JPS6163290A - 新制癌性抗生物質ｎｃｓ−ｃの製造法 - Google Patents
新制癌性抗生物質ｎｃｓ−ｃの製造法Info
- Publication number
- JPS6163290A JPS6163290A JP59262494A JP26249484A JPS6163290A JP S6163290 A JPS6163290 A JP S6163290A JP 59262494 A JP59262494 A JP 59262494A JP 26249484 A JP26249484 A JP 26249484A JP S6163290 A JPS6163290 A JP S6163290A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ncs
- soluble
- substance
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000126 substance Substances 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000003327 cancerostatic effect Effects 0.000 title abstract 2
- 241000187747 Streptomyces Species 0.000 claims abstract description 11
- 239000003972 antineoplastic antibiotic Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract 3
- 239000000706 filtrate Substances 0.000 claims abstract 2
- QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 claims description 7
- 229950009268 zinostatin Drugs 0.000 claims description 7
- 101710204212 Neocarzinostatin Proteins 0.000 claims description 5
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims description 2
- QZGIWPZCWHMVQL-DZANSKTCSA-N zinostatin Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3(C3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-DZANSKTCSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 239000000843 powder Substances 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 238000004949 mass spectrometry Methods 0.000 abstract description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006149 azo coupling reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 230000036647 reaction Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 108010045882 preneocarzinostatin Proteins 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical group Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910001562 pearlite Inorganic materials 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59262494A JPS6163290A (ja) | 1984-12-12 | 1984-12-12 | 新制癌性抗生物質ｎｃｓ−ｃの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59262494A JPS6163290A (ja) | 1984-12-12 | 1984-12-12 | 新制癌性抗生物質ｎｃｓ−ｃの製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54130181A Division JPS6030679B2 (ja) | 1979-10-09 | 1979-10-09 | 新制癌性抗生物質ｎｃｓ−ｃ |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61278118A Division JPS62244385A (ja) | 1986-11-21 | 1986-11-21 | 新制癌性抗生物質ｎｃｓ−ｃの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6163290A true JPS6163290A (ja) | 1986-04-01 |
| JPS6219156B2 JPS6219156B2 (enrdf_load_stackoverflow) | 1987-04-27 |
Family
ID=17376572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59262494A Granted JPS6163290A (ja) | 1984-12-12 | 1984-12-12 | 新制癌性抗生物質ｎｃｓ−ｃの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6163290A (enrdf_load_stackoverflow) |
-
1984
- 1984-12-12 JP JP59262494A patent/JPS6163290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6219156B2 (enrdf_load_stackoverflow) | 1987-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1770204B1 (de) | Adriamycin und dessen Salze mit pharmakologisch vertraeglichen anorganischen und organischen Saeuren sowie diese enthaltende therapeutische Zusammensetzungen | |
| DE1939341C2 (de) | Cephalosporinderivate und Verfahren zur ihrer Herstellung | |
| CH630957A5 (de) | Verfahren zur herstellung von neuen antibiotischen verbindungen auf basis eines bohemsaeurekomplexes. | |
| JPS5920354B2 (ja) | 抗真菌および抗原生動物性抗生物質ならびにその製造法 | |
| JPS6012039B2 (ja) | 新規抗生物質その製法および抗菌性および抗カビ性組成物 | |
| DE68912355T2 (de) | Antibiotische Antitumor-Verbindung und Methode zu deren Herstellung. | |
| JPS6163290A (ja) | 新制癌性抗生物質ｎｃｓ−ｃの製造法 | |
| CH467336A (de) | Verfahren zur Herstellung eines neuen Antibiotikums | |
| DE3044970A1 (de) | 3',4'-dideoxyparomomycin, verfahren zu dessen herstellung und diese verbindung enthaltende arzneimittel | |
| EP0660825B1 (de) | Entzündungshemmende makrolactame (cyclamenol) | |
| DE2532589A1 (de) | Polypeptid und verfahren zur herstellung desselben und mittel mit einem gehalt desselben | |
| US3089816A (en) | Lemacidine and process for its manufacture | |
| JPS6241237B2 (enrdf_load_stackoverflow) | ||
| JPH07278041A (ja) | 抗腫瘍性物質ｂｅ−２４８１１及びその製造法 | |
| JPS6030679B2 (ja) | 新制癌性抗生物質ｎｃｓ−ｃ | |
| JP2546239B2 (ja) | 新規物質オバリシン | |
| DE2516615A1 (de) | Neues antibiotikum bn-130 und verfahren zur herstellung desselben | |
| DE2610557A1 (de) | Neues naphthacenderivat, seine herstellung und dieses enthaltende zusammensetzungen | |
| JP2775001B2 (ja) | 新抗生物質ｙｓ―８２２ａおよびその製造法 | |
| JPS59161396A (ja) | 新規抗生物質スピカマイシン | |
| KR800000003B1 (ko) | α-아미노-γ-메틸포스페닐 낙산의 제조방법 | |
| DE1593327C (de) | Verfahren zur Herstellung von Delta hoch 1,4 -Androstadien-3,17-dion, Delta hoch 1,4 -Androstadien-3,11,17-trion bzw. Delta hoch 1,4 -Androstadien-1 lalpha-ol-3,17-dion | |
| JPS6311341B2 (enrdf_load_stackoverflow) | ||
| DE2424707A1 (de) | Antibiotikum nr. 1998, seine salze mit saeuren, verfahren zu seiner herstellung, mikroorganismen zur durchfuehrung des verfahrens und arzneimittel | |
| JPS635078B2 (enrdf_load_stackoverflow) |