The United Nations on Friday failed to adopt a resolution brought by China and Russia that would have extended sanctions relief on Iran for another six months under the nuclear deal.

The vote was 4 to 9, with Algeria, China, Pakistan, and Russia in favor and Denmark, France, Greece, Panama, Sierra Leone, Slovenia, Somalia, the United Kingdom and the United States against.

Guyana and South Korea abstained.

The vote came after Britain, France and Germany triggered the deal’s “snapback” measure, which reinstates sanctions on Iran following stalled talks on its nuclear program.

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The sanctions, which will go into effect unless there’s a last minute deal on Friday, will include freezing Iranian assets abroad, halting arms deals with Tehran and penalizing any development of Iran’s ballistic missile program. 

“We had hoped that European colleagues and the U.S. would think twice, and they would opt for the path of diplomacy and dialogue instead of their clumsy blackmail, which merely results in escalation of the situation in the region,” Dmitry Polyanskiy, deputy Russian ambassador to the U.N., said during the meeting.

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Iran’s foreign minister, Abbas Araghchi, had also been meeting with his French, German and British counterparts in the lead up to the U.N. vote. 

A European diplomat told The Associated Press the meeting “did not produce any new developments, any new results.”

On Tuesday, Ayatollah Ali Khamenei, Iran’s supreme leader, also said that Iran would not “surrender to pressure” and that negotiations with the U.S. would be a “dead end.” 

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In an interview on Friday, Iranian President Masoud Pezeshkian called the decision “unfair, unjust and illegal.”

The Associated Press contributed to this report.