CA2118489A1 - 5-O-Desosaminylerythronolide a Derivatives - Google Patents
5-O-Desosaminylerythronolide a DerivativesInfo
- Publication number
- CA2118489A1 CA2118489A1 CA 2118489 CA2118489A CA2118489A1 CA 2118489 A1 CA2118489 A1 CA 2118489A1 CA 2118489 CA2118489 CA 2118489 CA 2118489 A CA2118489 A CA 2118489A CA 2118489 A1 CA2118489 A1 CA 2118489A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- desosaminylerythronolide
- derivatives
- represented
- carbon atoms
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical group C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
- 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
- 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
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
Abstract
Object: To provide novel macrolide antibiotics having a strong antibacterial activity.
Constitution: 5-O-desosaminylerythronolide A
derivatives represented by the formula:
(see fig. I) [wherein -A~ is a group of -N(R3)- (wherein R3 is a hydrogen atom or an alkyl group having 1 - 3 carbon atoms) or a group represented by -N=, and R1 and R2 are each a hydrogen atom or an alkyl group having 1 - 3 carbon atoms] which is a tricyclic carbamate of 5-O-desosaminylerythronolide A derivative having a ketone at the 3-position, being substituted by a methoxy group at the 6-position, and a pharmaceutically acceptable acid addition salt thereof; and a compound represented by the formula:
(see fig. II) (wherein R4 is an acetyl group or a propionyl group) which is an intermediate useful for the preparation of the 3-ketone forms of 5-O-desosaminylerythronolide A
derivatives.
Constitution: 5-O-desosaminylerythronolide A
derivatives represented by the formula:
(see fig. I) [wherein -A~ is a group of -N(R3)- (wherein R3 is a hydrogen atom or an alkyl group having 1 - 3 carbon atoms) or a group represented by -N=, and R1 and R2 are each a hydrogen atom or an alkyl group having 1 - 3 carbon atoms] which is a tricyclic carbamate of 5-O-desosaminylerythronolide A derivative having a ketone at the 3-position, being substituted by a methoxy group at the 6-position, and a pharmaceutically acceptable acid addition salt thereof; and a compound represented by the formula:
(see fig. II) (wherein R4 is an acetyl group or a propionyl group) which is an intermediate useful for the preparation of the 3-ketone forms of 5-O-desosaminylerythronolide A
derivatives.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10149292 | 1992-04-22 | ||
JP04-101492 | 1992-04-22 | ||
PCT/JP1993/000517 WO1993021200A1 (en) | 1992-04-22 | 1993-04-21 | 5-o-desosaminylerythronolide a derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2118489A1 true CA2118489A1 (en) | 1993-10-23 |
CA2118489C CA2118489C (en) | 1999-07-13 |
Family
ID=14302174
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002118489A Expired - Fee Related CA2118489C (en) | 1992-04-22 | 1993-04-21 | 5-o-desosaminylerythronolide a derivatives |
CA002118488A Expired - Fee Related CA2118488C (en) | 1992-04-22 | 1993-04-21 | 5-o-desosaminylerythronolide a derivative |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002118488A Expired - Fee Related CA2118488C (en) | 1992-04-22 | 1993-04-21 | 5-o-desosaminylerythronolide a derivative |
Country Status (12)
Country | Link |
---|---|
US (2) | US5591837A (en) |
EP (2) | EP0638585B1 (en) |
KR (2) | KR0166996B1 (en) |
AT (2) | ATE135707T1 (en) |
AU (2) | AU662420B2 (en) |
BR (1) | BR1100235A (en) |
CA (2) | CA2118489C (en) |
DE (2) | DE69301916T2 (en) |
DK (2) | DK0638585T3 (en) |
ES (2) | ES2096915T3 (en) |
GR (2) | GR3019787T3 (en) |
WO (2) | WO1993021200A1 (en) |
Families Citing this family (58)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE38426E1 (en) | 1995-10-09 | 2004-02-10 | Aventis Pharma S.A. | 5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials |
FR2739620B1 (en) * | 1995-10-09 | 1997-12-19 | Roussel Uclaf | NOVEL DERIVATIVES OF 5-0-DESOSAMINYL 6-O-METHYL ERYTHRONOLIDE A, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO THE PREPARATION OF BIOLOGICALLY ACTIVE PRODUCTS |
US5747466A (en) * | 1995-11-08 | 1998-05-05 | Abbott Laboratories | 3-deoxy-3-descladinose derivatives of erythromycins A and B |
US6274715B1 (en) * | 1995-11-08 | 2001-08-14 | Abbott Laboratories | Tricyclic erythromycin derivatives |
ATE259823T1 (en) * | 1995-11-08 | 2004-03-15 | Abbott Lab | TRICYCLIC ERYTHROMYCIN DERIVATIVES |
US5750510A (en) * | 1997-04-04 | 1998-05-12 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
UA51730C2 (en) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-0-substituted ketolides having antibacterial activity |
KR100576988B1 (en) * | 1996-09-04 | 2006-05-10 | 아보트 러보러터리즈 | 6-0-substituted ketolides having antibacterial activity |
IL129946A0 (en) | 1996-11-27 | 2000-02-29 | Taisho Pharmaceutical Co Ltd | Erythromycin a derivatives |
FR2757168B1 (en) * | 1996-12-12 | 1999-06-11 | Hoechst Marion Roussel Inc | NOVEL ERYTHROMYCIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
WO1998040392A1 (en) * | 1997-03-10 | 1998-09-17 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
US6140479A (en) * | 1997-03-24 | 2000-10-31 | Taisho Pharmaceuticals Co., Ltd. | Erythromycin a derivatives |
US6162794A (en) * | 1997-05-09 | 2000-12-19 | Pfizer Inc. | Erythromycin derivatives |
PL337066A1 (en) * | 1997-05-29 | 2000-07-31 | Abbott Lab | Polycyclic derivatives of erythromycin |
US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
US5780605A (en) * | 1997-09-08 | 1998-07-14 | Abbott Laboratories | 6,9-bridged erythromycin derivatives |
US5780604A (en) * | 1997-09-26 | 1998-07-14 | Abbott Laboratories | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides |
US6124269A (en) * | 1997-10-29 | 2000-09-26 | Abbott Laboratories | 2-Halo-6-O-substituted ketolide derivatives |
CO4990960A1 (en) * | 1997-10-29 | 2000-12-26 | Abbott Lab | 2-HALO-6-O SUBSTITUTED CETOLIDE DERIVATIVES |
PA8461401A1 (en) * | 1997-10-29 | 2000-05-24 | Pfizer Prod Inc | TRICYCLIC ERYTHROMYCINE DERIVATIVES |
HN1998000159A (en) * | 1997-10-29 | 1999-02-09 | Monsanto Co | DERIVATIVES OF 9- AMINO - 3 CETO ERITROMICINA |
FR2777282B1 (en) * | 1998-04-08 | 2001-04-20 | Hoechst Marion Roussel Inc | NEW DERIVATIVES OF 2-FLUORO 3-DE ((2,6-DIDEOXY 3-C-METHYL 3-0-METHYL-ALPHA-L-RIBOHEXOPYRANOSYL) OXYL) 6-O-METHYL 3-OXO ERYTHROMYCIN, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO THE SYNTHESIS OF ACTIVE INGREDIENTS OF MEDICINES |
PT952157E (en) * | 1998-04-24 | 2003-11-28 | Pfizer Prod Inc | DERIVATIVES 9A, 11B-9-OXIMA-3-CETO-6-O-METHYLERITROMYCIN DERIVATIVES |
WO1999062920A1 (en) * | 1998-06-03 | 1999-12-09 | Pfizer Products Inc. | Tricyclic 3-keto derivatives of 6-o-methylerythromycin |
FR2784682B1 (en) | 1998-10-15 | 2002-12-06 | Hoechst Marion Roussel Inc | NOVEL 2-HALOGEN DERIVATIVES OF 5-0-DESOSAMINYLERYTHRONOLIDE A, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS |
US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
US6355620B1 (en) | 1999-05-14 | 2002-03-12 | Abbott Laboratories | C-2 modified erythromycin derivatives |
US6569836B2 (en) | 1999-12-02 | 2003-05-27 | Abbott Laboratories | 6-O-alkyl-2-nor-2-substituted ketolide derivatives |
US6946446B2 (en) | 2000-02-24 | 2005-09-20 | Abbott Laboratories | Anti-infective agents useful against multidrug-resistant strains of bacteria |
EP1146051A3 (en) * | 2000-04-10 | 2001-10-31 | Pfizer Products Inc. | Erythromycin A derivatives |
NZ536402A (en) * | 2002-05-13 | 2006-08-31 | Enanta Pharm Inc | 6,11 bicyclic erythromycin derivatives |
US6841664B2 (en) | 2002-07-25 | 2005-01-11 | Enanra Pharmaceuticals, Inc. | 6,11-4-carbon bridged ketolides |
US7910558B2 (en) * | 2002-05-13 | 2011-03-22 | Enanta Pharmaceuticals, Inc. | Bridged macrocyclic compounds and processes for the preparation thereof |
US6878691B2 (en) * | 2002-05-13 | 2005-04-12 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
US6764998B1 (en) | 2003-06-18 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | 6,11-4C-bicyclic 9a-azalide derivatives |
WO2005070918A1 (en) * | 2002-05-13 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | Process for the preparation of t-11 bicyclic erythromycin derivatives |
US7273853B2 (en) * | 2002-05-13 | 2007-09-25 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
US6753318B1 (en) * | 2002-07-25 | 2004-06-22 | Enanta Pharmaceuticals, Inc. | 6,11-4-carbon bridged erythromycin derivatives |
US7135573B2 (en) * | 2002-05-13 | 2006-11-14 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of O-(6-Pyrazol-1-yl-pyridin-3-ylmethyl)-hydroxylamine |
US7064110B2 (en) * | 2002-05-13 | 2006-06-20 | Enanta Pharmaceuticals, Inc. | 6-11 bicycle ketolide derivatives |
US6645941B1 (en) | 2003-03-26 | 2003-11-11 | Enanta Pharmaceuticals, Inc. | 6,11-3C-bicyclic 9a-azalide derivatives |
US7276487B2 (en) * | 2003-09-23 | 2007-10-02 | Enanta Pharmaceuticals, Inc. | 9a, 11-3C-bicyclic 9a-azalide derivatives |
WO2005067564A2 (en) * | 2004-01-07 | 2005-07-28 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic erythromycin derivatives |
US7265094B2 (en) * | 2004-01-09 | 2007-09-04 | Enanta Pharmaceuticals, Inc. | 9N-substituted 6-11 bicyclic erythromycin derivatives |
US7163906B2 (en) * | 2004-11-04 | 2007-01-16 | Chevron Phillips Chemical Company, Llp | Organochromium/metallocene combination catalysts for producing bimodal resins |
US7229972B2 (en) | 2004-12-07 | 2007-06-12 | Enanta Pharmaceuticals, Inc. | 3,6-Bicyclolides |
KR100924610B1 (en) | 2004-12-07 | 2009-11-02 | 이난타 파마슈티칼스, 인코포레이티드 | 3,6-bicyclolides |
US7312201B2 (en) | 2004-12-13 | 2007-12-25 | Enanta Pharmaceuticals, Inc. | Tetracyclic bicyclolides |
WO2006065721A2 (en) | 2004-12-13 | 2006-06-22 | Enanta Pharmaceuticals, Inc. | 11, 12-lactone bicyclolides |
US7384922B2 (en) * | 2005-05-04 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | 6-11 bridged oxime erythromycin derivatives |
CN101454334B (en) | 2006-05-01 | 2013-04-10 | 大正制药株式会社 | Macrolide derivatives |
US20070298811A1 (en) * | 2006-06-21 | 2007-12-27 | Lockheed Martin Corporation | System for predicting bandwidth capacity |
WO2009006403A2 (en) * | 2007-06-29 | 2009-01-08 | Georgia Tech Research Corporation | Non-peptide macrocyclic histone deacetylase (hdac) inhibitors and methods of making and using thereof |
US8871728B2 (en) | 2007-06-29 | 2014-10-28 | Georgia Tech Research Corporation | Non-peptide macrocyclic histone deacetylese (HDAC) inhibitors and methods of making and using thereof |
ES2691252T3 (en) * | 2007-09-17 | 2018-11-26 | Enanta Pharmaceuticals, Inc. | Biaryl macrolides with bridge in 6.11 |
US8354383B2 (en) * | 2007-09-17 | 2013-01-15 | Enanta Pharmaceuticals, Inc. | 6,11-bridged biaryl macrolides |
US8273720B2 (en) * | 2007-09-17 | 2012-09-25 | Enanta Pharmaceuticals, Inc. | 6,11-bicyclolides: bridged biaryl macrolide derivatives |
TW200946109A (en) * | 2008-05-09 | 2009-11-16 | Enanta Pharm Inc | Anti-bacterial activity of 9-hydroxy derivatives 6, 11-bicyclolides |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5175150A (en) * | 1985-08-31 | 1992-12-29 | Kitasato, Kenkyusho | Erythromycin derivative |
US4742049A (en) * | 1986-06-04 | 1988-05-03 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
CA2096969C (en) * | 1990-11-28 | 2000-11-21 | Masato Kashimura | 6-0-methylerythromycin a derivatives |
US5523399A (en) * | 1991-12-27 | 1996-06-04 | Taisho Pharmaceutical Co., Ltd. | 5-O-desosaminylerythronolide derivatives |
-
1993
- 1993-04-21 AT AT93909403T patent/ATE135707T1/en not_active IP Right Cessation
- 1993-04-21 DE DE69301916T patent/DE69301916T2/en not_active Expired - Fee Related
- 1993-04-21 US US08/318,795 patent/US5591837A/en not_active Expired - Fee Related
- 1993-04-21 KR KR1019940703541A patent/KR0166996B1/en not_active IP Right Cessation
- 1993-04-21 WO PCT/JP1993/000517 patent/WO1993021200A1/en active IP Right Grant
- 1993-04-21 AT AT93909404T patent/ATE145212T1/en not_active IP Right Cessation
- 1993-04-21 DK DK93909404.1T patent/DK0638585T3/en active
- 1993-04-21 DK DK93909403.3T patent/DK0638584T3/en active
- 1993-04-21 AU AU40223/93A patent/AU662420B2/en not_active Ceased
- 1993-04-21 US US08/318,862 patent/US5631355A/en not_active Expired - Fee Related
- 1993-04-21 EP EP93909404A patent/EP0638585B1/en not_active Expired - Lifetime
- 1993-04-21 AU AU40222/93A patent/AU661585B2/en not_active Ceased
- 1993-04-21 WO PCT/JP1993/000516 patent/WO1993021199A1/en active IP Right Grant
- 1993-04-21 EP EP93909403A patent/EP0638584B1/en not_active Expired - Lifetime
- 1993-04-21 CA CA002118489A patent/CA2118489C/en not_active Expired - Fee Related
- 1993-04-21 CA CA002118488A patent/CA2118488C/en not_active Expired - Fee Related
- 1993-04-21 ES ES93909404T patent/ES2096915T3/en not_active Expired - Lifetime
- 1993-04-21 DE DE69305987T patent/DE69305987T2/en not_active Expired - Fee Related
- 1993-04-21 KR KR1019940703540A patent/KR100244729B1/en not_active IP Right Cessation
- 1993-04-21 ES ES93909403T patent/ES2087737T3/en not_active Expired - Lifetime
-
1996
- 1996-04-29 GR GR960401167T patent/GR3019787T3/en unknown
- 1996-12-11 GR GR960403431T patent/GR3021992T3/en unknown
-
1997
- 1997-04-07 BR BR1100235-2A patent/BR1100235A/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
KR100244729B1 (en) | 2000-02-15 |
BR1100235A (en) | 2002-04-30 |
EP0638584A4 (en) | 1994-12-23 |
CA2118488C (en) | 2002-11-05 |
GR3021992T3 (en) | 1997-03-31 |
KR950700921A (en) | 1995-02-20 |
AU661585B2 (en) | 1995-07-27 |
EP0638585B1 (en) | 1996-11-13 |
AU4022393A (en) | 1993-11-18 |
GR3019787T3 (en) | 1996-07-31 |
CA2118488A1 (en) | 1993-10-23 |
WO1993021200A1 (en) | 1993-10-28 |
EP0638584B1 (en) | 1996-03-20 |
DE69305987T2 (en) | 1997-03-06 |
ATE145212T1 (en) | 1996-11-15 |
KR0166996B1 (en) | 1999-01-15 |
EP0638584A1 (en) | 1995-02-15 |
CA2118489C (en) | 1999-07-13 |
AU662420B2 (en) | 1995-08-31 |
US5631355A (en) | 1997-05-20 |
EP0638585A1 (en) | 1995-02-15 |
KR950700920A (en) | 1995-02-20 |
DK0638585T3 (en) | 1996-12-02 |
US5591837A (en) | 1997-01-07 |
DE69301916D1 (en) | 1996-04-25 |
AU4022293A (en) | 1993-11-18 |
EP0638585A4 (en) | 1995-04-19 |
DE69305987D1 (en) | 1996-12-19 |
DE69301916T2 (en) | 1996-08-08 |
WO1993021199A1 (en) | 1993-10-28 |
ATE135707T1 (en) | 1996-04-15 |
ES2087737T3 (en) | 1996-07-16 |
DK0638584T3 (en) | 1996-04-15 |
ES2096915T3 (en) | 1997-03-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed | ||
MKLA | Lapsed |
Effective date: 20040421 |