US 12,280,023 B2
Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia
Benjamin Pelcman, Stockholm (SE); and Tore Bengtsson, Vaxholm (SE)
Assigned to ATROGI AB, Solna (SE)
Filed by ATROGI AB, Stockholm (SE)
Filed on Apr. 11, 2023, as Appl. No. 18/133,060.
Application 18/133,060 is a continuation of application No. 16/646,497, granted, now 11,648,216, previously published as PCT/GB2018/052594, filed on Sep. 13, 2018.
Claims priority of application No. 1714734 (GB), filed on Sep. 13, 2017.
Prior Publication US 2023/0364035 A1, Nov. 16, 2023
Int. Cl. A61P 3/10 (2006.01); A61K 31/137 (2006.01); A61K 31/167 (2006.01); A61K 45/06 (2006.01); C07C 215/30 (2006.01); C07C 215/34 (2006.01); C07C 215/42 (2006.01); C07C 215/60 (2006.01); C07C 215/68 (2006.01); C07C 233/43 (2006.01)
CPC A61K 31/137 (2013.01) [A61K 31/167 (2013.01); A61P 3/10 (2018.01); C07C 215/34 (2013.01); C07C 215/42 (2013.01); C07C 215/68 (2013.01); C07C 233/43 (2013.01)] 28 Claims
 
1. A compound of formula IB

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 represents C4-12 alkyl optionally substituted by one or more halo;
R2 and R3 each independently represent H or C1-3 alkyl optionally substituted by one or more halo;
or R2 and R3 may be linked together to form, together with the carbon atom to which they are attached, a 3- to 6-membered ring, which ring optionally is substituted by one or more groups independently selected from halo and C1 alkyl optionally substituted by one or more halo;
X represents Cl, Br, Ra, —CN, —N3, —N(Rb)Rc, —NO2, —ONO2, —ORd, —S(O)pRe or —S(O)qN(Rf)Rg;
Ra represents C1-6 alkyl optionally substituted by one or more groups independently selected from G;
each Rb, Rc, Rd, Re, Rf and R independently represents H or C1-6 alkyl optionally substituted by one or more groups independently selected from G;
or alternatively any of Rb and Rc and/or Rf and Rg may 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, C1-3 alkyl optionally substituted by one or more halo, and ═O;
G represents halo, —CN, —N(Ra1)Rb1, —ORc1, —S(O)pRd1, —S(O)qN(Re1)Rf1 or ═O;
each Ra1, Rb1, Rc1, Rd1, Re1 and Rf1 independently represents H or C1-6 alkyl optionally substituted by one or more halo;
or alternatively any of Ra1 and Rb1 and/or Re1 and Rf1 may 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, C1-3 alkyl optionally substituted by one or more halo, and ═O;
m represents 2;
n represents 1;
each p independently represents 0, 1 or 2; and
each q independently represents 1 or 2,
wherein alkyl groups may be straight-chain or, when there is a sufficient number of carbon atoms, be branched-chain, and/or cyclic or part cyclic.