Substituted 5-benzyl-2,4-diaminopyrimidines

Details Substituted 5-benzyl-2,4-diaminopyrimidines Substituted 5-benzyl-2,4-diaminopyrimidines

2002-07-18

2004-11-23

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C544S326000, C544S327000, C544S328000

Reexamination Certificate

active

06821980

ABSTRACT:

BACKGROUND OF THE INVENTION
A Substituted 5-benzyl-2,4-diaminopyrimidines are used in combating or preventing infectious diseases, as described, for example, in EP-A 0 793 656.
SUMMARY OF THE INVENTION
The present invention provides substituted 5-benzyl-2,4-diaminopyrimidines of the formula
in which
R
1
is C2-C3 alkyl;
R
2
denotes phenyl, naphthyl or heterocyclyl bonded via one of its C atoms, wherein phenyl, naphthyl or heterocyclyl can be mono- or polysubstituted; and
R
3
represents C2-C6 alkyl, C2-C6 alkenyl, cycloalkyl, cycloalkylalkyl, heterocyclylalkyl, alkylsulphonyl, phenylsulphonyl, cycloalkylsulphonyl, cycloalkylalkylsulphonyl, cycloalkylalkylsulphamoyl, heterocyclylsulphonyl, heterocyclylalkylsulphonyl or dialkylsulphamoyl, wherein these groups can be unsubstituted or substituted,
and acid addition salts of these compounds.
The compounds of the present invention are useful as antibacterial agents.
The present invention also provides a pharmaceutical composition comprising a compound of formula A and a carrier.
The present invention also provides a pharmaceutical composition comprising a compound of formula A, a sulphonamide compound, and a carrier, wherein the ratio in parts by weight of the compound of formula A to sulphonamide is between 1:40 and 1:1.
In addition, the present invention provides a process for the preparation of a compound of formula A according to claim
1
, comprising
a) reacting a compound of the formula
with a compound of the formula:
R
2
Y  C
in which R
1
, R
2
and R
3
have the meaning according to claim
1
, wherein any phenolic hydroxyl groups and amino/alkylamino groups present are protected, one of the symbols X and Y represents a leaving group and the other represents a group which withdraws with this leaving group,
protective groups present are split off and, optionally, aromatic substituents on R
2
/R
3
are derivatized, or
b) reacting a compound of the formula
with a compound of the formula
R
3
Z  E
in the presence of a base,
wherein any phenolic hydroxyl groups and amino/alkylamino groups present are protected and Z represents a leaving group,
protective groups present are split off and, optionally, aromatic substituents on R
2
/R
3
are derivatized, and optionally, either or both of the following steps:
to prepare compounds of the formula A wherein R
2
and/or R
3
has a sulphonyl group —SO
2
—, a corresponding compound wherein R
2
and/or R
3
has a corresponding sulphanyl group —S— or sulphinyl group —SO—, is subjected to an oxidation,
converting a compound of the formula A into a pharmaceutically acceptable acid addition salt


REFERENCES:
patent: 4515948 (1985-05-01), Kompis et al.
patent: WO 96/16046 (1996-05-01), None
Baccanari et al, Biochemistry, 20, pp. 1710-1716 (1981).
Hartman et al., FEB, 242, pp. 157-160 (1988).
Locher et al., Can. J. Infect. Dis., 6, Suppl. C, p. 469C (1995).
Burdeska et al., FEBS, 266, pp. 159-162 (1990).
Dale et al., J. Mol. Biol., 266, pp. 23-30 (1997).

Affiliated with

Also associated with

Rating

Substituted 5-benzyl-2,4-diaminopyrimidines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted 5-benzyl-2,4-diaminopyrimidines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted 5-benzyl-2,4-diaminopyrimidines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3309240