ZA200205697B - Method for preparing and isolating 9-deoxo-9(z)-hydroxyiminoerythromycin A. - Google Patents
Method for preparing and isolating 9-deoxo-9(z)-hydroxyiminoerythromycin A. Download PDFInfo
- Publication number
- ZA200205697B ZA200205697B ZA200205697A ZA200205697A ZA200205697B ZA 200205697 B ZA200205697 B ZA 200205697B ZA 200205697 A ZA200205697 A ZA 200205697A ZA 200205697 A ZA200205697 A ZA 200205697A ZA 200205697 B ZA200205697 B ZA 200205697B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- organic solvent
- oxime
- water
- ethyl acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
- 239000002904 solvent Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 238000006317 isomerization reaction Methods 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 229960003276 erythromycin Drugs 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229930006677 Erythromycin A Natural products 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 238000007614 solvation Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000002923 oximes Chemical class 0.000 description 10
- 239000000725 suspension Substances 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin 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)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- -1 lithium hydroxide Chemical class 0.000 description 3
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (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 |
|---|---|---|---|
| FR9916106A FR2802534B1 (fr) | 1999-12-20 | 1999-12-20 | Procede pour preparer et isoler la 9-deoxo-9 (z)- hydroxyiminoerythromycine a |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200205697B true ZA200205697B (en) | 2003-09-29 |
Family
ID=9553516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200205697A ZA200205697B (en) | 1999-12-20 | 2002-07-17 | Method for preparing and isolating 9-deoxo-9(z)-hydroxyiminoerythromycin A. |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1242439B1 (pt) |
| JP (1) | JP2003518133A (pt) |
| CN (1) | CN1215077C (pt) |
| AR (1) | AR027021A1 (pt) |
| AT (1) | ATE240967T1 (pt) |
| AU (1) | AU776674B2 (pt) |
| BR (1) | BRPI0016506B8 (pt) |
| CA (1) | CA2394623C (pt) |
| DE (1) | DE60002922T2 (pt) |
| DK (1) | DK1242439T3 (pt) |
| ES (1) | ES2202215T3 (pt) |
| FR (1) | FR2802534B1 (pt) |
| NZ (1) | NZ519802A (pt) |
| PL (2) | PL200527B1 (pt) |
| PT (1) | PT1242439E (pt) |
| TR (1) | TR200300174T3 (pt) |
| WO (1) | WO2001046211A1 (pt) |
| ZA (1) | ZA200205697B (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103713080A (zh) * | 2013-12-25 | 2014-04-09 | 挑战（天津）动物药业有限公司 | 一种加米霉素的含量检测方法 |
| CN105461770B (zh) * | 2015-12-25 | 2018-11-06 | 湖北回盛生物科技有限公司 | 一种9-脱氧-9-同型红霉素a(z)肟的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912331A (en) * | 1991-03-15 | 1999-06-15 | Merck & Co., Inc. | Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A |
| CA2062932A1 (en) * | 1991-03-15 | 1992-09-16 | Robert R. Wilkening | 9-deoxo-9(z)-hydroxyiminoerythromycin a and o-derivatives thereof |
| CA2064634C (en) * | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| US5808017A (en) * | 1996-04-10 | 1998-09-15 | Abbott Laboratories | Process for preparing erythromycin A oxime |
| US5945405A (en) * | 1997-01-17 | 1999-08-31 | Abbott Laboratories | Crystal form O of clarithromycin |
| US6504017B1 (en) * | 1997-07-08 | 2003-01-07 | Biochemie S.A. | Erthromycin a oxime solvates |
-
1999
- 1999-12-20 FR FR9916106A patent/FR2802534B1/fr not_active Expired - Lifetime
-
2000
- 2000-12-19 PT PT00990066T patent/PT1242439E/pt unknown
- 2000-12-19 DK DK00990066T patent/DK1242439T3/da active
- 2000-12-19 BR BRPI0016506A patent/BRPI0016506B8/pt not_active IP Right Cessation
- 2000-12-19 CN CNB008174040A patent/CN1215077C/zh not_active Expired - Lifetime
- 2000-12-19 PL PL355573A patent/PL200527B1/pl unknown
- 2000-12-19 TR TR2003/00174T patent/TR200300174T3/xx unknown
- 2000-12-19 ES ES00990066T patent/ES2202215T3/es not_active Expired - Lifetime
- 2000-12-19 CA CA2394623A patent/CA2394623C/en not_active Expired - Lifetime
- 2000-12-19 DE DE60002922T patent/DE60002922T2/de not_active Expired - Lifetime
- 2000-12-19 AU AU26870/01A patent/AU776674B2/en not_active Expired
- 2000-12-19 NZ NZ519802A patent/NZ519802A/en unknown
- 2000-12-19 EP EP00990066A patent/EP1242439B1/fr not_active Expired - Lifetime
- 2000-12-19 PL PL385113A patent/PL201837B1/pl unknown
- 2000-12-19 JP JP2001547120A patent/JP2003518133A/ja active Pending
- 2000-12-19 AT AT00990066T patent/ATE240967T1/de active
- 2000-12-19 WO PCT/FR2000/003595 patent/WO2001046211A1/fr active IP Right Grant
- 2000-12-20 AR ARP000106764A patent/AR027021A1/es active IP Right Grant
-
2002
- 2002-07-17 ZA ZA200205697A patent/ZA200205697B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1411465A (zh) | 2003-04-16 |
| PT1242439E (pt) | 2003-10-31 |
| TR200300174T3 (tr) | 2003-07-21 |
| JP2003518133A (ja) | 2003-06-03 |
| PL200527B1 (pl) | 2009-01-30 |
| CN1215077C (zh) | 2005-08-17 |
| DE60002922T2 (de) | 2004-05-19 |
| PL355573A1 (en) | 2004-05-04 |
| AU2687001A (en) | 2001-07-03 |
| DK1242439T3 (da) | 2003-09-15 |
| NZ519802A (en) | 2005-03-24 |
| DE60002922D1 (de) | 2003-06-26 |
| FR2802534A1 (fr) | 2001-06-22 |
| ATE240967T1 (de) | 2003-06-15 |
| BR0016506B1 (pt) | 2013-11-26 |
| WO2001046211A1 (fr) | 2001-06-28 |
| FR2802534B1 (fr) | 2002-02-01 |
| CA2394623C (en) | 2012-07-24 |
| EP1242439A1 (fr) | 2002-09-25 |
| BR0016506A (pt) | 2002-08-27 |
| AR027021A1 (es) | 2003-03-12 |
| EP1242439B1 (fr) | 2003-05-21 |
| CA2394623A1 (en) | 2001-06-28 |
| AU776674B2 (en) | 2004-09-16 |
| ES2202215T3 (es) | 2004-04-01 |
| PL201837B1 (pl) | 2009-05-29 |
| BRPI0016506B8 (pt) | 2021-05-25 |
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