GB831091A - Improvements in the production of derivatives of phenothiazine-10-carboxylic acid esters and their decarboxylation products and esters of 3-halogen-phenothiazine-n-carboxylic acids with amino alcohols - Google Patents
Improvements in the production of derivatives of phenothiazine-10-carboxylic acid esters and their decarboxylation products and esters of 3-halogen-phenothiazine-n-carboxylic acids with amino alcoholsInfo
- Publication number
- GB831091A GB831091A GB3084156A GB3084156A GB831091A GB 831091 A GB831091 A GB 831091A GB 3084156 A GB3084156 A GB 3084156A GB 3084156 A GB3084156 A GB 3084156A GB 831091 A GB831091 A GB 831091A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenothiazine
- ethanol
- esters
- methyl
- group
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
The invention comprises esters of the formula <FORM:0831091/IV (b)/1> (wherein R1 is an alkylene chain of 2 to 4 carbon atoms which may bear an alkyl group or a chlorine atom to form a side group, R2 and R3 are alkyl groups having 1 to 8 carbon atoms or cycloalkyl groups having 5 to 8 ring atoms, or two of the substituents R1, R2 and R3 may be joined to form an alkylene chain thus forming together with the nitrogen atom a saturated heterocyclic ring of 5 to 7 ring atoms which may have nitrogen or oxygen as additional hetero atoms and to which the COO-group is directly connected when R1 forms part of the ring) and hydrochlorides thereof; and the preparation of these compounds and of compounds of the above general formula wherein the substituent in the 3-position may be any halogen atom, the phenothiazine nucleus may be further substituted, e.g. by alkyl or alkoxy groups or halogen atoms, no limitation is placed on the number of carbon atoms in R2 and R3 and the heterocyclic tertiary amino group may bear further substituents, by esterifying the appropriate phenothiazine-10-carboxylic acid chloride with the appropriate tertiary amino alcohol. This process may be combined with the additional step of heating the so-formed esters to a temperature between about 150 DEG and about 220 DEG C. until no more carbon dioxide is split off to form 3-halogeno-phenothiazines bearing an -R1NR2R3 group in the 10-position, isolated as free bases or as their hydrochlorides. This process may also occur during the esterification reaction or during distillation of the ester, if these are carried out at sufficiently high temperatures. The invention also particularly comprises esters of the formula <FORM:0831091/IV (b)/2> (wherein Z is an aliphatic hydrocarbon radical of 1 to 8 carbon atoms) and hydrochlorides thereof. Suitable tertiary amino alcohols for use in the above process include N : N-diethylamino - ethanol, N : N - dimethylamino - ethanol, 1 - (N : N - dimethylamino) - propanol(3), 2-pyrrolidino-, 2-piperidino-, 2-morpholinoand 2-hexamethyleneimino-ethanol, 3-dimethylamino - 2 - chloro - propanol - (1), 2 - methylamino - propanol - (1) or - butanol - (1), N - cyclohexyl - N - methyl - amino - ethanol, N : N - dicyclohexylamino - ethanol, 3 - (N - iso - butyl - N - methyl - amino) - butanol - (1), N - hydroxyethyl - piperazine, N - methyl - N1-hydroxyethyl - piperazine, N : N1 - bis - (hydroxyethyl)-piperazine and N-methyl or N-ethyl - 3 - hydroxy - pyrrolidine or - piperidine. An hydrogen chloride binding agent, such as a molar excess of the amino alcohol or a base such as pyridine, quinoline or dimethylaniline, or sodium acetate or an alkali or alkaline earth metal hydroxide or carbonate or magnesium oxide, may be used in the esterification process, but such agent may be omitted, in which case a hydrochloride of the ester is formed. The splitting off of carbon dioxide is facilitated by catalysts such as copper powder, and this process may be conducted at reduced pressure. Examples are given. 3-Halogeno-phenothiazine 10-carboxylic acid chlorides are prepared by reacting the 3-halogeno-phenothiazine with phosgene, preferably at elevated temperature and pressure.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB37494A DE1011887B (en) | 1955-10-12 | 1955-10-12 | Process for the preparation of phenthiazine cartridges with basic substitution in the 10-position |
Publications (1)
Publication Number | Publication Date |
---|---|
GB831091A true GB831091A (en) | 1960-03-23 |
Family
ID=6965213
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3084156A Expired GB831091A (en) | 1955-10-12 | 1956-10-10 | Improvements in the production of derivatives of phenothiazine-10-carboxylic acid esters and their decarboxylation products and esters of 3-halogen-phenothiazine-n-carboxylic acids with amino alcohols |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH342956A (en) |
DE (1) | DE1011887B (en) |
GB (1) | GB831091A (en) |
LU (1) | LU34349A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3239517A (en) * | 1964-10-12 | 1966-03-08 | Toldy Lajos | Phenothiazines having antihypertensive effect |
US3254079A (en) * | 1963-01-17 | 1966-05-31 | Schering Corp | Amino alcohol ethers of phenothiazines |
US9409119B2 (en) | 2010-12-22 | 2016-08-09 | Kabushiki Kaisha Toshiba | Acid gas absorbent, acid gas removal method, and acid gas removal device |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1137734B (en) * | 1958-09-03 | 1962-10-11 | Spofa Vereinigte Pharma Werke | Process for the preparation of basic 1,3-dihalophen-thiazine derivatives |
-
0
- LU LU34349D patent/LU34349A1/xx unknown
-
1955
- 1955-10-12 DE DEB37494A patent/DE1011887B/en active Pending
-
1956
- 1956-04-13 CH CH342956D patent/CH342956A/en unknown
- 1956-10-10 GB GB3084156A patent/GB831091A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3254079A (en) * | 1963-01-17 | 1966-05-31 | Schering Corp | Amino alcohol ethers of phenothiazines |
US3239517A (en) * | 1964-10-12 | 1966-03-08 | Toldy Lajos | Phenothiazines having antihypertensive effect |
US9409119B2 (en) | 2010-12-22 | 2016-08-09 | Kabushiki Kaisha Toshiba | Acid gas absorbent, acid gas removal method, and acid gas removal device |
EP2468385B1 (en) * | 2010-12-22 | 2016-11-02 | Kabushiki Kaisha Toshiba | Acid gas absorbent, acid gas removal method and acid gas removal device |
Also Published As
Publication number | Publication date |
---|---|
CH342956A (en) | 1959-12-15 |
LU34349A1 (en) | |
DE1011887B (en) | 1957-07-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB831091A (en) | Improvements in the production of derivatives of phenothiazine-10-carboxylic acid esters and their decarboxylation products and esters of 3-halogen-phenothiazine-n-carboxylic acids with amino alcohols | |
ES417890A1 (en) | Penicillanic acid derivatives | |
GB1155017A (en) | Hydrazine Compounds and process for their manufacture | |
US3067237A (en) | Lower-alkyl mono-or bis-(alkanesulfonamido) benzoate esters | |
GB1480593A (en) | Xanthene and thioxanthene derivatives having pharmaceutical activity | |
GB815279A (en) | Novel benzomorpholone derivatives and a process for the manufacture thereof | |
US2863873A (en) | Esters of nicotinic acid | |
GB904242A (en) | Homopiperazino derivatives and a process for their production | |
GB813218A (en) | Nor-tropines and nor-pseudo-tropines and process for their production | |
US3081229A (en) | Phenothiazines with antihistaminic and antipsychotic activity | |
GB770498A (en) | -a-acylamino--ß-amino-propio-nitrophenones and derivatives and process for their preparation | |
GB962797A (en) | Steroid-21-amino-acid esters and process for their manufacture | |
GB1123466A (en) | Process for the production of cyanamide dicarboxylic acid esters | |
GB1060834A (en) | A method for the preparation of 5-hydroxy-5-amino-alkyl-10,11-dihydro-5h-dibenzo-[a,d]cycloheptadienes and novel compounds preparable according to the method | |
GB950321A (en) | Derivatives of iodophenyl-propionic acids and improvements in and relating to x-ray contrast media | |
GB1076202A (en) | Cyclohepta[b]-pyrrole derivatives | |
US3538223A (en) | Beta-(3-indolylmethyl)-butyric acid lactone compositions | |
GB833474A (en) | Piperazine derivatives | |
GB834300A (en) | Improvements in and relating to quinoline derivatives and the manufacture thereof | |
US3287454A (en) | 1-substituted 4-isonicotinoylamino-piperazines | |
ES433593A1 (en) | Antibacterial cyanoquinoxaline 1,4-dioxides | |
GB720649A (en) | Method of preparing substituted oxazol-5-one compounds | |
GB763406A (en) | Novel 6-aminomethyl-5-hydroxy-indane derivatives and a process for the manufacture thereof | |
ES412484A1 (en) | Procedure for the preparation of carbostirilic derivatives. (Machine-translation by Google Translate, not legally binding) | |
GR16973B (en) | METHOD OF MANUFACTURING PRODUCERS OF 1, 3 - DYALKYLOXANTHINS. |