Shikimate analogues and methods of use

Patent metadata

Field	Value
Publication number	US-2020031791-A1
Application number	US-201916592340-A
Country	US
Kind code	A1
Filing date	Oct 3, 2019
Priority date	Feb 15, 2016
Publication date	Jan 30, 2020
Grant date	—

Abstract

The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, devices and kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating and neutralizing irritant or odoriferous compounds on animate or inanimate surfaces or in atmospheres. Examples of such irritant and odoriferous compounds include urushiols from poison ivy, oak, and sumac and mercaptans of skunk spray.

First claim

What is claimed is:

1 . A composition comprising at least one shikimate analogue, and one or more secondary compounds, the at least one shikimate analogue comprising Structural Formula I or Structural Formula II:

wherein,
X is O, N, S, or is absent;
R 1 is selected from the group consisting of H, (C1-C8)alkyl, (C1-C8)alkenyl, (C1-C8)alkynyl, cyano, halo, nitro, thio, substituted phenyl, phenylmethyl, and substituted naphthalenyl;
R 2 is selected from the group consisting of H, (C1-C8)alkyl, (C1-C8)alkenyl, (C1-C8)alkynyl, cyano, halo, nitro, thio, substituted phenyl, phenylmethyl, and substituted naphthalenyl, or is absent;
R 3 is selected from the group consisting of fluoro, chloro, bromo, iodo, hydroxyl, substituted phosphate, —O-tosyl, —O-mesyl, (C1-C8)alkoxy, (C2-C8)acyloxy, substituted phenoxy, substituted naphthalenyloxy, substituted naphthalenylmethoxy, (C1-C12)primary amino, (C1-C12)secondary amino, (C1-C12)tertiary amino, and (C1-C12)cyclic amino, (C1-C8)ammonio, (C1-C8)carboxamino, (C1-C8)imino, azido, (C1-C8)azo, cyanato, isocyanato, nitrooxy, cyano, isocyano, nitrosooxy, nitro, nitroso, (C1-C8)substituted carbamoyl, hydroxyamino, morpholino, anilino, indol, pyrrol, imidazole, benzimidazol, pyrazol, guanidino, piperazino, polyamino, and N-methylated polyamino;
R 4 is selected from the group consisting of H, (C1-C8)alkyl, (C1-C8)alkenyl, (C1-C8)alkynyl, cyano, halo, nitro, thio, substituted phenyl, hydroxyl, (C1-C8)alkoxy, (C2-C8)acyloxy, (C1-C8)carboxamino, substituted phenoxy, phenylmethoxy, [1-(methoxycarbonyl)ethenyl]oxy, and (1-carboxyethenyl)oxy;
R 5 selected from the group consisting of H, (C1-C8)alkyl, (C1-C8)alkenyl, (C1-C8)alkynyl, cyano, halo, nitro, thio, substituted phenyl, hydroxyl, (C1-C8)alkoxy, (C2-C8)acyloxy, (C1-C8)carboxamino, substituted phenoxy, phenylmethoxy, [1-(methoxycarbonyl)ethenyl]oxy, and (1-carboxyethenyl)oxy; and
R 6 is selected from the group consisting of H, (C1-C8)alkyl, (C1-C8)alkenyl, (C1-C8)alkynyl, cyano, halo, nitro, thio, substituted phenyl, hydroxyl, (C1-C8)alkoxy, (C2-C8)acyloxy, (C1-C8)carboxamino, substituted phenoxy, phenylmethoxy, [1-(methoxycarbonyl)ethenyl]oxy, and (1-carboxyethenyl)oxy, with the proviso that at least one of the one or more secondary compounds is not water.

2 . The composition of claim 1 , wherein the at least one shikimate analogue has Structural Formula I, wherein X=O, R 1 is (C1-C8)alkyl, R 2 is absent, R 3 is selected from the group consisting of fluoro, chloro, bromo, iodo, and (C1-C8)alkoxy, R 4 =OH, R 5 =OH, and R 6 =OH.

3 . The composition of claim 1 , wherein the at least one shikimate analogue has Structural Formula I, wherein X=O, R 1 =CH 3 , R 2 is absent, R 3 =Cl, R 4 =OH, R 5 =OH, and R 6 =OH (Pericosine A).

4 . The composition of claim 1 , wherein the at least one shikimate analogue has Structural Formula I, wherein X=O, R 1 =CH 3 , R 2 is absent, R 3 =OCH 3 , R 4 =OH, R 5 =OH, and R 6 =OH (Pericosine C).

5 . The composition of claim 1 , wherein the at least one shikimate analogue is selected from the group consisting of Pericosine A, Pericosine B, Pericosine C, and Pericosine D.

6 . The composition of claim 1 , wherein at least one of the one or more secondary compounds is not methanol, ethanol, or a propanol.

7 . The composition of claim 1 , wherein the one or more secondary compounds is selected from the group consisting of organic bases, inorganic bases, and organic/inorganic bases.

8 . The composition of claim 1 , wherein the one or more secondary compounds is an amine or a salt thereof.

9 . The composition of claim 8 , wherein the amine is an alkyl amine.

10 . The composition of claim 9 wherein the alkyl amine is selected from the group consisting of methyl amine, ethyl amine, dimethyl amine, diethyl amine, trimethyl amine, triethyl amine, diethanolamine, triethanolamine, and trimethylammonia.

11 . The composition of claim 8 , wherein the amine is an acyclic or cyclic polyamine.

12 . The composition of claim 11 , wherein the acyclic or cyclic polyamine is selected from the group consisting of spermine, spermidine, tris(2-aminoethyl)amine, cycler, cyclam, 1,4,7-triazacyclononane, 1,1,1-tris(aminomethyl)ethane, ethylenediamine, 1,4-diazabicyclo[2.2.2]octane (DABCO), diethylenetriamine, triethylenetetramine, 1,3-diaminopropane, putrescine, cadaverine, sym-norspermidine, sym-homospermidine, norspermine, thermospermine, carboxyspermidine, norcarboxyspermidine, caldopentamine, caldohexamine, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, N-methylethylenediamine, 1,4-diaminobutane, 3-(methylamino)propylamine, N,N′-dimethylethylenediamine, N-methyl-1,3-diaminopropane, 1-dimethylamino-2-propylamine, 3-(dimethylamino)-1-propylamine, N,N,N′,N′-tetramethyldiaminomethane, N,N,N′-trimethylethylenediamine, N-isopropylethylenediamine, N-propylethylenediamine, 2-(aminomethyl)-2-methyl-1,3-propanediamine, 1,2-diamino-5-bromo-3-chlorobenzene, 3,5-dichloro-1,2-diaminobenzene, 4-bromo-1,2-diaminobenzene, 4,5-dichloro-o-phenylenediamine, 4-chloro-1,3-diaminobenzene, 2-nitro-1,4-phenylenediamine, 3-nitro-1,2-phenylenediamine, 4-nitro-o-phenylenediamine, m-phenylenediamine, o-phenylenediamine, p-phenylenediamine, trans-4-cyclohexene-1,2-diamine, cis-4-cyclohexene-1,2-diamine, hexamethylenetetramine, 4-aminobenzylamine, N,N′-bis(2-aminoethyl)-1,3-propanediamine, methyl 3,4-diaminobenzoate, 1,2-diamino-3,5-dimethylbenzene, 4,5-dimethyl-1,2-phenylenediamine, 4-(2-aminoethyl)aniline, aniline, m-xylylenediamine, phenylethylenediamine, o-xylylenediamine, p-xylylenediamine, 1,8-diaminooctane, N,N-dimethyldipropylenetriamine, 1,2-bis(3-aminopropylamino)ethane, N-tosylethylenediamine, 2,2,4(2,4,4)-trimethyl-1,6-hexanediamine, 1,4-diaminonaphthalene, 1,5-diaminonaphthalene, 1,8-diaminonaphthalene, 4-tert-butyl-2,6-diaminoanisole, 2,2′-oxydianiline, 4,4′-oxydianiline, 3,3′-diaminobenzidine, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 4,4′-ethylenedianiline, 2,4,6-triethyl-1,3,5-benzenetrimethanamine, and 1,8-anthracenedimethanamine.

13 . The composition of claim 8 , wherein the amine is selected from the group consisting monoamines, polyamines, or polymeric amines coated on or crosslinked with a polymer particle.

14 . The composition of claim 8 , wherein the amine is selected from the group consisting monoamines, polyamines, or polymeric amines coated on or crosslinked with a polymeric film.

15 . The composition of claim 8 , wherein the amine is selected from the group consisting monoamines, polyamines, or polymeric amines functionalized on or infused into a hydrogel.

16 . The composition of claim 8 , wherein the amine is selected from the group consisting cyclic polyamine homopolymers and heteropolymers comprising at least one of polyvinylamine, polyethyleneimine, polyvicinalamine, polyamidoamine, polyallyamines, and polyetheramines.

17 . The composition of claim 1 , wherein the one or more secondary compounds is a pyridine or pyridinium selected from the group consisting of pyridine, alkylated pyridines, 2,6-lutidine, 2,4-lutidine, pyridazine, pyrimidine, pyrazine, 4-bromopyridine, 2,6-di-tert-butylpyridine, pyridine-2,6-dicarboxylic acid, pyridinium cations, and salts of the above.

18 . The composition of claim 1 , wherein the one or more secondary compounds is an imidazole or alkylated imidazole.

19 . The composition of claim 1 , wherein the one or more secondary compounds is a pyrrole or alkylated pyr

Assignees

• Univ Oklahoma

Inventors

• Du Lin
• Cichewicz Robert
• Nicholas Ken
• You Jianlan

Classifications

• A61L2300/216

  with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C259/06

  having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C69/757

  having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety · CPC title

• A61L15/46

  Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria · CPC title