IP Library › Granted Patent US 7,662,831

Granted Patent B2

US 7,662,831 · App. 11/828,525 · Granted Feb 16, 2010

Tetracyclic indoles as potassium channel modulators

Assignee: Wyeth LLC

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Patent No.: US 7,662,831
App. No.: 11/828,525
Granted: Feb 16, 2010
Kind: B2

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Abstract

The present invention is directed to compounds of Formula I: that are potassium channel modulators and pharmaceutical compositions thereof. The present invention is further directed to methods of treatment using the compounds and pharmaceutical compositions of the invention. The present invention is still further directed to synthetic processes for producing the compounds of the invention.

Claims (216)

1. A compound of Formula I:

or pharmaceutically acceptable salt thereof; wherein:

R 1 is H, amino, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, C 1-12 haloalkoxy, C 1-12 alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, —OR 2 , —SR 2 , or —NR 3 R 4 ; wherein said C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, C 1-12 haloalkoxy, C 1-12 alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups;

L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl,arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups;

L 2 is a C 2-5 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , OC(O)R v , OC(O)NR y R z , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, or heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 7 groups;

each R 2 , R 3 , and R 4 is, independently, H, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3, or 4 R 8 groups;

each R 5 or R 8 is, independently, OR a , SR a , C(O)R b , C(O)NR e R f , C(O)OR b , OC(O)R b , OC(O)NR e R f , NR e R f , NR c C(O)R d , NR c C(O)OR d , NR c C(O)NR d , S(O)R b , S(O)NR e R f , S(O) 2 R b , NR c S(O) 2 R d , NR b S(O) 2 NR e R f , C(═NR a )R b , C(═NR a )NR b , C(═NR a )OR b , OC(═NR a )R b , OC(═NR a )NR b , NR c C(═NR a )R d , NR c C(═NR a )OR d , NR c C(═NR a )NR d , halogen, cyano, nitro, hydroxyl, carboxy, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3 or 4 R 9 groups;

each R 9 is, independently, OR a′ , SR a′ , C(O)R b′ , C(O)NR e′ R f′ , C(O)OR b′ , OC(O)R b′ , OC(O)NR e′ R f′ , NR e′ R f′ , NR c′ C(O)R d′ , NR c′ C(O)OR d′ , NR c′ C(O)NR d′ , S(O)R b′ , S(O)NR e′ R f′ , S(O) 2 R b′ , NR c′ S(O) 2 R d′ , NR b S(O) 2 NR e′ R f′ , halogen, cyano, nitro, hydroxyl, carboxy, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylalkyloxy, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkyloxy, heterocycloalkylalkyloxy, aryl, arylalkyl, aryloxy, arylalkyloxy, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, amino, alkylamino, dialkylamino, acyl, formyl, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, dialkylcarbamyloxy, acyloxy, carboxy, alkylsulfonyl, alkylsulfinyl, thio, or alkylthio;

each R 6 is, independently, OR o′ , SR o′ , C(O)R p′ , C(O)NR s′ R t′ , C(O)OR p′ , OC(O)R p′ , OC(O)NR s′ R t′ , NR s′ R t′ , NR q′ C(O)R r′ , NR q′ C(O)OR r′ , NR q′ C(O)NR r′ , S(O)R p′ , S(O)NR s′ R t′ , S(O) 2 R p′ , NR q′ S(O) 2 R r′ , NR p′ S(O) 2 NR s′ R t′ , halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

each R 7 is, independently, OR u′ , SR u′ , C(O)R v′ , C(O)NR y′ R z′ , C(O)OR v′ , OC(O)R v′ , OC(O)NR y′ R z′ , NR y′ R z′ , NR w′ C(O)R x′ , NR w′ C(O)OR x′ , NR w′ C(O)NR x′ , S(O)R v′ , S(O)NR y′ R z′ , S(O) 2 R v′ , NR w′ S(O) 2 R x′ , NR v S(O) 2 NR y′ R z′ , halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

each R a , R b , R c , R d , R e , or R f is, independently, H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted with 1, 2, or 3 R g groups;

or any R c and R d , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring, wherein said heterocycloalkyl ring is optionally substituted with 1, 2, or 3 R g′ groups;

or any R e and R f , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring, wherein said heterocycloalkyl or heteroaryl ring is optionally substituted with 1, 2, or 3 R g ″groups;

each R g , R g′ , or R g ″ is, independently, halogen, cyano, nitro, hydroxyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylalkyloxy, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkyloxy, heterocycloalkylalkyloxy, aryl, arylalkyl, aryloxy, arylalkyloxy, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, amino, alkylamino, dialkylamino, acyl, formyl, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, dialkylcarbamyloxy, acyloxy, carboxy, alkylsulfonyl, alkylsulfinyl, thio, or alkylthio;

each R a′ , R b′ , R c′ , R d′ , R e′ , or R f′ is, independently, H, C 1-6 alkyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl,

or any R c′ and R d′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R e′ and R f′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

each R o R p , R q , R r , R s , R t , R u , R v , R y , or R z , is, independently, H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted with 1, 2, or 3 groups independently selected from halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, amino, alkylamino, dialkylamino, acyl, formyl, acyloxy, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, and dialkylcarbamyloxy;

or any R q and R r , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R s and R t , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R w and R x , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R y and R z , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring; and

each R o′ , R p′ , R q′ , R r′ , R s′ , R t′ , R u′ , R v′ , R y′ , or R z′ , is, independently, H, C 1-6 alkyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

or any R q′ and R r′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocyclic ring;

or any R s′ and R t′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R w′ and R x′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R y′ and R z′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

provided that the compound is not N-(4-oxo-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl)-acetamide, or pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein R 1 is H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, or heteroarylalkynyl, wherein said C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups.

3. The compound of claim 1 wherein R 1 is H, C 1-12 alkyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, wherein said C 1-12 alkyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups.

4. The compound of claim 1 wherein R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, wherein said C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups.

5. The compound of claim 1 wherein R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, or heteroaryl, wherein said C 1-12 alkyl, C 2-12 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, and heteroaryl are each optionally substituted by 1, 2, 3, or 4 R 5 groups.

6. The compound of claim 1 wherein R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, or heteroaryl.

7. The compound of claim 1 wherein R 1 is methyl, ethyl, n-butyl, isobutyl, tert-butyl, neopentyl, n-pentyl, n-hexyl, cyclohexyl, cyclopentylethyl, benzyl, phenylethyl, or thiophen-2-yl.

8. The compound of claim 1 wherein L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups.

9. The compound of claim 1 wherein L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 6 groups.

10. The compound of claim 1 wherein L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , C(O)R p , NR s R t , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; wherein said C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 6 groups.

11. The compound of claim 1 wherein L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , C(O)R p , NR s R t , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl.

12. The compound of claim 1 wherein L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 oxo groups.

13. The compound of claim 1 wherein L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1 oxo group.

14. The compound of claim 1 wherein L 2 is a C 2-5 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , OC(O)R v , OC(O)NR y R z , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 7 groups.

15. The compound of claim 1 wherein L 2 is a C 2-3 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 7 groups.

16. The compound of claim 1 wherein L 2 is a C 2-3 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , C(O)R v , NR y R z , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl, are each optionally substituted by 1, 2, or 3 R 7 groups.

17. The compound of claim 1 wherein L 2 is a C 2-3 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , C(O)R v , NR y R z , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl.

18. The compound of claim 1 wherein L 2 is an unsubstituted C 2-3 alkylene bridge.

19. The compound of claim 1 wherein:

L 1 is an unsubstituted C 6 alkylene bridge; and

L 2 is an unsubstituted C 2 alkylene bridge.

20. The compound of claim 1 wherein:

L 1 is an unsubstituted C 5 alkylene bridge; and

L 2 is an unsubstituted C 3 alkylene bridge.

21. The compound of claim 1 wherein:

L 1 is a C 5 alkylene bridge substituted with 1 oxo group; and

L 2 is an unsubstituted C 3 alkylene bridge.

22. The compound of claim 1 wherein:

L 1 is an unsubstituted C 5 alkylene bridge; and

L 2 is an unsubstituted C 2 alkylene bridge.

23. The compound of claim 1 wherein:

L 1 is an unsubstituted C 4 alkylene bridge; and

L 2 is an unsubstituted C 3 alkylene bridge.

24. The compound of claim 1 wherein:

R 1 is H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, or heteroarylalkynyl, wherein said C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl is optionally substituted by 1, 2, 3, or 4 R 5 groups;

L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups; and

L 2 is a C 2-5 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , OC(O)R v , OC(O)NR y R z , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 7 groups.

25. The compound of claim 1 wherein:

R 1 is H, C 1-12 alkyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, wherein said C 1-12 alkyl, C 1-12 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups;

L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups; and

L 2 is a C 2-5 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , OC(O)R v , OC(O)NR y R z , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 7 groups.

26. The compound of claim 1 wherein:

L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 6 groups; and

L 2 is a C 2-3 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , SR u , C(O)R v , C(O)NR y R z , C(O)OR v , NR y R z , NR w C(O)R x , NR w C(O)OR x , NR w C(O)NR x , S(O)R v , S(O)NR y R z , S(O) 2 R v , NR w S(O) 2 R x , NR v S(O) 2 NR y R z , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 7 groups.

27. The compound of claim 1 wherein:

R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, wherein said C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, 3, or 4 R 5 groups;

L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , C(O)R p , NR s R t , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted by 1, 2, or 3 R 6 groups; and

L 2 is a C 2-3 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR u , C(O)R v , NR y R z , oxo, halogen, amino, C 1-6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl, are each optionally substituted by 1, 2, or 3 R 7 groups.

28. The compound of claim 1 wherein:

R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, or heteroaryl, wherein said C 1-12 alkyl, C 2-12 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, and heteroaryl are each optionally substituted by 1, 2, 3, or 4 R 5 groups;

29. The compound of claim 1 wherein:

R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, or heteroaryl, wherein said C 1-12 alkyl, C 2-12 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, and heteroaryl are optionally substituted by 1, 2, 3, or 4 R 5 groups;

L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1 oxo group; and

L 2 is an unsubstituted C 2-3 alkylene bridge.

30. The compound of claim 1 wherein:

R 1 is C 1-12 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, arylalkyl, or heteroaryl;

L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1 oxo group; and

L 2 is an unsubstituted C 2-3 alkylene bridge.

31. The compound of claim 1 wherein:

R 1 is methyl, ethyl, n-butyl, isobutyl, tert-butyl, neopentyl, n-pentyl, n-hexyl, cyclohexyl, cyclopentylethyl, benzyl, phenylethyl, or thiophen-2-yl;

L 1 is a C 4-6 alkylene bridge which is optionally substituted with 1 oxo group; and

L 2 is an unsubstituted C 2-3 alkylene bridge.

32. The compound of claim 1 wherein said compound is:

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-3,3-dimethylbutanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-2,2-dimethylpropanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylhexanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-3-phenylpropanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylthiophene-2-carboxamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-3-methylbutanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylpropanamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylcyclohexanecarboxamide;

N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylpentanamide;

N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-yl-3,3-dimethylbutanamide;

N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylacetamide;

N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylpentanamide;

N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-yl-2-phenylacetamide;

N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-yl-3-methylbutanamide;

3-cyclopentyl-N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylpropanamide;

N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl-3,3-dimethylbutanamide;

N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-ylhexanamide;

N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl-3-methylbutanamide;

N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-ylacetamide;

N-4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-ylhexanamide;

3,3-dimethyl-N-4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-ylbutanamide;

N-4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-ylheptanamide; or

3,3-dimethyl-N-(8-oxo-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl)butanamide;

or pharmaceutically acceptable salt thereof.

33. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

34. A synthetic process comprising reacting a compound of Formula VIII:

with a compound of Formula IX:

under conditions and for a time sufficient to produce a compound of Formula I:

wherein:

L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups;

each R 9 is, independently, OR a′ , SR a′ , C(O)R b′ , C(O)NR e′ R f′ , C(O)OR b′ , OC(O)R b′ , OC(O)NR e′ R f′ , NR e′ R f′ , NR c′ C(O)R d′ , NR c′ C(O)OR d′ , NR c′ C(O)NR d′ , S(O)R b , S(O)NR e′ R f′ , S(O) 2 R b′ , NR c′ S(O) 2 R d′ , NR b′ S(O) 2 NR e′ R f′ , halogen, cyano, nitro, hydroxyl, carboxy, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylalkyloxy, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkyloxy, heterocycloalkylalkyloxy, aryl, arylalkyl, aryloxy, arylalkyloxy, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, amino, alkylamino, dialkylamino, acyl, formyl, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, dialkylcarbamyloxy, acyloxy, carboxy, alkylsulfonyl, alkylsulfinyl, thio, or alkylthio;

each R 7 is, independently, OR u′ , SR u′ , C(O)R v′ , C(O)NR y′ R z′ , C(O)OR v′ , OC(O)R v′ , OC(O)NR y′ R z′ , NR y′ R z′ , NR w′ C(O)R x′ , NR w′ C(O)OR x′ , NR w′ C(O)NR x′ , S(O)R v′ , S(O)NR y′ R z′ , S(O) 2 R v′ , NR w′ S(O) 2 R x′ , NR v′ S(O) 2 NR y′ R z′ , halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

or any R c′ and R d′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R e′ and R f′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R q and R r , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R s and R t , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R w and R x , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R y and R z , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R q′ and R r′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocyclic ring;

or any R s′ and R t′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

or any R w′ and R x′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R y′ and R z′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

Y is halogen, C 1-12 alkoxy, hydroxyl, amino, OC(O)R yy , or OC(O)R 1 ; and

R yy is C 1-12 alkyl;

provided that the compound of Formula I is not N-(4-oxo-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl)-acetamide, or pharmaceutically acceptable salt thereof.

35. The synthetic process of claim 34 wherein Y is halogen.

36. The synthetic process of claim 34 wherein Y is chloro.

37. The synthetic process of claim 34 wherein the compound of Formula VIII is produced by a process comprising:

(a) reacting a compound of Formula IV:

with a nitrating agent under conditions and for a time sufficient to produce a compound of Formula VII: and

(b) reducing the nitro group of the compound of Formula VII under conditions and for a time sufficient to produce a compound of Formula VIII.

38. The synthetic process of claim 37 wherein said nitrating agent comprises nitric acid, N 2 O 4 , N 2 O 5 , esters of nitric acid, metallic nitrites, or nitronium salts.

39. The synthetic process of claim 37 wherein said nitrating agent comprises potassium nitrate.

40. The synthetic process of claim 37 wherein said reducing comprises reacting a compound of Formula VII with a reducing agent comprising zinc, tin, iron, lithium aluminum hydride, a sulfide, hot liquid paraffin, aluminum hydride-aluminum chloride, hydrazine, sodium dihydro(trithio)borate, or hydrogen gas.

41. The synthetic process of claim 37 wherein the compound of Formula IV is produced by a process comprising reacting a compound of Formula II:

with a compound of Formula III:

under conditions and for a time sufficient to form a compound of Formula IV; wherein X is halogen.

42. The synthetic process of claim 41 wherein X is chloro.

43. The synthetic process of claim 37 wherein the compound of Formula IV is produced by a process comprising reacting a compound of Formula V:

with a compound of Formula VI:

in the presence of a Fischer indole catalyst under conditions and for a time sufficient to form said compound of Formula IV.

44. The synthetic process of claim 43 wherein said Fischer indole catalyst comprises a protic acid, Lewis acid, or metallic halide.

45. The synthetic process of claim 43 wherein said Fischer indole catalyst is sulfuric acid, hydrochloric acid, polyphosphoric acid, zinc chloride, aluminum chloride, boron trifluoride, or iron chloride.

46. The synthetic process of claim 43 wherein said Fischer indole catalyst is sulfuric acid.

47. A synthetic process comprising reacting a compound of Formula XV:

with a compound of Formula III:

under conditions and for a time sufficient to produce a compound of Formula I:

wherein:

L 1 is a C 3-6 alkylene bridge which is optionally substituted with 1, 2, 3, or 4 groups independently selected from OR o , SR o , C(O)R p , C(O)NR s R t , C(O)OR p , OC(O)R p , OC(O)NR s R t , NR s R t , NR q C(O)R r , NR q C(O)OR r , NR q C(O)NR r , S(O)R p , S(O)NR s R t , S(O) 2 R p , NR q S(O) 2 R r , NR p S(O) 2 NR s R t , oxo, halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl; wherein said C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, and heteroarylalkynyl are each optionally substituted by 1, 2, or 3 R 6 groups;

each R 9 is, independently, OR a′ , SR a′ , C(O)R b′ , C(O)NR e′ R f′ , C(O)OR b′ , OC(O)R b′ , OC(O)NR e′ R f′ , NR e′ R f′ , NR c′ C(O)R d′ , NR c′ C(O)OR d′ , NR c′ C(O)NR d′ , S(O)R b′ , S(O)NR e′ R f′ , S(O) 2 R b′ , NR c′ S(O) 2 R d′ , NR b′ S(O) 2 NR e′ R f′ , halogen, cyano, nitro, hydroxyl, carboxy, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylalkyloxy, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkyloxy, heterocycloalkylalkyloxy, aryl, arylalkyl, aryloxy, arylalkyloxy, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, amino, alkylamino, dialkylamino, acyl, formyl, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, dialkylcarbamyloxy, acyloxy, carboxy, alkylsulfonyl, alkylsulfinyl, thio, or alkylthio;

each R 6 is, independently, OR o′ , SR o′ , C(O)R p′ , C(O)NR s′ R t′ , C(O)OR p′ , OC(O)R p′ , OC(O)NR s′ R t′ , NR s′ R t′ , NR q′ C(O)R r′ , NR q C(O)OR r′ , NR q′ C(O)NR r′ , S(O)R p′ , S(O)NR s′ R t′ , S(O) 2 R p′ , NR q′ S(O) 2 R r′ , NR p′ S(O) 2 NR s′ R t′ , halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

each R 7 is, independently, OR u′ , SR u′ , C(O)R v′ , C(O)NR y′ R z′ , C(O)OR v′ , OC(O)R v′ , OC(O)NR y′ R z′ , NR y′ R z′ , NR w′ C(O)R x′ , NR w′ C(O)OR x′ , NR w′ C(O)NR x′ , S(O)R v′ , S(O)NR y′ R z′ , S(O) 2 R v′ , NR w′ S(O) 2 R x′ , NR v′ S(O) 2 NR y′ R z′ , halogen, cyano, nitro, hydroxyl, amino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

or any R c′ and R d′ , together with the moiety to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring;

or any R e′ and R f′ , together with the nitrogen atom to which they are attached, form a 3-, 4-, 5-, 6- 7- or 8-membered heterocycloalkyl ring or 5-, 6-, 7- or 8-membered heteroaryl ring;

each R o , R p , R q , R r , R s , R t , R u , R v , R y , or R z , is, independently, H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are each optionally substituted with 1, 2, or 3 groups independently selected from halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, amino, alkylamino, dialkylamino, acyl, formyl, acyloxy, carbamyl, alkylcarbamyl, dialkylcarbamyl, alkylcarbamyloxy, and dialkylcarbamyloxy;