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US3966718A Expired / Lapsed US ⏱️ 0.0 years remaining

7-β-Acylamino-ceph-3-ems and salts and esters therefor

Assignee: Beecham Group PLC
•
Filing: 1974-01-17
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Granted: 1976-06-29
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Expires: 1994-01-17
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Abstract

Abstract Antimicrobially active substituted ceph-3-ems, procedure for their preparation and intermediates for use in the procedure are described. These cephalosporins are characterized by having a 2- or 3- pyridyl group attached to the carbon atom of the methylene group in the 3-position by a carbon-carbon bond and not a carbon-nitrogen bond.

Inventors

  • 👤 Edward George Brain
  • 👤 Neal Frederick Osborne

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 01:43
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 190 words
A 7-β-acylamino-ceph-3-em compound of the formula (II): ##EQU13## or a pharmaceutically acceptable acid addition salt thereof, wherein Py is 2-pyridyl or 3-pyridyl, R 1 is COOH, a salt of COOH selected from the sodium, potassium, calcium, magnesium, aluminum, triethylamine, procaine, dibenzylamine, triethanolamine, 1-ephenamine and ethylpiperidine or a hydrolyzable ester which breaks down in the body to the free acid selected from acetoxymethyl, pivaloyloxymethyl, α-acetoxymethyl, α-acetoxybenzyl, α-pivaloyloxyethyl, phthalide, and 3,4 dimethyl phthalide R is ##EQU14## in which R 2 is hydrogen, lower alkyl, C 3-6 cycloalkyl, cyclohexenyl, cyclohexadienyl, phenyl, p-hydroxyphenyl, thienyl, pyridyl, isoxazolyl, 3-O-chlorophenyl-5-methyl-isoxazol-4-yl, sydnonyl or tetrazolyl, X is hydrogen, hydroxy, halogen, COOH or its phenyl or indanyl ester, azido, amino, ureido, guanidino, triazolyl, tetrazolyl, cyano, formyloxy, lower alkanoyloxy or lower alkoxy; and n and m are each 0, 1, 2 or 3; or ##EQU15## in which n is 1, 2, 3 or 4 and X is as defined in (i) above, or ##EQU16## in which R 4 is lower alkyl, benzyl, phenyl, C 3-6 cycloalkyl, cyclohexenyl, cyclohexadienyl, thienyl or pyridyl, R 5 and R 6 are each hydrogen, lower alkyl, phenyl, benzyl or phenylethyl, and Z is oxygen or sulphur.
Claim 2
Dependent Claim 190 words
A 7-β-acylamino-ceph-3-em compound of the formula (II): ##EQU13## or a pharmaceutically acceptable acid addition salt thereof, wherein Py is 2-pyridyl or 3-pyridyl, R 1 is COOH, a salt of COOH selected from the sodium, potassium, calcium, magnesium, aluminum, triethylamine, procaine, dibenzylamine, triethanolamine, 1-ephenamine and ethylpiperidine or a hydrolyzable ester which breaks down in the body to the free acid selected from acetoxymethyl, pivaloyloxymethyl, α-acetoxymethyl, α-acetoxybenzyl, α-pivaloyloxyethyl, phthalide, and 3,4 dimethyl phthalide R is ##EQU14## in which R 2 is hydrogen, lower alkyl, C 3-6 cycloalkyl, cyclohexenyl, cyclohexadienyl, phenyl, p-hydroxyphenyl, thienyl, pyridyl, isoxazolyl, 3-O-chlorophenyl-5-methyl-isoxazol-4-yl, sydnonyl or tetrazolyl, X is hydrogen, hydroxy, halogen, COOH or its phenyl or indanyl ester, azido, amino, ureido, guanidino, triazolyl, tetrazolyl, cyano, formyloxy, lower alkanoyloxy or lower alkoxy; and n and m are each 0, 1, 2 or 3; or ##EQU15## in which n is 1, 2, 3 or 4 and X is as defined in (i) above, or ##EQU16## in which R 4 is lower alkyl, benzyl, phenyl, C 3-6 cycloalkyl, cyclohexenyl, cyclohexadienyl, thienyl or pyridyl, R 5 and R 6 are each hydrogen, lower alkyl, phenyl, benzyl or phenylethyl, and Z is oxygen or sulphur.
Claim 3
Dependent Claim 28 words
A compound of claim 1 wherein the acid addition salt is the sulphate, nitrate, phosphate, borate, hydrochloride, hydrobromide, hydroiodide, acetate, tartrate, malate, citrate, succinate, benzoate, ascorbate, or methanesulphonate.
Claim 4
Dependent Claim 2 words
7β-(D-.alpha.-aminophenylacetamido)-3(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 5
Dependent Claim 2 words
7β-(D-.alpha.-aminophenylacetamido)-3(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 6
Dependent Claim 1 words
7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em.
Claim 7
Dependent Claim 1 words
7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em.
Claim 8
Dependent Claim 2 words
7β-(DL-.alpha.-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 9
Dependent Claim 2 words
7β-(DL-.alpha.-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 10
Dependent Claim 2 words
7.beta.-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 11
Dependent Claim 2 words
7.beta.-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 12
Dependent Claim 2 words
7β-(D-α-hydroxyphenylacetamido)-3(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 13
Dependent Claim 2 words
7β-(D-α-hydroxyphenylacetamido)-3(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 14
Dependent Claim 20 words
A pharmaceutically acceptable salt of a compound selected from the group 7β-(D-α-aminophenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em, 7β-(DL-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-hydroxyphenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 15
Dependent Claim 20 words
A pharmaceutically acceptable salt of a compound selected from the group 7β-(D-α-aminophenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em, 7β-(DL-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-hydroxyphenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid.
Claim 16
Dependent Claim 48 words
A pharmaceutically acceptable ester of a compound selected from the group 7β-(D-α-aminophenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em, 7β-(DL-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl-3-cephem-4-carboxylic acid, 7β-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-hydroxyphenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, said ester being a hydrolyzable ester which breaks down in the body to the free acid and selected from acetoxymethyl, pivaloyloxymethyl, α-acetoxyethyl, α-acetoxybenzyl, α-pivaloyloxyethyl, phthalide and 3,4 dimethylphthalide.
Claim 17
Dependent Claim 48 words
A pharmaceutically acceptable ester of a compound selected from the group 7β-(D-α-aminophenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-2-amino-2-p-hydroxyphenylacetamido)-4-carboxy-3-(3-pyridylmethyl)ceph-3-em, 7β-(DL-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl-3-cephem-4-carboxylic acid, 7β-(D-α-amino-2-thienylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, 7β-(D-α-hydroxyphenylacetamido)-3-(3-pyridylmethyl)-3-cephem-4-carboxylic acid, said ester being a hydrolyzable ester which breaks down in the body to the free acid and selected from acetoxymethyl, pivaloyloxymethyl, α-acetoxyethyl, α-acetoxybenzyl, α-pivaloyloxyethyl, phthalide and 3,4 dimethylphthalide.

References Cited (Backward Citations)

US3225038A Cited
US3352858A Cited
US3449338A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-29 1979-12-29 1980-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-29 1983-12-29 1984-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-29 1987-12-29 1988-06-29 $7700.00 Window Closed / Lapsed

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