ES2620442T3 - Uso de derivados de tetraquis(N-alquilpiridinio)-porfirina para la destrucción de microbios o la prevención de su crecimiento - Google Patents
Uso de derivados de tetraquis(N-alquilpiridinio)-porfirina para la destrucción de microbios o la prevención de su crecimiento Download PDFInfo
- Publication number
- ES2620442T3 ES2620442T3 ES09790946.9T ES09790946T ES2620442T3 ES 2620442 T3 ES2620442 T3 ES 2620442T3 ES 09790946 T ES09790946 T ES 09790946T ES 2620442 T3 ES2620442 T3 ES 2620442T3
- Authority
- ES
- Spain
- Prior art keywords
- prevention
- tmp
- erythema
- irritation
- alkylpyridinium
- 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.)
- Active
Links
- 230000002265 prevention Effects 0.000 title abstract 2
- 230000006378 damage Effects 0.000 title 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 title 1
- 238000011282 treatment Methods 0.000 abstract description 5
- 150000004032 porphyrins Chemical class 0.000 abstract description 3
- 230000000699 topical effect Effects 0.000 abstract 2
- 241000894006 Bacteria Species 0.000 abstract 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 206010015150 Erythema Diseases 0.000 description 14
- 231100000321 erythema Toxicity 0.000 description 13
- 230000007794 irritation Effects 0.000 description 12
- 206010030113 Oedema Diseases 0.000 description 10
- -1 lauryl methyl Chemical group 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 208000004210 Pressure Ulcer Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007682 dermal toxicity Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
Una composición tópica que comprende la porfirina de fórmula I:**Fórmula** en la que R1 es un grupo alquilo C12, y R2-R4 son metilo; y X- es un anión; para su uso en el tratamiento o la prevención de una enfermedad causada por un microbio en un mamífero; en la que el microbio se selecciona entre una bacteria y un hongo, y comprendiendo la composición tópica un vehículo farmacéutico.
Description
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TABLA 1 EVALUACIÓN DE DRAIZE1 DE LAS REACCIONES DÉRMICAS REACCIONES CUTÁNEAS PUNTUACIÓN
Eritema y formación de escaras (zona más gravemente afectada graduada):
Sin eritema 0 Eritema muy leve (apenas perceptible) 1 Eritema bien definido 2 Eritema de moderado a grave 3 Eritema grave (enrojecimiento de color remolacha) a ligera formación de escaras (lesiones 4 en profundidad)
NOTA: las zonas de ensayo que reciben una puntuación de "4" para el eritema requieren una descripción adicional en cuanto al grado de la lesión tisular.
Formación del edema (zona más gravemente afectada graduada):
Sin edema 0 Edema muy leve (apenas perceptible) 1 Edema ligero (bordes de la zona bien definidos por un levantamiento definido) 2 Edema moderado (elevación de aproximadamente 1 mm) 3 Edema grave (elevado más de 1 mm y que se extiende más allá de la zona de exposición) 4
1Draize, J. H. 1959. “Dermal Toxicity”. Páginas 46-59 en Appraisal of the Safety of Chemicals in Food, Drugs and Cosmetics. The Association of Food and Drug Officials of the United States, Bureau of Food and Drugs, Austin, TX.
TABLA 2 EVALUACIÓN DEL ÍNDICE DE IRRITACIÓN PRIMARIO ÍNDICE EVALUACIÓN
- 0,00
- Sin irritación
- 0,04-0,99 1,00-1,99 2,00–2,99
- Irritación apenas perceptible Irritación ligera Irritación leve
- 3,00-5,99
- Irritación moderada
- 6,00-8,00
- Irritación grave
- Resultados
Citotoxicidad de las porfirinas hacia diferentes tipos de células. Se evaluó la fototoxicidad de los derivados de porfirina lauril-metil-pirifrina y TMP en células HEKn. Se encontró que los compuestos eran no tóxicos o ligeramente tóxicos para las células a oscuras (> 60 % de tasa de supervivencia), hasta una concentración de 300 µM. Tras la exposición a la luz visible, las porfirinas mostraron citotoxicidad a todos los tipos de células, con tasas de supervivencia celular por debajo del 20 % a la concentración más alta estudiada.
Ensayo de irritación cutánea en ratones. En la Figura 1, se representan imágenes globales de ratones de diferentes grupos de tratamiento. Se expresaron los resultados individuales de la puntuación dérmica por eritema en la superficie erosionada (Figura 2); la superficie intacta (Figura 3); el edema de la zona erosionada (Figura 4); y la superficie intacta (Figura 5). Tras 24 horas, se observó un eritema muy leve en la mayor parte de lauril-metil-pirifrina 300 µM (6/6), TMP 30 µM (4/6) y TMP 300 µM (5/6) y lauril-metil-pirifrina 30 µM (2/6), con eritema bien definido en TMP 300 µM (6/6). Se observó un ligero edema en los ratones de ambos tratamientos de lauril-metil-pirifrina 300 µM y TMP 300 µM. Tras 72 horas, se observó un eritema muy leve en el tratamiento con lauril-metil-pirifrina 30 µM, y se observó una ligera diferencia con otros grupos de tratamiento. En la superficie intacta, no se observó eritema ni edema en ninguno de los ratones de lauril-metil-pirifrina y TMP, a excepción de TMP 300 µM con eritema y edema muy ligeros. Se calculó el índice de irritación primario de lauril-metil-pirifrina 3 µM en 0,00, 0,175 para lauril-metilpirifrina 30 µM, 1,4 para lauril-metil-pirifrina 300 µM, 0,6 para TMP 3 µM, 1,1 para TMP 30 µM y 2,9 para TMP 300 µM. Por lo tanto, la lauril-metil-pirifrina 3 µM no tiene ningún efecto de irritación sobre la piel; la lauril-metilpirifrina 30 µM y la TMP 3 µM tienen irritación apenas perceptible; la lauril-metil-pirifrina 300 µM y TMP 30 µM tienen ligera irritación; TMP 300 µM puede considerarse que tiene irritación leve.
8
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8440308P | 2008-07-29 | 2008-07-29 | |
| US84403P | 2008-07-29 | ||
| PCT/US2009/052128 WO2010014728A1 (en) | 2008-07-29 | 2009-07-29 | Use of tetrakis (n-alkylpyridinium) -porphyrin derivatives for killing microbes or preventing growth |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2620442T3 true ES2620442T3 (es) | 2017-06-28 |
Family
ID=41349499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09790946.9T Active ES2620442T3 (es) | 2008-07-29 | 2009-07-29 | Uso de derivados de tetraquis(N-alquilpiridinio)-porfirina para la destrucción de microbios o la prevención de su crecimiento |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8633311B2 (es) |
| EP (1) | EP2317857B1 (es) |
| JP (1) | JP2012504553A (es) |
| CN (1) | CN102245027A (es) |
| CA (1) | CA2733001A1 (es) |
| CL (1) | CL2011000186A1 (es) |
| ES (1) | ES2620442T3 (es) |
| MX (1) | MX2011001005A (es) |
| WO (1) | WO2010014728A1 (es) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102159214A (zh) | 2008-07-16 | 2011-08-17 | 药品循环公司 | 用于实体肿瘤的治疗的布鲁顿酪氨酸激酶的抑制剂 |
| MX2020004501A (es) | 2010-06-03 | 2021-11-09 | Pharmacyclics Llc | El uso de inhibidores de la tirosina quinasa de bruton (btk). |
| EA201490265A1 (ru) | 2011-07-13 | 2014-12-30 | Фармасайкликс, Инк. | Ингибиторы тирозинкиназы брутона |
| FR2987259B1 (fr) * | 2012-02-29 | 2014-02-21 | Oreal | Utilisation comme agent antipelliculaire de composes catalytiques d'oxydation choisi parmi les porphyrines, les phthalocyanines et les porphyrazines |
| CA3218491A1 (en) | 2012-06-04 | 2013-12-12 | Pharmacyclics Llc | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| BR112015001690A2 (pt) | 2012-07-24 | 2017-11-07 | Pharmacyclics Inc | mutações associadas com a resistência a inibidores da tirosina quinase de bruton (btk) |
| US20160008468A1 (en) * | 2013-02-27 | 2016-01-14 | Thomas J Lewis | Disease detection and treatment through activation of compounds using external energy |
| WO2015023703A1 (en) | 2013-08-12 | 2015-02-19 | Pharmacyclics, Inc. | Methods for the treatment of her2 amplified cancer |
| CN103601727A (zh) * | 2013-10-23 | 2014-02-26 | 中国医学科学院生物医学工程研究所 | 一种新型的胺类化合物修饰原卟啉的用途 |
| CN103800437A (zh) * | 2013-12-31 | 2014-05-21 | 芜湖乐锐思信息咨询有限公司 | 一种治疗虫霉病的中药 |
| US9885086B2 (en) | 2014-03-20 | 2018-02-06 | Pharmacyclics Llc | Phospholipase C gamma 2 and resistance associated mutations |
| WO2016022942A1 (en) | 2014-08-07 | 2016-02-11 | Pharmacyclics Llc | Novel formulations of a bruton's tyrosine kinase inhibitor |
| AU2016226279B2 (en) | 2015-03-03 | 2021-11-11 | Pharmacyclics Llc | Pharmaceutical formulations of Bruton's tyrosine kinase inhibtor |
| CN105830760B (zh) * | 2016-01-28 | 2019-01-11 | 中国计量学院 | 一种成功使茭白植株孕茭的菰黑粉菌人工接种方法 |
| WO2019032683A2 (en) * | 2017-08-08 | 2019-02-14 | Board Of Trustees Of Michigan State University | LIGHT-EMITTING ORGANIC SALTS FOR ENHANCED PHOTODYNAMIC THERAPY AND IMAGING |
| JP7241736B2 (ja) * | 2017-08-16 | 2023-03-17 | サンコー・エナジー・インコーポレイテッド | 植物における微生物病原体の光力学的阻害 |
| CN108179114B (zh) * | 2017-11-27 | 2021-08-20 | 南京晓庄学院 | 产抗厌氧菌化合物的菌株和发酵方法、抗厌氧菌化合物提取及制备方法和使用方法 |
| CN109136386B (zh) * | 2018-07-25 | 2021-12-24 | 华南农业大学 | 一种用于卡耶塔环孢子虫快速分型和溯源的定量pcr方法及试剂盒 |
| CN110205264B (zh) * | 2019-05-22 | 2020-09-04 | 暨南大学 | 水霉拮抗菌jd03及其发酵液与活性化合物在制备防治水霉病的产品中的应用 |
| CN110846248A (zh) * | 2019-11-19 | 2020-02-28 | 天津大学 | 一种用于多环芳烃降解的人工混菌体系及其应用方法 |
| CN111172047B (zh) * | 2020-02-12 | 2021-08-03 | 中国农业大学 | 一种桔假丝酵母菌及其应用 |
| NO347612B1 (en) * | 2020-06-17 | 2024-01-29 | Mowi ASA | Method for removing crustacean ectoparasites from farmed salmonid fish using water-soluble tetrapyrrole compounds and light |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9114290D0 (en) * | 1991-07-02 | 1991-08-21 | Courtaulds Plc | Polymer compositions |
| US6066628A (en) | 1997-01-09 | 2000-05-23 | Emory University | Non-iron metalloporphyrins and methods of use |
| US6462070B1 (en) | 1997-03-06 | 2002-10-08 | The General Hospital Corporation | Photosensitizer conjugates for pathogen targeting |
| IT1297080B1 (it) | 1997-11-26 | 1999-08-03 | Andrea Carnevali | Composizione per il trattamento di ustioni, eritemi solari, abrasioni, piaghe e irritazioni cutanee |
| US8974363B2 (en) | 1997-12-11 | 2015-03-10 | Provectus Pharmatech, Inc. | Topical medicaments and methods for photodynamic treatment of disease |
| ATE335513T1 (de) | 1998-10-16 | 2006-09-15 | Gen Hospital Corp | Photosensitizer-konjugate zur zielrichtung von intrazellulare pathogene |
| DE19910561A1 (de) | 1999-03-10 | 2000-09-14 | Schaffer Moshe | Verwendung von Porphyrinderivaten in Aquarien |
| DE19962505A1 (de) * | 1999-12-23 | 2001-07-05 | Schaffer Moshe | Mikrobizide Wirkung von Porphyrinen im Dunkeln |
| AU2001275855A1 (en) | 2000-06-29 | 2002-01-14 | University Of North Carolina At Chapel Hill | Inactivation of pathogens by porphyrins |
| US6573258B2 (en) | 2000-09-27 | 2003-06-03 | Frontier Scientific, Inc. | Photodynamic porphyrin antimicrobial agents |
| US6884797B2 (en) | 2001-03-30 | 2005-04-26 | Robert F. Hofmann | Targeted oxidative therapeutic formulation |
| US7439271B2 (en) | 2001-06-27 | 2008-10-21 | The Gillette Company | Reduction of hair growth |
| ITVR20010110A1 (it) | 2001-10-23 | 2003-04-23 | Giulio Jori | Procedimento di sterilizzazione microbiologica dell'acqua mediante agenti fotoattivabili. |
| AU2003212790B2 (en) | 2002-01-08 | 2006-05-25 | Emory University | Porphyrins with virucidal activity |
| GB2397067B (en) | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
| NL1022597C2 (nl) | 2003-02-05 | 2004-08-06 | Photobiochem N V | Toepassing van een fotosensitizerverbinding voor de bereiding van een farmaceutisch preparaat, werkwijze voor het bereiden van een farmaceutisch preparaat en een werkwijze voor het behandelen van een zoogdier. |
| EP1457113A1 (en) | 2003-03-12 | 2004-09-15 | Salbert Co Ltd | Alkylated porphyrins as pesticides acting both in the presence and absence of light |
| JP2006527196A (ja) | 2003-06-06 | 2006-11-30 | ユーカリオン，インコーポレイテッド | 経口で生体利用可能な低分子量メタロポルフィリン |
| GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
| CA2632183A1 (en) | 2005-08-25 | 2007-03-01 | Philip R. Houle | Treatment systems for delivery of sensitizer solutions |
| US20080015189A1 (en) | 2006-06-20 | 2008-01-17 | The General Hospital Corporation | Antimicrobial photoinactivation using chalcogen analogs of benzo(A)phenoxazinium dyes |
| GB0712287D0 (en) | 2007-06-22 | 2007-08-01 | Ucl Business Plc | Antimicrobial Conjugates |
| US8440309B2 (en) | 2011-01-31 | 2013-05-14 | Confluent Surgical, Inc. | Crosslinked polymers with the crosslinker as therapeutic for sustained release |
-
2009
- 2009-07-29 EP EP09790946.9A patent/EP2317857B1/en not_active Not-in-force
- 2009-07-29 JP JP2011521292A patent/JP2012504553A/ja not_active Withdrawn
- 2009-07-29 CA CA2733001A patent/CA2733001A1/en not_active Abandoned
- 2009-07-29 ES ES09790946.9T patent/ES2620442T3/es active Active
- 2009-07-29 CN CN2009801382585A patent/CN102245027A/zh active Pending
- 2009-07-29 WO PCT/US2009/052128 patent/WO2010014728A1/en active Application Filing
- 2009-07-29 MX MX2011001005A patent/MX2011001005A/es not_active Application Discontinuation
- 2009-07-29 US US13/056,441 patent/US8633311B2/en active Active
-
2011
- 2011-01-28 CL CL2011000186A patent/CL2011000186A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2011001005A (es) | 2011-09-01 |
| US20120016289A1 (en) | 2012-01-19 |
| CA2733001A1 (en) | 2010-02-04 |
| CL2011000186A1 (es) | 2012-03-02 |
| CN102245027A (zh) | 2011-11-16 |
| JP2012504553A (ja) | 2012-02-23 |
| WO2010014728A1 (en) | 2010-02-04 |
| EP2317857B1 (en) | 2016-12-28 |
| EP2317857A1 (en) | 2011-05-11 |
| US8633311B2 (en) | 2014-01-21 |
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