2 —,
a group represented by the formula —CH 2 N(R 20 )CON(R 21 )—,
a group represented by the formula —CH 2 —A 336 —,
a group represented by the formula —CH 2 O—, or
a group represented by the formula —CH 2 S(O) p —,
A 336 is:
a divalent nitrogen-containing heterocyclic group which may be substituted with a hydroxyl group or a C 1-6 alkoxy group,
R 332 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an amino group, a hydroxyl group, an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A, and
p is an integer of 0 to 2, or
R 32 and R 33 combine together to represent oxo group,
an oxime group,
a protected oxime group,
a group represented by the formula 3:
a group represented by the formula 4:
or
a group represented by the formula 5:
wherein R 334 is:
a group represented by the formula —OH, or
by the formula —SH,
R 335 is a hydrogen atom, or a C 1-6 alkyl group,
R 34 is:
a group represented by the formula —R 336 ,
a group represented by the formula —A 337 —X 338 —R 336 , or
a group represented by the formula —A 337 —X 338 —A 338 —X 339 —R 336 , and
R 336 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an amino group, hydroxyl group, an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A,
R 4 is:
a hydrogen atom,
a group represented by the formula —R 041 ,
a group represented by the formula —CH 2 —CH(OH)—CH 2 —NHR 041 , or
a group represented by the formula —CH 2 —CH(OH)—CH 2 —NH—A 041 —X 042 —R 041 ,
wherein A 041 is:
a divalent C 1-10 aliphatic hydrocarbon group, or
a divalent heterocyclic group, and
R 041 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A, or
R 4 may combine with R 6 to form a cyclic carbonate [—CON(R 22 )—],
one of R 5 and R 6 is hydrogen atom, and the other is:
a hydrogen atom,
a hydroxyl group,
a protected hydroxyl group,
an amino group,
a protected amino group,
a group represented by the formula —X 051 —R 051 , or
a group represented by the formula —X 051 —A 051 —X 052 —R 051 ,
wherein X 051 is:
a group represented by the formula —O—,
a group represented by the formula —OCON(R 22 )—,
a group represented by the formula —N(R 22 )—, or
a group represented by the formula —N(R 22 )CO—, and
R 051 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A, or
R 5 and R 6 combine together to represent
an oxo group,
an oxime group,
a protected oxime group,
a group represented by the formula ═N—X 053 —R 052 , or,
a group represented by the formula ═N—X 053 —A 052 —X 054 —R 052 ,
wherein X 053 is:
a group represented by the formula —O—, or
a group represented by the formula —CO—, and
R 052 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group A)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group A,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group A, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group A,
R 7 is:
a hydrogen atom, or
a protective group of hydroxyl group,
R 8 and R 9 , which are the same or different, represent
a hydrogen atom,
a C 1-6 alkyl group, or
a protective group of an amino group,
X 332 , X 333 , X 334 , X 336 , X 337 , X 338 , X 339 , X 042 , X 052 , and X 054 mentioned above, which are the same or different, represent
a single bond,
a group represented by the formula —O—,
a group represented by the formula —OCO—,
a group represented by the formula —OCO 2 —,
a group represented by the formula —OCON(R 25 )—,
a group represented by the formula —S(O) r —,
a group represented by the formula —SO 2 N(R 25 )—,
a group represented by the formula —OCS—,
a group represented by the formula —CO—,
a group represented by the formula —CO 2 —,
a group represented by the formula —CON(R 25 )—,
a group represented by the formula —CH═N—,
a group represented by the formula —CH═N—O—,
a group represented by the formula —C(R 25 )═N—,
a group represented by the formula —C(R 25 )═N—O—,
a group represented by the formula —C(R 25 )═N—N(R 26 )—,
a group represented by the formula —CH═N—N(R 25 )—,
a group represented by the formula —CS—,
a group represented by the formula —C(S)O—,
a group represented by the formula —CSN(R 25 )—,
a group represented by the formula —O—N═C(R 25 )—,
a group represented by the formula —N═CH—,
a group represented by the formula —N(R 25 )—,
a group represented by the formula —N(R 25 )CO—,
a group represented by the formula —N(R 25 )CS—,
a group represented by the formula —N(R 25 )SO 2 —,
a group represented by the formula —N(R 25 )CO 2 —, or
a group represented by the formula —N(R 25 )CON(R 26 )—,
r is an integer of 0 to 2,
A 331 , A 332 , A 333 , A 334 , A 335 , A 337 , A 338 , A 051 , and A 052 mentioned above, which are the same or different, represent
a divalent C 1-6 aliphatic hydrocarbon group which may be substituted with a hydroxyl group, a C 1-6 alkoxy group, an amino group, a C 1-6 alkylamino group, or a heterocyclic group,
an arylene group which may be substituted with a hydroxyl group or a C 1-6 alkoxy group, or
a divalent heterocyclic group which may be substituted with a hydroxyl group or a C 1-6 alkoxy group, and
R 20 , R 21 , R 22 , R 25 , and R 26 mentioned above, which are the same or different, represent
a hydrogen atom, or a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group A, or a salt thereof.
2. The 10a-azalide compound according to claim 1 or a salt thereof, wherein R 2 and R 3 combine together to represent an oxo group, or
one of them is a hydrogen atom, and the other is:
a hydroxyl group,
a protected hydroxyl group,
a group represented by the formula —X 031 —R 031 , or a group represented by the formula (II):
wherein X 031 is:
a group represented by the formula —O—,
a group represented by the formula —OCO—, or
a group represented by the formula —OCON(R 20 )—,
R 031 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B,
the group B is a group consisting of hydroxyl group, a halogen atom, an amino group, a carboxyl group, a cyano group, a C 1-6 alkyl group, a C 1-6 alkylamino group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 2-7 alkoxycarbonyl group, a nitro group, a saturated heterocyclic group and a C 1-11 acyl group,
one of R 32 and R 33 is hydrogen atom, and the other is:
a hydrogen atom,
a hydroxyl group,
a protected hydroxyl group,
an amino group,
a protected amino group,
a group represented by the formula —X 331 —R 331 ,
a group represented by the formula —X 331 —A 331 —X 332 —R 331 ,
a group represented by the formula —X 331 —A 331 —X 332 —A 332 —X 333 —R 331 , or
a group represented by the formula —X 331 —A 331 —X 332 —A 332 —X 333 —A 333 —X 334 —R 331 ,
wherein X 331 is:
a group represented by the formula —O—,
a group represented by the formula —OCO—,
a group represented by the formula —OCON(R 20 )—,
a group represented by the formula —N(R 20 )—,
a group represented by the formula —N(R 20 )CO—, or
a group represented by the formula —OCSN(R 20 )—, and
R 331 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B, or
one of R 32 and R 33 is a hydroxyl group, and the other is:
a group represented by the formula —X 335 —R 332
a group represented by the formula —X 335 —A 334 —X 336 —R 332 , or
a group represented by the formula —X 335 —A 334 —X 336 —A 335 —X 337 —R 332 ,
wherein X 335 is:
a single bond,
a group represented by the formula —CH 2 N(R 20 )—,
a group represented by the formula —CH 2 N(R 20 )CO—,
a group represented by the formula —CH 2 N(R 20 )CO 2 —,
a group represented by the formula —CH 2 N(R 20 )CON(R 21 )—,
a group represented by the formula —CH 2 O—, or
a group represented by the formula —CH 2 S(O) p —,
R 332 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an amino group, hydroxyl group, an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B, and
p is an integer of 0 to 2, or
R 32 and R 33 combine together to represent an oxo group,
an oxime group,
a protected oxime group,
a group represented by the formula 7:
or
a group represented by the formula 8:
wherein R 334 is:
a group represented by the formula —OH, or
by the formula —SH,
R 4 is:
a hydrogen atom,
a group represented by the formula —R 041 ,
a group represented by the formula —CH 2 —CH(OH)—CH 2 —NHR 041 , or
a group represented by the formula —CH 2 —CH(OH)—CH 2 —NH—A 041 —X 042 —R 041
wherein A 041 is:
a divalent C 1-10 aliphatic hydrocarbon group, or
a divalent heterocyclic group, and
R 041 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B, or
R 4 may combine with R 6 to form a cyclic carbonate [—CON(R 22 )—],
one of R 5 and R 6 is a hydrogen atom, and the other is:
a hydrogen atom,
a hydroxyl group,
a protected hydroxyl group,
an amino group,
a protected amino group,
a group represented by the formula —X 051 —R 051 , or
a group represented by the formula —X 051 —A 051 —X 052 —R 051 ,
wherein X 051 is:
a group represented by the formula —O—,
a group represented by the formula —OCON(R 22 )—,
a group represented by the formula —N(R 22 )—, or
a group represented by the formula —N(R 22 )CO—, and
R 051 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B, or
R 5 and R 6 combine together to represent
an oxo group,
an oxime group,
a protected oxime group,
a group represented by the formula ═N—X 053 —R 052 , or
a group represented by the formula ═N—X 053 —A 052 —X 054 —R 052 ,
wherein X 053 is:
a group represented by the formula —O—, or
a group represented by the formula —CO—, and
R 052 is:
a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkenyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
a C 2-6 alkynyl group which may be substituted with 1 to 3 groups selected from the group consisting of “an aryl group, a heterocyclic group, and a biaryl group (the aryl group, the heterocyclic group, and the biaryl group may be substituted with 1 to 3 groups selected from the group B)”,
an aryl group which may be substituted with 1 to 3 groups selected from the group B,
a heterocyclic group which may be substituted with 1 to 3 groups selected from the group B, or
a biaryl group which may be substituted with 1 to 3 groups selected from the group B,
X 332 , X 333 , X 334 , X 336 , X 337 , X 042 , X 052 , and X 054 mentioned above, which are the same or different, represent
a single bond,
a group represented by the formula —O—,
a group represented by the formula —OCO—,
a group represented by the formula —OCO 2 —,
a group represented by the formula —OCON(R 25 )—,
a group represented by the formula —S(O) r —,
a group represented by the formula —SO 2 N(R 25 )—,
a group represented by the formula —OCS—,
a group represented by the formula —CO—,
a group represented by the formula —CO 2 —,
a group represented by the formula —CON(R 25 )—,
a group represented by the formula —CH═N—,
a group represented by the formula —CH═N—O—,
a group represented by the formula —C(R 25 )═N—,
a group represented by the formula —C(R 25 )═N—O—,
a group represented by the formula —C(R 25 )═N—N(R 26 )—,
a group represented by the formula —CH═N—N(R 25 )—,
a group represented by the formula —CS—,
a group represented by the formula —C(S)O—,
a group represented by the formula —CSN(R 25 )—,
a group represented by the formula —O—N═C(R 25 )—,
a group represented by the formula —N═CH—,
a group represented by the formula —N(R 25 )—,
a group represented by the formula —N(R 25 )CO—,
a group represented by the formula —N(R 25 )CS—,
a group represented by the formula —N(R 25 )SO 2 —,
a group represented by the formula —N(R 25 )CO 2 —, or
a group represented by the formula —N(R 25 )CON(R 26 )—, and
r is an integer of 0 to 2,
A 331 , A 332 , A 333 , A 334 , A 335 , A 051 , and A 052 mentioned above, which are the same or different, represent
a divalent C 1-10 aliphatic hydrocarbon group which may be substituted with hydroxyl group, a C 1-6 alkoxy group, or a heterocyclic group,
an arylene group which may be substituted with hydroxyl group or a C 1-6 alkoxy group, or
a divalent heterocyclic group which may be substituted with hydroxyl group or a C 1-6 alkoxy group, and
R 20 , R 21 , R 22 , R 25 , and R 26 mentioned above, which are the same or different, represent
a hydrogen atom, or a C 1-6 alkyl group which may be substituted with 1 to 3 groups selected from the group B.
3. The 10a-azalide compound according to claim 2 or a salt thereof, wherein one of R 2 and R 3 is a hydrogen atom, and the other is:
a group represented by the formula (II),
R 4 is a hydrogen atom, or a methyl group
one of R 5 and R 6 is a hydrogen atom, and the other is:
a hydroxyl group, or an amino group, or
R 5 and R 6 combine together to represent
an oxo group, or an oxime group,
R 7 is a hydrogen atom, and
R 8 and R 9 are methyl groups.
4. The 10a-azalide compound according to claim 3 or a salt thereof, wherein one of R 32 and R 33 is a hydroxyl group, and the other is:
a group represented by the formula —CH 2 N(R 20 )—R 332 ,
a group represented by the formula —CH 2 N(R 20 )-A 334 —X 336 —R 332 , or
a group represented by the formula —CH 2 N(R 20 )-A 334 —X 336 —A 335 —X 337 —R 332 .
5. The 10a-azalide compound according to claim 3 or a salt thereof, wherein one of R 32 and R 33 is a hydroxyl group, and the other is:
a group represented by the formula —CH 2 N(R 20 )-A 334 —X 336 —R 332 .
6. The 10a-azalide compound according to claim 5 or a salt thereof, wherein A 334 is a C 2-6 alkylene group, and X 336 is:
a group represented by the formula —N(R 25 )—.
7. The 10a-azalide compound according to claim 3 or a salt thereof, wherein one of R 32 and R 33 is a hydrogen atom, and the other is:
a group represented by the formula —OCON(R 20 )—R 331 ,
a group represented by the formula —OCON(R 20 )-A 331 —X 332 —R 331 , or
a group represented by the formula —OCON(R 2 )-A 331 —X 332 —A 332 —X 333 —R 331 .
8. The 10a-azalide compound according to claim 3 or a salt thereof, wherein one of R 32 and R 33 is a hydrogen atom, and the other is:
a group represented by the formula) —OCON(R 20 )-A 331 —X 332 —R 331 .
9. The 10a-azalide compound according to claim 8 or a salt thereof, wherein A 331 is a C 2-6 alkylene group, X 332 is:
a group represented by the formula —N(R 25 )—.
10. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 1 , and a physiologically acceptable salt thereof as an active ingredient.
11. The medicament composition according to claim 10 , for treatment of a bacterial infectious disease.
12. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 2 , and a physiologically acceptable salt thereof as an active ingredient.
13. The medicament composition according to claim 12 , for treatment of a microbial infectious disease.
14. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 3 , and a physiologically acceptable salt thereof as an active ingredient.
15. The medicament composition according to claim 14 , for treatment of a microbial infectious disease.
16. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 4 , and a physiologically acceptable salt thereof as an active ingredient.
17. The medicament composition according to claim 16 , for treatment of a microbial infectious disease.
18. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 5 , and a physiologically acceptable salt thereof as an active ingredient.
19. The medicament composition according to claim 18 , for treatment of a microbial infectious disease.
20. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 6 , and a physiologically acceptable salt thereof as an active ingredient.
21. The medicament composition according to claim 20 , for treatment of a microbial infectious disease.
22. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 7 , and a physiologically acceptable salt thereof as an active ingredient.
23. The medicament composition according to claim 22 , for treatment of a microbial infectious disease.
24. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 8 , and a physiologically acceptable salt thereof as an active ingredient.
25. The medicament composition according to claim 24 , for treatment of a microbial infectious disease.
26. A medicament composition containing a substance selected from the group consisting of the 10a-azalide compound according to claim 9 , and a physiologically acceptable salt thereof as an active ingredient.
27. The medicament composition according to claim 26 , for treatment of a microbial infectious disease.
28. A method of treatment of a microbial infection, comprising administering an effective amount of the medicament according to claim 1 to a mammal to treat the microbial infection.
29. A method of treatment of a bacterial infection, comprising administering an effective amount of the medicament according to claim 1 to a mammal to treat the bacterial infection.
30. The medicament composition according to claim 10 , for treatment of a microbial infectious disease.