RU2018112720A - Производные пантотената для лечения неврологических заболеваний - Google Patents
Производные пантотената для лечения неврологических заболеваний Download PDFInfo
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- RU2018112720A RU2018112720A RU2018112720A RU2018112720A RU2018112720A RU 2018112720 A RU2018112720 A RU 2018112720A RU 2018112720 A RU2018112720 A RU 2018112720A RU 2018112720 A RU2018112720 A RU 2018112720A RU 2018112720 A RU2018112720 A RU 2018112720A
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- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical class OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 title claims 9
- 208000012902 Nervous system disease Diseases 0.000 title 1
- 208000025966 Neurological disease Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 238000000034 method Methods 0.000 claims 16
- 230000001771 impaired effect Effects 0.000 claims 6
- 230000007170 pathology Effects 0.000 claims 6
- 210000002569 neuron Anatomy 0.000 claims 5
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims 4
- 108090000790 Enzymes Proteins 0.000 claims 4
- 102000004190 Enzymes Human genes 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- 229940055726 pantothenic acid Drugs 0.000 claims 4
- 235000019161 pantothenic acid Nutrition 0.000 claims 4
- 239000011713 pantothenic acid Substances 0.000 claims 4
- 108090000623 proteins and genes Proteins 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 108010021592 Pantothenate kinase Proteins 0.000 claims 2
- 102100024122 Pantothenate kinase 1 Human genes 0.000 claims 2
- 238000009825 accumulation Methods 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 230000026731 phosphorylation Effects 0.000 claims 2
- 238000006366 phosphorylation reaction Methods 0.000 claims 2
- XHFVGHPGDLDEQO-ZETCQYMHSA-N (R)-4'-phosphopantothenic acid Chemical compound OP(=O)(O)OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O XHFVGHPGDLDEQO-ZETCQYMHSA-N 0.000 claims 1
- -1 1H-indol-3-yl-methyl Chemical group 0.000 claims 1
- 206010008754 Choreoathetosis Diseases 0.000 claims 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000019505 Deglutition disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000014094 Dystonic disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 208000010428 Muscle Weakness Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 206010044565 Tremor Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005516 coenzyme A Substances 0.000 claims 1
- 229940093530 coenzyme a Drugs 0.000 claims 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims 1
- 230000003955 neuronal function Effects 0.000 claims 1
- 231100000862 numbness Toxicity 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 208000018198 spasticity Diseases 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/222—Amides of phosphoric acids
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
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- C07—ORGANIC CHEMISTRY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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- C07F9/09—Esters of phosphoric acids
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
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- Life Sciences & Earth Sciences (AREA)
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- Molecular Biology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (42)
1. Соединение формулы:
или его фармацевтически приемлемая соль, выбранные из группы, состоящей из:
2. Соединение по п.1, где R, R' и R" представляют собой метил.
3. Соединение по п.1, где R представляет собой метил, R' представляет собой этил, и R" представляет собой бензил.
4. Соединение по п.1, где R представляет собой метил, и R' и R" представляют собой метилциклопропил.
5. Соединение по п.1, где R представляет собой 1H-индол-3-ил-метил, R' представляет собой бензил, и R" представляет собой этил.
6. Фармацевтическая композиция, содержащая соединение по любому из пп.1-5 и фармацевтически приемлемое вспомогательное вещество.
7. Фармацевтическая композиция по п.6, где фармацевтическая композиция представляет собой стандартную лекарственную форму.
8. Способ лечения заболевания, связанного с недостатком пантотенаткиназы, 4'-фосфопантотената или кофермента A у субъекта, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
9. Способ лечения нейродегенерации, связанной с пантотенаткиназой, у субъекта, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
10. Способ по п.9, где субъект страдает от нейродегенерации с накоплением в мозге железа.
11. Способ лечения клеток или ткани, вовлеченных в патологию, характеризующуюся нарушенным нейронным функционированием у субъекта, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
12. Способ по п.11, где патология выбрана из дистонии, экстрапирамидальных эффектов, дисфагии, оцепенелости и/или негибкости конечностей, хореоатетоза, тремора, деменции, спастичности, мышечной слабости и судорог.
13. Способ лечения клеток или ткани, вовлеченных в патологию, характеризующуюся нарушением нейронов, вызванным нарушением гена, связанного с ферментом пантотенкиназой, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
14. Способ лечения патологии, характеризующейся нарушением нейронов, вызванным нарушением гена, связанного с ферментом пантотенкиназой, у субъекта, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
15. Способ лечения клеток или ткани, вовлеченных в патологию, характеризующуюся нарушением нейронов, вызванным нарушением экспрессии гена, связанного с ферментом пантотенкиназой, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
16. Способ лечения патологии, характеризующейся нарушением нейронов, вызванным нарушением экспрессии гена, связанного с ферментом пантотенкиназой у субъекта, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
17. Способ лечения субъекта, содержащего нейроны с избыточным накоплением железа, включающий введение субъекту эффективного количества соединения по любому из пп.1-5.
18. Способ по любому из пп.8-17, где субъект представляет собой ребенка.
19. Способ по п.18, где ребенок имеет возраст 10-15 лет.
20. Способ по любому из пп.8-17, где субъект представляет собой взрослого.
21. Способ получения соединение по любому из пп.1-5, включающий:
защиту обеих гидроксильных групп пантотеновой кислоты;
этерификацию кислотной группы деблокированной пантотеновой кислоты, получая соединение формулы:
где каждая Pg независимо представляет собой защитную группу, и R" представляет собой определенный в любом из пп.1-5;
(с) деблокирование гидроксильных групп;
фосфорилирование деблокированного соединения соединением формулы:
где L представляет собой уходящую группу (например, галоген), и R и R' представляют собой определенные в любом из пп.1-5; и
необязательно получение соли соединения, полученного на стадии (d).
22. Способ получения соединение по любому из пп.1-5, включающий:
этерификацию пантотеновой кислоты со спиртом формулы R"OH, получая соединение формулы:
где R" представляет собой определенный в любом из пп.1-5;
фосфорилирование этерифицированного соединения соединением формулы:
где L представляет собой уходящую группу (например, галоген), и R и R' представляют собой определенные в любом из пп.1-5; и
необязательно получение соли соединения, полученного на стадии (b).
23. Способ по п.22, где стадия (a) включает воздействие на пантотеновую кислоту условиями этерификации по Фишеру.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261639602P | 2012-04-27 | 2012-04-27 | |
| US61/639,602 | 2012-04-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2014147739A Division RU2653497C2 (ru) | 2012-04-27 | 2013-04-26 | Производные пантотената для лечения неврологических заболеваний |
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| RU2018112720A true RU2018112720A (ru) | 2019-02-28 |
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| RU2018112720A RU2018112720A (ru) | 2012-04-27 | 2013-04-26 | Производные пантотената для лечения неврологических заболеваний |
| RU2014147739A RU2653497C2 (ru) | 2012-04-27 | 2013-04-26 | Производные пантотената для лечения неврологических заболеваний |
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| RU2014147739A RU2653497C2 (ru) | 2012-04-27 | 2013-04-26 | Производные пантотената для лечения неврологических заболеваний |
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| Country | Link |
|---|---|
| US (3) | US8673883B2 (ru) |
| EP (3) | EP3112372B1 (ru) |
| JP (3) | JP6254151B2 (ru) |
| KR (1) | KR20150035550A (ru) |
| CN (2) | CN106977544B (ru) |
| AU (3) | AU2013251345B2 (ru) |
| BR (1) | BR112014026817A2 (ru) |
| CA (1) | CA2879314A1 (ru) |
| CY (2) | CY1118198T1 (ru) |
| DK (2) | DK2841438T3 (ru) |
| ES (2) | ES2708813T3 (ru) |
| HK (1) | HK1207863A1 (ru) |
| HR (2) | HRP20161389T1 (ru) |
| HU (2) | HUE029474T2 (ru) |
| IN (1) | IN2014DN09584A (ru) |
| LT (2) | LT3112372T (ru) |
| MX (1) | MX360149B (ru) |
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| SM (1) | SMT201600395B (ru) |
| TR (1) | TR201819263T4 (ru) |
| WO (1) | WO2013163576A1 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3112372T (pt) * | 2012-04-27 | 2019-01-17 | Retrophin Inc | Derivados do pantotenato para o tratamento de distúrbios neurológicos |
| US9896464B2 (en) | 2013-10-25 | 2018-02-20 | Retrophin, Inc. | Pantothenate derivatives for the treatment of neurological disorders |
| EP2868662A1 (en) * | 2013-11-04 | 2015-05-06 | Acies Bio d.o.o. | Stable pantetheine derivatives for the treatment of pantothenate kinase associated neurodegeneration (pkan) and methods for the synthesis of such compounds |
| AU2016366977A1 (en) | 2015-12-08 | 2018-07-12 | Retrophin, Inc. | Cyclic phosphates and cyclic phosphoramidates for the treatment of neurologic disorders |
| MX2019009342A (es) * | 2017-02-07 | 2019-10-02 | Retrophin Inc | Formulaciones de fosmetpantotenato solido. |
| WO2023173196A1 (en) | 2022-03-18 | 2023-09-21 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676976A (en) | 1950-12-04 | 1954-04-27 | Nat Res Dev | Synthesis of pantothenic acid-4' phosphate |
| US2870188A (en) | 1955-10-03 | 1959-01-20 | Hoffmann La Roche | Process for the manufacture of pantothenic acid 4'-phosphate and its salts |
| RU2002110463A (ru) * | 1999-09-21 | 2004-02-27 | Басф Акциенгезелльшафт (De) | Способ и микроорганизмы для получения пантосоединений |
| AU2002326412A1 (en) | 2001-07-20 | 2003-03-03 | Oregon Health And Science University | Novel human nucleic acids encoding a pantothenate kinase and methods of use |
| HUP0500383A2 (hu) * | 2002-07-03 | 2005-08-29 | Basf Ag | Mikroorganizmusok és eljárások pantotenát fokozott termelésére |
| CA2618335C (en) | 2005-08-15 | 2015-03-31 | F.Hoffmann-La Roche Ag | Antiviral phosphoramidates of 4'-substituted pronucleotides |
| PT3112372T (pt) * | 2012-04-27 | 2019-01-17 | Retrophin Inc | Derivados do pantotenato para o tratamento de distúrbios neurológicos |
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