Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Para-n-benzene - sulfoxy-n containing doai – and said benzene...
Reexamination Certificate
1999-10-06
2001-02-27
Weddington, Kevin E. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Para-n-benzene - sulfoxy-n containing doai, and said benzene...
C514S646000, C514S647000, C514S649000
Reexamination Certificate
active
06194399
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to pharmaceutical compositions comprising aryldiamine derivatives and methods for using aryldiamine derivatives as antibacterial agents. The invention also relates to novel aryldiamine derivatives, their preparation, to pharmaceutical compositions containing them, and to methods of using them to alleviate bacterial infections.
BACKGROUND OF THE INVENTION
New classes of antibacterial agents are needed to address both the growing resistance of bacteria to present therapies and the general lack of efficacy of existing antibiotics against slow-growing organisms. Although bacterial infections were once considered well controlled, the threat posed by the emergence of multidrug-resistant organisms is now well accepted. Desirable characteristics for new antibacterial products include activity against drug resistant organisms, reduced propensity for resistance development, greater biological half-life in humans, reduced liability for allergic reactions, and broad spectrum antibacterial activity.
SUMMARY OF THE INVENTION
The present invention provides pharmaceutical compositions and formulations comprising aryldiamine compounds of generic structure (I):
wherein:
(a) R
1
, R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary or tertiary amine, or amide;
(b) X is hydrogen, NO
2
, CN, halogen, OH, SO
2
, branched or straight-chained C
1
-C
6
alkyl, alkoxy, or vinyl, positioned on the aromatic ring at any of positions 2, 4,5 or 6;
(c) wherein when R
1
, R
2
, R
3
, and R
4
are branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine or amide, R
1
, R
2
, R
3
, and R
4
are optionally interrupted with at least one heteroatom, or optionally substituted with a hydroxy, halogen, nitro, trihalomethyl group, carbonyl moiety, a substituted or unsubstituted, branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine, hydrazone, alkoxy, or aryloxy; and
(d) wherein when R
1
, R
2
, R
3
, and R
4
are branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine or amide, optionally at least one of R
1
and R
2
, together, and R
3
and R
4
, together, form a ring system, wherein the ring system is optionally interrupted by at least one heteroatom, and optionally substituted with a hydroxy, halogen, nitro, trihalomethyl group, carbonyl moiety, C
1
to C
12
alkyl, primary, secondary, or tertiary amine, alkoxy, or aryloxy;
or a salt thereof, and a pharmaceutically acceptable carrier or diluent.
In one embodiment, the invention is also directed to novel aryidiamine compounds of structure (I) wherein X is NO
2
positioned at the 4-position of the aromatic ring, R
1
, and R
3
are hydrogen, R
2
is —CH
2
CH
2
OC
6
H
5
, and R
4
is —CH
2
CH
2
NH
2
, or R
3
is hydrogen, R
4
is —CH
2
CH
2
NH
2
, and NR
1
R
2
is
The present invention also provides methods for inhibiting microbial replication and preventing and/or treating microbial infections in an animal, comprising administering an antibacterial effective amount of the pharmaceutical formulations of the invention to an animal in need of such treatment. The microbial infections which may be treated by the composition of the invention include drug resistant microbial infections and multi-drug resistant microbial infections.
DETAILED DESCRIPTION OF THE INVENTION
All patents, patent applications and literature references cited herein are hereby incorporated in their entirety. In the case of inconsistencies, the present disclosure, including definitions, will control.
Definitions
As used herein, the term “carbonyl moiety” refers to any chemical moiety comprising a carbonyl functional group, e.g., a ketone, aldehyde, carboxylic acid, acid halide, amide, peptide, anhydride and ester.
As used herein, the term “heteroatom” includes nitrogen, oxygen and sulfur, as well as any atom other than a carbon.
As used herein, “fused or polycyclic ring system” refers to a saturated or unsaturated cyclic compound. “Fused ring system” refers to cyclic compounds wherein at least two adjacent carbon centers join one or more cyclic structures, e.g., compounds represented by the formulas:
As used herein, “polycyclic ring system” refers to a compound having two or more cyclic compounds bonded in tandem, e.g., compounds represented by the formula:
Additionally, fused or polycyclic ring systems may optionally be substituted by one or more heteroatoms, halogens, C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl) and nitro groups.
Similarly, as used herein, the term “ring system” refers to a saturated or unsaturated cyclic compound, which may be optionally substituted by one or more heteroatoms, halogens, C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl) and nitro groups.
As used herein, the term “primary, secondary, or tertiary amine” refers to amine compounds having one, two, or three functional groups, respectively, including, but not limited to, heteroatoms, halogens, C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl) and nitro groups.
Further, as used herein, the term “hydrazone” refers to the reaction product of an aldehyde or ketone and hydrazine (NH
2
NH
2
). For example, a hydrazone may be represented by the formula:
wherein R may be hydrogen or alkyl. In a preferred embodiment, the hydrazone is represented by the formula:
The present invention is directed to pharmaceutical formulations comprising aryldiamine compounds of generic structure (I):
(a) wherein R
1
, R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine, amide;
(b) X is hydrogen, NO
2
, CN, halogen, OH, SO
2
, branched or straight-chained C
1
-C
6
alkyl, alkoxy, or vinyl, positioned on the aromatic ring at any of positions 2, 4,5 or 6;
(c) wherein when R
1
, R
2
, R
3
, and R
4
are branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine or amide, R
1
, R
2
, R
3
, and R
4
are optionally interrupted with at least one heteroatom, or optionally substituted with a hydroxy, halogen, nitro, trihalomethyl group, carbonyl moiety, a substituted or unsubstituted, branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine, hydrazone, alkoxy, or aryloxy; or
(d) wherein when R
1
, R
2
, R
3
, and R
4
are branched or straight-chained C
1
to C
12
alkyl, aryl, vinyl, alkyl(aryl), vinyl(aryl), primary, secondary, or tertiary amine or amide, optionally at least one of R
1
and R
2
, together, and R
3
and R
4
, together, form a ring system, wherein the ring system is optionally interrupted by at least one heteroatom, and optionally substituted with a hydroxy, halogen, nitro, trihalomethyl group, carbonyl moiety, C
1
to C
12
alkyl, primary, secondary, or tertiary amine, alkoxy, or aryloxy;
or a salt thereof, and a pharmaceutically acceptable carrier or diluent.
In one embodiment, the invention is directed to the pharmaceutical formulations comprising a compound of structure (I) wherein X is NO
2
positioned at the 4-position of the aromatic ring, R
1
and R
3
are hydrogen, R
2
is —CH
2
CH
2
OC
6
H
5
, and R
4
is —CH
2
CH
2
NH
2
; or R
3
is hydrogen, R
4
is —CH
2
CH
2
NH
2
, and NR
1
R
2
is
The present invention also provides methods for inhibiting microbial replication and preventing and/or treating microbial infections in an animal, comprising administering an antibacterial effective amount of the pharmaceutical formulations of the invention to an animal in need of such treatment.
The following are particular species of the generic formulas identified above:
A. N
1
-(2-aminoethyl)-4-nitro-N
3
-(2-ph
Lam Kelvin
Xiang Yi Bin
Darby & Darby
Scriptgen Pharmaceuticals Inc.
Weddington Kevin E.
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