# US 5,708,187 A · 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta ›7,6-B!indoles: New 5-HT.sub.1F agonists

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- Number: US 5,708,187 A
- Document ID: US5708187A
- Status: Granted
- Kind: A
- Application number: 08/671,465
- Filed: 1996-06-27
- Granted: 1998-01-13
- Earliest claimed: 1996-06-27
- Assignees: Eli Lilly and Company
- Inventors: Michael Edward Flaugh; Anton Daniel Kiefer, Jr.; Clint Duane Walker; Yao-Chang Xu
- Web page: https://patentgrep.com/patent/US5708187A

## CPC

- C07D 209/94: containing carbocyclic rings other than six-membered
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This invention provides novel 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta›7,6-b!indoles. These compounds are 5-HT.sub.1F agonists which are useful for the treatment of migraine and associated disorders.

## Claims

### Claim 1

A compound of formula: ##STR26## wherein: R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.4 alkyl,or --CH.sub.2 CH.sub.2 -Aryl where Aryl is phenyl, phenyl monosubstituted with halo, or 1-(C.sub.1 -C.sub.6 alkyl)pyrazol-4-yl;
X is --NHC(O)R.sup.3, --NHC(Y)NHR.sup.4, --NHC(O)OR.sup.5, or --NHSO.sub.2 R.sub.7 ;
R.sup.3 is C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, phenyl, substituted phenyl, naphthyl, (C.sub.1 -C.sub.4 alkylene)-phenyl, thienylmethyl, or a heterocycle;
R.sup.4 is C.sub.1 -C.sub.6 alkyl, phenyl, or phenyl disubstituted with halo;
R.sup.5 is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl or phenyl monosubstituted with halo;
R.sup.6 is C.sub.1 -C.sub.6 alkyl, phenyl, or phenyl monosubstituted with halo or C.sub.1 -C.sub.4 alkoxy;
R.sup.7 is dimethylamino, phenyl or phenyl monosubstituted with halo or C.sub.1 -C.sub.4 alkyl;
m is 0 or 1;
n is 1 or 2; and
Y is S or O; and pharmaceutically acceptable salts and hydrates thereof.

### Claim 2 (depends on 1)

The compound of claim 1 where n is 1.

### Claim 3 (depends on 1)

The compound of claim 1 where n is 2.

### Claim 4 (depends on 1, 2)

The compound of claim 1, 2, or 3 where m is 0.

### Claim 5 (depends on 1, 2)

The compound of claim 1, 2, or 3 where m is 1.

### Claim 6 (depends on 1, 2)

The compound of claim 1, 2, or 3 where X is --NHC(O)R.sup.3.

### Claim 7 (depends on 6)

The compound of claim 6 where R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.4 alkyl.

### Claim 8 (depends on 7)

The compound of claim 7 where R.sup.1 and R.sup.2 are methyl.

### Claim 9 (depends on 8)

The compound of claim 8 where R.sup.3 is phenyl monosubstituted with halogen.

### Claim 10 (depends on 9)

The compound of claim 9 where the halogen is fluorine.

### Claim 11 (depends on 10)

The compound of claim 10 where the compound is R-(+)-6-(4-fluorobenzoyl)amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-car bazole, and pharmaceutically acceptable salts, solvates or hydrates thereof .