2,3-Dihydro-imidazo (2,1-b)benzothiazoles compositions useful as anti-parkinsonism agents
AssigneeJanssen Pharmaceutica NV
InventorVictor Sipido
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Abstract
This invention relates to a novel series of 2,3-dihydro-imidazo[2,1-b]benzothiazoles which display monoamine oxidase inhibiting activities.
Claims3
A composition to treat Parkinsonism, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat Parkinsonism, of a compound selected from the group consisting of a 2,3-dihydroimidazo[2,1-b]benzothiazole which may structurally be represented by the formula ##STR41## and the pharmaceutically acceptable acid addition salts thereof, the pharmaceutically acceptable imidazo[2,1-b]benzothiazolium salts of formula ##STR42## and metal salt complexes thereof with a transition metal salt, wherein:
- R.sup.1 and R.sup.3 are each independently selected from the group consisting of hydrogen and lower alkyl;
- R.sup.2 and R.sup.4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl, aryl-lower alkyl, lower alkyloxy-lower alkyl or aryloxy-lower alkyl;
- R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each independently selected from the group consisting of hydrogen;
- halo;
- nitro;
- alkyl having from 1 to 20 carbon atoms;
- cycloalkyl having from 3 to 6 carbon atoms;
- hydroxy;
- lower alkyloxy;
- aryloxy;
- .alpha.-hydroxy-arylmethyl;
- amino;
- mono- and dialkyl-amino;
- mono-, di- and trihalo-lower alkylamino;
- lower alkenylamino;
- lower alkynylamino;
- (aryllower alkyl)amino;
- (lower alkyloxy-lower alkyl)amino;
- (hydroxy-lower alkyl)amino;
- (aryloxy-lower alkyl)amino;
- [mono- and di(lower alkyl)amino-lower alkyl]amino;
- lower alkanoylamino;
- N-(lower alkyl)lower alkanoylamino;
- aminocarbonylamino;
- (1-lower alkyl-4-piperidinyl)amino;
- cycloalkylamino wherein said cycloalkyl represents a mino-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms;
- and a radical of the formula ##STR43## wherein R.sup.10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl;
- or, when taken together R.sup.5 and R.sup.6, R.sup.6 and R.sup.7, or R.sup.7 and R.sup.8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus;
- R.sup.9 is a member selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl and aryllower alkyl;
- and
- X is a pharmaceutically acceptable anion and n represents the valency of the anion;
- wherein aryl as used in the foregoing definitions is phenyl, optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl;
- and aroyl is arylcarbonyl.
A composition of treat Parkinsonism, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat Parkinsonism, of a compound selected from the group consisting of N-ethyl-2,3-dihydroimidazo[2,1-b]benzothiazol-6-amine, the pharmaceutically acceptable acid additions salts thereof, the corresponding imidazo[2,1-b]benzothiazolium salts and the metal salt complexes thereof.
A method of treating Parkinsonism in warm-blooded animals, which comprises the systemic administration to said warm-blooded animals, in need of same, or an amount, which is effective to treat Parkinsonism, of a compound selected from the group consisting of a 2,3-dihydroimidazo[2,1-b]benzothiazole which may structurally be represented by the formula ##STR44## and the pharmaceutically acceptable acid addition salts thereof, the pharmaceutically acceptable imidazo[2,1-b]benzothiazolium salts of formula ##STR45## and metal salt complexes thereof with a transition metal salt, wherein:
- R.sup.1 and R.sup.3 are each independently selected from the group consisting of hydrogen and lower alkyl;
- R.sup.2 and R.sup.4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl, aryl-lower alkyl, lower alkyloxy-lower alkyl or aryloxy-lower alkyl;
- R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each independently selected from the group consisting of hydrogen;
- halo;
- nitro;
- alkyl having from 1 to 20 carbon atoms;
- cycloalkyl having from 3 to 6 carbon atoms;
- hydroxy;
- lower alkyloxy;
- aryloxy;
- .alpha.-hydroxy-arylmethyl;
- amino;
- mono- and dialkyl-amino;
- mono-, di- and trihalo-lower alkylamino;
- lower alkenylamino;
- lower alkynylamino;
- (aryl-lower alkyl)amino;
- (lower alkyloxy-lower alkyl)amino;
- (hydroxylower alkyl)amino;
- (aryloxy-lower alkyl)amino;
- [mono- and di(lower alkyl)amino-lower alkyl]amino;
- lower alkanoylamino;
- N-(lower alkyl)-lower alkanoylamino;
- aminocarboxylamino;
- (1-lower alkyl-4-piperidinyl)amino;cycloalkylamino wherein said cycloalkyl represents a mono-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms;
- and a radical of the formula ##STR46## wherein R.sup.10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl;
- or, when taken together R.sup.5 and R.sup.6, R.sup.6 and R.sup.7, or R.sup.7 and R.sup.8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus;
- R.sup.9 is a member selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl and aryl lower alkyl;
- and
- X is a pharmaceutically acceptable anion and n represents the valency of the anion;
- wherein aryl as used in the foregoing definitions is phenyl, optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl;
- and aroyl is arylcarbonyl.
Dependencies are inferred from the claim text.