CN1125076C - 制备阿泽红霉素的方法 - Google Patents
制备阿泽红霉素的方法 Download PDFInfo
- Publication number
- CN1125076C CN1125076C CN98108489A CN98108489A CN1125076C CN 1125076 C CN1125076 C CN 1125076C CN 98108489 A CN98108489 A CN 98108489A CN 98108489 A CN98108489 A CN 98108489A CN 1125076 C CN1125076 C CN 1125076C
- Authority
- CN
- China
- Prior art keywords
- formaldehyde
- reduction
- azithromycin
- ether
- imino
- 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 - Fee Related
Links
- 229960004099 azithromycin Drugs 0.000 title claims abstract description 17
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 230000009467 reduction Effects 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 235000019846 buffering salt Nutrition 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000006485 reductive methylation reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 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 24
- 229960003276 erythromycin Drugs 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 229930006677 Erythromycin A Natural products 0.000 description 12
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
- Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT102006A PT102006B (pt) | 1997-05-19 | 1997-05-19 | Novo processo de preparacao de azitromicina |
| PT102006 | 1997-05-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1199736A CN1199736A (zh) | 1998-11-25 |
| CN1125076C true CN1125076C (zh) | 2003-10-22 |
Family
ID=20085680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98108489A Expired - Fee Related CN1125076C (zh) | 1997-05-19 | 1998-05-18 | 制备阿泽红霉素的方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6013778A (enExample) |
| EP (1) | EP0879823B1 (enExample) |
| JP (1) | JP3899181B2 (enExample) |
| CN (1) | CN1125076C (enExample) |
| AT (1) | ATE231516T1 (enExample) |
| AU (1) | AU722688B2 (enExample) |
| CA (1) | CA2237747C (enExample) |
| DE (1) | DE69810842T2 (enExample) |
| ES (1) | ES2191256T3 (enExample) |
| HU (1) | HUP9801094A3 (enExample) |
| IL (1) | IL124397A (enExample) |
| IN (1) | IN189736B (enExample) |
| NZ (1) | NZ330228A (enExample) |
| PT (1) | PT102006B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861411B1 (en) | 1997-12-02 | 2005-03-01 | Pfizer, Inc. | Method of treating eye infections with azithromycin |
| TW546302B (en) * | 1998-05-08 | 2003-08-11 | Biochemie Sa | Improvements in macrolide production |
| FR2791680B1 (fr) * | 1999-03-29 | 2001-06-29 | Merial Sas | Procede utile pour reduire les intermediaires imidates issus d'un rearrangement de beckmann d'un macrocycle 8a-azalide |
| US7056893B2 (en) | 1999-03-31 | 2006-06-06 | Insite Vision, Inc. | Topical treatment for prevention of ocular infections |
| US6239113B1 (en) | 1999-03-31 | 2001-05-29 | Insite Vision, Incorporated | Topical treatment or prevention of ocular infections |
| FR2806724B1 (fr) * | 2000-03-24 | 2003-12-05 | Merial Sas | Procede pour la preparation de derives 9-deoxo-8a-aza- (8a-alkyl)-8a-homoerythromycine a a partir de la 9-deoxo-9 (z)-hydroxyiminoerythromycine a |
| ES2260047T3 (es) | 2000-07-25 | 2006-11-01 | Laboratorio Silanes, S.A. De C.V. | Proceso de etapa unica para la preparacion de 7,16-deoxi-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihidroxi-6-etil-3,5,9,11,13,15-hexametilbiciclo(11.2.1)hexadeca-1(2)-en-ona y obtencion de una forma nueva de 9-deoxo-9a-metil-9a-homoeritromicina a. |
| ATE306491T1 (de) | 2000-08-23 | 2005-10-15 | Wockhardt Ltd | Verfahren zur herstellung von wasserfreiem azithromycin |
| RU2279439C2 (ru) * | 2000-11-27 | 2006-07-10 | Сандоз Аг | Азитромицин в форме моногидрата и способ его получения |
| HRP20030430B1 (hr) * | 2000-11-27 | 2011-11-30 | Biochemie S.A. | Makrolidni solvati |
| ES2179756B1 (es) * | 2000-11-30 | 2004-10-01 | Ercros Industrial, S.A. | Procedimiento de obtencion de azaeritromicina. |
| KR100491183B1 (ko) | 2001-03-21 | 2005-05-25 | 한미약품 주식회사 | 아지트로마이신의 제조방법 및 이 방법에 사용되는9-데옥소-9에이-아자-9에이-호모에리트로마이신 에이의결정성 수화물 |
| ITMI20021209A1 (it) * | 2002-06-04 | 2003-12-04 | Chemi Spa | Processo di preparazione di azitromicina ad elevata purezza |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| US7683162B2 (en) * | 2004-08-30 | 2010-03-23 | Taro Pharmaceutical Industries Limited | Process of preparing a crystalline azithromycin monohydrate |
| CN1304407C (zh) * | 2004-09-03 | 2007-03-14 | 南京圣和药业有限公司 | 一种阿奇霉素的精制方法 |
| ATE493416T1 (de) | 2007-05-04 | 2011-01-15 | Mallinckrodt Inc | Verbessertes verfahren zur herstellung von 6- alpha-hydroxy-n-alkylierten opiaten |
| AU2008276385B2 (en) | 2007-07-17 | 2013-07-18 | SpecGx LLC | Preparation of N-alkylated opiates by reductive amination |
| NZ607842A (en) | 2008-09-30 | 2013-12-20 | Mallinckrodt Llc | Processes for the selective amination of ketomorphinans |
| JP5685543B2 (ja) * | 2008-10-24 | 2015-03-18 | メリアル リミテッド | マクロライド系化合物の合成方法 |
| US8946419B2 (en) | 2009-02-23 | 2015-02-03 | Mallinckrodt Llc | (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives |
| EP2440562B1 (en) | 2009-06-11 | 2016-08-10 | Mallinckrodt LLC | Preparation of 6-alpha-amino n-substituted morphinans by catalytic hydrogen transfer |
| ES2465066T3 (es) | 2009-06-11 | 2014-06-05 | Mallinckrodt Llc | Aminación reductora de 6-ceto-normorfinanos por transferencia de hidrógeno catalítica |
| CN103717601A (zh) | 2011-06-09 | 2014-04-09 | 马林克罗特有限公司 | 通过催化氢转移对6-酮基吗啡喃的还原胺化 |
| BR112014005421A2 (pt) | 2011-09-08 | 2017-04-04 | Mallinckrodt Llc | produção de alcaloides sem o isolamento de intermediários |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI8110592A8 (en) * | 1981-03-06 | 1996-06-30 | Pliva Pharm & Chem Works | Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof |
| US4474768A (en) * | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| PH19293A (en) * | 1982-11-15 | 1986-03-04 | Pfizer | Epimeric azahomoerythromycin,pharmaceutical composition containing the same and method of use thereof |
| ES2104386T3 (es) * | 1993-05-19 | 1997-10-01 | Pfizer | Compuesto intermedio para la acitromicina. |
-
1997
- 1997-05-19 PT PT102006A patent/PT102006B/pt not_active IP Right Cessation
-
1998
- 1998-04-17 AU AU61938/98A patent/AU722688B2/en not_active Ceased
- 1998-04-20 NZ NZ330228A patent/NZ330228A/xx unknown
- 1998-04-21 JP JP11041098A patent/JP3899181B2/ja not_active Expired - Fee Related
- 1998-04-27 IN IN1094DE1998 patent/IN189736B/en unknown
- 1998-05-10 IL IL12439798A patent/IL124397A/xx not_active IP Right Cessation
- 1998-05-15 CA CA002237747A patent/CA2237747C/en not_active Expired - Fee Related
- 1998-05-15 HU HU9801094A patent/HUP9801094A3/hu active IP Right Revival
- 1998-05-18 US US09/080,856 patent/US6013778A/en not_active Expired - Fee Related
- 1998-05-18 CN CN98108489A patent/CN1125076C/zh not_active Expired - Fee Related
- 1998-05-19 AT AT98303945T patent/ATE231516T1/de active
- 1998-05-19 DE DE69810842T patent/DE69810842T2/de not_active Expired - Fee Related
- 1998-05-19 EP EP98303945A patent/EP0879823B1/en not_active Expired - Lifetime
- 1998-05-19 ES ES98303945T patent/ES2191256T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2191256T3 (es) | 2003-09-01 |
| ATE231516T1 (de) | 2003-02-15 |
| IL124397A (en) | 2003-09-17 |
| EP0879823A1 (en) | 1998-11-25 |
| HUP9801094A2 (hu) | 1998-12-28 |
| JP3899181B2 (ja) | 2007-03-28 |
| HU9801094D0 (en) | 1998-07-28 |
| PT102006B (pt) | 2000-06-30 |
| CA2237747A1 (en) | 1998-11-19 |
| CA2237747C (en) | 2007-04-10 |
| PT102006A (pt) | 1998-12-31 |
| JPH10316699A (ja) | 1998-12-02 |
| IN189736B (enExample) | 2003-04-19 |
| DE69810842D1 (de) | 2003-02-27 |
| DE69810842T2 (de) | 2003-11-20 |
| NZ330228A (en) | 1999-06-29 |
| AU6193898A (en) | 1998-11-19 |
| IL124397A0 (en) | 1998-12-06 |
| US6013778A (en) | 2000-01-11 |
| CN1199736A (zh) | 1998-11-25 |
| EP0879823B1 (en) | 2003-01-22 |
| HUP9801094A3 (en) | 2000-03-28 |
| AU722688B2 (en) | 2000-08-10 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |