CHICAGO: A Chicago businessman was charged with helping an old friend from military school in Pakistan plot the deadly 2008 Mumbai attacks that killed 166 people, officials said.

Tahawwur Hussain Rana, 49, has been held in jail since his October arrest on charges of helping plot an attack on the Danish newspaper that published incendiary cartoons of the prophet Mohammed in 2005.

Prosecutors allege that Rana helped his friend David Coleman Headley, a key suspect in the Mumbai attacks, by allowing him to use his immigration company as a cover for surveillance trips to India and Denmark.

Rana was charged Thursday with three separate counts of providing material support for terrorism in the Mumbai attacks, the Denmark terror plot, and to the banned Pakistani militant group Lashkar-e-Taiba.

Also indicted on conspiracy charges related to the Denmark plot were Ilyas Kashmiri, an alleged terror kingpin in Pakistan who prosecutors accuse of being in regular contact with Al-Qaeda leaders, and Abdur Rehman Hashim Syed, a retired major in the Pakistani military. Neither man is in US custody.

Headley, 49, has pleaded not guilty to 12 terrorism related charges and remains in custody where he is cooperating with prosecutors.

The Washington-born son of a former Pakistani diplomat and American mother, Headley reportedly befriended Bollywood stars and even dated an actress during his lengthy surveillance trips to Mumbai.

The indictment alleges that Rana acted as a messenger while Headley scoped out the Mumbai terror targets, taking photos and video and entering their positions on a GPS device.

Nearly a year after the bloody 60-hour siege which began November 26, 2008, Headley was allegedly recorded discussing five future targets with Rana.

Prosecutors said the targets included Bollywood, the Indian temple Somnath, the National Defense College in Delhi, Shiv Sena, a political party in India with roots in Hindu nationalism and the Danish newspaper.

Headley had already begun the planning for a second Indian attack during a March 2009 surveillance trip whose targets included the National Defense College and Chabad Houses in "several cities" in India, the indictment alleges.

He was also working on the Danish newspaper plot weeks before the Mumbai attack was carried out, the indictment alleges.

Headley is accused of once again using Rana's immigration business as a cover in order to arrange a visit to the Copenhagen and Aarhus offices of Jyllands-Posten, Denmark's highest circulating daily.

During a February meeting in Pakistan, Kashmiri allegedly told Headley that they should use a truck bomb to attack the newspaper and directed him to meet with European contacts who could provide the money, weapons and manpower for the attack.

Headley and Rana were arrested in October on terror charges related to the plot to attack Jyllands-Posten and kill an editor and the cartoonist.

Headley was charged last month with spending two years casing Mumbai, even taking boat tours around the city's harbor to scope out landing sites for the attackers.

Rana, a Pakistani-born Canadian citizen who owns the Chicago-based First World Immigration Services that Headley allegedly used as a cover, insists that he is a pacifist who was "duped" by his friend.

A date has not yet been set for Rana's arraignment on the new charges.