I have Christe Jones H&C Plantation chips with the same font as Anna's but they do not have the center circle. CJ's would date 1950's - 1965 or so. CJ's are UFC's. Skey's would date 1937-65.
No way to tell if there is a conection between the CJ's and the small key's.
I think ID's on either one are lost to history.