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US4414225A Expired / Lapsed US ⏱️ 0.0 years remaining

Azepine derivatives and their anti-thrombotic compositions and methods

Assignee: Boehringer Ingelheim Pharma GmbH and Co KG
•
Filing: 1982-02-12
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Granted: 1983-11-08
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Expires: 2002-02-12
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Abstract

Abstract Compounds of the formula <IMAGE> wherein n and m are each 1, 2 or 3, and the sum of n+m is 4; R1 is alkyl; alkenyl; unsubstituted, mono- or di-substituted aralkyl; unsubstituted, mono- or di-substituted benzoyl; alkoxycarbonyl; aralkoxycarbonyl; or, when m and n are each 2 and/or R2 and R3 are other than both hydrogen at the same time, also hydrogen; one of R2 and R3 is hydrogen or amino, and the other is carboxyl or alkoxycarbonyl; or, when R3 is hydrogen, R2 is hydrogen; amino; alkoxycarbonyl-amino; (unsubstituted or mono-substituted phenyl)-aminocarbonyl-; (unsubstituted or mono-substituted phenyl)ethylaminocarbonyl; azidocarbonyl; or hydrazinocarbonyl; X is oxygen, sulfur or <IMAGE> where R4 is hydrogen; alkyl; phenyl-alkyl; or phenyl; non-toxic, pharmacologically acceptable acid addition salts thereof; and, when R2 or R3 is carboxyl, non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as antithrombotics.

Inventors

  • 👤 Robert Sauter
  • 👤 Gerhart Griss
  • 👤 Wolfgang Grell
  • 👤 Rudolf Hurnaus
  • 👤 Bernhard Eisele
  • 👤 Walter Haarmann
  • 👤 Eckhard Rupprecht

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 05:54
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P3/00; A61P3/06; A61P7/00; A61P7/02; C07D223/00; C07D223/02; C07D223/06; C07D491/00; C07D491/02; C07D491/04; C07D495/00; C07D495/02; C07D495/04

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 104 words
A compound of the formula ##STR9## wherein X is oxygen, sulfur, imino, methylimino, phenylimino or benzylimino; R 1 is alkyl of 1 to 3 carbon atoms; unsubstituted mono- or di-substituted benzyl, where the substituents are chlorine or bromine; chloro-hydroxybenzyl; bromo-hydroxybenzyl; unsubstituted or mono-substituted benzoyl, where the substituent is chlorine or bromine; alkoxycarbonyl of 2 to 4 carbon atoms; allyl; dodecyl, chloromethoxybenzoyl; or benzyloxycarbonyl; and R 2 is hydrogen, alkoxycarbonyl of 2 to 4 carbon atoms or carboxyl; a non-toxic, pharmacologically acceptable acid addition salt thereof; or, when R 2 is carboxyl, a non-toxic, pharmacologically acceptable salt thereof formed with an inorganic or organic base.
Claim 2
Dependent Claim 104 words
A compound of the formula ##STR9## wherein X is oxygen, sulfur, imino, methylimino, phenylimino or benzylimino; R 1 is alkyl of 1 to 3 carbon atoms; unsubstituted mono- or di-substituted benzyl, where the substituents are chlorine or bromine; chloro-hydroxybenzyl; bromo-hydroxybenzyl; unsubstituted or mono-substituted benzoyl, where the substituent is chlorine or bromine; alkoxycarbonyl of 2 to 4 carbon atoms; allyl; dodecyl, chloromethoxybenzoyl; or benzyloxycarbonyl; and R 2 is hydrogen, alkoxycarbonyl of 2 to 4 carbon atoms or carboxyl; a non-toxic, pharmacologically acceptable acid addition salt thereof; or, when R 2 is carboxyl, a non-toxic, pharmacologically acceptable salt thereof formed with an inorganic or organic base.
Claim 3
Dependent Claim 51 words
A compound of claim 1, where X is sulfur; R 1 is dodecyl, benzyl, chlorobenzyl or chlorobenzoyl; and R 2 is hydrogen or carboxyl, a non-toxic, pharmacologically acceptable acid addition salt thereof; or, when R 2 is carboxyl, a non-toxic, pharmacologically acceptable salt thereof formed with an inorganic or organic base.
Claim 4
Dependent Claim 8 words
The compound of claim 1 which is 6-(2-chlorobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine.
Claim 5
Dependent Claim 17 words
A compound of claim 1, which is 6-(2-chlorobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 16 words
A compound of claim 1, which is 6-benzyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine-2-carboxylic acid or a non-toxic, pharmacologically acceptable salt thereof.
Claim 7
Dependent Claim 22 words
An antithrombotic pharmaceutical composition consisting essentially of an inert pharmaceutical carrier and an effective antithrombotic amount of a compound of claim 1.
Claim 8
Dependent Claim 31 words
The method of preventing or relieving thrombosis in a warm-blooded animal, which comprises perorally, parenterally or rectally administering to said animal an effective antithrombotic amount of a compound of claim 1.

References Cited (Backward Citations)

US3758501A Cited
US3846446A Cited
US3849441A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-11-07 1987-05-09 1987-11-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-11-07 1991-05-09 1991-11-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-11-07 1995-05-09 1995-11-08 $7700.00 Window Closed / Lapsed

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