The Upjohn Co.

Martha A Warpehoski

Robert C Kelly

Wendell Wierenga

1,2,8,8a-Tetrahydrocyclopropa[3]pyrrolo(3,2-e)indol-4(5H)-ones, and related compounds of formulas I and intermediate therefor II ##STR1## wherein R.sub.2, R.sub.2 ', R.sub.3, R.sub.5, R.sub.50 and X are as defined in the specification, e.g., (7bR,8aS)-1,2,8,8a -tetrahydro-7-methyl-2-[[5-(((1H-indol-2-yl)carbonyl)amino)-1H-indol-2-yl] carbonyl]cyclopropa[pyrrolo[3,2-e]indol-4(5H)-one (U-71,184), as purified, and its racemic form (U-68,415), and related compounds, are useful as ultraviolet light absorbers and as antibacterials. The lead compounds are useful as antitumor drug compounds in standard laboratory animal tests.

1,2,8,8a-tetrahydrocyclopropa (C) pyrrolo [3,2-e)]-indol-4(5H)-ones and

1,2,8,8a-Tetrahydrocyclopropa[3]pyrrolo(3,2-e)indol-4(5H)-ones, and related compounds of formulas I and intermediate therefor II ##STR1## wherein R.sub.2, R.sub.2 ', R.sub.3, R.sub.5, R.sub.50 and X are as defined in the specification, e.g., (7bR,8aS)-1,2,8,8a-tetrahydro-7-methyl-2-[[5-(((1H-indol-2-yl)carbonyl)ami no)-1H-indol-2-yl]carbonyl]cyclopropa[pyrrolo[3,2-e]indol-4(5H)-one (U-71,184), as purified, and its racemic form (U-68,415), and related compounds, are useful as ultraviolet light absorbers and as antibacterials. The lead compounds are useful as antitumor drug compounds in standard laboratory animal tests.

1,2,8,8A-tetrahydrocyclopropa(c)pyrrolo(3,2-e)-indol-4-(5H)-ones and

An improved process for preparing sulfonylated indoline compounds of the formula ##STR1## via reduction of a nitrodiol of the formula ##STR2## where R.sub.1 and R.sub.3 are defined in the specification, to obtain the corresponding aminodiol ##STR3## and then the aminodiol (III) is sulfonylated and cyclized in situ to obtain the sulfonylated indoline compound (I). The substituted indoline compounds (I) are useful in overall processes for making 1,2,8,8a-cyclopropa[c]benzo[1,2-b:4,3-b']dipyrrol-4(5H)-ones which have useful light absorber, anti-bacterial and anti-tumor pharmaceutical use properties.

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Comstock Township, MI, United States of America

Martha A Warpehoski