GB915155A - New phenothiazine derivatives and processes for preparing same - Google Patents
New phenothiazine derivatives and processes for preparing sameInfo
- Publication number
- GB915155A GB915155A GB9620/61A GB962061A GB915155A GB 915155 A GB915155 A GB 915155A GB 9620/61 A GB9620/61 A GB 9620/61A GB 962061 A GB962061 A GB 962061A GB 915155 A GB915155 A GB 915155A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- chloride
- reacting
- prepared
- hexamethyleneimine
- 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
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title abstract 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- -1 inorganic acid halides Chemical class 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 150000002990 phenothiazines Chemical class 0.000 abstract 2
- 229940058015 1,3-butylene glycol Drugs 0.000 abstract 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 1
- UDSOIUSFQZZUPF-UHFFFAOYSA-N 3-chlorobutyl acetate Chemical compound CC(Cl)CCOC(C)=O UDSOIUSFQZZUPF-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 229950000688 phenothiazine Drugs 0.000 abstract 1
- JIFBZEZAAPHGBB-UHFFFAOYSA-N phenothiazine-10-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C3=CC=CC=C3SC2=C1 JIFBZEZAAPHGBB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
The invention comprises phenothiazine derivatives of the general formula: <FORM:0915155/IV (b)/1> and acid addition salts thereof, wherein Y represents a hydrogen or a chlorine atom, Z represents a C1-4 alkylene radical and Am represents a hexamethyleneimino radical and the preparation thereof (a) by reacting in the presence of a condensing agent a phenothiazine of the general formula: <FORM:0915155/IV (b)/2> with a reactive ester of an amino alcohol of the general formula: HO-Z-Am (b) by reacting a reactive ester of a compound of the general formula: <FORM:0915155/IV (b)/3> with an amine of the general formula Am-H or (c) by heating a compound of the general formula: <FORM:0915155/IV (b)/4> until 1 mol of carbon dioxide is split off. g -Hexamethyleneimino - n - butyl chloride is obtained from 1,3-butylene glycol by reaction with acetyl chloride to form 3-chloro-n-butyl acetate, reaction of the latter with hexamethyleneimine and conversion of the g -hexamethyleneiminobutanol to the chloride. g - Hexamethyleneimino - b - methylpropyl chloride is obtained by adding hydrogen bromide to b -methallyl chloride and reacting the g -bromo-b -methylpropyl chloride with hexamethyleneimine. g -Hexamethyleneiminopropanol is prepared by reducing of b -hexamethyleneiminopropionic acid ethyl ester with lithium aluminium hydride. Hydrohalic and sulphonic esters of 10-phenothiazinyl-alkanols are prepared by reacting the alkanols with inorganic acid halides, methane sulphonic or aryl sulphonic acid chlorides or by reacting the metal compounds of the 10-unsubstituted phenothiazines with non-geminal dihalo-alkanes. 10-Phenothiazinyl carboxylic acid hexamethyleneiminoalkyl esters are prepared by condensing the 10-phenothiazinyl carboxylic acid halide with HO-Z-Am. Hexamethyleneimine is prepared by reduction of e -caprolactam.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302460 | 1960-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB915155A true GB915155A (en) | 1963-01-09 |
Family
ID=4246914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9620/61A Expired GB915155A (en) | 1960-03-17 | 1961-03-16 | New phenothiazine derivatives and processes for preparing same |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1264M (en) |
| GB (1) | GB915155A (en) |
-
1961
- 1961-03-16 GB GB9620/61A patent/GB915155A/en not_active Expired
- 1961-06-15 FR FR865057A patent/FR1264M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR1264M (en) | 1962-04-24 |
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