GB811959A - New phenthiazine derivatives and their preparation - Google Patents

New phenthiazine derivatives and their preparation

Info

Publication number
GB811959A
GB811959A GB9885/57A GB988557A GB811959A GB 811959 A GB811959 A GB 811959A GB 9885/57 A GB9885/57 A GB 9885/57A GB 988557 A GB988557 A GB 988557A GB 811959 A GB811959 A GB 811959A
Authority
GB
United Kingdom
Prior art keywords
phenothiazine
methanesulphonyl
methanesulphonylphenothiazine
dimethylamino
prepared
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
GB9885/57A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB811959A publication Critical patent/GB811959A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D279/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/101,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/141,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18[b, e]-condensed with two six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

The invention comprises phenothiazine derivatives of the general formula (I) <FORM:0811959/IV (b)/1> and their acid addition and quaternary ammonium salts (wherein X is a sulphur atom or SO group, R1 and R2 are each an alkyl group containing not more than five carbon atoms or one of R1 and R2 is hydrogen and the other is an alkyl group as above, or R1 and R2 together with the adjacent nitrogen atom form a heterocyclic group, e.g. pyrrolidino, piperidino, morpholino, piperazino, or 4-alkyl-, 4-hydroxyalkyl- or 4-acyloxyalkylpiperazino, and B is a straight or branched divalent aliphatic hydrocarbon group containing two to five carbon atoms, unsubstituted or substituted by <FORM:0811959/IV (b)/2> wherein A is a single bond or methylene group) and their preparation by known methods for the preparation of 10-aminoalkylphenothiazines. For therapeutic purposes the bases of general formula (I) are preferably converted into acid addition salts and quaternary ammonium derivatives with, respectively, acids and halides having pharmaceutically acceptable anions, examples of which are supplied. Examples describe the preparation of 3-methanesulphonyl - 10 - (3 - dimethylaminopropyl)-, (3-dimethylamino - 2 - methylpropyl) -, (3 - pyrrolidino - 2 - methylpropyl) -, (3 - 41 - methyl-11 - piperazinyl - 2 - methylpropyl) -, (3 - 41-methyl - 11 - piperazinylpropyl) - and (3 - pyrrolidinopropyl)-phenothiazine from 3-methanesulphonylphenothiazine and the appropriate tertiary - aminoalkyl halides; 3 - methanesulphonyl - 10 - (2 - dimethylaminopropyl) and (2:3 - bis - dimethylaminopropyl) - phenothiazine by thermal decarboxylation of 3-dimethylamino-2-propyl and 1:3-bis-dimethylamino - 2 - propyl - 3 - methanesulphonylphenothiazine - 10 - carboxylate respectively; 3-methanesulphonyl - 10 - (3 - piperidinopropyl), (3 - diethylaminopropyl) -, (3 - 41 - hydroxyethyl - 11 - piperazinylpropyl) - and (3 - methylaminopropyl) - phenothiazine by reacting 3-methanesulphonyl - 10 - (3 - toluene - p - sulphonyloxypropyl) - phenothiazine with the appropriate amine; 3 - methanesulphonyl - 10-(3 - 41 - acetoxyethyl - 11 - piperazinylpropyl)-phenothiazine by acetylating the corresponding hydroxy compound; 3-methanesulphonyl-10-(3 - dimethylaminopropyl) - phenothiazine by reductive methylation of the corresponding primary amine; 3-methanesulphonyl-10-(3-dimethylaminopropyl) phenothiazine by the cyclisation of 2-bromo-21-(3-dimethylaminopropylamino) - 41 - methanesulphonyldiphenyl sulphide, and 3 - methanesulphonyl - 9 - oxy - 10-(3 - dimethylamino - 2 - methylpropyl) - phenothiazine by the oxidation of the corresponding phenothiazine. Hydrochlorides, fumarates, oxalates, methanesulphonates, maleates and picrates of some of these compounds are also described. 3 - Methanesulphonylphenothiazine is obtained (with the 1-isomer) by the action of sulphur in the presence of iodine on 3-methanesulphonyldiphenylamine, prepared by decarboxylating 2 - carboxy - 31 - methanesulphonyldiphenylamine. 3 - Dimethylamino - 2 - propyl 3 - methanesulphonylphenothiazine - 10 - carboxylate (and its hydrochloride) are prepared from 1-dimethylaminopropan - 2 - ol and 3 - methanesulphonylphenothiazine - 10 - carbonyl chloride, obtained in turn by the action of phosgene on 3-methanesulphonylphenothiazine; 1:3 - bis - dimethylamino - 2 - propyl 3 - methanesulphonylphenothiazine - 10 - carboxylate is prepared similarly from 1:3-bis-dimethylaminopropan-2-ol. 3 - Methanesulphonyl - 10 - (3 - toluene - p-sulphonyloxypropyl) pehnothiazine is prepared by condensing p - toluenesulphonyl chloride with 3 - methanesulphonyl - 10 - (3 - hydroxypropyl) phenothiazine, prepared by acid hydrolysis of 3 - methanesulphonyl - 10 - (3-tetrahydropyranyloxy) phenothiazine obtained in turn by condensing 3-tetrahydropyranyloxy-1-chloropropane with 3-methanesulphonylphenothiazine. 3 - Methanesulphonyl - 10 - (3 - aminopropyl)-phenothiazine is prepared by treating 3-methanesulphonyl - 10 - (3 - toluene - p - sulphonyloxypropyl) phenothiazine with ammonia. 2 - Bromo - 21 - (3 - dimethylaminopropylamino) - 41 - methanesulphonyldiphenyl sulphide is obtained by condensing 1-dimethylamino - 3 - chloropropane with 2 - bromo - 21-amino - 41 - methanesulphonyldiphenyl sulphide.
GB9885/57A 1956-04-07 1957-03-26 New phenthiazine derivatives and their preparation Expired GB811959A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR811959X 1956-04-07

Publications (1)

Publication Number Publication Date
GB811959A true GB811959A (en) 1959-04-15

Family

ID=9263160

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9885/57A Expired GB811959A (en) 1956-04-07 1957-03-26 New phenthiazine derivatives and their preparation

Country Status (3)

Country Link
DE (1) DE1094751B (en)
GB (1) GB811959A (en)
NL (1) NL97976C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105837528A (en) * 2016-05-30 2016-08-10 大连理工大学 Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine
CN110615742A (en) * 2019-09-20 2019-12-27 广东省禾基生物科技有限公司 Magnolol derivative and preparation method and application thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL120362C (en) * 1961-04-26
NL278471A (en) * 1961-05-15
BE635096A (en) * 1962-07-19

Family Cites Families (3)

* 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
BE528164A (en) * 1953-04-10
DE939630C (en) * 1953-10-25 1956-03-01 Basf Ag Process for the preparation of heterocyclic compounds with a ring-shaped imino group substituted by basic groups

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105837528A (en) * 2016-05-30 2016-08-10 大连理工大学 Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine
CN110615742A (en) * 2019-09-20 2019-12-27 广东省禾基生物科技有限公司 Magnolol derivative and preparation method and application thereof

Also Published As

Publication number Publication date
DE1094751B (en) 1960-12-15
NL97976C (en)

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