The parent company of iHeartCommunications, which syndicates programs by conservative talk-show hosts Rush Limbaugh and Sean Hannity, appears to be headed toward bankruptcy.

In a statement filed last week with the Securities and Exchange Commission, the federal agency charged with regulating companies that offer investments to the public, iHeartCommunications' parent company, iHeartMedia Inc., said that it had "substantial doubt" that it would be in business by the middle of next year.

Beyond syndicating shows by Limbaugh, Hannity and other hosts like Steve Harvey and Ryan Seacrest, iHeartCommunications owns and operates more than 800 radio stations. It also sells ads on thousands of billboards across the country.