IP Library Granted Patent US 9,351,992
Granted Patent B2
US 9,351,992 · App. 12/739,287 · Granted May 31, 2016

Non-anticoagulant polysaccharide compositions

Inventors: Mallikarjun Sundaram (Flemington, NJ); Takashi Kei Kishimoto (Lexington, MA); Sucharita Roy (Tyngsboro, MA)
Assignee: MOMENTA PHARMACEUTICALS, INC.
A61K31/727C08B37/0078C08L5/10C12P19/04
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Quick Facts
Patent No.
US 9,351,992
App. No.
12/739,287
Granted
May 31, 2016
Kind
B2
Abstract

Preparations of polysaccharides lacking substantial anticoagulant activity are provided herein. Methods of making and using such preparations are provided.

Claims (32)

1. A pharmaceutical composition comprising a low molecular weight heparin preparation and a pharmaceutically acceptable carrier, wherein the low molecular weight heparin preparation is produced by a process comprising digesting unfractionated heparin (UFH) with a heparinase that cleaves at the pentasaccharide site comprising:

(1) digesting UFH with Bacteroides thetaiotaomicron Heparinase I;

(2) monitoring absorbance at 232 nm during the step of digesting; and

(3) quenching the digestion reaction when the absorbance at 232 nm reaches between 1.7 and 2.0, wherein the low molecular weight heparin preparation has an anti-Xa activity of 10-40 IU/mg and an anti-IIa activity of 5-15 IU/mg, a weight average molecular weight between 3,500 and 5,500 and a molecular weight distribution such that 30-50% of the oligosaccharides of the preparation have a molecular weight <3000 Da; 40-55% of the oligosaccharides have a molecular weight between 3000-8000 Da, and 5-30% of the oligosaccharides have a molecular weight >8000 Da, wherein the preparation has no glycol split uronic acid residues, and wherein the preparation consists essentially of polysaccharides of Formula I:

U 2S —H x,y,z —[U w —H x,y,z ] n

wherein n is an integer such that n=1-20;

w=−2OS or −2OH;

x=—NS or —NAc;

y=−3OS or −3OH;

z=−6OS or −6OH;

wherein U indicates a uronic acid residue and H indicates a hexosamine residue;

and wherein w, x, y, and z are independently the same or different on each U or H residue.

2. The pharmaceutical composition of claim 1 , wherein the Heparinase I is present at about 1.0 to 5.0 IU/g UFH.

3. The pharmaceutical composition of claim 1 , wherein the step of digesting does not include treatment with a thiol reducing agent.

4. The pharmaceutical composition of claim 1 , wherein the preparation has an anti-Xa activity less than 40, 30, or 20 IU/mg.

5. The pharmaceutical composition of claim 1 , wherein the low molecular weight heparin preparation has an anti-IIa activity of 5 to less than 10 IU/mg.

6. The pharmaceutical composition of claim 1 , wherein the preparation has polysaccharide chains having greater than 40% U 2S H NS,6S disaccharide residues.

7. The pharmaceutical composition of claim 1 , wherein the preparation has polysaccharide chains having greater than 50% U 2S H NS,6S disaccharide residues and a degree of desulfation less than 40%.

8. The pharmaceutical composition of claim 7 , wherein the polysaccharides of the preparation have greater than 50% U 2S H NS,6S disaccharide residues.

9. The pharmaceutical composition of claim 7 , wherein the polysaccharides of the preparation have greater than 60% U 2S H NS,6S disaccharide residues.

10. The pharmaceutical composition of claim 7 , wherein the polysaccharides of the preparation have greater than 70% U 2S H NS,6S disaccharide residues.

11. The pharmaceutical composition of claim 7 , wherein the polysaccharides of the preparation have greater than 80% U 2S H NS,6S disaccharide residues.

12. The pharmaceutical composition of claim 7 , wherein the polysaccharides of the preparation have a degree of desulfation less than 30%.

13. The pharmaceutical composition of claim 12 , wherein the polysaccharides of the preparation have a degree of desulfation less than 20%.

14. The pharmaceutical composition of claim 13 , wherein the polysaccharides of the preparation have a degree of desulfation less than 10%.

15. The pharmaceutical composition of claim 1 , wherein less than 2% of the polysaccharide chains of the preparation comprise the tetrasaccharide UH NAc,6S GH NS,3S,6S .

16. The pharmaceutical composition of claim 1 , wherein about 20-30% of the polysaccharide chains of the preparation comprise the pentasaccharide H NAc,6S GH NS,3S,6S I 2S H NS,6S .

17. The pharmaceutical composition of claim 1 , wherein about 20-30% of the polysaccharide chains of the preparation comprise the tetrasaccharide U 2S H NAc,6S GH NS,3S,6S .

18. The pharmaceutical composition of claim 1 , wherein the preparation has a polydispersity of about 1.6 to 2.1.

19. The pharmaceutical composition of claim 1 , wherein the preparation has anti-metastatic activity.

20. The pharmaceutical composition of claim 1 , wherein the preparation binds to one or more of: VEGF, FGF, SDF-1, or P-selectin.

21. The pharmaceutical composition of claim 20 , wherein the preparation inhibits an activity of one or more of: VEGF, FGF, SDF-1, or P-selectin.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2016
From: SUNDARAM, MALLIKARJUN; KISHIMOTO, TAKASHI KEI; ROY, SUCHARITA
To: MOMENTA PHARMACEUTICALS, INC.
Reel/Frame 037640/0346 →
Continuity (2)
Provisional Application 60985080 · Nov 2, 2007
Related Publication 20100298260A1 · Nov 25, 2010