HUP0104600A2 - Új intermedierek és eljárás azokból makrolid antibiotikum előállítására - Google Patents
Új intermedierek és eljárás azokból makrolid antibiotikum előállításáraInfo
- Publication number
- HUP0104600A2 HUP0104600A2 HU0104600A HUP0104600A HUP0104600A2 HU P0104600 A2 HUP0104600 A2 HU P0104600A2 HU 0104600 A HU0104600 A HU 0104600A HU P0104600 A HUP0104600 A HU P0104600A HU P0104600 A2 HUP0104600 A2 HU P0104600A2
- Authority
- HU
- Hungary
- Prior art keywords
- erythromycin
- formula
- oxime
- water
- general formula
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000003120 macrolide antibiotic agent Substances 0.000 title 1
- 229940041033 macrolides Drugs 0.000 title 1
- 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 abstract 4
- 229960003276 erythromycin Drugs 0.000 abstract 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 2
- 229930006677 Erythromycin A Natural products 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 abstract 2
- 229960002626 clarithromycin Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 tetrafluoroborate Chemical compound 0.000 abstract 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KYTWXIARANQMCA-RWJQBGPGSA-N (3r,4s,5s,6r,7r,9r,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-oxacyclotetradecan-2 Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=NO)[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-RWJQBGPGSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A találmány egyrészt a (III) általános képletű eritromicin A 9-O-benzoditid-oxim köztitermékekre - a képletben Y1 és Y2 hidrogénatomotvagy trimetil-szilil-csoportot jelent - vonatkozik, amelyekklaritromicin szintéziséhez használhatók, továbbá eritromicin A 9-oximvagy hidrokloridsója és 1,3-benzoditiol-2-ilium-tetrafluoroborátreagáltatása útján állíthatók elő. A találmány tárgya továbbá eljárásaz (I) képletű klaritromicin előállítására, amelynek során 1) valamely(II) általános képletű eritromicin A 9-oximot vagy hidrokloridsóját1,3-benzotiol-2-ilium-tetrafluoroboráttal reagáltatnak egy aprotikusnem poláros szerves oldószerben piridin jelenlétében, majd 2) egy ígykapott (III') általános képletű eritromicin A 9-O-BDT-oxim-származékothexametil-diszilazánnal reagáltatnak sók jelenlétében, majd 3) egy ígykapott (V) általános képletű 2'-O,4''-O-bisz(trimetil-szilil)-eritromicin A 9-O-BDT-oxim-származék 6-helyzetű hidroxilcsoportjátmetilezik metil-jodiddal egy aprotikus poláros oldószerben egy erősbázis jelenlétében, majd 4) egy így kapott (VII) általános képletű 2'-O,4''-O-bisz(trimetil-szilil)-6-O-metil-eritromicin A 9-O-BDToximszármazék védőcsoportját eltávolítják, és 5) egy így kapott(I).BSDA képletű vegyületet egyszerűen vízben vagy víz és egy vízzelelegyedő szerves oldószer elegyében kevernek, és végül szűréssel aképződött (I) képletű vegyületet elkülönítik. Ó
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19980050425 | 1998-11-24 | ||
| KR1019990050802A KR100317907B1 (ko) | 1998-11-24 | 1999-11-16 | 신규한 중간체, 이를 이용한 마크로라이드계 항생제의제조방법 |
| PCT/KR1999/000708 WO2000031099A1 (en) | 1998-11-24 | 1999-11-24 | Novel intermediates, process for preparing macrolide antibiotic agent therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0104600A2 true HUP0104600A2 (hu) | 2002-03-28 |
| HUP0104600A3 HUP0104600A3 (en) | 2003-12-29 |
Family
ID=26634358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0104600A HUP0104600A3 (en) | 1998-11-24 | 1999-11-24 | Novel intermediates, process for preparing macrolide antibiotic agent therefrom |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6600025B1 (hu) |
| EP (1) | EP1133511B1 (hu) |
| JP (1) | JP3848837B2 (hu) |
| KR (1) | KR100317907B1 (hu) |
| CN (1) | CN1354753A (hu) |
| AT (1) | ATE234321T1 (hu) |
| AU (1) | AU751874B2 (hu) |
| BR (1) | BR9915646A (hu) |
| CA (1) | CA2352162A1 (hu) |
| CZ (1) | CZ20011803A3 (hu) |
| DE (1) | DE69905935T2 (hu) |
| DK (1) | DK1133511T3 (hu) |
| ES (1) | ES2190275T3 (hu) |
| HU (1) | HUP0104600A3 (hu) |
| IL (1) | IL143331A0 (hu) |
| MX (1) | MXPA01005248A (hu) |
| PL (1) | PL348607A1 (hu) |
| PT (1) | PT1133511E (hu) |
| RU (1) | RU2208615C2 (hu) |
| TR (1) | TR200101474T2 (hu) |
| WO (1) | WO2000031099A1 (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7601695B2 (en) | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| ES2221807B1 (es) * | 2003-06-24 | 2005-12-16 | Ercros Industrial, S.A. | Un procedimiento para la obtencion de claritromicina. |
| US7767797B1 (en) * | 2004-09-30 | 2010-08-03 | Synovo Gmbh | Macrocyclic compounds and methods of use thereof |
| US7582611B2 (en) * | 2005-05-24 | 2009-09-01 | Pfizer Inc. | Motilide compounds |
| WO2007008537A2 (en) * | 2005-07-07 | 2007-01-18 | Elan Pharma International, Limited | Nanoparticulate clarithromycin formulations |
| WO2009023191A2 (en) * | 2007-08-09 | 2009-02-19 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of clarithromycin |
| WO2009055557A1 (en) | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| AU2009308180B2 (en) | 2008-10-24 | 2016-01-07 | Cempra Pharmaceuticals, Inc. | Methods for treating gastrointestinal diseases |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| ES2608285T3 (es) | 2009-09-10 | 2017-04-07 | Cempra Pharmaceuticals, Inc. | Procedimientos para el tratamiento de paludismo, tuberculosis y enfermedades por MAC |
| US8975386B2 (en) * | 2010-03-22 | 2015-03-10 | Cempra Pharmaceuticals, Inc. | Crystalline forms of a macrolide, and uses therefor |
| PL2571506T3 (pl) | 2010-05-20 | 2017-10-31 | Cempra Pharmaceuticals Inc | Sposoby sporządzania makrolidów i ketolidów oraz ich produktów pośrednich |
| EP2613630A4 (en) | 2010-09-10 | 2014-01-15 | Cempra Pharmaceuticals Inc | FLUOROCETOLIDES FORMING HYDROGEN LINKS TO TREAT DISEASES |
| EP2830632A4 (en) | 2012-03-27 | 2015-10-21 | Cempra Pharmaceuticals Inc | PARENTERAL FORMULATIONS FOR THE ADMINISTRATION OF MACROLIDE ANTIBIOTICS |
| US9861616B2 (en) | 2013-03-14 | 2018-01-09 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| RU2015138797A (ru) | 2013-03-15 | 2017-04-24 | Семпра Фармасьютикалс, Инк. | Конвергентные способы получения макролидных антибактериальных агентов |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5872229A (en) * | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| US5719272A (en) * | 1996-04-02 | 1998-02-17 | Abbott Laboratories | 2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives |
| US5864023A (en) * | 1997-02-13 | 1999-01-26 | Abbott Laboratories | 3'-N'oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives |
| US5929219A (en) * | 1997-09-10 | 1999-07-27 | Abbott Laboratories | 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same |
| IL136089A0 (en) * | 1997-12-01 | 2001-05-20 | Abbott Lab | Chemical synthesis of 6-0-alkyl erythromycin c |
| WO1999032500A2 (en) * | 1997-12-22 | 1999-07-01 | Biochemie S.A. | Intermediates in macrolide production |
| AU2658899A (en) * | 1998-02-04 | 1999-08-23 | Teva Pharmaceutical Industries Ltd. | Process for making clarithromycin |
-
1999
- 1999-11-16 KR KR1019990050802A patent/KR100317907B1/ko active IP Right Grant
- 1999-11-24 AT AT99958490T patent/ATE234321T1/de not_active IP Right Cessation
- 1999-11-24 JP JP2000583926A patent/JP3848837B2/ja not_active Expired - Fee Related
- 1999-11-24 CA CA002352162A patent/CA2352162A1/en not_active Abandoned
- 1999-11-24 DE DE69905935T patent/DE69905935T2/de not_active Expired - Fee Related
- 1999-11-24 HU HU0104600A patent/HUP0104600A3/hu unknown
- 1999-11-24 WO PCT/KR1999/000708 patent/WO2000031099A1/en active IP Right Grant
- 1999-11-24 PL PL99348607A patent/PL348607A1/xx unknown
- 1999-11-24 CN CN99813690A patent/CN1354753A/zh active Pending
- 1999-11-24 US US09/856,383 patent/US6600025B1/en not_active Expired - Fee Related
- 1999-11-24 RU RU2001117216/04A patent/RU2208615C2/ru not_active IP Right Cessation
- 1999-11-24 TR TR2001/01474T patent/TR200101474T2/xx unknown
- 1999-11-24 DK DK99958490T patent/DK1133511T3/da active
- 1999-11-24 EP EP99958490A patent/EP1133511B1/en not_active Expired - Lifetime
- 1999-11-24 CZ CZ20011803A patent/CZ20011803A3/cs unknown
- 1999-11-24 BR BR9915646-6A patent/BR9915646A/pt not_active IP Right Cessation
- 1999-11-24 PT PT99958490T patent/PT1133511E/pt unknown
- 1999-11-24 ES ES99958490T patent/ES2190275T3/es not_active Expired - Lifetime
- 1999-11-24 MX MXPA01005248A patent/MXPA01005248A/es not_active Application Discontinuation
- 1999-11-24 IL IL14333199A patent/IL143331A0/xx unknown
- 1999-11-24 AU AU15847/00A patent/AU751874B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PT1133511E (pt) | 2003-06-30 |
| DE69905935T2 (de) | 2003-09-04 |
| KR100317907B1 (ko) | 2001-12-24 |
| EP1133511B1 (en) | 2003-03-12 |
| RU2208615C2 (ru) | 2003-07-20 |
| CN1354753A (zh) | 2002-06-19 |
| TR200101474T2 (tr) | 2001-12-21 |
| KR20000057013A (ko) | 2000-09-15 |
| BR9915646A (pt) | 2001-08-07 |
| JP2002530423A (ja) | 2002-09-17 |
| ES2190275T3 (es) | 2003-07-16 |
| DK1133511T3 (da) | 2003-07-14 |
| EP1133511A1 (en) | 2001-09-19 |
| US6600025B1 (en) | 2003-07-29 |
| PL348607A1 (en) | 2002-06-03 |
| ATE234321T1 (de) | 2003-03-15 |
| CA2352162A1 (en) | 2000-06-02 |
| DE69905935D1 (de) | 2003-04-17 |
| HUP0104600A3 (en) | 2003-12-29 |
| JP3848837B2 (ja) | 2006-11-22 |
| CZ20011803A3 (cs) | 2001-10-17 |
| AU751874B2 (en) | 2002-08-29 |
| AU1584700A (en) | 2000-06-13 |
| IL143331A0 (en) | 2002-04-21 |
| MXPA01005248A (es) | 2003-08-19 |
| WO2000031099A1 (en) | 2000-06-02 |
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