NO851278L - Fremgangsmaate for fremstilling av acyltripeptider og mellomprodukter for anvendelse ved fremgangsmaaten - Google Patents
Fremgangsmaate for fremstilling av acyltripeptider og mellomprodukter for anvendelse ved fremgangsmaatenInfo
- Publication number
- NO851278L NO851278L NO851278A NO851278A NO851278L NO 851278 L NO851278 L NO 851278L NO 851278 A NO851278 A NO 851278A NO 851278 A NO851278 A NO 851278A NO 851278 L NO851278 L NO 851278L
- Authority
- NO
- Norway
- Prior art keywords
- solution
- mmol
- acid
- formula
- benzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000543 intermediate Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
- 230000003308 immunostimulating effect Effects 0.000 claims description 6
- 239000003022 immunostimulating agent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229960001438 immunostimulant agent Drugs 0.000 claims description 3
- CYHLSXUFTJOESF-UHFFFAOYSA-N benzyl n-(hydrazinecarbonylamino)carbamate Chemical group NNC(=O)NNC(=O)OCC1=CC=CC=C1 CYHLSXUFTJOESF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- 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 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 16
- -1 L-alanyl-D-glutamyl moieties Chemical group 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 239000004472 Lysine Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- DPJJBVHPCYIRJZ-SECBINFHSA-N (2r)-2-(heptanoylamino)pentanedioic acid Chemical compound CCCCCCC(=O)N[C@@H](C(O)=O)CCC(O)=O DPJJBVHPCYIRJZ-SECBINFHSA-N 0.000 description 4
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical class OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 4
- 108010016626 Dipeptides Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 102000002704 Leucyl aminopeptidase Human genes 0.000 description 3
- 108010004098 Leucyl aminopeptidase Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 230000002766 immunoenhancing effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- GBCAVSYHPPARHX-UHFFFAOYSA-M n'-cyclohexyl-n-[2-(4-methylmorpholin-4-ium-4-yl)ethyl]methanediimine;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1CCCCC1N=C=NCC[N+]1(C)CCOCC1 GBCAVSYHPPARHX-UHFFFAOYSA-M 0.000 description 3
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- 239000012047 saturated solution Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 125000002221 trityl group Chemical class [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- DQUJEUCGKDJODK-KDURUIRLSA-N (2R,6S)-2,6-bis(phenylmethoxycarbonylamino)heptanedioic acid Chemical compound C(C1=CC=CC=C1)OC(=O)N[C@@H](CCC[C@@H](NC(=O)OCC1=CC=CC=C1)C(=O)O)C(=O)O DQUJEUCGKDJODK-KDURUIRLSA-N 0.000 description 1
- QXKPBCBCFMFTAE-FOLQHYEOSA-N (2R,6S)-2,6-diaminoheptanedioic acid (2S)-2,6-diaminohexanoic acid Chemical compound N[C@@H](CCCCN)C(=O)O.N[C@@H](CCC[C@@H](N)C(=O)O)C(=O)O QXKPBCBCFMFTAE-FOLQHYEOSA-N 0.000 description 1
- LQGBFOWBAMWUHN-MOPGFXCFSA-N (2R,6S)-2-amino-6-[bis(phenylmethoxycarbonyl)amino]heptanedioic acid Chemical compound C(C1=CC=CC=C1)OC(=O)N([C@@H](CCC[C@@H](N)C(=O)O)C(=O)O)C(=O)OCC1=CC=CC=C1 LQGBFOWBAMWUHN-MOPGFXCFSA-N 0.000 description 1
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- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- PCHGTXYLEAQWOM-UHFFFAOYSA-N hydron;methyl 2-acetamido-6-aminohexanoate;chloride Chemical compound Cl.COC(=O)C(NC(C)=O)CCCCN PCHGTXYLEAQWOM-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical class [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- IESDGNYHXIOKRW-LEOABGAYSA-N tuftsin Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCNC(N)=N)C(O)=O IESDGNYHXIOKRW-LEOABGAYSA-N 0.000 description 1
- 229940035670 tuftsin Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/16—Eight-membered rings
- C07D313/18—Eight-membered rings not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/595,169 US4565653A (en) | 1984-03-30 | 1984-03-30 | Acyltripeptide immunostimulants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851278L true NO851278L (no) | 1985-10-01 |
Family
ID=24382038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851278A NO851278L (no) | 1984-03-30 | 1985-03-29 | Fremgangsmaate for fremstilling av acyltripeptider og mellomprodukter for anvendelse ved fremgangsmaaten |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4565653A (de) |
| EP (1) | EP0157572A3 (de) |
| JP (1) | JPS60224699A (de) |
| KR (1) | KR870000372B1 (de) |
| AU (2) | AU552919B2 (de) |
| CA (1) | CA1270098A (de) |
| DD (1) | DD239406A5 (de) |
| DK (1) | DK142485A (de) |
| EG (1) | EG17928A (de) |
| ES (1) | ES8605821A1 (de) |
| FI (1) | FI851271L (de) |
| GR (1) | GR850783B (de) |
| HU (1) | HU198086B (de) |
| IL (1) | IL74758A (de) |
| NO (1) | NO851278L (de) |
| NZ (1) | NZ211634A (de) |
| PH (1) | PH21303A (de) |
| PL (1) | PL252659A1 (de) |
| PT (1) | PT80181B (de) |
| ZA (1) | ZA852335B (de) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1295784C (en) * | 1985-11-25 | 1992-02-11 | James Patrick Rizzi | Peptide immunostimulants |
| JPH0718039B2 (ja) * | 1986-03-26 | 1995-03-01 | 株式会社豊田自動織機製作所 | 粉末付加亜鉛めっき鋼板の製造方法 |
| WO1988001613A1 (en) * | 1986-08-27 | 1988-03-10 | Pfizer Inc. | Crystalline n-(s-3-methylheptanoyl)-d-gamma-glutamyl-glycyl-d-alanine, and processes and intermediates therefor |
| WO1988001612A1 (en) * | 1986-08-27 | 1988-03-10 | Pfizer Inc. | Processes and intermediates for n-(s-3-alkyl-heptanoyl)-d-gamma-glutamyl-glycyl-d-alanine |
| DE3700173A1 (de) * | 1987-01-05 | 1988-07-14 | Hoechst Ag | Verfahren zur herstellung von lipophilen aminosaeurederivaten sowie lipophile aminosaeurederivate |
| DE3820528A1 (de) * | 1988-06-16 | 1989-12-21 | Bayer Ag | Mittel zur insekten- und milbenabwehr |
| US5134225A (en) * | 1989-02-21 | 1992-07-28 | Pfizer Inc. | Processes and intermediates for N-(S-3-alkyl-heptanoyl)-D-gamma-glutamyl-D-alanine |
| US5185464A (en) * | 1989-02-21 | 1993-02-09 | Pfizer Inc. | Crystalline N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor |
| US5136020A (en) * | 1989-02-21 | 1992-08-04 | Pfizer Inc. | Crystalline n-(s-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor |
| US5245079A (en) * | 1989-02-21 | 1993-09-14 | Pfizer Inc. | Processes and intermediates for N-(S-3-alkyl-heptanoyl)-D-gamma-glutamyl-glycyl-D-alanine |
| US5248820A (en) * | 1989-02-21 | 1993-09-28 | Pfizer Inc. | Crystalline N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor |
| WO1994008947A1 (en) * | 1992-10-15 | 1994-04-28 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Novel amino acid derivative |
| US5798387A (en) * | 1992-10-15 | 1998-08-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Amino acid derivatives |
| US5545553A (en) * | 1994-09-26 | 1996-08-13 | The Rockefeller University | Glycosyltransferases for biosynthesis of oligosaccharides, and genes encoding them |
| US7795210B2 (en) * | 2001-10-10 | 2010-09-14 | Novo Nordisk A/S | Protein remodeling methods and proteins/peptides produced by the methods |
| US7399613B2 (en) * | 2001-10-10 | 2008-07-15 | Neose Technologies, Inc. | Sialic acid nucleotide sugars |
| US7157277B2 (en) * | 2001-11-28 | 2007-01-02 | Neose Technologies, Inc. | Factor VIII remodeling and glycoconjugation of Factor VIII |
| US8008252B2 (en) * | 2001-10-10 | 2011-08-30 | Novo Nordisk A/S | Factor VII: remodeling and glycoconjugation of Factor VII |
| WO2004099231A2 (en) * | 2003-04-09 | 2004-11-18 | Neose Technologies, Inc. | Glycopegylation methods and proteins/peptides produced by the methods |
| US7173003B2 (en) * | 2001-10-10 | 2007-02-06 | Neose Technologies, Inc. | Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF |
| US7696163B2 (en) | 2001-10-10 | 2010-04-13 | Novo Nordisk A/S | Erythropoietin: remodeling and glycoconjugation of erythropoietin |
| US7214660B2 (en) | 2001-10-10 | 2007-05-08 | Neose Technologies, Inc. | Erythropoietin: remodeling and glycoconjugation of erythropoietin |
| MXPA04012496A (es) * | 2002-06-21 | 2005-09-12 | Novo Nordisk Healthcare Ag | Glicoformos del factor vii pegilados. |
| BRPI0408358A (pt) * | 2003-03-14 | 2006-03-21 | Neose Technologies Inc | polìmeros hidrossolúveis ramificados e seus conjugados |
| EP1613261A4 (de) * | 2003-04-09 | 2011-01-26 | Novo Nordisk As | Intrazelluläre bildung von peptidkonjugaten |
| US8791070B2 (en) | 2003-04-09 | 2014-07-29 | Novo Nordisk A/S | Glycopegylated factor IX |
| AU2004240553A1 (en) | 2003-05-09 | 2004-12-02 | Neose Technologies, Inc. | Compositions and methods for the preparation of human growth hormone glycosylation mutants |
| WO2005012484A2 (en) | 2003-07-25 | 2005-02-10 | Neose Technologies, Inc. | Antibody-toxin conjugates |
| US7842661B2 (en) * | 2003-11-24 | 2010-11-30 | Novo Nordisk A/S | Glycopegylated erythropoietin formulations |
| US20080305992A1 (en) * | 2003-11-24 | 2008-12-11 | Neose Technologies, Inc. | Glycopegylated erythropoietin |
| US8633157B2 (en) * | 2003-11-24 | 2014-01-21 | Novo Nordisk A/S | Glycopegylated erythropoietin |
| US20070254834A1 (en) * | 2003-11-24 | 2007-11-01 | Defrees Shawn | Glycopegylated Erythropoietin |
| EP1694274B1 (de) * | 2003-12-03 | 2013-04-24 | BioGeneriX AG | Glykopegylierter Granulocyten-Kolonie-stimulierender Faktor |
| US20060040856A1 (en) * | 2003-12-03 | 2006-02-23 | Neose Technologies, Inc. | Glycopegylated factor IX |
| US7956032B2 (en) * | 2003-12-03 | 2011-06-07 | Novo Nordisk A/S | Glycopegylated granulocyte colony stimulating factor |
| US20080318850A1 (en) * | 2003-12-03 | 2008-12-25 | Neose Technologies, Inc. | Glycopegylated Factor Ix |
| CA2552892C (en) * | 2004-01-08 | 2014-08-05 | Neose Technologies, Inc. | O-linked glycosylation of peptides |
| WO2006010143A2 (en) | 2004-07-13 | 2006-01-26 | Neose Technologies, Inc. | Branched peg remodeling and glycosylation of glucagon-like peptide-1 [glp-1] |
| US8268967B2 (en) * | 2004-09-10 | 2012-09-18 | Novo Nordisk A/S | Glycopegylated interferon α |
| EP1814573B1 (de) | 2004-10-29 | 2016-03-09 | ratiopharm GmbH | Remodellierung und glykopegylierung von fibroblasten-wachstumsfaktor (fgf) |
| JP2008526864A (ja) * | 2005-01-06 | 2008-07-24 | ネオス テクノロジーズ インコーポレイテッド | 糖断片を用いる糖結合 |
| ES2449195T3 (es) * | 2005-01-10 | 2014-03-18 | Ratiopharm Gmbh | Factor estimulante de colonias de granulocitos glicopegilado |
| WO2006105426A2 (en) * | 2005-03-30 | 2006-10-05 | Neose Technologies, Inc. | Manufacturing process for the production of peptides grown in insect cell lines |
| EP1871795A4 (de) * | 2005-04-08 | 2010-03-31 | Biogenerix Ag | Zusammensetzungen und verfahren zur herstellung von glycosylierungsmutanten eines proteaseresistenten menschlichen wachstumshormons |
| US20080255026A1 (en) * | 2005-05-25 | 2008-10-16 | Glycopegylated Factor 1X | Glycopegylated Factor Ix |
| US20070105755A1 (en) | 2005-10-26 | 2007-05-10 | Neose Technologies, Inc. | One pot desialylation and glycopegylation of therapeutic peptides |
| AU2006280932A1 (en) * | 2005-08-19 | 2007-02-22 | Novo Nordisk A/S | Glycopegylated factor VII and factor Vila |
| US20090048440A1 (en) * | 2005-11-03 | 2009-02-19 | Neose Technologies, Inc. | Nucleotide Sugar Purification Using Membranes |
| CN101516388B (zh) * | 2006-07-21 | 2012-10-31 | 诺和诺德公司 | 通过o-联糖基化序列的肽的糖基化 |
| WO2008057683A2 (en) * | 2006-10-03 | 2008-05-15 | Novo Nordisk A/S | Methods for the purification of polypeptide conjugates |
| DK2068907T3 (en) * | 2006-10-04 | 2018-01-15 | Novo Nordisk As | GLYCEROL BOND PEGYLED SUGAR AND GLYCOPE Peptides |
| US20080207487A1 (en) * | 2006-11-02 | 2008-08-28 | Neose Technologies, Inc. | Manufacturing process for the production of polypeptides expressed in insect cell-lines |
| KR20100016160A (ko) * | 2007-04-03 | 2010-02-12 | 바이오제너릭스 에이지 | 글리코페길화 ｇ―ｃｓｆ를 이용하는 치료 방법 |
| US20090053167A1 (en) * | 2007-05-14 | 2009-02-26 | Neose Technologies, Inc. | C-, S- and N-glycosylation of peptides |
| JP2010531135A (ja) * | 2007-06-04 | 2010-09-24 | ノボ ノルディスク アクティーゼルスカブ | Ｎ−アセチルグルコサミニルトランスフェラーゼを使用したｏ結合型グリコシル化 |
| WO2008154639A2 (en) * | 2007-06-12 | 2008-12-18 | Neose Technologies, Inc. | Improved process for the production of nucleotide sugars |
| US8207112B2 (en) * | 2007-08-29 | 2012-06-26 | Biogenerix Ag | Liquid formulation of G-CSF conjugate |
| CN102037004A (zh) * | 2008-01-08 | 2011-04-27 | 生物种属学股份公司 | 使用寡糖基转移酶的多肽的糖缀合 |
| ES2476690T3 (es) | 2008-02-27 | 2014-07-15 | Novo Nordisk A/S | Moléculas conjugadas del Factor VIII |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322341A (en) * | 1980-05-13 | 1982-03-30 | Fujisawa Pharmaceutical Co | Peptide, process for preparation thereof and use thereof |
| DK156252C (da) * | 1979-07-31 | 1989-12-18 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af di-, tri- eller tetrapeptidderivater eller salte deraf |
| DE3070278D1 (en) * | 1979-10-11 | 1985-04-18 | Fujisawa Pharmaceutical Co | Peptides, processes for their preparation and pharmaceutical compositions containing them |
| GR81332B (de) * | 1980-12-01 | 1984-12-11 | Fujisawa Pharmaceutical Co | |
| US4493794A (en) * | 1980-12-31 | 1985-01-15 | Fujisawa Pharmaceutical Co., Ltd. | Peptide, process for preparation thereof and use thereof |
-
1984
- 1984-03-30 US US06/595,169 patent/US4565653A/en not_active Expired - Fee Related
-
1985
- 1985-03-26 EP EP85302065A patent/EP0157572A3/de not_active Withdrawn
- 1985-03-26 PH PH32046A patent/PH21303A/en unknown
- 1985-03-27 ES ES541620A patent/ES8605821A1/es not_active Expired
- 1985-03-28 CA CA000477796A patent/CA1270098A/en not_active Expired - Fee Related
- 1985-03-28 GR GR850783A patent/GR850783B/el unknown
- 1985-03-28 ZA ZA852335A patent/ZA852335B/xx unknown
- 1985-03-28 DD DD85274551A patent/DD239406A5/de not_active IP Right Cessation
- 1985-03-28 EG EG201/85A patent/EG17928A/xx active
- 1985-03-28 PT PT80181A patent/PT80181B/pt not_active IP Right Cessation
- 1985-03-29 NZ NZ211634A patent/NZ211634A/xx unknown
- 1985-03-29 PL PL25265985A patent/PL252659A1/xx unknown
- 1985-03-29 IL IL74758A patent/IL74758A/xx unknown
- 1985-03-29 AU AU40523/85A patent/AU552919B2/en not_active Ceased
- 1985-03-29 NO NO851278A patent/NO851278L/no unknown
- 1985-03-29 KR KR1019850002106A patent/KR870000372B1/ko not_active IP Right Cessation
- 1985-03-29 DK DK142485A patent/DK142485A/da not_active Application Discontinuation
- 1985-03-29 FI FI851271A patent/FI851271L/fi not_active Application Discontinuation
- 1985-03-29 HU HU851217A patent/HU198086B/hu unknown
- 1985-03-29 JP JP60066380A patent/JPS60224699A/ja active Pending
-
1986
- 1986-04-22 AU AU56476/86A patent/AU566460B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DK142485A (da) | 1985-10-01 |
| ES541620A0 (es) | 1986-04-01 |
| PH21303A (en) | 1987-09-28 |
| HU198086B (en) | 1989-07-28 |
| HUT37443A (en) | 1985-12-28 |
| AU566460B2 (en) | 1987-10-22 |
| DK142485D0 (da) | 1985-03-29 |
| JPS60224699A (ja) | 1985-11-09 |
| FI851271L (fi) | 1985-10-01 |
| KR850006939A (ko) | 1985-10-25 |
| US4565653A (en) | 1986-01-21 |
| PT80181A (en) | 1985-04-01 |
| EP0157572A2 (de) | 1985-10-09 |
| IL74758A (en) | 1988-06-30 |
| PT80181B (en) | 1987-03-20 |
| ZA852335B (en) | 1986-11-26 |
| NZ211634A (en) | 1988-10-28 |
| IL74758A0 (en) | 1985-06-30 |
| DD239406A5 (de) | 1986-09-24 |
| GR850783B (de) | 1985-11-25 |
| KR870000372B1 (ko) | 1987-03-06 |
| FI851271A0 (fi) | 1985-03-29 |
| AU5647686A (en) | 1986-09-04 |
| EP0157572A3 (de) | 1987-01-07 |
| AU4052385A (en) | 1985-10-03 |
| EG17928A (en) | 1991-08-30 |
| CA1270098A (en) | 1990-06-05 |
| PL252659A1 (en) | 1985-11-19 |
| ES8605821A1 (es) | 1986-04-01 |
| AU552919B2 (en) | 1986-06-26 |
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