# US 5,703,107 A · 3-aminoindolyl derivatives

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- Number: US 5,703,107 A
- Document ID: US5703107A
- Status: Granted
- Kind: A
- Application number: 08/554,212
- Filed: 1995-11-06
- Granted: 1997-12-30
- Earliest claimed: 1990-11-02
- Assignees: Merrell Pharmaceuticals Inc.
- Inventors: Francesco G. Salituro; Bruce M. Baron
- Web page: https://patentgrep.com/patent/US5703107A

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 209/42: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 403/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention is directed to a new class of 3-amido and 3-sulfamido-indolyl NMDA antagonists and their use in the treatment of a number of disease states.

## Claims

### Claim 1

A compound of the formula: ##STR87## in which Z is represented by H, C.sub.1 -C.sub.4 alkyl, phenyl, substituted phenyl in which the phenyl ring may be optionally substituted with up to 3 substituents, wherein each substitutent is independently selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, CF.sub.3, OCF.sub.3, OH, CN, NH.sub.2 and NO.sub.2, or a phenylalkyl substitutent in which the phenyl ring may be optionally substituted with up to 3 substitutents, wherein each substituent is independently selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, CF.sub.3, OCF.sub.3, OH, CN, NH.sub.2 and NO.sub.2 ; R is represented by hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, OCF.sub.3, OH, NO.sub.2, or CN; B is represented by hydrogen, C.sub.1 -C.sub.4 alkyl, phenylalkyl substitutent in which the phenyl ring may be optionally substituted with up to 3 substitutents, wherein each substituent is independently selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, CF.sub.3, OCF.sub.3, OH, CN, NH.sub.2 and NO.sub.2, or --CH.sub.2 --COR.sub.1 wherein R.sub.1 is represented by a substituent selected from the group consisting of --OH, --OR.sub.3, --NR.sub.4 R.sub.5, --OCH.sub.2 OR.sub.3, and --O--(CH.sub.2).sub.m --NR.sub.6 R.sub.7, in which m is an integer of from 1-4; R.sub.3 is represented by C.sub.1-4 alkyl, phenyl, substituted phenyl in which the phenyl ring may be optionally substituted with up to 3 substituents, wherein each substitutent is independently selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, CF.sub.3, OCF.sub.3, OH, CN, NH.sub.2 and NO.sub.2 or a phenylalkyl substitutent in which the phenyl ring may be optionally substituted with up to 3 substitutents, wherein each substituent is independently selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, CF.sub.3, OCF.sub.3, OH, CN, NH.sub.2 and NO.sub.2 ; R.sub.4 and R.sub.5 are each independently represented by hydrogen or a C.sub.1-4 alkyl; R.sub.6 and R.sub.7 are each independently represented by hydrogen or a C.sub.1-4 alkyl; X is represented by CO; A is represented by a substituent selected from the group consisting of: ##STR88## in which L is represented by a substituent selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, OCF.sub.3, OH, NO.sub.2, NH.sub.2, phenylalkyl, acetyloxy or CN; and the pharmaceuticaly acceptable salts thereof with the proviso that with respect to a substituted phenyl ring, there may not be more than one NH.sub.2 or NO.sub.2 nor both an alkoxy and a hydroxy on any one phenyl ring.

### Claim 2 (depends on 1)

A compound according to claim 1 in which said compound is 3-›(phenacyl)methylamino!-2-tetrazole-4,6-dichloroindole.

### Claim 3 (depends on 1)

A compound according to claim 1 in which said compound is 3-›(tetrazoleacyl)amino!-2-carboxy-4,6-dichloroindole.

### Claim 4 (depends on 1)

A compound according to claim 1 in which said compound is 3-›(tetrazoleacyl)amino!-2-carbotetrazole-4,6-dichloroindole.

### Claim 5 (depends on 1)

A compound according to claim 1 in which said compound is 3-›(phenacyl)methylamino!-2-carbonylaminotetrazole-6-chloroindole.

### Claim 6 (depends on 1)

A method for treatment of epilepsy comprising administering to a patient in need thereof an anti-epileptic amount of a compound according to claim 1.

### Claim 7 (depends on 1)

A method for the treatment of anxiety comprising administering an anxiolytic amount of a compound according to claim 1.

### Claim 8 (depends on 1)

A method for producing an analgesic effect comprising administering to a patient in need thereof an analgesic amount of a compound according to claim 1.