(Bloomberg) -- Russia failed to overturn a ruling in the Netherlands that ordered Moscow to pay around $50 billion in the bankruptcy case of Yukos Oil Co., once the largest Russian oil and gas company.

The Amsterdam Court of Appeal dismissed Russia’s latest legal challenge in a saga that has dragged on for nearly two decades. The latest verdict is unlikely to result in an immediate payment to the former shareholders of Yukos. Russia has previously said it isn’t bound to pay the largest arbitration payout ever.

The arbitration awards in the case remain valid, the court said in a statement on Tuesday. It added that Russia’s claim that the shareholders committed fraud during arbitration proceedings was made too late but even if it had been made in time, the penalty would have still been upheld.

The three major shareholders of Yukos - Veteran Petroleum Ltd, Yukos Universal Ltd. and Hulley Enterprises Ltd - started arbitration proceedings against the Russian federation in 2005. The owners of the now defunct Yukos Oil claimed Russia was politically motivated when it imposed several tax demands that ultimately led the firm to bankruptcy. State-owned Rosneft PJSC then took over most of Yukos’ assets. 

The arrest of Russia’s richest man, Mikhail Khodorkovsky, and the seizure of Yukos came at a time in the early days of Vladimir Putin’s presidency when the head of state sought to reestablish the Kremlin as the country’s center of power.

A court in The Hague previously ruled in favor of the shareholders and ordered Russia to pay $50 billion in compensation in 2014. The Russian state attempted to challenge the arbitration awards and ask that they be set aside. Part of the judgment was overturned in 2021 by the Netherlands’ highest court, which asked that a lower court review one ground of the case again.

After a Dutch arbitration court ordered Russia to pay the damages in 2014, former Yukos shareholders sought to seize assets in countries including France, Belgium, the U.S., the Netherlands and India. In Belgium and France, state assets that had been frozen were unblocked following Russian protests. 

In February the former Yukos shareholders had their first success in seizing Russian assets. They obtained a charging order over a vacant plot of land in the expensive Kensington neighborhood of London. The plot was bought by the Russian Federation for £8 million in 2006.

“We will continue to focus our attention on the ongoing enforcement against Russian state assets in The Netherlands, England, and the United States, and we do not rule out we will start enforcement proceedings in other countries as well,” said Tim Osborne, director of GML Ltd., a holding company belonging to the former majority shareholders in Yukos.

In November last year, a UK judge denied Russia immunity from a case bought by the Yukos shareholders and concluded the state would have to answer at trial for why it hasn’t paid out a record arbitration award which now amounts to nearly $60 billion including interest.

--With assistance from Diederik Baazil.

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