CH471779A - Procédé de préparation de dérivés de l'érythromycine - Google Patents
Procédé de préparation de dérivés de l'érythromycineInfo
- Publication number
- CH471779A CH471779A CH519667A CH519667A CH471779A CH 471779 A CH471779 A CH 471779A CH 519667 A CH519667 A CH 519667A CH 519667 A CH519667 A CH 519667A CH 471779 A CH471779 A CH 471779A
- Authority
- CH
- Switzerland
- Prior art keywords
- erythromycin
- compound
- oxide
- desdimethylamino
- preparation
- Prior art date
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 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 229960003276 erythromycin Drugs 0.000 claims description 6
- 238000000197 pyrolysis Methods 0.000 claims description 6
- IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 claims description 5
- 241000242678 Schistosoma Species 0.000 claims description 4
- 239000003610 charcoal Substances 0.000 claims description 4
- -1 erythromycin B N-oxide Chemical class 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000002035 prolonged effect Effects 0.000 claims description 4
- LUIPOVCSQJTWHA-RWJQBGPGSA-N (2s,3r,4s,6r)-2-[[(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-n,n,6-trimethyloxan-4-amine oxide Chemical compound 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-])O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 LUIPOVCSQJTWHA-RWJQBGPGSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 241000416162 Astragalus gummifer Species 0.000 claims description 2
- 241000273930 Brevoortia tyrannus Species 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims description 2
- 229930006677 Erythromycin A Natural products 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 229920001615 Tragacanth Polymers 0.000 claims description 2
- 230000002411 adverse Effects 0.000 claims description 2
- 238000002144 chemical decomposition reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 235000013601 eggs Nutrition 0.000 claims description 2
- IDRYSCOQVVUBIJ-PPGFLMPOSA-N erythromycin B Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@H]([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)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 IDRYSCOQVVUBIJ-PPGFLMPOSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 239000007928 intraperitoneal injection Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 201000004409 schistosomiasis Diseases 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
Classifications
-
- 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
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US542219A US3361737A (en) | 1966-04-13 | 1966-04-13 | 3'-desdimethylamino-delta3', 4'-erythromycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH471779A true CH471779A (fr) | 1969-04-30 |
Family
ID=24162835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH519667A CH471779A (fr) | 1966-04-13 | 1967-04-12 | Procédé de préparation de dérivés de l'érythromycine |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3361737A (oth) |
| BE (1) | BE696949A (oth) |
| CH (1) | CH471779A (oth) |
| ES (1) | ES338996A1 (oth) |
| GB (1) | GB1125544A (oth) |
| GR (1) | GR33603B (oth) |
| NL (1) | NL6704887A (oth) |
| SE (1) | SE346993B (oth) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928387A (en) * | 1974-02-04 | 1975-12-23 | Hoffmann La Roche | Antibiotic 1745A/X and methods for the production thereof |
| US4152424A (en) * | 1975-07-23 | 1979-05-01 | Hoffmann-La Roche Inc. | Antibiotic 1745A/X and methods for the production thereof |
| EP0431874A1 (en) * | 1989-12-08 | 1991-06-12 | Beecham Group p.l.c. | Novel compounds |
-
1966
- 1966-04-13 US US542219A patent/US3361737A/en not_active Expired - Lifetime
-
1967
- 1967-04-03 GR GR670133603A patent/GR33603B/el unknown
- 1967-04-05 GB GB15717/67A patent/GB1125544A/en not_active Expired
- 1967-04-06 NL NL6704887A patent/NL6704887A/xx unknown
- 1967-04-06 ES ES338996A patent/ES338996A1/es not_active Expired
- 1967-04-12 CH CH519667A patent/CH471779A/fr not_active IP Right Cessation
- 1967-04-12 SE SE05073/67A patent/SE346993B/xx unknown
- 1967-04-13 BE BE696949D patent/BE696949A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1125544A (en) | 1968-08-28 |
| US3361737A (en) | 1968-01-02 |
| BE696949A (oth) | 1967-10-13 |
| NL6704887A (oth) | 1967-10-16 |
| ES338996A1 (es) | 1968-09-01 |
| SE346993B (oth) | 1972-07-24 |
| GR33603B (el) | 1967-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |