Compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them

1. A compound of the formula (I)

wherein R 1 represents hydrogen, hydroxy, halogen, linear or branched (C 1 -C 12 ) alkyl, linear or branched (C 1 -C 12 ) alkoxy, or substituted or unsubstituted arylalkyl;

R 2 represents hydrogen, halogen, linear or branched (C 1 -C 12 ) alkyl, linear or branched (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkanoyl, aroyl, arylalkanoyl, or substituted or unsubstituted arylalkyl;

R 3 represents hydrogen or a substituted or unsubstituted group which is linear or branched (C 1 -C 12 )alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, (C 1 -C 12 )alkanoyl, aroyl, arylalkyl, arylalkanoyl, alkoxyalkyl, alkoxycarbonyl, aryloxycarbonyl, alkylaminocarbonyl, or arylaminocarbonyl;

R 4 represents hydrogen;

Y represents oxygen;

R 5 represents hydrogen or a substituted or unsubstituted group which is alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl;

Ar represents substituted or unsubstituted group which is divalent phenylene, or naphthylene;

X represents a bond;

R 6 represents —OSO 2 R 8 , —SO 2 R 8 , —SOR 8 , —SR 8 , —SO 2 NR 8 R 9 , or —SO 2 OR 8 , wherein R 8 and R 9 which may be the same or different, independently represent hydrogen, substituted or unsubstituted alkyl, aryl, arylalkyl, alkoxycarbonyl or arylalkoxycarbonyl; or with the provisio that R 6 is hydrogen, when R 13 is at the third position of the phenyl ring and does not represent hydrogen;

R 13 represents hydrogen, —OSO 2 R 8 , —SO 2 R 8 , —SOR 8 , —SR 8 , —SO 2 NR 8 R 9 , —SO 2 OR 8 , wherein R 8 and R 9 , which may be the same or different, independently represent hydrogen, substituted or unsubstituted alkyl, aryl, arylalkyl, alkoxycarbonyl or arylalkoxycarbonyl;

n is 1 to 6, and m is 0 to 6;

and stereoisomers, tautomeric forms, pharmaceutically acceptable salts, and pharmaceutically acceptable solvates of the compound of the formula (I).

2. The compound of formula (I) as claimed in claim 1 , wherein:

R 1 is hydrogen or linear or branched (C 1 -C 6 )alkyl;

R 2 is hydrogen or linear or branched (C 1 -C 6 )alkyl;

R 3 is hydrogen, linear or branched (C 1 -C 12 )alkyl, (C 3 -C 7 )cycloalkyl, aryl or arylalkyl;

R 4 hydrogen;

R 5 is hydrogen, (C 1 -C 12 )alkyl or (C 3 -C 7 )cycloalkyl;

R 6 is —OSO 2 R 8 ;

R 8 is hydrogen, linear or branched (C 1 -C 6 )alkyl or substituted or unsubstituted aryl;

R 9 is hydrogen, linear or branched (C 1 -C 6 )alkyl;

R 13 is hydrogen or —OSO 2 R 8 ;

X represents a bond;

Y is oxygen;

m is an integer from 0 to 1; and

n is an integer from 1 to 2.

3. The compound of formula (I) as claimed in claim 2 , wherein

R 1 is hydrogen;

R 2 is hydrogen;

R 3 is hydrogen, or linear or branched (C 1 -C 12 )alkyl;

R 4 is hydrogen;

R 5 is hydrogen or (C 1 -C 12 )alkyl;

R 6 is —OSO 2 R 8 ;

R 8 is or linear or branched (C 1 -C 6 )alkyl, or substituted aryl group wherein the substituent is linear or branched (C 1 -C 6 )alkyl;

R 9 is linear or branched (C 1 -C 6 )alkyl;

R 13 is hydrogen or —OSO 2 R 8 ; and

X represents a bond.

4. The compound according to claim 1 , wherein the pharmaceutically acceptable salt is selected from the group consisting of Li, Na, K, Ca, Mg, Fe, Cu, Zn, Al, Mn; N,N′-diacetylethylenediamine, betaine, caffeine, 2-diethylaminoethanol, 2-dimethylaminoethanol, N-ethylmorpholine, N-ethylpiperidine, glucamine, glucosamine, hydrabamine, isopropylamine, methylglucamine, morpholine, piperazine, piperidine, procaine, theobromine, valinol, diethylamine, triethylamine, trimethylamine, tripropylamine, tromethamine, adamentyl amine, diethanolamine, meglumine, ethylenediamine, N,N′-diphenylethylenediamine, N,N′-dibenzylethylenediamine, N-benzyl phenylethylamine, choline, choline hydroxide, dicyclohexylamine, metformin, benzylamine, phenylethylamine, dialkylamine, trialkylamine, thiamine, aminopyrimidine, aminopyridine, purine, pyrimidine, spermidine; alkylphenylamine, glycinol, phenyl glycinol; glycine, alanine, valine, leucine, isoleucine, norleucine, tyrosine, cystine, cysteine, methionine, proline, hydroxy proline, histidine, ornithine, lysine, arginine, serine, threonine, phenylalanine; unnatural amino acids; D-isomers or substituted amino acids; salts of acidic amino acids selected from aspartic acid or glutamic acid; guanidine, substituted guanidine wherein the substituents are selected from nitro, amino, alkyl, alkenyl or alkynyl; ammonium, substituted ammonium salts; sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides (HCI, HBr, HI), acetates, tartrates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, salicylates, hydroxynaphthoates, benzenesulfonates, ascorbates, glycerophosphates, or ketoglutarate salt.

5. The compound according to claim 1 , wherein the substituent on the group represented by R 3 is selected from the group consisting of hydrogen linear or branched groups selected from (C 1 -C 12 )alkyl, (C 3 -C 7 )cycloalkyl, aryl or arylalkyl.

6. The compound according to claim 1 , wherein the substituent on the group represented by R 5 is selected from the group consisting of hydrogen linear or branched groups selected from (C 1 -C 12 )alkyl, or (C 3 -C 7 )cycloalkyl.

7. The compound according to claim 1 , wherein the substituent on the group represented by R 6 is —OSO 2 R 8 .

8. The compound according to claim 1 , wherein the substituents on the group represented by R 13 are selected from the group consisting of hydrogen or —OSO 2 R 8 .

9. The compound according to claim 1 , wherein the substituents on the groups represented by, R 8 or R 9 are selected from the group consisting of hydrogen, linear or branched (C 1 -C 6 )alkyl, or substituted or unsubstituted aryl group wherein the substituent is linear or branched (C 1 -C 6 )alkyl.

10. A composition comprising a) the compound of claim 1 in accordance with the formula (I) its pharmaceutically acceptable salts, or its pharmaceutically acceptable solvates, and b) a pharmaceutically acceptable carrier, diluent, or excipients.

11. The composition of claim 10 , wherein, for said compound, said salt or said solvate,

R 1 is hydrogen, linear or branched (C 1 -C 6 )alkyl;

R 2 is hydrogen, linear or branched (C 1 -C 6 )alkyl;

R 3 is hydrogen, linear or branched (C 1 -C 12 )alkyl, (C 1 -C 7 )cycloalkyl;

R 4 is hydrogen;

R 5 is hydrogen, (C 1 -C 12 )alkyl or (C 3 -C 7 )cycloalkyl;

R 6 is —OSO 2 R 8 ;

R 8 is hydrogen, linear or branched (C 1 -C 6 )alkyl or substituted or unsubstituted aryl;

R 9 is hydrogen, linear or branched (C 1 -C 6 )alkyl, t-butyloxycarbonyl or benzyloxycarbonyl;

R 13 is hydrogen or —OSO 2 R 8 ;

X represents a bond;

Y is oxygen;

m is an integer from 0 to 1; and

n is an integer from 1 to 2.

12. The composition of claim 10 , wherein

R 1 hydrogen;

R 2 is hydrogen;

R 3 is hydrogen, or linear or branched (C 1 -C 12 )alkyl;

R 4 is hydrogen;

R 5 hydrogen or (C 1 -C 12 )alkyl;

R 6 is —OSO 2 R 8 ;

R 8 is or linear or branched (C 1 -C 6 )alkyl, or substituted aryl group wherein the substituent is linear or branched (C 1 -C 6 )alkyl;

R 9 is linear or branched (C 1 -C 6 )alkyl, t-butyloxycarbonyl or benzyloxycarbonyl;

R 13 is hydrogen or —OSO 2 R 8 ; and

X represents a bond.

13. The composition of claim 10 , which is in the form of a tablet, capsule, powder, syrup, solution or suspension.

14. The composition of claim 10 , further comprising insulin.