Patent US4262004A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4262004A Expired / Lapsed US ⏱️ 0.0 years remaining

2,3-Dihydro-imidazo[2,1-b]benzothiazole compositions to treat depressions

Assignee: Janssen Pharmaceutica NV
•
Filing: 1979-06-21
•
Granted: 1981-04-14
•
Expires: 1999-06-21
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract This invention relates to a novel series of 2,3-dihydro-imidazo[2,1-b]benzothiazoles which display monoamine oxidase inhibiting activities.

Inventors

  • 👤 Victor Sipido

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 02:23
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; C07C; C07C205/00; C07C205/07; C07C205/11; C07C205/12; C07C331/00; C07C331/16; C07C331/28; C07C335/00; C07C335/04; C07C335/16; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/82; C07D277/84

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 341 words
A composition to treat depressions, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat depressions, 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 ##STR42## and the pharmaceutically acceptable acid addition salts thereof, the imidazo[2,1-b]benzothiazolium salts of formula ##STR43## and metal salt complexes thereof with a transition metal salt, wherein: R 1 and R 3 are each independently selected from the group consisting of hydrogen and lower alkyl; R 2 and R 4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl, aryllower alkyl, lower alkyloxy-lower alkyl or aryloxylower alkyl; R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen; halo; nitro; alkyl having from 1 to 20 carbon atoms; cyclalkyl having from 3 to 6 carbon atoms; hydroxy; lower alkyloxy; aryloxy; α-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; (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 mono-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms; and a radical of the formula ##STR44## wherein R 10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl; or, when taken together R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus; R 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.
Claim 2
Dependent Claim 341 words
A composition to treat depressions, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat depressions, 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 ##STR42## and the pharmaceutically acceptable acid addition salts thereof, the imidazo[2,1-b]benzothiazolium salts of formula ##STR43## and metal salt complexes thereof with a transition metal salt, wherein: R 1 and R 3 are each independently selected from the group consisting of hydrogen and lower alkyl; R 2 and R 4 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl, aryllower alkyl, lower alkyloxy-lower alkyl or aryloxylower alkyl; R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen; halo; nitro; alkyl having from 1 to 20 carbon atoms; cyclalkyl having from 3 to 6 carbon atoms; hydroxy; lower alkyloxy; aryloxy; α-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; (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 mono-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms; and a radical of the formula ##STR44## wherein R 10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl; or, when taken together R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus; R 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.
Claim 3
Dependent Claim 57 words
A composition to treat depressions, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat depressions, of a compound selected from the group consisting of N-ethyl-2,3-dihydroimidazo[2,1-b]benzothiazol-6-amine, the pharmaceutically acceptable acid addition salts thereof, are pharmaceutically acceptable corresponding imidazo[2,1-b]benzothiazolium salts thereof, and the metal salt complexes thereof with a transition metal salt.
Claim 4
Dependent Claim 57 words
A composition to treat depressions, comprising an inert carrier and, as an active ingredient, an amount, which is effective to treat depressions, of a compound selected from the group consisting of N-ethyl-2,3-dihydroimidazo[2,1-b]benzothiazol-6-amine, the pharmaceutically acceptable acid addition salts thereof, are pharmaceutically acceptable corresponding imidazo[2,1-b]benzothiazolium salts thereof, and the metal salt complexes thereof with a transition metal salt.
Claim 5
Independent Claim 343 words
A method of treating depressions in patients, which comprises the systemic administration to said patients, in need of same, of an effective anti-depressive amount 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 ##STR45## and the pharmaceutically acceptable acid addition salts thereof, and imidazo[2,1-b]benzothiazolium salts of formula ##STR46## and metal salt complexes thereof with a transition metal salt, wherein: R 1 and R 3 are each independently selected from the group consisting of hydrogen and lower alkyl; R 2 and R 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 5 , R 6 , R 7 and R 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; α-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; (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 mono-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms; and a radical of the formula ##STR47## wherein R 10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl; or, when taken together R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus; R 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.
Claim 6
Independent Claim 343 words
A method of treating depressions in patients, which comprises the systemic administration to said patients, in need of same, of an effective anti-depressive amount 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 ##STR45## and the pharmaceutically acceptable acid addition salts thereof, and imidazo[2,1-b]benzothiazolium salts of formula ##STR46## and metal salt complexes thereof with a transition metal salt, wherein: R 1 and R 3 are each independently selected from the group consisting of hydrogen and lower alkyl; R 2 and R 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 5 , R 6 , R 7 and R 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; α-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; (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 mono-, bi-, tri- or tetracyclic hydrocarbon radical having from 3 to 10 carbon atoms; and a radical of the formula ##STR47## wherein R 10 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower alkynyl; or, when taken together R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 may form a tri- or tetramethylene bridge or complete a fused benzene nucleus; R 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.

References Cited (Backward Citations)

US4042583A Cited
US3974286A Cited
US4104500A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-04-13 1984-10-13 1985-04-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-04-13 1988-10-13 1989-04-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-04-13 1992-10-13 1993-04-14 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag