MXPA05000796A - Aditivos de acidos polialquilenglicolicos. - Google Patents
Aditivos de acidos polialquilenglicolicos.Info
- Publication number
- MXPA05000796A MXPA05000796A MXPA05000796A MXPA05000796A MXPA05000796A MX PA05000796 A MXPA05000796 A MX PA05000796A MX PA05000796 A MXPA05000796 A MX PA05000796A MX PA05000796 A MXPA05000796 A MX PA05000796A MX PA05000796 A MXPA05000796 A MX PA05000796A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- pag
- residue
- compound
- ester
- Prior art date
Links
- 229920001515 polyalkylene glycol Polymers 0.000 title claims abstract description 33
- 239000002253 acid Substances 0.000 title claims description 46
- 239000000654 additive Substances 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims abstract description 71
- 229960000074 biopharmaceutical Drugs 0.000 claims abstract description 40
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 13
- 229920001184 polypeptide Polymers 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 165
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 claims description 94
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 claims description 94
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 229920001223 polyethylene glycol Polymers 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000003827 glycol group Chemical group 0.000 claims description 20
- 101000987219 Sus scrofa Pregnancy-associated glycoprotein 1 Proteins 0.000 claims description 19
- 230000008030 elimination Effects 0.000 claims description 19
- 238000003379 elimination reaction Methods 0.000 claims description 19
- 150000004820 halides Chemical class 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000007822 coupling agent Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 101000629400 Homo sapiens Mesoderm-specific transcript homolog protein Proteins 0.000 claims description 3
- 102100026821 Mesoderm-specific transcript homolog protein Human genes 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 abstract description 28
- 108090000623 proteins and genes Proteins 0.000 abstract description 28
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 16
- 230000021615 conjugation Effects 0.000 abstract description 6
- 150000003384 small molecules Chemical class 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 235000000346 sugar Nutrition 0.000 abstract description 3
- 150000008163 sugars Chemical class 0.000 abstract description 3
- 150000002334 glycols Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 239000000203 mixture Substances 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 polyethylene Polymers 0.000 description 21
- 229960004132 diethyl ether Drugs 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 10
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
- 102000003951 Erythropoietin Human genes 0.000 description 9
- 108090000394 Erythropoietin Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229940105423 erythropoietin Drugs 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000006320 pegylation Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 230000005847 immunogenicity Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 210000001995 reticulocyte Anatomy 0.000 description 3
- 229940005605 valeric acid Drugs 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- PVVTWNMXEHROIA-UHFFFAOYSA-N 2-(3-hydroxypropyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(CCCO)=NC(=O)C2=C1 PVVTWNMXEHROIA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QYXNFROWLZPWPC-FXQIFTODSA-N Asn-Glu-Gln Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O QYXNFROWLZPWPC-FXQIFTODSA-N 0.000 description 2
- CPYHLXSGDBDULY-IHPCNDPISA-N Asn-Trp-Phe Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O CPYHLXSGDBDULY-IHPCNDPISA-N 0.000 description 2
- 241000132092 Aster Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- MAGNEQBFSBREJL-DCAQKATOSA-N Gln-Glu-Lys Chemical compound C(CCN)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)N MAGNEQBFSBREJL-DCAQKATOSA-N 0.000 description 2
- PJBVXVBTTFZPHJ-GUBZILKMSA-N Glu-Leu-Asp Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)O)N PJBVXVBTTFZPHJ-GUBZILKMSA-N 0.000 description 2
- MWMJCGBSIORNCD-AVGNSLFASA-N Glu-Leu-Leu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O MWMJCGBSIORNCD-AVGNSLFASA-N 0.000 description 2
- RVKIPWVMZANZLI-UHFFFAOYSA-N H-Lys-Trp-OH Natural products C1=CC=C2C(CC(NC(=O)C(N)CCCCN)C(O)=O)=CNC2=C1 RVKIPWVMZANZLI-UHFFFAOYSA-N 0.000 description 2
- 101000987586 Homo sapiens Eosinophil peroxidase Proteins 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- GVIGVIOEYBOTCB-XIRDDKMYSA-N Ser-Leu-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CO)CC(C)C)C(O)=O)=CNC2=C1 GVIGVIOEYBOTCB-XIRDDKMYSA-N 0.000 description 2
- WQOHKVRQDLNDIL-YJRXYDGGSA-N Tyr-Thr-Ser Chemical compound [H]N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(O)=O WQOHKVRQDLNDIL-YJRXYDGGSA-N 0.000 description 2
- 108010092854 aspartyllysine Proteins 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
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- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- WTGINEVKLCVRCK-UHFFFAOYSA-N ethyl 15-bromopentadecanoate Chemical compound CCOC(=O)CCCCCCCCCCCCCCBr WTGINEVKLCVRCK-UHFFFAOYSA-N 0.000 description 2
- GKSCTYSHDIGNGC-UHFFFAOYSA-N ethyl 3-bromo-2-(bromomethyl)propanoate Chemical compound CCOC(=O)C(CBr)CBr GKSCTYSHDIGNGC-UHFFFAOYSA-N 0.000 description 2
- OPXQLUFLTHEZST-UHFFFAOYSA-N ethyl 3-bromobutanoate Chemical compound CCOC(=O)CC(C)Br OPXQLUFLTHEZST-UHFFFAOYSA-N 0.000 description 2
- IVIDHIPPKWHGHJ-UHFFFAOYSA-N ethyl 3-bromohexanoate Chemical compound CCCC(Br)CC(=O)OCC IVIDHIPPKWHGHJ-UHFFFAOYSA-N 0.000 description 2
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 2
- OOBFNDGMAGSNKA-UHFFFAOYSA-N ethyl 7-bromoheptanoate Chemical compound CCOC(=O)CCCCCCBr OOBFNDGMAGSNKA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 102000044890 human EPO Human genes 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- SHCRSWJVWSAMKQ-UHFFFAOYSA-N methyl 10-bromodecanoate Chemical compound COC(=O)CCCCCCCCCBr SHCRSWJVWSAMKQ-UHFFFAOYSA-N 0.000 description 2
- HFNPVFKUZYCDIB-UHFFFAOYSA-N methyl 11-bromoundecanoate Chemical compound COC(=O)CCCCCCCCCCBr HFNPVFKUZYCDIB-UHFFFAOYSA-N 0.000 description 2
- WJYBMWHJTZBYSO-UHFFFAOYSA-N methyl 3-bromobutanoate Chemical compound COC(=O)CC(C)Br WJYBMWHJTZBYSO-UHFFFAOYSA-N 0.000 description 2
- HDQHWBXUKZBPDN-UHFFFAOYSA-N methyl 3-chlorobutanoate Chemical compound COC(=O)CC(C)Cl HDQHWBXUKZBPDN-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000017854 proteolysis Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- PFNCOYVEMJYEED-UHFFFAOYSA-N 16-bromohexadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCBr PFNCOYVEMJYEED-UHFFFAOYSA-N 0.000 description 1
- GABSTWMSOFZKEJ-UHFFFAOYSA-N 17-bromoheptadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCBr GABSTWMSOFZKEJ-UHFFFAOYSA-N 0.000 description 1
- DJQVPXPEXAWGRE-UHFFFAOYSA-N 2,3-dihydrotriazolo[4,5-b]pyridin-7-one Chemical compound O=C1C=CN=C2NNN=C12 DJQVPXPEXAWGRE-UHFFFAOYSA-N 0.000 description 1
- KNLOTZNPRIFUAR-UHFFFAOYSA-N 2-bromodecanoic acid Chemical compound CCCCCCCCC(Br)C(O)=O KNLOTZNPRIFUAR-UHFFFAOYSA-N 0.000 description 1
- MELJYLJLJXTLGX-UHFFFAOYSA-N 2-bromononanoic acid Chemical compound CCCCCCCC(Br)C(O)=O MELJYLJLJXTLGX-UHFFFAOYSA-N 0.000 description 1
- ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- TWHDOEYLXXQYOZ-FXQIFTODSA-N Gln-Asn-Gln Chemical compound C(CC(=O)N)[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)O)N TWHDOEYLXXQYOZ-FXQIFTODSA-N 0.000 description 1
- IQACOVZVOMVILH-FXQIFTODSA-N Glu-Glu-Ser Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(O)=O IQACOVZVOMVILH-FXQIFTODSA-N 0.000 description 1
- DAHLWSFUXOHMIA-FXQIFTODSA-N Glu-Ser-Gln Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(O)=O DAHLWSFUXOHMIA-FXQIFTODSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
- KRBMQYPTDYSENE-BQBZGAKWSA-N His-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CNC=N1 KRBMQYPTDYSENE-BQBZGAKWSA-N 0.000 description 1
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- C08G65/32—Polymers modified by chemical after-treatment
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Landscapes
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| US7153829B2 (en) | 2002-06-07 | 2006-12-26 | Dyax Corp. | Kallikrein-inhibitor therapies |
| PT2298278E (pt) | 2002-06-07 | 2016-02-25 | Dyax Corp | Prevenção e redução da perda de sangue e resposta inflamatória |
| CN100337689C (zh) * | 2002-07-24 | 2007-09-19 | 弗·哈夫曼-拉罗切有限公司 | 聚亚烷基二醇酸加合物 |
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| EP1725262B1 (en) * | 2004-03-15 | 2021-05-26 | Nektar Therapeutics | Polymer-based compositions and conjugates of hiv entry inhibitors |
| US20080255305A1 (en) * | 2004-05-17 | 2008-10-16 | Mcmaster University | Biological Molecule-Reactive Hydrophilic Silicone Surface |
| WO2006019950A2 (en) | 2004-07-16 | 2006-02-23 | Nektar Therapeutics Al, Corporation | Conjugates of a gm-csf moiety and a polymer |
| US7235530B2 (en) | 2004-09-27 | 2007-06-26 | Dyax Corporation | Kallikrein inhibitors and anti-thrombolytic agents and uses thereof |
| DE602006005686D1 (de) * | 2005-08-26 | 2009-04-23 | Novo Nordisk As | Verfahren zur modifizierung eines makromolekularen systems |
| JP5021649B2 (ja) * | 2005-08-26 | 2012-09-12 | ノヴォ ノルディスク アクティーゼルスカブ | 高分子システムを変性する方法 |
| US8133707B2 (en) * | 2006-01-17 | 2012-03-13 | Enzon Pharmaceuticals, Inc. | Methods of preparing activated polymers having alpha nitrogen groups |
| AR067537A1 (es) * | 2007-07-17 | 2009-10-14 | Hoffmann La Roche | Purificacion de polipeptidos pegilados |
| CL2008002054A1 (es) | 2007-07-17 | 2009-05-29 | Hoffmann La Roche | Metodo para la regeneracion de una columna de cromatografia de intercambio cationico despues de la elusion de eritropoyetina monopeguilada y metodo para obtener una eritropoyetina monopeguilada, incorporando el metodo de regeneracion de la columna de intercambio cationico. |
| WO2009026334A2 (en) * | 2007-08-21 | 2009-02-26 | Genzyme Corporation | Treatment with kallikrein inhibitors |
| KR101671537B1 (ko) * | 2008-08-11 | 2016-11-01 | 넥타르 테라퓨틱스 | 다분지형 중합체 알카노에이트 컨쥬게이트 |
| JP2013516389A (ja) | 2009-01-06 | 2013-05-13 | ダイアックス コーポレーション | カリクレイン阻害剤による粘膜炎治療 |
| ES2905545T3 (es) | 2010-01-06 | 2022-04-11 | Takeda Pharmaceuticals Co | Proteínas de unión a calicreína plasmática |
| US10040761B2 (en) * | 2010-06-25 | 2018-08-07 | Nof Corporation | Branched hetero polyethylene glycol and intermediate |
| US10894087B2 (en) | 2010-12-22 | 2021-01-19 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
| US20130331443A1 (en) | 2010-12-22 | 2013-12-12 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
| KR102011156B1 (ko) | 2011-01-06 | 2019-08-16 | 다이액스 코포레이션 | 혈장 칼리크레인 결합 단백질 |
| WO2013151776A1 (en) | 2012-04-03 | 2013-10-10 | Sangart, Inc. | Succinimide-activated nitroxyl compounds and methods for the use thereof for nitroxylation of proteins |
| CN102816227A (zh) * | 2012-08-30 | 2012-12-12 | 深圳赛保尔生物药业有限公司 | 回收促红细胞生成素的方法 |
| EP2968597B1 (en) | 2013-03-15 | 2021-08-18 | Schindler, William | Polyalkylene oxide valerate hemoglobin conjugates |
| IL247942B (en) | 2014-03-27 | 2022-09-01 | Dyax Corp | Compositions and methods for drops in macular edema as a result of diabetes |
| US11286307B2 (en) | 2015-12-11 | 2022-03-29 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating hereditary angioedema attack |
| WO2020203583A1 (ja) * | 2019-03-29 | 2020-10-08 | 日油株式会社 | 末端カルボキシル基含有ポリエチレングリコールの製造方法および活性化ポリエチレングリコールの製造方法 |
| AU2021209045A1 (en) | 2020-01-13 | 2022-07-28 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating pediatric hereditary angioedema attack |
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| US5382657A (en) * | 1992-08-26 | 1995-01-17 | Hoffmann-La Roche Inc. | Peg-interferon conjugates |
| HUT75533A (en) * | 1993-11-10 | 1997-05-28 | Schering Corp | Improved interferon polymer conjugates |
| US5672662A (en) * | 1995-07-07 | 1997-09-30 | Shearwater Polymers, Inc. | Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications |
| TW517067B (en) | 1996-05-31 | 2003-01-11 | Hoffmann La Roche | Interferon conjugates |
| DE69735292T2 (de) * | 1996-10-25 | 2006-10-19 | Gilead Sciences, Inc., Foster City | Gefaesszellen wachstumsfaktor (vegf) nukleinsäureligand-komplexe |
| WO2000044785A1 (en) | 1999-01-29 | 2000-08-03 | F. Hoffmann-La Roche Ag | Gcsf conjugates |
| AU3714800A (en) | 1999-03-02 | 2000-09-21 | Schering Corporation | Hiv therapy |
| CZ299516B6 (cs) | 1999-07-02 | 2008-08-20 | F. Hoffmann-La Roche Ag | Konjugát erythropoetinového glykoproteinu, zpusobjeho výroby a použití a farmaceutická kompozice sjeho obsahem |
| MXPA02003540A (es) | 1999-10-08 | 2003-09-12 | Nektar Therapeutics Al Corp | Derivados de poli(etilenglicol) heterobifuncionales y los metodos para su preparacion. |
| CA2394980C (en) * | 1999-12-22 | 2008-05-13 | Shearwater Corporation | Sterically hindered derivatives of water soluble polymers |
| US20020065397A1 (en) | 2000-10-12 | 2002-05-30 | Joseph Roberts | Protecting therapeutic compositions from host-mediated inactivation |
| EP1345628B1 (en) * | 2000-12-20 | 2011-04-13 | F. Hoffmann-La Roche AG | Conjugates of erythropoietin (epo) with polyethylene glycol (peg) |
| CN100337689C (zh) * | 2002-07-24 | 2007-09-19 | 弗·哈夫曼-拉罗切有限公司 | 聚亚烷基二醇酸加合物 |
-
2003
- 2003-07-16 CN CNB038175088A patent/CN100337689C/zh not_active Expired - Fee Related
- 2003-07-16 BR BR0313212-9A patent/BR0313212A/pt not_active Application Discontinuation
- 2003-07-16 EP EP03766196A patent/EP1526872A1/en not_active Withdrawn
- 2003-07-16 JP JP2004525225A patent/JP4451308B2/ja not_active Expired - Fee Related
- 2003-07-16 WO PCT/EP2003/007736 patent/WO2004012773A1/en not_active Ceased
- 2003-07-16 MX MXPA05000796A patent/MXPA05000796A/es active IP Right Grant
- 2003-07-16 KR KR1020057001328A patent/KR100608415B1/ko not_active Expired - Fee Related
- 2003-07-16 CA CA2492775A patent/CA2492775C/en not_active Expired - Fee Related
- 2003-07-16 RU RU2005105580/04A patent/RU2318004C2/ru not_active IP Right Cessation
- 2003-07-16 PL PL03375265A patent/PL375265A1/xx unknown
- 2003-07-16 AU AU2003258518A patent/AU2003258518B2/en not_active Ceased
- 2003-07-22 US US10/625,033 patent/US7193031B2/en not_active Expired - Fee Related
- 2003-07-22 AR AR20030102624A patent/AR040654A1/es not_active Application Discontinuation
-
2006
- 2006-03-22 US US11/386,876 patent/US7504477B2/en not_active Expired - Fee Related
-
2008
- 2008-07-14 JP JP2008182692A patent/JP5112203B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7193031B2 (en) | 2007-03-20 |
| AR040654A1 (es) | 2005-04-13 |
| US20060167218A1 (en) | 2006-07-27 |
| PL375265A1 (en) | 2005-11-28 |
| AU2003258518A1 (en) | 2004-02-23 |
| RU2005105580A (ru) | 2006-01-20 |
| US7504477B2 (en) | 2009-03-17 |
| JP2006502250A (ja) | 2006-01-19 |
| KR20050025663A (ko) | 2005-03-14 |
| JP4451308B2 (ja) | 2010-04-14 |
| CN1671422A (zh) | 2005-09-21 |
| JP2009062516A (ja) | 2009-03-26 |
| KR100608415B1 (ko) | 2006-08-02 |
| US20040106747A1 (en) | 2004-06-03 |
| RU2318004C2 (ru) | 2008-02-27 |
| CA2492775A1 (en) | 2004-02-12 |
| CN100337689C (zh) | 2007-09-19 |
| WO2004012773A1 (en) | 2004-02-12 |
| JP5112203B2 (ja) | 2013-01-09 |
| CA2492775C (en) | 2011-06-21 |
| AU2003258518B2 (en) | 2007-01-18 |
| BR0313212A (pt) | 2005-06-28 |
| EP1526872A1 (en) | 2005-05-04 |
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