PL80837B1 - Process for producing bleomycin antibiotics[gb1292081a] - Google Patents
Process for producing bleomycin antibiotics[gb1292081a] Download PDFInfo
- Publication number
- PL80837B1 PL80837B1 PL1970138814A PL13881470A PL80837B1 PL 80837 B1 PL80837 B1 PL 80837B1 PL 1970138814 A PL1970138814 A PL 1970138814A PL 13881470 A PL13881470 A PL 13881470A PL 80837 B1 PL80837 B1 PL 80837B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- diaminopropane
- bleomycin
- amino
- Prior art date
Links
- 229960001561 bleomycin Drugs 0.000 title claims abstract description 71
- 108010006654 Bleomycin Proteins 0.000 title claims abstract description 67
- 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 title claims abstract description 66
- 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 9
- 229940088710 antibiotic agent Drugs 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 31
- -1 amino compound Chemical class 0.000 claims abstract description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 241001147844 Streptomyces verticillus Species 0.000 claims abstract description 10
- 235000015097 nutrients Nutrition 0.000 claims abstract description 6
- RYPPRSLFGARBNU-UHFFFAOYSA-O N[S+](C(N=N)=N)NC(=N)N Chemical compound N[S+](C(N=N)=N)NC(=N)N RYPPRSLFGARBNU-UHFFFAOYSA-O 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims description 18
- 239000002609 medium Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 238000000855 fermentation Methods 0.000 claims description 9
- 230000004151 fermentation Effects 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229940063675 spermine Drugs 0.000 claims description 8
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229940063673 spermidine Drugs 0.000 claims description 7
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 5
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 5
- JDCNYLYKGQBHJN-UHFFFAOYSA-M 3-aminopropyl(dimethyl)sulfanium;bromide Chemical compound [Br-].C[S+](C)CCCN JDCNYLYKGQBHJN-UHFFFAOYSA-M 0.000 claims description 4
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005700 Putrescine Substances 0.000 claims description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000001963 growth medium Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NQONXAAXIFYYMX-UHFFFAOYSA-N n'-(1-phenylethyl)propane-1,3-diamine Chemical compound NCCCNC(C)C1=CC=CC=C1 NQONXAAXIFYYMX-UHFFFAOYSA-N 0.000 claims description 3
- FCUCMGJGCDPONA-UHFFFAOYSA-N n'-(3-pyrrolidin-1-ylpropyl)propane-1,3-diamine Chemical compound NCCCNCCCN1CCCC1 FCUCMGJGCDPONA-UHFFFAOYSA-N 0.000 claims description 3
- RFLHDXQRFPJPRR-UHFFFAOYSA-N n'-benzylpropane-1,3-diamine Chemical compound NCCCNCC1=CC=CC=C1 RFLHDXQRFPJPRR-UHFFFAOYSA-N 0.000 claims description 3
- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 claims description 3
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 claims description 2
- SLCCHLCXVOABIB-UHFFFAOYSA-M 3-aminopropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCN SLCCHLCXVOABIB-UHFFFAOYSA-M 0.000 claims description 2
- UMVURPVUDFDTNF-UHFFFAOYSA-N 3-n-(3-aminopropyl)butane-1,3-diamine Chemical compound NCCC(C)NCCCN UMVURPVUDFDTNF-UHFFFAOYSA-N 0.000 claims description 2
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 claims description 2
- VPBWZBGZWHDNKL-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCC1 VPBWZBGZWHDNKL-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 2
- LLRMJSJSADDGPK-UHFFFAOYSA-N n'-(3-methoxypropyl)propane-1,3-diamine Chemical compound COCCCNCCCN LLRMJSJSADDGPK-UHFFFAOYSA-N 0.000 claims description 2
- MIFWXJNZWLWCGL-UHFFFAOYSA-N n'-butylpropane-1,3-diamine Chemical compound CCCCNCCCN MIFWXJNZWLWCGL-UHFFFAOYSA-N 0.000 claims description 2
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 claims description 2
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 claims description 2
- 238000002255 vaccination Methods 0.000 claims description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- LJSUIIHXGIFTAO-UHFFFAOYSA-N 3-(3-aminopropylamino)propan-1-ol Chemical compound NCCCNCCCO LJSUIIHXGIFTAO-UHFFFAOYSA-N 0.000 claims 1
- ZWKZYPOYNDWCBV-UHFFFAOYSA-N 3-acetamidopropyl(dimethyl)sulfanium;bromide Chemical compound [Br-].C[S+](C)CCCNC(C)=O ZWKZYPOYNDWCBV-UHFFFAOYSA-N 0.000 claims 1
- RBRKJNDIJJTXAW-UHFFFAOYSA-M 3-aminopropyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCN RBRKJNDIJJTXAW-UHFFFAOYSA-M 0.000 claims 1
- KGFUGLZSONHTTJ-UHFFFAOYSA-N 3-piperazin-1-ylpropane-1,1-diamine Chemical compound NC(N)CCN1CCNCC1 KGFUGLZSONHTTJ-UHFFFAOYSA-N 0.000 claims 1
- QYPPJABKJHAVHS-UHFFFAOYSA-N Agmatine Natural products NCCCCNC(N)=N QYPPJABKJHAVHS-UHFFFAOYSA-N 0.000 claims 1
- 102100027373 Melanin-concentrating hormone receptor 2 Human genes 0.000 claims 1
- 101710089759 Melanin-concentrating hormone receptor 2 Proteins 0.000 claims 1
- QYPPJABKJHAVHS-UHFFFAOYSA-P agmatinium(2+) Chemical compound NC(=[NH2+])NCCCC[NH3+] QYPPJABKJHAVHS-UHFFFAOYSA-P 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 1
- GVXYYRZMASRTPS-UHFFFAOYSA-N dimethylsulfanium chloride Chemical compound [Cl-].C[SH+]C GVXYYRZMASRTPS-UHFFFAOYSA-N 0.000 claims 1
- JZMXQIATXJJSKG-UHFFFAOYSA-N n'-(3-piperidin-1-ylpropyl)propane-1,3-diamine Chemical compound NCCCNCCCN1CCCCC1 JZMXQIATXJJSKG-UHFFFAOYSA-N 0.000 claims 1
- LODTWIFFAAIPNA-UHFFFAOYSA-N n'-[3-(1-phenylethylamino)propyl]propane-1,3-diamine Chemical compound NCCCNCCCNC(C)C1=CC=CC=C1 LODTWIFFAAIPNA-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000003641 microbiacidal effect Effects 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000009835 boiling Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229920005654 Sephadex Polymers 0.000 description 12
- 239000012507 Sephadex™ Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 108700004675 bleomycetin Proteins 0.000 description 6
- QYOAUOAXCQAEMW-UTXKDXHTSA-N bleomycin A5 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)NCCCNCCCCN)[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 QYOAUOAXCQAEMW-UTXKDXHTSA-N 0.000 description 6
- 229910000365 copper sulfate Inorganic materials 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 235000019713 millet Nutrition 0.000 description 5
- 229910000368 zinc sulfate Inorganic materials 0.000 description 5
- 229960001763 zinc sulfate Drugs 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 3
- IEDNWKCHZCVHLS-UHFFFAOYSA-N n'-(3-morpholin-4-ylpropyl)propane-1,3-diamine Chemical compound NCCCNCCCN1CCOCC1 IEDNWKCHZCVHLS-UHFFFAOYSA-N 0.000 description 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- MYGVPKMVGSXPCQ-UHFFFAOYSA-N (3-amino-4-hydroxy-4-oxobutyl)-dimethylsulfanium chloride Chemical compound [Cl-].C[S+](C)CCC(N)C(O)=O MYGVPKMVGSXPCQ-UHFFFAOYSA-N 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
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- 244000005700 microbiome Species 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- KETPHVGICLLJJT-UHFFFAOYSA-N 2-(4-aminobutyl)guanidine;hydrochloride Chemical compound Cl.NCCCCN=C(N)N KETPHVGICLLJJT-UHFFFAOYSA-N 0.000 description 1
- PDUMWBLAPMSFGD-UHFFFAOYSA-N 2-amino-4-sulfanylbutanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)CCS PDUMWBLAPMSFGD-UHFFFAOYSA-N 0.000 description 1
- UGQZFFGZKJEVIY-UHFFFAOYSA-N 2-amino-5-(dimethylamino)pentanoic acid Chemical compound CN(C)CCCC(N)C(O)=O UGQZFFGZKJEVIY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 1
- IVGOIQBXIIAVDQ-UHFFFAOYSA-M 3-aminopropyl(dimethyl)sulfanium;bromide;hydrobromide Chemical compound Br.[Br-].C[S+](C)CCCN IVGOIQBXIIAVDQ-UHFFFAOYSA-M 0.000 description 1
- RMUAXNHYNCXOIU-UHFFFAOYSA-M 3-aminopropyl(dimethyl)sulfanium;chloride Chemical compound [Cl-].C[S+](C)CCCN RMUAXNHYNCXOIU-UHFFFAOYSA-M 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- QMMDZIHRBCNPRP-UHFFFAOYSA-N 3-n-(3-aminopropyl)pentane-1,3-diamine Chemical compound NCCC(CC)NCCCN QMMDZIHRBCNPRP-UHFFFAOYSA-N 0.000 description 1
- RKOPOQDWXOQCAB-UHFFFAOYSA-N 4-aminobutanimidamide Chemical compound NCCCC(N)=N RKOPOQDWXOQCAB-UHFFFAOYSA-N 0.000 description 1
- PTAYFGHRDOMJGC-UHFFFAOYSA-N 4-aminobutyl(diaminomethylidene)azanium;hydrogen sulfate Chemical compound OS(O)(=O)=O.NCCCCN=C(N)N PTAYFGHRDOMJGC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241000501348 Merope tuber Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FOUFFVYWFNBHHH-YNGSZULRSA-N [(2r,3s,4s,5r,6r)-2-[(2r,3s,4s,5s,6s)-2-[(1r,2s)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2r,3s,4s)-5-[[(2s,3r)-1-[2-[4-[4-[3-[4-(3-aminopropylamino)butylamino]propylcarbamo 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)NCCCNCCCCNCCCN)[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=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C FOUFFVYWFNBHHH-YNGSZULRSA-N 0.000 description 1
- NBLHOLNNKJBEDC-XOGQCRKLSA-N [(2r,3s,4s,5r,6r)-2-[(2r,3s,4s,5s,6s)-2-[(1r,2s)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2r,3s,4s)-5-[[(2s,3r)-1-[2-[4-[4-[4-(diaminomethylideneamino)butylcarbamoyl]-1,3-th 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)NCCCCN=C(N)N)[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=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C NBLHOLNNKJBEDC-XOGQCRKLSA-N 0.000 description 1
- GMYNGXLEGQPRFK-UHFFFAOYSA-N [2-[2-[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[3-hydroxy-5-[[3-hydroxy-1-[2-[4-[4-(3-methylsulfinylpropylcarbamoyl)-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]-1-oxobutan-2-yl]amin Chemical compound N=1C(C=2SC=C(N=2)C(=O)NCCCS(C)=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 GMYNGXLEGQPRFK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 201000007691 actinomycosis Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 108700035333 bleomycin A6 Proteins 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- ISPYRSDWRDQNSW-UHFFFAOYSA-L manganese(II) sulfate monohydrate Chemical compound O.[Mn+2].[O-]S([O-])(=O)=O ISPYRSDWRDQNSW-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HUWUUMUEMQWJKZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-benzylpropane-1,3-diamine Chemical compound NCCCN(CCCN)CC1=CC=CC=C1 HUWUUMUEMQWJKZ-UHFFFAOYSA-N 0.000 description 1
- ZKKMLXOYLORBLV-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-ethylpropane-1,3-diamine Chemical compound NCCCN(CC)CCCN ZKKMLXOYLORBLV-UHFFFAOYSA-N 0.000 description 1
- PLSMCAPPTOOFNL-UHFFFAOYSA-N n'-(3-piperazin-1-ylpropyl)propane-1,3-diamine Chemical compound NCCCNCCCN1CCNCC1 PLSMCAPPTOOFNL-UHFFFAOYSA-N 0.000 description 1
- WUSFNOHQQLRSCV-UHFFFAOYSA-N n'-[(4-methylphenyl)methyl]propane-1,3-diamine Chemical compound CC1=CC=C(CNCCCN)C=C1 WUSFNOHQQLRSCV-UHFFFAOYSA-N 0.000 description 1
- ZHQKHTUJPJVUBJ-UHFFFAOYSA-N n'-[2-(4-methylphenyl)ethyl]propane-1,3-diamine Chemical compound CC1=CC=C(CCNCCCN)C=C1 ZHQKHTUJPJVUBJ-UHFFFAOYSA-N 0.000 description 1
- DDODLJWYWDHQFZ-UHFFFAOYSA-N n'-[2-(dimethylamino)ethyl]propane-1,3-diamine Chemical compound CN(C)CCNCCCN DDODLJWYWDHQFZ-UHFFFAOYSA-N 0.000 description 1
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 description 1
- LPMORQDXGOUXEM-UHFFFAOYSA-N n-(3-aminopropyl)-n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCNCCCN LPMORQDXGOUXEM-UHFFFAOYSA-N 0.000 description 1
- AHLVXXNNSWMQRR-UHFFFAOYSA-N n-(3-aminopropyl)-n',n'-dimethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCNCCCN AHLVXXNNSWMQRR-UHFFFAOYSA-N 0.000 description 1
- UKXSMVIDPJCDAQ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1 UKXSMVIDPJCDAQ-UHFFFAOYSA-N 0.000 description 1
- LPRTUAMEQDRMAZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]propanamide Chemical compound CCC(=O)NCCCN(C)C LPRTUAMEQDRMAZ-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1077469A JPS4832354B1 (en, 2012) | 1969-02-15 | 1969-02-15 | |
| JP44087589A JPS4832355B1 (en, 2012) | 1969-11-04 | 1969-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL80837B1 true PL80837B1 (en) | 1975-08-30 |
Family
ID=26346103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970138814A PL80837B1 (en) | 1969-02-15 | 1970-02-14 | Process for producing bleomycin antibiotics[gb1292081a] |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | USRE30451E (en, 2012) |
| AT (1) | AT295743B (en, 2012) |
| BE (1) | BE745926A (en, 2012) |
| BG (1) | BG17632A3 (en, 2012) |
| CA (1) | CA923055A (en, 2012) |
| CH (1) | CH545343A (en, 2012) |
| CS (1) | CS150904B2 (en, 2012) |
| DE (1) | DE2006446C3 (en, 2012) |
| DK (1) | DK123605B (en, 2012) |
| ES (1) | ES376555A1 (en, 2012) |
| FI (1) | FI46178C (en, 2012) |
| FR (1) | FR2034552B1 (en, 2012) |
| GB (1) | GB1292081A (en, 2012) |
| IL (1) | IL33879A (en, 2012) |
| NL (1) | NL147187B (en, 2012) |
| NO (1) | NO132875C (en, 2012) |
| PL (1) | PL80837B1 (en, 2012) |
| RO (1) | RO54829A (en, 2012) |
| SE (1) | SE360677B (en, 2012) |
| YU (1) | YU36389B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS5739751B2 (en, 2012) * | 1972-03-03 | 1982-08-23 | ||
| FR2199455A2 (en) * | 1972-09-20 | 1974-04-12 | Nippon Kayaku Kk | Bleomycin derivs |
| FR2199456A2 (en) * | 1972-09-20 | 1974-04-12 | Microbial Chem Res Found | Bleomycin derivs |
| GB1540466A (en) * | 1975-10-29 | 1979-02-14 | Meiji Seika Kaisha | Antibiotic polypeptides sf-1771 and sf-1881-b and production thereof |
| CA1090728A (en) * | 1976-02-04 | 1980-12-02 | Eli Lilly And Company | Antibiotic a-7413 mixture comprising factors a,b,c and d and a process for producing it |
| US4246400A (en) * | 1979-07-13 | 1981-01-20 | Bristol-Myers Company | Tallysomycin compounds |
| JPS58116497A (ja) | 1981-12-29 | 1983-07-11 | Microbial Chem Res Found | 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 |
| JPS58116496A (ja) | 1981-12-29 | 1983-07-11 | Nippon Kayaku Co Ltd | アミドｎ置換ブレオマイシン類 |
| JPS606698A (ja) | 1983-06-27 | 1985-01-14 | Microbial Chem Res Found | 新規な３−（４′−アミノブチルアミノ）プロピルアミノブレオマイシン誘導体及びその製造法 |
| RU2355758C2 (ru) * | 2007-04-27 | 2009-05-20 | Государственное учреждение научно-исследовательский институт по изысканию новых антибиотиков имени Г.Ф. Гаузе РАМН (ГУ НИИНА им.Г.Ф.Гаузе РАМН) | ШТАММ Streptomyces griseocarneus subsp. bleomycini ВКПМ-S887 - ПРОДУЦЕНТ БЛЕОМИЦИНА A2 И СПОСОБ ПОЛУЧЕНИЯ АНТИБИОТИКА БЛЕОМИЦИНА A2 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1970
- 1970-02-05 GB GB5666/70A patent/GB1292081A/en not_active Expired
- 1970-02-10 IL IL33879A patent/IL33879A/en unknown
- 1970-02-10 FR FR7004581A patent/FR2034552B1/fr not_active Expired
- 1970-02-11 CA CA074574A patent/CA923055A/en not_active Expired
- 1970-02-12 DK DK70170AA patent/DK123605B/da not_active IP Right Cessation
- 1970-02-12 DE DE2006446A patent/DE2006446C3/de not_active Expired
- 1970-02-13 NL NL707002104A patent/NL147187B/xx not_active IP Right Cessation
- 1970-02-13 ES ES376555A patent/ES376555A1/es not_active Expired
- 1970-02-13 CH CH207470A patent/CH545343A/de not_active IP Right Cessation
- 1970-02-13 AT AT133070A patent/AT295743B/de not_active IP Right Cessation
- 1970-02-13 YU YU00358/70A patent/YU36389B/xx unknown
- 1970-02-13 FI FI700399A patent/FI46178C/fi active
- 1970-02-13 SE SE01858/70A patent/SE360677B/xx unknown
- 1970-02-13 BE BE745926D patent/BE745926A/xx not_active IP Right Cessation
- 1970-02-13 CS CS1037A patent/CS150904B2/cs unknown
- 1970-02-14 BG BG013968A patent/BG17632A3/xx unknown
- 1970-02-14 PL PL1970138814A patent/PL80837B1/pl unknown
- 1970-02-14 NO NO526/70A patent/NO132875C/no unknown
- 1970-02-16 RO RO62478A patent/RO54829A/ro unknown
-
1979
- 1979-05-24 US US06/041,996 patent/USRE30451E/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2006446C3 (de) | 1978-08-31 |
| NO132875C (en, 2012) | 1976-01-21 |
| BE745926A (fr) | 1970-07-16 |
| CH545343A (de) | 1973-12-15 |
| DK123605B (da) | 1972-07-10 |
| AT295743B (de) | 1972-01-10 |
| BG17632A3 (bg) | 1973-11-10 |
| YU35870A (en) | 1981-11-13 |
| DE2006446A1 (en, 2012) | 1970-10-22 |
| RO54829A (en, 2012) | 1973-07-20 |
| NL7002104A (en, 2012) | 1970-08-18 |
| FI46178C (fi) | 1973-01-10 |
| FR2034552B1 (en, 2012) | 1974-01-11 |
| NO132875B (en, 2012) | 1975-10-13 |
| ES376555A1 (es) | 1972-06-16 |
| CA923055A (en) | 1973-03-20 |
| YU36389B (en) | 1983-06-30 |
| DE2006446B2 (de) | 1977-09-29 |
| FR2034552A1 (en, 2012) | 1970-12-11 |
| IL33879A0 (en) | 1970-04-20 |
| SE360677B (en, 2012) | 1973-10-01 |
| NL147187B (nl) | 1975-09-15 |
| GB1292081A (en) | 1972-10-11 |
| CS150904B2 (en, 2012) | 1973-09-17 |
| FI46178B (en, 2012) | 1972-10-02 |
| USRE30451E (en) | 1980-12-16 |
| IL33879A (en) | 1973-05-31 |
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