EP1043973A1 - Pharmaceutical compositions comprising micelles comprising lipophilic glucocorticosteroid and only one surfactant - Google Patents
Pharmaceutical compositions comprising micelles comprising lipophilic glucocorticosteroid and only one surfactantInfo
- Publication number
- EP1043973A1 EP1043973A1 EP98964662A EP98964662A EP1043973A1 EP 1043973 A1 EP1043973 A1 EP 1043973A1 EP 98964662 A EP98964662 A EP 98964662A EP 98964662 A EP98964662 A EP 98964662A EP 1043973 A1 EP1043973 A1 EP 1043973A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- surfactant
- glucocorticosteroid
- micelles
- composition
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Definitions
- the present invention relates to a pharmaceutical composition
- a pharmaceutical composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant
- the invention further relates to a process for the preparation of the pharmaceutical composition and use of the pharmaceutical composition for the manufacture of a medicament for treating allergic and/or infla - matory diseases in the respiratory tract or for treating intestinal diseases and methods for treatment of the diseases in a mammal, including man.
- Rhinitis and asthma are today effectively treated by the use of glucocorticosteroids such as e.g. mometasone furoate, budesonide, and fluticasone propionate.
- glucocorticosteroids such as e.g. mometasone furoate, budesonide, and fluticasone propionate.
- Patent applications that can be mentioned in this context are WO 92/13873 and WO 96/19199 both to Astra AB of Sweden.
- the glucocorticosteroid compositions are used in the form of powders in dry powder inhalers, as solutions or suspensions in pressurized metered dose inhalers (pMDIs).
- pMDIs pressurized metered dose inhalers
- a suspension in water is a user-friendly form of administration as the solution is easily accepted by the mucosa.
- the glucocorticosteroid crystals are in contact with the water which can affect the stability of the glucocorticosteroid.
- a glucocorticosteroid ester may be chemically degraded for example by ester hydrolysis when using such a compound.
- the compositions in the form of suspensions may be less stable than solutions e.g.
- compositions for trans- mucosal membrane administration of protein or peptide drugs wherein the compositions comprise the drug in mixtures with at least one bile salt or fusidate or a derivative thereof and at least one non-ionic detergent of the formula RO(CHR'CH 2 O) n R, wherein one R is H and the other R represents the radical of a saturated or unsaturated cyclic or acyclic organic alcohol of 6-40 carbons.
- EP 0179583 Al to Merck & Co. Inc. discloses a system for enhancing the water dissolution rate and solubility of poorly soluble drugs.
- the compositions of EP 0179583 Al involve combining the poorly water-soluble drug with the surfactant in appropriate ratios and by an appropriate method that results in the formation of an anhydrous product.
- the examples are directed to anhydrous compositions of the antiparasitic agents ivermectin or abamectin and a surfactant.
- IBD inflammatory bowel diseases
- a pharmaceutical composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocortico- steroid and one and only one pharmaceutically acceptable surfactant.
- the composition comprises one and only one non- ionic surfactant.
- composition is used for treating allergic and/or inflammatory diseases in the respiratory tract.
- composition is used for treating intestinal diseases.
- a process for the preparation of a pharmaceutical composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant, the process comprising the steps of: a) dissolving the glucocorticosteroid in the surfactant; b) adding an aqueous medium to the solution from step a) and stirring the solution.
- composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant, for the manufacture of a medicament for treating allergic and inflammatory diseases in the respiratory tract is obtained.
- composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant for the manufacture of a medicament for treating intestinal diseases is obtained.
- Another aspect of the invention is a method for treatment of allergic and/or inflammatory diseases in the respiratory tract of a mammal, including man.
- the method is characterized by administration to the mammal in need of such treatment of an therapeutically effective amount of a pharmaceutical composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant.
- a last aspect of the invention is a method for treatment of intestinal diseases in a mammal, including man.
- the method is characterized by administration to the mammal in need of such treatment of an therapeutically effective amount of a pharmaceutical composition comprising micelles in an aqueous medium, wherein the micelles comprise a lipophilic glucocorticosteroid and one and only one pharmaceutically acceptable surfactant.
- lipophilic glucocorticosteroids and their esters can be incorporated in micelles formed by a surfactant, especially a non-ionic surfactant, in an aqueous medium.
- a surfactant especially a non-ionic surfactant
- micelles are molecular aggregates formed in the solution of a surfactant.
- Surfactants in a dilute aqueous solution exist primarily as monomers, but at higher concentrations a number of surfactant molecules aggregate to form micelles. Thereby a stable formulation is obtained in which the lipophilic glucocorticosteroid/glucocorticosteroid ester is protected and is possible to be absorbed.
- the micelles will act as non-aqueous reservoirs for the lipophilic glucocorticosteroid and will positively affect the pharmacokinetic and deposition of the glucocorticosteroid molecule.
- the glucocorticosteroid will also be more easy to dose accurately as well as for the patient to administer accurately.
- lipophilic reference can be made to the above mentioned reference where on p. 155 it is stated that "lipophilic drugs may be wetted by oils and semipolar liquids.”
- compositions comprising the lipophilic glucocorticosteroids used in the invention in an aqueous medium are very difficult to dissolve in water and then to obtain a stable composition. It was found in the present invention that by dissolving the lipophilic glucocorticosteroid in a surfactant, preferably a non-ionic surfactant, stable compositions can be obtained with the glucocorticosteroid in micellar form.
- a surfactant preferably a non-ionic surfactant
- the inventor of the present invention has further found that use of the stable compositions comprising e.g. rofleponide palmitate incorporated in micelles formed by a surfactant, causes less irritation in the lung after oral inhalation by human patients, than is experienced after oral inhalation of the same surfactant on its own.
- the present compositions comprise one and only one surfactant.
- the surfactant used in the present compositions can be non-ionic, zwitterionic, anionic or cationic. It is, however, preferred, to use a non-ionic surfactant, since this normally reduces the risk of side-effects after administration. Examples of non-ionic, zwitterionic, anionic or cationic surfactants which may be used in the present invention can be found in Wade and Weller, Handbook of Pharmaceutical Excipients, 1994, The Pharmaceutical Press, London.
- the non-ionic surfactants used according to the present invention are suitably selected from poloxamers, e.g. poloxamer 188; polyoxyethylene alkyl ethers, e.g.poloxyl 10 stearyl ether, poloxyl 20 stearyl ether; polyoxyethylene stearates, e.g. polyoxyl 8 stearate, poloxyl 12 stearate; polyoxyethyleneglycolhydroxystearates, e.g. polyoxyethyleneglycol 12- hydroxystearates, and polyoxyethylene sorbitan fatty acid esters.
- a preferred group of non- ionic surfactants is polyoxyethylene sorbitan fatty acid esters, e.g.
- polyoxyethylene 20 sorbitan monolaurate, monopalmitate, monostearate or monooleate also known as poly- sorbate 20, polysorbate 40, polysorbate 60 and polysorbate 80, respectively
- suitable commercial polysorbates are Tween 20, Tween 40, Tween 60 and Tween 80.
- a further preferred group of non-ionic surfactants is polyoxyethyleneglycol 12-hydroxy- stearates and an especially preferred compound is polyoxyethyleneglycol 660 12-hydroxy- stearate.
- lipophilic glucocorticosteroids relate to lipophilic glucocorticosteroids per se, as well as their pharmaceutically acceptable solvates, esters, acetals and salts, and solvates of any of these.
- glucocorticosteroids examples include betamethasone, fluticasone (e.g. as propionate), budesonide, tipredane, dexamethasone, beclomethasone (e.g. as dipropionate), prednisolone, fluocinolone (e.g. as acetonide), triamcinolone (e.g. as acetonide), mometasone (e.g. as furoate), rofleponide (e.g.
- mometasone furoate beclomethasone dipropionate or fluticasone propionate or glucocorticosteroids with an asymmetric acetal structure, e.g. comprising 16 ⁇ ,17 ⁇ -butylidenedioxy group, such as budesonide or rofleponide or pharmaceutically acceptable solvates, esters, acetals or salts, or where applicable, solvates thereof.
- the most preferred lipophilic glucocorticosteroid ester is rofleponide palmitate.
- the amount of surfactant used in the composition should be less than 5 % (w/w) of the total composition weight.
- the amount of surfactant is less than 3 % (w/w) and most preferably less than 1 % (w/w) of the total composition weight.
- the concentration of the surfactant must, however, be higher than the critical micellar concentration (CMC), being the lowest concentration at which micelles are formed in an aqueous medium.
- CMC critical micellar concentration
- the CMC value depends primarily upon the temperature and the concentration of possible additives. It lies within the competence of the skilled person to determine the CMC for each indivi-dual composition and thus prepare suitable micelles according to the present invention.
- the amount of the glucocorticosteroid used depends on the field of use. If the glucocorticosteroid is used for treating diseases in the respiratory tract by inhalation a suitable daily dose is from 10 to 2400 ⁇ g, preferably from 10 to 1600 ⁇ g. If the glucocorticosteroid is used for treating intestinal diseases a suitable daily dose is from 400 to 4000 ⁇ g, preferably from 800 to 3000 ⁇ g.
- composition according to the invention may also contain one or more pharmaceutically acceptable additives such as buffers and other pH modifiers, antioxidants, complexing agents to further increase the stability, viscosity regulating agents andisotonicity modifying agents.
- pharmaceutically acceptable additives such as buffers and other pH modifiers, antioxidants, complexing agents to further increase the stability, viscosity regulating agents andisotonicity modifying agents.
- Compounds used as such agents are compounds generally used in drug formulations e.g. EDTA for complexing and carboxymethyl cellulose (CMC) for regulating viscosity.
- substances for adjusting the isotonicity can be mentioned glucose, mannitol, salts, glycerol and propylene-glycol.
- alkaline buffers are used such that the pH of the composition is from 4 to 7. It is, however, preferred to use one or more antioxidants), which may be water-soluble to a smaller or larger degree.
- antioxidants include, without limitation, tocopherols, especially ⁇ -tocopherol, and preferably racemic ⁇ -tocopherol, butylhydroxyanisole (BHA), butylhydroxytoluene (BHT) and ascorbic acid.
- BHA butylhydroxyanisole
- BHT butylhydroxytoluene
- ascorbic acid ascorbic acid
- the aqueous medium is added to the glucocorticosteroid- surfactant solution and the mixture is stirred, preferably intensely stirred, to obtain a stable and homogeneous solution.
- the aqueous medium is of the same temperature as the one of the glucocorticosteroid-surfactant solution before it is added to the solution. If other pharmaceutically acceptable additives are used they are suitably added to the aqueous medium before mixing with the glucocorticosteroid-surfactant solution if they are water soluble. Otherwise they are added to the surfactant solution.
- glucose is dissolved in the aqueous medium in an isotonic amount.
- the surfactant used can be a solid compound at ambient temperature or a more or less fluid compound. If a solid surfactant is used it should be heated in order to melt it in a first step of the process. The glucocorticosteroid is then dissolved in the melted surfactant. This is a preferred embodiment of the invention.
- the glucocorticosteroid can be dissolved directly in the surfactant at ambient temperature or it may be suitable to increase the temperature of the surfactant to more readily dissolve the glucocorticosteroid. Then the water is added.
- a further possibility is to dissolve the surfactant in a conventional organic solvent, e.g. ethanol, and then to dissolve the glucocorticosteroid in this solution or vice versa.
- the organic solvent then has to be evaporated before the aqueous medium is added. It is impor- tant that the organic solvent is removed from the composition otherwise the composition will have a stinging effect in the nose of the patient if the composition is used for the manufacture of a medicament for treating allergic and/or inflammatory diseases in the respiratory tract.
- the composition according to the invention can be made sterile in a conventional manner, e.g. by using dry heat, steam or irradiation.
- the composition according to the invention is used for the manufacture of a medicament for treating allergic and/or inflammatory diseases in the respiratory tract.
- the composition can then be administered via the upper and lower respiratory tract, including nasal or oral inhalation.
- the composition according to the invention can be used in common devices for aqueous solutions for nasal and oral inhalation e.g. in a spray pump or in a nebulizer.
- nebulisation reference is made to "Medication Nebulizer Performance", Chest 1 10(2), (1996), pp. 498-505.
- the composition according to the invention is also used for the manufacture of a medicament for treating intestinal diseases such as inflammatory bowel diseases (IBD), ulcerative colitis and Crohn's disease.
- the compositions can then be administered by rectal administration.
- the invention also relates to a method for treatment of allergic and/or inflammatory diseases in the respiratory tract of a mammal, including man.
- the composition according to the invention is administered in a therapeutically effective amount to the mammal in need of such a treatment, preferably by nasal or oral inhalation.
- the invention also relates to a method of treatment of intestinal diseases in a mammal, including man.
- the composition according to the invention is administered in a therapeutically effective amount to the mammal in need of such a treatment, preferably by rectal administration.
- Solutol® HS 15 polyethyleneglycol 660 12-hydroxystearate manufactured by BASF of Germany is melted in a beaker at 35°C-40°C. 100 mg rofleponide palmitate is added to the melt and dissolved.
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9704833A SE9704833D0 (en) | 1997-12-22 | 1997-12-22 | New formulation |
SE9704833 | 1997-12-22 | ||
PCT/SE1998/002426 WO1999032089A1 (en) | 1997-12-22 | 1998-12-22 | Pharmaceutical compositions comprising micelles comprising lipophilic glucocorticosteroid and only one surfactant |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1043973A1 true EP1043973A1 (en) | 2000-10-18 |
Family
ID=20409536
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98964662A Withdrawn EP1043973A1 (en) | 1997-12-22 | 1998-12-22 | Pharmaceutical compositions comprising micelles comprising lipophilic glucocorticosteroid and only one surfactant |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP1043973A1 (en) |
JP (1) | JP2001526210A (en) |
KR (1) | KR20010024789A (en) |
CN (1) | CN1283106A (en) |
AR (1) | AR017220A1 (en) |
AU (1) | AU1993599A (en) |
BR (1) | BR9813811A (en) |
CA (1) | CA2315782A1 (en) |
EE (1) | EE200000388A (en) |
HU (1) | HUP0102365A3 (en) |
ID (1) | ID26945A (en) |
IL (1) | IL136880A0 (en) |
NO (1) | NO20003220L (en) |
NZ (1) | NZ505073A (en) |
PL (1) | PL341361A1 (en) |
SE (1) | SE9704833D0 (en) |
SK (1) | SK9532000A3 (en) |
TR (1) | TR200001977T2 (en) |
WO (1) | WO1999032089A1 (en) |
ZA (1) | ZA9811461B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE9902674D0 (en) * | 1999-07-12 | 1999-07-12 | Astra Ab | New composition |
SE0000332D0 (en) * | 2000-01-31 | 2000-01-31 | Astrazeneca Ab | New use |
US6787532B2 (en) * | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
SE0100901D0 (en) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | New composition |
UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
EP1661556A4 (en) * | 2003-08-20 | 2010-05-19 | Ajinomoto Kk | Medicinal preparation having improved dissolution properties |
US8497258B2 (en) | 2005-11-12 | 2013-07-30 | The Regents Of The University Of California | Viscous budesonide for the treatment of inflammatory diseases of the gastrointestinal tract |
CN100579510C (en) * | 2006-04-13 | 2010-01-13 | 新疆维吾尔自治区包虫病临床研究所 | Precursor micelle preparation and its production process |
US20090143343A1 (en) | 2007-11-13 | 2009-06-04 | Meritage Pharma, Inc. | Compositions for the treatment of inflammation of the gastrointestinal tract |
WO2009064460A2 (en) | 2007-11-13 | 2009-05-22 | Meritage Pharma, Inc. | Gastrointestinal delivery systems |
CN102149368B (en) * | 2008-09-12 | 2017-02-08 | 重症药物有限公司 | Improvements in the absorption of therapeutic agents across mucosal membranes or the skin |
CN101982168B (en) * | 2010-11-02 | 2012-05-23 | 山东大学 | Quercetin nano-micelle preparation and preparation method thereof |
CN102793678B (en) * | 2011-05-26 | 2017-06-30 | 邓世明 | A kind of preparation method of the Docetaxel injection without tween |
DE102011108948A1 (en) * | 2011-07-29 | 2013-01-31 | Achim Göpferich | Aqueous, colloidal solutions of lipophilic substances, in particular drug solutions |
JP5456802B2 (en) * | 2012-01-23 | 2014-04-02 | 株式会社Cac | Cell migration promoter and transdermal absorbent for wound treatment |
US10596115B2 (en) * | 2013-07-17 | 2020-03-24 | Council Of Scientific & Industrial Research | Pharmaceutical composition for the treatment of diminution of bone tissue |
KR102086316B1 (en) * | 2019-09-09 | 2020-03-09 | 한국콜마주식회사 | Cosmetic composition having excellent percutaneous absorption property |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0179583A1 (en) * | 1984-10-04 | 1986-04-30 | Merck & Co. Inc. | A system for enhancing the water dissolution rate and solubility of poorly soluble drugs |
US4994439A (en) * | 1989-01-19 | 1991-02-19 | California Biotechnology Inc. | Transmembrane formulations for drug administration |
AR002009A1 (en) * | 1994-12-22 | 1998-01-07 | Astra Ab | PHARMACEUTICAL COMPOSITION, PROCEDURE FOR THE MANUFACTURE OF A PROLIPOSOMA POWDER AS USED IN SUCH COMPOSITION, PROCEDURE FOR LAMANUFACTURE OF SUCH COMPOSITION, USE OF SUCH PHARMACEUTICAL COMPOSITION IN THE MANUFACTURE OF A DISPOSAL MEDICINAL PRODUCT. |
-
1997
- 1997-12-22 SE SE9704833A patent/SE9704833D0/en unknown
-
1998
- 1998-12-14 ZA ZA9811461A patent/ZA9811461B/en unknown
- 1998-12-17 AR ARP980106453A patent/AR017220A1/en not_active Application Discontinuation
- 1998-12-22 JP JP2000525082A patent/JP2001526210A/en active Pending
- 1998-12-22 AU AU19935/99A patent/AU1993599A/en not_active Abandoned
- 1998-12-22 SK SK953-2000A patent/SK9532000A3/en unknown
- 1998-12-22 NZ NZ505073A patent/NZ505073A/en unknown
- 1998-12-22 CA CA002315782A patent/CA2315782A1/en not_active Abandoned
- 1998-12-22 IL IL13688098A patent/IL136880A0/en unknown
- 1998-12-22 EP EP98964662A patent/EP1043973A1/en not_active Withdrawn
- 1998-12-22 WO PCT/SE1998/002426 patent/WO1999032089A1/en not_active Application Discontinuation
- 1998-12-22 BR BR9813811-1A patent/BR9813811A/en not_active IP Right Cessation
- 1998-12-22 KR KR1020007006879A patent/KR20010024789A/en not_active Application Discontinuation
- 1998-12-22 CN CN98812507A patent/CN1283106A/en active Pending
- 1998-12-22 EE EEP200000388A patent/EE200000388A/en unknown
- 1998-12-22 HU HU0102365A patent/HUP0102365A3/en unknown
- 1998-12-22 TR TR2000/01977T patent/TR200001977T2/en unknown
- 1998-12-22 ID IDW20001131A patent/ID26945A/en unknown
- 1998-12-22 PL PL98341361A patent/PL341361A1/en unknown
-
2000
- 2000-06-21 NO NO20003220A patent/NO20003220L/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9932089A1 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
US10912783B2 (en) | 2015-07-23 | 2021-02-09 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
US10532059B2 (en) | 2016-04-01 | 2020-01-14 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
Also Published As
Publication number | Publication date |
---|---|
WO1999032089A1 (en) | 1999-07-01 |
SE9704833D0 (en) | 1997-12-22 |
NO20003220D0 (en) | 2000-06-21 |
HUP0102365A2 (en) | 2001-11-28 |
EE200000388A (en) | 2002-02-15 |
CA2315782A1 (en) | 1999-07-01 |
BR9813811A (en) | 2000-10-03 |
ZA9811461B (en) | 1999-06-22 |
AU1993599A (en) | 1999-07-12 |
NO20003220L (en) | 2000-08-22 |
JP2001526210A (en) | 2001-12-18 |
ID26945A (en) | 2001-02-22 |
CN1283106A (en) | 2001-02-07 |
NZ505073A (en) | 2002-09-27 |
HUP0102365A3 (en) | 2002-01-28 |
PL341361A1 (en) | 2001-04-09 |
KR20010024789A (en) | 2001-03-26 |
IL136880A0 (en) | 2001-06-14 |
AR017220A1 (en) | 2001-08-22 |
SK9532000A3 (en) | 2000-11-07 |
TR200001977T2 (en) | 2000-12-21 |
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