Compositions for Inhibition of Insect Sensing

Patent metadata

Field	Value
Publication number	US-2019075798-A1
Application number	US-201816186106-A
Country	US
Kind code	A1
Filing date	Nov 9, 2018
Priority date	May 6, 2011
Publication date	Mar 14, 2019
Grant date	—

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 compound having a structure represented by a formula:

wherein m, n, p, and q are independently 0 or 1;
wherein L 1 and L 2 are independently divalent organic groups having from 1 to 8 non-hydrogen members;
wherein Q 1 is —O—, —S(O)—, or —SO 2 —;
wherein Q 2 is —O—, —S—, or —NR 4 ;
wherein R 7 is optionally substituted and selected from monocyclic aryl, bicyclic aryl, monocyclic heteroaryl, bicyclic heteroaryl, and tricyclic heteroaryl;
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 R 1 is taken together with a substituent of R 7 to form a five-, six-, or seven-membered heterocycloalkyl ring;
wherein R 4 is optionally substituted and selected from (C1-C5) alkyl, (C1-C5) alkenyl, (C6-C10) aryl, (≤C10) aralkyl, (≤C8) heteroaryl, and (≤C8) heteroaralkyl; and
wherein R 5 is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and
wherein R 6a and R 6b are independently selected from hydrogen, optionally substituted (C1-C5 alkyl), or optionally substituted (C1-C5) alkenyl,
or R 6a and R 6b , along with the intermediate carbon, together comprise a C3-C6 cycloalkyl ring or a C2-C5 heterocycloalkyl ring; or salt thereof, wherein the compound is not

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

wherein m, n, p, and q are independently 0 or 1;
wherein L 1 and L 2 are independently divalent organic groups having from 1 to 8 non-hydrogen members;
wherein Q 1 is —O—, —S(O)—, or —SO 2 —;
wherein Q 2 is —O—, —S—, or —NR 4 ;
wherein R 7 is optionally substituted and selected from monocyclic aryl, bicyclic aryl, monocyclic heteroaryl, bicyclic heteroaryl, and tricyclic heteroaryl;
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 R 1 is taken together with a substituent of R 7 to form a five-, six-, or seven-membered heterocycloalkyl ring;
wherein R 4 is optionally substituted and selected from (C1-C5) alkyl, (C1-C5) alkenyl, (C6-C10) aryl, (≤C10) aralkyl, (≤C8) heteroaryl, and (≤C8) heteroaralkyl; and
wherein R 5 is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and
wherein R 6a and R 6b are independently selected from hydrogen, optionally substituted (C1-C5 alkyl), or optionally substituted (C1-C5) alkenyl,
or R 6a and R 6b , along with the intermediate carbon, together comprise a C3-C6 cycloalkyl ring or a C2-C5 heterocycloalkyl ring; or salt thereof, 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.

3 . The formulation of claim 2 , wherein the compound has a structure 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 R 1 is taken together with R 2 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl;
R 2 is hydrogen, hydroxy, nitro, halo, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl,
or R 2 is taken together with R 1 to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl;
R 3 is hydrogen, hydroxy, nitro, halo, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl;
R 4 is optionally substituted and selected from (C1-C5) alkyl, (C1-C5) alkenyl, (C6-C10) aryl, (≤C10) aralkyl, (≤C8) heteroaryl, and (≤C8) heteroaralkyl;
R 5 is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and
R 6 is hydrogen, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl.

4 . The formulation of claim 3 , 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.

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

6 . The formulation of claim 3 , 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, —CI, —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; wherein R 4 is ethyl, propyl, or cyclopropyl; and wherein R 11 is hydrogen, hydroxy, —F, —CI, —Br, —I, —NH 2 , or —NO 2 .

8 . The formulation of claim 3 , wherein the compound is represented by the formula:

wherein R 11 is —H, —OH, —F, —CI, —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 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, —CI, —Br, —I, —NH 2 , or —NO 2 .

10 . The formulation of claim 3 , wherein the compound is represented by the formula:

wherein R 11 is —H, —OH, —F, —CI, —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 .

11 . The formulation of claim 10 , wherein the compound is represented by the formula:

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

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• A01N47/18

  containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title