	US 12,378,216 B2
	Heteroaryl(heterocyclyl)methanol compounds useful in the treatment of hyperglycaemia
Benjamin Pelcman, Stockholm (SE); and Tore Bengtsson, Vaxholm (SE)
Assigned to ATROGI AB, Solna (SE)
Appl. No. 17/439,638
Filed by ATROGI AB, Stockholm (SE)
PCT Filed Mar. 20, 2020, PCT No. PCT/GB2020/050760 § 371(c)(1), (2) Date Sep. 15, 2021, PCT Pub. No. WO2020/188299, PCT Pub. Date Sep. 24, 2020.
Claims priority of application No. 1903832 (GB), filed on Mar. 20, 2019.
Prior Publication US 2022/0194920 A1, Jun. 23, 2022
Int. Cl. C07D 401/06 (2006.01); A61K 31/44 (2006.01); A61K 31/4427 (2006.01); A61K 31/4439 (2006.01); A61K 31/444 (2006.01); A61K 45/06 (2006.01); A61P 3/10 (2006.01)

CPC C07D 401/06 (2013.01) [A61K 31/44 (2013.01); A61K 31/4427 (2013.01); A61K 31/4439 (2013.01); A61K 31/444 (2013.01); A61K 45/06 (2013.01); A61P 3/10 (2018.01)]

7 Claims

1. A compound of formula IC′

or a pharmaceutically acceptable salt thereof, wherein:

z represents 1 to 3;

n1 represents 1 to 4

each R¹independently represents C_1-6alkyl, C_2-6alkenyl, or C_2-6alkynyl each optionally substituted by one or more halo;

any two R¹groups when attached to the same carbon may form together a 3- to 6-membered ring, which optionally is substituted by one or more groups independently selected from halo, C_1-6alkyl, C_2-6alkenyl, and C_2-6alkynyl each optionally substituted by one more halo;

either

one of R^1xand R^1yrepresents an R¹group and the other represents H, or

both of R^1xand R^1yrepresent an R¹group;

wherein where one of R^1xand R^1yrepresents an R¹group and the other represents H, then

when z represents 1 then mx represents 0 to 6, when z represents 2 then mx represents 0 to 8, and

when z represents 3 then mx represents 0 to 10;

wherein where both of R^1xand R^1yrepresent an R¹group, then

when z represents 1 then mx represents 0 to 5, when z represents 2 then mx represents 0 to 7, and

when z represents 3 then mx represents 0 to 9;

each X¹independently represents, as appropriate, halo, R^a, —CN, —N(R^b)R^c, or —OR^d;

R^arepresents C_1-6alkyl, C_2-6alkenyl, or C_2-6alkynyl each optionally substituted by one or more groups independently selected from G¹;

each R^b, R^c, and R^dindependently represents H, C_1-6alkyl, C_2-6alkenyl, or C_2-6alkynyl each optionally substituted by one or more groups independently selected from G²;

or alternatively any of R^band R^cmay be linked together to form, together with the nitrogen atom to which they are attached, a 4- to 6-membered ring, which ring optionally contains one further heteroatom and which ring optionally is substituted by one or more groups independently selected from halo, C_1-3alkyl, C_2-3alkenyl, and C_2-3alkynyl each optionally substituted by one or more halo and ═O;

G¹and G²represents halo, —CN, —N(R^a1)R^b1, —OR^c1, —S(O)^pR^d1, —S(O)_qN(R^e1)R^f1or ═O;

each R^a1, R^b1, R^c1, R^d1, R^e1and R^f1independently represents H, or C_1-6alkyl, C_2-6alkenyl, or C_2-6alkynyl each optionally substituted by one or more halo;

or alternatively any of R^a1and R^b1and/or R^e1and R^f1may be linked together to form, together with the nitrogen atom to which they are attached, a 4- to 6-membered ring, which ring optionally contains one further heteroatom and which ring optionally is substituted by one or more groups independently selected from halo, C_1-3alkyl, C_2-3alkenyl, and C_2-3alkynyl each optionally substituted by one or more halo and ═O;

each p independently represents 0, 1 or 2; and

each q independently represents 1 or 2,

wherein alkyl, alkenyl and alkynyl groups may be straight-chain or, when there is a sufficient number of carbon atoms, be branched-chain and/or cyclic or part cyclic.