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(19) TZZ ¥_T (11) EP 2 854 763 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 9/00 (2006.01) A61K 9/48 (2006.01) 26.09.2018 Bulletin 2018/39 (86) International application number: (21) Application number: 13728632.4 PCT/US2013/043447 (22) Date of filing: 30.05.2013 (87) International publication number: WO 2013/181449 (05.12.2013 Gazette 2013/49) (54) FORMULATIONS FOR VAGINAL DELIVERY OF ANTIPROGESTINS FORMULIERUNGEN ZUR VAGINALEN ABGABE VON ANTIPROGESTINEN FORMULATIONS D’ADMINISTRATION VAGINALE D’ANTIPROGESTINES (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • PODOLSKI, Joseph, S. GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO The Woodlands, TX 77381 (US) PL PT RO RS SE SI SK SM TR •HSU,Kuang Designated Extension States: The Woodlands, TX 77381 (US) ME (74) Representative: Nederlandsch Octrooibureau (30) Priority: 31.05.2012 US 201261653674 P P.O. Box 29720 2502 LS The Hague (NL) (43) Date of publication of application: 08.04.2015 Bulletin 2015/15 (56) References cited: EP-A1- 1 593 376 WO-A1-2011/039680 (73) Proprietor: Repros Therapeutics Inc. US-A1- 2008 248 102 US-A1- 2011 046 098 The Woodlands, TX 77380 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 854 763 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 854 763 B1 Description FIELD OF THE INVENTION 5 [0001] In several embodiments, the present invention relates to mucoadhesive pharmaceutical compositions and their use for local administration of active agents such as antiprogestins to the vaginal mucosa. In related embodiments, the mucoadhesive compositions are administered for the treatment of a variety of progesterone related conditions. BACKGROUND OF THE INVENTION 10 [0002] The effect of the steroid hormone progesterone on the reproductive system has been well-documented. For example, progesterone is vital to establishing and maintaining pregnancy and exerts actions on various tissues of the reproductive system. The action of progesterone on tissues outside the reproductive system has been reported but is less well characterized. 15 [0003] Antiprogestins, compounds which inhibit the action of progesterone, have considerable potential for use in the pharmacological regulation of fertility and a variety of conditions and diseases such as breast cancer and endometriosis. The first reported antiprogestin, mifepristone (RU 486), is one of a number of 19-nortestsosterone derivatives with strong affinity for both the progesterone and glucocorticoid receptors and with antiprogestational and antiglucocorticoid activity. A variety of antiprogestins based on the 19-norprogesterone backbone have also been synthesized. 20 [0004] US2011/046098 A1 discloses methods for administering compositions comprising progesterone receptor an- tagonist (e.g. antiprogestin, such as CDB-4124) for the treatment of endometrial proliferation, fibroids, endometriosis. The compounds can be administered to a patient via any conventional route (e.g. topically, transmucosally). The ad- ministration form can be a tablet, capsule, pill, etc. The composition can be administered in an amount of 1 mg/kg to 1 mg/kg body weight. 25 [0005] Several drawbacks are associated with the use of known antiprogestins, rendering them less than ideal for chronic administration, particularly when delivered orally. If these and other limitations associated with antiprogestin treatment could be improved, a significant advance in the treatment of hormone-dependent disorders would result. SUMMARY OF THE INVENTION 30 [0006] The scope of the invention is defined by the claims. Any references in the description to methods of treatment refer to the compounds, pharmaceutical compositions and medicaments of the present invention for use in a method for treatment of the human (or animal) body by therapy (or for diagnosis). [0007] In one embodiment, the present invention provides a mucoadhesive capsule comprising pullulan and a capsule 35 fill formulation comprising a selective progesterone receptor modulator (SPRM) and one or more excipients for delivering the active agent to the vaginal mucosa of a female for the treatment of a progesterone-dependent condition selected from the group consisting of endometriosis and pain associated therewith, adenomyosis, endometriomas of the ovary, dysmenorrhea, uterine fibroids, endometrial hyperproliferation, ovarian cancer, and cervical cancer. [0008] In other embodiments, the present disclosure provides methods for the treatment of a variety of progesterone 40 related conditions in a patient in need of such treatment by administering a mucoadhesive capsule comprising pullulan and a capsule fill formulation comprising an antiprogestin and one or more excipients to the vaginal mucosa of the patient. [0009] In other embodiments, the present disclosure provides a kit comprising a mucoadhesive capsule comprising pullulan and a capsule fill formulation comprising an active agent, preferably an anitprogestin and one or more excipients for delivering the agent to the vaginal mucosa in combination with an vaginal applicator. 45 [0010] Progesterone-related conditions that may be treated with the mucoadhesive capsules of the invention include, without limitation, endometriosis and pain associated therewith, adenomyosis, endometriomas of the ovary, dysmenor- rhea, endocrine hormone-dependent tumors, uterine fibroids, endometrial hyperproliferation, ovarian cancer, cervical cancer and breast cancer. Compositions of the instant invention may also be used to induce menses, to induce labor and for contraception. 50 BRIEF DESCRIPTION OF THE DRAWINGS [0011] 55 Fig. 1 illustrates the area under the curve (AUC) of CDB-4124 and its monodemethylated metabolite CDB-4453, following administration of CDB-4124 to human females with uterine fibroids at 1 mg, 3 mg, 6 mg, 9 mg and 12 mg oral doses compared with vaginal administration of a 12 mg dose. Fig. 2 illustrates a comparison of the Cmax (peak serum concentration) of CDB-4124 and CDB-4453 following 1 2 EP 2 854 763 B1 mg, 3 mg, 6 mg, 9 mg, and 12 mg oral doses to human females with uterine fibroids compared with vaginal admin- istration of a 12 mg dose. Fig. 3 illustrates pharmacokinetic data observed at steady state over a 24 hour period following administration of 1 mg, 3 mg, 6 mg, 9 mg and 12 mg oral versus 12 mg vaginal doses of CDB-4124. 5 Fig. 4A-B illustrates pharmacokinetic data observed over a 24 hour period in rabbits following the last of 10 daily doses of 12 mg CDB-4124 delivered vaginally. Panel A illustrates CDB-4124; Panel B illustrates CDB-4453. Fig. 5 illustrates the applicator used to vagnially deliver pullulan capsules comprising 12 mg CDB-4124 to human females. 10 DETAILED DESCRIPTION OF THE INVENTION [0012] While the present invention is capable of being embodied in various forms, the description below of several embodiments is made with the understanding that the present disclosure is to be considered as an exemplification of the invention, and is not intended to limit the invention to the specific embodiments illustrated. Headings are provided 15 for convenience only and are not to be construed to limit the invention in any way. Embodiments illustrated under any heading may be combined with embodiments illustrated under any other heading. [0013] It is to be understood that any ranges, ratios and ranges of ratios that can be formed by any of the numbers or data present herein represent further embodiments of the present invention. This includes ranges that can be formed that do or do not include a finite upper and/or lower boundary. Accordingly, the skilled person will appreciate that many 20 such ratios, ranges and ranges of ratios can be unambiguously derived from the data and numbers presented herein and all represent embodiments of the invention. [0014] Before the present compounds, compositions and methods are disclosed and described, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. It must be noted that, as used in the present specification and the appended claims, the singular forms "a," "an" 25 and "the" include plural referents unless the context clearly dictates otherwise. Definitions [0015] The term "capsule" refers to a hard shell pharmaceutical capsule. The capsule consists of a body and cap and 30 may comprise a fill formulation containing a pharmacologically active agent. [0016] The term "oral" administration means that the active agent is in a formulation designed to be ingested, i.e. designed to be delivered to the gastrointestinal system for absorption. [0017] The term "effective dosage" means an amount of the composition’s active component sufficient to treat a particular condition. 35 [0018] The term "selective progesterone receptor modulators" means compounds that affect functions of progesterone receptor in a tissue-specific manner. The compounds act as progesterone receptor antagonists in some tissues (for example, in breast tissue) and as progesterone receptor agonists in other tissues (for example, in the uterus). [0019] The term "treat"
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