Back to results
US 5,332,837 AGranted
CC-1065 analogs
AssigneeThe Upjohn Company
InventorsRobert C. Kelly, David G. Martin, Paul A. Aristoff
Life of this patent
Estimating the term…
Abstract
This invention concerns 2-acyl-4,5,8,8a-tetrahydro-4-oxycyclopropan[c]pyrrol(3,2-e) indole derivatives of Formula I': ##STR1## the compounds of Formula I' are useful as uv light absorber substances, as chemical intermediates and as prodrugs of known spirocyclopropylpyrroloindole CC-1065 analogs. Representative Formula I' compounds have been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.
Claims20
A compound of formula ##STR17## where X.sub.8 is --O--, --S-- or --NH--;
- wherein W is selected from C.sub.1 -C.sub.5 alyl, phenyl or hydrogen;
- wherein X is selected from azido, a halogen atom, cyanate, thiocyanate, isocyanate, thioisocyanate, phosphate diester (--PO(OR).sub.2), phosphonyl (--O--PO.sub.2 R), thiophosphonyl (--O--PSOR), sulfinyl (--O--SOR) or sulfonyl (--O--SO.sub.2 R);
- wherein Y is selected from --C(O)R, --C(S)R, --C(O)OR.sub.1, --S(O).sub.2 R.sub.1, --C(O)NR.sub.2 R.sub.3, --C(S)NR.sub.2 R.sub.3, or --C(O)NHSO.sub.2 R.sub.4 ;
- wherein Z is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, phenyl or hydrogen;
- wherein R is selected from the group consisting of C.sub.1 -C.sub.20 alkyl;
- C.sub.2 -C.sub.6 alkenyl;
- C.sub.2 -C.sub.6 alkynyl;
- phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- naphthyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, C.sub.1 -C.sub.3 alkylthio or nitro;
- wherein R.sub.1 is selected from C.sub.1 -C.sub.20 alkyl or phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- wherein R.sub.2 and R.sub.3, being the same or different, are selected from hydrogen, C.sub.1 -C.sub.20 alkyl or phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- with the proviso that both R.sub.2 and R.sub.3 cannot be phenyl or substituted phenyl;
- and
- wherein R.sub.4 is selected from C.sub.1 -C.sub.10 alkyl;
- phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- naphthyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, C.sub.1 -C.sub.3 alkylthio or nitro.
13 more elements
A compound according to claim 30 where X .sub.8 is --O--.
A compound of claim 30, having the 1(S)-configuration of the stereoisomer of ##STR18## where X .sub.8 is --O--, --S-- or --NH--;
- wherein W is selected from C.sub.1 -C.sub.5 alkyl, phenyl or hydrogen;
- wherein X is selected from azido, a halogen atom, cyanate, thiocyanate, isocyanate, thioisocyanate, phosphate diester (--PO(OR).sub.2), phosphonyl (--O--PO.sub.2 R), thiophosphonyl (--O--PSOR), sulfinyl (--O--SOR) or sulfonyl (--O--SO.sub.2 R);
- wherein Y is selected from --C(O)R, --C(S)R, --C(O)OR.sub.1, --S(O).sub.2 R.sub.1, --C(O)NR.sub.2 R.sub.3, --C(S)NR.sub.2 R.sub.3, or --C(O)NHSO.sub.2 R.sub.4 ;
- wherein Z is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, phenyl or hydrogen;
- wherein R is selected from the group consisting of C.sub.1 -C.sub.20 alkyl;
- C.sub.2 -C.sub.6 alkenyl;
- C.sub.2 -C.sub.6 alkynyl;
- phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- naphthyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, C.sub.1 -C.sub.3 alkylthio or nitro;
- wherein R.sub.1 is selected from C.sub.1 -C.sub.20 alkyl or phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- wherein R.sub.2 and R.sub.3, being the same or different, are selected from hydrogen, C.sub.1 -C.sub.20 alkyl, or phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- with the proviso that both R.sub.2 and R.sub.3 cannot be phenyl or substituted phenyl;
- and
- wherein R.sub.4 is selected from C.sub.1 -C.sub.10 alkyl;
- phenyl optionally substituted with one, two or three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, or nitro;
- naphthyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, C.sub.1 -C.sub.3 alkylthio or nitro.
13 more elements
(S)-N-[2-[[1-(chloromethyl)-1,6-dihydro -8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2,-b 4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)-2-benzo furancarboxamide.
Dependencies are inferred from the claim text.