Manhattan federal prosecutors late Wednesday indicted four additional Turkish men, including a former economic minister, in the politically charged case against prominent Turkish gold trader Reza Zarrab for massive violations of U.S. sanctions on Iran.

The new charges expanded the case on the eve of a scheduled October trial and added to the challenges faced by former New York Mayor Rudy Giuliani, hired by Zarrab to try to broker a deal for his release between Turkish president Recep Erdogan and the Trump administration.

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Erdogan has criticized the case and former U.S. Attorney Preet Bharara, under whom it was filed. The new indictment says former economic minister Mehmet Caglayan took bribes to aid the scheme and a Turkish government-owned bank helped to facilitate it.

None of the new defendants are in custody. On Thursday, U.S. District Judge Richard Berman set a Sept. 25 hearing on the new indictment.