US Patent No. 9,611,264

N-[2-(3-AMINO-2,5-DIMETHYL-1,1-DIOXIDO-5,6-DIHYDRO-2H-1,2,4-THIADIAZIN-5-YL)-1,3-THIAZOL-4-YL] AMIDES


Patent No. 9,611,264
Issue Date April 04, 2017
Title N-[2-(3-amino-2,5-dimethyl-1,1-dioxido-5,6-dihydro-2h-1,2,4-thiadiazin-5-yl)-1,3-thiazol-4-yl] Amides
Inventorship Michael Aaron Brodney, Newton, MA (US)
Christopher Ryan Butler, Canton, MA (US)
Lei Zhang, Auburndale, MA (US)
Patrick Robert Verhoest, Newton, MA (US)
Romelia del Carmen Salomon Ferrer, San Diego, CA (US)
Assignee Pfizer Inc., New York, NY (US)

Claim of US Patent No. 9,611,264

1. A compound of Formula I

wherein
R1 is a 5- to 6-membered heteroaryl, having one to four heteroatoms independently selected from N, O or S, wherein at least one
of the heteroatoms is N and wherein said N is optionally substituted with R5; and wherein said 5- to 6-membered heteroaryl is optionally substituted on carbon with one to three R4;

R2 and R3 are each independently hydrogen, C1-6alkyl, C3-6cycloalkyl or 3- to 7-membered heterocycloalkyl; wherein the C1-6alkyl is optionally substituted with a C1-3alkoxy or with one to three fluoro; and the C3-6cycloalkyl and 3- to 7-membered heterocycloalkyl are each optionally and independently substituted with one to three fluoro,
C1-3alkyl or C1-3alkoxy;

or R2 and R3, taken together with the carbon to which they are attached, form a C3-6cycloalkyl ring or 3- to 7-membered heterocycloalkyl ring, each of which is optionally and independently substituted with
one to three fluoro, C1-3alkyl or C1-3alkoxy;

R4 at each occurrence is independently selected from the group consisting of halo, hydroxy, cyano, C1-6alkyl, C1-6alkoxy, C3-6alkenyl, C3-6alkenyloxy, C3-6alkynyl, C3-6alkynyloxy, C1-6alkoxy-C1-6alkyl, C3-6cycloalkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C3-6cycloalkyl-C1-6alkoxy, 4- to 6-membered heterocycloalkyl and 4- to 6-membered heterocycloalkyl-C1-6alkyl; wherein said C1-6alkyl, C1-6alkoxy, C3-6alkenyl, C3-6alkenyloxy, C3-6alkynyl, C3-6alkynyloxy, C1-6alkoxy-C1-6alkyl, C3-6cycloalkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C3-6cycloalkyl-C1-6alkoxy, 4- to 6-membered heterocycloalkyl and 4- to 6-membered heterocycloalkyl-C1-6alkyl are each optionally substituted with one to three substituents independently selected from fluoro, chloro, hydroxy,
cyano, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, methoxy, fluoromethoxy, difluoromethoxy and trifluoromethoxy;
and

R5 is hydrogen or C1-6alkyl optionally substituted with one to three fluoro;

or a tautomer thereof or a pharmaceutically acceptable salt of said compound
or tautomer.