Two former executives of Russian oil firm Yukos have been sentenced to more than 10 years in prison each.
Two more Yukos executives will be joining Mr Khodorkovsky in prison
A Moscow court found them guilty of embezzlement and money-laundering in the latest twist in the Yukos saga.
The verdict came as the Russian state receiver prepares to auction off Yukos assets, estimated to be worth $22bn.
Yukos former boss Mikhail Khodorkovsky is already serving an eight-year sentence in a case critics of the Kremlin say was politically-motivated.
Lawyers for the two men, Vladimir Malakhovsky and Vladimir Pereverzin, condemned the verdicts as groundless.
The Moscow court heard prosecutors state that the men had siphoned off $13bn in an oil price-fixing scam.
Mr Malakhovsky, ex-head of Yukos-owned Ratibor, was sentenced to 12 years imprisonment.
Mr Pereverzin, former deputy director of Yukos' foreign debt department received a sentence of 11 years.
The prosecution alleged that the men bought oil at artificially low prices from Yukos' subsidiaries and then sold it on at higher prices.
A third defendant in the case, Antonio Valdes Garcia, fled police custody in January.
Mr Valdes Garcia, who holds Russian and Spanish citizenship, headed up Yukos subsidiary Fargoil.
The auction of Yukos assets, featuring five oil refineries, relates to $26bn of unpaid taxes the Russian government claims it is owed by the Yukos group.