GB866418A - Phenoxazine derivatives - Google Patents

Phenoxazine derivatives

Info

Publication number
GB866418A
GB866418A GB1938/59A GB193859A GB866418A GB 866418 A GB866418 A GB 866418A GB 1938/59 A GB1938/59 A GB 1938/59A GB 193859 A GB193859 A GB 193859A GB 866418 A GB866418 A GB 866418A
Authority
GB
United Kingdom
Prior art keywords
reacting
general formula
phenoxazine
nrr1
acetyl
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
GB1938/59A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB866418A publication Critical patent/GB866418A/en
Expired legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises: (a) compounds of the general formula: <FORM:0866418/IV (b)/1> (wherein Ac represents an acyl radical, A represents a straight or branched chain alkylene radical of 1-6 carbon atoms, and R and R1 represent straight-chain alkyl radicals which may form, with the nitrogen atom, a 5- or 6-membered heterocyclic ring which may contain an additional nitrogen or oxygen atom and, when a piperazine ring, may be Nsubstituted by an alkyl, cyanoalkyl or hydroxyalkyl radical of 1-6 carbon atoms) and their acid addition salts and quaternary ammonium compounds ; (b) the preparation of the bases of (a) by the following processes: (i) reacting a compound of the general formula: <FORM:0866418/IV (b)/2> with an appropriate alkali metal compound to form its alkali metal derivative and reacting this, without isolation, with a reactive ester of a basic alcohol HO-A-NRR1; (ii) heating an ester of the general formula: <FORM:0866418/IV (b)/3> or an acid addition salt thereof to about 140-222 DEG C.; (c) the combination of process (ii) with the preparation of the esters by reacting a compound of the second general formula above with phosgene and reacting the resulting phenoxazine-10-carbonyl chloride with a basic alcohol HO-A-NRR1; (d) the preparation of 3-acetyl-10-g - (N1-b -hydroxy- and -cyano-ethylpiperazyl-N)-propylphenoxazine by refluxing 3-acetyl-phenoxazine and 1-bromo-3-chloropropane in dioxan in the presence of sodamide to form 3-acetyl-10-(g -chloropropyl)- phenoxazine and boiling this with N-b -hydroxy- or -cyanoethylpiperazine in xylene. In process (i) the basic alcohol ester is preferably a halide Hal-A-NRR1 (wherein Hal represents a chlorine, bromine or iodine atom) in the form of its hydrohalide salt (using an additional molecular proportion of alkaline condensing agent). In either process the carbonyl group may initially be functionally converted and subsequently liberated. The compounds (a) are useful as ganglion-blocking, hypotensive and potentiating agents.
GB1938/59A 1958-01-25 1959-01-19 Phenoxazine derivatives Expired GB866418A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE866418X 1958-01-25

Publications (1)

Publication Number Publication Date
GB866418A true GB866418A (en) 1961-04-26

Family

ID=6802010

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1938/59A Expired GB866418A (en) 1958-01-25 1959-01-19 Phenoxazine derivatives

Country Status (1)

Country Link
GB (1) GB866418A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014533264A (en) * 2011-11-15 2014-12-11 イッサム リサーチ デベロップメント カンパニー オブ ザ ヘブリュー ユニバーシティー オブ エルサレム リミテッド Tricyclic compounds, compositions containing them and their use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014533264A (en) * 2011-11-15 2014-12-11 イッサム リサーチ デベロップメント カンパニー オブ ザ ヘブリュー ユニバーシティー オブ エルサレム リミテッド Tricyclic compounds, compositions containing them and their use

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