Phosphoramidates, phosphinic amides and related compounds and the use thereof to modulate the activity of endothelin

A compound of formula I:

• ##STR11## or a pharmaceutically acceptable salt or ester thereof, wherein:
• Ar.sup.1 is selected from:
• ##STR12## in which each group is unsubstituted or substituted with one or more substituents R;
• and each R, which may be the same or different, is independently selected from H, NH.sub.2, NO.sub.2, halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, substituted or unsubstituted amido, substituted or unsubstituted ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms and are either straight or branched chains or cyclic, and the aryl and heteroaryl groups have from about 4 to about 16 atoms;
• A and B are each independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring.

A compound of formula I:

• ##STR13## or a pharmaceutically salt or ester thereof, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group selected from the group consisting of quinolyl, thienyl, furyl, isoquinolyl, pyrrolyl, indolyl, oxadiazolyl, isoxazolyl, isothiazolyl, benzofuranyl and benzothienyl;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 0 or 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from aryl and heteroaryl groups;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• and
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, or cycloalkynyl.

A compound of formula I:

• ##STR14## or a pharmaceutically acceptable salt or ester thereof, wherein:
• Ar.sup.1 is an optionally substituted isoxazolyl or N-pyridazinyl;
• and
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring.

A compound of formula I:

• ##STR15## or a pharmaceutically acceptable salt or ester thereof, wherein:
• Ar.sup.1 is an optionally substituted isoxazolyl or N-pyridazinyl;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 0 or 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from among phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazinyl, thienyl and furyl;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• and
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl.

A pharmaceutical composition, comprising an effective amount of a compound of formula (I):

• or a pharmaceutically acceptable salt or ester of a compound of formula (I) in a pharmaceutically acceptable carrier, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two or three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from O, S, and N;
• A and B are independently selected from among alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, thioalkoxy, alkylamino, alkylthio, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disorder when a single dose of the composition is administered.

A method for the treatment of endothelin-mediated diseases, comprising administering an effective amount of one or more compounds of formula (I):

• ##STR19## or pharmaceutically acceptable salts of the compounds of formula (I), wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• and
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl portions have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the effective amount is sufficient to ameliorate one or more of the symptoms of the disease.

A method for inhibiting the binding of an endothelin peptide to endothelin.sub.A or endothelin.sub.B receptors, comprising contacting the receptors with an endothelin peptide and with one or more compounds of formula (I):

• ##STR20## or pharmaceutically acceptable salts of the compounds of formula (I), wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• and
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the contacting is effected prior to, simultaneously with or subsequent to contacting the receptors with the endothelin peptide.

A method for altering endothelin receptor-mediated activity, comprising contacting endothelin receptors with one or more compounds of formula (I):

• ##STR21## or pharmaceutically acceptable salts of the compounds of formula (I), wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group, having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• and
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring.

A pharmaceutical composition formulated for single dosage administration, comprising an effective amount of one or more compounds of formula (I):

• ##STR22## or pharmaceutically acceptable salts or esters of the compounds of formula (I), wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• and
• A and B are independently selected from among alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, thioalkoxy, alkylamino, alkylthio, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disease.

An article of manufacture, comprising packaging material and a compound of formula (I):

• ##STR23## or a pharmaceutically acceptable salt of a compound of formula (I) contained within the packaging material, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• and
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the compound or salt thereof is effective for antagonizing the effects of endothelin, ameliorating the symptoms of an endothelin-mediated disorder, or inhibiting the binding of an endothelin peptide to an ET receptor with an IC.sub.50 of less than about 10 .mu.M;
• and the packaging material includes a label that indicates that the compound or salt thereof is used for antagonizing the effects of endothelin, inhibiting the binding of endothelin to an endothelin receptor or treating an endothelin-mediated disorder.

A compound of formula I:

• ##STR24## or a pharmaceutically acceptable salt or ester thereof, wherein:
• Ar.sup.1 is selected from:
• ##STR25## in which each group is unsubstituted or substituted with one or more substituents R;
• and each R, which may be the same or different, is independently selected from H, NH.sub.2, NO.sub.2, halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, substituted or unsubstituted amido, substituted or unsubstituted ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms and are either straight or branched chains or cyclic, and the aryl and heteroaryl groups have from about 4 to about 16 atoms;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 0 or 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from aryl and heteroaryl groups;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• and
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, or cycloalkynyl.

A method for the treatment of endothelin-mediated diseases, comprising administering an effective amount of one or more compounds of formula I:

• ##STR26## or pharmaceutically acceptable salts or esters thereof, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group selected from the group consisting of quinolyl, thienyl, furyl, isoquinolyl, pyrrolyl, pyridyl, indolyl, oxadiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyrimidyl, benzofuranyl and benzothienyl;
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and the effective amount is sufficient to ameliorate one or more of the symptoms of the disease.

A pharmaceutical composition formulated for single dosage administration, comprising an effective amount of one or more compounds of formula I:

• ##STR27## or pharmaceutically acceptable salts or esters thereof, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group selected from the group consisting of quinolyl, thienyl, furyl, isoquinolyl, pyrrolyl, pyridyl, indolyl, oxadiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyrimidyl, benzofuranyl and benzothienyl;
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• and
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disease.

A pharmaceutical composition formulated for single dosage administration, comprising an effective amount of one or more compounds of formula (I):

• ##STR28## or pharmaceutically acceptable salts or esters thereof, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 0 or 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from aryl and heteroaryl groups;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• and
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disease.

A pharmaceutical composition formulated for single dosage administration, comprising an effective amount of one or more compounds of formula (I):

• ##STR29## or pharmaceutically acceptable salts or esters thereof, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 0 or 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from aryl and heteroaryl groups;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• and
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disease.

A pharmaceutical composition, comprising an effective amount of a compound of formula I:

• ##STR30## or a pharmaceutically acceptable salt or ester of a compound of formula I in a pharmaceutially acceptable carrier, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group selected from the group consisting of quinolyl, thienyl, furyl, isoquinolyl, pyrrolyl, pyridyl, indolyl, oxadiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyrimidyl, benzofuranyl and benzothienyl;
• A and B are independently selected from among halide, pseudohalide, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, alkoxy, thioalkoxy, alkylamino, alkylthio, haloalkyl, alkylsufinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsufinyl, arylsulfonyl, heteroaryloxy, heteroarylamino, heteroarylthio, haloaryl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, arylcarbonyl, formyl, amido and ureido, in which the alkyl, alkenyl and alkynyl groups have from 1 up to about 14 carbon atoms, and are either straight or branched chains or cyclic, and in which the aryl and heteroaryl groups have from 4 to 16 atoms in the ring;
• the amount is effective for ameliorating the symptoms of an endothelin-mediated disorder when a single dose of the composition is administered.

A pharmaceutical composition, comprising a compound of formula (I):

• ##STR31## or a pharmaceutically acceptable salt or ester of a compound of formula I in a pharmaceutically acceptable carrier, wherein:
• Ar.sup.1 is an optionally substituted heteroaryl group having one ring or two to three fused or unfused rings and from 3 up to about 21 atoms in the ring(s), in which the heteroaryl groups have one to three heteroatoms selected from among O, S and N;
• A has the formula Ar.sup.2 --X.sub.p ;
• B has the formula Ar.sup.3 --Y.sub.o in which o and p are 1;
• Ar.sup.2 and Ar.sup.3 are each independently selected from aryl and heteroaryl groups;
• and
• X and Y are each independently selected from among O, N, NR.sup.13, S or (CH.sub.2).sub.n in which n is 0 to 10;
• R.sup.13 has up to about 30 carbon atoms and is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, halide, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R.sup.14 and S(O).sub.n R.sup.14 in which n is 0-2;
• and
• R.sup.14 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl;
• R.sup.13 and R.sup.14 are unsubstituted or are substituted with one or more substituents each selected independently from Z, which is hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl.