EA030246B1 - Полимерные соединения-иммуномодулирующие средства - Google Patents
Полимерные соединения-иммуномодулирующие средства Download PDFInfo
- Publication number
- EA030246B1 EA030246B1 EA201171480A EA201171480A EA030246B1 EA 030246 B1 EA030246 B1 EA 030246B1 EA 201171480 A EA201171480 A EA 201171480A EA 201171480 A EA201171480 A EA 201171480A EA 030246 B1 EA030246 B1 EA 030246B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- polymer
- solution
- alkyl
- compound according
- poly
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 214
- 230000002519 immonomodulatory effect Effects 0.000 title abstract description 45
- 239000002539 nanocarrier Substances 0.000 claims abstract description 191
- 239000000203 mixture Substances 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 238000000034 method Methods 0.000 claims abstract description 86
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 37
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 37
- 229920000728 polyester Polymers 0.000 claims abstract description 19
- 230000028993 immune response Effects 0.000 claims abstract description 16
- 229960005486 vaccine Drugs 0.000 claims abstract description 13
- 239000004952 Polyamide Substances 0.000 claims abstract description 11
- 229920002647 polyamide Polymers 0.000 claims abstract description 11
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 10
- 239000004417 polycarbonate Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- -1 hydroxy, phenyl Chemical group 0.000 claims description 54
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 32
- 229920001577 copolymer Polymers 0.000 claims description 29
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 25
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229920001610 polycaprolactone Polymers 0.000 claims description 17
- 238000005227 gel permeation chromatography Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000004632 polycaprolactone Substances 0.000 claims description 14
- 229920000954 Polyglycolide Polymers 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 235000014655 lactic acid Nutrition 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 230000004913 activation Effects 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- 239000004310 lactic acid Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 53
- 239000000243 solution Substances 0.000 description 188
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 35
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 25
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 22
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
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- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 description 13
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
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