Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1999-10-06
2000-12-12
Peselev, Elli
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 72, 536 74, 536 185, A61K 3170, C07H 1708
Patent
active
06159945&
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to novel 9-amino-3-keto-11,12-carbazate or carbamate derivatives of 6-O-methylerythromycin A. The compounds of this invention are useful as antibiotic agents in mammals, including man, as well as in fish and birds. The compounds of the present invention are broad-spectrum macrolide antibiotics that are effective against infections caused by certain gram-positive and gram-negative bacteria as well as protozoa. Various derivatives of erythromycin A useful as antibiotic agents are referred to in U.S. patent application Ser. No. 60/049,349, filed Jun. 11, 1997, and U.S. patent application Ser. No. 60/046,150, filed May 9, 1997, both of which are incorporated herein by reference in their entirety.
SUMMARY OF THE INVENTION
The present invention relates to compounds of the formula I ##STR2## or a pharmaceutically acceptable salt thereof, wherein: X is --CR.sup.5 R.sup.6 -- or --NR.sup.5 -- or --O--; formula XI ##STR3## wherein in said ring of formula XI, r and p are each independently an integer ranging from 1 to 3, q is 0 or 1, and R.sup.9 is --CH.sub.2 --, --O--, --S--, --C(O)--, --C(S)--, --SO.sub.2 --, --CH.dbd.--CH--, --CH(OH)CH(OH)--, or --NH--; and wherein the (CH.sub.2).sub.r and (CH.sub.2).sub.p portions of said ring of formula XI are optionally substituted by 1 to 4 substituents, and the nitrogen atom where R.sup.9 is --NH-- is optionally substituted by 1 substituent, and each hydrogen atom of R.sup.9 where R.sup.9 is --CH.sub.2 --, --CH.dbd.CH--, or --CH(OH)CH(OH) is optionally substituted by one substituent, said optional substituents being independently selected from the group consisting of --C(O)O(C.sub.1 -C.sub.10 alkyl), C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 alkanoyl, halo, nitro, cyano, 4-10 membered heterocyclic, C.sub.1 -C.sub.10 alkyl, --NR.sup.5 R.sup.6, C.sub.6 -C.sub.10 aryl, --S(O).sub.n (C.sub.1 -C.sub.10 alkyl) wherein n is an integer ranging from 0 to 2, and --SO.sub.2 NR.sup.5 R.sup.6 ;
each R.sup.1 and R.sup.2 is independently selected from H and C.sub.1 -C.sub.12 alkyl, wherein one or two carbons of said alkyl are optionally replaced by a heteroatom selected from O, S and N, and are optionally substituted by 1 to 3 substituents selected from the group consisting of --C(O)O(C.sub.1 -C.sub.10)alkyl, --O(C.sub.1 -C.sub.10)alkyl, C.sub.1 -C.sub.10 alkanoyl, halo, nitro, cyano, C.sub.1 -C.sub.10 alkyl, 4-10 membered heterocyclic, C.sub.6 -C.sub.10 aryl, --N(C.sub.1 -C.sub.10)alkyl, --S(C.sub.1 -C.sub.10)alkyl), --SO(C.sub.1 -C.sub.10)alkyl, --SO.sub.2 (C.sub.1 -C.sub.10)alkyl and --SO.sub.2 N(C.sub.1 -C.sub.10)alkyl;
or R.sup.1 and R.sup.2 are taken together with the nitrogen atom to which they are linked to form --N.dbd.CR.sup.7 R.sup.8 ;
or R.sup.1 and R.sup.2 are taken together with the nitrogen atom to which they are linked to form a heterocyclic ring of the formula XI ##STR4## wherein in said ring of formula XI, r and p are each independently an integer ranging from 1 to 3, q is 0 or 1, and R.sup.9 is --CH.sub.2 --, --O--, --S--, --C(O)--, --C(S)--, --SO.sub.2 --, --CH.dbd.CH--, --CH(OH)CH(OH)--, or --NH--; and wherein the (CH.sub.2).sub.r and (CH.sub.2).sub.p portions of said ring of formula XI are optionally substituted by 1 to 4 substituents, and the nitrogen atom where R.sup.9 is --NH-- is optionally substituted by 1 substituent, and each hydrogen atom of R.sup.9 where R.sup.9 is --CH.sub.2 --, --CH.dbd.CH--, or --CH(OH)CH(OH) is optionally substituted by one substituent, said optional substituents being independently selected from the group consisting of --C(O)O(C.sub.1 -C.sub.10 alkyl), C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 alkanoyl, halo, nitro, cyano, 4-10 membered heterocyclic, C.sub.1 -C.sub.10 alkyl, --NR.sup.5 R.sup.6, C.sub.6 -C.sub.10 aryl, --S(O).sub.n (C.sub.1 -C.sub.10 alkyl) wherein n is an integer ranging from 0 to 2, and --SO.sub.2 NR.sup.5 R.sup.6 ;
R.sup.3 is H, R.sup.7, --C(O)R.sup.7, C(O)R.sup.10, --C(O)OR.sup.7, --C(O)OR.sup.10, or --(CR.sup.5 R.sup.6).sub.m R.sup.10, wherein m is an integer r
Appleman Jolene W.
Ginsburg Paul H.
Peselev Elli
Pfizer Inc.
Richardson Peter C.
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