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US5109017A
Expired / Lapsed
US
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(2-thienyl)alkylamine derivatives having neuroprotective properties
Assignee: AstraZeneca AB
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Filing: 1990-09-26
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Granted: 1992-04-28
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Expires: 2010-09-26
Abstract
Abstract Compounds of the formula I, ##STR1## in which: R 1 represents hydrogen or C 1-6 alkyl, R 2 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl or C 3-6 cycloalkyl, R 3 represents one or more radicals selected from hydrogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, halogen, trifluoromethyl, amino, lower alkylamino or dilower alkylamino, R 4 represents one or more radicals selected from hydrogen or C 1-6 alkyl, A represents an alpha-amino acid acyl group or an alkoxycarbonyl group, and pharmaceutically acceptable salts thereof are useful as pharmaceuticals, in particular they possess N-methyl-(d)-aspartate (NMDA) blocking properties and are useful in the treatment and/or prevention of neurological disorders such as stroke, cerebral ischaemia, cerebral palsy, hypoglycaemia, epilepsy, Alzheimer's disease, Huntington's chorea, Olivo-ponto-cerebellar atrophy, perinatal asphyxia and anoxia.
Inventors
- 👤 Richard J. Schmiesing
- 👤 Ronald C. Griffith
- 👤 Robert J. Murray
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 19:22
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/20
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
186 words
A compound of the formula I, ##STR4## in which: R 1 represents hydrogen or C 1-6 alkyl, R 2 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl or C 3-6 cycloalkyl, R 3 represents one or more radicals selected from hydrogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, halogen, trifluoromethyl, amino, lower alkylamino or dilower alkylamino, R 4 represents one or more radicals selected from hydrogen or C 1-6 alkyl, A represents COC(R 5 R 6 )N (R 7 R 8 ) or COOC 1-6 alkyl, R 5 represents hydrogen, C 1-6 alkyl, hydroxy-C 1-2 alkyl, mercaptomethyl, (methylthio)C 1-2 alkyl, carboxy-C 1-2 alkyl, 2-(C 1-3 alkoxy)ethyl, (aminocarbonyl)C 1-2 alkyl, amino-C 1-4 alkyl, 3-imidazolylmethyl, phenylmethyl or (4-hydroxyphenyl)-methyl or, in addition R 5 together with the adjacent nitrogen may represent a piperidine, pyrrolidine or a 2-pyrrolidinone ring, R 6 , R 7 and R 8 independently represent hydrogen or C 1-6 alkyl, or, in addition R 7 and R 8 taken together with the nitrogen to which they are attached may represent a C 4-5 N heterocyclic ring, or pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
186 words
A compound of the formula I, ##STR4## in which: R 1 represents hydrogen or C 1-6 alkyl, R 2 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl or C 3-6 cycloalkyl, R 3 represents one or more radicals selected from hydrogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, halogen, trifluoromethyl, amino, lower alkylamino or dilower alkylamino, R 4 represents one or more radicals selected from hydrogen or C 1-6 alkyl, A represents COC(R 5 R 6 )N (R 7 R 8 ) or COOC 1-6 alkyl, R 5 represents hydrogen, C 1-6 alkyl, hydroxy-C 1-2 alkyl, mercaptomethyl, (methylthio)C 1-2 alkyl, carboxy-C 1-2 alkyl, 2-(C 1-3 alkoxy)ethyl, (aminocarbonyl)C 1-2 alkyl, amino-C 1-4 alkyl, 3-imidazolylmethyl, phenylmethyl or (4-hydroxyphenyl)-methyl or, in addition R 5 together with the adjacent nitrogen may represent a piperidine, pyrrolidine or a 2-pyrrolidinone ring, R 6 , R 7 and R 8 independently represent hydrogen or C 1-6 alkyl, or, in addition R 7 and R 8 taken together with the nitrogen to which they are attached may represent a C 4-5 N heterocyclic ring, or pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
21 words
A compound according to claim 1 in which A is represented by COC(R 5 R 6 )N(R 7 R 8 ).
Claim 4
Dependent Claim
27 words
A compound according to claim 2 in which R 5 , R 6 , R 7 and R 8 are selected from hydrogen or C 1-6 alkyl.
Claim 5
Dependent Claim
19 words
A compound according to claim 2 in which R 1 and R 2 are selected from hydrogen or methyl.
Claim 6
Dependent Claim
21 words
A compound according to claim 3 in which R 5 , R 6 , R 7 and R 8 are hydrogen.
Claim 7
Dependent Claim
17 words
A compound according to claim 2 in which R 3 is hydrogen and R 4 is methyl.
Claim 8
Dependent Claim
25 words
A compound according to claim 1 which is, N-methyl-N-[1-(3-methyl-2-thienyl)-2-(2-aminophenyl)-ethyl]-2-aminoacetamide, N-[1-(3-methyl-2-thienyl)-2-phenylethyl]-2-aminoacetamide, N-methyl-N-[1-(3-methyl-2-thienyl)-2-phenylethyl]-2-aminoacetamide, N-ethyl-N-[1-(2-thienyl)-2-phenylethyl]-2-aminoacetamide, N-ethyl-N-[1-(3-methyl-2-thienyl)-2-phenylethyl]-2-aminoacetamide, N-[1-(2-thienyl)-2-phenylethyl]-2-aminoacetamide, N-[1-methyl-l-(3-methyl-2-thienyl)-2-phenylethyl]-2-aminoacetamide, or N-[1-methyl-l-(2-thienyl)-2-phenylethyl]-2-aminoacetamide, or a pharmaceuticaly acceptable acid addition salt thereof.
Claim 9
Dependent Claim
34 words
A method of treatment of neurological disorders, which method comprises administering to a patient suffering from that disorder an effective amount of one or more compounds of formula I, as defined in claim 1.
Claim 10
Dependent Claim
21 words
A pharmaceutical composition comprising a compound of formula I, as defined in claim 1, in admixture with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
EP0322582A2
Cited
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