BROOMFIELD - Three executives of Arca Biopharma Inc. and an investor have bought company stock to raise about $325,000 in a private placement, according to Securities and Exchange Commission documents.

Michael Bristow, chief executive of Broomfield-based Arca BioPharma, John Zabriskie, a director, and Chris Ozeroff, Arca's senior vice president and general counsel, bought shares, as did Jean-Francois Formela, an investor, according to SEC documents. After expenses, the net proceeds of the private placement are expected to be $280,000.

Arca's chief financial officer Philip Wheeler said in an email that the company wished not to comment past its filings with the SEC. The company is noncompliant with Nasdaq listing standards and has said it will file for an appeal. A Nasdaq spokesman said he could not comment about specific companies.

Arca's heart disease drug Gencaro received a U.S. patent in January.

The company received a delisting warning from Nasdaq on April 12. In general, companies publicly traded on the Nasdaq stock exchange must meet certain standards to continue to be publicly traded.

Companies that meet Nasdaq's equity standard, for example, must have stockholder equity of $2.5 million; have at least 500,000 publicly held shares; must have $1 million in stock value; have stock that trades for at least $1 per share; and have at least 300 public stockholders.

Arca's delisting notice from Nasdaq the company 180 days to come back into compliance with a Nasdaq requirement that its stock trade for $1 per share or more. The company's stock had been below $1 per share for the preceding 30 business days when the warning was made, according to the SEC document.

Nasdaq notified Arca on Wednesday, Oct. 10, the deadline for the 180-day period, that the company still did not satisfy a listing requirement, according to an SEC document.

The company's stock has traded between 26 cents and $2.45 per share in the last year. It was trading at 26 cents mid-day Thursday, Oct 25.

Arca has received delisting notices from Nasdaq in each of the last three years, according to SEC documents. The company regained compliance in 2010 and again in 2011.