Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Reexamination Certificate
2000-02-08
2003-10-21
Barts, Samuel (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
C562S507000
Reexamination Certificate
active
06635673
ABSTRACT:
BACKGROUND OF THE INVENTION
Compounds of formula
wherein R
1
is hydrogen or a lower alkyl radical and n is 4, 5, or 6 are known in U.S. Pat. No. 4,024,175 and its divisional U.S. Pat. No. 4,087,544. The uses disclosed are: protective effect against cramp induced by thiosemicarbazide; protective action against cardiazole cramp; the cerebral diseases, epilepsy, faintness attacks, hypokinesia, and cranial traumas; and improvement in cerebral functions. The compounds are useful in geriatric patients. The patents are hereby incorporated by reference.
SUMMARY OF THE INVENTION
The compounds of the invention are those of formulas 1 and 1A
wherein R to R
14
are as defined below.
The compounds of the invention and their pharmaceutically acceptable salts and the prodrugs of the compounds, are useful in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), and inflammation, especially arthritis.
The invention is also a pharmaceutical composition of a compound of formulas 1 and 1A.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of the instant invention and their pharmaceutically acceptable salts are as defined by formulas 1 and 1A
or a pharmaceutically acceptable salt thereof wherein:
R is hydrogen or a lower alkyl;
R
1
to R
14
are each independently selected from hydrogen, straight or branched alkyl of from 1 to 6 carbons, phenyl, benzyl, fluorine, chlorine, bromine, hydroxy, hydroxymethyl, amino, aminomethyl, trifluoromethyl, —CO
2
H, —CO
2
R
15
, —CH
2
CO
2
H, —CH
2
CO
2
R
15
, —OR
15
wherein R
15
is a straight or branched alkyl of from 1 to 6 carbons, phenyl, or benzyl, and R
1
to R
8
are not simultaneously hydrogen.
Preferred compounds of the invention are those of Formula I wherein R
1
to R
14
are selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl straight or branched, phenyl, or benzyl.
More preferred compounds are those of Formula I wherein R
1
to R
14
are selected from hydrogen, methyl, ethyl, or benzyl.
The most preferred compounds are selected from:
(1&agr;,3&agr;,4&agr;)-(1-Aminomethyl-3,4-dimethyl-cyclopentyl)-acetic acid;
(1&agr;,3&agr;,4&agr;)-(1-Aminomethyl-3,4-diethyl-cyclopentyl)-acetic acid;
(1&agr;,3&agr;,4&agr;)-(1-Aminomethyl-3,4-diisopropyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-ethyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-ethyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-isopropyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-isopropyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-ethyl-4-isopropyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-ethyl-4-isopropyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-ethyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-ethyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-isopropyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-tert-butyl-4-isopropyl-cyclopentyl)-acetic acid;
(1&agr;,3&agr;,4&agr;)-(1-Aminomethyl-3,4-di-tert-butyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-methyl-4-phenyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-methyl-4-phenyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-benzyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&agr;,4&agr;)]-(1-Aminomethyl-3-benzyl-4-methyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-methyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-ethyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-isopropyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-tert-butyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-phenyl-cyclopentyl)-acetic acid;
(1S-cis)-(1-Aminomethyl-3-benzyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-methyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-ethyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-isopropyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-tert-butyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-phenyl-cyclopentyl)-acetic acid;
(1R-cis)-(1-Aminomethyl-3-benzyl-cyclopentyl)-acetic acid;
(S)-(1-Aminomethyl-3,3-dimethyl-cyclopentyl)-acetic acid;
(S)-(1-Aminomethyl-3,3-diethyl-cyclopentyl)-acetic acid;
(1-Aminomethyl-3,3,4,4-tetramethyl-cyclopentyl)-acetic acid;
(1-Aminomethyl-3,3,4,4-tetraethyl-cyclopentyl)-acetic acid;
(1&agr;,3&bgr;,4&bgr;)-(1-Aminomethyl-3,4-dimethyl-cyclopentyl)-acetic acid,
(1&agr;,3&bgr;,4&bgr;)-(1-Aminomethyl-3,4-diethyl-cyclopentyl)-acetic acid;
(1&agr;,3&bgr;,4&bgr;)-(1-Aminomethyl-3,4-diisopropyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-ethyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-ethyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-isopropyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-isopropyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-ethyl-4-isopropyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-ethyl-4-isopropyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-methyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-ethyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-ethyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-isopropyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-tert-butyl-4-isopropyl-cyclopentyl)-acetic acid;
(1&agr;,3&bgr;,4&bgr;)-(1-Aminomethyl-3,4-di-tert-butyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-methyl-4-phenyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-methyl-4-phenyl-cyclopentyl)-acetic acid;
[1R-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-benzyl-4-methyl-cyclopentyl)-acetic acid;
[1S-(1&agr;,3&bgr;,4&bgr;)]-(1-Aminomethyl-3-benzyl-4-methyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-methyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-ethyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-isopropyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-tert-butyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-phenyl-cyclopentyl)-acetic acid;
(1R-trans)-(1-Aminomethyl-3-benzyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-methyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-ethyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-isopropyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-tert-butyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-phenyl-cyclopentyl)-acetic acid;
(1S-trans)-(1-Aminomethyl-3-benzyl-cyclopentyl)-acetic acid;
(R)-(1-Aminomethyl-3,3-dimethyl-cyclopentyl)-acetic acid;
(R)-(1-Aminomethyl-3,3-diethyl-cyclopentyl)-acetic acid;
cis-(1-Aminomethyl-3-methyl-cyclobutyl)-acetic acid;
cis-(1-Aminomethyl-3-ethyl-cyclobutyl)-acetic acid;
cis-(1-Aminomethyl-3-isopropyl-cyclobutyl)-acetic acid;
cis-(1-Aminomethyl-3-tert-butyl-cyclobutyl)-acetic acid;
cis-(1-Aminomethyl-3-phenyl-cyclobutyl)-acetic acid;
cis-(1-Aminomethyl-3-benzyl-cyclobutyl)-
Bryans Justin Stephen
Horwell David Christopher
Thorpe Andrew John
Wustrow David Juergen
Yuen Po-Wai
Ashbrook Charles W.
Barts Samuel
DeBenedictis Karen
Ganjeizadeh Mehdi
Warner-Lambert & Company
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