Method of inducing differentiation of dendritic cells
Abstract
The present invention is related to compounds having general formula Z-OC (CR n1 R n2 )—CO-Z wherein Z=OH or NH 2 and n1=n2=1 to 8, 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—CR 3 R 4 —CR 2 (NHR 1 )—COOH, ZOC—CR 5 R 6 —CR 3 R 4 —CR 1 (NHR 2 )—COOH, ZOC—CR 7 R 8 —CR 5 R 6 —CR 3 R 4 —CR 1 N 2 )—COOH wherein Z=OH or NH 2 ; R 1 to R 8 denotes H, SO 3 H, or OSO 3 H. In addition, the dicarboxylic acids and their amides ZOC—(CH 2 ) n —CR 1 R 2 —COOH, where Z=OH or NH 2 ; and n=1, 2, 3. The groups R 1 /R 2 =H/SO 3 H or OSO 3 H or CH 2 —SO 3 H or CH 2 —OSO 3 H 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.
Claims
exact text as granted — not AI-modified1 . 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 Z-OC (C R n1 R n2 )—CO-Z wherein Z=OH or NH 2 and n1=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 T-cells thereby initiate primary protective Th1 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 ZOC—CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 , to R 4 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
4 . A method as claimed in claim 1 , wherein said compound having a structure as herein and bearing general formula ZOC—CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 to R 6 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
5 . A method as claimed in claim 1 , wherein said compound having structure as herein and bearing general formula ZOC—CR 7 R 8 —CR 5 R—CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 to R 8 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
6 . A method as claimed in claim 1 , wherein said compound in non-toxic to monocytes.
7 . A method as claimed in claim 1 , wherein said compound in non-toxic 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:
I. [L-Aspartic acid, N-Sulfonic acid], II. [2α,3-dicarboxy, propane-1-sulfonic acid], III. [2α,3-dicarboxy, propane-1-sulfate], IV. [1α,2-carboxy ethane sulfonic acid], V. [1α,2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2β,3-carboxy,propane-1-sulfonic acid], VIII. [2β,3-carboxy,propane-1-sulfate], IX. [1β,2-carboxy ethane-1-sulfonic acid], X. [1β,2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3α-sulfonic acid], XII. [D-aspartic acid, 3α-sulfate], XIII. [D-aspartic acid, 30-sulfonic acid], XIV. [D-aspartic acid, 3β-sulfate], XV. [L-asparagine,N-sulfonic acid], XVI. [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [1α-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3α-sulfonic acid], XXI. [L-asparagine, 3α-sulfate], XXII. [L-asparagine, 3β-sulfonic acid], XXIII. [L-asparagine, 30-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1β-carboxy, 2-carboxamido, ethane sulfonic acid], XVIII. [1β-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3α-sulfonic acid], XXX. [D-asparagine, 3α-sulfate], XXXI. [D-asparagine, 30-sulfonic acid], XXXII. [D-asparagine, 3β-sulfate], XXIII. [L-glutamic acid, N-sulfonic acid], XXIV. [2α,4-dicarboxy, butane-1-sulfonic acid], XXXV. [2α,4-dicarboxy, butane-1-sulfate], XXVI. [1α,3-dicarboxy, propane sulfonic acid], XXVII. [1α,3-dicarboxy, propane sulfate], XVIII. [1β,3-dicarboxy, propane sulfate], XXIX. [1β,3-dicarboxy, propane sulfonic acid],
11 . A method as claimed in claim 4 , wherein the compound is selected from the group consisting of:
I. [D-glutamic acid, N-sulfonic acid], II. 2β,4-dicarboxy, butane-1-sulfonic acid], III. [2β,4-dicarboxy, butane-1-sulfate], IV. [D-glutamic acid, 3α-sulfonic acid], V. [D-glutamic acid, 3α-sulfate], VI. [D-glutamic acid, 3β-sulfonic acid], VII. [D-glutamic acid, 3β-sulfate], VIII. [D-glutamic acid, 4α-sulfonic acid], IX. [D-glutamic acid, 4α-sulfate], X. [D-glutamic acid, 4β-sulfonic acid], XI. [D-glutamic acid, 3β-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV. [2α-carboxy, 4-carboxamido, butane-1-sulfate], XV. [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [1α-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1β-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [D-glutamine, 3α-sulfonic acid], XXIII. [D-glutamine, 3α-sulfate], XXIV. [D-glutamine, 3β-sulfonic acid], XXV. [D-glutamine, 3β-sulfate], XXVI. [D-glutamine, 4α-sulfonic acid], XXVII. [D-glutamine, 4α-sulfate], XXVIII. [D-glutamine, 4β-sulfonic acid], XXIX. [D-glutamine, 4β-sulfate], XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2α,5-dicarboxy-1-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-213, 5-dicarboxy-1-sulfonic acid], XXXVII. [Pentane-2β,5-dicarboxy-1-sulfate], XXXVIII. [Butane-1β,4-dicarboxy-1-sulfonic acid], XXXIX. [Butane-1β,4-dicarboxy-1-sulfate],
12 . A method as claimed in claim 5 , wherein the compound is selected from the group consisting of
I. [D-homoglutamic acid, 3α-sulfonic acid], II. [D-homoglutamic acid, 3α-sulfate], III. [D-homoglutamic acid, 30-sulfonic acid], IV. [D-homoglutamic acid, 3β-sulfate], V. [D-homoglutamic acid, 4α-sulfonic acid], VI. [D-homoglutamic acid, 4α-sulfate], VII. [D-homoglutamic acid, 4β-sulfonic acid], VIII. [D-homoglutamic acid, 413-sulfate], IX. [D-homoglutamic acid, 5α-sulfate], X. [D-homoglutamic acid, 5α-sulfate], XI. [D-homoglutamic acid, 51-sulfonic acid], XII. [D-homoglutamic acid, 5β-sulfate], XIII. [L-homoglutamine, N-sulfonic acid], XIV. [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XV. [Pentane-2α-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-2β-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Butane-1β-carboxy, 4-carboxamido-1-sulfonic acid], XXI. [Butane-1β-carboxy, 4-carboxamido-1-sulfate], XXII. [D-homoglutamine, 3α-sulfonic acid], XXIII. [D-homoglutamine, 3α-sulfate], XXIV. [D-homoglutamine, 3β-sulfonic acid], XXV. [D-homoglutamine, 3β-sulfate], XXVI. [D-homoglutamine, 4α-sulfonic acid], XXVII. [D-homoglutamine, 4α-sulfate], XVIII. [D-homoglutamine, 413-sulfonic acid], XXIX. [D-homoglutamine, 4β-sulfate], XXX. [D-homoglutamine, 5α-sulfonic acid], XXXI. [D-homoglutamine, 5α-sulfate], XXXII. [D-homoglutamine, 50-sulfonic acid] and XXIII. [D-homoglutamine, 5β-sulfate].
13 . A method as claimed in claim 3 , wherein novel sulfonic acid/sulfate derivatives of the formulae ZOC—CR 3 R 4 —CR 1 R 2 -COOH wherein: Z=OH or NH 2 , R 1 , to R 4 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
I. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =NHSO 3 H is the same meaning as is before defined; II. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; III. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; IV. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =SO 3 H is the same meaning as is before defined; V. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =OSO 3 H is the same meaning as is before defined; VI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =NHSO 3 H is the same meaning as is before defined; VII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; VIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; IX. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =SO 3 H is the same meaning as is before defined; X. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =OSO 3 H is the same meaning as is before defined; XI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XIV. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =NHSO 3 H is the same meaning as is before defined; XVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XVII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =SO 3 H is the same meaning as is before defined; XIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =OSO 3 H is the same meaning as is before defined; XX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XXI. A compound as claimed in claim 1 , wherein Z=NH 2 , R=R 4 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XXII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =NHSO 3 H is the same meaning as is before defined; XXV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =SO 3 H is the same meaning as is before defined; XXVIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =OSO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XXX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XXXI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XXXII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined.
14 . A method as claimed in claim 4 , wherein novel sulfonic acid/sulfate derivatives of the formulae ZOC—CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH, wherein: Z=OH or NH 2 , R 1 , to R 6 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
I. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =NHSO 3 H is the same meaning as is before defined; II. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; III. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; IV. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =SO 3 H is the same meaning as is before defined; V. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =&=H, R 1 =OSO 3 H is the same meaning as is before defined; VI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =OSO 3 H is the same meaning as is before defined; VII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =SO 3 H is the same meaning as is before defined; VIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =NHSO 3 H is the same meaning as is before defined; IX. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; X. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; XI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XIV. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XV. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; XVI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; XVII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; XIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =&=H, R 1 =NHSO 3 H is the same meaning as is before defined; XX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XXI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =F4=R 5 =R 6 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XXII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =SO 3 H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =OSO 3 H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =OSO 3 H is the same meaning as is before defined; XXV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =SO 3 H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R=R 3 =R 4 =R 5 =R 6 =H, R 2 =NHSO 3 H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XXX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XXXI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XXXII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XXXIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; XXXIV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; XXXV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; XXXVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined.
15 . A method as claimed in claim 5 , wherein novel sulfonic acid/sulfate derivatives of the formulae ZOC—CR 7 R 8 —CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH, wherein: Z=OH or NH 2 , R 1 , to R 8 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
I. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =NHSO 3 H is the same meaning as is before defined; II. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =—CH 2 SO 3 H is the same meaning as is before defined; III. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; IV. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =SO 3 H is the same meaning as is before defined; V. A compound as claimed in claim 1 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =OSO 3 H is the same meaning as is before defined; VI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NHSO 3 H is the same meaning as is before defined; VII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; VIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; IX. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =SO 3 H is the same meaning as is before defined; X. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =OSO 3 H is the same meaning as is before defined; XI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 5 =R(=R 7 =R 8 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XIV. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XV. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; XVI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; XVII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; XIX. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =SO 3 H is the same meaning as is before defined; XX. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =OSO 3 H is the same meaning as is before defined; XXI. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =SO 3 H is the same meaning as is before defined; XXII. A compound as claimed in claim 1 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =OSO 3 H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R=R 5 =R 6 =R 7 =R 8 =H, R 1 =NHSO 3 H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XXV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =SO 3 H is the same meaning as is before defined; XXVII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =OSO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NHSO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R=R 4 R 5 =R 7 =R 8 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; XXX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =SO 3 H is the same meaning as is before defined; XXXI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =OSO 3 H is the same meaning as is before defined; XXXII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R=R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XXIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R=R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XXIV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XXXV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XXVI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; XVII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R=R 8 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; XL. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =SO 3 H is the same meaning as is before defined; XLI. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =OSO 3 H is the same meaning as is before defined; XLII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =SO 3 H is the same meaning as is before defined; XLIII. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =OSO 3 H is the same meaning as is before defined;
16 . A method as claimed in claim 10 , wherein said compound is non-toxic salts selected from the group consisting of:
I. [L-Aspartic acid, N-Sulfonic acid], II. [2α,3-dicarboxy, propane-1-sulfonic acid], III. [2α,3-dicarboxy, propane-1-sulfate], IV. [1α,2-carboxy ethane sulfonic acid], V. [1α,2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2β,3-carboxy,propane-1-sulfonic acid], VIII. [2β,3-carboxy,apropane-1-sulfate], IX. [1β,2-carboxy ethane-1-sulfonic acid], X. [1β,2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3α-sulfonic acid], XII. [D-aspartic acid, 3α-sulfate], XIII. [D-aspartic acid, 3β-sulfonic acid], XIV. [D-aspartic acid, 3β-sulfate], XV. [L-asparagine,N-sulfonic acid], XVI. [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [1α-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3α-sulfonic acid], XXI. [L-asparagine, 3α-sulfate], XXII. [L-asparagine, 3β-sulfonic acid], XXIII. [L-asparagine, 3β-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [lP-carboxy, 2-carboxamido, ethane sulfonic acid], XVIII. [1β-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3α-sulfonic acid], XXX. [D-asparagine, 3α-sulfate], XXXI. [D-asparagine, 3β-sulfonic acid], XXXII. [D-asparagine, 3β-sulfate], XXIII. [L-glutamic acid, N-sulfonic acid], XXIV. [2α,4-dicarboxy, butane-1-sulfonic acid], XXV. [2α,4-dicarboxy, butane-1-sulfate], XXVI. [1α,3-dicarboxy, propane sulfonic acid], XVII. [1α,3-dicarboxy, propane sulfate], VIII. [1β,3-dicarboxy, propane sulfate], XXIX. [1 β,3-dicarboxy, propane sulfonic acid],
17 . A method as claimed in claim 11 , wherein said compound is non-toxic salts selected from the group consisting of:
I. [D-glutamic acid, N-sulfonic acid], II. [2β,4-dicarboxy, butane-1-sulfonic acid], III. [2β,4-dicarboxy, butane-1-sulfate], IV. [D-glutamic acid, 3α-sulfonic acid], V. [D-glutamic acid, 3α-sulfate], VI. [D-glutamic acid, 3β-sulfonic acid], VII. [D-glutamic acid, 3β-sulfate], VIII. [D-glutamic acid, 4α-sulfonic acid], IX. [D-glutamic acid, 4α-sulfate], X. [D-glutamic acid, 4β-sulfonic acid], XI. [D-glutamic acid, 3β-sulfate], XII. [L-glutamine, N-sulfonic acid], XIII. [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV. [2α-carboxy, 4-carboxamido, butane-1-sulfate], XV. [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI. [1α-carboxy, 3-carboxamido, propane-1-sulfate], XVII. [1β-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX. [D-glutamine, N-sulfonic acid], XX. [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [D-glutamine, 3α-sulfonic acid], XXIII. [D-glutamine, 3α-sulfate], XXIV. [D-glutamine, 3β-sulfonic acid], XXV. [D-glutamine, 3β-sulfate], XXVI. [D-glutamine, 4α-sulfonic acid], XXVII. [D-glutamine, 4α-sulfate], XXVIII. [D-glutamine, 4β-sulfonic acid], XXIX. [D-glutamine, 413-sulfate], XXX. [L-homoglutamic acid, N-sulfonic acid], XXXI. [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXII. [Pentane-2α,5-dicarboxy-1-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-2β,5-dicarboxy-1-sulfonic acid], XXXVII. [Pentane-2β,5-dicarboxy-1-sulfate], XXXVIII. [Butane-1β,4-dicarboxy-1-sulfonic acid], XXXIX. [Butane-1β,4-dicarboxy-1-sulfate],
18 . A method as claimed in claim 12 , wherein said compound is non-toxic salts selected from the group consisting of:
I. [D-homoglutamic acid, 3α-sulfonic acid], II. [D-homoglutamic acid, 3α-sulfate], III. [D-homoglutamic acid, 3β-sulfonic acid], IV. [D-homoglutamic acid, 3β-sulfate], V. [D-homoglutamic acid, 4α-sulfonic acid], VI. [D-homoglutamic acid, 4α-sulfate], VII. [D-homoglutamic acid, 40-sulfonic acid], VIII. [D-homoglutamic acid, 4β-sulfate], IX. [D-homoglutamic acid, 5α-sulfate], X. [D-homoglutamic acid, 5α-sulfate], XI. [D-homoglutamic acid, 5β-sulfonic acid], XII. [D-homoglutamic acid, 50-sulfate], XIII. [L-homoglutamine, N-sulfonic acid], XIV. [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XV. [Pentane-2α-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-2β-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Butane-I p -carboxy, 4-carboxamido-1-sulfonic acid], XXI. [Butane-1β-carboxy, 4-carboxamido-1-sulfate], XXII. [D-homoglutamine, 3α-sulfonic acid], XXIII. [D-homoglutamine, 3α-sulfate], XXIV. [D-homoglutamine, 3β-sulfonic acid], XXV. [D-homoglutamine, 31-sulfate], XXVI. [D-homoglutamine, 4α-sulfonic acid], XXVII. [D-homoglutamine, 4α-sulfate], XVIII. [D-homoglutamine, 4β-sulfonic acid], XXIX. [D-homoglutamine, 413-sulfate], XXX. [D-homoglutamine, 5α-sulfonic acid], XXXI. [D-homoglutamine, 5α-sulfate], XXXII. [D-homoglutamine, 51-sulfonic acid] and XXIII. [D-homoglutamine, 5β-sulfate].
19 . A method as claimed in claim 16 , 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. [2α,3-dicarboxy, propane-1-sulfonic acid], III. [2α,3-dicarboxy, propane-1-sulfate], IV. [1α,2-carboxy ethane sulfonic acid], V. [1α,2-carboxy ethane sulfate], VI. [D-aspartic acid, N-sulfonic acid], VII. [2β,3-carboxy,propane-1-sulfonic acid], VIII. [2β,3-carboxy,propane-1-sulfate], LX. [1β,2-carboxy ethane-1-sulfonic acid], X. [1β,2-carboxy ethane-1-sulfate], XI. [D-aspartic acid, 3α-sulfonic acid], XII. [D-aspartic acid, 3α-sulfate], XIII. [D-aspartic acid, 3β-sulfonic acid], XIV. [D-aspartic acid, 3β-sulfate], XV. [L-asparagine,N-sulfonic acid], XVI. [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII. [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII. [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX. [1α-carboxy, 2-carboxamido, ethane sulfate], XX. [L-asparagine, 3α-sulfonic acid], XXI. [L-asparagine, 3α-sulfate], XXII. [L-asparagine, 3β-sulfonic acid], XXIII. [L-asparagine, 3β-sulfate, XXIV. [D-asparagine, N-sulfonic acid], XXV. [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII. [1β-carboxy, 2-carboxamido, ethane sulfonic acid], XVIII. [1β-carboxy, 2-carboxamido, ethane sulfate], XXIX. [D-asparagine, 3α-sulfonic acid], XXX. [D-asparagine, 3α-sulfate], XXXI. [D-asparagine, 3β-sulfonic acid], XXXII. [D-asparagine, 3β-sulfate],
20 . A method as claimed in claim 17 , 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. [2α,4-dicarboxy, butane-1-sulfonic acid], III. [2α,4-dicarboxy, butane-1-sulfate], IV. [1α,3-dicarboxy, propane sulfonic acid], V. [1α,3-dicarboxy, propane sulfate], VI. [1β,3-dicarboxy, propane sulfate], VII. [1β,3-dicarboxy, propane sulfonic acid], VIII. [D-glutamic acid, N-sulfonic acid], IX. [2β,4-dicarboxy, butane-1-sulfonic acid], X. [2β,4-dicarboxy, butane-1-sulfate], XI. [D-glutamic acid, 3α-sulfonic acid], XII. [D-glutamic acid, 3α-sulfate], XIII. [D-glutamic acid, 3β-sulfonic acid], XIV. [D-glutamic acid, 3β-sulfate], XV. [D-glutamic acid, 4α-sulfonic acid], XVI. [D-glutamic acid, 4α-sulfate], XVII. [D-glutamic acid, 41-sulfonic acid], XVIII. [D-glutamic acid, 3β-sulfate], XIX. [L-glutamine, N-sulfonic acid], XX. [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI. [2α-carboxy, 4-carboxamido, butane-1-sulfate], XXII. [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXIII. [1α-carboxy, 3-carboxamido, propane-1-sulfate], XXIV. [1βP-carboxy, 3-carboxamido, propane-1-sulfate], XXV. [1β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI. [D-glutamine, N-sulfonic acid], XXVII. [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XVIII. [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXIX. [D-glutamine, 3α-sulfonic acid], XXX. [D-glutamine, 3α-sulfate], XXXI. [D-glutamine, 31-sulfonic acid], XXXII. [D-glutamine, 3β-sulfate], XXXIII. [D-glutamine, 4α-sulfonic acid], XXXIV. [D-glutamine, 4α-sulfate], XXXV. [D-glutamine, 4β-sulfonic acid], XXXVI. [D-glutamine, 4β-sulfate], XXXVII. [L-homoglutamic acid, N-sulfonic acid], XXXVIII. [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXIX. [Pentane-2α,5-dicarboxy-1-sulfate], XL. [Butane-1α,4-dicarboxy-1-sulfonic acid], XLI. [Butane-1α,4-dicarboxy-1-sulfate],
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. [D-homoglutamic acid, N-sulfonic acid], II. [Pentane-2β,5-dicarboxy-1-sulfonic acid], III. [Pentane-2β,5-dicarboxy-1-sulfate], IV. [Butane-1β,4-dicarboxy-1-sulfonic acid], V. [Butane-1β,4-dicarboxy-1-sulfate], VI. [D-homoglutamic acid, 3α-sulfonic acid], VII. [D-homoglutamic acid, 3α-sulfate], VIII. [D-homoglutamic acid, 3β-sulfonic acid], IX. [D-homoglutamic acid, 3β-sulfate], X. [D-homoglutamic acid, 4α-sulfonic acid], XI. [D-homoglutamic acid, 4α-sulfate], XII. [D-homoglutamic acid, 4β-sulfonic acid], XIII. [D-homoglutamic acid, 4β-sulfate], XIV. [D-homoglutamic acid, 5α-sulfate], XV. [D-homoglutamic acid, 5α-sulfate], XVI. [D-homoglutamic acid, 513-sulfonic acid], XVII. [D-homoglutamic acid, 5β-sulfate], XVIII. [L-homoglutamine, N-sulfonic acid], XIX. [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XX. [Pentane-2α-carboxy, 5-carboxamido-1-sulfate], XXI. [Butane-i 1α-carboxy, 4-carboxamido-1-sulfonic acid], XXII. [Butane-1α-carboxy, 4-carboxamido-1-sulfate], XXIII. [D-homoglutamine, N-sulfonic acid], XXIV. [Pentane-2β-carboxy, 5-carboxamido-1-sulfonic acid], XXV. [Butane-i p -carboxy, 4-carboxamido-1-sulfonic acid], XXVI. [Butane-1β-carboxy, 4-carboxamido-1-sulfate], XXVII. [D-homoglutamine, 3α-sulfonic acid], XVIII. [D-homoglutamine, 3α-sulfate], XXIX. [D-homoglutamine, 3β-sulfonic acid], XXX. [D-homoglutamine, 3β-sulfate], XXXI. [D-homoglutamine, 4α-sulfonic acid], XXXII. [D-homoglutamine, 4α-sulfate], XXIII. [D-homoglutamine, 4β-sulfonic acid], XXIV. [D-homoglutamine, 4β-sulfate], XXXV. [D-homoglutamine, 5α-sulfonic acid], XXVI. [D-homoglutamine, 5α-sulfate], XXVII. [D-homoglutamine, 513-sulfonic acid] and XVIII. [D-homoglutamine, 5β-sulfate].
22 . Use of a composition comprising general formula Z-OC (C R n1 R n2 )—CO-Z wherein Z=OH or NH 2 and n1=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 T-cells thereby initiate primary protective Th1 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 ZOC—CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 , to R 4 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
25 . Use of the composition as claimed in claim 22 , wherein said compound having a structure as herein and bearing general formula ZOC—CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 to R 6 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
26 . Use of the composition as claimed in claim 22 , wherein said compound having structure as herein and bearing general formula ZOC—CR 7 R 8 —CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 to R 8 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
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 [L-Aspartic acid, N-Sulfonic acid], II [2α,3-dicarboxy, propane-1-sulfonic acid], III [2α,3-dicarboxy, propane-1-sulfate], IV [1α,2-carboxy ethane sulfonic acid], V [1α,2-carboxy ethane sulfate], VI [D-aspartic acid, N-sulfonic acid], VII [2β,3-carboxy,propane-1-sulfonic acid], VIII [2β,3-carboxy,propane-1-sulfate], IX [1β,2-carboxy ethane-1-sulfonic acid], X [1β,2-carboxy ethane-1-sulfate], XI [D-aspartic acid, 3α-sulfonic acid], XII [D-aspartic acid, 3α-sulfate], XIII [D-aspartic acid, 3β-sulfonic acid], XIV [D-aspartic acid, 3β-sulfate], XV [L-asparagine,N-sulfonic acid], XVI [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX [1α-carboxy, 2-carboxamido, ethane sulfate], XX [L-asparagine, 3α-sulfonic acid], XXI [L-asparagine, 3α-sulfate], XXII [L-asparagine, 3β-sulfonic acid], XXIII [L-asparagine, 3β-sulfate, XXIV [D-asparagine, N-sulfonic acid], XXV [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII [1β-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII [1β-carboxy, 2-carboxamido, ethane sulfate], XXIX [D-asparagine, 3α-sulfonic acid], XXX [D-asparagine, 3α-sulfate], XXXI [D-asparagine, 3β-sulfonic acid], XXXII [D-asparagine, 3β-sulfate], XXXIII [L-glutamic acid, N-sulfonic acid], XXXIV [2α,4-dicarboxy, butane-1-sulfonic acid], XXXV [2α,4-dicarboxy, butane-1-sulfate], XXXVI [1α,3-dicarboxy, propane sulfonic acid], XXXVII [1α,3-dicarboxy, propane sulfate], XXXVIII [1β,3-dicarboxy, propane sulfate], XXXIX [1β,3-dicarboxy, propane sulfonic acid],
32 . Use of the composition as claimed in claim 22 , wherein the compound is selected from the group consisting of:
I [D-glutamic acid, N-sulfonic acid], II 213, 4-dicarboxy, butane-1-sulfonic acid], III [2β,4-dicarboxy, butane-1-sulfate], IV [D-glutamic acid, 3α-sulfonic acid], V [D-glutamic acid, 3α-sulfate], VI [D-glutamic acid, 3β-sulfonic acid], VII [D-glutamic acid, 3β-sulfate], VIII [D-glutamic acid, 4α-sulfonic acid], IX [D-glutamic acid, 4α-sulfate], X [D-glutamic acid, 4β-sulfonic acid], XI [D-glutamic acid, 3β-sulfate], XII [L-glutamine, N-sulfonic acid], XIII [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV [2α-carboxy, 4-carboxamido, butane-1-sulfate], XV [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI [1α-carboxy, 3-carboxamido, propane-1-sulfate], XVII [1β-carboxy, 3-carboxamido, propane-1-sulfate], XVIII [1β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX [D-glutamine, N-sulfonic acid], XX [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXII [D-glutamine, 3α-sulfonic acid], XXIII [D-glutamine, 3α-sulfate], XXIV [D-glutamine, 30-sulfonic acid], XXV [D-glutamine, 30-sulfate], XXVI [D-glutamine, 4α-sulfonic acid], XXVII [D-glutamine, 4α-sulfate], XXVIII [D-glutamine, 40-sulfonic acid], XXIX [D-glutamine, 4β-sulfate], XXX [L-homoglutamic acid, N-sulfonic acid], XXXI [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXII [Pentane-2α,5-dicarboxy-1-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-2β,5-dicarboxy-1-sulfonic acid], XXXVII [Pentane-2β,5-dicarboxy-1-sulfate], 3(WXVIII [Butane-1β,4-dicarboxy-1-sulfonic acid], XXIX [Butane-1β,4-dicarboxy-1-sulfate],
33 . Use of the composition as claimed in claim 22 , wherein the compound is selected from the group consisting of XXIV. [D-homoglutamic acid, 3α-sulfonic acid],
XXXV. [D-homoglutamic acid, 3α-sulfate], XXVI. [D-homoglutamic acid, 30-sulfonic acid], XVII. [D-homoglutamic acid, 3β-sulfate], XVIII. [D-homoglutamic acid, 4α-sulfonic acid], XXIX. [D-homoglutamic acid, 4α-sulfate], XL. [D-homoglutamic acid, 40-sulfonic acid], XLI. [D-homoglutamic acid, 4β-sulfate], XLII. [D-homoglutamic acid, 5α-sulfate], XLIII. [D-homoglutamic acid, 5α-sulfate], XLIV. [D-homoglutamic acid, 5β-sulfonic acid], XLV. [D-homoglutamic acid, 50-sulfate], XLVI. [L-homoglutamine, N-sulfonic acid], XLVII. [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XLVIII. [Pentane-2α-carboxy, 5-carboxamido-1-sulfate], XLIX. [Butane-1α-carboxy, 4-carboxamido-1-sulfonic acid], L. [Butane-1α-carboxy, 4-carboxamido-1-sulfate], LI. [D-homoglutamine, N-sulfonic acid], LII. [Pentane-2β-carboxy, 5-carboxamido-1-sulfonic acid], LIII. [Butane-i , -carboxy, 4-carboxamido-1-sulfonic acid], LIV. [Butane-i 1-carboxy, 4-carboxamido-1-sulfate], LV. [D-homoglutamine, 3α-sulfonic acid], LVI. [D-homoglutamine, 3α-sulfate], LVII. [D-homoglutamine, 3β-sulfonic acid], LVIII. [D-homoglutamine, 3β-sulfate], LIX. [D-homoglutamine, 4α-sulfonic acid], LX. [D-homoglutamine, 4α-sulfate], LXI. [D-homoglutamine, 4β-sulfonic acid], LXII. [D-homoglutamine, 4β-sulfate], LXIII. [D-homoglutamine, 5α-sulfonic acid], LXIV. [D-homoglutamine, 5α-sulfate], LXV. [D-homoglutamine, 5β-sulfonic acid] and LXVI. [D-homoglutamine, 5-sulfate].
34 . Use of the composition as claimed in claim 22 , wherein novel sulfonic acid/sulfate derivatives of the formulae ZOC—CR 3 R 4 —CR 1 R 2 —COOH wherein: Z=OH or NH 2 , R 1 , to R 4 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H XXIII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =NHSO 3 H is the same meaning as is before defined;
XXIV. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XXXV. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XXVI. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =SO 3 H is the same meaning as is before defined; XVII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =H, R 1 =OSO 3 H is the same meaning as is before defined; XVIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =NHSO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; XL. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; XLI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =SO 3 H is the same meaning as is before defined; XLII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =H, R 2 =OSO 3 H is the same meaning as is before defined; XLIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XLIV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; XLV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; XLVI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =NHSO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XLIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; L. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =SO 3 H is the same meaning as is before defined; LI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =H, R 1 =OSO 3 H is the same meaning as is before defined; LII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; LIV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; LV. A compound as claimed in claim 1 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; LVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =NHSO 3 H is the same meaning as is before defined; LVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; LIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =SO 3 H is the same meaning as is before defined; LX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =H, R 2 =OSO 3 H is the same meaning as is before defined; LXI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LXII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; LXIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; LXIV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =H, R 2 =NH 2 , R 4 =OSO 3 H 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 ZOC—CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH, wherein: Z=OH or NH 2 , R 1 , to R 6 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H XVII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =NHSO 3 H is the same meaning as is before defined;
XVIII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; XXIX. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XL. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =SO 3 H is the same meaning as is before defined; XLI. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =OSO 3 H is the same meaning as is before defined; XLII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =OSO 3 H is the sane meaning as is before defined; XLIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =SO 3 H is the same meaning as is before defined; XLIV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =NHSO 3 H is the same meaning as is before defined; XLV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; XLVI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; XLIX. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; L. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; LI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; LII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; LIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; LIV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; LV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =NHSO 3 H is the same meaning as is before defined; LVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; LVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =SO 3 H is the same meaning as is before defined; LIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =H, R 1 =OSO 3 H is the same meaning as is before defined; LX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =OSO 3 H is the same meaning as is before defined; LXI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =SO 3 H is the same meaning as is before defined; LXII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =NHSO 3 H is the same meaning as is before defined; LXIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; LXIV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; LXV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LXVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R=R 4 =R 5 =R 6 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; LXVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; LXVIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; LXIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; LXX. A compound as claimed in claim 22 , wherein Z=NH 2 , R=R 4 =R 3 =&=H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; LXXI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; LXXII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =H, R 2 =NH 2 , R 6 =OSO 3 H 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 ZOC—CR 7 R 8 —CR 5 R 6 —CR 3 R 4 —CR 1 R 2 —COOH, wherein: Z=OH or NH 2 , R 1 , to R 8 denotes H, NH 2 , SO 3 H, or OSO 3 H, CH 2 —SO 3 H, CH 2 —OSO 3 H, NHSO 3 H
XLIV. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =NHSO 3 H is the same meaning as is before defined; XLV. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =—CH 2 SO 3 H is the same meaning as is before defined; XLVI. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; XLVII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =SO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=OH, R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =OSO 3 H is the same meaning as is before defined; XLIX. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NHSO 3 H is the same meaning as is before defined; L. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; LI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =CH 2 OSO 3 H is the same meaning as is before defined; LII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =SO 3 H is the same meaning as is before defined; LIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =OSO 3 H is the same meaning as is before defined; LIV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 5 =Z6=R 7 =R 8 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; LVI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; LVII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; LVIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; LIX. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; LX. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; LXI. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; LXII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =SO 3 H is the same meaning as is before defined; LXIII. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =OSO 3 H is the same meaning as is before defined; LXIV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =SO 3 H is the same meaning as is before defined; LXV. A compound as claimed in claim 22 , wherein Z=OH, R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =OSO 3 H is the same meaning as is before defined; LXVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =NHSO 3 H is the same meaning as is before defined; LXVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 SO 3 H is the same meaning as is before defined; LXVIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =CH 2 OSO 3 H is the same meaning as is before defined; LXIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =SO 3 H is the same meaning as is before defined; LXX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 2 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 1 =OSO 3 H is the same meaning as is before defined; LXXI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NHSO 3 H is the same meaning as is before defined; LXXII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =CH 2 SO 3 H is the same meaning as is before defined; LXXIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =SO 3 H is the same meaning as is before defined; LXXIV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =OSO 3 H is the same meaning as is before defined; LXXV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =SO 3 H is the same meaning as is before defined; LXXVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 5 =F 6 =R 7 =R 8 =H, R 2 =NH 2 , R 3 =OSO 3 H is the same meaning as is before defined; LXXVII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =SO 3 H is the same meaning as is before defined; LXXVIII. A compound as claimed in claim 22 , wherein Z—NH 2 , R 1 =R 3 =R 5 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 4 =OSO 3 H is the same meaning as is before defined; LXXIX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =SO 3 H is the same meaning as is before defined; LXXX. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 7 =R 8 =H, R 2 =NH 2 , R 5 =OSO 3 H is the same meaning as is before defined; LXXXI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =SO 3 H is the same meaning as is before defined; IOLXXXII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 8 =H, R 2 =NH 2 , R 6 =OSO 3 H is the same meaning as is before defined; LXXXIII. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 5 =R=H, R 2 =NH 2 , R 7 =SO 3 H is the same meaning as is before defined; I LXXXIV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 4 =R 3 =R 6 =R 5 =R 8 =H, R 2 =NH 2 , R 7 =OSO 3 H is the same meaning as is before defined; LXXXV. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =SO 3 H is the same meaning as is before defined; LXXXVI. A compound as claimed in claim 22 , wherein Z=NH 2 , R 1 =R 3 =R 5 =R 4 =R 7 =R 6 =H, R 2 =NH 2 , R 8 =OSO 3 H is the same meaning as is before defined;
37 . Use of the composition as claimed in claim 22 , wherein said compound is non-toxic salts selected from the group consisting of:
I [L-Aspartic acid, N-Sulfonic acid], II [2α,3-dicarboxy, propane-1-sulfonic acid], III [2α,3-dicarboxy, propane-1-sulfate], IV [1α,2-carboxy ethane sulfonic acid], V [1α,2-carboxy ethane sulfate], VI [D-aspartic acid, N-sulfonic acid], VII [2β,3-carboxy,propane-1-sulfonic acid], VIII [2β,3-carboxy,propane-1-sulfate], IX [1β,2-carboxy ethane-1-sulfonic acid], X [1β,2-carboxy ethane-1-sulfate], XI [D-aspartic acid, 3α-sulfonic acid], XII [D-aspartic acid, 3α-sulfate], XIII [D-aspartic acid, 3β-sulfonic acid], XIV [D-aspartic acid, 3β-sulfate], XV [L-asparagine, N-sulfonic acid], XVI [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX [1α-carboxy, 2-carboxamido, ethane sulfate], XX [L-asparagine, 3α-sulfonic acid], XXI [L-asparagine, 3α-sulfate], XXII [L-asparagine, 3β-sulfonic acid], XXIII [L-asparagine, 3β-sulfate, XXIV [D-asparagine, N-sulfonic acid], XXV [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII [1β-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII [1β-carboxy, 2-carboxamido, ethane sulfate], XXIX [D-asparagine, 3α-sulfonic acid], XXX [D-asparagine, 3α-sulfate], XXXI [D-asparagine, 3β-sulfonic acid], XXXII [D-asparagine, 30-sulfate], XXXIII [L-glutamic acid, N-sulfonic acid], XXXIV [2α,4-dicarboxy, butane-1-sulfonic acid], XXXV [2α,4-dicarboxy, butane-1-sulfate], XXXVI [1α,3-dicarboxy, propane sulfonic acid], XXVII [1α,3-dicarboxy, propane sulfate], XVIII [1β,3-dicarboxy, propane sulfate], XXXIX [1β,3-dicarboxy, propane sulfonic acid],
38 . Use of the composition as claimed in claim 22 , wherein said compound is non-toxic salts selected from the group consisting of:
I [D-glutamic acid, N-sulfonic acid], II [2β,4-dicarboxy, butane-1-sulfonic acid], III [2β,4-dicarboxy, butane-1-sulfate], IV [D-glutamic acid, 3α-sulfonic acid], V [D-glutamic acid, 3α-sulfate], VI [D-glutamic acid, 3β-sulfonic acid], VII [D-glutamic acid, 3β-sulfate], VIII [D-glutamic acid, 4α-sulfonic acid], IX [D-glutamic acid, 4α-sulfate], X [D-glutamic acid, 4β-sulfonic acid], XI [D-glutamic acid, 3β-sulfate], XII [L-glutamine, N-sulfonic acid], XIII [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XIV [2α-carboxy, 4-carboxamido, butane-1-sulfate], XV [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVI [1α-carboxy, 3-carboxamido, propane-1-sulfate], XVII [1β-carboxy, 3-carboxamido, propane-1-sulfate], XVIII [1β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XIX [D-glutamine, N-sulfonic acid], XX [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXII [D-glutamine, 3α-sulfonic acid], XXIII [D-glutamine, 3α-sulfate], XXIV [D-glutamine, 3β-sulfonic acid], XXV [D-glutamine, 3β-sulfate], XXVI [D-glutamine, 4α-sulfonic acid], XXVII [D-glutamine, 4α-sulfate], XXVIII [D-glutamine, 4β-sulfonic acid], XXIX [D-glutamine, 413-sulfate], XXX [L-homoglutamic acid, N-sulfonic acid], XXXI [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXII [Pentane-2α,5-dicarboxy-1-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-2β,5-dicarboxy-1-sulfonic acid], XXXVII [Pentane-2β,5-dicarboxy-1-sulfate], XXXVIII [Butane-1β,4-dicarboxy-1-sulfonic acid], XXXIX [Butane-1β,4-dicarboxy-1-sulfate],
39 . Use of the composition as claimed in claim 22 , wherein said compound is non-toxic salts selected from the group consisting of:
I [D-homoglutamic acid, 3α-sulfonic acid], II [D-homoglutamic acid, 3α-sulfate], III [D-homoglutamic acid, 3β-sulfonic acid], IV [D-homoglutamic acid, 3β-sulfate], V [D-homoglutamic acid, 4α-sulfonic acid], VI [D-homoglutamic acid, 4α-sulfate], VII [D-homoglutamic acid, 4β-sulfonic acid], VIII [D-homoglutamic acid, 4β-sulfate], IX [D-homoglutamic acid, 5α-sulfate], X [D-homoglutamic acid, 5α-sulfate], XI [D-homoglutamic acid, 5β-sulfonic acid], XII [D-homoglutamic acid, 5β-sulfate], XIII [L-homoglutamine, N-sulfonic acid], XIV [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XV [Pentane-2α-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-2β-carboxy, 5-carboxamido-1-sulfonic acid], XX [Butane-1β-carboxy, 4-carboxamido-1-sulfonic acid], XXI [Butane-1β-carboxy, 4-carboxamido-1-sulfate], XXII [D-homoglutamine, 3α-sulfonic acid], XXIII [D-homoglutamine, 3α-sulfate], XXIV [D-homoglutamine, 3β-sulfonic acid], XXV [D-homoglutamine, 3β-sulfate], XXVI [D-homoglutamine, 4α-sulfonic acid], XXVII [D-homoglutamine, 4α-sulfate], XXVIII [D-homoglutamine, 413-sulfonic acid], XXIX [D-homoglutamine, 4β-sulfate], XXX [D-homoglutamine, 5α-sulfonic acid], XXXI [D-homoglutamine, 5α-sulfate], XXXII [D-homoglutamine, 50-sulfonic acid] and XXXIII [D-homoglutamine, 5β-sulfate].
40 . Use of the composition as claimed in claim 22 , 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 [2α,3-dicarboxy, propane-1-sulfonic acid], III [2α,3-dicarboxy, propane-1-sulfate], IV [1α,2-carboxy ethane sulfonic acid], V [1α,2-carboxy ethane sulfate], VI [D-aspartic acid, N-sulfonic acid], VII [2β,3-carboxy,propane-1-sulfonic acid], VIII [2β,3-carboxy,propane-1-sulfate], IX [1β,2-carboxy ethane-1-sulfonic acid], X [1β,2-carboxy ethane-1-sulfate], XI [D-aspartic acid, 3α-sulfonic acid], XII [D-aspartic acid, 3α-sulfate], XIII [D-aspartic acid, 3β-sulfonic acid], XIV [D-aspartic acid, 30-sulfate], XV [L-asparagine,N-sulfonic acid], XVI [2α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XVII [2α-carboxy, 3-carboxamido, propane-1-sulfate], XVIII [1α-carboxy, 2-carboxamido, ethane sulfonic acid], XIX [1α-carboxy, 2-carboxamido, ethane sulfate], XX [L-asparagine, 3α-sulfonic acid], XXI [L-asparagine, 3α-sulfate], XXII [L-asparagine, 3β-sulfonic acid], XXIII [L-asparagine, 30-sulfate, XXIV [D-asparagine, N-sulfonic acid], XXV [2β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI [2β-carboxy, 3-carboxamido, propane-1-sulfate], XXVII [1β-carboxy, 2-carboxamido, ethane sulfonic acid], XXVIII [1-carboxy, 2-carboxamido, ethane sulfate], XXLX [D-asparagine, 3α-sulfonic acid], XXX [D-asparagine, 3α-sulfate], XXXI [D-asparagine, 30-sulfonic acid], XXXII [D-asparagine, 3β-sulfate], 41. Use of the composition as claimed in claim 22 , 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 [2α,4-dicarboxy, butane-1-sulfonic acid], III [2α,4-dicarboxy, butane-1-sulfate], IV [1α,3-dicarboxy, propane sulfonic acid], V [1α,3-dicarboxy, propane sulfate], VI [1β,3-dicarboxy, propane sulfate], VII [1β,3-dicarboxy, propane sulfonic acid], VIII [D-glutamic acid, N-sulfonic acid], IX [2β,4-dicarboxy, butane-1-sulfonic acid], X [2β,4-dicarboxy, butane-1-sulfate], XI [D-glutamic acid, 3α-sulfonic acid], XII [D-glutamic acid, 3α-sulfate], XIII [D-glutamic acid, 3β-sulfonic acid], XIV [D-glutamic acid, 313-sulfate], XV [D-glutamic acid, 4α-sulfonic acid], XVI [D-glutamic acid, 4α-sulfate], XVII [D-glutamic acid, 4β-sulfonic acid], XVIII [D-glutamic acid, 3β-sulfate], XIX [L-glutamine, N-sulfonic acid], XX [2α-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXI [2α-carboxy, 4-carboxamido, butane-1-sulfate], XXII [1α-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXIII [1α-carboxy, 3-carboxamido, propane-1-sulfate], XXIV [1β-carboxy, 3-carboxamido, propane-1-sulfate], XXV [1β-carboxy, 3-carboxamido, propane-1-sulfonic acid], XXVI [D-glutamine, N-sulfonic acid], XXVII [2β-carboxy, 4-carboxamido, butane-1-sulfonic acid], XXVIII [2β-carboxy, 4-carboxamido, butane-1-sulfate], XXIX [D-glutamine, 3α-sulfonic acid], XXX [D-glutamine, 3α-sulfate], XXXI [D-glutamine, 3β-sulfonic acid], XXXII [D-glutamine, 3β-sulfate], XXXIII [D-glutamine, 4α-sulfonic acid], XXXIV [D-glutamine, 4α-sulfate], XXXV [D-glutamine, 4β-sulfonic acid], XXXVI [D-glutamine, 4β-sulfate], XXXVII [L-homoglutamic acid, N-sulfonic acid], XXXVIII [Pentane-2α,5-dicarboxy-1-sulfonic acid], XXXIX [Pentane-2α,5-dicarboxy-1-sulfate], XL [Butane-1α,4-dicarboxy-1-sulfonic acid], XLI [Butane-1α,4-dicarboxy-1-sulfate], 42. Use of the composition as claimed in claim 22 , 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-2β,5-dicarboxy-1-sulfonic acid], III [Pentane-2β,5-dicarboxy-1-sulfate], IV [Butane-1β,4-dicarboxy-1-sulfonic acid], V [Butane-1β,4-dicarboxy-1-sulfate], VI [D-homoglutamic acid, 3α-sulfonic acid], VII [D-homoglutamic acid, 3α-sulfate], VIII [D-homoglutamic acid, 3β-sulfonic acid], IX [D-homoglutamic acid, 313-sulfate], X [D-homoglutamic acid, 4α-sulfonic acid], XI [D-homoglutamic acid, 4α-sulfate], XII [D-homoglutamic acid, 413-sulfonic acid], XIII [D-homoglutamic acid, 4β-sulfate], XIV [D-homoglutamic acid, 5α-sulfate], XV [D-homoglutamic acid, 5α-sulfate], XVI [D-homoglutamic acid, 5β-sulfonic acid], XVII [D-homoglutamic acid, 5β-sulfate], XVIII [L-homoglutamine, N-sulfonic acid], XIX [Pentane-2α-carboxy, 5-carboxamido-1-sulfonic acid], XX [Pentane-2α-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-2β-carboxy, 5-carboxamido-1-sulfonic acid], XXV [Butane-1β-carboxy, 4-carboxamido-1-sulfonic acid], XXVI [Butane-1β-carboxy, 4-carboxamido-1-sulfate], XXVII [D-homoglutamine, 3α-sulfonic acid], XXVIII [D-homoglutamine, 3α-sulfate], XXIX [D-homoglutamine, 3β-sulfonic acid], XXX [D-homoglutamine, 30-sulfate], XXXI [D-homoglutamine, 4α-sulfonic acid], XXXII [D-homoglutamine, 4α-sulfate], XXXIII [D-homoglutamine, 4β-sulfonic acid], XXXIV [D-homoglutamine, 4β-sulfate], XXXV [D-homoglutamine, 5α-sulfonic acid], XXXVI [D-homoglutamine, 5α-sulfate], XXVII [D-homoglutamine, 50-sulfonic acid] and XXVIII [D-homoglutamine, 5β-sulfate].Join the waitlist — get patent alerts
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