van Boeckel, Constant Adriaan Anton; Petitou, Maurice; Duchaussoy, Philippe; Dreef-Tromp, Cornelia Maria; Basten, Johannes Egbertus Maria;

Carbohydrate derivatives

The invention relates to a carbohydrate derivative having formula I ##STR1## wherein R.sup.1 is (1-4C)alkoxy; R.sup.2, R.sup.3 and R.sup.4 are independently (1-4C)alkoxy or OSO.sub.3.sup.-, the total number of sulfate groups is 4, 5, or 6; and the twisted lines represent bonds either above or below the plane of the six-membered ring to which they are attached; or a pharmaceutically acceptable salt thereof. The compounds of the invention have antithrombotic activity and may be used for treating or preventing thrombosis and for inhibiting smooth muscle cell proliferation.

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What is claimed is:

1. A carbohydrate derivative having the formula I ##STR12##

wherein R.sup.1 is (1-4C)alkoxy;

each of R.sup.2, R.sup.3 and R.sup.4 are independently (1-4C)alkoxy or OSO.sub.3.sup.- ;

the total number of sulfate groups is 4, 5 or 6;

and the twisted lines represent bonds either above or below the plane of the six-membered ring to which they are attached;

or a pharmaceutically acceptable salt thereof.

2. The carbohydrate derivative of claim 1, wherein the D-unit of formula I has the structure ##STR13##

R.sup.1 is methoxy; and each of R.sup.2, R.sup.3 and R.sup.4 are independently methoxy or OSO.sub.3.sup.-.

3. The carbohydrate derivative of claim 2, wherein R.sup.2 is methoxy.

4. The carbohydrate derivative of claim 3, wherein R.sup.3 is methoxy.

5. The carbohydrate derivative of claim 4, wherein R.sup.4 is methoxy.

6. A pharmaceutical composition comprising the carbohydrate derivative of claim 1 and pharmaceutically suitable auxiliaries.

7. A method of treating or preventing thrombosis, or inhibiting smooth muscle cell proliferation, comprising administering to a patient in need thereof an effective amount of the carbohydrate derivative of claim 1.

8. A process for preparing a pharmaceutical composition, comprising admixing the carbohydrate derivative of claim 1 with pharmaceutically acceptable auxiliaries.

9. The carbohydrate derivative of claim 1, which has the structure: ##STR14##