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US3932385A Expired / Lapsed US ⏱️ 0.0 years remaining

Penicillins having a 6β-(α-etherified oximino) acylamido group

Assignee: Glaxo Laboratories Ltd
•
Filing: 1972-11-07
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Granted: 1976-01-13
•
Expires: 1992-11-07
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Abstract

Abstract The invention provides novel antibiotic compounds which are 6β-acylamidopenam-3-carboxylic acids, and non-toxic derivatives thereof, characterized in that the acylamido group has the structure ##EQU1## WHERE R is a hydrogen atom or an organic group and R a is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. The compounds may be either syn or anti isomers or may exist as mixtures e.g. containing at least 75 percent of one isomer. These antibiotic compounds possess high antibacterial activity against a range of gram positive organisms including penicillinase - producing staphylococci coupled with high activity against strains of the gram-negative organism Haemophilus influenzae. The invention is also concerned with the administration of the compounds.

Inventors

  • 👤 Martin Christopher Cook
  • 👤 Gordon Ian Gregory
  • 👤 Janice Bradshaw

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 20:21
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D307/54; C07D307/77; C07D307/78; C07D307/79; C07D499/00

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 180 words
A penicillin antibiotic of the formula ##EQU24## wherein R u is naphthyl; thienyl; benzothienyl or any of these groups substituted by chlorine, bromine, iodine, fluorine, hydroxy, lower alkyl, nitro, amino, lower alkylamino, diloweralkylamino, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl and R e is alkyl of 1-16 carbon atoms; alkenyl of 2-16 carbon atoms; alkynyl of 2-16 carbon atoms; cycloalkyl of 3-7 carbon atoms; cycloalkenyl of 4-7 carbon atoms; phenyl; naphthyl; a heterocyclic radical selected from the group consisting of thienyl; furyl; pyridyl; pyrimidyl; pyrrolyl; N-methylpyrrolyl; N-benzyloxymethylpyrrolyl; thiazolyl; isothiazolyl; diazolyl; triazolyl; tetrazolyl; thiadiazolyl; thiatriazolyl; oxazolyl; oxadiazolyl; 3- or 4-isoxazolyl; sydnone; benzothienyl; benzofuryl; indolyl; benzimidazolyl; benzoxazolyl and purinyl; phenyl lower alkyl; diphenylmethyl; triphenylmethyl; naphthyl lower alkyl; heterocyclic lower alkyl in which the heterocyclic moiety is derived from said heterocyclic radical, or any of these groups substituted by hydroxy, lower alkoxy, phenoxy, benzyloxy, mercapto, lower alkylthio, phenylthio, benzylthio, amino, chlorine, bromine, iodine, fluorine, nitro, azido, carboxy, lower carbalkoxy, formyl, acetyl, propionyl, benzoyl, acetoxy, propionyloxy, pivaloyloxy, cyano, phthalimido, acetamido, benzamido, lower alkoxycarbonylamino or benzyloxycarbonylamino; or a physiologically acceptable salt thereof.
Claim 2
Dependent Claim 180 words
A penicillin antibiotic of the formula ##EQU24## wherein R u is naphthyl; thienyl; benzothienyl or any of these groups substituted by chlorine, bromine, iodine, fluorine, hydroxy, lower alkyl, nitro, amino, lower alkylamino, diloweralkylamino, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl and R e is alkyl of 1-16 carbon atoms; alkenyl of 2-16 carbon atoms; alkynyl of 2-16 carbon atoms; cycloalkyl of 3-7 carbon atoms; cycloalkenyl of 4-7 carbon atoms; phenyl; naphthyl; a heterocyclic radical selected from the group consisting of thienyl; furyl; pyridyl; pyrimidyl; pyrrolyl; N-methylpyrrolyl; N-benzyloxymethylpyrrolyl; thiazolyl; isothiazolyl; diazolyl; triazolyl; tetrazolyl; thiadiazolyl; thiatriazolyl; oxazolyl; oxadiazolyl; 3- or 4-isoxazolyl; sydnone; benzothienyl; benzofuryl; indolyl; benzimidazolyl; benzoxazolyl and purinyl; phenyl lower alkyl; diphenylmethyl; triphenylmethyl; naphthyl lower alkyl; heterocyclic lower alkyl in which the heterocyclic moiety is derived from said heterocyclic radical, or any of these groups substituted by hydroxy, lower alkoxy, phenoxy, benzyloxy, mercapto, lower alkylthio, phenylthio, benzylthio, amino, chlorine, bromine, iodine, fluorine, nitro, azido, carboxy, lower carbalkoxy, formyl, acetyl, propionyl, benzoyl, acetoxy, propionyloxy, pivaloyloxy, cyano, phthalimido, acetamido, benzamido, lower alkoxycarbonylamino or benzyloxycarbonylamino; or a physiologically acceptable salt thereof.
Claim 3
Dependent Claim 26 words
A penicillin antibiotic of the formula ##EQU25## wherein R x is naphthyl; thienyl; or; benzothienyl and Bu t is tert-butyl or a physiologically acceptable salt thereof.
Claim 4
Dependent Claim 26 words
A penicillin antibiotic of the formula ##EQU25## wherein R x is naphthyl; thienyl; or; benzothienyl and Bu t is tert-butyl or a physiologically acceptable salt thereof.
Claim 5
Dependent Claim 58 words
A penicillin antibiotic of the formula ##EQU26## wherein R u is naphthyl; thienyl; benzothienyl or any of these groups substituted by chlorine, bromine, iodine, fluorine, hydroxy, lower alkyl, nitro, amino, lower alkylamino, diloweralkylamino, lower alkanoyl, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl and R k is methyl or ethyl or a physiologically acceptable salt thereof.
Claim 6
Dependent Claim 58 words
A penicillin antibiotic of the formula ##EQU26## wherein R u is naphthyl; thienyl; benzothienyl or any of these groups substituted by chlorine, bromine, iodine, fluorine, hydroxy, lower alkyl, nitro, amino, lower alkylamino, diloweralkylamino, lower alkanoyl, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl and R k is methyl or ethyl or a physiologically acceptable salt thereof.
Claim 7
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-methoxyimino-2-(benzo-[b]-thien-2-yl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 8
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-methoxyimino-2-(thien-2-yl)acetamido]2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 9
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-ethoxyimino-2-(thien-2-yl)acetamido]2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 10
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-bromoethoxyimino-2-(thien-2-yl)acetamido[-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 11
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-t-butoxyimino-2-(thien-2-yl)acetamido]-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 12
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-(1-ethoxyethoxy)imino-2-(thien-2-yl)acetamido]2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 13
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-benzyloxyimino-2-(thien-2-yl)acetamido]2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 14
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-(thien-2-ylmethoxyimino-2-(thien-2-yl)acetamido]2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 15
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-methoxyimino-2-(naphth-1-yl)acetamido]-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 16
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-t-butoxyimino-2-(naphth-1-yl)acetamido]-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 17
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-benzyloxyimino-2-(naphth-1-yl)acetamido]-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 18
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-methoxyimino-2-(benzo[b]thien-3-yl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 19
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-t-butoxyimino-2-(benzo[b]thien-3-yl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 20
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-benzyloxyimino-2-(benzo[b]thien-2-yl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (syn-isomer).
Claim 21
Dependent Claim 10 words
The compound of claim 1 which is 6β-[2-ethoxyimino-2-(thien-3-yl)-acetamido]-2,2-dimethylpenam-3.alpha.-carboxylic acid (syn-isomer).
Claim 22
Dependent Claim 11 words
The compound of claim 1 which is 6β-[2-phenoxyimino-2-(2-thienyl)acetamido]-2,2-dimethylpenam-3α-carboxylic acid (syn isomer).
Claim 23
Dependent Claim 12 words
The compound of claim 1 which is 6β-[2-cyclopentyloxyimino-2-(2-thienyl)acetamido] -2,2-dimethylpenam-3α-carboxylic acid (syn isomer).

References Cited (Backward Citations)

US3546219A Cited
US3573294A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-12 1979-07-14 1980-01-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-12 1983-07-14 1984-01-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-12 1987-07-14 1988-01-13 $7700.00 Window Closed / Lapsed

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