US 11,834,456 B2
11,13-modified saxitoxins for the treatment of pain
John Mulcahy, Redwood City, CA (US); Hassan Pajouhesh, Mountain View, CA (US); George Miljanich, Redwood City, CA (US); Anton Delwig, Albany, CA (US); Jacob Beckley, Bozeman, MT (US); Grant Masaaki Shibuya, South San Francisco, CA (US); and Justin Du Bois, Menlo Park, CA (US)
Assigned to SITEONE THERAPEUTICS, INC., Bozeman, MT (US); and THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY, Stanford, CA (US)
Filed by SITEONE THERAPEUTICS, INC., South San Francisco, CA (US); and THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY, Stanford, CA (US)
Filed on Jan. 26, 2022, as Appl. No. 17/585,530.
Application 17/585,530 is a continuation of application No. 16/499,205, granted, now 11,236,097, previously published as PCT/US2018/025301, filed on Mar. 29, 2018.
Claims priority of provisional application 62/478,523, filed on Mar. 29, 2017.
Prior Publication US 2022/0259218 A1, Aug. 18, 2022
Int. Cl. C07D 487/14 (2006.01)
CPC C07D 487/14 (2013.01) 17 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
as a pharmaceutically acceptable salt or salts thereof,
wherein
X2 is —C(R4)(R4a)— or —N(R8)—;
each R4 and R4a is independently hydrogen or C1-6 alkyl;
R7 is hydrogen or C1-6alkyl;
R7a is

OG Complex Work Unit Chemistry
one R7b is halo, C1-6alkyl, halo-C1-6alkyl, aryl-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, aryloxy, nitro, C1-6alkylthio, halo-C1-6alkylthio,
C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, —C(O)(heterocycloalkyl), or cyano; where the aryl in aryloxy and aryl-C1-6alkyl are optionally substituted with 1, 2, or 3 groups independently selected from C1-6alkyl, halo, and halo-C1-6alkyl;
the other R7b is hydrogen, halo, C1-6 alkyl, halo-C1-6 alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, aryloxy, nitro, C1-6alkylthio, halo-C1-6alkylthio,
C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, —C(O)(heterocycloalkyl), or cyano; where the aryl in aryloxy and aryl-C1-6 alkyl are optionally substituted with 1, 2, or 3 groups independently selected from C1-6alkyl, halo, and halo-C1-6alkyl; and
R8 is hydrogen; C1-6alkyl; carboxy-C1-6-alkyl; halo-C1-6-alkyl; hydroxy-C1-6-alkyl; or phenyl optionally substituted with 1, 2, or 3 groups independently selected from halo, C1-6alkyl, halo-C1-6 alkyl, hydroxy, C1-6alkoxy, halo-C1-6 alkoxy, nitro, and cyano; or
a hydrate, solvate, stereoisomer, tautomer, or mixture thereof provided that the compound is not selected from Group A:
Group A
or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, tautomer, or mixture thereof.