GB861779A - Piperazino derivatives and methods for their manufacture - Google Patents
Piperazino derivatives and methods for their manufactureInfo
- Publication number
- GB861779A GB861779A GB29074/57A GB2907457A GB861779A GB 861779 A GB861779 A GB 861779A GB 29074/57 A GB29074/57 A GB 29074/57A GB 2907457 A GB2907457 A GB 2907457A GB 861779 A GB861779 A GB 861779A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- group
- lower alkyl
- alkyl group
- phenthiazine
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/16—[b, f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0861779/IV (b)/1> and their pharmaceutically acceptable acid addition salts (wherein R is a lower alkyl group, R1 is a hydrogen atom or a lower alkyl group, Y is an alkylene group with 2 to 5 carbon atoms, and A is a free, etherified or esterified hydroxy lower alkyl group), and the preparation thereof by reacting a compound of the general formula <FORM:0861779/IV (b)/2> with a compound of the general formula <FORM:0861779/IV (b)/3> preferably in the presence of an acceptor for PQ, and followed, if necessary, by the conversion of A1 into A and Y1 into Y (wherein of P and Q, one is attached directly to the relevant nitrogen atom and the other is connected to the relevant nitrogen atom through a divalent group Y1, A1 being A or a group convertible into A, and Y1 being Y or a group convertible into Y, P and Q being groups of opposite polarity capable of being eliminated as the compound PQ during the course of the reaction). In the examples, A, when representing an etherified or esterified hydroxy lower alkyl group, may be a hydroxyethoxyethyl group, an acetoxyethyl group, an ethoxycarboxyethyl group, a carbamoylethyl or dimethylcarbamoylethyl group. A lower alkyl group contains less than 6 carbon atoms. 10 - (3 - Chloropropyl) - 2 - acetylphenthiazine is made from 2-acetyl-phenthiazine and 1-bromo-3-chloropropane. Similarly made are 10-(4) - chlorobutyl) - 2 - acetyl - phenthiazine and 10-(3-chloropropyl)-2-propionylphenthiazine. 2 - (2 - Acetyl - 10 - phenthiazinyl) - ethyl chloride is made from 2-acetyl-phenthiazine and 2-chloro-ethyl-p-toluenesulphonate. 2 - Acetyl - phenthiazine is reacted with 1, 2 oxidopropane to give 3 - (2 - acetyl - 10 - phenthiazinyl) - propan - 2 - ol, treatment of which with phosphorus tribromide yields the corresponding bromo compound. 2 - Propionyl - phenthiazine is reacted with 3 - bromo - propan - 1 - ol to give 3 - (2 - propionyl - 10 - phenthiazioyl) - propan - 1 - ol, treatment of which with p-toluenesulphonyl chloride yields the corresponding p-toluene-sulphonic acid ester. 10 - Acetyl - phenthiazine is reacted with butyric anhydride to give 2-butyryl-10-acetyl-phenthiazine, hydrolysis of which yields 2-butyrylphenthiazine. 1 - (2 - Hydroxyethyl) - 4 - [3 - (2 - acetyl - 10-phenthiazinyl)propyl]-piperazine is reacted with thionyl chloride to give the corresponding chloro compound or reacted phenyl chlorocarbonate to yield the corresponding phenyl carbonic ester. 1 - (2 - Hydroxyethyl) - 2,5 - dimethylpiperazine is made from 2,5-dimethyl piperazine and ethylene oxide; and 1 - (2 - hydroxyethyl) - 4 - (3-chloropropyl)-piperazine is made from 1-(2-hydroxyethyl)-piperazine and 1-bromo-3-chloropropane.ALSO:Compounds of the general formula <FORM:0861779/VI/1> (wherein R is a lower alkyl group, R1 is a hydrogen atom or a lower alkyl group, Y is an alkylene group with 2 to 5 carbon atoms, and A is a free, etherified or esterified hydroxy lower alkyl group) are preferably compounded in the form of soluble, pharmaceutically acceptable, acid addition salts, e.g. the dihydrochloride, dicitrate, dimaleate or ditartrate. They are preferably administered orally in tablets or elixirs in conjunction with suitable carriers and other types of oral, pharmaceutical dosage units. For parenteral administration, the compounds in the form of non-toxic, acid addition salts are prepared in sterile solutions or suspensions. The compounds may be used, advantageously in conjunction with barbiturates, to reduce anxiety.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS356132X | 1956-08-09 | ||
US861779XA | 1956-09-21 | 1956-09-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB861779A true GB861779A (en) | 1961-02-22 |
Family
ID=25746761
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25135/57A Expired GB866791A (en) | 1956-08-09 | 1957-08-09 | A process for preparing new physiologically effective salts of the aminoalkyl derivatives of homophenothiazine |
GB29074/57A Expired GB861779A (en) | 1956-08-09 | 1957-09-16 | Piperazino derivatives and methods for their manufacture |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25135/57A Expired GB866791A (en) | 1956-08-09 | 1957-08-09 | A process for preparing new physiologically effective salts of the aminoalkyl derivatives of homophenothiazine |
Country Status (4)
Country | Link |
---|---|
CH (2) | CH356133A (en) |
DE (1) | DE1141286B (en) |
FR (1) | FR1187023A (en) |
GB (2) | GB866791A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3188320A (en) * | 1965-06-08 | Peepaeation of io-[j-(n-methylformamido) peopylj-lo.ll-dihydeo |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2694705A (en) * | 1954-11-16 | Nx c c ox a a | ||
GB666457A (en) * | 1948-10-30 | 1952-02-13 | Henri Morren | Carbonyl chlorides and monocarboxyamides of piperazine and process for the preparation thereof |
DE910301C (en) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Process for the production of new phenthiazine derivatives |
CH298685A (en) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Process for the preparation of a novel derivative of phenothiazine. |
DE922467C (en) * | 1951-11-25 | 1955-01-17 | Cassella Farbwerke Mainkur Ag | Process for the preparation of N-derivatives of phenothiazine |
-
1957
- 1957-07-24 CH CH356133D patent/CH356133A/en unknown
- 1957-07-24 CH CH356132D patent/CH356132A/en unknown
- 1957-08-09 FR FR1187023D patent/FR1187023A/en not_active Expired
- 1957-08-09 GB GB25135/57A patent/GB866791A/en not_active Expired
- 1957-09-16 GB GB29074/57A patent/GB861779A/en not_active Expired
- 1957-09-20 DE DESCH22823A patent/DE1141286B/en active Pending
Also Published As
Publication number | Publication date |
---|---|
FR1187023A (en) | 1959-09-04 |
CH356133A (en) | 1961-08-15 |
GB866791A (en) | 1961-05-03 |
DE1141286B (en) | 1962-12-20 |
CH356132A (en) | 1961-08-15 |
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