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Title:
NOVEL MOLECULE FOR INDUCING DIFFERENTIATION OF DENDRITIC CELLS
Document Type and Number:
WIPO Patent Application WO/2005/037775
Kind Code:
A1
Abstract:
The present invention is related to compound having general formula Z-OC (C Rn1Rn2) -CO-Z wherein Z &equals OH or NH2 and n1 &equals n2 &equals 1 to useful for modulation of immune response by inducing differentiation of dendritic cells consisting novel class of amino acid derivatives (sulfonic acid / sulfate derivatives of naturally occurring amino acids, and their amides) of the general formula ZOC-CR3R4-CR2(NHR1)-COOH, ZOC-CR5R6-CR3R4-CR1(NHR2)-COOH, ZOC-CR7R8-CR5R6-CR3R4-CR1(NHR2)-COOH wherein Z&equals OH or NH2; R1 to R8 denotes H, SO3H, or OSO3H. In addition, the dicarboxylic acids and their amides ZOC-(CH2)n-CR1R2-COOH, where Z&equals OH or NH2; and n&equals 1,2,3. The groups R1 / R2 &equals H / SO3H or OSO3H or CH2-SO3H or CH2-OSO3H and vice versa. The factors also contain different divalent metal cations such as Mg, Ca and Zn. The composition consists of varying amounts of the above amino acid / dicarboxylic acid derivatives or their pharmaceutically acceptable alkali / alkaline earth metal salts or their salts, the processes for the preparation of the aforesaid compounds useful for the differentiation and maturation of dendritic cells.

Inventors:
CHATTERJI ANIL (IN)
NATARAJAN KRISHNAMURTHY (IN)
MANIVEL VENKATASAMY (IN)
RAO KANURY VENKATA SUBBA (IN)
SUBRAYAN PARAMESWARAN PERUNNIN (IN)
SINGH VINOD KUMAR (IN)
ANAND RAMASAMY VIJAYA (IN)
DESA EHRLICH (IN)
Application Number:
PCT/IN2003/000432
Publication Date:
April 28, 2005
Filing Date:
December 31, 2003
Export Citation:
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Assignee:
COUNCIL SCIENT IND RES (IN)
CHATTERJI ANIL (IN)
NATARAJAN KRISHNAMURTHY (IN)
MANIVEL VENKATASAMY (IN)
RAO KANURY VENKATA SUBBA (IN)
SUBRAYAN PARAMESWARAN PERUNNIN (IN)
SINGH VINOD KUMAR (IN)
ANAND RAMASAMY VIJAYA (IN)
DESA EHRLICH (IN)
International Classes:
A61K31/16; A61K31/185; A61K31/19; A61K31/194; A61K31/195; A61K31/255; C07C305/06; C07C307/02; C07C309/17; C07C309/18; (IPC1-7): C07C309/18; A61K31/19; A61K31/194; A61K31/195; A61P37/02; C07C309/17
Domestic Patent References:
WO2002006308A22002-01-24
Foreign References:
US20030044470A12003-03-06
Other References:
I.A.KOSTANYAN: "L-GlutamicAcid, a Modulator of the Physiological State of Myeloid Blood Cells", RUSSIAN J. BIOORG. CHEM. ENG. TRANSL., vol. 25, no. 11, 1999, pages 816 - 820, XP009032996
G.SIMMONET: "Modulation of Neuropeptide FF release from Rat Spinal Cord Slices by Glutamate. Involvment of NDMA Receptors", EUROPEAN J. PHARMACOLOGY, no. 271, 1994, pages 185 - 192, XP002288048
ROBERT WEISSERT: "Action of Treosulfan in myelin-oligodendrocyte-glycoprotein-induced experimental autoimmune encephalomyelitis and human lymphocytes", JOURNAL OF NEUROIMMUNOLOGY, no. 144, 28 August 2003 (2003-08-28), pages 28 - 37, XP002286267
Attorney, Agent or Firm:
Hariharan, Rajeshwari (84-C C6 LANE OFF CENTRAL AVENU, SAINIK FARMS 2 NEW DELHI, IN)
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Claims:
CLAIMS
1. I. A method for modulation of immune response by differentiation of dendritic cells, said method comprising the step of administration a pharmaceutical acceptable amount of a compound having general formula ZOC (C Rn Rn2)COZ wherein Z = OH or NH2 and nl = n2 =1 to 8 and subject to need thereof optionally with an additive, excipient, diluents or carrier.
2. A method as claimed in claim 1, wherein said compound useful in vaccine formulation to prevent more efficient and faster presentation of antigens to Tcells thereby initiate primary protective Thl immune response and help in the clearance of the pathogen.
3. A method as claimed in claim 1, wherein said compound having a structure as herein and bearing general formula ZOCCR3R4CR, R2COOH wherein: Z=OH or NH2, R1, to R4 denotes H, NH2, SO3H, or OS03H, CH2SO3H, CH2OSO3H, NHS03H Structure 1.
4. A method as claimed in claim 1, wherein said compound having a structure as herein and bearing general formula ZOCCR5R6CR3R4CRIR2COOH wherein: Z=OH or NH2, R, to R6 denotes H, NH2, S03H, or OS03H, CH2SO3H, CH2 OSO3H, NHS03H Struccure 2.
5. A method as claimed in claim 1, wherein said compound having structure as herein and bearing general formula ZOCCR7R8CR5R6CR3R4CR1R2COOH wherein: Z=OH or NH2, R, to R8 denotes H, NH2, S03H, or OS03H, CH2SO3H, CH2 OSO, H, NHS03H structure 3.
6. A method as claimed in claim 1, wherein said compound in nontoxic to monocytes.
7. A method as claimed in claim 1, wherein said compound in nontoxic to macrophages.
8. A method as claimed in, claim 1, wherein additives are different divalent metal cations such as Mg, Ca and Zn.
9. A method as claimed in claim 1, wherein additives are amino acid/dicarboxylic acid derivatives and their pharmaceutically acceptable selected alkali/alkaline earth metal salts.
10. A method as claimed in claim 3, wherein the compound is selected from the group consisting of : 1. [LAspartic acid, NSulfonic acid3, II. [2a, 3dicarboxy, propane1sulfonic acid], III. [2a, 3dicarboxy, propane1sulfate], IV. [1 a, 2carboy ethane sulfonic acid], V. [I α,2carboxy ethane sulfate], VI. [Daspartic acid, Nsulfonic acid], VII. [2#,3carboxy,propane1sulfonic acid], VIII. [2#,3carboxy,propane1sulfate], IX. [I (3, 2carboxy ethane1sulfonic acid], X. [I #, 2carboxy ethaneIsulfate], XI. [Daspartic acid, 3asulfonic acid], XII. [Daspartic acid, 3asulfate], XIII. [Daspartic acid, 3psulfonic acid], XIV. [Daspartic acid, 3psulfate], XV. [Lasparagine, Nsulfonic acid], XVI. [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII. [2acarboxy, 3carboxamido, propane1sulfate], XVIII. [I acarboxy, 2carboxamido, ethane sulfonic acid], XIX. [1#carboxy, 2carboxamido, ethane sulfate), XX. [Lasparagine, 3asulfonic acid], XXI. [Lasparagine, 3asulfate], XXII. [Lasparagine, 3#sulfonic acid], XXIII. [Lasparagine, 3#sulfate, XXIV. [Dasparagine, Nsulfonic acid], XXV. [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI. [2#carboxy, 3carboxamido, propánelsulfate], XXVII. [I #carboxy, 2carboxamido, ethane sulfonic acid], XXVIII. [1 #carboxy, 2carboxamido, ethane sulfate], XXIX. [Dasparagine, 3asulfonic acid], XXX. [Dasparagine, 3asulfate], XXXI. [Dasparagine, 3#sulfonic acid], XXXII. [Dasparagine, 3#sulfate], XXXIII. [Lglutamic acid, Nsulfonic acid], XXXIV. [2a, 4dicarboxy, butane1sulfonic acid], XXXV. [2a, 4dicarboxy, butane1sulfate], XXXVI. [1α, 3dicarboxy, propane sulfonic acid], XXXVII. [1α, 3dicarboxy, propane sulfate], XXXVIII. [1#, 3dicarboxy, propane sulfate], XXXIX. [1#, 3dicarboxy, propane sulfonic acid], 11. A method as claimed in claim 4, wherein the compound is selected from the group consisting of : I. [Dglutamic acid, Nsulfonic acid], II. 2#, 4dicarboxy, butane1sulfonic acid], III. [2p, 4dicarboxy, butane1sulfate], IV. [Dglutamic acid, 3asulfonic acid], V. [Dglutamic acid, 3asulfate], VI. [Dglutamic acid, 3#sulfonic acid], VII. [Dglutamic acid, 3#sulfate], VIII. [Dglutamic acid, 4αsulfonic acid], IX. [Dglutamic acid, 4asulfate], X. [Dglutamic acid, 4#sulfonic acid], XI. [Dglutamic acid. 3#sulfate], XII. [Lglutamine, Nsulfonic acid], XIII. [2acarboxy, 4carboxamido, butane1sulfonic acid], XIV. [2αcarboxy, 4carboxamido, butane1sulfate], XV. [I acarboxy, 3carboxamido, propane1sulfonic acid], XVI. [í acarboxy, 3carboxamido, propane1sulfate], XVII. [1#carboxy, 3carboxamido, propane1sulfate], XVIII. [I pcarboxy, 3carboxamido, propane1sulfonic acid], XIX. [Dglutamine, Nsulfonic acid], XX. [2#carboxy, 4carboxamido, butane1sulfonic acid], XXI. [2pcarboxy, 4carboxamido, butane1sulfate], XXII. [Dglutamine, 3asulfonic acid], XXIII. [Dglutamine, 3asulfate], XXIV. [Dglutamine, 3#sulfonic acid], XXV. [Dglutamine, 3#sulfate], XXVI. [Dglutamine, 4asulfonic acid], XXVII. [Dglutamine, 4asulfate], XXVIII. [Dglutamine, 4#sulfonic acid], XXIX. [Dglutamine, 4#sulfate], XXX. [Lhomoglutamic acid, Nsulfonic acid3, XXXI. [Pentane2a, 5dicarboxylsulfonic acid], XXXII. [Pentane2a, 5dicarboxy1sulfate], XXXIII. [Butane1α, 4dicarboxy1sulfonic acid], XXXIV. [ButaneI (x, 4dicarboxyIsulfate], XXXV. [Dhomoglutamic acid, Nsulfonic acid], XXXVI. [Pentane2#, 5dicarboxy1sulfonic acid], XXXVII. [Pentane2#, 5dicarboxy1sulfate], XXXVIII. [Butane1#, 4dicarboxy1sulfonic acid], XXXIX. [Butane1#, 4dicarboxy1sulfate], 12 ; A method as claimed in claim S, wherein the compound is selected from the group consisting of I. [Dhomogiutamic acid, 3asulfonic acid], II. [Dhomoglutamic acid, 3asulfate], III. [Dhomoglutamic acid, 3 (3sulfonic acid], IV. [Dhomoglutamic acid, 3psulfate], V. [Dhomoglutamic acid, 4asulfonic acid], VI. [Dhomoglutamic acid, 4asulfate], VII. [Dhomoglutamic acid, 4psulfonic acid], VIII. [Dhomoglutamic acid, 4#sulfate], IX. [Dhomoglutamic acid, 5αsulfate], X. [Dhomoglutamic acid, Sasulfate], XI. [Dhomoglutamic acid, 5 (3sulfonic acid], XII. [Dhomoglutamic acid, 5#sulfate], XIII. [Lhomoglutamine, Nsulfonic acid], XIV. [Pentane2acarboxy, 5carboxamido1sulfonic acid], XV. [Pentane2acarboxy, 5carboxamido1sulfate], XVI. [Butane1αcarboxy, 4carboxamido1sulfonic acid], XVII. [Butanelacarboxy, 4carboxamido1sulfate], XVIII. [Dhomoglutamine, Nsulfonic acid], XIX. [Pentane2#carboxy, 5carboxamido1sulfonic acid], XX. [Butane1 # carboxy, 4carboxamido1sulfonic acid], XXI. [Butane1 # carboxy, 4carboxamido1sulfate], XXII. [Dhomoglutamine, 3asulfonic acid], X, YIII. [Dhomoglutamine, 3asulfate], XXIV. [Dhomoglutamine, 3psulfbnic acid], XXV. [Dhomoglutamine, 3#sulfate], XXVI. [Dhomoglutamine, 4asulfonic acid], XXVII. [Dhomoglutamine, 4asulfate], XXVIII. [Dhomoglutamine, 4psulfonic acid], XXIX. [Dhomoglutamine, 4#sulfate], XXX. [Dhomoglutamine, Sasulfonic acid], XXXI. [Dhomoglutamine, 5asulfate], XXXII. [Dhomoglutamine, Sßsulfonic acid] and XXXIII. [Dhomoglutamine, 5psulfate].
11. 13 A method as claimed in claim 3, wherein novel sulfonic acid/sulfate derivatives of the formulae ZOCCR3R4CRIR2COOH wherein: Z=OH or NH2, Ri, to R4 denotes H, NH2, S03H, or OS03H, CH2SO3H, CH2 OS03H, NHS03H 1. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=H, R1= NHS03H is the same meaning as is before defined; II. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=H, R1= CH2SO3H is the same meaning as is before defined; III. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=H, R1= CH2OS03H is the same meaning as is before defined; IV. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=H, R1=SO3H is the same meaning as is before defined; V. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=H, R1=OSO3H is the same meaning as is before defined ; VI. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=H, R2= NHS03H is the same meaning as is before defined ; VII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=H, R2= CH2S03H is the same meaning as is before defined; VIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=H, R2= CH2OS03H is the same meaning as is before defined; IX. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=H, R2=SO3H is the same meaning as is before defined ; X. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=H, R2=OS03H is the same meaning as is before defined ; XI. A compound as claimed in claim 1, wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined; XII. A compound as claimed in claim 1, wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined; XIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=H, R2=NH2, R4=SO3H is the same meaning as is before defined; XIV. A compound as claimed in claim 1, wherein Z=OH, R1=R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined; XV. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=H, R1=NHSO3H is the same meaning as is before defined; XVI. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=H, R1=CH2SO3H is the same meaning as is before defined ; XVII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=H, Rl= CH2OSO3H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=H, Rl=S03H is the same meaning as is before defined; XIX. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=H, Rl=OS03H is the same meaning as is before defined; XX. A compound as claimed in claim 1, wherein Z=NH2, Rl=R4=H, R2=NH2, R3= S03H is the same meaning as is before defined ; XXI. A compound as claimed in claim 1, wherein Z=NH2, Rl=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined; XXII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=H, R2=NH2, R4= S03H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=H, R2= NH2, Rut= OS is the same meaning as is before defined; XXIV. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=R4=H, R2= NHS03H is the same meaning as is before defined ; XXV. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=R4=H, R2= CH2OSO3H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=R4=H, R2=S03H is the same meaning as is before defined; XXVIII. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=R4=H, R2=OS03H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=H, R2=NH2, R3= S03H is the same meaning as is before defined; XXX. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined ; XXXI. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=H, R2=NH2, R4=S03H is the same meaning as is before defined; XXXII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined.
12. A method as claimed in claim 4, wherein novel sulfonic acid/sulfate derivatives of the formulae ZOCCR5R6CR3R4CRIR2COOH, wherein: Z=OH or NH2, Ri, to R6 denotes H, NH2, SO3H, or OSO3H, CH2SO3H, CH2OSO3H, NHS03H I. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined; II. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6=H, R1=CH2SO3H is the same meaning as is before defined; III. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6=H, Rl=CH2OSO3H is the same meaning as is before defined; IV. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4= R5=R6=H, Rl= S03H is the same meaning as is before defined; V. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6=H, R1=OSO3H is the same meaning as is before defined; VI. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6=H, R2=OS03H is the same meaning as is before defined; VII. A compound as claimed in claim 1, wherein Z=OH, R, =R3=R4=Rs=R6=H, R2= S03H is the same meaning as is before defined ; VIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6=H, R2=NHSO3H is the same meaning as is before defined ; IX. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6=H, R2= CH2SO3H is the same meaning as is before defined; X. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6=H, R2= CH2OSO3H is the same meaning as is before defined; XI. A compound as claimed in claim 1, wherein Z=OH, Rl=R4=R5=R6=H, R2= NH2, R3=S03H is the same meaning as is before defined; XII. A compound as claimed in claim 1, wherein Z=OH, R1=R4=R5=R6=H, R2= NH2, R3=OS03H is the same meaning as is before defined; XIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R5=R6=H, R2= NH2, R4= S03H is the same meaning as is before defined; XIV. A compound as claimed in claim 1, wherein Z=OH, Ri=R3=R5=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined ; XV.A compound as claimed in claim 1, wherein Z=OH, R1=R4=R3=R6H, R2= NH2, R5=S03H is the same meaning as is before defined; XVI. A compound as claimed in claim 1, wherein Z=OH, Rl=R4=R3=R6=H, R2= NH2, R5=OS03H is the same meaning as is before defined; XVII. A compound as claimed in claim 1, wherein Z=OH, Rl=R3=R5=R4=H, R2= NH2, R6=SO3H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1, wherein Z=OH, Rl=R3=R5=R4=H, R2= NH2, R6=OS03H is the same meaning as is before defined; XIX. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6=H, Rl=NHS03H is the same meaning as is before defined; XX. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=CH2SO3H is the same meaning as is before defined ; XXI. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=CH2OSO3H is the same meaning as is before defined; XXII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=SO3H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6=H, Rl= OS03H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=R4=R5=R6=H, R2= OSO3H is the same meaning as is before defined; XXV. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= S03H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= NHS03H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2=CH2SO3H is the same meaning as is before defined ; XXVIII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= CH20S03H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1, wherein Z=NH2, Rl=R4=R5=R6=H, R2= NH2, R3=S03H is the same meaning as is before defined ; XXX. A compound as claimed in claim 1, wherein Z=NH2, Rl=R4=R5=R6=H, R2= NH2, R3=OSO3H is the same meaning as is before defined ; XXXI. A compound as claimed in claim 1, wherein Z=NH2, Rj=R3=R5=R6=H, R2= NH2, R4=S03H is the same meaning as is before defined ; XXXII. A compound as claimed in claim 1, wherein Z=NH2, RI =R3=R5=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined; XXXIII. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, R5=S03H is the same meaning as is before defined; XXXIV. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, Rs=OS03H is the same meaning as is before defined; XXXV. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=SO3H is the same meaning as is before defined; XXXVI. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=OS03H is the same meaning as is before defined.
13. A method as claimed in claim 5, wherein novel sulfonic acid/sulfate derivatives of the formulae ZOCCR7R8CR5R6CR3R4CRIR2COOH, wherein : Z=OH or NH2, R1, to R8 denotes H, NH2, SO3H, or OS03H, CH2SO3H, CH2OS03H, NHS03H I. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, Rl=NHS03H is the same meaning as is before defined; II. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1=CH2SO3H is the same meaning as is before defined; III. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, Rl=CH20SO3H is the same meaning as is before defined ; IV. A compound as claimed in claim 1, wherein Z=OH, R2R3=R4= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined; V. A compound as claimed in claim 1, wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1=OSO3H is the same meaning as is before defined ; VI. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6 R7=R8=H, R2=NHS03H is the same meaning as is before defined; VII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined; VIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2OSO3H is the same meaning as is before defined; IX. A compound as claimed in claim 1, wherein Z=OH, Rl=R3=R4= R5=R6=R7=Rg=H, R2=S03H is the same meaning as is before defined ; X. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=OS03H is the same meaning as is before defined; XI. A compound as claimed in claim 1, wherein Z=OH, R1=R4= R5=R6 R7=R8=H, R2=NH2, R3=S03H is the same meaning as is before defined; XII. A compound as claimed in claim 1, wherein Z=OH, R1=R4=R5=R6=R7=R8=H, R2=NH2, R3=OSO3H is the same meaning as is before defined; XIII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R5=R6= R7=R8=H, R2= NH2, R4=S03H is the same meaning as is before defined; XIV. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R5=R6=R7=R8=H, R2=NH2, R4=OSO3H is the same meaning as is before defined; XV. A compound as claimed in claim 1, wherein Z=OH, R1=R4= R3=R6 R7=R8=H, R2=NH2, R5=S03H is the same meaning as is before defined; XVI. A compound as claimed in claim 1, wherein Z=OH, Ri=R4=R3=R6= R7=R8=H, R2=NH2, R5=OS03H is the same meaning as is before defined; XVII. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R5=R4= R7=R$=H, R2=NH2, R6=SO3H is the same meaning as is before defined; XVIII. A compound as claimed in claim. 1, wherein Z=OH, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=OS03H is the same meaning as is before defined; XIX. A compound as claimed in claim 1, wherein Z=OH, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined ; XX. A compound as claimed in claim 1, wherein Z=OH, Ri=R4=R3=R6=R5=R8=H, R2=NH2, R7=OS03H is the same meaning as is before defined; XXI. A compound as claimed in claim 1, wherein Z=OH, R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=SO3H is the same meaning as is before defined ; XXII. A compound as claimed in claim 1, wherein Z=OH,.
14. R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=OSO3H is the same meaning as is before defined ; XXIII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=NHSO3H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R$=H, Ri=CH2S03H is the same meaning as is before defined; XXV. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=CH2OSO3H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=OSO3H is the same meaning as is before defined; XXVIII. A compound as claimed in claim 1, wherein Z=NH2, R, =R3=R4=R5=R6= R7=Rs=H, R2=NHS03H is the same meaning as is before defined ; XXIX. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined ; XXX. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R4= R5=R6=R7=R$=H, R2=S03H is the same meaning as is before defined ; XXXI. A compound as claimed in claim 1, wherein Z=NH2, R) =R3=R4=R5=R6= R7=R8=H, R2=OSO3H is the same meaning as is before defined; XXXII. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R5=R6= R7=R8=H, R2=NH2, R3=S03H is the same meaning as is before defined; XXXIII. A compound as claimed. in claim 1, wherein Z=NH2, RI=P, 4=R5=R6= R7=R8=H, R2=NH2, R3=OS03H is the same meaning as is before defined; XXXIV. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R6=R7=R8= H, R2=NH2, R4=S03H is the same meaning as is before defined; XXXV. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R6=R7=R8= H, R2=NH2, R4=OS03H is the same meaning as is before defined ; XXXVI. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined ; XXXVII. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R3=R6= R7=R8=H, R2=NH2, R5=OSO3H. is the same meaning as is before defined; (XXVIII. A compound as claimed in claim 1, wherein Z=NH2, R) =R3==Rs=R4= R7=R8=H, R2=NH2, R6=SO3H is the same meaning as is before defined; XXXIX. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=OS03H is the same meaning as is before defined; XL. A compound as claimed in claim 1, wherein Z=NH2, R, =R4=R3=R6=R5=R8=H, R2=NH2, R7=S03H is the same meaning as is before defined ; XLI. A compound as claimed in claim 1, wherein Z=NH2, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=OS03H is the same meaning as is before defined; XLII. A compound as claimed in claim 1, wherein Z=NH2, R1=R3=R5=R4=R7=R6=H, R2= NH2, R8=SO3H is the same meaning as is before defined ; XLIII. A compound as claimed in claim 1., wherein Z=NH2, Ri=R3=R5=R4=R7=R6=H, R2=NH2, R8=OS03H is the same meaning as is before defined ;.
15. A method as claimed in claim 10, wherein said compound is nontoxic salts selected from the group consisting of : I. [LAspartic acid, NSulfonic acid], II. [2a, 3dicarboxy, propane1sulfonic acid], III. [2a, 3dicarboxy, propane1sulfate], IV. [I a, 2carboxy ethane sulfonic acid], V. [1 a, 2carboxy ethane sulfate], VI. [Daspartic acid, Nsulfonic acid], VII. [2p, 3carboxy, propane1sulfonic acid], VIII. [2#,3carboxy,propane1sulfate], IX. [1#, 2carboxy ethane1sulfonic acid], X. [1 #, 2carboxy ethane1sulfate], XI. [Daspartic acid, 3asulfonic acid], XII. [Daspartic acid, 3asulfate], XIII. [Daspartic acid, 3#sulfonic acid], XIV. [Daspartic acid, 3psulfate], XV. [Lasparagine, Nsulfonic acid], XVI. [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII. [2acarboxy, 3carboxamido, propane1sulfate], XVIII. [1αcarboxy, 2carboxamido, ethane sulfonic acid], XIX. [I acarboxy, 2carboxamido, ethane sulfate], XX. [Lasparagine, 3asulfonic acid], XXI. [Lasparagine, 3asulfate], XXII. [Lasparagine, 3#sulfonic acid], XXIII. [Lsparagine, 3#sulfate, XXIV. [Dasparagine, Nsulfonic acid], .
16. XXV. [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI. [2pcarboxy, 3carboxamido, propane1sulfate], XXVII. [1#carboxy, 2carboxamido, ethane sulfonic acid], XXVIII. [1 (3carboxy, 2carboxamido, ethane sulfate], XXIX. [Dasparagine, 3asulfonic acid], XXX. [Dasparagine, 3asulfate], XXXI. [Dasparagine, 3#sulfonic acid], XXXII. [Dasparagine, 3psulfate], XXXIII. [Lglutamic acid, Nsulfonic acid], XXXIV. [2a, 4dicarboxy, butane1sulfonic acid], XXXV. [2a, 4dicarboxy, butane1sulfate], XXXVI. [la, 3dicarboxy, propane sulfonic acid], XXXVII. [I a, 3dicarboxy, propane sulfate], XXXVIII. [1#, 3dicarboxy, propane sulfate], XXXIX. [1#, 3dicarboxy, propane sulfonic acid],.
17. A method as claimed in claim 11, wherein said compound is nontoxic salts selected from the group consisting of : I. [Dglutamic acid, Nsulfonic acid], II. [2p, 4dicarboxy, butane1sulfonic acid], III. [2p, 4dicarboxy, butane1sulfate], IV. [Dglutamic acid, 3asulfonic acid], V. [Dglutamic acid, 3asulfate], VI. [Dglutamic acid, 3psulfonic acid], VII. [Dglutamic acid, 3psulfate], VIII. [Dglutamic acid, 4asulfonic acid], IX. [Dglutamic acid, 4asulfate], X. [Dglutamic acid, 4psulfonic acid], XI. [Dglutamic acid, 3psulfate], XII. [Lglutamine, Nsulfonic acid], XIII. [2acarboxy, 4carboxamido, butane1sulfonic acid], XIV. [2acarboxy, 4carboxamido, butane1sulfate], XV. [1αcarboxy, 3carboxamido, propane1sulfonic acid], XVI. [I acarboxy, 3carboxamido, propane1sulfate], XVII. [1#carboxy, 3carboxamido, propane1sulfate], XVIII. [1#carboxy, 3carboxamido, propane1sulfonic acid], XIX. [Dglutamine, Nsulfonic acid], XX. [2pcarboxy, 4carboxamido, butane1sulfonic acid], XXI. [2#carboxy, 4carboxamido, butane1sulfate], XXII. [Dglutamine, 3asulfonic acid], XXIII. [Dglutamine, 3asulfate], XXIV. [Dglutamine, 3ßsulfonic acid], XXV. [Dglutamine, 3psulfate], XXVI. [Dglutamine, 4asulfonic acid], XXVII. [Dglutamine, 4asulfate], XXVIII. [Dglutamine, 4psulfonic acid], XXIX. [Dglutamine, 4ßsulfate], XXX. [Lhomoglutamic acid, Nsulfonic acid], XXXI. [Pentane2a, 5dicarboxy1sulfonic acid], XXXII. [Pentane2a, 5dicarboxy1sulfate], XXXIII. [ButaneI a, 4dicarboxy1sulfonic acid], XXXIV. [Butanela, 4dicarboxy1sulfate], XXXV. [Dhomoglutamic acid, Nsulfonic acid], XXXVI. [Pentane2ß, 5dicarboxy1sulfonic acid], XXXVII. [Pentane2#, 5dicarboxy1sulfate], XXXVIII. [Butane1#, 4dicarboxy1sulfonic acid], XXXIX. [Butane1) 3, 4dicarboxylsulfate],.
18. A method as claimed in claim 12, wherein said compound is nontoxic salts selected from the group consisting of : I. [Dhomoglutamic acid, 3αsulfonic acid], II. [Dhomoglutamic acid, 3asulfate], III. [Dhomoglutamic acid, 3 (3sulfonic acid], IV. [Dhomoglutamic acid, 3#sulfate], V. [Dhomoglutamic acid, 4asulfonic acid], VI. [Dhomoglutamic acid, 4asulfate], VII. [Dhomoglutamic acid, 4 (3sulfonic acid], VIII. [Dhomoglutamic acid, 4#sulfate], IX. [Dhomoglutamic acid, 5asulfate], X. [Dhomoglutamic acid, 5αsulfate], [Dhomoglutamic acid, 5asulfate], XI. [Dhomoglutamic acid, 5psulfonic acid], XII. [Dhomoglutamic acid, 5psulfate], XIII. [Lhomoglutamine, Nsulfonic acid], XIV. [Pentane2acarboxy, 5carboxamido1sulfonic acid], XV. [Pentane2acarboxy, 5carboxamido1sulfate], XVI. [Butane1αcarboxy, 4carboxamido1sulfonic acid], XVII. [Butane1αcarboxy, 4carboxamido1sulfate], XVIII. [Dhomoglutamine, Nsulfonic acid], XIX. [Pentane2pcarboxy, 5carboxamidolsulfonic acid], XX. [Butane1 pcarboxy, 4carboxamido1sulfonic acid], XXI. [Butane1 pcarboxy, 4carboxamido1sulfate], XXII. [Dhomoglutamine, 3asulfonic acid], XXIII. [Dhomoglutamine, 3αsulfate], XXIV. [Dhomoglutamine, 3psulfonic acid], XXV. [Dhomoglutamine, 3 (3sulfate], XXVI. [Dhomoglutamine, 4αsulfonic acid], XXVII. [Dhomoglutamine, 4asulfate], XXVIII. [Dhomoglutamine, 4 (3sulfonic acid], XXIX. [Dhomoglutamine, 4#sulfate], XXX. [Dhomoglutamine, 5asulfonic acid], XXXI. [Dhomoglutamine, 5αsulfate], XXXII. [Dhomoglutamine, 5 (3sulfonic acid] and XXXIII. [Dhomoglutamine, 5#sulfate].
19. A method as claimed in claim 16, wherein said compound is selected from the group consisting of aspartic acid, asparagine and corresponding deamino analogs: I. [LAspartic acid, NSulfonic acid], II. [2a, 3dicarboxy, propane1sulfonic acid], III. [2a, 3dicarboxy, propane1sulfate], IV. [I a, 2carboxy ethane sulfonic acid], V. [1 a, 2carboxy ethane sulfate], VI. [Daspartic acid, Nsulfonic acid], VII. [2p, 3carboxy, propane1sulfonic acid], VIII. [2 P, 3carboxy, propane1sulfate], IX. [1#, 2carboxy etl1ane1sulfonic acid], X. [1#,2carboxy ethane1sulfate], XI. [Daspartic acid, 3asulfonic acid], XII. [Daspartic acid, 3αsulfate], XIII. [Daspartic acid, 3psulfonic acid], XIV. [Daspartic acid, 3ßsulfate], XV. [Lasparagine, Nsulfonic acid], XVI. [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII. [2acarboxy, 3carboxamido, propane1sulfate], XVIII. [1αcarboxy, 2carboxamido, ethane sulfonic acid], XIX. [lacarboxy, 2carboxamido, ethane sulfate], XX. [Lasparagine, 3 asulfonic acid], XXI. [Lasparagine, 3asulfate], XXII. [Lasparagine, 3psulfonic acid], XXIII. [Lasparagine, 3psulfate, XXIV. [Dasparagine, Nsulfonic acid], XXV. [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI. [2 (3carboxy, 3carboxamido, propane1sulfate], XXVII. [1 pcarboxy, 2carboxamido, ethane sulfonic acid], XXVIII. [1 pcarboxy, 2carboxamido, ethane sulfate], XXIX. [Dasparagine, 3αsulfonic acid], XXX. [Dasparagine, 3asulfate], XXXI. [Dasparagine, 3 (3sulfonic acid], XXXII. [Dasparagine, 3psulfate],.
20. A method as claimed in claim 17, wherein said compound is selected from the group consisting of glutamic acid, glutamine and corresponding deamino analogs: I. [Lglutamic acid, Nsulfonic acid], II. [2a, 4dicarboxy, butane1sulfonic acid], III. [2a, 4dicarboxy, butane1sulfate], IV. [l a, 3dicarboxy, propane sulfonic acid], V. [I a, 3dicarboxy, propane sulfate], VI. [I P, 3dicarboxy, propane sulfate], VII. [1#, 3dicarboxy, propane sulfonic acid], VIII. [Dglutamic acid, Nsulfonic acid], IX. [2p, 4dicarboxy, butane1sulfonic acid], X. [2p, 4dicarboxy, butane1sulfate], XI. [Dglutamic acid, 3asulfonic acid], XII. [Dglutamic acid, 3asulfate], XIII. [Dglutamic acid, 3psulfonic acid], XIV. [Dglutamic acid, 3psulfate], XV. [Dglutamic acid, 4asulfonic acid], XVI. [Dglutamic acid, 4asulfate], XVII. [Dglutamic acid, 4(3sulfonic acid], XVIII. [Dglutamic acid, 3ßsulfate], XIX. [Lglutamine, Nsulfonic acid], XX. [2αcarboxy, 4carboxamido, butane1sulfonic acid], XXI. [2acarboxy, 4carboxamido, butane1sulfate], XXII. [lacarboxy, 3carboxamido, propane1sulfonic acid], XXIII. [lacarboxy, 3carboxamido, propane1sulfate], XXIV. [1 pcarboxy, 3carboxamido, propane1sulfate], XXV. [Ipcarboxy, 3carboxamido, propane1sulfonic acid], XXVI. [Dglutamine, Nsulfonic acid], XXVII. [2ßcarboxy, 4carboxamido, butane1sulfonic acid], XXVIII. [2pcarboxy, 4carboxamido, butane1sulfate], XXIX. [Dglutamine, 3asulfonic acid], XXX. [Dglutamine, 3asulfate], XXXI. [Dglutamine, 3psulfonic acid], XXXII. [Dglutamine, 3psulfate], XXXIII. [Dglutamine, 4asulfonic acid], XXXIV. [Dglutamine, 4asulfate], XXXV. [Dglutamine, 4psulfonic acid], XXXVI. [Dglutamine, 4ßsulfate], XXXVII. [Lhomoglutamic acid, Nsulfonic acid], XXXVIII. [Pentane2a, 5dicarboxy1sulfonic acid], XXXIX. [Pentane2a, 5dicarboxy1sulfate], XL. [Butanela, 4dicarboxy1sulfonic acid], XLI. [Butane1α, 4dicarboxy1sulfate],.
21. A method as claimed in claim 18, wherein said compound is selected from the group consisting of homoglutamic acid, homoglutamine and corresponding de amino analogs: I. [Dhomoglutamic acid, Nsulfonic acid], II. [Pentane2#, 5dicarboxy1sulfonic acid], III. [Pentane2#, 5dicarboxy1sulfate], IV. [Butane1 4dicarboxy1sulfonic acid], V. [Butane1 ß, 4dicarboxy1sulfate], VI. [Dhomoglutamic acid, 3asulfonic acid], VII. [Dhomoglutamic acid, 3asulfate], VIII. [Dhomoglutamic acid, 3isulfonic acid], IX. [Dhomoglutamic acid, 3psulfate], X. [Dhomoglutamic acid, 4asulfonic acid], XI. [Dhomoglutamic acid, 4asulfate], XII. [Dhomoglutamic acid, 4psulfonic acid], XIII. [Dhomoglutamic acid, 4psulfate], XIV. [Dhomoglutamic acid, 5asulfate], XV. [Dhomoglutamic acid, 5asulfate], XVI. [Dhomoglutamic acid, 5psulfonic acid], XVII. [Dhomoglutamic acid, 5#sulfate], XVIII. [Lhomoglutamine, Nsulfonic acid], XIX. [Pentane2acarboxy, 5carboxamido1sulfonic acid], XX. [Pentane2acarboxy, 5carboxamido1sulfate], XXI. [Butanelacarboxy, 4carboxamido1sulfonic acid], XXII. [ButaneI acarboxy, 4carboxamido1sulfate], XXIII. [Dhomoglutamine, Nsulfonic acid], XXIV. [Pentane2#carboxy, 5carboxamido1sulfonic acid], XXV. [Butane1 ßcarboxy, 4carboxamido1sulfonic acid], XXVI. [Butane1 # carboxy, 4carboxamido1sulfate], XXVII. [Dhomoglutamine, 3asulfonic acid], XXVIII. [Dhomoglutamine, 3asulfate], XXIX. [Dhomoglutamine, 3ßsulfonic acid], XXX. [Dhomoglutamine, 3#sulfate], XXXI. [Dhomoglutamine, 4asulfonic acid], XXXII. [Dhomoglutamine, 4asulfate], XXXIII. [Dhomoglutamine, 4psulfonic acid], XXXIV. [Dhomoglutamine, 4#sulfate], XXXV. [Dhomoglutamine, 5asulfonic acid], XXXVI. [Dhomoglutamine, 5asulfate], XXXVII. [Dhomoglutamine, 5psulfonic acid] and (XXVIII. [Dhomoglutamine, 5ßsulfate].
22. Use of a composition comprising general formula ZOC (C Rn1Rn2)COZ wherein Z = OH or NH2 and nl = n2 =1 to 8 together with an additive, excipient, diluents or carrier for modulation of immune response by differentiation of dendritic cells, by administration a pharmaceutical acceptable amount to a subject need thereof.
23. Use of the composition as claimed in claim 22, wherein said compound useful in vaccine formulation to prevent more efficient and faster presentation of antigens to Tcells thereby initiate primary protective Thl immune response and help in the clearance of the pathogen.
24. Use of the composition as claimed in claim 22, wherein said compound having a structure as herein and bearing general formula ZOCCR3R4CR1R2COOH wherein: Z=OH or NH2, R1, to R4 denotes H, NH2, SO3H, or OSO3H, CH2SO3H, CH2OS03H, NHS03H Structure 1.
25. Use of the composition as claimed in claim 22, wherein said compound having a structure as herein and bearing general formula ZOCCR5R6CR3R4CRIR2COOH wherein : Z=OH or NH2, R, to R6 denotes H, NH2, S03H, or OS03H, CH2SO3H, CH2OSO3H, NHS03H Structure 2.
26. Use of the composition as claimed in claim 22, wherein said compound having structure as herein and bearing general formula ZOCCR7R8CR5R6CR3R4 CRIR2COOH wherein: Z=OH or. NH2, R, to Rg denotes H, NH2, SO3H, or OSO3H, CH2SO3H, CH2OS03H, NHS03H structure 3.
27. Use of the composition as claimed in claim 22, wherein said compound in non toxic to monocytes.
28. Use of the composition as claimed in claim 22, wherein said compound in non toxic to macrophages.
29. Use of the composition as claimed in claim 22, wherein additives are different divalent metal cations such as Mg, Ca and Zn.
30. Use of the composition as claimed in claim 22, wherein additives are amino acid/ dicarboxylic acid derivatives and their pharmaceutically acceptable selected alkali/ alkaline earth metal salts.
31. Use of the composition as claimed in claim 22, wherein the compound is selected from the group consisting of : I [LAspartic acid, NSulfonic acid], II [2a, 3dicarboxy, propane1sulfonic acid], III [2a, 3dicarboxy, propane1sulfate], IV [I a, 2carboxy ethane sulfonic acid], V [1 a, 2carboxy ethane sulfate], VI [Daspartic acid, Nsulfonic acid], VII [2#,3carboxy,propane1sulfonic acid], VIII [2p, 3carboxy, propane1sulfate], IX [Iß, 2carboxy ethane1sulfonic acid], X [I ß, 2carboxy ethane1sulfate], XI [Daspartic acid, 3asulfonic acid], XII [Daspartic acid, 3asulfate], XIII [Daspartic acid, 3psulfonic acid], XIV [Daspartic acid, 3psulfate], XV [Lasparagine, Nsulfonic acid], XVI [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII [2acarboxy, 3carboxamido, propane1sulfate], XVIII [I acarboxy, 2carboxamido, ethane sulfonic acid], XIX [lacarboxy, 2carboxamido, ethane sulfate], XX [Lasparagine, 3asulfonic acid], XXI [Lasparagine, 3asulfate], XXII [Lasparagine, 3psulfonic acid], XXIII [Lasparagine, 3psulfate, XXIV [Dasparagine, Nsulfonic acid], XXV [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI [2pcarboxy, 3carboxamido, propane1sulfate], XXVII [lpcarboxy, 2carboxamido, ethane sulfonic acid], XXVIII [1#carboxy, 2carboxamido, ethane sulfate], XXIX [Dasparagine, 3asulfonic acid], XXX [Dasparagine, 3asulfate], XXXI [Dasparagine, 3psulfonic acid], XXXII [Dasparagine, 3psulfate], XXXIII [Lglutamic acid, Nsulfonic acid], XXXIV [2a, 4dicarboxy, butane1sulfonic acid], XXXV [2a, 4dicarboxy, butane1sulfate], XXXVI [la, 3dicarboxy, propane sulfonic acid], XXXVII [la, 3dicarboxy, propane sulfate], XXXVIII [I P, 3dicarboxy, propane sulfate], XXXIX [1 #, 3dicarboxy, propane sulfonic acid],.
32. Use of the composition as claimed in claim 22, wherein the compound is selected from the group consisting of : <BR> <BR> <BR> <BR> I [Dglutamic acid, Nsulfonic acid],<BR> <BR> <BR> <BR> <BR> <BR> <BR> II 2#, 4dicarboxy, butane1sulfonic acid], III [2p, 4dicarboxy, butane1sulfate], IV [Dglutamic acid, 3asulfonic acid], V [Dglutamic acid, 3asulfate], VI [Dglutamic acid, 3psulfonic acid], VII [Dglutamic acid, 3#sulfate], VIII [Dglutamic acid, 4asulfonic acid], IX [Dglutamic acid, 4asulfate], X [Dglutamic acid, 4#sulfonic acid], XI [Dglutamic acid, 3ßsulfate], XII [Lglutamine, Nsulfonic acid], XIII [2acarboxy, 4carboxamido, butane1sulfonic acid], XIV [2acarboxy, 4carboxamido, butane1sulfate], XV [1 acarboxy, 3carboxamido, propane1sulfonic acid], XVI [lacarboxy, 3carboxamido, propane1sulfate], XVII [1#carboxy, 3carboxamido, propane1sulfate], XVIII [I pcarboxy, 3carboxamido, propane1sulfonic acid], XIX [Dglutamine, Nsulfonic acid], XX [2#carboxy, 4carboxamido, butane1sulfonic acid], XXI [2pcarboxy, 4carboxamido, butane1sulfate], XXII [Dglutamine, 3asulfonic acid], XXIII [Dglutamine, 3asulfate], XXIV [Dglutamine, 3psulfonic acid], XXV [Dglutamine, 3#sulfate], XXVI [Dglutamine, 4asulfonic acid], XXVII [Dglutamine, 4αsulfate], XXVIII [Dglutamine, 4psulfonic acid], XXIX [Dglutamine, 4psulfate], XXX [Lhomoglutamic acid, Nsulfonic acid], XXXI [Pentane2a, 5dicarboxy1sulfonic acid], XXXII [Pentane2a, 5dicarboxy1sulfate], XXXIII UButanela, 4dicarboxy1sulfonic acid], XXXIV [Butane1α, 4dicarboxy1sulfate], XXXV [Dhomoglutamic acid, Nsulfonic acid], XXXVI [Pentane2p, 5dicarboxy1sulfonic acid], XXXVII [Pentane2p, 5dicarboxy1sulfate], XXXVIII [Butane1#, 4dicarboxy1sulfonic acid], XXXIX [Butane1 #, 4dicarboxy1sulfate],.
33. Use of the composition as claimed in claim 22, wherein the compound is selected from the group consisting of XXXIV. [Dhomoglutamic acid, 3asulfonic acid], XXXV. [Dhomoglutamic acid, 3asulfate], XXXVI. [Dhomoglutamic acid, 3psulfonic acid], XXXVII. [Dhomoglutamic acid,. 3psulfate], XXXVIII. [Dhomoglutamic acid, 4asulfonic acid], XXXIX. [Dhomoglutamic acid, 4asulfate], XL. [Dhomoglutamic acid, 4psulfonic acid], XLI. [Dhomoglutamic acid, 4#sulfate], XLII. [Dhomoglutamic acid, Sasulfate], XLIII. [Dhomoglutamic acid, Sasulfate], XLIV. [Dhomoglutamic acid, 5psulfonic acid], XLV. [Dhomoglutamic acid, 5psulfate], XLVI. [Lhomoglutamine, Nsulfonic acid], XLVII. [Pentane2acarboxy, 5carboxamido1sulfonic acid], XLVIII. [Pentane2acarboxy, 5carboxamido1sulfate], XLIX. [Butane1αcarboxy, 4carboxamido1sulfonic acid], L. [Butanelacarboxy, 4carboxamido1sulfate], LI. [Dhomoglutamine, Nsulfonic acid], <BR> <BR> <BR> <BR> <BR> LII. [Pentane2 (3carboxy, 5carboxamido1sulfonic acid],<BR> <BR> <BR> <BR> <BR> <BR> <BR> LIII. [Butane1 # carboxy, 4carboxamido1sulfonic acid], LIV. [Butane1 # carboxy, 4carboxamido1sulfate], LV. [Dhomoglutamine, 3asulfonic acid], LVI. [Dhomoglutamine, 3asulfate], LVII. [Dhomoglutamine, 3psulfonic acid], LVIII. [Dhomoglutamine, 3ßsulfate], LIX. [Dhomoglutamine, 4asulfonic acid], LX. [Dhomoglutamine, 4asulfate], LXI. [Dhomoglutamine, 4psulfonic acid], LXII. [Dhomoglutamine, 4psulfate], LXIII. [Dhomoglutamine, 5asulfonic acid], LXIV. [Dhomoglutamine, 5αsulfate], LXV. [Dhomoglutamine, 5psulfonic acid] and LXVI. [Dhomoglutamine, 5psulfate].
34. Use of the composition as claimed in claim 22, wherein novel sulfonic acid /sulfate derivatives of the formulae ZOCCR3R4CRxR2COOH wherein: Z=OH or NH2, Ri, to R4 denotes H, NH2, SO3H, or OS03H, CH2SO3H, CH2OS03H, NHS03H XXXIII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=H, R NHS03H is the same meaning as is before defined; XXXIV. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=H, Rut= CH2S03H is the same meaning as is before defined; XXXV. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=H, R1= CH20SO3H is the same meaning as is before defined; XXXVI. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=H, R1=SO3H is the same meaning as is before defined ; KXXVII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=H, R=OSO3H is the same meaning as is before defined; (XXVIII. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=H, R2= NHS03H is the same meaning as is before defined ; XXXIX. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined; XL. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=H, R2= CH2OSO3H is the same meaning as is before defined; XLI. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=H, R2=SO3H is the same meaning as is before defined; XLII. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=H, R2=OS03H is the same meaning as is before defined; XLIII. A compound as claimed in claim 22, wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined ; XLIV. A compound as claimed in claim 22, wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined; XLV. A compound as claimed in claim 22, wherein Z=OH, R1=R3=H, R2=NH2, R4=S03H is the same meaning as is before defined; XLVI. A compound as claimed in claim 22, wherein Z=OH, R, =R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=H, R, =NHS03H is the same meaning as is before defined ; XLVIII. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=H, R=CH2$O3H is the same meaning as is before defined; XLIX. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=H, R, = CH20S03H is the same meaning as is before defined; L. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=H, Rl=SO3H is the same meaning as is before defined; LI. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=H, R1=OSO3H is the same meaning as is before defined ; LII. A compound as claimed in claim 22, wherein Z=NH2, RI=R4==H, R2=NH2, R3= S03H is the same meaning as is before defined ; LIII. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined ; LIV. A compound as claimed in claim 22, wherein Z=NH2, Rl=R3=H, R2=NH2, R4= S03H is the same meaning as is before defined; LV. A compound as claimed in claim 1, wherein Z=NH2, Rl=R3=H, R2= NH2, R4= OS03H is the same meaning as is before defined; LVI. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=H, R2= NHS03H is the same meaning as is before defined; LVII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=H, R2= CH2OS03H is the same meaning as is before defined; LIX. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=H, R2=SO3H is the same meaning as is before defined; LX. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=H, R2=OSO3H is the same meaning as is before defined ; LXI. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=H, R2=NH2, R3= SO3H is the same meaning as is before defined ; LXII. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=H, R2=NH2, R3= OSO3H is the same meaning as is before defined; LXIII.'A compound as claimed in claim 22, wherein Z=NH2, R1=R3=H, R2=NH2, R4=SO3H is the same meaning as is before defined ; LXIV. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined.
35. Use of the composition as claimed in claim 22, wherein novel sulfonic acid /sulfate derivatives of the formulae ZOCCR5R6CR3R4CRIR2COOH, wherein: Z=OH or NH2, Ri, to R6 denotes H, NH2, S03H, or OS03H, CH2 S03H, CH2OS03H, NHS03H XXXVII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined ; XXXVIII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6=H, Rl= CH2SO3H is the same meaning as is before defined ; XXXIX. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6=H, R, =CH2OS03H is the same meaning as is before defined; XL. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4= R5=R6=H, R1= SO3H is the same meaning as is before defined; XLI. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6=H, R1=OSO3H is the same meaning as is before defined ; XLII. A compound as claimed in claim 22, wherein Z=OH, R) =R3=R4=R5=R6=H, R2=OS03H is the same meaning as is before defined; XLIII. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R4=R5=R6=H, R2= S03H is the same meaning as is before defined ; XLIV. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=R5=R6=H, R2= NHSO3H is the same meaning as is before defined ; XLV. A compound as claimed in claim 22, wherein Z=OH, R, =R3=R4= R5=R6=H R2= CH2SO3H is the same meaning as is before defined ; XLVI. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=R5=R6=H, R2= CH2OSO3H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22, wherein Z=OH, R1=R4=R5=R6=H, R2= NH2, R3=SO3H is the same meaning as is before defined; XLVIII. A compound as claimed in claim 22, wherein Z=OH, R1=R4=R5=R6=H, R2= NH2, R3=OSO3H is the same meaning as is before defined ; XLIX. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R5=R6=H, R2= NH2, R4= SO3H is the same meaning as is before defined; L. A compound as claimed in claim 22, wherein Z=OH, R) =R3=R5=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined; LI. A compound as claimed in claim 22, wherein Z=OH, R1=R4= R3=R6=H, R2= NH2, R5=SO3H is the same meaning as is before defined; LII. A compound as claimed in claim 22, wherein Z=OH, R1=R4=R3=R6=H, R2= NH2, R5=OS03H is the same meaning as is before defined; LIII. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=Rs=R4=H, R2= NH2, R6=SO3H is the same meaning as is before defined; LIV. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R5=R4=H, R2= NH2, R6=OS03H is the same meaning as is before defined; LV. A compound as claimed in claim 22, wherein Z=NH R2=R3=Ra=Rs=R6=H, Ri=NHS03H is the same meaning as is before defined; LVI. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=Rt= R5=R6=H, R1=CH2SO3H is the same meaning as is before defined; LVII. A compound as claimed in claim 22, wherein. Z=NH2, R2=R3=R4=R5=R6=H, Rl= CH20S03H is the same meaning as is before defined ; LVIII. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=SO3H is the same meaning as is before defined; LIX. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=R5=R6=H, R1= OSO3H is the same meaning as is before defined ; LX. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= OSO3H is the same meaning as is before defined ; LXI. A compound as claimed in claim 22, wherein Z=NH2, R, =R3=R4=R5=R6=H, R2= S03H is the same meaning as is before defined; LXII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= NHSO3H is the same meaning as is before defined ; LXIII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2=CH2SO3H is the same meaning as is before defined ; LXIV. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= CH2OSO3H is the same meaning as is before defined; LXV. A compound as claimed in claim 22, wherein Z=NH2, Ri=R4=R5=R6=H, R2= NH2, R3=SO3H is the same meaning as is before defined; LXVI. A compound as claimed in claim 22, wherein Z=NH2, Ri=R4=R5=R6=H,. R2= NH2, R3=OS03H is the same meaning as is before defined; LXVII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R6=H, R2= NN2, R4=S03H is the same meaning as is before defined LXVIII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R6=H, R2= NH2, R4=OSO3H is the same meaning as is before defined; LXIX. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, R5=SO3H is the same meaning as is before defined; LXX. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, R5=OSO3H is the same meaning as is before defined; LXXI. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=S03H is the same meaning as is before defined; LXXII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=OS03H is the same meaning as is before defined.
36. Use of the composition as claimed in claim 22, wherein novel sulfonic acid/sulfate derivatives of the formulae ZOCCR7R8CR5R6CR3R4CR1R2COOH, wherein : Z=OH or NH2, Ri, to k8 denotes H, NH2, S03H, or OS03H, CH2SO3H, CH2OSO3H, NHS03H XLIV. A compound as claimed in claim 22. wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=} R, =NHS03H is the same meaning as is before defined; XLV. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R, =CH2SO3H is the same meaning as is before defined ; XLVI. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6= R7=Rs=H, R1=CH2OSO3H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=Rt= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined ; XLVIII. A compound as claimed in claim 22, wherein Z=OH, R2=R3=R4=R5=R6= R7=Rs=H, R1=OSO3H is the same meaning as is before defined; XLIX. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R4=R5=R6 R7=Rs=H, R2=NHS03H is the same meaning as is before defined; L. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined; LI. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2OSO3H is the same meaning as is before defined; LII. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R4= R5=R6=R7=R8=H, R2=SO3H is the same meaning as is before defined; LIII. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R4=R5=R6= R7=Rs=H, R2=OS03H is the same meaning as is before defined; LIV. A compound as claimed in claim 22, wherein Z=OH, R1=R4= R5=R6= R7=R8=H, R2=NH2, R3=S03H is the same meaning as is before defined; LV. A compound as claimed in claim 22, wherein Z=OH, R1=R4=R5=R6=R7=R8=H, R2=NH2, R3=OSO3H is the same meaning as is before defined ; LVI. A compound as claimed in claim im 22, wherein Z=OH, R1=R3=R5=R6= R7=R8=H, R2= NH2, R4=S03H is the same meaning as is before defined ; LVII. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R5=R6=R7=R8=H, R2=NH2, R4=OSO3H is the same meaning as is before defined ; LVIII. A compound as claimed in claim 22, wherein Z=OH, R1=R4= R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined; LIX. A compound as claimed in claim 22, wherein Z=OH, RI=R, =R3=R6= R7=Rs=H, R2=NH2, R5=OSO3H is the same meaning as is before defined; LX. A compound as claimed in claim 22, wherein Z=OH, Rj=R3=R5=R4= R7=R8=H, R2=NH2, R6=SO3H is the same meaning as is before defined ; LXl. A compound as claimed in claim 22, wherein Z=OH, Rl=R3=R5=R4= R7=R8=H, R2=NH2, R6=OSO3H is the same meaning as is before defined ; LXII. A compound as claimed in claim 22, wherein Z=OH, Rj=R4=R3=R6=R5=R8=H, R2=NH2, R7=S03H is the same meaning as is before defined; LXIII. A compound as claimed in claim 22, wherein Z=OH, Rl=R4=R3=R6=R5=R8=H, R2=NH2, R7=OSO3H is the same meaning as is before defined ; LXIV. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R5=R4=R7=R6=H, R2=NH2, Rs=S03H is the same meaning as is before defined; LXV. A compound as claimed in claim 22, wherein Z=OH, R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=OSO3H is the same meaning as is . before defined ; LXVI. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=NHSO3H is the same meaning as is before defined; LXVII. A compound, as claimed in claim 22, wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, Ri=CH2S03H is the same meaning as is before defined; LXVIII. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4=R5=R6= R7=Rs=H, R, =CH20S03H is the same meaning as is before defined; LXIX. A compound as claimed in claim 22, wherein Z=NH2, R2=R3=R4= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined; LXX. A compound as claimed in claim 22, wherein Z==NH2, R2=R3=R4=R5=R6= R7=Rs=H, R1=OSO3H is the same meaning as is before defined; LXXI. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6= R7=R8=H, R2=NHS03H is the same meaning as is before defined ;.
37. LXXII. A compound as claimed in claim 22, wherein Z=NH Rl=R3=R4=RS=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4= R5=R6=R7=R8=H, R2=SO3H is the same meaning as is before defined; LXXIV. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R4=R5=R6= R7=Rs=H, R2=OS03H is the same meaning as is before defined; LXXV. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R5=6= R7=R8=H, R2=NH2, R3=SO3H is the same meaning as is before defined; LXXVI. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R5=R6= R7=R8=H, R2=NH2, R3=OSO3H is the same meaning as is before defined; LXXVII. A compound as claimed in claim 22, wherein Z=NH2, Ri=R3=R5=R6=R7=Rs= H, R2=NH2, R4=S03H is the same meaning as is before defined; A compound as claimed in claim 22, wherein Z=NH2, Rl=R3=R5=R6=R7=R8= H, R2=NH2, R4=OS03H is the same meaning as is before defined ; LXXIX. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R3=R6= R7=Rs=H, R2=NH2, R5=S03H is the same meaning as is before defined; LXXX. A compound as claimed in claim 22, wherein Z=NH2, R ; =R4=R3=R6= R7=Rs=H, R2=NH2, R5=OS03H is the same meaning as is before defined; LXXXI. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4= R7=Rs=H, R2=NH2, R6=SO3H is the same meaning as is before defined; LXXXII. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=OSO3H is the same meaning as is before defined; 15LXXXIII. A compound as claimed in claim 22, wherein Z=NH2, R, =R4R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined; LXXXIV. A compound as claimed in claim 22, wherein Z=NH2, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=OSO3H is the same meaning as is before defined ; LXXXV. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4=R7=R6=H, R2= NH2, R8=SO3H is the same meaning as is before defined; LXXXVI. A compound as claimed in claim 22, wherein Z=NH2, R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=OSO3H is the same meaning as is before defined ;.
38. Use of the composition as claimed in claim 22, wherein said compound is non toxic salts selected from the group consisting of : I [LAspartic acid, NSulfonic acid], II [ a, 3dicarboxy, propane1sulfonic acid], III [2a, 3dicarboxy, propaneIsulfate], IV [1α,2carboxy ethane sulfonic acid], V [1 a, 2carboxy ethane sulfate], VI [Daspartic acid, Nsulfonic acid], VII [2ß,3carboxy,propane1sulfonic acid], VIII [2p, 3carboxy, propane1sulfate], IX [1ß,2carboxy ethane1sulfonic acid], X [1ß,2carboxy ethane1sulfate], XI [Daspartic acid, 3αsulfonic acid], XII [Daspartic acid, 3αsulfate], XIII [Daspartic acid, 3ßsulfonic acid], XIV [Daspartic acid, 3psulfate], XV [Lasparagine, Nsulfonic acid], XVI [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII [2acarboxy, 3carboxamido, propane1sulfate], XVIII [1αcarboxy, 2carboxamido, ethane sulfonic acid], XIX [I acarboxy, 2carboxamido, ethane sulfate], XX [Lasparagine, 3asulfonic acid], XXI [Lasparagine, 3asulfate], XXII [Lasparagine, 3psulfonic acid], XXIII [Lasparagine, 3ßsulfate, XXIV [Dasparagine, Nsulfonic acid], XXV [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI [2pcarboxy, 3carboxamido, propane1sulfate], XXVII [I icarboxy, 2carboxamido, ethane sulfonic acid], XXVIII [1ßcarboxy, 2carboxamido, ethane sulfate], XXIX [Dasparagine, 3asulfonic acidl, XXX [Dasparagine, 3αsulfate], XXXI [Dasparagine, 3ßsulfonic acid], XXXII [Dasparagine, 3psulfate], XXXIII [Lglutamic acid, Nsulfonic acid), XXXIV [2a, 4dicarboxy, butaneIsulfonic acid], XXXV [2a, 4dicarboxy, butane1sulfate], XXXVI [1α, 3dicarboxy, propane sulfonic acid], XXXVIl 11a, 3dicarboxy, propane sulfate], XXXVIII [1ß, 3dicarboxy, propane sulfate], XXXIX [I P, 3dicarboxy, propane sulfonic acid],.
39. Use of the composition as claimed in claim 22, wherein said compound is non toxic salts selected from the group consisting of : I [Dglutamic acid, Nsulfonic acid], II [2ß, 4dicarboxy, butane1sulfonic acid], III [2p, 4dicarboxy, butane1sulfate], IV [Dglutamic acid, 3αsulfonic acid], V [Dglutamic acid, 3asulfate], VI [Dglutamic acid, 3ßsulfonic acid], VII [Dglutamic acid, 3ßsulfate], VIII [Dglutamic acid, 4asulfonic acid], IX [Dglutamic acid, 4αsulfate], X [Dglutamic acid, 4ßsulfonic acid], XI [Dglutamic acid, 3psulfate], XII [Lglutamine, Nsulfonic acid], XIII [2acarboxy, 4carboxamido, butaneIsulfonic acid], XIV [2acarboxy, 4carboxamido, butane1sulfate], XV [I acarboxy, 3carboxamido, propane1sulfonic acid], XVI [) acarboxy, 3carboxamido, propane1sulfate], XVII [I ßcarboxy, 3carboxamido, propane1sulfate], XVIII [l pcarboxy, 3carboxamido, propane1sulfonic acid], XIX [Dglutamine, Nsulfonic acid], XX [2ßcarboxy, 4carboxamido, butaneIsulfonic acid], XXI [2ßcarboxy, 4carboxamido, butane1sulfate], XXII [Dglutamine, 3αsulfonic acid], XXIII [Dglutamine, 3αsulfate], XXIV [Dglutamine, 3ßsulfonic acid], XXV [Dglutamine, 3ßsulfate], XXVI [Dgiutamine, 4asulfonic acid], XXVII [Dglutamine, 4asulfate], XXVIII [Dglutamine, 4ßsulfonic acid], XXIX [Dglutamine, 4ßsulfate], XXX [Lhomoglutamic acid, Nsulfonic acid], XXXI [Pentane2α, 5dicarboxy1sulfonic acid], XXXII [Pentane2α, 5dicarboxy1sulfate],<BR> XXXIII [ButaneI a, 4dicarboxy1sulfonic acid], XXXIV [Butanela, 4dicarboxy1sulfate], XXXV [Dhomoglutamic acid, Nsulfonic acid ;, <BR> <BR> XXXVI [Pentane2ß, 5diearboxylsulfonie aeid], XXXVII [Pentane2p, 5dicarboxy1sulfate], XXXVIII [Butane1 (3, 4dicarboxy1sutfonic acid], XXXIX [Butane1ß, 4dicarboxy1sulfate],.
40. Use of the composition as claimed in claim 22, wherein said compound is non toxic salts selected from the group consisting of : I [Dhomoglutamic acid, 3asulfonic acid], II [Dhomoglutamic acid, 3asulfate], III [Dhomoglutamic acid, 3isulfonic acid], IV [Dhomoglutamic acid, 3ßsulfate], V [Dhomoglutamic acid, 4asulfonic acid], VI [Dhomoglutamic acid, 4asulfateJ, VII [Dhomoglutamic acid, 43sulfonic acid], VIII [Dhomoglutamic acid, 4ßsulfate], IX [Dhomoglutamic acid, 5αsulfate], X [Dhomoglutamic acid, 5αsulfate], XI [Dhomoglutamic acid, 5psulfonic acid], XII [Dhomoglutamic acid, 5ßsulfate], XIII [Lhomoglutamine, Nsulfonic acid], XIV [Pentane2acarboxy, 5carboxamidolsulfonic acid], XV [Pentane2αcarboxy, 5carboxamido1sulfate], XVI [Butane1αcarboxy, 4carboxamido1sulfonic acid], XVII [Butane1αcarboxy, 4carboxamido1sulfate], XVIII [Dhomoglutamine, Nsulfonic acid], XIX [Pentane2ßcarboxy, 5carboxamido1sulfonic acid], XX [Butane1ßcarboxy, 4carboxamido1sulfonic acid], XXI [Butane1ßcarboxy, 4carboxamido1sulfate], XXII [Dhomoglutamine, 3asulfonic acid], XXIII [Dhomoglutamine, 3asulfate], XXIV [Dhomoglutamine, 3ßsulfonic acid], XXV [Dhomoglutamine, 3(3sulfate], XXVI [Dhomoglutamine, 4asulfonic acid], XXVII [Dhomoglutamine, 4asulfate], XXVIII [Dhomoglutamine, 4psulfonic acid], XXIX [Dhomoglutamine, 4ßsulfate], XXX [Dhomoglutamine, Sasulfonic acid], XXXI [Dhomoglutamine, 5asulfate], XXXII [Dhomoglutamine, 5psulfonic acid] and XXXIII [Dhomoglutamine, 5ßsulfate].
41. Use of the composition as claimed in claim 22, wherein said compound is selected from the group consisting of aspartic acid, asparagine and corresponding deamino analogs : I [LAspartic acid, NSulfonic acid], II [2a, 3dicarboxy, propane1sulfonic acid], III [2a, 3dicarboxy, propane1sulfate], IV [I a, 2carboxy ethane sulfonic acid], V [I a, 2carboxy ethane sulfate], VI [Daspartic acid, Nsulfonic acid], VII [2p, 3carboxy, propane1sulfonic acid], VIII [2ß,3carboxy,propane1sulfate], IX [I ß, 2carboxy ethane1sulfonic acid], X [I ß, 2carboy ethane1sulfate], XI [Daspartic acid, 3asulfonic acid], XII [Daspartic acid, 3asulfate], XIII [Daspartic acid, 3 (3sulfonic acid], XIV [Daspartic acid, 3ßsulfate], XV [Lasparagine, Nsulfonic acid], XVI [2acarboxy, 3carboxamido, propane1sulfonic acid], XVII [2acarboxy, 3carboxamido, propaneIsulfate], XVIII [I acarboxy, 2carboxamido, ethane sulfonic acid], XIX [1 acarboxy, 2carboxamido, ethane sulfate], XX [Lasparagine, 3asulfonic acid], XXI [Lasparagine, 3asulfate], XXII [Lasparagine, 3ßsulfonic acid], XXIII [Lasparagine, 3ßsulfate, XXIV [Dasparagine, Nsulfonic acid], XXV [2pcarboxy, 3carboxamido, propane1sulfonic acid], XXVI [2ßcarboxy, 3carboxamido, propane1sulfate], XXVII [1ßcarboxy, 2carboxamido, ethane sulfonic acid], XXVIII [1ßcarboxy, 2carboxamido, ethane sulfate], XXIX [Dasparagine, 3asulfonic acid], XXX [Dasparagine, 3asulfate], XXXI [Dasparagine, 3ßsulfonic acid], XXXII [Dasparagine, 3psulfate],.
42. Use of the composition as claimed in claim 22, wherein said compound is selected from the group consisting of glutamic acid, glutamine and corresponding deamino analogs: 1 [Lglutamic acid, Nsulfonic acid], II [2a, 4dicarboxy, butane1sulfonic acid], III [2a, 4dicarboxy, butane1sulfate], IV [I a, 3dicarboxy, propane sulfonic acid], V [I a, 3dicarboxy, propane sulfate], VI [1ß,3dicarboxy, propane sulfate], VII [I ß, 3dicarboxy, propane sulfonic acid], VIII [Dglutamic acid, Nsulfonic acid], IX [2ß, 4dicarboxy, butane1sulfonic acid], X [2ß, 4dicarboxy, butane1sulfate], Xl [Dglutamic acid, 3asulfonic acid], XII [Dglutamic acid, 3αsulfate], XIII [Dglutamic acid, 3psulfonic acid], XIV [Dglutamic acid, 3psulfate], XV [Dglutamic acid, 4asulfonic acid], XVI [Dglutamic acid, 4asulfate], XVII [Dglutamic acid, 4ßsulfonic acid], XVIII [Dglutamic acid, 3psulfate], XIX [Lglutamine, Nsulfonic acid], XX [2αcarboxy, 4carboxamido, butane1sulfonic acid], XXI [2αcarboxy, 4carboxamido, butane1sulfate], XXII [1αcarboxy, 3carboxamido, propane1sulfonic acid], XXIII [1αcarboxy, 3carboxamido, propane1sulfate], XXIV [I pcarboxy, 3carboxamido, propane1sulfate], XXV [Ißcarboxy, 3carboxamido, propane1sulfonic acid], XXVI [Dglutamine, Nsulfonic acid], XXVII [2pcarboxy, 4carboxamido, butane1sulfonic acid], XXVIII [2pcarboxy, 4carboxamido, butane1sulfate], XXIX [Dglutamine, 3αsulfonic acid], XXX [Dglutamine, 3αsulfate], XXXI [Dglutamine, 3psulfonic acid], XXXII [Dglutamine, 3ßsulfate], XXXIII [Dglutamine, 4asulfonic acid], XXXIV [Dglutamine, 4asulfate], XXXV [Dglutamine, 4psulfonic acid], XXXVI [Dglutamine, 4ßsulfate], XXXVII [Lhomoglutamic acid, Nsulfonic acid], XXXVIII [Pentane2α, 5dicarboxy1sulfonic acid], XXXIX [Pentane2a, 5dicarboxy1sulfate], XL [Butanela, 4dicarboxyIsulfonic acid], XLI [Butane1α, 4dicarboxy1sulfate],.
43. Use of the composition as claimed in claim 22, wherein said compound is selected from the group consisting of homoglutamic acid, homoglutamine and corresponding deamino analogs : I [Dhomoglutamic acid, Nsulfonic acid], II [Pentane2ß, 5dicarboxy1sulfonic acid], III [Pentane2ß, 5dicarboxy1sulfate], IV [Butane1ß, 4dicarboxy1sulfonic acid], V [Butane1ß, 4dicarboxy1sulfate], VI [Dhomoglutamic acid, 3asulfonic acid], VII [Dhomoglutamic acid, 3asulfate], VIII [Dhomoglutamic acid, 3psulfonic acid], IX [Dhomoglutamic acid, 3psulfate], X [Dhomoglutamic acid, 4asulfonic acid], XI [Dhomoglutamic acid, 4αsulfate], XII [Dhomoglutamic acid, 4ßsulfonic acid], XIII [Dhomoglutamic acid, 4ßsulfate], XIV [Dhomoglutamic acid, 5αsulfate], XV [Dhomoglutamic acid, Sasulfate], XVI [Dhomoglutamic acid, 5psulfonic acid], XVII [Dhomoglutamic acid, 5psulfate], XVIII [Lhomoglutamine, Nsulfonic acid], XIX [Pentane2acarboxy, 5carboxamido1sulfonic acid], XX [Pentane2acarboxy, 5carboxamido1sulfate], XXI [ButaneI acarboxy, 4carboxamido1sulfonic acid], XXII [Butane1αcarboxy, 4carboxamido1sulfate], XXIII [Dhomoglutamine, Nsulfonic acid], XXIV [Pentane2 (3carboxy, 5carboxamido1sulfonic acid], XXV [ButaneI pcarboxy, 4carboxamido1sulfonic acid], XXVI [Butane1ßcarboxy, 4carboxamido1sulfate], XXVII [Dhomoglutamine, 3asulfonic acid], XXVIII [Dhomoglutamine, 3asulfate], XXIX [Dhomoglutamine, 3ßsulfonic acid], XXX [Dhomoglutamine, 3ßsulfate], XXXI [Dhomoglutamine, 4asulfonic acid], XXXII [Dhomoglutamine, 4asulfate], XXXIII [Dhomoglutamine, 4 (3sulfonic acid], XXXIV [Dhomoglutamine, 4 (3sulfate], XXXV [Dhomoglutamine, 5αsulfonic acid], XXXVI [Dhomogtutamine, 5asulfate], XXXVII [Dhomoglutamine, 5ßsulfonic acid] and , <XXVIII [Dhomoglutamine, 5psulfate]. AMENDED CLAIMS [Received by The International Bureau on 19 February 2005 (19.02. 05) ; original claim 1 amended; remaining claims unchanged 1. A method for modulating immune response by differentiation of dendritic cells, said method comprising the step of administrating a pharmaceutically acceptable amount of a compound having general formula ZOC (C Rn1Rn2)COZ wherein Z = OH or NH2 and nl = n2 =1 to 8 to the subject in need thereof optionally with an additive, excipient, diluents or carrier.
44. 2 A method as claimed in claim 1, wherein said compound useful in vaccine formulation to prevent more efficient and faster presentation of antigens to Tcells thereby initiate primary protective Thl immune response and help in the clearance of the pathogen.
45. 3 A method as claimed in claim It wherein said compound having a structure as herein and bearing general formula ZOCCR3R4CR1R2COOH wherein: Z=OH or NHz, RI, to R4 denotes H, NH2, SO3H, or OS03H, CH2SO3H, CH2OSO3H, NHS03 Stzucture 1.
46. A method as claimed in claim 1, wherein said compound having a structure as herein and bearing general formula ZOCCR5R6CR3R4CR1R2COOH wherein: Z=OH or NH2, Ri to Rz denotes H, NH2, SO3H, or OSO3H, CH2SO3H, CH2 OSO3H, NHSOgH Structure 2 STATEMENT UNDER ARTICLE 19 (1) After reviewing the citations of International Search report, the Applicants have amended the claims and amended claims are attached herewith. Comments on the citations are as below: 1. DI XP 009032996 and D2 XP 0022SS048 : None of the citations disclose compounds useful in differentiation of dendritic cells. They merely disclosed the compounds capable of modulating cancer cells and neuropeptides None of the compounds are disclosed in this citation which can be used for the differentiation of dendritic cells. The present invention discloses sulfated/sulfonated analogues of aspartic acid, asparagines, glutamine, glutamic acid, homoglutamic acid and homoglutamine in combination with divalent metal ions (Ca, Mg, Zn). In view of the above, the Applicants request to the learned Examiner to allow the claimed, Finally, the applicant believes that the amendments made to the claims are falling within the scope of claims and no additional matter is added.
Description:
NOVEL MOLECULE FOR INDUCING DIFFERENTIATION OF DENDRITIC CELLS FIELD OF INVENTION: The present invention relates to compounds general formula Z-OC (C RnRn2)-CO-Z wherein Z = OH or NH2 and nl = n2 =1 to 8. for modulation of immune response by differentiation of dendritic cells containing novel class of amino acid/dicarboxylic acid derivatives of the general formula ZOC-CR3R4-CR, R2-COOH, ZOC-CR5R6-CR3R,- CRl R2-COOH, ZOC-CR7Rs-CR5R-CR3R4-CRIR2-COOH.

BACKGROUND AND PRIOR ART REFERENCES: Indian green mussels (Perna viridis) are the cheap source of proteins and considered as a delicacy. Extract prepared from green mussels by enzyme-acid hydrolysis process showed various biological activities. In our earlier patent (US patent application #20030044470) we have shown the inhibition of osteoclast differentiation and activation in the crude extract. In same continuation, attempts have been made to purify the active compound that showed inhibition of osteoclast differentiation and activation. The purification of the crude extract was done using HPLC, g el filtration and T LC m ethods. T he p urified c ompound was again checked for the above activity. The compound was characterized using NMR and LC-MS/MS techniques. This compound was synthesized and checked for the presence of the above biological activity. This patent in particular describes the synthesis of the compound and also its activity for inhibition of osteoclast formation.

Novel class of amino acid/dicarboxylic acid derivatives (sulfonic acid/sulfate derivatives of naturally occurring amino acids and their amides) along with calcium is for their activation to show inhibition of the dendritic cells. Amino acid derivatives and calcium ion when used separately did not show any activity on differentiation of dendritic cells. The following classes of compounds are identified.

(1) Natural acidic amino acids (Aspartic acid, Glutamic acid and their amides), (2) Unnatural amino acids, amides such as homoglutamic acid, (3) Dicarboxylic acids such as succinic acid, glutaric acid, and adipic acid (4) N-sulfonyl, C-sulfonyl/sulfate derivatives of the above acids (5) Alkali and alkaline earth metals such as Na, K, Mg, Zn and Ca as their suitable salts A number of molecules are known to induce the differentiation and maturation of dendritic cells from precursors. Some of the recent ones are listed below:

1. The most studied is differentiation of DCs with GM-CSF which is the conventional method to generate DCs from bone marrow ; The DCs obtained in this manner are immature in nature.

2. Maturation of DCs is normally obtained by stimulating the immature DCs with Tumor Necrosis Factor-alpha (TNF-0). Recently TNF-0 has been shown to induce the differentiation of DCs from monocytes.

3. CD40 ligand (CD401) that is normally expressed on T cells also induces the maturation of DCs. An alternative for CD401 is the use of commercially available anti-CD40 monoclonal antibody.

4. Stimulation with the extracellular endotoxin, Lipopolysaccharide (LPS) from Escherichia coli is also a common method to mature DCs 5. Atrial natriuretic peptide (ANP) a cardiovascular hormone secreted mainly by the cardiac atria regulates the volume-pressure homeostasis. The action of ANP is mediated by its receptor, guanylyl cyclase-coupled receptor A (GC-A) and has recently been shown to induce the maturation of DCs by increasing cytokine secretion and increases in various cell surface molecule expression.

6. The imidazoquinoline compounds imiquimod and R-848 are low-molecular-weight anti-viral compounds that are immune response modifiers and induce the synthesis of interferon-alpha and other cytokines in a variety of cell types. These compounds have potent anti-viral and anti-tumor properties and have recently been shown to induce the activation of macrophages and splenocytes and induce the maturation of Dendritic cells.

7. Stimulation of Flt3 receptor tyrosine kinase through its cognate ligand expands early hematopoietic progenitor and Dendritic cells (DCs) in humans and mice.

8. Prostaglandin E2, found at high concentrations under the skin has been shown to facilitate initiation of skin immune responses by promoting the migration and maturation of Langerhans cells, a DC subtype found under the epidermis and in the dermis of the skin.

9. Fermented mistletoe extract often used for adjuvant treatment of cancer patients, significantly stimulated the maturation of pre-differentiated immature DC, as evidenced by a heightened expression of CD83. Like the positive control TNF- alpha, the mistletoe extract significantly activated CD80 and CD86 as well as HLA class I and II molecules on these cells.

10. Lysophosphatidylcholine (LPC) is a major lipid component of oxidized low density lipoprotein with reported pro-inflammatory activities. It is now reported that LPC acts through G protein-coupled receptors on differentiating monocytes to generate mature dendritic cells with the ability to stimulate IL-2 and IFN-gamma production by allogeneic T lymphocytes.

OBJECTIVE OF INVENTION The objective of the invention relates to compounds compounds general formula Z-OC (C Rn) Rn2)-CO-Z wherein Z = OH or NH2 and nl = n2 =1 to 8. for modulation of immune response by differentiation dendritic cells containing novel class of amino acid/ dicarboxylic acid derivatives (sulfonic acid/sulfate derivatives of naturally occurring amino acids and their amides). : C ompounds f or i nduction o f d ifferentiation o f d endritic cells containing novel class of amino acid/dicarboxylic acid derivatives of the general formula ZOC-CR3R4-CRIR2-COOH, ZOC-CR5R6-CR3R4-CRIR2-COOH, ZOC-CR7R8- CR5R6-CR3R4-CRIR2-COOH wherein Z= OH or NH2 ; RI, to R8 denotes H, NH2, SO3H, or OSOiH, CH2-SO3H, CH2-OS03H, NHS03H. wherein all the symbols are the same meaning as hereinafter defined and non-toxic salts thereof as an active ingredient.

Another objective of the present invention relates to a method for modulation of immune response controlled by differentiating dendricts cells.

Another objective of the present invention relates to use of compound in vaccine formulation or in protection based studies to promote more efficient and faster presentation of the antigens to T-cell thereby initiative primary protective Thl immune response and help in clearance in pathogens.

Another objective of the present invention relates to novel compound useful in vaccination, cancer therapy and other immunomodulatory regiments.

The further objective of the present invention relates to administration a pharmaceutical acceptable amount of a compound optionally with an additive, excipient, diluents or carrier for modulation of immune response.

SUMMARY OF THE INVENTION This invention is related to compounds compounds general formula Z-OC (C R, Rn2)-CO- Z wherein Z = OH or NH2 and nl = n2 =1 to 8. for modulation of immune response by differentiation for induction of differentiation of dendritic cells containing novel class of amino acid/dicarboxylic acid derivatives (sulfonic acid/sulfate derivatives of naturally occurring amino acids and their amides). More particularly, this invention is related to:

1) Compounds for induction of differentiation of dendritic cells containing novel class o f amino a cid/d icarboxylic acid derivatives o f t he general formula ZOC- CR3R4-CRR2-COOH, ZOC-CR5R6-CR3R4-CRwR2-COOH, ZOC-CR7R-CRsR6- CR3R-CRR2-COOH wherein Z= OH or NlI2 ; RI, to Rg denotes H, NH2, S03H, or OS03H, CH2-SO3H, CH2-OS03H, NHS03H. wherein all the symbols are the same meaning as hereinafter defined and non-toxic salts thereof as an active ingredient, 2) The compounds inducing differentiation of dendritic cells also contain different divalent metal cations such as Mg, Ca and Zn, wherein all the symbols are the same meaning as hereinafter defined and non-toxic salts thereof as an active ingredient, 3) The composition consists of varying amounts of the above amino acid/dicarboxylic acid derivatives and their pharmaceutically acceptable selected alkali/alkaline earth metal salts, wherein all the symbols are the same meaning as hereinafter defined and non-toxic salts thereof as an active ingredient, 4) The process for the preparation of the aforesaid compounds, useful in inducing differentiation of dendritic cells.

DETAILED DESCRIPTION OF THE INVENTION The present invention is relates to a compound of general formula Z-OC (C Rn) Rn2)-CO-Z wherein Z = OH or NH2 and nl = n2 =1 to 8.

Yet another embodiments of a present invention relates to a compound having a structure as shown below and bearing general formula ZOC-CR3R4-CRlR2-COOH wherein: Z=OH or NHS, RI, to R4 denotes H, NH2, S03H, or OS03H, CH2-SO3H, CH2-OS03H, NHS03H Structure 1 Yet another embodiments of a present invention relates to a compound having a structure as shown below and bearing general formula ZOC-CR5R6-CR3R4-CR1R2-COOH wherein: Z=OH or NH2, R, to R6 denotes H, NH2, SO3H, or OS03H, CH2-SO3H, CH2-OS03H, NHSO3H

Structure 2 Yet another embodiments of a present invention relates to a compound having a structure as shown below and bearing general formula ZOC-CR7R8-CR5R6-CR3R4- CRIR2-COOH wherein: Z=OH or NH2, Pi to R8 denotes H, NH2, S03H, or OS03H, CH2-SO3H, CH2-OS03H, NHS03H structure 3 Yet another embodiments of a present invention relates to a compound formula (Ia), wherein the compound is selected from the group consisting of : I, [L-Aspartic acid, N-Sulfonic acid], II. [2α,3-dicarboxy, propane-1-sulfonic acid], III. [2a, 3-dicarboxy, propane-1-sulfate], IV. [1 a, 2-carboxy ethane sulfonic acid], V. [la, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2p. 3-carboxy, propane-1-sulfonic acid], VIII. [2p, 3-carboxy, propane-1-sulfate], IX. [I (3, 2-carboxy ethane-1-sulfonic acid], X. [1ß,2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3a-sulfonic acid],

XII. [D-aspartic acid, 3a-sulfate], XIII. [D-aspartic acid, 3ß-sulfonic acid], XIV. [D-aspartic acid, 3ß-sulfate], XV. [L-asparagine, N-sulfonic acid], XVI. [2a-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3a-sulfate], XXII. [L-asparagine, 3p-sulfonic acid], XXIII. [L-asparagine, 3i-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2p-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1ß-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [1 0-carboy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid], XXX. [D-asparagine, 3a-sulfate], XXXI. [D-asparagine, 3ß-sulfonic acid], XXXII. [D-asparagine, 3p-sulfate], XXXIII. [L-glutamic acid, N-sulfonic acid], XXXIV. [2a, 4-dicarboxy, butane-1-sulfonic acid], XXXV. [2a, 4-dicarboxy, butane-1-sulfate], XXXVI. [la, 3-dicarboxy, propane sulfonic acid], XXXVII. [la, 3-dicarboxy, propane sulfate], XXXVIII. [lj3, 3-dicarboxy, propane sulfate], XXXIX. [1 ß, 3-dicarboxy, propane sulfonic acid], Yet another embodiment of a present invention relates to a compound formula (Ib) wherein the compound is selected from the group consisting of : I. [D-glutamic acid, N-sulfonic acid], II. 2 (3, 4-dicarboxy, butane-1-sulfonic acid], III. [2p, 4-dicarboxy, butane-1-sulfate],

IV. [D-glutamic acid, 3a-sulfonic acid], V. [D-glutamic acid, 3α-sulfate], VI. [D-glutamic acid, 3ß-sulfonic acid], VII. [D-glutamic acid, 3ß-sulfate], VIII. [D-glutamic acid, 4a-sulfonic acid], IX. [D-glutamic acid, 4a-sulfate], X. [D-glutamic acid, 4p-sulfonic acid], XI. [D-glutamic acid, 3p-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV. [2a-carboxy, 4-carboxamido, butane-1-sulfate], XV. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [la-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], <BR> <BR> <BR> <BR> <BR> XVIII. [1 (3-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [2ß-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2ß-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [D-glutamine, 3α-sulfonic acid], XXIII. [D-glutamine, 3a-sulfate], XXIV. [D-glutamine, 3p-sulfonic acid], XXV. [D-glutamine, 3ß-sulfate], XXVI. [D-glutamine, 4a-sulfonic acid], XXVII. [D-glutamine, 4a-sulfate], XXVIII. [D-glutamine, 40-sulfonic acid], XXIX. [D-glutamine, 4p-sulfate], XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2a, 5-dicarboxy-l-sulfate], XXXIII. [Butane-1α, 4-dicarboxy-1-sulfonic acid], XXXIV. [Butane-1α, 4-dicarboxy-1-sulfate], XXXV. [D-homoglutamic acid, N-sulfonic acid], XXXVI. [Pentane-2p, 5-dicarboxy-l-sulfonic acid],

XXXVII. [Pentane-2ß, 5-dicarboxy-1-sulfate], XXXVIII. [Butane-1ß, 4-dicarboxy-1-sulfonic acid], XXXIX. [Butane-1ß, 4-dicarboxy-1-sulfate], Yet another embodiment of a present invention relates to a compound formula (Ic) wherein the compound is selected from the group consisting of I. [D-homoglutamic acid, 3a-sulfonic acid], II. [D-homoglutamic acid, 3a-sulfate], III. [D-homoglutamic acid, 3p-sulfonic acid] ; IV. [D-homoglutamic acid, 3ß-sulfate], V. [D-homoglutamic acid, 4a-sulfonic acid], VI. [D-homoglutamic acid, 4a-sulfate], VII. [D-homoglutamic acid, 4ß-sulfonic acid], VIII. [D-homoglutamic acid, 4p-sulfate], IX. D-homoglutamic acid, 5a-sulfate], X. [D-homoglutamic acid, 5a-sulfate3, XI. [D-homoglutamic acid, 5p-sulfonic acid], XII. [D-homoglutamic acid, 5 (3-sulfate), XIII. [L-homoglutamine, N-sulfonic acid], XIV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid], XV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfate], XVI. [Butane-la-carboxy, 4-carboxamido-1-sulfonic acid], XVII. [Butane-la-carboxy, 4-carboxamido-1-sulfate], XVIII. [D-homoglutamine, N-sulfonic acid], XIX. [Pentane-2ß-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Butane-1 p-carboxy, 4-carboxamido-1-sulfonic acid], XXI. butane-1 P-carboxy, 4-carboxamido-1-sulfate], XXII. [D-homoglutamine, 3a-sulfonic acid], XXIII. [D-homoglutamine, 3a-sulfate], XXIV. [D-homoglutamine, 3p-sulfonic acid], XXV. [D-homoglutamine, 3p-sulfate], XXVI. [D-homoglutamine, 4a-sulfonic acid], XXVII. [D-homoglutamine, 4a-sulfate], XXVIII. [D-homoglutamine, 4ß-sulfonic acid],

XXIX. [D-homoglutamine, 4ß-sulfate], XXX. [D-homoglutamine, 5a-sulfonic acid], XXXI. [D-homoglutamine, 5a-sulfate], XXXII. [D-homoglutamine, 5ß-sulfonic acid] and XXXIII. [D-homoglutamine, 5ß-sulfate].

Yet another embodiment of a present invention relates to a compound Novel sulfonic acid/ sulfate derivatives of the formulae ZOC-CR3R4-CRlR2-COOH wherein: Z=OH or NH2, R,, to R4 denotes H, NH2, S03H, or OSO3H, CH2-SO3H, CH2-OSO3H, NHSO3H I. A compound wherein Z=OH, R2=R3=R4=H, R1=NHSO3H is the same meaning as is before defined; II. A compound wherein Z=OH, R2=R3=R4=H, R1= CH2SO3H is the same meaning as is before defined; III. A compound wherein Z=OH, R2=R3=R4=H, R1= CH2OSO3H is the same meaning as is before defined; IV. A compound wherein Z=OH, R2=R3=R4=H, Rl=SO3H is the same meaning. as is before defined; V. A compound wherein Z=OH, R2=R3=R4=H, Rl=OS03H is the same meaning as is before defined; VI. A compound wherein Z=OH, R1=R3=R4=H, R2= NHS03H is the same meaning as is before defined ; VII. A compound wherein Z=OH, Ri=R3=R4=H, R2= CH2S03H is the. same meaning as is before defined; VIII. A compound wherein Z=OH, Rl=R3=R4=H, R2= CH20SO3H is the same meaning as is before defined; IX. A compound wherein Z=OH, R1=R3=R4=H, R2=SO3H is the same meaning as is before defined ; X. A compound wherein Z=OH, Rl=R3=R4=H, R2=OS03H is the same meaning as is before defined; XI. A compound wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined; XII. A compound wherein Z=OH, Ri=R4=H, R2=NH2, R3=S03H is the same meaning as is before defined; XIII. A compound wherein Z=OH, R1=R3=H, R2=NH2, R4=SO3H is the same meaning as is before defined;

XIV. A compound wherein Z=OH, R1=R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined ; XV. A compound wherein Z=NH2, R2=R3=R4=H, R1=NHSO3H is the same meaning as is before defined; XVI. A compound wherein Z=NH2, R2=R3=R4=H, Rl=CH2S03H is the same meaning as is before defined ; XVII. A compound wherein Z=NH2, R2=R3=R4=H, R1=CH2OSO3H is the same meaning as is before defined ; XVIII. A compound wherein Z=NH2, R2=R3=R4=H, R1=SO3H is the same meaning as is wherein Z=NH2, R2=R3=R4=H, R1=OSO3H is the same meaning as is before defined ; XIX. A compound wherein Z=NH2, Rl=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined ; XX. A compound wherein Z=NH2, Rl=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined ; XXI. A compound wherein Z=NH2, R, =R3=H, R2=NH2, R4= S03H is the same meaning as is before defined; XXII. A compound wherein Z=NH2, R1=R3=H, R2=NH2, R4= OS03H is the same meaning as is before defined ; XXIII. A compound wherein Z=NH2, R1=R3=R4=H, R2= NHS03H is the same meaning as is before defined ; XXIV. A compound wherein Z=NH2, Rl=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined ; XXV. A compound wherein Z=NH2, R1=R3=R4=H, R2=CH2OSO3H is the same meaning as is before defined ; XXVI. A compound wherein Z=NH2, R, =R3=R4=H, R2=SO3H is the same meaning as is before defined ; XXVII. A compound wherein Z=NH2, R, =R3=R4=H, R2=OS03H is the same meaning as is before defined ; XXVIII. A compound wherein Z=NH2, R1=R4=H, R2=NH2, R3= S03H is the same meaning as is before defined ; XXIX. A compound wherein Z=NH2, Rl=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined ;

XXX. A compound wherein Z=NH2, Rl=R3=H, R2=NH2, R4=S03H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, Rl=R3=H, R2=NH2, R4=OS03H is the same meaning as is before defined.

Yet another embodiment of a present invention relates to a compound novel sulfonic acid/ sulfate derivatives of the formulae ZOC-CR5R6-CR3R4-CRIR2-COOH, wherein: Z=OH or NH2, R, to R6 denotes H, NH2 ; S03H, or OS03H, CH2-SO3H, CH2- OSO2H, NHS03H I. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined ; II. A compound wherein Z=OH, R2=R3=R4=Rs=R6=H, R1= CH2SO3H is the same meaning as is before defined; III. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, R1=CH2OSO3H is the same meaning as is before defined; IV. A compound wherein Z=OH, R2=R3=R4= R5=R6=H, Rl= S03H is the same meaning as is before defined; V. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, Rl=OS03H is the same meaning as is before defined; VI. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2=OS03H is the same meaning as is before defined; VII. A compound wherein Z=OH, Rl=R3=R4=R5=R6=H, R2= S03H is the same meaning as is before defined; VIII. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2=NHSO3H is the same meaning as is before defined; IX. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2=CH2SO3H is the same meaning as is before defined; X. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2=CH2OSO3H is the same meaning as is before defined; XI. A compound wherein Z=OH, Rl=R4=R5=R6=H, R2= NH2, R3=SO3H is the same meaning as is before defined; XII. A compound wherein Z=OH, R1=R4=R5=R6=H, R2=NH2, R3=OSO3H is the same meaning as is before defined; XIII. A compound wherein Z=OH, Rw=R3=R5=R6=H, R2= NH2, R4=SO3H is the same meaning as is before defined;

XIV. A compound wherein Z=OH, R1=R=R5=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined; XV. A compound wherein Z=OH, R1=R4=R3=R6=H, R2=NH2, R5=SO3H is the same meaning as is before defined; XVI. A compound wherein Z=OH, Rl=R4=R3=R6=H, R2= NH2, R5=OSO3H is the same meaning as is before defined; XVII. A compound wherein Z=OH, R1=R3=R5=R4=H, R2=NH2, R6=SO3H is the same meaning as is before defined ; XVIII. A compound wherein Z=OH, R1=R3=R5=R4=H, R2=NH2, R6=OSO3H is the same meaning as is before defined ; XIX. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined; XX. A compound wherein Z=NH2, R2=R3=P, 4= R5=R6=H, RI=CH2SO3H is the same meaning as is before defined; XXI. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1= CH20SO3H is the same meaning as is before defined; XXII. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=SO3H is the same meaning as is before defined; XXIII. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=OSO3H is the same meaning as is before defined ; XXIV. A compound wherein Z=NH2, RI=R3=R4=RS=R6=H, R2= OS03H is the same meaning as is before defined; XXV. A compound wherein Z=NH2, R1=R3=R4=R5=R6=H, R2=SO3H is the same meaning as is before defined; XXVI. A compound wherein Z=NH2, R1=R3=R4=R5=R6=H, R2=NHSO3H is the same meaning as is before defined; XXVII. A compound wherein Z=NH2, Rl=R3=R4=R5=R6=H, R2=CH2SO3H is the same meaning as is before defined; XXVIII. A compound wherein Z=NH2, R, =R3=R4=R5=R6=H, R2= CH20SO3H is the same meaning as is before defined; XXIX. A compound wherein Z=NH2, R1=R4=R5=R6=H, R2=NH2, R3=SO3H is the same meaning as is before defined;

XXX. A compound wherein Z=NH2, R1=R4=R5=R6=H, R2= NH2, R3=OS03H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, Rt=R3=Rs=R6=H, Rz= NN2, R4=S03H is the same meaning as is before defined; XXXII. A compound wherein Z=NH2, Ri=R3=R5=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined; XXXIII. A compound, wherein Z=NH2, R1=R4=R3=R6=H, R2=NH2, R5=SO3H is the same meaning as is before defined ; XXXIV. A compound wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, R5=OS03H is the same meaning as is before defined; XXXV. A compound wherein Z=NH2, R1=R3=R5=R4=H, R2=NH2, R6=SO3H is the same meaning as is before defined ; XXXVI. A compound wherein Z=NH2, RI=R3=R5=R4=H, R2= NH2, R6=OS03H is the same meaning as is before defined.

Yet another embodiment of a present invention relates to a compound Novel sulfonic acid/ sulfate derivatives of the formulae ZOC-CR7RS-CR5R6-CR3R4-CRtR2-COOH as claimed in claim 4, wherein: Z=OH or NH2, Ri, to R8 denotes H, NH2, S03H, or OS03H, CH2- S03H, CH2-OS03H, NHS03H I. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1=NHSO3H is the same meaning as is before defined; II. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1= - CH2SO3H is the same meaning as is before defined; III. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, Ri=CH2OS03H is the same meaning as is before defined; IV. A compound wherein Z=OH, R2=R3=R4= R5=R6=R7=R8=Hv Rl=SO3H is the same meaning as is before defined; V. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1=OSO3H is the same meaning as is before defined; VI. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=NHS03H is the same meaning as is before defined; VII. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined ; VIII. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2OSO3H is the same meaning as is before defined;

IX. A compound wherein Z=OH, R1=R3=R4= R5=R6=R7=R8=H, R2=SO3H is the same meaning as is before defined; X. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=OS03H is the same meaning as is before defined; XI. A compound wherein Z=OH, R1=R4= R5=R6= R7=R8=H, R2=NH2, R3=S03H is the same meaning as is before defined; XII. A compound wherein Z=OH, R1=R4=R5=R6=R7=R8=H, R2=NH2, R3=OS03H is the same meaning as is before defined; XIII. A compound wherein Z=OH, Rl=R3=R5=R6= R7=R8=H, R2= NH2, R4=S03H is the same meaning as is before defined; XIV. A compound wherein Z=OH, Rl=R3=Rs=R6=R7=R8=H, R2=NH2, R4=OS03H is the same meaning as is before defined; XV. A compound wherein Z=OH, R, =R4= R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined; XVI. A compound wherein Z=OH, RI=R4=R3=R6= R7=R8=H, R2=NH2, R5=OS03H is the same meaning as is before defined; XVII. A compound wherein Z=OH, R=R3=R5=R4= R7=Rs=H, R2=NH2, R6=SO3H is the same meaning as is before defined; XVIII. A compound wherein Z=OH, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=OS03H is the same meaning as is before defined; XIX. A compound wherein Z=OH, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined; XX. A compound wherein Z=OH, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=OS03H is the same meaning as is before defined; XXI. A compound wherein Z=OH, R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=SO3H is the same meaning as is before defined ; XXII. A compound wherein Z=OH, R1=R3=R5=R4=R7=R6=H, R2=NH2, R8=OS03H is the same meaning as is before defined ; XXIII. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R ; =NHS03H is the same meaning as is before defined; XXIV. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=CH2SO3H is the same meaning as is before defined; XXV. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=CH2OSO3H is the same meaning as is before defined ;

XXVI. A compound wherein Z=NH2, R2=R3=R4= @= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined; XXVII. A compound wherein Z=NH2, R2=R3=R4=Rs=R6= R7=R8=H, R1=OSO3H is the same meaning as is before defined; XXVIII. A compound wherein Z=NH2, RI=R3=R4=Rs=R6= R7=R8=H, R2=NHS03H is the same meaning as is before defined; XXIX. A compound wherein Z=NH2, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined; XXX. A compound wherein Z=NH2, RI=R3=R4= R5=R6=R7=Rg=H, R2=SO3H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, R1=R3=R4=R5=R6= R7=R8=H, R2=OS03H is the same meaning as is before defined; XXXII. A compound wherein Z=NH2, Rl=R4=R5=R6= R7=R8=H, R2=NH2, R3=S03H is the same meaning as is before defined; XXXIII. A compound wherein Z=NH2, Ri=R4=R5=R6= R7=R8=H, R2=NH2, R3=OS03H is the same meaning as is before defined; XXXIV. A compound wherein Z=NH2, R1=R3=R5=R6=R7=R8= H, R2=NH2, R4=S03H is the same meaning as is before defined ; XXXV. A compound wherein Z=NH2, R1=R3=R5=R6=R7=R8= H, R2=NH2, R4=OS03H is the same meaning as is before defined; XXXVI. A compound wherein Z=NH2, RI=R44=R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined; XXXVII. A compound wherein Z=NH2, R1=R4=R3=R6= R7=R8=H, R2=NH2, Rs=OS03H is the same meaning as is before defined; XXXVIII. A compound wherein Z=NH2, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=SO3H is the same meaning as is before defined; XXXIX. A compound wherein Z=NH2, R=R3=R5=R4= R7=R8=H, R2=NH2, R6=OS03H is the same meaning as is before defined; XL. A compound wherein Z=NH2, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined; XLI. A compound wherein Z=NH2, R, =R4=R3=R6=R5=R8=H, R2=NH2, R7=OS03H is the same meaning as is before defined ; XLII. A compound wherein Z=NH2, R1=R3=R5=R4=R7=R6=H, R2= NH2, R8=SO3H is the same meaning as is before defined;

XLIII. A compound wherein Z=NH2, R1=R3=R5=R4=R7=R6=H, R2=NH2, Rs=OS03H is the same meaning as is before defined; Yet another embodiment of a present invention relates to a compound wherein said compound is non-toxic salts selected from the group consisting of : I. [L-Aspartic acid, N-Sulfonic acid], II. [2a, 3-dicarboxy, propane-1-sulfonic acid], III. [2a, 3-dicarboxy, propane-1-sulfate], IV. [la, 2-carboxy ethane sulfonic acid], V. [la, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid3, VII. [2ß,3-carboxy, propane-1-sulfonic acid], VIII. [2ß,3-carboxy, propane-1-sulfate], IX. [1 (3, 2-carboxy ethane-1-sulfonic acid], X. [1ß, 2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3a-sulfonic acid], XII. [D-aspartic acid, 3a-sulfate], XIII. [D-aspartic acid, 3p-sulfonic acid], XIV. [D-aspartic acid, 3p-sulfate], XV. [L-asparagine, N-sulfonic acid], XVI. [2a-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [la-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3a-sulfate], XXII. [L-asparagine, 3p-sulfonic acid], XXIII. [L-asparagine, 3p-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2p-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [I ß-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [ p-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid],

XXX. [D-asparagine, 3a-sulfate], XXXI. [D-asparagine, 3p-sulfonic acid], XXXII. [D-asparagine, 3ß-sulfate], XXXIII. [L-glutamic acid, N-sulfonic acid], XXXIV. [2a, 4-dicarboxy, butane-1-sulfonic acid], XXXV. [2a, 4-dicarboxy, butane-1-sulfate], XXXVI. [la, 3-dicarboxy, propane sulfonic acid], XXXVII. [1 a, 3-dicarboxy, propane sulfate], XXXVIII. [1ß, 3-dicarboxy, propane sulfate], XXXIX. [1 P, 3-dicarboxy, propane sulfonic acid], Yet another embodiment of a present invention relates to a compound wherein said compound is non-toxic salts selected from the group consisting of : I. [D-glutamic acid, N-sulfonic acid], II. [2ß, 4-dicarboxy, butane-1-sulfonic acid], III. [2ß, 4-dicarboxy, butane-1-sulfate], IV. [D-glutamic acid, 3a-sulfonic acid], V. [D-glutamic acid, 3a-sulfate], VI. [D-glutamic acid, 3ß-sulfonic acid], VII. [D-glutamic acid, 3p-sulfate], VIII. [D-glutamic acid, 4a-sulfonic acid], IX. [D-glutamic acid, 4a-sulfate], X. [D-glutamic acid ; 4 (3-sulfonic acid], XI. [D-glutamic acid, 3p-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV. [2a-carboxy, 4-carboxamido, butane-1-sulfate], XV. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [la-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1ß-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [-2p-c'arboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2ß-carboxy, 4-carboxamido, butane-1-sulfate],

XXII. [D-glutamine, 3a-sulfonic acid], XXIII. [D-glutamine, 3a-sulfate], XXIV. [D-glutamine, 3ß-sulfonic acid], XXV. [D-glutamine, 3p-sulfate], XXVI. [D-glutamine, 4a-sulfonic acid], XXVII. [D-glutamine, 4a-sulfate], XXVIII. [D-glutamine, 4p-sulfonic acid], XXIX. [D-glutamine, 4p-sulfate],- XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2a, 5-dicarboxy-1-sulfate], XXXIII. [Butane-1α, 4-dicarboxy-1-sulfonic acid], XXXIV. [Butane-la, 4-dicarboxy-1-sulfate], XXXV. [D-homoglutamic acid, N-sulfonic acid], XXXVI. [Pentane-2ß, 5-dicarboxy-1-sulfonic acid], XXXVII. [Pentane-2p, 5-dicarboxy-1-sulfate], XXXVIII. [Butane-1ß, 4-dicarboxy-1-sulfonic acid], XXXIX. [Butane-1ß, 4-dicarboxy-1-sulfate], Yet another embodiment of a present invention relates to a compound said compound is non-toxic salts selected from the group consisting of : I. [D-homoglutamic acid, 3a-sulfonic acid], II. [D-homoglutamic acid, 3a-sulfate], III. [D-homoglutamic acid, 3 (3-sulfonic acid], IV. [D-homoglutamic acid, 3ß-sulfate], V. [D-homoglutamic acid, 4a-sulfonic acid], VI. [D-homoglutamic acid, 4a-sulfate], VII. [D-homoglutamic acid, 4ß-sulfonic acidl, VIII. [D-homoglutamic acid, 4p-sulfate], IX. [D-homoglutamic acid, Sa-sulfate], X. [D-homoglutamic acid, 5a-sulfate], XI. [D-homoglutamic acid, 5p-sulfonic acid], XII. [D-homoglutamic acid, 5ß-sulfate], XIII. [L-homoglutamine, N-sulfonic acid],

XIV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid], XV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfate], XVI. [Butane-la-carboxy, 4-carboxamido-1-sulfonic acid], XVII. [Butane-la-carboxy, 4-carboxamido-1-sulfate], XVIII. [D-homoglutamine, N-sulfonic acid], XIX. [Pentane-2p-carboxy, 5-carboxamido-l-sulfonic acid], XX. [Butane-1 ß -carboxy, 4-carboxamido-1-sulfonic acid], XXI. [Butane-1 j3-carboxy, 4-carboxamido-1-sulfate], XXII. [D-homoglutamine, 3a-sulfonic acid], XXIII. [D-homoglutamine, 3α-sulfate], XXIV. [D-homoglutamine,') P-sulfonic acid], XXV. [D-homoglutamine, 3p-sulfate], XXVI. [D-homoglutamine, 4a-sulfonic acid], XXVII. [D-homoglutamine, 4a-sulfate], XXVIII. [D-homoglutamine, 4ß-sulfonic acid], XXIX. [D-homoglutamine, 4ß-sulfate], XXX. [D-homoglutamine, Sa-sulfonic acid], XXXI. [D-homoglutamine, 5a-sulfate], XXXII. [D-homoglutamine, 5p-sulfonic acid] and XXXIII. [D-homoglutamine, 5ß-sulfate].

Yet another embodiment of a present invention relates to a compound said compound is selected from the group consisting of aspartic acid, asparagine and corresponding de-amino analogs: I. [L-Aspartic acid, N-Sulfonic acid], II. [2a, 3-dicarboxy, propane-1-sulfonic acid], III. [2a, 3-dicarboxy, propane-1-sulfate], IV. [la, 2-carboxy ethane sulfonic acid], V. [1α, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2, 3-carboxy, propane-1-sulfonic acid], VIII. [2 P, 3-carboxy, propane-1-sulfate], IX. [1ß, 2-carboxy ethane-1-sulfonic acid], X. [1ß,2-carboxy ethane-1-sulfate],

XI. [D-aspartic acid, 3a-sulfonic acid], XII. [D-aspartic acid, 3a-sulfate], XIII. [D-aspartic acid, 3ß-sulfonic acid], XIV. [D-aspartic acid, 3ß-sulfate], XV. [L-asparagine, N-sulfonic acid], XVI. [2a-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [la-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3a-sulfate], XXII. [L-asparagine, 3p-sulfonic acid], XXIII. [L-asparagine, 3p-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2p-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [Ip-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [I(3-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid], XXX. [D-asparagine, 3a-sulfate], XXXI. [D-asparagine, 3p-sulfonic acid], XXXII. [D-asparagine, 3p-sulfate], Yet another embodiment of a present invention relates to a compound said compound is selected from the group consisting of glutamic acid, glutamine and corresponding de- amino analogs: I. [L-glutamic acid, N-sulfonic acid], II. [2a, 4-dicarboxy, butane-1-sulfonic acid], III. [2a, 4-dicarboxy, butane-1-sulfate], IV. [la, 3-dicarboxy, propane sulfonic acid], V. [laz 3-dicarboxy, propane sulfate], VI. [I P, 3-dicarboxy, propane sulfate], VII. [I P, 3-dicarboxy, propane sulfonic acid], VIII. [D-glutamic acid, N-sulfonic acid],

IX. [2ß, 4-dicarboxy, butane-1-sulfonic acid], X. [2p, 4-dicarboxy, butane-1-sulfate], XI. [D-glutamic acid, 3a-sulfonic acid], XII. [D-glutamic acid, 3a-sulfate], XIII. [D-glutamic acid, 3p-sulfonic acid], XIV. [D-glutamic acid, 3p-sulfate], XV. [D-glutamic acid, 4a-sulfonic acid], XVI. [D-glutamic acid, 4a-sulfate], XVII. [D-glutamic acid, 4p-sulfonic acid], XVIII. [D-glutamic acid, 3p-sulfate], XIX. [L-glutamine, N-sulfonic acid], XX. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2a-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXIII. [la-carboxy, 3-carboxamido, propane-1-sulfate], XXIV. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], XXV. [1ß-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [D-glutamine, N-sulfonic acid], XXVII. [2ß-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXVIII. [2p-carboxy, 4-carboxamido, butane-1-sulfate], XXIX. [D-glutamine, 3a-sulfonic acid], XXX. [D-glutamine, 3a-sulfate], XXXI. [D-glutamine, 3ß-sulfonic acid], XXXII. [D-glutamine, 3p-sulfate], XXXIII. [D-glutamine, 4a-sulfonic acid], XXXIV. [D-glutamine, 4a-sulfate], XXXV. [D-glutamine, 4p-sulfonic acid], XXXVI. [D-glutamine, 4p-sulfate], XXXVII. [L-homoglutamic acid, N-sulfonic acid], XXXVIII. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXIX. [Pentane-2a, 5-dicarboxy-1-sulfate], XL. [Butane-1α, 4-dicarboxy-1-sulfonic acid], XLI. [Butane-la, 4-dicarboxy-1-sulfate],

Yet another embodiment of a present invention relates to a compound wherein said compound is selected from the group consisting of homoglutamic acid, homoglutamine and corresponding de-amino analogs : I. [D-homoglutamic acid, N-sulfonic acid], II. [Pentane-2ß, 5-dicarboxy-l-sulfonic acid], III. [Pentane-2ß, 5-dicarboxy-1-sulfate], IV. [Butane-1 (3, 4-dicarboxy-1-sulfonic acid], V. [Butane-1ß, 4-dicarboxy-1-sulfate], VI. [D-homoglutamic acid, 3a-sulfonic acid], VII. [D-homoglutamic acid, 3a-sulfate], VIII. [D-homoglutamic acid, 3p-sulfonic acid], IX. [D-homoglutamic acid, 3p-sulfate], X. [D-homoglutamic acid, 4a-sulfonic acid], XI. [D-homoglutamic acid, 4a-sulfate], XII. [D-homoglutamic acid, 4p-sulfonic acid], XIII. [D-homoglutamic acid, 4p-sulfate], XIV. [D-homoglutamic acid, 5α-sulfate], XV. [D-homoglutamic acid, Sa-sulfate], XVI. [D-homoglutamic acid, 5p-sulfonic acid], XVII. [D-homoglutamic acid, 5p-sulfate], XVIII. [L-homoglutamine, N-sulfonic acid], XIX. [Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Pentane-2a-carboxy, 5-carboxamido-1-sulfate], XXI. [Butane-1α-carboxy, 4-carboxamido-1-sulfonic acid], XXII. [Butane-1α-carboxy, 4-carboxamido-1-sulfate], XXIII. [D-homoglutamine, N-sulfonic acid], XXIV. [Pentane-2ß-carboxy, 5-carboxamido-1-sulfonic acid], XXV. [Butane-1 P-carboxy, 4-carboxamido-1-sulfonic acid], XXVI. [Butane-1 0-carboy, 4-carboxamido-1-sulfate], XXVII. [D-homoglutamine, 3a-sulfonic acid], XXVIII. [D-homoglutamine, 3a-sulfate], XXIX. [D-homoglutamine, 3p-sulfonic acid], XXX. [D-homoglutamine, 3p-sulfate],

XXXI. [D-homoglutamine, 4a-sulfonic acid], XXXII. [D-homoglutamine, 4a-sulfate], XXXIII. [D-homoglutamine, 4p-sulfonic acid], XXXIV. [D-homoglutamine, 4p-sulfate], XXXV. [D-homoglutamine, Sa-sulfonic acid], XXXVI. [D-homoglutamine, Sa-sulfate], XXXVII. [D-homoglutamine, 5(3-sulfonic acid] and XXXVIII. [D-homoglutamine, 5p-sulfate].

Still another embodiment of the present invention relates to a process for preparing L- glutamyl N-sulfonic acid from glutamic acid mono tertiary butyl ester comprising the steps of : a) adding L-glutamyl acid mono tertiary butyl ester portion wise to a solution of SOzClz in dry CH2C12 at 0°C) and Et3N (3 eq. ) to obtain a solution, b) stirring the solution for a time period in the range of 5 to 10 hrs at room temperature unless thin layer chromatography (TLC) shows complete consumption of starting material and evaporating the solvent present in TLC and crude is drying in vaccum, c) adding water to dried crude and stirring the slurry for a time period in the range of 0.5 to 3 hr, d) adding 45 ml CH2Cl2 and 3 equivalent of TFA at 0°Cto the solution and stirring for 24 hrs e) evaporating the solvent and drying in vacuum to obtain the product L- glutamyl, N-sulfonic acid.

A further e mbodiment o.. f t he p resent i nvention r elates t o for p reparing L-glutamyl, N- sulfonic acid from glutamyl acid di tertiary butyl ester comprising the steps of : a. adding L-aspartic acid di tertiary butyl ester portion wise to a solution of S02C12 in dry CH2CI2 at 0°C) and Et3N (3 eq. ) to obtain a solution, b. stirring the solution for a time period in the range of 5 to 10 hrs at room temperature unless thin layer chromatography shows complete consumption of starting material evaporating the solvent present in TLC and crude is drying in vaccum, c. adding water to dried crude and stirring the slurry for a time period in the range of 0.5 to 3 hr,

d. adding 45 ml CH2C12 and 3 equivalent of TFA at 0°Cto the solution and stirring for 24 hrs e. evaporating the solvent and drying in vacuum to obtain the product L- aspartyl, N-sulfonic acid.

A further e mbodiment o f t he p resent i nvention r elates t o a p rocess for p reparing L- Aspartyl, N-sulfonic acid from L-aspartic acid di tertiary butyl ester comprising the steps of : a. adding L-aspartic acid di tertiary butyl ester portion wise to a solution of SO2CI2 in dry CH2CI2 at 0°C) and Et3N (3 eq. ) to obtain a solution, b. stirring the solution for a time period in the range of 5 to 10 hrs at room temperature unless thin layer chromatography shows complete consumption of starting material evaporating the solvent and drying the crude in vacuum, c. adding water to dried crude and stirring the slurry for a time period in the range of 0.5 to 3 hr, d. adding 45 ml CH2C12 and 3 equivalent of TFA at 0°Cto the solution and stirring for 24 hrs e. evaporating the solvent and drying in vacuum to obtain the product L- aspartyl, N-sulfonic acid.

A Further another embodiment of the present invention relates to process for preparing L- Homoglutamyl, N-sulfonic acid from L-Homoglutamic acid di tertiary butyl ester comprising the steps of : a. adding L-Homoglutamic acid di tertiary butyl ester portion-wise to a solution of SO2C12 in dry CH2CI2 at 0°C and Et3N, b. stirring the solution for 8 hrs at r. t. till TLC showed complete consumption of starting material evaporating the solvent and drying the crude in vacuum, c. adding water to it to obtain a slurry which is stirred for 1 hr, d. adding to the slurry 45 ml CHzC12 followed by 3 eq of TFA at 0°C and stirring the resulting solution for 24 hrs, e. evaporating and drying the solution in vacuum to obtain the product L- homoglutamyl, N-sulfonic acid.

A further embodiment of the present invention relates to a Pharmaceutical composition comprising the effective amount of a compound selected from the general formula Z-OC (C Rn1Rn2) -CO-Z wherein Z = OH or NH2 and nl = n2 =1 to 8 along with an additive, excipient, diluents or carrier.

Yet another embodiment of the present invention relates to said composition useful in vaccine formulation to prevent more efficient and faster presentation of antigens to T-cells thereby initiate primary protective Thl immune response and help in the clearance of the pathogen.

Yet another embodiment of the present invention relates to said composition having a structure as herein and bearing general formula ZOC-CR3R4-CR1R2-COOH wherein: Z=OH or NH2, Rl, to R4 denotes H, NH2, S03H, or OS03H, CH2-S03H, CH2-OSO3H, NHSO3H

Structure 1 Yet another embodiment of the present invention relates, wherein said compound having a structure as herein and bearing general formula ZOC-CR5R6-CR3R4-CR1R2-COOH wherein: Z=OH or NH2, R, to RG denotes H, NH2, SO3H, or OS03H, CH2-SO3H, CH2- OS03H, NHS03H

Structure 2 Yet another embodiment of the present invention relates said compound having structure as herein and bearing general formula ZOC-CR7R8-CR5R6-CR3R4-CR1R2-COOH wherein : Z=OH or NH2, Ri to Rs denotes H, NH2, SO3H, or OS03H, CH2-SO3H, CH2- OSO3H, NHS03H ac=ucture 3

Yet another embodiment of the present invention relates to said compound in non-toxic to monocytes.

Yet another embodiment of the present invention relates said compound in non-toxic to macrophages.

Yet another embodiment of the present invention relates additives are different divalent metal cations such as Mg, Ca and Zn.

Yet another embodiment of the present invention wherein, additives are amino acid/ dicarboxylic acid derivatives and their pharmaceutically acceptable selected alkali/alkaline earth metal salts.

Yet another embodiment of the present invention, wherein the compound is selected from the group consisting of : I. [L-Aspartic acid, N-Sulfonic acid], II. [2a, 3-dicarboxy, propane-1-sulfonic acid], III. [2a, 3-dicarboxy, propane-1-sulfate], IV. [la, 2-carboxy ethane sulfonic acid], V. [la, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2ß,3-carboxy, propane-1-sulfonic acid], VIII. [2p, 3-carboxy, propane-1-sulfate], IX. [I ß2-carboxy ethane-1-sulfonic acid], X. [lß, 2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3a-sulfonic acid], XII. [D-aspartic acid, 3a-sulfate], XIII. [D-aspartic acid, 3p-sulfonic acid], XIV. [D-aspartic acid, 3p-sulfate], XV. [L-asparagine, N-sulfonic acid], XVI. [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [la-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3a-sulfate],

XXII. [L-asparagine, 3(3-sulfonic acid], XXIII. [L-asparagine, 3p-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2ß-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1ß-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [1 p-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid], XXX. [D-asparagine, 3α-sulfate], XXXI. [D-asparagine, 0--sulfonic acid], XXXII. [D-asparagine, 3ß-sulfate], XXXIII. [L-glutamic acid, N-sulfonic acid], XXXIV. [2a, 4-dicarboxy, butane-1-sulfonic acid], XXXV. [2a, 4-dicarboxy, butane-1-sulfate],

XXXVI. [la, 3-dicarboxy, propane sulfonic acid], XXXVII. [la, 3-dicarboxy, propane sulfate], XXXVIII. [1ß, 3-dicarboxy propane sulfate], XXXIX. [l ß, 3-dicarboxy, propane sulfonic acid], Yet another embodiment of the present invention, wherein the compound is

selected from the group consisting of : I. [D-glutamic acid, N-sulfonic acid], II. 2ß. 4-dicarboxy, butane-1-sulfonic acid], III. [2ß, 4-dicarboxy, butane-1-sulfate], IV. [D-glutamic acid, 3α-sulfonic acid], V. [D-glutamic acid, 3a-sulfate], VI. [D-glutamic acid, 3ß-sulfonic acid], VII. [D-glutamic acid, 3ß-sulfate], VIII. [D-glutamic acid, 4α-sulfonic acid], IX. [D-glutamic acid, 4α-sulfate], X. [D-glutamic acid, 4 (3-sulfonic acid], XI. [D-glutamic acid, 3ß-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid],

XIV. [2a-carboxy, 4-carboxamido, butane-1-sulfate],.

XV. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [1α-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1ß-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [2p-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2ß-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [D-glutamine, 3a-sulfonic acid], XXIII. [D-glutamine, 3α-sulfate], XXIV. [D-glutamine, 3ß-sulfonic acid], XXV. [D-glutamine, 3p-sulfate], XXVI. [D-glutamine, 4a-sulfonic acid], XXVII. [D-glutamine, 4α-sulfate], XXVIII. [D-glutamine, 4p-sulfonic acid], XXIX. [D-glutamine, 4p-sulfate], XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2a, 5-dicarboxy-1-sulfate], XXXIII. [Butane-1α, 4-dicarboxy-1-sulfonic acid], XXXIV. [Butane-la, 4-dicarboxy-1-sulfate], XXXV. [D-homoglutamic acid, N-sulfonic acid], XXXVI. [Pentane-2ß, 5-dicarboxy-1-sulfonic acid], XXXVII. [Pentane-2ß, 5-dicarboxy-1-sulfate],

XXXVIII. [butane-1ß, 4-dicarboxy-1-sulfonic acid],

XXXIX. [Butane-1ß, 4-dicarboxy-1-sulfate], Yet another embodiment of the present invention, wherein the compound is selected from the group consisting of I. [D-homoglutamic acid, 3a-sulfonic acid], II. [D-homoglutamic acid, 3a-sulfate], III. [D-homoglutamic acid, 3p-sulfonic acid], IV. [D-homoglutamic acid, 3ß-sulfate], V. [D-homoglutamic acid, 4a-sulfonic acid], VI. [D-homoglutamic acid, 4a-sulfate], VII. [D-homoglutamic acid, 4ß-sulfonic acid], VIII. [D-homoglutamic acid, 4p-sulfate], IX. [D-homoglutamic acid, 5a-sulfate],

X. [D-homoglutamic acid, 5α-sulfate], XI. [D-homoglutamic acid, 5p-sulfonic acid], XII. [D-homoglutamic acid, 5j3-sulfate], XIII. [L-homoglutamine, N-sulfonic acid], XIV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid],

KV. [Pentane-2a-carboxy, 5-carboxamido-1-sulfate], XVI. [Butane-1α-carboxy, 4-carboxamido-1-sulfonic acid], XVII. [Butane-1α-carboxy, 4-carboxamido-1-sulfate], XVIII. [D-homoglutamine, N-sulfonic acid], XIX. [Pentane-2p-carboxy, 5-carboxamido-1-sulfonic acid], <BR> <BR> <BR> @ 5XX. [Butane-1 ß -carboxy, 4-carboxamido-1-sulfonic acid], XXI. [Butane-1 (3-carboxy, 4-carboxamido-1-sulfate], XXII. [D-homoglutamine, 3a-sulfonic acid], XXIII. [D-homoglutamine, 3a-sulfate], XXIV. [D-homoglutamine, 3ß-sulfonic acid],

(V. [D-homoglutamine, 36-sulfate], XXVI. [D-homoglutamine, 4a-sulfonic acid], XXVII. [D-homoglutamine, 4a-sulfate], XXVIII. [D-homoglutamine, 4i-sulfonic acid], XXIX. [D-homoglutamine, 4ß-sulfate], 25XX. [D-homoglutamine, 5α-sulfonic acid], XXXI. [D-homoglutamine, 5a-sulfate], XXXII. [D-homoglutamine, 5p-sulfonic acid] and XXXIII. [D-homoglutamine, 5ßsulfate].

Yet another embodiment of the present invention, wherein novel sulfonic acid/sulfate

derivatives of the formulae ZOC-CR3Ra-CRIR2-COOH wherein: Z=OH or NHS, RI, to R4 denotes H, NH2, S03H, or OSO3H, CH2-SO3H, CH2-OS03H, NHS03H I. A compound wherein Z=OH, R2=R3=R4=H, R1= NHS03H is the same meaning as is before defined;

II. A compound wherein Z=OH, R2=R3=R4=H, Rl= CH2SO3H is the same meaning as is before defined; III. A c ompound w herein Z=OH, R2=R3=R4=H, R1=CH2OSO3H is the same meaning as is before defined ; IV. A compound wherein Z=OH, R2=R3=R4=H, R1=SO3H is the same meaning as is before defined; V. A compound wherein Z=OH, R2=R3=R4=H, R1=OSO3H is the same meaning as is before defined ; VI. A compound wherein Z=OH, RI=R3=R4=H, R2= NHS03H is the same meaning as is before defined; VII. A compound wherein Z=OH, R1=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined; VIII. A c ompound w herein Z=OH, R 1=R3=R4=H, R 2= C H20SO3H i s t he s ame meaning as is before defined; IX. A compound wherein Z=OH, R1=R3=R4=H, R2=S03H is the same meaning as is before defined; X. A compound wherein Z=OH, Rl=R3=R4=H, R2=OS03H is the same meaning as is before defined; XI. A compound wherein Z=OH, RI=R4=H, R2=NH2, R3=S03H is the same meaning as is before defined; XII. A compound wherein Z=OH, R1=R4=H, R2=NH2, R3=SO3H is the same meaning as is before defined ; XIII. A compound wherein Z=OH, Rl=R3=H, R2=NH2, R4=S03H is the same meaning as is before defined; XIV. A compound wherein Z=OH, R1=R3=H, R2=NH2, R4=OSO3H is the same meaning as is before defined; XV. A compound wherein Z=NH2, R2=R3=R4=H, Rl=NHS03H is the same meaning as is before defined; XVI. A compound wherein Z=NH2, R2=R3=R4=H, R1=CH2SO3H is the same meaning as is before defined; XVII. A compound wherein Z=NH2, R2=R3=R4=H, Rl= CH20S03H is the same meaning as is before defined; XVIII. A compound wherein Z=NH2, R2=R3=R4, R1=SO3H is the same meaning as is before defined;

XIX. A compound wherein Z=NHz, R2=R3=R4=H, R1=OSO3H is the same meaning as is before defined; XX. A compound wherein Z-NH2, R1=R4=H, R2=NH2, R3= S03H is the same meaning as is before defined; XXI. A compound wherein Z=NH2, Ri=R4=H, R2=NH2, R3= OS03H is the same meaning as is before defined; XXII. A compound wherein Z=NH2, R1=R3=H, R2=NH2, R4= SO3H is the same meaning as is before defined; XXIII. A compound wherein Z=NH2, R1=R3=H, R2= NH2, R4= OS03H is the same meaning as is before defined; XXIV. A compound wherein Z=NH2, RI=R3=R4=H, R2= NHS03H is the same meaning as is before defined; XXV. A compound wherein Z=NH2, RI=R3=R4=H, R2= CH2SO3H is the same meaning as is before defined ; XXVI. A compound wherein Z=NH2, Rl=R3=R4=H, R2= CH20SO3H is the same meaning as is before defined; XXVII. A compound wherein Z=NH2, Rl=R3=R4=H, R2=S03H is the same meaning as is before defined; XXVIII. A compound wherein Z=NH2, R1=R3=R4=H, R2=OSO3H is the same meaning as is before defined; XXIX. A compound wherein Z=NH2, RI=R4=H, R2=NH2, R3= S03H is the same meaning as is before defined; XXX. A compound wherein Z=NH2, R1=R4=H, R2=NH2, R3= OSO3H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, Rl=R3=H, R2=NH2, R4=S03H is the same meaning as is before defined; XXXII. A compound wherein Z=NH2, R1=R3=H, R2=NH2, R4=OSO3H is the same meaning as is before defined.

Yet another embodiment of the present invention, wherein novel sulfonic acid/ sulfate derivatives of the formulae ZOC-CRsR6-CR3R4-CRiR2-COOH, wherein: Z=OH or NH2, Ri, to R6 denotes H, NH2, S03H, or OS03H, CH2-SO3H, CH2- OS03H, NHS03H I. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined; II. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, R1= CH2SO3H is the same meaning as is before defined; III. A compound wherein Z=OH, R2=R3=R4=R5=R6=H, R1=CH2OSO3H is the same meaning as is before defined;

IV. A compound wherein Z=OH, R2=R3=R4= R5=R6=H, R1= SO3H is the. same meaning as is before defined; V. A compound wherein Z=OH, R2==R3==R4=R5=R6=H, R) =OS03H is the same meaning as is before defined; VI. A compound wherein Z=OH, R, =R3=R4=Rs=R6=H, R2=OS03H is the same

meaning as is before defined; VII. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2= SO3H is the same meaning as is before defined; VIII. A compound wherein Z=OH, R1=R3=R4=R5=R6=H, R2= NHS03H is the same meaning as is before defined;

IX. A compound wherein Z=OH, R1=R3=R4= R5=R6=H, R2= CH2S03H is the same meaning as is before defined; X. A compound wherein Z=OH, RI=R3=R4= Rs=R6=H, R2= CH20S03H is the same meaning as is before defined ; XI. A compound wherein Z=OH, R1=R4=R5=R6=H, R2= NH2, R3=SO3H is the same

meaning as is before defined; XII. A compound wherein Z=OH, R, =R4=Rs=R6=H, R2= NH2, R3=OS03H is the same meaning as is before defined; XIII. A compound wherein Z=OH, R, =R3=R5=R6=H, R2= NH2, R4= S03H is the same meaning as is before defined ;

nv. A compound wherein Z=OH, R1=R3=R5=R6=H, R2= NHz, R4=OS03H is the same meaning as is before defined; XV. A compound wherein Z=OH, R1=R4= R3=R6=H, R2= NH2, R5=SO3H is the same meaning as is before defined; XVI. A compound wherein Z=OH, Rl=R4=R3=R6=H, R2= NH2, R5=OSO3H is the

same meaning as is before defined; XVII. A compound wherein Z=OH, R1=R3=R5=R4=H, R2= NH2, R6=SO3H is the same meaning as is before defined; XVIII. A compound wherein Z=OH, R1=R3=R5=R4=H, R2= NH2, R6=OSO3H is the same meaning as is before defined; XIX. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=NHSO3H is the same meaning as is before defined ; XX. A compound wherein Z=NH2, R2=R3=R4= R5=R6=H, R1=CH2SO3H is the same meaning as is before defined; XXI. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R, = CH20S03H is the same meaning as is before defined; XXII. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1=SO3H is the same meaning as is before defined; XXIII. A compound wherein Z=NH2, R2=R3=R4=R5=R6=H, R1= OS03H is the same

meaning as is before defined; XXIV. A compound wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= OSO3H is the same meaning as is before defined; XXV. A compound wherein Z=NH2, R1=R3=R4=R5=R6=H, R2= SO3H is the same meaning as is before defined ;.

XXVI. A compound wherein Z=NH2, Rl=R3=R4=R5=R6=H, R2= NHSO3H is the same meaning as is before defined; XXVII. A compound wherein Z=NH2, RI=R3=R4=R5=R6=H, R2=CH2S03H is the same meaning as is before defined; XXVIII. A compound wherein Z=NH2, R,=R3=R4=Rs=R6=H, R2= CH2OS03H is the same

meaning as is before defined; XXIX. A compound wherein Z=NH2, R1=R4=R5=R6=H, R2= NH2, R3=SO3H is the same meaning as is before defined; XXX. A compound wherein Z=NH2, R, =R4=Rs=R6=H, R2= NH2, R3=OS03H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, R1=R3=R5=R6=H, R2= NH2, R4=SO3H is the same meaning as is before defined; XXXII. A compound wherein Z=NH2, R=R3=Rs=R6=H, R2= NH2, R4=OS03H is the same meaning as is before defined; XXXIII. A compound wherein Z=NH2, R1=R4=R3=R6=H, R2= NH2, R5=SO3H is the same

meaning as is before defined; XXXIV. A compound wherein Z=NH2, R=R4=R3=R6=H, R2= NH2, Rs=OSO3H is the same meaning as is before defined; XXXV. A compound wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=SO3H is the same meaning as is before defined; XXXVI. A compound wherein Z=NH2, R1=R3=R5=R4=H, R2= NH2, R6=OSO3H is the same meaning as is before defined.

Yet another embodiment of the present invention, wherein novel sulfonic acid/sulfate

derivatives of the formulae ZOC-CR7R8-CR5R6-CR3R4-CR1R2-COOH, wherein: Z=OH or NH2, Ri, to Rs denotes H, NH2, S03H, or OSO3H, CHZ-S03H, CH2-OS03H, NHSO3H 1. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1=NHSO3H is the same meaning as is before defined ; II. A compound wherein Z=OH, R2=R3=R4=R5=R6= R7=R8=H, R1= - CH2SO3H is the same meaning as is before defined ; III. A compound wherein Z=OH, R2=R3=R4=Rs=R6= R7=R8=H, Rl=CH20SO3H is the same meaning as is before defined; IV. A compound wherein Z=OH, R2=R3=R4= R5=R6=R7=R8=H, R1=SO3H is the same meaning as is before defined; V. A compound wherein Z=OH, R2=R3=R4=Rs=R6= R7=R8=H, Rl=OS03H is the same meaning as is before defined; VI. A compound wherein Z=OH, Rl=R3=R4=R5=R6= R7=R8=H, R2=NHSO3H is the same meaning as is before defined ; VII. A compound wherein Z=OH, Rl=R3=R4=R5=R6= R7=R8=H, R2=CH2SO3H is the same meaning as is before defined ; VIII. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=CH2OSO3H is the same meaning as is before defined; IX. A compound wherein Z=OH, Rl=R3=R4= R5=R6=R7=R8=H, R2=S03H is the same meaning as is before defined; X. A compound wherein Z=OH, R1=R3=R4=R5=R6= R7=R8=H, R2=OSO3H is the same meaning as is before defined ; XI. A compound wherein Z=OH, R1=R4= R5=R6= R7=R8=H, R2=NH2, R3=SO3H is the same meaning as is before defined; XII. A compound wherein Z=OH, R1=R4=R5=R6=R7=R8=H, R2=NH2, R3=OSO3H is the same meaning as is before defined; XIII. A compound wherein Z=OH, Ri=R3=R5=R6= R7=Rg=H, R2= NH2, R4=S03H is the same meaning as is before defined ; XIV. A compound wherein Z=OH, Rl=R3=R5=R6=R7=R8=H, R2=NH2, R4=OSO3H is the same meaning as is before defined;

XV. A compound wherein Z=OH, Rl=R4= R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined; XVI. A compound wherein Z=OH, R1=R4=R3=R6= R7=R8=H, R2=NH2; R5=OS03H is the same meaning as is before defined; XVII. A compound wherein Z=OH, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=SO3H is the same meaning as is before defined; XVIII. A compound wherein Z=OH, R1=R3=R5=R4= R7=R8=H, R2=NH2, R6=OS03H is the same meaning as is before defined; XIX. A compound wherein Z=OH, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined; XX. A compound wherein Z=OH, Ri=R4=R3=R6=R5=Rs=H, R2=NH2, R7=OS03H is the same meaning as is before defined; XXI. A compound wherein Z=OH, RI=R3=R5=R4=R7=R6=H, R2=NH2, R8=SO3H is the same meaning as is before defined ; XXII. A compound wherein Z=OH, Rl=R3=Rs=R4=R7=R6=H, R2=NH2, Rg=OS03H is the same meaning as is before defined; XXIII. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=NHSO3H is the same meaning as is before defined ; XXIV. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, RI=CH ? SO3H is the same meaning as is before defined; XXV. A compound wherein Z=NH2, R2=R3=R4=R5=R6= R7=R8=H, Rt=CH20S03H is the same meaning as is before defined; XXVI. A compound wherein Z=NH2, R2=R3=R4= R5=R6=R7=Rs=H, Ri=S03H is the same meaning as is before defined ; XXVII. A compound wherein Z-NH2, R2=R3=R4=R5=R6= R7=R8=H, R1=OSO3H is the same meaning as is before defined; XXVIII. A compound wherein Z=NH2, R=R3=R4=R5=R6= R7=Rs=H, R2=NHS03H is the same meaning as is before defined ; XXIX. A compound wherein Z=NH2, R, =R3=R4=R5=R6= R7=Rs=H, R2=CH2S03H is the same meaning as is before defined ;

XXX. A compound wherein Z=NH2, R1=R3=R4= R5=R6=R7=R8=H, R2=SO3H is the same meaning as is before defined; XXXI. A compound wherein Z=NH2, R1=R3=R4=R5=R6= R7=R8=H, R2=OSO3H is the same meaning as is before defined; XXXII. A compound wherein Z=NH2, Ri=R4=R5=R6= R7=RR=H, R2=NH2, R3=SO3H is the same meaning as is before defined ; XXXIII. A compound wherein Z=NH2, R1=R4=R5=R6= R7=R8=H, R2=NH2, R3=OS03H is the same meaning as is before defined; XXXIV. A compound wherein Z=NH2, Ri=R3=R5=R6=R7=Ps= H, R2=NH2, R4=S03H is the same meaning as is before defined; XXXV. A compound wherein Z=NH2, R1=R3=R5=R6=R7=R8= H, R2=NH2, R4=OS03H is the same meaning as is before defined; XXXVI. A compound wherein Z=NH2, R1=R4=R3=R6= R7=R8=H, R2=NH2, R5=SO3H is the same meaning as is before defined ;

XXXVII. As compound wherein Z=NH2, R1=R4=R3=R6= R7=R8=H, R2=NH2, R5=OSO3H is the same meaning as is before defined; XXXVIII. A compound wherein Z=NH2, Rl=R3=R5=R4= R7=R8=H, R2=NH2, R6=S03H is the same meaning as is before defined; XXXIX. A compound wherein Z=NH2, R1=R3=R5=R4= R7=R8=H, R2=NH2,

R6=OS03H is the same meaning as is before defined; XL. A compound wherein Z-NH2, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=SO3H is the same meaning as is before defined; XLI. A compound wherein Z=NH2, R1=R4=R3=R6=R5=R8=H, R2=NH2, R7=OS03H is the same meaning as is before defined; XLII. A compound wherein Z=NH2, Rl=R3=R5=R4=R7=R6=H, R2= NH2, R8=S03H is the same meaning as is before defined; XLIII. A compound wherein Z=NH2, RI=R3=R5=R4=R7=R6=H, R2=NH2, R8=OSO3H is the same meaning as is before defined;

Yet another embodiment of the present invention, wherein said compound is non-toxic salts selected from the group consisting of : I. [L-Aspartic acid, N-Sulfonic acid], II. [2a, 3-dicarboxy, propane-1-sulfonic acid], III. [2 «, 3-dicarboxy, propane-1-sulfate], IV. [I a, 2-carboy ethane sulfonic acid], V. [1 a, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2ß, 3-carboxy, propane-1-sulfonic acid], VIII. [2ß, 3-carboxy, propane-1-sulfate], IX. [1ß 2-carboxy ethane-1-sulfonic acid], X. [1ß 2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3a-sulfonic acid], XII. [D-aspartic acid, 3a-sulfate], XIII. [D-aspartic acid, 3 (3=sulfonic acid], XIV. [D-aspartic acid, 3 p-sulfate], XV : [L-asparagine, N-sulfonic acid], XVI. [2a-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [la-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3a-sulfate], XXII. [L-asparagine, 3p-sulfonic acid], XXIII. [L-asparagine, 3p-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2p-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1 p-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [Iß-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid], XXX. [D-asparagine, 3a-sulfate], XXXI. [D-asparagine, 3 (3-sulfonic acid] ; XXXII. [D-asparagine, 3ß-sulfate], XXXIII. [L-glutamic acid, N-sulfonic acid], XXXIV. [2a, 4-dicarboxy, butane-1-sulfonic acid], XXXV. [2a, 4-dicarboxy, butane-1-sulfate],

XXXVI. [la, 3-dicarboxy, propane sulfonic acid], XXXVII. [1α, 3-dicarboxy, propane sulfate], XXXVIII. [1ß, 3-dicarboxy, propane sulfate], XXXIX. [1ß, 3-dicarboxy, propane sulfonic acid], Yet another embodiment of the present invention relates to a composition, wherein said

compound is non-toxic salts selected from the group consisting of : I. [D-glutamic acid, N-sulfonic acid], II. [2p, 4-dicarboxy, butane-1-sulfonic acid], III. [2p, 4-dicarboxy, butane-1-sulfate], IV. [D-glutamic acid, 3a-sulfonic acid], V. [D-glutamic acid, 3a-sulfate], VI. [D-glutamic acid, 3p-sulfonic acid], VII. [D-glutamic acid, 3ß-sulfate], VIII. [D-glutamic acid, 4a-sulfonic acid], IX. [D-glutamic acid, 4a-sulfate], X. [D-glutamic acid, 4ß-sulfonic acid], XI. [D-glutamic acid, 3 (3-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV. [2a-carboxy, 4-carboxamido, butane-1-sulfate], XV. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [la-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [lp-carboxy,. 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [2ß-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2ß-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [D-glutamine, 3a-sulfonic acid], XXIII. [D-glutamine, 3α-sulfate],

XXIV. [D-glutamine, 3ß-sulfonic acid], XXV. [D-glutamine, 3ß-sulfate], XXVI. [D-glutamine, 4a-sulfonic acid], XXVII. [D-glutamine, 4α-sulfate], XXVIII. [D-glutamine, 4ß-sulfonic acid], XXIX. [D-glutamine, 4ß-sulfate], XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2a, 5-dicarboxy-1-sulfate],

XXXIII. [Butane-la, 4-dicarboxy-l-sulfonic acid], XXXIV. [Butane-1α, 4-dicarboxy-1-sulfate], XXXV. [D-homoglutamic acid, N-sulfonic acid], XXXVI. [Pentane-2ß, 5-dicarboxy-1-sulfonic acid], XXXVII. [Pentane-2ß, 5-dicarboxy-1-sulfate],

(XXVIII. [Butane-1 (3, 4-dicarboxy-1-sulfonic acid],

XXXIX. [Butane-1 (3, 4-dicarboxy-1-sulfate], Yet another embodiment of the present invention, wherein said compound is non-toxic salts selected from the group consisting of : I. [D-homoglutamic acid, 3α-sulfonic acid], II. [D-homoglutamic acid, 3a-sulfate], III. [D-homoglutamic acid, 3p-sulfonic acid], IV. [D-homoglutamic acid, 3p-sulfate], V. [D-homoglutamic acid, 4a-sulfonic acid], VI. [D-homoglutamic acid, 4a-sulfate], VII. [D-homoglutamic acid, 4p-sulfonic acid], VIII. [D-homoglutamic acid, 4p-sulfate], IX. [D-homoglutamic acid, 5a-sulfate], X. [D-homoglutamic acid, 5a-sulfate], XI. [D-homoglutamic acid, 5p-sulfonic acid], XII. [D-homoglutamic acid, 5p-sulfate], XIII. [L-homoglutamine, N-sulfonic acid], XIV. [Pentane-2a-carboxy, 5-carboxamido-l-sulfonic acid], XV. [Pentane-2α-carboxy, 5-carboxamido-1-sulfate],

XVI. [Butane-1α-carboxy, 4-carboxamido-1-sulfonic acid], XVII. [Butane-la-carboxy, 4-carboxamido-1-sulfate], XVIII. [D-homoglutamine, N-sulfonic acid], XIX. [Pentane-2ß-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Butane-1 ß-carboxy, 4-carboxamido-1-sulfonic acid], XXI. [Butane-1 ß-carboxy, 4-carboxyamido-1-sulfate], XXII. [D-homoglutamine, 3a-sulfonic acid], XXIII. [D-homoglutamine, 3a-sulfate], XXIV. [D-homoglutamine, 3ß-sulfonic acid], XXV. [D-homoglutamine, 3p-sulfate], XXVI. [D-homoglutamine, 4a-sulfonic acid], XXVII. [D-homoglutamine, 4a-sulfate], XXVIII. [D-homoglutamine, 4 (3-sulfonic acid], XXIX. [D-homoglutamine, 4p-sulfate], XXX. [D-homoglutamine, Sa-sulfonic acid], XXXI. [D-homoglutamine, Sa-sulfate], XXXII. [D-homoglutamine, 5p-sulfonic acid] and XXXIII. [D-homoglutamine, 5ß-sulfate].

Yet another embodiment of the present invention, wherein said compound is selected from the group consisting of aspartic acid, asparagine and corresponding de-amino analogs: I. [L-Aspartic acid, N-Sulfonic acid], II. [2a, 3-dicarboxy, propane-1-sulfonic acid], III. [2a, 3-dicarboxy, propane-1-sulfate], IV. [1 a, 2-carboxy ethane sulfonic acid], V. [1 a, 2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2ß, 3-carboxy, propane-l-sulfonic acid], VIII. [2ß,3-carboxy,propane-1-sulfate], IX. [I P, 2-carboxy ethane-1-sulfonic acid], X. [1ß,2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3a-sulfonic acid], XII. [D-aspartic acid, 3a-sulfate],

XIII. [D-aspartic acid, 3ß-sulfonic acid], XIV. [D-aspartic acid, 3@-sulfate], XV. [L-asparagine, N-sulfonic acid], XVI. [2a-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2a-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [la-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [la-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3a-sulfonic acid], XXI. [L-asparagine, 3α-sulfate], XXII. [L-asparagine, 3p-sulfonic acid], XXIII. [L-asparagine, 3ß-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2p-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2p-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1ß-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII. [1ß-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3a-sulfonic acid], XXX. [D-asparagine, 3a-sulfate], XXXI. [D-asparagine, 3p-sulfonic acid], XXXII. [D-asparagine, 3ß-sulfate], Yet another embodiment of the present invention, wherein said compound is selected from the group consisting of glutamic acid, glutamine and corresponding de-amino analogs: I. [L-glutamic acid, N-sulfonic acid], II. [2a, 4-dicarboxy, butane-1-sulfonic acid], III. [2a, 4-dicarboxy, butane-1-sulfate], IV. [la, 3-dicarboxy, propane sulfonic acid], V. [la, 3-dicarboxy, propane sulfate], VI. [1ß, 3-dicarboxy, propane sulfate], VII. [l ß, 3-dicarboxy, propane sulfonic acid], VIII. [D-glutamic acid, N-sulfonic acid], IX. [2 (3, 4-dicarboxy, butane-1-sulfonic acid], X. [2ß, 4-dicarboxy, butane-1-sulfate], XI. [D-glutamic acid, 3α-sulfonic acid],

XII. [D-glutamic acid, 3a-sulfate], XIII. [D-glutamic acid, 3p-sulfonic acid], XIV : [D-glutamic acid, 3p-sulfate], XV. [D-glutamic acid, 4a-sulfonic acid], XVI. [D-glutamic acid, 4a-sulfate], XVII. [D-glutamic acid, 4p-sulfonic acid], XVIII. [D-glutamic acid, 3f3-sulfate], XIX. [L-glutamine, N-sulfonic acid], XX. [2a-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2a-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [la-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXIII. [la-carboxy, 3-carboxamido, propane-1-sulfate], XXIV. [1ß-carboxy, 3-carboxamido, propane-1-sulfate], XXV. [1 (3-carboxy, 3-carboxamido, propane-1-sulfonic acid), XXVI. [D-glutamine, N-sulfonic acid], XXVII. [2ß-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXVIII. [2p-carboxy, 4-carboxamido, butane-1-sulfate], XXIX. [D-glutamine, 3a-sulfonic acid], XXX. [D-glutamine, 3a-sulfate], XXXI. [D-glutamine, 3ß-sulfonic acid], XXXII. [D-glutamine, 3ß-sulfate], XXXIII. [D-glutamine, 4a-sulfonic acid], XXXIV. [D-glutamine, 4a-sulfate], XXXV. [D-glutamine, 4ß-sulfonic acid],

XXXVI. [D-glutamine, 4ß-sulfate], XXXVII. [L-homoglutamic acid, N-sulfonic acid], XXXVIII. [Pentane-2a, 5-dicarboxy-1-sulfonic acid], XXXIX. [Pentane-2a, 5-dicarboxy-1-sulfate], XL. [Butane-1α, 4-dicarboxy-1-sulfonic acid],

XLI. [Butane-la, 4-dicarboxy-1-sulfate], Still another embodiment of the present invention, wherein said compound is selected from the group consisting of homoglutamic acid, homoglutamine and corresponding de-amino analogs :

I. [D-homoglutamic acid, N-sulfonic acid], II. [Pentane-2ß, 5-dicarboxy-1-sulfonic acid], III. [Pentane-2ß, 5-dicarboxy-1-sulfate], IV. [Butane-lp, 4-dicarboxy-l-sulionicacid], V. [Butane-1 ß, 4-dicarboxy-1-sulfate], VI. [D-homoglutamic acid, 3a-sulfonic acid], VII. [D-homoglutamic acid, 3a-sulfate], VIII. [D-homoglutamic acid, 3ß-sulfonic acid], IX. [D-homoglutamic acid, 3p-sulfate], X. [D-homoglutamic acid, 4a-sulfonic acid], XI. [D-homoglutamic acid, 4a-sulfate], XII. [D-homoglutamic acid, 4ß-sulfonic acid], XIII. [D-homoglutamic acid, 4p-sulfate], XIV. [D-homoglutamic acid, Sa-sulfate], XV. [D-homoglutamic acid, 5a-sulfate], XVI. [D-homoglutamic acid, 5ß-sulfonic acid], XVII. [D-homoglutamic acid, 5ß-sulfate], XVIII. [L-homoglutamine, N-sulfonic acid], XIX. [Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Pentane-2a-carboxy, 5-carboxamido-1-sulfate], XXI. [Butane-la-carboxy, 4-carboxamido-1-sulfonic acid], XXII. [Butane-la-carboxy, 4-carboxamido-1-sulfate], XXIII. [D-homoglutamine, N-sulfonic acid], XXIV. [Pentane-2 (3-carboxy, 5-carboxamido-1-sulfonic acid], XXV. [Butane-1 (3-carboxy, 4-carboxamido-1-sulfonic acid], XXVI. [Butane-1 (3-carboxy, 4-carboxamido-1-sulfate], XXVII. [D-homoglutamine, 3a-sulfonic acid], XXVIII. [D-homoglutamine, 3a-sulfate], XXIX. [D-homoglutamine, 3ß-sulfonic acid], XXX. [D-homoglutamine, 3ß-sulfate], XXXI. [D-homoglutamine, 4a-sulfonic acid], XXXII. [D-homoglutamine, 4a-sulfate], XXXIII. [D-homoglutamine, 4ß-sulfonic acid], XXXIV. [D-homoglutamine, 4 (3-sulfate], XXXV. [D-homoglutamine, 5a-sulfonic acid], XXXVI. [D-homoglutamine, Sa-sulfate], XXXVII. [D-homoglutamine, 5p-sulfonic acid] and

XXXVIII. [D-homoglutamine, Sß-sulfate].

Still another embodiment of a present invention relates to a compound incubation of BM leukocyte precursors with different concentrations of the synthetic compound increases the cell surface densities of CD 11 c, CD80, CD54 and CDl lc to various levels with maximum up regulation at 200 mM.

Still further another embodiment of a present invention relates to a compound it gives the fold increase in the levels of molecules of cells stimulated with either 15 ng/ml of GM- CSF or 200 mM of the synthetic compound at 48 h of incubation.

Yet another embodiment of a present invention relates to a compound wherein the viability of the cultures is more than 99% at the end of the incubation period at this concentration of the synthetic compound.

Yet another embodiment of a present invention relates to a compound useful for inhibition of mononuclear TRAP-positive osteoclasts.

Yet another embodiment of a present invention relates to a compound useful for inhibition of fusion of mononuclear cells into multinuclear osteoclasts.

Yet another embodiment of a present invention relates to a compound useful for inhibition of bone resorption.

Yet another embodiment of a present invention relates to a compound has non-toxic to monocytes.

Yet another embodiment of a present invention relates to a compound has non-toxic to macrophages.

Further embodiment of a present invention relates to a method for inhibition of osteoclast formation comprising the step of administering a pharmaceutically acceptable amount of a compound to a subject in need thereof optionally with an additive, excipient, diluent or carrier.

Yet a nother e mbodiment o f a p resent i nvention r elates t o a m ethod w herein d osage t he compound is 5 to 10 mgl kg body weight Yet another embodiment of a present invention relates to a method wherein the period of administration is 25-30 days.

Further embodiment of a present invention relates to a method for inhibition of mononuclear TRAP-positive osteoclasts comprising the step of administering a pharmaceutically acceptable amount of a compound subject in need thereof optionally with an additive, excipient, diluent or carrier.

Yet another embodiment of a present invention relates to a method wherein dosage of the compound is 5 to 10 mg/kg body weight Yet another embodiment of a present invention relates to a method wherein the period of administration is 25-30 days.

Further embodiment of a present invention relates to a method for inhibition of multinuclear TRAP-positive osteoclasts comprising the step of administering a pharmaceutically acceptable amount of a compound to a subject in need thereof optionally with an additive, excipient, diluent or carrier.

Yet another embodiment of a present invention relates to a method wherein the dosage of the compound is 5 to 10 mg/kg body weight.

Yet another embodiment of a present invention relates to a method wherein the period of administration is 5to 30 days.

Still further embodiment of a present invention relates to a method for modulation of immune response controlled by differentiation of dendricts cells comprising the step of administration a pharmaceutical acceptable amount of a compound to a subject in need thereof optionally with an additive, excipient, diluents or carrier.

Yet another embodiment of a present invention relates to a compound useful to induce differentiation of dendritic cells and modulation of immune response controlled by dendritic cell.

Yet another embodiment of a present invention relates to a compound useful in vaccine fonnulation to prevent more efficicent and faster presentation of antigens to T-cells thereby initiate primary protective Thl immune response and help in the clearance of the pathogen.

The compounds for differentiation of dendritic cells also contained different divalent metal ions such as Mg, Ca and Zn. The composition consisted of varying amounts of the above acid amino acid/dicarboxylic acid derivatives and their pharmaceutically acceptable salts.

Non toxic salts of the present invention are contained all pharmaceutically acceptable salts, for example, general salts, acid addition salt, hydrate salts.

The compounds of the formulae (Ia), (Ib) and (Ic) of the present invention may be converted into the corresponding salts. Non toxic and water soluble salts are preferable.

Suitable salts for example are as follows:

Salts of alkaline earth metals (Mg, Ca etc) Ammonium Salts Salts of pharmaceutically acceptable organic amines (tetramethyl ammonium, triethyl amine, methyl amine, cyclopentyl amine, benzylamine, phenethylamine, piperidine, monoethanolamine, diethanolamine, tris (hydroxymethyl) amine, lysine, arginine, N-methyl glucamine, etc. a) a process for the preparation of sulfonic acid/sulfate derivatives of the formula (Ia) (Ib) (Ic) and non-toxic salts thereof : b) a process for the preparation of sulfonic acid/sulfate derivatives of the formula and non-toxic salts thereof : c) a process for the preparation of sulfonic acid/sulfate derivatives of the formula) and non-toxic salts thereof : d) In the compound of the present invention of the formula (Ia) wherein the compound is selected from the group consisting of aspartic, acid, asparagine and corresponding de- amino analogs : e) In the compound of the present invention of the formula (Ib) wherein the compound is selected from the group consisting of glutamic acid, glutamine and corresponding de- amino analogs: In the compound of the present invention of the formula (Ic) wherein the compound is selected from the group consisting of homoglutamic acid, homoglutamine and corresponding de-amino analogs: Among the various Antigen Presenting Cells (APCs) of the immune system. Dendritic Cells (DCs) constitute the most potent APCs and act as a bridge between the innate and the acquired arm of the immune system. This is largely attributed to the ability of DCs to take-up pico-to femtomoles of antigen and to stimulate primary naive quiescent T cells, thereby initiating a primary immune response. DCs exist in various states of activation that translates into distinct functions. For example, DCs arising from the Bone Marrow (BM) are essentially immature DCs. These DCs exhibit low levels of T cell costimulatory molecules such as CD80, CD86, CD40 & CD54 and also low levels of surface MHC class I and class II molecules. Further, these DCs express a range of phagocytic, endocytic and scavenger receptors and owing to the above features are thus programmed for antigen capture and uptake. Upon contact with various inflammatory stimuli such as, TNF bacterial endotoxins (e. g. LPS), CD40 ligand (CD401), CpG containing bacterial DNA,

double stranded viruses and certain (but not all) antigens, DCs undergo a process of maturation, wherein they now upregulate their surface levels of costimulatory molecules and MHC-peptide complexes (now exported to the cell surface following degradation and loading onto MHC trimers) and are thus programmed for antigen presentation and T lymphocyte stimulation. The transformation from the immature to the mature stage is a tightly regulated process often requiring T cell help. During maturation these DCs also secrete a range of cytokines such as TNF-I2, IL-12, IFN-0 and low levels of IL-10.

Owing to secretion of pro-inflammatory cytokines, DCs are thought to drive pro- inflammatory or Thl responses and help in the clearance of the pathogen. Therefore, factors/molecules that increase the population of immature DCs in the immune system offer a dded a dvantage for t he h ost's fight a gainst i nfectious p athogens. In t his c ontext efforts have been focused on finding and generating ways to increase the DC numbers in the immune system. These have included the use of recombinant DCs or even pathogens that have been transformed to express Granulocyte Macrophage-Colony Stimulating Factor (GM-CSF), the growth factor that is conventionally used to generate DCs in vitro.

A number of studies have identified pathogen and host products such as proteins that induce the maturation of different DC subsets. Owing to their fully mature status these DCs are more programmed for antigen presentation and T cell stimulation and have reduced capacity to capture antigens of pathogens. Immature DCs that are de novo differentiated from precursors offer better advantage than mature DCs because of their ability to scavenge pathogens followed by their uptake and processing and subsequent presentation to T lymphocytes. Our observation on the ability of'the molecule'to induce differentiation of Dendritic Cells from mouse bone marrow leukocyte precursors, therefore, assumes paramount importance and is a significant step towards modulation of immune responses controlled by DCs. As the D Cs differentiated by'the molecule'are immature in nature and resemble very closely to the DCs differentiated by GM-CSF they will be efficient not only at antigen capture but also be effective T cell simulators.

Among the many applications, the two most important ones would include the use of'the molecule'in vaccine formulations or in protection based studies that would promote more efficient and faster presentation of the antigens to T cells thereby initiate primary protective Tht immune responses and help in the clearance of the pathogen. Further,'the molecule'offers a cheap alternative to GM-CSF for commercial purposes to generate DCs in vitro for research based studies.

Basically, immuno-supression is a common clinical feature in many infectious diseases.

This immuno-supression cripples the ability of the immune systems to get rid of the infectious agents eventuating in the death of the host. It has been found that the host recovering from disease after chemotherapy shows a significant improvement of antigen- specific immune functions. Despite the urgency of the need, and immuno-potentiator which c an b e o f h uman u se r emains a waited. The c umulative i ncidence o f t he d iseases obviates the need for a drug (s) that restores the immune response of the affected individual to a normal level.

In response to any invasion by a pathogen, the complex multicellular organisms have evolved a defense mechanism to make their internal environment more hostile to invaders.

All immune systems have one feature in common : they respond to infection by switching from a resting to an active state. The innate response limits the infection and activates Antigen Presenting Cells (APCs) to trigger adaptive immunity, which increases specificity and generates memory. Consequently, the immune responses that occur during an encounter with antigens-be it infectious agents or allergens are primarily characterized by the plasticity of their nature and magnitude. This feature provides an important advantage y that permits the immune system to tailor its defense strategy to particular groups of antigens. Interactions between APCs such as Dendritic cells (DCs) and macrophages and the different subsets of T cells (CD4+ and CD8+) in the T cell rich areas of the lymph nodes and spleen, amplify the consequent immune responses. Following this interaction, T helper (Th) cell precursors then differentiate into effectors. that secrete either pro-inflammatory or suppressor/regulatory cytokines such as Interferon (IFN)-0 Tumor Necrosis Factor (TNF)- 0, and Interleukin (IL)-1, or IL-4, IL-10 and Transforming Growth Factor (TGF)-O, respectively.

Among the most potent of the APCs are the macrophages and different subsets of DCs, that together virtually regulate the antigen capture and presentation of the innate arm of the immune system. DCs are professional APCs that are continuously produced by the stem cells in the hematopoeitic tissues. DCs exist at various states of activation that are primarily classified as immature (iDCs) and mature (mDCs). iDCs are programmed for antigen capture, which upon contact with various stimuli, such as bacterial products, CD40 ligand, (TNF)-G, and certain antigens undergo a process of maturation wherein they now become programmed for antigen presentation and T-cell stimulation. Consequently, agents that promote the maturation of iDCs play a vital role in shaping the early immune

responses elicited during an infection. Along with macrophages, that constitute the all important phagocytic component of the innate immune system DCs activate the effector cells such as the various subsets of T-cells, Natural Killer (NK) cells and NK-T cells by secreting a profile of cytokines that would eventually prime these effector cells to carryout their functions. These range from stimulating the adaptive arm of the immune system for the generation of antibody mediated responses, to stimulation of the cytotoxic activity by the CD8+ T-cells against the infected cells/tissues. The invention may provide a novel compound that will be useful in vaccination, cancer therapy and other immunomodulatory regiments.

The preferable specific compounds of the formulae (Ia), (Ib) and (Ic) are the derivatives of aspartic acid, asparagine and corresponding de-amino analogs (Table 1), glutamic acid, glutamine and corresponding de-amino analogs (Table 2) and homoglutamic acid, homoglutamine and corresponding de-amino analogs (Table 3) and non toxic salts thereof and example compounds.

BRIEF DESCRIPTION OF DRAWINGS: 1. Plate A represents surface level of CD 80.

2. Plate B represents surface level of CD 54.

3. Plate C represents surface level of CD llc.

4. Plate D represents surface level of CD H-2D (MHC class 1).

BREIF DESCRIPTION OF THE ACCOMPANYING PLATES Plate 1. Compound 1 induces differentiation of dendritic cells from BALB/c mouse bone marrow Enriched leukocyte precursors from 4 to 6 weeks old mice were stimulated with varying concentrations of compound as given in example-3 for 48 h. Cells were stained for the surface levels of indicated markers. Panels A-D represent surface levels of CD80, CD54, CD lie and H-2D (MHC class I), respectively. Results obtained with Granulocyte Macrophage-Colony Stimulating Factor (GM-CSF) are also shown for comparison. Panels a to d in each Panel shows the surface levels of indicated markers on cells stimulated with 15 ng/ml of GM-CSF, 10 llg/ml, 5 ug/ml and 1 llg/ml of compound 1, respectively. The Green line represents staining of stimulated cells while the black line depicts staining of unstimulated cells.

Differentiation of Dendritic cells The fine suspension obtained above was transferred into a 50 ml sterile centrifuge tube and centrifuged for 10 minutes at 1200 rpm. After removing the supernatant, RBC lysis buffer

remove unwanted tissue etc. Microbeads (I-A, CD45R and CD90) were added to this clear solution and incubated for one hour at 4°C with shaking to eliminate other lymphocytes and macrophages and MHC positive cells. This suspension was then finally passed through a MACS (Magnetic Activated Cell Sorting) column to get essentially and predominately leukocyte precursors. The cell pellet was suspended in complete medium (RPMI 1640, 10% Foetal Calf Serum, Sodium pyruvate (1 mM) and 2-Mercaptoethanol (50 mM). About 2.5-3 x 106 leukocyte precursors were plated in each well of a 24 well culture plate in lml culture volume. Cells were stimulated with either 15 ng per ml of Granulocyte Macrophage-Colony Stimulating Factor (GM-CSF) or 50 micro gram per ml of the compound (neutralized with 1 M Tris HCI to achieve a pH of 7.0). The plate was incubated for 48 hours at 37°C in a C02 incubator.

Evaluation of cell surface znarker expression In order to evaluate the upregulation of various cell surface markers associated with Dendritic cells, flow cytometry on the cells stimulated with GM-CSF or the compound was carried out using fluorescent labeled antibodies to various molecules (CDl lc, I-Ad, CD80, CD86, H2-Dd, CD54, CD40).

Effect of compound as given in example 3 on RANKL-induced osteoclast differentiation from haemopoietic precursors of monocytes/macrophage lineage. Mice osteoclast precursors were incubated in the presence of M-CSF and RANKL in the absence and presence of the compound. Photomicrographs showing TRAP-positive osteoclasts in the absence A) and presence of B) of the compound. This compound significantly inhibited osteoclast formation.

6. Effect of compound as described in example 4 on RANKL-induced osteoclast differentiation from haemopoietic precursors of monocytes/macrophage lineage. Photomicrographs showing TRAP- positive osteoclasts induced by M-CSF and RANKL in the absence A) and presence of B) of compound. This compound showed no inhibitory effect on osteoclast differentiation.

LIST OF TABLES Table 1 structure 1 1. L-Aspartic acid, N-Sulfonic acid Z=OH, R1=NHSO3H, R2=R3=R4=H 2. L-Aspartic acid, 2p-sulfonic acid Z=OH, Rl=NH2, R3=R4=H, R2=SO3H 3. L-Aspartic acid, 2p-sulfate Z=OH, R1=NH2, R3=R4=H, R2=OS03H 4. L-aspartic acid, 3a-sulfonic acid Z=OH, R1=NH2, R2=R4=H, R3=S03H 5. L-aspartic acid, 3a-sulfate Z=OH, R1=NH2, R2=R4=H, R3=OS03H 6. L-aspartic acid, 3p-sulfonic acid Z=OH, Ri=NH2, R2=R3=H R4=S03H 7. L-aspartic acid, 3ß-sulfate Z=OH, R1=NH2, R2=R3=H, R4=OSO3H 8. 2a. 3-dicarboxy, propane-l-sulfonic acid Z=OH, R1=R3=R4=H, R2=CH2SO3H 9. 2a, 3-dicarboxy, propane-1-sulfate Z=OH, R1=R3=R4=H, R2=CH2OSO3H 10. 1a, 2-carboxy ethane sulfonic acid Z=OH, Ri=R3=R4=H, R2=S03H 11. 1α,2-carboxy ethane sulfate Z=OH, R1=R3=R4=H, R2=OSO3H

12. D-aspartic acid, N-sulfonic acid Z=OH, R2=NHS03H, R1=R3=R4=H 13. 2ß,3-carboxy,propane-1-sulfonic acid Z=OH, R2=H, R1=CH2SO3H 14. 2ß,3-carboxy,propane-1-sulfate Z=OH, R2=H, R1=CH2OSO3H 15. 1ß,2-carboxy ethane-1-sulfonic acid Z=OH, R2=H, R1=SO3H 16. 1 ß, 2-carboxy ethane-1-sulfate Z=OH, R2=H, R1=OSO3H 17. D-aspartic acid, 2a-sulfonic acid Z=OH, R2=NH2, R3=R4=H, R1=SO3H 18. D-aspartic acid, 2a-sulfonic acid Z=OH, R2=NH2, R3=R4=H, R1=SO3H 19. D-Aspartic acid, 3a-sulfonic acid Z=OH, R2=NH2, R1=R4=H, R3=SO3H 20. D-Aspartic acid, 3a-sulfate Z=OH, R2=NH2, R1=R4=H, R3=OSO3H 21. D-Aspartic acid, 3ß-sulfonic acid Z=OH, R2=NH2, R1=R3=H, R4=S03H 22. D-aspartic acid, 3ß-sulfate Z=OH, R2=NH2, Rl=R3=H, R4=OS03H 23. L-asparagine, N-sulfonic acid Z=NH2, Rl=NHS03H, R2=R3=R4=H 24.2a-carboxy, 3-carboxamido, propane-1-sulfonic acid Z=NH2, Rl H, R2=CH2SO3H 25.2a-carboxy, 3-carboxamido, propane-1-sulfate Z=NH2, RI=H, R2=CH2OSO3H 26. la-carboxy, 2-carboxamido, ethane sulfonic acid Z=NH2, R1=H, R2=S03H 27. la-carboxy, 2-carboxamido, ethane sulfateZ=NH2, R1=H, R2=OSO3H 28. L-asparagine, 2ß-sulfonic acid Z=R1=NH2, R2=R4=H, R2=SO3H 29. L-asparagine, 2ß-sulfateZ=R1=NH2, R2=R4=H, R3=OSO3H 30. L-asparagine, 3a-sulfonic acid Z=R1=NH2, R2=R4=H, R3=SO3H 31. L-asparagine, 3α-sulfateZ=R1=NH2, R2=R4=H, R3=OS03H 32. L-asparagine, 3ß-sulfonic acid Z=R1=NH2, R2=R3=H, R4=SO3H 33. L-asparagine, 3p-sulfateZ=R, =NH2, R2=R3=H, R4=OS03H 34. D-asparagine, N-sulfonic acid Z=NH2, R2=NHS03H, R1=R3=R4=H 35. 2p-carboxy, 3-carboxamido, propane-1-sulfonic acidZ=NH2, R2 to R4=H, R1=CH2SO3H 36. 2p-carboxy, 3-carboxamido, propane-1-sulfateZ=NH2, R2 to R4=H, R, =CH2S03H 37. Ip-carboxy, 2-carboxamido, ethane sulfonic acid] Z=OH, R2 to R4=H, R, =S03H 38. 1ß-carboxy, 2-carboxamido, ethane sulfate Z=OH, R2 to R4=H, R1=OSO3H 39. D-asparagine, 2a-sulfonic acid Z=R2=NH2, R3=R4=H, R1=SO3H

40. D-asparagine, 2α-sulfateZ=R2=NH2, R3=R4=H, R1=OSO3H 41. D-asparagine, 3a-sulfonic acid Z=R2=NH2, Ri=R4=H, R3=S03H 42. D-asparagine, 3cc-sulfateZ=R2=NH2, RI=R4=H, R3=OS03H 43. D-asparagine, 3p-sulfonic acid Z=R2=NH2, R1=R3=H, R4=SO3H 44. D-asparagine, 3ß-sulfateZ=R2=NH2, R1=R3=H, R4=OSO3H Table 2 Structure 2 1. L-glutamic acid,'N-sulfonic acid Z=OH, R1=NHSO3H, R2=R3=R4=R5=R6=H 2. 2a, 4-dicarboxy, butane-1-sulfonic acid Z=OH, RI, R3 to R6=H, R2=CH2SO3H 3. 2a, 4-dicarboxy, butane-1-sulfate Z=OH, RI, R3. to R6=H, R2=CH20S03H 4- 1α, 3-dicarboxy, propane sulfonic acid Z=OH, Ri, R3 to R6=H, R2=SO3H 5. la, 3-dicarboxy, propane sulfate Z=OH, RI, R3 to R6=H, R2=OSO3H 6.1 ß. 3-dicarboxy, propane sulfate Z=OH, R2 to R6=H, R1-OSO3H 7. 1ß, 3-dicarboxy, propane sulfonic acid Z=OH, R2 to R6=H, R1=SO3H 8. L-glutamic acid, 2ß-sulfonic acid Z=OH, R1=NH2, R3 to R6=H, R2=SO3H 9. L-glutamic acid, 2ß-sulfateZ=OH, R1=NH2, R3 to R6=H, R2=OS03H 10. L-glutamic acid, 3a-sulfonic acid Z=OH, R1=NH2, R2=H, R4 to R6=H, R3=SO3H 11. L-glutamic acid, 3a-sulfate Z=OH, R1=NH2, R2=H, R4 to R6=H, R3=OS03H 12. L-glutamic acid, 3ß-sulfonic acid Z=OH, R1=NH2, R2=R3=R5=R6=H, R4=SO3H 13. L-glutamic acid, 3(3-sulfate Z=OH, Ri=NH2, R2=R3=R5=R6=H, R4=OS03H 14. L-glutamic acid, 4a-sulfonic acid Z=OH, R1=NH2, R2=R3=R4=R6=H, R5=SO3H

15. L-glutamic acid, 4a-sulfate Z=OH, R, =NH2, R2=R3=R4=R6=H, R5=OS03H 16. L-glutamic acid, 4p-sulfonic acid Z=OH, Ri=NH2, R2 to R5=H, R6=SO3H 17. L-glutamic acid, 4 (3-sulfate Z=OH, R1=NH2, R2 to R5=H, R6=OSO3H 18. D-glutamic acid, N-sulfonic acidZ=OH, R2=NHS03H, R1, R3 to R6=H 19. 2ß, 4-dicarboxy, butane-1-sulfonic acid Z=OH, R2 to R6=H, Ri=CH2S03H 20. 2ß, 4-dicarboxy, butane-1-sulfate Z=OH, R2 to R6=H, R1=CH2OSO3H 21. D-glutamic acid, 2a-sulfonic acid Z=OH, R2=NH2, R3 to R6 H, R1=SO3H 22. D-glutamic acid, 2a-sulfate Z=OH, R2=NH2, R3 to R6 H, R1=OSO3H 23. D-glutamic acid, 3α-sulfonic acid Z=OH, R2=NH2, Ri, R4 to R6 H, R3=SO3H 24. D-glutamic acid, 3a-sulfate Z=OH, R2=NH2, Rl, R4 to R6 H, R3=OS03H 25. D-glutamic acid, 3ß-sulfonic acid Z=OH, R2=NH2, Ri=R3=R5=R6=H, R4=S03H 26. D-glutamic acid, 3ß-sulfate Z=OH, R2=NH2, R1=R3=R5=R6=H, R4=OSO3H 27. D-glutamic acid, 4a-sulfonic acid Z=OH, R2=NH2, R1=R3=R4=R6=H, R5=SO3H 28. D-glutamic acid, 4a-sulfate Z=OH, R2=NH2, R1=R3=R4=R6=H, R5=OSO3H 29. D-glutamic acid, 4ß-sulfonic acid Z=OH, R2=NH2, Ri=R3=R4=R5=H, R6=SO3H 30. D-glutamic acid, 4ß-sulfate Z=OH, R2=NH2, R1=R3=R4=R5=H, R6=OS03H 31. L-glutamine, N-sulfonic acid Z=NH2, R1=NHSO3H, R2 to R6=H 32. L-glutamine, 2ß-sulfonic acid Z=R1=NH2, R3 to R6 33. L-glutamine, 2ß-sulfate Z=R1=NH2, R3 to R6 =H, R2=OS03H 34. L-glutamine, 3a-sulfonic acid Z=R1=NH2, R2=H, R3 to R6=H, R3=SO3H 35. L-glutamine, 3α-sulfateZ=R1=NH2, R2=H, R3 to R6=H, R3=OS03H 36. L-glutamine, 3ß-sulfonic acid Z=RI=NH2, R2=R3=R5=R6=H, R4=S03H 37. L-glutamine, 3ß-sulfate Z=R1=NH2, R2=R3=R5=R6=H, R4=OSO3H 38. L-glutamine, 4a-sulfonic acidZ=R1=NH2, R2=R3=R4=R6=H, R5=SO3H 39. L-glutamine,-4a-sulfate Z=R, =NH2, R2=R3=R4=R6=H, R5=OS03H 40. L-glutamine, 4 (3-sulfonic acid Z=R, =NH2, R2 to R5=H, R6=SO3H 41. L-glutamine, 4ß-sulfate Z=R1=NH2, R2 to R5=H, R6=OS03H 42. 2a-carboxy, 4-carboxamido, butane-1-sulfonic acid Z=NH2, Ri, R3 to R6=H, R2=CH2SO3H

43. 2a-carboxy, 4-carboxamido, butane-1-sulfate Z=NH2, Ri, R3 to R6=H, R2=CH2OSO3H 44. la-carboxy, 3-carboxamido, propane-1-sulfonic acid Z= NH2, Ri, R3 to R6=H, R2=SO3H 45. 1 a-carboxy, 3-carboxamido, propane-1-sulfateZ= NH2, R,, R3 to R6=H, R2=OSO3H 46. 1ß-carboxy, 3-carboxamido, propane-1-sulfateZ= NH2, R2 to R6=H, R1=OSO3H 47. 1ß-carboxy, 3-carboxamido, propane-1-sulfonic acidZ= NH2, R2 to R6=H, R1=SO3H 48. D-glutamine, N-sulfonic acidZ=NH2, R2=NHS03H ; R1=H, R3 to R6=H 49. 2p-carboxy, 4-carboxamido, butane-1-sulfonic acidZ= NH2, R2 to R6=H, R1=CH2SO3H 50. 2ß-carboxy, 4-carboxamido, butane-1-sulfateZ= NH2, R2 to R6=H, R1=CH2OSO3H 51. D-glutamine, 2a-sulfonic acid Z= NH2, R2=NH2, R3 to R6=H, R1=SO3H 52. D-glutamine, 2a-sulfate Z=NH2, R2=NH2, R3 to R6=H, R1=OSO3H 53. D-glutamine, 3a-sulfonic acid Z=NH2, R2=NH2, R1, R4 to R6 H, R3=SO3H 54. D-glutamine, 3a-sulfate Z=R2=NH2, Rl, R4 to R6 H, R3=OS03H 55. D-glutamine, 3p-sulfonic acid Z=R2=NH2, R1=R3=R5=R6=H, R4=SO3H 56. D-glutamine, 3p-sulfate Z=R2=NH2, RI=R3=R5=R6=H, R4=OS03H 57. D-glutamine, 4a-sulfonic acid Z=R2=NH2, R1=R3=R4=R6=H, R5=SO3H 58. D-glutamine, 4a-sulfate Z=R2=NH2, R1=R3=R4=R6=H, R5=OSO3H 59. D-glutamine, 4ß-sulfonic acid Z=R2=NH2, R1=R3=R4=R5=H, R6=SO3H 60. D-glutamine, 4ß-sulfate Z=R2=NH2, R1=R3=R4=R5=H, R6=OSO3H Table 3 structure 3

1. L-homoglutamic acid, N-sulfonic acid Z=OH, R1=NHSO3H, R2 to R8=H 2. Pentane-2a, 5-dicarboxy-l-sulfonic acid Z=OH, Ri, R3 to R8=H, R2=CH2SO3H 3. Pentane-2a, 5-dicarboxy-1-sulfate Z=OH, RI, R3 to R8=H, R2=CH2OSO3H 4. Butane-la, 4-dicarboxy-1-sulfonic acid Z= OH, R 1, R3 to R8=H, R2=SO3H 5. Butane-la, 4-dicarboxy-1-sulfate Z=OH, R1, R3 to R8=H, R2=OSO3H 6. L-homoglutamic acid, 2p-sulfonic acid Z=OH, R1=NH2, R3 to R8=H, R2=SO3H 7. L-homoglutamic acid, 2ß-sulfate Z=OH, R1=NH2, R3 to R8=H, R2=OS03H 8. L-homoglutamic acid, 3α-sulfonic acid Z=OH, R1=NH2, R2=H, R4 to R8 H, R3=SO3H 9. L-homoglutamic acid, 3a-sulfate Z=OH, R1=NH2, R2=H, R4 to R8 H, R3=OSO3H 10. -homoglutamic acid, 3ß-sulfonic acid Z=OH, R1=NH2, R2=R3=H, R5 to R8=H, R4=S03H . 11. L-homoglutamic acid, 3ß-sulfate Z=OH, R1=NH2, R2=R3=H, R5 to R8=H, R4=OS03H 12. L-homoglutamic acid, 4a-sulfonic acid Z=OH, RI=NH2, R2=R3=R4=H, R6 to R8=H, R5=S03H 13. L-homoglutamic acid, 4a-sulfate Z=OH, R1=NH2, R2=R3=R4=H, R6 to Rs=H, R5=OS03H 14. L-homoglutamic acid, 4(3-sulfonic acid Z=OH, R1=NH2, R2=R5=H, R7=R8=H, R6=SO3H 15. L-homoglutamic acid, 4ß-sulfate Z=OH, R1=NH2, R2=R5=H, R7=R8=H, R6=OS03H 16. L-homoglutamic acid, Sa-sulfonic acid Z=OH, R1=NH2, R2 to R6=H, R8 =H, R7=SO3H 17. L-homoglutamic acid, 5a-sulfate Z=OH, R1=NH2, R2 to R6=H, R8 =H, R7=OS03H 18. L-homoglutamic acid, 5 (3-sulfonic acid Z=OH, R1=NH2, R2 to R7 =H, R8=S03H 19. L-homoglutamic acid, 5ß-sulfate Z=OH, R1=NH2, R2 to R7 =H, R8=OSO3H 20. D-homoglutamic acid, N-sulfonic acid Z=OH, R2=NHSO3H, R1, R3 to R8=H

21. Pentane-2p, 5-dicarboxy-1-sulfonic acid Z=OH, R2 to R8=H, R1=CH2SO3H 22. Pentane-2ß, 5-dicarboxy-1-sulfate Z=OH, R2 to R8=H, R1=CH2OSO3H 23. Butane-1ß,4-dicarboxy-1-sulfonic acid Z=OH, R2 to R8=H, R1=SO3H 24. Butane-1ß,4-dicarboxy-1-sulfate Z=OH, R2 to R8=H, R1=OSO3H 25. D-homoglutamic acid, 2α-sulfonic acid Z=OH, R2=NH2, R3 to R8=H, R1=SO3H 26. D-homoglutamic acid, 2a-sulfate Z=OH, R2=NH2, R3 to R8=H, R1=OSO3H 27. D-homoglutamic acid, 3α-sulfonic acid Z=OH, R2=NH2, RI, R4 to R8 H, R3=SO3H 28. D-homoglutamic acid, 3a-sulfate Z=OH, R2=NH2, Ri, R4 to Rs H, R3=OSO3H 29. D-homoglutamic acid, 3ß-sulfonic acid Z=OH, R2=NH2, R1=R3=H, Rs to R8=H, R4=S03H 30. D-homoglutamic acid, 3ß-sulfate Z=OH, R2=NH2, R1=R3=H, R5 to R8=H, R4=OSO3H 31. D-homoglutamic acid, 4a-sulfonic acid Z=OH, R2=NH2, R, =R3=R4=H, R6 to R8=H, R5=S03H 32. D-homoglutamic acid, 4a-sulfate Z=OH, R2=NH2, R1=R3=R4=H, R6 to Rg=H, R5=OSO3H 33. D-homoglutamic acid, 4i-sulfonic acid Z=OH, R2=NH2, R1=H, R3 to R5=H, R7=R8=H, R6=SO3H 34. D-homoglutamic acid, 4ß-sulfate Z=OH, R2=NH2, R1=H, R3 to R5=H, R7=Rs=H, R6=OS03H 35. D-homoglutamic acid, Sa-sulfonic acid Z=OH, R2=NH2, Ri=R8=H, R3 to R6=H, R7=SO3H 36. D-homoglutamic acid, Sa-sulfate Z=OH, R2=NH2, R1=R8=H, R3 to R6=H, R7=OSO3H 37. D-homoglutamic acid, 5 (3-sulfonic acid Z=OH, R2=NH2, R1=H, R3 to R7=H, R8=SO3H 38. D-homoglutamic acid, sus-sulfate Z=OH, R2=NH2, R1=H, R3 to R7=H, R8=OS03H 39. L-homoglutamine, N-sulfonic acid Z=NH2, R1=NHSO3H, R2 to R8=H

40. Pentane-2a-carboxy, 5-carboxamido-1-sulfonic acid Z=NH2, Ri and R3 to Rs=H, R2=CH2SO3H 41. Pentane-2a-carboxy, 5-carboxamido-1-sulfate Z=NH2, Ri and R3 to R8=H, R2=CH2OSO3H 42. Butane-la-carboxy, 4-carboxamido-1-sulfonic acid Z=NH2, R, and R3 to R8=H, R2=SO3H 43. Butane-la-carboxy, 4-carboxamido-1-sulfate Z=NH2, Ri and R3 to R8=H, R2=OS03H 44. L-homoglutamine, 2 (3-sulfonic acid Z=R1=NH2, R3 to R8=H, R2=SO3H 45. L-homoglutamine, 2ß-sulfate Z=R1=NH2, R3 to R8=H, R2=OS03H 46. L-homoglutamine, 3a-sulfonic acid Z=R1=NH2, R2=H, R4 to Rs=H, R3=SO3H 47. L-homoglutamine, 3a-sulfateZ=RI=NH2, R2=H, R4 to R8=H, R3=OS03H 48. L-homoglutamine, 3ß-sulfonic acid Z=R1=NH2, R2=R3=H, R5 to Rg=H, R4=S03H 49. L-homoglutamine, 3ß-sulfate Z=R1=NH2, R2=R3=H, R5 to R8=H, R4=OS03H 50. L-homoglutamine, 4a-sulfonic acid Z=R1=NH2, R2=R3=R4=H, R6 to R8=H, R5=SO3H 51. L-homoglutamine, 4a-sulfate Z=R1=NH2, R2=R3=R4=H, R6 to R8=H, R5=OSO3H 52. L-homoglutamine, 4 (3-sulfonic acid Z=R1=NH2, R2=R5=H, R7=R8=H, R6=S03H 53. L-homoglutamine, 4ß-sulfate Z=R1=NH2, R2=R5=H, R7=R8=H, R6=OSO3H 54. L-homoglutamine, 5a-sulfonic acid Z=Rf=NH2, R2 to R6=H, R8=H, R7=SO3H 55. L-homoglutamine, 5a-sulfate Z=R1=NH2, R2 to R6=H, R8=H, R7=OS03H 56. L-homoglutamine, 5 (3-sulfonic acid Z=R1=NH2, R2 to R7=H, R8=SO3H 57. L-homoglutamine, 5ß-sulfate Z=R1=NH2, R2 to R7=H, R8=OSO3H 58. D-homoglutamine, N-sulfonic acid Z=NH2, R2=NHS03H, R, and R3 to R8=H 59. Pentane-2p-carboxy, 5-carboxamido-l-sulfonic acid Z=NH2, R2 to R8=H, R1=CH2SO3H

60. Pentane-2p-carboxy, 5-carboxamido-1-sulfate Z=NH2, R2 to R8=H, R1=CH2OSO3H 61. Butane-1 ß-carboxy, 4-carboxamido-1-sulfonic acid Z=NH2, R2 to R8=H, R1=SO3H 62. Butane-1 (3-carboxy, 4-carboxamido-1-sulfate Z=NH2, R2 to R8=H, RI=OS03H 63. D-homoglutamine, 2a-sulfonic acid Z=R2=NH2, R3 to R8 H, R, =S03H 64. D-homoglutamine, 2a-sulfate Z=R2=NH2, R3 to R8 H, R1=OSO3H 65. D-homoglutamine, 3a-sulfonic acid Z=R2=NH2, R1, R4 to R8 H, R3=SO3H 66. D-homoglutamine, 3a-sulfate Z=R2=NH2, Rl, R4 to Rs H, R3=OS03H 67. D-homoglutamine, 3#-sulfonic a cid Z=R2=NR2, R I=R3=H, R5 to R8=H, R4=S03H 68. D-homoglutamine,. 3p-sulfate Z=R2=NH2, R1=R3=H, Rs to R8=H, R4=OS03H 69.. D-homoglutamine, 4α-sulfonic acid Z=R2=NH2, R1=R3=R4=H, R6 to R8=H, R5=SO3H 70. D-homoglutamine, 4a-sulfate Z=R2=NH2, R1=R3=R4=H, R6 to R8=H, R5=OSO3H 71. D-homoglutamine, 4#-sulfonic acid Z=R2=NH2, R1=H, R3 to R5=H, R7=R8=H, R6=SO3H 72. D-homoglutamine, 4#-sulfate Z=R2=NH2, R1=H, R3 to R5=H, R7=R8=H, R6=OS03H 73. D-homoglutamine, 5a-sulfonic acid Z=R2=NH2, R1=R8=H, R3 to R6 =H, R7=SO3H 74. D-homoglutamine, 5a-sulfate Z=R2=NH2, R1=R8=H, R3 to R6=H, R7=OS03H 75. D-homoglutamine, 5 (3-sulfonic acid Z=R2=NH2, R1\H, R3 to R7=H, Rs=S03H 76. D-homoglutamine, 5#-sulfate Z=R2=NH2, R1=H, R3 to R7=H, R8=OSO3H EXAMPLES: The following reference example and examples illustrate the present invention but do not limit the present invention.

The solvents in the parenthesis show the developing and eluting solvents and the ratios of the solvent used are by volume in the chromatographic separation or TLC.

The solvents in the parenthesis in NMR show the solvents used in measurement.

Reference example 1 L-glutamyl, N-sulfonic acid from glutamic acid mono tertiary butyl ester Glutamic acid monotertiary butyl ester (1 eq. ) was added portion-wise to a solution of SO2CI2 (2 eq. ) in dry CH2Cl2 at 0°C followed by Et3N (3 eq. ). Resulting solution stirred for 8 hrs at r. t. when TLC showed complete consumption of starting material. Solvent was evaporated and the crude was dried in vacuum. 3 ml water was added to it and the slurry was stirred for 1 hr. To the slurry was added 45 ml CH2C12 followed by 3 eq of TFA at 0° C. The resulting solution was stirred at r. t. for 24 hrs. The solvent was evaporated and dried in vacuum. The pseudo molecular ion, [M-H]-at 226.0049 confirmed the structure of the product L-glutamyl, N-sulfonic acid (calculated for C5H8NO7S ; 226. 0026).

Reference example 2 L-glutamyl, N-sulfonic acid from glutamic acid di tertiary butyl ester Glutamic acid ditertiary butyl ester (1 eq. ) was added portion-wise to a solution of S02Cl2 (2 eq. ) in dry CH2CI2 at 0°C followed by Et3N (3 eq. ). Resulting solution stirred for 8 hrs at r. t. when TLC showed complete consumption of starting material. Solvent was evaporated and the crude was dried in vacuum. 3 ml water was added to it and the slurry was stirred for I hr. To the slurry was added 45 ml CH2Cl2 followedby3 eq of TFA at 0°C. The resulting solution was stirred at r. t. for 24 hrs. The solvent was evaporated and dried in vacuum. T he p seudo m olecular i on, [M-H]-at 226.0049 confirmed the structure of the product L-glutamyl, N-sulfonic acid (calculated for C5H8NO7S ; 226.0026).

Reference example 3 L-Aspartyl, N-sulfonic acid from L-aspartic acid di tertiary butyl ester L-aspartic acid di tertiary butyl ester (1 eq. ) was added portion-wise to a solution of SO2CI2 (2 eq. ) in dry CH2CI2 at 0°C followed by Et3N (3 eq.). Resulting solution stirred for 8 hrs at r. t. when TLC showed complete consumption of starting material. Solvent was evaporated and the crude was dried in vacuum. 3 ml water was added to it and the slurry was stirred for 1 hr. To the slurry was added 45 ml CH2C12 followed by 3 eq of TFA at 0°C. The resulting solution was stirred at r. t. for 24 hrs. The solvent was evaporated and dried in vacuum. The pseudo molecular ion, [M-H]-at 211.9885 confirmed the structure of . the product L-aspartyl, N-sulfonic acid (calculated for G4H6NO7S ; 211.9870).

Reference example 4 L-Homoglutamyl, N-sulfonic acid from L-Homoglutamic acid di tertiary butyl ester L-Homoglutamic acid di tertiary butyl ester (1 eq. ) was added portion-wise to a solution of

SO2CI2 (2 eq. ) in dry CH2CI2 at 0°C followed by Et3N (3 eq. ). Resulting solution stirred for 8 hrs at r. t. when TLC showed complete consumption of starting material. Solvent was evaporated and the crude was dried in vacuum. 3 ml water was added to it and the slurry was stirred for 1 hr. To the slurry was added 45 ml CH2CI2 followed by 3 eq of TFA at 0"C. The resulting solution was stirred at r. t. for 24 hrs. The solvent was evaporated and dried in vacuum. The pseudo molecular ion, [M-H]-at 240.0169 confirmed the structure of the product L-Homoglutamyl, N-sulfonic acid (calculated for C6H10N07S ; 240.0182).

Reference example 5 The calcium salt of L-glutamyl-N-sulphonic acid was prepared by adding 1 M equivalent of CaCl2 solution and incubated at temperature ranging from 30+5° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for dendritic celll differentiation (Table A).

Table A. Stimulation of BM precursors with the synthetic compound differentiates cells with DC specific markers.

Fold increase in Relative MFI over unstimulated control Surface markers Viability Group CD80 CD54 H-2Dd CDl lc % of Viable cells GM-CSF 3.3 4.0 2.0 5.0 180 Compound 2.5 4.0 3.0 2.0 150 Table-A gives the fold increase in the levels of some of the molecules of cells stimulated with either 15 ng/ml of GM-CSF or 50 micro gram per ml of the synthetic compound at 48h of incubation over unstimulated controls. The viability of the cultures was more then 99% at the end of the incubation period at this concentration of the synthetic compound.

The data suggests that'the compound'induces the differentiation of DCs from BM precursors.

Reference example 6 The L-glutamyl-N-sulphonic acid prepared as described in Examples 1 & 2 was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for dendritic cell differentiation (Table B).

Reference example 7 The calcium salt of L-glutamic acid was prepared by adding 1 M equivalent of CaCI2 solution and incubated at temperature ranging from 30+5° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for dendritic cell differentiation (Table B).

Reference example 8 The L-glutamic acid was reconstituted in sterilized distilled water and assessed in'a ose- dependent manner for dendritic cell differentiation (Table B).

Table B: Stimulation of BM precursors with the synthetic compound differentiates cells with DC specific markers Fold increase in Relative MFI over unstimulated control Surface markers Viability Group CD80 CD54 H-2Dd CDl lc % of Viable cells GM-CSF 3. 3. 4.0 2.0 5.0 180 Example 6 1.5 2.0 1.2 1.0 115 Example 7 1.0 1.0 N. D. 1.0 90 Example 8 1.0 0. 9. N. D. 1.1 95 , Reference example 9 Isolation of bone marrow For each set of experiment a group of 4 BALB/c mice were sacrificed by transferring the animals in a chloroform chamber. The hind limbs of the mouse were removed carefully and placed in a Petri dish with HBSS (Hanks Balanced Saline Solution) wash buffer. The tibias and femurs were cleared of all surrounding and attached tissues. This was followed by chipping the ends of bones. The bone marrow was flushed out by injecting HBSS solution into the bone with the help of a hypodermal syringe (No. 26 gauge). The bone marrow was finally made into a fine suspension by syringing in and out of the fluid several times using an 18 gauge syringe needle.

Reference example 10 The calcium salt of L-glutamyl-N-sulphonic acid was prepared by adding 1 M equivalent of CaCi2 solution and incubated at temperature ranging from 30+5° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependerit manner for inhibition of osteoclast differentiation (Table A).

Table A: Effect of compound 1 (L-glutamyl-N-sulphonic acid, Ca salt) on osteoclast formation

Culture Number of TRAP-positive multinuclear % inhibition conditions cells/well of 96 well plate (Mean SEM) M-CSF 0 M-CSF + 138. 00 ~ 9.37 -. RANKL M-CSF + 109. 67 9. 79 21. 01 RANKL + compound 1 (0.5 llg/ml) M-CSF + 52. 17 ~ 6. 42 62.19 RANKL+ compound 1 (1. 5, ug/ml) M-CSF + 14. 67 1. 98 89.36 RANKL + compound 1 (3. 0 ml) M-CSF + 2. 83 i 1.05 97.94 RANKL + compound 1 (5.0 µg/ml) Culture of murine bone marrow cells in the presence of M-CSF and RANKL induces the formation of o steoclasts, which w ere d etected as TRAP-positive c ells. A dose dependent inhibition in t he number of osteoclast cells generated as observed with increasing dose of compound 1. Values given are the mean + SD of five separate experiments Reference example 11 The calcium salt of L-glutamic acid was prepared by adding 1 M equivalent of Cad2 solution and incubated at temperature ranging from 305° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for inhibition of osteoclast differentiation (Table B).

Table B: Effect of L-glutamic acid, calcium salt on osteoclast formation Culture Number of TRAP-positive % inhibition conditions multinuclear cells/well of 96 well plate (Mean SEM) M-CSF 0 M-CSF + 158. 33 ~ 12. 00 RANKL M-CSF + 167.17 ~ 7. 95 0 RANKL+ compound 2 (0. 5 lg/ml) M-CSF + 152.83 10.47 3.47 RANKL+ compound 2 (1. 5 µg/ml) M-CSF + 130. 50il3. 57 17.37 RANKL + compound 2 (3.0 g/ml) M-CSF + 119. 50il0. 00 24.52 RANKL + compound 2 (5. 0 µg/ml)

For detail see legend to example 5 Reference example 12 The L-glutamyl-N-sulphonic acid prepared as described in Examples 1 & 2 was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for inhibition of osteoclast differentiation (Table D).

Table-D: Effect of L-glutamyl-N-sulphonic acid on osteoclast formation Culture Number of TRAP-positive % inhibition conditions multinuclear cells/well of 96 well plate (Mean ~ SEM) M-CSF 0 M-CSF + 146. 83ill. 89 RANKL M-CSF + 154. 67 ~ 8. 43 0 RANKL + compound 3 (0.5 lg/ml) M-CSF + 150.33 ~ 8. 82 0 RANKL + compound 3 (1. 5 lg/ml) M-CSF+ 112. 67 ~ 8.63 23.23 RANKL + compound 3 (3.0 lg/ml) M-CSF + 110. 00 6. 72 25.08 RANKL + compound 3 (5.0 pLg/ml)

For detail see legend to example 5 Reference example 13 The L-glutamic acid was reconstituted in sterilized distilled water and assessed in a dose dependent manner for inhibition of osteoclast differentiation (Table E).

Table E: Effect of L-glutamic acid on osteoclast formation

Culture Number of TRAP-positive % inhibition conditions multinuclear cells/well of 96 well plate (Mean SEM) M-CSF 0- M-CSF + 156. 00il2. 26 0 RANKL M-CSF + 173. 33 6. 50 0 RANKL+ compound 4 (0. 5 µg/ml) M-CSF + 155.00~8. 23 0.64 RANKL + compound 4 (1.5 g/ml) M-CSF + 145. 83il4. 71 7.05 RANKL + compound 4 (3. 0 g/ml) M-CSF + 112. 67~ 10. 74 27.77 RANKL+ compound 4 (5. 0 ug/m !) For detail see legend to example 5 Reference example 14 The L-Aspartic acid, N-sulphonic acid as prepared in example 3 was mixed with 1 M equivalent of CaCi, solution and incubated at temperature ranging from 30+5° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for inhibition of osteoclast differentiation (Table F).

Table F: Effect of L-Aspartic acid, N-sulphonic acid calcium salt on osteoclast formation Culture Number of TRAP-positive % inhibition conditions multinuclear cells/well of 96 well plate Mean ~ SEM M-CSF 0- M-CSF + 158. 33ill. 26 0 RANKL M-CSF + 127.30 ~ 5.50 19. 70 RANKL+ compound 4 (0.5 ml) M-CSF + 86. 23 7. 23 45.16 RANKL+ compound 4 (1. 5 pg/ml) M-CSF + 44. 50~4. 80 71.90 RANKL + compound 4 (3. 0/ml) M-CSF + 26. 67 0. 73 83. 26 RANKL + compound 4 (5.0 g/ml)

For detail see legend to example 5 Reference example 15 L-homoglutamic a cid, N-sulphonic acid as prepared in example 4 w as mixed with 1 M equivalent of CaCl2 solution and incubated at temperature ranging from 30+5° C. The resulting complex was freeze-dried. The freeze-dried compound was reconstituted in sterilized distilled water and assessed in a dose-dependent manner for inhibition of osteoclast differentiation (Table G).

Table G: Effect of L-homoglutamic acid, N-sulphonic acid, calcium salt on osteoclast formation Culture Number of TRAP-positive % inhibition conditions multinuclear cells/well of 96 well plate (Mean ~ SEM M-CSF 0 M-CSF + 146.. 83 ~ 12.00 - RANKL M-CSF + 138. 57 7. 95 5.55 RANKL + compound 2 (0.5 lg/ml) M-CSF + 106. 23 ~ 10.47 27. 60 RANKL + compound 2 (1. 5g/ml) M-CSF + 78.57 13. 57 46. 40 RANKL + compound 2 (3.0 Klg/ml) M-CSF + 46. 22~10. 00 68.50 RANKL + compound 2 (5. 0 g/ml)

For detail see legend to example 5 Reference example 16 Ae Ilt vitro osteoclastogenesis assay For ira vitro osteoclastogenesis bone marrow cells were isolated from 5-to S-wk-old Balb/c mice.

Mice were sacrificed by cervical dislocation and femora and tibiae were aseptically removed and dissected free of adherent soft tissues. The bone ends were cut, and the marrow cavity was flushed out with medium MEM from one end of the bone using a sterile 21-gauge needle. The bone marrow suspension was carefully agitated with a plastic Pasteur pipette to obtain a single-cell suspension. The cells were washed twice and resuspended (106 c ells/ml) i n a MEM containing 10% FBS. Stromal cell-free, M-CSF-dependent, osteoclast precursor cells were prepared from these cells as previously described (Wani et al. 1999). Briefly, bone marrow cells were incubated for 24 h in aMEM containing 10% FBS in the presence of M-CSF (10 ng/ml) at a density of 3 x 105 c ells/ml i n a 7 5 c f lask. A fter 2 4 h, n onadherent c ells w ere h arvested and I ayered o n a Ficoll-Hypaque gradient. Cells at the gradient interface were collected, washed and resuspended (5 x 10'/ml) in aMEM containing 10% FBS. In this study, we called these stromal cell-free, M-CSF- dependent, nonadherent cells as osteoclast precursors. These osteoclast precursors were added to 96-well plates (100 ul/well) containing plastic coverslips. Each well received further 100 ul of medium containing M-CSF (30 ng/ml), RANKL (30 ng/ml) without or with various concentrations of purified compound. Cultures were fed every 2-3 days and after incubation for 6 days osteoclast formation w as e valuated b y t artrate-resistant a cid p hosphatase (TRAP) s taining. T he n umber o f TRAP-positive multinucleated cells (MNCs) containing 3 or more nuclei was scored.

Characterization of osteoclasts by TRAP staining Osteoclast formation was evaluated by quantification of TRAP-positive MNCs as described previously (Khapli et al. 2003). TRAP is preferentially expressed at high levels in osteoclast and is considered, especially in the mouse, to be an osteoclast marker. Cytochemical staining for TRAP is widely used for identifying the osteoclasts i rt v ivo and in vitro. It is claimed to be specific for osteoclasts in bone. After incubation, cells on cover slips were washed in PBS, fixed in 10% formalin for 10 min and stained for acid phosphatase in the presence of 0.05 M sodium tartrate.

The substrate used was napthol AS-BI phosphate. Only those cells that were strongly TRAP- positive (dark red) counted by light microscopy.

In Vitro Bone resorption assay Osteoclast has the ability to excavate authentic resorption lacunae in vivo and in vitro. Bone resorption is the unique function of the osteoclast and is therefore the most useful means of distinguishing it from other cell types. M-CSF-dependent, non-adherent bone marrow cells were incubated for 10 days on bovine cortical bone slices in the presence of M-CSF, RANKL with or without various concentrations of compounds. Bone slices were examined for resorption pits by reflected light microscopy as previously described (Wani et al. 1999).