They had been there since sometime in the late 1950s, and used to have very prominent signage directly facing Bush Street:
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That appears to be the back of a Ford Pinto wagon in that shot. That was a mid-year introduction, on sale in February of 1972, so that photo can't be earlier than that.
By the time I moved to Ukiah in March of 1976, the exterior remodel had been done (not my photo, found online):
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In fact, I drove past it several times before I knew it was there, since Bush is a one-way street and the sign faced the direction traffic goes. It wasn't until I parked on Bush and got out of the car that I saw it.
How about a photo from...Monday?
The only currently active ground-level retail in the building is a Subway.
And here's something---archive-dot-org has city directories.
The 1930 edition of the Polk's Crocker-Langley San Francisco City Directory shows Dow Jones and the Pacific Edition of the Wall Street Journal at 415 Bush.
It still appears as Dow Jones and the Pacific Edition of the Wall Street Journal in the 1957 edition---the year before KFRC moved in:
The 1930 edition is the earliest where "415 Bush" appears, so it's possible and perhaps likely that there were only three tenants between 1908 and 1985---The Old Poodle Dog, Dow Jones/Wall Street Journal and KFRC.
I've been meaning to write up a longer history, but travel and other things have made it hard to have a sustained period to concentrate on the matter and to write up what I've found. So here's an AP-broadcast-wire-level summary.
The building was constructed for the Old Poodle Dog after the 1906 earthquake. Before the quake, the restaurant was at the corner of Grant and Bush, where the Hotel Triton is now. The Old Poodle Dog actually dated to 1849, when it set up in some tents in what's now Chinatown. Prohibition dealt a blow to the Old Poodle Dog, which was the scene of a raid in 1921. Members of the Spreckels family were having a dinner, complete with wine, on the second floor of the building. Indicative of the family's status, a local Republican official tried to hold off the SFPD from raiding the dinner, but the raid happened anyway. The restaurant closed the next year. One or two of the owners (it's a bit unclear which) returned to France, disgusted that they couldn't serve wine at a fine dining establishment.
Yet...a new version of the Old Poodle Dog opened the next year, across from the Palace Hotel, probably where the House of Shields is now. This hung on until Prohibition ended, surviving until 1986 at various locations. Its last space was at the Crocker Galleria.
Back on Bush Street, the upper floors of the building were going to be converted into a gym. That may or may not have happened, with the newspapers of the time not being that great about follow-ups. In any event, the Wall Street Journal moved into the space, making it the paper's West Coast headquarters. I don't know if that operation included printing presses and Linotypes. The paper moved out in 1957, gaining a notice from Herb Caen, who reported that the Old Poodle Dog was considering moving back into the building, which was still the property of the restaurant's then-owner. Another Caen item from 1958 reported on KFRC's impending move to 415 Bush.
There's more to the story...that Prohibition raid, in particular, became controversial...but this summary hits the highlights.
After 1985...I haven't tried to dig into those years, and my time in San Francisco started in 1999. The area has gradually became less of a French restaurant row. Claude Lane now seems empty, and has been that way for about 15 years. Le Central is still up the street on Bush, as is Cafe de la Presse.
Our hotel this time was on that block. Returning in the evening after spending more time in Berkeley and Oakland than we expected to, the street scene was generally very quiet.