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Details for Patent: 6,903,070

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Details for Patent: 6,903,070

Title: Glycopeptide carboxy-saccharide derivatives
Abstract:Disclosed are glycopeptide derivatives substituted at the C-terminus and/or the R-terminus with a substituent that comprises one or more saccharide groups and a carboxy group; and pharmaceutical compositions containing such glycopeptide derivatives. The disclosed glycopeptide derivatives are useful as antibacterial agents.
Inventor(s): Linsell; Martin S. (San Mateo, CA), Fatheree; Paul R. (San Francisco, CA), Leadbetter; Michael R. (San Leandro, CA), Zhu; Yan (Foster City, CA), Judice; J. Kevin (El Granada, CA)
Assignee: Theravance, Inc. (South San Francisco, CA)
Filing Date:Jun 23, 2003
Application Number:10/601,847
Claims:1. A compound of the formula: ##STR12##

wherein R.sup.3 and R.sup.5 are selected from the group consisting of: (a) R.sup.5 is hydrogen; and R.sup.3 is a group of formula (i): ##STR13## (b) R.sup.5 is hydrogen; and R.sup.3 is a group of formula (ii): ##STR14## (c) R.sup.3 is --OH; and R.sup.5 is a group of formula (iii): ##STR15##

and (d) R.sup.3 is --OH; and R.sup.3 is a group of formula (iv): ##STR16## R.sup.20 is --R.sup.a --Y--R.sup.b --(Z).sub.x, --R.sup.f, --C(O)R.sup.f, or --C(O)--R.sup.a --Y--R.sup.b --(Z).sub.x ; Y is selected from the group consisting of oxygen, sulfur, --S--S--, --NR.sup.c --, --S(O)--, --SO.sub.2 --, --NR.sup.c C(O)--, --OSO.sub.2 --, --OC(O)--, --NR.sup.c SO.sub.2 --, --C(O)NR.sup.c --, --C(O)O--, --SO.sub.2 NR.sup.c --, --SO.sub.2 O--, --P(O)(OR.sup.c)O--, --P(O)(OR.sup.c)NR.sup.c --, --OP(O)(OR.sup.c)O--, --OP(O)(OR.sup.c)NR.sup.c --, --OC(O)O--, --NR.sup.c C(O)O--, --NR.sup.c C(O)NR.sup.c --, --OC(O)NR.sup.c --, --C(.dbd.O)-- and --NR.sup.c SO.sub.2 NR.sup.c --; each Z is independently selected from hydrogen, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclic; R.sup.a is selected from the group consisting of alkylene, substituted alkylene, alkenylane, substituted alkenylene, alkynylene and substituted alkynylene; R.sup.b is selected from the group consisting of a covalent bond, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene and substituted alkynylene, provided R.sup.b is not a covalent bond when Z is hydrogen; each R.sup.c is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, heterocyclic and --C(O)R.sup.d ; each R.sup.d is independently selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl and heterocyclic; R.sup.f is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, heteroaryl, or heterocyclic; and x is 1 or 2; or a pharmaceutically-acceptable salt, stereoisomer or prodrug thereof.

2. The compound of claim 1, wherein R.sup.20 is selected from the group consisting of: --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.8 CH.sub.3 ; --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.7 CH.sub.3 ; --CH.sub.2 CH.sub.2 --NHSO.sub.2 --(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --NHSO.sub.2 --(CH.sub.2).sub.11 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.10 CH.sub.3 ; --CH.sub.2 CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 CH.sub.3 ; --CH.sub.2 CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.3 --CH.dbd.CH--(CH.sub.2).sub.4 CH.sub.3 (trans); --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.7 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S(O)--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.6 Ph; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-[4-(CH.sub.3).sub.2 CHCH.sub.2 --]-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-CF.sub.3 -Ph)-Ph; --CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --S(O)--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --S(O)--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(3,4-di-Cl-PhCH.sub.2 O--)-Ph; --CH.sub.2 CH.sub.2 --NHSO.sub.2 --CH.sub.2 -4-[4-(4-Ph)-Ph]-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --NHSO.sub.2 --CH.sub.2 -4(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --NHSO.sub.2 --CH.sub.2 -4-(Ph-C.ident.C--)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --NHSO.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 --NHSO.sub.2 -4-(naphth-2-yl)-Ph; --CH.sub.2 -4-(4-Cl-Ph)-Ph; and --CH.sub.2 -4-(4-Cl-PhCH.sub.2 --O)-Ph.

3. The compound of claim 1, wherein R.sup.5 is hydrogen; and R.sup.3 is a group of formula (i).

4. The compound of claim 3, wherein R.sup.20 is selected from the group consisting of: --(CH.sub.2).sub.11 CH.sub.3 ; --(CH.sub.2).sub.12 CH.sub.3 ; --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --O--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-CF.sub.3 -Ph)-Ph; --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --O--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-CH.sub.3 -PhCH.sub.2 O)-Ph; --CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(4-Cl-PhCH.sub.2 O)-Ph; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 Ph; and --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.8 Ph.

5. The compound of claim 1, wherein R.sup.5 is hydrogen; and R.sup.3 is a group of formula (ii).

6. The compound of claim 5, wherein R.sup.20 is selected from the group consisting of: --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --O--(CH.sub.2).sub.9 CH.sub.3 ; and --CH.sub.2 -4-(4-Cl-Ph)-Ph.

7. The compound of claim 1, wherein R.sup.3 is --OH; and R.sup.5 is a group of formula (iii).

8. The compound of claim 7, wherein R.sup.20 is selected from the group consisting of: --CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; and --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.9 CH.sub.3.

9. The compound of claim 1, wherein R.sup.3 is --OH; and R.sup.5 is a group of formula (iv).

10. The compound of claim 9, wherein R.sup.20 is selected from the group consisting of: --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 CH.sub.2 --O--(CH.sub.2).sub.9 CH.sub.3 ; --CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-CF.sub.3 -Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-Cl-Ph)-Ph; --CH.sub.2 CH.sub.2 --NH--CH.sub.2 -4-(4-CH.sub.3 -PhCH.sub.2 O)-Ph; --CH.sub.2 CH.sub.2 --S--CH.sub.2 -4-(4-Cl-PhCH.sub.2 O)-Ph; --CH.sub.2 CH.sub.2 --NH--(CH.sub.2).sub.8 Ph; and --CH.sub.2 CH.sub.2 --S--(CH.sub.2).sub.8 Ph.

11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of any of claims 1 to 10.

12. The pharmaceutical composition of claim 11, wherein the composition further comprises a cyclodextrin.

13. The pharmaceutical composition of claim 12, wherein the cyclodextrin is hydroxypropyl-.beta.-cyclodextrin.

14. A method of treating a mammal having a bacterial disease, the method comprising administering to the mammal a therapeutically effective amount of a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of any of claims 1 to 10.
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