A solicitor has found himself on the wrong side of the law after allegedly assaulting a woman and a police officer in the same night.

Hector Ekes, 47, was due to appear in Sydney Downing Centre Local Court on Monday after he was charged with assaulting a woman in Darlinghurst on October 23 last year.

Police allege the former high-flying lawyer also assaulted a police officer in the execution of his duty within the same 30-minute time frame.

Since the night of the alleged assaults, police claim Mr Ekes has twice breached the conditions of an apprehended violence order put in place to protect the woman.

According to police, the most recent breach was committed just over two weeks ago in Darlinghurst.

Mr Ekes is prohibited from being in the company of the woman within 12 hours of drinking alcohol, which was allegedly the foundation of his previous breach.

However, the court heard the former partner at Gardner Ekes is currently struggling with mental illness.

His lawyer Daniel Brezniak said Mr Ekes is currently in hospital, making him unable to attend court on Monday.

He said the defence would be making a section 14 application to have the charges dismissed on mental health grounds.

If the application is unsuccessful, the court heard the matter will be set down for a hearing.

Mr Ekes will return to court on October 7 to make the mental health application.

The apprehended violence order to protect his female victim has been adjourned to the same date.

The court heard he will remain on bail until that date.

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