GB905692A - Phenothiazine derivatives, and their preparation - Google Patents
Phenothiazine derivatives, and their preparationInfo
- Publication number
- GB905692A GB905692A GB30544/59A GB3054459A GB905692A GB 905692 A GB905692 A GB 905692A GB 30544/59 A GB30544/59 A GB 30544/59A GB 3054459 A GB3054459 A GB 3054459A GB 905692 A GB905692 A GB 905692A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- reacting
- compound
- low molecular
- action
- 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
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 230000002005 ganglioplegic effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- -1 inorganic acid halides Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0905692/IV (b)/1> (wherein X represents a hydrogen or halogen atom or a low molecular (i.e. C1-4) alkyl or alkoxy group, R1 and R2 represent low molecular alkyl radicals which can be bound to each other directly or through an oxygen atom or the nitrogen atom of a low molecular alkylimino, alkanoyloxyalkylimino or hydroxyalkylimino group, and n is a number from 1 to 3) and the preparation thereof by reacting a compound of the general formula <FORM:0905692/IV (b)/2> with a reactive ester of an aminoalcohol of the general formula <FORM:0905692/IV (b)/3> or by reacting a compound of the general formula <FORM:0905692/IV (b)/4> (wherein Y represents a reactive esterified hydroxy group) with a secondary amine HNR1R2 or by treating a compound of the general formula <FORM:0905692/IV (b)/5> with a low molecular alkylating agent. The products and their acid addition salts have antiallergic and sedative activity, whilst quaternary ammonium salts derived therefrom (e.g. by the action of aliphatic or araliphatic halides or sulphates) have a ganglioplegic action. The bases can also be made by reacting a compound of the second general formula above with phosgene, reacting the resulting 5-chlorocarbonyl compound with an amino-alcohol of the third general formula above, and heating the resulting ester of the general formula <FORM:0905692/IV (b)/6> until carbon dioxide is split off. Reactive esters of the fourth general formula above are prepared by reacting compounds of the second general formula above with haloethoxyethanols or a haloethoxyethoxyethanols and esterifying the resulting hydroxy compounds with strong inorganic or organic acids, e.g. halogen hydracids (by the action of inorganic acid halides), sulphuric acid or organic sulphonic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6379058A CH368178A (en) | 1958-09-10 | 1958-09-10 | Process for the preparation of new basic substituted heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB905692A true GB905692A (en) | 1962-09-12 |
Family
ID=4525221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30544/59A Expired GB905692A (en) | 1958-09-10 | 1959-09-08 | Phenothiazine derivatives, and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH368178A (en) |
| ES (1) | ES251967A1 (en) |
| GB (1) | GB905692A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020658A1 (en) * | 1991-05-17 | 1992-11-26 | Novo Nordisk A/S | Novel heterocyclic carboxylic acids |
| WO2009073154A1 (en) * | 2007-11-28 | 2009-06-11 | Nektar Therapeutics Al, Corporation | Oligomer-tricyclic conjugates |
| WO2011091050A1 (en) * | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
-
1958
- 1958-09-10 CH CH6379058A patent/CH368178A/en unknown
-
1959
- 1959-09-08 GB GB30544/59A patent/GB905692A/en not_active Expired
- 1959-09-09 ES ES0251967A patent/ES251967A1/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020658A1 (en) * | 1991-05-17 | 1992-11-26 | Novo Nordisk A/S | Novel heterocyclic carboxylic acids |
| US5348965A (en) * | 1991-05-17 | 1994-09-20 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids |
| WO2009073154A1 (en) * | 2007-11-28 | 2009-06-11 | Nektar Therapeutics Al, Corporation | Oligomer-tricyclic conjugates |
| JP2011504928A (en) * | 2007-11-28 | 2011-02-17 | ネクター セラピューティックス | Oligomer-tricyclic substance conjugate |
| US8569380B2 (en) | 2007-11-28 | 2013-10-29 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| AU2008331868B2 (en) * | 2007-11-28 | 2015-02-12 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| US9725431B2 (en) | 2007-11-28 | 2017-08-08 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| WO2011091050A1 (en) * | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
Also Published As
| Publication number | Publication date |
|---|---|
| ES251967A1 (en) | 1960-03-16 |
| CH368178A (en) | 1963-03-31 |
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