RU2013110845A - Пептидомиметические макроциклы - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/52—Cyclic peptides containing at least one abnormal peptide link with only normal peptide links in the ring
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/04—Antineoplastic agents specific for metastasis
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- 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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- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
- C07K14/4746—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used p53
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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Abstract
1. Пептидомиметический макроцикл, содержащий аминокислотную последовательность, которая, по меньшей мере, примерно на 60% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.2. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 60% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4, причем макроцикл не содержит триазол или тиоэфир.3. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 80% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.4. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 90% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.5. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла выбрана из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.6. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит спираль.7. Пептидомиметический макроцикл по п.1, где пептидомиметическ�
Claims (24)
1. Пептидомиметический макроцикл, содержащий аминокислотную последовательность, которая, по меньшей мере, примерно на 60% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.
2. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 60% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4, причем макроцикл не содержит триазол или тиоэфир.
3. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 80% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.
4. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла, по меньшей мере, примерно на 90% идентична аминокислотной последовательности, выбранной из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.
5. Пептидомиметический макроцикл по п.1, где аминокислотная последовательность указанного пептидомиметического макроцикла выбрана из группы, включающей в себя аминокислотные последовательности, приведенные в таблице 1, 2, 3 или 4.
6. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит спираль.
7. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит α-спираль.
8. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит α,α-дизамещенную аминокислоту.
9. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит поперечный линкер, соединяющий α-положения, по меньшей мере, двух аминокислот.
10. Пептидомиметический макроцикл по п.9, где, по меньшей мере, одна из двух указанных аминокислот представляет собой α,α-дизамещенную аминокислоту.
11. Пептидомиметический макроцикл по любому из пп.1-10, где пептидомиметический макроцикл имеет формулу:
Формула I
где:
каждый A, C, D и E независимо обозначает природную или неприродную аминокислоту, а D и E независимо и необязательно содержат кэпирующую группу;
B представляет собой природную или неприродную аминокислоту, аналог аминокислоты, 
, [-NH-L3-CO-], [-NH-L3-SO2-] или [-NH-L3-];
R1 и R2 независимо обозначают -H, алкил, алкенил, алкинил, арилалкил, циклоалкил, циклоалкилалкил, гетероалкил или гетероциклоалкил, незамещенный или замещенный галогеном;
R3 обозначает водород, алкил, алкенил, алкинил, арилалкил, гетероалкил, циклоалкил, гетероциклоалкил, циклоалкилалкил, циклоарил или гетероциклоарил, необязательно замещенный R5;
L обозначает макроцикл-образующий линкер формулы -L1-L2-;
L1 и L2 независимо обозначают алкилен, алкенилен, алкинилен, гетероалкилен, циклоалкилен, гетероциклоалкилен, циклоарилен, гетероциклоарилен или [-R4-K-R4-]n, каждый из которых необязательно замещен R5;
каждый R4 обозначает алкилен, алкенилен, алкинилен, гетероалкилен, циклоалкилен, гетероциклоалкилен, арилен или гетероарилен;
каждый K обозначает O, S, SO, SO2, CO, CO2 или CONR3;
каждый R5 независимо обозначает галоген, алкил, -OR6, -N(R6)2, -SR6, -SOR6, -SO2R6, -CO2R6, флуоресцентный фрагмент, радиоизотоп или терапевтическое средство;
каждый R6 независимо обозначает -H, алкил, алкенил, алкинил, арилалкил, циклоалкилалкил, гетероциклоалкил, флуоресцентный фрагмент, радиоизотоп или терапевтическое средство;
R7 обозначает -H, алкил, алкенил, алкинил, арилалкил, циклоалкил, гетероалкил, циклоалкилалкил, гетероциклоалкил, циклоарил или гетероциклоарил, необязательно замещенный R5, или часть циклической структуры, содержащую остаток D;
R8 обозначает -H, алкил, алкенил, алкинил, арилалкил, циклоалкил, гетероалкил, циклоалкилалкил, гетероциклоалкил, циклоарил или гетероциклоарил, необязательно замещенный R5, или часть циклической структуры, содержащую остаток E;
v и w независимо обозначают целые числа в диапазоне 1-1000;
u обозначает целое число в диапазоне 1-10;
x, y и z независимо обозначают целые числа в диапазоне 0-10; и
n обозначает целое число в диапазоне 1-5.
12. Пептидомиметический макроцикл по п.11, где L не содержит тиоэфир или триазол.
13. Пептидомиметический макроцикл по п.1, где пептидомиметический макроцикл содержит поперечный линкер, соединяющий скелетную аминогруппу первой аминокислоты со второй аминокислотой, входящей в состав пептидомиметического макроцикла.
14. Пептидомиметический макроцикл по п.13, где пептидомиметический макроцикл имеет формулу (IV) или (IVa):
где:
каждый A, C, D и E независимо обозначает природную или неприродную аминокислоту, а D и E независимо и необязательно содержат кэпирующую группу;
B обозначает природную или неприродную аминокислоту, аналог аминокислоты, , [-NH-L3-CO-], [-NH-L3-SO2-] или [-NH-L3-];
R1 и R2 независимо обозначают -H, алкил, алкенил, алкинил, арилалкил, циклоалкил, циклоалкилалкил, гетероалкил или гетероциклоалкил, незамещенный или замещенный галогеном, или часть циклической структуры, содержащей остаток E;
R3 обозначает водород, алкил, алкенил, алкинил, арилалкил, гетероалкил, циклоалкил, гетероциклоалкил, циклоалкилалкил, циклоарил или гетероциклоарил, необязательно замещенный R5;
L1 и L2 независимо обозначают алкилен, алкенилен, алкинилен, гетероалкилен, циклоалкилен, гетероциклоалкилен, циклоарилен, гетероциклоарилен или [-R4-K-R4-]n, каждый из которых необязательно замещен R5;
каждый R4 обозначает алкилен, алкенилен, алкинилен, гетероалкилен, циклоалкилен, гетероциклоалкилен, арилен или гетероарилен;
каждый K обозначает O, S, SO, SO2, CO, CO2 или CONR3;
каждый R5 независимо обозначает галоген, алкил, -OR6, -N(R6)2, -SR6, -SOR6, -SO2R6, -CO2R6, флуоресцентный фрагмент, радиоизотоп или терапевтическое средство;
каждый R6 независимо обозначает -H, алкил, алкенил, алкинил, арилалкил, циклоалкилалкил, гетероциклоалкил, флуоресцентный фрагмент, радиоизотоп или терапевтическое средство;
R7 обозначает -H, алкил, алкенил, алкинил, арилалкил, циклоалкил, гетероалкил, циклоалкилалкил, гетероциклоалкил, циклоарил или гетероциклоарил, необязательно замещенный R5;
v и w независимо обозначают целые числа в диапазоне 1-1000;
u обозначает целое число в диапазоне 1-10;
x, y и z независимо обозначают целые числа в диапазоне 0-10; и
n обозначает целое число в диапазоне 1-5.
15. Пептидомиметический макроцикл по п.14, где L1 и L2 по отдельности или в сочетании не содержат тиоэфир или триазол.
16. Пептидомиметический макроцикл по п.11, где L1 и L2 независимо обозначают алкилен, алкенилен или алкинилен.
17. Пептидомиметический макроцикл по п.11, где L1 и L2 независимо обозначают C3-C10 алкилен или алкенилен.
18. Пептидомиметический макроцикл по п.17, где L1 и L2 независимо обозначают C3-C6 алкилен или алкенилен.
19. Пептидомиметический макроцикл по п.11, где R1 и R2 обозначают H.
20. Пептидомиметический макроцикл по п.11, где R1 и R2 независимо обозначают алкил.
21. Пептидомиметический макроцикл по п.11, где R1 и R2 обозначают метил.
22. Способ лечения рака у субъекта, включающий в себя введение субъекту пептидомиметического макроцикла по п.1.
23. Способ модуляции активности p53 и/или HDM2 и/или HDMX у субъекта, включающий в себя введение субъекту пептидомиметического макроцикла по п.1.
24. Способ препятствования взаимодействию белков p53 и HDM2 и/или p53 и HDMX у субъекта, включающий в себя введение субъекту пептидомиметического макроцикла по п.1.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37363810P | 2010-08-13 | 2010-08-13 | |
| US37370110P | 2010-08-13 | 2010-08-13 | |
| US61/373,638 | 2010-08-13 | ||
| US61/373,701 | 2010-08-13 | ||
| US37416310P | 2010-08-16 | 2010-08-16 | |
| US61/374,163 | 2010-08-16 | ||
| PCT/US2011/047692 WO2012021876A2 (en) | 2010-08-13 | 2011-08-13 | Peptidomimetic macrocycles |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2016111360A Division RU2016111360A (ru) | 2010-08-13 | 2011-08-13 | Пептидомиметические макроциклы |
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| Publication Number | Publication Date |
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| RU2013110845A true RU2013110845A (ru) | 2014-09-20 |
| RU2582678C2 RU2582678C2 (ru) | 2016-04-27 |
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| RU2016111360A RU2016111360A (ru) | 2010-08-13 | 2011-08-13 | Пептидомиметические макроциклы |
| RU2013110845/04A RU2582678C2 (ru) | 2010-08-13 | 2011-08-13 | Пептидомиметические макроциклы |
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| US (5) | US8859723B2 (ru) |
| EP (1) | EP2603600B1 (ru) |
| JP (3) | JP2013535514A (ru) |
| KR (4) | KR102104762B1 (ru) |
| CN (2) | CN103282510A (ru) |
| BR (1) | BR112013003248A2 (ru) |
| CA (1) | CA2807685C (ru) |
| DK (1) | DK2603600T3 (ru) |
| ES (1) | ES2711526T3 (ru) |
| MX (1) | MX355543B (ru) |
| PL (1) | PL2603600T3 (ru) |
| PT (1) | PT2603600T (ru) |
| RU (2) | RU2016111360A (ru) |
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Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7960506B2 (en) | 2006-12-14 | 2011-06-14 | Aileron Therapeutics, Inc. | Bis-sulfhydryl macrocyclization systems |
| CA2939778C (en) | 2007-01-31 | 2019-01-29 | Dana-Farber Cancer Institute, Inc. | Stabilized p53 peptides and uses thereof |
| BRPI0807578A2 (pt) | 2007-02-23 | 2021-06-15 | Aileron Therapeutics, Inc. | macrociclo peptidomimético, composto, kit e métodos para sintetizar um macrociclo peptidomimético |
| EP2508531B1 (en) | 2007-03-28 | 2016-10-19 | President and Fellows of Harvard College | Stitched polypeptides |
| WO2010034034A1 (en) | 2008-09-22 | 2010-03-25 | Aileron Therapeutics, Inc. | Peptidomimetic macrocycles |
| BRPI0920899A2 (pt) | 2008-11-24 | 2016-04-26 | Aileron Therapeutics Inc | macrociclos peptidomiméticos com propriedades melhoradas |
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