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Details for Patent: 4,774,231

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Details for Patent: 4,774,231

Title: Disaccharides formed by patterns having a glucosamine and uronic acid structure, preparation thereof and biological applications
Abstract:1,4.alpha.disaccharides of formula: ##STR1## with Z representing a nitrogenous functional group, M hydrogen or a sulphate or acetyl group, R an alkyl radical of 1 to 4 carbon atoms and A functional group such as an acid group, or a derivative.
Inventor(s): Petitou; Maurice (Paris, FR), Sinay; Pierre (Orleans, FR), Choay; Jean (Paris, FR), Lormeau; Jean-Claude (Maromme, FR)
Assignee: Choay S.A. (Paris, FR)
Filing Date:Jul 21, 1986
Application Number:06/888,527
Claims:1. A process for synthesizing a heparinic disaccharide which process comprises the steps of condensing I with II ##STR8## wherein Y groups Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, and Y.sub.5 are selected from the group consisting of a precursor to an SO.sub.3 group, and a precursor to an OH group, wherein at least one Y group is a precursor to an SO.sub.3 group and at least one Y group is a precursor to an OH group,

wherein the precursor to an OH group is stable and does not migrate to other carbon positions during removal of the Y groups which are the precursor to an SO.sub.3 group and during the introduction of SO.sub.3 groups to replace the Y groups which are the precursor to an SO.sub.3 group,

further wherein R.sub.1 is a protecting group which forms an ester at the carboxyl group, which protecting group is removable following removal of Y groups which are the precusor to an OH group, further wherein R is an inert protecting group, which protecting group is stable during removal of the other protecting groups, further wherein R.sub.2 is a reactive group, which reactive group allows the formation of a 1-4 alpha type linkage during the condensation,

further wherein R.sub.3 is an OH group,

further wherein D is a nitrogen containing group, which nitrogen containing group is a precursor to an amine,

wherein the process further comprises the steps of removing the Y groups which are the precursor to an SO.sub.3 group, substituting SO.sub.3 groups at the carbon positions left free thereby,

removing the Y groups which are the precursor to an OH group and converting the nitrogen containing group into an amine.

2. The process of claim 1 which further comprises converting the amine group to a group which is selected from the group consisting of NHCOCH.sub.3 and NHSO.sub.3.

3. The process of claim 1 which further comprises removing the protecting group which forms an ester at the carboxyl and forming a salt with an alkaline metal cation.

4. The process of claim 1 which further comprises forming a salt between an alkaline metal cation and the SO.sub.3 groups.

5. The process of claim 1 wherein

the precursor to an SO.sub.3 group is acetyl,

the precursor to an OH group is benzyl,

R.sub.1 is an alkyl group having from 1 to 4 carbons,

R is selected from the group consisting of an alkyl group having from one to four carbons, and a lower aryl group,

R.sub.2 is a halogen,

D is N.sub.3.

6. The process of claim 5 wherein R.sub.2 is a halogen which is selected from the group consisting of Br and Cl.

7. A process for synthesizing a heparinic disaccharide which process comprises the steps of condensing I with II ##STR9## wherein Y.sub.3 is a precursor to an SO.sub.3 group, and Y groups Y.sub.1, Y.sub.2, Y.sub.4, and Y.sub.5 are a precursor to an OH group,

wherein the precursor to an OH group is stable and does not migrate to other carbon positions during removal of the precursor to an SO.sub.3 group and the introduction of SO.sub.3 groups to replace the Y groups which are the precursor to an SO.sub.3 group,

further wherein R.sub.1 is a protecting group which forms an ester at the carboxyl group which protecting group is removable following removal of the Y groups which are the precursor to an OH group,

further wherein R is an inert protecting group, which protecting group is stable during removal of the other protecting groups,

further wherein R.sub.2 is a reactive group, which reactive group allows the formation of a 1-4 alpha type linkage during the condensation,

further wherein R.sub.3 is an OH group,

further wherein D is a nitrogen containing group, which nitrogen containing group is a precursor to an amine,

wherein the process further comprises the steps of removing Y.sub.3, substituting an SO.sub.3 group at the carbon position left free thereby,

removing the Y groups which are a precursor to an OH group and converting the nitrogen containing group into an amine.

8. The process of claim 7 which further comprises converting the amine group to a group which is selected from the group consisting of NHCOCH.sub.3 and NHSO.sub.3.

9. The process of claim 7 which further comprises removing the protecting group which forms an ester at the carboxyl and forming a salt with an alkaline metal cation.

10. The process of claim 7 which further comprises forming a salt between an alkaline metal cation and the SO.sub.3 group.

11. The process of claim 7 wherein

the precursor to an SO.sub.3 group is acetyl,

the precursor to an OH group is benzyl,

R.sub.1 is an alkyl group having from 1 to 4 carbons,

R is selected from the group consisting of an alkyl group having from one to four carbons, and a lower aryl group,

R.sub.2 is a halogen,

D is N.sub.3.

12. The process of claim 11 wherein R.sub.2 is a halogen which is selected from the group consisting of Br and Cl.

13. A process for synthesizing a heparinic disaccharide which process comprises the steps of condensing I with II ##STR10## wherein R.sub.2 is a halogen, wherein the process further comprises the steps of removing the acetyl group at carbon six of I, substituting an SO.sub.3 group at the carbon position left free thereby,

removing the benzyl group and converting the N.sub.3 group into an amine.

14. The process of claim 13 which further comprises converting the amine group to a group which is selected from the group consisting of NHCOCH.sub.3 and NHSO.sub.3.

15. The process of claim 14 which further comprises removing the methyl group which forms an ester at the carboxyl and forming a salt with an alkaline metal cation.

16. The process of claim 13 which further comprises forming a salt between an alkaline metal cation and the SO.sub.3.

17. The process of claim 13 wherein R.sub.2 is a halogen which is selected from the group consisting of Br and Cl.

18. The process of claim 4 wherein the acetylation of the NH.sub.2 group is carried out at pH8.

19. The process of claim 14 wherein the sulfatation of the NH.sub.2 group is carried out at pH 9-10.

20. The process of claim 13 wherein the condensation reaction is carried out in an organic solvent.

21. The process of claim 20 wherein the organic solvent is dichloromethane.

22. The process of claim 13 wherein the condensation reaction is carried out in the presence of silver triflate.

23. The process of claim 13 wherein the condensation reaction is carried out in the presence of a proton acceptor.

24. The process of claim 23 wherein the proton acceptor is sym-collidine.

25. The process of claim 13 wherein the condensation reaction is carried out in dichloromethane in the presence of silver triflate and sym-collidine.

26. The process of claim 13 further comprising the step, following the substituting of the SO.sub.3 group, of passing the compound formed over an Na.sup.+ resin.
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