San Antonio-based iHeartMedia Inc. is taking its bondholders back to court, seeking hundreds of millions of dollars in damages over a previous legal dispute that the radio and billboard giant said delayed plans to refinance its debt and cost it real money.

IHeartMedia won a Bexar County state district court lawsuit in May against the same group of bondholders, which was threatening to force the company into technical default on roughly $6 billion of its debt.

The dispute stems from a December transaction in which iHeartMedia transferred some of its ClearChannel Holdings stock from one subsidiary to another. Investors claimed the move violated the company’s credit agreements.

The court sided with iHeartMedia in May, but the company now says that the dispute delayed its ability to refinance some of its debt and that it cost more money to restructure its bonds as a result.

The company had roughly $20.8 billion in outstanding debt as of March 31. Many of its bonds have fallen in value since they were originally issued as iHeartMedia’s finances weakened, allowing the company to repurchase and retire some of its old debt at a discount earlier this month.

IHeartMedia subsidiary Broader Media purchased senior debt due in 2018 that carried a 10 percent interest rate and had an original face value of $383 million for $222 million. But the company said the purchase was more than $100 million higher than it would have paid in February.

The transaction was postponed while the court weighed whether iHeartMedia violated its debt covenants.

“Because of the increase in price of iHeart’s debt, (the bondholders’) misconduct has cost iHeart and Broader Media additional damages of up to $375 million, and total damages between $100 (million) and $475 million,” according to iHeartMedia’s lawsuit.

The lawsuit adds that bondholder actions have damaged the company’s business relations and reputation “in an amount to be proven at trial.”

“IHeart suffered special damages in the form of economic loss to its business, including the lost discount and reduced interest expense on repurchased debt,” the lawsuit states.

IHeartMedia filed the new lawsuit Tuesday because it wanted to “reaffirm our position that such debt repurchases are permissible,” the company said in a statement. “We believe these repurchases are in the best interests of the company and its stakeholders. We intend to take any other actions necessary to protect the company and will continue to explore opportunities to strengthen our capital structure.”

Jones Day lawyer Bruce Bennett, who represents the bondholders, did not immediately respond Thursday to a request for comment.

“The closer to 2019, the more power senior debtholders have,” Jack Kranefuss, senior director for corporate credit rater Fitch Ratings in New York, said in late June. “It increases the chances of iHeart having to go through some sort of bankruptcy.”

IHeartMedia is trying to extend the maturity on some of its $20.8 billion in debt due over the next seven years, Kranefuss said. Almost half of the company’s notes need to be repaid by 2019, according to company securities disclosures.

At some point, even selling its 850 radio stations won’t be enough to repay the company’s crushing debt load under its current terms because the company is too highly leveraged, Kranefuss added.

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