Cooling composition

Patent metadata

Field	Value
Publication number	US-11174249-B2
Application number	US-201816630889-A
Country	US
Kind code	B2
Filing date	Jul 12, 2018
Priority date	Jul 14, 2017
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

Described herein is a composition of matter comprisingi) at least one compound of formula (I)in the form of any of its stereoisomers; and wherein R1 represents a phenyl group optionally substituted by one or two C1-3 alkyl or alkoxy groups or by one or two halides group; R2 and R3 represent, independently from each other a heterocyclic group comprising from 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3 alkyl groups; andii) at least a C1-6 linear or branched alkyl lactate.Also described herein is a method of using the composition of matter as part of a flavoring or perfuming composition or of a flavoring or perfuming consumer product. Also described herein is a process to prepare the composition of matter and the polymorph of compound of formula (I).

First claim

The invention claimed is:

1. A composition comprising:
i) from 0.1 wt % to 20 wt %, relative to the total weight of the composition, of at least one compound selected from the group consisting of N-(1H-pyrazol-5-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-ethylphenoxy)-N-(1H-pyrazol-5-yl)-N-(thiophen-2-ylmethyl)acetamide and 2-(4-ethylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; and
ii) from 80 wt % to 99.9 wt %, relative to the total weight of the composition, of ethyl lactate.

2. A process for preparing a composition comprising
i) at least one compound of formula (I)

in the form of any of its stereoisomers; and wherein R 1 represents a phenyl group optionally substituted by one or two C 1-3 alkyl or alkoxy groups or by one or two halide groups; R 2 and R 3 represent, independently from each other a heterocyclic group comprising from 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C 1-3 alkyl groups; and
ii) at least a C 1-6 linear or branched alkyl lactate;

the process comprising the steps of
a) preparing the at least one compound of formula (I) by reacting a compound of formula

wherein R 1 has the same meaning as defined above; and X represents a hydroxyl group, a C 1-10 alkoxy group or a chloride atom;
with a compound of formula

wherein R 2 and R 3 each have the same meaning as defined above;
b) crystallizing the reaction mixture obtained in step a);
c) filtering the solution of the crystallized product obtained in step b);
d) drying the crystallized product obtained in step c); and
e) solubilizing the dried crystallized product obtained in step d) in the C 1-6 linear or branched alkyl lactate.

3. The process according to claim 2 , characterized in that X represents a C 1-5 alkoxy group.

4. The process according to claim 2 , characterized in that the step a) is carried out in the presence of a base.

5. The process according to claim 4 , characterized in that the base is an alkali metal alkoxide, carbonate or hydroxide.

6. The process according to claim 2 , characterized in that the steps c) to e) of the process are performed in the same equipment.

7. A crystalline form of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide characterized by main peaks in its powder X-ray diffraction pattern obtained using copper K-alpha, radiation at 6.86, 12.46, 15.87, 17.38, 17.70, 17.93, 18.43, 19.46, 20.61, 22.08, 23.03, 23.43, 24.36, 26.11, 27.59, and 34.68.

8. The process according to claim 2 , characterized in that R 1 represents a phenyl group substituted by one or two C 1-3 alkyl or alkoxy groups or by one or two halide groups.

9. The process according to claim 2 , characterized in that R 1 represents a phenyl group substituted by one or two C 1-2 alkyl or alkoxy groups or by one or two fluoro groups.

10. The process according to claim 2 , characterized in that R 1 represents a phenyl group substituted by one or two methyl, ethyl, or methoxy groups or by one fluoro group.

11. The process according to claim 2 , characterized in that R 2 and R 3 represent, independently from each other a heterocyclic group comprising from 1 to 3 heteroatoms selected from nitrogen and sulfur.

12. The process according to claim 2 , characterized in that R 2 represents a heterocyclic group comprising from one to two nitrogen atoms.

13. The process according to claim 2 , characterized in that R 2 represents a pyrazolyl group.

14. The process according to claim 2 , characterized in that R 3 represents a heterocyclic group comprising from one to two sulfur atoms.

15. The process according to claim 2 , characterized in that R 3 represents a thiophenyl group.

16. The process according to claim 2 , characterized in that the C 1-6 linear or branched alkyl lactate is ethyl lactate.

17. The composition according to claim 1 , characterized in that the composition comprises from 0.5 wt % to 15 wt % of the at least one compound, relative to the total weight of the composition and from 85 wt % to 99.5 wt % of the ethyl lactate, relative to the total weight of the composition.

18. The process according to claim 2 , characterized in that the compound of formula (I) is N-(1H-pyrazol-5-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-ethylphenoxy)-N-(1H-pyrazol-5-yl)-N-(thiophen-2-ylmethyl)acetamide or 2-(4-ethylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide.

19. A flavoring composition comprising:
i) the composition as defined in claim 1 ;
ii) at least one ingredient selected from the group consisting of a flavor carrier, a flavoring co-ingredient and a mixture thereof; and
iii) optionally at least one flavor adjuvant.

20. The flavoring composition according to claim 19 , characterized in that the composition comprises at least one cooling agent.

21. The flavoring composition according to claim 20 , characterized in that the cooling agent is selected from the group consisting of menthol, menthol methyl ether, menthone glyceryl acetal (FEMA GRAS' 3807), menthone glyceryl ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl-N-ethyloxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849), (1R,2S,5R)—N-(4-(cyanomethyl)phenyl)menthylcarboxamide (FEMA GRAS 4496), (1R,2S,5R)—N-(2-(pyridin-2-yl)ethyl)menthylcarboxamide (FEMA GRAS 4549), menthane carboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14, WS-23 (2-Isopropyl-N,2,3-trimethylbutyramide, FEMA GRAS 3804), WS-30, and mixtures thereof.

22. A flavored consumer product comprising the composition as defined in claim 1 .

23. The flavored consumer product according to claim 22 , characterized in that the flavored consumer product is a seasoning, a condiment, a meat-based product, a soup, a carbohydrate-based product, a dairy or fat product, a savory product, a confectionery, an oral care product, an imitation product, a pet or animal food, or a beverage.

24. The flavored consumer product according to claim 23 , characterized in that the flavored consumer product is a stock, a savory cube, a powder mix, a flavored oil, a sauce, a relish sauce, a barbecue sauce, a dressing sauce, a gravy sauce, a sweet sauce, a sour sauce, a salad dressing or a mayonnaise, a poultry, a beef or pork based product, a seafood, a surimi, a fish sausage, a clear soup, a cream soup, a chicken or beef soup or a tomato or asparagus soup, an instant noodle, rice, pasta, a potatoes flake or fried, a pizza, a tortilla, a wrap, a noodle, a spread, a cheese, a regular or low fat margarine, a butter/margarine blend, a butter, a peanut butter, a shortening, a processed or flavored cheese, a snack, a biscuit, a chip, a crisp, an egg product, a potato/tortilla chip, a

Assignees

• Firmenich & Cie

Inventors

• Huboux Alexandre
• Fieber Wolfgang
• Beaussoubre Pascal

Classifications

• A61K8/4986

  with sulfur as the only hetero atom · CPC title

• A23L27/2054

  having nitrogen as the only hetero atom · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61K8/365

  Hydroxycarboxylic acids; Ketocarboxylic acids · CPC title