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(12) Patent Application Publication (10) Pub. No.: US 2011/0135719 A1 Besins Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2011/0135719 A1 Besins Et Al US 2011 0135719A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0135719 A1 Besins et al. (43) Pub. Date: Jun. 9, 2011 (54) PHARMACEUTICAL COMPOSITION BASED (30) Foreign Application Priority Data ON MICRONIZED PROGESTERONE, PREPARATION METHOD AND USES Nov. 13, 2001 (FR) ...................................... O1 (14653 THEREOF Publication Classification (75) Inventors: Antoine Besins, Bruxelles (BE); (51) Int. Cl. Jerome Besse, Listrac Medoc (FR) A 6LX 3/57 (2006.01) A69/48 (2006.01) (73) Assignee: Besins Manufacturing Belgium A6IP5/24 (2006.01) (21) Appl. No.: 12/916,795 (52) U.S. Cl. .......................... 424/451; 514/177; 514/170 (22) Filed: Nov. 1, 2010 (57) ABSTRACT Related U.S. Application Data The present invention relates to a pharmaceutical composi tion comprising micronized progesterone, soya bean lecithin, (63) Continuation of application No. 12/071,822, filed on and at least one oil selected from the group consisting of Feb. 27, 2008, now Pat. No. 7,829,115, which is a Sunflower oil, olive oil, sesame see oil, colza oil, almond oil, continuation of application No. 10/495,242, filed on to the method for the preparation thereof and to the uses May 6, 2004, now Pat. No. 7,431,941, filed as appli thereof for treating a physiological condition linked to insuf cation No. PCT/FR02/03879 on Nov. 13, 2002. ficiency of progesterone secretion. Patent Application Publication Jun. 9, 2011 Sheet 1 of 4 US 2011/0135719 A1 FIG. 1 I III UI II I III. Y. H || ||N|N II|| || NA I IVNA IN I I \\ I III VIII HAHII MRIVN 0 1 0, 1 1 10 100 1000 3000 PARTICLE SIZE GAL 221.01 CAPS START BATCH QBO1249020, 10/15/01 10:48:30 T. PFO098 CAPS BATCH 5439. 10/02/01 11:33:35 (UTROGESTANG) CAPSULE) Patent Application Publication Jun. 9, 2011 Sheet 2 of 4 US 2011/0135719 A1 FIG. 2 100 90 80 70 60 50 40 BO 20 10 30 60 90 120 150 180 210 2.0 20 300 330 360 TIME (MINUTES) -- UTROGESTAN 100 mg - BATCH 5604 -É3-- 100 mg SOFT PROGESTERONE CAPSULE - BATCH QBO 1187020 Patent Application Publication Jun. 9, 2011 Sheet 3 of 4 US 2011/0135719 A1 FIG. 3 PROGESTERONE: MEAN CONCENTRATION - TIME N - 60 mem CAPSULE ACCORDING TO THE INVENTION -- UTROGESTANE 20000 15000 10000 5000 0 0.0 3,0 6.0 9.0 120 15,0 18.0 21.0 24,0 27.0 300 33,0 36,0 TIME (hrs) Patent Application Publication Jun. 9, 2011 Sheet 4 of 4 US 2011/0135719 A1 FIG. 4 PROGESTERONE: Lin (MEAN CONCENTRATION) - TEMPS N = 60 1200 c -- CAPSULE ACCORDING TO THE INVENTION 3. 10,00+ 1"444N -- UTROGESTAN& 2 k 8.00 Z z 6.00 O 2. O O 4,00 a. t O S 2.00 - 0.0 30 6,0 90 120 150 18.0 210 240 27.0 30,0 33,O 360 TIME (hrs) US 2011/0135719 A1 Jun. 9, 2011 PHARMACEUTICAL COMPOSITION BASED 0012. The oil which serves as a basis for the oily suspen ON MICRONIZED PROGESTERONE, sion in UTROGESTANR) is peanut oil. PREPARATION METHOD AND USES 0013 Peanut (Arachis hypogae) is a leguminous plant, a THEREOF bushy annual plant with yellow flowers, of the Papilionacea family. CROSS-REFERENCE TO RELATED 0014. In the last 15 years, peanut allergy has become a APPLICATIONS considerable allergological problem. (0015. Dutau et al. (La Presse Médicale Medical Press), 0001. This application is a continuation of U.S. applica vol. 28, p. 1553) observe that the prevalence of peanut allergy tion Ser. No. 12/071,822, filed Feb. 27, 2008, which is a has recently been estimated at 1.3% in the general population. continuation of U.S. application Ser. No. 10/495,242, filed The increased use of peanut in food, very often in a masked May 6, 2004, which is the U.S. National Stage of PCT/FR02/ form, perhaps explains this development. 03879, filed Nov. 13, 2002, the entire contents of which are 0016 Early sensitizations have been described in infants incorporated herein by reference in its entirety. The applica who have never consumed peanuts in conventional form, but tion also claims priority to FR 01/14653, filed Nov. 13, 2001. who were apparently sensitized in utero or via maternal milk, through maternalized milks having contained plant fats (pea BACKGROUND nut oil) or through medicinal preparations in oily solution. 0002 The present invention relates to a pharmaceutical (0017 UTROGESTANR) may be prescribed in many cases composition containing micronized progesterone, Soya bean of therapeutic indications, including as a Supplement to the lecithin, and at least one oil selected from the group consist luteal phase during cycles of in vitro fertilization (IVF), and ing of Sunflower oil, olive oil, Sesame seed oil, colza oil and in the case of a danger of abortion or of prevention of repeat almond oil. It also relates to pharmaceutical products com abortion due to luteal insufficiency, up to the 12th week of prising said pharmaceutical composition. pregnancy. It is therefore possible, in theory, for a fetus to be 0003. The invention also relates to the method for manu exposed to UTROGESTANR) in utero. facturing this pharmaceutical composition, as well as to the 0018 To date, while the allergenic effects of peanut are uses thereof. definite, a controversy still exists regarding the ability of 0004 Progesterone is a hormone which is synthesized, in peanut oil to engender allergenic reactions. Many publica women, essentially by the ovary during the postovulation or tions may be cited on this subject, including: Taylor et al., J. luteal phase (more precisely by the cells of the corpus luteum) Allergy Clin. Immunol. Vol. 68, p. 372 (1981); Moneret and, to a lesser degree, by the adrenal glands and the placenta Vautrinet al., Pediatr. Allergy Immunol. Vol. 5, p. 184 (1994); during the second part of pregnancy. Non-endocrine synthe Sabbah and Lauret, Allergie et Immunologie, vol. 26, p. 380 sis of progesterone, in particular in neurons, is also possible. (1994); de Montis et al., Arch. Pediatr., vol. 2. p. 25 (1995)). 0005. A consequence of insufficiency of progesterone 0019 Given this fact, the applicant company devoted itself secretion in a woman is a loss of its biological effects: proges to developing a novel pharmaceutical composition, replacing tative effect, anti-androgen effect (action on the skin) and the peanut oil with other oils which do not have high risks of anti-Oestrogen effect (the consequence being hyperoestro allergenicity, while at the same time endeavouring to con genemia: hot flushes, psychogenic difficulties of the anxious serve the advantages of the prior formula. or depressive type, weight gain, etc.). This progesterone insufficiency may lead to functional difficulties and diverse BRIEF DESCRIPTION OF THE DRAWINGS clinical manifestations, in particular: 0020 FIG. 1 illustrates the results of a comparative par 0006 premenstrual syndromes, ticle size study between UTROGESTANR) capsules (dashed 0007 menstrual irregularities due to disovulation or line) and capsules described herein containing Sunflower oil anovulation, (solid line). 0008 benign mastopathies, 0021 FIG. 2 illustrates the results of a comparative disso 0009 perimenopause and menopause. lution study between UTROGESTANR) capsules (0) and 0010. However, oral administration of progesterone suf capsules described herein containing sunflower oil (). fers from a serious handicap due to the poor intestinal absorp 0022 FIG. 3 illustrates the results of a bioequivalence tion and to the intense hepatic metabolism (short plasmatic study between UTROGESTANR) capsules (+) and capsules half-life) of this hormone. Only the vaginal, rectal and intra described herein containing sunflower oil (), with respect to muscular pathways would, to date, make it possible to main mean plasma concentration (pg/ml). tain blood progesterone level at the physiological level of the 0023 FIG. 4 illustrates the results of a bioequivalence luteal phase, for several hours. study between UTROGESTANR) capsules (+) and capsules 0011. The LABORATOIRES BESINS-ISCOVESCO described herein containing sunflower oil (), with respect to have already proposed a solution in order to improve the the natural log (Ln) of mean plasma concentration (pg/ml). quality and intensity of the digestive absorption of natural progesterone, in Patent Application FR 76 36007. Specifi DETAILED DESCRIPTION cally, they have developed a formulation of soft capsules containing micronized progesterone in oily suspension. The 0024. After much study and research, during which sev synergistic effect of the micronization and the use of mol eral plant oils were tested, sunflower oil, olive oil, sesame ecules containing long-chain fatty acids has made it possible seed oil, colza oil and almond oil were selected. Specifically, to indisputably increase the bioavailability of progesterone the use of these oils makes it possible to rule out the risks of taken orally. This formulation has known a great deal of allergic reactions, while at the same time conserving all of the success worldwide. It is sold in France under the trade mark physicochemical and kinetic characteristics of the prior UTROGESTANCR). UTROGESTANR) formulation, characteristics which were US 2011/0135719 A1 Jun. 9, 2011 the cause of its success. Given that the method manufacturing micronized progesterone in Suspension became apparent the prior UTROGESTANR) formulation on an industrial scale between the composition based on peanut oil and that con comprise steps which are very delicate to carry out, it is to the taining the oils used in accordance with the invention. credit of the applicant company to have Succeeded in modi 0033. With regard to the other oils tested, the particle size fying the formulation without increasing the production dif was not the same in the presence or absence of the Soya bean ficulties. lecithin. The main advantage of the oils selected according to 0025.
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