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US4349545A
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Novel erythromycin a derivatives
Assignee: RUSSEL UCLAF A CORPOF FRANCE
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Filing: 1981-01-08
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Granted: 1982-09-14
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Expires: 2001-01-08
Abstract
Abstract Novel erythromycin derivatives in the syn form or anti form or mixtures of the syn and anti forms of the formula ##STR1## wherein A is a linear or branched alkylene of 1 to 6 carbon atoms, R is selected from the group consisting of optionally substituted alkoxy of 1 to 6 carbon atoms, optionally substituted alkenyloxy and alkynyloxy of 2 to 6 carbon atoms, optionally substituted alkylthio of 1 to 6 carbon atoms, optionally substituted alkenylthio and alkynylthio of 2 to 6 carbon atoms with the thio group optionally oxidized to the sulfoxide or sulfone form, optionally substituted aryloxy and arylthio, optionally substituted aralkyloxy and arylalkylthio, the thio derivatives optionally oxidized to sulfoxide or sulfone, ##STR2## optionally substituted quaternary ammonium group, halogen, optionally substituted 1,2-epoxyethyl and the group resulting from opening of the epoxy with a nucleophilic reactant, ##STR3## a free or protected formyl, --COOR', thiocyanate, --CN, acyl and carbamoyl, R 1 and R 2 are individually selected from the group consisting of hydrogen, and optionally substituted alkyl of 1 to 6 carbon atoms or taken together with the nitrogen atom to which they are attached form an optionally substituted, optionally unsaturated heterocycle which can contain another heteroatom, B is selected from the group consisting of optionally substituted alkyl and alkoxy of 1 to 6 carbon atoms, optionally substituted aryl and aryloxy and optionally substituted aralkyl and aralkoxy of 1 to 6 alkyl carbon atoms, R' is selected from the group consisting of hydrogen, a cation and an ester group, R a is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having very good antibiotic activity and their preparation.
Inventors
- 👤 Solange Gouin d'Ambrieres
- 👤 Andre Lutz
- 👤 Jean-Claude Gasc
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:00
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
323 words
An erythromycin compound selected from the group consisting of a compound in the syn form or antiform or mixtures of the syn and anti forms of the formula ##STR23## wherein A is a linear or branched alkylene of 1 to 6 carbon atoms, R is selected from the group consisting of optionally substituted alkoxy of 1 to 6 carbon atoms, optionally substituted alkenyloxy and alkynyloxy of 2 to 6 carbon atoms, optionally substituted alkylthio of 1 to 6 carbon atoms, optionally substituted alkenylthioand alkynyllthio of 2 to 6 carbon atoms with the thio groups optionally oxidized to the sulfoxide or sulfone form, optionally substituted aryloxy and arylthio, optionally substituted aralkyloxy and arylalkylthio of 1 to 6 alkyl carbon atoms the thio derivatives optionally oxidized to sulfoxide or sulfone ##STR24## optionally substituted quaternary ammonium group, halogen, optionally substituted 1,2-epoxyethyl and the group resulting from opening of the epoxy with a nucleophilic reactant, ##STR25## a free or protected formyl, --COOR', thiocyanate, --CN, acyl and carbamoy, the said optional substitutents on the R groups being at least one member of the group consisting of halogen and alkoxy and alkylthio of 1 to 6 carbon atoms R 1 and R 2 are individually selected from the group consisting of hydrogen and optionally substituted alkyl of 1 to 6 carbon atoms or taken together with the nitrogen atom to which they are attached form an optionally substituted, optionally unsaturated heterocycle which can contain another heteroatom, B is selected from the group consisting of optionally substituted alkyl and alkoxy of 1 to 6 carbon atoms, optionally substituted aryl and aryloxy and optionally substituted aralkyl and aralkoxy of 1 to 6 alkyl carbon atoms, R' is selected from the group consisting of hydrogen, a cation and an ester group, R a is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
323 words
An erythromycin compound selected from the group consisting of a compound in the syn form or antiform or mixtures of the syn and anti forms of the formula ##STR23## wherein A is a linear or branched alkylene of 1 to 6 carbon atoms, R is selected from the group consisting of optionally substituted alkoxy of 1 to 6 carbon atoms, optionally substituted alkenyloxy and alkynyloxy of 2 to 6 carbon atoms, optionally substituted alkylthio of 1 to 6 carbon atoms, optionally substituted alkenylthioand alkynyllthio of 2 to 6 carbon atoms with the thio groups optionally oxidized to the sulfoxide or sulfone form, optionally substituted aryloxy and arylthio, optionally substituted aralkyloxy and arylalkylthio of 1 to 6 alkyl carbon atoms the thio derivatives optionally oxidized to sulfoxide or sulfone ##STR24## optionally substituted quaternary ammonium group, halogen, optionally substituted 1,2-epoxyethyl and the group resulting from opening of the epoxy with a nucleophilic reactant, ##STR25## a free or protected formyl, --COOR', thiocyanate, --CN, acyl and carbamoy, the said optional substitutents on the R groups being at least one member of the group consisting of halogen and alkoxy and alkylthio of 1 to 6 carbon atoms R 1 and R 2 are individually selected from the group consisting of hydrogen and optionally substituted alkyl of 1 to 6 carbon atoms or taken together with the nitrogen atom to which they are attached form an optionally substituted, optionally unsaturated heterocycle which can contain another heteroatom, B is selected from the group consisting of optionally substituted alkyl and alkoxy of 1 to 6 carbon atoms, optionally substituted aryl and aryloxy and optionally substituted aralkyl and aralkoxy of 1 to 6 alkyl carbon atoms, R' is selected from the group consisting of hydrogen, a cation and an ester group, R a is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
41 words
A compound of claim 1 wherein R is selected from the group consisting of halogen, dialkylamino, alkoxy optionally substituted with alkoxy or dialkylamino, aryloxy or aralkoxy optionally substituted with a halogen and alkylthio or aryl alkylthio optionally substituted with a halogen.
Claim 4
Dependent Claim
84 words
A compound of claim 1 having the formula ##STR26## wherein n is an integer from 1 to 6, R' is selected from the group consisting of alkoxy and alkoxyalkoxy of 1 to 6 carbon atoms, phenoxy or benzyloxy optionally substituted with a chlorine and dialkylamino of 1 to 7 alkyl carbon atoms and R a ' is selected from the group consisting of hydrogen and acyl of an alkanoic acid of 2 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 5
Dependent Claim
53 words
A compound of claim 3 wherein R' is selected from the group consisting of CH 3 --(CH 2 ) n1 --O-- and CH 3 --(CH 2 ) n1 --O--(CH 2 ) n2 --O-- and n 1 is an integer from 0 to 3 and n 2 is an integer from 1 to 3.
Claim 6
Dependent Claim
26 words
A compound of claim 3 wherein R' is ##STR27## and R 1 ' and R 2 ' are individually alkyl of 1 to 3 carbon atoms.
Claim 7
Dependent Claim
28 words
A compound of claim 1 selected from the group consisting of 9-[O-({2-methoxy-ethoxy}-methyl)-oxime] of erythromycin, 9-[O-(2-dimethylamino-ethyl)-oxime] of erythromycin, 9-[O-(2-diethylamino-ethyl)-oxime] of erythromycin and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
21 words
An antibiotic composition comprising an antibiotically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 9
Dependent Claim
41 words
A composition of claim 7 wherein R is selected from the group consisting of halogen, dialkylamino, alkoxy optionally substituted with alkoxy or dialkylamino, aryloxy or aralkoxy optionally substituted with a halogen and alkylthio or aryl alkylthio optionally substituted with a halogen.
Claim 10
Dependent Claim
87 words
A composition of claim 7 wherein the compound has the formula ##STR28## wherein n is an integer from 1 to 6, R' is selected from the group consisting of alkoxy and alkoxyalkoxy of 1 to 6 carbon atoms, phenoxy or benzyloxy optionally substituted with a chlorine and dialkylamino of 1 to 7 alkyl carbon atoms and R a ' is selected from the group consisting of hydrogen and acyl of an alkanoic acid of 2 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 11
Dependent Claim
56 words
A composition of claim 9 wherein R' is selected from the group consisting of CH 3 --(CH 2 ) n .sbsb.1 --O-- and CH 3 --(CH 2 ) n .sbsb.1 --O--(CH 2 ) n .sbsb.2 --O-- and n 1 is an integer from 0 to 3 and n 2 is an integer from 1 to 3.
Claim 12
Dependent Claim
26 words
A composition of claim 9 wherein R' is ##STR29## and R 1 ' and R 2 ' are individually alkyl of 1 to 3 carbon atoms.
Claim 13
Dependent Claim
28 words
A composition of claim 7 selected from the group consisting of 9-[O-({2-methoxy-ethoxy}-methyl)-oxime] of erythromycin, 9-[O-(2-dimethylamino-ethyl)-oxime] of erythromycin, 9-[O-(2-diethylamino-ethyl)-oxime] of erythromycin and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
26 words
A method of combatting bacterial infections in warm-blooded animals comprising administering to warm-blooded animals an antibacterically effective amount of at least one compound of claim 1.
Claim 15
Dependent Claim
40 words
A method of claim 13 wherein R is selected from group consisting of halogen, dialkylamino, alkoxy optionally substituted with alkoxy or dialkylamino, aryloxy or aralkoxy optionally substituted with a halogen and alkylthio or aryl alkylthio optionally substituted with a halogen.
Claim 16
Dependent Claim
87 words
A method of claim 13 wherein the compound has the formula ##STR30## wherein n is an integer from 1 to 6, R' is selected from the group consisting of alkoxy and alkoxyalkoxy of 1 to 6 carbon atoms, phenoxy or benzyloxy optionally substituted with a chlorine and dialkylamino of 1 to 7 alkyl carbon atoms and R a ' is selected from the group consisting of hydrogen and acyl of an alkanoic acid of 2 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
53 words
A method of claim 15 wherein R' is selected from the group consisting of CH 3 --(CH 2 ) n .sbsb.1 --O-- and CH 3 (CH 2 ) n .sbsb.1 --O--(CH 2 )n.sbsb.2--O-- and n 1 is an integer from 0 to 3 and n 2 is an integer from 1 to 3.
Claim 18
Dependent Claim
26 words
A method of claim 15 wherein R' is ##STR31## and R 1 ' and R 2 ' are individually alkyl of 1 to 3 carbon atoms.
Claim 19
Dependent Claim
32 words
A method of claim 13 wherein the compounds are selected from the group consisting of 9-[O-({2-methoxy-ethoxy}-methyl)-oxime] of erythromycin, 9-[O-(2-dimethylamino-ethyl)-oxime] of erythromycin, 9-[O-(2-diethylamino-ethyl)-oxime] of erythromycin and their non-toxic, pharmaceutically acceptable acid addition salts.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-13 | 1986-03-15 | 1986-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-13 | 1990-03-15 | 1990-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-13 | 1994-03-15 | 1994-09-14 | $7700.00 | Window Closed / Lapsed |