Amino Acid Derivatives and Their Uses

Patent metadata

Field	Value
Publication number	US-2016145203-A1
Application number	US-201514938334-A
Country	US
Kind code	A1
Filing date	Nov 11, 2015
Priority date	Nov 11, 2014
Publication date	May 26, 2016
Grant date	—

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:

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.

First claim

What is claimed is:

1 . A compound 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:

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 compound of claim 1 wherein R 1 is a C 7 -C 17 alkyl group.

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

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

5 . The compound of claim 4 having the formula:

6 . The compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 . A composition comprising a compound of claim 1 and a vehicle wherein said composition is in a form selected form the group consisting of a mouthwash, mouth rinse, mouth spray, toothpaste, tooth gel, sub-gingival gel, mousse, foam, denture care product, dentifrice, lozenge, and chewable tablet.

18 . The composition of claim 17 wherein said composition is a mouthwash comprising a compound of claim 4 ; a carrier comprising water; and at least one surfactant selected from the group consiting of anionic, non-ionic, betaine surfactants and combinations of two or more thereof.

19 . The composition of claim 18 further comprising at least one essential oil selected from the group consiting of menthol, thymol, eucalyptol, methyl salicylate, and combinations of two or more thereof.

20 . A method of inhbiting plaque in the oral cavity comprising contacting a surface of the oral cavity with a compound of claim 1 .

Assignees

• Johnson & Johnson Consumer Inc

Inventors

• Gambogi Robert J
• Geonnotti Iii Anthony R
• Giano Michael C
• Petersen Latrisha

Classifications

• C07C237/22

  having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K) · CPC title

• A61K8/44

  Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof · CPC title

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title

• C07C279/12 Primary

  being further substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• A61K8/43 Primary

  Guanidines · CPC title