Belfast-born property developer Paddy McKillen has lost his High Court case in London against the millionaire Barclay brothers.
Mr McKillen had sued the brothers over control of three top London hotels.
It is expected that Mr McKillen will appeal the decision.
He had sued the Barclay Brothers alleging they had improperly taken control of Coroin, the holding company for Claridges, the Berkeley and the Connaught Hotels in London.
During a lengthy case, lawyers for Mr McKillen had argued that the Barclays' use of the shareholding of Irish financier Derek Quinlan should have triggered a pre-emption agreement, whereby Mr McKillen as an existing shareholder would have been given the option to purchase the Quinlan shareholding first.
However, in a written judgment Mr Justice David Williams dismissed Mr McKillen's claim because he said the alleged breaches of the pre-emption agreement had not been established during the case.
The judge also said Mr McKillen had not been able to establish any conduct that had been unfairly prejudicial to him.
Mr McKillen had also challenged the transfer of £660m of debt in Coroin to a company controlled by the Barclay Brothers, alleging that NAMA should have consulted Coroin before selling the debt.
However, last June the Court of Appeal in London had ruled in favour of NAMA on the question of consultation.
In today's judgment, Mr Justice David Richards said that because of the earlier ruling, Mr McKillen could no longer rely on his claim of invalidity by NAMA.
McKIllen to do 'everything in his power'
Mr McKillen says he will do everything in his power to gain control of the company which controls three of London's top hotels.
The Belfast-born developer was speaking after losing a case at the High Court in London against the billionaire Barclay Brothers, owners of the Ritz Hotel and Telegraph newspapers.
But speaking by telephone from France today, Mr McKillen maintained that after today's judgement the Barclay Brothers still could not take over the Quinlan shareholding without it being offered to him first.
He said he would continue to do everything in his power to buy Mr Quinlan's shareholding and that he had the funding to do so.
However, commenting on today's judgement a spokesman for the Barclay Brothers said that the judge had conducted an extensive review of Mr McKillen's sources of funding and rejected his case that he had could have made the purchase.
The spokesman said the judge's conclusions would come as a further blow to Mr McKillen and underline once again the validity of the stance taken by the Barclay interests.
Today's judgement is unlikely to end the fight for Coroin, the company which controls the three London hotels. The Barclays still hold 28 percent of the shares. Derek Quinlan holds 35% while Paddy McKillen still has his 36%.
Mr McKillen said his lawyers were studying today's lengthy judgement with a view to an appeal, that he was ready and able to buy the Quinlan shareholding whenever it was offered and that he would never give up his right to the hotels.