Benzoic acids, their derivatives and process for preparing them

• US 4,221,815 A
• Filed: 01/02/1976
• Issued: 09/09/1980
• Est. Priority Date: 01/03/1975
• Status: Expired due to Term

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Geisen, Karl, Hitzel, Volker, Weyer, Rudi, Pfaff, Werner
• Primary Examiner(s): Breitenstein, G. T.
• Application Number:
  US05/646,378
• Time in Patent Office: 1,712 Days
• Field of Search: 260/519, 260/518 R, 560/38, 560/42, 560/45, 560/47, 560/48, 562/442, 562/455, 562/456, 562/457, 562/458, 562/451, 424/319, 424/309, 424/316
• US Class Current: 514/563
• CPC Class Codes: C07D 213/82 in position 3
• CPC Class Codes: C07D 215/48 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 307/79 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 311/58 other than with oxygen or sulphur atoms in position 2 or 4
• CPC Class Codes: C07D 333/38 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.

Claims

1. A benzoic acid derivative of the formula ##STR16## in which T'"'"' is hydrogen or halogen;

W'"'"' represents a carboxyl group, an ester or a salt thereof;

R is hydrogen, alkyl, alkoxy, alkenoxy, alkoxy-alkoxy, phenoxy, halogen, anilino or trifluoromethyl;

R₁ and R₂, independently of each other, are hydrogen, alkyl, alkoxy or halogen;

Y'"'"' is a hydrocarbon radical of 2 to 3 carbon atoms; and

Z'"'"' is hydrogen, halogen or alkyl,

5. An oral antidiabetic composition containing, as the essential active component, a hypoglycemically effective amount of a compound defined in claim 1.

9. A method of treatment which comprises orally administering to a diabetic patient an effective amount of a compound defined in claim 1.

2. A benzoic acid derivative of the formula ##STR17## and the esters and physiologically tolerable salts thereof in which T'"'"' is hydrogen, chlorine or bromine;

R is hydrogen, alkyl, alkoxy, alkenoxy, alkoxy-alkoxy, phenoxy, halogen, anilino or trifluoromethyl;

R₁ and R₂, independently of each other, are hydrogen, alkyl, alkoxy or halogen;

Y'"'"' is a hydrocarbon radical of 2 to 3 carbon atoms; and

Z'"'"' is hydrogen, halogen or alkyl,

3. A compound as defined in claim 2 in which R is alkoxy or alkenoxy, R₁ and R₂ are hydrogen, alkyl, alkoxy or halogen and Z'"'"' is hydrogen or alkyl.

4. The compound of claim 3 which is 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-benzoic acid.

6. An oral antidiabetic composition containing, as the essential active component, a hypoglycemically effective amount of a compound defined in claim 2.

7. An oral antidiabetic composition containing, as the essential active component, a hypoglycemically effective amount of a compound defined in claim 3.

8. An oral antidiabetic composition containing, as the essential active component, a hypoglycemically effective amount of the compound defined in claim 4.

10. A method of treatment which comprises orally administering to a diabetic patient an effective amount of a compound defined in claim 2.

11. A method of treatment which comprises orally administering to a diabetic patient an effective amount of a compound defined in claim 3.

12. A method of treatment which comprises orally administering to a diabetic patient an effective amount of the compound defined in claim 4.