GB1453677A - Antibacterial cyanoquinoxaline 1,4-dioxides - Google Patents
Antibacterial cyanoquinoxaline 1,4-dioxidesInfo
- Publication number
- GB1453677A GB1453677A GB3703274A GB3703274A GB1453677A GB 1453677 A GB1453677 A GB 1453677A GB 3703274 A GB3703274 A GB 3703274A GB 3703274 A GB3703274 A GB 3703274A GB 1453677 A GB1453677 A GB 1453677A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- dioxides
- cyanobenzofurazan
- acetoacetamide
- Prior art date
- 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
Links
- BJVCGEWLQTXZLH-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbonitrile Chemical class C1=CC=C2N([O-])C(C#N)=C[N+](=O)C2=C1 BJVCGEWLQTXZLH-UHFFFAOYSA-N 0.000 title abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- KTYXSXUKPAXKOW-UHFFFAOYSA-N 2,1,3-benzoxadiazole-5-carbonitrile Chemical compound C1=C(C#N)C=CC2=NON=C21 KTYXSXUKPAXKOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 abstract 1
- -1 6-cyanobenzofurazan 1-oxide Chemical compound 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1453677 Cyano - quinoxaline 1,4 - dioxides PFIZER Inc 22 Aug 1974 [7 Jan 1974] 37032/74 Heading C2C Novel compounds of the Formula I wherein the cyano substituent is at the 6 or 7 position and each of R<SP>1</SP> and R<SP>2</SP> is hydrogen, C 1-4 alkyl, 2-hydroxyethyl, 3-hydroxypropyl, CH 2 CH 2 NR<SP>3</SP>R<SP>4</SP> or CH 2 CH 2 CH 2 NR<SP>3</SP>R<SP>4</SP> in which R<SP>3</SP> and R<SP>4</SP> are C 1-3 alkyl and, where applicable, acid-addition salts thereof may be prepared by reacting 5- or 6-cyanobenzofurazan 1-oxide with an acetoacetamide of the formula in the presence of a basic catalyst. The acetoacetamide may be prepared in situ by reacting diketene with an amine R<SP>1</SP>R<SP>2</SP>NH. 5- and 6-Cyanobenzofurazan are claimed in copending Application 24469/76. Pharmaceutical compositions of the compounds of the Formula I with the usual excipients show antibacterial activity when administered orally, parenterally or topically. The compounds may also be used as animal growth promotants when admixed with an animal feed. The compounds may also be used as industrial antimicrobials, for example, in the treatment of water, in slime control and paint and wood preservation and as disinfectants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43117074A | 1974-01-07 | 1974-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1453677A true GB1453677A (en) | 1976-10-27 |
Family
ID=23710775
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2446976A Expired GB1453678A (en) | 1974-01-07 | 1974-08-22 | Sbustituted benzofurazan 1-oxides |
| GB3703274A Expired GB1453677A (en) | 1974-01-07 | 1974-08-22 | Antibacterial cyanoquinoxaline 1,4-dioxides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2446976A Expired GB1453678A (en) | 1974-01-07 | 1974-08-22 | Sbustituted benzofurazan 1-oxides |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6011034B2 (en) |
| AR (1) | AR203585A1 (en) |
| AT (1) | AT347467B (en) |
| BE (1) | BE824065A (en) |
| BG (1) | BG25990A3 (en) |
| CA (1) | CA1033739A (en) |
| CH (1) | CH602670A5 (en) |
| CS (1) | CS191253B2 (en) |
| DD (1) | DD116825A1 (en) |
| DE (1) | DE2500447A1 (en) |
| DK (1) | DK140838C (en) |
| ES (1) | ES433593A1 (en) |
| FI (1) | FI59998C (en) |
| FR (1) | FR2256758B1 (en) |
| GB (2) | GB1453678A (en) |
| HU (1) | HU170490B (en) |
| IE (1) | IE40469B1 (en) |
| IT (1) | IT1047758B (en) |
| LU (1) | LU71601A1 (en) |
| NL (1) | NL7500097A (en) |
| RO (1) | RO76604A (en) |
| SU (1) | SU633478A3 (en) |
| YU (1) | YU36512B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6249221A (en) * | 1985-08-28 | 1987-03-03 | Tsuchiya:Kk | Optical fiber liquid level measuring sensor using reflector |
| JP5352255B2 (en) * | 2009-01-28 | 2013-11-27 | 日本エンバイロケミカルズ株式会社 | Quinoxaline compound or salt thereof, and industrial bactericidal composition |
-
1974
- 1974-08-22 GB GB2446976A patent/GB1453678A/en not_active Expired
- 1974-08-22 GB GB3703274A patent/GB1453677A/en not_active Expired
- 1974-12-12 IE IE2560/74A patent/IE40469B1/en unknown
- 1974-12-24 FR FR7442753A patent/FR2256758B1/fr not_active Expired
-
1975
- 1975-01-03 BE BE1006365A patent/BE824065A/en not_active IP Right Cessation
- 1975-01-04 ES ES433593A patent/ES433593A1/en not_active Expired
- 1975-01-06 CA CA217,360A patent/CA1033739A/en not_active Expired
- 1975-01-06 HU HUPI442A patent/HU170490B/hu unknown
- 1975-01-06 FI FI750017A patent/FI59998C/en not_active IP Right Cessation
- 1975-01-06 DK DK1775A patent/DK140838C/en not_active IP Right Cessation
- 1975-01-06 YU YU00007/75A patent/YU36512B/en unknown
- 1975-01-06 DE DE19752500447 patent/DE2500447A1/en not_active Ceased
- 1975-01-06 NL NL7500097A patent/NL7500097A/en not_active Application Discontinuation
- 1975-01-06 SU SU752097436A patent/SU633478A3/en active
- 1975-01-07 CS CS75116A patent/CS191253B2/en unknown
- 1975-01-07 IT IT47535/75A patent/IT1047758B/en active
- 1975-01-07 JP JP50004618A patent/JPS6011034B2/en not_active Expired
- 1975-01-07 DD DD183530A patent/DD116825A1/xx unknown
- 1975-01-07 LU LU71601A patent/LU71601A1/xx unknown
- 1975-01-07 RO RO7581062A patent/RO76604A/en unknown
- 1975-01-07 BG BG028670A patent/BG25990A3/en unknown
- 1975-01-07 CH CH10475A patent/CH602670A5/xx not_active IP Right Cessation
- 1975-01-07 AT AT7475A patent/AT347467B/en not_active IP Right Cessation
- 1975-01-07 AR AR257213D patent/AR203585A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DK140838C (en) | 1980-04-21 |
| AU7691074A (en) | 1976-07-01 |
| IE40469B1 (en) | 1979-06-06 |
| BG25990A3 (en) | 1979-01-12 |
| FI59998B (en) | 1981-07-31 |
| HU170490B (en) | 1977-06-28 |
| FI59998C (en) | 1981-11-10 |
| AR203585A1 (en) | 1975-09-22 |
| DK1775A (en) | 1975-08-25 |
| JPS6011034B2 (en) | 1985-03-22 |
| BE824065A (en) | 1975-07-03 |
| LU71601A1 (en) | 1975-12-09 |
| CH602670A5 (en) | 1978-07-31 |
| GB1453678A (en) | 1976-10-27 |
| CS191253B2 (en) | 1979-06-29 |
| IE40469L (en) | 1975-07-07 |
| FI750017A (en) | 1975-07-08 |
| CA1033739A (en) | 1978-06-27 |
| DK140838B (en) | 1979-11-26 |
| YU36512B (en) | 1984-02-29 |
| JPS50105678A (en) | 1975-08-20 |
| ATA7475A (en) | 1978-05-15 |
| SU633478A3 (en) | 1978-11-15 |
| DE2500447A1 (en) | 1975-07-17 |
| NL7500097A (en) | 1975-07-09 |
| FR2256758B1 (en) | 1979-05-04 |
| ES433593A1 (en) | 1977-02-16 |
| IT1047758B (en) | 1980-10-20 |
| DD116825A1 (en) | 1975-12-12 |
| AT347467B (en) | 1978-12-27 |
| RO76604A (en) | 1981-04-30 |
| FR2256758A1 (en) | 1975-08-01 |
| YU775A (en) | 1982-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
