EP0067685A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Alpha-phenyl-2-(aza)benzothiazolylthioglycolic acids and derivatives thereof
Assignee: Wyeth LLC
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Filing: 1982-06-11
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Granted: —
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Expires: 2002-06-11
Abstract
Abstract Compounds having the formula I wherein R, is hydrogen, halo, nitro, amino, lower alkyl, lower alkoxy, trifluoromethyl or hydroxy R 2 is hydrogen, fluorine, chlorine, bromine, lower alkyl, lower alkoxy, amino, nitro or trifluoromethyl; R 3 is hydroxy, lower alkoxy, amino, hydroxy(lower)alkylamino, N-(lower)alkanoylamino(lower)alkoxy or N-arylcarbamoyl-(lower)alkylthio; X is CH or N, and the dotted lines represent optional double bonds in the 5, 6 and 7, 8-positions and their pharmacologically acceptable salts are useful as pharmaceuticals, particularly as immuno modulating agents. Processes for making the compounds having formula I and their pharmacologically acceptable salts are also described. The compounds are new per se, provided that, where R 3 is hydroxy, then R, is nitro.
Inventors
- 👤 Peter Hsing-Lien Wei
- 👤 Francis Joseph Gregory
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 17:54
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
86 words
A pharmaceutical composition comprising a compound having the formula I wherein R 1 is hydrogen, halo, nitro, amino, lower alkyl, lower alkoxy, trifluoromethyl or hydroxy; R 2 is hydrogen, fluorine, chlorine, bromine, lower alkyl, lower alkoxy, amino, nitro or trifluoromethyl; R 3 is hydroxy, lower alkoxy, amino, hydroxy(lower)-alkylamino, N-(lower)alkanoylamino(lower)alkoxy or N-arylcarbamoyl(lower)alkylthio; X is CH or N, and the dotted lines represent optional double bonds in the 5, 6 and 7,8- positions, or a pharmacologically acceptable salt thereof in association or combination with a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
86 words
A pharmaceutical composition comprising a compound having the formula I wherein R 1 is hydrogen, halo, nitro, amino, lower alkyl, lower alkoxy, trifluoromethyl or hydroxy; R 2 is hydrogen, fluorine, chlorine, bromine, lower alkyl, lower alkoxy, amino, nitro or trifluoromethyl; R 3 is hydroxy, lower alkoxy, amino, hydroxy(lower)-alkylamino, N-(lower)alkanoylamino(lower)alkoxy or N-arylcarbamoyl(lower)alkylthio; X is CH or N, and the dotted lines represent optional double bonds in the 5, 6 and 7,8- positions, or a pharmacologically acceptable salt thereof in association or combination with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
11 words
A composition as claimed in Claim 1, in unit dosage form.
Claim 4
Dependent Claim
30 words
A composition as claimed in Claim 1 or 2 in the form of one or more tablets or capsules or in the form of a sterile solution containing other solutes.
Claim 5
Dependent Claim
55 words
A composition as claimed in any one of Claims 1 to 3, wherein the compound having formula I is selected from a-(2-benzothiazolylthio)benzene acetic acid; a-(5-chlorobenzothiazol-2-ylthio)benzeneacetic acid; a-(5-chlorobenzothiazol-2-ylthio)-a-(p-chlorophenyl)acetic acid; α-(p-chlorophenyl)-α-(benzo- thiazol-2-ylthio)acetic acid; a-(5-chloro-2-benzo- thiazolylthio)benzene acetic acid, ethyl ester; a-(5-chlorobenzothiazol-2-ylthio)-a-phenylacetamide; a-[(5-chloro-2-benzothiazolyl)thio]-N-(2-hydroxyethyl)-benzene-acetamide; a-[(5-chloro-2-benzothiazolyl)thio]-benzene acetic acid,[2-(acetylamino)ethyl]ester; α-[(5-chloro-2-benzothiazolyl)thio]benzeneethanethioic acid,S-[2-(2-naphthalenylamino)-2-oxoethyl]ester; a-[(5-chlorothiazolo[5,4-b]pyridin-2-yl)thio]-a-phenylacetic acid; a-[5-chlorothiazolo[5,4-b]pyridin-2-yl)thio]-α-(p-chlorophenyl)acetic acid; a-phenyl- a-[(4,5,6,7-tetrahydrobenzothiazol-2-yl)thio]acetic acid and a-[(6-nitro-2-benzothiazolyl)thio]benzene- acetic acid.
Claim 6
Dependent Claim
37 words
For use as an immunomodulating agent, a compound have the formula I (wherein R1 , R 2 , R 3' X and the dotted lines are as defined in Claim 1) or a pharmacologically acceptable salt thereof.
Claim 7
Dependent Claim
41 words
A compound as claimed in Claim 5, which is selected from a-(2-benzothiazolylthio)benzene acetic acid; a-(5-chlorobenzothiazol-2-ylthio)benzene acetic acid; α-(5-chlorobenzothiazol-2-ylthio)-α-(p-chlorophenyl) acetic acid; α-(p-chlorophenyl)-α-(benzothiazol-2- ylthio)acetic acid; α-[(5-chlorothiazolo [5 4-b] pyridin-2-yl)thio]-a-phenylacetic acid; a-(5-chloro- thiazolo[5,4-b]pyridin-2-yl)thio-a-(p-chlorophenyl) acetic acid; a-phenyl-a-[(4,5,6,7-tetrahydrobenzo- thiazol-2-yl)thio]acetic acid and the pharmacologically acceptable salts thereof.
Claim 8
Dependent Claim
48 words
A compound having the formula I or a pharmacologically acceptable salt thereof, wherein R 1 , R 2 , R 3 , X and the dotted lines are as defined in Claim 1 subject to the proviso that, where R 3 is hydroxy, then R 1 is nitro.
Claim 9
Dependent Claim
23 words
A compound selected from a-[(6-nitro-2-benzothiazolyl)-thio]-benzeneacetic acid and the pharmacologically acceptable salts thereof; a-[(5-chloro-2-benzothiazolyl)thio]benzene ethanethioic acid,S-[2-(2-naphthalenylamino)-2-oxoethyl]ester; a-[(5-chloro-2-benzothiazolyl)thio]benzeneacetic acid,[2-(acetylamino)ethyl]ester; a-[(5-chloro-2-benzothiazolyl)-thio]-N-(2-hydroxyethyl)benzeneacetamide; and α-(5-chloro-2-benzothiazolylthio)benzeneacetic acid, ethyl ester.
Claim 10
Dependent Claim
23 words
A compound selected from a-[(6-nitro-2-benzothiazolyl)-thio]-benzeneacetic acid and the pharmacologically acceptable salts thereof; a-[(5-chloro-2-benzothiazolyl)thio]benzene ethanethioic acid,S-[2-(2-naphthalenylamino)-2-oxoethyl]ester; a-[(5-chloro-2-benzothiazolyl)thio]benzeneacetic acid,[2-(acetylamino)ethyl]ester; a-[(5-chloro-2-benzothiazolyl)-thio]-N-(2-hydroxyethyl)benzeneacetamide; and α-(5-chloro-2-benzothiazolylthio)benzeneacetic acid, ethyl ester.
Claim 11
Dependent Claim
1 words
a-(5-Chlorobenzothiazol-2-ylthio)-a-phenylacetamide.
Claim 12
Dependent Claim
1 words
a-(5-Chlorobenzothiazol-2-ylthio)-a-phenylacetamide.
Claim 13
Dependent Claim
152 words
A process for the preparation of a compound having the formula: (wherein R 1 , R 2 , R 3 , X and the dotted lines are as defined in Claim 1) or a pharmacologically acceptable salt thereof, which comprises (a) reacting a compound having the formula II (wherein R 1 , X and the dotted lines are as defined in Claim 1) or a salt thereof with a compound having the formula (wherein Hal is chlorine or bromine and R 2 and R 3 are as defined in Claim 1 subject to the proviso that, where R 3 is hydroxy, then R 1 in formula II is nitro) or a salt thereof; or (b) reacting a compound having the formula IV with a compound having the formula R 3 H (wherein R 1 , R 2 , R 3 , X and the dotted lines are as defined in Claim 1).
References Cited (Backward Citations)
EP0021773A1
Cited
EP0030632A2
Cited
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