Methods of enhancing sweet taste of compositions using substituted thieno{2,3-D}pyrimidines

• US 8,541,421 B2
• Filed: 03/18/2011
• Issued: 09/24/2013
• Est. Priority Date: 06/08/2007
• Status: Active Grant

• Current Assignee: Senomyx Inc
• Original Assignee: Senomyx Inc
• Inventors: Tachdjian, Catherine, Tang, Xiao-Qing, Werner, Sara, Rinnova, Marketa, Chen, Qing, Servant, Guy, Li, Xiaodong, Zhang, Feng, Liu, Haitian, Zlotnik, Albert, Zoller, Mark, Klebansky, Boris, Fine, Richard, Kang, Xinshan
• Primary Examiner(s): Willis, Douglas M
• Application Number:
  US13/051,586
• Publication Number:
  US 20110230502A1
• Time in Patent Office: 921 Days
• Field of Search: 424/452, 424/461, 424/479, 424/493, 514/260.1, 544/278
• US Class Current: 514/260.1
• CPC Class Codes: A23L 2/39 Dry compositions
• CPC Class Codes: A23L 2/60 Sweeteners
• CPC Class Codes: A23L 27/30 Artificial sweetening agents
• CPC Class Codes: A23L 27/31 containing amino acids, nucleotides, peptides or derivatives
• CPC Class Codes: A23L 27/33 containing sugars or derivatives
• CPC Class Codes: A23L 27/34 Sugar alcohols
• CPC Class Codes: A23L 27/88 Taste or flavour enhancing agents
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/06 Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
• CPC Class Codes: A61P 1/08 for nausea, cinetosis or vertigo; Antiemetics
• CPC Class Codes: A61P 1/12 Antidiarrhoeals
• CPC Class Codes: A61P 1/14 Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 1/18 for pancreatic disorders, e.g. pancreatic enzymes
• CPC Class Codes: A61P 13/10 of the bladder
• CPC Class Codes: A61P 27/00 Drugs for disorders of the senses
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: A61P 3/04 : Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 : Antihyperlipidemics
• CPC Class Codes: A61P 3/10 : for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 5/00 : Drugs for disorders of the endocrine system
• CPC Class Codes: C07D 215/42 : attached in position 4
• CPC Class Codes: C07D 215/54 : attached in position 3
• CPC Class Codes: C07D 215/56 : with oxygen atoms in position 4
• CPC Class Codes: C07D 239/70 : condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 239/84 : Nitrogen atoms
• CPC Class Codes: C07D 239/94 : Nitrogen atoms
• CPC Class Codes: C07D 239/95 : with hetero atoms directly attached in positions 2 and 4
• CPC Class Codes: C07D 285/16 : Thiadiazines; Hydrogenated thiadiazines
• CPC Class Codes: C07D 417/04 : directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems
• CPC Class Codes: C07D 491/04 : Ortho-condensed systems
• CPC Class Codes: C07D 491/056 : with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
• CPC Class Codes: C07D 493/04 : Ortho-condensed systems
• CPC Class Codes: C07D 495/04 : Ortho-condensed systems
• CPC Class Codes: C07D 495/14 : Ortho-condensed systems
• CPC Class Codes: C07D 513/04 : Ortho-condensed systems
• CPC Class Codes: C07D 513/20 : Spiro-condensed systems
• CPC Class Codes: G01N 33/566 : using specific carrier or receptor proteins as ligand binding reagents where possible specific carrier or receptor proteins are classified with their target compounds

Abstract

The present invention provides, in part, substituted thieno[2,3-d]pyrimidines and methods of contacting compositions with such compounds to enhance the sweet taste of said compositions.

Claims

1. A method of enhancing the sweet taste of a comestible composition comprising contacting the comestible composition with a compound of Formula (IIa):

2. The method of claim 1, wherein A is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, —

CN, —

S(O)_cR⁹, —

NR⁹R¹⁰, —

CONR⁹R¹⁰, —

CO₂R⁹, or —

NR⁹CO₂R¹⁰.

3. The method of claim 1, wherein A is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, —

CN, —

S(O)_cR⁹, —

NR⁹R¹⁰, —

CONR⁹R¹⁰, —

CO₂R⁹, or —

NR⁹CO₂R¹⁰.

4. The method of claim 1, wherein R¹⁷ is hydrogen, alkyl, or substituted alkyl.

5. The method of claim 1, wherein

A is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, —

CN, —

S(O)_cR⁹, —

NR⁹COR¹⁰, —

NR⁹R¹⁰, —

CONR⁹R¹⁰, —

CO₂R⁹, or —

NR⁹CO₂R¹⁰; and

R¹⁷ is hydrogen, alkyl, or substituted alkyl.

6. The method of claim 1, wherein

R²⁶ is hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, —

OR³¹, —

OCOR³¹, —

NR³¹R³², —

CONR³¹R³² or —

CO₂R³¹; and

R²⁷ is hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, —

OR³³, —

OCOR³³, —

NR³³R³⁴, —

CONR³³R³⁴ or —

CO₂R³³.

7. The method of claim 1, wherein

R²⁶ is hydrogen, alkyl, or substituted alkyl;

and

R²⁷ is hydrogen, alkyl, or substituted alkyl.

8. The method of claim 1, wherein

A is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, —

CN, —

NO₂, —

S(O)_cR⁹, —

NR⁹R¹⁰, —

CONR⁹R¹⁰, —

CO₂R⁹ or —

NR⁹CO₂R¹⁰;

R¹⁷ is hydrogen, alkyl, or substituted alkyl;

R²⁶ is hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, —

OR³¹, —

OCOR³¹, —

NR³¹R³², —

CONR³¹R³² or —

CO₂R³¹; and

R²⁷ is hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, heteroalkyl, substituted heteroalkyl, —

OR³³, —

OCOR³³, —

NR³³R³⁴, —

CONR³³R³⁴ or —

CO₂R³³.

9. The method of claim 1, wherein

A is —

OH, —

NH₂, —

NHCH₃, —

N(CH₃)₂, —

NHOCH₃, —

NHC(O)CH₃, —

NHC(O)OCH₃, —

NHC(O)NH₂, —

NHC(S)NH₂, —

NHC(NH)NH₂, —

CN, —

CH₂OH, —

CH₂NH₂, —

CH₂NHCH₃, —

CH₂N(CH₃)₂, —

CO₂H, —

CONH₂, —

CONHCH₃ or —

CH₂NHC(O)CH₃;

R¹⁷ is hydrogen, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, or benzyl;

R²⁶ is hydrogen, —

CF₃, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or t-butyl; and

R²⁷ is hydrogen, —

CF₃, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or t-butyl.

10. The method of claim 1, wherein the compound is selected from the group consisting of

11. The method of claim 1, wherein the compound has a concentration from 0.0001 ppm to 10 ppm.

12. The method of claim 1, wherein the compound has a concentration from 0.0001 ppm to 100 ppm.

13. The method of claim 1, wherein the compound has a concentration from 0.01 ppm to 100 ppm.

14. The method of claim 1, wherein the comesible composition is a food or beverage product.

15. The method of claim 14, wherein the food or beverage product is selected from the group consisting of confectioneries, bakery products, dairy products, sweet and savory snacks, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dried foods, chilled foods, oils and fats, baby foods, spreads, a cooking aid product, a meal solution product, a meal enhancement product, a seasoning, a seasoning blend, cake, cookie, pie, candy, chewing gum, gelatin, ice creams, sorbet, pudding, jam, jelly, salad dressing, condiments, cereals, canned fruits, fruit sauces, a carbonated or non-carbonated beverage, a beverage mix, a beverage concentrate, soda, juice, an alcoholic beverage, and combinations thereof.