GB1208114A - Process for the manufacture of substituted tetraazaphenalenes, and compounds produced thereby - Google Patents
Process for the manufacture of substituted tetraazaphenalenes, and compounds produced therebyInfo
- Publication number
- GB1208114A GB1208114A GB4467967A GB4467967A GB1208114A GB 1208114 A GB1208114 A GB 1208114A GB 4467967 A GB4467967 A GB 4467967A GB 4467967 A GB4467967 A GB 4467967A GB 1208114 A GB1208114 A GB 1208114A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- radical
- tetraazaphenalene
- prepared
- formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,208,114. Tetraazaphenalenes. J. R. GEIGY A.G. 2 Oct., 1967 [3 Oct., 1966], No. 44679/67. Heading C2C. Compounds of the Formula I wherein R 1 represents a hydrogen atom or an alkyl C 1-4 or phenyl radical, R 2 represents a hydrogen atom or a phenyl radical, R 3 represents a hydrogen, chlorine or bromine atom, or an alkoxy C 1-4 , carboxyl or hydroxyl radical are prepared by eliminating the radical X from a compound of the Formula II wherein X is a chlorine or bromine atom or a mercapto or hydrazine radical, the elimination being performed by known methods and, when required, converting the 1,2,8,9 - tetraazaphenalene so obtained into a pharmaceutically acceptable addition salt with an organic or inorganic acid, or transforming it with a lower alkylating agent into a quaternary ammonium compound. Known methods described include (1) when X is a halogen atom the compound of Formula II is reduced using either hydroiodic acid or catalytically activated hydrogen or (2) when X is the mercapto radical the compound of Formula II is treated with catalytically activated nickel or (3) when X is the hydrazine radical the compound of Formula II is treated with an aqueous solution of pH between 7 and 8À5 in the presence of a cuprous salt. α,α - Dibromo - 3 - methyl phthalic anhydride is prepared from 3 - methylphthalic anhydride and N - bromosuccinamide. It is converted by treatment with hydrazine hydrate to 3 - hydroxy - 1,2,8,9 - tetraazaphenalene. This is converted to 3 - chloro - 1,2,8,9 - tetraazaphenalene by reaction with phosphoryl chloride. 3 - Mercapto - 1,2,8,9 - tetraazaphenalene is obtained by reaction of the 3 - hydroxy compound with phosphorus pentasulphide. 3 - hydrazino - 1,2,8,9 - tetraazaphenalene dihydrochloride is obtained from the 3 - chloro compound and hydrazine hydrate in the presence of hydrochloric acid. 7 - Carboxy - 3 - hydroxy phthalide is prepared from α,α - dibromo - 3 - methylphthalic anhydride and sodium hydroxide. 8 - Carboxy - 2 - phenyl - 1(2H)phthalazinone is prepared from hydrazine and 7 - carboxy - 3 - hydroxy phthalide. The carbomethoxy and carboethoxy derivatives are prepared by esterification.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58398066A | 1966-10-03 | 1966-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1208114A true GB1208114A (en) | 1970-10-07 |
Family
ID=24335405
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4467967A Expired GB1208114A (en) | 1966-10-03 | 1967-10-02 | Process for the manufacture of substituted tetraazaphenalenes, and compounds produced thereby |
| GB44680/67A Expired GB1204522A (en) | 1966-10-03 | 1967-10-02 | Substituted tetraazaphenalenes and their salts, a process for their production and compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44680/67A Expired GB1204522A (en) | 1966-10-03 | 1967-10-02 | Substituted tetraazaphenalenes and their salts, a process for their production and compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| AT (3) | AT273980B (en) |
| BE (2) | BE704585A (en) |
| CH (2) | CH515909A (en) |
| DE (2) | DE1695039A1 (en) |
| DK (2) | DK120755B (en) |
| ES (2) | ES345681A1 (en) |
| FI (2) | FI47770C (en) |
| FR (3) | FR1550404A (en) |
| GB (2) | GB1208114A (en) |
| GR (2) | GR37757B (en) |
| IL (2) | IL28709A (en) |
| NL (2) | NL6713374A (en) |
| NO (1) | NO122482B (en) |
| SE (2) | SE329401B (en) |
-
1967
- 1967-09-30 CH CH1363967A patent/CH515909A/en not_active IP Right Cessation
- 1967-09-30 CH CH1364067A patent/CH486477A/en not_active IP Right Cessation
- 1967-10-02 BE BE704585D patent/BE704585A/xx unknown
- 1967-10-02 DK DK487767A patent/DK120755B/en unknown
- 1967-10-02 IL IL2870967A patent/IL28709A/en unknown
- 1967-10-02 NL NL6713374A patent/NL6713374A/xx unknown
- 1967-10-02 AT AT891467A patent/AT273980B/en active
- 1967-10-02 FR FR1550404D patent/FR1550404A/fr not_active Expired
- 1967-10-02 DE DE19671695039 patent/DE1695039A1/en active Pending
- 1967-10-02 NL NL6713378A patent/NL6713378A/xx unknown
- 1967-10-02 NO NO16994967A patent/NO122482B/no unknown
- 1967-10-02 GB GB4467967A patent/GB1208114A/en not_active Expired
- 1967-10-02 FI FI263267A patent/FI47770C/en active
- 1967-10-02 SE SE1346067A patent/SE329401B/xx unknown
- 1967-10-02 ES ES345681A patent/ES345681A1/en not_active Expired
- 1967-10-02 DK DK487867A patent/DK123653B/en unknown
- 1967-10-02 AT AT891667A patent/AT273981B/en active
- 1967-10-02 IL IL2871067A patent/IL28710A/en unknown
- 1967-10-02 GR GR670137757A patent/GR37757B/en unknown
- 1967-10-02 FI FI263167A patent/FI47769C/en active
- 1967-10-02 GR GR670137758A patent/GR37758B/en unknown
- 1967-10-02 ES ES345680A patent/ES345680A1/en not_active Expired
- 1967-10-02 GB GB44680/67A patent/GB1204522A/en not_active Expired
- 1967-10-02 AT AT880368A patent/AT276411B/en active
- 1967-10-02 BE BE704584D patent/BE704584A/xx unknown
- 1967-10-02 SE SE1346167A patent/SE335346B/xx unknown
- 1967-10-02 DE DE19671695038 patent/DE1695038A1/en active Pending
- 1967-12-29 FR FR134300A patent/FR7210M/fr not_active Expired
- 1967-12-29 FR FR134301A patent/FR7211M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GR37757B (en) | 1969-07-11 |
| AT273980B (en) | 1969-09-10 |
| FR1550404A (en) | 1968-12-20 |
| DK123653B (en) | 1972-07-17 |
| GR37758B (en) | 1969-07-11 |
| ES345680A1 (en) | 1968-11-16 |
| DK120755B (en) | 1971-07-12 |
| CH515909A (en) | 1971-11-30 |
| FI47769B (en) | 1973-11-30 |
| DE1695038A1 (en) | 1971-04-08 |
| BE704584A (en) | 1968-04-02 |
| IL28709A (en) | 1973-01-30 |
| FI47770C (en) | 1974-03-11 |
| NO122482B (en) | 1971-07-05 |
| DE1695039A1 (en) | 1971-04-08 |
| BE704585A (en) | 1968-04-02 |
| AT273981B (en) | 1969-09-10 |
| GB1204522A (en) | 1970-09-09 |
| ES345681A1 (en) | 1968-11-16 |
| AT276411B (en) | 1969-11-25 |
| FI47769C (en) | 1974-03-11 |
| NL6713378A (en) | 1968-04-04 |
| NL6713374A (en) | 1968-04-04 |
| CH486477A (en) | 1970-02-28 |
| SE329401B (en) | 1970-10-12 |
| SE335346B (en) | 1971-05-24 |
| FR7211M (en) | 1969-08-25 |
| FI47770B (en) | 1973-11-30 |
| FR7210M (en) | 1969-08-25 |
| IL28710A (en) | 1973-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed |