GB813428A - New pyrrolidine compounds and the production thereof - Google Patents
New pyrrolidine compounds and the production thereofInfo
- Publication number
- GB813428A GB813428A GB30921/56A GB3092156A GB813428A GB 813428 A GB813428 A GB 813428A GB 30921/56 A GB30921/56 A GB 30921/56A GB 3092156 A GB3092156 A GB 3092156A GB 813428 A GB813428 A GB 813428A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- phenthiazine
- alkyl
- propyl
- ethyl
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises phenthiazines of the general formula: <FORM:0813428/IV (b)/1> and their acid addition and quaternary salts (X represents a hydrogen or chlorine atom, R represents a hydrogen atom or an alkyl, alkenyl or benzyl radical) and a process for their preparation by reacting phenthiazine or 2-chloro-phenthiazine with a reactive ester of 3-pyrrolidylmethanol (or an N-alkyl, alkenyl or benzyl derivative thereof), and if desired N-alkylating, alkenylating or benzylating the product and/or forming acid addition or quaternary salts, e.g. with hydrochloric, sulphuric, phosphoric, methane sulphonic, fumaric, maleic or citric acids, or with alkyl halogenides, sulphates or sulphonic acid alkyl esters, respectively. Specified reactive esters are those with hydrogen halides and with alkyl and aryl sulphonic acids, and the reaction is preferably performed in a solvent such as benzene, toluene or cumene in the presence of an alkali metalamide, hydride or hydroxide. Specified groups denoted by R include benzyl, methyl, ethyl, propyl, butyl, amyl, hexyl, vinyl, allyl, propenyl, crotyl and butenyl. In examples: (1) phenthiazine is reacted with sodamide in xylene and then boiled with 3-bromomethyl-1-ethyl pyrrolidine hydrobromide giving 10-[11-ethylpyrrolidyl - (31) - methyl] - phenthiazine, characterized as its hydrochloride and methosulphate; (2) as in (1), but using 3-chloromethyl-1-n-propyl pyrrolidine to give 10-[1-n-propylpyrrolidyl - (31) - methyl] - phenthiazine, its hydrochloride and methosulphate; (3), similarly are prepared the following 10-substituted phenthiazines: 1-methylpyrrolidyl-3-methyl -, 1 - isopropylpyrrolidyl - 3 - methyl -, 1 - allylpyrrolidyl - 3 - methyl -, 1 - n - butylpyrrolidyl - 3 - methyl -, and 1 - benzylpyrrolidyl-3-methyl- (as its HCl salt); (4) similarly from 2-chlorophenthiazine are prepared 10 - [pyrrolidyl - (31) - methyl] - 2 - chlorophenthiazines which are substituted on the pyrrolidyl N-atom by methyl, ethyl, n-propyl, isopropyl and n-butyl groups, together with corresponding HCl salts. Specification 772,179 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH813428X | 1955-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB813428A true GB813428A (en) | 1959-05-13 |
Family
ID=4538723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30921/56A Expired GB813428A (en) | 1955-10-10 | 1956-10-10 | New pyrrolidine compounds and the production thereof |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH334150A (en) |
| DE (1) | DE1049382B (en) |
| GB (1) | GB813428A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3140284A (en) * | 1960-02-05 | 1964-07-07 | Cilag Chemie | New phenothiazine derivatives and a process for the production thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1168913B (en) * | 1962-02-01 | 1964-04-30 | Cilag Chemie | Process for the preparation of new 10- [pyrrolidyl- (3 ') -methyl] -phenthiazines |
| US3435114A (en) * | 1965-11-08 | 1969-03-25 | Mead Johnson & Co | Topical antihistaminic compositions containing methdilazine sulfoxide |
-
0
- DE DENDAT1049382D patent/DE1049382B/en active Pending
-
1955
- 1955-10-10 CH CH334150D patent/CH334150A/en unknown
-
1956
- 1956-10-10 GB GB30921/56A patent/GB813428A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3140284A (en) * | 1960-02-05 | 1964-07-07 | Cilag Chemie | New phenothiazine derivatives and a process for the production thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1049382B (en) | 1959-01-29 |
| CH334150A (en) | 1958-11-15 |
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