# US 5,705,511 A · Fused pyrrolocarbazoles

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- Number: US 5,705,511 A
- Document ID: US5705511A
- Status: Granted
- Kind: A
- Application number: 08/526,798
- Filed: 1995-09-11
- Granted: 1998-01-06
- Earliest claimed: 1994-10-14
- Assignees: Cephalon, Inc.
- Inventors: Robert L. Hudkins; Ernest Knight, Jr.
- Web page: https://patentgrep.com/patent/US5705511A

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 17/06: Antipsoriatics
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 491/14: Ortho-condensed systems
- C07D 495/14: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed herein are compounds referred to as "fused pyrrolocarbazoles" which possess a variety of functional pharmacological activities including effect on the function and/or survival of trophic factor responsive cells; inhibition of enzymatic activity; inhibition of inflammation-associated responses; inhibition of cell growth associated with hyperproliferative states; and inhibition of developmentally programmed motoneuron death. The disclosed compounds are represented by the following general formula: ##STR1## Methodologies for the synthetic production of fused pyrrolocarbazoles are also disclosed, as well as exemplary uses of the compounds.

## Claims

### Claim 1

A fused pyrrolocarbazole defined by the formula: ##STR16## wherein: a) B and F, independently, and each together with the carbon atoms to which they are attached, form either
1) an unsaturated 6-membered carbocyclic aromatic ring in which from one to three carbon atom(s) may be replaced by nitrogen atom(s); or
2) an unsaturated 5-membered carbocyclic aromatic ring in which either
i) one carbon atom is replaced with an oxygen, nitrogen, or sulfur atom; or
ii) two carbon atoms are replaced with a sulfur and nitrogen atom, or an oxygen and nitrogen atom;
b) R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer selected from the group consisting of 1-4; and --OCH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 are each independently selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ; c) R.sup.2 is selected from the group consisting of H, --SO.sub.2 R.sup.9 ; --CO.sub.2 R.sup.9, --COR.sup.9, alkyl of 1-8 carbons, alkenyl of 2-8 carbons, alkynyl of 2-8 carbons, and a monosaccharide of 5-7 carbons wherein each hydroxyl group of said monosaccharide is independently selected from a group consisting of an unsubstituted hydroxyl group and a replacement moiety replacing said hydroxyl group, said replacement moiety 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 1-8carbons, alkenyl of 2-8 carbons, or alkynyl of 2-8 carbons is unsubstituted; or
2) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons, or alkynyl of 2-8 carbons is independently substituted with a moiety selected from the group consisting of 1-3 aryl of 6-10 carbons; phenyl, naphthyl; 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 selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons, and heteroaryl wherein y is an integer selected from the group consisting of 1 and 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.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, --PO(OR.sup.11).sub.2, and OR.sup.14 where R.sup.14 is the residue of an amino acid after the hydroxyl group of the carboxyl group is removed; and wherein either
i) R.sup.12 and R.sup.13 are each independently selected from the group consisting of H alkyl of 1-4 carbons, aryl of 6-10 carbons, and heteroaryl; or
ii) R.sup.12 and R.sup.13 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 ;
d) R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, aryl, 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 OH, --CH.sub.2 OR.sup.14, --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 wherein is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --CH.sub.2).sub.n S(O).sub.y R.sup.9, --CH.sub.2 SR.sup.15 where R.sup.15 is an 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 2-8 carbons; alkynyl of 2-8 carbons; wherein either
1) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons or alkynyl of 2-8 carbons is unsubstituted; or
2) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons or alkynyl of 2-8 carbons as defined in (c)(2), above;
e) X is selected from the group consisting of
1) an unsubstituted alkylene of 1-3 carbons; and
2) an alkylene of 1-3 carbons substituted by R.sup.2, OR.sup.10, --SR.sup.10, R.sup.15, where R.sup.15 is selected from the group consisting of an alkyl of 1-4 carbons; phenyl, naphthyl, arylalkyl of 7-14 carbons, and
3) --CH.dbd.CH--, --CH(OH)CH(OH)--, --O--, --S--, --S(.dbd.O )--, S(.dbd.O).sub.2 --, --C(.dbd.O)--, --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)--, --C(R.sup.10).sub.2 --, --C(.dbd.NOR.sup.11)CH(R.sup.15)--, --CH(R.sup.15)C(.dbd.NOR.sup.11)--, --CH.sub.2 Z--, --Z--CH.sub.2 --, --CH.sub.2 ZCH.sub.2 --, wherein Z is selected from the group consisting of C(R.sup.11)(OR.sup.11), O, S, C(.dbd.O), C(.dbd.NOR.sup.11), and NR.sup.11 ;
f) A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2 ; and a group wherein A.sup.1 and A.sup.2 together form a moiety selected from the group consisting of .dbd.O; .dbd.S; and .dbd.NR.sup.11, and
g) B.sup.1 and B.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --NCR.sup.11).sub.2 ; and a group wherein B.sup.1 and B.sup.2 are selected from the group consisting of .dbd.O, .dbd.S; and .dbd.NR.sup.11 with the proviso that at least one of the pairs A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O.

### Claim 2 (depends on 1)

The fused pyrrolocarbazole of claim 1 defined by the formula: ##STR17## wherein: a) R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl; --OR.sup.10, where R.sup.10 is selected from the group consisting of H, alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer selected from the group consisting of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 are each independently selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
b) R.sup.2 is selected from the group consisting of H, --SO.sub.2 R.sup.9 ; --CO.sub.2 R.sup.9, --COR.sup.9, alkyl of 1-8 carbons, alkenyl of 2-8 carbons, alkynyl of 2-8 carbons; and a monosaccharide of 5-7 carbons wherein each hydroxyl group of said monosaccharide is independently selected from the group consisting of an unsubstituted hydroxyl group and a replacement moiety replacing said hydroxyl group, said replacement moiety 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 2-8 carbons, or alkynyl of 2-8 carbons is unsubstituted; or
2) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons, or alkynyl of 2-8 carbons is independently substituted with a moiety selected from the group consisting of 1-3 aryl of 6-10 carbons, phenyl and naphthyl; 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 selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons, and heteroaryl wherein y is an integer selected from the group consisting of 1 and 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.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, --PO(OR.sup.11).sub.2, or OR.sup.14 where R.sup.14 is the residue of an amino acid after the hydroxyl group of the carboxyl group is removed; and wherein either
i) R.sup.12 and R.sup.13 are each independently selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons, and heteroaryl; or
ii) R.sup.12 and R.sup.13 are combined together to form a linking group of the general formula --(CH.sub.2).sub.2 --X.sub.1 --(CH.sub.2).sub.2 ;
c) R.sup.3, R.sup.4, R.sup.5 and R.sup.6, are each independently selected from the group consisting of H, aryl, 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 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer of 1-4, --CH.sub.2).sub.n S(O).sub.y R.sup.9, --CH.sub.2 SR.sup.15 where R.sup.15 is an 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 2-8 carbons; alkynyl of 2-8 carbons; wherein either
1) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons or alkynyl of 2-8 carbons is unsubstituted; or
2) each alkyl of 1-8 carbons, alkenyl of 2-8 carbons or alkynyl of 2-8 carbons is defined in (b)(2), above;
d) X is selected from the group consisting of
1) an unsubstituted alkylene of 1-3 carbons; and
2) an alkylene of 1-3 carbons substituted by R.sup.2, OR.sup.10, --SR.sup.10, R.sup.15, where R.sup.15 is selected from the group consisting of an alkyl of 1-4 carbons; phenyl, naphthyl, arylalkyl of 7-14 carbons; and
3) --CH.dbd.CH--, --CH(OH)CH(OH)--, --O--, --S--, --S(.dbd.O)--, --C(.dbd.O).sub.2 --, --C(.dbd.O)--, --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)--, --C(R.sup.10).sub.2 --, --C(.dbd.NOr.sup.11)CH(R.sup.15)--, --CH(R.sup.15)--, --CH(R.sup.15)C(.dbd.NOR.sup.11)--, --CH.sub.2 Z--, --Z--CH.sub.2 --, --CH.sub.2 ZCH.sub.2 --, wherein Z is selected from the group consisting of C(R.sup.11)(OR.sup.11), O, S, C(.dbd.O), C(.dbd.NOR.sup.11), and NR.sup.11 ;
e) A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2, and a group wherein A.sup.1 and A.sup.2 together form a moiety selected from the group consisting of .dbd.O; .dbd.S, and .dbd.NR.sup.11 ; and
f) B.sup.1 and B.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2 ; and a group wherein B.sup.1 and B.sup.2 together form a moiety selected from the group consisting of .dbd.O; .dbd.S, and .dbd.NR.sup.11 ; with the proviso that at least one of the pairs of A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O.

### Claim 3 (depends on 2)

The fused pyrrolocarbazole of claim 2 defined by a formula selected from the group consisting of: ##STR18## wherein: a) A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OH; and .dbd.O; and B.sup.1 and B.sup.2 are selected from the group consisting of H, H; H, --OH; and .dbd.O; provided that at least one of A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O;
b) R.sup.1 is H;
c) R.sup.2 is selected from the group consisting of H, allyl, hydroxyethyl, and alkyl of 1-4 carbons;
d) R.sup.3, R.sup.4, R.sup.5, and R.sup.6, are each independently selected from the group consisting of H, F, Cl, Br, I, alkyl of 1-4 carbons, alkoxyl of 1-4 carbons, heteroarylalkenyl, heteroarylalkyl, cyanoethyl, cyanovinyl, aryl of 6-10 carbons, alkynyl, arylalkenyl, alkoxycarbonylalkenyl, and haloalkenyl;
e) X is selected from the group consisting of
1) an unsubstituted alkylene of 1-3 carbons;
2) an alkylene of 1-3 carbons substituted by R.sup.2, --OR.sup.11, --SR.sup.11, R.sup.15 ; phenyl, naphthyl, arylalkyl of 7-11 carbons; and
3) --CH.dbd.CH--, --CH(OH)CH(OH)--, --O--, --S--, --S(.dbd.O)--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(=NOR.sup.11)--, --C(OR.sup.11)(R.sup.11)--, --X(.dbd.O)CH(R.sup.15)--, --CH(R.sup.15)C(.dbd.O)--, --C(R.sup.10).sub.2 --, --C(.dbd.NOR.sup.11)CH(R.sup.15)--, --CH(R.sup.15)C(.dbd.NOR.sup.11)--, --CH.sub.2 Z--, --Z--CH.sub.2 --, --CH.sub.2 ZCH.sub.2 --, where Z is selected from the group consisting of C(R.sup.11)(OR.sup.11), O, S, C(.dbd.O), C(.dbd.NOR.sup.11), and NR.sup.11.

### Claim 4 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein:
a) A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OH; and .dbd.O; and B.sup.1 and B.sup.2 are selected from the group consisting of H, H; H, --OH; and O; provided that at least one of A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O;
b) R.sup.1 is H;
c) R.sup.2 is selected frown the group consisting of H, CH.sub.3, CH.sub.2 CH.dbd.CH.sub.2, and CH.sub.2 CH.sub.2 OH;
d) each R.sup.3, R.sup.4, R.sup.5, and R.sup.6, independently, is selected from the group consisting of H, F, Cl, Br, I, CH.sub.3, OCH.sub.3, HC.dbd.CHC.sub.6 H.sub.5, HC.dbd.CHCO.sub.2 H.sub.5, C.sub.6 H.sub.5, HC.dbd.CH-2-pyr, HC.dbd.CH-4-pyr, H.sub.2 CCH.sub.2 -2-pyr, HC.dbd.CHCN, C.dbd.CH, n-pentyl, HC.dbd.CH-2-phthalimide, and HC.dbd.CHI; and
e) X is selected from the group consisting of --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --S--, --O--, and --C(.dbd.O)--.

### Claim 5 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 6 (depends on 1)

The fused pyrrolocarbazole of claim 1, wherein R.sup.2 is selected from the group consisting of H, --SO.sub.2 R.sup.9 ; --CO.sub.2 R.sup.9, --COR.sup.9, alkyl of 1-4carbons, alkenyl of 2-4 carbons, alkynyl of 2-4 carbons, and a monosaccharide of 5-7 carbons wherein each hydroxyl group of said monosaccharide is independently selected from a group consisting of an unsubstituted hydroxyl group and a replacement moiety replacing said hydroxyl group, said replacement moiety selected from the group consisting of H, alkyl of 1-4 carbons, alkylcarbonyloxy of 2-5 carbons and alkoxy of 1-4 carbons.

### Claim 7 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein R.sup.2 is selected from the group consisting of alkyl of 1-8 carbons, alkenyl of 2-8 carbons, and alkynyl of 2-8 carbons is independently substituted with a moiety selected from the group consisting of phenyl and naphthyl.

### Claim 8 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein R.sup.2 is selected from the group consisting of alkyl of 1-8 carbons, alkenyl of 2-8 carbons, and alkynyl of 2-8 carbons is independently substituted with a moiety consisting of --S(O).sub.y R.sup.11, where R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 9 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, aryl, heteroaryl; F, Cl, Br, I, --CN, CF.sub.3, --NO.sub.2, OH, --OR.sup.9, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, --OCOR.sup.9, --OCONHR.sup.9, NH.sub.2, --CH.sub.2 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 1-4 carbons, alkenyl of 2-4 carbons; alkynyl of 2-4 carbons.

### Claim 10 (depends on 9)

The fused pyrrolocarbazole of claim 9, wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently 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 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 2-8 carbons; alkynyl of 2-8 carbons.

### Claim 11 (depends on 9)

The fused pyrrolocarbazole of claim 9 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, phenyl, naphthyl, 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 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 2-8 carbons; and alkynyl of 2-8 carbons.

### Claim 12 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein R.sup.12 and R.sup.13 are each independently selected from the group consisting of phenyl and naphthyl.

### Claim 13 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein X is selected from the group consisting of an alkylene of 1-3 carbons substituted by R.sup.2 group, --SR.sup.10, R.sup.15, where R.sup.15 is selected from the group consisting of an alkyl of 1-4 carbons; phenyl, naphthyl, and benzyl.

### Claim 14 (depends on 1)

The fused pyrrolocarbazole of claim 1 wherein X is an alkylene of 1-3 carbons substituted by OR.sup.10.

### Claim 15 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 16 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein R.sup.2 is selected from the group consisting of H, --SO.sub.2 R.sup.9, --CO.sub.2 R.sup.9, --COR.sup.9, alkyl of 1-4 carbons, alkenyl of 2-4 carbons, alkynyl of 2-4 carbons, and a monosaccharide of 5-7 carbons wherein each hydroxyl group of said monosaccharide is independently selected from a group consisting of an unsubstituted hydroxyl group and a replacement moiety replacing said hydroxyl group, said replacement moiety selected from the group consisting of H, alkyl of 1-4 carbons, alkylcarbonyloxy of 2-5 carbons and alkoxy of 1-4 carbons.

### Claim 17 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein R.sup.2 is selected from the group consisting of alkyl of 1-8 carbons, alkenyl of 2-8 carbons, and alkynyl of 2-8 carbons is independently substituted with a moiety selected from the group consisting of phenyl and naphthyl.

### Claim 18 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein R.sup.2 is selected from the group consisting of alkyl of 1-8 carbons, alkenyl of 2-8 carbons, and alkynyl of 2-8 carbons is independently substituted with a moiety consisting of --S(O).sub.y R.sup.11, where R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 19 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, aryl, heteroaryl; F, Cl, Br, I, --CN, CF.sub.3, --NO.sub.2, OH, --OR.sup.9, --OCH.sub.2).sub.n NR.sup.7 R.sup.8, --OCOR.sup.9, --OCONHR.sup.9, NH.sub.2, --CH.sub.2 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 1-4 carbons, alkenyl of 2-4 carbons; and alkynyl of 2-4 carbons.

### Claim 20 (depends on 19)

The fused pyrrolocarbazole of claim 19 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently 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 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 2-8 carbons; and alkynyl of 2-8 carbons.

### Claim 21 (depends on 19)

The fused pyrrolocarbazole of claim 19 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, phenyl, naphthyl, 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 OH, --CH.sub.2 OR.sup.14, --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 wherein y is an integer selected from the group consisting of 1 and 2; --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, wherein n is an integer selected from the group consisting of 1-4, --(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 2-8 carbons; and alkynyl of 2-8 carbons.

### Claim 22 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein R.sup.12 and R.sup.13 are each independently selected from the group consisting of phenyl and naphthyl.

### Claim 23 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein X is selected from the group consisting of an alkylene of 1-3 carbons substituted by R.sup.2, --SR.sup.10, and R.sup.15, where R.sup.15 is selected from the group consisting of an alkyl of 1-4 carbons; phenyl, naphthyl, and benzyl.

### Claim 24 (depends on 2)

The fused pyrrolocarbazole of claim 2 wherein X is an alkylene of 1-3 carbons substituted by OR.sup.10.

### Claim 25 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein R.sup.2 is methyl.

### Claim 26 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from the group consisting of H, F, Cl, Br, I, methyl, methoxyl, pyridylyinyl, pyridylethyl, cyanoethyl, cyanovinyl, phenyl, alkynyl, styryl, ethoxycarbonylvinyl and haloalkenyl.

### Claim 27 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein X is an unsubstituted alkylene selected from the group consisting of --CH.sub.2 and --CH.sub.2 CH.sub.2.

### Claim 28 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein X is an alkylene selected from the group consisting of substituted --CH.sub.2 and --CH.sub.2 CH.sub.2 wherein each alkylene of 1-3 carbons is substituted with one R.sup.2 or OR.sup.11 group.

### Claim 29 (depends on 28)

The fused pyrrolocarbazole of claim 28 wherein the substituent is OR.sup.11.

### Claim 30 (depends on 3)

The fused pyrrolocarbazole of claim 3 wherein X is selected from the group consisting of an alkylene of 1-3 carbons substituted by R.sup.2, --SR.sup.10, and R.sup.15, where R.sup.15 is selected from the group consisting of an alkyl of 1-4 carbons; phenyl, naphthyl, and benzyl.

### Claim 31

A method for preparing a D-ring-fused pyrrolocarbazole, the method comprising the steps of:
a) obtaining an indole defined by Formula IV: ##STR19## wherein: R.sup.2 is selected from the group consisting of H, SO.sub.2 R.sup.9, CO.sub.2 R.sup.9, and alkyl of 1-4 carbons;
R.sup.3a and R.sup.4a are each independently selected from the group consisting of H, F, Cl, Br, I, --OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.7 R.sup.8, --SR.sup.11, where R.sup.11 is selected from the group consisting of H, aklyl of 1-4 carbons, aryl of 6-10 carbons and heteroaryl; alkyl, aryl, heteroaryl, --(CH.sub.2).sub.n S, --(CH.sub.2).sub.n OR.sup.9, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ;
b) reacting said indole with a 2-indanone defined by the general formula: ##STR20## wherein: R.sup.5a and R.sup.6a are each independently selected from the group consisting of H, F, CI, Br, I, alkyl, aryl, heteroaryl, CN, NO.sub.2, OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, CO.sub.2 R.sup.9, SO.sub.2 R.sup.9, SR.sup.11, --(CH.sub.2).sub.n S(O).sub.y R.sup.9, wherein y is an integer selected from the group consisting of 1 and 2; --(CH.sub.2).sub.n SR.sup.11, NR.sup.7 R.sup.8, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8, and X is selected from the group consisting of an alkylene group of 1-3 carbons and --C(R.sup.10).sub.2 --;
under conditions capable of forming a 2-(2-cycloalkenyl)indolo tertiary alcohol defined by Formula V: ##STR21## c) eliminating the hydroxyl group of the alcohol of said Formula V to form a 2-(2-cycloalkenyl)indole defined by Formula VI: ##STR22## d) reacting said Formula VI with an imide defined by the general formula: ##STR23## wherein: R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 independently are selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
under conditions which form a tetrahydropyrrolocarbazole defined by Formula VII: ##STR24## and e) dehydrogenating the tetrahydrocarbazole ring of said Formula VII under conditions which form a fused pyrrolocarbazole defined by Formula VIII. ##STR25## wherein: R.sup.2, R.sup.3a and R.sup.4a are as defined in (a) above; R.sup.5a, R.sup.6a and X are as defined in (b) above; and R.sup.1 is defined as in (d) above.

### Claim 32

A method for making regiospecific D-ring-fused pyrrolocarbazole lactam isomers, said method comprising the steps of:
a) obtaining a fused pyrrolocarbazole defined by Formula VIII: ##STR26## wherein: R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 independently are selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
R.sup.2 is selected from the group consisting of H, SO.sub.2 R.sup.9, CO.sub.2 R.sup.9, and alkyl of 1-4 carbons;
R.sup.3a and R.sup.4a are each independently selected from the group consisting of H, F, Cl, Br, I, --OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.7 R.sup.8, --SR.sup.11, where R.sup.11 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl of6-10 carbons and heteroaryl; alkyl, aryl, heteroaryl, --(CH.sub.2).sub.n SR.sup.11, --(CH.sub.2).sub.n OR.sup.9, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; R.sup.5a and R.sup.6a are each independently selected from the group consisting of H, F, Cl, Br, I, alkyl, aryl, heteroaryl, CN, NO.sub.2, OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, CO.sub.2 R.sup.9, SO.sub.2 R.sup.9, SR.sup.11, --(CH.sub.2).sub.n S(O).sub.y R.sup.9, wherein y is an integer selected from the group consisting of 1 and 2; --(CH.sub.2).sub.n SR.sup.11, NR.sup.7 R.sup.8, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8, and X is selected from the group consisting of an alkylene group of 1-3 carbons and --C(R.sup.10).sub.2 --;
b) reducing the imide group of said fused pyrrolocarbazole under conditions which form fused pyrrolocarbazole lactam isomers defined by Formula IX and Formula X: ##STR27## wherein: R.sup.1 is defined in (a) above; and
R.sup.2, R.sup.3a, R.sup.4a R.sup.5a, R.sup.6a and X are as defined in (a)(2) above; and
c) separating the isomer of Formula IX from the isomer of Formula X under conditions which produce substantially pure regiospecific D-ring-fused pyrrolocarbazole lactam isomers.

### Claim 33

A method of making regiospecific D-ring fused pyrrolocarbazole lactam isomer, said method comprising the steps of:
a) obtaining a compound defined by Formula XI: ##STR28## wherein: R.sup.2 is selected from the group consisting of H, SO.sub.2 R.sup.9, CO.sub.2 R.sup.9, and alkyl of 1-4 carbons;
R.sup.3a and R.sup.4a are each independently selected from the group consisting of H, F, Cl, Br, I, --OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.7 R.sup.8, --SR.sup.11, where R.sup.11 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons and heteroaryl; alkyl, aryl, heteroaryl, --(CH.sub.2).sub.n SR.sup.11, --(CH.sub.2).sub.n OR.sup.9, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; R.sup.5a and R.sup.6a are each independently selected from the group consisting of H, F, Cl, Br, I, alkyl, aryl, heteroaryl, CN, NO.sub.2, OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, CO.sub.2 R.sup.9, SO.sub.2 R.sup.9, SR.sup.11, --CH.sub.2).sub.n S(O).sub.y R.sup.9, wherein y is an integer selected from the group consisting of 1 and 2; --(CH.sub.2).sub.n SR.sup.11, NR.sup.7 R.sup.8, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8, and X is selected from the group consisting of S, O, CO, alkylene of 1-3 carbons, --C(R.sup.10).sub.2 --, --CH.sub.2 Z--, where Z is selected from the group consisting of C(R.sup.11)(OR.sup.11), O, S, C(.dbd.NOR.sup.11), and NR.sup.11 ; --ZCH.sub.2 --, and --CH.sub.2 ZCH.sub.2 --;
b) reacting said Formula XI with a lower alkyl .beta.-cyanoacrylate under conditions which form regiospecific tetrahydrocarbazole cyano-ester isomers defined by Formula XII and Formula XV: ##STR29## wherein R is a lower alkyl group; c) separating the isomer of Formula XII from the isomer of Formula XV under conditions which produce substantially pure regiospecific tetrahydrocarbazole cyano-ester isomers;
d) (1) dehydrogenating the tetrahydrocarbazole ring of the isomer of Formula XII sufficient to form a carbazole cyano-ester defined by Formula XIII: ##STR30## and (2) dehydrogenating the tetrahydrocarbazole ring of the isomer of Formula XV sufficient to form a carbazole cyano-ester defined by Formula XVI: ##STR31## and e) (1) reacting the carbazole cyano-ester of Formula XIII under reductive conditions which produce regiospecific fused pyrrolocarbazoles defined by Formula XIV: ##STR32## wherein: R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 independently are selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
R.sup.2, R.sup.3a, R.sup.4a R.sup.5a, R.sup.6a and X are as defined in (a) above; and
(2) reacting the carbazole cyano-ester of Formula XVI under reductive conditions which produce regiospecific fused pyrrolocarbazoles defined by Formula XVII: ##STR33## wherein: R.sup.1 is defined as in (e)(1) above; R.sup.2, R.sup.3a, R.sup.4a R.sup.5a, R.sup.6a and X are as defined in (a) above.

### Claim 34

A method of making a D-ring-fused pyrrolocarbazole, said method comprising the steps of:
a) obtaining an indole defined by Formula IV: ##STR34## wherein: R.sup.2 is selected from the group consisting of H, SO.sub.2 R.sup.9, CO.sub.2 R.sup.9, and alkyl of 1-4 carbons;
R.sup.3a and R.sup.4a are each independently selected from the group consisting of H, F, Cl, Br, I, --OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.7 R.sup.8, --SR.sup.11, where R.sup.11 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons and heteroaryl; alkyl, aryl, heteroaryl, --(CH.sub.2).sub.n SR.sup.11, --(CH.sub.2).sub.n OR.sup.9, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ;
b) reacting said indole with a 2-benzocycloalkanone defined by the general formula: ##STR35## wherein: R.sup.5a and R.sup.6a are each independently selected from the group consisting of H, F, Cl, Br, I, alkyl, aryl, heteroaryl, CN, NO.sub.2, OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, CO.sub.2 R.sup.9, SO.sub.2 R.sup.9, SR.sup.11, --(CH.sub.2).sub.n S(O).sub.y R.sup.9, where y is an integer selected from the group consisting of 1 and 2; --(CH.sub.2).sub.n SR.sup.11, NR.sup.7 R.sup.8, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8, and X is an alkylene 2-3 carbons;
under conditions which form Formula V: ##STR36## c) eliminating the hydroxyl group to form the corresponding Formula VI; ##STR37## d) reacting said Formula VI with an imide defined by the general formula: ##STR38## wherein: R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 independently are selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
under conditions which form a tetrahydroarylalkylpyrrolocarbazole defined by Formula XVIII: ##STR39## and e) (1) dehydrogenating the D-ring of said pyrrolocarbazole under conditions which produce a fused pyrrolocarbazole defined by Formula XIX: ##STR40## i) wherein A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2 ; and a group wherein A.sup.1 and A.sup.2 together form a moiety selected from the group consisting of .dbd.O; .dbd.S; and .dbd.NR.sup.11 ; and
ii) B.sup.1 and B.sup.2 are selected from the group consisting of: H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2 ; and a group wherein B.sup.1 and B.sup.2 are selected from the group consisting of .dbd.O, .dbd.S; and .dbd.NR.sup.11 with the proviso that at least one of the pairs A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O; and
iii) R.sup.1 is defined in (d) above; R.sup.2, R.sup.3a, R.sup.4a are as defined in (a) above; R.sup.5a, R.sup.6a and X are as defined in (b) above; and
e) (2) dehydrogenating the E-ring of said pyrrolocarbazote under conditions which produce a fused pyrrolocarbazole defined by Formula XX: ##STR41## i) wherein A.sup.1 and A.sup.2 are selected from the group consisting of H, H; H, --OR.sup.11 ; H, --SR.sup.11 ; H, --N(R.sup.11).sub.2 ; and a group wherein A.sup.1 and A.sup.2 together form a moiety selected from the group consisting of .dbd.O; .dbd.S; and .dbd.NR.sup.11 ; and
ii) B.sup.1 and B.sup.2 are selected from the group consisting of: H, H; H, --OR.sup.11 ; H, --SR.sup.1 ; H, --N(R.sup.11).sub.2 ; and a group wherein B.sup.1 and B.sup.2 are selected from the group consisting of .dbd.O, .dbd.S; and .dbd.NR.sup.11 with the proviso that at least one of the pairs A.sup.1, A.sup.2 or B.sup.1, B.sup.2 is .dbd.O; and
iii) R.sup.1 is defined in (d) above; R.sup.2, R.sup.3a, R.sup.4a are as defined in (a) above; and R.sup.5a, R.sup.6a and X are as defined in (b) above.

### Claim 35

A method of making a D-ring-fused pyrrolocarbazole, said method comprising the steps of:
a) obtaining a lower alkyl stannylindole defined by Formula XXI: ##STR42## wherein: R.sup.2 is selected from the group consisting of --CO.sub.2 H, --SO.sub.2 R.sup.9, --CO.sub.2 R.sup.9 and alkyl;
R.sup.3a and R.sup.4a are each independently selected from the group consisting of H, F, Cl, Br, I, --OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, NR.sup.7 R.sup.8, --SR.sup.11, where R.sup.11 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl of 6-10 carbons and heteroaryl; alkyl, aryl, heteroaryl, --(CH.sub.2).sub.n SR.sup.11, --(CH.sub.2).sub.n OR.sup.9, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ;
b) coupling said Formula XXI with a compound defined by the general formula: ##STR43## wherein: R.sup.5a and R.sup.6a are each independently selected from the group consisting of H, F, Cl, Br, I, alkyl, aryl, heteroaryl, CN, NO.sub.2, OR.sup.9, --O(CH.sub.2).sub.n NR.sup.7 R.sup.8, CO.sub.2 R.sup.9, SO.sub.2 R.sup.9, SR.sup.11, --(CH.sub.2).sub.n S(O).sub.y R.sup.9, where y is an integer selected from the group consisting of 1 and 2; --(CH.sub.2).sub.n SR.sup.11, NR.sup.7 R.sup.8, and --(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; X is selected from the group consisting of S, O, CO, alkylene of 1-3 carbons, --C(R.sup.10).sub.2 --, --CH.sub.2 Z--, where Z is selected from the group consisting of C(R.sup.11)(OR.sup.11), O, S, C(.dbd.NOR.sup.11), and NR.sup.11 ; --ZCH.sub.2, and CH.sub.2 ZCH.sub.2 --; and Y is Br, I, or --OSO.sub.2 CF.sub.3 ;
under conditions which form an indole defined by Formula XXII: ##STR44## c) separately reacting said Formula XXII with either: i) an imide defined by the general formula: ##STR45## or ii) a lower alkyl .beta.-cyanoacrylate;
each independently under conditions which form an indolo-imide defined by Formula XXIII: ##STR46## and d) cyclizing said Formula XXIII under conditions which form a fused pyrrolocarbazole defined by Formula XXIV: ##STR47## wherein: R.sup.1 is selected from the group consisting of H, alkyl of 1-4 carbons, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; COR.sup.9, where R.sup.9 is selected from the group consisting of alkyl of 1-4 carbons, and aryl, --OR.sup.10, where R.sup.10 is selected from the group consisting of H and alkyl of 1-4 carbons; --CONH.sub.2, --NR.sup.7 R.sup.8, --(CH.sub.2).sub.n NR.sup.7 R.sup.8, wherein n is an integer selected from the group consisting of 1-4; and --O(CH.sub.2).sub.n NR.sup.7 R.sup.8 ; wherein either
1) R.sup.7 and R.sup.8 independently are selected from the group consisting of H and 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 is selected from the group consisting of O, S and CH.sub.2 ;
R.sup.2, R.sup.3a, R.sup.4a are as defined in (a) above; and R.sup.5a, R.sup.6a and X are as defined in (b) above.

### Claim 36 (depends on 31)

The process of claim 31 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 37 (depends on 31)

The process of claim 31 wherein R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 38 (depends on 32)

The process of claim 32 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 39 (depends on 32)

The process of claim 32 wherein R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 40 (depends on 33)

The process of claim 33 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 41 (depends on 33)

The process of claim 33 wherein R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 42 (depends on 33)

The process of claim 33 wherein the lower alkyl .beta.-cyanoacrylate is ethyl-.beta.-cyanoacrylate.

### Claim 43 (depends on 34)

The process of claim 34 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 44 (depends on 34)

The process of claim 34 wherein R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 45 (depends on 35)

The process of claim 35 wherein R.sup.9 is selected from the group consisting of phenyl and naphthyl.

### Claim 46 (depends on 35)

The process of claim 35 wherein R.sup.11 is selected from the group consisting of phenyl and naphthyl.

### Claim 47 (depends on 1)

A method for effecting the function and/or survival of a trophic factor responsive cell comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 1.

### Claim 48 (depends on 2)

A method for effecting the function and/or survival of a trophic factor responsive cell comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 2.

### Claim 49 (depends on 3)

A method for effecting the function and/or survival of a trophic factor responsive cell comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 3.

### Claim 50 (depends on 4)

A method for effecting the function and/or survival of a trophic factor responsive cell comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 4.

### Claim 51 (depends on 47)

The method of claim 47 wherein said effecting is in the form of enhancement.

### Claim 52 (depends on 47)

The method of claim 47 wherein said effecting is in the form of inhibition.

### Claim 53 (depends on 47)

The method of claim 47 wherein said trophic factor responsive cell is a neuron.

### Claim 54 (depends on 53)

The method of claim 53 wherein said neuron is selected from the group comprising cholinergic neurons and sensory neurons.

### Claim 55 (depends on 1)

A method for inhibiting the kinase activity of a protein kinase, said method comprising contacting said protein kinase with at least one fused pyrrolocarbazole of claim 1.

### Claim 56 (depends on 2)

A method for inhibiting the kinase activity of a protein kinase, said method comprising contacting said protein kinase with at least one fused pyrrolocarbazole of claim 2.

### Claim 57 (depends on 3)

A method for inhibiting the kinase activity of a protein kinase, said method comprising contacting said protein kinase with at least one fused pyrrolocarbazole of claim 3.

### Claim 58 (depends on 4)

A method for inhibiting the kinase activity of a protein kinase, said method comprising contacting said protein kinase with at least one fused pyrrolocarbazole of claim 4.

### Claim 59 (depends on 55)

The method of claim 55 wherein said protein kinase is selected from the group consisting of protein kinase C and trk tyrosine kinase.

### Claim 60 (depends on 1)

A method for inhibiting the induction by interferon-.gamma. of indoleamine 2,3-dioxygenase comprising the step of contacting cells which transcribe interferon-.gamma. specific genes with at least one fused pyrrolocarbazole of claim 1.

### Claim 61 (depends on 2)

A method for inhibiting the induction by interferon-.gamma. of indoleamine 2,3-dioxygenase comprising the step of contacting cells which transcribe interferon-.gamma. specific genes with at least one fused pyrrolocarbazole of claim 2.

### Claim 62 (depends on 3)

A method for inhibiting the induction by interferon-.gamma. of indoleamine 2,3-dioxygenase comprising the step of contacting cells which transcribe interferon-.gamma. specific genes with at least one fused pyrrolocarbazole of claim 3.

### Claim 63 (depends on 4)

A method for inhibiting the induction by interferon-.gamma. of indoleamine 2,3-dioxygenase comprising the step of contacting cells which transcribe interferon-.gamma. specific genes with at least one fused pyrrolocarbazole of claim 4.

### Claim 64 (depends on 1)

A method for enhancing the survival of a cell at risk of dying comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 1.

### Claim 65 (depends on 2)

A method for enhancing the survival of a cell at risk of dying comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 2.

### Claim 66 (depends on 3)

A method for enhancing the survival of a cell at risk of dying comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 3.

### Claim 67 (depends on 4)

A method for enhancing the survival of a cell at risk of dying comprising the step of contacting said cell with at least one fused pyrrolocarbazole of claim 4.

### Claim 68 (depends on 64)

The method of claim 64 wherein said cell is at risk of dying due to a process selected from the group consisting of aging, trauma, and disease.

### Claim 69 (depends on 68)

The method of claim 68 wherein said cell is a neuron.