US 11,702,426 B2
Macrocyclic deaza-purinones for the treatment of viral infections
Jean-François Bonfanti, Andé (FR); Jérôme Michel Claude Fortin, Igoville (FR); Philippe Muller, Andé (FR); Frédéric Marc Maurice Doublet, Isneauville (FR); Pierre Jean-Marie Bernard Raboisson, Wavre (BE); and Eric Pierre Alexandre Arnoult, Le Vaudreuil (FR)
Assigned to JANSSEN SCIENCES IRELAND UNLIMITED COMPANY, Ringaskiddy (IE)
Filed by JANSSEN SCIENCES IRELAND UNLIMITED COMPANY, County Cork (IE)
Filed on Oct. 27, 2020, as Appl. No. 17/81,478.
Application 17/081,478 is a continuation of application No. 16/389,751, filed on Apr. 19, 2019, granted, now 10,829,494.
Application 16/389,751 is a continuation of application No. 14/781,291, granted, now 10,266,543, issued on Apr. 23, 2019, previously published as PCT/EP2014/056270, filed on Mar. 28, 2014.
Claims priority of application No. 13161865 (EP), filed on Mar. 29, 2013.
Prior Publication US 2021/0122760 A1, Apr. 29, 2021
Int. Cl. C07D 491/18 (2006.01); C07D 471/18 (2006.01); C07D 498/18 (2006.01); C07D 498/22 (2006.01); C07D 491/22 (2006.01)
CPC C07D 491/18 (2013.01) [C07D 471/18 (2013.01); C07D 491/22 (2013.01); C07D 498/18 (2013.01); C07D 498/22 (2013.01)] 11 Claims
 
1. A process of making a compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically accepted salt thereof, wherein:
n is 1, 2, or 3;
X is selected from the group consisting of oxygen, NH, or sulfur;
Y is phenyl or pyridyl, optionally substituted by one or more substituents independently selected from the group consisting of C1-6alkyl, C1-4alkoxy, trifluoromethyl or halogen; and
Z is selected from the group consisting of C1-10 alkyl, C1-6 alkyl-NH—, and C1-10alkyl-O—, wherein said alkyl is unsaturated or saturated;
wherein the process comprises:
(A) contacting a compound of formula (I-A):

OG Complex Work Unit Chemistry
with a ruthenium catalyst in order to provide a compound of formula (I-B):

OG Complex Work Unit Chemistry
wherein:
Z′ for each occurrence is, independently, C1-4 alkyl, C1-2 alkyl-N (Boc)-, or C1-4 alkyl-O—;
(B) optionally contacting the compound of formula (I-B) with H2 and Wilkinson's catalyst to provide a compound of formula (I-C):

OG Complex Work Unit Chemistry
(C) contacting the compound of formula (I-B) or the compound of formula (I-C) with iron, and optionally contacting the resulting compound with trifluoroacetic acid, to provide the compound of formula (I).