SU695557A3 - Способ получени 7-0-алкилногарола - Google Patents
Способ получени 7-0-алкилногаролаInfo
- Publication number
- SU695557A3 SU695557A3 SU772552298A SU2552298A SU695557A3 SU 695557 A3 SU695557 A3 SU 695557A3 SU 772552298 A SU772552298 A SU 772552298A SU 2552298 A SU2552298 A SU 2552298A SU 695557 A3 SU695557 A3 SU 695557A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloroform
- methanol
- solution
- reduced pressure
- ethanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- -1 n-buto ol Chemical compound 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- NNEGMXMRXKXKMQ-ZEOBNFASSA-N disnogamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C[C@@](C)(O)C1 NNEGMXMRXKXKMQ-ZEOBNFASSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/748,716 US4086245A (en) | 1976-12-09 | 1976-12-09 | Antibiotics 7-O-alkylnogarols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU695557A3 true SU695557A3 (ru) | 1979-10-30 |
Family
ID=25010622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772552298A SU695557A3 (ru) | 1976-12-09 | 1977-12-09 | Способ получени 7-0-алкилногарола |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4086245A (enExample) |
| JP (1) | JPS5373584A (enExample) |
| AU (1) | AU507632B2 (enExample) |
| BE (1) | BE861697A (enExample) |
| CA (1) | CA1074306A (enExample) |
| CH (1) | CH633012A5 (enExample) |
| DE (1) | DE2754134A1 (enExample) |
| FR (1) | FR2373544A1 (enExample) |
| GB (1) | GB1554517A (enExample) |
| HK (1) | HK9585A (enExample) |
| IL (1) | IL53282A (enExample) |
| NL (1) | NL7712718A (enExample) |
| SU (1) | SU695557A3 (enExample) |
| ZA (1) | ZA776830B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2489437C2 (ru) * | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183860A (en) * | 1978-07-17 | 1980-01-15 | The Upjohn Company | Antibiotics 7(S)-O-alkylnogarols |
| GB2049689B (en) * | 1979-04-23 | 1983-05-18 | Upjohn Co | Nogamycin analogues and their preparation |
| US4767847A (en) * | 1979-07-25 | 1988-08-30 | The Upjohn Company | Nobamycin its analogs and process therefore |
| US4238398A (en) * | 1979-10-31 | 1980-12-09 | The Upjohn Company | Antibiotics 7(R)-O-alkylnogalarols |
| US4318790A (en) * | 1980-03-17 | 1982-03-09 | The Upjohn Company | Photochemical process for preparing N-demethyl-derivatives of nogalamycin |
| US4329450A (en) * | 1981-02-25 | 1982-05-11 | The Upjohn Company | Nogalamycin analog containing compounds |
| JP6179692B1 (ja) * | 2015-12-21 | 2017-08-16 | 新日鐵住金株式会社 | アズロール型ｋ５５電縫油井管及び熱延鋼板 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183157A (en) * | 1963-02-01 | 1965-05-11 | Upjohn Co | Antibiotic nogalamycin and method of producing |
| US3501569A (en) * | 1967-06-29 | 1970-03-17 | Upjohn Co | Antibiotics nogalarol,o-methylnogalarol and nogalarene and production thereof |
-
1976
- 1976-12-09 US US05/748,716 patent/US4086245A/en not_active Expired - Lifetime
-
1977
- 1977-10-27 CA CA289,682A patent/CA1074306A/en not_active Expired
- 1977-11-02 IL IL53282A patent/IL53282A/xx unknown
- 1977-11-03 GB GB45679/77A patent/GB1554517A/en not_active Expired
- 1977-11-15 ZA ZA00776830A patent/ZA776830B/xx unknown
- 1977-11-18 NL NL7712718A patent/NL7712718A/xx not_active Application Discontinuation
- 1977-11-24 CH CH1443477A patent/CH633012A5/de not_active IP Right Cessation
- 1977-11-24 AU AU30923/77A patent/AU507632B2/en not_active Expired
- 1977-11-30 JP JP14288577A patent/JPS5373584A/ja active Granted
- 1977-12-05 DE DE19772754134 patent/DE2754134A1/de active Granted
- 1977-12-08 FR FR7737012A patent/FR2373544A1/fr active Granted
- 1977-12-09 BE BE183327A patent/BE861697A/xx not_active IP Right Cessation
- 1977-12-09 SU SU772552298A patent/SU695557A3/ru active
-
1985
- 1985-01-31 HK HK95/85A patent/HK9585A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2489437C2 (ru) * | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
Also Published As
| Publication number | Publication date |
|---|---|
| IL53282A0 (en) | 1978-01-31 |
| FR2373544A1 (fr) | 1978-07-07 |
| AU3092377A (en) | 1979-05-31 |
| AU507632B2 (en) | 1980-02-21 |
| ZA776830B (en) | 1978-09-27 |
| DE2754134A1 (de) | 1978-06-15 |
| DE2754134C2 (enExample) | 1988-09-01 |
| NL7712718A (nl) | 1978-06-13 |
| CA1074306A (en) | 1980-03-25 |
| US4086245A (en) | 1978-04-25 |
| IL53282A (en) | 1981-11-30 |
| JPS6148518B2 (enExample) | 1986-10-24 |
| FR2373544B1 (enExample) | 1982-07-02 |
| HK9585A (en) | 1985-02-08 |
| JPS5373584A (en) | 1978-06-30 |
| CH633012A5 (de) | 1982-11-15 |
| BE861697A (fr) | 1978-06-09 |
| GB1554517A (en) | 1979-10-24 |
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