DK2554565T3 - Multifunktioneal polyoxyalkylen-forbindelse, fremgangsmåde til fremstilling af samme og mellemprodukt af samme - Google Patents
Multifunktioneal polyoxyalkylen-forbindelse, fremgangsmåde til fremstilling af samme og mellemprodukt af samme Download PDFInfo
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- DK2554565T3 DK2554565T3 DK11765686.8T DK11765686T DK2554565T3 DK 2554565 T3 DK2554565 T3 DK 2554565T3 DK 11765686 T DK11765686 T DK 11765686T DK 2554565 T3 DK2554565 T3 DK 2554565T3
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 196
- 238000000034 method Methods 0.000 title description 29
- 239000013067 intermediate product Substances 0.000 title 1
- 125000000524 functional group Chemical group 0.000 claims abstract description 42
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 27
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
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- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
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- 239000004202 carbamide Substances 0.000 claims description 5
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
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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 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000007529 inorganic bases Chemical class 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000007810 chemical reaction solvent Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
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- 150000003839 salts Chemical class 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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- 150000001241 acetals Chemical class 0.000 description 6
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- 238000006482 condensation reaction Methods 0.000 description 6
- 238000006266 etherification reaction Methods 0.000 description 6
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- RECJHOHNSXVBQN-UHFFFAOYSA-N [5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl]methanol Chemical compound CC1(C)OCC(CO)(CO)CO1 RECJHOHNSXVBQN-UHFFFAOYSA-N 0.000 description 5
- 238000006359 acetalization reaction Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 4
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
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- 229920000642 polymer Polymers 0.000 description 4
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- 108090000623 proteins and genes Proteins 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- JKHVDAUOODACDU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(2,5-dioxopyrrol-1-yl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCN1C(=O)C=CC1=O JKHVDAUOODACDU-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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- BWKIBIZZLRPKFY-UHFFFAOYSA-N 1,2,3-benzothiadiazole-5-carbaldehyde Chemical compound O=CC1=CC=C2SN=NC2=C1 BWKIBIZZLRPKFY-UHFFFAOYSA-N 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
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- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 2
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 2
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000014207 opsonization Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 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
- C08G65/2603—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 oxygen
- C08G65/2606—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 oxygen containing hydroxyl groups
-
- 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
-
- 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
- C08G65/2603—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 oxygen
- C08G65/2606—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 oxygen containing hydroxyl groups
- C08G65/2609—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 oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- 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
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
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- 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
- C08G65/333—Polymers modified by chemical after-treatment with organic 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
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33331—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing imide group
- C08G65/33337—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing imide group cyclic
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- 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
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
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- 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)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
Claims (9)
1. Polyfunktionel polyoxyalkylenforbindelse repræsenteret ved den følgende formel (1):
(1) hvor Z betegner en hydroxylgruppe-fjernet rest af pentaerythritol eller dipentaeryt-hritol; R betegner en carbonhydridgruppe med 1 til 24 carbonatomer; OA1 repræsenterer en oxyalkylengruppe med 2 til 4 carbonatomer; L1 repræsenterer en alkylengruppe med 1 til 24 carbonatomer, som kan have en esterbinding, en urethanbinding, en amidbinding, en etherbinding, en carbonatbinding, en sekundær aminogruppe, en urinstofbinding, en thio-etherbinding eller en thioesterbinding i en alkylenkæde eller i en terminal ende; X betegner en funktionel gruppe, der er i stand til at danne en kovalent binding med et bio-relateret stof; R, OA1 og L1 er ens eller forskellige fra hinanden i ét molekyle; m, som er et gennemsnitligt antal mol af oxyalkylengruppen, er 100 til 800; p betegner 0 eller 1; r1 + r2 er 4 eller 6; og r1 og r2 er et helt tal på 2 eller mere.
2. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor R er en methylgruppe, og OA1 betegner en oxyethylengruppe.
3. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor X er en funktionel gruppe, der er i stand til kemisk binding til en aminogruppe, en carboxylgruppe, en mer-captogruppe, en aldehydgruppe, en umættet binding eller en azidogruppe.
4. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor X er en funktionel gruppe, der indbefatter en aktiv ester, et aktivt carbonat, et aldehyd, et isocyanat, et isothiocyanat, et epoxid, en thiol, et maleimid, et hydrazid, en dithiopyridin, en sulfon, en amin, en oxyamin, en a-haloacetyl, en carboxylsyre, en umættet binding eller et azid.
5. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor X er en funktionel gruppe valgt blandt følgende:
hvor Y1 betegner et hydrogenatom eller en carbonhydridgruppe med 1 til 5 carbona-tomer, og Y3 betegner et hydrogenatom eller en carbonhydridgruppe med 1 til 5 carbona-tomer; Y2 betegner en carbonhydridgruppe med 1 til 10 carbonatomer, der kan indeholde et halogenatom; Y4 betegner et hydrogenatom eller en sulfonylgruppe; og W er et halogenatom valgt blandt Cl, Br og I.
6. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor Z er en hydroxylgrup-pe-fjernet rest af pentaerythritol og r1 = r2 = 2.
7. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor Z er en hydroxylgrup-pe-fjernet rest af dipentaerythritol, r1 = 2 og r2 = 4.
8. Polyfunktionel polyoxyalkylenforbindelse ifølge krav 1, hvor Z er en hydroxylgrup-pe-fjernet rest af dipentaerythritol, r1 = 4 og r2 = 2.
9. Polyoxyalkylenforbindelse ifølge krav 1, repræsenteret ved den følgende formel (2):
(2) hvor Z, R, OA1, m, r1 og r2 er som defineret i krav 1, og R og OA1 er ens eller forskellige fra hinanden i ét molekyle.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010081180 | 2010-03-31 | ||
| PCT/JP2011/058110 WO2011125786A1 (ja) | 2010-03-31 | 2011-03-30 | 多官能性ポリオキシアルキレン化合物、その製造方法及び中間体 |
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| DK2554565T3 true DK2554565T3 (da) | 2018-05-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| DK11765686.8T DK2554565T3 (da) | 2010-03-31 | 2011-03-30 | Multifunktioneal polyoxyalkylen-forbindelse, fremgangsmåde til fremstilling af samme og mellemprodukt af samme |
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| US (1) | US8816099B2 (da) |
| EP (1) | EP2554565B1 (da) |
| JP (1) | JP5866789B2 (da) |
| KR (1) | KR101737153B1 (da) |
| CN (1) | CN102822235B (da) |
| DK (1) | DK2554565T3 (da) |
| WO (1) | WO2011125786A1 (da) |
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| JP6106104B2 (ja) | 2014-01-16 | 2017-03-29 | 信越化学工業株式会社 | 末端にアミノ基を有する狭分散ポリアルキレングリコール誘導体の製造方法 |
| JP6106103B2 (ja) | 2014-01-16 | 2017-03-29 | 信越化学工業株式会社 | 末端にアミノ基を有する狭分散ポリアルキレングリコール誘導体の製造方法、並びにこれに用いる新規なアセタール基含有アルコール化合物及びそのアルカリ金属塩 |
| CN108350165B (zh) * | 2015-09-04 | 2021-08-17 | 巴斯夫欧洲公司 | 用于纯化粗聚醚多元醇的方法 |
| EP3604385B1 (en) * | 2017-03-30 | 2024-05-01 | NOF Corporation | Heterobifunctional monodispersed polyethylene glycol and conjugate using the same |
| KR102542988B1 (ko) * | 2018-03-13 | 2023-06-13 | 니치유 가부시키가이샤 | 주쇄 및 측쇄에 단분산 폴리에틸렌 글리콜을 가지는 헤테로이관능성 화합물 |
| EP4265667B1 (en) * | 2020-12-15 | 2025-07-23 | NOF Corporation | Method for producing maleimide polyethylene glycol derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH02242823A (ja) | 1989-03-02 | 1990-09-27 | Kiyouseki Seihin Gijutsu Kenkyusho:Kk | シアノエチル化ポリエーテルポリオール及び該化合物を有効成分として含有する冷凍機油 |
| IT1270994B (it) | 1994-03-18 | 1997-05-26 | Bracco Spa | Macromolecole ramificate a struttura poliossialchilica e loro usi |
| JP3537525B2 (ja) | 1994-05-31 | 2004-06-14 | 日本油脂株式会社 | アミノ基含有ポリオキシアルキレン化合物 |
| JP4078032B2 (ja) | 1998-03-12 | 2008-04-23 | ネクター セラピューティックス エイエル，コーポレイション | 近位の反応性基を持つポリ（エチレングリコール）誘導体 |
| US6251382B1 (en) | 1998-04-17 | 2001-06-26 | Enzon, Inc. | Biodegradable high molecular weight polymeric linkers and their conjugates |
| US6824766B2 (en) | 1998-04-17 | 2004-11-30 | Enzon, Inc. | Biodegradable high molecular weight polymeric linkers and their conjugates |
| US6153655A (en) | 1998-04-17 | 2000-11-28 | Enzon, Inc. | Terminally-branched polymeric linkers and polymeric conjugates containing the same |
| JP4123856B2 (ja) | 2001-07-31 | 2008-07-23 | 日油株式会社 | 生体関連物質の修飾剤およびポリオキシアルキレン誘導体の製造方法 |
| JP4412461B2 (ja) | 2002-11-20 | 2010-02-10 | 日油株式会社 | 修飾された生体関連物質、その製造方法および中間体 |
| US8003117B2 (en) * | 2002-11-20 | 2011-08-23 | Nof Corporation | Polyalkylene glycol derivative and modified bio-related substance |
| GB0329825D0 (en) | 2003-12-23 | 2004-01-28 | Celltech R&D Ltd | Biological products |
| JP5013830B2 (ja) | 2006-11-29 | 2012-08-29 | 株式会社ネオス | 新規な含フッ素ペンタエリスリトール誘導体及びそれを用いた湿式コーティング膜の製造方法 |
| CN101583380B (zh) | 2006-11-30 | 2013-07-10 | 尼克塔治疗公司 | 用于制备聚合物轭合物的方法 |
| CN102112412B (zh) | 2008-07-31 | 2013-12-18 | 株式会社日本触媒 | 水硬性材料用减缩剂和水硬性材料用减缩剂组合物 |
| JP5519972B2 (ja) | 2008-07-31 | 2014-06-11 | 株式会社日本触媒 | 水硬性材料用収縮低減剤 |
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- 2011-03-30 JP JP2011075867A patent/JP5866789B2/ja active Active
- 2011-03-30 CN CN201180016971.XA patent/CN102822235B/zh active Active
- 2011-03-30 DK DK11765686.8T patent/DK2554565T3/da active
- 2011-03-30 KR KR1020127025473A patent/KR101737153B1/ko active Active
- 2011-03-30 EP EP11765686.8A patent/EP2554565B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR101737153B1 (ko) | 2017-05-17 |
| US8816099B2 (en) | 2014-08-26 |
| CN102822235B (zh) | 2015-11-25 |
| EP2554565B1 (en) | 2018-05-02 |
| JP2011225860A (ja) | 2011-11-10 |
| JP5866789B2 (ja) | 2016-02-17 |
| WO2011125786A1 (ja) | 2011-10-13 |
| CN102822235A (zh) | 2012-12-12 |
| EP2554565A4 (en) | 2016-02-10 |
| US20110245509A1 (en) | 2011-10-06 |
| EP2554565A1 (en) | 2013-02-06 |
| KR20130018728A (ko) | 2013-02-25 |
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