Granted Patent
B2
US 12,358,942 · App. 18/455,324 · Granted Jul 15, 2025
Crystalline 19-nor C3,3-disubstituted C21-n-pyrazolyl steroid
Inventors:
Paul Steven Watson (Carrboro, NC); Bret Berner (Half Moon Bay, CA); John Gregory Reid (Wellington, FL); Jian Wang (Branchburg, NJ); James J. Doherty (Bedford, MA); Stephen Jay Kanes (Swarthmore, PA)
Assignee:
Sage Therapeutics, Inc.
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Abstract
This invention relates to a crystalline 19-nor C3,3-disubstituted C21-pyrazolyl steroid of Formula (I), and compositions thereof. Also disclosed herein are methods of making the same and methods of using the same.
Claims (6)
1. A crystalline solid form of Compound 1:
having an XRPD pattern comprising peaks between and including 9.3 to 9.7 degrees in 2θ, between and including 10.6 to 11.0 degrees in 2θ, between and including 13.0 to 13.4 degrees in 2θ, between and including 14.7 to 15.1 degrees in 2θ, between and including 15.8 to 16.2 degrees in 2θ, between and including 18.1 to 18.5 degrees in 2θ, between and including 18.7 to 19.1 degrees in 2θ, between and including 20.9 to 21.3 degrees in 2θ, between and including 21.4 to 21.8 degrees in 2θ, and between and including 23.3 to 23.7 degrees in 2θ.
2. The crystalline solid form of claim 1 , wherein the peak between and including 9.3 to 9.7 is 9.5 degrees in 2θ, the peak between and including 10.6 to 11.0 is 10.8 degrees in 2θ, the peak between and including 13.0 to 13.4 is 13.2 degrees in 2θ, the peak between and including 14.7 to 15.1 is 14.9 degrees in 2θ, the peak between and including 15.8 to 16.2 degrees is 16.0 in 2θ, the peak between and including 18.1 to 18.5 degrees is 18.3 in 2θ, the peak between and including 18.7 to 19.1 is 18.9 degrees in 2θ, the peak between and including 20.9 to 21.3 is 21.1 degrees in 2θ, the peak between and including 21.4 to 21.8 is 21.6 degrees in 2θ, and the peak between and including 23.3 to 23.7 is 23.5 degrees in 2θ.
3. A crystalline solid form of Compound 1:
having an XRPD pattern comprising peaks between and including 9.3 to 9.7 degrees in 2θ, between and including 10.6 to 11.0 degrees in 2θ, between and including 13.0 to 13.4 degrees in 2θ, between and including 18.7 to 19.1 degrees in 2θ, and between and including 21.4 to 21.8 degrees in 2θ.
4. The crystalline solid form of claim 3 , wherein the peak between and including 9.3 to 9.7 is 9.5 degrees in 2θ, the peak between and including 10.6 to 11.0 is 10.8 degrees in 2θ, the peak between and including 13.0 to 13.4 is 13.2 degrees in 2θ, the peak between and including 18.7 to 19.1 is 18.9 degrees in 2θ, and the peak between and including 21.4 to 21.8 is 21.6 degrees in 2θ.
Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 2, 2023
From: KANES, STEPHEN J.
To: SAGE THERAPEUTICS, INC.
Reel/Frame 065098/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 2, 2023
From: DOHERTY, JAMES J.
To: SAGE THERAPEUTICS, INC.
Reel/Frame 065098/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 2, 2023
From: WATSON, PAUL STEVEN; BERNER, BRET; REID, JOHN GREGORY; WANG, JIAN
To: SAGE THERAPEUTICS, INC.
Reel/Frame 065102/0208 →
Continuity (4)
Continuation
16326977
Provisional Application
62378582
· Aug 23, 2016
References Cited (281)
US 9365611B2
· Martinez Botella et al.
· 2016
[cited by applicant]
US 9512165B2
· Martinez Botella et al.
· 2016
[cited by applicant]
US 9630986B2
· Covey et al.
· 2017
[cited by applicant]
US 9676812B2
· Covey
· 2017
[cited by applicant]
US 9725481B2
· Martinez Botella et al.
· 2017
[cited by applicant]
US 9765110B2
· Covey
· 2017
[cited by applicant]
US 20050080107A1
· Shinohar
· 2005
[cited by applicant]
US 20100152840A1
· Seguin et al.
· 2010
[cited by applicant]
US 20110152840A1
· Lee et al.
· 2011
[cited by applicant]
US 20140050789A1
· Rogawski et al.
· 2014
[cited by applicant]
US 20140057885A1
· Reddy et al.
· 2014
[cited by applicant]
US 20140148412A1
· Hogenkamp
· 2014
[cited by applicant]
US 20150018327A1
· Reddy
· 2015
[cited by applicant]
US 20150175651A1
· Salituro et al.
· 2015
[cited by applicant]
US 20150291654A1
· Upasani et al.
· 2015
[cited by applicant]
US 20150313915A1
· Rogawski et al.
· 2015
[cited by applicant]
US 20160068563A1
· Martinez Botella et al.
· 2016
[cited by applicant]
US 20160152658A1
· Botella et al.
· 2016
[cited by applicant]
US 20160229887A1
· Martinez Botella et al.
· 2016
[cited by applicant]
US 20170232006A1
· Covey et al.
· 2017
[cited by applicant]
US 20170233433A1
· Martinez Botella et al.
· 2017
[cited by applicant]
US 20170348327A1
· Kanes et al.
· 2017
[cited by applicant]
US 20180133229A1
· Rogawski et al.
· 2018
[cited by applicant]
US 20180179247A1
· Botella et al.
· 2018
[cited by applicant]
US 20180311258A1
· Robichaud et al.
· 2018
[cited by applicant]
US 20190008873A1
· Salituro et al.
· 2019
[cited by applicant]
US 20190038639A1
· Reddy et al.
· 2019
[cited by applicant]
US 20190142845A1
· Rogawski et al.
· 2019
[cited by applicant]
US 20190177358A1
· Martinez Botella et al.
· 2019
[cited by applicant]
US 20190233465A1
· Robichaud et al.
· 2019
[cited by applicant]
US 20190269699A1
· Reddy
· 2019
[cited by applicant]
US 20190350944A1
· Salituro et al.
· 2019
[cited by applicant]
US 20200113916A1
· Covey et al.
· 2020
[cited by applicant]
US 20200113917A1
· Kanes et al.
· 2020
[cited by applicant]
US 20200223884A1
· Upasani et al.
· 2020
[cited by applicant]
US 20200276209A1
· Colquhoun et al.
· 2020
[cited by applicant]
US 20200281943A1
· Hoffmann et al.
· 2020
[cited by applicant]
US 20200291059A1
· Salituro et al.
· 2020
[cited by applicant]
US 20200306262A1
· Doherty
· 2020
[cited by applicant]
US 20200306265A1
· Kanes et al.
· 2020
[cited by applicant]
US 20210017218A1
· Martinez Botella et al.
· 2021
[cited by applicant]
US 20210040141A1
· Upasani et al.
· 2021
[cited by applicant]
US 20210061850A1
· Martinez Botella et al.
· 2021
[cited by applicant]
US 20210087223A1
· Martinez Botella et al.
· 2021
[cited by applicant]
US 20210100817A1
· Rogawski et al.
· 2021
[cited by applicant]
US 20210101928A1
· Robichaud et al.
· 2021
[cited by applicant]
US 20210113590A1
· Robichaud et al.
· 2021
[cited by applicant]
US 20210308149A1
· Covey et al.
· 2021
[cited by applicant]
US 20210338692A1
· Kanes et al.
· 2021
[cited by applicant]
US 20210347812A1
· Robichaud et al.
· 2021
[cited by applicant]
US 20210363175A1
· Salituro et al.
· 2021
[cited by applicant]
US 20210369734A1
· Doherty
· 2021
[cited by applicant]
US 20220110949A1
· Doherty et al.
· 2022
[cited by applicant]
US 20220213137A1
· Martinez Botella et al.
· 2022
[cited by applicant]
US 20220315621A1
· Robichaud et al.
· 2022
[cited by applicant]
US 20220323462A1
· Kanes et al.
· 2022
[cited by applicant]
US 20220372067A1
· Blanco-Pillado et al.
· 2022
[cited by applicant]
US 20230018765A1
· Kanes et al.
· 2023
[cited by applicant]
US 20230021308A9
· Robichaud et al.
· 2023
[cited by applicant]
US 20230046825A1
· Blanco-Pillado et al.
· 2023
[cited by applicant]
US 20230057130A1
· Watson et al.
· 2023
[cited by applicant]
US 20230085354A1
· Robichaud et al.
· 2023
[cited by applicant]
US 20230111081A1
· Rogawski et al.
· 2023
[cited by applicant]
US 20230141665A1
· Salituro et al.
· 2023
[cited by applicant]
US 20230149424A1
· Reddy
· 2023
[cited by applicant]
US 20230201224A1
· Kanes et al.
· 2023
[cited by applicant]
US 20230285417A1
· Watson et al.
· 2023
[cited by applicant]
US 20230287037A1
· Upasani et al.
· 2023
[cited by applicant]
US 20230310459A1
· Hoffmann et al.
· 2023
[cited by applicant]
US 20230346801A1
· Kanes
· 2023
[cited by applicant]
US 20230355639A1
· Kanes et al.
· 2023
[cited by applicant]
US 20230414636A1
· Kanes
· 2023
[cited by applicant]
US 20240122945A1
· Bonthapally et al.
· 2024
[cited by applicant]
US 20240197754A1
· Rogawski et al.
· 2024
[cited by applicant]
US 20240216395A1
· Lasser et al.
· 2024
[cited by applicant]
US 20240216396A1
· Lasser et al.
· 2024
[cited by applicant]
US 20240245711A1
· Lasser et al.
· 2024
[cited by applicant]
CN 108727453A
· 2018
[cited by applicant]
RU 2675855C2
· 2018
[cited by applicant]
WO 1991016897A1
· 1991
[cited by applicant]
WO 2001051919A2
· 2001
[cited by applicant]
WO 2003066590A1
· 2003
[cited by applicant]
WO 2013043985A1
· 2013
[cited by applicant]
WO 2013056181A1
· 2013
[cited by applicant]
WO 2013112605A2
· 2013
[cited by applicant]
WO 2013188792A2
· 2013
[cited by applicant]
WO 2014028398A2
· 2014
[cited by applicant]
WO 2014031792A2
· 2014
[cited by applicant]
WO 2014085668A1
· 2014
[cited by applicant]
WO 2014100228A1
· 2014
[cited by applicant]
WO 2014169831A1
· 2014
[cited by applicant]
WO 2014169832A1
· 2014
[cited by applicant]
WO 2014169833A1
· 2014
[cited by applicant]
WO 2014169836A1
· 2014
[cited by applicant]
WO WO2014169833
· 2014
[cited by examiner]
WO 2015010054A2
· 2015
[cited by applicant]
WO 2015027227A1
· 2015
[cited by applicant]
WO 2015180679A1
· 2015
[cited by applicant]
WO 2015195962A1
· 2015
[cited by applicant]
WO 2016040322A1
· 2016
[cited by applicant]
WO 2016061527A1
· 2016
[cited by applicant]
WO 2016061537A1
· 2016
[cited by applicant]
WO 2016082789A1
· 2016
[cited by applicant]
WO 2016123056A1
· 2016
[cited by applicant]
WO 2016134301A1
· 2016
[cited by applicant]
WO 2016164763A1
· 2016
[cited by applicant]
WO 2016209847A1
· 2016
[cited by applicant]
WO 2016205721A1
· 2016
[cited by applicant]
WO 2017044659A1
· 2017
[cited by applicant]
WO 2017066626A1
· 2017
[cited by applicant]
WO 2017087864A1
· 2017
[cited by applicant]
WO 2017156418A1
· 2017
[cited by applicant]
WO 2017156103A1
· 2017
[cited by applicant]
WO 2018013613A1
· 2018
[cited by applicant]
WO 2018013615A1
· 2018
[cited by applicant]
WO 2018039378A1
· 2018
[cited by applicant]
WO 2019018119A1
· 2019
[cited by applicant]
WO 2019045121A1
· 2019
[cited by applicant]
WO 2019051264A1
· 2019
[cited by applicant]
WO 2019051477A1
· 2019
[cited by applicant]
WO 2019055764A1
· 2019
[cited by applicant]
WO 2019094724A1
· 2019
[cited by applicant]
WO 2019113494A1
· 2019
[cited by applicant]
WO 2019126741A1
· 2019
[cited by applicant]
WO 2019126761A1
· 2019
[cited by applicant]
WO 2019140272A1
· 2019
[cited by applicant]
WO 2019241442A1
· 2019
[cited by applicant]
WO 2020077255A1
· 2020
[cited by applicant]
WO 2020082065A1
· 2020
[cited by applicant]
WO 2020118060A1
· 2020
[cited by applicant]
WO 2020132504A1
· 2020
[cited by applicant]
WO 2020243027A1
· 2020
[cited by applicant]
WO 2020243488A1
· 2020
[cited by applicant]
WO 2020264495A1
· 2020
[cited by applicant]
WO 2020264509A1
· 2020
[cited by applicant]
WO 2020264512A1
· 2020
[cited by applicant]
WO 2021113786A1
· 2021
[cited by applicant]
WO 2021188778A1
· 2021
[cited by applicant]
WO 2021195297A1
· 2021
[cited by applicant]
WO 2021195301A1
· 2021
[cited by applicant]
WO 2021262836A1
· 2021
[cited by applicant]
WO 2022020363A1
· 2022
[cited by applicant]
WO 2022020363A9
· 2022
[cited by applicant]
WO 2022115381A1
· 2022
[cited by applicant]
WO 2022165017A1
· 2022
[cited by applicant]
WO 2022177718A1
· 2022
[cited by applicant]
WO 2022197901A1
· 2022
[cited by applicant]
WO 2022221195A1
· 2022
[cited by applicant]
WO 2022232494A1
· 2022
[cited by applicant]
WO 2022232504A1
· 2022
[cited by applicant]
WO 2023158668A1
· 2023
[cited by applicant]
WO 2023163879A1
· 2023
[cited by applicant]
Anonymous: “Archive History for NCT03000530”, Aug. 4, 2017, Retrieved from the Internet: <URL:https://www.clinicaltrials.gov/ct2/his> tory/NCT03000530?V-_6=View#StudyPageTop; [retrieved on Nov. 20, 2018].
[cited by applicant]
“API Form Screening and Selection in Drug Disclovery Stage”, Pharm Stage 2007, v.6, n.10, pp. 20-25.
[cited by applicant]
Balbach, S., et al., “Pharmaceutical evaluation of early development candidates “The 100 mg approach””, International Journal of Pharmaceutica, 2004, vol. 275, pp. 1-12.
[cited by applicant]
Bavin, “Polymorphism in Process Development”, Chemistry and Industry, vol. 21, pp. 527-529, Aug. 21, 1989.
[cited by applicant]
Bernstein, BE., “Rett Syndrome Medication” [online], Updated Feb. 6, 2017, [retrieved on May 3, 2018]. Retrieved from the website Medscape, using internet URL: <https://emedicine.medscape.com/article/916377-medication>.
[cited by applicant]
Brittain, H. G., Polymorphism in Pharmaceutical Solids, Informa Healthcare, 2009.
[cited by applicant]
Byrn, S., et al., “Pharmaceutical Solids: A Strategic Approach to Regulatory Considerations”, Pharmaceutical Research 1995, vol. 12, No. 7, pp. 945-954.
[cited by applicant]
Caira, M.R., “Crystalline Polymorphism of Organic Compounds”, Topics in Current Chemistry, vol. 198, 1998, pp. 163-208.
[cited by applicant]
Carlson et al., “An Integrated High Throughput Workflow for Pre-formulations: Polymorph and Salt Selection Studies”, Pharm. Chem, Drug Development, vol. 2, No. 7, pp. 10-15, 2003.
[cited by applicant]
Censi, R. et al., Polymorph Impact on the Bioavailability and Stability of Poorly Soluble Drugs. Molecules, Oct. 15, 2015, vol. 20, No. 10, pp. 18759-18776.
[cited by applicant]
“Crystallization of Polymorphs and Pseudo-polymorphs and its Control”, Pharm Stage 2007, v.6, n. 10, pp. 48-53.
[cited by applicant]
Gunduz-Bruce, et al., “Sage-217 in Subjects with Major Depressive Disorder: Efficacy and Safety Results from Open-Label Part A of a Phase 2a Study”, Poster, (Presented on Sep. 2-5, 2017 at the 30th ECNP Congress, Paris,…
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2016/062874 dated Jan. 30, 2017.
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2017/041600 dated Dec. 1, 2017.
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2017/041605 dated Dec. 12, 2017.
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2018/050012 dated Dec. 7, 2018.
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2018/051048 dated Jan. 11, 2019.
[cited by applicant]
International Search Report and Written Opinion for Corresponding International Application No. PCT/US2018/064546 dated Apr. 9, 2019.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2018/067277 dated May 24, 2019.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2018/067306 dated May 28, 2019.
[cited by applicant]
Kawaguchi, Y., et al., “Drug and Crystal Polymorphism”, Journal of Human Environmental Engineering, 2002, v.4, pp. 310-317.
[cited by applicant]
Lee, E. H., A practical guide to pharmaceutical polymorph screening & selection. Asian Journal of Pharmaceutical Sciences, May 16, 2014, vol. 9, No. 4, pp. 163-175.
[cited by applicant]
Newman, A., Specialized Solid Form Screening Techniques. Organic Process Research & Development, Oct. 30, 2012, vol. 13, No. 3, pp. 457-471.
[cited by applicant]
Pharmaceutical Affairs Bureau Notification, No. 568, May 1, 2001, 45 pages.
[cited by applicant]
Sage Therapeutics: “Sage Therapeutics Advances SAGE-217 into Placebo-Controlled Phase 2 Clinical Trial in Major Depressive Disorder”, Feb. 13, 2017, Retrieved from the Internet: <URL:https://investor.sagerx.com/static-f…
[cited by applicant]
Singhal, D., et al., “Drug Polymorphism and dosage form design: a practical perspective”, Advanced Drug Delivery Reviews, 2004, vol. 56, pp. 335-347.
[cited by applicant]
Supplemental European Search Report, European Patent Application No. 14826212.4, mailed Feb. 16, 2017.
[cited by applicant]
Yamano, M., “Approach to Crystal Plymorph in Process Research of New Drug”, Journal of Synthetic Organic Chemistry, Japan, 2007, v.65, n.9, pp. 907-913.
[cited by applicant]
Zonana, et al., “The Neurobiology of Postpartum Depression”, CNS Spectrums, (2005), pp. 792-799, 805.
[cited by applicant]
Cited By (1)