Derivatives of N-phenylbenzamide with anti-ulcer and anti-allergy

• US 5,232,937 A
• Filed: 08/19/1991
• Issued: 08/03/1993
• Est. Priority Date: 02/22/1989
• Status: Expired due to Term

• Current Assignee: Rottapharm SpA (Mylan N.V.)
• Original Assignee: Rotta Research Laboratorium Spa
• Inventors: Rovati, Angelo L., Makovec, Francesco, Peris, Walter
• Primary Examiner(s): GERSTL, ROBERT
• Application Number:
  US07/752,435
• Time in Patent Office: 715 Days
• Field of Search: 558/393, 562/435, 562/450, 548/253, 514/381, 514/522, 514/563
• US Class Current: 514/381
• CPC Class Codes: C07C 233/81 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
• CPC Class Codes: C07C 235/56 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 255/57 containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
• CPC Class Codes: C07C 255/60 at least one of the singly-bound nitrogen atoms being acylated
• CPC Class Codes: C07D 257/04 Five-membered rings

Abstract

Derivatives of N-phenylbenzamide with general formula (1) in which R₁ is a cyano, nitro, halogen, hydrozy, C₁ -C₄ alkyl methyl, methoxy or tetrazol-5-yl group, R₂ is hydrogen, hydroxy, or methoxy, R₃ is a tetrazol-5-yl group or hydrogen, R₄ and R₅ are hydrogen if R₃ is tetrazolyl but are independently selected from the group consisting of carboxy, methoxycarbonyl, ethoxycarbonyl and carbamoyl if R₃ is hydrogen, and R₆ is hydrogen or methyl. The derivatives have an anti-ulcer and anti-allergy activity.

Claims

1. Pharmaceutically active derivatives of N-phenylbenzamide having the formula (I) ##STR2## in which R₁ is a cyano, nitro, halogen, hydroxy, C₁ -C₄ alkyl, methoxy or tetrazol-5-yl group,

R₂ is a hydrogen, hydroxy, or methoxy group,

R₃ is a tetrazol-5-yl group or hydrogen,

R₄ and R₅ are hydrogen if R₃ is tetrazolyl or R₄ and R₅ are independently selected from the group consisting of carboxy, methoxycarbonyl, ethoxycarbonyl and carbamoyl if R₃ is hydrogen, and R₆ is hydrogen or methyl, and their pharmaceutically acceptable salts.

2. Derivatives of N-phenylbenzamide according to claim 1, of formula (I) in which R₁ is selected from the cyano group and the tetrazol-5-yl group, in which R₂ is hydrogen, R₃ is a tetrazol-5-yl group if R₄ and R₅ are hydrogen or R₃ is hydrogen if R₄ and R₅ are both carboxy groups.

3. A derivative of N-phenylbenzamide according to claim 1, of formula (I), in which R₁ is the cyano group, R₂, R₄ and R₅ are hydrogen and R₃ is the tetrazolyl group.

4. A derivative of N-phenylbenzamide according to claim 1, of formula (I), in which R₁ is the cyano group, R₂ and R₃ are hydrogen and R₄ and R₅ are both carboxy groups.

5. A derivative of N-phenylbenzamide according to claim 1, of formula (I) in which R₁ and R₃ are both the tetrazol-5-yl group and R₂, R₄ and R₅ are hydrogen.

6. Pharmaceutical compositions including a compound according to claim 1 or a pharmaceutically acceptable salt thereof as the active ingredient and a pharmaceutically accaptable carrier.

7. A method comprising administering to a patient in need of treatment of a gastrointestinal disorder characterized by excessive secretion, a therapeutically effective amount of an N-phenylbenzamide derivative of claim 1.

8. A method comprising administering to a patient in need of treatment of allergic disorders resulting from antigen-antibody reactions or from mediators of an immune response, a therapeutically effective amount of an N-phenylbenzamide derivative of claim 1.