By Marcus Leach

Microsoft have been ordered to pay $290 million for infringing a small Canadian companies patent.

The US Supreme Court denied Microsoft's appeal after i4i sued the technology giants, claiming they owned the technology behind a text manipulation tool used in Microsoft's Word application.

Lower courts had declared Microsoft knowingly and willingly broke the patent for the technology that gave Word 2003 and 2007 improved means of using a documents contents.

Microsoft were ordered to pay for the infringement of i4i's patent, as well as stop selling Word versions containing infringing technology.

"While the outcome is not what we had hoped for, we will continue to advocate for changes to the law that will prevent abuse of the patent system and protect inventors who hold patents representing true innovation," Microsoft said in a statement.

Microsoft now sells versions of Word that do not contain the technology in question.

"Microsoft tried to gut the value of patents by introducing a lower standard for invalidating patents," Loudon Owen, chairman of i4i, said.

"It is now 100% clear that you can only invalidate a patent based on 'clear and convincing' evidence."

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