CA3006028A1 - Pharmaceutical compositions comprising levodopa amide and uses thereof - Google Patents
Pharmaceutical compositions comprising levodopa amide and uses thereof Download PDFInfo
- Publication number
- CA3006028A1 CA3006028A1 CA3006028A CA3006028A CA3006028A1 CA 3006028 A1 CA3006028 A1 CA 3006028A1 CA 3006028 A CA3006028 A CA 3006028A CA 3006028 A CA3006028 A CA 3006028A CA 3006028 A1 CA3006028 A1 CA 3006028A1
- Authority
- CA
- Canada
- Prior art keywords
- buffer
- acid
- pharmaceutical composition
- lda
- inhibitor
- 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.)
- Abandoned
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 146
- -1 levodopa amide Chemical class 0.000 title claims abstract description 47
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229960004502 levodopa Drugs 0.000 title claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 229960003638 dopamine Drugs 0.000 claims abstract description 27
- 210000004556 brain Anatomy 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 230000002829 reductive effect Effects 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000035475 disorder Diseases 0.000 claims abstract description 19
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 16
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 109
- 239000000872 buffer Substances 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 65
- 229940123736 Decarboxylase inhibitor Drugs 0.000 claims description 40
- 239000003954 decarboxylase inhibitor Substances 0.000 claims description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 229940024606 amino acid Drugs 0.000 claims description 30
- 235000001014 amino acid Nutrition 0.000 claims description 30
- 150000001413 amino acids Chemical class 0.000 claims description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 150000002337 glycosamines Chemical class 0.000 claims description 28
- 239000003963 antioxidant agent Substances 0.000 claims description 21
- 235000006708 antioxidants Nutrition 0.000 claims description 21
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 19
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims description 19
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 18
- 229960004205 carbidopa Drugs 0.000 claims description 18
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical group NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
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- 239000003112 inhibitor Substances 0.000 claims description 15
- 239000008363 phosphate buffer Substances 0.000 claims description 15
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 13
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- 238000011260 co-administration Methods 0.000 claims description 8
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- YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical group C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 claims description 8
- 229960004644 moclobemide Drugs 0.000 claims description 8
- 229950001673 opicapone Drugs 0.000 claims description 8
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 claims description 8
- 229960000245 rasagiline Drugs 0.000 claims description 8
- NEMGRZFTLSKBAP-LBPRGKRZSA-N safinamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1OCC1=CC=CC(F)=C1 NEMGRZFTLSKBAP-LBPRGKRZSA-N 0.000 claims description 8
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- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims description 8
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- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 6
- 239000004201 L-cysteine Substances 0.000 claims description 6
- 235000013878 L-cysteine Nutrition 0.000 claims description 6
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Landscapes
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| US201562259324P | 2015-11-24 | 2015-11-24 | |
| US62/259,324 | 2015-11-24 | ||
| PCT/IL2016/051261 WO2017090039A2 (en) | 2015-11-24 | 2016-11-23 | Pharmaceutical compositions comprising levodopa amide and uses thereof |
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| CA3006028A1 true CA3006028A1 (en) | 2017-06-01 |
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| CA3006028A Abandoned CA3006028A1 (en) | 2015-11-24 | 2016-11-23 | Pharmaceutical compositions comprising levodopa amide and uses thereof |
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| EP (1) | EP3380076A2 (enExample) |
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| WO (1) | WO2017090039A2 (enExample) |
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| PL3116475T3 (pl) | 2014-03-13 | 2021-02-08 | Neuroderm Ltd | Kompozycje inhibitora dekarboksylazy dopa |
| US10258585B2 (en) | 2014-03-13 | 2019-04-16 | Neuroderm, Ltd. | DOPA decarboxylase inhibitor compositions |
| WO2019038637A1 (en) | 2017-08-21 | 2019-02-28 | Neuroderm Ltd | FORMS OF CRYSTALLINE SALT OF LEVODOPA AMIDE AND METHODS OF MAKING AND USING THEM |
| WO2019038639A1 (en) | 2017-08-21 | 2019-02-28 | Neuroderm Ltd | FREE LEOPODOPA CRYSTALLINE AMIDE BASE AND METHODS OF MAKING AND USING SAME |
| WO2019038638A1 (en) | 2017-08-21 | 2019-02-28 | Neuroderm Ltd | PROCESS FOR PREPARING AMIDE OF PURIFIED LEVODOPA |
| WO2019145773A1 (en) | 2017-12-15 | 2019-08-01 | Nos Life Sciences Corporation | Liposomal-encapsulated formulations |
| WO2020178810A1 (en) * | 2019-03-04 | 2020-09-10 | Neuroderm, Ltd. | Pharmaceutical compositions comprising levodopa amide derivatives and uses thereof |
| US11701340B2 (en) * | 2019-04-17 | 2023-07-18 | Vici Health Sciences., Llc | Liquid pharmaceutical compositions |
| PH12022550512A1 (en) * | 2019-09-05 | 2023-09-04 | Neuroderm Ltd | Liquid compositions comprising a levodopa amino acid conjugate and uses thereof |
| JP7506371B2 (ja) * | 2020-01-20 | 2024-06-26 | 国立大学法人浜松医科大学 | ドーパミン減少抑制剤 |
| US11213502B1 (en) | 2020-11-17 | 2022-01-04 | Neuroderm, Ltd. | Method for treatment of parkinson's disease |
| US11844754B2 (en) | 2020-11-17 | 2023-12-19 | Neuroderm, Ltd. | Methods for treatment of Parkinson's disease |
| US11331293B1 (en) | 2020-11-17 | 2022-05-17 | Neuroderm, Ltd. | Method for treatment of Parkinson's disease |
| CN116270675A (zh) * | 2023-03-21 | 2023-06-23 | 山东省分析测试中心 | N-乙酰氨基葡萄糖在防治mptp诱导神经元损伤中的应用 |
| US12161612B2 (en) | 2023-04-14 | 2024-12-10 | Neuroderm, Ltd. | Methods and compositions for reducing symptoms of Parkinson's disease |
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| WO2004069146A2 (en) | 2003-02-07 | 2004-08-19 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | L-dopa amide derivatives and uses thereof |
| SI2432454T1 (sl) | 2009-05-19 | 2017-09-29 | Neuroderm Ltd | Sestavki za kontinuirano dajanje zaviralcev dopa-dekarboksilaze |
| EP2648716A4 (en) * | 2010-12-10 | 2015-05-20 | Synagile Corp | PRODUCT COMPOSITIONS OF SUVUTABLY PERFUSABLE LÉVODOPA |
| US20150217046A1 (en) * | 2012-06-05 | 2015-08-06 | Synagile Corporation | Dosing regimens for subcutaneously infusible acidic compositions |
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2016
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- 2016-11-23 WO PCT/IL2016/051261 patent/WO2017090039A2/en not_active Ceased
- 2016-11-23 CA CA3006028A patent/CA3006028A1/en not_active Abandoned
- 2016-11-23 CN CN201680079822.0A patent/CN108495617A/zh not_active Withdrawn
- 2016-11-23 JP JP2018526784A patent/JP2018535230A/ja active Pending
- 2016-11-23 BR BR112018010564-3A patent/BR112018010564A2/pt not_active IP Right Cessation
- 2016-11-23 US US15/360,165 patent/US20170296491A1/en not_active Abandoned
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| CL2018001395A1 (es) | 2018-10-12 |
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| BR112018010564A2 (pt) | 2018-11-21 |
| IL259484A (en) | 2018-07-31 |
| ZA201803485B (en) | 2019-08-28 |
| RU2018119194A (ru) | 2019-12-25 |
| WO2017090039A3 (en) | 2017-08-31 |
| US20170296491A1 (en) | 2017-10-19 |
| WO2017090039A2 (en) | 2017-06-01 |
| AU2016358511A1 (en) | 2018-06-21 |
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