WO2003014136A1 - 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME - Google Patents
11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME Download PDFInfo
- Publication number
- WO2003014136A1 WO2003014136A1 PCT/JP2002/008081 JP0208081W WO03014136A1 WO 2003014136 A1 WO2003014136 A1 WO 2003014136A1 JP 0208081 W JP0208081 W JP 0208081W WO 03014136 A1 WO03014136 A1 WO 03014136A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- represents hydrogen
- hydrogen
- alkyl
- same
- hydroxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 3
- 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 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- 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
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
11a-Azalide compounds represented by the following general formula (1) or pharmaceutically acceptable salts thereof: (1) wherein R1 represents hydrogen, C1-10 alkyl, etc.; R2represents hydrogen, hydroxy, etc.; R3 represents hydrogen, acetyl, etc.; R4 and R5 represent each hydrogen, C1-10 alkyl, etc.; R6 represents hydrogen, hydroxy, etc.; R7 represents hydrogen, or R6 and R7 form together carbonyl, etc.; R8 represents hydrogen, halogeno, etc.; X represents carbonyl, etc.; Y represents a group of the following general formula (14): (14) (wherein k is an integer of 2 to 4; and R24 and R25 are the same or different and each represents hydrogen, C1-10 alkyl, etc.); and Z represents oxygen, etc. These compounds are useful as novel antibiotics showing an antibacterial effect not only on the existing erythromycin-sensitive strains but also on erythromycin-tolerant strains (for example, tolerant pneumococci and streptococci).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003519085A JP4311203B2 (en) | 2001-08-08 | 2002-08-07 | 11a-azalide compound and method for producing the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001-240263 | 2001-08-08 | ||
| JP2001240263 | 2001-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003014136A1 true WO2003014136A1 (en) | 2003-02-20 |
Family
ID=19070904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2002/008081 WO2003014136A1 (en) | 2001-08-08 | 2002-08-07 | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP4311203B2 (en) |
| WO (1) | WO2003014136A1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108744A2 (en) * | 2003-05-19 | 2004-12-16 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| WO2005019238A1 (en) * | 2003-08-22 | 2005-03-03 | Meiji Seika Kaisha, Ltd. | Novel azalide and azalactam derivatives and process for the production of the same |
| US7015203B2 (en) | 1998-01-02 | 2006-03-21 | Pfizer Inc. | Macrolides |
| JP2006528667A (en) * | 2003-05-13 | 2006-12-21 | グラクソ グループ リミテッド | Novel 14- and 15-membered ring compounds |
| JP2006528947A (en) * | 2003-05-13 | 2006-12-28 | グラクソ グループ リミテッド | 4 "-substituted macrolide |
| JP2007500193A (en) * | 2003-05-13 | 2007-01-11 | グラクソ グループ リミテッド | Novel 14- and 15-membered ring compounds |
| JP2007502313A (en) * | 2003-05-13 | 2007-02-08 | グラクソ グループ リミテッド | New 14- and 15-membered ring compounds |
| EP1985620A1 (en) * | 2006-02-07 | 2008-10-29 | Taisho Pharmaceutical Co., Ltd | 10a-AZALIDE COMPOUND |
| WO2009019868A1 (en) | 2007-08-06 | 2009-02-12 | Taisho Pharmaceutical Co., Ltd. | 10a-azalide compound crosslinked at position-10a and position-12 |
| WO2009139181A1 (en) | 2008-05-15 | 2009-11-19 | 大正製薬株式会社 | 10a-azalide compound having 4-membered ring structure |
| WO2017194452A1 (en) * | 2016-05-11 | 2017-11-16 | Fidelta D.O.O. | Seco macrolide compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06247996A (en) * | 1993-02-25 | 1994-09-06 | Taisho Pharmaceut Co Ltd | 6-o-methylerythromycin a derivative |
| EP0895999A1 (en) * | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| WO2000031097A1 (en) * | 1998-11-20 | 2000-06-02 | Pfizer Products Inc. | 13-membered azalides and their use as antibiotic agents |
-
2002
- 2002-08-07 WO PCT/JP2002/008081 patent/WO2003014136A1/en active Application Filing
- 2002-08-07 JP JP2003519085A patent/JP4311203B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06247996A (en) * | 1993-02-25 | 1994-09-06 | Taisho Pharmaceut Co Ltd | 6-o-methylerythromycin a derivative |
| EP0895999A1 (en) * | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| WO2000031097A1 (en) * | 1998-11-20 | 2000-06-02 | Pfizer Products Inc. | 13-membered azalides and their use as antibiotic agents |
Non-Patent Citations (1)
| Title |
|---|
| WADDELL SHERMAN T. ET AL.: "Chimeric azalides with simplified western portions", TETRAHEDRON LETTERS, vol. 34, no. 34, 20 August 1993 (1993-08-20), pages 5385 - 5388, XP002959892 * |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7015203B2 (en) | 1998-01-02 | 2006-03-21 | Pfizer Inc. | Macrolides |
| JP2007500193A (en) * | 2003-05-13 | 2007-01-11 | グラクソ グループ リミテッド | Novel 14- and 15-membered ring compounds |
| JP2006528667A (en) * | 2003-05-13 | 2006-12-21 | グラクソ グループ リミテッド | Novel 14- and 15-membered ring compounds |
| JP2006528947A (en) * | 2003-05-13 | 2006-12-28 | グラクソ グループ リミテッド | 4 "-substituted macrolide |
| JP2007502313A (en) * | 2003-05-13 | 2007-02-08 | グラクソ グループ リミテッド | New 14- and 15-membered ring compounds |
| WO2004108744A3 (en) * | 2003-05-19 | 2005-03-24 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| WO2004108744A2 (en) * | 2003-05-19 | 2004-12-16 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| WO2005019238A1 (en) * | 2003-08-22 | 2005-03-03 | Meiji Seika Kaisha, Ltd. | Novel azalide and azalactam derivatives and process for the production of the same |
| US7365174B2 (en) | 2003-08-22 | 2008-04-29 | Meiji Seika Kaisha, Ltd. | Azalide and azalactam derivatives and method for producing the same |
| EP1985620A4 (en) * | 2006-02-07 | 2012-08-15 | Taisho Pharmaceutical Co Ltd | 10a-AZALIDE COMPOUND |
| EP1985620A1 (en) * | 2006-02-07 | 2008-10-29 | Taisho Pharmaceutical Co., Ltd | 10a-AZALIDE COMPOUND |
| JP5015016B2 (en) * | 2006-02-07 | 2012-08-29 | 大正製薬株式会社 | 10a-azalide compounds |
| US8097708B2 (en) | 2006-02-07 | 2012-01-17 | Taisho Pharmaceutical Co., Ltd. | 10a-Azalide compound |
| WO2009019868A1 (en) | 2007-08-06 | 2009-02-12 | Taisho Pharmaceutical Co., Ltd. | 10a-azalide compound crosslinked at position-10a and position-12 |
| US8293715B2 (en) | 2007-08-06 | 2012-10-23 | Taisho Pharmaceutical Co., Ltd. | 10a-Azalide compound crosslinked at 10a- and 12-positions |
| WO2009139181A1 (en) | 2008-05-15 | 2009-11-19 | 大正製薬株式会社 | 10a-azalide compound having 4-membered ring structure |
| US8299035B2 (en) | 2008-05-15 | 2012-10-30 | Taisho Pharmaceutucal Co., Ltd. | 10a-azalide compound having 4-membered ring structure |
| WO2017194452A1 (en) * | 2016-05-11 | 2017-11-16 | Fidelta D.O.O. | Seco macrolide compounds |
| CN109311929A (en) * | 2016-05-11 | 2019-02-05 | 菲德尔塔公司 | SECO Macrocyclic lactone compounds |
| US10919910B2 (en) | 2016-05-11 | 2021-02-16 | Fidelta D.O.O. | Seco macrolide compounds |
| CN109311929B (en) * | 2016-05-11 | 2022-10-04 | 塞尔维塔公司 | SECO macrolide compounds |
| US11512096B2 (en) | 2016-05-11 | 2022-11-29 | Selvita D.O.O. | Seco macrolide compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4311203B2 (en) | 2009-08-12 |
| JPWO2003014136A1 (en) | 2004-11-25 |
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