IE920516A1 - Steroid Formulations - Google Patents
Steroid FormulationsInfo
- Publication number
- IE920516A1 IE920516A1 IE051692A IE920516A IE920516A1 IE 920516 A1 IE920516 A1 IE 920516A1 IE 051692 A IE051692 A IE 051692A IE 920516 A IE920516 A IE 920516A IE 920516 A1 IE920516 A1 IE 920516A1
- Authority
- IE
- Ireland
- Prior art keywords
- formulation
- formulation according
- tipredane
- surfactant
- active ingredient
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 238000009472 formulation Methods 0.000 title claims description 39
- 150000003431 steroids Chemical class 0.000 title description 2
- DXEXNWDGDYUITL-FXSSSKFRSA-N Tipredane Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](SC)(SCC)[C@@]1(C)C[C@@H]2O DXEXNWDGDYUITL-FXSSSKFRSA-N 0.000 claims description 17
- 229950001669 tipredane Drugs 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 239000007900 aqueous suspension Substances 0.000 claims description 7
- 210000001331 nose Anatomy 0.000 claims description 7
- 230000009974 thixotropic effect Effects 0.000 claims description 7
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical group C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 229920001983 poloxamer Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 230000002335 preservative effect Effects 0.000 claims description 4
- 230000000172 allergic effect Effects 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 229960000502 poloxamer Drugs 0.000 claims description 3
- 230000008105 immune reaction Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 210000002850 nasal mucosa Anatomy 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- -1 acetoglycerides Chemical class 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001993 poloxamer 188 Polymers 0.000 description 2
- 229940044519 poloxamer 188 Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 206010051496 Rhinalgia Diseases 0.000 description 1
- 208000036284 Rhinitis seasonal Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 210000001989 nasopharynx Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Otolaryngology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Description
Steroid formulations This invention relates to novel pharmaceutical formulations, in particular to aqueous suspension formulations containing tipredane.
US Patent No 4,361,559 discloses a large number of 3-ketoandrostenes which are described as having useful anti-inflammatory activity, including useful activity in the topical treatment of allergy and asthma. This patent also specifically discloses (110,17a)-17-(ethylthio)-9afluoro-110-hydroxy-17-(methylthio)-androsta-1,4-diene-3-one which is known by the INN generic name tipredane.
We have now found that tipredane has useful anti-inflammatory activity when administered to the nose.
The most favoured vehicle for administering a drug to the nose is water as this is likely to give maximum bioavailability. However, tipredane has a water solubility below 0.002 mg/ml at room temperature. Although it may be possible to increase water solubility by the use of 2Q co-solvents or solubilising agents, such co-solvents and agents frequently cause nasal stinging and/or interact with the active ingredient. Attempts at increasing the aqueous solubility of tipredane using 0-cyclodextrin derivatives were also unsuccessful.
Tipredane has a relatively poor oil solubility, which prevents the preparation of satisfactory emulsion formulations.
In general, powder formulations of non water soluble drugs for application to the nose are not favoured, in that 30 the drug is being presented to the nose in a form that is unlikely to be readily bioavailable.
Propellant driven powder formulations are not favoured for tipredane, in that CFC driven formulations are unsatisfactory environmentally and HFC propellants are 35difficult to formulate. - 2 Surprisingly, we have now found that it is possible to formulate tipredane as an aqueous suspension and control nasal inflammatory conditions.
According to the invention there is provided an aqueous suspension formulation containing, as active ingredient, tipredane.
The formulation according to the invention is advantageous in that it is more efficacious, has a longer effect, produces fewer or less severe side-effects, or has other advantageous properties when compared with comparable formulations of other compounds or with other, known formulations of the active ingredient. In addition, the stability of the active ingredient may be enhanced in the formulation of the invention, which is surprising in view of the known tendency of the active ingredient to oxidise.· The active ingredient is preferably present in the formulation at a concentration of from 0.005% to 1.5% w/w, more preferably from 0.01 to 0.1% and especially from 0.2% 20 to 0.4% w/w.
The formulation will generally contain a surfactant. Although ionic surfactants such as sodium lauryl sulphate may be used, we prefer the surfactant to be a non-ionic surfactant. Non-ionic surfactants that may be mentioned 25 include glycol and glycerol esters, acetoglycerides, macrogol esters, macrogol ethers and sorbiton esters. We have found that the block copolymers of poloxyethylenepolyoxypropylene, known as poloxamers with the general formula HO(C2H4O)a(C3H6O)b(C2H4O)aH, in 30which a is 2 to 130 and b is 15 to 67 give particularly stable formulations.
We prefer poloxamers with an average molecular weight of between 4000 and 20,000, more particularly between 6000 and 15,000. A particularly preferred poloxamer that may be 35mentioned is that known as poloxamer 188 (poloxalkol) in which a in the general formula averages 75 and b averages 30. This has a molecular weight of about 8350.
The concentration of the surfactant in the formulation will depend inter alia on the particular surfactant used, but will in general be from 0.05% to 10% w/w, more preferably from 0.05% to 5% w/w, especially from 0.05% to 0.5% w/w. We have found that the use of such low concentrations of surfactant, eg about 0.1 %w/w, leads to particularly stable formulations which show improved resistance to oxidation.
The formulation may, if desired, contain an effective proportion of a pharmaceutically acceptable preservative or sterilising agent. Suitable preservatives include 15 pharmaceutically acceptable quarternary ammonium compounds. The preferred preservatives amongst the quarternary ammonium compounds are the alkyl benzyl dimethyl ammonium chlorides and mixtures thereof, eg that known generically as benzalkonium chloride·.
The preservative may be used at a concentration of from about 0.005% to 0.10%, preferably 0.005% to 0.05%, eg about 0.01% w/w.
The formulation will generally also contain a pseudoplastic thixotropic viscosity modifying agent.
Suitable thixotropic viscosity modifying agents which may be used include carboxy vinyl polymers, alginates, cellulose and its derivatives, for example hydroxypropyl methylcellulose and dispersible cellulose, which is a co-blend of microcrystalline cellulose and sodium carboxymethyl cellulose sold commercially as Avicel RC-591. If present, the thixotropic viscosity modifying agent will be at a concentration at which the resulting viscosity of the formulation is suitable for its intended use. The viscosity of the formulation may be varied between quite 35wide limits (typically between 0.5 and 5.0% w/w) but, in - 4 general, will be relatively low at high shear rates (to enable dispensing, eg as a spray from a conventional nasal pump) and relatively high at low shear rates.
We prefer the formulation according to the invention to be isotonic with the nasal mucosa. The formulation may therefore contain a tonicity adjusting agent, eg glycerol, at a concentration of from about 0.1% to 2.0%, more preferably 0.5% to 1.0% w/w.
The formulation may additionally contain conventional excipients eg electrolytes. A particularly preferred electrolyte is sodium chloride. Sodium chloride is useful as a flocculating agent and may also alter the tonicity of the formulation.
In general, the overall proportion and concentration of excipients may be varied within fairly wide ranges, provided that the resulting solution is stable and non-irritant when applied to the nasal tissues.
As a particularly preferred aspect of the invention, 2Q there is provided an aqueous formulation comprising a) from 0.1 to 1.25% w/w of tipredane as active ingredient, b) from 0.05% to 10% w/w of a non-ionic surfactant, c) from 0.5 to 5% w/w of a thixotropic viscosity 25 modifying agent, and d) from 0.1 to 2.0% w/w of a tonicity adjusting agent.
The formulation of the invention may be made up, for example, by dispersing the active ingredient, using the surfactant as wetting agent, and dispersing or dissolving 30the thixotropic viscosity modifying agent (if included) and other excipients (if included) in freshly distilled water, adding to this solution an aqueous solution of the preservative (if included), making the solution up to the desired volume with distilled water, and stirring. The 35formulation is preferably made up under aseptic conditions. -5According to another aspect of the invention there is provided a method of treatment of conditions of the nose, in which conditions allergic or immune reactions play a contributory part, which method oomprises administration of a formulation according to the invention to a patient suffering from, or susceptible to, such a condition.
The dosage administered will ot course vary with the condition to ba treated and with its severity. However, in general, a dosage of about 400pg is indicated. The doss may be administered up to four times to each nostril at any one dosing session and from 1 to 4 times a days. We prefer to administer the formulation once or twice daily.
Conditions of the nose in which may be treated the method of the invention include seasonal rhinitis, eg hay fever; perenial rhinitis; nasal polype and allergic manifestations of the nasopharynx.
The invention ic illustrated, but in no way limited, by the following Example.
SxaBgls Ingredients Active ingredient 0.308 w/w (equivalent to 400/tg per actuation) Poloxamer 186 0.100 Sodium chloride Ph.JSw/USP 0.584 Glycerol 1.000 Benzalkonium chloride1 0.010 Avioel RC-591 2.000 Purified water Ph.8w/BP/USP to 100.00 Μ i * added as a 504 w/v solution The formulation has been found to be chemically and physically stable when using an identical vehicle containing tipredane at the following strengths t 0.0096% w/v (equivalent to 12.5pg per actuation) 0.0192% v/V 0.0385% W/V 0.0770% V/V 0.1540% V/V 0.692% V/V 1.231% V/V (equivalent to 33jig per actuation) (equivalent to 90gg per actuation) (equivalent to lOOpg per actuation) (equivalent to 200gg per actuation) (equivalent to 9θ0μ$ per actuation) (equivalent to 1600gg per actuation) Manufacturing process Tipredane is dispersed in an aqueous solution of poloxamer 188, glycerol, sodlua chloride and benzalkonium chloride. This is added to a dispersion of alcrocryetalline cellulose co-blend in water and alxed until homogeneous. The suspension is aade to weight with aore water before filling into bottles.
The tipredane is preferably aiarcnlsed material, with a mean particle size of 5pg and not aore then 20% by weight of the tipredane having e particle size of > 10gm.
If necessary, the pH of the aqueous suspension can be adjusted by addition of acid or base as appropriate, to give a pH of between 4.5 and 7.S.
Claims (12)
1. An aqueous suspension formulation containing, as active ingredient, tipredane.
2. A formulation according to claim 1 which includes a surfactant.
3. A formulation according to claim 2, wherein the surfactant is a non-ionic surfactant.
4. A formulation according to claim 2 or claim 3, wherein the surfactant is a poloxamer.
5. A formulation according to any one of the preceding claims, which includes a pharmaceutically acceptable preservative.
6. A formulation according to any one of the preceding claims, which includes a thixotropic viscosity modifying agent.
7. A formulation according to claim 6, wherein the viscosity modifying agent is cellulose or a derivative thereof. 20
8. . A formulation according to any one of the preceding claims which is isotonic with the nasal mucosa.
9. An aqueous suspension formulation which comprises a) from 0.1 to 1.25% w/w of tipredane as active ingredient, 25 b) from 0.05% to 10% w/w of a non-ionic surfactant, c) from 0.5 to 5% w/w of a thixotropic viscosity modifying agent, and d) from 0.1 to 2.0% w/w of a tonicity adjusting agent.
10. The use of tipredane in the manufacture of a 3omedicament for the treatment of the nose in which allergic or immune reactions play a contributory part. -811.
11.An aqueous suspension formulation according to claim 1, substantially as hereinbefore described.
12. Use according to claim 10, substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919103824A GB9103824D0 (en) | 1991-02-23 | 1991-02-23 | Formulation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE920516A1 true IE920516A1 (en) | 1992-08-26 |
Family
ID=10690478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE051692A IE920516A1 (en) | 1991-02-23 | 1992-02-18 | Steroid Formulations |
Country Status (13)
| Country | Link |
|---|---|
| CN (1) | CN1065010A (en) |
| AU (1) | AU1247192A (en) |
| BE (1) | BE1004177A4 (en) |
| FR (1) | FR2673104A1 (en) |
| GB (1) | GB9103824D0 (en) |
| GR (1) | GR1001511B (en) |
| IE (1) | IE920516A1 (en) |
| IL (1) | IL101010A0 (en) |
| IT (1) | IT1254627B (en) |
| MX (1) | MX9200748A (en) |
| PT (1) | PT100150A (en) |
| WO (1) | WO1992014473A1 (en) |
| ZA (1) | ZA921247B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0551626A1 (en) * | 1991-12-19 | 1993-07-21 | LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. | Thermoreversible gel as a liquid pharmaceutical carrier for a galenic formulation |
| US5976573A (en) * | 1996-07-03 | 1999-11-02 | Rorer Pharmaceutical Products Inc. | Aqueous-based pharmaceutical composition |
| JP2005281315A (en) * | 1997-07-02 | 2005-10-13 | Aventis Pharmaceuticals Holdings Inc | Aqueous pharmacological composition |
| TWI243687B (en) | 1998-04-21 | 2005-11-21 | Teijin Ltd | Pharmaceutical composition for application to mucosa |
| US20030059440A1 (en) * | 1998-09-01 | 2003-03-27 | Tim Clarot | Composition and method for moisturizing nasal tissue |
| AR026072A1 (en) * | 1999-10-20 | 2002-12-26 | Nycomed Gmbh | PHARMACEUTICAL COMPOSITION CONTAINING CICLESONIDE FOR MUCOSA APPLICATION |
| AR026073A1 (en) | 1999-10-20 | 2002-12-26 | Nycomed Gmbh | PHARMACEUTICAL COMPOSITION AQUATIC CONTAINING CICLESONIDE |
| DE10064950A1 (en) * | 2000-12-23 | 2002-07-11 | Impetus Ag Basel | Thixotropic nasal spray |
| EP1645266A1 (en) * | 2004-10-08 | 2006-04-12 | Hisamitsu Medical Co., Ltd. | Aqueous suspension for nasal drops |
| EP2057982A1 (en) * | 2007-11-09 | 2009-05-13 | Archimedes Development Limited | Intranasal compositions |
| WO2013049539A1 (en) * | 2011-09-30 | 2013-04-04 | Mcneil-Ppc, Inc. | A method of blocking or trapping allergens |
| WO2019073298A1 (en) * | 2017-10-11 | 2019-04-18 | Lifescience As | N-acetylneuraminic acid compositions and methods of use |
| AU2020220560A1 (en) * | 2019-02-11 | 2021-09-02 | Reckitt Benckiser Health Limited | Novel composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4361559A (en) * | 1981-08-20 | 1982-11-30 | E. R. Squibb & Sons, Inc. | Antiinflammatory 17,17-bis (substituted thio) androstenes |
| US4782047A (en) * | 1986-05-22 | 1988-11-01 | Syntex Pharmaceuticals International Ltd. | Aqueous steroid formulations for nasal administration |
| US4868170A (en) * | 1987-11-13 | 1989-09-19 | E. R. Squibb & Sons, Inc. | Steriod lotion formulation |
| IE67185B1 (en) * | 1990-02-02 | 1996-03-06 | Fisons Plc | Propellant compositions |
-
1991
- 1991-02-23 GB GB919103824A patent/GB9103824D0/en active Pending
-
1992
- 1992-02-18 GR GR920100064A patent/GR1001511B/en unknown
- 1992-02-18 IE IE051692A patent/IE920516A1/en unknown
- 1992-02-19 WO PCT/GB1992/000290 patent/WO1992014473A1/en active Application Filing
- 1992-02-19 AU AU12471/92A patent/AU1247192A/en not_active Abandoned
- 1992-02-19 IL IL101010A patent/IL101010A0/en unknown
- 1992-02-20 ZA ZA921247A patent/ZA921247B/en unknown
- 1992-02-21 MX MX9200748A patent/MX9200748A/en unknown
- 1992-02-21 BE BE9200182A patent/BE1004177A4/en not_active IP Right Cessation
- 1992-02-21 PT PT100150A patent/PT100150A/en not_active Application Discontinuation
- 1992-02-21 IT ITMI920393A patent/IT1254627B/en active IP Right Grant
- 1992-02-22 CN CN92101619A patent/CN1065010A/en active Pending
- 1992-02-24 FR FR9202105A patent/FR2673104A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE1004177A4 (en) | 1992-10-06 |
| WO1992014473A1 (en) | 1992-09-03 |
| ZA921247B (en) | 1992-10-28 |
| MX9200748A (en) | 1992-10-01 |
| ITMI920393A0 (en) | 1992-02-21 |
| FR2673104A1 (en) | 1992-08-28 |
| ITMI920393A1 (en) | 1993-08-21 |
| AU1247192A (en) | 1992-09-15 |
| PT100150A (en) | 1993-05-31 |
| GB9103824D0 (en) | 1991-04-10 |
| IL101010A0 (en) | 1992-11-15 |
| IT1254627B (en) | 1995-09-28 |
| CN1065010A (en) | 1992-10-07 |
| GR1001511B (en) | 1994-02-28 |
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