GB1377573A

GB1377573A – Acrloxyalkyl ester derivatives of penicillin and cephalosporin
– Google Patents

GB1377573A – Acrloxyalkyl ester derivatives of penicillin and cephalosporin
– Google Patents
Acrloxyalkyl ester derivatives of penicillin and cephalosporin

Info

Publication number
GB1377573A

GB1377573A
GB1571572A
GB1571572A
GB1377573A
GB 1377573 A
GB1377573 A
GB 1377573A
GB 1571572 A
GB1571572 A
GB 1571572A
GB 1571572 A
GB1571572 A
GB 1571572A
GB 1377573 A
GB1377573 A
GB 1377573A
Authority
GB
United Kingdom
Prior art keywords
acid
april
give
group
compound
Prior art date
1971-04-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB1571572A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Yamanouchi Pharmaceutical Co Ltd

Original Assignee
Yamanouchi Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1971-04-05
Filing date
1972-04-05
Publication date
1974-12-18

1971-04-05
Priority claimed from JP2128871A
external-priority
patent/JPS538714B1/ja

1971-08-11
Priority claimed from JP6024271A
external-priority
patent/JPS4826794A/ja

1972-04-05
Application filed by Yamanouchi Pharmaceutical Co Ltd
filed
Critical
Yamanouchi Pharmaceutical Co Ltd

1974-12-18
Publication of GB1377573A
publication
Critical
patent/GB1377573A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Abstract

1377573 Penicillin and cephalosporin esters YAMANOUCHI PHARMACEUTICAL CO Ltd 5 April 1972 [5 April 1971 19 April 1971 20 April 1971 11 Aug 1971] 15715/72 Heading C2C Novel acyloxyalkyl esters of ampicillin, cephaloglycin and cephalexin having the general Formula (I) wherein A is a group of formula in which R1 and R2 each represents an unsubstituted or substituted alkyl, cycloalkyl, alkenyl or phenyl group wherein the substituent is a phenyl group, a phenoxy group or a halogen atom or atoms, and R3 is a hydrogen atom or an acetoxy group, and acid addition salts of the said esters, are prepared by esterifying 6-aminopenicillanic acid, 7-aminocephalosporanic acid or 7-aminodesacetoxy-cephalosporanic acid, or an N-acylated derivative of these compounds, by reacting the alkali metal salt thereof with an acyloxyalkyl halide of formula wherein R1 and R2 are as defined above and X is a halogen atom. The resulting ester is then N-acylated by reaction with an acylating derivative of phenylglycine (e.g. the acid chloride hydrochloride) to give the desired compound (I) or, if an N-acylated starting compound was used, the product is reacted with phosphorus halide in the presence of a tertiary amine to give an imide halide, converted to an imino-ether by reaction with an alkanol and the imino-ether is reacted with phenylglycine or an acylating derivative thereof, followed by hydrolysis with water or an alkanol to give the compound (I). Alternatively the acyloxyalkyl ester of a penicillin may be oxidized to the S-oxide which is heated in the presence of an acid to effect ring expansion to the corresponding ester of desacetoxycephalosporanic acid. The latter is then treated with phosphorus halide, an alkanol and then with phenylglycine as described above to give the required N-acyl group of the compound (I).

GB1571572A
1971-04-05
1972-04-05
Acrloxyalkyl ester derivatives of penicillin and cephalosporin

Expired

GB1377573A
(en)

Applications Claiming Priority (4)

Application Number
Priority Date
Filing Date
Title

JP2128871A

JPS538714B1
(en)

1971-04-05
1971-04-05

JP2517071

1971-04-19

JP2552671

1971-04-20

JP6024271A

JPS4826794A
(en)

1971-08-11
1971-08-11

Publications (1)

Publication Number
Publication Date

GB1377573A
true

GB1377573A
(en)

1974-12-18

Family
ID=27457553
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB1571572A
Expired

GB1377573A
(en)

1971-04-05
1972-04-05
Acrloxyalkyl ester derivatives of penicillin and cephalosporin

Country Status (6)

Country
Link

BE
(1)

BE781659A
(en)

CA
(1)

CA996929A
(en)

CH
(1)

CH589653A5
(en)

DE
(1)

DE2215039A1
(en)

FR
(1)

FR2132447B1
(en)

GB
(1)

GB1377573A
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US7091197B2
(en)

2002-08-23
2006-08-15
Pfizer Inc.
Beta-lactamase inhibitor prodrug

Families Citing this family (6)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

CA1094545A
(en)

*

1976-02-16
1981-01-27
Michael Gregson
Cephalosporin antibiotics

GR63088B
(en)

*

1976-04-14
1979-08-09
Takeda Chemical Industries Ltd
Preparation process of novel cephalosporins

JPS60224693A
(en)

*

1984-04-20
1985-11-09
Takeda Chem Ind Ltd
Cephalosporin ester derivative

EP2121593B1
(en)

*

2006-12-10
2015-06-17
Chongxi Yu
Transdermal delivery systems of beta-lactam antibiotics

US9969751B2
(en)

2009-06-10
2018-05-15
Techfields Pharma Co., Ltd.
High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds

KR20220130239A
(en)

2012-05-16
2022-09-26
테크필즈 파마 코., 엘티디.
High penetration prodrug compositions and pharmaceutical composition thereof for treatment of pulmonary conditions

1972

1972-03-23
CA
CA137,884A
patent/CA996929A/en
not_active
Expired

1972-03-28
DE
DE19722215039
patent/DE2215039A1/en
active
Pending

1972-03-29
CH
CH473772A
patent/CH589653A5/en
not_active
IP Right Cessation

1972-04-05
GB
GB1571572A
patent/GB1377573A/en
not_active
Expired

1972-04-05
BE
BE781659A
patent/BE781659A/en
unknown

1972-04-05
FR
FR7211910A
patent/FR2132447B1/fr
not_active
Expired

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US7091197B2
(en)

2002-08-23
2006-08-15
Pfizer Inc.
Beta-lactamase inhibitor prodrug

Also Published As

Publication number
Publication date

BE781659A
(en)

1972-07-31

DE2215039A1
(en)

1972-10-26

CH589653A5
(en)

1977-07-15

FR2132447A1
(en)

1972-11-17

CA996929A
(en)

1976-09-14

FR2132447B1
(en)

1976-04-16

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(en)

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(en)

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(en)

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(en)

1973-03-14

Penicillin derivatives and process for producing penicillin deri vatives

GB1459949A
(en)

1976-12-31

Penicillin compounds their production and their medicinal use

GB1410852A
(en)

1975-10-22

Substituted 4-biphenylyl-butenoic acids esters and amides and pharmaceutical compositions containing them

GB1347979A
(en)

1974-02-27

Penicillins

Legal Events

Date
Code
Title
Description

1975-04-30
PS
Patent sealed

1979-11-28
PCNP
Patent ceased through non-payment of renewal fee

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