CS214881B2 - Method of making the maytanacine or maytanasinol propionate - Google Patents
Method of making the maytanacine or maytanasinol propionate Download PDFInfo
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- CS214881B2 CS214881B2 CS776677A CS667777A CS214881B2 CS 214881 B2 CS214881 B2 CS 214881B2 CS 776677 A CS776677 A CS 776677A CS 667777 A CS667777 A CS 667777A CS 214881 B2 CS214881 B2 CS 214881B2
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- CS
- Czechoslovakia
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- volume
- maytansinol
- ethyl acetate
- added
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- MQYZCKOGTWYJAZ-UHFFFAOYSA-N ansamitocin P1 Natural products CN1C(=O)CC(OC(C)=O)C2(C)OC2C(C)C(OC(=O)N2)CC2(O)C(OC)C=CC=C(C)CC2=CC(OC)=C(Cl)C1=C2 MQYZCKOGTWYJAZ-UHFFFAOYSA-N 0.000 title claims description 24
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- QWPXBEHQFHACTK-KZVYIGENSA-N (10e,12e)-86-chloro-12,14,4-trihydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-15,16-dihydro-14h-7-aza-1(6,4)-oxazina-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-6-one Chemical compound CN1C(=O)CC(O)C2(C)OC2C(C)C(OC(=O)N2)CC2(O)C(OC)\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 QWPXBEHQFHACTK-KZVYIGENSA-N 0.000 claims description 33
- QWPXBEHQFHACTK-UHFFFAOYSA-N Maytansinol Natural products CN1C(=O)CC(O)C2(C)OC2C(C)C(OC(=O)N2)CC2(O)C(OC)C=CC=C(C)CC2=CC(OC)=C(Cl)C1=C2 QWPXBEHQFHACTK-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
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- 239000001362 calcium malate Substances 0.000 description 1
- OLOZVPHKXALCRI-UHFFFAOYSA-L calcium malate Chemical compound [Ca+2].[O-]C(=O)C(O)CC([O-])=O OLOZVPHKXALCRI-UHFFFAOYSA-L 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229930182817 methionine Natural products 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YZYDOFGGDSDUPX-UHFFFAOYSA-M sodium;carbonic acid;chloride Chemical compound [Na+].[Cl-].OC(O)=O YZYDOFGGDSDUPX-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
-
- 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52037167A JPS6010718B2 (ja) | 1977-03-31 | 1977-03-31 | メイタンシノ−ル，メイタナシンおよびメイタンシノ−ル・プロピオネ−トの製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214881B2 true CS214881B2 (en) | 1982-06-25 |
Family
ID=12490032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776677A CS214881B2 (en) | 1977-03-31 | 1977-10-13 | Method of making the maytanacine or maytanasinol propionate |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6010718B2 (pl) |
| AT (1) | AT362058B (pl) |
| AU (1) | AU507869B2 (pl) |
| CA (1) | CA1092999A (pl) |
| CH (1) | CH631740A5 (pl) |
| CS (1) | CS214881B2 (pl) |
| DE (1) | DE2746253C2 (pl) |
| DK (1) | DK143570C (pl) |
| ES (1) | ES463206A1 (pl) |
| FR (1) | FR2385798A1 (pl) |
| GB (1) | GB1554395A (pl) |
| HU (1) | HU177391B (pl) |
| IE (1) | IE45888B1 (pl) |
| IT (1) | IT1094003B (pl) |
| NL (1) | NL7711273A (pl) |
| PL (1) | PL108863B1 (pl) |
| PT (1) | PT67853B (pl) |
| SE (1) | SE7711543L (pl) |
| SU (1) | SU938746A3 (pl) |
| YU (1) | YU243777A (pl) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6010720B2 (ja) * | 1977-11-18 | 1985-03-19 | 武田薬品工業株式会社 | 抗生物質ｃ―１５００３ ｐ―４の製造法 |
| JPS6016236B2 (ja) * | 1977-11-18 | 1985-04-24 | 武田薬品工業株式会社 | 抗生物質ｃ―１５００３ ｐ―３の製造法 |
| JPS55162791A (en) * | 1979-06-05 | 1980-12-18 | Takeda Chem Ind Ltd | Antibiotic c-15003pnd and its preparation |
| EP0028683A1 (en) * | 1979-09-21 | 1981-05-20 | Takeda Chemical Industries, Ltd. | Antibiotic C-15003 PHO and production thereof |
| US6573074B2 (en) | 2000-04-12 | 2003-06-03 | Smithkline Beecham Plc | Methods for ansamitocin production |
| US6333410B1 (en) | 2000-08-18 | 2001-12-25 | Immunogen, Inc. | Process for the preparation and purification of thiol-containing maytansinoids |
| US7432088B2 (en) | 2003-05-08 | 2008-10-07 | Immunogen Inc. | Methods for the production of ansamitocins |
| CN116239607B (zh) * | 2023-01-04 | 2024-04-09 | 山东大学 | 一种美登素衍生物及其生物合成方法与应用 |
-
1977
- 1977-03-31 JP JP52037167A patent/JPS6010718B2/ja not_active Expired
- 1977-09-23 AU AU29073/77A patent/AU507869B2/en not_active Expired
- 1977-10-07 FR FR7730340A patent/FR2385798A1/fr active Granted
- 1977-10-07 SU SU772533351A patent/SU938746A3/ru active
- 1977-10-10 YU YU02437/77A patent/YU243777A/xx unknown
- 1977-10-13 CS CS776677A patent/CS214881B2/cs unknown
- 1977-10-13 NL NL7711273A patent/NL7711273A/xx not_active Application Discontinuation
- 1977-10-13 SE SE7711543A patent/SE7711543L/ not_active Application Discontinuation
- 1977-10-13 HU HU77TA1458A patent/HU177391B/hu unknown
- 1977-10-14 ES ES463206A patent/ES463206A1/es not_active Expired
- 1977-10-14 AT AT736377A patent/AT362058B/de not_active IP Right Cessation
- 1977-10-14 IE IE2100/77A patent/IE45888B1/en unknown
- 1977-10-14 GB GB42821/77A patent/GB1554395A/en not_active Expired
- 1977-10-14 CA CA288,732A patent/CA1092999A/en not_active Expired
- 1977-10-14 DK DK458977A patent/DK143570C/da not_active IP Right Cessation
- 1977-10-14 CH CH1260477A patent/CH631740A5/de not_active IP Right Cessation
- 1977-10-14 DE DE2746253A patent/DE2746253C2/de not_active Expired
- 1977-10-15 PL PL1977201539A patent/PL108863B1/pl not_active IP Right Cessation
-
1978
- 1978-03-30 IT IT21819/78A patent/IT1094003B/it active
- 1978-03-30 PT PT67853A patent/PT67853B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH631740A5 (en) | 1982-08-31 |
| PT67853B (en) | 1980-05-05 |
| PL108863B1 (en) | 1980-05-31 |
| YU243777A (en) | 1982-06-30 |
| DK458977A (da) | 1978-10-01 |
| PT67853A (en) | 1978-04-01 |
| IE45888L (en) | 1978-09-30 |
| DE2746253A1 (de) | 1978-10-05 |
| HU177391B (en) | 1981-09-28 |
| SE7711543L (sv) | 1978-10-01 |
| FR2385798B1 (pl) | 1980-04-25 |
| IT7821819A0 (it) | 1978-03-30 |
| AU507869B2 (en) | 1980-02-28 |
| IT1094003B (it) | 1985-07-26 |
| DK143570C (da) | 1982-02-08 |
| SU938746A3 (ru) | 1982-06-23 |
| DE2746253C2 (de) | 1986-08-21 |
| AU2907377A (en) | 1979-03-29 |
| AT362058B (de) | 1981-04-27 |
| ES463206A1 (es) | 1978-08-16 |
| FR2385798A1 (fr) | 1978-10-27 |
| ATA736377A (de) | 1980-09-15 |
| GB1554395A (en) | 1979-10-17 |
| IE45888B1 (en) | 1982-12-29 |
| NL7711273A (nl) | 1978-10-03 |
| CA1092999A (en) | 1981-01-06 |
| JPS6010718B2 (ja) | 1985-03-19 |
| PL201539A1 (pl) | 1978-09-25 |
| JPS53121998A (en) | 1978-10-24 |
| DK143570B (da) | 1981-09-07 |
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