GB1363506A

GB1363506A – Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations
– Google Patents

GB1363506A – Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations
– Google Patents
Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations

Info

Publication number
GB1363506A

GB1363506A
GB4309071A
GB4309071A
GB1363506A
GB 1363506 A
GB1363506 A
GB 1363506A
GB 4309071 A
GB4309071 A
GB 4309071A
GB 4309071 A
GB4309071 A
GB 4309071A
GB 1363506 A
GB1363506 A
GB 1363506A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
pharmaceutically acceptable
group
amino
Prior art date
1970-09-17
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
GB4309071A
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.)

Astra Lakemedel AB

Original Assignee
Astra Lakemedel AB
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.)
1970-09-17
Filing date
1971-09-15
Publication date
1974-08-14

1970-09-17
Priority claimed from SE7012688A
external-priority
patent/SE374747B/xx

1970-11-20
Priority claimed from SE1572070A
external-priority
patent/SE380806B/en

1971-09-15
Application filed by Astra Lakemedel AB
filed
Critical
Astra Lakemedel AB

1974-08-14
Publication of GB1363506A
publication
Critical
patent/GB1363506A/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

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

A61P31/04—Antibacterial agents

Abstract

1363506 Penicillins ASTRA LAKEMEDEL AB 15 Sept 1971 [17 Sept 1970 20 Nov 1970] 43090/71 Heading C2A The invention comprises compounds of structural Formula I and pharmaceutically acceptable acid addition salts thereof,; wherein R is an alkyl group containing two to seven carbon atoms; a radical of Formula II wherein R2 is H or OH and R3 is H or halogen; or a radical of formula and wherein R1 represents a group of formula where R4 represents an alkyl group containing 1 to 4 carbon atoms and R5 represents hydrogen, methyl or ethyl. A process for preparing compounds of Formula I comprises reacting compounds of Formula VIII wherein A is amino, substituted amino or a group which is convertible into an amino group and R11 represents hydrogen or a cation with a compound of formula X-R1 wherein X represents halogen or a functionally equivalent group to give a compound of Formula IX if necessary the group A is converted to’ amino and, if desired, the free base is converted to a salt by reaction with a pharmaceutically acceptable acid. An alternative process for preparing compounds of Formula I comprises reacting compounds of formula with compounds of Formula XI to give compounds of Formula IX, in which formula -CO-Y1 and X1-NH- represent groups which react together to form a -CONH- linkage; if necessary the group A is converted into an amino group and, if desired, the free base is converted to a salt by reaction with a pharmaceutically acceptable acid. The compounds of Formula IX wherein A is azido have been prepared by the abovementioned alternative process. The preparation and use as intermediates of compounds of structural Formula XI where X1 is H are described. Pharmaceutical preparations comprise, as an active ingredient at least one compound of Formula I or a pharmaceutically acceptable salt thereof in association with a pharmaceutically acceptable carrier. A method for the treatment of infectious diseases in animals other than man comprises administering to a host suffering from such a disease a therapeutically acceptable amount of a compound of Formula I or Formula IX where A is azido, or pharmaceutically acceptable salts thereof.

GB4309071A
1970-09-17
1971-09-15
Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations

Expired

GB1363506A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

SE7012688A

SE374747B
(en)

1970-09-17
1970-09-17

SE1572070A

SE380806B
(en)

1970-11-20
1970-11-20

PROCEDURE FOR MAKING NEW ESTRAS OF ALFA-AMINOPENICILLINS

Publications (1)

Publication Number
Publication Date

GB1363506A
true

GB1363506A
(en)

1974-08-14

Family
ID=26655897
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB4309071A
Expired

GB1363506A
(en)

1970-09-17
1971-09-15
Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations

Country Status (21)

Country
Link

US
(2)

US3873521A
(en)

JP
(2)

JPS5317597B1
(en)

AR
(2)

AR201730A1
(en)

AT
(2)

AT311557B
(en)

BE
(1)

BE772723A
(en)

BR
(1)

BR7106116D0
(en)

CA
(2)

CA960211A
(en)

CH
(5)

CH583239A5
(en)

CS
(2)

CS187312B2
(en)

DD
(1)

DD94815A5
(en)

DK
(6)

DK132759C
(en)

ES
(3)

ES395145A1
(en)

FI
(4)

FI55203C
(en)

FR
(1)

FR2106578B1
(en)

GB
(1)

GB1363506A
(en)

HU
(1)

HU165868B
(en)

IE
(1)

IE35642B1
(en)

IT
(1)

IT1049876B
(en)

NL
(3)

NL164860C
(en)

NO
(4)

NO140931C
(en)

SU
(2)

SU553936A3
(en)

Cited By (7)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4389408A
(en)

1980-04-30
1983-06-21
Kanebo Ltd.
Novel ampicillin esters and production thereof

GB2123821A
(en)

*

1982-06-29
1984-02-08
Astra Laekemedel Ab
???-Halogeno diethyl carbonates and their use in the preparation of antibiotics

EP0112130A1
(en)

*

1982-12-09
1984-06-27
Teva Pharmaceutical Industries Limited
Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids, their preparation and use

JPS59122441A
(en)

*

1982-11-04
1984-07-14
アストラ・ラケメデル・アクチェボラグ
Novel 1-bromoethylethylcarbonate compound and manufacture

GB2168050A
(en)

*

1982-06-29
1986-06-11
Astra Laekemedel Ab
Intermediates useful in the preparation of antibiotics

US4619785A
(en)

*

1982-06-29
1986-10-28
Astra Lakemedel Aktiebolag
Novel synthesis route for bacampicillin

AU581694B2
(en)

*

1984-11-09
1989-03-02
Astra Lakemedel Aktiebolag
Stabilized of bacampicillin hydrochloride compositions

Families Citing this family (19)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1426869A
(en)

*

1972-03-13
1976-03-03
Astra Laekemedel Ab
Penicillins

US4089963A
(en)

*

1972-03-13
1978-05-16
Astra Pharmaceutical Products, Inc.
Esters of amidinopenicillanic acids, pharmaceutical preparations and method for treating infectious diseases

GB1425933A
(en)

*

1972-03-13
1976-02-25
Astra Laekemedel Ab
Cephalosporins

GB1437088A
(en)

*

1972-05-25
1976-05-26
Beecham Group Ltd
Esters of penicillins and cephalosporins

NL7401782A
(en)

*

1973-02-14
1974-08-16

GB1550359A
(en)

*

1975-08-07
1979-08-15
Beecham Group Ltd
Antibiotic compositions for oral administration

US4247461A
(en)

*

1979-11-16
1981-01-27
Bristol-Myers Company
Esterification process using methoxymethyl-P-toluenesulfonate

US4340539A
(en)

*

1980-01-21
1982-07-20
Bristol-Myers Company
Derivatives of 6-bromo penicillanic acid

FR2482587A1
(en)

*

1980-05-14
1981-11-20
Poudres & Explosifs Ste Nale

PROCESS FOR THE SYNTHESIS OF A-CHLORINATED CHLOROFORMIATES AND NEW A-CHLORINATED CHLOROFORMIATES

US4321253A
(en)

*

1980-08-22
1982-03-23
Beatty Morgan L
Suspension of microencapsulated bacampicillin acid addition salt for oral, especially pediatric, administration

US4479947A
(en)

*

1981-07-13
1984-10-30
Merck & Co., Inc.
Oral absorption enhancement of carboxylic acid pharmaceuticals using (5-alkyl-2-oxo-1,3-dioxolen-4-yl)methyl ester group

CA1202617A
(en)

*

1982-03-19
1986-04-01
Norman B. Jones
Bacampicillin napsylate

FR2532933B1
(en)

*

1982-06-29
1987-11-13
Astra Laekemedel Ab

IMPROVEMENTS IN THE PREPARATION OF ANTIBIOTICS

JPS5927900A
(en)

*

1982-08-09
1984-02-14
Wakunaga Seiyaku Kk
Oligonucleotide derivative and its preparation

US4606865A
(en)

*

1982-09-20
1986-08-19
Astra Lakemedel Aktiebolag
Methods for the preparation of α-bromodiethylcarbonate

DK149079C
(en)

*

1982-10-06
1986-06-23
Novo Industri As

PROCEDURE FOR PREPARING AN IMMOBILIZED ENZYME PREPARATION

IL67637A0
(en)

*

1983-01-07
1983-05-15
Orvet Bv
Preparation of 1′-ethoxycarbonyl-oxyethyl esters of penicillins and novel intermediates

FR2551058B1
(en)

*

1983-08-26
1986-09-26
Poudres & Explosifs Ste Nale

PROCESS FOR THE PREPARATION OF A-CHLORINATED CHLOROFORMIATES

US4855455A
(en)

*

1988-01-22
1989-08-08
W. R. Grace & Co.-Conn.
Preparation of amino acid derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

FR1021654A
(en)

*

1949-07-07
1953-02-23
Lphivens Kemiske Fabrik Ved A

Process for the production of amino ethers-salts of penicillin and compounds related thereto

GB1241844A
(en)

*

1968-08-23
1971-08-04
Beecham Group Ltd
Penicillins

US3697507A
(en)

*

1968-09-26
1972-10-10
Leo Pharm Prod Ltd
Esters of {60 -aminobenzylpenicillin

US3660575A
(en)

*

1968-09-26
1972-05-02
Leo Pharm Prod Ltd
Esters of alpha-aminobenzylpenicillin in dosage unit form

1971

1971-09-07
US
US178426A
patent/US3873521A/en
not_active
Expired – Lifetime

1971-09-14
AT
AT537872A
patent/AT311557B/en
not_active
IP Right Cessation

1971-09-14
SU
SU1696133A
patent/SU553936A3/en
active

1971-09-14
AT
AT795771A
patent/AT309681B/en
not_active
IP Right Cessation

1971-09-14
FR
FR7133107A
patent/FR2106578B1/fr
not_active
Expired

1971-09-15
CA
CA122,881A
patent/CA960211A/en
not_active
Expired

1971-09-15
IE
IE1167/71A
patent/IE35642B1/en
unknown

1971-09-15
FI
FI2580/71A
patent/FI55203C/en
active

1971-09-15
IT
IT28678/71A
patent/IT1049876B/en
active

1971-09-15
GB
GB4309071A
patent/GB1363506A/en
not_active
Expired

1971-09-16
BR
BR6116/71A
patent/BR7106116D0/en
unknown

1971-09-16
CH
CH1362371A
patent/CH583239A5/xx
not_active
IP Right Cessation

1971-09-16
CS
CS716617A
patent/CS187312B2/en
unknown

1971-09-16
ES
ES195145A
patent/ES395145A1/en
not_active
Expired

1971-09-16
CH
CH860075A
patent/CH589654A5/xx
not_active
IP Right Cessation

1971-09-16
HU
HUAA684A
patent/HU165868B/hu
unknown

1971-09-16
CH
CH859975A
patent/CH577513A5/xx
not_active
IP Right Cessation

1971-09-16
NO
NO3449/71A
patent/NO140931C/en
unknown

1971-09-16
CS
CS71442A
patent/CS187316B2/cs
unknown

1971-09-16
DK
DK453871A
patent/DK132759C/en
not_active
IP Right Cessation

1971-09-17
JP
JP7184971A
patent/JPS5317597B1/ja
active
Pending

1971-09-17
NL
NL7112789.A
patent/NL164860C/en
not_active
IP Right Cessation

1971-09-17
DD
DD157795A
patent/DD94815A5/xx
unknown

1971-09-17
BE
BE772723A
patent/BE772723A/en
not_active
IP Right Cessation

1972

1972-01-31
NO
NO236/72A
patent/NO140930C/en
unknown

1972-04-12
AR
AR241427A
patent/AR201730A1/en
active

1972-04-14
ES
ES401745A
patent/ES401745A1/en
not_active
Expired

1973

1973-03-08
US
US05/339,364
patent/US3939270A/en
not_active
Expired – Lifetime

1973-03-27
SU
SU731899287A
patent/SU1153830A3/en
active

1973-10-25
CA
CA184,183A
patent/CA1008447A/en
not_active
Expired

1974

1974-09-27
DK
DK509774A
patent/DK509774A/da
unknown

1974-09-27
DK
DK509674A
patent/DK150200C/en
not_active
IP Right Cessation

1974-12-19
NO
NO74744606A
patent/NO142670C/en
unknown

1974-12-31
FI
FI3814/74A
patent/FI59600C/en
active

1975

1975-01-08
ES
ES433637A
patent/ES433637A1/en
not_active
Expired

1975-04-08
AR
AR258235A
patent/AR210991A1/en
active

1975-06-24
JP
JP7921675A
patent/JPS5537996B2/ja
not_active
Expired

1975-08-20
DK
DK375975A
patent/DK375975A/da
unknown

1976

1976-04-20
CH
CH493776A
patent/CH613207A5/xx
not_active
IP Right Cessation

1977

1977-09-21
CH
CH1155377A
patent/CH602745A5/xx
not_active
IP Right Cessation

1977-10-13
FI
FI773032A
patent/FI57951C/en
not_active
IP Right Cessation

1978

1978-01-31
NL
NL7801086A
patent/NL7801086A/en
active
Search and Examination

1978-12-08
NO
NO784144A
patent/NO142671C/en
unknown

1979

1979-04-27
FI
FI791386A
patent/FI59103C/en
not_active
IP Right Cessation

1980

1980-03-17
NL
NLAANVRAGE8001563,A
patent/NL171160C/en
not_active
IP Right Cessation

1980-03-27
DK
DK133380A
patent/DK150201C/en
not_active
IP Right Cessation

1982

1982-04-07
DK
DK163482A
patent/DK158519C/en
not_active
IP Right Cessation

Cited By (10)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4389408A
(en)

1980-04-30
1983-06-21
Kanebo Ltd.
Novel ampicillin esters and production thereof

GB2123821A
(en)

*

1982-06-29
1984-02-08
Astra Laekemedel Ab
???-Halogeno diethyl carbonates and their use in the preparation of antibiotics

GB2168050A
(en)

*

1982-06-29
1986-06-11
Astra Laekemedel Ab
Intermediates useful in the preparation of antibiotics

GB2168699A
(en)

*

1982-06-29
1986-06-25
Astra Laekemedel Ab
alpha -Bromodiethyl carbonate and its use in the preparation of antibiotics

GB2169287A
(en)

*

1982-06-29
1986-07-09
Astra Laekemedel Ab
Improvements in the preparation of ampicillin

US4619785A
(en)

*

1982-06-29
1986-10-28
Astra Lakemedel Aktiebolag
Novel synthesis route for bacampicillin

JPS59122441A
(en)

*

1982-11-04
1984-07-14
アストラ・ラケメデル・アクチェボラグ
Novel 1-bromoethylethylcarbonate compound and manufacture

EP0112130A1
(en)

*

1982-12-09
1984-06-27
Teva Pharmaceutical Industries Limited
Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids, their preparation and use

JPS59112944A
(en)

*

1982-12-09
1984-06-29
テバ・フア−マシユ−テイカル・インダストリ−ズ・リミテツド
Ethoxycarbonyloxyethyl ester of non-steroidal antiinflammatory carboxylic acid, manufacture and medicinal composition

AU581694B2
(en)

*

1984-11-09
1989-03-02
Astra Lakemedel Aktiebolag
Stabilized of bacampicillin hydrochloride compositions

Also Published As

Publication number
Publication date

DK158519C
(en)

1990-11-05

DK509774A
(en)

1975-05-26

CS187312B2
(en)

1979-01-31

FI55203B
(en)

1979-02-28

IE35642B1
(en)

1976-04-14

JPS5136491A
(en)

1976-03-27

NO140930B
(en)

1979-09-03

FI773032A
(en)

1977-10-13

NO140930C
(en)

1979-12-12

NL7801086A
(en)

1978-05-31

NO784144L
(en)

1972-03-20

DK375975A
(en)

1975-08-20

IE35642L
(en)

1972-03-17

FI381474A
(en)

1974-12-31

FI791386A
(en)

1979-04-27

NO140931B
(en)

1979-09-03

NL7112789A
(en)

1972-03-21

JPS5537996B2
(en)

1980-10-01

NO142670C
(en)

1980-09-24

CS187316B2
(en)

1979-01-31

AT309681B
(en)

1973-08-27

NO140931C
(en)

1979-12-12

NL164860C
(en)

1981-02-16

DK133380A
(en)

1980-03-27

FI59600C
(en)

1981-09-10

US3873521A
(en)

1975-03-25

DK132759B
(en)

1976-02-02

CA960211A
(en)

1974-12-31

FI59103C
(en)

1981-06-10

DK163482A
(en)

1982-04-07

AT311557B
(en)

1973-11-26

DD94815A5
(en)

1973-01-05

BR7106116D0
(en)

1973-03-20

JPS5317597B1
(en)

1978-06-09

FR2106578A1
(en)

1972-05-05

AR210991A1
(en)

1977-10-14

ES395145A1
(en)

1974-11-16

FI59103B
(en)

1981-02-27

CH577513A5
(en)

1976-07-15

CH613207A5
(en)

1979-09-14

CH602745A5
(en)

1978-07-31

SU1153830A3
(en)

1985-04-30

DK509674A
(en)

1975-06-02

BE772723A
(en)

1972-03-17

CH589654A5
(en)

1977-07-15

DK150200B
(en)

1987-01-05

CH583239A5
(en)

1976-12-31

HU165868B
(en)

1974-12-28

IT1049876B
(en)

1981-02-10

ES401745A1
(en)

1976-05-16

FI59600B
(en)

1981-05-29

SU553936A3
(en)

1977-04-05

NL171160C
(en)

1983-02-16

US3939270A
(en)

1976-02-17

DK150201C
(en)

1987-07-06

FR2106578B1
(en)

1975-06-06

FI57951B
(en)

1980-07-31

AR201730A1
(en)

1975-04-15

NO142671C
(en)

1980-09-24

FI55203C
(en)

1979-06-11

NO142671B
(en)

1980-06-16

DK150200C
(en)

1987-07-06

CA1008447A
(en)

1977-04-12

NL171160B
(en)

1982-09-16

NL8001563A
(en)

1980-06-30

DE2144457B2
(en)

1977-05-05

DE2144457A1
(en)

1972-03-30

NO744606L
(en)

1972-03-20

ES433637A1
(en)

1976-11-16

NO142670B
(en)

1980-06-16

DK158519B
(en)

1990-05-28

FI57951C
(en)

1980-11-10

DK132759C
(en)

1976-07-05

DK150201B
(en)

1987-01-05

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Process for the preparation of alpha-amino-penicillins and such penicillins and intermediates and pharmaceutical preparations

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(en)

1983-10-01

Novel 3-phenyl-1-indanamines, pharmaceutical compositions and methods of preparation.

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(en)

1973-05-08

Trimethoxybenzoyl-aminoalkanoic acids

JPS61118391A
(en)

1986-06-05

Cephalin derivative, manufacture and medicine

GB1505899A
(en)

1978-03-30

3,4-dihydrocarbostyril derivatives

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1980-11-01

Novel hydroxamic acid compounds, method for preparation thereof and medicaments containing such compounds

KR870007098A
(en)

1987-08-14

Fluorinated diaminoalkyne derivatives and preparation method thereof

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1976-03-03

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(en)

1978-10-01

2,4 – dichlorophenyl – imidazolyl – ethan – ones and -ols a process for their preparation and their use as medicaments

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(en)

1969-12-10

N-Substituted Nor-Morphines

ES8101062A1
(en)

1982-04-16

Basically substituted urea compounds, process for producing the same and pharmaceutical compositions containing the same.

IE40758B1
(en)

1979-08-15

New basic enol ethers,their salts,process for their preparation and pharmaceutical preparations containing the same

Legal Events

Date
Code
Title
Description

1974-12-27
PS
Patent sealed [section 19, patents act 1949]

1991-10-16
PE20
Patent expired after termination of 20 years

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