A former client hit Perkins Coie with a $150 million lawsuit on Friday, alleging the firm failed to seek and secure key patents that would have generated royalties from wildly successful products such as Apple’s AirPods and Amazon.com’s Echo Dot.

Muzik Inc., which makes high-end headphones, said it began working in 2012 with Sean Grygiel on protecting its inventions relating to voice controls and how smartphones and so-called smart devices communicate. The company said its “fatal mistake” was to keep working with Grygiel when he moved from Fish & Richardson to Perkins Coie in 2014.