GB808636A - Basically substituted heterocyclic compounds - Google Patents
Basically substituted heterocyclic compoundsInfo
- Publication number
- GB808636A GB808636A GB23777/56A GB2377756A GB808636A GB 808636 A GB808636 A GB 808636A GB 23777/56 A GB23777/56 A GB 23777/56A GB 2377756 A GB2377756 A GB 2377756A GB 808636 A GB808636 A GB 808636A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxo
- compounds
- sodium
- dihydrophthalazines
- dihydrophthalazine
- 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
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 title 1
- -1 aryloxy radicals Chemical class 0.000 abstract 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 abstract 1
- GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 abstract 1
- SUUOMYNOHWCWIK-UHFFFAOYSA-N 5-chloro-N,N-dimethylpentan-2-amine Chemical compound CN(C(C)CCCCl)C SUUOMYNOHWCWIK-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical class CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003873 salicylate salts Chemical class 0.000 abstract 1
- ZBIISBRWGXZJKH-UHFFFAOYSA-N sodium;1-(diethylamino)ethanolate Chemical compound [Na+].CCN(CC)C(C)[O-] ZBIISBRWGXZJKH-UHFFFAOYSA-N 0.000 abstract 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0808636/IV (b)/1> and salts thereof, wherein R is a benzene ring and <FORM:0808636/IV (b)/2> is the residue of a tertiary amine, which may optionally bear substituents which do not react with halogenoalkyl compounds, such as alkyl alkoxy and aryloxy radicals and the corresponding thio radicals, in the 4-position and/or in the residue R. The compounds are made by reacting the corresponding 1 - oxo - 1 : 2 - dihydrophthalazine, suitably in the form of its alkalimetal salt, with a teritary aminoalkyl halide preferably at 40-60 DEG C. Suitable tertiary aminoalkyl halides include the diethylamino-, dibutylamino-, piperidino-, morpholino- and N-methylanilino-, ethyl chlorides and 1-dimethylamino - 2 - chloropropane and 2 - dimethylamino - 5 - chloropentane. The products are suitable isolated in the form of their acid addition salts such as the hydrochlorides, hydrobromides, sulphates, picrates, benzoates, salicylates and gentisates. Examples describe the preparation of 2-(b -diethylaminoethyl), 2-(b -dimethylaminoethyl), 2 - (a - methyl - b - dimethylaminoethyl), 2 - (b - piperidinoethyl) and 2 - (b - dibutylaminoethyl), 1 - oxo - 1 : 2 - dihydrophthalazine and also the 2-(b -diethylaminoethyl), 4 - methyl -, 4 - methoxy -, 4ethylthio -, and 4 - b - diethylaminoethoxy-, 1-oxo-1 : 2-dihydrophthalazines. 4 - Substituted - phthalazines. The 4 - b - diethylaminoethoxy -, 4 - methoxy - and 4 - ethylthio - 1 - oxo - 1 : 2 - dihydrophthalazines used as starting materials are prepared by treating 1 : 4-dichlorophthalazine with sodium diethylaminoethoxide, sodium methoxide and sodium ethylmercaptide respectively to replace one halogen atom and replacing the second halogen atom by hydrolysis.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE808636X | 1955-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808636A true GB808636A (en) | 1959-02-11 |
Family
ID=6723129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23777/56A Expired GB808636A (en) | 1955-08-02 | 1956-08-01 | Basically substituted heterocyclic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB808636A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164593A1 (en) * | 1984-05-17 | 1985-12-18 | Fisons Corporation | Anti-inflammatory phthalazinones |
| WO2002090333A1 (en) * | 2001-05-04 | 2002-11-14 | Astrazeneca Ab | Novel pyridinone and related heterocyclic derivatives |
| WO2009051504A1 (en) * | 2007-10-15 | 2009-04-23 | Uniwersytet Lodski | Benzo- and pyridopyridazinones with analgesic and antiinflammatory activity |
| JP2017526696A (en) * | 2014-09-05 | 2017-09-14 | ジェネンテック， インコーポレイテッド | Phthalazine derivatives of formula (I) as PCAF and GCN5 inhibitors for use in the treatment of cancer - Patents.com |
-
1956
- 1956-08-01 GB GB23777/56A patent/GB808636A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164593A1 (en) * | 1984-05-17 | 1985-12-18 | Fisons Corporation | Anti-inflammatory phthalazinones |
| WO2002090333A1 (en) * | 2001-05-04 | 2002-11-14 | Astrazeneca Ab | Novel pyridinone and related heterocyclic derivatives |
| WO2009051504A1 (en) * | 2007-10-15 | 2009-04-23 | Uniwersytet Lodski | Benzo- and pyridopyridazinones with analgesic and antiinflammatory activity |
| JP2017526696A (en) * | 2014-09-05 | 2017-09-14 | ジェネンテック， インコーポレイテッド | Phthalazine derivatives of formula (I) as PCAF and GCN5 inhibitors for use in the treatment of cancer - Patents.com |
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