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N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use

a technology of alkylcarbonyl-amino lactone and alkylcarbonyl-amino acid ester, which is applied in the field of refreshing, soothing and cooling compounds, can solve the problems of limited utility of menthol in relieving sensory discomfort, no compound currently known to the art has the potency or duration of action, and no other compound can achieve the effect of increasing alertness, reducing sleepiness and fatigue, and increasing alertness

Inactive Publication Date: 2011-04-07
WEI EDWARD T
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0023]FIG. 1 is a bar graph showing duration of cooling (hours) for eight compounds (in order): D-Ala-OEt, D-Ala-OMe, D-Hsl, Sar-OEt, WS-5, WS-12, WS-3, and (−)-menthol.

Problems solved by technology

Menthol's utility in relief of sensory discomfort is, however, limited by its short duration of action and by its multimodal actions on sensory processes—including odor, harshness of taste, and irritation.
The unpleasant effects of menthol can be easily experienced, for example, when menthol-containing ointments are brought near the eye surface.
The menthol vapors hurt the eye and causes tearing.
None of the compounds currently known to the art have the potency or duration of action to qualify them as possible medications for use in disorders of eye discomfort such as itch (allergic conjunctivitis), pain, and dryness.

Method used

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  • N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use
  • N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use
  • N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use

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Embodiment Construction

[0024]A class of compounds that is suitable to be used as an active ingredient in (e.g., pharmaceutical) preparations for use on the skin of the eyelids and on the ocular surface has been found.

[0025]These compounds are suitable, for example, for use as agents to reduce discomfort such as itch, a sense of dryness and irritation, and pain.

[0026]These compounds have one or more of the following properties:[0027](i) a refreshing, soothing, and cooling action on the surface of the skin and, in pathological states, act as an anti-irritant, anti-pruritic, and / or anti-nociceptive agent[0028](ii) a minimal irritant action on the eye when the compound is applied to facial skin near and on the ocular surface;[0029](iii) a rapid onset of action of less than 5 minutes, preferably less than 1 minute;[0030](iv) a duration of action that exceeds 1 hour, for example, when applied onto the upper eyelids at a concentration of 0.2 to 2 mg / ml in a towelette; and[0031](v) a robust cool, soothing, and re...

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Abstract

The present invention generally relates to refreshing, soothing, and cooling compounds that affect sensory processes. More particularly, the present invention pertains to certain N-alkylcarbonyl-amino acid ester as described herein; compositions and articles comprising such compounds; and methods of treatment, for example, methods of increasing alertness, and decreasing fatigue or sleepiness, and alleviating ocular discomforts of irritation, itch, and pain.

Description

RELATED APPLICATIONS[0001]This application is a continuation-in-part of U.S. patent application 20080227857, filed Mar. 23, 2006, inventor Wei, entitled “N-Alkylcarbonyl-Amino Acid Ester and N-Alkylcarbonyl-Amino Lactone Compounds and Their Use”, incorporated by reference.[0002]This application is related to:[0003]U.S. Provisional Application No. 60 / 667,166 filed 29 Mar. 2005;[0004]U.S. Provisional Application No. 60 / 683,384 filed 20 May 2005;[0005]U.S. Provisional Application No. 60 / 702,505 filed 26 Jul. 2005;[0006]U.S. patent application Ser. No. 11 / 203,728 filed 13 Aug. 2005; and[0007]U.S. Provisional Application No. 60 / 772,374 filed 9 Feb. 2006;[0008]the contents of each of which are incorporated herein by reference in their entirety.TECHNICAL FIELD[0009]The present invention generally relates to refreshing, soothing, and cooling compounds that affect sensory processes. More particularly, the present invention pertains to certain N-alkylcarbonyl-amino acid ester and N-alkylcarbo...

Claims

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Application Information

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IPC IPC(8): A61K31/215C07C233/63A61P29/00A61P17/04
CPCC07B2200/07C07D307/33C07C2101/14C07C233/63C07C2601/14A61P1/02A61P1/08A61P11/00A61P11/06A61P11/14A61P17/00A61P17/04A61P17/06A61P25/00A61P25/34A61P29/00A61P3/00A61P31/04C07C233/05C07C233/08C07D277/24C07C243/38C07C255/57C07D213/86C07D307/68C07D307/84C07D307/85C07D333/38
Inventor WEI, EDWARD T.
Owner WEI EDWARD T
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