GB1479711A

GB1479711A – Acylureido cephalosporins
– Google Patents

GB1479711A – Acylureido cephalosporins
– Google Patents
Acylureido cephalosporins

Info

Publication number
GB1479711A

GB1479711A
GB27970/73A
GB2797073A
GB1479711A
GB 1479711 A
GB1479711 A
GB 1479711A
GB 27970/73 A
GB27970/73 A
GB 27970/73A
GB 2797073 A
GB2797073 A
GB 2797073A
GB 1479711 A
GB1479711 A
GB 1479711A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
ester
salt
reacting
Prior art date
1973-06-12
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
GB27970/73A
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.)

Beecham Group PLC

Original Assignee
Beecham Group PLC
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.)
1973-06-12
Filing date
1973-06-12
Publication date
1977-07-13

1973-06-12
Application filed by Beecham Group PLC
filed
Critical
Beecham Group PLC

1973-06-12
Priority to GB27970/73A
priority
Critical
patent/GB1479711A/en

1974-05-29
Priority to IE2264/77A
priority
patent/IE39295B1/en

1974-05-29
Priority to IE2265/77A
priority
patent/IE39296B1/en

1974-05-29
Priority to IE1132/74A
priority
patent/IE39294B1/en

1974-06-03
Priority to IL44959A
priority
patent/IL44959A/en

1974-06-05
Priority to ZM85/74A
priority
patent/ZM8574A1/en

1974-06-06
Priority to AU69843/74A
priority
patent/AU475246B2/en

1974-06-10
Priority to MW24/74*UA
priority
patent/MW2474A1/en

1974-06-11
Priority to FI179174A
priority
patent/FI179174A/fi

1974-06-11
Priority to DK311874A
priority
patent/DK311874A/da

1974-06-11
Priority to DE19742428139
priority
patent/DE2428139A1/en

1974-06-11
Priority to NO742117A
priority
patent/NO742117L/no

1974-06-11
Priority to AT482074A
priority
patent/AT335060B/en

1974-06-11
Priority to SE7407713A
priority
patent/SE7407713L/xx

1974-06-11
Priority to DD179086A
priority
patent/DD111581A5/xx

1974-06-11
Priority to JP49066446A
priority
patent/JPS5047990A/ja

1974-06-12
Priority to ES427234A
priority
patent/ES427234A1/en

1974-06-12
Priority to PL17185574A
priority
patent/PL89964B1/pl

1974-06-12
Priority to ZA00743748A
priority
patent/ZA743748B/en

1974-06-12
Priority to CH361378A
priority
patent/CH613456A5/en

1974-06-12
Priority to RO7913074A
priority
patent/RO63098A/en

1974-06-12
Priority to CH806474A
priority
patent/CH609350A5/xx

1974-06-12
Priority to PL18935374A
priority
patent/PL94613B1/en

1974-06-12
Priority to BE145344A
priority
patent/BE816238A/en

1974-06-12
Priority to RO8634574A
priority
patent/RO63740A/en

1974-06-12
Priority to RO7486344A
priority
patent/RO64674A/en

1974-06-12
Priority to NL7407815A
priority
patent/NL7407815A/xx

1974-06-12
Priority to FR7420301A
priority
patent/FR2233067A1/en

1974-06-12
Priority to CH361278A
priority
patent/CH611303A5/en

1975-11-19
Priority to SU752189959A
priority
patent/SU688130A3/en

1976-05-06
Priority to US05/683,792
priority
patent/US4312982A/en

1977-01-12
Priority to NO770104A
priority
patent/NO770104L/no

1977-05-24
Priority to SE7706081A
priority
patent/SE7706081L/en

1977-07-13
Publication of GB1479711A
publication
Critical
patent/GB1479711A/en

1977-08-11
Priority to IL52704A
priority
patent/IL52704A0/en

1977-11-07
Priority to AR269874A
priority
patent/AR219722A1/en

1977-11-15
Priority to FI773446A
priority
patent/FI773446A/fi

1977-11-15
Priority to FI773447A
priority
patent/FI773447A/fi

1977-12-01
Priority to DK533177A
priority
patent/DK533177A/en

1981-09-29
Priority to NL8104456A
priority
patent/NL8104456A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

C07D501/14—Compounds having a nitrogen atom directly attached in position 7

C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3

C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids

C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3

C07D501/36—Methylene radicals, substituted by sulfur atoms

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

C07D501/14—Compounds having a nitrogen atom directly attached in position 7

C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3

C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids

Abstract

1479711 Acylureido cephalosporins BEECHAM GROUP Ltd 4 June 1974 [12 June 1973 20 Oct 1973] 27970/73 and 48968/73 Heading C2C Novel cephalosporins of Formula (I) where Y is O or S, R1 is an organic radical of up to 20C; R2 is C 1-3 alkyl, or benzyl, or R1 and R2 together with the C and N atoms to which they are attached form a 5, 6 or 7-membered ring; R3 is cyclohexadienyl, phenyl, phenyl substituted by one or more functional groups selected from hydroxy, halogen, nitro, C 1-3 alkoxy, amino, 2- or 3-thienyl, C 3-7 cycloalkyl, or C 1-4 alkyl; R4 is acetoxy or a group of the formula or a pharmaceutically acceptable salt or ester thereof, may be obtained by (a) reacting a compound of Formula (II) or a salt, ester or silyl derivative thereof wherein the dotted line represents a bond in the 2- or 3-position, and n is 0 or 1, with a reactive N-acylating derivative of an acid of the Formula (III) R1C( =Y).N(R2).CONH.CH(R3).COOH and wherein any reactive groups may be blocked, or (b) reacting a compound (IV) or a salt, ester or silyl derivative thereof. wherein the dotted line represents a bond in the 2- or 3-position, with a compound of formula R1.C(=Y).N(R2)COCl or (c) in the case of compounds of Formula (I), where R4 is other than acetoxy, reacting a compound of Formula (VI) or a salt, ester or silyl derivative thereof where the dotted line represents a bond in the 2 or 3 position, n is 0 or 1, and wherein any reactive groups may be blocked, with the appropriate nucleophile, and after reaction (a), (b) or (c) carrying out one or more of the following steps, if necessary; (i) converting a #2 isomer to a #3 isomer, (ii) removal of any silyl groups by alcoholysis or hydrolysis, (iii) reduction of a sulphoxide compound to form a desired sulphide compound, (iv) removal of any blocking groups in the acyl side chain R 1 , (v) conversion of an ester compound to a free acid compound or salt thereof.

GB27970/73A
1973-06-12
1973-06-12
Acylureido cephalosporins

Expired

GB1479711A
(en)

Priority Applications (39)

Application Number
Priority Date
Filing Date
Title

GB27970/73A

GB1479711A
(en)

1973-06-12
1973-06-12
Acylureido cephalosporins

IE2264/77A

IE39295B1
(en)

1973-06-12
1974-05-29
7-amino-3-thiomethyl cephem 4-carboxylic acid derivatives

IE2265/77A

IE39296B1
(en)

1973-06-12
1974-05-29
Carboxymethyl thiols

IE1132/74A

IE39294B1
(en)

1973-06-12
1974-05-29
Acylureido cephalosporins

IL44959A

IL44959A
(en)

1973-06-12
1974-06-03
-acylureido-cephalosporins and their preparation

ZM85/74A

ZM8574A1
(en)

1973-06-12
1974-06-05
Cephalosporins

AU69843/74A

AU475246B2
(en)

1973-06-12
1974-06-06
Cephalosporins

MW24/74*UA

MW2474A1
(en)

1973-06-12
1974-06-10
Cephalosporins

FI179174A

FI179174A
(en)

1973-06-12
1974-06-11

DK311874A

DK311874A
(en)

1973-06-12
1974-06-11

DE19742428139

DE2428139A1
(en)

1973-06-12
1974-06-11

CEPHALOSPORINE, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING THESE COMPOUNDS

NO742117A

NO742117L
(en)

1973-06-12
1974-06-11

AT482074A

AT335060B
(en)

1973-06-12
1974-06-11

PROCESS FOR PRODUCING NEW CEPHALOSPORINES

SE7407713A

SE7407713L
(en)

1973-06-12
1974-06-11

DD179086A

DD111581A5
(en)

1973-06-12
1974-06-11

JP49066446A

JPS5047990A
(en)

1973-06-12
1974-06-11

CH361378A

CH613456A5
(en)

1973-06-12
1974-06-12
Process for the preparation of cephalosporins

PL17185574A

PL89964B1
(en)

1973-06-12
1974-06-12

ZA00743748A

ZA743748B
(en)

1973-06-12
1974-06-12
Cephalosporins

ES427234A

ES427234A1
(en)

1973-06-12
1974-06-12
A procedure for the preparation of a cefalosporine. (Machine-translation by Google Translate, not legally binding)

RO7913074A

RO63098A
(en)

1973-06-12
1974-06-12

PROCESS FOR THE PREPARATION OF CEPHALOSPORIMES

CH806474A

CH609350A5
(en)

1973-06-12
1974-06-12

PL18935374A

PL94613B1
(en)

1973-06-12
1974-06-12

METHOD OF MAKING CEPHALOSPORIN

BE145344A

BE816238A
(en)

1973-06-12
1974-06-12

CEPHALOSPORINS

RO8634574A

RO63740A
(en)

1973-06-12
1974-06-12

PROCESS FOR THE PREPARATION OF CEPHALOSPORINS

RO7486344A

RO64674A
(en)

1973-06-12
1974-06-12

PROCESS FOR THE PREPARATION OF CEPHALOSPORINS

NL7407815A

NL7407815A
(en)

1973-06-12
1974-06-12

FR7420301A

FR2233067A1
(en)

1973-06-12
1974-06-12
N-(thio)acyl carbamoyl-glycylamino-cephalosporin ic acids – as antibiotics esp. active against pseudomonas and gram neg. organisms producing cephalosporinase

CH361278A

CH611303A5
(en)

1973-06-12
1974-06-12
Process for the preparation of cephalosporins

SU752189959A

SU688130A3
(en)

1973-06-12
1975-11-19
Method of obtaining cephalosporines or salts thereof

US05/683,792

US4312982A
(en)

1973-06-12
1976-05-06
α-Acylureidocephalosporins and salts and esters thereof

NO770104A

NO770104L
(en)

1973-06-12
1977-01-12

SE7706081A

SE7706081L
(en)

1973-06-12
1977-05-24

PROCEDURE FOR THE PREPARATION OF CEPHALOSPORINS

IL52704A

IL52704A0
(en)

1973-06-12
1977-08-11
Novel derivatives of 7-amino-cephem-4-carboxylic acid

AR269874A

AR219722A1
(en)

1973-06-12
1977-11-07

ACID 7-AMINO-3- (1-CARBOXIMETIL-1H-TETRAZOLE-5-ILTIO) -METILCEF-3-EM-4-CARBOXILICO, INTERMEDIATE COMPOUND USEFUL FOR THE PREPARATION OF CEPHALOSPORINS, WITHOUT APPLICATION AS A THERAPEUTIC AGENT

FI773446A

FI773446A
(en)

1973-06-12
1977-11-15

FI773447A

FI773447A
(en)

1973-06-12
1977-11-15

DK533177A

DK533177A
(en)

1973-06-12
1977-12-01

LEMIC COMPOUNDS FOR USE AS AN INTERMEDIATE IN THE MANUFACTURE OF CEPHALOSPORINE

NL8104456A

NL8104456A
(en)

1973-06-12
1981-09-29
N-(thio)acyl carbamoyl-glycylamino-cephalosporin ic acids – as antibiotics esp. active against pseudomonas and gram neg. organisms producing cephalosporinase

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

GB27970/73A

GB1479711A
(en)

1973-06-12
1973-06-12
Acylureido cephalosporins

GB4896873

1973-10-20

Publications (1)

Publication Number
Publication Date

GB1479711A
true

GB1479711A
(en)

1977-07-13

Family
ID=26259100
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB27970/73A
Expired

GB1479711A
(en)

1973-06-12
1973-06-12
Acylureido cephalosporins

Country Status (16)

Country
Link

US
(1)

US4312982A
(en)

JP
(1)

JPS5047990A
(en)

AR
(1)

AR219722A1
(en)

AU
(1)

AU475246B2
(en)

BE
(1)

BE816238A
(en)

CH
(1)

CH609350A5
(en)

DD
(1)

DD111581A5
(en)

DE
(1)

DE2428139A1
(en)

DK
(1)

DK311874A
(en)

GB
(1)

GB1479711A
(en)

IE
(1)

IE39294B1
(en)

IL
(2)

IL44959A
(en)

MW
(1)

MW2474A1
(en)

NL
(1)

NL7407815A
(en)

SE
(2)

SE7407713L
(en)

ZM
(1)

ZM8574A1
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4298605A
(en)

1978-06-22
1981-11-03
Chugai Seiyaku Kabushiki Kaisha
Cephalosporin derivatives

Families Citing this family (10)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4071683A
(en)

*

1973-10-30
1978-01-31
Bayer Aktiengesellschaft
Oxoimidazolidinylthiocarbonyl derivatives of ceph-3-em-4-carboxylic acids

US4086340A
(en)

1974-02-18
1978-04-25
Bayer Aktiengesellschaft
Cephalosporins and their production

US4107304A
(en)

1974-02-18
1978-08-15
Bayer Aktiengesellschaft
Oxo-imidazolidine substituted cephalosporins and antibacterial compositions and methods of combatting bacteria employing them

US4224442A
(en)

*

1975-03-03
1980-09-23
Eli Lilly And Company
7-Ureido acetamido substituted cephalosporin antibiotics

US4061630A
(en)

*

1976-02-20
1977-12-06
Eli Lilly And Company
7-Substituted-ureido-3-carbamoyloxymethyl cephalosporin antibiotics

US4061861A
(en)

*

1976-06-21
1977-12-06
Eli Lilly And Company
7-[α-(2,3-DIHYDRO-2-OXO-1H-benzimidazol-1-ylcarbonyl-amino)arylacetamido]cephalosporins

FR2362146A1
(en)

*

1976-08-17
1978-03-17
Fujisawa Pharmaceutical Co

PROCESS FOR THE PREPARATION OF 7- (N-SUBSTITUE-2-PHENYLGLYCINAMIDO) -3-SUBSTITUE-3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS AND NEW PRODUCTS THUS OBTAINED, WITH ANTIBACTERIAL ACTIVITY

JPS5346996A
(en)

*

1976-10-13
1978-04-27
Sangyo Kagaku Kenkyu Kyokai
Antifungal compound

US4217348A
(en)

1978-09-28
1980-08-12
E. R. Squibb & Sons, Inc.
Cephalosporins having an oxazolidonyloxamido substituted acyl sidechain

US4436903A
(en)

*

1980-12-22
1984-03-13
Ciba-Geigy Corporation
Process for the production of 7 β-substituted-3-unsubstituted-3-cephem-4-carboxylic acid compounds

Family Cites Families (10)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3687949A
(en)

*

1969-01-21
1972-08-29
Bristol Myers Co
Synthetic cephalosporins

US3673183A
(en)

*

1969-11-17
1972-06-27
Squibb & Sons Inc
{60 -ureidocephalosporanic acid compounds

US3741962A
(en)

*

1971-05-21
1973-06-26
Squibb & Sons Inc
Alpha-thioureidocephalosporanic acid compounds

CH570407A5
(en)

*

1972-03-29
1975-12-15
Ciba Geigy Ag

US4086340A
(en)

*

1974-02-18
1978-04-25
Bayer Aktiengesellschaft
Cephalosporins and their production

US4107304A
(en)

*

1974-02-18
1978-08-15
Bayer Aktiengesellschaft
Oxo-imidazolidine substituted cephalosporins and antibacterial compositions and methods of combatting bacteria employing them

US3925368A
(en)

*

1974-04-01
1975-12-09
Lilly Co Eli
Acylureido substituted cephalosporins

US3956292A
(en)

*

1974-04-01
1976-05-11
Eli Lilly And Company
7-(α-FUROYLUREIDOARYL AND CYCLOHEXADIENYLACETAMIDO) CEPHALOSPORIN ANTIBIOTICS

US4224442A
(en)

*

1975-03-03
1980-09-23
Eli Lilly And Company
7-Ureido acetamido substituted cephalosporin antibiotics

US4061630A
(en)

*

1976-02-20
1977-12-06
Eli Lilly And Company
7-Substituted-ureido-3-carbamoyloxymethyl cephalosporin antibiotics

1973

1973-06-12
GB
GB27970/73A
patent/GB1479711A/en
not_active
Expired

1974

1974-05-29
IE
IE1132/74A
patent/IE39294B1/en
unknown

1974-06-03
IL
IL44959A
patent/IL44959A/en
unknown

1974-06-05
ZM
ZM85/74A
patent/ZM8574A1/en
unknown

1974-06-06
AU
AU69843/74A
patent/AU475246B2/en
not_active
Expired

1974-06-10
MW
MW24/74*UA
patent/MW2474A1/en
unknown

1974-06-11
DE
DE19742428139
patent/DE2428139A1/en
active
Pending

1974-06-11
DK
DK311874A
patent/DK311874A/da
unknown

1974-06-11
JP
JP49066446A
patent/JPS5047990A/ja
active
Pending

1974-06-11
SE
SE7407713A
patent/SE7407713L/xx
unknown

1974-06-11
DD
DD179086A
patent/DD111581A5/xx
unknown

1974-06-12
BE
BE145344A
patent/BE816238A/en
unknown

1974-06-12
NL
NL7407815A
patent/NL7407815A/xx
not_active
Application Discontinuation

1974-06-12
CH
CH806474A
patent/CH609350A5/xx
not_active
IP Right Cessation

1976

1976-05-06
US
US05/683,792
patent/US4312982A/en
not_active
Expired – Lifetime

1977

1977-05-24
SE
SE7706081A
patent/SE7706081L/en
not_active
Application Discontinuation

1977-08-11
IL
IL52704A
patent/IL52704A0/en
unknown

1977-11-07
AR
AR269874A
patent/AR219722A1/en
active

Cited By (4)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4298605A
(en)

1978-06-22
1981-11-03
Chugai Seiyaku Kabushiki Kaisha
Cephalosporin derivatives

US4301161A
(en)

1978-06-22
1981-11-17
Chugai Seiyaku Kabushiki Kaisha
Cephalosporin derivatives

US4328224A
(en)

1978-06-22
1982-05-04
Chugai Seiyaku Kabushiki Kaisha
Cephalosporin derivatives

US4341776A
(en)

1978-06-22
1982-07-27
Chugai Seiyaku Kabushiki Kaisha
Cephalosporin derivatives

Also Published As

Publication number
Publication date

AU475246B2
(en)

1976-08-19

DK311874A
(en)

1975-02-17

IL52704A0
(en)

1977-10-31

BE816238A
(en)

1974-12-12

SE7706081L
(en)

1977-05-24

US4312982A
(en)

1982-01-26

AR219722A1
(en)

1980-09-15

AU6984374A
(en)

1975-12-11

DD111581A5
(en)

1975-02-20

DE2428139A1
(en)

1975-01-09

SE7407713L
(en)

1974-06-11

IL44959A
(en)

1978-07-31

IE39294B1
(en)

1978-09-13

JPS5047990A
(en)

1975-04-28

NL7407815A
(en)

1974-12-16

ZM8574A1
(en)

1976-08-23

IE39294L
(en)

1974-12-12

IL44959A0
(en)

1974-09-10

CH609350A5
(en)

1979-02-28

MW2474A1
(en)

1975-08-13

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(en)

1978-01-18

3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation

GB1387656A
(en)

1975-03-19

Cephalosporin compounds

US4193918A
(en)

1980-03-18

Process for the preparation of hydroxy-alpha-amino-benzyl penicillin

GB1397647A
(en)

1975-06-11

Thiophene derivatives

GB1390754A
(en)

1975-04-16

Penicillin and cephalosporin esters

GB1331505A
(en)

1973-09-26

Derivatives of thiophene acetic acid and processes for preparing them

GB1459999A
(en)

1976-12-31

Penicillin and cephalosporin intermediates

GB1390402A
(en)

1975-04-09

Substituted imidazolecarboxamides

GB1476312A
(en)

1977-06-10

Penicillins and cephalosporins

GB1430908A
(en)

1976-04-07

Derivatives of cephalosporin

SU735169A3
(en)

1980-05-15

Method of preparing cephalosporin derivatives

ES427234A1
(en)

1976-09-01

A procedure for the preparation of a cefalosporine. (Machine-translation by Google Translate, not legally binding)

ES434923A1
(en)

1976-12-16

Cephalosporin esters

GB1377817A
(en)

1974-12-18

Penicillins and cephalosporins

SE7707246L
(en)

1977-12-31

PROCEDURE FOR PREPARING NEW PENICILL ASSOCIATIONS

Legal Events

Date
Code
Title
Description

1977-11-23
PS
Patent sealed [section 19, patents act 1949]

1979-05-16
48S
Specification amended (sect. 8/1949)

1979-05-23
SPA
Amended specification published

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