GB857546A - Trifluoromethyl-phenothiazine derivatives - Google Patents

Trifluoromethyl-phenothiazine derivatives

Info

Publication number
GB857546A
GB857546A GB37978/56A GB3797856A GB857546A GB 857546 A GB857546 A GB 857546A GB 37978/56 A GB37978/56 A GB 37978/56A GB 3797856 A GB3797856 A GB 3797856A GB 857546 A GB857546 A GB 857546A
Authority
GB
United Kingdom
Prior art keywords
phenthiazine
reacting
appropriate
compounds
compound
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
GB37978/56A
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.)
Olin Corp
Original Assignee
Olin Corp
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 Olin Corp filed Critical Olin Corp
Publication of GB857546A publication Critical patent/GB857546A/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
    • 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
    • C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
    • 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
    • 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
    • C07D279/28—[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 with other substituents attached to the ring system

Abstract

The invention comprises compounds of the general formula: <FORM:0857546/IV(b)/1> and the acid addition salts thereof wherein A is a C1-8 alkylene radical B is a basic nitrogen containing radical with fewer than twelve carbon atoms, R is a hydrogen atom, a C1-8 alkyl group or tri-fluoro methyl and n is zero, one or two, excepting those compounds claimed in Specification 857,547 and the preparation thereof (wherein the trifluoromethyl group is in one of the position two or four) by reacting an appropriate phenthiazine unsubstituted in the 10-position with halide, B-A-X wherein X is a halogen atom; (wherein n is zero or two) by reacting a B-substituted C1-8 alkanoyl halide with an appropriate phenthiazine and reducing the resulting carbonyl compound, or reacting the said phenthiazine with a halo-(C1-8-alkanoyl)-halide, treating the product with a compound of the formula BH; (wherein B is an -NH2 group and n is zero or two) by reacting an appropriate phenthiazine with a nitrile of the formula R1-CH=CR1CN in which R1 is hydrogen or a lower alkyl group and the resulting 10-propionitrile compound is reduced; a process for the separation of compounds of the general formula: <FORM:0857546/IV(b)/2> in which A, B and R have the meaning above by reacting an appropriate phenthiazine with one mole of an oxidising agent, also for the preparation of compounds of the general formula: <FORM:0857546/IV(b)/3> by reacting an appropriate phenthiazine with two moles of an oxidising agent per mole of the phenthiazine, and the preparation of the acid addition salts of the compounds of the invention by reacting the free base with approximately an equivalent of the acid HX. 10-(41-dimethylamino butyl)-2-trifluoromethyl-phenthiazine hydrochloride is also prepared by reacting 2-trifluoromethyl phenthiazine with 2-tetrahydropyranyl-4-chlorobutyl ether hydrolysing the product to the 4-hydroxy butyl compound converting this to the corresponding chloro compound with thionyl chloride and finally reacting this with dimethylamine and forming the hydrochloride salt.
GB37978/56A 1955-12-23 1956-12-12 Trifluoromethyl-phenothiazine derivatives Expired GB857546A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US857546XA 1955-12-23 1955-12-23

Publications (1)

Publication Number Publication Date
GB857546A true GB857546A (en) 1960-12-29

Family

ID=22193722

Family Applications (2)

Application Number Title Priority Date Filing Date
GB37978/56A Expired GB857546A (en) 1955-12-23 1956-12-12 Trifluoromethyl-phenothiazine derivatives
GB31044/60A Expired GB857547A (en) 1955-12-23 1956-12-12 Trifluoromethyl-phenothiazine derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB31044/60A Expired GB857547A (en) 1955-12-23 1956-12-12 Trifluoromethyl-phenothiazine derivatives

Country Status (5)

Country Link
CY (1) CY280A (en)
DE (1) DE1095836B (en)
FR (1) FR1209854A (en)
GB (2) GB857546A (en)
NL (1) NL106170C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017222466A1 (en) * 2016-06-23 2017-12-28 Bioimics Ab Anti-infective heterocyclic compounds and uses thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL108827C (en) * 1956-04-09
GB1517385A (en) * 1975-08-29 1978-07-12 Eisai Co Ltd Phenothiazine derivatives
US8637503B2 (en) 2003-05-16 2014-01-28 Board Of Regents, The University Of Texas System Phenothiazine enantiomers as agents for the prevention of bone loss
CA2662215A1 (en) 2006-09-01 2008-03-06 Immune Control, Inc. Novel compositions and methods for treatment of diseases related to activated lymphocytes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE910301C (en) * 1950-12-21 1954-04-29 Rhone Poulenc Sa Process for the production of new phenthiazine derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017222466A1 (en) * 2016-06-23 2017-12-28 Bioimics Ab Anti-infective heterocyclic compounds and uses thereof
CN109641889A (en) * 2016-06-23 2019-04-16 百欧伊米克思有限公司 Anti-infective heterocyclic compound and application thereof
JP2019518771A (en) * 2016-06-23 2019-07-04 バイオイミクス・アクチボラグ Anti-infective heterocyclic compound and use thereof
US11130741B2 (en) 2016-06-23 2021-09-28 Bioimics Ab Anti-infective heterocyclic compounds and uses thereof

Also Published As

Publication number Publication date
FR1209854A (en) 1960-03-04
DE1095836B (en) 1960-12-29
NL106170C (en)
GB857547A (en) 1960-12-29
CY280A (en) 1964-03-18

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