CA2619709C - A method of modifying a macromolecular system - Google Patents
A method of modifying a macromolecular system Download PDFInfo
- Publication number
- CA2619709C CA2619709C CA2619709A CA2619709A CA2619709C CA 2619709 C CA2619709 C CA 2619709C CA 2619709 A CA2619709 A CA 2619709A CA 2619709 A CA2619709 A CA 2619709A CA 2619709 C CA2619709 C CA 2619709C
- Authority
- CA
- Canada
- Prior art keywords
- group
- macromolecule
- general formula
- integer
- compound
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920002521 macromolecule Polymers 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000006239 protecting group Chemical group 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000011159 matrix material Substances 0.000 claims description 14
- 125000005544 phthalimido group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 description 35
- 229920005989 resin Polymers 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 150000003141 primary amines Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229940117927 ethylene oxide Drugs 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 9
- 238000011068 loading method Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 6
- -1 primary amine primary amine Chemical class 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 239000012317 TBTU Substances 0.000 description 5
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 5
- 238000007046 ethoxylation reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 125000005543 phthalimide group Chemical class 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Chemical group 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- NDKDFTQNXLHCGO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)acetic acid Chemical compound C1=CC=C2C(COC(=O)NCC(=O)O)C3=CC=CC=C3C2=C1 NDKDFTQNXLHCGO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZRWPUFFVAOMMNM-UHFFFAOYSA-N Patulin Chemical compound OC1OCC=C2OC(=O)C=C12 ZRWPUFFVAOMMNM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical group 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- MBCZNRXYDIFUJF-UHFFFAOYSA-N fulvene;piperidine Chemical compound C=C1C=CC=C1.C1CCNCC1 MBCZNRXYDIFUJF-UHFFFAOYSA-N 0.000 description 2
- 238000006698 hydrazinolysis reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- HOXDYOFMLGYVGR-UHFFFAOYSA-N (benzylamino)methanol Chemical compound OCNCC1=CC=CC=C1 HOXDYOFMLGYVGR-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- MNAUPUGVFAEVOA-UHFFFAOYSA-N 2-aminoethanol;benzaldehyde Chemical compound NCCO.O=CC1=CC=CC=C1 MNAUPUGVFAEVOA-UHFFFAOYSA-N 0.000 description 1
- HOCPDSKONPQIQM-UHFFFAOYSA-N 4-(2-bromoethyl)isoindole-1,3-dione Chemical compound BrCCC1=CC=CC2=C1C(=O)NC2=O HOCPDSKONPQIQM-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 0 C*(CCO*)OCC*(C)OCCN(C(c1c2cccc1)=O)C2=O Chemical compound C*(CCO*)OCC*(C)OCCN(C(c1c2cccc1)=O)C2=O 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108050000194 Expansin Proteins 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- XHEZLQRARQJFLN-UHFFFAOYSA-N OCCOCCOCCN(C(c1ccccc11)=O)C1=O Chemical compound OCCOCCOCCN(C(c1ccccc11)=O)C1=O XHEZLQRARQJFLN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical group 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000005375 primary alkyl halides Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPCT/DK2005/000547 | 2005-08-26 | ||
| PCT/DK2005/000547 WO2006021218A1 (en) | 2004-08-27 | 2005-08-26 | Polyether polymer matrix |
| EP06075482 | 2006-03-02 | ||
| EP06075482.7 | 2006-03-02 | ||
| PCT/DK2006/000461 WO2007022780A1 (en) | 2005-08-26 | 2006-08-25 | A method of modifying a macromolecular system |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2619709A1 CA2619709A1 (en) | 2007-03-01 |
| CA2619709C true CA2619709C (en) | 2012-05-01 |
Family
ID=37085311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2619709A Expired - Fee Related CA2619709C (en) | 2005-08-26 | 2006-08-25 | A method of modifying a macromolecular system |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7897698B2 (https=) |
| EP (2) | EP2045282B1 (https=) |
| JP (1) | JP5021649B2 (https=) |
| AT (1) | ATE425204T1 (https=) |
| CA (1) | CA2619709C (https=) |
| DE (1) | DE602006005686D1 (https=) |
| ES (1) | ES2323733T3 (https=) |
| WO (1) | WO2007022780A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102635693B1 (ko) | 2015-09-30 | 2024-02-14 | 다우 글로벌 테크놀로지스 엘엘씨 | 알데하이드 모이어티에 아미노 및 폴리메릴 기의 첨가를 통한 작용성 폴리머의 제조 방법 |
| WO2017058910A1 (en) | 2015-09-30 | 2017-04-06 | Dow Global Technologies Llc | Multi- or dual-headed compositions useful for chain shuttling and process to prepare the same |
| EP4435013A3 (en) | 2016-09-30 | 2024-12-25 | Dow Global Technologies LLC | Process for preparing multi- or dual-headed compositions useful for chain shuttling |
| TWI756272B (zh) | 2016-09-30 | 2022-03-01 | 美商陶氏全球科技有限責任公司 | 適用於鏈梭移之封端多頭或雙頭組合物及其製備方法 |
| JP7096236B2 (ja) | 2016-09-30 | 2022-07-05 | ダウ グローバル テクノロジーズ エルエルシー | チェーンシャトリングに有用なマルチヘッドまたはデュアルヘッド組成物、およびそれを調製するプロセス |
| KR102823188B1 (ko) | 2017-12-29 | 2025-06-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 이중 헤드 유기 알루미늄 조성물 |
| SG11202005532YA (en) | 2017-12-29 | 2020-07-29 | Dow Global Technologies Llc | Capped dual-headed organoaluminum compositions |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2631656C2 (de) * | 1976-07-14 | 1983-02-10 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung eines Hydroxysuccinimidoester-Derivats zur Bindung von biologisch aktiven Proteinen aneinander und/oder an flüssige oder feste Trägerstoffe |
| US5483008A (en) * | 1992-02-07 | 1996-01-09 | Research Development Corporation Of Japan | Polyether having heterofunctional groups at both ends, process for the preparation thereof and polymerization initiator therefor |
| JP3465307B2 (ja) * | 1993-08-05 | 2003-11-10 | 日本油脂株式会社 | ポリアルキレンオキシド誘導体および製造方法 |
| JP3465306B2 (ja) * | 1993-08-05 | 2003-11-10 | 日本油脂株式会社 | ポリアルキレンオキシド誘導体および製造方法 |
| JP3508207B2 (ja) * | 1994-05-30 | 2004-03-22 | 日本油脂株式会社 | ポリオキシアルキレン誘導体の製造方法 |
| US5672662A (en) * | 1995-07-07 | 1997-09-30 | Shearwater Polymers, Inc. | Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications |
| GB9713979D0 (en) | 1997-07-03 | 1997-09-10 | Univ Nottingham | Method for attaching peg to macromolecules |
| JP4581248B2 (ja) * | 1998-05-07 | 2010-11-17 | 日油株式会社 | 片末端に保護されていてもよいアミノ基を有するポリオキシエチレン誘導体及びその製造方法 |
| CN1284603C (zh) * | 1999-10-08 | 2006-11-15 | 内科塔治疗亚拉巴马公司 | 杂双官能聚乙二醇衍生物和它们的制备方法 |
| EP1118334A1 (en) * | 2000-01-11 | 2001-07-25 | Aventis Behring Gesellschaft mit beschränkter Haftung | Method for the production of conjugates and uses thereof for the prevention and treatment of allergic reactions and autoimmune diseases |
| WO2001062827A2 (en) | 2000-02-22 | 2001-08-30 | Shearwater Corporation | N-maleimidyl polymer derivatives |
| NO314588B1 (no) * | 2000-09-04 | 2003-04-14 | Bionor Immuno As | HIV-peptider, antigener, vaksinesammensetning, immunoassay- testsett og en fremgangsmåte for å påvise antistoffer indusert av HIV |
| AU2002258913A1 (en) * | 2001-04-23 | 2002-11-05 | Wisconsin Alumni Research Foundation | Bifunctional-modified hydrogels |
| WO2004012773A1 (en) | 2002-07-24 | 2004-02-12 | F. Hoffmann-La Roche Ag | Polyalkylene glycol acid additives |
| EP1581582B2 (en) | 2003-01-06 | 2017-06-07 | Nektar Therapeutics | Thiol-selective water-soluble polmer derivatives |
| JP3770246B2 (ja) * | 2003-04-11 | 2006-04-26 | 日本油脂株式会社 | ポリオキシアルキレン誘導体の製造方法 |
| EP1794209B1 (en) * | 2004-08-27 | 2008-10-08 | Novo Nordisk A/S | Polyether polymer matrix |
-
2006
- 2006-08-25 EP EP09150865A patent/EP2045282B1/en not_active Not-in-force
- 2006-08-25 JP JP2008527308A patent/JP5021649B2/ja not_active Expired - Fee Related
- 2006-08-25 US US11/990,455 patent/US7897698B2/en not_active Expired - Fee Related
- 2006-08-25 CA CA2619709A patent/CA2619709C/en not_active Expired - Fee Related
- 2006-08-25 ES ES06775948T patent/ES2323733T3/es active Active
- 2006-08-25 DE DE602006005686T patent/DE602006005686D1/de active Active
- 2006-08-25 AT AT06775948T patent/ATE425204T1/de not_active IP Right Cessation
- 2006-08-25 EP EP06775948A patent/EP1922355B1/en not_active Not-in-force
- 2006-08-25 WO PCT/DK2006/000461 patent/WO2007022780A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE602006005686D1 (de) | 2009-04-23 |
| EP2045282A1 (en) | 2009-04-08 |
| WO2007022780A1 (en) | 2007-03-01 |
| ATE425204T1 (de) | 2009-03-15 |
| ES2323733T3 (es) | 2009-07-23 |
| EP1922355B1 (en) | 2009-03-11 |
| JP2009506141A (ja) | 2009-02-12 |
| CA2619709A1 (en) | 2007-03-01 |
| US20090209710A1 (en) | 2009-08-20 |
| JP5021649B2 (ja) | 2012-09-12 |
| EP2045282B1 (en) | 2011-03-23 |
| EP1922355A1 (en) | 2008-05-21 |
| US7897698B2 (en) | 2011-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100512483B1 (ko) | 신규한 폴리에틸렌글리콜-말레이미드 유도체의 합성방법 | |
| US5235028A (en) | Polyethylene glycol derivatives for solid-phase applications | |
| KR100948532B1 (ko) | 분지형 중합체 및 그의 공액체 | |
| US7868132B2 (en) | Method for preparing multi-arm poly (ethylene glycol) amines | |
| EP0546055B1 (en) | Polyethylene glycol derivatives for solid-phase applications | |
| KR101793704B1 (ko) | 막 향상된 고분자 합성 | |
| CN104245791B (zh) | 多臂聚乙二醇衍生物、其中间体以及它们的制造方法 | |
| CA2619709C (en) | A method of modifying a macromolecular system | |
| CN107573498A (zh) | 末端具有多个羟基的聚氧乙烯衍生物 | |
| US5545698A (en) | Polyethylene glycol derivatives for solid-phase applications | |
| CN102822235B (zh) | 多官能聚氧化烯化合物、其生产方法及其中间体 | |
| JP5612467B2 (ja) | Ｆｍｏｃをベースとした加水分解性リンカーの調製方法 | |
| KR20080056267A (ko) | 보호된 아민 염을 이용하는 말단 아민기를 갖는 중합체의제조방법 | |
| ES2363122T3 (es) | Método para modificar un sistema macromolecular. | |
| KR102580547B1 (ko) | 멀티 암형 폴리에틸렌 글리콜 유도체의 제조 방법 | |
| JP2012180518A (ja) | 高分子システムを変性する方法 | |
| WO2011056799A1 (en) | Methods for preparing polyethylene glycol maleimide using n-(2-hydroxyethyl) maleimide as a starting material | |
| Siyad et al. | Synthetic evaluation of disulphide-bonded sarafotoxin on a poly (oxy ether) grafted dendrimeric poly (alkyl amine) support for polymer assisted organic synthesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140826 |