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US4081546A Expired / Lapsed US ⏱️ 0.0 years remaining

3-substituted aminocycloalkyl esters of penicillin antibiotics

Assignee: Beecham Group PLC
•
Filing: 1977-06-20
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Granted: 1978-03-28
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Expires: 1997-06-20
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Abstract

Abstract A class of substituted aminocycloalkyl esters of penicillins have improved pharmacokinetic properties and are hydrolysed to the antibacterially active penicillin.

Inventors

  • 👤 Harry Ferres

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 20:44
CPC Classifications
C; C07; C07D; C07D499/00

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 157 words
A penicillin ester of formula (I) or a pharmaceutically acceptable acid addition salt thereof: ##STR12## wherein R 1 and R 2 are the same or different and each represents a C 1-6 alkyl group or R 1 and R 2 taken together represents an alkylene chain optionally interrupted with an oxygen or nitrogen atoms forming a 5- or 6-membered heterocyclic ring; Z represents an optionally substituted straight or branched saturated or unsaturated divalent hydrocarbon radical wherein the optional substituents are selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen; X represents hydrogen, amino, carboxy, alkoxycarbonyl, phenoxycarbonyl, alkylphenoxycarbonyl or indanyl; R represents phenyenoptionally substituted with hydroxy or halogne; naphthyl optionally substituted with C 1-6 alkoxy; phenoxy optionally substituted with C 1-6 alkoxy; 2- or 3-thienyl, pyridyl, tetrazolyl, or the group RCHX represents phenyl optionally substituted with C 1-6 alkoxy or isoxazolyl optionally substituted with halogen or C 1-6 alkyl.
Claim 2
Dependent Claim 157 words
A penicillin ester of formula (I) or a pharmaceutically acceptable acid addition salt thereof: ##STR12## wherein R 1 and R 2 are the same or different and each represents a C 1-6 alkyl group or R 1 and R 2 taken together represents an alkylene chain optionally interrupted with an oxygen or nitrogen atoms forming a 5- or 6-membered heterocyclic ring; Z represents an optionally substituted straight or branched saturated or unsaturated divalent hydrocarbon radical wherein the optional substituents are selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen; X represents hydrogen, amino, carboxy, alkoxycarbonyl, phenoxycarbonyl, alkylphenoxycarbonyl or indanyl; R represents phenyenoptionally substituted with hydroxy or halogne; naphthyl optionally substituted with C 1-6 alkoxy; phenoxy optionally substituted with C 1-6 alkoxy; 2- or 3-thienyl, pyridyl, tetrazolyl, or the group RCHX represents phenyl optionally substituted with C 1-6 alkoxy or isoxazolyl optionally substituted with halogen or C 1-6 alkyl.
Claim 3
Dependent Claim 27 words
A penicillin ester as claimed in claim 1 wherein the group Z together with the two carbon atoms to which it is attached, forms a 6-membered ring.
Claim 4
Dependent Claim 17 words
A penicillin ester as claimed in claim 1 wherein R 1 and R 2 are both methyl.
Claim 5
Dependent Claim 20 words
A penicillin ester as claimed in claim 1 wherein the side-chain group R.CHX.CONH-- represents phenylacetamido, 2-aminophenylacetamido, 2-amino-p-hydroxyphenylacetamido, 2,6-dimethoxybenzamido, or 3-(2'-chlorophenyl)-5-methyl-4-isoxazolylcarbonylamino.
Claim 6
Dependent Claim 3 words
2-N,N-Dimethylaminocyclohexanyl benzylamido penicillanate.
Claim 7
Dependent Claim 3 words
2-N,N-Dimethylaminocyclohexanyl benzylamido penicillanate.
Claim 8
Dependent Claim 4 words
2-N,N-Dimethylaminocyclohexanyl 2,6-Dimethoxy benzamido penicillanate.
Claim 9
Dependent Claim 4 words
2-N,N-Dimethylaminocyclohexanyl 2,6-Dimethoxy benzamido penicillanate.
Claim 10
Dependent Claim 3 words
2-N,N-Dimethylaminocyclohexanyl 3-(2'-chlorophenyl)-5-methylisoxazolyl-4-carboxamido penicillanate.
Claim 11
Dependent Claim 3 words
2-N,N-Dimethylaminocyclohexanyl 3-(2'-chlorophenyl)-5-methylisoxazolyl-4-carboxamido penicillanate.
Claim 12
Dependent Claim 32 words
A pharmaceutical composition for the treatment of penicillin-responsive bacterial infections comprising a penicillin ester as claimed in claim 1 in an antibacterially effective amount together with a pharmaceutically acceptable carrier or excipient.

References Cited (Backward Citations)

GB675422A Cited
GB727481A Cited
US2650218A Cited
US3652546A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-03-27 1981-09-26 1982-03-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-03-27 1985-09-26 1986-03-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-03-27 1989-09-26 1990-03-28 $7700.00 Window Closed / Lapsed

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