Patent US5391577A successfully refreshed from Google Patents.
US5391577A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-phenylalkyl substituted α-amino carboxamide derivatives and process for their preparation
Assignee: Newron Pharmaceuticals SpA
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Filing: 1993-05-25
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Granted: 1995-02-21
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Expires: 2013-05-25
Abstract
Abstract N-phenylalkyl substituted alpha -amino carboxamide derivatives of formula (I) <IMAGE> (I) wherein R is C1-C8 alkyl, C3-C8 cycloalkyl, furyl, thienyl, pyridyl or unsubstituted or substituted phenyl; A is a -(CH2)m- or -(CH2)p-X-(CH2)q- group wherein X is -O-, -S- or -NR4-; R1, R2, R3, R'3, R4, n, m, p and q are as herein defined; and each of R5 and R6 is independently hydrogen or C1-C6 alkyl, and the pharmaceutically acceptable salts thereof, are active on the central nervous system and can be used as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agents in mammals.
Inventors
- 👤 Philippe Dostert
- 👤 Paolo Pevarello
- 👤 Franco Heidempergher
- 👤 Mario Varasi
- 👤 Alberto Bonsignori
- 👤 Romeo Roncucci
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:27
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; A; A61; A61P; A61P25/00; A61P25/08; A61P25/20; A61P25/24; A61P25/26; C07C; C07C237/00; C07C237/02; C07C237/04; C07C237/06; C07C323/00; C07C323/50; C07C323/62; C07C323/63; C07C327/00; C07C327/02; C07C327/04; C07C327/06; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/58; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/32
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
116 words
A compound selected from the group consisting of: 2-[4-(3-phenylpropyloxy)benzyl]aminopropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]aminoacetamide; (4-benzyloxybenzyl)aminoacetamide; [4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminoacetamide; 2-[4-(3-chlorobenzyloxy)benzyl]amino-3-hydroxypropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]amino-N-methylpropionamide; 2-(4-benzyloxybenzyl)amino-N-methylpropionamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N-methylpropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]aminopropionamide; 2-[4-(3-methoxybenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(4-chlorobenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 1-[(4-benzyloxybenzyl)amino]cyclopentane-1-N-methylcarboxamide; 2-(4-benzyloxybenzyl)amino-N-methylacetamide; 1-[(4-benzyloxybenzyl)amino]cyclopropane-1-N-methylcarboxamide; 1-[(4-benzyloxybenzyl)amino]cyclopentane-1-carboxamide; 2-(4-benzyloxybenzyl)amino-3-methyl-N-methylbutanamide; 2-(4-benzyloxybenzyl)amino-3-phenyl-N-methylpropionamide; 1-[(4-benzyloxybenzyl)amino]cyclopropane-1-carboxamide; 2-(4-benzyloxybenzyl)aminopropionamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N-methyl-butanamide; 2-(4-benzyloxybenzyl)amino-4-methyl-N-methylpentanamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-propionamide; 2-[4-(2-methylbenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(3-methylbenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(3-trifluoromethylbenzyloxy)benzyl]amino-3-hydroxy-N-4-methylpropionamide; 2-[4-(2-trifluoromethylbenzyloxy)benzyl]amino-3-hydroxy-N-methylpropionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-N-methylpropionamide; 2-[4-(2-chlorobenzyloxy)benzyl]aminopropionamide; 2-(4-phenyloxybenzyl)aminopropionamide; 2-(4-benzylbenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-phenylethyloxybenzyl)aminopropionamide; 2-(4-benzylthiobenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-phenylethylbenzyl)amino-3-hydroxy-N-methyl-propionamide; 2-[4-(2-phenylethyloxy)benzyl]amino-3-hydroxy-N-methylpropionamide; 2-[4-(2-fluorobenzyloxy)benzyl]aminopropionamide; 2-(4-phenyloxymethylbenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-benzylaminobenzyl)amino-3-hydroxy-N-methyl-propionamide; 2-(4-benzyloxyphenethyl)aminopropionamide; 2-[4-(2-chlorobenzyloxy)phenethyl]aminopropionamide; 2-[4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminopropionamide; 2-[(4-benzyl)-α-methyl-benzyl]aminopropionamide, 2-(4-benzyloxybenzyl)aminobutanamide; 2-(2-benzyloxybenzyl)aminopropionamide; 2-(3-benzyloxybenzyl)aminopropionamide; 2-(4-cyclohexylmethylaminobenzyl)aminopropionamide; 2-(4-cyclopropylmethylaminobenzyl)aminopropionamide; 2-(4-phenylaminomethylbenzyl)aminopropionamide; 2-[4-(3-furfuryloxy)benzyl]aminopropionamide; 2-[4-(2-furfuryloxy)benzyl]aminopropionamide; 2-[4-(3-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(2-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(4-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(3-thienyloxy)benzyl]aminopropionamide; 2-[4-(2-thienyloxy)benzyl]aminopropionamide; 2-[N-(4-benzyloxybenzyl)-N-methyl]amino-3-hydroxy-N-methyl propionamide; 2-[N-(4-phenyloxymethylbenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylethylbenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylbenzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-benzylthiobenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylaminobenzyl)-N-methyl]aminopropionamide; 2-[N-(4-(2-chlorobenzyloxy)benzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(3-fluorobenzyloxy)benzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(2-fluorobenzyloxy)benzyl-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(3-fluorobenzyloxy)benzyl-N-methyl]amino-propionamide; 2-[N-(4-(2-chlorobenzyloxy)benzyl-N-methyl]amino propionamide; [4-(3-chlorobenzyloxy)phenylethyl]aminoacetamide; [4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminoacetamide; 2-[(4-benzyl)phenylethyl]aminoacetamide; 2-[2-(4-benzylamino)phenylethyl]aminoacetamide; 2-(4-benzyloxybenzyl)amino-N,N-dimethylacetamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N,N-dimethylpropionamide; 2-(4-benzylbenzyl)amino-N,N-dimethylacetamide; 2-(4-benzylaminobenzyl)amino-N,N-dimethylacetamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(3-fluorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(2-fluorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(3-fluorobenzyloxy)benzyl]amino-N,N-dimethyl propionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-N,N-dimethyl propionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethyl propionamide; 2-(4-benzyloxybenzyl)amino-N,N-dimethylpropionamide; 2-[N-(4-benzyloxybenzyl)-N-methyl]amino-N-methyl propionamide, as single (S) or (R) isomers or as a mixture thereof, and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
116 words
A compound selected from the group consisting of: 2-[4-(3-phenylpropyloxy)benzyl]aminopropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]aminoacetamide; (4-benzyloxybenzyl)aminoacetamide; [4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminoacetamide; 2-[4-(3-chlorobenzyloxy)benzyl]amino-3-hydroxypropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]amino-N-methylpropionamide; 2-(4-benzyloxybenzyl)amino-N-methylpropionamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N-methylpropionamide; 2-[4-(3-chlorobenzyloxy)benzyl]aminopropionamide; 2-[4-(3-methoxybenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(4-chlorobenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 1-[(4-benzyloxybenzyl)amino]cyclopentane-1-N-methylcarboxamide; 2-(4-benzyloxybenzyl)amino-N-methylacetamide; 1-[(4-benzyloxybenzyl)amino]cyclopropane-1-N-methylcarboxamide; 1-[(4-benzyloxybenzyl)amino]cyclopentane-1-carboxamide; 2-(4-benzyloxybenzyl)amino-3-methyl-N-methylbutanamide; 2-(4-benzyloxybenzyl)amino-3-phenyl-N-methylpropionamide; 1-[(4-benzyloxybenzyl)amino]cyclopropane-1-carboxamide; 2-(4-benzyloxybenzyl)aminopropionamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N-methyl-butanamide; 2-(4-benzyloxybenzyl)amino-4-methyl-N-methylpentanamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-propionamide; 2-[4-(2-methylbenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(3-methylbenzyloxy)benzyl]amino-3-hydroxy-N-methyl propionamide; 2-[4-(3-trifluoromethylbenzyloxy)benzyl]amino-3-hydroxy-N-4-methylpropionamide; 2-[4-(2-trifluoromethylbenzyloxy)benzyl]amino-3-hydroxy-N-methylpropionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-N-methylpropionamide; 2-[4-(2-chlorobenzyloxy)benzyl]aminopropionamide; 2-(4-phenyloxybenzyl)aminopropionamide; 2-(4-benzylbenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-phenylethyloxybenzyl)aminopropionamide; 2-(4-benzylthiobenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-phenylethylbenzyl)amino-3-hydroxy-N-methyl-propionamide; 2-[4-(2-phenylethyloxy)benzyl]amino-3-hydroxy-N-methylpropionamide; 2-[4-(2-fluorobenzyloxy)benzyl]aminopropionamide; 2-(4-phenyloxymethylbenzyl)amino-3-hydroxy-N-methylpropionamide; 2-(4-benzylaminobenzyl)amino-3-hydroxy-N-methyl-propionamide; 2-(4-benzyloxyphenethyl)aminopropionamide; 2-[4-(2-chlorobenzyloxy)phenethyl]aminopropionamide; 2-[4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminopropionamide; 2-[(4-benzyl)-α-methyl-benzyl]aminopropionamide, 2-(4-benzyloxybenzyl)aminobutanamide; 2-(2-benzyloxybenzyl)aminopropionamide; 2-(3-benzyloxybenzyl)aminopropionamide; 2-(4-cyclohexylmethylaminobenzyl)aminopropionamide; 2-(4-cyclopropylmethylaminobenzyl)aminopropionamide; 2-(4-phenylaminomethylbenzyl)aminopropionamide; 2-[4-(3-furfuryloxy)benzyl]aminopropionamide; 2-[4-(2-furfuryloxy)benzyl]aminopropionamide; 2-[4-(3-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(2-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(4-pyridyl)methyloxybenzyl]aminopropionamide; 2-[4-(3-thienyloxy)benzyl]aminopropionamide; 2-[4-(2-thienyloxy)benzyl]aminopropionamide; 2-[N-(4-benzyloxybenzyl)-N-methyl]amino-3-hydroxy-N-methyl propionamide; 2-[N-(4-phenyloxymethylbenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylethylbenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylbenzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-benzylthiobenzyl)-N-methyl]aminopropionamide; 2-[N-(4-benzylaminobenzyl)-N-methyl]aminopropionamide; 2-[N-(4-(2-chlorobenzyloxy)benzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(3-fluorobenzyloxy)benzyl)-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(2-fluorobenzyloxy)benzyl-N-methyl]amino-3-hydroxy-N-methylpropionamide; 2-[N-(4-(3-fluorobenzyloxy)benzyl-N-methyl]amino-propionamide; 2-[N-(4-(2-chlorobenzyloxy)benzyl-N-methyl]amino propionamide; [4-(3-chlorobenzyloxy)phenylethyl]aminoacetamide; [4-(3-chlorobenzyloxy)-α-methyl-benzyl]aminoacetamide; 2-[(4-benzyl)phenylethyl]aminoacetamide; 2-[2-(4-benzylamino)phenylethyl]aminoacetamide; 2-(4-benzyloxybenzyl)amino-N,N-dimethylacetamide; 2-(4-benzyloxybenzyl)amino-3-hydroxy-N,N-dimethylpropionamide; 2-(4-benzylbenzyl)amino-N,N-dimethylacetamide; 2-(4-benzylaminobenzyl)amino-N,N-dimethylacetamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(3-fluorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(2-fluorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethylpropionamide; 2-[4-(3-fluorobenzyloxy)benzyl]amino-N,N-dimethyl propionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-N,N-dimethyl propionamide; 2-[4-(2-chlorobenzyloxy)benzyl]amino-3-hydroxy-N,N-dimethyl propionamide; 2-(4-benzyloxybenzyl)amino-N,N-dimethylpropionamide; 2-[N-(4-benzyloxybenzyl)-N-methyl]amino-N-methyl propionamide, as single (S) or (R) isomers or as a mixture thereof, and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
22 words
A compound according to claim 1 which is in the form of an acid addition salt with hydrochloric acid or methanesulphonic acid.
Claim 4
Dependent Claim
31 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and, as an active principle, a therapeutically effective amount of a compound or salt as claimed in claim 1 or 2.
Claim 5
Dependent Claim
33 words
A method for the treatment of a patient having epilepsy, which method comprises administering to said patient a therapeutically effective amount of a compound or salt as claimed in claim 1 or 2.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-02-20 | 1998-08-22 | 1999-02-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-02-20 | 2002-08-22 | 2003-02-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-02-20 | 2006-08-22 | 2007-02-21 | $7700.00 | Window Closed / Lapsed |