Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.

Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.

The invention relates to chiral imidodiphosphates and derivatives thereof having the general formula I, ##STR00001## The compounds are suitable as chiral Brønsted acid catalysts, phase-transfer catalysts, chiral anions for organic salts, metal salts or metal complexes for catalysis.

The invention relates to chiral imidodiphosphates and derivatives thereof having the general formula I, ##STR00001## The compounds are suitable as chiral Brønsted acid catalysts, phase-transfer catalysts, chiral anions for organic salts, metal salts or metal complexes for catalysis.

A salt having a group represented by the formula (aa):

##STR00001##

wherein X.sup.a and X.sup.b independently each represent an oxygen atom or a sulfur atom,
the ring W represents a C3-C36 heterocyclic ring which has an ester bond or a thioester bond, said heterocyclic ring optionally further having an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group each by which a methylene group has been replaced, and said heterocycilic ring optionally having a hydroxyl group, a cyano group, a carboxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C2-C13 alkoxycarbonyl group, a C2-C13 acyl group, a C2-C13 acyloxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or any combination of these groups each by which a hydrogen atom has been replaced, and
* represents a binding position.

A salt having a group represented by the formula (aa):

##STR00001##

wherein X.sup.a and X.sup.b independently each represent an oxygen atom or a sulfur atom,
the ring W represents a C3-C36 heterocyclic ring which has an ester bond or a thioester bond, said heterocyclic ring optionally further having an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group each by which a methylene group has been replaced, and said heterocycilic ring optionally having a hydroxyl group, a cyano group, a carboxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C2-C13 alkoxycarbonyl group, a C2-C13 acyl group, a C2-C13 acyloxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or any combination of these groups each by which a hydrogen atom has been replaced, and
* represents a binding position.

A salt represented by formula (I): ##STR00001##
wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, a hydroxy group or a C.sub.1 to C.sub.12 hydrocarbon group in which a methylene group may be replaced by a —O— or —CO—; m and n independently represent 1 or 2; Ar represents an optionally substituted phenyl group; Q.sup.1 and Q.sup.2 independently represent a fluorine atom or a C.sub.1 to C.sub.6 perfluoroalkyl group, A.sup.1 represents a single bond, a C.sub.1 to C.sub.24 alkanediyl group or the like, and Y represents an optionally substituted C.sub.1 to C.sub.18 alkyl group or monovalent C.sub.3 to C.sub.18 alicyclic hydrocarbon group, and a methylene group therein may be replaced by a —O—, O— or —SO.sub.2—, provided that the alkyl group or the alicyclic hydrocarbon group has at least one substituent, or at least one methylene group contained therein is replaced by a —O—, —CO— or —SO.sub.2—.

A salt represented by formula (I): ##STR00001##
wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, a hydroxy group or a C.sub.1 to C.sub.12 hydrocarbon group in which a methylene group may be replaced by a —O— or —CO—; m and n independently represent 1 or 2; Ar represents an optionally substituted phenyl group; Q.sup.1 and Q.sup.2 independently represent a fluorine atom or a C.sub.1 to C.sub.6 perfluoroalkyl group, A.sup.1 represents a single bond, a C.sub.1 to C.sub.24 alkanediyl group or the like, and Y represents an optionally substituted C.sub.1 to C.sub.18 alkyl group or monovalent C.sub.3 to C.sub.18 alicyclic hydrocarbon group, and a methylene group therein may be replaced by a —O—, O— or —SO.sub.2—, provided that the alkyl group or the alicyclic hydrocarbon group has at least one substituent, or at least one methylene group contained therein is replaced by a —O—, —CO— or —SO.sub.2—.

An electrolyte, including: a compound of Formula I, and at least one of a compound of Formula II or a compound of Formula III,

##STR00001##

R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently selected from hydrogen, fluoro, substituted or unsubstituted C.sub.1-C.sub.10 alkyl, substituted or unsubstituted C.sub.2-C.sub.10 alkenyl, substituted or unsubstituted C.sub.2-C.sub.10 alkynyl, substituted or unsubstituted C.sub.6-C.sub.12 aryl, substituted or unsubstituted C.sub.1-C.sub.10 alkoxy, or substituted or unsubstituted C.sub.6-C.sub.12 aryloxy, wherein when substituted, the substituent is fluoro, cyano or C.sub.1-C.sub.10 alkyl; and a, d and f are each independently selected from an integer from 1 to 5, and b, c, e, g, h and i are each independently selected from an integer from 0 to 5.

An electrolyte, including: a compound of Formula I, and at least one of a compound of Formula II or a compound of Formula III,

##STR00001##

R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently selected from hydrogen, fluoro, substituted or unsubstituted C.sub.1-C.sub.10 alkyl, substituted or unsubstituted C.sub.2-C.sub.10 alkenyl, substituted or unsubstituted C.sub.2-C.sub.10 alkynyl, substituted or unsubstituted C.sub.6-C.sub.12 aryl, substituted or unsubstituted C.sub.1-C.sub.10 alkoxy, or substituted or unsubstituted C.sub.6-C.sub.12 aryloxy, wherein when substituted, the substituent is fluoro, cyano or C.sub.1-C.sub.10 alkyl; and a, d and f are each independently selected from an integer from 1 to 5, and b, c, e, g, h and i are each independently selected from an integer from 0 to 5.