CA2625532C - Agent for applying to mucosa containing a hydrophobic group binding type glycosaminoglycan - Google Patents
Agent for applying to mucosa containing a hydrophobic group binding type glycosaminoglycan Download PDFInfo
- Publication number
- CA2625532C CA2625532C CA2625532A CA2625532A CA2625532C CA 2625532 C CA2625532 C CA 2625532C CA 2625532 A CA2625532 A CA 2625532A CA 2625532 A CA2625532 A CA 2625532A CA 2625532 C CA2625532 C CA 2625532C
- Authority
- CA
- Canada
- Prior art keywords
- glycosaminoglycan
- hydrophobic group
- agent
- mucosa
- group
- 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.)
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- 229920002683 Glycosaminoglycan Polymers 0.000 title claims abstract description 126
- 125000001165 hydrophobic group Chemical group 0.000 title claims abstract description 95
- 210000004877 mucosa Anatomy 0.000 title abstract description 104
- 210000005081 epithelial layer Anatomy 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 73
- -1 phenylethenyl Chemical group 0.000 claims description 46
- 125000006850 spacer group Chemical group 0.000 claims description 27
- 230000002265 prevention Effects 0.000 claims description 20
- 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 description 15
- 229920002674 hyaluronan Polymers 0.000 claims description 15
- 229960003160 hyaluronic acid Drugs 0.000 claims description 15
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 12
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000000600 disaccharide group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 50
- 208000035475 disorder Diseases 0.000 abstract description 49
- 239000004480 active ingredient Substances 0.000 abstract description 9
- 230000003902 lesion Effects 0.000 abstract description 7
- 206010061218 Inflammation Diseases 0.000 abstract description 6
- 230000004054 inflammatory process Effects 0.000 abstract description 6
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 83
- 239000000126 substance Substances 0.000 description 80
- 229940114081 cinnamate Drugs 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
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- 239000007864 aqueous solution Substances 0.000 description 42
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 210000004087 cornea Anatomy 0.000 description 33
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- 230000002950 deficient Effects 0.000 description 21
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000002209 hydrophobic effect Effects 0.000 description 18
- 229960003299 ketamine Drugs 0.000 description 18
- NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 17
- 210000000214 mouth Anatomy 0.000 description 17
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 17
- 229960001600 xylazine Drugs 0.000 description 17
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
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- 206010002091 Anaesthesia Diseases 0.000 description 13
- 230000037005 anaesthesia Effects 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 12
- 206010013781 dry mouth Diseases 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
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- 208000005946 Xerostomia Diseases 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 241000699800 Cricetinae Species 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 210000005252 bulbus oculi Anatomy 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
- 238000002695 general anesthesia Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000002834 transmittance Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 description 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000006196 drop Substances 0.000 description 6
- 238000010253 intravenous injection Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000201841 Celosia Species 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003889 eye drop Substances 0.000 description 5
- 229940012356 eye drops Drugs 0.000 description 5
- 210000004400 mucous membrane Anatomy 0.000 description 5
- 239000013642 negative control Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- 206010013774 Dry eye Diseases 0.000 description 4
- 206010037508 Punctate keratitis Diseases 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 description 4
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 4
- 229940014041 hyaluronate Drugs 0.000 description 4
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 4
- 230000002085 persistent effect Effects 0.000 description 4
- 238000011907 photodimerization Methods 0.000 description 4
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 2
- GZAJOEGTZDUSKS-UHFFFAOYSA-N 5-aminofluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C21OC(=O)C1=CC(N)=CC=C21 GZAJOEGTZDUSKS-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005297170 | 2005-10-12 | ||
| JP2005-297170 | 2005-10-12 | ||
| JP2006-160478 | 2006-06-09 | ||
| JP2006160478 | 2006-06-09 | ||
| PCT/JP2006/320801 WO2007043702A1 (en) | 2005-10-12 | 2006-10-12 | Agent for applying to mucosa and method for production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2625532A1 CA2625532A1 (en) | 2007-04-19 |
| CA2625532C true CA2625532C (en) | 2013-10-01 |
Family
ID=37942916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2625532A Active CA2625532C (en) | 2005-10-12 | 2006-10-12 | Agent for applying to mucosa containing a hydrophobic group binding type glycosaminoglycan |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20080306022A1 (enExample) |
| EP (1) | EP1942912B1 (enExample) |
| JP (3) | JP4387445B2 (enExample) |
| KR (4) | KR20130109259A (enExample) |
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| AU (1) | AU2006300207C1 (enExample) |
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| GB0327723D0 (en) | 2003-09-15 | 2003-12-31 | Vectura Ltd | Pharmaceutical compositions |
| KR20130109259A (ko) * | 2005-10-12 | 2013-10-07 | 세이가가쿠 고교 가부시키가이샤 | 점막에 적용하는 작용제 및 그것의 제조 방법 |
| US8889652B2 (en) | 2006-12-06 | 2014-11-18 | Seikagaku Corporation | Pharmaceutical agent having long-lasting effect of treating arthritic disorders |
| JP2009046454A (ja) * | 2007-08-22 | 2009-03-05 | Shiseido Co Ltd | 口腔内用組成物 |
| ITMI20072237A1 (it) * | 2007-11-27 | 2009-05-28 | Sigea Srl | Esteri misti butirrico-formico di polisaccaridi acidi, loro preparazione ed uso come dermocosmetici |
| CN102177180A (zh) | 2008-04-04 | 2011-09-07 | 犹他州大学研究基金会 | 烷基化半合成的糖胺聚糖醚及其制备和使用方法 |
| EP2360188B1 (en) * | 2008-11-05 | 2014-09-17 | National University Corporation Tokyo Medical and Dental University | Hyaluronic acid derivative and pharmaceutical composition thereof |
| FR2958646B1 (fr) | 2010-04-07 | 2012-05-18 | Adocia | Polysaccharides comportant des groupes fonctionnels carboxyles substitues par un derive d'acide hydrophobe. |
| CA2703532C (en) * | 2010-05-10 | 2018-05-01 | Eva Turley | Topically administered, skin-penetrating glycosaminoglycan formulations suitable for use in cosmetic and pharmaceutical applications |
| CA2830933A1 (en) | 2011-03-23 | 2012-09-27 | University Of Utah Research Foundation | Methods for treating or preventing urological inflammation |
| US9067299B2 (en) | 2012-04-25 | 2015-06-30 | Applied Materials, Inc. | Printed chemical mechanical polishing pad |
| EP3238728B1 (en) * | 2014-12-26 | 2020-09-02 | Seikagaku Corporation | Agent comprising hyaluronic acid having an aminoalkyl cinnamate covalently bonded thereto for improving subjective symptoms in eyes |
| CN104940221A (zh) * | 2015-05-13 | 2015-09-30 | 北京大清生物技术有限公司 | 一种用于膀胱和尿道上皮损伤修复的组合物 |
| JP6887377B2 (ja) * | 2015-05-29 | 2021-06-16 | 生化学工業株式会社 | グリコサミノグリカン誘導体とケモカイン受容体活性調節材とを含む組成物 |
| WO2017030184A1 (ja) * | 2015-08-20 | 2017-02-23 | 生化学工業株式会社 | 眼用デバイス適用剤 |
| JP6356374B2 (ja) * | 2016-05-26 | 2018-07-11 | 株式会社オフテクス | 加水分解ヒアルロン酸誘導体及びカチオン系殺菌剤を含有するコンタクトレンズ用液剤 |
| WO2018053111A1 (en) | 2016-09-15 | 2018-03-22 | University Of Utah Research Foundation | In situ gelling compositions for the treatment or prevention of inflammation and tissue damage |
| WO2018069763A1 (en) * | 2016-10-14 | 2018-04-19 | i.com medical GmbH | Method for establishing, restoring, and preserving homeostasis of the ocular surface |
| JP7216006B2 (ja) | 2017-03-22 | 2023-01-31 | ジェネンテック， インコーポレイテッド | ヒドロゲル架橋ヒアルロン酸プロドラッグ組成物及び方法 |
| RU2652581C1 (ru) * | 2017-07-03 | 2018-04-26 | федеральное государственное бюджетное образовательное учреждение высшего образования "Приволжский исследовательский медицинский университет" Министерства здравоохранения Российской Федерации | Способ лечения роговично-конъюнктивального ксероза |
| CN111228653A (zh) | 2018-11-13 | 2020-06-05 | 格莱科米拉治疗公司 | 用电离辐射加强癌症治疗的方法 |
| EP4039279A4 (en) | 2019-10-03 | 2023-11-01 | Seikagaku Corporation | TRANSMUCOSAL MEDICINAL ACTIVE DELIVERY SYSTEM FOR THE BLADDER SUBMUCOSA |
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| AU3327000A (en) * | 1999-03-24 | 2000-10-09 | Seikagaku Corporation | Artificial saliva |
| ATE250924T1 (de) | 2000-04-07 | 2003-10-15 | Medidom Lab | Cyklosporin, hyaluronsäure und polysorbate enthaltenes augenarzneimittel |
| JP2001329002A (ja) * | 2000-05-25 | 2001-11-27 | Denki Kagaku Kogyo Kk | 修飾ヒアルロン酸ゲルとその製造方法及びそれを含有する医用材料 |
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2006
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- 2006-10-12 JP JP2008519554A patent/JP4387445B2/ja active Active
- 2006-10-12 EP EP06811990.8A patent/EP1942912B1/en not_active Not-in-force
- 2006-10-12 CN CN201210562963.1A patent/CN103120702B/zh not_active Expired - Fee Related
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