CA1112798A - Polymeric orthoesters and process for making same - Google Patents
Polymeric orthoesters and process for making sameInfo
- Publication number
- CA1112798A CA1112798A CA274,870A CA274870A CA1112798A CA 1112798 A CA1112798 A CA 1112798A CA 274870 A CA274870 A CA 274870A CA 1112798 A CA1112798 A CA 1112798A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- alkenyl
- alkyl
- monomer
- orthoester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002905 orthoesters Chemical class 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 10
- -1 hydrocarbon radicals Chemical class 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 229920005862 polyol Polymers 0.000 claims abstract description 10
- 150000003077 polyols Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000000379 polymerizing effect Effects 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims 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 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 24
- 239000003814 drug Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 239000002685 polymerization catalyst Substances 0.000 abstract description 2
- 239000003755 preservative agent Substances 0.000 abstract description 2
- 230000002794 monomerizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229960000890 hydrocortisone Drugs 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- LMMTVYUCEFJZLC-UHFFFAOYSA-N 1,3,5-pentanetriol Chemical compound OCCC(O)CCO LMMTVYUCEFJZLC-UHFFFAOYSA-N 0.000 description 2
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000005724 cycloalkenylene group Chemical group 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WEAYWASEBDOLRG-UHFFFAOYSA-N pentane-1,2,5-triol Chemical compound OCCCC(O)CO WEAYWASEBDOLRG-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LMHUODLTQFEHDT-UHFFFAOYSA-N (2-methyl-3-propan-2-ylhexan-3-yl)oxymethanediol Chemical compound CCCC(C(C)C)(C(C)C)OC(O)O LMHUODLTQFEHDT-UHFFFAOYSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- ZGMNAIODRDOMEK-UHFFFAOYSA-N 1,1,1-trimethoxypropane Chemical compound CCC(OC)(OC)OC ZGMNAIODRDOMEK-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 1
- AGQSMVCZSRTXFB-UHFFFAOYSA-N 1-(dihexoxymethoxy)hexane Chemical compound CCCCCCOC(OCCCCCC)OCCCCCC AGQSMVCZSRTXFB-UHFFFAOYSA-N 0.000 description 1
- JSPNRYDMYDINGQ-UHFFFAOYSA-N 1-butoxypropane-1,1-diol Chemical compound CCCCOC(O)(O)CC JSPNRYDMYDINGQ-UHFFFAOYSA-N 0.000 description 1
- LBKIRBXELMWQRC-UHFFFAOYSA-N 1-methoxypropane-1,1-diol Chemical compound CCC(O)(O)OC LBKIRBXELMWQRC-UHFFFAOYSA-N 0.000 description 1
- FGGPMAFZNRKKSL-UHFFFAOYSA-N 1-propoxypropane-1,1-diol Chemical compound CCCOC(O)(O)CC FGGPMAFZNRKKSL-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- KNCMKWVOMRUHKZ-UHFFFAOYSA-N 2,5-dimethylhex-3-ene Chemical compound CC(C)C=CC(C)C KNCMKWVOMRUHKZ-UHFFFAOYSA-N 0.000 description 1
- IVSFJTXTBRZCCK-UHFFFAOYSA-N 2-(hydroxymethyl)hexane-1,6-diol Chemical compound OCCCCC(CO)CO IVSFJTXTBRZCCK-UHFFFAOYSA-N 0.000 description 1
- QZSPXPXMJSVFSC-UHFFFAOYSA-N 2-(hydroxymethyl)pentane-1,5-diol Chemical compound OCCCC(CO)CO QZSPXPXMJSVFSC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- OOJRTGIXWIUBGG-UHFFFAOYSA-N 2-methylpropane-1,2,3-triol Chemical compound OCC(O)(C)CO OOJRTGIXWIUBGG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AYCYMMUVFQPEFT-UHFFFAOYSA-N 3-[4-(hydroxymethyl)phenyl]propane-1,2-diol Chemical compound OCC(O)CC1=CC=C(CO)C=C1 AYCYMMUVFQPEFT-UHFFFAOYSA-N 0.000 description 1
- HBFVGNNUERJWAP-UHFFFAOYSA-N 3-methoxybutane-1,2,4-triol Chemical compound COC(CO)C(O)CO HBFVGNNUERJWAP-UHFFFAOYSA-N 0.000 description 1
- VSUKEMYYCIDKFI-UHFFFAOYSA-N 3-methyl-4-propan-2-ylpentane-1,2,5-triol Chemical compound CC(C)C(CO)C(C)C(O)CO VSUKEMYYCIDKFI-UHFFFAOYSA-N 0.000 description 1
- RVNKRIBMXCUOLM-UHFFFAOYSA-N 3-methylpent-2-en-2-yloxymethanediol Chemical compound CCC(C)=C(C)OC(O)O RVNKRIBMXCUOLM-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- YIKDSCWDMKAAAT-UHFFFAOYSA-N 4-methylhex-3-en-3-yloxymethanediol Chemical compound CCC(C)=C(CC)OC(O)O YIKDSCWDMKAAAT-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- 101100172879 Caenorhabditis elegans sec-5 gene Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- BYRRPYMBVHTVKO-UHFFFAOYSA-N [Na].[Ti] Chemical compound [Na].[Ti] BYRRPYMBVHTVKO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PKMNZOFQIRXQDO-UHFFFAOYSA-N heptane;hexane Chemical compound CCCCCC.CCCCCCC PKMNZOFQIRXQDO-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- YJYVGZNSBDSYPN-UHFFFAOYSA-N oct-5-ene-1,2,8-triol Chemical compound OCCC=CCCC(O)CO YJYVGZNSBDSYPN-UHFFFAOYSA-N 0.000 description 1
- FVGBHSIHHXTYTH-UHFFFAOYSA-N pentane-1,1,1-triol Chemical compound CCCCC(O)(O)O FVGBHSIHHXTYTH-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000003128 rodenticide Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US675,185 | 1976-04-08 | ||
| US05/675,185 US4066747A (en) | 1976-04-08 | 1976-04-08 | Polymeric orthoesters housing beneficial drug for controlled release therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112798A true CA1112798A (en) | 1981-11-17 |
Family
ID=24709398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA274,870A Expired CA1112798A (en) | 1976-04-08 | 1977-03-28 | Polymeric orthoesters and process for making same |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US4066747A (enExample) |
| JP (1) | JPS52123500A (enExample) |
| AU (1) | AU507701B2 (enExample) |
| CA (1) | CA1112798A (enExample) |
| CH (1) | CH633567A5 (enExample) |
| DE (1) | DE2715502A1 (enExample) |
| FR (1) | FR2347396A1 (enExample) |
| GB (1) | GB1518638A (enExample) |
| IT (1) | IT1082732B (enExample) |
| SE (1) | SE421321B (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387215A (en) * | 1973-03-30 | 1983-06-07 | Bailey William J | Polycyclic ring-opened polymers |
| US4328204A (en) * | 1977-03-02 | 1982-05-04 | Ethicon, Inc. | Absorbable polymer-drug compounds and method for making same |
| US4211674A (en) * | 1978-04-10 | 1980-07-08 | Polak's Frutal Works B.V. | Cyclic acetals and ketals and their use in perfume compositions |
| US4282201A (en) * | 1979-02-02 | 1981-08-04 | Alza Corporation | Pharmaceutical comprising drug and polymer |
| DE2928636A1 (de) * | 1979-07-16 | 1981-02-12 | Hoechst Ag | Strahlungsempfindliches gemisch und verfahren zur herstellung von reliefbildern |
| US4425473A (en) | 1980-02-04 | 1984-01-10 | Toagosei Chemical Industry Co., Ltd. | Polymerizable bicyclic orthoester compounds |
| US4304767A (en) * | 1980-05-15 | 1981-12-08 | Sri International | Polymers of di- (and higher functionality) ketene acetals and polyols |
| US4346709A (en) * | 1980-11-10 | 1982-08-31 | Alza Corporation | Drug delivery devices comprising erodible polymer and erosion rate modifier |
| US4322323A (en) * | 1980-12-01 | 1982-03-30 | Alza Corporation | Erodible device comprising surfactant for modifying the rate of erosion of the device |
| US4489056A (en) * | 1982-06-30 | 1984-12-18 | Merck & Co., Inc. | Acid anhydrides as rate controlling agent for the erosion of polymers which latter polymers have beneficial substances dispersed throughout their matrix or where the polymer matrix surrounds the beneficial substance |
| US4530840A (en) * | 1982-07-29 | 1985-07-23 | The Stolle Research And Development Corporation | Injectable, long-acting microparticle formulation for the delivery of anti-inflammatory agents |
| JPS6067531A (ja) * | 1983-09-22 | 1985-04-17 | Toshiba Corp | 樹脂組成物 |
| US4841968A (en) * | 1986-09-26 | 1989-06-27 | Southern Research Institute | Antithrombotic/thrombolytic suture and methods of making and using the same |
| US4969872A (en) * | 1989-03-08 | 1990-11-13 | Alza Corporation | Intravenous system for delivering a beneficial agent with delivery rate control via permeable surface area variance |
| AU6402490A (en) * | 1989-08-28 | 1991-04-08 | Pharmaceutical Delivery Systems, Inc. | Bioerodible polymers useful for the controlled release of therapeutic agents |
| US5030457A (en) * | 1989-08-28 | 1991-07-09 | Pharmaceutical Delivery Systems, Inc. | Bioerodible polymers useful for the controlled release of therapeutic agents |
| US5620700A (en) * | 1990-10-30 | 1997-04-15 | Alza Corporation | Injectable drug delivery system and method |
| US5461140A (en) * | 1992-04-30 | 1995-10-24 | Pharmaceutical Delivery Systems | Bioerodible polymers for solid controlled release pharmaceutical compositions |
| US6440457B1 (en) * | 1993-05-27 | 2002-08-27 | Alza Corporation | Method of administering antidepressant dosage form |
| US5912268A (en) * | 1995-05-22 | 1999-06-15 | Alza Corporation | Dosage form and method for treating incontinence |
| US6262115B1 (en) | 1995-05-22 | 2001-07-17 | Alza Coporation | Method for the management of incontinence |
| EP0747375A1 (en) * | 1995-06-05 | 1996-12-11 | General Electric Company | Method for making orthoester monomers |
| US6919373B1 (en) | 1996-11-12 | 2005-07-19 | Alza Corporation | Methods and devices for providing prolonged drug therapy |
| US20040062799A1 (en) * | 1997-09-29 | 2004-04-01 | Ayer Atul D. | Therapeutic composition and delivery system for administering drug |
| US6486248B2 (en) | 2001-01-08 | 2002-11-26 | Milliken & Company | Liquid colorant and method |
| ES2296956T5 (es) * | 2001-06-11 | 2011-07-12 | Xenoport, Inc. | Profármacos de análogos de gaba, composiciones y sus usos. |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) * | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
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| US20050208132A1 (en) * | 2002-07-29 | 2005-09-22 | Gayatri Sathyan | Methods and dosage forms for reducing side effects of benzisozazole derivatives |
| US20050232995A1 (en) * | 2002-07-29 | 2005-10-20 | Yam Nyomi V | Methods and dosage forms for controlled delivery of paliperidone and risperidone |
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| WO2004053192A1 (en) * | 2002-12-11 | 2004-06-24 | Xenoport, Inc. | Orally administered dosage forms of fused gaba analog prodrugs having reduced toxicity |
| US20040254246A1 (en) * | 2003-03-31 | 2004-12-16 | Barrett Ronald W. | Treating or preventing hot flashes using prodrugs of GABA analogs |
| EP2354120A1 (en) | 2003-08-20 | 2011-08-10 | XenoPort, Inc. | Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof |
| KR20110097942A (ko) * | 2003-08-20 | 2011-08-31 | 제노포트 인코포레이티드 | 아실옥시알킬 카르바메이트 프로드러그, 합성 및 사용 방법 |
| WO2005025562A1 (en) * | 2003-09-11 | 2005-03-24 | Xenoport, Inc. | Treating and/or preventing urinary incontinence using prodrugs of gaba analogs |
| MXPA06003043A (es) * | 2003-09-17 | 2006-05-31 | Xenoport Inc | Tratamiento o prevencion del sindrome piernas inquietas utilizando prodrogas de analogos gaba. |
| US7329413B1 (en) * | 2003-11-06 | 2008-02-12 | Advanced Cardiovascular Systems, Inc. | Coatings for drug delivery devices having gradient of hydration and methods for fabricating thereof |
| MX339690B (es) * | 2004-06-04 | 2016-06-06 | Xenoport Inc | Profarmacos de levodopa y sus composiciones y usos. |
| WO2005121070A1 (en) * | 2004-06-04 | 2005-12-22 | Xenoport, Inc. | Levodopa prodrugs, and compositions and uses thereof |
| US20060128676A1 (en) * | 2004-07-13 | 2006-06-15 | Pharmacofore, Inc. | Compositions of nicotinic agonists and therapeutic agents and methods for treating or preventing diseases or pain |
| US7566738B2 (en) * | 2004-11-03 | 2009-07-28 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use |
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| RU2440112C2 (ru) * | 2004-11-04 | 2012-01-20 | Ксенопорт, Инк. | Пероральная дозированная форма габапентина замедленного высвобождения |
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| JP4938771B2 (ja) * | 2005-06-20 | 2012-05-23 | ゼノポート，インコーポレーテッド | トラネキサム酸のカルバミン酸アシルオキシアルキルプロドラッグ、合成法、および使用 |
| EP1928450A2 (en) * | 2005-08-26 | 2008-06-11 | Xenoport, Inc. | Treating premature ejaculation using gabapentin and pregabalin prodrugs |
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| TW200843731A (en) * | 2006-12-21 | 2008-11-16 | Xenoport Inc | Catechol protected levodopa diester prodrugs, compositions, and methods of use |
| US8940315B2 (en) * | 2008-04-18 | 2015-01-27 | Medtronic, Inc. | Benzodiazepine formulation in a polyorthoester carrier |
| US8956642B2 (en) * | 2008-04-18 | 2015-02-17 | Medtronic, Inc. | Bupivacaine formulation in a polyorthoester carrier |
| US9290445B2 (en) * | 2008-10-20 | 2016-03-22 | Xenoport, Inc. | Methods of synthesizing a levodopa ester prodrug |
| US8399513B2 (en) * | 2008-10-20 | 2013-03-19 | Xenoport, Inc. | Levodopa prodrug mesylate hydrate |
| US20110060040A1 (en) * | 2009-09-04 | 2011-03-10 | Xenoport, Inc. | Uses of acyloxyalkyl carbamate prodrugs of tranexamic acid |
| WO2011056240A2 (en) | 2009-11-09 | 2011-05-12 | Xenoport, Inc. | Pharmaceutical compositions and oral dosage forms of a levodopa prodrug and methods of use |
| WO2011091164A1 (en) * | 2010-01-22 | 2011-07-28 | Xenoport, Inc. | Oral dosage forms having a high loading of a tranexamic acid prodrug |
| US9089531B2 (en) | 2010-09-28 | 2015-07-28 | The Regents Of The University Of California | GABA agonists in the treatment of disorders associated with metabolic syndrome and GABA combinations in treatment or prophylaxis of type I diabetes |
| HK1259018A1 (zh) | 2015-10-01 | 2019-11-22 | Elysium Therapeutics, Inc. | 抗过量和滥用的多聚亚单元阿片样物质前药 |
| US10335406B2 (en) | 2015-10-01 | 2019-07-02 | Elysium Therapeutics, Inc. | Opioid compositions resistant to overdose and abuse |
| JP7234130B2 (ja) | 2017-03-17 | 2023-03-07 | エリージウム セラピューティクス， インコーポレイテッド | 過剰摂取および乱用に対して抵抗性のポリサブユニットオピオイドプロドラッグ |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2636884A (en) * | 1953-04-28 | J-moxoeane | ||
| US3328427A (en) * | 1963-10-31 | 1967-06-27 | Celanese Corp | Mono, ortho and oxetane esters of trimethylol compounds |
| DE1592655C2 (de) * | 1966-07-13 | 1972-03-30 | Gewerkschaft Victor, Chemische Werke, 4620 Castrop Rauxel | Düngemittelgranulat mit kontollierter Nährstoffabgabe |
| US4015970A (en) * | 1968-09-06 | 1977-04-05 | Airwick Industries, Inc. | Granular products for soil treatment |
| US3887699A (en) * | 1969-03-24 | 1975-06-03 | Seymour Yolles | Biodegradable polymeric article for dispensing drugs |
| US3696123A (en) * | 1970-03-19 | 1972-10-03 | Siegfried H Schroeter | Dihydrocarbonoxyoxethanes |
| US3673216A (en) * | 1970-05-01 | 1972-06-27 | Gen Electric | Alkoxyoxetanes |
| US3914402A (en) * | 1973-06-14 | 1975-10-21 | Alza Corp | Ophthalmic dosage form, for releasing medication over time |
| US3911098A (en) * | 1974-02-11 | 1975-10-07 | American Cyanamid Co | Medicament carrier |
-
1976
- 1976-04-08 US US05/675,185 patent/US4066747A/en not_active Expired - Lifetime
-
1977
- 1977-02-28 GB GB8424/77A patent/GB1518638A/en not_active Expired
- 1977-03-28 CA CA274,870A patent/CA1112798A/en not_active Expired
- 1977-04-01 SE SE7703816A patent/SE421321B/xx not_active IP Right Cessation
- 1977-04-04 AU AU23933/77A patent/AU507701B2/en not_active Expired
- 1977-04-06 FR FR7710402A patent/FR2347396A1/fr active Granted
- 1977-04-06 JP JP3937477A patent/JPS52123500A/ja active Granted
- 1977-04-06 DE DE19772715502 patent/DE2715502A1/de active Granted
- 1977-04-06 CH CH437077A patent/CH633567A5/de not_active IP Right Cessation
- 1977-04-07 IT IT67771/77A patent/IT1082732B/it active
- 1977-09-28 US US05/837,309 patent/US4155740A/en not_active Expired - Lifetime
- 1977-09-28 US US05/837,310 patent/US4119579A/en not_active Expired - Lifetime
- 1977-09-28 US US05/837,308 patent/US4136252A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1082732B (it) | 1985-05-21 |
| US4066747A (en) | 1978-01-03 |
| DE2715502A1 (de) | 1977-10-20 |
| CH633567A5 (de) | 1982-12-15 |
| SE7703816L (sv) | 1977-10-09 |
| SE421321B (sv) | 1981-12-14 |
| DE2715502C2 (enExample) | 1988-01-28 |
| FR2347396B1 (enExample) | 1980-12-12 |
| GB1518638A (en) | 1978-07-19 |
| FR2347396A1 (fr) | 1977-11-04 |
| AU507701B2 (en) | 1980-02-21 |
| JPS52123500A (en) | 1977-10-17 |
| US4119579A (en) | 1978-10-10 |
| AU2393377A (en) | 1978-10-12 |
| US4136252A (en) | 1979-01-23 |
| US4155740A (en) | 1979-05-22 |
| JPS619968B2 (enExample) | 1986-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |