LT3199B - Biodegradable non-crosslinked polymers of low or zero-water-solubility - Google Patents
Biodegradable non-crosslinked polymers of low or zero-water-solubility Download PDFInfo
- Publication number
- LT3199B LT3199B LTIP388A LTIP388A LT3199B LT 3199 B LT3199 B LT 3199B LT IP388 A LTIP388 A LT IP388A LT IP388 A LTIP388 A LT IP388A LT 3199 B LT3199 B LT 3199B
- Authority
- LT
- Lithuania
- Prior art keywords
- polymer
- groups
- polymers
- water
- added
- Prior art date
Links
- 229920006037 cross link polymer Polymers 0.000 title claims description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 144
- 125000000962 organic group Chemical group 0.000 claims abstract description 9
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 9
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 229920001184 polypeptide Polymers 0.000 claims abstract description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- -1 oxy, iminocarbonyl carbonyl Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000003111 delayed effect Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000007943 implant Substances 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 210000004872 soft tissue Anatomy 0.000 claims description 2
- 238000012800 visualization Methods 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 241001122767 Theaceae Species 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 45
- 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 41
- 239000011541 reaction mixture Substances 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 238000004587 chromatography analysis Methods 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002808 molecular sieve Substances 0.000 description 14
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 238000010526 radical polymerization reaction Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006065 biodegradation reaction Methods 0.000 description 9
- 238000003776 cleavage reaction Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000007017 scission Effects 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XKYNLGVLGFPYRQ-UHFFFAOYSA-N butoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound CCCCOC(=O)OCOC(=O)C(C)=C XKYNLGVLGFPYRQ-UHFFFAOYSA-N 0.000 description 8
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229920002988 biodegradable polymer Polymers 0.000 description 7
- 239000004621 biodegradable polymer Substances 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WAIFIHKBNYUZGZ-UHFFFAOYSA-N 1-(2-methylprop-2-enoylamino)propan-2-yloxycarbonyloxymethyl acetate Chemical compound CC(=C)C(=O)NCC(C)OC(=O)OCOC(C)=O WAIFIHKBNYUZGZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 108090000371 Esterases Proteins 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- MKEVFCHVGWJVEU-UHFFFAOYSA-N ethoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)OCOC(=O)C(C)=C MKEVFCHVGWJVEU-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- TVDCUCKBZCDWRS-UHFFFAOYSA-N phenylmethoxycarbonyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)OCC1=CC=CC=C1 TVDCUCKBZCDWRS-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- GALGFDDHBGDRFQ-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)OC(C)OC(=O)C(C)=C GALGFDDHBGDRFQ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 description 5
- LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- FDIHYONBFVCOPU-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl benzoate Chemical compound CC(=C)C(=O)OCOC(=O)C1=CC=CC=C1 FDIHYONBFVCOPU-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000005690 diesters Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 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
- 150000003254 radicals Chemical class 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- HRBNXCSWUDHDLM-UHFFFAOYSA-N 1-methoxycarbonyloxyethyl 2-methylprop-2-enoate Chemical compound COC(=O)OC(C)OC(=O)C(C)=C HRBNXCSWUDHDLM-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PDQDJZLOMGSJFK-UHFFFAOYSA-N acetyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(C)=O PDQDJZLOMGSJFK-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- MBUCWFHXWNITCQ-UHFFFAOYSA-N butyl chloromethyl carbonate Chemical compound CCCCOC(=O)OCCl MBUCWFHXWNITCQ-UHFFFAOYSA-N 0.000 description 3
- MULZXZRAWSJCCF-UHFFFAOYSA-N carbonochloridoyloxymethyl acetate Chemical compound CC(=O)OCOC(Cl)=O MULZXZRAWSJCCF-UHFFFAOYSA-N 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 3
- MFSHZGFPADYOTO-UHFFFAOYSA-N chloromethyl methyl carbonate Chemical compound COC(=O)OCCl MFSHZGFPADYOTO-UHFFFAOYSA-N 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000007857 degradation product Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000012377 drug delivery Methods 0.000 description 3
- 239000002961 echo contrast media Substances 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000005291 magnetic effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RGPYVAUWRFGVHX-UHFFFAOYSA-N 1-[1-(2-methylprop-2-enoylamino)propan-2-yloxycarbonyloxy]ethyl acetate Chemical compound CC(=C)C(=O)NCC(C)OC(=O)OC(C)OC(C)=O RGPYVAUWRFGVHX-UHFFFAOYSA-N 0.000 description 2
- YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JTAMKVMVSJVIKP-UHFFFAOYSA-N 2-chloroethyl methyl carbonate Chemical compound COC(=O)OCCCl JTAMKVMVSJVIKP-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- MYCQSOCJLZBPAT-UHFFFAOYSA-N 2-methylprop-2-enoic acid;potassium Chemical compound [K].CC(=C)C(O)=O MYCQSOCJLZBPAT-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- BEPWYFBLGRQFFK-UHFFFAOYSA-N benzyl chloromethyl carbonate Chemical compound ClCOC(=O)OCC1=CC=CC=C1 BEPWYFBLGRQFFK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- GHGHDTQEVUBIBQ-UHFFFAOYSA-N carbonochloridoyloxymethyl benzoate Chemical compound ClC(=O)OCOC(=O)C1=CC=CC=C1 GHGHDTQEVUBIBQ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- QVISUHUAVCZFMP-UHFFFAOYSA-N carboxyoxymethyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCOC(O)=O QVISUHUAVCZFMP-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 2
- DRTIZOYLKCWDKR-UHFFFAOYSA-N chloromethyl 1-(2-methylprop-2-enoylamino)propan-2-yl carbonate Chemical compound CC(=C)C(=O)NCC(C)OC(=O)OCCl DRTIZOYLKCWDKR-UHFFFAOYSA-N 0.000 description 2
- RTFGZMKXMSDULM-UHFFFAOYSA-N chloromethyl ethyl carbonate Chemical compound CCOC(=O)OCCl RTFGZMKXMSDULM-UHFFFAOYSA-N 0.000 description 2
- LHXLWSDJXYETLZ-UHFFFAOYSA-N chloromethyl morpholine-4-carboxylate Chemical compound ClCOC(=O)N1CCOCC1 LHXLWSDJXYETLZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- Acoustics & Sound (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Biological Depolymerization Polymers (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyamides (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929204918A GB9204918D0 (en) | 1992-03-06 | 1992-03-06 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP388A LTIP388A (en) | 1994-09-25 |
| LT3199B true LT3199B (en) | 1995-03-27 |
Family
ID=10711636
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP388A LT3199B (en) | 1992-03-06 | 1993-03-05 | Biodegradable non-crosslinked polymers of low or zero-water-solubility |
| LTIP391A LT3216B (en) | 1992-03-06 | 1993-03-05 | Contrast agent |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP391A LT3216B (en) | 1992-03-06 | 1993-03-05 | Contrast agent |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5574097A (ro) |
| EP (1) | EP0629214B1 (ro) |
| JP (1) | JP3281381B2 (ro) |
| CN (1) | CN1038940C (ro) |
| AT (1) | ATE144540T1 (ro) |
| AU (1) | AU670069B2 (ro) |
| BG (1) | BG99070A (ro) |
| BR (1) | BR9306043A (ro) |
| CA (1) | CA2130671A1 (ro) |
| CZ (1) | CZ281738B6 (ro) |
| DE (1) | DE69305628T2 (ro) |
| DK (1) | DK0629214T3 (ro) |
| ES (1) | ES2093413T3 (ro) |
| FI (1) | FI944078A0 (ro) |
| GB (1) | GB9204918D0 (ro) |
| GR (1) | GR3022075T3 (ro) |
| HU (1) | HUT69070A (ro) |
| IL (1) | IL104962A (ro) |
| LT (2) | LT3199B (ro) |
| LV (1) | LV10294B (ro) |
| MD (2) | MD940199A (ro) |
| NO (1) | NO303123B1 (ro) |
| NZ (1) | NZ249547A (ro) |
| OA (1) | OA10097A (ro) |
| PH (1) | PH30746A (ro) |
| PL (1) | PL174125B1 (ro) |
| RU (1) | RU2114865C1 (ro) |
| SK (1) | SK105694A3 (ro) |
| WO (1) | WO1993018070A1 (ro) |
| ZA (2) | ZA931594B (ro) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2164237A1 (en) * | 1994-12-08 | 1996-06-09 | Takeharu Tabuchi | Acrylic monomer |
| US6309999B1 (en) * | 1999-03-19 | 2001-10-30 | Chandra P. Sharma | Process for the preparation of an immunoadsorbent matrix |
| US6720445B2 (en) | 2000-12-21 | 2004-04-13 | Beacon Laboratories, Inc. | Acetyloxymethyl esters and methods for using the same |
| AU2002310409C1 (en) | 2001-06-11 | 2008-04-17 | Xenoport, Inc. | Orally administered dosage forms of GABA analog prodrugs having reduced toxicity |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| AUPR951501A0 (en) * | 2001-12-14 | 2002-01-24 | Smart Drug Systems Inc | Modified sustained release pharmaceutical system |
| PT1509256E (pt) | 2002-05-24 | 2009-10-15 | Angiotech Int Ag | Composições e métodos de revestimento de implantes médicos |
| 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 |
| JP2007514472A (ja) * | 2003-11-20 | 2007-06-07 | アンジオテック インターナショナル アーゲー | 軟組織移植片および瘢痕化抑制剤 |
| EP1811986B1 (en) | 2004-11-04 | 2014-03-26 | XenoPort, Inc. | Gabapentin prodrug sustained release oral dosage forms |
| AU2005100176A4 (en) * | 2005-03-01 | 2005-04-07 | Gym Tv Pty Ltd | Garbage bin clip |
| EP2428235B1 (de) | 2007-11-23 | 2014-06-04 | Technische Universität Wien | Verwendung von durch Polymerisation härtbaren Zusammensetzungen zur Herstellung biologisch abbaubarer, bioverträglicher, vernetzter Polymere |
| WO2011157777A1 (de) * | 2010-06-17 | 2011-12-22 | Basf Se | Polymere mit saccharid-seitengruppen und ihre verwendung |
| RU2543895C2 (ru) * | 2013-05-17 | 2015-03-10 | Общество С Ограниченной Ответственностью "Научно-Производственный Центр "Амфион" | Гидрогелевый материал на основе сшиваемого поливинилового спирта |
| JP7115914B2 (ja) | 2017-06-23 | 2022-08-09 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| GB201810788D0 (en) * | 2018-06-29 | 2018-08-15 | Biocompatibles Uk Ltd | Biodegradable polymer |
| RU2687231C1 (ru) * | 2018-08-03 | 2019-05-08 | Сергей Борисович Врублевский | Способ получения пигментов |
| CN109928879A (zh) * | 2019-03-05 | 2019-06-25 | 贵州大学 | 一种丙烯酸酯碳酸酯及其均聚物和共聚物材料 |
| CN111892707B (zh) * | 2020-06-18 | 2021-08-13 | 中山大学 | 一种阳离子聚酰胺材料及其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180646A (en) | 1975-01-28 | 1979-12-25 | Alza Corporation | Novel orthoester polymers and orthocarbonate polymers |
| EP0130935B1 (fr) | 1983-07-01 | 1987-04-15 | Battelle Memorial Institute | Polypeptide biodégradable et son utilisation pour le relargage progressif de médicaments |
| WO1992004392A1 (en) | 1990-09-07 | 1992-03-19 | Holmes, Michael, John | Polymers containing diester units |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356166A (en) * | 1978-12-08 | 1982-10-26 | University Of Utah | Time-release chemical delivery system |
| US4276885A (en) | 1979-05-04 | 1981-07-07 | Rasor Associates, Inc | Ultrasonic image enhancement |
| US4718433A (en) | 1983-01-27 | 1988-01-12 | Feinstein Steven B | Contrast agents for ultrasonic imaging |
| US4741956A (en) * | 1986-07-09 | 1988-05-03 | Exxon Research And Engineering Company | Biodegradable coatings of ionomer polymer |
| DE58908194D1 (de) | 1988-02-05 | 1994-09-22 | Schering Ag | Ultraschallkontrastmittel, verfahren zu deren herstellung und deren verwendung als diagnostika und therapeutika. |
| GB9003821D0 (en) | 1990-02-20 | 1990-04-18 | Danbiosyst Uk | Diagnostic aid |
| US5137928A (en) | 1990-04-26 | 1992-08-11 | Hoechst Aktiengesellschaft | Ultrasonic contrast agents, processes for their preparation and the use thereof as diagnostic and therapeutic agents |
| AU636481B2 (en) | 1990-05-18 | 1993-04-29 | Bracco International B.V. | Polymeric gas or air filled microballoons usable as suspensions in liquid carriers for ultrasonic echography |
-
1992
- 1992-03-06 GB GB929204918A patent/GB9204918D0/en active Pending
-
1993
- 1993-03-05 AU AU36423/93A patent/AU670069B2/en not_active Ceased
- 1993-03-05 DE DE69305628T patent/DE69305628T2/de not_active Expired - Fee Related
- 1993-03-05 RU RU94045151A patent/RU2114865C1/ru active
- 1993-03-05 LT LTIP388A patent/LT3199B/lt not_active IP Right Cessation
- 1993-03-05 WO PCT/GB1993/000469 patent/WO1993018070A1/en active IP Right Grant
- 1993-03-05 DK DK93905526.5T patent/DK0629214T3/da active
- 1993-03-05 PL PL93305024A patent/PL174125B1/pl unknown
- 1993-03-05 CN CN93104053A patent/CN1038940C/zh not_active Expired - Fee Related
- 1993-03-05 SK SK1056-94A patent/SK105694A3/sk unknown
- 1993-03-05 EP EP93905526A patent/EP0629214B1/en not_active Expired - Lifetime
- 1993-03-05 IL IL10496293A patent/IL104962A/en not_active IP Right Cessation
- 1993-03-05 ZA ZA931594A patent/ZA931594B/xx unknown
- 1993-03-05 AT AT93905526T patent/ATE144540T1/de not_active IP Right Cessation
- 1993-03-05 LV LVP-93-170A patent/LV10294B/en unknown
- 1993-03-05 JP JP51546393A patent/JP3281381B2/ja not_active Expired - Fee Related
- 1993-03-05 CA CA002130671A patent/CA2130671A1/en not_active Abandoned
- 1993-03-05 ZA ZA931599A patent/ZA931599B/xx unknown
- 1993-03-05 ES ES93905526T patent/ES2093413T3/es not_active Expired - Lifetime
- 1993-03-05 US US08/290,875 patent/US5574097A/en not_active Expired - Fee Related
- 1993-03-05 LT LTIP391A patent/LT3216B/lt not_active IP Right Cessation
- 1993-03-05 HU HU9402563A patent/HUT69070A/hu unknown
- 1993-03-05 NZ NZ249547A patent/NZ249547A/en unknown
- 1993-03-05 BR BR9306043A patent/BR9306043A/pt not_active Application Discontinuation
- 1993-03-05 CZ CZ942152A patent/CZ281738B6/cs unknown
- 1993-03-08 PH PH45821A patent/PH30746A/en unknown
-
1994
- 1994-07-11 MD MD94-0199A patent/MD940199A/ro unknown
- 1994-07-14 MD MD94-0206A patent/MD940206A/ro unknown
- 1994-08-24 OA OA60557A patent/OA10097A/en unknown
- 1994-09-05 NO NO943273A patent/NO303123B1/no not_active IP Right Cessation
- 1994-09-05 FI FI944078A patent/FI944078A0/fi unknown
- 1994-09-28 BG BG99070A patent/BG99070A/bg unknown
-
1996
- 1996-12-18 GR GR960403520T patent/GR3022075T3/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180646A (en) | 1975-01-28 | 1979-12-25 | Alza Corporation | Novel orthoester polymers and orthocarbonate polymers |
| EP0130935B1 (fr) | 1983-07-01 | 1987-04-15 | Battelle Memorial Institute | Polypeptide biodégradable et son utilisation pour le relargage progressif de médicaments |
| WO1992004392A1 (en) | 1990-09-07 | 1992-03-19 | Holmes, Michael, John | Polymers containing diester units |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19990305 |