Compositions for inhibition of insect sensing

Patent metadata

Field	Value
Publication number	US-10813355-B2
Application number	US-201816186106-A
Country	US
Kind code	B2
Filing date	Nov 9, 2018
Priority date	May 6, 2011
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

In one aspect, the invention relates to chemical modulators of insect olfactory receptors. In particular, compounds and compositions are provided that can inhibit sensory (e.g., host targeting) functions in airborne insects such as mosquitoes. Methods of employing such agents, and articles incorporating the same, are also provided. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

First claim

What is claimed is:

1. A topical formulation comprising a compound, or a salt thereof, represented by a formula:

wherein R 1 is hydrogen, optionally substituted C1-C4 alkyl, optionally substituted phenyl, optionally substituted benzyl, or a structure represented by a formula selected from:

or wherein R 1 is taken together with R 2 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl;
wherein R 2 is hydrogen,
or wherein R 2 is taken together with R 1 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl;
wherein R 3 is optionally substituted (C1-C5) alkyl or optionally substituted (C1-C5) alkenyl;
wherein—R 4 is optionally substituted and selected from (C1-C5) alkyl and (C1-C5) alkenyl;
wherein R 5 is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and
wherein R 6 is hydrogen, optionally substituted (C1-C5 alkyl), or optionally substituted (C1-C5) alkenyl,
wherein the compound is not

and
at least one agent selected from film forming agents, ester containing solvents, gelling agents, skin conditioning agents and emollients, antioxidants, structuring agents, emulsifiers, silicone containing compounds, essential oils, thickening agents, and vehicles.

2. The formulation of claim 1 , wherein R 2 is hydrogen, or R 2 is taken together with R 1 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; wherein R 3 is optionally substituted (C1-C5) alkyl or optionally substituted (C1-C5) alkenyl; and wherein R 4 is optionally substituted and selected from (C1-C5) alkyl and (C1-C5) alkenyl.

3. The formulation of claim 1 , wherein R 1 , R 2 , and R 6 are hydrogen; wherein R 4 is (C1-C5) alkyl; and wherein R 5 is optionally substituted (≤C6) heteroaryl.

4. The formulation of claim 1 , wherein the compound is represented by the formula:

wherein R 1 is hydrogen or optionally substituted C1-C4 alkyl; wherein R 2 is hydrogen; wherein R 4 is optionally substituted (C1-C5) alkyl; and wherein R 11 is hydrogen, hydroxy, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 .

5. The formulation of claim 4 , wherein R 1 is hydrogen; wherein R 2 is hydrogen; wherein R 3 is methyl, ethyl, n-propyl, or isopropyl; wherein R 4 is ethyl, propyl, or cyclopropyl; and wherein R 11 is hydrogen, hydroxy, —F, —Cl, —Br, —I, —NH 2 , or —NO 2 .

6. The formulation of claim 1 , wherein the compound is represented by the formula:

wherein R 11 is —H, —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 .

7. The formulation of claim 6 , wherein R 1 is hydrogen; wherein R 2 is hydrogen; wherein R 3 is methyl, ethyl, n-propyl, or isopropyl; and wherein R 11 is hydrogen, hydroxy, —F, —Cl, —Br, —I, —NH 2 , or —NO 2 .

8. The formulation of claim 1 , wherein the compound is represented by the formula:

wherein R 11 is —H, —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 .

9. The formulation of claim 8 , wherein the compound is represented by the formula:

10. The formulation of claim 9 , wherein R 1 is hydrogen; wherein R 2 is hydrogen; and wherein R 3 is methyl, n-propyl, or isopropyl.

11. The formulation of claim 1 , wherein the compound is selected from:

12. The formulation of claim 1 , wherein the compound is selected from:

13. A method comprising providing to an insect envionment the formulation of claim 1 .

14. The method of claim 13 , wherein R 2 is hydrogen, or R 2 is taken together with R 1 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; wherein R 3 is optionally substituted (C1-C5) alkyl or optionally substituted (C1-C5) alkenyl; and wherein R 4 is optionally substituted and selected from (C1-C5) alkyl and (C1-C5) alkenyl.

15. The method of claim 13 , wherein R 1 , R 2 , and R 6 are hydrogen; wherein R 4 is (C1-C5) alkyl; and wherein R 5 is optionally substituted (≤C6) heteroaryl.

16. The method of claim 13 , wherein the compound is represented by the formula:

17. The method of claim 16 , wherein R 1 is hydrogen; wherein R 2 is hydrogen; and wherein R 3 is methyl, n-propyl, or isopropyl.

18. The method of claim 13 , wherein the compound is selected from:

19. The method of claim 13 , wherein the compound is selected from:

20. The method of claim 13 , wherein the insect environment is a human.

Assignees

• Univ Vanderbilt

Inventors

• Zwiebel Laurence
• Pask Gregory M
• Rinker David C
• Romaine Ian M
• Sulikowski Gary A
• Reid Paul R
• Waterson Alex G
• Kim Kwangho
• Jones Patrick L
• Taylor Robert W

Classifications

• Y02A50/30

  Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• A01N47/16

  the nitrogen atom being part of a heterocyclic ring · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title