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US 5,616,724 AGranted
Fused pyrrolo[2,3-c]carbazole-6-ones
AssigneeCephalon, Inc.
InventorsRobert L. Hudkins, James L. Diebold, Ernest Knight, Jr.
Life of this patent
Estimating the term…
Abstract
Disclosed in this patent document are synthetic, biologically active molecules referred to as fused pyrrolo[2,3-c]carbazole-6-ones. These molecules are represented by the following general formulae: ##STR1## Methods for making and using the fused pyrrolo[2,3-c]carbazole-6-ones are also disclosed.
Claims16
A fused pyrrolo[2,3-c]carbazole-6-one represented by a formula selected from the group consisting of:
- ##STR4## wherein:
- a) R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons substituted or unsubstituted aryl, arylalkyl, heteroaryl, heteroarylalkyl;
- C(.dbd.O)R.sup.9, where R.sup.9 is alkyl of 1-4 carbons or aryl;
- (CH.sub.2).sub.n OR.sup.9, where n is an integer of 1-4;
- OR.sup.10, where R.sup.10 is H or alkyl of 1-4 carbons;
- (CH.sub.2).sub.n OR.sup.14, where R.sup.14 is the residue of an amino acid after the hydroxyl group of the carboxyl group is removed;
- OR.sup.14, NR.sup.7 R.sup.8 ;
- (CH.sub.2).sub.n NR.sup.7 R.sup.8, and O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ;
- and either
- (1) R.sup.7 and R.sup.8 independently are H or alkyl of 1-4 carbons;
- or
- (2) R.sup.7 and R.sup.8 are combined together to form a linking group of the general formula --(CH.sub.2).sub.2 --X.sup.1 --(CH.sub.2).sub.2 --, where X.sup.1 O, S or CH.sub.2 ;
- b) R.sup.2 is selected form the group consisting of H, SO.sub.2 R.sup.9, CO.sub.2 R.sup.9, C(.dbd.O)R.sup.9, alkyl of 1-8 carbons, alkenyl of 1-8 carbons, alkynyl of 1-8 carbons, and a monosaccharide of 5-7 carbons, wherein each hydroxyl group of said monosaccharide is independently selected from the group consisting of unsubstituted hydroxyl and a replacement moiety replacing said hydroxyl group selected from the group consisting of H, alkyl of 1-4 carbons, alkylcarbonyloxy of 2-5 carbons, and alkoxy of 1-4 carbons;
- wherein either
- 1) each alkyl of 1-8 carbons, alkenyl of 1-8 carbons, or alkynyl of 1-8 carbons is unsubstituted;
- or
- 2) each alkyl of 1-8 carbons, alkenyl of 1-8 carbons, or alkynyl of 1-8 carbons independently is substituted with 1-3 groups selected from the group consisting of aryl of 6-10 carbons, heteroaryl, F, Cl, Br, I, CN, NO.sub.2, OH, OR.sup.9, O(CH.sub.2).sub.n NR.sup.7 R.sup.8, OCOR.sup.9, OCONHR.sup.9, O-tetrahydropyranyl, NH.sub.2, NR.sup.7 R.sup.8, NR.sup.10 COR.sup.9 ;
- NR.sup.10 CO.sub.2 R.sup.9, NR.sup.10 CONR.sup.7 R.sup.8, NHC(.dbd.NH)NH.sub.2, NR.sup.10 SO.sub.2 R.sup.9 ;
- S(O).sub.y R.sup.11, wherein R.sup.11 is H, alkyl of 1-4 carbons, aryl of 6-10 carbons, or heteroaryl, and y is 1 or 2;
- SR.sup.11, CO.sub.2 R.sup.9, CONR.sup.7 R.sup.8, CHO, COR.sup.9, CH.sub.2 OR.sup.7, CH.sub.2 OR.sup.9, CH.dbd.NNR.sup.11 R.sup.12, CH.dbd.NOR.sup.11, CH.dbd.NR.sup.9, CH.dbd.NNHCH(N.dbd.NH)NH.sub.2 ;
- SO.sub.2 NR.sup.12 R.sup.13, wherein either
- (1a) R.sup.12 and R.sup.13, independently, are H, alkyl of 1-4 carbons, aryl of 6-10 carbons, or heteroaryl;
- or
- (2a) R.sup.12 and R.sup.13 are combined together to form a --(CH.sub.2).sub.2 --X.sup.1 --(CH.sub.2).sub.2 linking group;
- PO(OR.sup.11).sub.2, NHR.sup.14, NR.sup.10 R.sup.14, OR.sup.14, and a monosaccharide of 5-7 carbons wherein each hydroxyl group of said monosaccharide is independently selected from the group consisting of unsubstituted hydroxyl and a replacement moiety replacing said hydroxyl group selected from the group consisting of H, alkyl of 1-4 carbons, alkylcarbonyloxy of 2-5 carbons, and alkoxy of 1-4 carbons;
- c) each R.sup.3 and R.sup.4, independently, is selected from the group consisting of H, aryl of 6-10 carbons, heteroaryl, F, Cl, Br, I, CN, CF.sub.3, NO.sub.2, OH, OR.sup.9, O(CH.sub.2).sub.n NR.sup.7 R.sup.8, OCOR.sup.9, OCONHR.sup.9, NH.sub.2, (CH.sub.2).sub.n OR.sup.9, (CH.sub.2).sub.n OR.sup.10, (CH.sub.2).sub.n OR.sup.14, OR.sup.14, NHR.sup.14, NR.sup.7 R.sup.8, NR.sup.7 (CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.10 COR.sup.9, NR.sup.10 CONR.sup.7 R.sup.8, SR.sup.11, S(O).sub.y R.sup.11, CO.sub.2 R.sup.9, COR.sup.9, CONR.sup.7 R.sup.8, CHO, CH.dbd.NOR.sup.11, CH.dbd.NR.sup.9, CH.dbd.NNR.sup.11 R.sup.12, (CH.sub.2).sub.n SR.sup.9, (CH.sub.2).sub.n S(O).sub.y R.sup.9 ;
- CH.sub.2 SR.sup.15, where R.sup.15 is alkyl of 1-4 carbons;
- CH.sub.2 S(O).sub.y R.sup.14, (CH.sub.2).sub.n NR.sup.7 R.sup.8, (CH.sub.2).sub.n NHR.sup.14, alkyl of 1-8 carbons, alkenyl of 1-8 carbons, and alkynyl of 1-8 carbons;
- and either
- 1) each alkyl of 1-8 carbons, alkenyl of 1-8 carbons or alkynyl of 1-8 carbons is unsubstituted;
- or
- 2) each alkyl of 1-8 carbons, alkenyl of 1-8 carbons, or alkynyl of 1-8 carbons is independently substituted as described in b)2) above;
- d) R.sup.5 is selected from the group consisting of H, alkyl of 1-8 carbons, alkenyl of 1-8 carbons, and alkynyl of 1-8 carbons;
- and either
- 1) each alkyl, alkenyl, or alkenyl group is unsubstituted;
- or
- 2) each alkyl, alkenyl, or alkynyl group is substituted with 1-3 groups selected from the group consisting of F, Cl, Br, I, CN, CF.sub.3, NO.sub.2, OH, OR.sup.9, O(CH.sub.2).sub.n NR.sup.7 R.sup.8, OCOR.sup.9, OCONHR.sup.9, NH.sub.2, (CH.sub.2).sub.n OR.sup.9, (CH.sub.2).sub.n OR.sup.14, NR.sup.7 R.sup.8, NR.sup.7 (CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.10 COR.sup.9, NR.sup.10 CONR.sup.7 R.sup.8, SR.sup.11, S(O).sub.y R.sup.11, CO.sub.2 R.sup.9, COR.sup.9, CONR.sup.7 R.sup.8, CHO, CH.dbd.NOR.sup.11, CH.dbd.NR.sup.9, CH.dbd.NNR.sup.11 R.sup.12, (CH.sub.2).sub.n SR.sup.9, (CH.sub.2).sub.n S(O).sub.y R.sup.9, CH.sub.2 SR.sup.15, CH.sub.2 S(O).sub.y R.sup.14, (CH.sub.2).sub.n NR.sup.7 R.sup.8, and (CH.sub.2).sub.n NHR.sup.14 ;
- e) X is selected from the group consisting of --N--, --O--, --S--, --S(.dbd.O)--, --S(.dbd.O).sub.2 --, alkylene of 1-3 carbons, --C(.dbd.O)--, --C(R.sup.2).dbd.C(R.sup.2)--, --(CR.sup.2).sub.2 --, --CH.dbd.CH--, --CH(OH)--CH(OH)--, --C(.dbd.NOR.sup.11)--, --C(OR.sup.11)(R.sup.11)--, --C(.dbd.O)CH(R.sup.15)--, --CH(R.sup.15)C(.dbd.O)--;
- --CH.sub.2 --Z--, --Z--CH.sub.2 --, --CH.sub.2 ZCH.sub.2 --, where Z is selected from the group consisting of --C(OR.sup.11)(R.sup.11)--, O, S, C(.dbd.O), and NR.sup.11 ;
- and alkylene of 1-3 carbons substituted with a group selected from the group consisting of one R.sup.5 substituent group, SR.sup.10, OR.sup.10, OR.sup.14, R.sup.15, phenyl, naphthyl, and arylalkyl of 7-14 carbons.
37 more elements
Dependencies are inferred from the claim text.