EP2410975A1 - A medicinal antibacterial cream and a process to make it - Google Patents

A medicinal antibacterial cream and a process to make it

Info

Publication number
EP2410975A1
EP2410975A1 EP10716072A EP10716072A EP2410975A1 EP 2410975 A1 EP2410975 A1 EP 2410975A1 EP 10716072 A EP10716072 A EP 10716072A EP 10716072 A EP10716072 A EP 10716072A EP 2410975 A1 EP2410975 A1 EP 2410975A1
Authority
EP
European Patent Office
Prior art keywords
cream
added
amount
group
combination
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Withdrawn
Application number
EP10716072A
Other languages
German (de)
English (en)
French (fr)
Inventor
Madhavan Srinivasan
Neelakandan Narayanan Chulliel
Sulur Subramaniam Vanangamudi
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP2410975A1 publication Critical patent/EP2410975A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the word healing as related to compromised skin conditions are not only about prevention, control, elimination of the source cause such as bacteria or fungi but also to restore the skin to its pre-infection state.
  • Patent applications EP2092935 and PCT/IN2008/000577 provide an insight into the typical way steroids such as Mometasone Furoate are used towards topical prescription derma products.
  • US 6,899,897 discloses a biological dressing comprising a sticky film of gum resin - benzoin, a pharmacologically active agent - clotrimazole is left on the skin or mucous membrane after the volatile solvent - ethanol has evaporated.
  • the composition further may include penetration enhancer. It claims novelty over the assertion that the dressing disclosed herewith is a clean and inexpensive vehicle/carrier of topically applied medications increasing the convenience and effectiveness of the treatment and decreasing the necessary time for the treatment. This is apparently associated with less waste and lower cost and improved treatment.
  • the film formed is apparently extends retention on the skin since it is resistant to water and abrasion by clothing.
  • Figure 1 Non-homogeneous nature of creams containing chitosan with non- compatible excipient such as carbomer
  • biopolymer examples include, but are not limited to chitosan and the like.
  • Chitosan is a linear polysaccharide composed of randomly distributed ⁇ -(l-4)- linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It is known to have a number of commercial uses in agriculture and horticulture, water treatment, chemical industry, pharmaceuticals and biomedics.
  • Chitosan due to its unique physical property accelerates wound healing and wound repair. It is positively charged and soluble in acidic to neutral solution. Chitosan is bioadhesive and readily binds to negatively charged surfaces such as mucosal membranes. Chitosan enhances the transport of polar drugs across epithelial surfaces. Chitosan's properties allow it to rapidly clot blood, and it has recently gained approval in the USA for use in bandages and other hemostatic agents.
  • Chitosan is no nailer genie, and has natural anti-bacterial properties, further supporting its use. As a micro-film forming biomaterial, Chitosan helps in reducing the width of the wound, controls the oxygen permeability at the site, absorbs wound discharge and gets degraded by tissue enzymes which are very much required for healing at a faster rate. It also reduces the itching by providing a soothing effect. It also acts like a moisturizer. It is also useful in treatment of routine minor cuts and wounds, burns, keloids, diabetic ulcers and venous ulcers. Chitosan used in the present invention comes in various molecular weights ranging from lkdal to 5000kdal.
  • the molecular weight of the chitosan plays an important role in the formulation.
  • Higher molecular weight chitosan imparts a higher viscosity to the system and lower molecular weight chitosan imparts a lower viscosity to the system.
  • Topical Antibacterials are intended to target skin for bacterial infections caused by Staphylococcus aureus, Staphylococcus epidermidis, Methicillin - resistance Staphylococcus aureus (MRSA) etc.
  • Topical antibacterial agents include, but are not limited to, Sodium Fusidate, Calcium Mupirocin, Gentamycin, Neomycin, Silver Sulphadiazine, Ciprofloxacin, Framycetin Sulphate, Quinidochlor, Povidone-Iodine, Sisomicin, Nitrofural and the like.
  • Hydrocarbon bases e.g. hard paraffin, soft paraffin
  • Absorption bases e.g. wool fat, bees wax
  • the acidic scale of pH is from 1 to 7, and the base scale of pH is from 7 to 14.
  • Human skins pH value is some where between 4.5 and 6. Newborn baby's skin pH is closer to neutral (pH 7), but it quickly turns acidic. Nature has designed this probably to protect young children's skin, since acidity kills bacteria. As people become older, the skin becomes more and more neutral, and won't kill as many bacteria as before. This is why the skin gets weak and starts having problems.
  • the pH value goes beyond 6 when a person actually has a skin problem or skin disease. This shows that it is necessary to choose topicals that have a pH value close to that of skin of a young adult.
  • cream formulations are available as creams. Active compounds in cream formulations are available in ionized state, whereas in case of ointments these are present in non-ionized state.
  • the cream formulations are the first choice of the formulators in design and development of topical dosage forms, as the cream formulations are cosmetically elegant, and also as the active compound is available in ionized state, and the drug can penetrate the skin layer fast which makes the formulation totally patient friendly.
  • the pH of the cream of the present invention with a functional biopolymer such as Chitosan, steroids, anti fungal agent is from about 3 to 6.
  • a functional biopolymer such as Chitosan, steroids, anti fungal agent
  • ointments that are commercially available are greasy and cosmetically non elegant.
  • the active compound in an ointment is in non-ionized form, the penetration of skin is slow.
  • Topical antibacterial agents have profound efficacy in primary & secondary bacterial skin infections of varied etiology due to its antibacterial properties.
  • a drawback of the monotherapy with any topical antibacterial has been the relatively slow onset of the effect. .
  • chitosan By employing antibacterial & chitosan in a formulation, the properties of both antibacterials and chitosan are optimized.
  • chitosan is film forming, biocompatible, non-allergenic material it helps in protecting the skin by acting as a barrier. It further controls the superficial bleeding caused by scratching and also arrests the mobility of pathogens due to its cationic charge.
  • chitosan in the formulation takes care of many attributes, which are considered to be very much essential in treating skin ailments.
  • the combination of chitosan with antibacterial is unique and novel since this is not available commercially across the globe.
  • Another inventive aspect of the present invention is that the addition of a functional excipient in the cream base is not a straight forward process of mere addition.
  • the inventor has found that the compatibility of the functional excipient such as chitosan with other agents in the cream is of critical importance. This is because incompatibility would compromise the stability of the final product.
  • the inventors have found that well known excipients such as Xanthan Gum and carbopol which have been variously used as stabilising agents, cannot be used in combination with functional biopolymers such as chitosan.
  • Excipients for topical dosage forms include Polymers, Surfactants, Waxy Materials, Emulsifiers etc. Polymers are used as gelling agents, suspending agents, viscosity builders, release modifiers, diluents, etc. Surfactants are used as wetting agents, emulsifiers, solubilising agents release enhancers, etc.
  • Polymers & Surfactants may or may not possess ionic charge. They may be anionic or cationic or non-ionic in nature. If anionic excipients are included in the formulation they interact with cationic formulation excipients and produce products which are not homogenous, aesthetically not appealing and give rise to unwanted by products, possible allergens, impurities, toxic substances etc due to incompatibility.
  • the final product was also not aesthetically appealing without homogeneity.
  • the attached figure 1 clearly explains the interaction between chitosan and unsuitable anionic excipients. Based on the observations and thorough knowledge about the excipients, the inventors arrived at a robust formula without any possible interactions.
  • tablettes 1 to 5 are examples of products that do not form homogeneous creams, and produce non-homogeneous creams of the type illustrated in figure 1. Yet the proportions stated in these examples are some things that a person skilled in the art may use based currently available knowledge. Only after a thorough and extensive trials and errors would it be possible to arrive at right types and proportions of excipients.
  • antibacterials provide relief against bacterial infections.
  • the aspects such as like skin protection, bleeding at the site, mobility of pathogens from one site to another, etc are not addressed so far in a single dose therapy.
  • This present invention with its single-dose application fills this gap by incorporating chitosan and tapping the required benefits of skin protection (by way of film forming property), stopping the bleeding (by way of blood clotting property) and immobilization of pathogenic microbes (due to its cationic electrostatic property).
  • Therapeutic value addition by incorporation of a functional excipient in the form of a chitosan which is a biopolymer in the cream matrix.
  • the value addition is an integrated sub-set of the following functional attributes of the biopolymer: formulation of a micro-film on the skin surface accelerated blood clotting as compared to creams that do not contain film- forming biopolymers electrostatic immobilisation of surface microbes due to cationic charge of the biopolymer - significant enhancement of the skin epithelisation or regeneration
  • inventive efforts involved in developing the platform technology covered by incorporation of a functional biopolymer in prescription dermaceutical products are: in identification of the complementary therapeutic value that such incorporation delivers in identification of issues related to physio -chemical stability of the product resulting from the incorporation of the biopolymer in providing a single dose format where the bacterial infection has been identified.
  • the unique innovative formulation of the present invention takes care of the skin conditions by treating them along with controlling the superficial bleeding at the site. It is well understood that if the superficial bleeding is left untreated, it will lead to secondary microbial infections.
  • the present invention advantageously provides a solution to this unmet need.
  • the present invention with its single-dose therapy reduces the overall treatment time of a serious skin disorder significantly.
  • a novel dermaceutical cream for topical treatment of bacterial skin infections, and for related wound healing wherein said cream comprises an antibacterial agent, and a biopolymer provided in a cream base, said cream base comprising at least one of each of a preservative, a primary and a secondary emulsifier, a waxy material, a co-solvent, an acid, and water, preferably purified water.
  • said antibacterial agent is added in an amount between about 0.5% w/w and about 15% w/w, more preferably between 0.5 and 5.0% w/w; and, said biopolymer is in the form of chitosan, added in an amount between about 0.01% and about 1% by weight, preferably from about 0.01% w/w to about 0.5% w/w and most preferably about 0.25% w/w, said chitosan being US pharmacopeia conformant with regard to its functional excipient category and selected from any grades such as long chain, medium chain & short chain, and has a molecular weight in the range between 5OkDa to 5000 kDa,
  • said primary and secondary emulsifiers are selected from a group comprising Cetostearyl alcohol, Cetomacrogol-1000, Cetyl alcohol, Stearyl alcohol, Polysorbate-80, Span-80 and the like and added in an amount from about 1% (w/w) to 20% (w/w); said waxy materials is selected from a group comprising white soft paraffin, liquid paraffin, hard paraffin and the like, or any combination thereof, from about 5% (w/w) to 50% (w/w); said co-solvent is selected from a group comprising Propylene Glycol, Hexylene Glycol, PolyEthylene Glycol-400 and the like, or any combination thereof, and added in an amount from about 5% (w/w) to 50% (w/w); said acid is selected from a group comprising HCl, H 2 SCU, HNO 3 , Lactic acid and the like, or any combination thereof, and added in an amount from about 0.005% (w/w) to 0.5% (w/w/
  • Embodiment no. 3 is a diagrammatic representation of Embodiment no. 3:
  • a buffering agent which is selected from a group comprising Di Sodium Hydrogen Ortho Phosphate, Sodium Hydrogen Ortho Phosphate, Calcium lactate and the like, or any combination thereof, and added in an amount from about 0.05% (w/w) to 1.00% (w/w).
  • Embodiment no. 4 A novel cream as disclosed in the preferred embodiment no. 1 and the embodiments no. 2 and 3, further comprising an antioxidant which is selected from a group comprising Butylated Hydroxy Anisole, Butylated Hydroxy Toluene and the like, or any combination thereof, and added in an amount from about 0.05% (w/w) to 5% (w/w).
  • an antioxidant which is selected from a group comprising Butylated Hydroxy Anisole, Butylated Hydroxy Toluene and the like, or any combination thereof, and added in an amount from about 0.05% (w/w) to 5% (w/w).
  • Embodiment no. 5 A novel cream as disclosed in the preferred embodiment no. 1 and the embodiments no.2 to 4, further comprising a chelating agent which is selected from a group comprising Disodium EDTA and the like, or any combination thereof, and added in an amount from about 0.05% (w/w) to 1% (w/w).
  • a chelating agent which is selected from a group comprising Disodium EDTA and the like, or any combination thereof, and added in an amount from about 0.05% (w/w) to 1% (w/w).
  • Embodiment no. 6 A novel cream as disclosed in the preferred embodiment no. 1 and the embodiments no. 2 to 4, further comprising a humectant which is selected from a group comprising Glycerin, Sorbitol, and the like, or any combination thereof, and added in an amount from about 5% (w/w) to 50% (w/w).
  • a humectant which is selected from a group comprising Glycerin, Sorbitol, and the like, or any combination thereof, and added in an amount from about 5% (w/w) to 50% (w/w).
  • Embodiment no. 7 A novel cream as disclosed in the preferred embodiment no. 1 and the embodiments no. 2 to 4, further comprising a stabilizer which is selected from a group comprising Guar gum and the like, or any combination thereof, and added in an amount from about 0.1 % (w/w) to 5% (w/w).
  • a stabilizer which is selected from a group comprising Guar gum and the like, or any combination thereof, and added in an amount from about 0.1 % (w/w) to 5% (w/w).
  • Embodiment no. 8 A process of making a cream is disclosed, said process comprising the steps of providing an antibacterial agent, and a biopolymer in a cream base comprising at least one of each of a preservative, a primary and a secondary emulsifier, a waxy material, a co-solvent, an acid, and water, preferably purified water, and mixing all the ingredients together to form a homogeneous cream.
  • Embodiment no. 9 A process of making a cream as disclosed in the embodiment no. 7, wherein the ingredients further comprise any of a group comprising a buffering agent, an antioxidant, a chelating agent, a humectant, a stabilizer or any combination thereof.
  • Embodiment no. 10 A novel cream as disclosed in any of the foregoing embodiments, wherein chitosan has a molecular weight range of lkdal to 5000kdal.
  • Example-I Table 6:_Sodium Fusidate + Chitosan Cream
  • Example-III Table 8: Framycetin Sulphate + Chitosan Cream
  • Example-IV Table 9: Silver Sulphadiazine + Chitosan Cream
  • APIs-stability experiments were carried out (see tables 10- 21) using the product of the present invention. Tests were carried out to observe (or measure as appropriate) the physical appearance of the product, the pH value and assay of the APIs over a period of time.
  • Each gram of product of the present invention used for the tests contained appropriate amount of antibacterials.
  • Each gm contains: Sodium Fusidate BP Equivalent to Fusidic
  • Measured parameter pH; Limits of measured parameter: 3-6 Method of measurement: Di ital H Meter
  • composition Each gm contains!) Calcium Mupirocin USP equivalent to
  • Measured parameter pH; Limits of measured parameter: 3-6 Method of measurement: Digital pH Meter
  • topically applied cream of the present invention is due to the pronounced antibacterial activity of the actives against the organisms responsible for skin infections, the unique ability of actives to penetrate intact skin and wound healing & soothing properties of chitosan.
  • the cream of the present invention incorporates a biopolymer without compromising the stability of the cream matrix and without adversely affecting the functioning of known active pharmaceutical ingredients. This has been achieved through a careful selection of functional excipients to bypass undesirable aspects of physio- chemical compatibility/stability and bio-release.
  • the cream of the present invention provides an integrated uni-dose or a single-dose therapy hitherto unavailable in prescription dermaceutical formulations.
  • the novel cream of the present invention is adequately stable/efficacious at ambient conditions and does not need special temperature control during transportation/storage - hence will go a long way in achieving these social objectives.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Birds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
EP10716072A 2009-03-25 2010-03-24 A medicinal antibacterial cream and a process to make it Withdrawn EP2410975A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN701MU2009 2009-03-25
PCT/IB2010/051280 WO2010109417A1 (en) 2009-03-25 2010-03-24 A medicinal antibacterial cream and a process to make it

Publications (1)

Publication Number Publication Date
EP2410975A1 true EP2410975A1 (en) 2012-02-01

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EP10716072A Withdrawn EP2410975A1 (en) 2009-03-25 2010-03-24 A medicinal antibacterial cream and a process to make it

Country Status (7)

Country Link
EP (1) EP2410975A1 (pt)
JP (1) JP2012521410A (pt)
CN (1) CN102365075A (pt)
BR (1) BRPI1006455A2 (pt)
IL (1) IL215126A0 (pt)
MX (1) MX2011009934A (pt)
WO (1) WO2010109417A1 (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9044488B2 (en) 2009-04-13 2015-06-02 Vanangamudi Sulur Subramaniam Medicinal cream made using silver sulphadiazine and chitosan and a process to make it
WO2012049545A1 (en) * 2010-10-12 2012-04-19 Sulur Subramaniam Vanangamudi A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer and a process to make it
WO2012049541A1 (en) * 2010-10-15 2012-04-19 Sulur Subramaniam Vanangamudi A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer and a corticosteroid, and a process to make it
WO2012049543A1 (en) * 2010-10-15 2012-04-19 Sulur Subramaniam Vanangamudi A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer and a corticosteroid, and a process to make it
CN105640795B (zh) * 2014-11-28 2019-06-07 上海家化联合股份有限公司 一种含多元醇和乳酸的温和性组合物的制备与应用
KR20220087501A (ko) * 2019-10-24 2022-06-24 비샤간 바난가무디 술루르 박테리아 감염 및 상처 치유를 위한 약제학적 조성물을 함유하는 국소 항생제
GB2597445B (en) * 2020-07-21 2022-11-09 Hydrodyne Systems Ltd An Antimicrobial Cosmetic Preparation

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3253982B2 (ja) * 1991-03-13 2002-02-04 ピアス株式会社 にきび用化粧料
DE19826503A1 (de) * 1998-06-13 1999-12-16 Beiersdorf Ag Kosmetische und dermatologische Zubereitungen mit einem Gehalt an Chitosan und Phospholipiden
DE19852212A1 (de) * 1998-11-12 2000-05-18 Beiersdorf Ag Zubereitungen vom Emulsionstyp W/O mit erhöhtem Wassergehalt, enthaltend ferner ein oder mehrere Alkylmethiconcopolyole und/oder Alkyl-Dimethiconpolyole sowie kationische Polymere
US20030206958A1 (en) * 2000-12-22 2003-11-06 Cattaneo Maurizio V. Chitosan biopolymer for the topical delivery of active agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010109417A1 *

Also Published As

Publication number Publication date
JP2012521410A (ja) 2012-09-13
WO2010109417A1 (en) 2010-09-30
IL215126A0 (en) 2011-12-29
CN102365075A (zh) 2012-02-29
MX2011009934A (es) 2011-10-06
BRPI1006455A2 (pt) 2018-02-27

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