FILE – In this April 24, 2007, file photo, a hearse carries the body of James Filiaggi from Southern Ohio Correctional Facility in Lucasville, Ohio, following his execution for killing his ex-wife in 1994. Magistrate Judge Michael Merz in Dayton, Ohio, declared Ohio's new three-drug lethal injection process unconstitutional on Thursday, Jan. 26, 2017, and delayed three executions, including the execution of Ronald Phillips that had been scheduled Feb. 15, 2017. (AP Photo/Scott Osborne, File)

FILE – In this April 24, 2007, file photo, a hearse carries the body of James Filiaggi from Southern Ohio Correctional Facility in Lucasville, Ohio, following his execution for killing his ex-wife in 1994. Magistrate Judge Michael Merz in Dayton, Ohio, declared Ohio's new three-drug lethal injection process unconstitutional on Thursday, Jan. 26, 2017, and delayed three executions, including the execution of Ronald Phillips that had been scheduled Feb. 15, 2017. (AP Photo/Scott Osborne, File)

COLUMBUS, Ohio (AP) — Ohio’s efforts to restart executions, including a law shielding the source of its drugs, hit a new setback Thursday as a federal judge declared the state’s latest lethal injection process unconstitutional and delayed three executions, including one scheduled next month.

The ruling by Magistrate Judge Michael Merz in Dayton followed a weeklong hearing over the three-drug method Ohio planned to use Feb. 15 on death row inmate Ronald Phillips.

It was the latest in several delays over the years for Phillips, who in the past had his execution delayed by court rulings and by his request, ultimately denied, to donate organs to family members after his death.

The 43-year-old Phillips was sentenced to die for raping and killing his girlfriend’s 3-year-old daughter, Sheila Marie Evans, in 1993.

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The judge agreed with attorneys for Phillips and two other condemned killers that the first drug in the process, the sedative midazolam, couldn’t pass a constitutional bar of causing “substantial risk of serious harm” previously set by the U.S. Supreme Court.

The judge also barred the state from using the second and third drugs in the protocol that paralyze inmates and stop their hearts.

Using those drugs is “completely inconsistent with the position” the state previously took when it announced it would no longer use them in executions, the judge said.

Lawyers for death row inmates successfully argued that a compounded dose of the anesthetic pentobarbital was “a sufficiently available alternative method” to satisfy the U.S. Supreme Court’s constitutional test, the judge said.

Merz wrote that he recognizes yet another delay in executions does not serve the goal of crime deterrence through speedy executions.

“However, when executions are routinely delayed decades in Ohio, it is very debatable how much loss in deterrence there is from waiting until a case can be tried on the merits,” Merz said.

The state appealed Thursday afternoon to the 6th U.S. Circuit Court of Appeals in Cincinnati. Messages were left with the attorneys representing the condemned inmates.

Executions have been on hold in Ohio since January 2014, when Dennis McGuire gasped and snorted during the 26 minutes it took him to die, the longest execution since the state resumed putting prisoners to death in 1999.

The state used a two-drug method with McGuire, starting with midazolam in its first use for executions in the country.

Ohio then discontinued that method, but it struggled to find new supplies of drugs as drugmakers placed them off-limits for executions.

In October, the prisons agency said it would use midazolam; rocuronium bromide, which causes paralysis; and potassium chloride, which stops the heart. The state hasn’t said where it got the drugs.

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Records show Ohio has enough on hand for dozens of executions. The state says that doesn’t take into account the drugs’ expiration dates and other factors.

The initial dose of midazolam would have been 50 times greater than that used for McGuire.

The state prisons director has also said Ohio is trying to buy supplies of a reversal drug if midazolam fails to properly render an inmate unconscious.

Attorneys challenging Ohio’s new three-drug method said midazolam is unlikely to relieve an inmate’s pain.

The drug, which is meant to sedate inmates, also was used in a problematic 2014 execution in Arizona. But last year, the U.S. Supreme Court upheld the use of midazolam in an Oklahoma case.

The state said the three-drug method is similar to its past execution process, which survived court challenges. State attorneys also say the Supreme Court ruling last year makes clear the use of midazolam is allowable.

The leader of the state’s execution team testified on Jan. 4 that McGuire’s execution was unlike anything he’d seen before.

The man testifying anonymously as Team Member No. 10 said he “was wondering what was going on” during the 2014 execution.

A second execution team member, identified as Team Member No. 21, testified that he didn’t believe McGuire suffered.

Thursday’s ruling also delays the March 15 execution of Gary Otte, sentenced to die for robbing and killing two people over two days in February in Parma in suburban Cleveland. It also delays the April 12 execution of Raymond Tibbetts, sentenced to die for killing his wife and the man who’d let the couple stay with him in Cincinnati.

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Andrew Welsh-Huggins can be reached on Twitter at https://twitter.com/awhcolumbus. His work can be found at http://bigstory.ap.org/content/andrew-welsh-huggins