US2022378675A1PendingUtilityA1
Compounds reducing malodour perception and the use thereof
Est. expiryJan 30, 2037(~10.6 yrs left)· nominal 20-yr term from priority
Inventors:Pierre ChatelainMarkus GautschiThierry GranierYannick QuesnelCharles Stanley SellAlex Veithen
C07C 69/618C07C 47/277C07C 69/003A61K 8/42C07C 69/734C07C 49/217A61K 8/361C07C 57/42C07C 57/03C07C 33/30A61Q 15/00A61K 8/34C07C 233/11C07C 33/20C07C 43/166C11B 9/0061C11B 9/0065C07C 255/57C07C 43/23C07C 2601/08A61K 8/37C07C 59/64A61K 8/35C07C 43/176C07C 255/50A61K 8/40C07C 47/232C07C 233/09C07C 255/34C07C 33/483C07C 69/65
71
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References
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Claims
Abstract
The present invention relates to new malodour-counteracting agents of formula (I) or stereoisomers thereof, particularly useful in blocking the olfactory perception of androstenone, Formula (I), wherein R1, R2, R3, R4, R5, R6, R7 and X have the same meaning as that defined in the claims. The present invention also relates to consumer products comprising said agents. The present invention also relates to the use of said agents to suppress or attenuate undesirable odour, as well as to methods to suppress or attenuate undesirable odour employing said compounds.
Claims
exact text as granted — not AI-modified1 - 24 . (canceled)
25 . A process for the preparation of a compound of formula (I)
comprising the steps of:
(a) coupling a compound of a formula A with a compound of formula B, thereby obtaining a compound of formula C, and
(b1) contacting compound of formula C with phosphorane derivatives D thereby obtaining compound of formula (I);
or (b2) contacting compound of formula C phosphonate derivative F thereby obtaining compound of formula (I);
wherein
X is selected from the group consisting of —C(═O)OR 8 , cyano, —C(═O)—C 1-6 alkyl, —C(═O)—NR 9 R 10 , hydroxyC 1-6 alkyl, —C(═O)H, and C 1-6 alkoxyC 1-6 alkyl;
R 1 is hydrogen or C 1-6 alkyl;
R 2 is hydrogen or a group selected from C 1-7 alkyl and C 2-7 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl;
R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 8 is hydrogen or C 1-6 alkyl;
R 9 is hydrogen or C 1-6 alkyl;
R 10 is hydrogen or C 1-6 alkyl;
R 11 is C 6-12 aryl or C 1-12 alkyl; and
R 12 is C 1-12 alkyl.
26 . The process according to claim 25 , wherein the process comprises the steps of (a) and (b1).
27 . The process according to claim 25 , wherein the process comprises the steps of (a) and (b2).
28 . The process according to claim 25 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-4 alkyl, —C(═O)—OH, —C(═O)—C 1-4 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-4 alkyl, —C(═O)—N(C 1-4 alkyl) 2 , hydroxyC 1-4 alkyl, —C(═O)H, and C 1-4 alkoxyC 1-4 alkyl; R 1 is hydrogen or C 1-4 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano.
29 . The process according to claim 25 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-2 alkyl, —C(═O)OH, C(═O)—C 1-2 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-2 alkyl, —C(═O)—N(CH 3 ) 2 ), hydroxyC 1-2 alkyl, —C(═O)H, and C 1-2 alkoxyC 1-2 alkyl; R 1 is hydrogen or C 1-2 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
30 . The process according to claim 25 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)OH, —C(═O)—CH 3 , —C(═O)—CH 2 —CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—N(CH 3 ) 2 , —CH 2 —OH, —CH 2 —CH 2 —OH, —C(═O)H, —CH 2 —O—CH 3 , and —CH 2 —O—CH 2 —CH 3 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
31 . The process according to claim 25 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)—CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , and —C(═O)—N(CH 3 ) 2 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 5-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; wherein at least one of R 1 or R 2 is not hydrogen; R 3 is hydrogen; R 4 is hydrogen; R 5 is hydrogen; R 6 is hydrogen; and R 7 is hydrogen.
32 . The process according to claim 25 , wherein compound of formula (I) is selected from the group consisting of:
Compound
Structure
1
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33 . An in-vitro method for identifying compounds that antagonize the response of the OR7D4 olfactory receptor to androstenone comprising the steps of:
contacting at least one cell, or membrane thereof, expressing the nucleic acid sequence encoding OR7D4, with androstenone and at least one test compound of formula (I), and
measuring the effect of at least one test compound(s) on the response of OR7D4 to androstenone;
wherein
X is selected from the group consisting of —C(═O)OR 8 , cyano, —C(═O)—C 1-6 alkyl, —C(═O)—NR 9 R 10 , hydroxyC 1-6 alkyl, —C(═O)H, and C 1-6 alkoxyC 1-6 alkyl;
R 1 is hydrogen or C 1-6 alkyl;
R 2 is hydrogen or a group selected from C 1-7 alkyl and C 2-7 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl;
R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 8 is hydrogen or C 1-6 alkyl; R 9 is hydrogen or C 1-6 alkyl; and R 10 is hydrogen or C 1-6 alkyl.
34 . A method for reducing or eliminating the olfactory perception of androstenone or another OR7D4 activator, comprising the step of using a compound of formula (I) to reduce or eliminate the olfactory perception of androstenone or another OR7D4 activator;
wherein
X is selected from the group consisting of —C(═O)OR 8 , cyano, —C(═O)—C 1-6 alkyl, —C(═O)—NR 9 R 10 , hydroxyC 1-6 alkyl, —C(═O)H, and C 1-6 alkoxyC 1-6 alkyl;
R 1 is hydrogen or C 1-6 alkyl;
R 2 is hydrogen or a group selected from C 1-7 alkyl and C 2-7 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl;
R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, and cyano;
R 8 is hydrogen or C 1-6 alkyl; R 9 is hydrogen or C 1-6 alkyl; and R 10 is hydrogen or C 1-6 alkyl.
35 . The method according to claim 33 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-4 alkyl, —C(═O)—OH, —C(═O)—C 1-4 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-4 alkyl, —C(═O)—N(C 1-4 alkyl) 2 , hydroxyC 1-4 alkyl, —C(═O)H, and C 1-4 alkoxyC 1-4 alkyl; R 1 is hydrogen or C 1-4 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano.
36 . The method according to claim 33 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-2 alkyl, —C(═O)OH, C(═O)—C 1-2 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-2 alkyl, —C(═O)—N(CH 3 ) 2 ), hydroxyC 1-2 alkyl, —C(═O)H, and C 1-2 alkoxyC 1-2 alkyl; R 1 is hydrogen or C 1-2 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
37 . The method according to claim 33 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)OH, —C(═O)—CH 3 , —C(═O)—CH 2 —CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—N(CH 3 ) 2 , —CH 2 —OH, —CH 2 —CH 2 —OH, —C(═O)H, —CH 2 —O—CH 3 , and —CH 2 —O—CH 2 —CH 3 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
38 . The method according to claim 33 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)—CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , and —C(═O)—N(CH 3 ) 2 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 5-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; wherein at least one of R 1 or R 2 is not hydrogen; R 3 is hydrogen; R 4 is hydrogen; R 5 is hydrogen; R 6 is hydrogen; and R 7 is hydrogen.
39 . The method according to claim 33 , wherein said compound of formula (I) is selected from the group consisting of:
Compound
Structure
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40 . The method according to claim 34 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-4 alkyl, —C(═O)—OH, —C(═O)—C 1-4 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-4 alkyl, —C(═O)—N(C 1-4 alkyl) 2 , hydroxyC 1-4 alkyl, —C(═O)H, and C 1-4 alkoxyC 1-4 alkyl; R 1 is hydrogen or C 1-4 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 3-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, halo, C 1-6 alkyl, C 1-4 alkoxy, C 1-4 alkoxyC 1-4 alkyl, and cyano.
41 . The method according to claim 34 , wherein
X is selected from the group consisting of —CN, —C(═O)OC 1-2 alkyl, —C(═O)OH, C(═O)—C 1-2 alkyl, —C(═O)—NH 2 , —C(═O)—NHC 1-2 alkyl, —C(═O)—N(CH 3 ) 2 ), hydroxyC 1-2 alkyl, —C(═O)H, and C 1-2 alkoxyC 1-2 alkyl; R 1 is hydrogen or C 1-2 alkyl; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 2-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
42 . The method according to claim 34 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)OH, —C(═O)—CH 3 , —C(═O)—CH 2 —CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—N(CH 3 ) 2 , —CH 2 —OH, —CH 2 —CH 2 —OH, —C(═O)H, —CH 2 —O—CH 3 , and —CH 2 —O—CH 2 —CH 3 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 2-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 4 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 5 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; R 6 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano; and R 7 is selected from the group consisting of hydrogen, fluoro, chloro, C 1-6 alkyl, C 1-2 alkoxy, C 1-2 alkoxyC 1-2 alkyl, and cyano.
43 . The method according to claim 34 , wherein
X is selected from the group consisting of —CN, —C(═O)—O—CH 3 , —C(═O)—O—CH 2 —CH 3 , —C(═O)—CH 3 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , and —C(═O)—N(CH 3 ) 2 ; R 1 is hydrogen or —CH 3 ; R 2 is hydrogen or a group selected from C 5-7 alkyl and C 5-6 alkenyl, each group being optionally substituted with one or more C 5-6 cycloalkyl; wherein at least one of R 1 or R 2 is not hydrogen; R 3 is hydrogen; R 4 is hydrogen; R 5 is hydrogen; R 6 is hydrogen; and R 7 is hydrogen.
44 . The method according to claim 34 , wherein said compound of formula (I) is selected from the group consisting of:
Compound
Structure
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