DK2575767T3 - Hidtil ukendte lavmolekylære kationiske lipider til fremføring af oligonukleotider - Google Patents

Hidtil ukendte lavmolekylære kationiske lipider til fremføring af oligonukleotider Download PDF

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DK2575767T3
DK2575767T3 DK11790268.4T DK11790268T DK2575767T3 DK 2575767 T3 DK2575767 T3 DK 2575767T3 DK 11790268 T DK11790268 T DK 11790268T DK 2575767 T3 DK2575767 T3 DK 2575767T3
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compound
yloxy
amine
propan
dimethyl
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Brian W Budzik
Steven L Colletti
Jennifer R Davis
Ivory D Hills
Darla D Seifried
Matthew G Stanton
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Sirna Therapeutics Inc
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    • C07—ORGANIC CHEMISTRY
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/46—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/44—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
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    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Claims (7)

1. Kationisk lipid med formel A:
hvor: R1 og R2 er udvalgt uafhængigt blandt (C1-C6) alkyl eller cycloalkyl, heterocyclyl og polyamin, hvor alkyl eller cycloalkyl, heterocyclyl og polyamin eventuelt er substitueret med en til tre substituenter udvalgt blandt R', eller R1 og R2 sammen med nitrogenatomet, hvortil de er bundet, kan danne en monocyklisk heterocyklus med 4-7 led, der eventuelt foruden nitrogenatomet indeholder et eller to yderligere heteroatomer udvalgt blandt N, 0 og S, hvilken monocykliske heterocyklus eventuelt er substitueret med én til tre substituenter udvalgt blandt R'; R' er udvalgt uafhængigt blandt halogen, R", OR", SR", CN, C02R" eller CON(R")2; R" er udvalgt uafhængigt blandt H og (C1-C6) alkyl eller cycloalkyl, hvor alkyl eller cycloalkyl eventuelt er substitueret med halogen og OH; Li er Ci2-C22alkenyl, hvilken alkenyl eventuelt er substitueret med en eller flere substituenter udvalgt blandt R'; og L2 er udvalgt blandt C3-C9alkyl og C3_C9alkenyl, hvilken alkyl og alkenyl eventuelt er substitueret med en eller flere substituenter udvalgt blandt R'; eller et hvilket som helst farmaceutisk acceptabelt salt eller en hvilken som helst farmaceutisk acceptabel stereoisomer deraf.
2. Kationisk lipid med formel A ifølge krav 1, hvor: Ri og R2 hver er methyl; Li er Ci2-C22alkenyl; og L2 er udvalgt blandt C3-C9alkyl og C3-C9alkenyl; eller et hvilket som helst farmaceutisk acceptabelt salt eller en hvilken som helst farmaceutisk acceptabel stereoisomer deraf.
3. Kationisk lipid ifølge krav 1, der er udvalgt blandt: R-N,N-dimethyl-1-[(9Z,12Z)-octadeca-9,12-dien-l-yloxy]-3-(octyloxy)propan-2-amin (Forbindelse 2); S-N,N-dimethyl-1-[(9Z,12Z)-octadeca-9,12-dien-l-yloxy]-3-(octyloxy)propan-2-amin (Forbindelse 1); 1—{2 —[(9Z,12Z)-octadeca-9,12-dien-l-yloxy]-1-[(octyloxy)methyl]ethylJpyrrolidin (Forbindelse 3); (2 S)-N,N-dimethyl-1-[(9Z,12Z)-octadeca-9,12-dien-l-yloxy]-3-[(5Z)-oct-5-en-l-yloxy]propan-2-amin (Forbindelse 4); 1 —{2 — [ (9Z, 12Z)-octadeca-9,12-dien-l-yloxy]-1-[ (octyloxy)methyl]ethyl}azetidin (Forbindelse 5); (2 S)-1-(hexyloxy)-N,N-dimethyl-3-[(9 Z,12Z)-octadeca-9,12-dien- 1- yloxy] propan-2-amin (Forbindelse 6); (2 S)-1-(heptyloxy)-N,N-dimethyl-3-[ (9 Z,12Z)-octadeca-9,12-dien-l-yloxy] propan-2-amin (Forbindelse 7) ; N, N-dimethyl-1-(nonyloxy)-3-[(9Z,12Z)-octadeca-9,12-dien-l-yloxy] propan-2-amin (Forbindelse 8); N,N-dimethyl-1-[(9 Z)-octadec-9-en-l-yloxy]-3-(octyloxy)propan- 2- amin (Forbindelse 9) ; (2 S)-N,N-dimethyl-1-[(6Z,9Z,12Z)-octadeca-6,9,12-trien-l-yloxy]-3-(octyloxy)propan-2-amin (Forbindelse 10); (2S) -1-[(11Z, 14Z) -icosa-11,14-dien-l-yloxy]-N,N-dimethyl-3-(pentyloxy)propan-2-amin (Forbindelse 11); (2 S)-1-(hexyloxy)-3-[(11Z,14Z)-icosa-11,14-dien-l-yloxy]-N,N-dimethylpropan-2-amin (Forbindelse 12); 1-[ (11Z, 14Z)-icosa-11,14-dien-l-yloxy]-N,N-dimethyl-3-(octyloxy)propan-2-amin (Forbindelse 13); 1-[(13Z,16Z)-docosa-13,16-dien-l-yloxy]-N,N-dimethyl-3-(octyloxy)propan-2-amin (Forbindelse 14); (2 S)-1-[(13Z,16Z)-docosa-13,16-dien-l-yloxy]-3-(hexyloxy)-N,N-dimethylpropan-2-amin (Forbindelse 15); (2 S)-1-[(13Z)-docos-13-en-l-yloxy]-3-(hexyloxy)-N,N-dimethylpropan-2-amin (Forbindelse 16); 1- [(13Z)-docos-13-en-l-yloxy]-N,N-dimethyl-3-(octyloxy)propan- 2- amin (Forbindelse 17); 1- [(9 Z)-hexadec-9-en-l-yloxy]-N,N-dimethyl-3-(octyloxy)propan- 2- amin (Forbindelse 18) ; (2R)-N,N-dimethyl-1-[(1-methyloctyl)oxy]-3-[(9Z,12Z)-octadeca-9,12-dien-l-yloxy]propan-2-amin (Forbindelse 19); N, N-dimethyl-1-(octyloxy)-3-({8-[(lS,2S)-2-{[(IR,2R)-2-pentylcyclopropyl]methyl}cyclopropyl]octyl}oxy)propan-2-amiη (Forbindelse 21); og N,N-dimethyl-1-{[8-(2-octylcyclopropyl)octyl]oxy}-3-(octyloxy)propan-2-amin (Forbindelse 22); eller et hvilket som helst farmaceutisk acceptabelt salt eller en hvilken som helst farmaceutisk acceptabel stereoisomer deraf.
4. Anvendelse af et kationisk lipid ifølge et hvilket som helst af ovennævnte krav til fremstilling af lipidnanopartikler.
5. Kationisk lipid ifølge et hvilket som helst af kravene 1 til 3 som en bestanddel i en lipidnanopartikel til anvendelse til fremføring af oligonukleotider.
6. Kationisk lipid til anvendelse ifølge krav 5, hvor oligonukleotiderne er siRNA eller miRNA.
7. Kationisk lipid til anvendelse ifølge krav 5, hvor oligonukleotiderne er siRNA.
DK11790268.4T 2010-06-04 2011-05-31 Hidtil ukendte lavmolekylære kationiske lipider til fremføring af oligonukleotider DK2575767T3 (da)

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PCT/US2011/038490 WO2011153120A1 (en) 2010-06-04 2011-05-31 Novel low molecular weight cationic lipids for oligonucleotide delivery

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