GB903725A - Phenthiazine derivatives - Google Patents
Phenthiazine derivativesInfo
- Publication number
- GB903725A GB903725A GB35086/58A GB3508658A GB903725A GB 903725 A GB903725 A GB 903725A GB 35086/58 A GB35086/58 A GB 35086/58A GB 3508658 A GB3508658 A GB 3508658A GB 903725 A GB903725 A GB 903725A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyanophenthiazine
- reacting
- bromo
- general formula
- prepared
- 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title 1
- -1 alkali metal salt Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 abstract 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 abstract 1
- XBLPHYSLHRGMNW-UHFFFAOYSA-N 4-chloro-3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC=C1Cl XBLPHYSLHRGMNW-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0903725/IV (b)/1> (wherein A is a straight or branched alkylene radical of 2 or 3 carbon atoms, and R1 and R2 are identical or different C1-C3 alkyl radicals or together they form with the adjacent nitrogen atom a saturated heterocyclic ring which is unsubstituted or substituted by a methyl group) and certain acid addition salts thereof, and the preparation thereof by (a) reacting 3-cyanophenthiazine or an alkali metal salt thereof with an aminoalkyl halide Hal-A-NR1R2, or with an alkylene dihalide followed by reaction of the resulting product with an amine HNR1R2, or (b) heating a compound of the general formula <FORM:0903725/IV (b)/2> or a salt thereof, in the presence or absence of a solvent, or (c) cyclizing a compound of the general formula <FORM:0903725/IV (b)/3> by heating in the presence of an alkaline condensation medium, in the presence or absence of a solvent and preferably also in the presence of a hydrogen halide elimination catalyst. The products have analgesic, sympathicolytic, centrally suppressing and antihistaminic properties. 3-Cyanophenthiazine is prepared by reacting 3-chlorophenthiazine with cuprous cyanide. 2 - Bromo - 21 - (311 - dimethylaminopropyl) - amino-41-cyanodiphenyl sulphide is prepared by reacting 2-bromothiophenol with 3-nitro-4-chlorobenzonitrile to form 2-bromo-21-nitro-41-cyanodiphenyl sulphide, reducing this to the corresponding 21-amino-compound and condensing this with 1-dimethylamino-3-chloropropane. 3-Cyano-10-(31-chloropropyl)-phenthiazine is formed as an intermediate by condensing 3-cyanophenthiazine with 1-bromo-3-chloropropane. 3-Cyanophenthiazine-10-carboxlic acid pyrrolidinoethyl ester is prepared by reacting 3-cyanophenthiazine with phosgene and the resulting acid chloride with pyrrolidinoethanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0033288 | 1957-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB903725A true GB903725A (en) | 1962-08-15 |
Family
ID=7219682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35086/58A Expired GB903725A (en) | 1957-11-02 | 1958-10-31 | Phenthiazine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB903725A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2061788A1 (en) * | 2006-09-01 | 2009-05-27 | Immune Control, Inc. | Novel compositions and methods for treatment of diseases related to activated lymphocytes |
-
1958
- 1958-10-31 GB GB35086/58A patent/GB903725A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2061788A1 (en) * | 2006-09-01 | 2009-05-27 | Immune Control, Inc. | Novel compositions and methods for treatment of diseases related to activated lymphocytes |
| EP2061788A4 (en) * | 2006-09-01 | 2010-10-06 | Immune Control Inc | Novel compositions and methods for treatment of diseases related to activated lymphocytes |
| US7923445B2 (en) | 2006-09-01 | 2011-04-12 | Immune Control, Inc. | Methods for treatment of diseases related to activated lymphocytes |
| US7981885B2 (en) | 2006-09-01 | 2011-07-19 | Immune Control Inc. | Compositions for treatment of diseases related to activated lymphocytes |
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