GB929228A - Quinoxalino-[2, 3-b]-ú-benzothiazine derivatives and their preparation - Google Patents
Quinoxalino-[2, 3-b]-ú-benzothiazine derivatives and their preparationInfo
- Publication number
- GB929228A GB929228A GB183260A GB183260A GB929228A GB 929228 A GB929228 A GB 929228A GB 183260 A GB183260 A GB 183260A GB 183260 A GB183260 A GB 183260A GB 929228 A GB929228 A GB 929228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- acid
- quinoxalino
- prepared
- reacting
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 abstract 2
- -1 N-substituted o-aminothiophenol Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002908 adrenolytic effect Effects 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0929228/IV(a)/1> or <FORM:0929228/IV(a)/2> (wherein Y represents a hydrogen or halogen atom, Z represents an alkylene radical having 2-6 carbon atoms of which 2-4 are in the direct chain between N and Am, and Am represents a C2-8 dialkylamino group wherein the two alkyl radicals can be bound to each other direct or through an oxygen atom) and their acid addition salts, and the preparation thereof (a) by reacting, in the presence of a basic condensing agent, an 11H-quinoxalino [2.3-b]-p-benzothiazine of the general formula <FORM:0929228/IV(a)/3> with a reactive ester of an aminoalcohol HO-Z-Am, and, if desired, converting the product into an addition salt with an inorganic or organic acid, or (b) reacting a reactive ester of a compound of the general formula <FORM:0929228/IV(a)/4> or <FORM:0929228/IV(a)/5> with a secondary amine Am-H, or (c) condensing an N-substituted o-aminothiophenol of the general formula <FORM:0929228/IV(a)/6> with 2,3-dichloroquinoxaline in the presence of an acid-binding agent. The products have anti-allergic, serotonin-antagonistic, anti-convulsive, adrenolytic, sedative and anaesthetic-potentiating activity. Halogen substituted 11H-quinoxalino [2,3-b]-p-benzothiazines (of the formula given in (a) above, Y representing a halogen atom, e.g. chlorine in the 3-position) are prepared by condensing a halogen substituted 2-aminothiophenol with 2,3-dichloroquinoxaline. Reactive esters used as starting materials in process (b) are prepared by reacting alkali metal compounds of 11H-quinoxalino [2,3-b]-p-benzothiazines of the general formula given in (a) above with alkylene oxides and reacting the resulting hydroxyalkyl derivatives with inorganic acid halides, methanesulphonic acid chloride or arylsulphonic acid chlorides. N-(g - Dimethylaminopropyl)- o-aminothiophenol is prepared by refluxing 3-dimethylaminopropylbenzothiazolone-2 with ethanolic caustic potash. 3- Dimethylaminopropylbenzothiazolone-2 is prepared by refluxing benzothiazolone-2 with dimethyaminopropyl chloride and sodamide in benzene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6855659A CH370091A (en) | 1959-01-21 | 1959-01-21 | Process for the preparation of new heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB929228A true GB929228A (en) | 1963-06-19 |
Family
ID=4528830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB183260A Expired GB929228A (en) | 1959-01-21 | 1960-01-19 | Quinoxalino-[2, 3-b]-ú-benzothiazine derivatives and their preparation |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH370091A (en) |
| GB (1) | GB929228A (en) |
-
1959
- 1959-01-21 CH CH6855659A patent/CH370091A/en unknown
-
1960
- 1960-01-19 GB GB183260A patent/GB929228A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH370091A (en) | 1963-06-30 |
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