Compounds reducing malodour perception and the use thereof

A compound of formula (I) or a stereoisomer thereof,

• wherein
• X is selected from the group consisting of —CN, —C(═O)OR8, —C(═O)—C1-6alkyl, —C(═O)—NR9R10, —CH2—OH, —CH2—CH2—OH, —C(═O)H, and C1-6alkoxyC1-6alkyl;
• R1 is hydrogen or C1-6alkyl;
• R2 is a group selected from C5-6alkyl, C5-6alkenyl, 3-tert-butyl-1-methylpropyl, or C1alkyl substituted with a C5cycloalkyl;
• R3 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R8 is hydrogen or C1-6alkyl;
• R9 is hydrogen or C1-6alkyl;
• R10 is hydrogen or C1-6alkyl;
• with the following provisos:
• when X is —C(═O)—NR9R10 then R1 is —CH3;
• when X is —C(═O)H or —C(═O)OR8, then R4 is not C1-6alkoxy;
• and the compound of formula (I) is none of:
• methyl (2E,4E)-4-(4-fluorobenzylidene)-2-nonenoate;
• (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol,
• methyl (2E,4E)-4-[(4-methoxyphenyl)methylene]non-2-enoate;
• and
• (2E,4E)-4-benzylidenedec-2-enenitrile.

A compound selected from the group consisting of:

• Compound
• Structure
• 3
• 4
• 31
• 32
• 36
• 37
• 25
• 27
• 6
• 15
• 20
• 35
• 41

Use of a compound of formula (I) or a stereoisomer thereof to suppress or attenuate undesirable odour;

• wherein
• X is selected from the group consisting of —CN, —C(═O)OR8, —C(═O)—C1-6alkyl, —C(═O)—NR9R10, hydroxyC1-6alkyl, —C(═O)H, and C1-6alkoxyC1-6alkyl;
• R1 is hydrogen or C1-6alkyl;
• R2 is hydrogen or a group selected from C1-7alkyl, and C2-7alkenyl, each group being optionally substituted with one or more C3-6cycloalkyl;
• R3 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R8 is hydrogen or C1-6alkyl;
• R9 is hydrogen or C1-6alkyl;
• and
• R10 is hydrogen or C1-6alkyl;
• with the proviso that the compound of formula (I) is not (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol.

A method to suppress or attenuate undesirable odour, comprising the step of using a compound of formula (I) or a stereoisomer thereof to suppress or attenuate said undesirable odour;

• wherein
• X is selected from the group consisting of —CN, —C(═O)OR8, —C(═O)—C1-6alkyl, —C(═O)—NR9R10, hydroxyC1-6alkyl, —C(═O)H, and C1-6alkoxyC1-6alkyl;
• R1 is hydrogen or C1-6alkyl;
• R2 is hydrogen or a group selected from C1-7alkyl, and C2-7alkenyl, each group being optionally substituted with one or more C3-6cycloalkyl;
• R3 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R8 is hydrogen or C1-6alkyl;
• R9 is hydrogen or C1-6alkyl;
• and R10 is hydrogen or C1-6alkyl;
• with the proviso that the compound of formula (I) is not (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol.

A method to suppress or attenuate undesirable odour, preferably body malodour, preferably mammalian body malodour, preferably human axillary malodour, said method comprising the step of applying a malodour counteracting effective amount of a compound of formula (I) or a stereoisomer thereof, to the skin.

• wherein
• X is selected from the group consisting of —CN, —C(═O)OR8, —C(═O)—C1-6alkyl, —C(═O)—NR9R10, hydroxyC1-6alkyl, —C(═O)H, and C1-6alkoxyC1-6alkyl;
• R1 is hydrogen or C1-6alkyl;
• R2 is hydrogen or a group selected from C1-7alkyl, and C2-7alkenyl, each group being optionally substituted with one or more C3-6cycloalkyl;
• R3 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R8 is hydrogen or C1-6alkyl;
• R9 is hydrogen or C1-6alkyl;
• and
• R10 is hydrogen or C1-6alkyl;
• with the proviso that the compound of formula (I) is not (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol.

A method of counteracting malodour in an air space or a substrate, comprising the step of introducing a malodour counteracting effective amount of a compound of formula (I) or a stereoisomer thereof,

• wherein
• X is selected from the group consisting of —CN, —C(═O)OR8, —C(═O)—C1-6alkyl, —C(═O)—NR9R10, hydroxyC1-6alkyl, —C(═O)H, and C1-6alkoxyC1-6alkyl;
• R1 is hydrogen or C1-6alkyl;
• R2 is hydrogen or a group selected from C1-7alkyl, and C2-7alkenyl, each group being optionally substituted with one or more C3-6cycloalkyl;
• R3 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxyC1-6alkyl, and cyano;
• R8 is hydrogen or C1-6alkyl;
• R9 is hydrogen or C1-6alkyl;
• and
• R10 is hydrogen or C1-6alkyl;
• with the proviso that the compound of formula (I) is not (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol.