# US 5,344,826 A · Tricycle steroid analogs

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- Number: US 5,344,826 A
- Document ID: US5344826A
- Status: Granted
- Kind: A
- Application number: 08/136,150
- Filed: 1993-10-15
- Granted: 1994-09-06
- Earliest claimed: 1991-12-20
- Assignees: Washington University
- Inventors: Douglas F. Covey; Yuefei Hu; Charles F. Zorumski
- Web page: https://patentgrep.com/patent/US5344826A

## CPC

- C07C 69/716: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids}
- A61P 5/24: of the sex hormones
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 23/00: Anaesthetics
- A61P 23/02: Local anaesthetics
- A61P 25/02: for peripheral neuropathies
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/20: Hypnotics; Sedatives
- C07C 2603/16: Benz[e]indenes; Hydrogenated benz[e]indenes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Novel tricyclic steriod analogs are disclosed which are 1H-benz[e]indene dodecahydro compounds that are useful for enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex and can be represented by the following structural formulas: ##STR1## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl; R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different; R.sub.3 =H or CH.sub.3 ; R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different; R.sub.5 =H; R.sub.6 =H; R.sub.5,R.sub.6 =.dbd.O(carbonyl); R.sub.7 =H; R.sub.8 =a hydrogen bond accepting group. R.sub.7,R.sub.8 =.dbd.O(carbonyl); and R'=an ester group.

## Claims

### Claim 1

The method of enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex comprising administering to a warm blooded mammal an effective amount of a compound of the following structural formula: ##STR38## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl;
R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different;
R.sub.3 =H or CH.sub.3 ;
R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different;
R.sub.5 =H;
R.sub.6 =H;
R.sub.5,R.sub.6 =.dbd.O(carbonyl);
R.sub.7 =H;
R.sub.8 =a hydrogen bond accepting group;
R.sub.7,R.sub.8 =.dbd.O(carbonyl); and
R'=H or an ester group.

### Claim 2 (depends on 1)

The method of claim 1 in which the administered compound has the structure ##STR39## wherein R is .dbd.O, CN, ##STR40## or COCH.sub.3.

### Claim 3 (depends on 2)

The method of claim 2 in which R is .dbd.O.

### Claim 4 (depends on 2)

The method of claim 2 in which R is CN.

### Claim 5 (depends on 2)

The method of claim 2 in which R is ##STR41##

### Claim 6 (depends on 2)

The method of claim 2 in which R is COCH.sub.3.