Patent US3026140A successfully refreshed from Google Patents.
Patent EP0184921A2 successfully refreshed from Google Patents.
EP0184921A2
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EP
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Erythromycin derivatives
Assignee: Beecham Group PLC
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Filing: 1985-12-02
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Granted: —
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Expires: 2005-12-02
Abstract
Abstract An antibacterially active 9,11-O-methylene derivative of 9-dihydroerythromycin wherein the methylene group is optionally substituted by one or two hydrocarbon groups. In particular, compounds of formula I and their pharmaceutically acceptable esters and acid addition salts: wherein R and R 2 are each H, optionally substituted hydrocarbon, or optionally substituted 5 or 6-membered O or S heterocyclyl, or R 1 + R 2 is optionally substituted divalent hydrocarbon, R 3 is H or OH; R 4 is H, F or OH; R5 and R 6 are each H or CH 3 ; one of R 7 and R 8 is H, OH, alkoxy, alkanoyloxy optionally substituted NH 2 , or R 9 -SO 2 -O-, and the other of R 7 and R 8 is H, or R 7 + R 8 is oxo, oxime or substituted oxime; and R 9 is organic.
Inventors
- 👤 Eric Hunt
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-08 20:30
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
177 words
A compound of the general formula I or a pharmaceutically acceptable ester or acid addition salt thereof: wherein each of R 1 and R 2 , which may be identical or different, denotes hydrogen, an unsubstituted or substituted hydrocarbon group, or an unsubstituted or substituted 5- or 6-membered heterocyclyl group containing an oxygen or sulphur atom as the heteroatom, or R 1 and R 2 together denote an unsubstituted or substituted divalent hydrocarbon group, or an unsubstituted or substituted alkyleneoxyalkylene or alkylenethioalkylene group; R 3 denotes hydrogen or hydroxy; R 4 denotes hydrogen, fluorine or hydroxy; each of R 5 and R 6 , which may be identical or different, denotes hydrogen or methyl; one of R 7 and R 8 denotes hydrogen, hydroxy, alkoxy, alkanoyloxy, amino, substituted amino, or a group of the formula R 9- S0 2 -0-, and the other of R 7 and R 8 denotes hydrogen, or R 7 and R 8 together denote an oxo group, an oxime group, or a substituted oxime group; and R 9 denotes an organic group.
Claim 2
Dependent Claim
177 words
A compound of the general formula I or a pharmaceutically acceptable ester or acid addition salt thereof: wherein each of R 1 and R 2 , which may be identical or different, denotes hydrogen, an unsubstituted or substituted hydrocarbon group, or an unsubstituted or substituted 5- or 6-membered heterocyclyl group containing an oxygen or sulphur atom as the heteroatom, or R 1 and R 2 together denote an unsubstituted or substituted divalent hydrocarbon group, or an unsubstituted or substituted alkyleneoxyalkylene or alkylenethioalkylene group; R 3 denotes hydrogen or hydroxy; R 4 denotes hydrogen, fluorine or hydroxy; each of R 5 and R 6 , which may be identical or different, denotes hydrogen or methyl; one of R 7 and R 8 denotes hydrogen, hydroxy, alkoxy, alkanoyloxy, amino, substituted amino, or a group of the formula R 9- S0 2 -0-, and the other of R 7 and R 8 denotes hydrogen, or R 7 and R 8 together denote an oxo group, an oxime group, or a substituted oxime group; and R 9 denotes an organic group.
Claim 3
Dependent Claim
61 words
A compound as claimed in claim 1, wherein, in general formula I, each of R 1 and R 2 , which may be identical or different, denotes a hydrogen atom, an alkyl group, an aryl group, or a 5- or 6-membered heterocyclyl group containing an oxygen or sulphur atom as the heteroatom, each of which groups may be unsubstituted or substituted.
Claim 4
Dependent Claim
28 words
A compound as claimed in claim 1 or claim 2, wherein, in general formula I, at least one of R 1 and R 2 denotes a hydrogen atom.
Claim 5
Dependent Claim
41 words
A compound as claimed in claim 1, wherein, in general formula I, one of R 1 and R 2 denotes a hydrogen atom, and the other of R l and R 2 denotes an unsubstituted or substituted alkyl or aryl group.
Claim 6
Dependent Claim
36 words
A compound as claimed in any one of claims 1 to 4, wherein, in general formula I, R 3 denotes a hydroxy group, R 4 denotes a hydrogen atom, and R 6 denotes a methyl group.
Claim 7
Dependent Claim
24 words
The compounds: (i) 9,11-O-ethylidene-9-dihydroerythromycin A; (ii) 9,11-O-methylene-9-dihydroerythromycin A; (iii)9,11-O-isopropylidene-9-dihydroerythromycin A; (iv) 9,11-O-propylidene-9-dihydroerythromycin A; (v) 9,11-O-benzylidene-9-dihydroerythromycin A; (vi) 9,11-O-n-butylidene-9-dihydroerythromycin A; (vii)9,11-O-isobutylidene-9-dihydroerythromycin A; and (viii)9,11-O-furfurylidene-9-dihydroerythromycin A.
Claim 8
Dependent Claim
24 words
The compounds: (i) 9,11-O-ethylidene-9-dihydroerythromycin A; (ii) 9,11-O-methylene-9-dihydroerythromycin A; (iii)9,11-O-isopropylidene-9-dihydroerythromycin A; (iv) 9,11-O-propylidene-9-dihydroerythromycin A; (v) 9,11-O-benzylidene-9-dihydroerythromycin A; (vi) 9,11-O-n-butylidene-9-dihydroerythromycin A; (vii)9,11-O-isobutylidene-9-dihydroerythromycin A; and (viii)9,11-O-furfurylidene-9-dihydroerythromycin A.
Claim 9
Dependent Claim
19 words
A pharmaceutical composition comprising a compound as claimed in claim 1 together with a pharmaceutically acceptable carrier or excipient.
Claim 10
Dependent Claim
22 words
The use of a compound as claimed in claim 1 for the manufacture of a medicament for the treatment of bacterial infections.
Claim 11
Dependent Claim
194 words
A process for the preparation of a compound of the general formula I as given in claim 1 or a pharmaceutically acceptable ester or acid addition salt thereof, which comprises reacting a compound of the general formula II: wherein R 3 , R 4 , R5, R 6 , R 7 and R 8 are defined as in claim 1, in which compound of the general formula II any reactive group (other than the 9-hydroxy and 11-hydroxy groups) may optionally be protected, with: (i) a compound of the general formula III: in which R l and R 2 are defined as in claim 1, or a reactive derivative of such a compound; or (ii) a compound of the general formula IV in which R 1 and R 2 are defined as in claim 1, and each of X and Y, which may be identical or different, denotes a readily displaceable group; and thereafter removing any protecting group that may be present; and optionally (a) converting any one or more of groups R 5 , R 7 and R 8 to another such group; and/or (b) forming a pharmaceutically acceptable ester or acid addition salt.
Claim 12
Dependent Claim
125 words
A compound of the general formula V: in which R 13 denotes H or OH; R 14 denotes H, F or OH; R 15 denotes H or CH 3 ; R 16 denotes H or CH 3 ; one of R 17 and R 18 denotes H, OH, OZ, NZ 2 , NH 2 , NHZ, substituted NH 2 , substituted NHZ, alkanoyloxy, or R 9- S0 2 -O- (in which R 9 denotes an organic group), and the other of R 17 and R 1 8 denotes H, or R 17 and R 18 together denote oxo; R 19 denotes H or Z; and Z denotes a protecting group, more particularly an N-protecting group, preferably a substituted benzyloxycarbonyl group, or especially, a benzyloxycarbonyl group.
Claim 13
Dependent Claim
125 words
A compound of the general formula V: in which R 13 denotes H or OH; R 14 denotes H, F or OH; R 15 denotes H or CH 3 ; R 16 denotes H or CH 3 ; one of R 17 and R 18 denotes H, OH, OZ, NZ 2 , NH 2 , NHZ, substituted NH 2 , substituted NHZ, alkanoyloxy, or R 9- S0 2 -O- (in which R 9 denotes an organic group), and the other of R 17 and R 1 8 denotes H, or R 17 and R 18 together denote oxo; R 19 denotes H or Z; and Z denotes a protecting group, more particularly an N-protecting group, preferably a substituted benzyloxycarbonyl group, or especially, a benzyloxycarbonyl group.
References Cited (Backward Citations)
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