IP Library Granted Patent US 10,617,764
Granted Patent B2
US 10,617,764 · App. 15/038,235 · Granted Apr 14, 2020

Lyophilized anti-tissue factor antibody-drug conjugates

Inventors: Jesper Valbjørn (Veksø, DK); Xiaona Jing (Soborg, DK); Kelly Ann Roby (Bloomington, IN); Timothy Warren Paul (Bloomington, IN); Gregory Allan Sacha (Bargersville, IN); Nathan Alan Pease (Bloomington, IN); Bodil Willumsen (Basel, CH)
Assignee: GENMAB A/S
A61K47/48538A61K9/19A61K47/22C07K16/36A61K47/26C07K2317/21C07K2317/94
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Quick Facts
Patent No.
US 10,617,764
App. No.
15/038,235
Granted
Apr 14, 2020
Kind
B2
Abstract

Disclosed herein are surfactant free lyophilized formulations of antibody-drug conjugates (ADCs), such as anti-tissue factor ADCs, and reconstituted formulations, processes and uses thereof. The formulations are particularly suitable for an anti-TF ADC based on an auristatin derivative or other similarly hydrophobic drug. Typically, the excipients of the formulations comprise or consist of histidine, sucrose, trehalose, mannitol and glycine.

Claims (49)

1. A lyophilized formulation of an anti-tissue factor (TF) antibody-drug conjugate (ADC), the lyophilized formulation obtainable or obtained by lyophilizing an aqueous formulation comprising said anti-TF ADC and pharmaceutically acceptable excipients, wherein:

(a) the lyophilized formulation is free of surfactant,

(b) the anti-TF antibody portion of the ADC comprises a variable heavy (VH) region comprising a CDR1 region having the amino acid sequence set forth in SEQ ID NO: 6, a CDR2 region having the amino acid sequence set forth in SEQ ID NO: 7, and a CDR3 region having the amino acid sequence set forth in SEQ ID NO: 8, and a variable light (VL) region comprising a CDR1 region having the amino acid sequence set forth in SEQ ID NO:46, a CDR2 region having the amino acid sequence set forth in SEQ ID NO: 47, and a CDR3 region having the amino acid sequence set forth in SEQ ID NO: 48, and

(c) the drug portion of the ADC comprises vcMMAE.

2. The lyophilized formulation of claim 1 , wherein the pharmaceutically acceptable excipients comprise:

a) a buffer which limits pH shifts during the lyophilizing step so that pH is kept between about 5 and about 7,

b) at least one non-reducing sugar which forms an amorphous phase with the anti-TF ADC in solid state; and

c) at least one bulking agent.

3. The lyophilized formulation of claim 1 , wherein the aqueous formulation comprises a buffer selected from the group consisting of histidine, citrate, phosphate, carbonic acid, succinate, glycolate and a combination of any thereof.

4. The lyophilized formulation of claim 2 , wherein the aqueous formulation comprises the buffer at a concentration of about 20 to about 50 mM.

5. The lyophilized formulation of claim 2 , wherein the non-reducing sugar is selected from sucrose, trehalose and a combination thereof.

6. The lyophilized formulation of claim 2 , wherein the aqueous formulation comprises the non-reducing sugar at a concentration of about 10 to about 250 mM.

7. The lyophilized formulation of claim 2 , wherein the bulking agent is selected from mannitol and glycine.

8. The lyophilized formulation of claim 2 , wherein the aqueous formulation comprises the bulking agent at a concentration of about 50 mM to about 300 mM.

9. The lyophilized formulation of claim 1 , wherein the aqueous formulation comprises from about 5 g/L to about 30 g/L anti-TF ADC.

10. The lyophilized formulation of claim 1 , wherein the pH of the aqueous formulation is in a range from about 5.5 to 6.5.

11. The lyophilized formulation of claim 1 , comprising mannitol and sucrose, wherein the weight by weight ratio of mannitol to sucrose is between about 1:1 and about 30:1.

12. The lyophilized formulation of claim 1 , comprising mannitol and sucrose, wherein the weight by weight ratio of mannitol to anti-TF ADC is about 3:1 and the weight by weight ratio of mannitol to sucrose is about 1:1.

13. The lyophilized formulation of claim 1 , which is obtainable or obtained by lyophilizing an aqueous formulation comprising about 5 g/L to about 30 g/L anti-TF ADC and pharmaceutically acceptable excipients comprising:

a. about 20 to about 50 mM histidine or citrate buffer having a pH of about 5 to about 7;

b. about 10 to about 250 mM sucrose or trehalose; and

c. about 50 mM to about 300 mM mannitol or glycine.

14. The lyophilized formulation of claim 1 , wherein the aqueous formulation comprises from about 9 to about 11 g/L anti-TF ADC.

15. The lyophilized formulation of claim 1 , wherein the antibody comprises

a VH region comprising an amino acid sequence of SEQ ID NO: 5 and a VL region comprising an amino acid sequence of SEQ ID NO: 45.

16. The lyophilized formulation of claim 1 , wherein the average absolute number of drug moieties per antibody molecule is 1, 2, 3, 4, 5, 6, 7, or 8.

17. The lyophilized formulation of claim 1 , wherein the anti-TF antibody is a full-length antibody.

18. The lyophilized formulation of claim 1 , which is obtainable or obtained by lyophilizing an aqueous formulation comprising about 9 g/L to about 11 g/L anti-TF ADC and pharmaceutically acceptable excipients comprising: about 30 mM histidine buffer having a pH of about 5 to about 7; about 88 mM sucrose; and about 165 mM mannitol; wherein the antibody comprises a VH region comprising an amino acid sequence of SEQ ID NO: 5 and a VL region comprising an amino acid sequence of SEQ ID NO: 45.

19. The lyophilized formulation of claim 1 , wherein the anti-TF ADC is stable at 2-8° C. for pharmaceutical use for at least 6 months.

20. The lyophilized formulation of claim 19 , wherein the formulation is stable when it has less than 3.0% aggregates when stored at 5° C. for at least 6 months.

21. The lyophilized formulation of claim 19 wherein the stability is determined by SEC analysis according to Example 10.

22. The lyophilized formulation of claim 1 , which lyophilized formulation contains less than 3.0 wt. % moisture.

23. The lyophilized formulation of claim 1 , wherein the formulation is free of any inorganic salts.

24. An aqueous solution suitable for preparing a lyophilized formulation of an anti-TF ADC, comprising:

a. from about 7 to about 20 g/L anti-TF ADC of claim 1 ;

b. about 28 to 34 mM histidine;

c. about 84 to about 146 mM sucrose;

d. about 158 to about 274 mannitol.

25. A pharmaceutically acceptable liquid formulation obtained by reconstituting the lyophilized formulation of claim 1 in a sterile aqueous diluent.

26. The liquid formulation of claim 25 , comprising about 5 g/L to about 30 g/L anti-TF ADC, about 20 to about 50 mM histidine having a pH of about 5 to about 7; about 10 to about 250 mM sucrose or trehalose; and about 50 mM to about 300 mM mannitol or glycine.

27. A method for preparing a lyophilized formulation of claim 1 comprising the steps of:

a. cooling the aqueous solution at a rate of from 0.5° C./min to 1° C./min to a temperature of −40° C. or less;

b. holding isothermally for at least 120 min;

c. warming to between −20° C. and −15° C. at a rate of from 0.5° C./min to 3° C./min;

d. holding isothermally for at least 180 min;

e. applying vacuum using a pressure between 50 mTorr and 200 mTorr at a temperature between −30° C. and −10° C.;

f. increasing the temperature to between 35° C. and 50° C. at a rate of from 0.5° C./min and 1° C./min and

g. holding isothermally for at least 10 hours.

28. A method of preparing an injectable solution of an anti-TF ADC, comprising the step of reconstituting the lyophilized formulation of claim 1 in a sterile aqueous diluent.

Assignments (3)
SECURITY INTEREST Recorded Dec 15, 2025
From: GENMAB A/S; GENMAB B.V.; GENMAB HOLDING B.V.
To: MORGAN STANLEY SENIOR FUNDING, INC.
Reel/Frame 073933/0597 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Dec 15, 2025
From: GENMAB HOLDING B.V.; GENMAB A/S; GENMAB B.V.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 073949/0722 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 27, 2018
From: VALBJORN, JESPER; JING, XIAONA; ROBY, KELLY ANN; PAUL, TIMOTHY WARREN; SACHA, GREGORY ALLAN; PEASE, NATHAN ALAN; WILLUMSEN, BODIL
To: GENMAB A/S
Reel/Frame 047862/0617 →