# US 5,607,935 A · 2-heterocyclicethylamine derivatives and their use as pharmaceuticals

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,607,935 A
- Document ID: US5607935A
- Status: Granted
- Kind: A
- Application number: 08/232,029
- Filed: 1994-08-01
- Granted: 1997-03-04
- Earliest claimed: 1991-10-30
- Assignees: Fisons Limited
- Inventors: Ronald C. Griffith; Richard J. Schmiesing; Robert J. Griffith
- Web page: https://patentgrep.com/patent/US5607935A

## CPC

- C07D 213/40: Acylated substituent nitrogen atom
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/30: for treating abuse or dependence
- C07D 213/38: having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C07D 213/61: Halogen atoms or nitro radicals
- C07D 213/73: Unsubstituted amino or imino radicals
- C07D 213/81: Amides; Imides
- C07D 213/89: with hetero atoms directly attached to the ring nitrogen atom
- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07D 237/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 241/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 241/16: Halogen atoms; Nitro radicals
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I), wherein A represents CH.dbd.CH; Q represents pyrazine having substituents R.sup.6 and R.sup.7 ; R.sup.1 represents H or C.sub.1-6 alkyl; R.sup.2 represents H, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-6 cycloalkyl or NH.sub.2 CH.sub.2 CO--; R.sup.3 represents H, C.sub.1-6 alkyl, C.sub.3-6 alkenyl or C.sub.3-6 alkynyl; R.sup.4 and R.sup.5 independently represent H, OH, C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halogen, trifluoromethyl or NR.sup.8 R.sup.9 ; R.sup.6 and R.sup.7 independently represent H, OH, C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halogen, trifluoromethyl, C.sub.1-6 hydroxyalkyl, amidino, CONH.sub.2 or NR.sup.8 R.sup.9 ; in addition, R.sup.6 and R.sup.7 may independently represent O when substituted on N; R.sup.8 and R.sup.9 independently represent H or C.sub.1-6 alkyl; and pharmaceutically acceptable derivatives thereof. The compounds are useful as pharmaceuticals, in particular in the treatment of neurological disorders.

## Claims

### Claim 1

A compound of the formula I, ##STR14## wherein A represents CH.dbd.CH;
Q represents pyrazine having substituents R.sup.6 and R.sup.7 ;
R.sup.1 represents H or C.sub.1-6 alkyl;
R.sup.2 represents H, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-6 cycloalkyl or NH.sub.2 CH.sub.2 CO--;
R.sup.3 represents H, C.sub.1-6 alkyl, C.sub.3-6 alkenyl or C.sub.3-6 alkynyl;
R.sup.4 and R.sup.5 independently represent H, OH, C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halogen, trifluoromethyl or NR.sup.8 R.sup.9 ;
R.sup.6 and R.sup.7 independently represent H, OH, C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halogen, trifluoromethyl, C.sub.1-6 hydroxyalkyl, amidino, CONH.sub.2 or NR.sup.8 R.sup.9 ;
in addition, R.sup.6 and R.sup.7 may independently represent O when substituted on N;
R.sup.8 and R.sup.9 independently represent H or C.sub.1-6 alkyl;
and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound as claimed in claim 1, wherein Q represents 2-pyrazinyl.

### Claim 3 (depends on 1)

A compound as claimed in claim 1, wherein R.sup.1 represents C.sub.1-6 alkyl.

### Claim 4 (depends on 1)

A compound as claimed in claim 1, wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each represent H.

### Claim 5 (depends on 1)

A compound as claimed in claim 1, which is
.alpha.-Phenyl-2-(2-pyrazine)ethanamine,
.alpha.-Phenyl-2-[2-(3-methoxy)pyrazine]ethanamine,
.alpha.-Phenyl-2-[2-(3-chloro)pyrazine]ethanamine,
N-Ethyl-1-phenyl-2-(2-pyrazine)ethanamine,
N-Isopropyl-1-phenyl-2-(2-pyrazine)ethanamine,
N-Methyl-1-phenyl-2-(2-pyrazine)ethanamine,
or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

A pharmaceutical formulation comprising a compound of formula I, as defined in claim 1, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable adjuvant, diluent or carrier.

### Claim 7 (depends on 1)

A method of treatment of neurological disorders selected from the group consisting of stroke and cerebral ischaemia, which comprises administering to a patient in need of such treatment a therapeutically effective amount of a compound of formula I, as defined in claim 1, or a pharmaceutically acceptable salt thereof.