HRP20191114T1 - Kationski polimeri na bazi glikogena - Google Patents
Kationski polimeri na bazi glikogena Download PDFInfo
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- HRP20191114T1 HRP20191114T1 HRP20191114TT HRP20191114T HRP20191114T1 HR P20191114 T1 HRP20191114 T1 HR P20191114T1 HR P20191114T T HRP20191114T T HR P20191114TT HR P20191114 T HRP20191114 T HR P20191114T HR P20191114 T1 HRP20191114 T1 HR P20191114T1
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- alkyl
- alkylamino
- group
- alkylammonium
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- 229920002527 Glycogen Polymers 0.000 title claims 16
- 229940096919 glycogen Drugs 0.000 title claims 16
- 229920006317 cationic polymer Polymers 0.000 title claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 47
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 26
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 14
- 150000001449 anionic compounds Chemical class 0.000 claims 10
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 150000007529 inorganic bases Chemical class 0.000 claims 9
- 150000007530 organic bases Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 7
- -1 N,N-dimethylamino-ethyl Chemical group 0.000 claims 6
- 125000002091 cationic group Chemical group 0.000 claims 5
- 229920000642 polymer Polymers 0.000 claims 5
- 150000007523 nucleic acids Chemical class 0.000 claims 4
- 102000039446 nucleic acids Human genes 0.000 claims 4
- 108020004707 nucleic acids Proteins 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940063673 spermidine Drugs 0.000 claims 1
- 229940063675 spermine Drugs 0.000 claims 1
- 238000001890 transfection Methods 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
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- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/713—Double-stranded nucleic acids or oligonucleotides
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
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- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/18—Reserve carbohydrates, e.g. glycogen, inulin, laminarin; Derivatives thereof
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Claims (15)
1. Kationski polimer na bazi glikogena, naznačen time, da obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih:
(a)
u kojoj
su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i
n je cijeli broj veći od ili jednak 1; i
(b)
u kojoj
R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili od skupine koja sadrži dušik odabrane od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil,
{[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina;
kod X1 i X2 koji mogu biti isti ili različiti, radi se o skupini –OH ili skupini koja sadrži dušik
–NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i
m je cijeli broj veći od ili jednak 1;
uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2, i
uz uvjet da je navedeni kationski polimer na bazi glikogena različit od produkta koji se dobije reakcijom glikogena s N-(3-kloro-2-hidroksipropil)-trimetil-amonij-kloridom.
2. Kationski polimer na bazi glikogena prema zahtjevu 1, naznačen time, da su navedene skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: [N,N-di(C1-C3)alkilamino]-(C1-C3)alkil,
{[N,N-di(C1-C3)alkilamino]-(C1-C3)alkil-di(C1-C3)alkilamonij}-(C1-C3)alkil,
{[N,N-di(C1-C3)alkilamino]-(C1-C3)alkilamino}-(C1-C3)alkil, [tri(C1-C3)alkilamonij]-(C1-C3)alkil,
azociklil-(C1-C3)alkil, gdje su (C1-C3)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s hidroksil-skupinom.
3. Kationski polimer na bazi glikogena prema zahtjevu 2, naznačen time, da su navedene skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: N,N-dimetilamino-etil, N,N-dimetilamino-propil, N,N-dietilamino-etil, [(N,N-dimetilaminoetil)dimetilamonij]-etil, [(N,N-dimetilamino-propil)-dimetilamonij]-propil, [(N,N-dietilaminoetil)dietil-amonij]-etil, [trimetilamonij]-2-hidroksipropil, piperidil-N-etil ili morfolinil-N-etil.
4. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da R1 je atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: [N,N-di(C1-C3)alkilamino]-(C1-C3)alkil, {[N,N-di(C1-C3)alkilamino]-(C1-C3)alkil-di(C1-C3)alkilamonij}-(C1-C3)alkil, {[N,N-di(C1-C3)alkil-amino]-(C1-C3)alkilamino}-(C1-C3)alkil ili [tri(C1-C3)alkilamonij]-(C1-C3)alkil, gdje su (C1-C3)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s hidroksil-skupinom.
5. Kationski polimer na bazi glikogena prema zahtjevu 4, naznačen time, da je R1 atom vodika ili karboksimetil-skupina.
6. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da su X1 i X2 koji mogu biti isti ili različiti, skupina koja sadrži dušik –NHR2, u kojoj R2 je atom vodika ili H-[NH-(C1-C4)alkil]p-, gdje p je cijeli broj veći od ili jednak 1, a (C1-C4)alkil-skupine mogu biti iste ili različite.
7. Kationski polimer na bazi glikogena prema zahtjevu 6, naznačen time, da navedena skupina H-[NH-(C1-C4)alkil]p- je polietilenimin, s molekularnom masom od 50 do 3000 daltona, spermin (H2N(CH2)3NH(CH2)4NH(CH2)3NH2), ili spermidin (H2N(CH2)4NH(CH2)4NH2).
8. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da navedene ponavljajuće jedinice (a) i (b) obuhvaćaju sljedeće:
- najmanje jednu skupinu koja sadrži dušik, koja se može ionizirati na fiziološkoj pH-vrijednosti, odabranu iz skupine koja se sastoji od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-(C1-C6)alkilamino}- (C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil i azociklil-(C1-C6)alkil; i
- najmanje jednu skupinu koja sadrži dušik, koja se može ionizirati na pH-vrijednosti nižoj od fiziološke pH, odabranu iz skupine koja se sastoji od sljedećih: NH2-{[(C1-C3)alkil]-di(C1-C6)alkilamonij}-(C1-C6)alkil i{[N,N-di(C1-C3)alkil-amino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil.
9. Kompleks između kationskog polimera na bazi glikogena prema bilo kojem od zahtjeva 1 do 8 i jednog anionskog spoja, naznačen time, da je navedeni anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline.
10. Kompleks prema zahtjevu 9, naznačen time, da navedeni kompleks obuhvaća količinu spomenutog anionskog spoja koja iznosi između 5% i 60% po masi u odnosu na masu navedenog kationskog polimera na bazi glikogena.
11. Kompleks prema zahtjevu 10, naznačen time, da navedeni kompleks obuhvaća količinu spomenutog anionskog spoja koja iznosi između 10% i 50% po masi u odnosu na masu navedenog kationskog polimera na bazi glikogena.
12. Farmaceutski sastav, naznačen time, da obuhvaća (A) kompleks između (1) kationskog polimera na bazi glikogena koji obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih:
(a)
u kojoj
su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i
n je cijeli broj veći od ili jednak 1; i
(b)
u kojoj
R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil,gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina;
se kod X1 i X2 koji mogu biti isti ili različiti, radi o skupini –OH ili skupini koja sadrži dušik –NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i
m je cijeli broj veći od ili jednak 1;
uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2,
i (2) anionskog spoja, pri čemu je spomenuti anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline;
te (B) najmanje jedno farmaceutski prihvatljivo pomoćno sredstvo.
13. Farmaceutski sastav prema zahtjevu 12, naznačen time, da spomenuti anionski spoj je jedna nukleinska kiselina.
14. Farmaceutski sastav prema prethodnim zahtjevima 12 ili 13, naznačen time, da se upotrebljava za injektibilnu primjenu.
15. Kompleks, naznačen time, da je između (1) kationskog polimera na bazi glikogena koji obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih:
(a)
u kojoj
su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i
n je cijeli broj veći od ili jednak 1; i
(b)
kojoj
R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili od skupine koja sadrži dušik odabrane od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil,
{[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina;
se kod X1 i X2 koji mogu biti isti ili različiti, radi o skupini –OH ili skupini koja sadrži dušik –NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i
m je cijeli broj veći od ili jednak 1;
uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2,
i (2) anionskog spoja, pri čemu je spomenuti anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline,
te time, da se kompleks upotrebljava kao sredstvo za isporuku ili transfekciju spomenutog anionskog spoja.
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| Application Number | Priority Date | Filing Date | Title |
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| EP12159710 | 2012-03-15 | ||
| EP13704973.0A EP2825565B1 (en) | 2012-03-15 | 2013-02-21 | Glycogen-based cationic polymers |
| PCT/EP2013/053422 WO2013135471A1 (en) | 2012-03-15 | 2013-02-21 | Glycogen-based cationic polymers |
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| HRP20191114T1 true HRP20191114T1 (hr) | 2019-09-20 |
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| EP (1) | EP2825565B1 (hr) |
| JP (1) | JP6247234B2 (hr) |
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| AR095937A1 (es) | 2013-04-05 | 2015-11-25 | Acraf | Potenciador de la solubilidad en agua a base de glucógeno |
| KR102214865B1 (ko) | 2013-04-26 | 2021-02-15 | 마이렉서스 바이오테크놀로지스 인코퍼레이티드 | 파이토글리코겐 나노입자와 이를 제조하는 방법 |
| US20180036409A1 (en) * | 2014-12-29 | 2018-02-08 | Bonac Corporation | Composition containing nucleic acid molecule stably |
| CN104558246B (zh) * | 2015-01-20 | 2017-03-01 | 武汉理工大学 | 一种叶酸/生物素修饰的壳聚糖材料及其制备方法 |
| DE102015205088C5 (de) * | 2015-03-20 | 2024-09-26 | Kuka Deutschland Gmbh | Verfahren zum Ermitteln eines Kalibrierungsparameters eines Fahrzeuges sowie Fahrzeug hierzu |
| JP6872782B2 (ja) * | 2016-03-08 | 2021-05-19 | 国立大学法人京都大学 | カチオン性グルカンナノスフェア、複合体、核酸導入剤及びがん治療剤 |
| CA3020772A1 (en) * | 2016-04-14 | 2017-10-19 | Mirexus Biotechnologies Inc. | Anti-infective compositions comprising phytoglycogen nanoparticles |
| US20190117681A1 (en) * | 2016-05-04 | 2019-04-25 | Mirexus Biotechnologies Inc. | Glycogen and phytoglycogen nanoparticles as immunosuppressive compounds, and compositions and methods of use thereof |
| CN105949344B (zh) * | 2016-05-13 | 2019-05-17 | 中山大学 | 一种阳离子超支化多糖衍生物及其在增强血卟啉类光敏剂对肿瘤细胞光毒性方面的应用 |
| EP3661563A4 (en) | 2017-07-31 | 2021-11-10 | The Ohio State Innovation Foundation | BIOMIMETIC NANOMATERIALS AND USES THEREOF |
| WO2019140304A1 (en) * | 2018-01-11 | 2019-07-18 | Virgina Tech Intellectual Properties Inc. | Amphiphilic polysacchardides,polysaccharide-based hydrogels, and methods of manufacture |
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| GB8904370D0 (en) * | 1989-02-25 | 1989-04-12 | Cosmas Damian Ltd | Liquid delivery compositions |
| IT1255488B (it) | 1992-08-04 | 1995-11-06 | Angelini Francesco Ist Ricerca | Polisaccaridi del glicogeno |
| US7144713B1 (en) | 1995-10-02 | 2006-12-05 | Emd Biosciences, Inc. | Method for precipitating nucleic acid with visible carrier |
| GB9600272D0 (en) | 1996-01-06 | 1996-03-06 | Univ Nottingham | Polymers |
| US6106858A (en) * | 1997-09-08 | 2000-08-22 | Skyepharma, Inc. | Modulation of drug loading in multivescular liposomes |
| EP1399189A1 (en) | 2001-06-11 | 2004-03-24 | Universite De Montreal | Compositions and methods for enhancing nucleic acid transfer into cells |
| US20030147958A1 (en) | 2002-01-29 | 2003-08-07 | Cheol-Hee Ahn | Biodegradable multi-block copolymers of poly(amino acid)s and poly(ethylene glycol) for the delivery of bioactive agents |
| WO2003078576A2 (en) | 2002-03-12 | 2003-09-25 | Nitto Denko Corporation | Vector for transfection of eukaryotic cells |
| JPWO2005094894A1 (ja) * | 2004-03-31 | 2008-02-14 | 株式会社メドジェル | 細胞に核酸を導入するための製剤 |
| WO2007038769A1 (en) | 2005-09-28 | 2007-04-05 | Hetzel Adrian H | Electro-hydraulic timed angle controlled joint simulation torque calibration, certification and analysis device |
| UA97559C2 (uk) * | 2007-11-08 | 2012-02-27 | Оцука Фармасьютікал Ко., Лтд. | Комплекс нуклеїнової кислоти і композиція для доставки нуклеїнової кислоти |
| CN101235098A (zh) * | 2008-01-09 | 2008-08-06 | 浙江大学 | 功能性植物多糖的修饰方法 |
| WO2010072628A1 (en) * | 2008-12-22 | 2010-07-01 | Unilever Plc | Laundry compositions |
| ES2393529T3 (es) * | 2008-12-22 | 2012-12-26 | Unilever Nv | Composiciones de lavandería |
| US8575131B2 (en) | 2009-05-08 | 2013-11-05 | National University Corporation Kagoshima University | Glucuronic acid-containing glucan, process for production of same, and use of same |
| EP2275085A1 (en) * | 2009-07-07 | 2011-01-19 | University of Rostock | Biodegradable copolymer suitable for delivering nucleic acid materials into cells |
| CN102068698A (zh) * | 2009-11-24 | 2011-05-25 | 深圳先进技术研究院 | 纳米疫苗及其制备方法 |
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