CN1032235C - 卡达西叮发色团的生产方法 - Google Patents
卡达西叮发色团的生产方法 Download PDFInfo
- Publication number
- CN1032235C CN1032235C CN92110256A CN92110256A CN1032235C CN 1032235 C CN1032235 C CN 1032235C CN 92110256 A CN92110256 A CN 92110256A CN 92110256 A CN92110256 A CN 92110256A CN 1032235 C CN1032235 C CN 1032235C
- Authority
- CN
- China
- Prior art keywords
- kedarcidin
- chromophore
- chromophoric
- tumor
- 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.)
- Expired - Fee Related
Links
- 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 20
- RSXFZXJOBQZOOM-WXIIGEIKSA-N kedarcidin Chemical compound O([C@@H]\1COC(=O)C[C@H](C2=CC=C(C(=N2)Cl)O[C@@H]2[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@](C)(O)C3)[C@]34O[C@H]3C#C/C=C/1C#CC4=C2)NC(=O)C=1C(O)=CC2=CC(OC(C)C)=C(C(=C2C=1)OC)OC)[C@H]1C[C@H](O)[C@H](N(C)C)[C@H](C)O1 RSXFZXJOBQZOOM-WXIIGEIKSA-N 0.000 title claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- RSXFZXJOBQZOOM-INBIVCPUSA-N 143591-04-2 Chemical compound O([C@@H]\1COC(=O)C[C@H](C2=CC=C(C(=N2)Cl)O[C@@H]2[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@](C)(O)C3)[C@]34O[C@H]3C#C/C=C/1C#CC4=C2)NC(=O)C=1C(O)=CC2=CC(OC(C)C)=C(C(=C2C=1)OC)OC)[C@H]1C[C@H](O)[C@H](N(C)C)[C@H](C)O1 RSXFZXJOBQZOOM-INBIVCPUSA-N 0.000 claims description 28
- 239000003242 anti bacterial agent Substances 0.000 claims description 11
- 229940088710 antibiotic agent Drugs 0.000 claims description 11
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 claims description 5
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- 239000012141 concentrate Substances 0.000 claims 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 claims 1
- 238000003810 ethyl acetate extraction Methods 0.000 claims 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 8
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- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 4
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- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 4
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- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 208000001382 Experimental Melanoma Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
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- 239000002246 antineoplastic agent Substances 0.000 description 2
- FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 238000011765 DBA/2 mouse Methods 0.000 description 1
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- 241000589516 Pseudomonas Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000178647 Streptoalloteichus sp. Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
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- 235000018660 ammonium molybdate Nutrition 0.000 description 1
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- 230000036783 anaphylactic response Effects 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KGYGBOORGRYDGQ-UHFFFAOYSA-N benzene;methanol Chemical compound OC.C1=CC=CC=C1 KGYGBOORGRYDGQ-UHFFFAOYSA-N 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229910000333 cerium(III) sulfate Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 229950000081 metilsulfate Drugs 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
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- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/763,465 US5143906A (en) | 1991-09-26 | 1991-09-26 | Kedarcidin antitumor chromophore and pharmaceutical composition containing same |
| US763,465 | 1991-09-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1073447A CN1073447A (zh) | 1993-06-23 |
| CN1032235C true CN1032235C (zh) | 1996-07-10 |
Family
ID=25067899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN92110256A Expired - Fee Related CN1032235C (zh) | 1991-09-26 | 1992-08-26 | 卡达西叮发色团的生产方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5143906A (Direct) |
| EP (1) | EP0534137A3 (Direct) |
| JP (1) | JPH06179623A (Direct) |
| KR (1) | KR930005632A (Direct) |
| CN (1) | CN1032235C (Direct) |
| AU (1) | AU647300B2 (Direct) |
| CA (1) | CA2075453A1 (Direct) |
| FI (1) | FI923827A7 (Direct) |
| HU (1) | HU211108B (Direct) |
| IL (1) | IL102942A0 (Direct) |
| MX (1) | MX9204765A (Direct) |
| NO (1) | NO178892C (Direct) |
| NZ (1) | NZ244149A (Direct) |
| PL (1) | PL168918B1 (Direct) |
| RU (1) | RU2067117C1 (Direct) |
| TW (1) | TW215900B (Direct) |
| ZA (1) | ZA926421B (Direct) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3706729A (en) * | 1963-11-21 | 1972-12-19 | Andrew David Batcho | Antibiotics and processes for their preparation |
| US5001112A (en) * | 1988-04-12 | 1991-03-19 | Bristol-Myers Company | Antitumor antibiotic kedarcidin |
-
1991
- 1991-09-26 US US07/763,465 patent/US5143906A/en not_active Expired - Fee Related
-
1992
- 1992-05-13 TW TW081103762A patent/TW215900B/zh active
- 1992-08-05 AU AU20800/92A patent/AU647300B2/en not_active Ceased
- 1992-08-06 CA CA002075453A patent/CA2075453A1/en not_active Abandoned
- 1992-08-17 RU SU925052758A patent/RU2067117C1/ru active
- 1992-08-18 MX MX9204765A patent/MX9204765A/es unknown
- 1992-08-19 HU HU9202712A patent/HU211108B/hu not_active IP Right Cessation
- 1992-08-20 NO NO923260A patent/NO178892C/no unknown
- 1992-08-20 EP EP19920114277 patent/EP0534137A3/en not_active Ceased
- 1992-08-21 JP JP4264030A patent/JPH06179623A/ja active Pending
- 1992-08-25 PL PL92295725A patent/PL168918B1/pl unknown
- 1992-08-25 ZA ZA926421A patent/ZA926421B/xx unknown
- 1992-08-25 IL IL102942A patent/IL102942A0/xx unknown
- 1992-08-26 FI FI923827A patent/FI923827A7/fi not_active Application Discontinuation
- 1992-08-26 CN CN92110256A patent/CN1032235C/zh not_active Expired - Fee Related
- 1992-08-26 KR KR1019920015415A patent/KR930005632A/ko not_active Ceased
- 1992-08-31 NZ NZ244149A patent/NZ244149A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI923827A0 (fi) | 1992-08-26 |
| EP0534137A3 (en) | 1994-07-06 |
| NO178892B (no) | 1996-03-18 |
| IL102942A0 (en) | 1993-01-31 |
| ZA926421B (en) | 1993-03-01 |
| HUT62908A (en) | 1993-06-28 |
| NO923260L (no) | 1993-03-29 |
| AU647300B2 (en) | 1994-03-17 |
| MX9204765A (es) | 1993-03-01 |
| NO178892C (no) | 1996-06-26 |
| JPH06179623A (ja) | 1994-06-28 |
| PL295725A1 (en) | 1993-04-05 |
| HU211108B (en) | 1995-10-30 |
| RU2067117C1 (ru) | 1996-09-27 |
| FI923827L (fi) | 1993-03-27 |
| TW215900B (Direct) | 1993-11-11 |
| PL168918B1 (pl) | 1996-05-31 |
| NZ244149A (en) | 1994-01-26 |
| AU2080092A (en) | 1993-04-01 |
| CA2075453A1 (en) | 1993-03-27 |
| KR930005632A (ko) | 1993-04-20 |
| FI923827A7 (fi) | 1993-03-27 |
| EP0534137A2 (en) | 1993-03-31 |
| CN1073447A (zh) | 1993-06-23 |
| NO923260D0 (no) | 1992-08-20 |
| US5143906A (en) | 1992-09-01 |
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