NOVEL ANTIBACTERIAL AGENTS
This invention relates to novel macrolides, to the preparation of novel macrolides, to the use of such novel macrolides preventing, treating, or ameliorating various conditions, and to the use of such novel macrolides as antibacterial agents.
1 .- 17 . (canceled)
18 . A compound of the formula
or a salt thereof, wherein:
Macrolide is an antibiotic or antibiotic scaffold;
A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ;
B is alkylene or unsaturated alkylene; and
C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted.
19 . The compound of claim 18 wherein A is CH 2 .
20 . The compound of claim 18 wherein B is (CH 2 ) n , where n is 0 to 10 .
21 . The compound of claim 18 wherein B is (CH 2 ) n , where n is 1 to 10.
22 . The compound of claim 18 wherein B is (CH 2 ) n , where n is 3 to 5.
23 . The compound of claim 18 wherein B is (CH 2 ) 3 .
24 . The compound of claim 18 wherein C is optionally substituted aryl.
25 . The compound of claim 18 wherein C is optionally substituted arylalkyl.
26 . A process for preparing a compound of the formula
or a salt thereof;
the process comprising contacting a compound of the formula
Macrolide-A-B-N 3
with a compound of the formula
H═C
and a copper catalyst;
wherein Macrolide is an antibiotic or antibiotic scaffold; A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ; B is alkylene or unsaturated alkylene;
and C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted.
27 . A process for preparing a compound of the formula
or a salt thereof;
the process comprising contacting a compound of the formula
Macrolide-A-B-H
with a compound of the formula
N 3 —C
and a copper catalyst;
wherein Macrolide is an antibiotic or antibiotic scaffold; A is CH 2 , C(O), C(O)O, C(O)NH, S(O) 2 , S(O) 2 NH, or C(O)NHS(O) 2 ; B is alkylene or unsaturated alkylene; and C is hydrogen; or C is hydroxy, alkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, heteroaryl, heteroarylalkyl, or heteroarylheteroalkyl, each of which is optionally substituted.