CONVERGENT PROCESSES FOR PREPARING MACROLIDE ANTIBACTERIAL AGENTS
The invention described herein relates to processes for preparing ketolide antibacterial agents. In particular, the invention relates to intermediates and processes for preparing ketolides that include a 1,2,3-triazole substituted side chain.
1 - 25 . (canceled)
26 . A composition comprising solithromycin that is substantially free of
wherein A-B is (CH 2 ) 4 .
27 . A compound of the formula:
wherein:
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 saturated C 0 C 10 ; or B is unsaturated C 2 C 10 ; or
AB taken together is alkylene, alkenylene, cycloalkylene, or arylene;
C is hydrogen, halogen, hydroxy, acyl, acyloxy, sulfonyl, ureyl, and carbamoyl, and alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted; and
R 100 is hydrogen or a hydroxyl protecting group.
28 . The compound of claim 27 wherein C is aryl, heteroaryl, arylalkyl, or heteroarylalkyl, each of which is optionally substituted.
29 . The compound of claim 27 wherein A is CH 2 .
30 . The compound of claim 27 wherein B is (CH 2 ) n , and n is an integer from 2-6.
31 . The compound of claim 27 of the formula
32 . The compound of claim 27 of the formula
33 . The compound of claim 32 wherein R 100 is hydrogen.
34 . An intermediate of the formulae
wherein:
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 saturated C 0 C 10 ; or B is unsaturated C 2 C 10 ; or
AB taken together is alkylene, alkenylene, cycloalkylene, or arylene;
C is hydrogen, halogen, hydroxy, acyl, acyloxy, sulfonyl, ureyl, and carbamoyl, and alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted; or C is C P , where C P is a protected form of C;
R 100 is hydrogen or a hydroxyl protecting group; and
N P is NH 2 or protected amino.
35 . The intermediate of claim 34 wherein C is aryl, heteroaryl, arylalkyl, or heteroarylalkyl, each of which is optionally substituted.
36 . The intermediate of claim 34 wherein A is CH 2 .
37 . The intermediate of claim 34 wherein B is (CH 2 ) n , and n is an integer from 2-6.
38 . The intermediate of claim 34 wherein B is (CH 2 ) n , and n is 2, 3, or
4 .
39 . The intermediate of claim 34 wherein R 100 is acyl.
40 . The intermediate of claim 34 of the formula
41 . The intermediate of claim 34 of the formula
42 . The intermediate of claim 34 of the formula
43 . The intermediate of claim 34 of the formula
44 . The intermediate of claim 34 of the formula