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US4093734A Expired / Lapsed US ⏱️ 0.0 years remaining

Amino-benzoic acid amides

Assignee: Boehringer Ingelheim GmbH
•
Filing: 1976-10-22
•
Granted: 1978-06-06
•
Expires: 1996-10-22
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Abstract

Abstract Compounds of the formula <IMAGE> wherein (A) WHEN THE AMINO-SUBSTITUENT IS IN THE P-POSITION WITH RESPECT TO THE CARBONYL GROUP, R1 is chlorine in the o-position with respect to the carbonyl group, R2 is hydrogen, and R3 is ethylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, N-methyl-cyclohexylamino, benzylamino or 1-ethyl-pyrrolidyl-(2)-aminomethyl, or (B) WHEN THE AMINO-SUBSTITUENT IS IN THE O-, M- OR P-POSITION WITH RESPECT TO THE CARBONYL GROUP, R1 is hydrogen, chlorine or bromine, R2 is trifluoromethyl, nitro or, when R4 is 1-(alkyl of 1 to 3 carbon atoms)-pyrrolidyl or 1-(alkyl of 1 to 3 carbon atoms)-piperidyl, also fluorine, chlorine, bromine or methyl, R3 is (alkyl of 1 to 5 carbon atoms)-amino, (cycloalkyl of 3 to 7 carbon atoms)-amino, benzylamino, quinuclidinyl-amino or -NH-(CH2)n-R4 where R4 is pyridyl, 1-(alkyl of 1 to 3 carbon atoms)-pyrrolidyl, 1-(alkyl of 1 to 3 carbon atoms)-piperidyl or, when n is 2 or 3, also imidazolonyl, pyrrolidino, piperidino or morpholino, and N IS 0, 1, 2 OR 3, AND NON-TOXIC, PHARMACOLOGICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF; THE COMPOUNDS AS WELL AS THEIR SALTS ARE USEFUL AS ANXIOLYTICS, ANTICONVULSIVES, ANTIEMETICS AND ANTIULCEROGENICS.

Inventors

  • 👤 Gerd Kruger
  • 👤 Johannes Keck
  • 👤 Klaus Reinhold Noll
  • 👤 Helmut Pieper
  • 👤 Harald Ziegler
  • 👤 Helmut Ballhause
  • 👤 Joachim Kahling

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 03:36
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; A; A61; A61P; A61P1/00; A61P1/04; A61P1/08; A61P25/00; A61P25/24; A61P25/26; C07D207/00; C07D207/02; C07D207/04; C07D207/08; C07D207/09; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/26; C07D211/36; C07D211/56; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D295/00; C07D295/04; C07D295/12; C07D295/125; C07D295/13; C07D453/00; C07D453/02

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 45 words
A compound of the formula ##STR11## wherein R 1 is hydrogen, chlorine or bromine, R 2 is methyl, fluorine, chlorine, bromine, trifluoromethyl or nitro, and R 4 is 1-(alkyl of 1 to 3 carbon atoms)-pyrrolidinyl (2), or a non-toxic, phamacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 45 words
A compound of the formula ##STR11## wherein R 1 is hydrogen, chlorine or bromine, R 2 is methyl, fluorine, chlorine, bromine, trifluoromethyl or nitro, and R 4 is 1-(alkyl of 1 to 3 carbon atoms)-pyrrolidinyl (2), or a non-toxic, phamacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 91 words
A compound of claim 1, where the --NH 2 substituent is in the o-- or p-- position with respect to the carbonyl group, substitnents R 1 and R 2 are in the 3- and 5- position, respectively, in relation to the carbonyl group, one of R 1 and R 2 is hydrogen, chlorine or bromine, the other of R 1 and R 2 is methyl, flourine, chlorine, bromine, trifluoromethyl or nitro, and R 4 is 1-(alkyl of 1 to 2 carbon atoms)-pyrrolidinyl-(2), or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim 33 words
A compound of claim 2, where R 1 is hydrogen, chlorine or bromine, R 2 is trifluoromethyl or nitro, and R 4 is 1-ethyl-pyrrolidinyl-(2), or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 19 words
A compound of claim 3, which is N-[1-ethylpyrrolidinyl-(2)-methyl]-2-amino-5-chloro-3-trifluoromethylbenzoic acid amide or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 19 words
A compound of claim 3, which is N-[1-ethylpyrrolidinyl-(2)-methyl]-4-amino-3-chloro-5-trifluoromethylbenzoic acid amide or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim 25 words
An anxiolytic or anticonvulsive pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective amount of a compound of claim 1.
Claim 8
Dependent Claim 36 words
The method of relieving anxiety and convulsions in a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective anxiolytic or anticonvulsive amount of a compound of claim 1.

References Cited (Backward Citations)

US3455940A Cited
US3821248A Cited
US3891671A Cited
US3923829A Cited
US3975434A Cited
US3900481A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-06-05 1981-12-05 1982-06-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-06-05 1985-12-05 1986-06-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-06-05 1989-12-05 1990-06-06 $7700.00 Window Closed / Lapsed

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