Developer Thomas McFeely has lost his appeal against the extension of his bankruptcy.
The Court of Appeal rejected all grounds of the Priory Hall developer's appeal against a decision of the High Court to extend his bankruptcy by almost five years.
The High Court extended the period of bankruptcy after it found he failed to co-operate with the bankruptcy trustee, Chris Lehane by not disclosing his interest in 12 apartments in Dublin.
The appeal court dismissed his claim his fundamental rights were breached when computers and documents were seized from a Dublin office.
The documents were seized when a bankruptcy inspector searched the offices of Coalport Building Company, of which Mr McFeely was a director until he resigned some years before his bankruptcy.
Mr McFeely claimed that raid by officers acting for Mr Lehane was the source for allegedly illegally obtained documents later used to back up the application to extend his bankruptcy.
Had that not happened, Mr McFeely would have exited bankruptcy in July 2015 but now faces being a bankrupt until 2020.
Mr Lehane argued the appeal was "entirely unmeritorious" and also said some evidence about his non-disclosure of assets was not obtained in the search.
The three judge appeal court unanimously ruled the High Court correctly found evidence arising from the unlawful search of the premises at Holles Street was admissible for the extension application.
The appeal court stressed the unlawful entry by State agents onto business premises is always a serious matter.
If the assignee's agents had entered premises occupied by the bankrupt, as distinct from these premises he was not occupying, that conclusion as to the admissibility of the evidence would be different, it said.
It also upheld the High Court findings of non co-operation with Mr Lehane.
It dismissed a claim that the extension of the bankruptcy for almost five years was disproportionate.
The time period was based on the High Court finding Mr McFeely's conduct was at the grave end of the spectrum, a finding that court was entitled to make, the judges held.
Costs will be decided later.
