Four men from Rochdale have lost appeals against their sentences for sex offences against a 15-year-old girl.
Lord Chief Justice Lord Thomas dismissed applications to reduce the jail terms of Freddy Kendakumana, Roheez Khan and Chola Chansa.
Abdul Huk had his appeal against both conviction and a four-year sentence for sexual activity with a child dismissed.
The girl, who had been in care, was given vodka and drugs in exchange for sex.
Kendakumana, 27, Chansa, 33, Khan, 27, and Huk, 37 were jailed in December last year at Manchester Crown Court.
A fifth man, Mohammed Rafiq Abubaker, was also found guilty of sexual activity with a child and did not lodge an appeal against his two-and-a-half-year sentence.
The offences took place in 2008 and 2009.'Vulnerable girls'
The four men appealed against their sentences, ranging from between four and eight-and-a-half years, on the grounds they were overly harsh.
But Lord Thomas, at the Court of Appeal sitting at Manchester Crown Court, said the judge during the trial had given them the correct sentences.
He told them: "It is a serious aggravating factor that she was exploited as a vulnerable person.
"And the judge was right to make clear that the courts must take every step open to them to protect vulnerable young girls from exploitation of this kind in whatever part of the country they live."
In a separate trial, nine men who ran a child sexual exploitation ring in the Heywood area of Rochdale were jailed in 2012.
On the same day the five men were jailed, a report was publishedhighlighting a "shocking" inability to protect seven vulnerable girls from sexual exploitation in the town.