By Christopher M. Matthews 

A federal judge allowed four men to withdraw their insider-trading guilty pleas on Thursday, the latest fallout from a pivotal appeals court ruling in December that has put new limitations on prosecutors' ability to pursue such cases.

The four men, who allegedly traded on tips about International Business Machine Corp.'s 2009 $1.2 billion acquisition of software company SPSS Inc., pleaded guilty in 2013 and 2014 to insider trading. But they asked to withdraw those pleas after a three-judge panel in the Second U.S. Circuit Court of Appeals overturned two insider-trading convictions in December and said prosecutors had been too aggressive in their interpretation of the law.

U.S. District Judge Andrew L. Carter Jr., who is presiding over the IBM case, agreed on Thursday, saying that in light of the Second Circuit ruling he would allow the four men to enter not guilty pleas. It is the first time since the December decision a judge has allowed similar insider-trading defendants to withdraw their guilty pleas.

The move comes as prosecutors face a Friday deadline to tell the Second Circuit whether they will ask for further review of its decision. The U.S. could ask for the entire court to look at the case or could appeal to the Supreme Court, which both require signoff from the Justice Department. It could also ask the same panel to re-review its decision, which doesn't require approval.

The stakes are high for the Manhattan U.S. attorney's office, which has had a recent run of insider-trading convictions in a closely watched effort that has featured charges against high-level traders at some of the country's biggest hedge funds. In the wake of the Second Circuit decision, a number of defendants have asked to have their cases tossed.

Most recently, on Thursday, former Galleon Group trader Zvi Goffer said in court papers he would ask a federal judge to toss his insider trading conviction and 10-year sentence. Legal experts said judges rarely allow defendants to pull pleas but Judge Carter's move could presage additional rescissions.

"This is but one ripple, and is yet a small one, from the Second Circuit's decision," said Columbia Law School Professor Daniel C. Richman. "I think it's fair to say there's more to come."

The Second Circuit's decision overturned the December 2012 convictions of former hedge-fund traders Todd Newman and Anthony Chiasson in New York federal court. The appeals court said prosecutors must prove traders knew that the person who provided an inside tip gained some sort of tangible reward for doing so. The court also dismissed prosecutors' contention that career advice or friendship constituted a reward, saying that, under that logic, "practically anything would qualify."

The defendants in the IBM case seized on the Second Circuit's statements about what constitutes a benefit. In court papers this month, the men-- Trent Martin, Thomas Conradt, David Weishaus and Daryl Payton--argued no benefit was provided to a lawyer who allegedly leaked the deal's details to Mr. Martin. They said there was only friendship and no benefits exchanged between the other defendants, who passed around Mr. Martin's tip.

A fifth defendant in the case, Benjamin Durant, pleaded not guilty and was scheduled to go to trial.

Prosecutors had argued the Second Circuit decision was incorrect, didn't apply to this case and the pleas should stand.

Lawyers for Mssrs. Martin, Conradt and Payton said Thursday Judge Carter made the correct decision. A lawyer for Mr. Weishaus declined to comment. A lawyer for Mr. Durant didn't immediately respond to a request for comment.

A spokesman for the Manhattan U.S. attorney's office declined to comment.

The Second Circuit's December ruling tarnished the Wall Street crackdown of New York U.S. Attorney Preet Bharara, which had yielded more than 80 convictions.

In addition to the IBM pleas, the ruling threatens to upend a handful of other convictions, including the marquee conviction of former SAC Capital portfolio manager Michael Steinberg.

On Thursday, Judge Carter said he was directly influenced by the appeals court's decision.

"Specifically, the Court was skeptical that the pleas were sufficient in light of [the ruling's] clarification of the personal benefit and tippee knowledge requirements of tipping liability for insider trading," he wrote in a three-page order.

The IBM case isn't necessarily over, as the indictment against the men remains pending. Mssrs. Durant and Payton have asked Judge Carter to toss that as well, which would end the case altogether, an issue the judge said he would address at a hearing Friday.

Mr. Richman said that while the Second Circuit decision was likely to undo other cases, its largest impact is the constraints it puts on prosecutors.

"It looks bound to be an obstacle to a range of cases that might otherwise be pursued," he said.

Write to Christopher M. Matthews at christopher.matthews@wsj.com

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