JP2019501262A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019501262A5 JP2019501262A5 JP2018533195A JP2018533195A JP2019501262A5 JP 2019501262 A5 JP2019501262 A5 JP 2019501262A5 JP 2018533195 A JP2018533195 A JP 2018533195A JP 2018533195 A JP2018533195 A JP 2018533195A JP 2019501262 A5 JP2019501262 A5 JP 2019501262A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorescent
- salt
- complex
- hyaluronic acid
- formula
- 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- Withdrawn
Links
- 229920002674 hyaluronan Polymers 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002105 nanoparticle Substances 0.000 claims description 9
- GRAVJJAQKJDGPM-UHFFFAOYSA-N 3-[2-[7-[3-(2-carboxyethyl)-1,1-dimethylbenzo[e]indol-3-ium-2-yl]hepta-2,4,6-trienylidene]-1,1-dimethylbenzo[e]indol-3-yl]propanoic acid;bromide Chemical group [Br-].OC(=O)CCN1C2=CC=C3C=CC=CC3=C2C(C)(C)\C1=C/C=C/C=C/C=C/C1=[N+](CCC(O)=O)C2=CC=C(C=CC=C3)C3=C2C1(C)C GRAVJJAQKJDGPM-UHFFFAOYSA-N 0.000 claims description 8
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 229930012538 Paclitaxel Natural products 0.000 claims description 3
- 239000000824 cytostatic agent Substances 0.000 claims description 3
- 230000001085 cytostatic effect Effects 0.000 claims description 3
- 229960004679 doxorubicin Drugs 0.000 claims description 3
- 229960001592 paclitaxel Drugs 0.000 claims description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- 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 12
- 229960003160 hyaluronic acid Drugs 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- 150000007530 organic bases Chemical class 0.000 claims 6
- 230000002209 hydrophobic effect Effects 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 4
- 238000011503 in vivo imaging Methods 0.000 claims 4
- 239000002798 polar solvent Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 230000004913 activation Effects 0.000 claims 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 230000032050 esterification Effects 0.000 claims 3
- 238000005886 esterification reaction Methods 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- 150000004665 fatty acids Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 230000009918 complex formation Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000000539 dimer Substances 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 238000007912 intraperitoneal administration Methods 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 239000012048 reactive intermediate Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 2
- 0 CC(C)(C(C=CC=C*=CC=C(C1(C)C)N(CCC(N=O)=O)c2c1c(cccc1)c1cc2)=I)c(c(cccc1)c1cc1)c1NCCC(O)=O Chemical compound CC(C)(C(C=CC=C*=CC=C(C1(C)C)N(CCC(N=O)=O)c2c1c(cccc1)c1cc2)=I)c(c(cccc1)c1cc1)c1NCCC(O)=O 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(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-MNSSHETKSA-N 0.000 description 1
- 229940099552 hyaluronan Drugs 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZPV2015-936 | 2015-12-23 | ||
| CZ2015-936A CZ307511B6 (cs) | 2015-12-23 | 2015-12-23 | Fluorescenční konjugát kyseliny hyaluronové nebo jeho sůl, hydrofobizovaný konjugát, způsoby jejich přípravy a použití |
| PCT/CZ2016/050048 WO2017108015A1 (en) | 2015-12-23 | 2016-12-22 | Fluorescent cypate conjugate of hyaluronic acid or salt thereof, hydrophobized conjugate, methods of perparation and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019501262A JP2019501262A (ja) | 2019-01-17 |
| JP2019501262A5 true JP2019501262A5 (https=) | 2020-01-30 |
Family
ID=59089116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018533195A Withdrawn JP2019501262A (ja) | 2015-12-23 | 2016-12-22 | ヒアルロン酸又はその塩の蛍光Ｃｙｐａｔｅ複合体，疎水化複合体，それらの調製方法及び使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20190001000A1 (https=) |
| EP (1) | EP3393527B1 (https=) |
| JP (1) | JP2019501262A (https=) |
| KR (1) | KR20180096761A (https=) |
| BR (1) | BR112018012554A2 (https=) |
| CZ (1) | CZ307511B6 (https=) |
| DK (1) | DK3393527T3 (https=) |
| ES (1) | ES2751091T3 (https=) |
| HU (1) | HUE045756T2 (https=) |
| PL (1) | PL3393527T3 (https=) |
| RU (1) | RU2018123820A (https=) |
| WO (1) | WO2017108015A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115501204B (zh) * | 2022-10-25 | 2023-07-21 | 河北工业大学 | 一种用于级联递送药物的透明质酸纳米给药系统的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180087B1 (en) | 2000-01-18 | 2001-01-30 | Mallinckrodt Inc. | Tunable indocyanine dyes for biomedical applications |
| US6669926B1 (en) | 2000-10-16 | 2003-12-30 | Mallinckrodt, Inc. | Hydrophilic light absorbing indole compounds for determination of physiological function in critically ill patients |
| WO2006078914A1 (en) * | 2005-01-21 | 2006-07-27 | Washington University In St. Louis | Compounds having rd targeting motifs |
| US7875260B2 (en) * | 2006-08-24 | 2011-01-25 | Baylor College Of Medicine | Imaging agents for functional imaging of lymphatic structures |
| US8758727B2 (en) | 2008-03-31 | 2014-06-24 | University Of Louisville Research Foundation, Inc. | Site specific fluorescence and contrast marker for same |
| CZ305040B6 (cs) | 2010-09-14 | 2015-04-08 | Contipro Biotech S.R.O. | Způsob přípravy vysoce substituovaných amidů kyseliny hyaluronové |
| JP2012149034A (ja) * | 2010-12-27 | 2012-08-09 | Canon Inc | 複合粒子、光音響イメージング用造影剤、及び光音響イメージング方法 |
| KR20130085294A (ko) * | 2012-01-19 | 2013-07-29 | 충남대학교산학협력단 | 림프노드 탐지용 형광 고분자 나노젤 및 이를 이용한 림프노드 확인 방법 |
| WO2014028861A1 (en) * | 2012-08-17 | 2014-02-20 | Apellis Pharmaceuticals, Inc. | Detection of high risk drusen |
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CN105008402B (zh) * | 2013-02-22 | 2018-09-18 | 佳能株式会社 | 近红外色素结合的透明质酸衍生物和包括其的光学成像用造影剂 |
-
2015
- 2015-12-23 CZ CZ2015-936A patent/CZ307511B6/cs not_active IP Right Cessation
-
2016
- 2016-12-22 JP JP2018533195A patent/JP2019501262A/ja not_active Withdrawn
- 2016-12-22 BR BR112018012554A patent/BR112018012554A2/pt not_active Application Discontinuation
- 2016-12-22 PL PL16840310T patent/PL3393527T3/pl unknown
- 2016-12-22 KR KR1020187021096A patent/KR20180096761A/ko not_active Withdrawn
- 2016-12-22 ES ES16840310T patent/ES2751091T3/es active Active
- 2016-12-22 DK DK16840310.3T patent/DK3393527T3/da active
- 2016-12-22 RU RU2018123820A patent/RU2018123820A/ru not_active Application Discontinuation
- 2016-12-22 EP EP16840310.3A patent/EP3393527B1/en not_active Not-in-force
- 2016-12-22 WO PCT/CZ2016/050048 patent/WO2017108015A1/en not_active Ceased
- 2016-12-22 US US16/061,748 patent/US20190001000A1/en not_active Abandoned
- 2016-12-22 HU HUE16840310A patent/HUE045756T2/hu unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Xu et al. | Hyaluronic acid-decorated redox-sensitive chitosan micelles for tumor-specific intracellular delivery of gambogic acid | |
| CN106946899B (zh) | 一种喜树碱类前药及其制备和应用 | |
| Wang et al. | The inhibition of tumor growth and metastasis by self-assembled nanofibers of taxol | |
| JP4704753B2 (ja) | ヒアルロン酸又はヒアルロン酸誘導体に共有結合したタキサン類 | |
| Li et al. | Tailored Trojan horse nanocarriers for enhanced redox-responsive drug delivery | |
| US20130296285A1 (en) | Design of Hydrolytically Releasable Prodrugs for Sustained Release Nanoparticle Formulations | |
| CN102037058A (zh) | 多西紫杉醇高分子衍生物、及其制造方法及其用途 | |
| JP2013516471A (ja) | 薬物の脂肪酸誘導体および類似体 | |
| CN108785683A (zh) | 一种还原响应性药物-药物共轭体的制备方法 | |
| JP6744429B2 (ja) | 化合物及びその応用、並びに白金錯体及びそのリポソーム | |
| WO2009070380A2 (en) | Water-soluble carbon nanotube compositions for drug delivery and medical applications | |
| CN108567764A (zh) | 一种基于羧甲基壳聚糖的新型水溶性靶向纳米药物载体及其制备方法 | |
| JP2018527360A (ja) | 修飾された細胞毒とその治療的使用 | |
| KR101971672B1 (ko) | 화학색전용 에멀전 조성물 및 그의 제조방법 | |
| CN108452317A (zh) | 一种基于果胶/阿霉素结合物的载药纳米粒子及其制备方法 | |
| Shan et al. | Synthesis and anti-tumor activity study of water-soluble PEG-celastrol coupling derivatives as self-assembled nanoparticles | |
| JP2019501262A5 (https=) | ||
| JP5613679B2 (ja) | 腹腔内投与用の抗がん剤含有ブロック共重合体、ミセル調製物及びそれを有効成分とする癌治療薬 | |
| CA2983829C (en) | Metal complexes with bisphosphonate or pyrophosphate useful as imaging agents | |
| Gao et al. | Biomimetic nanoprodrugs from fatty acid modified camptothecin and albumin for enhanced pharmacotherapy | |
| CN108467439A (zh) | 一种水溶性紫杉醇抗癌药物的制备方法 | |
| Li et al. | Design of zwitterionic polyester based nano-carriers for platinum (iv) prodrug delivery | |
| CN110177566A (zh) | 用于制备靶向肿瘤-脉管系统的抗肿瘤剂的方法 | |
| US8784866B2 (en) | Water-soluble carbon nanotube compositions for drug delivery and medicinal applications | |
| RU2018123820A (ru) | Флуоресцентный конъюгат гиалуроновой кислоты или ее соли, гидрофобизованный конъюгат, способы его получения и применение |