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5-substituted 4-amino-1h-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

A compound, CH2 technology, applied in the field of ingestible composition or pharmaceutical composition, regulating various conditions related to it, can solve the problem of sweetness residue and so on

Pending Publication Date: 2021-04-23
フィルメニッヒインコーポレイテッド
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also, high intensity sweeteners such as sucralose and aspartame have been reported to have sweetness delivery issues such as delayed onset and lingering

Method used

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  • 5-substituted 4-amino-1h-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof
  • 5-substituted 4-amino-1h-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof
  • 5-substituted 4-amino-1h-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0278] Example 1: 4-amino-5-(2-methyl-2-((5-methylpyrimidin-2-yl)amino)propoxy)-1H-benzo[c][1,2,6 ]thiadiazine 2,2-dioxide (100)

[0279]

Embodiment 1a

[0281] Example 1a: 2-amino-6-(2-methyl-2-((5-methylpyrimidin-2-yl)amino)propoxy)-benzonitrile

[0282]

Embodiment 1b

[0284] Example 1b: 2-Methyl-2-((5-methylpyrimidin-2-yl)amino)propan-1-ol

[0285]

[0286] 2-Amino-2-methylpropan-1-ol (1.60g, 17.9mmol, 2.3 equivalents), 2-chloro-5-methylpyrimidine (1.00g, 7.78mmol, 1 equivalent) and triethylamine (1.90 mL, 13.6 mmol, 1.75 eq) of the mixture was heated in the microwave at 170 °C for 2 h. The product was purified by silica gel chromatography (0% to 100% EtOAc in hexanes, gradient elution) to give the desired product as a slowly solidifying oil (469 mg, 33% yield) MS 182 (MH + ).

[0287] The compounds in Table 1 were prepared in a similar manner to the above using the corresponding aminoalcohols and halogenated heteroaryls purchased or synthesized according to known methods.

[0288] Table 1

[0289]

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Abstract

Disclosed herein are 5-Substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxide compounds useful as sweet flavor modifiers. Also disclosed herein are ingestible compositions that include one or more of these compounds in combination with a natural or artificial sweetener.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of priority to U.S. Provisional Application No. 62 / 715,669, filed August 7, 2018, which is hereby incorporated by reference as if set forth in its entirety herein. technical field [0003] In certain forms, the present disclosure generally relates to novel classes of 4-amino-2,2-dioxobenzo[c][1,2,6]thiadiazine derivatives. In some other forms, the invention relates to formulations, such as ingestible or pharmaceutical compositions, comprising such compounds. In some other forms, the present disclosure provides methods of using (or utilizing) such compounds in various foods, beverages, and other ingestible compositions, as well as in the treatment of various diseases associated with the modulation of T1R2 / T1R3 receptors. The method used in the method of the condition. In some embodiments, the present disclosure provides methods of using the compounds as flavor enhancers in one or more...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A23L27/30C07D417/14A61K31/549
CPCC07D417/12C07D417/14A23L27/88A23L2/52A23L2/56A23L2/60A23L27/2056A23L27/33A23V2002/00
Inventor J·R·福钦C·塔什特简G·赛尔温特B·W·晴T·戴维斯
Owner フィルメニッヒインコーポレイテッド
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