US 11,945,813 B2
5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof
Joseph R. Fotsing, San Diego, CA (US); Catherine Tachdjian, San Diego, CA (US); Guy Servant, San Diego, CA (US); Brett Weylan Ching, San Diego, CA (US); and Timothy Davis, Santee, CA (US)
Assigned to FIRMENICH INCORPORATED, Plainsboro, NJ (US)
Appl. No. 17/266,074
Filed by Firmenich Incorporated, Plainsboro, NJ (US)
PCT Filed Aug. 6, 2019, PCT No. PCT/US2019/045325
§ 371(c)(1), (2) Date Feb. 4, 2021,
PCT Pub. No. WO2020/033420, PCT Pub. Date Feb. 13, 2020.
Claims priority of provisional application 62/715,669, filed on Aug. 7, 2018.
Prior Publication US 2021/0309654 A1, Oct. 7, 2021
Int. Cl. C07D 417/14 (2006.01); A23L 2/56 (2006.01); A23L 2/60 (2006.01); A23L 27/00 (2016.01); A23L 27/20 (2016.01); A23L 27/30 (2016.01); C07D 417/12 (2006.01)
CPC C07D 417/14 (2013.01) [A23L 2/56 (2013.01); A23L 2/60 (2013.01); A23L 27/2056 (2016.08); A23L 27/33 (2016.08); A23L 27/88 (2016.08); C07D 417/12 (2013.01); A23V 2002/00 (2013.01)] 15 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
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.