US2004132993A1PendingUtilityA1
Antiviral and antimicrobial guanidine or biguanidine derivatives
Priority: Aug 28, 2000Filed: Nov 25, 2003Published: Jul 8, 2004
Est. expiryAug 28, 2020(expired)· nominal 20-yr term from priority
Inventors:B. Vithal Shetty
C07D 401/14C07D 215/56C07D 471/04A61P 31/04A61P 31/00A61P 31/12
41
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Claims
Abstract
Disclosed are guanidine and biguanidine derivatives which have anti-viral and anti-bacterial activity. Also disclosed are pharmaceutical compositions containing such compounds as an active ingredient, and anti-viral and anti-bacterial methods utilizing such compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound having one of the following structures:
wherein:
a) each A is the same or different, and is selected from the group consisting of i) hydrogen, ii) a nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lower alkyl, an aromatic group or a heterocyclic group, with the proviso that with respect to structures I-III, both A's cannot be the adamantane structure above at the same time;
b) B is a straight chain or branched C 1 -C 30 alkyl group, which may be interrupted by oxygen, sulfur, optionally substituted aromatic nuclei, sulphoxide, optionally substituted cyclohexane, nitrogen optionally substituted with —NH—C (NH)—NH—C(NH)-A where A is defined above, tris (2-aminoethyl)amine, a heterocycle of the following structure:
where D is 1-3 carbon atoms and Q is hydrogen, halogen or lower alkyl; or
where Q is hydrogen, halogen or lower alkyl; or
a hydrophilic moiety; and
c) R is hydrogen or C 1 -C 6 straight or branched alkyl.
2 . The compound of claim 1 , wherein A is an antibacterial agent selected from the group consisting of
where Z is one or more heterocyclic rings containing at least one N atom
or
which may be attached to the structure above through any available point of attachment;
where n is 0 to 3; R 4 , R 5 and R 6 are each independently hydrogen or lower alkyl or alkylene; G and M are independently O, S or NR 10 ; where R 10 is hydrogen, —C(N)—NH—CN, halogen, a single bond, or lower alkyl or alkylene;
E is nitrogen or CR 10 , where R 10 is hydrogen or halogen;
K is nitrogen or CR 7 , where R 7 is hydrogen, nitro, halogen, nitrile, carboxamide, carboxyl or an ester;
R is hydrogen or lower alkyl;
R 1 is hydrogen, a lower arylalkyl group having 1-6 carbon atoms, an alkyl group having 1-4 carbon atoms in the aliphatic part and 6 to 10 carbon atoms in the aromatic part, or an aryl group having 6 to 10 carbon atoms;
R 2 is an alkyl group having one to six carbon atoms; a cycloalkyl group having 3 to 7 carbon atoms optionally substituted with halogen; 2,4-difluorophenyl or 2- or 4-fluorophenyl; amino; lower alkylamino; propylamino; N-formyl-lower alkylamino or di-lower-alkylamino; a vinyl group; a 2-fluoroethyl group; a haloalkyl group or a 2-hydroxylkyl group; phenyl or substituted phenyl wherein the phenyl ring is substituted with one or two or three substituents independently selected from C1 to C6 alkyl, halogen, methylenedioxy and hydroxy; alkoxy or trifluoromethyl; 2-, 3-, or 4- pyridine; 2- or 3-thiophene; 2-imidazole; 2-oxazole or 2-thiazole; a pyridyl or adamantyl group; or a benzoxazine group;
R 3 is a hydrogen, amino, substituted amino, halogen or a lower alkyl group;
R 8 is hydrogen or lower alkyl; and X is methylene, O, S or NR 9 , where R 9 is hydrogen or lower alkyl.
3 . A compound according to claim 2 , wherein Z is selected from the group consisting of
where R 4 and R 5 are independently hydrogen or lower alkyl.
4 . A compound according to claim 1 , selected from the group consisting of:
5 . A compound according to claim 1 , wherein the compound has the following structure:
where each V is independently hydrogen or halogen.
6 . A compound having the following structure:
where each n is independently from 1-5;
Y 1 and Y 2 are the same or different, and are optionally substituted alkyl; optionally substituted aryl; an optionally substituted heterocycle; or a single bond;
X is optionally substituted alkyl; optionally substituted aryl; or an optionally substituted heterocycle; and
each Z is independently —C(NH)—NH—C(NH)-A
where A is the same or different, and is selected from the group consisting of i) hydrogen, ii) a nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lower alkyl, an aromatic group or a heterocyclic group
and pharmaceutically acceptable salts thereof.
7 . The compound of claim 6 , wherein both Y 1 and Y 2 are single bonds.
8 . The compound of claim 7 , wherein X is C 1 -C 10 alkyl.
9 . The compound of claim 6 , wherein Y 1 and Y 2 are lower alkyl and X is phenyl optionally substituted with halogen and/or lower alkyl.
10 . The compound of claim 9 wherein Y 1 and Y 2 are —CH 2 —
11 . The compound of claim 6 , wherein Y 1 and Y 2 are lower alkyl and X is pyridyl optionally substituted with halogen and/or lower alkyl.
12 . The compound of claim 11 , wherein Y 1 and Y 2 are —CH 2 —.
13 . A compound having the following structure:
where each n is independently from 1-5;
each m is independently from 0-12;
each Z is independently —C(NH)NH—C(NH)-A,
where each A is the same or different, and is selected from the group consisting of i) hydrogen, ii) a nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lower alkyl, an aromatic group or a heterocyclic group; and
T is hydrogen, lower alkyl optionally substituted aryl or an optionally substituted heterocycle; and X is from 0-8.
14 . The compound of claim 13 , wherein the compound has one of the following structures:
15 . A compound having the following structure:
where each A is the same or different, and is selected from the group consisting of i) hydrogen, ii) nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lower alkyl, an aromatic group or a heterocyclic group; with the priviso that at least one A is not hydrogen.
16 . A compound having the following structure:
wherein each n is independently from 1-5;
m is from 0-3;
each L is independently hydrogen, lower alkyl, optionally substituted aryl, or nitro;
X is CH or N;
each Z is independently —C(NH)NH—C(NH)-A where
each A is the same or different, and is selected from the group consisting of i) hydrogen, ii) a nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lower alkyl, an aromatic group or a heterocyclic group.
17 . A compound having the following structure:
where m is from 0-4;
each L is independently hydrogen, halogen, alkyl, aryl or nitro;
each W is independently hydrogen, halogen, alkyl, alkoxy, or aryl;
X and Y are each independently CH or N;
Y 1 and Y 2 are each independently optionally substituted alkyl or a single bond; and
each Z is independently —C(NH)—NH—C(NH)-A,
where each A is the same or different, and is selected from the group consisting of i) hydrogen, ii a nitrile, iii) an amino, iv) an antibacterial agent, v) an antibiotic, vi) a quinolone, vii) an azaquinolone, and viii) one of the following groups:
where R 12 is hydrogen or C 1 -C 6 straight or branched alkyl, and R 11 is hydrogen, lowere alkyl, an aromatic group or a heterocyclic group;
and pharmaceutically acceptable salts thereof.
18 . An antiviral and/or antibacterial composition which comprises:
a) an effective amount of a compound according to claim 1; b) a pharmaceutically acceptable carrier.
19 . A method for preventing or treating a viral and/or bacterial infection in a mammalian host, said method comprising administering to a mammal in need thereof an effective amount of a compound in accordance with claim 1 .
20 . A compound having the following structure:
where each n is independently from 1-5;
Y 1 and Y 2 are the same or different, and are optionally substituted alkyl; optionally substituted aryl; an optionally substituted heterocycle; or a single bond;
X is optionally substituted alkyl; optionally substituted aryl; or an optionally substituted heterocycle; and
each Z is independently —C(NH)—NH—CN or —(CH 2 ) m —NH—C(NH)—NHCN where m is from 1 to 6.
21 . A compound having the following structure:
where each n is independently from 1-5;
each m is independently from 0-12;
each Z is independently —C(NH)—NH—CN or —(CH 2 ) q —NH—C(NH)—NH—CN where q is from 1-6, and
T is hydrogen, lower alkyl optionally substituted aryl or an optionally substituted heterocycle; and x is from 0-8.Join the waitlist — get patent alerts
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