CN102058604A - Drug composition containing dienogest and estradiol valerate and preparation method thereof - Google Patents
Drug composition containing dienogest and estradiol valerate and preparation method thereof Download PDFInfo
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- CN102058604A CN102058604A CN2009102381914A CN200910238191A CN102058604A CN 102058604 A CN102058604 A CN 102058604A CN 2009102381914 A CN2009102381914 A CN 2009102381914A CN 200910238191 A CN200910238191 A CN 200910238191A CN 102058604 A CN102058604 A CN 102058604A
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- Prior art keywords
- dienogest
- estradiol valerate
- preparation
- pharmaceutical composition
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- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2 RSEPBGGWRJCQGY-RBRWEJTLSA-N 0.000 title claims abstract description 21
- 229940008227 dienogest and estradiol Drugs 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title abstract description 5
- 229940079593 drug Drugs 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 229960004756 ethanol Drugs 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 210000000214 mouth Anatomy 0.000 claims description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007884 disintegrant Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 abstract description 10
- 239000004480 active ingredient Substances 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- 229960004766 estradiol valerate Drugs 0.000 description 8
- AZFLJNIPTRTECV-FUMNGEBKSA-N dienogest Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)([C@](CC3)(O)CC#N)CC3)C3=C21 AZFLJNIPTRTECV-FUMNGEBKSA-N 0.000 description 6
- 229960003309 dienogest Drugs 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007779 soft material Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 239000000583 progesterone congener Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229920003081 Povidone K 30 Polymers 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 210000004696 endometrium Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010030247 Oestrogen deficiency Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 108010085012 Steroid Receptors Proteins 0.000 description 1
- 229960004998 acesulfame potassium Drugs 0.000 description 1
- 235000010358 acesulfame potassium Nutrition 0.000 description 1
- 239000000619 acesulfame-K Substances 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000000270 basal cell Anatomy 0.000 description 1
- 210000002459 blastocyst Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037182 bone density Effects 0.000 description 1
- -1 compound estradiol valerate Chemical class 0.000 description 1
- 210000004246 corpus luteum Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 150000002159 estradiols Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000001009 osteoporotic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000003998 progesterone receptors Human genes 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 102000005969 steroid hormone receptors Human genes 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a drug composition containing dienogest and estradiol valerate and a preparation method thereof. The composition takes dienogest and estradiol valerate as active ingredients, and the pharmaceutically acceptable auxiliary materials are added, thus the in-vitro dissolution is complete, the stability is good, the preparation process is simple and the industrial production is easy to realize.
Description
Technical field
The present invention relates to a kind of pharmaceutical composition that contains dienogest and estradiol valerate and preparation method thereof.
Background technology
Progestogen are the important chemical substances of a class, mainly are by ovary and corpus luteum secretion.The dependent interaction of progestogen mediations be on the basis of estrogen action, makes that endometrium continues to thicken, congested, glandular hyperplasia and branch, for blastocyst is implanted and embryo support implantation, promotion inner membrance basal cell are divided into Tui Mo and prepare.Add with progestogen in the time of owing to the discovery complementing estrogen and also can protect endometrium the eighties in 20th century, reduces the sickness rate of carcinoma of endometrium, can be used to eliminate the osteoporotic generation of menopausal women symptom, bone density improving and reduction clinically.
Dienogest can combine with progesterone receptor fully and not with other steroid receptors cross reaction, when therapeutic dose, do not have androgen, estrogen and glucocorticoid effect, metabolism and blood pressure are not made significant difference, can not offset the protective effect of estrogen to blood vessel wall.In recent years, dienogest is also receiving much concern aspect the anti-male fertility effect.Estradiol valerate is a kind of long-acting derivatives of estradiol, can not only alleviate the symptoms of menopause that causes because of estrogen deficiency, and postmenopausal osteoporosis is had the excellent prevention effect.At present, estradiol valerate has been widely used in clinical, and has obtained very good curative effect.
CN100462078C discloses a kind of compound estradiol valerate tablet and preparation method thereof, and wherein estradiol valerate adds with the form of superfine powder.Raw material can significantly improve the dissolution of medicine behind micronization, but loss is bigger, for the higher raw material of prices such as dienogest and estradiol valerate, adopts this technology can cause a large amount of losses of raw material, will certainly increase the production cost of enterprise.In addition, the not all production unit acceptable of special installation of micronization needs.For fear of above problem, and it is actual in conjunction with producing, the applicant utilizes pharmaceutically acceptable solvent that dienogest and estradiol valerate are prepared as solution, so not only preparation technology is simple, and medicine can be evenly dispersed in the compositions, thereby guaranteed the dissolution and the uniformity of dosage units of medicine.
Summary of the invention
The objective of the invention is to disclose a kind of pharmaceutical composition that contains dienogest and estradiol valerate and preparation method thereof, what be specifically related to is to be active component with dienogest and estradiol valerate, add acceptable accessories, wherein said composition exists with tablet, oral cavity disintegration tablet, granule, capsule form, not only external stripping fully, have good stability, and preparation technology is simple, is highly susceptible to suitability for industrialized production, can be used for the estrogenic succedaneum behind the postmenopausal women.
Described dienogest and estradiol valerate are to add with the solution form after being dissolved in certain solvent.
The solvent of described active component is selected from ethanol or dehydrated alcohol.
Contain gas-producing disintegrant in the described compositions.
Described gas-producing disintegrant is selected from the compositions of citric acid or tartaric acid and sodium bicarbonate or sodium carbonate.
Described compositions existence form is tablet, oral cavity disintegration tablet, granule, capsule.
The specific embodiment
The existence form of embodiment 1 this embodiment is a tablet
Preparation technology:
1. the dienogest and the estradiol valerate that take by weighing recipe quantity are dissolved in the adequate amount of ethanol, and be standby;
2. prepare 10% starch slurry as binding agent, standby;
3. with the solution mixing of lactose and active component, fling to ethanol, again with microcrystalline Cellulose, citric acid by the equivalent principle mixing that progressively increases;
4. add 10% starch slurry system soft material, 16 mesh sieves are granulated;
5.50 ℃ be dried to determination of water value L.O.D (90 ℃, 5min)＜3.5%;
6.20 mesh sieve granulate;
7. add sodium bicarbonate and magnesium stearate, mixing in proportion;
8. Φ 6mm plane chamfering stamping.
The existence form of embodiment 2 these embodiment is an oral cavity disintegration tablet
Preparation technology:
1. the dienogest and the estradiol valerate that take by weighing recipe quantity are dissolved in the adequate amount of ethanol, and be standby;
2. prepare the alcoholic solution (ethanol: water=50: 50), standby of 15% 30 POVIDONE K 30 BP/USP 30;
3. with the solution mixing of mannitol and active component, fling to ethanol, again with ethyl cellulose-RT-10, tartaric acid by the equivalent principle mixing that progressively increases,
4. add binding agent system soft material, 16 mesh sieves are granulated;
5.50 ℃ be dried to determination of water value L.O.D (90 ℃, 5min)＜3.5%;
9.24 mesh sieve granulate;
10. add sodium carbonate, acesulfame potassium and magnesium stearate, mixing in proportion;
11. Φ 6mm plane chamfering stamping.
The existence form of embodiment 3 these embodiment is a granule
Preparation technology:
1. the dienogest and the estradiol valerate that take by weighing recipe quantity are dissolved in the adequate amount of ethanol, and be standby;
2. prepare the alcoholic solution (ethanol: water=50: 50), standby of 15% 30 POVIDONE K 30 BP/USP 30;
3. with the solution mixing of mannitol and active component, fling to ethanol, again with microcrystalline Cellulose, tartaric acid by the equivalent principle mixing that progressively increases,
4. add binding agent system soft material, 14 mesh sieves are granulated;
5.50 ℃ be dried to determination of water value L.O.D (90 ℃, 5min)＜3.5%;
6.16 mesh sieve granulate;
7. add sodium carbonate, flavoring orange essence, mixing in proportion.
The existence form of embodiment 4 these embodiment is a capsule
Preparation technology:
1. the dienogest and the estradiol valerate that take by weighing recipe quantity are dissolved in the adequate amount of ethanol, and be standby;
2. prepare 10% starch slurry as binding agent, standby;
3. with the solution mixing of mannitol and active component, fling to ethanol, again with microcrystalline Cellulose, citric acid by the equivalent principle mixing that progressively increases,
4. add binding agent system soft material, 18 mesh sieves are granulated;
5.50 ℃ be dried to determination of water value L.O.D (90 ℃, 5min)＜3.5%;
6.30 mesh sieve granulate;
7. add sodium bicarbonate, magnesium stearate, mixing in proportion;
8.4# capsule shells is filled.
The sample of 5 couples of embodiment of embodiment, 1,2,3,4 preparations carries out dissolution determination
Sample 1,2,3,4 to embodiment 1,2,3,4 preparations carries out determination of dissolution rate respectively, wherein dissolution adopts " second method in 2005 editions two appendix XC dissolution methods of Chinese pharmacopoeia, dissolution medium is the 0.5%SDS aqueous solution of 900mL, and rotating speed is 75r/min, the 30min sampling.
Embodiment 6 raw materials adopt micronization and two kinds of forms of solution to add respectively, and the sample of preparation carries out dissolution determination
Adopt the technical scheme of embodiment 1, the feedstock production sample that adds micronization, two kinds of forms of solution respectively is 1,2, and the determination of dissolution rate method is identical with embodiment 5.
As seen from the above table, adopt the dissolution of sample of the feedstock production of two kinds of forms not have marked difference respectively.
The sample of 7 couples of embodiment of embodiment, 1,2,3,4 preparations carries out Determination of Content Uniformity, and its result is as follows:
According to " A+1.80S≤15 under 2005 editions two appendix XE items of Chinese pharmacopoeia, the uniformity of dosage units of each preparation is all good.
The oral cavity disintegration tablet of 8 couples of embodiment of embodiment, 2 preparations carries out the mensuration of disintegration
Assay method: select 6 experimenters, oral cavity disintegration tablet is placed on the tongue and timing, last Hubei Province and tongue last slice slightly rub, and stop timing when no solid or grittiness in mouth, and the result is as follows:
The sample of 9 couples of embodiment of embodiment, 1 preparation carries out accelerated stability test, and the result is as follows:
Hence one can see that, and this kind contains the sample of preparation of pharmaceutical compositions of dienogest and estradiol valerate, and not only dissolution height, content are even, quicken 6 months good stabilities, and cost are low, have development and application and are worth.
Claims (6)
1. pharmaceutical composition that contains dienogest and estradiol valerate and preparation method thereof is characterized in that said composition is is active component with dienogest and estradiol valerate, adds acceptable accessories.
2. pharmaceutical composition according to claim 1 is characterized in that described dienogest and estradiol valerate are to add with the solution form after being dissolved in certain solvent.
3. pharmaceutical composition according to claim 2 is characterized in that the solvent of described active component is selected from ethanol or dehydrated alcohol.
4. pharmaceutical composition according to claim 1 is characterized in that containing gas-producing disintegrant in the described compositions.
5. pharmaceutical composition according to claim 4 is characterized in that described gas-producing disintegrant is selected from the compositions of citric acid or tartaric acid and sodium bicarbonate or sodium carbonate.
6. pharmaceutical composition according to claim 1 is characterized in that said composition exists with tablet, oral cavity disintegration tablet, granule, capsular form.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102381914A CN102058604A (en) | 2009-11-17 | 2009-11-17 | Drug composition containing dienogest and estradiol valerate and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102381914A CN102058604A (en) | 2009-11-17 | 2009-11-17 | Drug composition containing dienogest and estradiol valerate and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102058604A true CN102058604A (en) | 2011-05-18 |
Family
ID=43994230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009102381914A Pending CN102058604A (en) | 2009-11-17 | 2009-11-17 | Drug composition containing dienogest and estradiol valerate and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102058604A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105979935A (en) * | 2013-12-12 | 2016-09-28 | 多内斯塔生物科学股份有限公司 | Orally disintegrating solid dosage unit containing an estetrol component |
| US10660903B2 (en) | 2015-06-18 | 2020-05-26 | Estetra Sprl | Orodispersible dosage unit containing an estetrol component |
| US10844088B2 (en) | 2011-07-19 | 2020-11-24 | Estetra Sprl | Process for the preparation of estetrol |
| US10888518B2 (en) | 2015-06-18 | 2021-01-12 | Estetra Sprl | Orodispersible tablet containing estetrol |
| US10894014B2 (en) | 2015-06-18 | 2021-01-19 | Estetra Sprl | Orodispersible tablet containing Estetrol |
| US11053274B2 (en) | 2011-06-01 | 2021-07-06 | Estetra S.P.R.L. | Process for the production of estetrol intermediates |
| US11053273B2 (en) | 2011-06-01 | 2021-07-06 | Estetra S.P.R.L. | Process for the production of estetrol intermediates |
| US11147771B2 (en) | 2015-06-18 | 2021-10-19 | Estetra Sprl | Orodispersible dosage unit containing an estetrol component |
| WO2022069956A1 (en) * | 2020-09-29 | 2022-04-07 | Millicent Pharma Limited | Orodispersible formulations |
| US11452733B2 (en) | 2018-04-19 | 2022-09-27 | Estetra Sprl | Compounds and their uses for alleviating menopause-associated symptoms |
| US11484539B2 (en) | 2018-04-19 | 2022-11-01 | Estetra Sprl | Compounds and their uses for alleviating menopause-associated symptoms |
| US11896602B2 (en) | 2016-08-05 | 2024-02-13 | Estetra Srl | Method for preventing pregnancy |
-
2009
- 2009-11-17 CN CN2009102381914A patent/CN102058604A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11053274B2 (en) | 2011-06-01 | 2021-07-06 | Estetra S.P.R.L. | Process for the production of estetrol intermediates |
| US11053273B2 (en) | 2011-06-01 | 2021-07-06 | Estetra S.P.R.L. | Process for the production of estetrol intermediates |
| US10844088B2 (en) | 2011-07-19 | 2020-11-24 | Estetra Sprl | Process for the preparation of estetrol |
| CN105979935B (en) * | 2013-12-12 | 2019-07-26 | 多内斯塔生物科学股份有限公司 | Orally disintegrating solid dosage unit containing an estritol component |
| CN105979935A (en) * | 2013-12-12 | 2016-09-28 | 多内斯塔生物科学股份有限公司 | Orally disintegrating solid dosage unit containing an estetrol component |
| US11147771B2 (en) | 2015-06-18 | 2021-10-19 | Estetra Sprl | Orodispersible dosage unit containing an estetrol component |
| US11793760B2 (en) | 2015-06-18 | 2023-10-24 | Estetra Srl | Orodispersible dosage unit containing an estetrol component |
| US10888518B2 (en) | 2015-06-18 | 2021-01-12 | Estetra Sprl | Orodispersible tablet containing estetrol |
| US10660903B2 (en) | 2015-06-18 | 2020-05-26 | Estetra Sprl | Orodispersible dosage unit containing an estetrol component |
| US11964055B2 (en) | 2015-06-18 | 2024-04-23 | Estetra Srl | Orodispersible dosage unit containing an estetrol component |
| US11957694B2 (en) | 2015-06-18 | 2024-04-16 | Estetra Srl | Orodispersible dosage unit containing an estetrol component |
| US10894014B2 (en) | 2015-06-18 | 2021-01-19 | Estetra Sprl | Orodispersible tablet containing Estetrol |
| US11896602B2 (en) | 2016-08-05 | 2024-02-13 | Estetra Srl | Method for preventing pregnancy |
| TWI801561B (en) * | 2018-04-19 | 2023-05-11 | 比利時商依思特拉私人有限責任公司 | Compounds and their uses for alleviating menopause-associated symptoms |
| US11666585B2 (en) | 2018-04-19 | 2023-06-06 | Estetra Srl | Compounds and their uses for alleviating menopause-associated symptoms |
| US11484539B2 (en) | 2018-04-19 | 2022-11-01 | Estetra Sprl | Compounds and their uses for alleviating menopause-associated symptoms |
| US11452733B2 (en) | 2018-04-19 | 2022-09-27 | Estetra Sprl | Compounds and their uses for alleviating menopause-associated symptoms |
| WO2022069956A1 (en) * | 2020-09-29 | 2022-04-07 | Millicent Pharma Limited | Orodispersible formulations |
| US12178824B2 (en) | 2020-09-29 | 2024-12-31 | Millicent Pharma Limited | Orodispersible formulations |
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Application publication date: 20110518 |