Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-04-07
2003-04-08
Chang, Ceila (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S315000, C514S317000, C514S331000, C514S432000, C514S459000, C546S208000, C546S209000, C546S210000, C546S235000, C546S245000, C546S246000, C548S131000, C548S134000, C548S250000, C549S013000, C549S018000, C549S426000
Reexamination Certificate
active
06545022
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.
Compounds of formula
wherein R
1
is a straight or branched alkyl group having from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms; R
2
is hydrogen or methyl; and R
3
is hydrogen, methyl, or carboxyl are known in U.S. Pat. No. 5,563,175 and various divisionals. These patents are hereby incorporated by reference. (See Suman-Chaulan N., et al.,
European Journal of Pharmacology
, 1993;244:293-301.)
SUMMARY OF THE INVENTION
The compounds of the instant invention are novel amines and their pharmaceutically acceptable salts useful in a variety of disorders. The disorders include: epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, inflammation, and gastrointestinal disorders such as irritable bowel syndrome.
The compounds of the invention are those of formulas 1D and 1E below.
Preferred compounds are those of formulas 1D and 1E wherein R is a sulfonamide selected from —NHSO
2
R
15
or —SO
2
NHR
15
wherein R
15
is straight or branched alkyl or trifluoromethyl.
Other preferred compounds are those of formulas 1D and 1E wherein R is a phosphonic acid, —PO
3
H
2
.
Other preferred compounds are those of formulas 1D and 1E wherein R is selected from:
Especially preferred are
DETAILED DESCRIPTION OF THE INVENTION
The amines of the instant invention are compounds of formula 1D and 1E and the pharmaceutically acceptable salts thereof.
The compounds of the invention are those of formula
or a pharmaceutically acceptable salt thereof wherein:
n is an integer of from 0 to 2;
R is sulfonamide,
amide,
phosphonic acid,
heterocycle,
sulfonic acid, or
hydroxamic acid; and
X is —O—, —S—, —S(O)—, —S(O)
2
—, or NR′
1
wherein R′
1
is hydrogen, straight or branched alkyl of from 1 to 6 carbons, benzyl, —C(O)R′
2
wherein R′
2
is straight or branched alkyl of 1 to 6 carbons, benzyl or phenyl or —CO
2
R′
3
wherein R′
3
is straight or branched alkyl of from 1 to 6 carbons, or benzyl wherein the benzyl or phenyl groups can be unsubstituted or substituted by from 1 to 3 substituents selected from halogen, trifluoromethyl, and nitro.
The following are specific compounds of the instant invention:
N-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-methanesulfonamide;
(4-Aminomethyl-tetrahydro-pyran4-ylmethyl)-phosphonic acid;
2-(4-Aminomethyl-tetrahydro-pyran-4-yl )-N-hydroxy-acetamide;
3-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-4H-[1,2,4]oxadiazol-5-one;
3-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-4H-[1,2,4]oxadiazole-5-thione;
C-[4-(1H-Tetrazol-5-ylmethyl)-tetrahydro-pyran-4-yl]-methylamine;
N-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-C,C,C-trifluoro-methanesulfonamide;
3-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-4H-[1,2,4]thiadiazol-5-one;
C-[4-(2-Oxo-2,3-dihydro-2&lgr;
4
-[1,2,3,5]oxathiadiazol-4-ylmethyl)-tetrahydro-pyran-4-yl]-methylamine;
(4-Aminomethyl-tetrahydro-pyran-4-yl)-methanesulfonamide;
(4-Aminomethyl-tetrahydro-pyran-4-yl)-methanesulfonic acid;
N-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-acetamide;
N-(4-Aminomethyl-tetrahydro-pyran-4-ylmethyl)-2-phenyl-acetamide;
N-(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-methanesulfonamide;
(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-phosphonic acid;
2-(4-Aminomethyl-tetrahydro-thiopyran-4-yl)-N-hydroxy-acetamide;
3-(4-Aminomethyl-tetrahydro-thiopyran-4-yl methyl)-4H-[1,2,4]oxadiazol-5-one;
3-(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-4H-[1,2,4]oxadiazole-5-thione;
C-[4-(1H-Tetrazol-5-ylmethyl)-tetrahydro-thiopyran-4-yl]-methylamine;
N-(4-Aminomethyl-tetrahydro-thiopyran-4-yl methyl)-C,C,C-trifluoro-methanesulfonamide;
3-(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-4H-[1,2,4]thiadiazol-5-one;
C-[4-(2-Oxo-2,3-dihydro-2&lgr;
4
-[1,2,3,5]oxathiadiazol-4-ylmethyl)-tetrahydro-thiopyran-4-yl]-methylamine;
(4-Aminomethyl-tetrahydro-thiopyran-4-yl)-methanesulfonamide;
(4-Aminomethyl-tetrahydro-thiopyran-4-yl)-methanesulfonic acid;
N-(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-acetamide;
N-(4-Aminomethyl-tetrahydro-thiopyran-4-ylmethyl)-2-phenyl-acetamide;
N-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-methanesulfonamide;
(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-phosphonic acid;
2-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-yl)-N-hydroxy-acetamide;
3-(4-Aminomethyl-1 -oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-4H-[1,2,4]oxadiazol-5-one;
3-(4-Aminomethyl-1 -oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-4H-[1,2,4]oxadiazole-5-thione;
C-[1-Oxo-4-(1H-tetrazol-5-ylmethyl)-hexahydro-1&lgr;
4
-thiopyran-4-yl]-methylamine;
N-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-C,C,C-trifluoro-methanesulfonamide;
3-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-4H-[1,2,4]thiadiazol-5-one;
C-[1-Oxo-4-(2-oxo-2,3-dihydro-2&lgr;
4
-[1,2,3,5]oxathiadiazol-4-ylmethyl)-hexahydro-1&lgr;
4
-thiopyran-4-yl]-methylamine;
4-Arminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-yl)- methanesulfonamide;
(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-yl)-methanesulfonic acid;
N-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-acetamide;
N-(4-Aminomethyl-1-oxo-hexahydro-1&lgr;
4
-thiopyran-4-ylmethyl)-2-phenyl-acetamide;
N-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-methanesulfonamide;
(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-phosphonic acid;
2-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-yl)-N-hydroxy-acetamide;
3-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-4H-[1,2,4]oxadiazol-5-one;
3-(4-Aminomethyl-1,1 -dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-4H-[1,2,4]oxadiazol-5-thione;
C-[1,1-Dioxo-4-(1H-tetrazol-5-ylmethyl)-hexahydro-1&lgr;
6
-thiopyran-4-yl]-methylamine;
N-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-C,C,C-trifluoro-methanesulfonamide;
3-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-4H-[1,2,4]thiadiazol-5-one;
C-[1,1-Dioxo-4-(2-oxo-2,3-dihydro-2&lgr;
4
-[1,2,3,5]oxathiadiazol-4-ylmethyl)-hexahydro-1&lgr;
6
-thiopyran-4-yl]-methylamine;
(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-yl)-methanesulfonamide;
(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-yl)-methanesulfonic acid;
N-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran4-ylmethyl)-acetamide;
N-(4-Aminomethyl-1,1-dioxo-hexahydro-1&lgr;
6
-thiopyran-4-ylmethyl)-2-phenyl-acetamide;
N-(4-Aminomethyl-piperidin-4-ylmethyl)-methanesulfonamide;
(4-Aminomethyl-piperidin-4-ylmethyl)-phosphonic acid;
2-(4-Aminomethyl-piperidin-4-yl)-N-hydroxy-acetamide;
3-(4-Aminomethyl-piperidin-4-ylmethyl)-4H-[1,2,4]oxadiazol-5-one;
3-(4-Aminomethyl-piperidin-4-ylmethyl)-4H-[1,2,4]oxadiazole-5-thione;
C-[4-(1H-Tetrazol-5-ylmethyl)-piperidin-4-yl]-methylamine;
N-(4-Aminomethyl-piperidin-4-ylmethyl)-C,C,C-trifluoro-methanesulfonamide,
3-(4-Aminomethyl-piperidin-4-ylmethyl)-4H-[1,2,4]thiadiazol-5-one;
C-[4-(2-Oxo-2,3-dihydro-2&lgr;
4
-[1,2,3,5]oxathiadiazol-4-yl-methyl)-piperidin-4-yl]-methylamine;
(4-Aminomethyl-piperidin-4-yl)-methanesulfonamide;
(4-Aminomethyl-piperidin-4-yl)-methanesulfonic acid;
N-(4-Aminomethyl-piperidin-4-ylmethyl)-acetamide;
N-(4-Aminomethyl-
Bryans Justin Stephen
Horwell David Christopher
Kneen Clare Octavia
Wustrow David Juergen
Chang Ceila
McDonnell & Boehnen Hulbert & Berghoff
Pfizer Inc.
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