# US 2014/0155440 A1 · Cysteine and cystine bioisosteres to treat schizophrenia and reduce drug cravings

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- Number: US 2014/0155440 A1
- Document ID: US20140155440A1
- Status: Published application
- Kind: A1
- Application number: 14/148,959
- Filed: 2014-01-07
- Published: 2014-06-05
- Earliest claimed: 2008-04-16
- Assignees: Marquette University; UWM Research Foundation, Inc.
- Inventors: James M. Cook; David A. Baker; Edward Merle Johnson, II; Wenyuan Yin; Ranjit Singh Verma
- Web page: https://patentgrep.com/patent/US20140155440A1

## CPC

- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07K 5/0606: {the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr}
- C07K 5/1008: {the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

The present invention provides cysteine and cystine bioisosteres for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing such bioisosteres and methods of using the bioisosteres for treatment of schizophrenia and drug addiction.

## Claims

### Claim 1

A compound having the formula:
wherein R1 is H, a branched or straight chain C1 to C5 alkyl, or
each R2 is independently H or
wherein R4 is a branched or unbranched C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, aryloxy, benzyl, or phenyl; and
each R3 is independently
wherein each R5 is independently H, a branched or unbranched C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, or benzyl;
or a salt or hydrate of said compound.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein R1 is H or

### Claim 3 (depends on 1)

The compound according to claim 1, wherein each R2 is independently H or

### Claim 4 (depends on 1)

The compound according to claim 1, wherein each R3 is independently

### Claim 5 (depends on 1)

The compound according to claim 1, wherein each R5 is independently H, —CH2CH3, —CH(CH3)2, or phenyl.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein the compound has the formula:

### Claim 7 (depends on 1)

A salt of the compound of claim 1, wherein the salt is a hydrochloride salt.

### Claim 8 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically-acceptable carrier.

### Claim 9 (depends on 1)

A method of treating schizophrenia in a subject, comprising administering to said subject an effective amount of a compound according to claim 1, whereby schizophrenia is treated in said subject.

### Claim 10 (depends on 9)

The method according to claim 9, wherein the step of administering to said subject is accomplished by oral delivery.

### Claim 11 (depends on 1)

A method of treating drug craving in a subject, comprising administering to said subject an effective amount of a compound according to claim 1, whereby drug craving is treated in said subject.

### Claim 12 (depends on 10)

The method according to claim 10, wherein the step of administering to said subject is accomplished by oral delivery.