FI120693B - Menetelmä tiettyjen atsasykloheksapeptidien valmistamiseksi - Google Patents
Menetelmä tiettyjen atsasykloheksapeptidien valmistamiseksi Download PDFInfo
- Publication number
- FI120693B FI120693B FI973281A FI973281A FI120693B FI 120693 B FI120693 B FI 120693B FI 973281 A FI973281 A FI 973281A FI 973281 A FI973281 A FI 973281A FI 120693 B FI120693 B FI 120693B
- Authority
- FI
- Finland
- Prior art keywords
- compound
- process according
- formula
- seq
- ethylenediamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 18
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910000085 borane Inorganic materials 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 3
- 229910007926 ZrCl Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- -1 Hydra-us Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 5
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 108010049047 Echinocandins Proteins 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- 241000144175 Lophium arboricola Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910007932 ZrCl4 Inorganic materials 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- OJVZUXCPPHYAGF-UHFFFAOYSA-N phenylsulfanylbenzene;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=CC=CC=1SC1=CC=CC=C1 OJVZUXCPPHYAGF-UHFFFAOYSA-N 0.000 description 1
- VBOGDLCGFBSZKS-UHFFFAOYSA-N phenylsulfanylbenzene;trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[SH+]C1=CC=CC=C1 VBOGDLCGFBSZKS-UHFFFAOYSA-N 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- 235000014101 wine Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods
- A61B17/04—Surgical instruments, devices or methods for suturing wounds; Holders or packages for needles or suture materials
- A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
- A61B17/06114—Packages or dispensers for needles or sutures
- A61B17/06133—Packages or dispensers for needles or sutures of parallelepipedal shape, e.g. made of rectangular or slightly oval panels
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods
- A61B17/04—Surgical instruments, devices or methods for suturing wounds; Holders or packages for needles or suture materials
- A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
- A61B17/06114—Packages or dispensers for needles or sutures
- A61B2017/06142—Packages or dispensers for needles or sutures having needle- or suture- retaining members, e.g. holding tabs or needle parks
-
- 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
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Dentistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medical Informatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38661895 | 1995-02-10 | ||
| US08/386,618 US5552521A (en) | 1995-02-10 | 1995-02-10 | Process for preparing certain aza cyclohexapeptides |
| PCT/US1996/001523 WO1996024613A1 (en) | 1995-02-10 | 1996-02-06 | A process for preparing certain aza cyclohexapeptides |
| US9601523 | 1996-02-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI973281A0 FI973281A0 (fi) | 1997-08-08 |
| FI973281L FI973281L (fi) | 1997-08-08 |
| FI120693B true FI120693B (fi) | 2010-01-29 |
Family
ID=23526350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI973281A FI120693B (fi) | 1995-02-10 | 1997-08-08 | Menetelmä tiettyjen atsasykloheksapeptidien valmistamiseksi |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5552521A (cs) |
| EP (1) | EP0808330B1 (cs) |
| CN (1) | CN1127515C (cs) |
| AR (2) | AR001081A1 (cs) |
| AT (1) | ATE309266T1 (cs) |
| AU (1) | AU692071B2 (cs) |
| BR (1) | BR9607721A (cs) |
| CA (1) | CA2211314C (cs) |
| CZ (2) | CZ286683B6 (cs) |
| DE (1) | DE69635405T2 (cs) |
| EA (1) | EA000564B1 (cs) |
| ES (1) | ES2249778T3 (cs) |
| FI (1) | FI120693B (cs) |
| HR (1) | HRP960054B1 (cs) |
| HU (1) | HU229780B1 (cs) |
| NZ (1) | NZ302967A (cs) |
| SK (1) | SK283115B6 (cs) |
| TW (1) | TW515805B (cs) |
| WO (1) | WO1996024613A1 (cs) |
| YU (1) | YU49459B (cs) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU692043B2 (en) * | 1994-08-23 | 1998-05-28 | Merck & Co., Inc. | An improved process for preparing side chain derivatives of cyclohexapeptidyl lipopeptides |
| ATE223226T1 (de) * | 1994-09-16 | 2002-09-15 | Merck & Co Inc | Azazyklohexapeptid-verbindungen |
| US5952300A (en) * | 1996-04-19 | 1999-09-14 | Merck & Co., Inc. | Antifungal compositions |
| HRP970318B1 (en) * | 1996-06-14 | 2002-06-30 | Merck & Co Inc | A process for preparing certain aza cyclohexapeptides |
| US6069126A (en) * | 1996-09-12 | 2000-05-30 | Merck & Co., Inc. | Antifungal combination therapy |
| US5936062A (en) * | 1997-06-12 | 1999-08-10 | Merck & Co., Inc. | Process for preparing certain aza cyclohexapeptides |
| AU1517900A (en) * | 1998-10-28 | 2000-05-15 | Eli Lilly And Company | Photochemical process for making 1-deoxy-2-keto derivatives |
| AR035808A1 (es) * | 2001-04-12 | 2004-07-14 | Merck & Co Inc | Proceso de deshidratacion capaz de minimizar la epimerizacion de un grupo hidroxilo por ciertas equinocandinas |
| US7214768B2 (en) * | 2002-04-08 | 2007-05-08 | Merck & Co., Inc. | Echinocandin process |
| EP1785432A1 (en) | 2005-11-15 | 2007-05-16 | Sandoz AG | Process and intermediates for the synthesis of caspofungin. |
| ES2401299T5 (es) | 2006-07-26 | 2016-04-06 | Sandoz Ag | Formulaciones de caspofungina |
| WO2009002481A1 (en) * | 2007-06-26 | 2008-12-31 | Merck & Co., Inc. | Lyophilized anti-fungal composition |
| US20090075870A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched caspofungin |
| US20090291996A1 (en) * | 2008-05-21 | 2009-11-26 | Ferenc Korodi | Caspofungin free of caspofungin Co |
| US8048853B2 (en) | 2008-06-13 | 2011-11-01 | Xellia Pharmaceuticals Aps | Process for preparing pharmaceutical compound and intermediates thereof |
| EP2183271A1 (en) * | 2008-06-25 | 2010-05-12 | TEVA Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Caspofungin free of caspofungin impurity a |
| US20100256074A1 (en) * | 2008-06-25 | 2010-10-07 | Chaim Eidelman | Processes for preparing high purity aza cyclohexapeptides |
| WO2010064219A1 (en) | 2008-12-04 | 2010-06-10 | Ranbaxy Laboratories Limited | Process for the preparation of a novel intermediate for caspofungin |
| US20120190815A1 (en) * | 2009-08-06 | 2012-07-26 | Tianhui Xu | Azacyclohexapeptide or its pharmaceutical acceptable salt, preparing method and use thereof |
| CN101792486A (zh) * | 2010-04-12 | 2010-08-04 | 浙江海正药业股份有限公司 | 一种合成醋酸卡泊芬净的方法 |
| CN102219832B (zh) | 2010-04-15 | 2013-08-21 | 上海天伟生物制药有限公司 | 一种氮杂环六肽或其盐的纯化方法 |
| CN103180336B (zh) * | 2010-09-28 | 2016-06-15 | 中化帝斯曼制药有限公司荷兰公司 | 用于分离环六肽的方法 |
| KR101514903B1 (ko) * | 2010-09-29 | 2015-04-23 | 샹하이 테크웰 바이오파마슈티컬 컴퍼니, 리미티드 | 사이클릭 리포펩타이드 화합물 또는 그의 염의 정제방법 |
| CN102367269B (zh) | 2010-11-10 | 2013-11-06 | 上海天伟生物制药有限公司 | 一种卡泊芬净类似物及其制备方法和用途 |
| CN102367268B (zh) | 2010-11-10 | 2013-11-06 | 上海天伟生物制药有限公司 | 一种卡泊芬净类似物及其用途 |
| CN102367267B (zh) | 2010-11-10 | 2013-09-04 | 上海天伟生物制药有限公司 | 一种卡泊芬净的制备方法 |
| KR101331984B1 (ko) | 2010-12-09 | 2013-11-25 | 종근당바이오 주식회사 | 카스포펀진 제조방법 및 그의 신규 중간체 |
| CN102219833A (zh) * | 2011-04-18 | 2011-10-19 | 深圳市健元医药科技有限公司 | 一种更加安全的棘白菌类抗真菌药的制备方法 |
| CN102746384B (zh) | 2011-04-22 | 2016-01-20 | 上海天伟生物制药有限公司 | 一种高纯度的卡泊芬净或其盐及其制备方法和用途 |
| AU2012248013B2 (en) | 2011-04-28 | 2016-07-14 | Unitris Biopharma Co., Ltd | Intermediate for synthesizing caspofungin and preparation method therefor |
| CN103483426A (zh) * | 2012-06-14 | 2014-01-01 | 博瑞生物医药技术(苏州)有限公司 | 一种氮杂环己肽的制备方法 |
| US9636407B2 (en) | 2012-11-20 | 2017-05-02 | Fresenius Kabi Usa, Llc | Caspofungin acetate formulations |
| EP3620462A1 (en) | 2018-09-04 | 2020-03-11 | Xellia Pharmaceuticals ApS | Process for the preparation of caspofungin |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704030A1 (de) * | 1976-02-12 | 1977-08-18 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und verwendung |
| IE910892A1 (en) * | 1990-03-19 | 1991-09-25 | Merck & Co Inc | Lipopeptide compounds |
| US5939384A (en) * | 1991-10-01 | 1999-08-17 | Merck & Co., Inc. | Cyclohexapeptidyl propanolamine compounds |
| US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US6268338B1 (en) * | 1993-04-30 | 2001-07-31 | Merck & Co., Inc. | Cyclohexapeptidyl amine compounds |
| AU692043B2 (en) * | 1994-08-23 | 1998-05-28 | Merck & Co., Inc. | An improved process for preparing side chain derivatives of cyclohexapeptidyl lipopeptides |
| ATE223226T1 (de) * | 1994-09-16 | 2002-09-15 | Merck & Co Inc | Azazyklohexapeptid-verbindungen |
-
1995
- 1995-02-10 US US08/386,618 patent/US5552521A/en not_active Expired - Lifetime
-
1996
- 1996-02-01 TW TW085101244A patent/TW515805B/zh not_active IP Right Cessation
- 1996-02-05 HR HR960054A patent/HRP960054B1/xx not_active IP Right Cessation
- 1996-02-06 ES ES96905366T patent/ES2249778T3/es not_active Expired - Lifetime
- 1996-02-06 EA EA199700170A patent/EA000564B1/ru not_active IP Right Cessation
- 1996-02-06 WO PCT/US1996/001523 patent/WO1996024613A1/en active IP Right Grant
- 1996-02-06 NZ NZ302967A patent/NZ302967A/en not_active IP Right Cessation
- 1996-02-06 EP EP96905366A patent/EP0808330B1/en not_active Expired - Lifetime
- 1996-02-06 AT AT96905366T patent/ATE309266T1/de active
- 1996-02-06 CA CA002211314A patent/CA2211314C/en not_active Expired - Lifetime
- 1996-02-06 CN CN96191834A patent/CN1127515C/zh not_active Expired - Lifetime
- 1996-02-06 DE DE69635405T patent/DE69635405T2/de not_active Expired - Lifetime
- 1996-02-06 BR BR9607721A patent/BR9607721A/pt not_active Application Discontinuation
- 1996-02-06 HU HU9901085A patent/HU229780B1/hu unknown
- 1996-02-06 SK SK1079-97A patent/SK283115B6/sk not_active IP Right Cessation
- 1996-02-06 AU AU49147/96A patent/AU692071B2/en not_active Expired
- 1996-02-06 CZ CZ19972525A patent/CZ286683B6/cs not_active IP Right Cessation
- 1996-02-07 AR AR33533596A patent/AR001081A1/es unknown
- 1996-02-09 YU YU8496A patent/YU49459B/sh unknown
-
1997
- 1997-01-14 AR ARP970100139A patent/AR005462A1/es not_active Application Discontinuation
- 1997-08-08 FI FI973281A patent/FI120693B/fi not_active IP Right Cessation
-
1999
- 1999-12-17 CZ CZ19994601A patent/CZ286767B6/cs not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI120693B (fi) | Menetelmä tiettyjen atsasykloheksapeptidien valmistamiseksi | |
| KR100249589B1 (ko) | 아자 사이클로헥사펩타이드의 제조방법 | |
| US5936062A (en) | Process for preparing certain aza cyclohexapeptides | |
| FI109542B (fi) | Menetelmä lääkeaineina käyttökelpoisten atsasykloheksapeptidiyhdisteiden valmistamiseksi | |
| US5159059A (en) | Process for reduction of certain cyclohexapeptide compounds | |
| AU712857B2 (en) | A process for preparing certain aza cyclohexapeptides | |
| KR101331984B1 (ko) | 카스포펀진 제조방법 및 그의 신규 중간체 | |
| WO1996008507A1 (en) | Aza cyclohexapeptide compounds | |
| HK1004676B (en) | A process for preparing certain aza cyclohexapeptides | |
| MXPA97006101A (en) | A procedure to prepare certain azaciclohexapepti | |
| CA2380176A1 (en) | Novel cyclohexapeptide compounds, processes for their production and their use as a pharmaceutical |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Ref document number: 120693 Country of ref document: FI |
|
| PC | Transfer of assignment of patent |
Owner name: MERCK SHARP & DOHME CORP. Free format text: MERCK SHARP & DOHME CORP. |
|
| PC | Transfer of assignment of patent |
Owner name: MERCK SHARP & DOHME CORP. |
|
| MA | Patent expired |