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Charter Communications Inc. billionaire Paul Allen’s unprofitable U.S. cable television company missed $73.7 million in interest payments due Thursday, moving it closer to a possible bankruptcy.

The company has 30 days to make good on the payments or risk a default, St. Louis-based Charter said today in a regulatory filing. The company said it’s working with bondholders on financial alternatives.

Charter, the biggest issuer of high-risk, high-yield bonds over the last decade, is saddled with $21 billion in debt as it tries to counter increasing competition. It is seeking to raise money after U.S. junk bond sales sank 73 percent last year while borrowing costs soared to a record.

"We view the probability of a Chapter 11 filing as likely," David Hamburger, a Citigroup Inc. analyst in New York, wrote in a note to investors Thursday.

Moody’s Investors Service downgraded Charter’s senior unsecured debt rating to Ca, the second lowest level of junk, in December, citing the need for a debt restructuring or potential bankruptcy this year.

Charter’s 10.25 percent notes due in 2010 fell 1.75 cents to 44.25 cents on the dollar at 11:33 a.m. in New York, according to Trace, the Financial Industry Regulatory Authority’s bond pricing service. The stock, which lost about 93 percent last year, fell 2 cents Thursday to about 11 cents in Nasdaq Stock Market trading.

Sharon Stern, a spokeswoman for Charter, declined to comment on why the company missed its interest payments. The company, in which Microsoft co-founder Allen bought a controlling interest in 1998, has lost money every year since going public in 1999.

Charter has sold $16.4 billion in U.S. junk bonds since 1999, the most of any company, according to data compiled by Bloomberg. Charter took advantage of investor demand for junk bonds that pushed U payday loans.S. company borrowing costs to record lows in June 2007, according to Merrill Lynch & Co. index data.

The cost to borrow surged last year as the subprime mortgage bond collapse spread to the broader credit markets, shutting the door to new financing for the riskiest companies. Yields on junk bonds rose to a record high of 21.82 percentage points more than U.S. Treasuries on Dec. 15, according to Merrill index data.

Borrowers sold about $40.6 billion worth of high-yield bonds last year, excluding conversions of bridge loans, down from $147.7 billion in 2007, according to Bloomberg data.

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Charter Chief Executive Neil Smit outlined efforts to reduce debt and extend maturities at an investors conference on Sept. 10. Charter paid $478 million in interest in the third quarter, according to a company filing with the Securities and Exchange Commission, and in September announced it would buy back as much as $100 million in senior notes to reduce interest expenses.

The missed interest payments today include obligations on three debt issues by CCH I Holdings LLC and five securities from Charter Communications Holdings LLC. About $1.17 billion in principal was outstanding on Sept. 30, according to the filing.

Charter is the fourth-biggest U.S. cable company and as of Sept. 30 served about 5.5 million customers.

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