RU2013118224A - Новые низкомолекулярные катионные липиды для доставки олигонуклеотидов - Google Patents
Новые низкомолекулярные катионные липиды для доставки олигонуклеотидов Download PDFInfo
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Abstract
1. Катионный липид по формуле A:где:Rи Rнезависимо друг от друга выбраны из H, алкила (C-C), гетероциклила и полиамина, где указанный алкил, гетероциклил и полиамин, необязательно, являются замещенными одним-тремя заместителями, выбранными из R', или Rи Rмогут быть взяты совместно с азотом, к которому они присоединены для образования моноциклического гетероцикла с 4-7 членами, необязательно содержащего в себе, в дополнение к данному азоту, один или два дополнительных гетероатома, выбранных из N, O и S, указанный моноциклический гетероцикл, необязательно, является замещенным с использованием от одного до трех заместителей, выбранных из R';Rнезависимо выбран из H и алкила (C-C), указанный алкил, необязательно, является замещенным с использованием от одного до трех заместителей, выбранных из R';R' независимо выбран из галогена, R", OR", SR", CN, COR" или CON(R");R" независимо выбран из H и алкила (C-C), где указанный алкил, необязательно, является замещенным с использованием галогена и OH;n представляет собой 0, 1, 2, 3, 4 или 5;Lвыбран из алкила C-Cи алкенила C-C, указанные алкил и алкенил, необязательно, являются замещенными с использованием одного или нескольких заместителей, выбранных из R'; иLвыбран из алкила C-Cи акленила C-C, указанные алкил и алкенил, необязательно, являются замещенными с использованием одного или нескольких заместителей, выбранных из R';или любая фармацевтически приемлемая соль или его стереоизомер.2. Катионный липид, представленный в формуле А по п.1, где:Rи R, каждый представляет собой метил;Rпредставляет собой H;n равен 0;Lвыбран из алкила C-Cи алкенила C-C; иLвыбран из алкила C-Cи алкенила C-C;или любая фармацевтически приемлемая соль или его стере�
Claims (10)
1. Катионный липид по формуле A:
где:
R1 и R2 независимо друг от друга выбраны из H, алкила (C1-C6), гетероциклила и полиамина, где указанный алкил, гетероциклил и полиамин, необязательно, являются замещенными одним-тремя заместителями, выбранными из R', или R1 и R2 могут быть взяты совместно с азотом, к которому они присоединены для образования моноциклического гетероцикла с 4-7 членами, необязательно содержащего в себе, в дополнение к данному азоту, один или два дополнительных гетероатома, выбранных из N, O и S, указанный моноциклический гетероцикл, необязательно, является замещенным с использованием от одного до трех заместителей, выбранных из R';
R3 независимо выбран из H и алкила (C1-C6), указанный алкил, необязательно, является замещенным с использованием от одного до трех заместителей, выбранных из R';
R' независимо выбран из галогена, R", OR", SR", CN, CO2R" или CON(R")2;
R" независимо выбран из H и алкила (C1-C6), где указанный алкил, необязательно, является замещенным с использованием галогена и OH;
n представляет собой 0, 1, 2, 3, 4 или 5;
L1 выбран из алкила C4-C24 и алкенила C4-C24, указанные алкил и алкенил, необязательно, являются замещенными с использованием одного или нескольких заместителей, выбранных из R'; и
L2 выбран из алкила C3-C9 и акленила C3-C9, указанные алкил и алкенил, необязательно, являются замещенными с использованием одного или нескольких заместителей, выбранных из R';
или любая фармацевтически приемлемая соль или его стереоизомер.
2. Катионный липид, представленный в формуле А по п.1, где:
R1 и R2, каждый представляет собой метил;
R3 представляет собой H;
n равен 0;
L1 выбран из алкила C4-C24 и алкенила C4-C24; и
L2 выбран из алкила C3-C9 и алкенила C3-C9;
или любая фармацевтически приемлемая соль или его стереоизомер.
3. Катионный липид, представленный формулой А по п.1, где:
R1 и R2, каждый представляет собой метил;
R3 представляет собой H;
n равен 2;
L1 выбран из алкила C4-C24 и алкенила C4-C24; и
L2 выбран из алкила C3-C9 и алкенила C3-C9;
или любая фармацевтически приемлемая соль или его стереоизомер.
4. Катионный липид, который выбран из:
(20Z,23Z)-N,N-диметилнонакоза-20,23-диен-10-амина (соединение 1);
(17Z,20Z)-N,N-диметилгексакоза-17,20-диен-9-амина (соединение 2);
(16Z,19Z)-N,N-диметилпентакоза-16,19-диен-8-амина (соединение 3);
(13Z,16Z)-N,N-диметилдокоза-13,16-диен-5-амина (соединение 4);
(12Z,15Z)-N,N-диметилгеникоза-12,15-диен-4-амина (соединение 5);
(14Z,17Z)-N,N-диметилтрикоза-14,17-диен-6-амина (соединение 6);
(15Z,18Z)-N,N-диметилтетракоза-15,18-диен-7-амина (соединение 7);
(18Z,21Z)-N,N-диметилгептакоза-18,21-диен-10-амина (соединение 8);
(15Z,18Z)-N,N-диметилтетракоза-15,18-диен-5-амина (соединение 9);
(14Z,17Z)-N,N-диметилтрикоза-14,17-диен-4-амина (соединение 10);
(19Z,22Z)-N,N-диметилоктакоза-19,22-диен-9-амина (соединение 11);
(18Z,21Z)-N,N-диметилгептакоза-18,21-диен-8-амина (соединение 12);
(17Z,20Z)-N,N-диметилгексакоза-17,20-диен-7-амина (соединение 13);
(16Z,19Z)-N,N-диметилпентакоза-16,19-диен-6-амина (соединение 14);
(22Z,25Z)-N,N-диметилгентриаконта-22,25-диен-10-амина (соединение 15);
(21Z,24Z)-N,N-диметилтриаконта-21,24-диен-9-амина (соединение 16);
(18Z)-N,N-диметилгептакоз-18-ен-10-амина (соединение 17);
(17Z)-N,N-диметилгексакоз-17-ен-9-амина (соединение 18);
(19Z,22Z)-N,N-диметилоктакоза-19,22-диен-7-амина (соединение 19); и
N,N-диметилгептакозан-10-амина (соединение 20);
(20Z,23Z)-N-этил-N-метилнонакоза-20,23-диен-10-амина (соединение 21);
1-[(11Z,14Z)-1-нониликоза-11,14-диен-1-ил]пирролидина (соединение 22);
(20Z)-N,N-диметилгептакоз-20-ен-10-амина (соединение 23);
(15Z)-N,N-диметилгептакоз-15-ен-10-амина (соединение 24);
(14Z)-N,N-диметилнонакоз-14-ен-10-амина (соединение 25);
(17Z)-N,N-диметилнонакоз-17-ен-10-амина (соединение 26);
(24Z)-N,N-диметилтритриаконт-24-ен-10-амина (соединение 27);
(20Z)-N,N-диметилнонакоз-20-ен-10-амина (соединение 28);
(22Z)-N,N-диметилгентриаконт-22-ен-10-амина (соединение 29);
(16Z)-N,N-диметилпентакоз-16-ен-8-амина (соединение 30);
(12Z,15Z)-N,N-диметил-2-нонилгеникоза-12,15-диен-1-амина (соединение 31);
(13Z,16Z)-N,N-диметил-3-нонилдокоза-13,16-диен-1-амина (соединение 32);
N,N-диметил-1-[(1S,2R)-2-октилциклопропил]гептадекан-8-амина (соединение 33);
1-[(1S,2R)-2-гексилциклопропил]-N,N-диметилнонадекан-10-амина (соединение 34);
N,N-диметил-1-[(1S,2R)-2-октилциклопропил]нонадекан-10-амина (соединение 35);
N,N-диметил-21-[(1S,2R)-2-октилциклопропил]геникозан-10-амина (соединение 36);
N,N-диметил-1-[(1S,2S)-2-{[(1R,2R)-2-пентилциклопропил]метил}циклопропил]нонадекан-10-амина (соединение 37);
N,N-диметил-1-[(1S,2R)-2-октилциклопропил]гексадекан-8-амина (соединение 38);
N,N-диметил-1-[(1R,2S)-2-ундецилциклопропил]тетрадекан-5-амина (соединение 39);
N,N-диметил-3-{7-[(1S,2R)-2-октилциклопропил]гептил}додекан-1-амина (соединение 40)
1-[(1R,2S)-2-гептилциклопропил]-N,N-диметилоктадекан-9-амина (соединение 41);
1-[(1S,2R)-2-децилциклопропил]-N,N-диметилпентадекан-6-амина (соединение 42);
N,N-диметил-1-[(1S,2R)-2-октилциклопропил]пентадекан-8-амина (соединение 43); и
(11E,20Z,23Z)-N,N-диметилнонакоза-11,20,23-триен-10-амина (соединение 44);
или любая фармацевтически приемлемая соль или его стереоизомер.
5. Катионный липид, который представляет собой:
(13Z,16Z)-N,N-диметил-3-нонилдокоза-13,16-диен-1-амин (соединение 32);
или любую фармацевтически приемлемую соль или его стереоизомер.
6. Композиция LNP, которая содержит в себе катионный липид по формуле А по п.1, холестерин, DSPC и PEG-DMG.
7. Композиция LNP, которая содержит в себе катионный липид (13Z,16Z)-N,N-диметил-3-нонилдокоза-13,16-диен-1-амин (соединение 32), холестерин, DSPC и PEG-DMG.
8. Применение катионного липида по п.1 для получения липидных наночастиц.
9. Применение катионного липида по п.1 в качестве компонента в липидной наночастице для доставки олигонуклеотидов.
10. Применение по п.9, где данные олигонуклеотиды представляют собой миРНК.
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US38448610P | 2010-09-20 | 2010-09-20 | |
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US61/514,270 | 2011-08-02 | ||
PCT/US2011/052328 WO2012040184A2 (en) | 2010-09-20 | 2011-09-20 | Novel low molecular weight cationic lipids for oligonucleotide delivery |
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WO2012019168A2 (en) | 2010-08-06 | 2012-02-09 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
KR101878361B1 (ko) | 2010-09-20 | 2018-08-20 | 시르나 쎄러퓨틱스 인코퍼레이티드 | 올리고뉴클레오티드 전달을 위한 신규 저분자량 양이온성 지질 |
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