US4229443A
Expired / Lapsed
US
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Derivatives of penicillanic acid
Assignee: Leo Pharma AS
•
Filing: 1977-06-14
•
Granted: 1980-10-21
•
Expires: 1997-06-14
Abstract
Abstract The present invention relates to new substituted 6 beta -amidinopenicillanic acids; pharmaceuticallyacceptable salts, easily hydrolyzable esters thereof and salts of such esters; to methods of producing the compounds; to intermediates in their preparation, to pharmaceutical compositions containing the compounds; to dosage units thereof; and to their use.
Inventors
- 👤 Ernst T. Binderup
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 00:32
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P31/00; A61P31/04; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/20; C07D211/22; C07D211/26; C07D211/28; C07D221/00; C07D221/02; C07D221/20; C07D221/22; C07D223/00; C07D223/02; C07D223/04; C07D233/00; C07D233/04; C07D499/00
Claims Analysis
Total Claims: 69
Claim 1
Independent Claim
282 words
An antibiotic compound of the general formulae I, II, and III ##STR27## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR28## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the groupings: ##STR29## represent saturated, monocyclic, bicyclic or spirocyclic ring systems, respectively, having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula IV: ##STR30## and salts of the compounds of the formulae I, II, and III with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formulae I, II, and III.
Claim 2
Dependent Claim
282 words
An antibiotic compound of the general formulae I, II, and III ##STR27## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR28## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the groupings: ##STR29## represent saturated, monocyclic, bicyclic or spirocyclic ring systems, respectively, having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula IV: ##STR30## and salts of the compounds of the formulae I, II, and III with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formulae I, II, and III.
Claim 3
Dependent Claim
268 words
An antibiotic compound of the general formula I ##STR31## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR32## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen ato form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR33## represents a saturated monocyclic ring system having from 4 to 11 carbon atoms; P stands for the penicillanic acid radical of the formula IV: ##STR34## and salts of the compounds of the formula I with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula I.
Claim 4
Dependent Claim
268 words
An antibiotic compound of the general formula I ##STR31## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR32## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen ato form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR33## represents a saturated monocyclic ring system having from 4 to 11 carbon atoms; P stands for the penicillanic acid radical of the formula IV: ##STR34## and salts of the compounds of the formula I with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula I.
Claim 5
Dependent Claim
269 words
An antibiotic compound of the general formula II ##STR35## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR36## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR37## represents a saturated, bicyclic ring system, having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula ##STR38## and salts of the compounds of the formula II with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula II.
Claim 6
Dependent Claim
269 words
An antibiotic compound of the general formula II ##STR35## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical having from 1 to 6 carbon atoms, which radical optionally can be substituted with an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having from 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR36## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR37## represents a saturated, bicyclic ring system, having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula ##STR38## and salts of the compounds of the formula II with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula II.
Claim 7
Dependent Claim
268 words
An antibiotic compound of the general formula III ##STR39## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted from an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR40## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR41## represents a saturated spirocyclic ring system having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula ##STR42## and salts of the compounds of the formula III with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula III.
Claim 8
Dependent Claim
268 words
An antibiotic compound of the general formula III ##STR39## in which -A- stands for a straight or branched, saturated or unsaturated aliphatic hydrocarbon radical, having from 1 to 6 carbon atoms, which radical optionally can be substituted from an amino radical; R 1 stands for hydrogen, or a lower alkyl radical having from 1 to 4 carbon atoms; R 2 stands for hydrogen, a lower alkyl radical having from 1 to 4 carbon atoms, or a monoacyl radical derived from a mono- or dibasic carboxylic acid, sulphuric acid, a sulphonic acid, a sulphinic acid, phosphoric acid, or a phosphonic acid, and R 2 can represent an unsubstituted or a lower alkyl or phenyl substituted radical selected from the group consisting of carbamoyl, guanyl and guanylcarbamoyl radicals; R 1 and R 2 together with the nitrogen atom can form a monocyclic, saturated ring having 4 to 8 carbon atoms; furthermore R 1 and R 2 together can represent a radical of the formula ##STR40## in which R 3 and R 4 each stands for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or in which R 3 and R 4 together with the nitrogen atom form a monocyclic, saturated ring having from 4 to 7 carbon atoms; the grouping: ##STR41## represents a saturated spirocyclic ring system having from 4 to 11 carbon atoms in total; P stands for the penicillanic acid radical of the formula ##STR42## and salts of the compounds of the formula III with pharmaceutically acceptable, non-toxic organic and inorganic acids or bases, and easily hydrolyzable pharmaceutically acceptable, non-toxic esters of the penicillanic acid derivatives of formula III.
Claim 9
Dependent Claim
45 words
A compound according to claim 2 in which -A- stands for a saturated or unsaturated carbon chain with from 1 to 3 carbon atoms, R 1 and R 2 stand for hydrogen, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 10
Dependent Claim
39 words
A compound according to claim 2 in which the grouping ##STR43## has from 5 to 8 carbon atoms, -A- contains from 1 to 3 carbon atoms and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 11
Dependent Claim
15 words
6-[4'-aminomethyl-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 12
Dependent Claim
15 words
6-[4'-aminomethyl-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 13
Dependent Claim
15 words
6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 14
Dependent Claim
15 words
6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 15
Dependent Claim
15 words
6-[4'-(2"-aminoethyl)-hexahydro-1'H-azepin-1'-yl)-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 16
Dependent Claim
15 words
6-[4'-(2"-aminoethyl)-hexahydro-1'H-azepin-1'-yl)-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 17
Dependent Claim
15 words
6-[4'-(3"-acetamidopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 18
Dependent Claim
15 words
6-[4'-(3"-acetamidopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 19
Dependent Claim
15 words
6-[4'-(3"-(N,N-dimethylamino-methyleneamino)-propyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 20
Dependent Claim
15 words
6-[4'-(3"-(N,N-dimethylamino-methyleneamino)-propyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 21
Dependent Claim
7 words
Bis-(6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamono]-penicillanoyloxy)-methane, and pharmaceutically acceptable, non-toxic salts thereof.
Claim 22
Dependent Claim
7 words
Bis-(6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamono]-penicillanoyloxy)-methane, and pharmaceutically acceptable, non-toxic salts thereof.
Claim 23
Dependent Claim
15 words
6-[(4'-(1",3"-diaminopropyl-2")-hexahydro-1'H-azepin-1'-yl)-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 24
Dependent Claim
15 words
6-[(4'-(1",3"-diaminopropyl-2")-hexahydro-1'H-azepin-1'-yl)-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 25
Dependent Claim
48 words
A compound according to claim 3 in which -A- stands for a saturated or unsaturated carbon chain with from 1 to 3 carbon atoms, and in which R 1 and R 2 stand for hydrogen, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 26
Dependent Claim
43 words
A compound according to claim 3 in which in the grouping ##STR44## the individual rings have a maximum of 7 carbon atoms, -A- contains from 1 to 3 carbon atoms, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 27
Dependent Claim
38 words
A compound according to claim 15 in which the numbers of carbon atoms in the heterocyclic part of the ring is 4 and the total number of the carbon atoms in the ring system are 7 or 8.
Claim 28
Dependent Claim
48 words
A compound according to claim 4 in which -A- stands for a saturated or unsaturated carbon chain with from 1 to 3 carbon atoms, and in which R 1 and R 2 stand for hydrogen, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 29
Dependent Claim
44 words
A compound according to claim 4 in which in the spirocyclic grouping ##STR45## the individual rings have a maximum of 7 carbon atoms, -A- contains from 1 to 3 carbon atoms, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 30
Dependent Claim
45 words
An antibacterial composition in dosage unit form for enteral or parenteral treatment of patients, which comprises as an active ingredient 0.025 g to 2.5 g of a compound as claimed in claim 2 calculated as the free acid together with a non-toxic pharmaceutically acceptable carrier.
Claim 31
Dependent Claim
35 words
An antibacterial composition in dosage unit form as claimed in claim 19 for oral treatment of patients said composition containing from 0.05 g to 1.5 g of the active ingredient, calculated as the free acid.
Claim 32
Dependent Claim
39 words
An antibacterial composition in dosage unit form as claimed in claim 20 and containing as the active component the compound 6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, or a pharmaceutically acceptable, non-toxic salt or easily hydrolyzable ester thereof, or a salt of such ester.
Claim 33
Dependent Claim
20 words
An antibacterial composition in dosage unit form as claimed in claim 21 in the form of tablets, pills or capsules.
Claim 34
Dependent Claim
46 words
An antibacterial composition in dosage unit form for parenteral treatment of patients, said composition comprising from 0.1 g to 1 g of a compound as claimed in claim 2, calculated as the free acid, as such or in the form of one of its non-toxic salts.
Claim 35
Dependent Claim
39 words
An antibacterial composition in dosage unit form as claimed in claim 23 and containing as the active ingredient the compound 6-[4'-(3"-aminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid, or a pharmaceutically acceptable, non-toxic salt or easily hydrolyzable ester thereof or a salt of such ester.
Claim 36
Dependent Claim
42 words
An antibacterial composition for treatment of patients said composition containing as the active ingredient a compound as claimed in claim 2 together with carrier subtances and auxiliary agents, containing from 1% to 95% of the active ingredient, calculated as the free acid.
Claim 37
Dependent Claim
50 words
An antibacterial composition for treatment of patients as claimed in claim 25 containing the active ingredient together with an active additive selected from the group consisting of known penicillins, cephalosporins, amidinopenicillanic acid derivatives, aminoglycoside antibiotics, trimethoprim or clavulanic acid, the ratio between the active compounds being between 1:20 and 20:1.
Claim 38
Dependent Claim
38 words
An antibacterial composition as claimed in claim 26 in dosage unit form for enteral and parenteral treatment of patients and containing from 0.025 g to 2.5 g in total of the active compounds, as present, in the composition.
Claim 39
Dependent Claim
35 words
A method of treating patients suffering from bacterial infections, which comprises administering to said patients a compound as claimed in claim 2 in daily doses from 0.2 to 30 g calculated as the free acid.
Claim 40
Dependent Claim
81 words
A compound of claim 2 wherein the penicillanic acid radical of formula IV is esterified, forming a diester of the formula V ##STR46## in which X and Y can be the same or different and can stand for an acyl radical of a compound of formula I, and Y furthermore can be the acyl ester of a conventional β-lactam antibiotic, R 5 stands for hydrogen, methyl, ethyl, or phenyl, and salts of such esters with pharmaceutically acceptable, non-toxic acids or bases.
Claim 41
Dependent Claim
87 words
A compound according to claim 2, in which R 1 and R 2 are selected from the group consisting of hydrogen and lower alkyl with from 1 to 4 carbon atoms; A is a straight or branched saturated hydrocarbon radical containing 1-6 carbon atoms which chain may optionally be substituted with an unsubstituted or mono- or di-lower alkylsubstituted amino group, the ##STR47## represents a saturated monocyclic ring containing 5-8 carbon atoms, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable, non-toxic, pharmaceutically acceptably esters thereof and their salts.
Claim 42
Dependent Claim
16 words
A compound as in claim 30 wherein R 1 and R 2 are hydrogen or methyl.
Claim 43
Dependent Claim
15 words
A compound as in claim 30 wherein R 1 and R 2 are both hydrogen.
Claim 44
Dependent Claim
18 words
A compound as in claim 30 wherein A is a straight carbon atom chain containing 1-3 carbon atoms.
Claim 45
Dependent Claim
17 words
A compound as in claim 30 wherein A is a branched carbon chain containing 3-6 carbon atoms.
Claim 46
Dependent Claim
16 words
A compound as in claim 34 wherein A may optionally be substituted with unsubstituted amino group.
Claim 47
Dependent Claim
16 words
A compound as in claim 30 wherein the group ##STR48## contains 5 or 6 carbon atoms.
Claim 48
Dependent Claim
12 words
A compound as in claim 36 wherein the group ##STR49## is piperidyl-1.
Claim 49
Dependent Claim
12 words
A compound as in claim 36 wherein the group ##STR50## is hexahydro-1H-azepin-1-yl.
Claim 50
Dependent Claim
45 words
A compound according to claim 2 in which -A- stands for a saturated or unsaturated hydrocarbon radical with from 1 to 3 carbon atoms, R 1 and R 2 stand for hydrogen, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 51
Dependent Claim
39 words
A compound according to claim 2 in which the grouping ##STR51## has from 5 to 8 carbon atoms, -A- contains from 1 to 3 carbon atoms, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 52
Dependent Claim
15 words
6-[4'-(2"-aminoethyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 53
Dependent Claim
15 words
6-[4'-(2"-aminoethyl)-1'-piperidyl-methyleneamino]-penicillanic acid, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and their salts.
Claim 54
Dependent Claim
16 words
6-[4'-(3"-N,N-Dimethylaminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid and pharmaceutically acceptable salts and easily hydrolyzable pharmaceutically acceptable esters thereof and their salts.
Claim 55
Dependent Claim
16 words
6-[4'-(3"-N,N-Dimethylaminopropyl)-1'-piperidyl-methyleneamino]-penicillanic acid and pharmaceutically acceptable salts and easily hydrolyzable pharmaceutically acceptable esters thereof and their salts.
Claim 56
Dependent Claim
16 words
6-[4'-(2"-Aminobutyl)-1'-piperidyl-methyleneamino]-penicillanic acid and pharmaceutically acceptable salts and easily hydrolyzable pharmaceutically acceptable esters thereof and their salts.
Claim 57
Dependent Claim
16 words
6-[4'-(2"-Aminobutyl)-1'-piperidyl-methyleneamino]-penicillanic acid and pharmaceutically acceptable salts and easily hydrolyzable pharmaceutically acceptable esters thereof and their salts.
Claim 58
Dependent Claim
84 words
A compound of claim 1 wherein the penicillanic acid radical of formula IV is esterified, forming a diester of the formula V ##STR52## in which X and Y can be the same or different and can stand for an acyl radical of a compound of formulae I, II and III, and Y furthermore can be the acyl ester of a conventional β-lactam antibiotic, R 5 stands for hydrogen, methyl, ethyl, or phenyl, and salts of such esters with pharmaceutically acceptable, non-toxic acids or bases.
Claim 59
Dependent Claim
81 words
A compound of claim 3 wherein the penicillanic acid radical of formula IV is esterified, forming a diester for the formula V ##STR53## in which X and Y can be the same of different and can stand for an acyl radical of a compound of formula II, and Y furthermore can be the acyl ester of a conventional β-lactam antibiotic, R 5 stands for hydrogen methyl, ethyl, or phenyl, and salts of such esters with pharmaceutically acceptable, non-toxic acids or bases.
Claim 60
Dependent Claim
81 words
A compound of claim 4 wherein the penicillanic acid radical of formula IV is esterified, forming a diester of the formula V ##STR54## in which X and Y can be the same or different and can stand for an acyl radical of a compound of formula III, and Y furthermore can be the acyl ester of a conventional β-lactam antibiotic, R 5 stands for hydrogen, methyl, ethyl, or phenyl, and salts of such esters with pharmaceutically acceptable, non-toxic acids or bases.
Claim 61
Dependent Claim
45 words
An antibacterial composition in dosage unit form for enteral or parenteral treatment of patients, which comprises as an active ingredient 0.025 g to 2.5 g of a compound as claimed in claim 1 calculated as the free acid together with a non-toxic, pharmaceutically acceptable carrier.
Claim 62
Dependent Claim
33 words
An antibacterial composition in dosage unit form as claimed in claim 48 for oral treatment of patients containing from 0.05 g to 1.5 g of the active ingredient, calculated as the free acid.
Claim 63
Dependent Claim
46 words
An antibacterial composition in dosage unit form for parenteral treatment of patients, said composition comprising from 0.1 g to 1 g of a compound as claimed in claim 1, calculated as the free acid, as such or in the form on one of its non-toxic salts.
Claim 64
Dependent Claim
41 words
An antibacterial composition for treatment of patients said composition containing as the active ingredient a compound as claimed in claim 1 together with carrier substances and auxillary agents, containing 1% to 95% of the active ingredient, calculated as the free acid.
Claim 65
Dependent Claim
49 words
An antibacterial composition for treatment of patients as claimed in claim 50 containing the active ingredient together with an active additive selected from the group consisting of known penicillins, cephalosporins, amidinopenicillanic acid derivatives, aminoglycoside antibiotics, trimethoprim or clavulanic acid, the ratio between the active compounds being 1:20 and 20:1.
Claim 66
Dependent Claim
38 words
An antibacterial composition as claimed in claim 51 in dosage unit form for enteral and parenteral treatment of patients and containing from 0.025 g to 2.5 g in total of the active compounds, as present, in the composition.
Claim 67
Dependent Claim
35 words
A method of treating patients suffering from bacterial infection, which comprises administering to said patients a compound as claimed in claim 1 in daily doses from 0.2 to 30 g calculated as the free acid.
Claim 68
Dependent Claim
20 words
The pharmaceutical composition as claimed in claim 26 wherein the ratio between the active compounds is between 1:5 and 5:1.
Claim 69
Dependent Claim
20 words
The pharmaceutical composition as claimed in claim 51 wherein the ratio between the active compounds is between 1:5 and 5:1.
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) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |