GB775279A - New phenothiazine derivatives and process for their manufacture - Google Patents

New phenothiazine derivatives and process for their manufacture

Info

Publication number
GB775279A
GB775279A GB21040/55A GB2104055A GB775279A GB 775279 A GB775279 A GB 775279A GB 21040/55 A GB21040/55 A GB 21040/55A GB 2104055 A GB2104055 A GB 2104055A GB 775279 A GB775279 A GB 775279A
Authority
GB
United Kingdom
Prior art keywords
ethyl
phenothiazine
piperidyl
chloro
methyl
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
Application number
GB21040/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB775279A publication Critical patent/GB775279A/en
Expired legal-status Critical Current

Links

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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0775279/IV(b)/1> wherein R1, R2, R3 and R4 represent hydrogen, methyl, chloro, bromo or methoxy and R5 represents hydrogen, methyl, ethyl, propyl or butyl, and hydrochlorides and tartrates thereof. The bases are obtained by reacting the appropriate phenthiazine with a 2-(N-methyl-piperidyl-21) - 1 - halogen - ethane of the formula: <FORM:0775279/IV(b)/2> wherein X is halogen, suitably in the presence of an alkali metal amide or hydroxide as condensing agent. The products may be purified by fractional distillation or chromatography. In Example (1) phenothiazine and 2-(N-methylpiperidyl - 21) - 1 - chloroethane are reacted in the presence of sodamide to form 1-[21-(N-methyl - piperidyl - 211) - ethyl] - phenothiazine. Similarly obtained are (2) 3-chloro-10-[21-(N-methyl - piperidyl - 211) - ethyl] - phenothiazine; (3) 3 - bromo - 10 - [21 - (N - methyl - piperidyl-211) - ethyl] - phenothiazine; (4) 1 - chloro - 10-[21 - (N - methyl - piperidyl -211) ethyl] - phenothiazine; (8) 3 - chloro - 10 - (21 - (N - ethylpiperidyl -211) - ethyl - 11] - phenothiazine; (9) 3 - bromo - 10 - [21 - (N - ethyl - piperidyl - 211) ethyl - 11) phenothiazine (with sodium hydroxide as condensing agent); (10) 3-chloro-10-[21 - (piperidyl - 211) ethyl - 11] phenothiazine; (11) 3 - bromo - 10 - [21 - (piperidyl - 211) ethyl-11] phenothiazine; (12) 3 - chloro - 10 - [21-(N - n - propyl - piperidyl - 211) ethyl - 11] phenothiazine; (13) 3 - chloro - 10 - [21 - (N-isopropyl - piperidyl - 211) ethyl - 11] phenothiazine; (14) 3 - chloro - 10 - [21 - (N - n-butyl - piperidyl - 211) ethyl - 11] phenothiazine. The products of Examples (1) to (4) and (8) to (11) are converted to hydrochlorides, and those of Examples (12) to (14) to tartrates. In Examples (5) and (6) dichloro-phenothiazines obtained by heatingdi-(m-chlorophenyl) amine with sulphur in the presence of iodine are separated by fractional crystallization from chlorobenzene and fractional distillation into isomers of m.p. 258-260 DEG (substance A), m.p. 142-144 DEG (substance B) and a steroisomer of substance B (which remains in solution). Substance A and B are converted to dichloro-10-[21-(N-methyl - piperidyl - 211 - ethyl] phenothiazines in Examples (5) and (6) by the above general method. In Example (7) a chloro-methoxy-phenthiazine prepared by heating (m-chloro-phenyl) - (m - methoxyphenyl) - amine with sulphur in the presence of iodine, dissolving the product in hot chlorobenzene and allowing it to recrystallize, is heated in the presence of sodamide with 2 - (N - methyl - piperidyl - 21)-1-chloroethane to form a chloro-methoxy-10-[21-(N - methylpiperidyl -211) - ethyl] phenothiazine.
GB21040/55A 1954-07-23 1955-07-20 New phenothiazine derivatives and process for their manufacture Expired GB775279A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH433138X 1954-07-23
CH335670X 1954-11-05

Publications (1)

Publication Number Publication Date
GB775279A true GB775279A (en) 1957-05-22

Family

ID=25736748

Family Applications (2)

Application Number Title Priority Date Filing Date
GB21040/55A Expired GB775279A (en) 1954-07-23 1955-07-20 New phenothiazine derivatives and process for their manufacture
GB31248/55A Expired GB775280A (en) 1954-07-23 1955-11-01 Phenothiazine derivatives and process for their manufacture

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB31248/55A Expired GB775280A (en) 1954-07-23 1955-11-01 Phenothiazine derivatives and process for their manufacture

Country Status (6)

Country Link
BE (2) BE540044A (en)
CH (3) CH334138A (en)
DE (1) DE1008737B (en)
FR (1) FR1161368A (en)
GB (2) GB775279A (en)
NL (2) NL95095C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945031A (en) * 1958-10-13 1960-07-12 Smith Kline French Lab Methylenedioxy substituted phenothiazines
US2945855A (en) * 1958-10-21 1960-07-19 Mead Johnson & Co 10-(1-substituted-3-pyrrolidylmethyl) phenothiazines
US9198916B1 (en) * 2014-05-27 2015-12-01 B&G Partners, Llc Compounds and methods for treating tumors

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE569809A (en) * 1957-07-31
BE569606A (en) * 1957-07-31
DE1181223B (en) * 1962-07-14 1964-11-12 Dresden Arzneimittel Process for the industrial production of phenthiazine bases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE833650C (en) * 1947-03-14 1952-03-10 Rhone Poulenc Sa Process for the preparation of derivatives of phenthiazine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945031A (en) * 1958-10-13 1960-07-12 Smith Kline French Lab Methylenedioxy substituted phenothiazines
US2945855A (en) * 1958-10-21 1960-07-19 Mead Johnson & Co 10-(1-substituted-3-pyrrolidylmethyl) phenothiazines
US9198916B1 (en) * 2014-05-27 2015-12-01 B&G Partners, Llc Compounds and methods for treating tumors

Also Published As

Publication number Publication date
CH335670A (en) 1959-01-31
GB775280A (en) 1957-05-22
BE540044A (en)
DE1008737B (en) 1957-05-23
CH344725A (en) 1960-02-29
CH334138A (en) 1958-11-15
FR1161368A (en) 1958-08-28
BE542588A (en)
NL95095C (en)
NL95120C (en)

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