Active Ingredients with Sialagogue and Tingling/Fizzy Effect, and Preparations Containing Same

Patent metadata

Field	Value
Publication number	US-2025066320-A1
Application number	US-202118722561-A
Country	US
Kind code	A1
Filing date	Dec 23, 2021
Priority date	Dec 23, 2021
Publication date	Feb 27, 2025
Grant date	—

Abstract

The present invention is in the field of flavoring agents and relates to new representatives of this group, in particular active ingredients with a mouth-watering effect, the use of these active ingredients and preparations comprising them, preferably preparations for nutrition, enjoyment or oral hygiene or oral pharmaceutical preparations.

First claim

1 . Active ingredient of the general formula (I)

or the general formula (II)

or the general formula (III)

wherein the radicals R1 to R5 and R7 can each be identical or different and independently of one another have the following meanings:
R1
H; or
OH; or
Q; or
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted 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 heterocyclyl group; or
is an optionally substituted heteroaryl group; or
R1 forms with the adjacent R2, together with the carbon atoms to which they are attached, an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring, or forms an optionally substituted four-, five-, six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

R2
H; or
OH; or
Q; or
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted 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 heterocyclyl group; or
is an optionally substituted heteroaryl group; or
R2 forms with one of the adjacent radicals R1 or R3, together with the carbon atoms to which they are attached, an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring, or forms an optionally substituted four-, five-, six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; and/or

R3
H; or
OH; or
Q; or
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted 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 heterocyclyl group; or
is an optionally substituted heteroaryl group; or
R3 forms with one of the adjacent R2 or R4, together with the carbon atoms to which they are attached, an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring, or forms an optionally substituted four-, five-, six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

R4
H; or
OH; or
Q; or
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted 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 heterocyclyl group; or
is an optionally substituted heteroaryl group; or
R4 forms with one of the adjacent R3 or R5, together with the carbon atoms to which they are attached, an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring, or forms an optionally substituted four-, five-, six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; and/or

R5
H; or
OH; or
Q; or
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted 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 heterocyclyl group; or
is an optionally substituted heteroaryl group; or
R5 forms with the adjacent radical R4, together with the carbon atoms to which they are attached, an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring or forms an optionally substituted four-, five-, six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; and/or

R7
an optionally substituted cycloalkyl group; or
an optionally substituted aryl group; or
an optionally substituted heterocyclyl group; or
is an optionally substituted heteroaryl group;

X
an optionally substituted alkyl group; or
an optionally substituted alkenyl group; or
an optionally substituted alkoxy group; or
an optionally substituted alkylthio group; or
is an optionally substituted acyl group R(C═O)—;

optionally one or both nitrogen atom(s) of the saturated six-membered ring in the general formula (I) or the nitrogen atom of the saturated six-membered ring in the general formula (II) or one or both nitrogen atom(s) of the saturated seven-membered ring in the general formula (III) is/are replaced by a C atom;
optionally the saturated six-membered ring in the general formula (I) or (II) or the saturated seven-membered ring in the general formula (III) is mono- or polysubstituted;
wherein
the group Q is a radical selected from the group consisting of: halogen, —OY, —SY, —NZZ, —NY, —N—OY, trihalomethyl, —CF 3 , —CN, —OCN, —SCN, —NO, —NO 2 , —NH 2 , —N 3 , —S(O) 2 Y, —S(O) 2 OY, —OS(O) 2 Y, —OS(O) 2 OY, —P(O)(OY) 2 , —P(O)(OY)(OY), —C(O)Y, —C(S)Y, —C(NY)Y, —C(O)OY, —C(S)OY, —C(O)NZZ, —C(NY)NZZ, —OC(O)Y, —OC(S)Y, —OC(O)OY, —OC(S)OY, —NYC(O)Y, —NYC(S)Y, —NYC(O)OY, —NYC(S)OY, —NYC(O)NZZ, —NYC(NY)Y or —NYC(NY)NZZ;
wherein
Y is selected from the group consisting of:
Hydrogen;
alkyl group;
alkoxy group;
alkylthio group;
Cycloalkyl group;
Aryl Group;
Heterocyclyl group;
heteroaryl group; and/or

Z represents Y or alternatively, two Z's together with the nitrogen atom to which they are attached represent a four, five, six or seven membered heterocyclyl ring or heteroaryl ring, wherein the heterocyclyl ring or heteroaryl ring may comprise one, two or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
the optionally substituted alkyl group is an optionally substituted C 1 - to C 10 -alkyl group;
the optionally substituted alkenyl group is an optionally substituted C 1 - to C 10 -alkenyl group;
the optionally substituted alkoxy group is an optionally substituted C 1 - to C 10 -alkoxy group;
the optionally substituted alkylthio group is an optionally substituted C 1 - to C 10 -alkylthio group;
in the acyl group R—(C═O)— the radical R represents hydrogen or an optionally substituted C 1 - to C 10 -alkyl group;
the optionally substituted cycloalkyl group is an optionally substituted four- to ten-membered, monocyclic cycloalkyl group or an optionally substituted nine- to twelve-membered polycyclic cycloalkyl group;
the optionally substituted aryl group is an optionally substituted fou

Assignees

• Symrise Ag

Inventors

• Hentschel Fabia
• Wiedwald Bernd
• Paetz Susanne
• Simchen Ulrike
• Backes Michael
• Minakar Judith

Classifications

• C07D295/192 Primary

  from aromatic carboxylic acids · CPC title

• C07D243/08

  not condensed with other rings · CPC title

• C07D211/16

  with acylated ring nitrogen atom · CPC title

• A61K31/55

  having seven-membered rings, e.g. azelastine, pentylenetetrazole · CPC title

• A61K31/496

  Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin · CPC title