WO2006089993B1 - Procedimiento de obtención de hidrogeles de ciclodextrinas con glicidiléteres, las composiciones obtenidas y sus aplicaciones - Google Patents
Procedimiento de obtención de hidrogeles de ciclodextrinas con glicidiléteres, las composiciones obtenidas y sus aplicacionesInfo
- Publication number
- WO2006089993B1 WO2006089993B1 PCT/ES2006/000096 ES2006000096W WO2006089993B1 WO 2006089993 B1 WO2006089993 B1 WO 2006089993B1 ES 2006000096 W ES2006000096 W ES 2006000096W WO 2006089993 B1 WO2006089993 B1 WO 2006089993B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogels
- cyclodextrins
- compositions
- ether
- cyclodextrin
- Prior art date
Links
- 239000000017 hydrogel Substances 0.000 title claims abstract 19
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract 16
- 238000000034 method Methods 0.000 title claims abstract 14
- 239000000203 mixture Substances 0.000 title claims abstract 12
- 229940097362 cyclodextrins Drugs 0.000 title claims abstract 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 title claims abstract 7
- 229920002907 Guar gum Polymers 0.000 claims abstract 7
- 239000000665 guar gum Substances 0.000 claims abstract 7
- 235000010417 guar gum Nutrition 0.000 claims abstract 7
- 229960002154 guar gum Drugs 0.000 claims abstract 7
- 229920003086 cellulose ether Polymers 0.000 claims abstract 6
- 239000003431 cross linking reagent Substances 0.000 claims abstract 6
- 239000003814 drug Substances 0.000 claims abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000013543 active substance Substances 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims abstract 4
- 241000196324 Embryophyta Species 0.000 claims abstract 2
- 241000282412 Homo Species 0.000 claims abstract 2
- 241001465754 Metazoa Species 0.000 claims abstract 2
- 238000013270 controlled release Methods 0.000 claims abstract 2
- 239000002537 cosmetic Substances 0.000 claims abstract 2
- 238000000605 extraction Methods 0.000 claims abstract 2
- 239000007943 implant Substances 0.000 claims abstract 2
- 231100000331 toxic Toxicity 0.000 claims abstract 2
- 230000002588 toxic effect Effects 0.000 claims abstract 2
- -1 methyl- Chemical group 0.000 claims 16
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 9
- 150000002170 ethers Chemical class 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 244000007835 Cyamopsis tetragonoloba Species 0.000 claims 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 2
- 238000004090 dissolution Methods 0.000 claims 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 2
- 238000010348 incorporation Methods 0.000 claims 2
- 229920000609 methyl cellulose Polymers 0.000 claims 2
- 239000001923 methylcellulose Substances 0.000 claims 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 claims 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 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 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 239000003124 biologic agent Substances 0.000 claims 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 238000000265 homogenisation Methods 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 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 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000003352 sequestering agent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- 238000002604 ultrasonography Methods 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
Classifications
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- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
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- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
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- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
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- Dispersion Chemistry (AREA)
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- Birds (AREA)
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- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Cosmetics (AREA)
Abstract
Procedimiento de obtención de hidrogeles a base de ciclodextrinas, de ciclodextrinas y éteres de celulosa, o de ciclodextrinas y goma guar o sus derivados, utilizando como agente reticulante moléculas que contienen dos o más grupos glicidiléter en su estructura; las composiciones obtenidas capaces de incorporar fármacos y sustancias activas, que forman complejos de inclusión con ciclodextrinas; su uso como componentes de dispositivos de liberación controlada, tales como formas farmacéuticas transdérmicas, formas transmucosales bucales, orales, rectales, oculares, óticas o vaginales, e implantes parenterales, destinadas a administrar fármacos o sustancias activas a humanos, animales o plantas, o como componentes de preparados cosméticos; y el uso de las composiciones como secuestrantes, en la extracción de moléculas tóxicas o biológicas en organismos vivos o de sustancias contaminantes en aguas.
Claims
1. Procedimiento de obtención de hidrogcles caracterizado por que los hidrogeles están constituidos por: i. ciclodextrinas o sus derivados, y éteres de celulosa hidrosolubles o sus derivados hidrosolubles ; o ii. ciclodextrinas o sus derivados, y gomas guar o sus derivados; iii, y, además, empleando como agente reticulante moléculas que contienen en su estructura dos o más grupos glicidiléter,
2. Procedimiento de obtención de hidrogeles, según la reivindicación 1, caracterizado porque en el caso i) comprende las siguientes etapas: a) disolución de la ciclodextrina o de in derivado de ciclodextrina y del éter de celulosa o de un derivado del éter de celulosa en agua o medio hidroalcohólico; b) ajuste del pH de la disolución; c) incorporación del agente reticulante y homogeneización de la mezcla; d) transferencia a un molde; e) mantenimiento en cámara termostatizada a temperatura comprendida entra 0 y 100°C; f) extracción del molde; g) lavado del hidrogcl; b) división en porciones de forma y tamaño adecuados.
3. Procedimiento de obtención de hidrogeles, según la reivindicación 1 caracterizado porque en el caso ii) comprende las siguientes etapas: a) disolución de la ciclodextrina o de un derivado de ciclodextrina, y de la goma guar o de un derivado de goma guar en agua o medio hidroalcohólico; y a continuación las etapas b) a h) de la reivindicación 2.
4. Procedimiento de obtención de hidrogeles, según las reivindicaciones 1, 2 y 3, caracterizado porque en las etapas a) y b) el medio de reacción es agua o medio hidroalcobólico y presenta un pH ácido, neutro o alcalino.
5- Procedimiento de obtención de hidrogeles, según las reivindicaciones 1, 2, 3 y 4, que incluye una etapa de secado de los hidrogeles en estufa de vacio o con corriente de aire, o por liofilización, entre las etapas g) y h) o después de la h).
6. Procedimiento de obtención de hidrogeles, según las reivindicaciones anteriores, caracterizado porque las ciclodextrinas o sus derivados son las α-, β- y γ- ciclodextrinas, las ciclodextrinas compuestas por más de ocho unidades de α-1.4- glucopiranosa, y los derivados metil-, etil-, butil-, hidroxietil-, 2-hidroxipropil- , 2- hidroxibutil-, acetil-, propionil-, butiril-, succinil-, benzoil-. palmitil-, toluensulfonil-, acetilmetil-, acetil outil-, glucosil-, maltosil-, carboximetil éter-, carboximetil etil-, fosfato éster-, 3-tr..τfietilainoi-iun-- sulfobutil éter- ciclodextrina- y los polímeros de ciclodextrina.
7. Procedimiento de obtención de hidrogeles, según las reivindicaciones 1 y 2, caracterizado porque los éteres de celnlosa o sus derivados son éteres iónicos o no iónicos, tales como metilcelulosa (MC), hidroxietilmetilcelulosa (HEMC), hidroxipropilcelulosa (HPC), hjdroxipropilmetilcelulosa (HPMC), hidroxietilcelulosa (HEC), elilhidroxío;ilcelulosa (EHEC), carboximetilcelulosa sódica (CMCNa), las sales de amonio cuaterrario de hidroxietilcelulosa con sustituyente trimetilarnonio y los copolímeros de hid: oxietil celulosa y cloruro de dimetil dialilamonio.
S. Procedir- iento de obtención de hidrogeles. según las reivindicaciones 1 y 3, caracterizado porqi. e las gomas guar o sus derivados son cualquier goma guar, cualquier goma guar modif cada o cualquier derivado de goma guar, como cualquier éter hidroxipropilado o carboxibidroxipropüado, cualquier derivado catióπico o cualquier producto resultanti; de su depolimerización.
9. Procedimiento de obtención de hidrogeles, según las reivindicaciones 1 a 5, caracterizado porque el agente reticulante es una sustancia que contiene en su estructura dos o más grupos glicidiléter; entendiéndose por glicidiléter: oxírano, epóxido, u óxido de alqueno; tales como: diglicidiléter. etüenglicoldiglicidileter, dietilenglicoJdiglieidileter, propilenglicoldiglicidiléter, polietilεnglicolpoliglicidileier, gliceroltriglicidileter, poliglicerolpoliglicidileter y bisfenol A diglicidilcter-
10. Procedimiento de obtención de hidrogeles, según las reivindicaciones 1, 2, 7 y 9, caracterizado porque la proporción de ciclodextrina o del derivado de ciclodextrina está comprendida intre el 1% y el 95%; la proporción de éter de celulosa o del derivado de éter de celulosa está comprendida entre el 0,05% y el 95%; y la proporción del agente reticulante está comprendida entre 98.95% y el 4% del total de los componentes del lήdrogel.
11. Procedimiento deobtención de hidrogeles, según las reivindicaciones 1, 3, 8 y 9, caracterizado porque la proporción de ciclodextriπa o del derivado de ciclodextrina está comprendida entre el 1% y el 95%: la proporción de goma guar o del derivado de goma guar está co.nprendida entre el 0.05% y el 95%; y la proporción del agente reticulante está comprendida entre 98.95% y el 4% del total de los componentes del hidrogel.
12. Procedí -niento de obtención de hidrogeles, según las reivindicaciones anteriores, que incluye una etapa de incorporación de fármaco o de sustancia activa por inmersión del hidrogel, húmedo o previamente desecado, en una disolución o en una suspensión del fármaco o de la sustancia activa, a temperatura comprendida entre 0 y 100°C y a la presión atmosférica, con ayuda o no de ultrasonidos. La incorporación también se puede levar a cabo en autoclave a temperatura comprendida entre 100 y 130°C
13. Composiciones obtenidas según las reivindicaciones anteriores.
14. Composiciones, según las reivindicaciones anteriores, que incorporan a los hidrogeles, fármacos, sustancias activas o nutrientes para su liberación controlada.
15. Composiciones, según las reivindicaciones anteriores, caracterizadas porque, en organismos vivos o en el medioambiente, capturan sustancias biológicas o tóxicas actuando como age ntes secuestrantes.
16. Uso de las composiciones, según las reivindicaciones anteriores, para la elaboración de un medicamento o un producto fitosanitario para el tratamiento de estados patológico 3 o fisiológicos en humanos, animales y plantas.
17.- Uso de las composiciones, según la reivindicación 18, para la elaboración de un medicamen:o para administrar por vía transdérmica, transmucosal, bucal, oral, rectal, ocular, nasal, ótica o vaginal, o como implante parenteral
18.- Uso de las composiciones, según las reivindicaciones 1 a 15, para la preparación de cosméticos.
19. Uso de las composiciones, según la reivindicación 15, para la elaboración de un agente secucsirante de sustancias biológicas o tóxicas para actuar en organismos vivos o en el medi'oambiente.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/887,167 US20090214604A1 (en) | 2005-02-25 | 2006-02-15 | Method of obtaining hydrogels of cyclodextrins with glycidyl ethers, compositions thus obtained and applications thereof |
EP06725794A EP1873167A4 (en) | 2005-02-25 | 2006-02-15 | METHOD FOR THE PRODUCTION OF HYDROGELS OF CYCLODEXTRINS WITH GLYCIDYL ETHERS, COMPOSITIONS OBTAINED THEREFOR AND APPLICATIONS THEREOF |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200500556A ES2310948B2 (es) | 2005-02-25 | 2005-02-25 | Procedimiento de obtencion de hidrogeles de ciclodextrinas con glicidileteres, las composiciones obtenidas y sus aplicaciones. |
ESP200500556 | 2005-02-25 |
Publications (3)
Publication Number | Publication Date |
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WO2006089993A2 WO2006089993A2 (es) | 2006-08-31 |
WO2006089993A3 WO2006089993A3 (es) | 2006-11-02 |
WO2006089993B1 true WO2006089993B1 (es) | 2006-11-30 |
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PCT/ES2006/000096 WO2006089993A2 (es) | 2005-02-25 | 2006-02-15 | Procedimiento de obtención de hidrogeles de ciclodextrinas con glicidiléteres, las composiciones obtenidas y sus aplicaciones |
Country Status (4)
Country | Link |
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US (1) | US20090214604A1 (es) |
EP (1) | EP1873167A4 (es) |
ES (1) | ES2310948B2 (es) |
WO (1) | WO2006089993A2 (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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ITMI20071321A1 (it) * | 2007-07-04 | 2009-01-05 | Sea Marconi Technologies Di Va | Nanospugne a base di ciclodestrine come veicolo per farmaci antitumorali |
US9345809B2 (en) | 2007-11-28 | 2016-05-24 | Fziomed, Inc. | Carboxymethylcellulose polyethylene glycol compositions for medical uses |
ES2335958B2 (es) | 2008-08-06 | 2010-11-02 | Universidad De Santiago De Compostela | Hidrogeles acrilicos con ciclodextrinas colgantes, su preparacion y su aplicacion como sistemas de liberacion y componentes de lentes de contacto. |
FI20115279A0 (fi) * | 2011-03-22 | 2011-03-22 | Teknologian Tutkimuskeskus Vtt Oy | Menetelmä hydrogeelin valmistamiseksi ksylaanipolysakkaridista ja hydrogeeli |
ES2371898B2 (es) * | 2011-09-29 | 2012-06-13 | Universidade De Santiago De Compostela | Nanogeles de ciclodextrina. |
EP2698392A1 (en) * | 2012-08-17 | 2014-02-19 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Polymer network material comprising a poly(glycidyl ether) structure, method of its production and use |
WO2018187404A1 (en) | 2017-04-05 | 2018-10-11 | Gelesis, Llc | Improved superabsorbent materials and methods of production thereof |
CN109081927B (zh) * | 2018-06-25 | 2020-07-03 | 天津科技大学 | 一种水凝胶的制备方法 |
CN109734934B (zh) * | 2019-01-11 | 2021-11-02 | 闽江学院 | 一种纳米纤维素温敏凝胶的制备方法 |
CN112915064A (zh) * | 2021-02-02 | 2021-06-08 | 大连海事大学 | 一种药物缓释载体水凝胶的制备方法及其应用 |
US20220332924A1 (en) * | 2021-04-09 | 2022-10-20 | Qatar Foundation For Education, Science And Community Development | Cyclodextrin-derived polymer nanoparticles for adsorption and synthesis thereof |
CN114304143A (zh) * | 2021-12-06 | 2022-04-12 | 盐城工学院 | 一种农药传递体系及其制备方法 |
US20230348796A1 (en) * | 2022-04-28 | 2023-11-02 | Saudi Arabian Oil Company | Polymer-metal salt composite for the dehydration of water from sweet gas and liquid condensate streams |
Family Cites Families (14)
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CH445129A (fr) * | 1964-04-29 | 1967-10-15 | Nestle Sa | Procédé pour la préparation de composés d'inclusion à poids moléculaire élevé |
HU181733B (en) * | 1980-08-07 | 1983-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing sorbents containing cyclodextrin on cellulose base |
HU191101B (en) * | 1983-02-14 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing water-soluble cyclodextrin polymers substituted with ionic groups |
JPS6020924A (ja) | 1983-07-14 | 1985-02-02 | Agency Of Ind Science & Technol | ビ−ズ状不溶性シクロデキストリンポリマ−の製法 |
US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
US4596795A (en) * | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
HU203899B (en) * | 1988-05-03 | 1991-10-28 | Forte Fotokemiai Ipar | Process for producing gelatine-cyclodextreine polymeres |
DE4033007A1 (de) * | 1990-10-18 | 1992-04-23 | Cassella Ag | Verwendung von phosphonsaeurediglycidylestern als vernetzer bei der herstellung von hydrogelen |
EP0916925A1 (en) | 1997-11-17 | 1999-05-19 | YASHIMA ELECTRIC CO., Ltd. | Inclination sensor |
US6048736A (en) * | 1998-04-29 | 2000-04-11 | Kosak; Kenneth M. | Cyclodextrin polymers for carrying and releasing drugs |
DE19911097A1 (de) | 1999-03-12 | 2000-09-14 | Basf Ag | Verfahren zur Herstellung von festen cyclodextrinhaltigen Dosierungsformen |
TW494548B (en) * | 2000-08-25 | 2002-07-11 | I-Ming Chen | Semiconductor chip device and its package method |
NO310176B1 (no) * | 2000-11-13 | 2001-06-05 | Wadlund As | Sammensetning for hud som inneholder kitosan-konjugert CLA og kitosankonjugert vitamin A eller et <beta>-cyklodekstrin-konjugertvitamin A samt fremgangsmåte for fremstilling og anvendelse avdenne |
US7297348B2 (en) | 2002-07-19 | 2007-11-20 | Omeros Corporation | Biodegradable triblock copolymers, synthesis methods therefore, and hydrogels and biomaterials made there from |
-
2005
- 2005-02-25 ES ES200500556A patent/ES2310948B2/es active Active
-
2006
- 2006-02-15 EP EP06725794A patent/EP1873167A4/en not_active Withdrawn
- 2006-02-15 WO PCT/ES2006/000096 patent/WO2006089993A2/es active Application Filing
- 2006-02-15 US US11/887,167 patent/US20090214604A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
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ES2310948B2 (es) | 2009-09-16 |
EP1873167A4 (en) | 2010-08-18 |
US20090214604A1 (en) | 2009-08-27 |
WO2006089993A2 (es) | 2006-08-31 |
WO2006089993A3 (es) | 2006-11-02 |
EP1873167A2 (en) | 2008-01-02 |
ES2310948A1 (es) | 2009-01-16 |
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