BG61268B1 - Polymers containing diester monomer units - Google Patents
Polymers containing diester monomer units Download PDFInfo
- Publication number
- BG61268B1 BG61268B1 BG97499A BG9749993A BG61268B1 BG 61268 B1 BG61268 B1 BG 61268B1 BG 97499 A BG97499 A BG 97499A BG 9749993 A BG9749993 A BG 9749993A BG 61268 B1 BG61268 B1 BG 61268B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- mmol
- group
- solution
- water
- general formula
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 160
- 239000000178 monomer Substances 0.000 title claims description 49
- 150000005690 diesters Chemical class 0.000 title claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 179
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 125000000962 organic group Chemical group 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229920006037 cross link polymer Polymers 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000007943 implant Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000012643 polycondensation polymerization Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229920000578 graft copolymer Polymers 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 238000013268 sustained release Methods 0.000 claims description 3
- 239000012730 sustained-release form Substances 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 abstract description 8
- 239000000032 diagnostic agent Substances 0.000 abstract description 5
- 229940039227 diagnostic agent Drugs 0.000 abstract description 5
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 167
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 127
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
- 239000000499 gel Substances 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 239000002904 solvent Substances 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 55
- 230000002829 reductive effect Effects 0.000 description 55
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 29
- -1 methylene diester Chemical class 0.000 description 28
- 229920002451 polyvinyl alcohol Polymers 0.000 description 28
- 239000012298 atmosphere Substances 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 239000012299 nitrogen atmosphere Substances 0.000 description 25
- 229920002401 polyacrylamide Polymers 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- 229920006395 saturated elastomer Polymers 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 238000001035 drying Methods 0.000 description 22
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- QYDMMTAPHLKXNJ-UHFFFAOYSA-N 3,3-dimethoxypropanoyloxymethyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OCOC(=O)CC(OC)OC QYDMMTAPHLKXNJ-UHFFFAOYSA-N 0.000 description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 238000004132 cross linking Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 11
- ZHESMCIWZWYNLC-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)C(C)=C ZHESMCIWZWYNLC-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ODUTZNVTSOAHCJ-UHFFFAOYSA-N 4-(prop-2-enoyloxymethoxycarbonyloxy)butyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)OCOC(=O)C=C ODUTZNVTSOAHCJ-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UMGLBHQOFQXXSI-UHFFFAOYSA-N hepta-2,5-dienedioic acid Chemical compound OC(=O)C=CCC=CC(O)=O UMGLBHQOFQXXSI-UHFFFAOYSA-N 0.000 description 9
- TYMBNRMIBWOQGH-UHFFFAOYSA-N 3,3-dimethoxypropanoic acid Chemical compound COC(OC)CC(O)=O TYMBNRMIBWOQGH-UHFFFAOYSA-N 0.000 description 8
- 108090000371 Esterases Proteins 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 239000004005 microsphere Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- JLFYPMYFFZMXEQ-UHFFFAOYSA-N 4-(1-prop-2-enoyloxyethoxycarbonyloxy)butyl prop-2-enoate Chemical compound C=CC(=O)OC(C)OC(=O)OCCCCOC(=O)C=C JLFYPMYFFZMXEQ-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 229920002988 biodegradable polymer Polymers 0.000 description 6
- 239000004621 biodegradable polymer Substances 0.000 description 6
- 238000006065 biodegradation reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000002872 contrast media Substances 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 6
- 230000005291 magnetic effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GXAODDSUFOEQCB-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxymethoxycarbonyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)OCOC(=O)C(C)=C GXAODDSUFOEQCB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229960002949 fluorouracil Drugs 0.000 description 5
- 238000002523 gelfiltration Methods 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- LICWDODMDFJCCC-UHFFFAOYSA-N 9-(oxiran-2-yl)nonanoic acid Chemical compound OC(=O)CCCCCCCCC1CO1 LICWDODMDFJCCC-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 4
- 229940043349 potassium metabisulfite Drugs 0.000 description 4
- 235000010263 potassium metabisulphite Nutrition 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- HJPLDEIWOANMRT-UHFFFAOYSA-N (4-hydroxybenzoyl)oxymethyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCOC(=O)C1=CC=C(O)C=C1 HJPLDEIWOANMRT-UHFFFAOYSA-N 0.000 description 3
- ANQBHOLHRHLQDA-UHFFFAOYSA-N 3-methoxyprop-2-enoyloxymethyl 3-methoxyprop-2-enoate Chemical compound COC=CC(=O)OCOC(=O)C=COC ANQBHOLHRHLQDA-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005574 MCPA Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 230000007071 enzymatic hydrolysis Effects 0.000 description 3
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000005298 paramagnetic effect Effects 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
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Classifications
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909019650A GB9019650D0 (en) | 1990-09-07 | 1990-09-07 | Chemical compounds |
| GB919114678A GB9114678D0 (en) | 1991-07-08 | 1991-07-08 | Chemical compounds |
| PCT/EP1991/001751 WO1992004392A1 (en) | 1990-09-07 | 1991-09-07 | Polymers containing diester units |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG97499A BG97499A (bg) | 1994-03-24 |
| BG61268B1 true BG61268B1 (en) | 1997-04-30 |
Family
ID=26297628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG97499A BG61268B1 (en) | 1990-09-07 | 1993-03-05 | Polymers containing diester monomer units |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5534250A (de) |
| EP (1) | EP0547126B1 (de) |
| JP (1) | JP3161728B2 (de) |
| AT (1) | ATE134668T1 (de) |
| AU (1) | AU662490B2 (de) |
| BG (1) | BG61268B1 (de) |
| BR (1) | BR9106819A (de) |
| CA (1) | CA2091165C (de) |
| CZ (1) | CZ282532B6 (de) |
| DE (1) | DE69117518T2 (de) |
| DK (1) | DK0547126T3 (de) |
| ES (1) | ES2084180T3 (de) |
| FI (1) | FI930991A (de) |
| GR (1) | GR3019624T3 (de) |
| HU (1) | HU221088B1 (de) |
| IE (1) | IE73487B1 (de) |
| IL (1) | IL99438A (de) |
| NO (1) | NO304432B1 (de) |
| OA (1) | OA10052A (de) |
| PH (1) | PH31064A (de) |
| RO (1) | RO112033B1 (de) |
| SG (1) | SG49084A1 (de) |
| SK (1) | SK278147B6 (de) |
| WO (1) | WO1992004392A1 (de) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9106673D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| EP0586524B2 (de) * | 1991-06-03 | 2000-11-02 | Nycomed Imaging As | Verbesserungen im bezug auf kontrastmittel |
| MX9205298A (es) * | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
| GB9204918D0 (en) | 1992-03-06 | 1992-04-22 | Nycomed As | Chemical compounds |
| ATE184491T1 (de) * | 1992-03-06 | 1999-10-15 | Nycomed Imaging As | Verbesserungen in bezug auf kontrastmittel |
| US5674468A (en) * | 1992-03-06 | 1997-10-07 | Nycomed Imaging As | Contrast agents comprising gas-containing or gas-generating polymer microparticles or microballoons |
| US6383470B1 (en) | 1992-09-26 | 2002-05-07 | Thomas Fritzsch | Microparticle preparations made of biodegradable copolymers |
| IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
| FR2705352B1 (fr) * | 1993-05-19 | 1995-08-04 | Cray Valley Sa | Procédé de dégradation de déchets de polyesters insaturés en vue de leur recyclage. |
| GB9318288D0 (en) * | 1993-09-03 | 1993-10-20 | Nycomed Imaging As | Improvements in or relating to contrast agents |
| GB9417941D0 (en) * | 1994-09-06 | 1994-10-26 | Nycomed Imaging As | Improvements in or relating to contrast agents |
| DE19726191A1 (de) * | 1997-06-20 | 1998-12-24 | Bayer Ag | Verwendung von Jod-phenyl-carbonat-haltigen Polycarbonaten zur Herstellung von speziellen Formteilen |
| GB9814507D0 (en) * | 1998-07-03 | 1998-09-02 | Univ Southampton | A method and apparatus for controlling pests |
| US7343710B2 (en) * | 1998-07-03 | 2008-03-18 | I.D.A Limited | Method and apparatus for controlling pests |
| US6498153B1 (en) * | 1998-12-31 | 2002-12-24 | Akzo Nobel N.V. | Extended release growth promoting two component composition |
| US6426145B1 (en) | 1999-05-20 | 2002-07-30 | Scimed Life Systems, Inc. | Radiopaque compositions for visualization of medical devices |
| DE10101387A1 (de) | 2001-01-13 | 2002-07-18 | Merck Patent Gmbh | Polyester mit Methacrylatendgruppen |
| NZ536308A (en) * | 2002-05-24 | 2009-01-31 | Angiotech Int Ag | Compositions and methods for coating medical implants |
| US8313760B2 (en) | 2002-05-24 | 2012-11-20 | Angiotech International Ag | Compositions and methods for coating medical implants |
| US20030235610A1 (en) * | 2002-06-21 | 2003-12-25 | Piedmont Pharmaceuticals, Llc | Liposomes containing biologically active compounds |
| AU2004293463A1 (en) * | 2003-11-20 | 2005-06-09 | Angiotech International Ag | Implantable sensors and implantable pumps and anti-scarring agents |
| US8012457B2 (en) | 2004-06-04 | 2011-09-06 | Acusphere, Inc. | Ultrasound contrast agent dosage formulation |
| AU2005100176A4 (en) * | 2005-03-01 | 2005-04-07 | Gym Tv Pty Ltd | Garbage bin clip |
| EP2150119B1 (de) * | 2007-05-02 | 2018-04-11 | Tyrx, Inc. | Dihydroxybenzoatpolymere und ihre verwendung |
| DE102008008522A1 (de) * | 2008-02-11 | 2009-08-13 | Magforce Nanotechnologies Ag | Implantierbare Nanopartikel-enthaltende Produkte |
| DK2334378T3 (da) | 2008-08-19 | 2014-07-07 | Xenoport Inc | Prodrugs af methylhydrogenfumarat, farmaceutiske sammensætninger deraf og fremgangsmåder til anvendelse |
| US20110015672A1 (en) * | 2009-07-17 | 2011-01-20 | Tyco Healthcare Group Lp | Method for Coating a Medical Device |
| WO2014031892A1 (en) | 2012-08-22 | 2014-02-27 | Xenoport, Inc. | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| WO2014031844A1 (en) | 2012-08-22 | 2014-02-27 | Xenoport, Inc. | Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| NZ631337A (en) | 2013-03-14 | 2017-01-27 | Alkermes Pharma Ireland Ltd | Prodrugs of fumarates and their use in treating various diseases |
| WO2014160633A1 (en) | 2013-03-24 | 2014-10-02 | Xenoport, Inc. | Pharmaceutical compositions of dimethyl fumarate |
| WO2014197860A1 (en) | 2013-06-07 | 2014-12-11 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| EP3041467A1 (de) | 2013-09-06 | 2016-07-13 | XenoPort, Inc. | Kristalline formen von (n,n-diethylcarbamoyl) methyl-methyl(2e)but-2-en-1,4-dioat, syntheseverfahren und verwendung |
| AU2015218587B2 (en) | 2014-02-24 | 2017-04-27 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
| US20220119588A1 (en) | 2019-02-04 | 2022-04-21 | Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division) | Recyclable and reworkable epoxy resins |
| WO2023168562A1 (zh) * | 2022-03-07 | 2023-09-14 | 上纬创新育成股份有限公司 | 含碳酸酯的不饱和化合物、其制备方法、其制备的固化物及降解固化物的方法 |
| CN118072865B (zh) * | 2024-04-22 | 2024-06-28 | 河北化工医药职业技术学院 | 一种有机降解材料分布模型构建方法及系统 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE95108C (de) * | ||||
| US2341334A (en) * | 1939-03-14 | 1944-02-08 | Du Pont | Interpolymers of alkylidene esters of alpha-methylene monocarboxylic acids with vinyl and vinylidene compounds |
| DE1104900B (de) * | 1953-11-23 | 1961-04-13 | Helmut Junghans Dr Ing | Armbanduhrwerk |
| US2839572A (en) * | 1956-03-29 | 1958-06-17 | Union Carbide Corp | Allylidene dicrotonates and process for their production |
| BE592804A (de) * | 1959-07-11 | |||
| US3293220A (en) * | 1962-10-11 | 1966-12-20 | Toyo Rayon Co Ltd | Process for heat stabilization of polyoxymethylene |
| JPS4926946B1 (de) * | 1970-12-24 | 1974-07-13 | ||
| DD95108A1 (de) * | 1971-12-06 | 1973-01-12 | ||
| US3894118A (en) * | 1974-01-21 | 1975-07-08 | Itt | Crosslinking agents for fluorocarbon polymers |
| NL174734C (nl) * | 1974-02-18 | 1984-08-01 | Tno | Werkwijze voor het bereiden van onder invloed van water afbreekbare kunststofmaterialen, alsmede voorwerpen, gevormd uit kunststofmaterialen verkregen onder toepassing van de werkwijze. |
| US4180646A (en) * | 1975-01-28 | 1979-12-25 | Alza Corporation | Novel orthoester polymers and orthocarbonate polymers |
| CH653558A5 (fr) * | 1979-11-23 | 1986-01-15 | Battelle Memorial Institute | Fil de suture muni d'un manchon protecteur. |
| JPS6014861A (ja) * | 1983-07-05 | 1985-01-25 | 株式会社日本メデイカル・サプライ | 癒着防止材 |
| US4481353A (en) * | 1983-10-07 | 1984-11-06 | The Children's Medical Center Corporation | Bioresorbable polyesters and polyester composites |
| NL8402178A (nl) * | 1984-07-10 | 1986-02-03 | Rijksuniversiteit | Entstuk, geschikt voor behandeling door reconstructieve chirurgie van beschadigingen van beenachtig materiaal. |
| DE3610808A1 (de) * | 1985-03-29 | 1986-10-02 | Pentron Corp., Wallingford, Conn. | Dental-klebmittel |
| JP2551756B2 (ja) * | 1985-05-07 | 1996-11-06 | 武田薬品工業株式会社 | ポリオキシカルボン酸エステルおよびその製造法 |
| WO1989002903A1 (en) * | 1987-09-30 | 1989-04-06 | Ecoplastics Limited | Production of photodegradable polyester plastics |
| NL8703115A (nl) * | 1987-12-23 | 1989-07-17 | Groningen Science Park | Biodegradeerbare polyurethanen, daarop gebaseerde voortbrengselen, en polyesterpolyol prepolymeren. |
-
1991
- 1991-09-06 PH PH43068A patent/PH31064A/en unknown
- 1991-09-07 DK DK91916326.1T patent/DK0547126T3/da active
- 1991-09-07 RO RO93-00306A patent/RO112033B1/ro unknown
- 1991-09-07 BR BR919106819A patent/BR9106819A/pt not_active Application Discontinuation
- 1991-09-07 SG SG1996005902A patent/SG49084A1/en unknown
- 1991-09-07 HU HU9300608A patent/HU221088B1/hu unknown
- 1991-09-07 AT AT91916326T patent/ATE134668T1/de not_active IP Right Cessation
- 1991-09-07 DE DE69117518T patent/DE69117518T2/de not_active Expired - Fee Related
- 1991-09-07 WO PCT/EP1991/001751 patent/WO1992004392A1/en active IP Right Grant
- 1991-09-07 AU AU85256/91A patent/AU662490B2/en not_active Ceased
- 1991-09-07 ES ES91916326T patent/ES2084180T3/es not_active Expired - Lifetime
- 1991-09-07 CA CA002091165A patent/CA2091165C/en not_active Expired - Fee Related
- 1991-09-07 EP EP91916326A patent/EP0547126B1/de not_active Expired - Lifetime
- 1991-09-07 SK SK157-93A patent/SK278147B6/sk unknown
- 1991-09-07 JP JP51546591A patent/JP3161728B2/ja not_active Expired - Fee Related
- 1991-09-07 US US07/982,746 patent/US5534250A/en not_active Expired - Lifetime
- 1991-09-08 IL IL9943891A patent/IL99438A/en not_active IP Right Cessation
- 1991-09-09 IE IE315491A patent/IE73487B1/en not_active IP Right Cessation
-
1993
- 1993-03-04 CZ CZ93337A patent/CZ282532B6/cs unknown
- 1993-03-05 FI FI930991A patent/FI930991A/fi unknown
- 1993-03-05 NO NO930807A patent/NO304432B1/no not_active IP Right Cessation
- 1993-03-05 OA OA60347A patent/OA10052A/en unknown
- 1993-03-05 BG BG97499A patent/BG61268B1/bg unknown
-
1995
- 1995-06-02 US US08/458,612 patent/US5693321A/en not_active Expired - Fee Related
-
1996
- 1996-04-10 GR GR960401021T patent/GR3019624T3/el unknown
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