New Coolants, and Preparations Containing Same

Patent metadata

Field	Value
Publication number	US-2025163006-A1
Application number	US-202318833384-A
Country	US
Kind code	A1
Filing date	Jan 27, 2023
Priority date	Jan 28, 2022
Publication date	May 22, 2025
Grant date	—

Abstract

The present invention relates to novel physiological coolants, mixtures of coolants containing these novel agents, mixtures of the coolants with flavors, the use of these coolants, and articles and end preparations for the consumer containing the physiological coolants or mixtures of coolants.

First claim

1 . Physiological coolant of the general formula (Va)

or the general formula (VIa)

where in formulae (Va) and (VIa) in each case
the radicals R1 and R2 may be identical or different and have the following meanings independently of one another:

R1 H; or
a group Q; or
an optionally substituted linear or branched alkyl group; or
an optionally substituted linear or branched alkenyl group; or
an optionally substituted linear or branched alkynyl group; or
an optionally substituted linear or branched alkoxy group; or
an optionally substituted linear or branched alkylthio group; or
an optionally substituted acyl group —R(C═O)—; or
an optionally substituted cycloalkyl group; or
an optionally substituted aryl group; or
an optionally substituted heterocycloalkyl group; or
is an optionally substituted heteroaryl group;

R2 H; or
a group Q; or
an optionally substituted linear or branched alkyl group; or
an optionally substituted linear or branched alkenyl group; or
an optionally substituted linear or branched alkynyl group; or
an optionally substituted linear or branched alkoxy group; or
an optionally substituted linear or branched alkylthio group; or
an optionally substituted acyl group R—(C═O)—; or
an optionally substituted cycloalkyl group; or
an optionally substituted aryl group; or
an optionally substituted heterocycloalkyl group; or
is an optionally substituted heteroaryl group;
or R1 and R2 together with the C atoms to which they are bonded form a conjugated or non-conjugated ring system;

Y is an optionally substituted branched alkyl group; or
an optionally substituted linear or branched alkenyl group; or
an optionally substituted linear or branched alkynyl group; or
an optionally substituted linear or branched alkoxy group; or
an optionally substituted acyl group R—(C═O)—; or
an optionally substituted alkylaryl group; or
is an optionally substituted alkylheteroaryl group;

Z in the general formula (Va) NH2; or
an NHRa group; or
an NRaRb group; or
an optionally substituted linear or branched alkyl group; or
an optionally substituted linear or branched alkenyl group; or
an optionally substituted linear or branched alkylthio group; or
an optionally substituted linear or branched alkoxy group; or
OH; or
an optionally substituted cycloalkyl group; or
an optionally substituted heterocycloalkyl group; or
an optionally substituted aryl group; or
is an optionally substituted heteroaryl group; or
NH and together with the X forms a heterocyclic ring;

Z in the general formula (VIa) NH 2 ; or
an NHRa group or an NRaRb group, with the exception of formula —NH-phenyl and —N(CH 3 )-phenyl; or
an optionally substituted linear or branched alkyl group; or
an optionally substituted linear or branched alkenyl group; or
an optionally substituted linear or branched alkylthio group; or
an optionally substituted linear or branched alkoxy group, with the exception of —OC2H5 and —OC(CH 3 ) 3 ; or
an optionally substituted cycloalkyl group; or
an optionally substituted heterocycloalkyl group; or
an optionally substituted aryl group; or
is an optionally substituted heteroaryl group; or
NH and together with the X forms a heterocyclic ring;

m is 1;
whereby
the group Q is a radical selected from the group consisting of: halogen, —OA, —SA, —NBB, —CF 3 , —CN, —OCN, —SCN, —NO, —NO 2 , —S(O) 2 a , —S(O) 2 OA, —OS(O) 2 a , —OS(O) 2 OA, —P(O)(OA) 2 , —P(O)(OA)(OA), —C(O)A, —C(S)A, —C(NA)A, —C(O)OA, —C(S)OA, —C(O)NBB, —C(NA)NBB, —OC(O)A, —OC(S)A, —OC(O)OA, —OC(S)OA, —NAC(O)A, —NAC(S)A, —NAC(O)OA, —NAC(S)OA, —NAC(O)NBB, —NAC(NA)A or —NAC(NA)NBB;
whereby
A is selected from the group consisting of:
Hydrogen,
optionally substituted linear or branched alkyl group, in particular optionally substituted C 1 - to C 10 -alkyl group, in particular optionally substituted C 1 - to C 6 -alkyl group, in particular optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkyl group,
optionally substituted linear or branched alkoxy group, in particular optionally substituted C 1 -C 6 -alkoxy group, in particular optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkoxy group,
optionally substituted linear or branched alkylthio group, in particular optionally substituted C 1 - to C 6 -alkylthio group, in particular optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkylthio group,
optionally substituted cycloalkyl group,
optionally substituted aryl group,
optionally substituted heterocycloalkyl group,
optionally substituted heteroaryl group; and/or
B represents A or alternatively, two B's together with the nitrogen atom to which they are attached represent a four, five, six or seven membered heterocycloalkyl ring or heteroaryl ring, wherein the heterocycloalkyl ring or heteroaryl ring may comprise one, two, three or four identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
the optionally substituted linear or branched alkyl group is an optionally substituted C 1 - to C 10 -alkyl group, in particular an optionally substituted C 1 - to C 6 -alkyl group, is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkyl group;
the optionally substituted linear or branched alkenyl group is an optionally substituted C 1 - to C 10 -alkenyl group, in particular an optionally substituted C 1 - to C 6 -alkenyl group, is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkenyl group;
the optionally substituted linear or branched alkynyl group is an optionally substituted C 1 - to C 10 -alkynyl group, in particular an optionally substituted C 1 - to C 6 -alkynyl group, is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkynyl group;
the optionally substituted linear or branched alkoxy group is an optionally substituted C 1 - to C 10 -alkoxy group, in particular an optionally substituted C 1 - to C 6 -alkoxy group, is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkoxy group;
the optionally substituted linear or branched alkylthio group is an optionally substituted C 1 - to C 10 -alkylthio group, in particular an optionally substituted C 1 - to C 6 -alkylthio group,
is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -alkylthio group;
in the acyl group R—(C═O)— the radical R represents hydrogen or an optionally substituted linear or branched C 1 - to C 10 -alkyl group, in particular an optionally substituted C 1 - to C 6 -alkyl group,
is in particular an optionally substituted C 1 -, C 2 -, C 3 - or C 4 -acyl group;
the optionally substituted cycloalkyl group is an optionally substituted three- to ten-membered, in particular three-, four-, five-, six- or seven-membered, monocyclic cycloalkyl group or an optionally substituted nine- to twelve-membered polycyclic, in particular bicyclic, cycloalkyl group;
the optionally substituted aryl group is an optionally substituted three- to ten-membered, in particular three-, four-, five-, six- or seven-membered, monocyclic aryl group or an optionally substituted nine- to twelve-membered polycyclic, in particular bicyclic aryl group;
the optionally substituted heterocycloalkyl group is an optionally substituted three- to ten-membered, in particular three-, four-, five-, six- or seven-membered monocyclic heterocycloalkyl group or an optionally substituted nine- to twelve-membered polycyclic, in particular bicyclic, heterocycloalkyl group, wherein the heterocycloalkyl group may comprise one, two, three or four identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
the optionally s

Assignees

• Symrise Ag

Inventors

• Minakar Judith
• Join Benoit
• Hans Joachim
• Backes Michael
• Wiebusch Rebecca
• Stuhlmann Dominik
• Matuszko Gabriela

Classifications

• C07D413/04

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

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/04

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

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title