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US4344946A Expired / Lapsed US ⏱️ 0.0 years remaining

2,6-Diamino-benzo[1,2-d:5,4-d']bisthiazoles and salts thereof

Assignee: Boehringer Ingelheim GmbH
•
Filing: 1980-08-28
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Granted: 1982-08-17
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Expires: 2000-08-28
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Abstract

Abstract Compounds of the formula <IMAGE> wherein R1 and R1', which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 2 carbon atoms; R2 and R2', which may be identical to or different from each other, are each hydrogen or <IMAGE> but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms, R5 is hydrogen, lower alkyl, lower alkylamino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino; R6 is hydrogen, lower alkyl, lower alkylamino-lower alkyl or lower alkoxy-lower alkyl; or R5 and R6, together with each other and the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring, where a 5- or 6-membered ring may comprise an additional sulfur or nitrogen heteroatom, and in the latter case said heterocyclic ring may optionally have one or two lower alkyl substituents, a lower alkoxy-carbonyl, a lower alkoxy-carbonyl-methyl, a hydroxy-lower alkyl, a trifluoroethyl, a cycloalkyl, a lower alkyl-cycloalkyl, a cyclohexylmethyl, a benzyl, a pyridyl, a piperidino, a phenyl, a fluoro-phenyl, a chloro-phenyl, a trifluoromethyl-phenyl, or an acetyl-phenyl substituent attached thereto; and R3 and R4, which may be identical to or different from each other, are each hydrogen, chlorine, bromine, lower alkyl, lower alkoxy, lower alkanoyl, hydroxycarbonyl, lower alkoxy-carbonyl, amino-carbonyl, phenyl, trifluoromethyl, nitro, cyano or amino; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as antiarthritics and antirheumatics.

Inventors

  • 👤 Ernest Cullen
  • 👤 Genus Possanza
  • 👤 Patrick B. Stewart

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 12:00
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; A; A61; A61P; A61P19/00; A61P19/02; A61P29/00

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 224 words
A compound of the formula ##STR11## wherein R 1 and R 1 ' are each hydrogen or alkyl of 1 to 2 carbon atoms; R 2 and R 2 ' are each hydrogen or ##STR12## but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms, R 5 is hydrogen, lower alkyl, lower alkyl-amino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino; R 6 is hydrogen, lower alkyl, lower alkyl-amino-lower alkyl or lower alkoxy-lower alkyl; or R 5 and R 6 , together with each other and the nitrogen atom to which they are attached, form a piperidino or piperazino ring and said heterocyclic rings may optionally have one or two lower alkyl substituents, a lower alkoxy-carbonyl, a lower alkoxy-carbonyl-methyl, a hydroxy-lower alkyl, a trifluoroethyl, a cycloalkyl of 5 to 7 carbon atoms, a lower alkyl-cycloalkyl of 5 to 7 carbon atoms, a cyclohexylmethyl, a benzyl, a pyridyl, a piperidino, a phenyl, a fluoro-phenyl, a chloro-phenyl, a trifluoromethyl-phenyl, or an acetyl-phenyl substituent attached thereto; and R 3 and R 4 are each hydrogen, chlorine, bromine, lower alkyl, lower alkoxy, lower alkanoyl, hydroxy-carbonyl, lower alkoxy-carbonyl, amino-carbonyl, phenyl, trifluoromethyl, nitro, cyano or amino; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 224 words
A compound of the formula ##STR11## wherein R 1 and R 1 ' are each hydrogen or alkyl of 1 to 2 carbon atoms; R 2 and R 2 ' are each hydrogen or ##STR12## but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms, R 5 is hydrogen, lower alkyl, lower alkyl-amino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino; R 6 is hydrogen, lower alkyl, lower alkyl-amino-lower alkyl or lower alkoxy-lower alkyl; or R 5 and R 6 , together with each other and the nitrogen atom to which they are attached, form a piperidino or piperazino ring and said heterocyclic rings may optionally have one or two lower alkyl substituents, a lower alkoxy-carbonyl, a lower alkoxy-carbonyl-methyl, a hydroxy-lower alkyl, a trifluoroethyl, a cycloalkyl of 5 to 7 carbon atoms, a lower alkyl-cycloalkyl of 5 to 7 carbon atoms, a cyclohexylmethyl, a benzyl, a pyridyl, a piperidino, a phenyl, a fluoro-phenyl, a chloro-phenyl, a trifluoromethyl-phenyl, or an acetyl-phenyl substituent attached thereto; and R 3 and R 4 are each hydrogen, chlorine, bromine, lower alkyl, lower alkoxy, lower alkanoyl, hydroxy-carbonyl, lower alkoxy-carbonyl, amino-carbonyl, phenyl, trifluoromethyl, nitro, cyano or amino; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 97 words
A compound of claim 1, where R 1 and R 1 ' are hydrogen, R 2 and R 2 ' are both --CO--CH 2 --NR 5 R 6 ; where R 5 and R 6 are each hydrogen, methyl, ethyl or, together with each other and the nitrogen atom to which they are attached, piperidino or piperazino, where the heterocycles may optionally have a methyl, piperidino, phenyl or trifluoromethyl-phenyl substituent attached thereto; and R 3 and R 4 are each hydrogen, chlorine, bromine, methyl, methoxy, cyano or trifluoromethyl; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim 84 words
A compound of claim 1, where R 1 and R 1 ' are both hydrogen; R 2 and R 2 ' are both --CO--CH 2 --NR 5 R 6 , where R 5 and R 6 are ethyl or, together with each other and the nitrogen atom to which they are attached, piperidino, methyl-piperidino, piperazino or methyl-piperazino; R 2 is hydrogen, methyl-piperazino, chlorine or bromine; and R 4 is hydrogen, chlorine, bromine, cyano or trifluoromethyl; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a nontoxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(piperidino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-chloro-8-trifluoromethyl-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-chloro-8-cyanobenzo[1,2-d:5,4-d']bisthiazole or a nontoxic, pharmacologically acceptable acid addition salt thereof.
Claim 9
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-methyl-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 10
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(4-methylpiperidino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 11
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4,8-dichloro-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 12
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-bromo-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 13
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-chloro-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 14
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-bromo-8-chloro-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 15
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(diethylamino-acetylamino)-4-chloro-8-bromo-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 16
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(dimethylamino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 17
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(o-methylpiperidino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 18
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(p-methylpiperazino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 19
Dependent Claim 17 words
A compound of claim 1, which is 2,6-bis-(ethylamino-acetylamino)-benzo[1,2-d:5,4-d]-bisthiazole or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 20
Dependent Claim 28 words
An antiarthritic or antirheumatic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective antiarthritic or antirheumatic amount of a compound of claim 1.
Claim 21
Dependent Claim 37 words
The method of relieving arthritis or rheumatism in a warm-blooded animal in need thereof, which comprises perorally, parenterally, rectally or topically administering to said animal an effective antiarthritic or antirheumatic amount of a compound of claim 1.

References Cited (Backward Citations)

US2140540A Cited
US2182815A Cited
US3489558A Cited
US3501293A Cited
US4065462A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-08-16 1986-02-15 1986-08-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-08-16 1990-02-15 1990-08-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-08-16 1994-02-15 1994-08-17 $7700.00 Window Closed / Lapsed

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