New York City’s efforts on climate change were dealt a blow in court Thursday, as a U.S. District Court judge dismissed a lawsuit the city brought against five oil and gas companies.

The city filed suit against BP, Shell, Chevron, ConocoPhillips and Exxon Mobil over the role the companies play in exacerbating climate change. According to the ruling, the companies are collectively responsible for over 11% of all carbon and methane pollution that has accumulated in the atmosphere since the Industrial Revolution.

They have also allegedly known for decades about the dire effects their businesses have on the environment; the ruling notes that the companies have known since the 1950s “that their fossil fuel products pose risks of severe impacts on the global climate” — yet despite knowing these risks, the companies “extensively promoted fossil fuels for pervasive use, while denying or downplaying these…