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(12) United States Patent (10) Patent No.: US 9,364,547 B2 Giliyar Et Al

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(12) United States Patent (10) Patent No.: US 9,364,547 B2 Giliyar Et Al US009364,547B2 (12) United States Patent (10) Patent No.: US 9,364,547 B2 Giliyar et al. (45) Date of Patent: *Jun. 14, 2016 (54) 17-HYDROXYPROGESTERONE ESTER (58) Field of Classification Search CONTAINING ORAL COMPOSITIONS AND USPC .................................................. 514/170, 182 RELATED METHODS See application file for complete search history. (71) Applicant: Lipocine Inc., Salt Lake City, UT (US) (56) References Cited (72) Inventors: Chandrashekar Giliyar, North Maple U.S. PATENT DOCUMENTS Grove, MN (US); Srinivasan Venkateshwaran, Salt Lake City, UT 3,164,520 A 1/1965 Raymond (US); Basawaraj Chickmath, 4,196,188 A 4, 1980 Besins Plymouth, MN (US); Satish Kumar (Continued) Nachaegari, Salt Lake City, UT (US); Nachiappan Chidambaram, Sandy, UT FOREIGN PATENT DOCUMENTS (US); Mahesh V. Patel, Salt Lake City, CN 1398590 A 2, 2003 UT (US) CN 1446540 A 10, 2003 (73) Assignee: LIPOCINE INC., Salt Lake City, UT (Continued) (US) OTHER PUBLICATIONS *) NotOt1Ce: Subjubject to anyy d1Sclaimer,disclai theh term off thisthi U.S. Appl. No. 14/801,737, filed Jul. 16, 2015; Chandrashekar patent is extended or adjusted under 35 Giliyar, Office Action dated Aug. 19, 2015. U.S.C. 154(b) by 26 days. (Continued) This patent is Subject to a terminal dis claimer. Primary Examiner — San-Ming Hui (21) Appl. No.: 14/261,057 (57) ABSTRACT (22) Filed: Apr. 24, 2014 The present invention provides for bioavailable oral dosage forms containingesters of 17-hydroxyprogesteroneas well as (65) Prior Publication Data related methods. The oral dosage forms can beformulated for pregnancy Support and can include atherapeutically effective US 2014/0271882 A1 Sep. 18, 2014 amount of an ester of 17-hydroxyprogesterone and a pharma Related U.S. Application Data ceutically acceptable carrier. In another embodiment, a phar maceutically acceptable oral dosage form for pregnancy Sup (62) Division of application No. 13/193,571, filed on Jul. port is provided. The pharmaceutically acceptable oral 28, 2011, now Pat. No. 8,951,996. dosage can include a therapeutically effective amount of an ester of 17-hydroxyprogesterone and a pharmaceutically (51) Int. Cl. acceptable carrier. The oral dosage form can, when measured A6 IK3I/56 (2006.01) using a USP Type-II dissolution apparatus in 900 mL of A6 IK 47/44 (2006.01) deionized water with 0.5 (w/v) of sodium lauryl sulfate at 50 (Continued) RPM at 37°C., release at least 20 wt % of the dose of the ester (52) U.S. Cl. of 17-hydroxyprogesterone after 60 minutes, or in the alter CPC. A61 K47744 (2013.01); A61K 8/63 (2013.01); native release at least 20 wt % more after 60 minutes than an A61 K9/0053 (2013.01); A61 K9/14 (2013.01); equivalently dosed oral dosage form without the carrier. (Continued) 20 Claims, 2 Drawing Sheets 100 -e-Example-1 s O H-Example 2 4. O 20 US 9,364,547 B2 Page 2 (51) Int. Cl. 2009/0098200 A1 4/2009 Temtsin Krayz et al. 2009/0123534 A1 5/2009 Besins et al. A6 IK9/48 (2006.01) 2009/0264395 A1 10/2009 Creasy A6 IK9/00 (2006.01) 2011/015284.0 A1 6, 2011 Lee et al. A 6LX3/57 (2006.01) 2011/0312927 A1 12/2011 Nachaegari et al. A6 IK9/20 (2006.01) 2011/0312928 A1 12/2011 Nachaegari et al. 2012/0148675 A1 6, 2012 Chickmath et al. A6 IK 9/14 (2006.01) 2013/0023505 A1 1/2013 Garfield et al. A6 IK 9/16 (2006.01) 2013/0029947 A1 1/2013 Nachaegari et al. A6 IK 8/63 (2006.01) A61O II/00 (2006.01) FOREIGN PATENT DOCUMENTS A6 IK 47/10 (2006.01) CN 150972O A T 2004 3C Z (2006.01)23. JPCN 2004f1557801623550 A 6/20046, 2005 A6 IK 47/20 (2006.01) JP 2006-524.238 10, 2006 A6 IK 47/22 (2006.01) WO WO90,08537 A1 8/1990 A6 IK 47/26 (2006.01) WO WO93, 12797 A1 7, 1993 WO WO95/05807 A1 3/1995 A6 IK 47/32 (2006.01) WO WOOO. 59482 A1 10, 2000 (52) U.S. Cl. WO WO 2003,077.923 A1 9, 2003 CPC ............... A61K 9/145 (2013.01); A61 K9/1617 WO WO 2004/080438 A1 9, 2004 (2939). All K%162.2939). A61& W. W. 3876%, A2 1 388 9/1635 (2013.01); A61 K9/1641 (2013.01); WO WO 2010/117873 A2 10/2010 A61 K9/1652 (2013.01); A61 K9/1676 WO WO 2011/O53666 5, 2011 (2013.01); A61 K9/2018 (2013.01); A61 K 9/2031 (2013.01); A61 K9/2054 (2013.01); OTHER PUBLICATIONS A61 K9/2059 (2013.01); A61 K9/4841 (2013.01); A61 K9/4858 (2013.01); A61 K U.S. Appl. No. 14/633,545, filed Feb. 27, 2015; Chandrashekar 9/4866 (2013.01); A61 K3I/57 (2013.01); Giliyar, Office Action dated Aug. 20, 2015. U.S. Appl. No. 13/644,929, filed Oct. 4, 2012; Satish Kumar A61K47/10 (2013.01); A61K 47/12 (2013.01); Nachaegari: Office Action dated Oct. 2, 2015. A61K47/14 (2013.01); A61K 47/20 (2013.01); U.S. Appl. No. 14/633,545, filed Feb. 27, 2015; Chandrashekar A61K47/22 (2013.01); A61K 47/26 (2013.01); Giliyar, Notice of Allowance dated Oct. 7, 2015. A61 K47732 (2013.01); A61O II/00 (2013.01); De Lignieres; Oral Micronized Progesterone; Clinical Therapeutics; A6 IK 2800/10 (2013.01) Jan. 1999: pp. 41-60; vol. 21. No. 1; Elsevier. Defranco etal; Vaginal Progesterone is Associated with a Decrease in (56) References Cited Risk for Early Preterm Birth and Improved Neonatal Outcome in U.S. PATENT DOCUMENTS Women with a Short Cervix: A Secondary Analysis from a Random ized, Double-Blind; Placebo-Controlled Trial; Ultrasound in 4,230,702 10, 1980 Eckert et al. Obsetrics and Gynecology; Oct. 2007: pp. 697-705; vol. 30, No. 5; 4,439.432 3, 1984 Peat John Wiley & Sons, Inc. 5,057,319 10, 1991 Gottwald et al. Emerald Performance Materials; Benzyl Benzoate; Product Informa 5,140,021 8, 1992 Maxson tion Bulletin; upon belief and knowledge prior to May 17, 2013: 3 5,314,882 5, 1994 Pantic et al. 5,543,150 8, 1996 Bologna et al. pages; Revision 01; Emerald Kalama Chemical, LLC. 5,620,705 4, 1997 Dong et al. EP application 12818254.0 filed Jan. 31, 2013; Lipocine, Inc.; Euro 5,633,011 5, 1997 Dong et al. pean Search Report dated Nov. 20, 2014. 5,645,856 7, 1997 Lacy EP Application 12822217.1: Filing date Aug. 3, 2012; Lipocine Inc.; 5,770.227 6, 1998 Dong et al. European Search Report dated Feb. 23, 2015. 5.948,766 9, 1999 Milan et al. FDA; 17a Alpha Hydroxyprogesterone Caproate for Prevention of 6,086,916 T/2000 Agnus Preterm Birth, Overview of FDA Background Document; Aug. 2, 6,096.338 8, 2000 Lacy 2006; 62 pages (see introduction); Food and Drug Administration. 6,117,450 9, 2000 Dittgen et al. Greene; Progesterone and Preterm Delivery Déja Vu All Over 6,294,192 B1 9, 2001 Patel Again; The New England Journal of Medicine; Jun. 12, 2003; pp. 6,500,814 B1 12, 2002 Hesch 6,544.553 B1 4, 2003 Hsia et al. 2453-2455; vol. 348, No. 24; Massachusetts Medical Society. 6,602,521 B1 8, 2003 Ting et al. Levy et al.; Pharmacokinetics of Natural Progesterone Administered 6,656,929 B1 12, 2003 Agnus et al. in the Formofa Vaginal Tablet; Human Reproduction; Mar. 1999: pp. 6,866,865 B2 3, 2005 Hsia et al. 606-610; vol. 14, No. 3.; European Society of Human Reproduction 6,923,988 B2 8, 2005 Patel et al. and Embryology. 7,431,941 B2 10, 2008 Besins et al. O'Brien et al; Progesterone Vaginal Gel for the Reduction of Recur 7,473,687 B2 1/2009 Hoffman et al. rent Preterm Birth: Primary Results From a Randomized, Double 7,943,602 B2 5, 2011 Bunschoten et al. Blind, Placebo-Controlled Trial: Ultrasound in Obstetrics and Gyne 7,976,871 B2 T/2011 Vaya et al. cology; Oct. 2007: pp. 687-696; vol. 30, No. 5; John Wiley & Sons, 8,133,507 B2 3/2012 Yum et al. Inc. 8,951,996 B2 2, 2015 Gilliyar et al. 2002/013 1988 A1 9, 2002 Foster et al. PCT Application PCT/US2011/041123; filed Jun. 20, 2011; Satish 2003/0077297 A1 4, 2003 Chen et al. Kumar Nachaegari; International Search Report mailed Feb. 21. 2003/0236236 A1 12, 2003 Chen et al. 2012. 2004/0052824 A1 3, 2004 Abou Chacra-Vernet et al. PCT Application PCT/US2013/063584; filed Oct. 4, 2013: Lipocine 2004/O131553 A1 T/2004 Besse Inc.; International Search report mailed Mar. 21, 2014. 2004/0266025 A1 12, 2004 Hickok et al. PCT/US2012/048708; Filed Jul. 27, 2012; Lipocine Inc., et al.; inter 2006, OOO9509 A1 1, 2006 Grubb et al. national search report dated Feb. 15, 2013. 2006/0275360 A1 12, 2006 Ahmed et al. PCT/US2012/049602; Filed Aug. 3, 2012; Lipocine Inc., et al.; inter 2008. O188829 A1 8, 2008 Creasy national search report dated Jan. 29, 2013. US 9,364,547 B2 Page 3 (56) References Cited U.S. Appl. No. 13/029,989, filed Feb. 17, 2011: Feng-Jing Chen; office action dated Nov. 18, 2013. OTHER PUBLICATIONS U.S. Appl. No. 13/193,571, filed Jul. 28, 2011; Chandrashekar Giliyar; office action dated Apr. 23, 2014. Rai et al.; Oral Micronized Progesterone for Prevention of Preterm U.S. Appl. No. 13/193,571, filed Jul. 28, 2011; Chandrashekar Birth; International Journal of Gynecology and Obstetrics; Jan.
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