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EP0324610A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Thieno[2,3-d]azepine derivatives, process for their preparation and pharmaceutical compositions containing them

Assignee: Lilly Industries Ltd
•
Filing: 1989-01-12
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Granted: —
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Expires: 2009-01-12
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Abstract

Abstract Compounds of the formula in which R¹ is hydrogen, hydroxy, nitro, cyano, halo, amino, acetamido, hydroxy-C₁₋₄ alkyl, carboxaldehydo, C₁₋₄ alkyl­carbonyl, carboxy, C₁₋₄ alkoxy-carbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl or C₁₋₄ alkoxy-C₁₋₄ alkyl, R² is hydrogen, hydroxy, nitro, cyano, halo, amino, carboxamido, acetamido, hydroxy-C₁₋₄alkyl, carboxaldehydo, C₁₋₄ alkylcarbonyl, carboxy, C₁₋₄ alkoxycarbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, oximino or aminomethyl, R³ is optionally substituted phenyl or optionally substituted phenyl ortho condensed with an optionally substituted ring selected from benzene, cyclohexane, cyclohexene, cyclopentane or cyclopentene, in which ring one of the carbon atoms may be replaced by oxygen, sulphur or nitrogen, and R⁴ is hydrogen, C₁₋₄ alkyl, C₂₋₄ alkenyl or optionally sub­stituted benzyl; and salts thereof; have central nervous system activity.

Inventors

  • 👤 Barry Peter Clark
  • 👤 David Edward Tupper

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 16:27
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A; A61; A61P; A61P25/00

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 122 words
A compound of the formula in which R¹ is hydrogen, hydroxy, nitro, cyano, halo, amino, acetamido, hydroxy-C₁₋₄ alkyl, carboxaldehydo, C₁₋₄ alkyl­carbonyl, carboxy, C₁₋₄ alkoxy-carbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl or C₁₋₄ alkoxy-C₁₋₄ alkyl, R² is hydrogen, hydroxy, nitro, cyano, halo, amino, carboxamido, acetamido, hydroxy-C₁₋₄alkyl, carboxaldehydo, C₁₋₄ alkylcarbonyl, carboxy, C₁₋₄ alkoxycarbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, oximino or aminomethyl, R³ is optionally substituted phenyl or optionally substituted phenyl ortho condensed with an optionally substituted ring selected from benzene, cyclohexane, cyclohexene, cyclopentane or cyclopentene, in which ring one of the carbon atoms may be replaced by oxygen, sulphur or nitrogen, and R⁴ is hydrogen, C₁₋₄ alkyl, C₂₋₄ alkenyl or optionally sub­stituted benzyl; and salts thereof.
Claim 2
Dependent Claim 122 words
A compound of the formula in which R¹ is hydrogen, hydroxy, nitro, cyano, halo, amino, acetamido, hydroxy-C₁₋₄ alkyl, carboxaldehydo, C₁₋₄ alkyl­carbonyl, carboxy, C₁₋₄ alkoxy-carbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl or C₁₋₄ alkoxy-C₁₋₄ alkyl, R² is hydrogen, hydroxy, nitro, cyano, halo, amino, carboxamido, acetamido, hydroxy-C₁₋₄alkyl, carboxaldehydo, C₁₋₄ alkylcarbonyl, carboxy, C₁₋₄ alkoxycarbonyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulphonyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, oximino or aminomethyl, R³ is optionally substituted phenyl or optionally substituted phenyl ortho condensed with an optionally substituted ring selected from benzene, cyclohexane, cyclohexene, cyclopentane or cyclopentene, in which ring one of the carbon atoms may be replaced by oxygen, sulphur or nitrogen, and R⁴ is hydrogen, C₁₋₄ alkyl, C₂₋₄ alkenyl or optionally sub­stituted benzyl; and salts thereof.
Claim 3
Dependent Claim 13 words
A compound according to claim 1 in which R³ is phenyl or benzofuranyl.
Claim 4
Dependent Claim 29 words
A compound according to either of claims 1 and 2 in which R¹ is hydrogen, halo or C₁₋₄ alkylthio, and R² is hydrogen, hydroxy-C₁₋₄ alkyl, halo or C₁₋₄ alkyl.
Claim 5
Dependent Claim 15 words
A compound according to any of the preceding claims in which R⁴ is C₁₋₄ alkyl.
Claim 6
Dependent Claim 35 words
A compound according to claim 1, in which R¹ is halogen or C₁₋₄ alkylthio, R² is hydrogen, hydroxy-C₁₋₄ alkyl, C₁₋₄ alkyl or halo, R³ is phenyl or benzofuranyl, and R⁴ is hydrogen or C₁₋₄ alkyl.
Claim 7
Dependent Claim 35 words
A compound according to claim 1, in which R¹ is hydrogen, halo or C₁₋₄ alkylthio, R² is hydrogen, hydroxymethyl, halo or C₁₋₄ alkyl, R³ is phenyl or benzofuranyl and R⁴ is hydrogen or C₁₋₄ alkyl.
Claim 8
Dependent Claim 29 words
A pharmaceutical formulation which comprises a compound according to any of claims 1 to 6 or a pharmaceutically-­acceptable salt thereof, in association with a pharmaceutically­acceptable diluent or carrier therefor.
Claim 9
Dependent Claim 15 words
A compound according to any of claims 1 to 6, for use as a pharmaceutical.
Claim 10
Dependent Claim 48 words
A process for producing a compound according to claim 1 which comprises cyclising a compound of the formula in which R¹, R², R³, and R⁴ have the above values, optionally followed when one or more of R¹, R² and R⁴ is hydrogen by introduction of an appropriate substituent.

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