RU2018144958A - Композиции, содержащие полисахаридную матрицу для контролируемого высвобождения активных ингредиентов - Google Patents
Композиции, содержащие полисахаридную матрицу для контролируемого высвобождения активных ингредиентов Download PDFInfo
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- RU2018144958A RU2018144958A RU2018144958A RU2018144958A RU2018144958A RU 2018144958 A RU2018144958 A RU 2018144958A RU 2018144958 A RU2018144958 A RU 2018144958A RU 2018144958 A RU2018144958 A RU 2018144958A RU 2018144958 A RU2018144958 A RU 2018144958A
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- compositions according
- cyclodextrin
- chitosan
- lactose
- hyaluronic acid
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- 239000000203 mixture Substances 0.000 title claims 20
- 239000004480 active ingredient Substances 0.000 title claims 5
- 150000004676 glycans Chemical class 0.000 title claims 4
- 229920001282 polysaccharide Polymers 0.000 title claims 4
- 239000005017 polysaccharide Substances 0.000 title claims 4
- 239000011159 matrix material Substances 0.000 title claims 3
- 238000013270 controlled release Methods 0.000 title 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 10
- 229920001661 Chitosan Polymers 0.000 claims 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 9
- 239000008101 lactose Substances 0.000 claims 9
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims 8
- 229920002674 hyaluronan Polymers 0.000 claims 8
- 229960003160 hyaluronic acid Drugs 0.000 claims 8
- 229920001542 oligosaccharide Chemical class 0.000 claims 8
- 150000002482 oligosaccharides Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 claims 3
- 239000001116 FEMA 4028 Substances 0.000 claims 3
- 229960004853 betadex Drugs 0.000 claims 3
- 229940097362 cyclodextrins Drugs 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 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 3
- 230000001154 acute effect Effects 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- -1 ester derivatives of β-cyclodextrin Chemical class 0.000 claims 2
- 210000002346 musculoskeletal system Anatomy 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims 2
- QGKBSGBYSPTPKJ-UZMKXNTCSA-N 2,6-di-o-methyl-β-cyclodextrin Chemical compound COC[C@H]([C@H]([C@@H]([C@H]1OC)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O3)[C@H](O)[C@H]2OC)COC)O[C@@H]1O[C@H]1[C@H](O)[C@@H](OC)[C@@H]3O[C@@H]1COC QGKBSGBYSPTPKJ-UZMKXNTCSA-N 0.000 claims 1
- TZIZWYVVGLXXFV-FLRHRWPCSA-N Triamcinolone hexacetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)CC(C)(C)C)[C@@]1(C)C[C@@H]2O TZIZWYVVGLXXFV-FLRHRWPCSA-N 0.000 claims 1
- 230000021736 acetylation Effects 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229940037157 anticorticosteroids Drugs 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 229960004752 ketorolac Drugs 0.000 claims 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- 229960002702 piroxicam Drugs 0.000 claims 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims 1
- 229960004221 triamcinolone hexacetonide Drugs 0.000 claims 1
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
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- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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Claims (17)
1. Композиции, содержащие клатрат, состоящий из циклодекстрина и активного ингредиента, где клатрат циклодекстрина и активного ингредиента однородно диспергирован в полисахаридной полимерной матрице в водном растворе, образованном гиалуроновой кислотой и/или ее солями и олигосахаридным производным хитозана с лактозой, полученным путем реакции восстановительного аминирования D-глюкозамина хитозана, имеющим степень замещения функциональной группы амина лактозой по меньшей мере 40%.
2. Композиции по п. 1, отличающиеся тем, что циклодекстрины выбраны из эфирных производных β-циклодекстрина и γ-циклодекстрина и их смесей, где одна или более гидроксильных групп замещены C1-6-алкильными, гидрокси-С1-6-алкильными, карбокси-С1-6-алкильными, C1-6 алкилоксикарбонильными и С1-4-сульфоалкильными группами.
3. Композиции по п. 2, отличающиеся тем, что циклодекстрины выбраны из 2,6-диметил-β-циклодекстрина, 2-гидроксиэтил-β-циклодекстрина, 2-гидроксипропил-β-циклодекстрина, (2-карбоксиметокси)пропил-β-циклодекстрина, 2-гидроксипропил-γ-циклодекстрина, сульфобутилового эфира (7)-β-циклодекстрина.
4. Композиции по п. 3, отличающиеся тем, что циклодекстрины выбраны из сульфобутилового эфира (7)-β-циклодекстрина, 2-гидроксипропил-β-циклодекстрина и 2-гидроксипропил-γ-циклодекстрина.
5. Композиции по п. 1, отличающиеся тем, что гиалуроновая кислота и/или ее соли имеют среднюю молекулярную массу от 500 до 10000 кДа.
6. Композиции по п. 5, отличающиеся тем, что гиалуроновая кислота и/или ее соли имеют среднюю молекулярную массу от 500 до 2000 кДа.
7. Композиции по п. 1, отличающиеся тем, что олигосахаридное производное хитозана с лактозой имеет среднюю молекулярную массу от 500 до 1000 кДа и степень остаточного ацетилирования от 10 до 20%.
8. Композиции по п. 1, отличающиеся тем, что олигосахаридное производное хитозана с лактозой имеет степень замещения от 50 до 70%.
9. Композиции по п. 1, отличающиеся тем, что циклодекстрин составляет от 1% до 30% масс./об.
10. Композиции по п. 1, отличающиеся тем, что полисахаридная матрица, образованная гиалуроновой кислотой и/или ее солями и олигосахаридным производным хитозана с лактозой составляет от 0,5% до 4% масс./об.
11. Композиции по п. 10, отличающиеся тем, что отдельные полисахаридные компоненты составляют от 0,25% до 2% масс./об.
12. Композиции по п. 11, отличающиеся тем, что массовые соотношения гиалуроновой кислоты и/или ее солей к олигосахаридному производному хитозана с лактозой составляют от 1:3 до 10:1 (гиалуроновая кислота: олигосахаридное производное хитозана с лактозой).
13. Композиции по п. 12, отличающиеся тем, что массовые соотношения гиалуроновой кислоты и/или ее солей к олигосахаридному производному хитозана с лактозой составляют от 1:1 и 5:1 (гиалуроновая кислота: олигосахаридное производное хитозана с лактозой).
14. Композиции по п. 1, отличающиеся тем, что активные ингредиенты выбраны из противоинфекционных средств и кортикостероидов и нестероидных противовоспалительных агентов.
15. Композиции по п. 14, отличающиеся тем, что активные ингредиенты выбраны из группы, состоящей из триамцинолона ацетонида, триамцинолона гексацетонида, диклофенака, пироксикама, кеторолака и их смесей.
16. Композиции по любому из пп. 1-14 для применения для локорегионарного лечения заболеваний костно-мышечной системы, характеризующихся острыми и хроническими воспалительными состояниями.
17. Композиции по п. 15, отличающиеся тем, что заболевания костно-мышечной системы представляют собой острые и хронические костно-суставные заболевания.
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| PCT/EP2017/068085 WO2018015364A1 (en) | 2016-07-19 | 2017-07-18 | Compositions comprising a polysaccharide matrix for the controlled release of active ingredients |
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| JP7703245B2 (ja) * | 2021-06-24 | 2025-07-07 | 上海雲晟研新生物科技有限公司 | ケトロラック液体組成物、その製造方法及び応用 |
| CN115850722B (zh) * | 2023-02-22 | 2023-05-09 | 翔鹏(北京)生物科技有限公司 | 一种高效透皮的超分子透明质酸钠制备方法及应用 |
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| US20070020299A1 (en) * | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid |
| ITMI20041245A1 (it) | 2004-06-22 | 2004-09-22 | Ibsa Inst Biochimique Sa | Composizioni farmaceutiche iniettabnili comprendenti diclofenac sodico e b-ciclodestrina |
| ITPD20060202A1 (it) | 2006-05-22 | 2007-11-23 | Univ Degli Studi Trieste | Miscele polimeriche di polisaccaridi anionici e cationici e loro impiego |
| EP2117513A2 (en) | 2007-02-05 | 2009-11-18 | Carbylan Biosurgery, Inc. | Polymer formulations for delivery of bioactive agents |
| US8273725B2 (en) | 2009-09-10 | 2012-09-25 | Genzyme Corporation | Stable hyaluronan/steroid formulation |
| EA201300341A1 (ru) | 2010-09-16 | 2013-09-30 | Шимода Байотек (Пти) Лтд. | Композиция фулвестранта и способы применения |
| SI2616064T1 (sl) | 2010-10-21 | 2019-12-31 | Rtu Pharmaceuticals Llc | Pripravki ketorolaka, pripravljeni za uporabo |
| RU2448120C1 (ru) * | 2010-11-01 | 2012-04-20 | Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" | Клатратные комплексы бета-циклодекстрина с 1-{[6-бром-1-метил-5-метокси-2-фенилтиометил-1-н-индол-3-ил]карбонил}-4-бензилпиперазином, обладающие противовирусной активностью, их получение и применение |
| KR101383941B1 (ko) | 2012-03-09 | 2014-04-10 | 동아에스티 주식회사 | 피록시캄 또는 약제학적으로 허용되는 그의 염과 히알루론산 또는 약제학적으로 허용되는 그의 염의 안정한 액상 조성물 및 그 제조방법 |
| US20150272877A1 (en) | 2012-10-26 | 2015-10-01 | Allergan, Inc. | Ketorolac-containing sustained release drug delivery systems |
| CN103142463B (zh) * | 2013-03-05 | 2015-09-09 | 宁夏康亚药业有限公司 | 眼用药物组合物,其制备方法及应用 |
| WO2014153384A1 (en) | 2013-03-19 | 2014-09-25 | Flexion Therapeutics, Inc. | Corticosteroid formulations for the treatment of joint pain and methods of use thereof |
| KR101439032B1 (ko) | 2013-06-13 | 2014-09-05 | 동아에스티 주식회사 | 피록시캄과 히알루론산을 포함하는 골관절염 치료를 위한 액상 조성물 |
| ITMI20132116A1 (it) | 2013-12-18 | 2015-06-19 | Apharm Srl | Associazione di glicosamminoglicani e ciclodestrine |
| CN105030663B (zh) * | 2015-07-07 | 2018-08-31 | 上海通用药业股份有限公司 | 一种溶液型醋酸曲安奈德注射液的制备方法 |
| CN104971039B (zh) * | 2015-07-07 | 2018-04-17 | 上海通用药业股份有限公司 | 一种含溶液型醋酸曲安奈德的医用产品 |
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| CA3028042A1 (en) | 2018-01-25 |
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| MX389461B (es) | 2025-03-20 |
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