Antimicrobial compositions and uses thereof

• US 9,801,845 B2
• Filed: 06/29/2016
• Issued: 10/31/2017
• Est. Priority Date: 07/02/2015
• Status: Active Grant

• Current Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Original Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Inventors: Arhancet, Graciela B., Mahoney, Matthew, Long, Scott, Grega, Mariya, Lichtenstein, Drew L., Kuttappan, Vivek, Monestel, Jeffery Escobar, Vazquez-Anon, Mercedes
• Primary Examiner(s): Rao, Deepak
• Assistant Examiner(s): DANIEL, LAURA M
• Application Number:
  US15/196,420
• Publication Number:
  US 20170000755A1
• Time in Patent Office: 489 Days
• Field of Search: None
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 41/00 Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: A23K 10/18 of live microorganisms
• CPC Class Codes: A23K 20/10 Organic substances
• CPC Class Codes: A23K 20/105 Aliphatic or alicyclic compounds
• CPC Class Codes: A23K 20/111 Aromatic compounds
• CPC Class Codes: A23K 20/142 Amino acids; Derivatives thereof
• CPC Class Codes: A23K 20/158 Fatty acids; Fats; Products containing oils or fats
• CPC Class Codes: A23K 20/163 Sugars; Polysaccharides
• CPC Class Codes: A23K 20/174 Vitamins
• CPC Class Codes: A23K 20/189 Enzymes
• CPC Class Codes: A23K 20/195 Antibiotics
• CPC Class Codes: A23K 20/28 Silicates, e.g. perlites, zeolites or bentonites
• CPC Class Codes: A23K 20/30 Oligoelements
• CPC Class Codes: A23K 30/00 Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
• CPC Class Codes: A23K 50/10 for ruminants
• CPC Class Codes: A23K 50/30 for swines
• CPC Class Codes: A23K 50/40 for carnivorous animals, e.g. cats or dogs
• CPC Class Codes: A23K 50/75 for poultry
• CPC Class Codes: A23K 50/80 : for aquatic animals, e.g. fish, crustaceans or molluscs
• CPC Class Codes: A23L 3/34635 : Antibiotics
• CPC Class Codes: A23L 3/3535 : Organic compounds containing sulfur
• CPC Class Codes: A23L 33/127 : Antibiotics
• CPC Class Codes: A61K 2300/00 : Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/225 : Polycarboxylic acids
• CPC Class Codes: A61K 31/23 : of acids having a carboxyl group bound to a chain of seven or more carbon atoms
• CPC Class Codes: A61K 31/795 : Polymers containing sulfur
• CPC Class Codes: A61K 31/80 : Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
• CPC Class Codes: A61K 45/06 : Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61L 2/16 : using chemical substances
• CPC Class Codes: A61P 31/02 : Local antiseptics
• CPC Class Codes: A61P 31/04 : Antibacterial agents

Abstract

Antimicrobial compositions comprising sulfur- or selenium-containing, fatty-acylated alpha-hydroxy acid compounds and methods of using said compounds or compositions to inhibit microbial growth.

Claims

1. An antimicrobial composition comprising at least one compound of Formula (I) and at least one agent chosen from an essential oil, a metal chelate, a mineral, an amino acid, an organic acid, a vitamin, an antioxidant, a polyunsaturated fatty acid, a prebiotic, a probiotic, a symbiotic, an enzyme, an ionophore, a mycotoxin binder, an antiparasitic agent, an antibiotic, a herbal extract, a pigment, or combination thereof, the compound of Formula (I) having the following structure:

2. The antimicrobial composition of claim 1, wherein R¹ is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl or substituted aryl, and R² is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, or substituted aryl.

3. The antimicrobial composition of claim 2, wherein R¹ is C₁-C₆ alkyl, and R² is C₄-C₂₄ alkyl or C₄-C₂₄ alkenyl, k is from 1 to 10, and n is from 1 to 3.

4. The antimicrobial composition of claim 3, wherein R¹ is methyl, R² is C₄-C₁₆ alkyl, Y is hydrogen or an alkali metal, Z is sulfur, and n is 2.

5. The antimicrobial composition of claim 1, wherein

the essential oil is chosen from cinnamon, lavender, oregano, rosemary, or thyme;

the metal chelate is an amino acid chelate or an organic acid chelate of calcium, chromium, copper, iron, magnesium, manganese, selenium, or zinc;

the mineral is a salt, chelate, or complex of calcium, chromium, copper, iodine, iron, magnesium, manganese, molybdenum, phosphorus, potassium, selenium, or zinc;

the enzyme is chosen from phytases, proteases, or carbohydrases;

the ionophore is chosen from bambermycin, decoquiate, declazuril, lasalocid, maduramicin, monensin, narasin, nicarazin, nystatin, robenedine, salinomycin, or semduramicin;

the mycotoxin binder is chosen from charcoal, activated carbon, phyllosilicates, tectosilicates, aluminosilicates, bentonites, zeolites, clinoptilolites, montmorillonites, cellulose, glucomannans, peptidoglycans, cholestyramine, polyvinylpyrrolidone, yeast cell wall extracts, or bacterial extracts, and

the antibiotic is chosen from bacitracin, carbadox, ceftiofur, enrofloxacin, florfenicol, laidlomycin, linomycin, oxytetracycline, roxarsone, tilmicosin, tylosin, or virginiamycin.

6. The antimicrobial composition of claim 1, wherein the composition is part of a feed supplement, feed premix, feed blend, pet food, pet treat, or packaging material.

7. A feed composition comprising at least one compound of Formula (I) and at least one nutritive agent, the compound of Formula (I) having the following structure:

8. The feed composition of claim 7, wherein R¹ is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl or substituted aryl, and R² is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, or substituted aryl.

9. The feed composition of claim 8, wherein R¹ is C₁-C₆ alkyl, and R² is C₄-C₂₄ alkyl or C₄-C₂₄ alkenyl, k is from 1 to 10, and n is from 1 to 3.

10. The feed composition of claim 9, wherein R¹ is methyl, R² is C₄-C₁₆ alkyl, Y is hydrogen or an alkali metal, Z is sulfur, and n is 2.

11. The feed composition of claim 7, wherein the nutritive agent is chosen from a carbohydrate source, a fat source, a protein source, an amino acid, an alpha hydroxy acid, or combination thereof.

12. The feed composition of claim 7, further comprising at least one agent chosen from an essential oil, a metal chelate, a mineral, an amino acid, an organic acid, a vitamin, an antioxidant, a polyunsaturated fatty acid, a prebiotic, a probiotic, a symbiotic, an enzyme, an ionophore, a mycotoxin binder, an antiparasitic agent, an antibiotic, a herbal extract, a pigment, a filler, a diluent, a binder, a pH modifier, an anti-caking agent, a disintegrant, a lubricant, a dispersant, a preservative, a flavoring agent, a sweetening agent, a taste masking agent, a coloring agent, or combination thereof.

13. The feed composition of claim 7, wherein the feed composition is part of a feed premix, grain mix, feed blend, pet food, or pet treat.

14. A method for inhibiting the growth of at least one microbe, the method comprising contacting the microbe with an effective amount of at least one compound of Formula (I):

15. The method of claim 14, wherein R¹ is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl or substituted aryl, and R² is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl or substituted aryl.

16. The method of claim 15, wherein R¹ is C₁-C₆ alkyl, and R² is C₄-C₂₄ alkyl or C₄-C₂₄ alkenyl, k is from 1 to 10, and n is from 1 to 3.

17. The method of claim 16, wherein R¹ is methyl, R² is C₄-C₁₆ alkyl, Y is hydrogen or an alkali metal, Z is sulfur, and n is 2.

18. The method of any claim 14, wherein the microbe is a gram positive bacterium.

19. The method of claim 14, wherein the microbe is within an alimentary canal organ or on a surface of a subject, the subject being human, swine, poultry, ruminant, companion animal, or aquatic organism.

20. The method of claim 19, wherein the compound of Formula (I) is administered orally to the subject as part of a composition further comprising at least one agent chosen from an essential oil, a metal chelate, a mineral, an amino acid, an organic acid, a vitamin, an antioxidant, a polyunsaturated fatty acid, a prebiotic, a probiotic, a symbiotic, an enzyme, an ionophore, a mycotoxin binder, an antiparasitic agent, an antibiotic, a herbal extract, a pigment, or combination thereof;

or the compound of Formula (I) is administered orally to the subject as part of a feed composition further comprising at least one nutritive agent chosen from a carbohydrate source, a fat source, a protein source, an amino acid, an alpha hydroxy acid, or combination thereof.

21. The method of claim 19, wherein the compound of Formula (I) is applied topically to the subject as part of a composition further comprising at least one agent chosen from an essential oil, a metal chelate, a mineral, an amino acid, an organic acid, a vitamin, an antioxidant, a polyunsaturated fatty acid, a prebiotic, a probiotic, a symbiotic, an enzyme, an ionophore, a mycotoxin binder, an antiparasitic agent, an antibiotic, a herbal extract, a pigment, or combination thereof.

22. The method of claim 14, wherein the microbe is within or on a surface of an object, the object being food or feed, food or feed product, food or feed preparation equipment, food or feed packing material, health care equipment, medical devices, or packaging for household, healthcare, or industrial products.