CH616417A5 - Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers - Google Patents
Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers Download PDFInfo
- Publication number
- CH616417A5 CH616417A5 CH61375A CH61375A CH616417A5 CH 616417 A5 CH616417 A5 CH 616417A5 CH 61375 A CH61375 A CH 61375A CH 61375 A CH61375 A CH 61375A CH 616417 A5 CH616417 A5 CH 616417A5
- Authority
- CH
- Switzerland
- Prior art keywords
- groups
- formula
- polymer
- methyl
- acid
- Prior art date
Links
- 229920000642 polymer Chemical class 0.000 title claims description 115
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical class O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 52
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 38
- MVXNGTMKSZHHCO-UHFFFAOYSA-N 3-methyl-1,4-dioxane-2,5-dione Chemical compound CC1OC(=O)COC1=O MVXNGTMKSZHHCO-UHFFFAOYSA-N 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 16
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims description 15
- 229920000954 Polyglycolide Polymers 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000004310 lactic acid Substances 0.000 claims description 13
- 235000014655 lactic acid Nutrition 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 11
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000004633 polyglycolic acid Substances 0.000 claims description 9
- 239000003356 suture material Substances 0.000 claims description 9
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 6
- LLZIQIHXYWEQCA-UHFFFAOYSA-N 3,3-dimethyl-1,4-dioxane-2,5-dione Chemical compound CC1(C)OC(=O)COC1=O LLZIQIHXYWEQCA-UHFFFAOYSA-N 0.000 claims description 5
- 229910014033 C-OH Inorganic materials 0.000 claims description 5
- 229910014570 C—OH Inorganic materials 0.000 claims description 5
- 229920001244 Poly(D,L-lactide) Polymers 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229940106681 chloroacetic acid Drugs 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims 2
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical group [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims 2
- ZQDORJLGXBBNPX-UHFFFAOYSA-N (2-chloroacetyl) 2-hydroxyacetate Chemical compound OCC(=O)OC(=O)CCl ZQDORJLGXBBNPX-UHFFFAOYSA-N 0.000 claims 1
- NIKVNJJACUGXFD-UHFFFAOYSA-N (2-chloroacetyl) 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(=O)CCl NIKVNJJACUGXFD-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- GZYXPXGNODDCBD-UHFFFAOYSA-N 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione Chemical compound CC1(C)OC(=O)C(C)(C)OC1=O GZYXPXGNODDCBD-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229940116333 ethyl lactate Drugs 0.000 claims 1
- 229920001432 poly(L-lactide) Polymers 0.000 claims 1
- 238000009877 rendering Methods 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 description 57
- 239000000463 material Substances 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 230000009102 absorption Effects 0.000 description 39
- 238000010521 absorption reaction Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 33
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000003814 drug Substances 0.000 description 16
- 229940079593 drug Drugs 0.000 description 15
- 239000004744 fabric Substances 0.000 description 14
- 238000001356 surgical procedure Methods 0.000 description 14
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- VAIZVCMDJPBJCM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;trihydrate Chemical compound O.O.O.FC(F)(F)C(=O)C(F)(F)F.FC(F)(F)C(=O)C(F)(F)F VAIZVCMDJPBJCM-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 208000027418 Wounds and injury Diseases 0.000 description 11
- 239000004753 textile Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 206010052428 Wound Diseases 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000002513 implantation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 208000035874 Excoriation Diseases 0.000 description 7
- 210000000481 breast Anatomy 0.000 description 7
- 230000035876 healing Effects 0.000 description 7
- 230000003301 hydrolyzing effect Effects 0.000 description 7
- 210000004185 liver Anatomy 0.000 description 7
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- MVXNGTMKSZHHCO-VKHMYHEASA-N (3s)-3-methyl-1,4-dioxane-2,5-dione Chemical compound C[C@@H]1OC(=O)COC1=O MVXNGTMKSZHHCO-VKHMYHEASA-N 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 229960004275 glycolic acid Drugs 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 235000011150 stannous chloride Nutrition 0.000 description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 210000000944 nerve tissue Anatomy 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229920001059 synthetic polymer Polymers 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 231100000241 scar Toxicity 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 230000023597 hemostasis Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- ZNLAHAOCFKBYRH-UHFFFAOYSA-N 1,4-dioxane-2,3-dione Chemical class O=C1OCCOC1=O ZNLAHAOCFKBYRH-UHFFFAOYSA-N 0.000 description 2
- IRTCJFCIQKNFPP-UHFFFAOYSA-N 2-methyl-1,4-dioxane Chemical compound CC1COCCO1 IRTCJFCIQKNFPP-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 239000011449 brick Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003433 contraceptive agent Substances 0.000 description 2
- 230000002254 contraceptive effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000009950 felting Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001172 regenerating effect Effects 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 210000000779 thoracic wall Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 210000001835 viscera Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- ZFUYBCIKAURZFJ-VKHMYHEASA-N (2S)-2-(2-chloroacetyl)oxypropanoic acid Chemical compound OC(=O)[C@H](C)OC(=O)CCl ZFUYBCIKAURZFJ-VKHMYHEASA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 206010039203 Road traffic accident Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010048629 Wound secretion Diseases 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000007654 attenuated familial adenomatous polyposis Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000000316 bone substitute Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002316 cosmetic surgery Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000459 effect on growth Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000004800 psychological effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229920006268 silicone film Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012414 sterilization procedure Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
- A61L17/105—Polyesters not covered by A61L17/12
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Surgery (AREA)
- Engineering & Computer Science (AREA)
- Materials For Medical Uses (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Dental Preparations (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43536574A | 1974-01-21 | 1974-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616417A5 true CH616417A5 (en) | 1980-03-31 |
Family
ID=23728099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH61375A CH616417A5 (en) | 1974-01-21 | 1975-01-20 | Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS50101367A (enExample) |
| AR (1) | AR205454A1 (enExample) |
| AT (1) | AT339902B (enExample) |
| BE (1) | BE824535A (enExample) |
| CA (1) | CA1052046A (enExample) |
| CH (1) | CH616417A5 (enExample) |
| CS (1) | CS196258B2 (enExample) |
| DD (1) | DD119259A5 (enExample) |
| DE (1) | DE2501448A1 (enExample) |
| DK (1) | DK15275A (enExample) |
| FR (1) | FR2279745A1 (enExample) |
| GB (1) | GB1494781A (enExample) |
| HU (1) | HU173692B (enExample) |
| IE (1) | IE40657B1 (enExample) |
| IN (1) | IN141151B (enExample) |
| IT (1) | IT1044114B (enExample) |
| NL (1) | NL7500689A (enExample) |
| PH (1) | PH12680A (enExample) |
| PL (1) | PL101805B1 (enExample) |
| RO (1) | RO70688A (enExample) |
| SE (1) | SE7500594L (enExample) |
| ZA (1) | ZA7538B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56157422A (en) * | 1980-05-07 | 1981-12-04 | Mitsui Toatsu Chem Inc | Acetylated polyglycolic acid and preparation thereof |
| DE3778111D1 (de) * | 1986-10-24 | 1992-05-14 | Boehringer Ingelheim Kg | Verfahren zur herstellung und reinigung thermolabiler verbindungen. |
| WO1988010260A1 (fr) * | 1987-06-16 | 1988-12-29 | Boehringer Ingelheim Kg | ''meso-lactide'' et son procede de preparation |
| EP0339882A1 (en) * | 1988-04-27 | 1989-11-02 | MITSUI TOATSU CHEMICALS, Inc. | Process for the production of lactide |
| DE4321355A1 (de) * | 1993-06-26 | 1995-01-05 | Basf Ag | Polylactid mit Langkettenverzweigungen |
| DE4440095A1 (de) * | 1994-11-10 | 1996-05-15 | Braun B Surgical Gmbh | Chirurgisches Nahtmaterial, seine Verwendung in der Chirurgie und Verfahren zu seiner Herstellung |
| EP0789080B1 (de) | 1996-02-08 | 2002-01-16 | Gesellschaft für ökologische Technologie und Systemanalyse e.V. | Verfahren zur Herstellung von organischen Aminiumlactaten und deren Verwendung zur Herstellung von Dilactid |
| FR2873371B1 (fr) * | 2004-07-26 | 2008-07-04 | Sod Conseils Rech Applic | Nouvelle methode de synthese de 2,5 dioxane 1,4 diones |
| CA2652078A1 (en) * | 2006-05-15 | 2007-11-22 | Tyco Healthcare Group Lp | Halogenated cyclic lactones and polymers made therefrom |
| BR112014003981A2 (pt) | 2011-08-23 | 2017-03-07 | Endo Pharmaceuticals Inc | compostos de pirimido-piridazinona e seu uso |
| HRP20181671T1 (hr) * | 2012-02-09 | 2018-12-14 | Novus International, Inc. | Heteroatom koji sadrži cikličke dimere |
-
1974
- 1974-12-24 CA CA216,765A patent/CA1052046A/en not_active Expired
- 1974-12-31 IE IE2680/74A patent/IE40657B1/xx unknown
-
1975
- 1975-01-01 AR AR257269A patent/AR205454A1/es active
- 1975-01-02 ZA ZA00750038A patent/ZA7538B/xx unknown
- 1975-01-03 IN IN23/CAL/1975A patent/IN141151B/en unknown
- 1975-01-09 GB GB1003/75A patent/GB1494781A/en not_active Expired
- 1975-01-10 PH PH16698A patent/PH12680A/en unknown
- 1975-01-13 RO RO7581101A patent/RO70688A/ro unknown
- 1975-01-14 CS CS75253A patent/CS196258B2/cs unknown
- 1975-01-15 DE DE19752501448 patent/DE2501448A1/de not_active Withdrawn
- 1975-01-20 BE BE152494A patent/BE824535A/xx unknown
- 1975-01-20 DK DK15275*BA patent/DK15275A/da not_active Application Discontinuation
- 1975-01-20 SE SE7500594A patent/SE7500594L/xx unknown
- 1975-01-20 AT AT39075A patent/AT339902B/de not_active IP Right Cessation
- 1975-01-20 PL PL1975177442A patent/PL101805B1/pl unknown
- 1975-01-20 HU HU75AE436A patent/HU173692B/hu unknown
- 1975-01-20 CH CH61375A patent/CH616417A5/de not_active IP Right Cessation
- 1975-01-20 IT IT47760/75A patent/IT1044114B/it active
- 1975-01-20 DD DD183736A patent/DD119259A5/xx unknown
- 1975-01-21 JP JP50008413A patent/JPS50101367A/ja active Pending
- 1975-01-21 FR FR7501823A patent/FR2279745A1/fr active Granted
- 1975-01-21 NL NL7500689A patent/NL7500689A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1494781A (en) | 1977-12-14 |
| NL7500689A (nl) | 1975-07-23 |
| FR2279745A1 (fr) | 1976-02-20 |
| CS196258B2 (en) | 1980-03-31 |
| IN141151B (enExample) | 1977-01-22 |
| DE2501448A1 (de) | 1975-07-24 |
| SE7500594L (enExample) | 1975-07-22 |
| HU173692B (hu) | 1979-07-28 |
| RO70688A (ro) | 1982-05-10 |
| IE40657L (en) | 1975-07-21 |
| JPS50101367A (enExample) | 1975-08-11 |
| AR205454A1 (es) | 1976-05-07 |
| AT339902B (de) | 1977-11-10 |
| FR2279745B1 (enExample) | 1978-02-24 |
| IE40657B1 (en) | 1979-07-18 |
| IT1044114B (it) | 1980-03-20 |
| DK15275A (enExample) | 1975-09-15 |
| DD119259A5 (enExample) | 1976-04-12 |
| ATA39075A (de) | 1977-03-15 |
| BE824535A (fr) | 1975-07-22 |
| ZA7538B (en) | 1976-01-28 |
| PH12680A (en) | 1979-07-18 |
| AU7708575A (en) | 1976-07-08 |
| CA1052046A (en) | 1979-04-03 |
| PL101805B1 (pl) | 1979-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4033938A (en) | Polymers of unsymmetrically substituted 1,4-dioxane-2,5-diones | |
| US3960152A (en) | Surgical sutures of unsymmetrically substituted 1,4-dioxane-2,5-diones | |
| DE2206144A1 (de) | Von lebenden saeugetiergeweben absorbierbare copolymere | |
| US3867190A (en) | Reducing capillarity of polyglycolic acid sutures | |
| US3982543A (en) | Reducing capillarity of polyglycolic acid sutures | |
| DE69730889T2 (de) | Resorbierbare Copolymere und Mischungen von 6,6-Dialkyl-1,4-dioxepan-2-on und seinem cyclischen Dimeren | |
| US3991766A (en) | Controlled release of medicaments using polymers from glycolic acid | |
| CA1124943A (en) | Synthetic absorbable surgical devices of poly-dioxanone | |
| US3875937A (en) | Surgical dressings of absorbable polymers | |
| JP5280839B2 (ja) | 吸収性／生分解性複合糸及びこれから形成された特性調節外科用インプラント | |
| US3739773A (en) | Polyglycolic acid prosthetic devices | |
| US3636956A (en) | Polylactide sutures | |
| US5486593A (en) | Medical devices fabricated from copolymers having recurring carbonate units | |
| DE69734905T2 (de) | Absorbierbare Polyoxaamide enthaltende Mischungen | |
| US5152781A (en) | Medical devices fabricated from homopolymers and copolymers having recurring carbonate units | |
| DE60311741T2 (de) | Alkyd-Lakton-Kopolymere für medizinische Anwendungen | |
| US5145945A (en) | Homopolymers and copolymers having recurring carbonate units | |
| DE3853591T2 (de) | Medizinische anordnungen, hergestellt aus homo- und kopolymeren mit wiederkehrender karbonateinheiten. | |
| DE19828416A1 (de) | Aliphatisches Polyester aus epsilon-Caprolacton, p-Dioxanon und Glycolid | |
| JPS58138463A (ja) | ｐ―ジオキサノンと２，５―モルホリンジオンの共重合体の製造方法 | |
| US5256764A (en) | Medical devices fabricated from homopolymers and copolymers having recurring carbonate units | |
| DE2515970A1 (de) | Verdichteter filz | |
| CH667586A5 (de) | Verfahren zum modifizieren einer chirurgischen vorrichtung, die dazu bestimmt ist, im koerper eine stuetz-, halterungs- oder verstaerkungsfunktion auszuueben. | |
| EP1181941B1 (de) | Beschichtungsmaterial für die Medizin aus resorbierbarem Material, Verfahren zu seiner Herstellung und Bereitstellung für die Medizin | |
| DE69925775T2 (de) | Thermisch verformbare biokompatible absorbierbare polymere Zwei-Phasen-Matrix für den Einsatz bei medizinischen Vorrichtungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |