CN1942171B - Liquids containing suspended glass particles - Google Patents
Liquids containing suspended glass particles Download PDFInfo
- Publication number
- CN1942171B CN1942171B CN2005800110373A CN200580011037A CN1942171B CN 1942171 B CN1942171 B CN 1942171B CN 2005800110373 A CN2005800110373 A CN 2005800110373A CN 200580011037 A CN200580011037 A CN 200580011037A CN 1942171 B CN1942171 B CN 1942171B
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- Prior art keywords
- particle
- liquid
- glassy
- density
- preparation according
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- Expired - Fee Related
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- 239000002245 particle Substances 0.000 title claims abstract description 44
- 239000011521 glass Substances 0.000 title claims abstract description 14
- 239000007788 liquid Substances 0.000 title claims description 24
- 150000002170 ethers Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229960005486 vaccine Drugs 0.000 claims description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 4
- 239000001506 calcium phosphate Substances 0.000 claims description 4
- 235000011010 calcium phosphates Nutrition 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 abstract description 6
- 238000010792 warming Methods 0.000 abstract description 2
- 238000004513 sizing Methods 0.000 abstract 2
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 230000005923 long-lasting effect Effects 0.000 abstract 1
- 238000004321 preservation Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 2
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- -1 hydrogen fluorine amine Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940124872 Hepatitis B virus vaccine Drugs 0.000 description 1
- 241000590428 Panacea Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229950008618 perfluamine Drugs 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 1
- JAJLKEVKNDUJBG-UHFFFAOYSA-N perfluorotripropylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F JAJLKEVKNDUJBG-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
Classifications
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Glass Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Present proposals to use perfluorocarbons as a medium to suspend glass particles presents the problem of aggregation of the particles within the suspending medium. Overcoming this problem requires careful particle sizing and density matching techniques. An additional disadvantage of the large scale use of perfluorocarbons is their contribution to global warming. The inventor has realised that by replacing perfluorocarbons with the more environmentally friendly fluorinated ethers such as hydrofluoroethers or hydrofluoropolyethers a long lasting suspension of glass particles can be achieved without the need for such rigorous particle sizing or density matching processes.
Description
The present invention relates to a kind of preparation, it comprises the active component that is deposited in the particle that is suspended in the glassy or unbodied material in the liquid.
Well-known is that saccharifying glass (sugar glass) has some ability organic, biological, phytological and protein material of preservation, and there is lot of documents to be devoted to propose to use this specific character of saccharifying glass to remove preservation medicine, particularly vaccine in theory.Other glassy mass have demonstrated similar preservation effect.
Because the most frequently used acceptable vaccine administration method is the drug administration by injection that passes through that has proposed, for example having been proposed in patent specification WO 02/32402 (Roser) suspends in a kind of liquid (perfluocarbon is perfluorodecalin for example) contains the water-soluble glass shape particle of vaccine to produce a kind of injectable preparation.It is highly stable and be considered to be used for medicine and medical usage is safe because of them to propose perfluocarbon.In patent specification PCT WO02/32402, also propose by in saccharifying glass (density about 1.5), adding the density that calcium phosphate (density about 2.7 to 2.8) increases this glassy mass, so that the Particle Density value that produces is matched with this density of liquid value 1.97, it is suspended in the liquid; Thereby keep them to be in suspended state.
Above-mentioned technology has shown huge hope, but the stability completely of perfluocarbon means that they will be stored in the troposphere lastingly, and if a large amount of the use, may in fact cause global warming.In addition, hydrophilic glassy microsphere particles has shown slight accumulative tendency in perfluocarbon, and perfluocarbon is strong hydrophobic.
According to the present invention, a kind of preparation is provided, it comprises the active component that is deposited in the glassy or unbodied particle, this particle suspension is in liquid, and wherein at least a component comprises the material of hydrogen fluorine ether, perfluor ether, hydrogen fluorine amine, perfluamine, hydrogen fluorine thioether, perfluor thioether, hydrogen perfluoroalkyl polyether, PFPE or following general formula:
R1-X-R2 or
R1-X-(CF2Y) n (CF2CF2Z) m-R2 or
R1-[(X-CF-R2)n-(X-CF2)m]OR3
Wherein X, Y and Z are defined as O (oxygen), ether, NR3 (N=nitrogen), amine or S (sulfur); And each R1, R2 and R3 are defined as nonfluorinated, partially fluorinated or fluorinated alkyl, cycloalkyl, aryl or aralkyl or organo-functional group, halogen group or cyano group fully.
Preferably, hydrogen fluorine ether or hydrogen perfluoroalkyl polyether are considered to ideal, therefore, provide a kind of preparation, and it is included in the active component in the glassy or unbodied particle, and this particle suspension is in the liquid that contains hydrogen fluorine ether or hydrogen perfluoroalkyl polyether.
The inventor finds, when blended glassy particle is added in hydrogen fluorine ether or the hydrogen perfluoroalkyl polyether, their shockingly disperse easily to form cream, even after this suspension has been placed some times, and glassy particle all seldom or not have a sign of luming.
The inventor has been developed now should theory: glassy particle has water-wetted surface, and the previous perfluocarbon that uses was strong hydrophobic.Because this reason is thought now and used in the early stage in the test of perfluocarbon, it is the result that they are ostracised by the hydrophobic property of perfluocarbon that glassy particle has the tendency of together luming.The fluorinated ether performance a bit more resembles the detergent of this particle, promotes this dispersion of nano-particles.
Many fluorinated ether classes at present during operation technique as anesthetis via inhalation.The use of a large amount of relatively during operation technique (going up to 200 grams) has shown the hypotoxicity of this group.
In addition, their density also is complementary with the density of the glassy mass that uses in above-mentioned preparation ideally.For example, with reference to the regulation that is limited in 3M:
HFE 7500 has 1.61 density,
HFE 7200 has 1.43 density, and
HFE 7100 has 1.52 density.
These values as one man are similar to the density of saccharifying glass: about 1.5.
Use another benefit of the present invention to be, when fluorinated ether is exposed to strong ultraviolet radiation and for example is present in stratosphere, be unsettled, and under normal condition, be high stability.This has been avoided relevant to perfluocarbon the known problem that causes damaging " greenhouse " effect when being released into atmosphere after use.
Yet to be fluorinated ether inexpensive relatively and be easy to obtain being higher than 98% high-purity for another advantage of the present invention.This is than the PFC class, and the latter's a exemplary can obtain only about 55% purity.
Because fluorinated ether and glassy mass have so good coupling, it has become and may take the method for new density matching.Past is by using additive formulate glass shape thing to mate its density to liquid PFC.Yet the suitable density that needn't reach as required of becoming is now forced the selection of glassy mass.The invention enables might go to select ideal glassy/the active component compositions; And then fluorinated ether may mix with a small amount of PFC class or other liquid phases that add, so that density of liquid and Particle Density are complementary.Even practicable employing is deposited in the ready-made compositions of the active component in the glassy mass; It is ground into particle also then is suspended in it in a kind of liquid that is complementary with Particle Density.
Particle and density of liquid are not to equate.Yet they should be very approaching, makes the influence of Brownian movement or other thermodynamics keep particle to be in suspended state.
With reference to above, disperse so effectively in fluorinated ether and other liquid because found particle, it is so eager that the as far as possible little needs that suspend with maintenance of particle have not been resembled over.The expert improves dry spray technique, and its past is thought for obtaining small particle diameter required by the inventor, be unwanted now, although the drying process with atomizing of normal business remains a kind of possible technology of preparation particle.Yet, for example lyophilization or grinding of alternative approach also applicatory now.It only needs the particle should be enough little of to allow to pass through hypodermic syringe.
Prospect the present invention, it will be applied to the preparation that the protein of vaccine, treatment or other pass the medication that patient skin injects usually.Yet other purposes of the present invention also are possible, for example: be used for medicinal liquid, its after efflorescence by oral or inhalation.Also possible is, has non-medical usage of the present invention, and it generally is applicable to any situation of the compositions that is desirably in preservation bioactive substance in the glass solid and need exists with liquid form.
Now describe into a kind of method of the present invention.
Obtain aseptic, big quantity of fluid Hepatitis B virus vaccine and aluminium hydroxide adjuvant from Panacea Biotech of Delhi.Itself and aseptic colloid calcium phosphate suspension and Raffinose solution obtain 10 microgram vaccines of the single adult's dosage in 50 milligrams of total solids with suitable mixed.The ratio of calculating calcium phosphate and Raffinose is the solid glass shape particle of hydrogen fluorine ether HFE 7,500 density matching of 1.61 kg/liter to provide with density.With the magnetic stirring apparatus continuous stirring time, this suspension by two flow nozzles with the nozzle air current injection of the speed of 2 milliliters of per minutes with 2.5 kilograms/hour.The droplet that obtains is used per hour 30 kilograms heated air stream drying in the chamber of GEANiro SD Micro aerosol apparatus.Keep feed flow rates constant by regulating inlet temperature, remain on 90 ℃ to regulate outlet temperature.Product is collected in the aseptic bottle, and is transferred in the laminar flow fume hood with 100 classification air-flows.Aseptic HFE7,500 by the speed adding with 1 milliliter in per 100 milligrams of powder, and stirs 10 minutes with this microsphere of abundant dispersion in the frequency sweep ultra sonic bath.In this laminar flow fume hood, liquid is disperseed to enter in the 2 milliliters aseptic serum phial by the volume with 0.6 milliliter, seals with the neoprene stopper jam-pack and with aluminium lid.This vaccine phial is used to be based upon the vitro stability research of this vaccine under the different storage temperatures.
Claims (10)
1. preparation, it comprises the active component that is deposited in glassy or the amorphous particle, and described particle is suspended in the liquid, and wherein said liquid contains at least a in hydrogen fluorine ether or the hydrogen perfluoroalkyl polyether.
2. preparation according to claim 1, wherein said particle contains saccharifying glass or glassy mass, and described saccharifying glass or glassy mass are the combination in any of sugar, metal carboxylate, aminoacid and/or calcium phosphate.
3. preparation according to claim 1, the density that wherein said particle has itself and described density of liquid are complementary, and make that described particle keeps suspending under normal condition.
4. preparation according to claim 1, wherein said liquid also contains perfluocarbon.
5. preparation according to claim 1, wherein said active component are vaccine.
6. preparation according to claim 1, wherein said particle makes by spray drying.
7. preparation according to claim 1, wherein said particle makes by lyophilization.
8. preparation according to claim 1, wherein said particle makes by grinding.
9. method for preparing according to the described preparation of claim 3, it comprises active component is deposited in the glassy or unbodied particle, suspend this particle in liquid, described liquid contains a kind of fluorinated ether, and select the density of perfluocarbon with the matching properties that obtains described needs, then with liquid and described mix particles.
10. preparation, it comprises the active component that is deposited in the glassy or unbodied particle, described particle is suspended in the liquid that contains hydrogen fluorine ether.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0408199.8 | 2004-04-13 | ||
| GBGB0408199.8A GB0408199D0 (en) | 2004-04-13 | 2004-04-13 | Liquids containing suspended sugar glass particles |
| GB0504501A GB2413075B (en) | 2004-04-13 | 2005-03-07 | Liquids containing suspended glass particles |
| GB0504501.8 | 2005-03-07 | ||
| PCT/GB2005/050050 WO2005099669A1 (en) | 2004-04-13 | 2005-04-13 | Liquids containing suspended glass particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1942171A CN1942171A (en) | 2007-04-04 |
| CN1942171B true CN1942171B (en) | 2011-04-06 |
Family
ID=32320732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800110373A Expired - Fee Related CN1942171B (en) | 2004-04-13 | 2005-04-13 | Liquids containing suspended glass particles |
Country Status (10)
| Country | Link |
|---|---|
| CN (1) | CN1942171B (en) |
| AT (1) | ATE457717T1 (en) |
| DE (1) | DE602005019398D1 (en) |
| DK (1) | DK1750668T3 (en) |
| ES (1) | ES2339783T3 (en) |
| GB (2) | GB0408199D0 (en) |
| MX (1) | MXPA06011895A (en) |
| PT (1) | PT1750668E (en) |
| RU (1) | RU2363447C2 (en) |
| ZA (1) | ZA200609158B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0517688D0 (en) * | 2005-08-31 | 2005-10-05 | Cambridge Biostability Ltd | Improvements in the stabilisation of biological materials |
| GB0523638D0 (en) | 2005-11-21 | 2005-12-28 | Cambridge Biostability Ltd | Pharmaceutical device for the administration of substances to patients |
| US9243626B2 (en) | 2012-11-19 | 2016-01-26 | Nordson Corporation | Adhesive dispensing system and method including a pump with integrated diagnostics |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6190701B1 (en) * | 1999-03-17 | 2001-02-20 | Peter M. Ronai | Composition and method for stable injectable liquids |
| WO2001037804A2 (en) * | 1999-11-22 | 2001-05-31 | Universal Preservation Technologies, Inc. | Preservation and formulation of bioactive materials |
| US20020188281A1 (en) * | 1997-09-29 | 2002-12-12 | Dellamary Luis A. | Stabilized bioactive preparations and method of use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07258027A (en) * | 1994-03-16 | 1995-10-09 | Shiseido Co Ltd | Makeup cosmetic |
| CN100339066C (en) * | 2000-10-13 | 2007-09-26 | 剑桥生物稳定性有限公司 | Stable injecta composition and method |
-
2004
- 2004-04-13 GB GBGB0408199.8A patent/GB0408199D0/en not_active Ceased
-
2005
- 2005-03-07 GB GB0504501A patent/GB2413075B/en active Active
- 2005-04-13 DK DK05731023.7T patent/DK1750668T3/en active
- 2005-04-13 PT PT05731023T patent/PT1750668E/en unknown
- 2005-04-13 RU RU2006137275/15A patent/RU2363447C2/en not_active IP Right Cessation
- 2005-04-13 DE DE602005019398T patent/DE602005019398D1/en active Active
- 2005-04-13 CN CN2005800110373A patent/CN1942171B/en not_active Expired - Fee Related
- 2005-04-13 MX MXPA06011895A patent/MXPA06011895A/en unknown
- 2005-04-13 AT AT05731023T patent/ATE457717T1/en not_active IP Right Cessation
- 2005-04-13 ES ES05731023T patent/ES2339783T3/en active Active
-
2006
- 2006-11-03 ZA ZA200609158A patent/ZA200609158B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020188281A1 (en) * | 1997-09-29 | 2002-12-12 | Dellamary Luis A. | Stabilized bioactive preparations and method of use |
| US6190701B1 (en) * | 1999-03-17 | 2001-02-20 | Peter M. Ronai | Composition and method for stable injectable liquids |
| WO2001037804A2 (en) * | 1999-11-22 | 2001-05-31 | Universal Preservation Technologies, Inc. | Preservation and formulation of bioactive materials |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006137275A (en) | 2008-05-20 |
| ES2339783T3 (en) | 2010-05-25 |
| GB2413075B (en) | 2009-01-21 |
| GB0408199D0 (en) | 2004-05-19 |
| MXPA06011895A (en) | 2007-11-20 |
| CN1942171A (en) | 2007-04-04 |
| PT1750668E (en) | 2010-04-07 |
| GB0504501D0 (en) | 2005-04-13 |
| DK1750668T3 (en) | 2010-05-10 |
| RU2363447C2 (en) | 2009-08-10 |
| ZA200609158B (en) | 2008-06-25 |
| DE602005019398D1 (en) | 2010-04-01 |
| GB2413075A (en) | 2005-10-19 |
| ATE457717T1 (en) | 2010-03-15 |
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