by Todd Feurer, CBS Chicago web producer

CHICAGO (CBS) — After striking out in three attempts to convince a federal judge in New York to release him from jail due to the COVID-19 pandemic, indicted singer R. Kelly is now taking a swing in a federal appeals court, arguing the judge’s “medical conclusions are poor at best.”

As he awaits multiple trials on sex crime charges, Kelly’s attorneys have filed three motions with U.S. District Judge Ann Donnelly in New York, requesting he be granted bail, and released to home confinement and electronic monitoring at his condo in the South Loop. Three times Donnelly has turned them down, ruling his attorneys have not shown he is at high risk of contracting the virus, and that he remains a flight risk and a danger to the community.

Kelly’s attorneys have argued his age of 53, and the fact he was recently diagnosed as pre-diabetic make him especially vulnerable to contracting the virus while locked up at the Metropolitan Correctional Center in downtown Chicago, but Donnelly has not been swayed, ruling that neither his age nor his prediabetes are considered high risk factors for COVID-19.

On Tuesday, Kelly’s attorneys filed a new motion with the 2nd U.S. Circuit Court of Appeals, asking the court to overturn Donnelly’s rulings.

“The Court’s medical conclusions are poor at best and the CDC claims are incorrect. They claim that because he is 53 not 75 he ‘s not at a high risk for COVID. Clearly risk increases with age but there is not a rule that only people 75 and older are at-risk. They are just at the highest risk, however 50-75 is also an at-risk group,” Kelly’s attorneys wrote in their filing with the appeals court.

Kelly’s lawyers also argued they cannot properly prepare for his upcoming trials — the first of which is scheduled for September — because they can only speak to him for 15 to 30 minutes at a time.

“Presently, none of Mr. Kelly’s attorneys are even allowed to visit with him at the MCC Chicago. No one is allowed in. There are no means by which to have lengthy conversations as they are limited to 15 minutes (occasionally 30). There are no means by which to review evidence with Mr. Kelly, show him documents , review photographs , or discuss strategy,” they wrote.

Defense attorneys also said Kelly has “literacy issues” that make it impossible to prepare for trial without meeting him in person. They are asking the appeals court to reverse Donnelly’s rulings, and order him released from custody, with any conditions they deem necessary.

Federal prosecutors have yet to respond to Kelly’s motion, but in the past have repeatedly argued he is a flight risk, and if released would also pose a risk of witness tampering. The feds have noted the charged Kelly now faces accuse him of threatening witnesses and paying bribes to keep witnesses from cooperating in the previous child pornography case against him in Cook County, which resulted in his acquittal in 2008.

Kelly, 53, faces sex crime charges in four separate jurisdictions in Chicago, New York, and Minnesota.

The federal charges in New York accuse Kelly of using his fame to recruit young women and girls for illegal sexual activity. The racketeering case also accuses him of kidnapping, sexual exploitation of a child, and forced labor. Jury selection in that case is now scheduled to begin on Sept. 29.

Federal prosecutors in Chicago have charged him with videotaping himself having sex with underage girls, and paying hush money and intimidating witnesses to cover up his crimes. That trial is scheduled for October.

Cook County prosecutors have charged Kelly with multiple counts of sexual assault and sexual abuse against four women years ago. The first of those trials is scheduled for September.

Minnesota prosecutors have charged him with engaging in prostitution with an underage girl. No trial date has been set in that case.

It’s unclear if any of Kelly’s trials will be held as currently scheduled, due to the coronavirus pandemic.

If convicted of all the charges, Kelly could face the rest of his life in prison.