A Texas judge has ruled against Microsoft in an ongoing patent dispute surrounding the firm's product activation technology.
The activation feature is built into several Microsoft products to protect against software piracy.
It requires users to register and activate new software such as Windows or Office via a phone call or over the internet before it can be used.
Judge Leonard Davis turned down Microsoft's request for a new trial and upheld a previous ruling which ordered the Redmond giant to pay $140m. Co-defendant Autodesk has been ordered to pay $18m.
The suit dates back to 2004 when Michigan-based start-up Z4 alleged that Microsoft's and Autodesk's product activation technologies infringed on two of its patents.
Z4 specialises in digital rights management technology for software vendors and digital content providers. The company claims to own 24 patents or pending patents.
Microsoft is expected to appeal against the judge's ruling. The software giant maintains that Z4 engaged in "inequitable conduct", a legal term indicating that the firm intentionally made errors in its patent filing.
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