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US 11,945,813 B2Granted
5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof
AssigneeFirmenich SA
InventorsJoseph R. Fotsing, Catherine Tachdjian, Guy Servant, Brett Weylan Ching, Timothy Davis
Life of this patent
Estimating the term…
Abstract
Disclosed herein are 5-Substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxide compounds useful as sweet flavor modifiers. Also disclosed herein are ingestible compositions that include one or more of these compounds in combination with a natural or artificial sweetener.
Claims15
A compound of formula (I):
- or a salt thereof, wherein:
- R1 and R2 are each independently hydrogen or C1-6 alkyl, or R1 and R2 together with the carbon to which they are attached is a C3-7 carbocyclyl;
- Ar1 is an aryl or heteroaryl, each optionally substituted with one or more R3;
- each R3 is independently selected from the group consisting of halo, cyano, nitro, oxo, —C(═O)OR3A, —NR3A(CH2)pOR3B, —NR3A(CH2)pR3B, (CH2)qOR3B, —(CH2)qR3B, —C(═O)R3A, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, —C(═O)NR3AR3B, —NR3AC(═O)R3B, and R3C;
- each R3A is independently selected from the group consisting of hydrogen, halo, cyano, —(CH2)qR3AA, (CH2)qN(R3AA)2, (C1-C6)alkyl, C3-7 carbocyclyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and heteroaryl(C1-C6)alkyl;
- each R3B is independently selected from the group consisting of hydrogen, halo, cyano, —(CH2)qR3BB, —(CH2)qN(R3BB)2, (C1-C6)alkyl, C3-7 carbocyclyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and heteroaryl(C1-C6)alkyl;
- each R3C is independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl, and C3-7 carbocyclyl, each optionally substituted with one or more R3CC;
- each R3AA is independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3-7 carbocyclyl, each optionally substituted with one or more R3CC;
- each R3BB is independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3-7 carbocyclyl, each optionally substituted with one or more R3CC;
- each R3CC is independently selected from the group consisting of halo, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3-7 carbocyclyl;
- each p is independently an integer selected from 1, 2, and 3;
- and
- each q is independently an integer selected from 0, 1, 2 and 3.
10 more elements
A compound of formula (II):
- or a salt thereof, wherein:
- Ar2 is an aryl or heteroaryl, each optionally substituted with one or more R4;
- each R4 is independently selected from the group consisting of halo, cyano, nitro, oxo, —C(═O)OR4A, —NR4A(CH2)mOR4B, —NR4A(CH2)mR4B, —(CH2)nOR4B, —(CH2)nR4B, —C(═O)R4A, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, —C(═O)NR4AR4B, —NR4AC(═O)R4B, and R4C;
- each R4A is independently selected from the group consisting of hydrogen, halo, cyano, —(CH2)nOH, —(CH2)nR4AA, —(CH2)nOR4AA, —(CH2)nN(R4AA)2, (C1-C6)alkyl, C3-7 carbocyclyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and heteroaryl(C1-C6)alkyl, said heterocycle, aryl and heteroaryl in R4A, each optionally substituted with one or more (C1-C6)alkyl or C3-7 carbocyclyl;
- each R4B is independently selected from the group consisting of hydrogen, halo, cyano, —(CH2)nOH, —(CH2)nR4BB, —(CH2)nOR4BB, —(CH2)nN(R4BB)2, (C1-C6)alkyl, C3-7 carbocyclyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkylC(═O)—, (C1-C6)alkylOC(═O)—, (C1-C6)alkylC(═O)O—, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and heteroaryl(C1-C6)alkyl;
- each R4C is independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl, and C3-7 carbocyclyl, each optionally substituted with one or more R4CC;
- each R4AA is independently selected from the group consisting of hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3_7 carbocyclyl, each optionally substituted with one or more R4CC;
- each R4BB is independently selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3-7 carbocyclyl, each optionally substituted with one or more R4CC;
- each R4CC is independently selected from the group consisting of halo, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, heterocycle, aryl, heteroaryl, heterocycle(C1-C6)alkyl, aryl(C1-C6)alkyl, and C3-7 carbocyclyl;
- each m is independently an integer selected from 0, 1, 2, and 3;
- and
- each n is independently an integer selected from 0, 1, 2 and 3.
9 more elements
Dependencies are inferred from the claim text.