GB1457066A

GB1457066A – Thiazolo 5,4-f-quinoline-8-carboxylic acid derivatives and a method for the preparation thereof
– Google Patents

GB1457066A – Thiazolo 5,4-f-quinoline-8-carboxylic acid derivatives and a method for the preparation thereof
– Google Patents
Thiazolo 5,4-f-quinoline-8-carboxylic acid derivatives and a method for the preparation thereof

Info

Publication number
GB1457066A

GB1457066A
GB4495174A
GB4495174A
GB1457066A
GB 1457066 A
GB1457066 A
GB 1457066A
GB 4495174 A
GB4495174 A
GB 4495174A
GB 4495174 A
GB4495174 A
GB 4495174A
GB 1457066 A
GB1457066 A
GB 1457066A
Authority
GB
United Kingdom
Prior art keywords
quinoline
carboxylate
ethyl
prepared
chloro
Prior art date
1973-10-17
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
GB4495174A
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.)

Sumitomo Chemical Co Ltd

Original Assignee
Sumitomo Chemical 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.)
1973-10-17
Filing date
1974-10-17
Publication date
1976-12-01

1973-10-17
Priority claimed from JP48117042A
external-priority
patent/JPS5064300A/ja

1973-10-18
Priority claimed from JP48117496A
external-priority
patent/JPS5064298A/ja

1973-11-22
Priority claimed from JP48131991A
external-priority
patent/JPS5082097A/ja

1973-11-26
Priority claimed from JP48133175A
external-priority
patent/JPS5083396A/ja

1973-12-13
Priority claimed from JP48140152A
external-priority
patent/JPS5089397A/ja

1973-12-13
Priority claimed from JP48140151A
external-priority
patent/JPS5089396A/ja

1974-10-17
Application filed by Sumitomo Chemical Co Ltd
filed
Critical
Sumitomo Chemical Co Ltd

1976-12-01
Publication of GB1457066A
publication
Critical
patent/GB1457066A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 – C07D507/00

C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 – C07D507/00 in which the condensed system contains two hetero rings

C07D513/04—Ortho-condensed systems

Abstract

1457066 Derivatives of thiazolo[5,4-f]quino line – 8 – carboxyclic acid; their preparation and their pharmaceutical compositions SUMITOMO CHEMICAL CO Ltd 17 Oct 1974 [17 Oct 1973 18 Oct 1973 22 Nov 1973 26 Nov 1973 13 Dec 1973 (2)] 44951/74 Heading C2C The invention comprises compounds of Formulµ I and IIIa wherein R1 represents a C 1-4 alkyl, C 2-4 alkenyl or a benzyl group, R3 represents a C 1-4 alkyl group and X represents a chlorine or bromine atom which compounds of Formula I are prepared by reacting 2,3,6,9-tetrahydro-6-hydroxy- 2,9 – dioxothiazolo[5,4-f]quinoline – 8 – carboxylic acid with a halide of formula or when R1 is a C 1-4 alkyl group with a dialkyl sulphate of formula and which compounds of Formula IIIa are prepared by a compound of the general Formula IVa wherein R3 and X are as defined above with a peroxide. 2 – Hydroxy- and 2 – methylsulphonyl – 6[bis- (21,21 – ethoxycarbonyl)ethenylamino]benzothiazole are prepared by reacting the corresponding 2- substituted – 6 – aminobenzothiazoles with diethylethoxymethylene malonate in D.M.F. at 100-110 C. Ethyl 9 – hydroxy – 2 – methyleulphonylthiazolo[5,4-f]quinoline – 8 – carboxylate and ethyl 2 – chloro – 9 – hydroxythiazolo[5,4-f]quinoline – 8- carboxylate are prepared by heating the corresponding 2 – substituted – 6 – [bis(21,21 – ethoxycarbonyl)ethenylamino] – benzothiazole at 250-257 C. Ethyl 2,9 – dichlorothiazolo[5,4-f]quinoline – 8- carboxylate and ethyl 9 – chloro – 2 – methylsulphonylthiazolo[5,4-f]quinoline – 8 – carboxylate are prepared by heating the corresponding 2- chloro – 2 – methylsulphonyl – 9 – hydroxythiazolo[5,4-f]quinoline – 8 – carboxylates or 2- methylsulphonyl – 6 – [bis(21,21 – ethoxycarbonyl)ethenylamino]benzothiazole with POCl 3 or a mixture of POCl 3 with PCl 3 or PCl 5 . Ethyl 9 – chloro – 2 – methylsulphonylthiazolo- [5,4-f]quinoline – 8 – carboxylate – 6 – onide is prepared by reacting ethyl 9-chloro-2-methylsulphonylthiazolo[5,4-f] – quinoline – 8 – carboxylate with H 2 O 2 and maleic anhydride at 0-5 C. 2,3,6,9 – Tetrahydro – 6 – hydroxy – 2,9 – dioxothiazolo[5,4-f]quinoline – 8 – carboxylic acid is prepared by hydrolysis of ethyl 2,9-dichlorothiazolo[5,4-f]quinoline – 8 – carboxylate – 6- onide or ethyl 9 – chloro – 2 – methylsulphonylthiazolo[5,4-f]quinoline – 8 – carboxylate – 6- onide with potassium and sodium hydroxide respectively. Pharmaceutical compositions having (a) antibacterial and (b) antifungal activity for oral, intraperitoneal, subcutaneous, intravenous or intramuscular administration comprise a compound of (a) Formula I and (b) Formula IIIa or a pharmacutically acceptable salt thereof respectively together with one or more pharmaceutically acceptable carrier or diluent.

GB4495174A
1973-10-17
1974-10-17
Thiazolo 5,4-f-quinoline-8-carboxylic acid derivatives and a method for the preparation thereof

Expired

GB1457066A
(en)

Applications Claiming Priority (6)

Application Number
Priority Date
Filing Date
Title

JP48117042A

JPS5064300A
(en)

1973-10-17
1973-10-17

JP48117496A

JPS5064298A
(en)

1973-10-18
1973-10-18

JP48131991A

JPS5082097A
(en)

1973-11-22
1973-11-22

JP48133175A

JPS5083396A
(en)

1973-11-26
1973-11-26

JP48140152A

JPS5089397A
(en)

1973-12-13
1973-12-13

JP48140151A

JPS5089396A
(en)

1973-12-13
1973-12-13

Publications (1)

Publication Number
Publication Date

GB1457066A
true

GB1457066A
(en)

1976-12-01

Family
ID=27552491
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB4495174A
Expired

GB1457066A
(en)

1973-10-17
1974-10-17
Thiazolo 5,4-f-quinoline-8-carboxylic acid derivatives and a method for the preparation thereof

Country Status (10)

Country
Link

US
(1)

US3954775A
(en)

CA
(1)

CA1039729A
(en)

CH
(1)

CH592100A5
(en)

DE
(1)

DE2449544A1
(en)

DK
(1)

DK543074A
(en)

FR
(1)

FR2248046B1
(en)

GB
(1)

GB1457066A
(en)

HU
(1)

HU171836B
(en)

NL
(1)

NL7413524A
(en)

NO
(1)

NO743723L
(en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

JPS5324028A
(en)

*

1976-08-19
1978-03-06
Sumitomo Chem Co Ltd
Systemic bactericide for plant

US4963677A
(en)

*

1987-12-30
1990-10-16
Orion Corporation Ltd.
Heterocyclic lactam compounds

FR2914906B1
(en)

*

2007-04-11
2009-10-30
Intertechnique Soc Par Actions

METHOD AND DEVICE FOR DETECTING FROST AND / OR GIVING CONDITIONS ON AIRCRAFT IN FLIGHT

Family Cites Families (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DE2056224A1
(en)

*

1969-11-17
1971-06-03
Danchi Seiyaku Co , Ltd , Tokio

New Thiazolochinohnderivate and Ver drive for their production

JPS4911239B1
(en)

*

1970-04-27
1974-03-15

US3799930A
(en)

*

1970-07-09
1974-03-26
Sumitomo Chemical Co
1,4-dihydro-1-substituted-4-oxo-3-quinolinecarboxlic acids and esters

1974

1974-10-11
CA
CA211,318A
patent/CA1039729A/en
not_active
Expired

1974-10-15
NL
NL7413524A
patent/NL7413524A/en
not_active
Application Discontinuation

1974-10-16
DK
DK543074A
patent/DK543074A/da
not_active
Application Discontinuation

1974-10-16
NO
NO743723A
patent/NO743723L/no
unknown

1974-10-16
CH
CH1385974A
patent/CH592100A5/xx
not_active
IP Right Cessation

1974-10-16
HU
HU74SU00000875A
patent/HU171836B/en
unknown

1974-10-17
FR
FR7435021A
patent/FR2248046B1/fr
not_active
Expired

1974-10-17
DE
DE19742449544
patent/DE2449544A1/en
not_active
Withdrawn

1974-10-17
GB
GB4495174A
patent/GB1457066A/en
not_active
Expired

1974-10-17
US
US05/515,753
patent/US3954775A/en
not_active
Expired – Lifetime

Also Published As

Publication number
Publication date

AU7434774A
(en)

1976-04-29

CH592100A5
(en)

1977-10-14

DK543074A
(en)

1975-06-16

US3954775A
(en)

1976-05-04

FR2248046B1
(en)

1978-07-21

CA1039729A
(en)

1978-10-03

HU171836B
(en)

1978-03-28

NL7413524A
(en)

1975-04-21

DE2449544A1
(en)

1975-04-30

FR2248046A1
(en)

1975-05-16

NO743723L
(en)

1975-05-12

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Legal Events

Date
Code
Title
Description

1977-04-14
PS
Patent sealed [section 19, patents act 1949]

1981-06-03
PCNP
Patent ceased through non-payment of renewal fee

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