JP2007504353A5 - - Google Patents
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- Publication number
- JP2007504353A5 JP2007504353A5 JP2006533421A JP2006533421A JP2007504353A5 JP 2007504353 A5 JP2007504353 A5 JP 2007504353A5 JP 2006533421 A JP2006533421 A JP 2006533421A JP 2006533421 A JP2006533421 A JP 2006533421A JP 2007504353 A5 JP2007504353 A5 JP 2007504353A5
- Authority
- JP
- Japan
- Prior art keywords
- poly
- group
- amine
- amino ester
- following formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000642 polymer Polymers 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 25
- -1 acrylate esters Chemical class 0.000 claims description 22
- 229920000023 polynucleotide Polymers 0.000 claims description 21
- 239000002157 polynucleotide Substances 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000011780 sodium chloride Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229920001212 Poly(beta amino esters) Polymers 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drugs Drugs 0.000 claims description 6
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229920003013 deoxyribonucleic acid Polymers 0.000 claims description 5
- 125000005842 heteroatoms Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229920000160 (ribonucleotides)n+m Polymers 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- 108010039918 Polylysine Proteins 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 229920000656 polylysine Polymers 0.000 claims description 3
- 230000002194 synthesizing Effects 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005012 alkyl thioether group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 239000008139 complexing agent Substances 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- 239000002105 nanoparticle Substances 0.000 claims 2
- 150000003384 small molecules Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 125000004954 trialkylamino group Chemical group 0.000 claims 2
- 108020004459 Small Interfering RNA Proteins 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000008079 hexane Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 1
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N iminomethylideneazanide Chemical compound [NH-]C#N ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 238000000614 phase inversion technique Methods 0.000 claims 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims 1
- 239000002924 silencing RNA Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000000935 solvent evaporation Methods 0.000 claims 1
- 229940063673 spermidine Drugs 0.000 claims 1
- 229940063675 spermine Drugs 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000003612 virological Effects 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000001415 gene therapy Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 0 *CCC1OCCO1 Chemical compound *CCC1OCCO1 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000001890 transfection Methods 0.000 description 2
- 229920002521 Macromolecule Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FKJVYOFPTRGCSP-UHFFFAOYSA-N NCCCN(CCO)CCO Chemical compound NCCCN(CCO)CCO FKJVYOFPTRGCSP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000001476 gene delivery Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 125000004430 oxygen atoms Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutic aid Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000004805 robotic Methods 0.000 description 1
- 230000002269 spontaneous Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/446,444 US7427394B2 (en) | 2000-10-10 | 2003-05-28 | Biodegradable poly(β-amino esters) and uses thereof |
US10/446,444 | 2003-05-28 | ||
PCT/US2004/016521 WO2004106411A2 (en) | 2003-05-28 | 2004-05-26 | Biodegradable poly(beta-amino esters) and uses thereof |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010069008A Division JP5558154B2 (ja) | 2003-05-28 | 2010-03-24 | 生分解性ポリ(β−アミノエステル)およびその使用 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2007504353A JP2007504353A (ja) | 2007-03-01 |
JP2007504353A5 true JP2007504353A5 (US20110009641A1-20110113-C00185.png) | 2010-05-13 |
JP4740864B2 JP4740864B2 (ja) | 2011-08-03 |
Family
ID=33489383
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006533421A Expired - Lifetime JP4740864B2 (ja) | 2003-05-28 | 2004-05-26 | 生分解性ポリ(β−アミノエステル)およびその使用 |
JP2010069008A Expired - Fee Related JP5558154B2 (ja) | 2003-05-28 | 2010-03-24 | 生分解性ポリ(β−アミノエステル)およびその使用 |
JP2014013391A Pending JP2014129536A (ja) | 2003-05-28 | 2014-01-28 | 生分解性ポリ(β−アミノエステル)およびその使用 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010069008A Expired - Fee Related JP5558154B2 (ja) | 2003-05-28 | 2010-03-24 | 生分解性ポリ(β−アミノエステル)およびその使用 |
JP2014013391A Pending JP2014129536A (ja) | 2003-05-28 | 2014-01-28 | 生分解性ポリ(β−アミノエステル)およびその使用 |
Country Status (9)
Families Citing this family (143)
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USRE43612E1 (en) | 2000-10-10 | 2012-08-28 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
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US20050123596A1 (en) * | 2003-09-23 | 2005-06-09 | Kohane Daniel S. | pH-triggered microparticles |
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US8071082B2 (en) * | 2006-07-21 | 2011-12-06 | Massachusetts Institute Of Technology | End-modified poly(beta-amino esters) and uses thereof |
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AU2007333225B2 (en) * | 2006-12-08 | 2014-06-12 | Massachusetts Institute Of Technology | Delivery of nanoparticles and/or agents to cells |
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US8969353B2 (en) | 2008-11-07 | 2015-03-03 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
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US9717694B2 (en) | 2009-05-15 | 2017-08-01 | The Johns Hopkins University | Peptide/particle delivery systems |
ES2713852T3 (es) | 2009-12-01 | 2019-05-24 | Translate Bio Inc | Derivado de esteroides para la administración de ARNm en enfermedades genéticas humanas |
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- 2004-05-26 WO PCT/US2004/016521 patent/WO2004106411A2/en active IP Right Grant
- 2004-05-26 PT PT04753364T patent/PT1639029E/pt unknown
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