# US 5,703,237 A · N-Aminoalkyl-2-anthraquinonecarboxamides; new dopamine receptor subtype specific ligands

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- Number: US 5,703,237 A
- Document ID: US5703237A
- Status: Granted
- Kind: A
- Application number: 08/634,278
- Filed: 1996-04-18
- Granted: 1997-12-30
- Earliest claimed: 1996-04-18
- Assignees: Neurogen Corporation
- Inventors: Xi Chen; Jan William Francis Wasley
- Web page: https://patentgrep.com/patent/US5703237A

## CPC

- C07D 295/13: to an acyclic saturated chain
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- 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 25/30: for treating abuse or dependence
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 211/70: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 215/40: attached in position 8
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed are compounds of the formula: ##STR1## or the pharmaceutically acceptable acid addition salts thereof wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are the same or different and represent hydrogen, halogen, alkyl, alkoxy, hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy; --O.sub.2 CR', --NHCOR', --COR', --SO.sub.m R', where R' is C.sub.1 -C.sub.6 alkyl and wherein m is 0, 1 or 2; or R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 independently represent --CONR'R", or --NR'R" where R' and R" independently represent hydrogen or C.sub.1 -C.sub.6 alkyl; R.sub.8 is hydrogen or lower alkyl; X represents an optionally substituted alkylene group; and Y represents a mono-, di- or trisubstituted cyclic amino group, which compounds are useful in treatment of affective disorders such as schizophrenia, depression, Alzheimer's disease, movement disorders such as Parkinsonism and dystonia, and other disorders which respond to dopaminergic blockade such as substance abuse and obsessive compulsive disorders. Further, compounds of this invention may be useful in treating the extrapyramidal side effects associated with the use of conventional neuroleptic agents.

## Claims

### Claim 1

A compound of the formula: ##STR24## wherein: R.sub.8 is hydrogen or lower alkyl;
X represents an alkylene group of 2 to 6 carbon atoms optionally substituted with one or more alkyl groups having from 1 to 4 carbon atoms; and
W is phenyl, naphthyl, 1-(5,6,7,8-tetrahydro)naphthyl, or dihydroindenyl, each of which is optionally substituted with up to three groups independently selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, thioalkoxy, hydroxy, amino, monoalkylamino, dialkylamino, cyano, nitro, trifluoromethyl or trifluoromethoxy.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R.sub.8 is hydrogen and X is alkylene of 3-5 carbon atoms.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein R.sub.8 is hydrogen, X is alkylene of 3-5 carbon atoms, and W is dihydroindenyl, phenyl or naphthyl, each of which is optionally substituted with up to three groups independently selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, and hydroxy.

### Claim 4 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(2,3-Dichlorophenyl)piperazin-1-yl!}butyl)-2-anthraquinonecarbo xamide hydrochloride.

### Claim 5 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(1-Naphthyl)piperazin-1-yl!}butyl)-2-anthraquinonecarboxamide hydrochloride.

### Claim 6 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(2,3-Dimethylphenyl)piperazin-1-yl!}butyl)-2-anthraquinonecarbo xamide hydrochloride.

### Claim 7 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(2-Methyl-3-chlorophenyl)piperazin-1-yl!}butyl)-2-anthraquinone carboxamide hydrochloride.

### Claim 8 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(2-Methylphenyl)piperazin-1-yl!}butyl)-2-anthraquinonecarboxami de hydrochloride.

### Claim 9 (depends on 1)

A compound according to claim 1, which is N-(1-{4-›4-(2-Methoxyphenyl)piperazin-1-yl!}butyl)-2-anthraquinonecarboxam ide hydrochloride.