Patent US4048306A successfully refreshed from Google Patents.
US4048306A
Expired / Lapsed
US
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Aldehyde-erythromycylamine condensation products
Assignee: Boehringer Ingelheim GmbH
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Filing: 1976-03-29
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Granted: 1977-09-13
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Expires: 1996-03-29
Abstract
Abstract The invention relates to novel erythromycin derivatives, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as antibacterials.
Inventors
- 👤 Roland Maier
- 👤 Eberhard Woitun
- 👤 Bernd Wetzel
- 👤 Wolfgang Reuter
- 👤 Hanns Goeth
- 👤 Uwe Lechner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:30
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/14; C07D295/145; A; A61; A61P; A61P31/00; A61P31/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6558; C07F9/65586; C07F9/6561; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
438 words
An erythromycylamine-aldehyde condensation product of the formula ##STR12## wherein R is hydroxyl; phenoxy; phenyl-(alkoxy of 1 to 3 carbon atoms); alkoxy of 1 to 4 carbon atoms; hydroxy-(alkoxy of 1 to 4 carbon atoms); (alkoxy of 1 to 3 carbon atoms)-(alkoxy of 1 to 4 carbon atoms); di(alkyl of 1 to 3 carbon atoms)amino-(alkoxy of 1 to 4 carbon atoms); (alkoxy of 1 to 3 carbon atoms)-carbonyl(alkoxy of 1 to 4 carbon atoms); mercapto; phenyl-mercapto, where the phenyl moiety is unsubstituted or methyl-, methoxy-, ethoxy-, isopropoxy- or propoxy-substituted; phenyl-(alkyl of 1 to 3 carbon atoms)-mercapto; (straight or branched alkyl of 1 to 5 carbon atoms)-mercapto; cyclohexyl-mercapto; hydroxy-(alkyl of 1 to 3 carbon atoms)-mercapto; di(alkyl of 1 to 3 carbon atoms)amino-(alkyl of 1 to 3 carbon atoms)-mercapto; (alkoxy of 1 to 3 carbon atoms)-carbonyl-(alkyl of 1 to 3 carbon atoms)-mercapto; cyano-(alkyl of 1 to 3 carbon atoms)-mercapto; --NR 2 R 3 , where R 2 and R 3 , which may be identical to or different from each other, are each hydrogen, phenyl, phenyl-(alkyl of 1 to 3 carbon atoms), alkyl of 1 to 4 carbon atoms or, together with each other and the nitrogen atom to which they are attached, a 5- to 6-membered monocyclic heterocyclic ring which may contain an oxygen, sulfur or additional nitrogen atom; ##STR13## where R 4 is straight or branched alkyl of 1 to 5 carbon atoms, benzyl or phenyl; --NH--CO--R 5 , where R 5 is straight or branched alkyl of 1 to 5 carbon atoms, mono- or dihalo-substituted-(alkyl of 1 to 5 carbon atoms), cyano-(alkyl of 1 to 5 carbon atoms), phenyl-(alkyl of 1 to 3 carbon atoms) where the phenyl moiety may be mono- or di- or trimethoxy- or mono- or di-halo-substituted and the alkyl moiety may be monohalo-substituted, phenoxy-(alkyl of 1 to 3 carbon atoms), phenyl-(alkenyl of 2 to 4 carbon atoms), phenyl or phenyl having one or more methyl, hydroxyl, methoxy, nitro or chloro substituents attached thereto; or R 5 is pyridyl; furyl; fluoro-furyl; thienyl; N-phenyl-carbamoyl; ##STR14## where R 6 and R 7 , which may be identical to or different from each other, are each methyl, ethyl, propyl or isopropyl; ##STR15## where R 8 is straight or branched alkyl of 1 to 5 carbon atoms; --NH--SO 2 --R 9 , where R 9 is alkyl of 1 to 4 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl; or --SO 2 --R 10 , where R 10 is alkyl of 1 to 3 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
438 words
An erythromycylamine-aldehyde condensation product of the formula ##STR12## wherein R is hydroxyl; phenoxy; phenyl-(alkoxy of 1 to 3 carbon atoms); alkoxy of 1 to 4 carbon atoms; hydroxy-(alkoxy of 1 to 4 carbon atoms); (alkoxy of 1 to 3 carbon atoms)-(alkoxy of 1 to 4 carbon atoms); di(alkyl of 1 to 3 carbon atoms)amino-(alkoxy of 1 to 4 carbon atoms); (alkoxy of 1 to 3 carbon atoms)-carbonyl(alkoxy of 1 to 4 carbon atoms); mercapto; phenyl-mercapto, where the phenyl moiety is unsubstituted or methyl-, methoxy-, ethoxy-, isopropoxy- or propoxy-substituted; phenyl-(alkyl of 1 to 3 carbon atoms)-mercapto; (straight or branched alkyl of 1 to 5 carbon atoms)-mercapto; cyclohexyl-mercapto; hydroxy-(alkyl of 1 to 3 carbon atoms)-mercapto; di(alkyl of 1 to 3 carbon atoms)amino-(alkyl of 1 to 3 carbon atoms)-mercapto; (alkoxy of 1 to 3 carbon atoms)-carbonyl-(alkyl of 1 to 3 carbon atoms)-mercapto; cyano-(alkyl of 1 to 3 carbon atoms)-mercapto; --NR 2 R 3 , where R 2 and R 3 , which may be identical to or different from each other, are each hydrogen, phenyl, phenyl-(alkyl of 1 to 3 carbon atoms), alkyl of 1 to 4 carbon atoms or, together with each other and the nitrogen atom to which they are attached, a 5- to 6-membered monocyclic heterocyclic ring which may contain an oxygen, sulfur or additional nitrogen atom; ##STR13## where R 4 is straight or branched alkyl of 1 to 5 carbon atoms, benzyl or phenyl; --NH--CO--R 5 , where R 5 is straight or branched alkyl of 1 to 5 carbon atoms, mono- or dihalo-substituted-(alkyl of 1 to 5 carbon atoms), cyano-(alkyl of 1 to 5 carbon atoms), phenyl-(alkyl of 1 to 3 carbon atoms) where the phenyl moiety may be mono- or di- or trimethoxy- or mono- or di-halo-substituted and the alkyl moiety may be monohalo-substituted, phenoxy-(alkyl of 1 to 3 carbon atoms), phenyl-(alkenyl of 2 to 4 carbon atoms), phenyl or phenyl having one or more methyl, hydroxyl, methoxy, nitro or chloro substituents attached thereto; or R 5 is pyridyl; furyl; fluoro-furyl; thienyl; N-phenyl-carbamoyl; ##STR14## where R 6 and R 7 , which may be identical to or different from each other, are each methyl, ethyl, propyl or isopropyl; ##STR15## where R 8 is straight or branched alkyl of 1 to 5 carbon atoms; --NH--SO 2 --R 9 , where R 9 is alkyl of 1 to 4 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl; or --SO 2 --R 10 , where R 10 is alkyl of 1 to 3 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and methoxyacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and glycolaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and phenoxyacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and acetylaminoacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and N-(m,m',p-trimethoxybenzoyl-aminoacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and o-toluylaminoacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and methylthioacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and (2-hydroxy-ethoxy)-acetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and (2-ethoxy)-acetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
23 words
A compound of claim 1, which is the condensation product of erythromycylamine and diethylphosphonoacetaldehyde, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
20 words
An antibacterial composition consisting essentially of an inert carrier and an effective antibacterial amount of a compound of claim 1.
Claim 14
Dependent Claim
29 words
The method of combatting bacterial infections in a warm-blooded host, which comprises perorally or parenterally administering to said host an effective antibacterial amount of a compound of claim 1.
References Cited (Backward Citations)
US3660376A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |