CH657859A5 - Derives d'aminopropylaminobleomycine et procede pour leur fabrication. - Google Patents
Derives d'aminopropylaminobleomycine et procede pour leur fabrication. Download PDFInfo
- Publication number
- CH657859A5 CH657859A5 CH7478/82A CH747882A CH657859A5 CH 657859 A5 CH657859 A5 CH 657859A5 CH 7478/82 A CH7478/82 A CH 7478/82A CH 747882 A CH747882 A CH 747882A CH 657859 A5 CH657859 A5 CH 657859A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- substituted
- amino
- groups
- benzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 71
- -1 methyloxy group Chemical group 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 46
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000004970 halomethyl group Chemical group 0.000 claims description 8
- MRNLLBXPSWMYCK-UHFFFAOYSA-N 2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[3-[4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(1h-imidazol-5-y Chemical compound N=1C(C=2SC=C(N=2)C(O)=O)=CSC=1CCNC(=O)C(C(O)C)NC(=O)C(C)C(O)C(C)NC(=O)C(C(OC1C(C(O)C(O)C(CO)O1)OC1C(C(OC(N)=O)C(O)C(CO)O1)O)C=1NC=NC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C MRNLLBXPSWMYCK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 108700023993 bleomycinic acid Proteins 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000005427 anthranyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- QXFKYWUVOXBSFV-UHFFFAOYSA-N cycloundecanecarbaldehyde Chemical compound O=CC1CCCCCCCCCC1 QXFKYWUVOXBSFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 229910010277 boron hydride Inorganic materials 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 32
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 28
- 239000010949 copper Substances 0.000 description 28
- 229910052802 copper Inorganic materials 0.000 description 27
- 239000012153 distilled water Substances 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 238000010521 absorption reaction Methods 0.000 description 24
- 229940095076 benzaldehyde Drugs 0.000 description 22
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 108010006654 Bleomycin Proteins 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 229960001561 bleomycin Drugs 0.000 description 11
- 229920001429 chelating resin Polymers 0.000 description 11
- 206010016629 fibroma Diseases 0.000 description 11
- 206010049444 fibromatosis Diseases 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000007853 buffer solution Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 206010061924 Pulmonary toxicity Diseases 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- IGGUWVNICWZJQU-UHFFFAOYSA-N cyclooctanecarbaldehyde Chemical compound O=CC1CCCCCCC1 IGGUWVNICWZJQU-UHFFFAOYSA-N 0.000 description 7
- 231100000374 pneumotoxicity Toxicity 0.000 description 7
- 230000002685 pulmonary effect Effects 0.000 description 7
- 230000007047 pulmonary toxicity Effects 0.000 description 7
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- CEQNYRUUCKQKLM-UHFFFAOYSA-N bis(3-aminopropyl)-diethylazanium Chemical class NCCC[N+](CC)(CC)CCCN CEQNYRUUCKQKLM-UHFFFAOYSA-N 0.000 description 5
- QQKBJFROHMTBDZ-UHFFFAOYSA-N bis(3-aminopropyl)-dimethylazanium Chemical class NCCC[N+](C)(C)CCCN QQKBJFROHMTBDZ-UHFFFAOYSA-N 0.000 description 5
- YPIVEQUKRJQETE-UHFFFAOYSA-N cyclotridecanecarbaldehyde Chemical compound O=CC1CCCCCCCCCCCC1 YPIVEQUKRJQETE-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FHKJZFASBMEEOR-UHFFFAOYSA-N 3,4-bis[(4-methoxyphenyl)methoxy]benzaldehyde Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=C(OC)C=C1 FHKJZFASBMEEOR-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 3
- MWSNYBOKRSGWAN-UHFFFAOYSA-N 2-(4-chlorophenyl)acetaldehyde Chemical compound ClC1=CC=C(CC=O)C=C1 MWSNYBOKRSGWAN-UHFFFAOYSA-N 0.000 description 3
- BLDFSDCBQJUWFG-UHFFFAOYSA-N 2-(methylamino)-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(NC)C(O)C1=CC=CC=C1 BLDFSDCBQJUWFG-UHFFFAOYSA-N 0.000 description 3
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- OSINZLLLLCUKJH-UHFFFAOYSA-N 4-methylcyclohexanemethanol Chemical compound CC1CCC(CO)CC1 OSINZLLLLCUKJH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 101001095088 Homo sapiens Melanoma antigen preferentially expressed in tumors Proteins 0.000 description 3
- 102100037020 Melanoma antigen preferentially expressed in tumors Human genes 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- FWMBCNGLMRSLPH-UHFFFAOYSA-N O.OC=O.CC(O)=O Chemical compound O.OC=O.CC(O)=O FWMBCNGLMRSLPH-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001962 electrophoresis Methods 0.000 description 3
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 229920001179 medium density polyethylene Polymers 0.000 description 3
- 239000004701 medium-density polyethylene Substances 0.000 description 3
- DWLUHTUYTBWOLO-UHFFFAOYSA-N methylenedioxybenzylamphetamine Chemical compound C=1C=C2OCOC2=CC=1CC(C)NCC1=CC=CC=C1 DWLUHTUYTBWOLO-UHFFFAOYSA-N 0.000 description 3
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical class CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 2
- OWKMBCMNEJTMAP-UHFFFAOYSA-N 3,4-bis[(3,4-dichlorophenyl)methoxy]benzaldehyde Chemical compound C1=C(Cl)C(Cl)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=C(Cl)C(Cl)=C1 OWKMBCMNEJTMAP-UHFFFAOYSA-N 0.000 description 2
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 2
- HBEMLFGLHHJCBQ-UHFFFAOYSA-N 4-(cyclooctylmethoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1CCCCCCC1 HBEMLFGLHHJCBQ-UHFFFAOYSA-N 0.000 description 2
- JYYIQZAJIGQRLX-UHFFFAOYSA-N 4-[(4-phenylmethoxyphenyl)methoxy]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC(C=C1)=CC=C1OCC1=CC=CC=C1 JYYIQZAJIGQRLX-UHFFFAOYSA-N 0.000 description 2
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001147844 Streptomyces verticillus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XQUGCIZPOFPGES-UHFFFAOYSA-N bis(3-aminopropyl)-benzyl-methylazanium Chemical class NCCC[N+](C)(CCCN)CC1=CC=CC=C1 XQUGCIZPOFPGES-UHFFFAOYSA-N 0.000 description 2
- MBJCCBPJQBXDKR-UHFFFAOYSA-N bis(3-aminopropyl)-dibutylazanium Chemical class CCCC[N+](CCCC)(CCCN)CCCN MBJCCBPJQBXDKR-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/003—Peptides being substituted by heterocyclic radicals, e.g. bleomycin, phleomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- Y10S930/19—Antibiotic
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56210449A JPS58116497A (ja) | 1981-12-29 | 1981-12-29 | アミノプロピルアミノブレオマイシン誘導体及びその製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH657859A5 true CH657859A5 (fr) | 1986-09-30 |
Family
ID=16589508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7478/82A CH657859A5 (fr) | 1981-12-29 | 1982-12-22 | Derives d'aminopropylaminobleomycine et procede pour leur fabrication. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4537880A (en, 2012) |
| JP (1) | JPS58116497A (en, 2012) |
| KR (1) | KR880002610B1 (en, 2012) |
| AT (1) | AT380021B (en, 2012) |
| CA (1) | CA1244824A (en, 2012) |
| CH (1) | CH657859A5 (en, 2012) |
| CS (1) | CS237334B2 (en, 2012) |
| DE (1) | DE3247199A1 (en, 2012) |
| DK (1) | DK576482A (en, 2012) |
| ES (1) | ES8402596A1 (en, 2012) |
| FR (1) | FR2519638B1 (en, 2012) |
| GB (1) | GB2112781B (en, 2012) |
| HU (1) | HU187836B (en, 2012) |
| IL (1) | IL67581A (en, 2012) |
| IT (1) | IT1210711B (en, 2012) |
| NL (1) | NL8204857A (en, 2012) |
| SE (1) | SE465034B (en, 2012) |
| YU (1) | YU43287B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952466A (en) * | 1997-11-12 | 1999-09-14 | Eli Lilly And Company | Reductive alkylation of glycopeptide antibiotics |
| ID18900A (id) * | 1996-11-21 | 1998-05-20 | Lilly Co Eli | Alkilasi menurun dari gliko peptida anti biotik |
| EP3002003A1 (de) * | 2014-09-30 | 2016-04-06 | Basf Se | Verwendung neuartiger cyclischer Carbaldehyde als Aromastoff |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US30451A (en) * | 1860-10-23 | Clothes-squeezer | ||
| GB1292081A (en) * | 1969-02-15 | 1972-10-11 | Zaidan Hojin Biseibutsu | Process for producing bleomycin antibiotics |
| US3846400A (en) * | 1969-02-15 | 1974-11-05 | Microbial Chem Res Found | Novel process for producing antibiotics bleomycin |
| DE2006448A1 (de) * | 1970-02-12 | 1971-08-19 | Konus Kessel Gesellschaft fur Wärmetechnik mbH &Co KG, 6832 Hocken heim | Kesselanlage zur Erwärmung von im Betneb nicht siedenden Flüssigkeiten |
| US3922262A (en) * | 1971-04-28 | 1975-11-25 | Nippon Kayaku Kk | N-Substituted derivatives of bleomycins |
| GB1360312A (en) * | 1971-04-28 | 1974-07-17 | Nippon Kayaku Kk | N-substituted derivatives of bleomycins |
| JPS5231875B2 (en, 2012) * | 1972-02-17 | 1977-08-17 | ||
| JPS5463089A (en) * | 1977-10-14 | 1979-05-21 | Nippon Kayaku Co Ltd | Preparation of 3-(s)-1' phenylethylaminopropylamino-bleomycin and its non-toxic salt |
| US4195018A (en) * | 1977-07-01 | 1980-03-25 | Nippon Kayaku Kabushiki Kaisha | 3-[(S)-1'-Phenylethylamino]propylaminobleomycin, non-toxic salt thereof, and method for producing same |
| US4267102A (en) * | 1979-03-05 | 1981-05-12 | Nippon Kayaku Kabushiki Kaisha | Bleomycin group antibiotics |
-
1981
- 1981-12-29 JP JP56210449A patent/JPS58116497A/ja active Granted
-
1982
- 1982-12-15 CA CA000417731A patent/CA1244824A/en not_active Expired
- 1982-12-16 NL NL8204857A patent/NL8204857A/nl not_active Application Discontinuation
- 1982-12-21 DE DE19823247199 patent/DE3247199A1/de not_active Withdrawn
- 1982-12-22 CH CH7478/82A patent/CH657859A5/fr not_active IP Right Cessation
- 1982-12-23 GB GB08236626A patent/GB2112781B/en not_active Expired
- 1982-12-27 ES ES518580A patent/ES8402596A1/es not_active Expired
- 1982-12-27 SE SE8207408A patent/SE465034B/sv not_active IP Right Cessation
- 1982-12-27 AT AT0469382A patent/AT380021B/de not_active IP Right Cessation
- 1982-12-28 DK DK576482A patent/DK576482A/da not_active Application Discontinuation
- 1982-12-28 CS CS829910A patent/CS237334B2/cs unknown
- 1982-12-28 YU YU2905/82A patent/YU43287B/xx unknown
- 1982-12-28 IL IL67581A patent/IL67581A/xx unknown
- 1982-12-28 HU HU824179A patent/HU187836B/hu not_active IP Right Cessation
- 1982-12-28 IT IT8249765A patent/IT1210711B/it active
- 1982-12-29 KR KR8205792A patent/KR880002610B1/ko not_active Expired
- 1982-12-29 FR FR8222035A patent/FR2519638B1/fr not_active Expired
-
1984
- 1984-07-27 US US06/635,096 patent/US4537880A/en not_active Expired - Fee Related
-
1985
- 1985-06-12 US US06/743,738 patent/US4568490A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2519638B1 (fr) | 1985-11-29 |
| KR880002610B1 (ko) | 1988-12-04 |
| HU187836B (en) | 1986-02-28 |
| SE8207408D0 (sv) | 1982-12-27 |
| KR840002853A (ko) | 1984-07-21 |
| SE8207408L (sv) | 1983-06-30 |
| CS237334B2 (en) | 1985-07-16 |
| ES518580A0 (es) | 1984-02-01 |
| FR2519638A1 (fr) | 1983-07-18 |
| IL67581A (en) | 1986-03-31 |
| IL67581A0 (en) | 1983-05-15 |
| US4537880A (en) | 1985-08-27 |
| JPS58116497A (ja) | 1983-07-11 |
| IT8249765A0 (it) | 1982-12-28 |
| ES8402596A1 (es) | 1984-02-01 |
| YU290582A (en) | 1984-12-31 |
| NL8204857A (nl) | 1983-07-18 |
| US4568490A (en) | 1986-02-04 |
| AT380021B (de) | 1986-03-25 |
| GB2112781B (en) | 1985-12-18 |
| DE3247199A1 (de) | 1983-07-07 |
| DK576482A (da) | 1983-06-30 |
| YU43287B (en) | 1989-06-30 |
| GB2112781A (en) | 1983-07-27 |
| JPS636078B2 (en, 2012) | 1988-02-08 |
| ATA469382A (de) | 1985-08-15 |
| IT1210711B (it) | 1989-09-20 |
| SE465034B (sv) | 1991-07-15 |
| CA1244824A (en) | 1988-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |