P-menthawe-3-carboxylic acid esters to treat airways diseases

A technology for upper respiratory tract and diseases, which is applied in the field of p-menthane 3-carboxylate for the treatment of respiratory diseases, and can solve the problems of sugar and calorie increase

Inactive Publication Date: 2010-12-01
爱德华·塔克·韦
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of long-term lozenge use are increased sugar and calories in the diet

Method used

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  • P-menthawe-3-carboxylic acid esters to treat airways diseases
  • P-menthawe-3-carboxylic acid esters to treat airways diseases
  • P-menthawe-3-carboxylic acid esters to treat airways diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0171] Synthesis of hydroxy p-menthane carboxylate

[0172] (1R,2S,5R)-2-Isopropyl-5-methyl-2-hydroxyethyl cyclohexanecarboxylate (CPS-004)

[0173] (1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexanecarboxylic acid 2,3-dihydroxypropyl ester (CPS-030)

[0174]The synthesis of compounds of formula 1 is familiar to those skilled in the chemical arts and begins with the reaction of an appropriate alkyl-substituted cycloalkylcarboxylic acid with thionyl chloride to form the carbonyl chloride. The carbonyl chloride is then reacted with an excess of the appropriate alcohol derivative, optionally in the presence of a suitable hydrogen chloride acceptor or base. Many suitable alcohols are available from commercial sources such as Sigma-Aldrich Co., St. Louis, MO. A suitable method is described by Watson et al., 1977, US Patent 4,033,994. For example, for the synthesis of CPS-004, 5-methyl-2-methyl-2- Isopropylcyclohexanecarboxylic acid. Thus, the Grignard reagent is generated in dry tetr...

Embodiment 2

[0176] Octanol / water partition coefficient

[0177] The log P (octanol / water partition coefficient) of the compound of formula 1 was calculated and shown in the table. It can be seen that these compounds are compatible with the carrier for incorporation and can be stored in a depot for metered delivery using an aerosol dispenser.

[0178] Log P values ​​are also given as parameters for the selection of primary supports and co-solvents. For example, CPS-160 has excellent water solubility with a low log P value, so it should be compatible with aqueous solvents containing 1% to 5% ethanol or propylene glycol. On the other hand, for long-term reduction of airway sensory irritation, such as in COPD, compound CPS-003 may be a better choice.

[0179]

[0180]

[0181] (*)CPS-004, (**)CPS-030

Embodiment 3

[0183] biometrics

[0184] CPS-004 and CPS-030 are liquids at room temperature. These compounds were tested by placing 0, 2, 5 and 8 mg of these compounds on a 6 inch glass rod and applying the compounds to the posterior 1 / 3 of the dorsal surface of the tongue. After depositing the test substance, the subject is instructed to keep the mouth closed and allow the test substance to distribute in the back of the mouth (oropharynx). The presence and duration of sensations from the oral cavity were then recorded.

[0185] Note that 2 mg of the substance has a cooling effect on the back of the mouth. CPS-004 and CPS-030 have similar potency. CPS-030 has a spicy taste, which is objectionable. The duration of the cooling sensation lasted 10 to 15 minutes, with higher doses producing a cooling sensation that was still perceptible after 30 minutes.

[0186] In the next set of experiments, CPS-004 or CPS-030 was mixed at 50 mg / ml in a solution of 5% ethanol-95% saline. 10 milliliter...

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Abstract

The present invention relates to methods and devices for treating sensory discomfort in the upper airways of a human; treating sensory discomfort in the oropharynx of a human; alleviating pain from pharyngitis in a human; alleviating cough in a human; and ameliorating the symptoms and signs of asthma, dyspnea, sleep apnea, snoring, or chronic obstructive pulmonary disease in a human. According to the invention, an active compound is delivered, preferably selectively delivered, to the oropharynx, preferably the oropharyngeal surfaces, more preferably the lower retropalatal oropharynx (LRO) of the patient. According to the invention, the active compound is a compound of the following formula, wherein -R is C2 to C4 hydroxyalkyl or polyhydroxyalkyl.

Description

[0001] related application [0002] This application is related to US Provisional Application No. 61 / 008,980, filed December 21, 2007, which is incorporated herein by reference in its entirety. technical field [0003] The present invention relates to treating people's upper respiratory tract feeling discomfort, treating people's pharynx feeling discomfort, relieving people's pharyngitis pain, alleviating people's cough and improving people's asthma, dyspnea, sleep apnea, snoring or symptoms of chronic obstructive pulmonary disease and Methods and equipment for signs. According to the present invention, the active compound is delivered, preferably selectively, to the oropharynx, preferably the oropharyngeal surface, more preferably the lower retropalatal oropharynx (LRO) of a patient. According to the present invention, the active compound is a compound of formula wherein -R is C 2 to C 4 Hydroxyalkyl or polyhydroxyalkyl: [0004] Background of the invention [0005]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/215A61P11/00A61P11/04A61P11/14A61K9/12
CPCA61K9/08A61K31/215A61P11/00A61P11/04A61P11/06A61P11/14A61P29/00
Inventor 爱德华·塔克·韦
Owner 爱德华·塔克·韦
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