Cynodictis lived about 20 million years ago
Next in evolutionary line from Miacis was an Oligocene animal called Cynodictis, which somewhat resembled the modern dog. Cynodictis lived about 20 million years ago. Its fifth toe, which would eventually become the dewclaw. Cynodictis also had 42 teeth. 
Tomarctus
After a few more intermediate stages the evolution of the dog moved on to the extremely doglike animal called Tomarctus, which lived 10 million years ago during the late Miocene epoch. Tomarctus probably developed the strong social instincts that still prevail in the dog.

To The Grey Wolf.