MANILA, Philippines -- A Japanese man was killed and his three companions wounded after an unidentified assailant shot them in front of a bar in Makati City late Thursday night, the police said.

Investigators said the killer had likely targeted Takahiro Asano, 42, who bore the brunt of the assault and died instantly from shots to the face and head.

Wounded were Agnes Macatangay, 27, Ruel Banares, 41, and Jaime Antonio Beech, 38, the police said.

The incident occurred at 11:15 p.m. at the smoking area outside Locked Up bar and restaurant at the corner of Filmore and Java Streets in Barangay (village) Palanan, Superintendent Manuel Santos Jr., chief of the Makati police investigation division, said.

The four were seated at a table when the assailant began shooting at them, Santos said.

Asano, a tenant at Royal Regent Condominium, died before reaching St. Claire Hospital, where the four were rushed after the shooting, according to a report by Police Officer 3 Nilo Sadsad.

His three companions were declared out of danger, the report said.

Eyewitnesses described the gunman to be 5'4" to 5'6" in height, long-haired and medium-built. He was wearing a brown shirt, denim pants and rubber shoes at the time of the incident and was last seen fleeing on foot on Java Street, apparently headed toward the South Superhighway, investigators said.

Santos said the motive for the killing remains unclear as they have not yet interviewed Asano's wounded companions, but added they are studying several angles.

The assailant, he said, had previously been seen in the area, apparently "casing" the regular haunts of the Japanese national.

The official said another angle they are studying is the possibility that Asano had been involved in a quarrel with other Japanese nationals based here.