CA1087345A - Orthoester polymers - Google Patents
Orthoester polymersInfo
- Publication number
- CA1087345A CA1087345A CA243,429A CA243429A CA1087345A CA 1087345 A CA1087345 A CA 1087345A CA 243429 A CA243429 A CA 243429A CA 1087345 A CA1087345 A CA 1087345A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- polymer
- alkoxy
- alkyl
- mer
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 112
- 150000002905 orthoesters Chemical class 0.000 title abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 25
- 229920005862 polyol Polymers 0.000 claims abstract description 10
- 150000003077 polyols Chemical class 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 91
- -1 tetramethylene, hexamethylene, decamethylene Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 239000013543 active substance Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 238000005809 transesterification reaction Methods 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 5
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 5
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 5
- 229920005604 random copolymer Polymers 0.000 claims description 5
- 229920001897 terpolymer Polymers 0.000 claims description 5
- 229920013641 bioerodible polymer Polymers 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- 239000000178 monomer Substances 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- HRKTYSDVSRVOIP-UHFFFAOYSA-N 2,2-diethoxyoxolane Chemical compound CCOC1(OCC)CCCO1 HRKTYSDVSRVOIP-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 14
- 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 14
- 239000007943 implant Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 229960000890 hydrocortisone Drugs 0.000 description 7
- DYASICXGKFJMSB-UHFFFAOYSA-N 2,3-dimethylideneoxolane Chemical compound C=C1CCOC1=C DYASICXGKFJMSB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 108010001478 Bacitracin Proteins 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229940076134 benzene Drugs 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- 150000000180 1,2-diols Chemical group 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QOWFPNDXNRVDKZ-UHFFFAOYSA-N 2,2-dibutoxyoxolane Chemical compound CCCCOC1(OCCCC)CCCO1 QOWFPNDXNRVDKZ-UHFFFAOYSA-N 0.000 description 2
- JOBZVUKGOHJJTN-UHFFFAOYSA-N 2,2-diethoxy-1,3-dioxolane Chemical compound CCOC1(OCC)OCCO1 JOBZVUKGOHJJTN-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- BYRRPYMBVHTVKO-UHFFFAOYSA-N [Na].[Ti] Chemical compound [Na].[Ti] BYRRPYMBVHTVKO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229960003071 bacitracin Drugs 0.000 description 2
- 229930184125 bacitracin Natural products 0.000 description 2
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000005879 dioxolanyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LMMTVYUCEFJZLC-UHFFFAOYSA-N 1,3,5-pentanetriol Chemical compound OCCC(O)CCO LMMTVYUCEFJZLC-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- CJSITSBWCLTCAP-UHFFFAOYSA-N 1,3-dioxocane Chemical compound C1CCOCOCC1 CJSITSBWCLTCAP-UHFFFAOYSA-N 0.000 description 1
- IWKQQZPURJLDMR-UHFFFAOYSA-N 2,2-diethoxy-4-methyl-1,3-dioxolane Chemical compound CCOC1(OCC)OCC(C)O1 IWKQQZPURJLDMR-UHFFFAOYSA-N 0.000 description 1
- NIRPFFFZNLRWCM-UHFFFAOYSA-N 2,2-diethoxy-5-methyloxolane Chemical compound CCOC1(OCC)CCC(C)O1 NIRPFFFZNLRWCM-UHFFFAOYSA-N 0.000 description 1
- FKHZHLLQZGIQTL-UHFFFAOYSA-N 2,2-diethoxyoxane Chemical compound CCOC1(OCC)CCCCO1 FKHZHLLQZGIQTL-UHFFFAOYSA-N 0.000 description 1
- OLDCAFDOAKNALV-UHFFFAOYSA-N 2,2-diethoxyoxecane Chemical compound CCOC1(OCC)CCCCCCCCO1 OLDCAFDOAKNALV-UHFFFAOYSA-N 0.000 description 1
- WQAKLZLMIIXHGV-UHFFFAOYSA-N 2,2-diethoxyoxepane Chemical compound CCOC1(OCC)CCCCCO1 WQAKLZLMIIXHGV-UHFFFAOYSA-N 0.000 description 1
- BBJAZTIBFQVFAK-UHFFFAOYSA-N 2,2-dimethoxy-6,7-dihydro-5H-pyrano[2,3-b]pyran Chemical compound COC1(C=CC2=C(OCCC2)O1)OC BBJAZTIBFQVFAK-UHFFFAOYSA-N 0.000 description 1
- WYUDMWKRUSJGIW-UHFFFAOYSA-N 2,2-dipropoxy-1,3-dioxolane Chemical compound CCCOC1(OCCC)OCCO1 WYUDMWKRUSJGIW-UHFFFAOYSA-N 0.000 description 1
- VEDIOARIGUYGIJ-UHFFFAOYSA-N 2,2-dipropoxyoxolane Chemical compound CCCOC1(OCCC)CCCO1 VEDIOARIGUYGIJ-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
- TWWSGIYXSHLTIA-UHFFFAOYSA-N 2-[2-(2-hydroxyethyl)cyclopentyl]ethanol Chemical compound OCCC1CCCC1CCO TWWSGIYXSHLTIA-UHFFFAOYSA-N 0.000 description 1
- HZMTXSJDSDRLEF-UHFFFAOYSA-N 2-ethoxy-4-methyl-2-propoxy-1,3-dioxolane Chemical compound CCCOC1(OCC)OCC(C)O1 HZMTXSJDSDRLEF-UHFFFAOYSA-N 0.000 description 1
- VBQKNJGYWOBPMY-UHFFFAOYSA-N 2-heptyloxolane Chemical compound CCCCCCCC1CCCO1 VBQKNJGYWOBPMY-UHFFFAOYSA-N 0.000 description 1
- HDGHQFQMWUTHKL-UHFFFAOYSA-N 2-methyl-1,3-dioxane Chemical compound CC1OCCCO1 HDGHQFQMWUTHKL-UHFFFAOYSA-N 0.000 description 1
- GCQZRSVHYPEACN-UHFFFAOYSA-N 2-methylideneoxolane Chemical compound C=C1CCCO1 GCQZRSVHYPEACN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ODUBKUYVESJSIY-UHFFFAOYSA-N 3,6-dimethylnonane-1,9-diol Chemical compound OCCC(C)CCC(C)CCCO ODUBKUYVESJSIY-UHFFFAOYSA-N 0.000 description 1
- ZDLGNSBLGNPTMB-UHFFFAOYSA-N 3-[1-(3-hydroxypropyl)cyclohexyl]propan-1-ol Chemical compound OCCCC1(CCCO)CCCCC1 ZDLGNSBLGNPTMB-UHFFFAOYSA-N 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- GPBBNPPLBQIADY-UHFFFAOYSA-N 4,4-dimethyloxane Chemical compound CC1(C)CCOCC1 GPBBNPPLBQIADY-UHFFFAOYSA-N 0.000 description 1
- YKFROQCFVXOUPW-UHFFFAOYSA-N 4-(methylthio) aniline Chemical compound CSC1=CC=C(N)C=C1 YKFROQCFVXOUPW-UHFFFAOYSA-N 0.000 description 1
- NJHHMWKDRDICRX-UHFFFAOYSA-N 5-ethoxy-2,2-dipropoxyoxolane Chemical compound C(CC)OC1(OC(CC1)OCC)OCCC NJHHMWKDRDICRX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 101100039010 Caenorhabditis elegans dis-3 gene Proteins 0.000 description 1
- 241000511343 Chondrostoma nasus Species 0.000 description 1
- 101150039033 Eci2 gene Proteins 0.000 description 1
- 101100001673 Emericella variicolor andH gene Proteins 0.000 description 1
- 102100021823 Enoyl-CoA delta isomerase 2 Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 229940124530 sulfonamide Drugs 0.000 description 1
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- 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
- 210000001519 tissue Anatomy 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC([O-])=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 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—
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
- A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
-
- 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
-
- 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
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S71/00—Chemistry: fertilizers
- Y10S71/904—Carrier
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/544,808 US4093709A (en) | 1975-01-28 | 1975-01-28 | Drug delivery devices manufactured from poly(orthoesters) and poly(orthocarbonates) |
| US544,808 | 1975-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087345A true CA1087345A (en) | 1980-10-07 |
Family
ID=24173683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,429A Expired CA1087345A (en) | 1975-01-28 | 1976-01-13 | Orthoester polymers |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4093709A (en, 2012) |
| JP (1) | JPS5410037B2 (en, 2012) |
| AR (1) | AR213619A1 (en, 2012) |
| AT (1) | AT356903B (en, 2012) |
| BE (1) | BE837935A (en, 2012) |
| BR (1) | BR7600499A (en, 2012) |
| CA (1) | CA1087345A (en, 2012) |
| CH (1) | CH635355A5 (en, 2012) |
| DE (1) | DE2602994C2 (en, 2012) |
| DK (1) | DK166360C (en, 2012) |
| ES (1) | ES444484A1 (en, 2012) |
| FR (1) | FR2299356A1 (en, 2012) |
| GB (1) | GB1502082A (en, 2012) |
| IL (1) | IL48799A (en, 2012) |
| IT (1) | IT1057070B (en, 2012) |
| MX (1) | MX142986A (en, 2012) |
| NL (1) | NL174728C (en, 2012) |
| SE (1) | SE418189B (en, 2012) |
| ZA (1) | ZA76493B (en, 2012) |
Families Citing this family (287)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131648A (en) * | 1975-01-28 | 1978-12-26 | Alza Corporation | Structured orthoester and orthocarbonate drug delivery devices |
| US4150108A (en) * | 1975-12-29 | 1979-04-17 | Graham Neil B | Injectable medicinal compositions |
| US4070347A (en) * | 1976-08-16 | 1978-01-24 | Alza Corporation | Poly(orthoester) co- and homopolymers and poly(orthocarbonate) co- and homopolymers having carbonyloxy functionality |
| US4115544A (en) | 1976-08-18 | 1978-09-19 | Alza Corporation | Ocular system made of bioerodible esters having linear ether |
| US4282201A (en) * | 1979-02-02 | 1981-08-04 | Alza Corporation | Pharmaceutical comprising drug and polymer |
| US4246397A (en) * | 1979-02-02 | 1981-01-20 | Alza Corporation | Polymers comprising heterocyclic system |
| US4259102A (en) * | 1979-02-02 | 1981-03-31 | Alza Corporation | Composition comprising useful agent such as fertilizers, housed in heterocyclic polymer |
| 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 |
| US4675189A (en) * | 1980-11-18 | 1987-06-23 | Syntex (U.S.A.) Inc. | Microencapsulation of water soluble active polypeptides |
| US4764380A (en) * | 1982-03-22 | 1988-08-16 | Alza Corporation | Drug delivery system comprising a volume increasing matrix containing a plurality of tiny pills |
| US4484923A (en) * | 1982-03-25 | 1984-11-27 | Alza Corporation | Method for administering immunopotentiator |
| US5248700A (en) * | 1982-05-14 | 1993-09-28 | Akzo Nv | Active agent containing solid structures for prolonged release of active agents |
| JPS5931701A (ja) * | 1982-08-16 | 1984-02-20 | Nitto Electric Ind Co Ltd | 液状活性物質含有膜及びその製造方法 |
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3252786A (en) * | 1962-09-28 | 1966-05-24 | Sun Oil Co | Slow release fertilizers and method of making |
| US3887699A (en) * | 1969-03-24 | 1975-06-03 | Seymour Yolles | Biodegradable polymeric article for dispensing drugs |
| US3960150A (en) * | 1971-09-09 | 1976-06-01 | Alza Corporation | Bioerodible ocular device |
| US4001388A (en) * | 1973-06-14 | 1977-01-04 | Alza Corporation | Ophthalmological bioerodible drug dispensing formulation |
| US4014987A (en) * | 1974-06-04 | 1977-03-29 | Alza Corporation | Device for delivery of useful agent |
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1975
- 1975-01-28 US US05/544,808 patent/US4093709A/en not_active Expired - Lifetime
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- 1976-01-06 IL IL48799A patent/IL48799A/xx unknown
- 1976-01-08 GB GB683/76A patent/GB1502082A/en not_active Expired
- 1976-01-13 CA CA243,429A patent/CA1087345A/en not_active Expired
- 1976-01-20 AR AR261971A patent/AR213619A1/es active
- 1976-01-20 ES ES444484A patent/ES444484A1/es not_active Expired
- 1976-01-26 SE SE7600760A patent/SE418189B/xx not_active IP Right Cessation
- 1976-01-27 FR FR7602109A patent/FR2299356A1/fr active Granted
- 1976-01-27 IT IT67178/76A patent/IT1057070B/it active
- 1976-01-27 DE DE2602994A patent/DE2602994C2/de not_active Expired
- 1976-01-27 AT AT55276A patent/AT356903B/de not_active IP Right Cessation
- 1976-01-27 BR BR7600499A patent/BR7600499A/pt unknown
- 1976-01-27 BE BE163823A patent/BE837935A/xx not_active IP Right Cessation
- 1976-01-27 CH CH100376A patent/CH635355A5/de not_active IP Right Cessation
- 1976-01-27 DK DK032076A patent/DK166360C/da not_active IP Right Cessation
- 1976-01-27 JP JP787276A patent/JPS5410037B2/ja not_active Expired
- 1976-01-28 ZA ZA760493A patent/ZA76493B/xx unknown
- 1976-01-28 MX MX163296A patent/MX142986A/es unknown
- 1976-01-28 NL NLAANVRAGE7600881,A patent/NL174728C/xx not_active IP Right Cessation
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1977
- 1977-08-24 US US05/827,223 patent/US4138344A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL174728C (nl) | 1984-08-01 |
| ES444484A1 (es) | 1977-09-16 |
| IL48799A (en) | 1979-01-31 |
| SE7600760L (sv) | 1976-09-20 |
| IT1057070B (it) | 1982-03-10 |
| ATA55276A (de) | 1979-10-15 |
| DK32076A (da) | 1976-07-29 |
| ZA76493B (en) | 1977-07-27 |
| DE2602994A1 (de) | 1976-07-29 |
| GB1502082A (en) | 1978-02-22 |
| DK166360C (da) | 1993-09-06 |
| AT356903B (de) | 1980-06-10 |
| DK166360B (da) | 1993-04-13 |
| BE837935A (fr) | 1976-05-14 |
| FR2299356B1 (en, 2012) | 1978-11-10 |
| FR2299356A1 (fr) | 1976-08-27 |
| SE418189B (sv) | 1981-05-11 |
| JPS51100194A (en, 2012) | 1976-09-03 |
| BR7600499A (pt) | 1976-08-31 |
| AR213619A1 (es) | 1979-02-28 |
| CH635355A5 (de) | 1983-03-31 |
| US4093709A (en) | 1978-06-06 |
| DE2602994C2 (de) | 1982-08-26 |
| AU1041676A (en) | 1977-08-18 |
| NL7600881A (nl) | 1976-07-30 |
| US4138344A (en) | 1979-02-06 |
| MX142986A (es) | 1981-02-03 |
| IL48799A0 (en) | 1976-03-31 |
| NL174728B (nl) | 1984-03-01 |
| JPS5410037B2 (en, 2012) | 1979-05-01 |
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