Two former executives of a defunct Wall Street broker-dealer were sentenced to prison on Friday for participating in a scheme to pay $5 million in bribes to an official at a Venezuelan state economic development bank in exchange for business.

Benito Chinea, the former chief executive officer of Direct Access Partners LLC, and Joseph DeMeneses, a managing director at the firm, were each sentenced by U.S. District Judge Denise Cote in Manhattan to four years in prison.

"The extent of the misconduct here is extraordinary," Cote said.

The sentences were a year shy of the five-year maximum that prosecutors sought. Cote also ordered Chinea to pay $3.68 million and DeMeneses $2.71 million in fines and forfeited ill-gotten gains.

The proceedings came four months after the executives pleaded guilty in December to engaging in a conspiracy following a broad U.S. probe into foreign bribery involving their firm and Venezuelan state-owned banks.

Prosecutors said Chinea, 48, and DeMeneses, 45, participated in a scheme from 2008 through 2012 to direct payments to Maria de los Angeles Gonzalez de Hernandez, a senior official at Banco de Desarrollo Económico y Social de Venezuela, or Bandes.

Direct Access employees sent $5 million in kickbacks to Gonzalez, generally through bank accounts she controlled in Switzerland and elsewhere, prosecutors said.

The 140-employee firm in exchange received trading business that generated more than $60 million in fees, authorities said.

While DeMeneses and Chinea were unaware of the arrangement at first, they later participated in the conspiracy, prosecutors said.

The scheme was uncovered during a periodic U.S. Securities and Exchange Commission review. The U.S. Justice Department and the SEC brought their first cases over it in May 2013, which helped push Direct Access's parent company into bankruptcy.

At Friday's hearing, Chinea sought forgiveness from "all of the committed and loyal employees for my actions in this matter, which I deeply regret." DeMeneses sought leniency, saying he regretted his actions.

Before charging Chinea and DeMeneses in April 2014, prosecutors secured guilty pleas and cooperation agreements from Gonzalez and three Direct Access employees, Jose Alejandro Hurtado, Ernesto Lujan and Tomas Alberto Clarke Bethancourt.

Those four people have yet to be sentenced. A related SEC civil lawsuit, which alleges a broader scheme involving a second bank, also remains pending.

The case is U.S. v. Chinea, U.S. District Court, Southern District of New York, No. 14-cr-00240.