← Back to Patent Explorer
US5631354A Expired / Lapsed US ⏱️ 0.0 years remaining

5-O-desosaminylerythronolide derivatives

Assignee: Taisho Pharmaceutical Co Ltd
•
Filing: 1992-12-25
•
Granted: 1997-05-20
•
Expires: 2012-12-25
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract PCT No. PCT/JP92/01714 Sec. 371 Date Jun. 21, 1994 Sec. 102(e) Date Jun. 21, 1994 PCT Filed Dec. 25, 1992 PCT Pub. No. WO93/13116 PCT Pub. Date Jul. 8, 1993Object: Provision of novel macrolide antibiotics having a strong antibacterial activity. Construction: Compounds represented by the formula: <IMAGE> which are obtained by introducing a certain substituted carbonyloxy group into 5-O-desosaminylerythronolide derivatives at the 3-position; and pharmaceutically acceptable acid addition salts thereof.

Inventors

  • 👤 Toshifumi Asaka
  • 👤 Yoko Misawa
  • 👤 Masato Kashimura
  • 👤 Shigeo Morimoto
  • 👤 Katsuo Hatayama

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 23:49
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; A; A61; A61P; A61P31/00; A61P31/04

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 578 words
A 5-0-desosaminylerythronolide derivative represented by the formula: ##STR37## wherein: Y is a group represented by the formula: ##STR38## (wherein R 1 is a hydrogen atom, a hydroxyl group, a halogen atom, a C 1 -C 3 alkyl group or an amino group, and n is an integer of 0 to 4), an oxygen atom, a vinylene group, or a group represented by the formula --CH 2 --NH--CO, R is a C 7 -C 15 aralkyl group; a C 7 -C 15 aralkyl group substituted by at least one member selected from the group consisting of a nitro group, a methoxy group, a methoxythio group, a methoxycarbonyl group, a carboxy group, a methylene group, a halogen atom, a trifluoromethyl group, an amino group and a demethylamino group; a phenyl group; a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C 1 -C 3 alkyl groups, C 1 -C 3 alkyl groups substituted by one or more halogen atoms, C 1 -C 4 alkylamino groups, C 2 -C 7 acylamino groups and C 1 -C 4 alkoxy groups; a naphthyl group; a thiazolyl group; an imidazolyl group; an amino-thiazolyl group; a biphenyl group; a thienyl group; a pyridyl group; a pyridyl group substituted by one or more nitro groups; a phenylthio group; a phenyloxy group substituted by one or more halogen atoms or nitro groups; or an indolyl group, A is a group represented by: the formula (i): ##STR39## wherein Z is an oxygen atom or a group represented by the formula ═N--O--R 4 (wherein R 4 is a hydrogen atom; a C 1 -C 8 alkyl group; --CH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 CH 2 OCH 3 ; --CH 2 CH 2 SCH 3 ; --CH 2 CH 2 (NH)CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 CH 2 N(CH 2 )(CH 2 Ph; a benzyl group; or a benzyl group having 1 to 5 substituents selected from the group consisting of halogen atoms and C 1 -C 4 alkyl groups), V is a hydroxyl group and W is a hydrogen atom or a hydroxyl group, or V and W represent, together with the carbon atoms at the 11- and 12-positions, a group represented by the formula: ##STR40## a group represented by the formula: ##STR41## (wherein R 5 is a hydrogen atom or a C 1 -C 3 alkyl group), a group represented by the formula (ii): ##STR42## (wherein R 6 is a hydrogen atom or a C 1 -C 3 alkyl group), or a group represented by the formula (iii): ##STR43## (wherein R 7 is a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 5 alkenyl group or C 3 -C 5 alkynyl group, and V and W are as defined above), R' is a hydrogen atom, a C 1 -C 5 alkyl group, a carbamoyl group or an acetyl group, R" is a hydrogen atom, a C 2 -C 15 alkoxycarbonyl group, 2-[2-(2-methoxyethyoxy) ethoxy]ethoxycarbonyl group, 2-[2-(2-ethoxyethoxy)ethoxy]ethoxycarbonyl group, a C 2 -C 15 acyl group, an ethylsuccinyl group, or a pyridylcarbonyl group or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 578 words
A 5-0-desosaminylerythronolide derivative represented by the formula: ##STR37## wherein: Y is a group represented by the formula: ##STR38## (wherein R 1 is a hydrogen atom, a hydroxyl group, a halogen atom, a C 1 -C 3 alkyl group or an amino group, and n is an integer of 0 to 4), an oxygen atom, a vinylene group, or a group represented by the formula --CH 2 --NH--CO, R is a C 7 -C 15 aralkyl group; a C 7 -C 15 aralkyl group substituted by at least one member selected from the group consisting of a nitro group, a methoxy group, a methoxythio group, a methoxycarbonyl group, a carboxy group, a methylene group, a halogen atom, a trifluoromethyl group, an amino group and a demethylamino group; a phenyl group; a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C 1 -C 3 alkyl groups, C 1 -C 3 alkyl groups substituted by one or more halogen atoms, C 1 -C 4 alkylamino groups, C 2 -C 7 acylamino groups and C 1 -C 4 alkoxy groups; a naphthyl group; a thiazolyl group; an imidazolyl group; an amino-thiazolyl group; a biphenyl group; a thienyl group; a pyridyl group; a pyridyl group substituted by one or more nitro groups; a phenylthio group; a phenyloxy group substituted by one or more halogen atoms or nitro groups; or an indolyl group, A is a group represented by: the formula (i): ##STR39## wherein Z is an oxygen atom or a group represented by the formula ═N--O--R 4 (wherein R 4 is a hydrogen atom; a C 1 -C 8 alkyl group; --CH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 CH 2 OCH 3 ; --CH 2 CH 2 SCH 3 ; --CH 2 CH 2 (NH)CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 CH 2 N(CH 2 )(CH 2 Ph; a benzyl group; or a benzyl group having 1 to 5 substituents selected from the group consisting of halogen atoms and C 1 -C 4 alkyl groups), V is a hydroxyl group and W is a hydrogen atom or a hydroxyl group, or V and W represent, together with the carbon atoms at the 11- and 12-positions, a group represented by the formula: ##STR40## a group represented by the formula: ##STR41## (wherein R 5 is a hydrogen atom or a C 1 -C 3 alkyl group), a group represented by the formula (ii): ##STR42## (wherein R 6 is a hydrogen atom or a C 1 -C 3 alkyl group), or a group represented by the formula (iii): ##STR43## (wherein R 7 is a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 5 alkenyl group or C 3 -C 5 alkynyl group, and V and W are as defined above), R' is a hydrogen atom, a C 1 -C 5 alkyl group, a carbamoyl group or an acetyl group, R" is a hydrogen atom, a C 2 -C 15 alkoxycarbonyl group, 2-[2-(2-methoxyethyoxy) ethoxy]ethoxycarbonyl group, 2-[2-(2-ethoxyethoxy)ethoxy]ethoxycarbonyl group, a C 2 -C 15 acyl group, an ethylsuccinyl group, or a pyridylcarbonyl group or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 180 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein: Y is a group represented by the formula: ##STR44## (wherein R 1 is a hydrogen atom, a hydroxyl group, a halogen atom or a C 1 -C 3 alkyl group, and n is 1) or an oxygen atom, R is a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C 1 -C 3 alkyl groups, C 1 -C 3 alkyl groups substituted with one or more halogen atoms, C 1 -C 4 alkylamino groups, C 2 -C 7 acylamino groups and C 1 -C 4 alkoxy groups; an aminothiazolyl group; a pyridyl group; or a phenyloxy group substituted with one or more halogen atoms or nitro groups; A is a group represented by the formula (i) or the formula (ii), R' is a hydrogen atom or a C 1 -C 5 alkyl group, R" is a hydrogen atom, 2-[2-(2-methoxyethoxy)ethoxy]ethoxycarbonyl group, 2-[2-(2-ethoxyethoxy)ethoxy]ethoxycarbonyl group, a C 2 -C 15 acyl group or a pyridylcarbonyl group.
Claim 4
Dependent Claim 105 words
A 5-0-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein: Y is a group represented by the formula: ##STR45## wherein R 1 is a hydrogen atom, a hydroxyl group, a halogen atom or a C 1 -C 3 alkyl group, and n is 0-4, and R is a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C 1 -C 3 alkyl groups substituted with one or more halogen atoms, C 1 -C 4 alkylamino groups, C 2 -C 7 acylamino groups and C 1 -C 4 alkoxy groups.
Claim 5
Dependent Claim 5 words
3-O-(4-nitrophenyl)acetyl-5-O-desosaminylerythronolide A 9-oxime 11,12-cyclic carbonate.
Claim 6
Dependent Claim 5 words
3-O-(4-nitrophenyl)acetyl-5-O-desosaminylerythronolide A 9-oxime 11,12-cyclic carbonate.
Claim 7
Dependent Claim 63 words
A 5-0-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein: Y is a group represented by the formula: ##STR46## wherein R 1 is a hydrogen atom, a hydroxyl group, a halogen atom or a C 1 -C 3 alkyl group, and n is 0-4, and R is a phenyl group substituted with at least one nitro group.
Claim 8
Dependent Claim 185 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein: A is (i); Z is an oxygen atom or a group represented by the formula ═N--O--R 4 (wherein R 4 is a hydrogen atom; a C 1 -C 8 alkyl group; --CH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 CH 2 OCH 3 ; --CH 2 CH 2 SCH 3 ; --CH 2 CH 2 (NH)CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 CH 2 N(CH 3 )CH 2 Ph; a benzyl group; or a benzyl group having 1 to 5 substituents selected from the group consisting of halogen atoms and C 1 -C 4 alkyl groups); and V and W represent, together with the carbon atoms at the 11- and 12-positions, a group represented by the formula: ##STR47##
Claim 9
Dependent Claim 185 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 5, wherein: A is (i); Z is an oxygen atom or a group represented by the formula ═N--O--R 4 (wherein R 4 is a hydrogen atom; a C 1 -C 8 alkyl group; --CH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 CH 2 OCH 3 ; --CH 2 CH 2 SCH 3 ; --CH 2 CH 2 (NH)CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 CH 2 N(CH 3 )CH 2 Ph; a benzyl group; or a benzyl group having 1 to 5 substituents selected from the group consisting of halogen atoms and C 1 -C 4 alkyl groups); and V and W represent, together with the carbon atoms at the 11- and 12-positions, a group represented by the formula: ##STR48##
Claim 10
Dependent Claim 185 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein: A is (i); Z is an oxygen atom or a group represented by the formula ═N--O--R 4 (wherein R 4 is a hydrogen atom; a C 1 -C 8 alkyl group, --CH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 CH 2 OCH 3 ; --CH 2 CH 2 SCH 3 ; --CH 2 CH 2 (NH)CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 OCH 2 CH 2 OCH 3 ; --CH 2 CH 2 N(CH 3 ) 2 ; --CH 2 CH 2 N(CH 3 )CH 2 Ph; a benzyl group; or a benzyl group having 1 to 5 substituents selected from the group consisting of halogen atoms and C 1 -C 4 alkyl groups); and V and W represent, together with the carbon atoms at the 11- and 12-positions, a group represented by the formula: ##STR49##
Claim 11
Dependent Claim 19 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein A is (ii).
Claim 12
Dependent Claim 19 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein A is (iii).
Claim 13
Dependent Claim 21 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein Y is an oxygen atom.
Claim 14
Dependent Claim 21 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein Y is a vinylene group.
Claim 15
Dependent Claim 21 words
A 5-O-desosaminylerythronolide derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein Y is --CH 2 --NH--CO--.

References Cited (Backward Citations)

US3923784A Cited
US4518590A Cited
EP0216169A2 Cited
US4742049A Cited
US4921839A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2000-05-19 2000-11-18 2001-05-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2004-05-19 2004-11-18 2005-05-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2008-05-19 2008-11-18 2009-05-20 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag