There were a few different changes that occurred along the way. The development of different classes of antibodies (IgM is the original antibody, which was followed by IgA, IgE, IgD, and IgG, in no particular order) and multiple antibodies that are found in other species that are not present in humans (camelids and sharks have unique antibodies, hcIgG and IgW, respectively) has clearly shown an evolutionary path for adaptive immunity in vertebrates. That's a whole hell of a lot of adaptive evolution, really.