Amino-benzoic acids and derivatives, and methods of use

A method for treating an animal to inhibit the formation of advanced glycosylation endproducts of a target protein within said animal, said method comprising administering to an animal in need of said treatment an effective amount of a pharmaceutical composition, said pharmaceutical composition comprising a compound selected from the group consisting of compounds of the formula ##STR43## wherein R.sub.1 is a hydroxy, lower alkoxy, amino or hydrazino group, or a group of the formula

• --NR.sub.4 R.sub.5,
• wherein R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is an alkyl group of 1-20 carbon atoms, an aryl group, a hydroxy lower alkyl group, a cycloloweralkyl group or a heterocyclic group containing 4-7 ring members and 1-3 heteroatoms;
• or R.sub.4 and R.sub.5 together with the nitrogen form a morpholino, piperidinyl, or piperazinyl group;
• or when R.sub.4 is hydrogen, then R.sub.5 can also be a hydroxy group;
• R.sub.2 is 0-3 amino or nitro groups, and/or a hydrazino group, a hydrazinosulfonyl group, a hydroxyethylamino or an amidino group;
• R.sub.3 is hydrogen or one or two fluoro, hydroxy, lower alkoxy, carboxy, loweralkylamino, diloweralkylamino or hydroxyloweralkylamino groups;
• with the proviso that when R.sub.1 is hydroxy or lower alkoxy, then R.sub.3 is a non-hydrogen substituent;
• with the further proviso that when R.sub.1 is hydrazino, then there must be at least two non-hydrogen substituents on the phenyl ring;
• and with the further proviso that when R.sub.3 is hydrogen, then R.sub.5 can also be an aminoimino, guanidyl, aminoguanidinyl or diaminoguanidyl group;
• their pharmaceutically acceptable salts;
• and mixtures thereof, and a carrier therefor.

A method of inhibiting the discoloration of teeth resulting from non-enzymatic browning in the oral cavity which comprises administration of an amount effective to inhibit the formation of advanced glycosylation endproducts of a composition comprising a compound selected from the group consisting of compounds of the formula ##STR44## wherein R.sub.1 is a hydroxy, lower alkoxy, amino or hydrazino group, or a group of the formula

• --NR.sub.4 R.sub.5,
• wherein R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is an alkyl group of 1-20 carbon atoms, an aryl group, a hydroxy lower alkyl group, a cycloloweralkyl group or a heterocyclic group containing 4-7 ring members and 1-3 heteroatoms;
• or R.sub.4 and R.sub.5 together with the nitrogen form a morpholino, piperidinyl, or piperazinyl group;
• or when R.sub.4 is hydrogen, then R.sub.5 can also be a hydroxy group;
• R.sub.2 is 0-3 amino or nitro groups, and/or a hydrazino group, a hydrazinosulfonyl group, a hydroxyethylamino or an amidino group;
• R.sub.3 is hydrogen or one or two fluoro, hydroxy, lower alkoxy, carboxy, loweralkylamino, dilower alkylamino or hydroxyloweralkylamino groups;
• with the proviso that when R.sub.1 is hydroxy or lower alkoxy, then R.sub.3 is a non-hydrogen substituent;
• with the further proviso that when R.sub.1 is hydrazino, then there must be at least two non-hydrogen substituents on the phenyl ring;
• and with the further proviso that when R.sub.1 is hydrogen, then R.sub.5 can also be an aminoimino, guanidyl, aminoguanidinyl or diaminoguanidyl group;
• with the further proviso that when R.sub.1 is hydrazino, then there must be at least two non-hydrogen substituents on the phenyl ring;
• and with the further proviso that when R.sub.3 is hydrogen, then R.sub.5 can also be an aminoimino, guanidyl, aminoguanidinyl or diaminoguanidyl group;
• and
• their pharmaceutically acceptable salts;
• and mixtures thereof.

A pharmaceutical composition for administration to an animal to inhibit the advanced glycosylation of a target protein within said animal, comprising a pharmaceutically effective amount of a compound selected from the group consisting of compounds of the formula ##STR45## wherein R.sub.1 is a hydroxy, lower alkoxy, amino or hydrazino group, or a group of the formula

• --NR.sub.4 R.sub.5,
• wherein R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is an alkyl group of 1-20 carbon atoms, an aryl group, a hydroxy lower alkyl group, a cycloloweralkyl group or a heterocyclic group containing 4-7 ring members and 1-3 heteroatoms;
• or R.sub.4 and R.sub.5 together with the nitrogen form a morpholino, piperidinyl, or piperazinyl group;
• or when R.sub.4 is hydrogen, then R.sub.5 can also be a hydroxy group;
• R.sub.2 is 0-3 amino or nitro groups, and/or a hydrazino group, a hydrazinosulfonyl group, a hydroxyethylamino or an amidino group;
• R.sub.3 is hydrogen or one or two fluoro, hydroxy, lower alkoxy, carboxy, loweralkylamino, diloweralkylamino or hydroxyloweralkylamino groups;
• with the proviso that when R.sub.1 is hydroxy or lower alkoxy, then R.sub.3 is a non-hydrogen substituent;
• with the further proviso that when R.sub.1 is hydrazino, then there must be at least two non-hydrogen substituents on the phenyl ring;
• and with the further proviso that when R.sub.3 is hydrogen, then R.sub.5 can also be an aminoimino, guanidyl, aminoguanidinyl or diaminoguanidyl group;
• and their pharmaceutically acceptable salts;
• and mixtures thereof.

A compound of the formula ##STR47## wherein R.sub.8 is a hydroxy, alkoxy, hydrazino group, or a group of the formula --NR.sub.6 R.sub.7

• wherein R.sub.6 is hydrogen and R.sub.7 is a morpholino,
• piperidinyl, homopiperidinyl, or piperazinyl group;
• or, R.sub.6 and R.sub.7, together with the nitrogen atom, form a morpholino, piperidino, or piperazinyl group;
• or
• when R.sub.6 is hydrogen, then R.sub.7 can also be a phenyl group;
• R.sub.9 is one or two hydroxy, alkoxy, lower alkylamino, diloweralkylamino or hydroxyloweralkylamino groups;
• with the proviso that when R.sub.8 is a hydroxy group, then R.sub.9 is a group other than hydroxy;
• and their pharmaceutically acceptable salts.