MX2008011584A - Polimeros. - Google Patents
Polimeros.Info
- Publication number
- MX2008011584A MX2008011584A MX2008011584A MX2008011584A MX2008011584A MX 2008011584 A MX2008011584 A MX 2008011584A MX 2008011584 A MX2008011584 A MX 2008011584A MX 2008011584 A MX2008011584 A MX 2008011584A MX 2008011584 A MX2008011584 A MX 2008011584A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- groups
- polymer
- process according
- pendant
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 227
- 238000000034 method Methods 0.000 claims abstract description 108
- 235000000346 sugar Nutrition 0.000 claims abstract description 102
- 230000008569 process Effects 0.000 claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 61
- 150000008163 sugars Chemical class 0.000 claims abstract description 53
- 125000002355 alkine group Chemical group 0.000 claims abstract description 34
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 32
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000006239 protecting group Chemical group 0.000 claims abstract description 27
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 19
- 239000002158 endotoxin Chemical group 0.000 claims abstract description 18
- 229920006008 lipopolysaccharide Chemical group 0.000 claims abstract description 16
- 230000001404 mediated effect Effects 0.000 claims abstract description 15
- 150000003904 phospholipids Chemical group 0.000 claims abstract description 15
- 125000003827 glycol group Chemical group 0.000 claims abstract description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000012546 transfer Methods 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000003446 ligand Substances 0.000 claims description 42
- 150000001540 azides Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 239000002523 lectin Substances 0.000 claims description 35
- 230000027455 binding Effects 0.000 claims description 32
- 108090001090 Lectins Proteins 0.000 claims description 31
- 102000004856 Lectins Human genes 0.000 claims description 31
- -1 dialkylaminoalkyl methacrylates Chemical class 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 25
- 210000004027 cell Anatomy 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 229920001223 polyethylene glycol Polymers 0.000 claims description 22
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 229910052723 transition metal Inorganic materials 0.000 claims description 20
- 150000003624 transition metals Chemical class 0.000 claims description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 18
- 150000001720 carbohydrates Chemical class 0.000 claims description 18
- 235000014633 carbohydrates Nutrition 0.000 claims description 18
- 125000000524 functional group Chemical group 0.000 claims description 18
- 238000010526 radical polymerization reaction Methods 0.000 claims description 18
- 239000002202 Polyethylene glycol Substances 0.000 claims description 17
- 229930182830 galactose Natural products 0.000 claims description 17
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical group C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 claims description 16
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 15
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 13
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 13
- 239000003875 Wang resin Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 229920001184 polypeptide Polymers 0.000 claims description 12
- 150000003254 radicals Chemical group 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 238000003821 enantio-separation Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000008103 glucose Substances 0.000 claims description 9
- AAFZZRHUEAQWKE-UHFFFAOYSA-N n-ethyl-1-pyridin-2-ylmethanimine Chemical compound CCN=CC1=CC=CC=N1 AAFZZRHUEAQWKE-UHFFFAOYSA-N 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 229960000956 coumarin Drugs 0.000 claims description 6
- 235000001671 coumarin Nutrition 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001042 affinity chromatography Methods 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 102000039446 nucleic acids Human genes 0.000 claims description 5
- 108020004707 nucleic acids Proteins 0.000 claims description 5
- 150000007523 nucleic acids Chemical class 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 4
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229960002442 glucosamine Drugs 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- WRXZCLBKDXISQA-UHFFFAOYSA-N 2-chloro-7-methoxyquinoline-3-carbaldehyde Chemical compound C1=C(C=O)C(Cl)=NC2=CC(OC)=CC=C21 WRXZCLBKDXISQA-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 3
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical group CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 3
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 230000006870 function Effects 0.000 claims description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 3
- CWKYKJQWSSZVDF-UHFFFAOYSA-N n-propyl-1-pyridin-2-ylmethanimine Chemical group CCCN=CC1=CC=CC=N1 CWKYKJQWSSZVDF-UHFFFAOYSA-N 0.000 claims description 3
- DYMYLBQTHCJHOQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) butanoate Chemical compound CCCC(=O)ON1C(=O)CCC1=O DYMYLBQTHCJHOQ-UHFFFAOYSA-N 0.000 claims description 2
- ZJIFDEVVTPEXDL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) hydrogen carbonate Chemical compound OC(=O)ON1C(=O)CCC1=O ZJIFDEVVTPEXDL-UHFFFAOYSA-N 0.000 claims description 2
- AASBXERNXVFUEJ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) propanoate Chemical compound CCC(=O)ON1C(=O)CCC1=O AASBXERNXVFUEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- AQYNZOSCOWGGTP-UHFFFAOYSA-N 2-pyridin-2-ylsulfanylpyridine Chemical compound C=1C=CC=NC=1SC1=CC=CC=N1 AQYNZOSCOWGGTP-UHFFFAOYSA-N 0.000 claims description 2
- BTBWSRPRAGXJJV-UHFFFAOYSA-N 2h-benzotriazole;carbonic acid Chemical compound OC(O)=O.C1=CC=C2NN=NC2=C1 BTBWSRPRAGXJJV-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- OSWFHBHIMFEISE-UHFFFAOYSA-N 4,4-di(nonan-5-yl)-2-pyridin-2-yl-3h-pyridine Chemical group C1=CC(C(CCCC)CCCC)(C(CCCC)CCCC)CC(C=2N=CC=CC=2)=N1 OSWFHBHIMFEISE-UHFFFAOYSA-N 0.000 claims description 2
- QXZGLTYKKZKGLN-UHFFFAOYSA-N 4-(2,5-dioxopyrrolidin-1-yl)oxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)ON1C(=O)CCC1=O QXZGLTYKKZKGLN-UHFFFAOYSA-N 0.000 claims description 2
- VHJFWJXYEWHCGD-UHFFFAOYSA-N 4-nonyl-2-(4-nonylpyridin-2-yl)pyridine Chemical compound CCCCCCCCCC1=CC=NC(C=2N=CC=C(CCCCCCCCC)C=2)=C1 VHJFWJXYEWHCGD-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000015861 cell surface binding Effects 0.000 claims description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
- KYMVBVBRCRFHIE-UHFFFAOYSA-N ethane-1,2-diimine Chemical compound N=CC=N KYMVBVBRCRFHIE-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003550 marker Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- 102220047090 rs6152 Human genes 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 1
- 101710141544 Allatotropin-related peptide Proteins 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 238000012644 addition polymerization Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229920001484 poly(alkylene) Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
- Polymerization Catalysts (AREA)
- Medicinal Preparation (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Graft Or Block Polymers (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| GB0604911A GB0604911D0 (en) | 2006-03-10 | 2006-03-10 | Polymers |
| US80958806P | 2006-05-31 | 2006-05-31 | |
| GB0617918A GB0617918D0 (en) | 2006-09-11 | 2006-09-11 | Polymers |
| PCT/GB2007/000840 WO2007104948A2 (en) | 2006-03-10 | 2007-03-12 | Polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008011584A true MX2008011584A (es) | 2008-12-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008011584A MX2008011584A (es) | 2006-03-10 | 2007-03-12 | Polimeros. |
Country Status (9)
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|---|---|
| US (1) | US8197847B2 (https=) |
| EP (1) | EP1996629A2 (https=) |
| JP (2) | JP5394074B2 (https=) |
| AU (1) | AU2007226348A1 (https=) |
| CA (1) | CA2642819C (https=) |
| IL (1) | IL193978A (https=) |
| MX (1) | MX2008011584A (https=) |
| WO (1) | WO2007104948A2 (https=) |
| ZA (1) | ZA200808637B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2444695T3 (es) | 2006-06-23 | 2014-02-26 | Alethia Biotherapeutics Inc. | Polinucleótidos y polipéptidos implicados en el cáncer |
| US8034396B2 (en) * | 2008-04-01 | 2011-10-11 | Tyco Healthcare Group Lp | Bioadhesive composition formed using click chemistry |
| FR2930252B1 (fr) * | 2008-04-18 | 2010-08-20 | Centre Nat Rech Scient | Polymeres thermo-reticulables par reaction de huisgen : application a la preparation des materiaux a proprietes electro-optiques stables |
| US8153729B2 (en) * | 2008-05-29 | 2012-04-10 | The Regents Of The University Of California | Highly efficient agents for dispersion of nanoparticles in matrix materials |
| CA2740900C (en) | 2008-11-03 | 2019-09-24 | Alethia Biotherapeutics Inc. | Antibodies that specifically block the biological activity of a tumor antigen |
| WO2010091142A1 (en) * | 2009-02-04 | 2010-08-12 | President And Fellows Of Harvard College | Compositions and methods for labeling and imaging phospholipids |
| US8969473B2 (en) | 2009-02-21 | 2015-03-03 | Sofradim Production | Compounds and medical devices activated with solvophobic linkers |
| US8877170B2 (en) * | 2009-02-21 | 2014-11-04 | Sofradim Production | Medical device with inflammatory response-reducing coating |
| EP2398850B1 (en) | 2009-02-21 | 2018-08-22 | Sofradim Production | Medical devices with an activated coating |
| US8663689B2 (en) * | 2009-02-21 | 2014-03-04 | Sofradim Production | Functionalized adhesive medical gel |
| EP2398584A2 (en) | 2009-02-21 | 2011-12-28 | Sofradim Production | Apparatus and method of reaching polymers by exposure to uv radiation to produce injectable medical devices |
| US8512728B2 (en) | 2009-02-21 | 2013-08-20 | Sofradim Production | Method of forming a medical device on biological tissue |
| AU2010215931A1 (en) | 2009-02-21 | 2011-10-13 | Covidien Lp | Medical devices having activated surfaces |
| US8535477B2 (en) * | 2009-02-21 | 2013-09-17 | Sofradim Production | Medical devices incorporating functional adhesives |
| WO2010096654A1 (en) | 2009-02-21 | 2010-08-26 | Tyco Healthcare Group Lp | Medical devices having activated surfaces |
| US8968733B2 (en) * | 2009-02-21 | 2015-03-03 | Sofradim Production | Functionalized surgical adhesives |
| WO2010095047A2 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Apparatus and method of reacting polymers passing through metal ion chelated resin matrix to produce injectable medical devices |
| CA2753171A1 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Crosslinked fibers and method of making same using uv radiation |
| CA2753162A1 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Amphiphilic compounds and self-assembling compositions made therefrom |
| AU2010215196B2 (en) | 2009-02-21 | 2015-04-16 | Covidien Lp | Crosslinked fibers and method of making same by extrusion |
| GB0912160D0 (en) | 2009-07-13 | 2009-08-26 | Warwick Effect Polymers Ltd | Polymer modified macromolecules |
| US8795331B2 (en) | 2010-03-25 | 2014-08-05 | Covidien Lp | Medical devices incorporating functional adhesives |
| US9272074B2 (en) * | 2010-03-25 | 2016-03-01 | Sofradim Production | Surgical fasteners and methods for sealing wounds |
| CN101824127B (zh) * | 2010-04-01 | 2011-10-19 | 江西科技师范学院 | 一种利用活性自由基无皂乳液聚合制备可交联嵌段共聚物的方法及其制备的化合物 |
| AU2011276443A1 (en) | 2010-06-29 | 2013-01-31 | Covidien Lp | Microwave-powered reactor and method for in situ forming implants |
| WO2012001532A2 (en) | 2010-07-01 | 2012-01-05 | Sofradim Production | Medical device with predefined activated cellular integration |
| WO2012014080A2 (en) | 2010-07-27 | 2012-02-02 | Sofradim Production | Polymeric fibers having tissue reactive members |
| CN102399352B (zh) * | 2010-09-15 | 2013-05-22 | 南开大学 | 一种含能热塑性弹性体及其合成方法 |
| JP5890324B2 (ja) * | 2011-01-27 | 2016-03-22 | 東亞合成株式会社 | カルボキシル基含有重合体の製造方法 |
| SI3173427T1 (sl) | 2011-03-31 | 2019-08-30 | ADC Therapeutics SA, | Protitelesa proti antigenu 1, povezanemu z ledvicami, in antigen vezavni fragmenti le-tega |
| KR102102239B1 (ko) | 2012-01-09 | 2020-04-21 | 에이디씨 테라퓨틱스 에스에이 | 유방암을 치료하기 위한 방법 |
| US9775928B2 (en) | 2013-06-18 | 2017-10-03 | Covidien Lp | Adhesive barbed filament |
| EP2944955A1 (en) * | 2014-05-13 | 2015-11-18 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Benchmark for LC-MS systems |
| WO2016066586A1 (en) | 2014-10-31 | 2016-05-06 | Illumina Cambridge Limited | Novel polymers and dna copolymer coatings |
| CN105001376A (zh) * | 2015-06-23 | 2015-10-28 | 天津大学 | 原子转移自由基聚合制备高容量蛋白质层析介质的方法 |
| GB201611849D0 (en) * | 2016-07-07 | 2016-08-24 | Univ Of Nottingham The | Sulfated glycopolymers |
| EP3604352B1 (en) * | 2017-03-30 | 2025-02-19 | Godo Shigen Co., Ltd. | Method for producing a polymer using a molecular-weight controlling agent for radical polymerization |
| JP2019112533A (ja) * | 2017-12-24 | 2019-07-11 | 国立大学法人千葉大学 | 貴金属分離回収可能なコポリマー及びそのコポリマーを用いた貴金属回収方法 |
| JP7846630B2 (ja) * | 2020-04-30 | 2026-04-15 | ダウ グローバル テクノロジーズ エルエルシー | Ａｔｒｐによりオレフィン－アクリレートブロックコポリマーを調製するための方法 |
| WO2023062931A1 (ja) * | 2021-10-15 | 2023-04-20 | デンカ株式会社 | 化合物及び当該化合物の製造方法 |
| CN115124658B (zh) * | 2022-07-01 | 2023-07-11 | 苏州大学 | 主链型“半氟”交替共聚物的接枝共聚物的“一锅”法合成 |
| JP2026031534A (ja) * | 2024-08-09 | 2026-02-24 | デンカ株式会社 | トリアゾール骨格含有重合体の製造方法、トリアゾール骨格含有重合体及び組成物 |
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| CA2375248C (en) * | 1999-06-17 | 2009-11-24 | Wisconsin Alumni Research Foundation | Methods and reagents making multivalent arrays and combinatorial libraries of multivalent arrays |
| US7244830B2 (en) * | 2001-01-12 | 2007-07-17 | Emory University | Glycopolymers and free radical polymerization methods |
| WO2004055160A2 (en) * | 2002-12-13 | 2004-07-01 | The Trustees Of Columbia University In The City Of New York | Biomolecular coupling methods using 1,3-dipolar cycloaddition chemistry |
| WO2006003352A1 (en) * | 2004-07-06 | 2006-01-12 | Warwick Effect Polymers Limited | Living radical polymerization initiator comprising a functional group capable of reacting with polyeptides or the like, comb polymer obtained therewith, polypeptide conjugates and drugs obtained therefrom |
| WO2005035727A2 (en) | 2003-10-09 | 2005-04-21 | Ambrx, Inc. | Polymer derivatives |
| WO2005087818A1 (en) | 2004-03-05 | 2005-09-22 | Carnegie Mellon University | Preparation of functional polymers |
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2007
- 2007-03-12 CA CA2642819A patent/CA2642819C/en not_active Expired - Fee Related
- 2007-03-12 WO PCT/GB2007/000840 patent/WO2007104948A2/en not_active Ceased
- 2007-03-12 AU AU2007226348A patent/AU2007226348A1/en not_active Abandoned
- 2007-03-12 JP JP2008558884A patent/JP5394074B2/ja not_active Expired - Fee Related
- 2007-03-12 MX MX2008011584A patent/MX2008011584A/es unknown
- 2007-03-12 EP EP07712880A patent/EP1996629A2/en not_active Withdrawn
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2008
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- 2008-10-09 ZA ZA2008/08637A patent/ZA200808637B/en unknown
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2013
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Also Published As
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| JP2013227591A (ja) | 2013-11-07 |
| CA2642819C (en) | 2015-06-09 |
| WO2007104948A2 (en) | 2007-09-20 |
| US8197847B2 (en) | 2012-06-12 |
| JP5394074B2 (ja) | 2014-01-22 |
| CA2642819A1 (en) | 2007-09-20 |
| WO2007104948A3 (en) | 2007-12-06 |
| JP5584337B2 (ja) | 2014-09-03 |
| AU2007226348A1 (en) | 2007-09-20 |
| IL193978A (en) | 2014-09-30 |
| JP2009529601A (ja) | 2009-08-20 |
| ZA200808637B (en) | 2009-12-30 |
| US20090082224A1 (en) | 2009-03-26 |
| EP1996629A2 (en) | 2008-12-03 |
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