Amino Acid Derivatives and Their Uses

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Patent No.: US None
App. No.: 15/955,798

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Abstract

Provided are compounds described by the Formula I: wherein: R 1 is a linear or branched, saturated or unsaturated aliphatic group having from 5 to 22 carbon atoms; R 2 is selected from the group consisting of the functional groups: —NH 2 ; and salts thererof; n is from 0 to 4; and R 3 is a linear or branched, saturated or unsaturated aliphatic group having from 1 to 6 carbon atoms. Also provided are compositions comprising, and methods of use of, the compounds of the present invention.

Claims (57)

1 . A method of inhibiting plaque in the oral cavity comprising contacting a surface of the oral cavity with a compound Formula I:

wherein:

R 1 is a linear or branched, saturated or unsaturated aliphatic group having from 5 to 22 carbon atoms;

R 2 is selected from the group consisting of the functional groups:

—NH 2 ;

and salts thererof, said salts having an anion X − preferably selected from the group consisting of acetate, benzoate, besylate, bromide, chloride, chlortheophyllinate, citrate, ethandisulfonate, fumarate, gluconate, hippurate, iodide, fluoride, lactate, laurylsulfate, malate, laeate, mesylate, methysulfate, napsylate, nitrate, octadecanoate, oxalate, pamoate, phosphate, polygalacturonate, succinate, sulfate, tartrate, and tosylate;

n is from 0 to 4; and

R 3 is a linear or branched, saturated or unsaturated aliphatic group having from 1 to 6 carbon atoms.

2 . The method of claim 1 wherein R 1 is a C 7 -C 17 alkyl group.

3 . The method of claim 2 wherein R 3 is a C 1 -C 6 alkyl group

4 . The method of claim 1 having a formula selected from the group consisting of:

[amino({[4-(methylcarbamoyl)-4-octanamidobutyl]amino})methylidene]azanium

[amino({[4-(ethylcarbamoyl)-4-octanamidobutyl]amino})methylidene]azanium

[amino({[4-(hexylcarbamoyl)-4-octanamidobutyl]amino})methylidene]azanium

[amino({[4-dodecanamido-4-(methylcarbamoyl)butyl]amino})methylidene]azanium

[amino({[4-dodecanamido-4-(ethylcarbamoyl)butyl]amino})methylidene]azanium

[amino({[4-dodecanamido-4-(hexylcarbamoyl)butyl]amino})methylidene]azanium

[amino({[4-(methylcarbamoyl)-4-octadecanamidobutyl]amino})methylidene]azanium

[amino({[4-(ethylcarbamoyl)-4-octadecanamidobutyl]amino})methylidene]azanium

[amino({[4-(hexylcarbamoyl)-4-octadecanamidobutyl]amino})methylidene]azanium

[amino({[5-dodecanamido-5-(ethylcarbamoyl)pentyl]amino})methylidene]azanium

N-[5-amino-1-(ethylcarbamoyl)pentyl]dodecanamide

N-[4-amino-1-(ethylcarbamoyl)butyl]dodecanamide

N-[2-amino-1-(ethylcarbamoyl)ethyl]dodecanamide

and

5 . The method of claim 4 having the formula:

6 . The method of claim 1 wherein R 2 is a guanidinyl functional group in its free base form or a salt thereof; n is 3 or 4; R 3 is an ethyl group; and R 1 is a linear or branched, saturated or unsaturated aliphatic group having from 9 to 16 carbon atoms.

7 . The method of claim 6 wherein n is 3 and R 1 is an alkyl group having from about 11 to about 13 carbon atoms.

8 . The method of claim 1 wherein R 2 is a guanidinyl functional group in its free base form or a salt thereof; n is 3; R 1 is a linear or branched, saturated or unsaturated aliphatic group having about 11 carbon atoms; and R 3 is a linear or branched, saturated or unsaturated aliphatic group having a carbon chain length of about 1 to 11 carbon atoms.

9 . The method of claim 8 wherein R 1 is an alkyl group having about 11 carbon atoms and R 3 is an alkyl group having a carbon chain length of about 2 to 8 carbon atoms.

10 . The c method of claim 1 wherein R 2 is a guanidinyl functional group in its free base form or a salt thereof; n is 3; R 1 is a linear or branched, saturated or unsaturated aliphatic group having about 7 carbon atoms; and R 3 is a linear or branched, saturated or unsaturated aliphatic group having a carbon chain length of about 7 to 16 carbon atoms.

11 . The method of claim 10 wherein R 1 is an alkyl group having about 7 carbon atoms and R 3 is an alkyl group having a carbon chain length of about 7 to 11 carbon atoms.

12 . The method of claim 1 wherein R 2 is an amine group in its free base form (—NH 2 ) or a salt thereof; and n is 1, 3, or 4.

13 . The method of claim 12 wherein n is 3; R 1 is a linear or branched, saturated or unsaturated aliphatic group having about 7 carbon atoms; and R 3 is a linear or branched, saturated or unsaturated aliphatic group having a carbon chain length of about 1 to 11 carbon atoms.

14 . The method of claim 13 wherein R 1 is an alkyl group having about 7 carbon atoms and R 3 is an alkyl group having a carbon chain length of about 8 to 11 carbon atoms.

15 . The method of claim 12 wherein n is 3; R 1 is a linear or branched, saturated or unsaturated aliphatic group having about 11 carbon atoms; and R 3 is a linear or branched, saturated or unsaturated aliphatic group having a carbon chain length of about 1 to 11 carbon atoms.

16 . The method of claim 15 wherein R 1 is an alkyl group having about 11 carbon atoms and R 3 is an alkyl group having a carbon chain length of about 2 to 6 carbon atoms.

17 . The method of claim 1 wherein the compound is selected from the group consisting of: