IP Library Granted Patent US 12,453,737
Granted Patent B2
US 12,453,737 · App. 17/265,678 · Granted Oct 28, 2025

Method for hydrating lyophilized cyclophosphamide composition and product thereof

Inventors: Hongzhen Yu (Shanghai, CN); Ziqiang Li (Shanghai, CN); Jiansheng Wan (Shanghai, CN); Xiaoxi Sheng (Shanghai, CN)
Assignees: Sinotherapeutics Inc.; Andorra Pharmaceuticals, LLC
A61K31/675A61K9/0019A61K9/08A61K9/19A61K47/02A61K47/10A61K47/26
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Quick Facts
Patent No.
US 12,453,737
App. No.
17/265,678
Granted
Oct 28, 2025
Kind
B2
Abstract

Provided are a hydration method for a lyophilized cyclophosphamide composition and a composition and preparation prepared thereby. The hydration method comprises: (a) providing an aqueous solution comprising cyclophosphamide and an optional pharmaceutically acceptable excipient; (b) freeze-drying the solution to obtain a lyophilized composition; and (c) hydrating the lyophilized composition by using liquid water to obtain the product.

Claims (26)

1. An injectable composition, comprising cyclophosphamide and mannitol,

wherein the porosity of the composition is greater than 96%, and

the composition has a moisture content of 7.8% to about 9.0%, based on cyclophosphamide monohydrate.

2. A method for making the injectable composition of claim 1 , comprising:

(a) providing an aqueous solution comprising cyclophosphamide and mannitol;

(b) freeze-drying the aqueous solution to give a solid composition; and

(c) hydrating the solid composition with vapor phase moisture from liquid water to give the injectable composition.

3. The method according to claim 2 , wherein the liquid water is a water solution.

4. The method according to claim 3 , wherein the water solution comprises a strong acid, a strong alkali, an inorganic salt, a glycerol, a pharmaceutically acceptable excipient or inorganic salt.

5. The method according to claim 4 , wherein the water solution provides a relative humidity during (c) of about 60% to about 98%.

6. The method according to claim 2 , wherein the hydrating is performed under a micro negative pressure of about 10-90 kPa.

7. The method of claim 4 , wherein the relative humidity during (c) is about 70% to about 95%.

8. The injectable composition of claim 1 ,

wherein the particle size distribution of the composition is characterized by a D50 value of less than 11.0 μm,

the bulk density of the composition is less than about 0.0600 g/mL, and

at least about 99% of the cyclophosphamide is retained after 3 weeks at 45° C.

9. The injectable composition of claim 8 , wherein a redissolving time of 500 mg of the composition in 25 ml of a 0.9% NaCl aqueous solution with cyclotron mixing in a glass vial oscillate at 250 rpm at room temperature is less than 2 minutes.

10. The injectable composition of claim 8 , wherein the tapped density of the composition is less than about 0.3000 g/mL.

11. The injectable composition of claim 8 , wherein the skeletal density of the composition is greater than 1.4700 g/mL.

12. The injectable composition of claim 8 , wherein the particle size distribution of the composition is characterized by a D90 value of less than 36.0 μm.

13. The injectable composition of claim 12 , wherein the particle size distribution of the composition is characterized by a D90 value of less than 29.0 μm.

14. The injectable composition of claim 8 , wherein the mannitol comprises δ-mannitol.

15. The injectable composition of claim 14 , wherein the mannitol consists of δ-mannitol.

16. The injectable composition of claim 8 , wherein the composition comprises less than 0.1% cyclophosphamide impurity B, as measured by HPLC, after the composition is maintained at a temperature of about 45° C. for up to 7 days.

17. The injectable composition of claim 8 , wherein the composition comprises less than 0.1% cyclophosphamide impurity A, as measured by HPLC, after the composition was maintained at a temperature of about 45° C. for up to 7 days.

18. The injectable composition of claim 1 , wherein the composition has a moisture content of 8.0% to about 9.0%, based on cyclophosphamide monohydrate.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2025
From: SINOTHERAPEUTICS INC.
To: SINOTHERAPEUTICS INC.; ANDORRA PHARMACEUTICALS, LLC
Reel/Frame 072187/0026 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2021
From: YU, HONGZHEN; LI, ZIQIANG; WAN, JIANSHENG; SHENG, XIAOXI
To: SINOTHERAPEUTICS INC.
Reel/Frame 055459/0586 →
Priority Claims (2)
CN 201810875707.5 · Aug 3, 2018 · national
CN 201811367499.4 · Nov 16, 2018 · national
Continuity (1)
Related Publication 20220133754A1 · May 5, 2022
References Cited (93)
US 4537883A · Alexander et al. · 1985 [cited by applicant]
US 4659699A · Francis · 1987 [cited by examiner]
US 4775533A · Grab · 1988 [cited by applicant]
US 4797388A · Francis · 1989 [cited by applicant]
US 5036060A · Alam et al. · 1991 [cited by applicant]
US 5066647A · Palepu et al. · 1991 [cited by applicant]
US 5130305A · Palepu et al. · 1992 [cited by applicant]
US 5227374A · Alexander et al. · 1993 [cited by applicant]
US 5268368A · Palepu · 1993 [cited by applicant]
US 5336669A · Palepu et al. · 1994 [cited by applicant]
US 5413995A · Alexander et al. · 1995 [cited by applicant]
US 5418223A · Palepu et al. · 1995 [cited by applicant]
US 5756552A · Takeuchi et al. · 1998 [cited by applicant]
US 9662342B2 · Palepu et al. · 2017 [cited by applicant]
US 10016447B2 · Patel et al. · 2018 [cited by applicant]
US 10149857B2 · Smith et al. · 2018 [cited by applicant]
US 10993952B2 · Chandrashekhar et al. · 2021 [cited by applicant]
US 20040105821A1 · Bernstein et al. · 2004 [cited by applicant]
US 20150029022A1 · Stebbins · 2015 [cited by applicant]
US 20150290226A1 · Chandrashekhar et al. · 2015 [cited by applicant]
US 20150320775A1 · Palepu et al. · 2015 [cited by applicant]
US 20170014374A1 · Zhang et al. · 2017 [cited by applicant]
US 20180055861A1 · Chandrashekhar et al. · 2018 [cited by applicant]
US 20180104264A1 · Kang et al. · 2018 [cited by applicant]
US 20180256608A1 · Smith et al. · 2018 [cited by applicant]
US 20200015557A1 · Shen et al. · 2020 [cited by applicant]
US 20200155579A1 · Yu et al. · 2020 [cited by applicant]
US 20220133754A1 · Yu · 2022 [cited by applicant]
CA 2053065A1 · 1992 [cited by applicant]
CA 2063058 · 1992 [cited by applicant]
CA 2063058A1 · 1992 [cited by applicant]
CA 2053065 · 1998 [cited by applicant]
CN 1923280 · 2007 [cited by applicant]
CN 1923280A · 2007 [cited by applicant]
CN 101564413 · 2009 [cited by applicant]
CN 101564413A · 2009 [cited by applicant]
CN 102058524 · 2011 [cited by applicant]
CN 102058524A · 2011 [cited by applicant]
CN 102258488 · 2011 [cited by applicant]
CN 102258488A · 2011 [cited by applicant]
CN 103536546 · 2014 [cited by applicant]
CN 107236004 · 2017 [cited by applicant]
CN 107236004A · 2017 [cited by applicant]
CN 107540711 · 2018 [cited by applicant]
CN 107540711A · 2018 [cited by applicant]
EP 0394045 · 1990 [cited by applicant]
EP 0394045A2 · 1990 [cited by applicant]
EP 1938798 · 2008 [cited by applicant]
EP 1938798A1 · 2008 [cited by applicant]
IN 0212MUM2013 · 2014 [cited by applicant]
WO 199408592 · 1994 [cited by applicant]
WO 2014068585 · 2014 [cited by applicant]
WO 2016046797 · 2016 [cited by applicant]
WO 2017207719 · 2017 [cited by applicant]
WO 2017207719A1 · 2017 [cited by applicant]
WO 2020025069 · 2020 [cited by applicant]
WO 2020100088 · 2020 [cited by applicant]
WO 2020100088A1 · 2020 [cited by applicant]
Patel K, Munjal B, Bansal AK. Effect of cyclophosphamide on the solid form of mannitol during lyophilization. European Journal of Pharmaceutical Sciences. Apr. 1, 2017;101:251-7. (Year: 2017). [cited by examiner]
International Search Report issued Nov. 11, 2019 in International Application No. PCT/CN2019/099251. [cited by applicant]
Written Opinion issued Nov. 11, 2019 in International Application No. PCT/CN2019/099251. [cited by applicant]
Beinjnen, et al., “Chemical stability of two sterile, parenteral formulations of cyclophosphamide (Endoxan) after reconstitution and dilution in commonly used infusion fluids,” vol. 46(4), pp. 111-116, Jul.-Aug. 1994. [cited by applicant]
Jan. 27, 2023, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Jan. 27, 203, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Jun. 29, 2023, 201980051898.6, CN. [cited by applicant]
Aug. 10, 2023, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Dec. 10, 2023, 283170, IL. [cited by applicant]
Definition of “Joule-Thomson effect”, printed from Wikipedia, the free encyclopedia on Apr. 22. 2023, 10 pages, found at http://en.wikipedia.org/wiki/Joule-Thomson_effect. [cited by applicant]
Product Description of “Cytoxan”, Rxlist, found at www.rxlist.com/cytoxan-drug.htm#description, pp. 1-3, (2020), printed on Aug. 9, 2023. [cited by applicant]
Nov. 11, 2019, PCT/CN2019/099251, WO. [cited by applicant]
Feb. 19, 2020, PCT/IB2019/059802, WO. [cited by applicant]
Apr. 16, 2021, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Jun. 24, 2021, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Oct. 21, 2021, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Nov. 12, 2021, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Jan. 28, 2022, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Mar. 10, 2022, U.S. Appl. No. 16/684,038, US. [cited by applicant]
May 11, 2022, 201980051898.6, CN. [cited by applicant]
Jul. 18, 2022, 202127025861, IN. [cited by applicant]
Sep. 21, 2022, U.S. Appl. No. 16/684,038, US. [cited by applicant]
Dec. 9, 2022, 201980051898.6, CN. [cited by applicant]
U.S. Appl. No. 16/684,038, filed Nov. 14, 2019. [cited by applicant]
Beijnen et al., “Chemical stability of two sterile, parenteral formulations of cyclophosphamide (Endoxan) after reconstitution and dilution in commonly used infusion fluids,” vol. 46(4), pp. 111-116, Jul.-Aug. 1992. [cited by applicant]
Kim, A.I. et al., “The physical state of mannitol after freeze-drying: effects of mannitol concentration, freezing rate, and a noncrystallizing cosolute”, Journal of Pharmaceutical Sciences, vol. 87, No. 8, pp. 931-935,… [cited by applicant]
“Understanding and interpreting particle size distribution calculations”, Horiba Scientific, Technical Note, result interpretation TN156, found at https://static.horiba.com/fileadmin/Horiba/Products/Scientific/Particle_… [cited by applicant]
Hiwale, P. et al., “Variables affecting reconstitution time of dry powder for injection”, Pharmaceutical Technology, vol. 32, No. 7, pp. 1-8, (2008). [cited by applicant]
Definition of “Bulk density” printed from Wikipedia, the free encyclopedia on Jun. 13, 2022 found at http://en.wikipedia.org/wiki/Bulk density. [cited by applicant]
“Particle size result interpretation; number vs. volume distributions”, Horiba Scientific, Technical Note, Number vs. Volume Distribution, TN154, pp. 1-2, (2021), found at https://static.horiba.com/fileadmin/Horiba/Prod… [cited by applicant]
Beijnen, J.H. et al., “Chemical stability of two sterile, parenteral formulations of cyclophosphamide (Endoxan) after reconstitution and dilution in commonly used infusion fluids”, PDA Journal of Pharmaceutical Science … [cited by applicant]
Entry for “Cytoxan and Lyophilized Cytoxan”, Physicians Desk Reference, 54 [cited by applicant]
International Search Report and Written Opinion dated Feb. 19, 2020 for PCT application No. PCT/IB2019/059802. [cited by applicant]
International Search Report dated Nov. 11, 2019 for PCT application No. PCT/CN2019/099251. [cited by applicant]
Extended European Search Report dated Apr. 19, 2022 for EP application No. 19844577.7. [cited by applicant]