JPH0443912B2 - - Google Patents

Info

Publication number: JPH0443912B2
Authority: JP; Japan
Prior art keywords: compounds; fermentation; pharmaceutically acceptable; formula; compound
Prior art date: 1982-02-24
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.): Expired - Lifetime

Application number

JP58029196A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58189190A (ja

Inventor

Esu Sutamupuwara Suretsushu

Shii Furenchi Jeimuzu

Bii Tsunatsuku Josefuino

Aaru Haarii Teimoshii

Eichi Bagii Richaado

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

Priority date (The priority date 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 date listed.)

1982-02-24

Filing date

1983-02-23

Publication date

1992-07-20

1983-02-23 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1983-11-04 Publication of JPS58189190A publication Critical patent/JPS58189190A/ja

1992-07-20 Publication of JPH0443912B2 publication Critical patent/JPH0443912B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 13
239000002246 antineoplastic agent Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
241000187747 Streptomyces Species 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000000855 fermentation Methods 0.000 description 22
230000004151 fermentation Effects 0.000 description 22
239000002609 medium Substances 0.000 description 18
239000011347 resin Substances 0.000 description 18
229920005989 resin Polymers 0.000 description 18
239000000203 mixture Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
239000007788 liquid Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
229960001866 silicon dioxide Drugs 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 11
239000011734 sodium Substances 0.000 description 11
238000000862 absorption spectrum Methods 0.000 description 10
239000000039 congener Substances 0.000 description 9
XBUIKNRVGYFSHL-IAVQPKKASA-M sodium;[(1e,3r,4r,6r,7z,9z,11e)-3,6,13-trihydroxy-3-methyl-1-[(2r)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl] hydrogen phosphate Chemical compound [Na+].OC/C=C/C=C\C=C/[C@H](O)C[C@@H](OP(O)([O-])=O)[C@@](O)(C)\C=C\[C@H]1CC=CC(=O)O1 XBUIKNRVGYFSHL-IAVQPKKASA-M 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
244000005700 microbiome Species 0.000 description 8
239000000243 solution Substances 0.000 description 8
229920001817 Agar Polymers 0.000 description 7
239000008272 agar Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
240000008042 Zea mays Species 0.000 description 6
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
235000002017 Zea mays subsp mays Nutrition 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
235000005822 corn Nutrition 0.000 description 6
239000002054 inoculum Substances 0.000 description 6
239000008363 phosphate buffer Substances 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
235000013312 flour Nutrition 0.000 description 5
238000000034 method Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000012010 growth Effects 0.000 description 4
208000032839 leukemia Diseases 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
238000003756 stirring Methods 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
238000005273 aeration Methods 0.000 description 3
230000000259 anti-tumor effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000003102 growth factor Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000005917 in vivo anti-tumor Effects 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000012546 transfer Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
229920001353 Dextrin Polymers 0.000 description 2
239000004375 Dextrin Substances 0.000 description 2
208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001529936 Murinae Species 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000005862 Whey Substances 0.000 description 2
102000007544 Whey Proteins Human genes 0.000 description 2
108010046377 Whey Proteins Proteins 0.000 description 2
238000013019 agitation Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
235000013365 dairy product Nutrition 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
235000015177 dried meat Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000010265 fast atom bombardment Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229910000160 potassium phosphate Inorganic materials 0.000 description 2
235000011009 potassium phosphates Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
235000010378 sodium ascorbate Nutrition 0.000 description 2
229960005055 sodium ascorbate Drugs 0.000 description 2
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
230000003068 static effect Effects 0.000 description 2
235000003276 Apios tuberosa Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241001149669 Hanseniaspora Species 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000588653 Neisseria Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000223252 Rhodotorula Species 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
241000235070 Saccharomyces Species 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000187180 Streptomyces sp. Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
JIAYUFWCNLGCTK-IGICQAMHSA-N [(1e,7e,9e,11e)-3,6,13-trihydroxy-1-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-3-methyltrideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate Chemical compound OC/C=C/C=C/C=C/C(O)CC(OP(O)(O)=O)C(O)(C)\C=C\C1OC(=O)C=CC1O JIAYUFWCNLGCTK-IGICQAMHSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
229910000175 cerite Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940097268 cobaltous chloride hexahydrate Drugs 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
238000012136 culture method Methods 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
ZMQRJWIYMXZORG-DSWNLJKISA-N fostriecin Chemical compound OC/C=C/C=C\C=C/[C@H](O)C[C@@H](OP(O)(O)=O)[C@@](O)(C)\C=C\[C@H]1CC=CC(=O)O1 ZMQRJWIYMXZORG-DSWNLJKISA-N 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000012092 media component Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration 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
239000011574 phosphorus Substances 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
235000021309 simple sugar Nutrition 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JNYIQRMXGCWKOU-UHFFFAOYSA-M sodium methanol chloride Chemical compound [Na+].[Cl-].OC JNYIQRMXGCWKOU-UHFFFAOYSA-M 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000010563 solid-state fermentation Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012137 tryptone Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000002424 x-ray crystallography Methods 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)
Pyrane Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

JP58029196A 1982-02-24 1983-02-23 Ｃｌ１５６５化合物類，その製造方法及びそれを有効成分とする抗腫瘍剤 Granted JPS58189190A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US35170482A	1982-02-24	1982-02-24
US351704		1982-02-24
US439973		1982-11-08
US447544		1999-11-23

Publications (2)

Publication Number	Publication Date
JPS58189190A JPS58189190A (ja)	1983-11-04
JPH0443912B2 true JPH0443912B2 (ko)	1992-07-20

Family

ID=23382017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58029196A Granted JPS58189190A (ja)	1982-02-24	1983-02-23	Ｃｌ１５６５化合物類，その製造方法及びそれを有効成分とする抗腫瘍剤

Country Status (1)

Country	Link
JP (1)	JPS58189190A (ko)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101550162B (zh) *	2008-04-03	2015-11-25	北京华昊中天生物技术有限公司	福司曲星衍生物及其药用用途

1983
- 1983-02-23 JP JP58029196A patent/JPS58189190A/ja active Granted

Also Published As

Publication number	Publication date
JPS58189190A (ja)	1983-11-04

Publication	Publication Date	Title
CZ390592A3 (en)	1993-08-11	Process for preparing 4,5-dihydrogendanamycin and hydroquinone thereof and the use of such compounds
JPS6215560B2 (ko)	1987-04-08
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JPH0452280B2 (ko)	1992-08-21
KR960013432B1 (ko)	1996-10-05	항균제 fr109615 및 이의 제조방법
KR100659680B1 (ko)	2006-12-21	항생 물질 카프라자마이신류 및 그 제조법
JPS6016236B2 (ja)	1985-04-24	抗生物質ｃ―１５００３ｐ―３の製造法
EP0087021B1 (en)	1987-06-10	Cl 1565 antibiotic compounds and their production
US4578383A (en)	1986-03-25	CL 1565 antibiotic compounds
FR2568892A1 (fr)	1986-02-14	Nouvel antibiotique sandramycine, procede de preparation de celui-ci, culture biologiquement pure du micro-organisme nocardioides sp, atcc no 39419, et composition pharmaceutique contenant la sandramycine
JPS61236792A (ja)	1986-10-22	新規アントラサイクリン抗生物質
JPH0232092A (ja)	1990-02-01	抗生物質ｂｕ―３６０８ｄおよびｂｕ―３６０８ｅ
US5756536A (en)	1998-05-26	Microbial transformation of taxol and cephalomannine
JPS60149520A (ja)	1985-08-07	抗腫瘍剤
JPH0443912B2 (ko)	1992-07-20
JPH03141290A (ja)	1991-06-17	抗腫瘍抗生物質ｂｍｙ―４１３３９
EP0042172B1 (en)	1984-11-07	Antibiotic compounds, pharmaceutical compositions containing such compounds, process for production thereof
JP3902530B2 (ja)	2007-04-11	新規抗生物質キガマイシン類とその用途
US4918100A (en)	1990-04-17	CL-1957B antibiotic compound and its production
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US4725621A (en)	1988-02-16	CL-1957E antibiotic compound and its production
JPS62238298A (ja)	1987-10-19	新規アントラサイクリン抗生物質ｄｃｐ−１及び２
US4696794A (en)	1987-09-29	CL-1957D antibiotic compound and its production
EP0399505B1 (en)	1994-08-31	Physiologically active compounds SN-198C and method and bacteria for their production
JPH0479354B2 (ko)	1992-12-15