JP2021505550A5 - - Google Patents
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- JP2021505550A5 JP2021505550A5 JP2020529484A JP2020529484A JP2021505550A5 JP 2021505550 A5 JP2021505550 A5 JP 2021505550A5 JP 2020529484 A JP2020529484 A JP 2020529484A JP 2020529484 A JP2020529484 A JP 2020529484A JP 2021505550 A5 JP2021505550 A5 JP 2021505550A5
- Authority
- JP
- Japan
- Prior art keywords
- anesthetic
- preparation
- polymer
- conjugate
- preparation according
- 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.)
- Granted
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- 229920000642 polymer Polymers 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 20
- 239000002202 Polyethylene glycol Substances 0.000 claims description 19
- 230000003444 anaesthetic effect Effects 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 12
- 210000005036 nerve Anatomy 0.000 claims description 11
- -1 PEG500 Polymers 0.000 claims description 10
- 229940043075 fluocinolone Drugs 0.000 claims description 9
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 9
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 239000003176 neuroleptic agent Substances 0.000 claims description 5
- 230000000701 neuroleptic effect Effects 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 229940127557 pharmaceutical product Drugs 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 229960003957 dexamethasone Drugs 0.000 claims description 4
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 4
- 239000003862 glucocorticoid Substances 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229960005205 prednisolone Drugs 0.000 claims description 4
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 4
- RPQXVSUAYFXFJA-HGRQIUPRSA-N saxitoxin Chemical compound NC(=O)OC[C@@H]1N=C(N)N2CCC(O)(O)[C@@]22N=C(N)N[C@@H]12 RPQXVSUAYFXFJA-HGRQIUPRSA-N 0.000 claims description 4
- RPQXVSUAYFXFJA-UHFFFAOYSA-N saxitoxin hydrate Natural products NC(=O)OCC1N=C(N)N2CCC(O)(O)C22NC(N)=NC12 RPQXVSUAYFXFJA-UHFFFAOYSA-N 0.000 claims description 4
- 229940037128 systemic glucocorticoids Drugs 0.000 claims description 4
- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 claims description 4
- 229950010357 tetrodotoxin Drugs 0.000 claims description 4
- CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 claims description 4
- 229940035674 anesthetics Drugs 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003193 general anesthetic agent Substances 0.000 claims description 3
- 208000004296 neuralgia Diseases 0.000 claims description 3
- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 2
- 206010002091 Anaesthesia Diseases 0.000 claims description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims description 2
- GZENKSODFLBBHQ-ILSZZQPISA-N Medrysone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GZENKSODFLBBHQ-ILSZZQPISA-N 0.000 claims description 2
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 2
- PPEKGEBBBBNZKS-UHFFFAOYSA-N Neosaxitoxin Natural products N=C1N(O)C(COC(=O)N)C2N=C(N)NC22C(O)(O)CCN21 PPEKGEBBBBNZKS-UHFFFAOYSA-N 0.000 claims description 2
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 2
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims description 2
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 claims description 2
- 229920002596 Polyethylene Glycol 900 Polymers 0.000 claims description 2
- 238000005741 Steglich esterification reaction Methods 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 229960003099 amcinonide Drugs 0.000 claims description 2
- ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 claims description 2
- 230000037005 anaesthesia Effects 0.000 claims description 2
- 229960002537 betamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 2
- 230000004071 biological effect Effects 0.000 claims description 2
- 229960002842 clobetasol Drugs 0.000 claims description 2
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 2
- 229960004544 cortisone Drugs 0.000 claims description 2
- LKFHUFAEFBRVQX-UHFFFAOYSA-N decanedioic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)CCCCCCCCC(O)=O LKFHUFAEFBRVQX-UHFFFAOYSA-N 0.000 claims description 2
- VRRIYZJUSNMZMP-PJPYAQQDSA-N decarbamoylsaxitoxin Chemical compound OC[C@@H]1N=C(N)N2CCC(O)(O)[C@]32NC(N)=N[C@H]31 VRRIYZJUSNMZMP-PJPYAQQDSA-N 0.000 claims description 2
- VRRIYZJUSNMZMP-UHFFFAOYSA-N decarbamoylsaxitoxin hydrate Natural products OCC1NC(=N)N2CCC(O)(O)C22NC(=N)NC12 VRRIYZJUSNMZMP-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 229960000676 flunisolide Drugs 0.000 claims description 2
- 229960002383 halcinonide Drugs 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 230000008595 infiltration Effects 0.000 claims description 2
- 238000001764 infiltration Methods 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 231100001231 less toxic Toxicity 0.000 claims description 2
- 238000002690 local anesthesia Methods 0.000 claims description 2
- 230000005923 long-lasting effect Effects 0.000 claims description 2
- 229960004584 methylprednisolone Drugs 0.000 claims description 2
- PPEKGEBBBBNZKS-HGRQIUPRSA-N neosaxitoxin Chemical compound N=C1N(O)[C@@H](COC(=O)N)[C@@H]2NC(=N)N[C@@]22C(O)(O)CCN21 PPEKGEBBBBNZKS-HGRQIUPRSA-N 0.000 claims description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229940125794 sodium channel blocker Drugs 0.000 claims description 2
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 2
- 229960005294 triamcinolone Drugs 0.000 claims description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 2
- POPFMWWJOGLOIF-XWCQMRHXSA-N Flurandrenolide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O POPFMWWJOGLOIF-XWCQMRHXSA-N 0.000 claims 1
- 229960004511 fludroxycortide Drugs 0.000 claims 1
- 229960001011 medrysone Drugs 0.000 claims 1
- 229960001664 mometasone Drugs 0.000 claims 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 102000003566 TRPV1 Human genes 0.000 description 1
- 108010025083 TRPV1 receptor Proteins 0.000 description 1
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 description 1
- 101150016206 Trpv1 gene Proteins 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024106268A JP2024114970A (ja) | 2017-12-01 | 2024-07-01 | 長時間の局所麻酔のための麻酔薬－ポリマー共有結合性コンジュゲート |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762593784P | 2017-12-01 | 2017-12-01 | |
| US62/593,784 | 2017-12-01 | ||
| PCT/US2018/063573 WO2019109065A1 (en) | 2017-12-01 | 2018-12-03 | Covalent anesthetic-polymer conjugates for prolonged local anesthesia |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024106268A Division JP2024114970A (ja) | 2017-12-01 | 2024-07-01 | 長時間の局所麻酔のための麻酔薬－ポリマー共有結合性コンジュゲート |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021505550A JP2021505550A (ja) | 2021-02-18 |
| JP2021505550A5 true JP2021505550A5 (enExample) | 2021-12-09 |
| JP7601375B2 JP7601375B2 (ja) | 2024-12-17 |
Family
ID=64734233
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020529484A Active JP7601375B2 (ja) | 2017-12-01 | 2018-12-03 | 長時間の局所麻酔のための麻酔薬－ポリマー共有結合性コンジュゲート |
| JP2024106268A Pending JP2024114970A (ja) | 2017-12-01 | 2024-07-01 | 長時間の局所麻酔のための麻酔薬－ポリマー共有結合性コンジュゲート |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024106268A Pending JP2024114970A (ja) | 2017-12-01 | 2024-07-01 | 長時間の局所麻酔のための麻酔薬－ポリマー共有結合性コンジュゲート |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20210275678A1 (enExample) |
| EP (1) | EP3717017A1 (enExample) |
| JP (2) | JP7601375B2 (enExample) |
| CN (1) | CN111867633B (enExample) |
| AU (1) | AU2018375002B2 (enExample) |
| CA (1) | CA3084034C (enExample) |
| WO (1) | WO2019109065A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021146553A1 (en) * | 2020-01-17 | 2021-07-22 | Children's Medical Center Corporation | Macromolecular prodrugs for light-emitting diodes and uses thereof |
| CN113805326A (zh) * | 2021-09-18 | 2021-12-17 | 吉林大学 | 原位拉伸多光子激光共聚焦成像仪、实时原位三维观测共混聚合物内部结构的方法 |
| US20250099421A1 (en) * | 2023-09-27 | 2025-03-27 | Relevium Medical | Analgesic Therapeutics Based on conjugation of Biocompatible Polymers to Ion Channel Modulators |
| CN119345382B (zh) * | 2024-12-23 | 2025-03-21 | 上海华之沃生物医药科技有限公司 | 替曲朵辛偶联物、制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001413A (en) | 1973-06-12 | 1977-01-04 | Astra Pharmaceutical Products, Inc. | Pharmaceutical local anesthetic composition employing saxitoxin |
| US5700485A (en) * | 1992-09-10 | 1997-12-23 | Children's Medical Center Corporation | Prolonged nerve blockade by the combination of local anesthetic and glucocorticoid |
| US6326020B1 (en) * | 1997-05-16 | 2001-12-04 | Children's Medical Center Corporation | Local anesthetic formulations |
| GB0218830D0 (en) * | 2002-08-13 | 2002-09-18 | Syngenix Ltd | Anaesthetic conjugate |
| US20040228831A1 (en) * | 2003-05-15 | 2004-11-18 | Belinka Benjamin A. | Polymeric conjugates for tissue activated drug delivery |
| US8980317B2 (en) * | 2008-12-23 | 2015-03-17 | Warsaw Orthopedic, Inc. | Methods and compositions for treating infections comprising a local anesthetic |
| BRPI1014854A2 (pt) * | 2009-03-30 | 2016-05-03 | Cerulean Pharma Inc | "conjugados polímero-agente, partículas, composições, e métodos de uso relacionados" |
| EA032840B8 (ru) * | 2011-06-22 | 2020-06-18 | Вайоми Терапеутикс Лимитед | Пролекарства на основе конъюгатов противогрибковых агентов и их применение |
| CN104427987A (zh) * | 2012-04-23 | 2015-03-18 | 儿童医学中心公司 | 延缓慢性神经病理性疼痛发作的调配物和方法 |
| PL2968225T3 (pl) * | 2013-03-15 | 2019-08-30 | The Children's Medical Center Corporation | Preparaty skojarzone neosaksytoksyny do przedłużonego znieczulenia miejscowego |
| US10449152B2 (en) * | 2014-09-26 | 2019-10-22 | Covidien Lp | Drug loaded microspheres for post-operative chronic pain |
| CN106310289B (zh) * | 2015-06-24 | 2020-10-13 | 天津键凯科技有限公司 | 一种聚乙二醇和麻醉药的结合物及其制备方法 |
-
2018
- 2018-12-03 US US16/768,818 patent/US20210275678A1/en not_active Abandoned
- 2018-12-03 EP EP18821915.8A patent/EP3717017A1/en active Pending
- 2018-12-03 WO PCT/US2018/063573 patent/WO2019109065A1/en not_active Ceased
- 2018-12-03 CA CA3084034A patent/CA3084034C/en active Active
- 2018-12-03 CN CN201880085421.5A patent/CN111867633B/zh active Active
- 2018-12-03 JP JP2020529484A patent/JP7601375B2/ja active Active
- 2018-12-03 AU AU2018375002A patent/AU2018375002B2/en active Active
-
2024
- 2024-07-01 JP JP2024106268A patent/JP2024114970A/ja active Pending
- 2024-08-27 US US18/817,160 patent/US20250195671A1/en active Pending
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