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Claims for Patent: RE37035

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Claims for Patent: RE37035

Title: Phenylacetic acid benzylamides
Abstract:Phenylacetic acid benzylamides having the following general structure ##STR1## wherein the substituents are defined herein, are disclosed, which compounds are hypoglcemic agents.
Inventor(s): Grell; Wolfgang (Biberach, DE), Hurnaus; Rudolf (Biberach, DE), Griss; Gerhart (late of Biberach, DE), Sauter; Robert (Laupheim, DE), Reiffen; Manfred (Biberach, DE), Rupprecht; Eckhard (Guntramsdorf, AT)
Assignee: Boehringer Ingelheim KG (Ingelheim, DE)
Application Number:08/946,602
Patent Claims: 1. A compound of the formula: ##STR19##

wherein

R.sub.1 represents an unbranched alkyleneimino group with 4 to 6 carbon atoms optionally mono- or di-(alkyl of 1 to 3 carbon atoms)-substituted;

R.sub.2 represents a hydrogen or halogen atom or a methyl or methoxy group;

R.sub.3 represents a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a phenyl group optionally substituted by a halogen atom or a methyl or methoxy group, an alkyl group with 1 or 2 carbon atoms substituted by a hydroxy, alkoxy, alkanoyloxy, tetrahydrofuranyl, tetrahydropyranyl, cyclocalkyl or phenyl group, in which the alkoxy part can contain from 1 to 3 carbon atoms, the alkanoyloxy part can contain 2 or 3 carbon atoms and the cycloalkyl part can contain 3 to 7 carbon atoms, an alkenyl group with 3 to 6 carbon atoms, an alkynyl group with 3 to 5 carbon atoms, a carboxy group or an alkoxycarbonyl group with a total of 2 to 5 carbon atoms;

R.sub.4 represents a hydrogen atom, a methyl, ethyl or allyl group; and

W represents a methyl, hydroxymethyl, formyl, carboxyl, alkoxycarbonyl, cyanomethyl, 2-cyanoethyl, 2-carboxyethenyl, alkoxycarbonylmethyl, 2-alkoxycarbonyl-ethyl or 2-alkoxycarbonylethenyl group, in which each alkoxy part can contain from 1 to 4 carbon atoms and can be substituted by a phenyl group; and

when R.sub.3 is other then hydrogen and/or the radical R.sub.1 contains an optically active carbon atom, the enantiomeres and the diastereomeres thereof or their mixtures; when W is carboxyl, a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the amino function in the R.sub.1 -position.

2. A compound of claim 1, wherein

R.sub.1 represents a pyrrolidino, piperidino, 4-methyl-piperidino, 3-methyl-piperidino, 3,3-dimethyl-piperidino, 3,5-dimethyl-piperidino or hexamethyleneimino group;

R.sub.2 represents a hydrogen, fluorine or chlorine atom;

R.sub.3 represents hydrogen atom, an alkyl group with 1 to 6 carbon atoms, a phenyl, methyl-phenyl, chloro-phenyl, methoxy-phenyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, tetrahydrofuran-2-yl-methyl, tetrahydropyran-2-yl-methyl, propargyl, hydroxymethyl, ethoxymethyl, acetoxymethyl, propionyloxymethyl, carboxy, methoxycarbonyl, ethoxycarbonyl or propoxycarbonyl group or an alkenyl group with 3 or 4 carbon atoms;

R.sub.4 represents a methyl, ethyl or allyl group; and

W represents a methyl, hydroxymethyl, formyl, carbonyl, benzyloxycarbonyl, carboxymethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyanomethyl, 2-carboxy-ethyl, 2-ethoxycarbonyl-ethyl, 2-cyano-ethyl, 2-carboxy-ethenyl, 2-ethoxycarbonyl-ethenyl or 2-cyano-ethenyl group or an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxy part; and

when R.sub.3 is other then hydrogen and/or R.sub.1 represents the 3-methyl-piperidino group, the enantiomeres and the diastereomeres thereof or their mixtures; when W is carboxyl, a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the amino function in the R.sub.1 -position.

3. A compound of claim 1, wherein

R.sub.1 represents a piperidino group;

R.sub.2 represents a hydrogen atom;

R.sub.3 represents an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 3 or 4 carbon atoms, a phenyl, tetrahydropyran-2-yl-methyl, cyclopropylmethyl or cyclohexylmethyl group;

R.sub.4 represents a methyl, ethyl or allyl group; and

W represents a carboxyl, methoxycarbonyl, ethoxycarbonyl or cyanomethyl group; and

the enantiomeres thereof or their mixtures; when W is carboxyl, a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the piperidino function.

4. A compound of claim 1, wherein

R.sub.1 represents a piperidino group;

R.sub.2 represents a hydrogen atom;

R.sub.3 represents an alkyl group with 3 to 6 carbon atoms, an alkenyl group with 3 or 4 carbon atoms, a phenyl, cyclopropylmethyl or cyclohexylmethyl group;

R.sub.4 represents a methyl or ethyl group; and

W represents a carboxyl group; and

the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the piperidino function.

5. A compound of claim 1, wherein

R.sub.1 represents a piperidino group;

R.sub.2 represents a hydrogen atom;

R.sub.3 represents an alkyl group with 3 to 6 carbon atoms, a 2-methyl-1-propen-1-yl, cyclomethylpropyl or cyclohexylmethyl group;

R.sub.4 represents a methyl or ethyl group; and

W represents a carboxyl group; and

the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the piperidino function.

6. A compound of claim 5, wherein

R.sub.3 represents a n-propyl, n-butyl, isobutyl, sec.butyl, n-pentyl, 2-methyl-1-propen-1-yl, cyclomethylpropyl or cyclohexylmethyl group;

the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof formed by an inorganic or organic acid with the piperidino function.

7. A compound of claim 5, wherein

R.sub.3 represents a n-propyl, n-butyl, isobutyl, sec.butyl or n-pentyl group; and

the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt thereof salt thereof formed by an inorganic or organic acid with the piperidino function.

8. The compound of claim 5, which is 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzo ic acid; the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt formed by an inorganic or organic acid with the piperidino function.

9. The compound of claim 5, which is 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmeth yl]benzoic acid; the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt formed by an inorganic or organic acid with the piperidino function.

10. The compound of claim 5, which is form (A) of 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmeth yl]-benzoic acid, recrystallized from acetone/petroleum ether, having a melting point of 90.degree.-92.degree. C.

11. The compound of claim 5, which is form (B) of 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmeth yl]-benzoic acid, recrystallized from ethanol/water, having a melting point of 140.degree.-142.degree. C.

12. The compound of claim 5, which is form (C) of 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmeth yl]-benzoic acid, recrystallized from methanol, having a melting point of 74.degree.-85.degree. C.

13. The compound of claim 5, which is 2-ethoxy-4-[N-(.alpha.-cyclohexylmethyl-2-piperidino-benzyl)-aminocarbonyl methyl]-benzoic acid; the enantiomeres thereof or their mixtures; a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt formed by an inorganic or organic acid with the piperidino function.

14. The (S)-enantiomer of a compound as claimed in anyone of the claims 1 to 13; when W is carboxy, a non-toxic salt thereof formed with an inorganic or organic base; or a non-toxic acid addition salt formed by an inorganic or organic acid with the amino function in the R.sub.1 -position.

15. A hypoglycemic pharmaceutical composition consisting essentially of an inert pharmaceutical carrier and an effective hypoglycemic amount of a compound of claim 1.
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