US20050100564A1 - Controlled release delivery system for nasal applications - Google Patents

Controlled release delivery system for nasal applications Download PDF

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Publication number
US20050100564A1
US20050100564A1 US10/772,964 US77296404A US2005100564A1 US 20050100564 A1 US20050100564 A1 US 20050100564A1 US 77296404 A US77296404 A US 77296404A US 2005100564 A1 US2005100564 A1 US 2005100564A1
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United States
Prior art keywords
weight
formulation
formulation according
oil
amount
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.)
Abandoned
Application number
US10/772,964
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English (en)
Inventor
Claudia Mattern
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Precisiobiotix Technologies Inc
Mattern Pharma AG
Udo Mattern
Original Assignee
Udo Mattern
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Udo Mattern filed Critical Udo Mattern
Assigned to MATTERN, UDO reassignment MATTERN, UDO ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MATTERN, CLAUDIA
Publication of US20050100564A1 publication Critical patent/US20050100564A1/en
Priority to US11/560,187 priority Critical patent/US20070149454A1/en
Assigned to M & P PATENT AKTIENGESELLSCHAFT, C/O FUNDATIONSANSTALT reassignment M & P PATENT AKTIENGESELLSCHAFT, C/O FUNDATIONSANSTALT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MATTERN, UDO
Priority to US12/796,165 priority patent/US20100311707A1/en
Priority to US13/194,853 priority patent/US8784882B2/en
Priority to US13/194,928 priority patent/US8574622B2/en
Priority to US13/316,494 priority patent/US8877230B2/en
Priority to US13/547,774 priority patent/US8784869B2/en
Assigned to MATTERN PHARMA AG reassignment MATTERN PHARMA AG MERGER (SEE DOCUMENT FOR DETAILS). Assignors: M & P PATNT AKTIENGESELLSCHAFT
Assigned to MATTERN PHARMA AG reassignment MATTERN PHARMA AG CORRECTIVE ASSIGNMENT TO CORRECT THE TO CORRECT THE ASSIGNOR FROM M & P PATNT AKTIENGESELLSCHAFT TO M & P PATENT AKTIENGESELLSCHAFT PREVIOUSLY RECORDED ON REEL 032291 FRAME 0349. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER EFFECTIVE 02/04/2014. Assignors: M & P PATENT AKTIENGESELLSCHAFT
Priority to US14/322,319 priority patent/US9238072B2/en
Priority to US14/965,137 priority patent/US9579280B2/en
Priority to US15/403,627 priority patent/US9962394B2/en
Assigned to ACERUS PHARMACEUTICALS SRL reassignment ACERUS PHARMACEUTICALS SRL RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: MIDCAP FUNDING V TRUST
Assigned to PRECISIOBIOTIX TECHNOLOGIES INC. reassignment PRECISIOBIOTIX TECHNOLOGIES INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PHAGELUX (CANADA), INC.
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0043—Nose
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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
    • 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
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26—Androgens

Definitions

  • the present invention relates to a formulation for the controlled release of sexual hormones to the systemic circulation after nasal application.
  • Nasal drug delivery offers many advantages that include rapid adsorption due to abundant capillary vessels, fast onset of action, avoidance of hepatic first-pass metabolism, utility for chronic medication and ease of administration.
  • lipophilic pharmaceutical compounds having a sufficiently low molecular weight in general are readily adsorbed by the mucous membrane of the nose.
  • pharmacokinetic profiles similar to those obtained after intravenous injection.
  • the inventor made intensive studies of various sexual hormone drug formulations and, as a result, surprisingly found that the incorporation of the drug into a special lipophilic or partly lipophilic system not only leads to a higher bioavailability in general caused by sustained serum levels in plasma, but also to a more favourable serum level profile.
  • the invention comprises a formulation for nasal application comprising a) at least one sexual hormone drug; b) at least one lipophilic or partly lipophilic carrier; and c) a compound or a mixture of compounds having surface tension decreasing activity, an amount effective for in situ generation of an emulsion upon contact of the formulation with water.
  • the lipophilic carrier comprises an oil.
  • said oil is a vegetable oil.
  • said oil is castor oil.
  • a preferred embodiment of the invention is characterized in that the amount of oil comprises between 30% and 98% by weight, preferably between 60 and 98% by weight, more preferably between 75% and 95% by weight, even more preferably between 85% and 95% by weight and most preferably around 90% by weight of the formulation.
  • component (c) comprises at least one surfactant selected from the group consisting of lecithin, fatty acid ester of polyvalent alcohols, of sorbitanes, of polyoxyethylensorbitans, of polyoxyethylene, of sucrose, of polyglycerol and/or at least one humectant selected from the group consisting of sorbitol, glycerine, polyethylene glycol, and macrogol glycerol fatty acid ester, or a mixture thereof.
  • surfactant selected from the group consisting of lecithin, fatty acid ester of polyvalent alcohols, of sorbitanes, of polyoxyethylensorbitans, of polyoxyethylene, of sucrose, of polyglycerol and/or at least one humectant selected from the group consisting of sorbitol, glycerine, polyethylene glycol, and macrogol glycerol fatty acid ester, or a mixture thereof.
  • component (c) comprises an oleoyl macrogolglyceride or a mixture of oleoyl macrogolglycerides.
  • component (c) is comprised within the formulation in an amount of from 1 to 20% by weight, preferably 1 to 10% by weight, more preferably 1 to 5% by weight, and most preferably at around 4% by weight.
  • a further embodiment comprises a viscosity regulating agent.
  • said viscosity regulating agent comprises a thickener or gelling agent selected from the group consisting of cellulose and cellulose derivatives, polysaccharides, carbomers, polyvinyl alcohol, povidone, colloidal silicon dioxide, cetyl alcohols, stearic acid, beeswax, petrolatum, triglycerides and lanolin, or a mixture thereof.
  • a thickener or gelling agent selected from the group consisting of cellulose and cellulose derivatives, polysaccharides, carbomers, polyvinyl alcohol, povidone, colloidal silicon dioxide, cetyl alcohols, stearic acid, beeswax, petrolatum, triglycerides and lanolin, or a mixture thereof.
  • said viscosity increasing agent is colloidal silicon dioxide.
  • the viscosity regulating agent is comprised within the formulation in an amount of from 0.5 to 10% by weight, preferably 0.5 to 5% by weight, more preferably 1 to 3% by weight, and most preferably at around 3% by weight.
  • the sexual hormone drug is testosterone.
  • the sexual hormone drug is comprised within the formulation in an amount of from 0.5 to 6% by weight, preferably 2 to 4% by weight, more preferably 0.5 to 2% by weight, and most preferably at around 2% by weight.
  • FIG. 1 shows the serum levels of free testosterone at baseline and after nasal application of testosterone.
  • the resultant formulation is chemically and physically stable and can be a suspension or a solution of the pharmacologically active substance.
  • it is filled into a preservative-free, airless multi-dose device able to accurately deliver doses of the above formulation, also at higher viscosities.
  • the drug or the drug particles should be efficiently trapped at the deposition site and be absorbed at a predictable rate across the mucous membrane of the patient, thereby limiting possible deactivation by metabolizing enzymes and/or protein-binding.
  • the term “sexual hormone drug” shall mean at least one sexual hormone (such as testosterone) or at least one biologic pro-drug of a sexual hormone (such as androstenedione, progesterone, 17- ⁇ -hydroxyprogesterone) or at least one derivative of a sexual hormone (such as mestanolone and 4-chloro-1-dehydromethyltestosterone) or a combination thereof.
  • the sexual hormone drug is testosterone.
  • the sexual hormone drug is comprised within the formulation in an amount of from 0.5 to 6% by weight, preferably 2 to 4% by weight, more preferably 0.5 to 2% by weight, and most preferably at around 2% by weight.
  • the drug of this invention may be introduced into the formulation also in a processed form such as microspheres, liposomes etc.
  • lipophilic carrier shall comprise, but not limited to, a vegetable oil such as castor oil, soybean oil, sesame oil or peanut oil, fatty acid ester such as ethyl- and oleyloleat, isopropylmyristate, medium chain triglycerides, glycerol esters of fatty acids, or polyethylene glycol, phospholipids, white soft paraffin, or hydrogenated castor oil. Particularly useful is castor oil.
  • the incorporation of the drug is also possible into an oil mixture.
  • the lipophilic part can be present in a formulation in an amount between 30% and 98% by weight, preferably between 60 and 98% by weight, more preferably between 75% and 95% by weight, even more preferably between 85% and 95% by weight and most preferably around 90% by weight of the formulation.
  • Componentn (C) shall comprise at least a surfactant such as, but not limited to, lecithin, fatty acid ester of polyvalent alcohols, of sorbitanes, of polyoxyethylensorbitans, of polyoxyethylene, of sucrose, of polyglycerol and/or at least one humectant such as sorbitol, glycerine, polyethylene glycol, or macrogol glycerol fatty acid ester.
  • a surfactant such as, but not limited to, lecithin, fatty acid ester of polyvalent alcohols, of sorbitanes, of polyoxyethylensorbitans, of polyoxyethylene, of sucrose, of polyglycerol and/or at least one humectant such as sorbitol, glycerine, polyethylene glycol, or macrogol glycerol fatty acid ester.
  • oleoyl macrogolglycerides such as Labrafil M 1944 CS, as available from G
  • the incorporation of the drug is also possible into a surfactant mixture.
  • the particular amount of surfactant that constitutes an effective amount is dependent on the particular oil or oil mixture (see above) used in the formulation. It is therefore not practical to enumerate specific amounts for use with specific formulations of the invention. Generally, however, the surfactant can be present in a formulation in an amount of from 1 to 20% by weight, preferably 1 to 10% by weight, more preferably 1 to 5% by weight, and most preferably at around 4% by weight.
  • viscosity regulating agent shall mean a thickener or gelling agent.
  • examples are, but not limited to, cellulose and derivatives thereof, polysaccharides, carbomers, polyvinyl alcohol, povidone, colloidal silicon dioxide, cetyl alcohols, stearic acid, beeswax, petrolatum, triglycerides or lanolin.
  • colloidal silicon dioxide such as Acrosil 200, as availble from Degussa).
  • the incorporation of the drug is also possible into a mixture of thickeners or gelling agents.
  • thickener/gelling agent(s) can be present in a formulation in an amount from 0.5 to 10% by weight, preferably 0.5 to 5% by weight, more preferably 1 to 3% by weight, and most preferably at around 3% by weight.
  • the formulation according to this invention may also be processed into powder form, e.g. by lyophilization or spray-drying.
  • formulations of the invention can be prepared very easily by conventional methods, i.e.:
  • the thickener or gelling agent is added to a sufficient amount of water and dispersed with high speed mixing and, if necessary, a surfactant (mixture 1).
  • a surfactant mixture 1
  • water and/or the lipophilic carrier are introduced and, if necessary, a surfactant (mixture 2).
  • mixture 2 the hormone is added very carefully avoiding introducing air.
  • Mixture 2 is added to mixture 1, if necessary pH and tonicity are adjusted and the final mixture is homogenised and sterilised.
  • Lipophilic carrier and emulsifier are filled into a stirrer vessel and about 75% of the viscosity regulating agent is mixed in.
  • the hormone is added under stirring until a homogenous dispersion of the active ingredient is obtained. Then the formulation is adjusted to the necessary viscosity with the rest of the viscosity regulating agent.
  • the formulation is preferably filled into a preservative-free, airless nasal spray device such as the COMOD system available from Ursatec.
  • “higher availability” is meant that after a single application a serum level of sexual hormone significantly higher than baseline is maintained for 6 hours, more preferably for 8 hours and most preferably for at least 10 hours.
  • the release of the hormone is sustained due to its solubility in the oily carrier and to the viscosity of the formulation remaining on the mucous membrane for a prolonged duration of time.
  • the dotted line shows the serum level after application of 1 spray per nostril once of the most preferred formulation (see Table 1).
  • the formulation for nasal application of this invention is different from conventional formulations, especially to those for sustained release, as it is mimicking the physiologic daily rhythm of testosterone release. It is also avoiding supra- and sub-normal testosterone levels, which is pleasant for the patient and a demand for hormone replacement therapy. As shown in FIG. 1 (upper line), a simple nasal spray containing testosterone is unsatisfactory in this sense.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Otolaryngology (AREA)
  • Reproductive Health (AREA)
  • Gynecology & Obstetrics (AREA)
  • Diabetes (AREA)
  • Pregnancy & Childbirth (AREA)
  • Pulmonology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Infusion, Injection, And Reservoir Apparatuses (AREA)
US10/772,964 2003-11-11 2004-02-04 Controlled release delivery system for nasal applications Abandoned US20050100564A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US11/560,187 US20070149454A1 (en) 2003-11-11 2006-11-15 Controlled Release Delivery System for Nasal Applications and Method of Treatment
US12/796,165 US20100311707A1 (en) 2003-11-11 2010-06-08 Controlled release delivery system for nasal applications and methods of treatment
US13/194,853 US8784882B2 (en) 2003-11-11 2011-07-29 Controlled release delivery system for nasal applications and method of treatment
US13/194,928 US8574622B2 (en) 2003-11-11 2011-07-30 Controlled release delivery system for nasal applications
US13/316,494 US8877230B2 (en) 2003-11-11 2011-12-10 Controlled release delivery system for nasal applications
US13/547,774 US8784869B2 (en) 2003-11-11 2012-07-12 Controlled release delivery system for nasal applications and methods of treatment
US14/322,319 US9238072B2 (en) 2003-11-11 2014-07-02 Controlled release delivery system for nasal applications and method of treatment
US14/965,137 US9579280B2 (en) 2003-11-11 2015-12-10 Controlled release delivery system for nasal applications and method of treatment
US15/403,627 US9962394B2 (en) 2003-11-11 2017-01-11 Controlled release delivery system for nasal applications and method of treatment

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03025769A EP1530965B1 (en) 2003-11-11 2003-11-11 Controlled release delivery system of sexual hormones for nasal application
EP03025769.5 2003-11-11

Related Child Applications (4)

Application Number Title Priority Date Filing Date
US11/560,187 Continuation-In-Part US20070149454A1 (en) 2003-11-11 2006-11-15 Controlled Release Delivery System for Nasal Applications and Method of Treatment
US11/560,187 Continuation US20070149454A1 (en) 2003-11-11 2006-11-15 Controlled Release Delivery System for Nasal Applications and Method of Treatment
US13/194,928 Continuation US8574622B2 (en) 2003-11-11 2011-07-30 Controlled release delivery system for nasal applications
US13/547,774 Continuation-In-Part US8784869B2 (en) 2003-11-11 2012-07-12 Controlled release delivery system for nasal applications and methods of treatment

Publications (1)

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US20050100564A1 true US20050100564A1 (en) 2005-05-12

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Family Applications (6)

Application Number Title Priority Date Filing Date
US10/772,964 Abandoned US20050100564A1 (en) 2003-11-11 2004-02-04 Controlled release delivery system for nasal applications
US11/560,187 Abandoned US20070149454A1 (en) 2003-11-11 2006-11-15 Controlled Release Delivery System for Nasal Applications and Method of Treatment
US12/796,165 Abandoned US20100311707A1 (en) 2003-11-11 2010-06-08 Controlled release delivery system for nasal applications and methods of treatment
US13/194,853 Expired - Lifetime US8784882B2 (en) 2003-11-11 2011-07-29 Controlled release delivery system for nasal applications and method of treatment
US13/194,928 Expired - Lifetime US8574622B2 (en) 2003-11-11 2011-07-30 Controlled release delivery system for nasal applications
US13/316,494 Expired - Lifetime US8877230B2 (en) 2003-11-11 2011-12-10 Controlled release delivery system for nasal applications

Family Applications After (5)

Application Number Title Priority Date Filing Date
US11/560,187 Abandoned US20070149454A1 (en) 2003-11-11 2006-11-15 Controlled Release Delivery System for Nasal Applications and Method of Treatment
US12/796,165 Abandoned US20100311707A1 (en) 2003-11-11 2010-06-08 Controlled release delivery system for nasal applications and methods of treatment
US13/194,853 Expired - Lifetime US8784882B2 (en) 2003-11-11 2011-07-29 Controlled release delivery system for nasal applications and method of treatment
US13/194,928 Expired - Lifetime US8574622B2 (en) 2003-11-11 2011-07-30 Controlled release delivery system for nasal applications
US13/316,494 Expired - Lifetime US8877230B2 (en) 2003-11-11 2011-12-10 Controlled release delivery system for nasal applications

Country Status (23)

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US (6) US20050100564A1 (es)
EP (1) EP1530965B1 (es)
JP (1) JP4616270B2 (es)
KR (1) KR100861443B1 (es)
AR (1) AR047722A1 (es)
AT (1) ATE319426T1 (es)
AU (1) AU2004286781B2 (es)
BR (1) BRPI0416370B8 (es)
CA (1) CA2541498C (es)
DE (1) DE60303854T2 (es)
DK (1) DK1530965T3 (es)
ES (1) ES2258694T3 (es)
HR (1) HRP20060147B1 (es)
MY (1) MY131483A (es)
NO (1) NO338665B1 (es)
PL (1) PL219338B1 (es)
PT (1) PT1530965E (es)
RU (1) RU2331423C2 (es)
SA (1) SA04250363B1 (es)
SI (1) SI1530965T1 (es)
TW (1) TWI350176B (es)
WO (1) WO2005044273A1 (es)
ZA (1) ZA200603115B (es)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120009249A1 (en) * 2006-10-04 2012-01-12 Claudia Mattern Controlled release delivery system for nasal application of neurotransmitters
WO2012156822A1 (en) 2011-05-15 2012-11-22 Trimel Pharmaceuticals Corp. Controlled release nasal testosterone gels, methods and pre-filled multi-dose applicator systems for pernasal administration
WO2012156821A1 (en) 2011-05-13 2012-11-22 Trimel Pharmaceuticals Corp. Intranasal lower dosage strength testosterone gel formulations and use thereof for treating anorgasmia or hypoactive sexual desire disorder
US8574622B2 (en) 2003-11-11 2013-11-05 M & P Patent Aktiengesellschaft Controlled release delivery system for nasal applications
US8609043B2 (en) 2004-12-28 2013-12-17 M & P Patent Aktiengesellschaft Use of a container of an inorganic additive containing plastic material
US8784869B2 (en) 2003-11-11 2014-07-22 Mattern Pharma Ag Controlled release delivery system for nasal applications and methods of treatment
US9757388B2 (en) 2011-05-13 2017-09-12 Acerus Pharmaceuticals Srl Intranasal methods of treating women for anorgasmia with 0.6% and 0.72% testosterone gels
US10111888B2 (en) 2011-05-13 2018-10-30 Acerus Biopharma Inc. Intranasal 0.15% and 0.24% testosterone gel formulations and use thereof for treating anorgasmia or hypoactive sexual desire disorder
US10668084B2 (en) 2011-05-13 2020-06-02 Acerus Biopharma Inc. Intranasal lower dosage strength testosterone gel formulations and use thereof for treating anorgasmia or hypoactive sexual desire disorder
US11234928B2 (en) 2017-11-27 2022-02-01 Aska Pharmaceutical Co., Ltd. Powder preparation for nasal administration
US11903951B2 (en) 2016-06-03 2024-02-20 M et P Pharma AG Nasal pharmaceutical compositions with a porous excipient

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US6399176B1 (en) 1996-10-01 2002-06-04 Magotteaux International S.A. Composite wear component
JP4222944B2 (ja) 2001-12-04 2009-02-12 マゴット アンテルナショナル エス．アー． 強化された摩耗抵抗性を持つ鋳造部品
KR101292492B1 (ko) 2004-05-11 2013-08-01 이모셔널 브레인 비.브이. 약제학적 제형물 및 여성 성기능 부전의 치료에서 그것의용도
EP1790343A1 (en) 2005-11-11 2007-05-30 Emotional Brain B.V. Pharmaceuticals formulations and uses thereof in the treatment of female sexual dysfunction
GB2437488A (en) * 2006-04-25 2007-10-31 Optinose As Pharmaceutical oily formulation for nasal or buccal administration
US8147980B2 (en) 2006-11-01 2012-04-03 Aia Engineering, Ltd. Wear-resistant metal matrix ceramic composite parts and methods of manufacturing thereof
EP1925307A1 (en) 2006-11-03 2008-05-28 Emotional Brain B.V. Use of 3-alpha-androstanediol in the treatment of sexual dysfunction
DE102010023949A1 (de) * 2010-06-16 2011-12-22 F. Holzer Gmbh In-situ Lecithin-Mikroemulsionsgel-Formulierung
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