JPS6152838B2 - - Google Patents
Info
- Publication number
- JPS6152838B2 JPS6152838B2 JP13475077A JP13475077A JPS6152838B2 JP S6152838 B2 JPS6152838 B2 JP S6152838B2 JP 13475077 A JP13475077 A JP 13475077A JP 13475077 A JP13475077 A JP 13475077A JP S6152838 B2 JPS6152838 B2 JP S6152838B2
- Authority
- JP
- Japan
- Prior art keywords
- erythromycin
- methanesulfonyl
- formylerythromycin
- present
- acetylerythromycin
- 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
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 18
- 229960003276 erythromycin Drugs 0.000 claims description 15
- 229930006677 Erythromycin A Natural products 0.000 claims description 14
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000187747 Streptomyces Species 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
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- -1 methanesulfonyl halide Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13475077A JPS5470290A (en) | 1977-11-11 | 1977-11-11 | Erythromycin a derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13475077A JPS5470290A (en) | 1977-11-11 | 1977-11-11 | Erythromycin a derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5470290A JPS5470290A (en) | 1979-06-05 |
| JPS6152838B2 true JPS6152838B2 (de) | 1986-11-14 |
Family
ID=15135689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13475077A Granted JPS5470290A (en) | 1977-11-11 | 1977-11-11 | Erythromycin a derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5470290A (de) |
-
1977
- 1977-11-11 JP JP13475077A patent/JPS5470290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5470290A (en) | 1979-06-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6069238A (en) | Spirocyclic C-glycosides | |
| JPH053476B2 (de) | ||
| JP3983803B2 (ja) | アンスラサイクリン系抗生物質の製造法 | |
| JP3029806B2 (ja) | コルヒチン誘導体をグリコシド化する方法、及びその生成物 | |
| KR960014102B1 (ko) | 타이로신유도체 및 그 제조법 | |
| US4914192A (en) | Mycaminosyl tylonolide derivatives | |
| JPS6152838B2 (de) | ||
| JP3194581B2 (ja) | ジベレリン分離法 | |
| JPS5827798B2 (ja) | 新規抗菌剤の中間体 | |
| JPH039919B2 (de) | ||
| US4935506A (en) | 3-phenylthiosialic acid derivative, sialic acid-containing oligosaccharide derivative and process for preparing these compounds | |
| JPS6016998A (ja) | アントラサイクリン誘導体の製造方法 | |
| SU1068038A3 (ru) | Способ получени производных 5,6-дидезокси-5-оксо-1,2,3,6-тетра- @ -/трифторацетил/-неамина | |
| JP2571059B2 (ja) | １，３，４−トリ−Ｏ−アシル−２−デオキシ−β−Ｄ−エリスロ−ペンタピラノ−スの製造方法 | |
| JPS635397B2 (de) | ||
| JP3061476B2 (ja) | エトポシド燐酸エステルの製造法 | |
| JPS6114158B2 (de) | ||
| JPH0529038B2 (de) | ||
| US4921978A (en) | Process for the preparation of a macrolide compound | |
| JPS6152160B2 (de) | ||
| JPH0510356B2 (de) | ||
| US4876245A (en) | Fluorine-containing macrolide compounds and their use | |
| KR820001219B1 (ko) | 반합성 4"-에리트로마이신 a 유도체의 제조방법 | |
| KR820001220B1 (ko) | 반합성 4"-에리트로마이신 a 유도체의 제조방법 | |
| JPH0616667A (ja) | ピラゾロ［１，５−ａピリジン誘導体の新規製造方法 |