Poor little boy, missing his buddies....
I wonder if you have some kind of doggie day care facility that you could let him go to, even if only for a few hours, a couple of times a week? Maybe that would get him energised again?
Or a friend that might pop over with her pup for a playdate...let your little boy know that there are 'others' out there? I don't know...and I'm so sorry that you're both going through this