RU2224510C2 - Терапевтические композиции - Google Patents
Терапевтические композиции Download PDFInfo
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- RU2224510C2 RU2224510C2 RU99121849/15A RU99121849A RU2224510C2 RU 2224510 C2 RU2224510 C2 RU 2224510C2 RU 99121849/15 A RU99121849/15 A RU 99121849/15A RU 99121849 A RU99121849 A RU 99121849A RU 2224510 C2 RU2224510 C2 RU 2224510C2
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- Prior art keywords
- esters
- hydroxybutyryl
- use according
- acetoacetate
- hydroxybutyrate
- Prior art date
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- 239000000203 mixture Substances 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- WHBMMWSBFZVSSR-GSVOUGTGSA-N (R)-3-hydroxybutyric acid Chemical compound C[C@@H](O)CC(O)=O WHBMMWSBFZVSSR-GSVOUGTGSA-N 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 7
- 230000002503 metabolic effect Effects 0.000 claims abstract 4
- 239000002243 precursor Substances 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract 3
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract 2
- 206010015037 epilepsy Diseases 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 150000002148 esters Chemical group 0.000 claims 16
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 3
- 229920000642 polymer Polymers 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- PUPZLCDOIYMWBV-SCSAIBSYSA-N (R)-butane-1,3-diol Chemical compound C[C@@H](O)CCO PUPZLCDOIYMWBV-SCSAIBSYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- -1 acetoacetic acid halide Chemical class 0.000 claims 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 claims 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 235000013305 food Nutrition 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 231100000189 neurotoxic Toxicity 0.000 claims 1
- 230000002887 neurotoxic effect Effects 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 2
- 230000002265 prevention Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Images
Classifications
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- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Изобретение относится к медицине и касается применения соединения, выбранного из D-β-гидроксимасляной кислоты и/или ее метаболического предшественника в качестве активного агента лекарственного средства или пищевого продукта для лечения диабета, реверсии, замедления или предотвращения действий нейродегенеративных расстройств и эпилепсии, новым соединениям и способу их синтеза. Изобретение позволяет повысить эффективность лечения. 5 с. и 16 з.п. ф-лы, 3 табл.
Description
Текст описания в факсимильном виде (см. графическую часть)-
Claims (21)
1. Применение соединения, выбранного из D-β-гидроксимасляной кислоты и/или метаболического предшественника D-β-гидроксимасляной кислоты, включающего D-β-гидроксибутирильные остатки, олиго- D-β-гидроксибутирильные остатки кислоты, или поли- D-β-гидроксибутирильные остатки или физиологически приемлемой соли любого из них в качестве активного агента лекарственного средства или пищевого продукта (I) для лечения диабета или инсулинрезистентных состояний и/или (II) для реверсии, замедления или предотвращения действий нейродегенеративных расстройств и эпилепсии.
2. Применение по п.1, отличающееся тем, что нейродегенеративное расстройство является расстройством, связанным с наличием нейротоксичных белковых бляшек.
3. Применение по п.1, отличающееся тем, что метаболический предшественник дополнительно включает остатки (R)-1,3-бутандиола или ацетоацетила.
4. Применение по п.3, отличающееся тем, что метаболический предшественник является сложным эфиром.
5. Применение по п.4, отличающееся тем, что сложные эфиры являются сложными эфирами одноатомных, двухатомных и трехатомных спиртов.
6. Применение по п.1, отличающееся тем, что сложные эфиры являются эфирами ацетоацетата.
7. Применение по п.1, отличающееся тем, что сложными эфирами являются сложные эфиры D-β-гидроксибутирата или сложные эфиры олигомеров или полимеров D-β-гидроксибутирата.
8. Применение по любому из п.1-7, отличающееся тем, что соединениями являются соединения формулы
или их физиологически приемлемые соли или эфиры, причем в каждом случае n выбирают таким образом, что полимер или олигомер легко метаболизируется при введении в организм человека или животного для обеспечения повышенного уровня кетоновых тел в крови.
9. Применение по п.8, отличающееся тем, что n является целым числом от 0 до 1000.
10. Применение по п.9, отличающееся тем, что n является целым числом от 0 до 200.
11. Применение по п.10, отличающееся тем, что n является целым числом от 3 до 5.
12. Применение по п.1, отличающееся тем, что в лекарственном средстве соотношение D-β-гидроксибутирата и ацетоацетата составляет от 1:1 до 20:1.
13. Соединение формулы
или его фармацевтически приемлемые соли или сложные эфиры, причем n выбирают таким образом, что полимер или олигомер легко метаболизируется при введении в организм человека или животного для обеспечения повышенного уровня кетоновых тел в крови.
14. Соединение по п.13, отличающееся тем, что сложные эфиры являются сложными эфирами одноатомных, двухатомных и трехатомных спиртов.
15. Соединение по п.14, отличающееся тем, что сложным эфиром является сложный эфир (R)-1,3-бутандиола.
16. Способ синтеза сложных эфиров D-β-гидроксибутирил-ацетоацетата или поли- или олиго- D-β-гидроксибутирил-ацетоацетата, включающий взаимодействие галогенида ацетоуксусной кислоты с D-β-гидроксибутиратом или поли- или олиго- D-β-гидроксибутиратом.
17. Способ по п.16, включающий взаимодействие ацетоуксусной кислоты с активирующим агентом для получения галогенида кислоты.
18. Способ синтеза сложных эфиров D-β-гидроксибутирил-ацетоацетата, включающий взаимодействие D-β-галогенбутирата с ацетоуксусной кислотой.
19. Способ синтеза D-β-гидроксибутирил-ацетоацетата или олиго- D-β-гидроксибутирил-ацетоацетата, включающий взаимодействие D-β-гидроксимасляной кислоты с дикетеном.
20. Способ по п.19, отличающийся тем, что реакцию проводят в присутствии ацетата натрия.
21. Способ по п.20, отличающийся тем, что реакцию проводят в атмосфере азота.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4085897P | 1997-03-17 | 1997-03-17 | |
| US60/040,858 | 1997-03-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99121849A RU99121849A (ru) | 2001-07-20 |
| RU2224510C2 true RU2224510C2 (ru) | 2004-02-27 |
Family
ID=21913362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99121849/15A RU2224510C2 (ru) | 1997-03-17 | 1998-03-17 | Терапевтические композиции |
Country Status (11)
| Country | Link |
|---|---|
| EP (2) | EP1017379B1 (ru) |
| JP (3) | JP4740426B2 (ru) |
| KR (1) | KR100839689B1 (ru) |
| CN (2) | CN1552315B (ru) |
| AU (2) | AU749638B2 (ru) |
| CA (1) | CA2283642C (ru) |
| DK (2) | DK2283834T3 (ru) |
| ES (1) | ES2530753T3 (ru) |
| RU (1) | RU2224510C2 (ru) |
| WO (2) | WO1998041201A1 (ru) |
| ZA (1) | ZA982253B (ru) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6323237B1 (en) | 1997-03-17 | 2001-11-27 | Btg International Limited | Therapeutic compositions |
| US6316038B1 (en) | 1997-03-17 | 2001-11-13 | Btg International Limited | Therapeutic compositions |
| ATE283056T1 (de) * | 1998-07-22 | 2004-12-15 | Metabolix Inc | Nahrungs- und therapeutische verwendung von hydroxyalkanoat oligomere |
| KR100805490B1 (ko) * | 1998-09-15 | 2008-02-20 | 비티지 인터내셔널 리미티드 | 치료 조성물 （ⅱ） |
| US8124589B2 (en) * | 2000-05-01 | 2012-02-28 | Accera, Inc. | Use of ketogenic compounds for treatment of age-associated memory impairment |
| US6835750B1 (en) | 2000-05-01 | 2004-12-28 | Accera, Inc. | Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism II |
| AU2001257451A1 (en) * | 2000-05-01 | 2001-11-12 | Accera, Inc. | Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism |
| CA2423358C (en) * | 2000-09-22 | 2011-05-17 | Orphan Medical, Inc. | Gamma-hydroxybutyrate compositions containing carbohydrate, lipid or amino acid carriers |
| DE10303974A1 (de) | 2003-01-31 | 2004-08-05 | Abbott Gmbh & Co. Kg | Amyloid-β(1-42)-Oligomere, Verfahren zu deren Herstellung und deren Verwendung |
| AU2004245567B2 (en) * | 2003-06-03 | 2011-06-23 | Oxford University Innovation Limited | Nutritional supplements and therapeutic compositions comprising (R)-3-hydroxybutyrate derivatives |
| WO2005021013A1 (ja) * | 2003-09-01 | 2005-03-10 | Earthus, Inc. | β−ヒドロキシ短〜中鎖脂肪酸重合体 |
| GB0410266D0 (en) * | 2004-05-07 | 2004-06-09 | Ketocytonyx Inc | Treatment of apoptosis |
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| WO2006020179A2 (en) | 2004-07-20 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric ketone compounds |
| US20060252775A1 (en) * | 2005-05-03 | 2006-11-09 | Henderson Samuel T | Methods for reducing levels of disease associated proteins |
| US20070135376A1 (en) | 2005-06-20 | 2007-06-14 | Accera, Inc. | Method to reduce oxidative damage and improve mitochondrial efficiency |
| AU2006320392B2 (en) | 2005-11-30 | 2013-01-17 | AbbVie Deutschland GmbH & Co. KG | Monoclonal antibodies against amyloid beta protein and uses thereof |
| ES2527661T3 (es) | 2005-11-30 | 2015-01-28 | Abbvie Inc. | Método de exploración, proceso para purificar oligómeros Abeta no difundibles, anticuerpos selectivos contra dichos oligómeros Abeta no difundibles y un proceso para fabricar dichos anticuerpos |
| BRPI0619905A2 (pt) * | 2005-12-15 | 2011-10-25 | Nestec Sa | composições e métodos para conservar função cerebral |
| JP5030553B2 (ja) * | 2006-11-24 | 2012-09-19 | 有限会社ノーベル医学研究所 | ドライマウスおよび／または唾液分泌障害を処置するための医薬 |
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| CN1315473C (zh) | 2007-05-16 |
| JP4740426B2 (ja) | 2011-08-03 |
| EP1017379A1 (en) | 2000-07-12 |
| JP2001515510A (ja) | 2001-09-18 |
| KR20000076379A (ko) | 2000-12-26 |
| JP5800453B2 (ja) | 2015-10-28 |
| CA2283642C (en) | 2012-05-15 |
| EP2283834A2 (en) | 2011-02-16 |
| AU6513298A (en) | 1998-10-12 |
| WO1998041200A1 (en) | 1998-09-24 |
| CN1552315B (zh) | 2010-11-10 |
| ES2530753T3 (es) | 2015-03-05 |
| ZA982253B (en) | 1999-09-17 |
| KR100839689B1 (ko) | 2008-06-18 |
| AU749638B2 (en) | 2002-06-27 |
| CN1552315A (zh) | 2004-12-08 |
| JP2009173677A (ja) | 2009-08-06 |
| AU6556998A (en) | 1998-10-12 |
| EP1017379A4 (en) | 2007-01-24 |
| DK1017379T3 (en) | 2015-02-16 |
| JP2015042644A (ja) | 2015-03-05 |
| DK2283834T3 (en) | 2016-08-15 |
| EP2283834A3 (en) | 2012-02-01 |
| CA2283642A1 (en) | 1998-09-24 |
| CN1256629A (zh) | 2000-06-14 |
| EP1017379B1 (en) | 2014-12-10 |
| WO1998041201A1 (en) | 1998-09-24 |
| EP2283834B1 (en) | 2016-07-13 |
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