Sugimasu is from sugiru, meaning to pass, to exceed, to go beyond. It is added to the stems of adjectives or -masu verbs to express a sense of "too much"
o sugimasu：I guess that the o is from 多い ooi, which means many. Hence the expression means something along the lines of "far too many." (if I am wrong, someone please correct me.)
oso sugimasu. Oso is from osoi,遅い which means slow or late. Hence, the expression means something like "(it) is too slow/too late"
Taka sugimasu. Taka is the stem of takai 高い which means expensive. The sentence means "(It is) too expensive." Sugimasen is the polite negative form of sugiru, so I assume "taka sugimasen" means "not too expensive".
I hope this helps.