AU598486B2 - Silylated erythromycin derivative antibiotics - Google Patents
Silylated erythromycin derivative antibiotics Download PDFInfo
- Publication number
- AU598486B2 AU598486B2 AU64916/86A AU6491686A AU598486B2 AU 598486 B2 AU598486 B2 AU 598486B2 AU 64916/86 A AU64916/86 A AU 64916/86A AU 6491686 A AU6491686 A AU 6491686A AU 598486 B2 AU598486 B2 AU 598486B2
- Authority
- AU
- Australia
- Prior art keywords
- hydrogen
- erythromycin
- methyl
- alkyl
- trimethylsilyl
- 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
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- 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 52
- 239000003242 anti bacterial agent Substances 0.000 title claims description 12
- 229940088710 antibiotic agent Drugs 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000003115 biocidal effect Effects 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002552 dosage form Substances 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- -1 ethylcyclohexyl Chemical group 0.000 description 13
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
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- 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 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
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- 230000001154 acute effect Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- CVBHEIRZLPKMSH-SNWVVRALSA-N erythromycin acistrate 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)OC(C)=O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 CVBHEIRZLPKMSH-SNWVVRALSA-N 0.000 description 3
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- 239000002054 inoculum Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
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- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US796818 | 1985-11-12 | ||
| US06/796,818 US4640910A (en) | 1985-11-12 | 1985-11-12 | Erythromycin A silylated compounds and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6491686A AU6491686A (en) | 1987-05-14 |
| AU598486B2 true AU598486B2 (en) | 1990-06-28 |
Family
ID=25169134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU64916/86A Expired - Fee Related AU598486B2 (en) | 1985-11-12 | 1986-11-07 | Silylated erythromycin derivative antibiotics |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4640910A (https=) |
| EP (1) | EP0222353B1 (https=) |
| JP (1) | JPS62120397A (https=) |
| KR (1) | KR870005004A (https=) |
| AT (1) | ATE66001T1 (https=) |
| AU (1) | AU598486B2 (https=) |
| CA (1) | CA1282059C (https=) |
| DE (1) | DE3680749D1 (https=) |
| DK (1) | DK536186A (https=) |
| ES (1) | ES2002212A6 (https=) |
| GR (1) | GR862517B (https=) |
| IL (1) | IL80146A0 (https=) |
| NZ (1) | NZ217665A (https=) |
| ZA (1) | ZA867294B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175150A (en) * | 1985-08-31 | 1992-12-29 | Kitasato, Kenkyusho | Erythromycin derivative |
| EP0260938B1 (en) * | 1986-09-18 | 1992-12-09 | Taisho Pharmaceutical Co. Ltd | Erythromycin a derivatives and method for preparing the same |
| KR960000434B1 (ko) * | 1986-12-17 | 1996-01-06 | 다이쇼 세이야꾸 가부시끼가이샤 | 에리스로마이신 a유도체 및 그의 제조 방법 |
| US4808411A (en) * | 1987-06-05 | 1989-02-28 | Abbott Laboratories | Antibiotic-polymer compositions |
| JP2654194B2 (ja) * | 1989-06-20 | 1997-09-17 | メルシャン株式会社 | アンゴラマイシン誘導体 |
| EP0559896B1 (en) * | 1990-11-28 | 1997-08-27 | Taisho Pharmaceutical Co. Ltd | 6-o-methylerythromycin a derivative |
| DK0623021T3 (da) * | 1992-01-21 | 1999-02-08 | Abbott Lab | 4"-deoxyerythromycinderivater |
| US5872229A (en) | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| US5837829A (en) * | 1996-04-02 | 1998-11-17 | Abbott Laboratories | 9-oximesilyl erythromycin a derivatives |
| US5712253A (en) * | 1996-06-18 | 1998-01-27 | Abbott Laboratories | Macrocyclic 13-membered ring derivatives of erythromycins A and B |
| US5929219A (en) | 1997-09-10 | 1999-07-27 | Abbott Laboratories | 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same |
| US5892008A (en) * | 1997-12-16 | 1999-04-06 | Abbott Laboratories | Process for the preparation of 6-O-methyl erythromycin a using 9-hydroxy erythromycin derivatives |
| AU2274799A (en) * | 1997-12-22 | 1999-07-12 | Biochemie S.A. | Intermediates in macrolide production |
| GB9915745D0 (en) * | 1999-07-06 | 1999-09-08 | Biochemie Sa | Organic compounds |
| WO2001044262A1 (en) | 1999-12-16 | 2001-06-21 | Teva Pharmaceutical Industries Ltd. | Processes for preparing clarithromycin polymorphs and novel polymorph iv |
| AU2261901A (en) | 2000-01-11 | 2001-07-24 | Teva Pharma | Processes for preparing clarithromycin polymorphs |
| KR20030047873A (ko) * | 2000-02-29 | 2003-06-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | 클라리트로마이신 및 클라리트로마이신 중간체의 제조방법, 실질적으로는 옥심이 제거된 클라리트로마이신 및이를 포함하는 약학적 조성물 |
| KR100361397B1 (ko) * | 2000-03-15 | 2002-11-23 | 한미약품공업 주식회사 | 에리스로마이신 에이 9-오-트로필옥심 유도체를 이용한클라리스로마이신의 제조방법 |
| AU2001263812B2 (en) * | 2000-03-28 | 2004-09-23 | Sandoz Ag | Granulated particles with masked taste |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041355A1 (en) * | 1980-06-04 | 1981-12-09 | Taisho Pharmaceutical Co. Ltd | Novel erythromycin compounds |
| EP0080819A1 (en) * | 1981-11-30 | 1983-06-08 | Taisho Pharmaceutical Co. Ltd | 11-0-Alkylerythromycin A derivatives |
| AU1189883A (en) * | 1982-03-01 | 1983-09-08 | Pzifer Inc. | 4"-epi-erythromycin a |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746956A (en) * | 1953-06-16 | 1956-05-22 | Dow Corning | Method of silylating organic compounds |
| US4336368A (en) * | 1981-04-20 | 1982-06-22 | Pfizer Inc. | 4 Deoxy-4-methylene oleandomycin and derivatives thereof |
| US4382086A (en) * | 1982-03-01 | 1983-05-03 | Pfizer Inc. | 9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A |
| US4429116A (en) * | 1982-12-27 | 1984-01-31 | Pfizer Inc. | Alkylated oleandomycin containing compounds |
-
1985
- 1985-11-12 US US06/796,818 patent/US4640910A/en not_active Expired - Fee Related
-
1986
- 1986-09-23 NZ NZ217665A patent/NZ217665A/en unknown
- 1986-09-24 ZA ZA867294A patent/ZA867294B/xx unknown
- 1986-09-25 IL IL80146A patent/IL80146A0/xx unknown
- 1986-10-07 GR GR862517A patent/GR862517B/el unknown
- 1986-11-06 ES ES8602929A patent/ES2002212A6/es not_active Expired
- 1986-11-07 AU AU64916/86A patent/AU598486B2/en not_active Expired - Fee Related
- 1986-11-07 CA CA000522503A patent/CA1282059C/en not_active Expired - Fee Related
- 1986-11-08 DE DE8686115523T patent/DE3680749D1/de not_active Expired - Fee Related
- 1986-11-08 AT AT86115523T patent/ATE66001T1/de not_active IP Right Cessation
- 1986-11-08 EP EP86115523A patent/EP0222353B1/en not_active Expired - Lifetime
- 1986-11-10 DK DK536186A patent/DK536186A/da not_active Application Discontinuation
- 1986-11-11 KR KR860009486A patent/KR870005004A/ko not_active Ceased
- 1986-11-12 JP JP61267886A patent/JPS62120397A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041355A1 (en) * | 1980-06-04 | 1981-12-09 | Taisho Pharmaceutical Co. Ltd | Novel erythromycin compounds |
| EP0080819A1 (en) * | 1981-11-30 | 1983-06-08 | Taisho Pharmaceutical Co. Ltd | 11-0-Alkylerythromycin A derivatives |
| AU1189883A (en) * | 1982-03-01 | 1983-09-08 | Pzifer Inc. | 4"-epi-erythromycin a |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62120397A (ja) | 1987-06-01 |
| ZA867294B (en) | 1987-05-27 |
| KR870005004A (ko) | 1987-06-04 |
| ES2002212A6 (es) | 1988-07-16 |
| GR862517B (en) | 1987-02-09 |
| AU6491686A (en) | 1987-05-14 |
| US4640910A (en) | 1987-02-03 |
| DE3680749D1 (de) | 1991-09-12 |
| DK536186D0 (da) | 1986-11-10 |
| DK536186A (da) | 1987-05-13 |
| CA1282059C (en) | 1991-03-26 |
| ATE66001T1 (de) | 1991-08-15 |
| EP0222353A3 (en) | 1987-09-23 |
| EP0222353B1 (en) | 1991-08-07 |
| IL80146A0 (en) | 1986-12-31 |
| JPH0312078B2 (https=) | 1991-02-19 |
| EP0222353A2 (en) | 1987-05-20 |
| NZ217665A (en) | 1990-04-26 |
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