GB832568A - Heterocyclic compounds and production thereof - Google Patents

Heterocyclic compounds and production thereof

Info

Publication number
GB832568A
GB832568A GB24530/57A GB2453057A GB832568A GB 832568 A GB832568 A GB 832568A GB 24530/57 A GB24530/57 A GB 24530/57A GB 2453057 A GB2453057 A GB 2453057A GB 832568 A GB832568 A GB 832568A
Authority
GB
United Kingdom
Prior art keywords
alkanoyl
dimethylaminoethyl
phenylalkanoyl
propionyl
dimethylaminopropyl
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
GB24530/57A
Inventor
Josef Schmitt
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.)
Clin Byla SA
Original Assignee
Clin Byla 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 Clin Byla SA filed Critical Clin Byla SA
Publication of GB832568A publication Critical patent/GB832568A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises derivatives of pyrrole, benzopyrrole and dibenzopyrrole having an alkanoyl or phenylalkanoyl group attached to a nuclear carbon atom and a dialkylaminoalkyl group attached to the nitrogen atom of the pyrrole ring, and acid addition salts, quaternary ammonium salts and oximes thereof. The preferred products comprise pyrrole and indole derivatives having the alkanoyl or phenylalkanoyl substituent in the 2-position and carbazole derivatives having the alkanoyl or phenylalkanoyl substituent in the 3-position. Suitably the alkanoyl or phenylalkanoyl group is an acetyl, propionyl or phenylacetyl group and the dialkylaminoalkyl group is chosen from dimethylaminoethyl-, diethylaminoethyl-, g -dimethylaminopropyl- and b -dimethylamino-b -methyl-ethyl groups. The compounds are prepared by condensing an alkanoyl- or phenylalkanoyl-substituted pyrrole, benzopyrrole or di - benzopyrrole with a dialkylaminoalkyl halide, such as the chloride, in the presence of an alkaline condensation agent, such as sodamide or an alkali metal or alkali metal hydride, hydroxide or carbonate, in an organic diluent, for example, toluene or dimethyl formamide. The reaction is suitably carried out in an inert atmosphere, for example under nitrogen. The products, which are used therapeutically, may be converted into acid addition or quaternary salts or into the oxime of the carbonyl group by conventional methods. In examples, there are prepared 2-propionyl-1-g -dimethylaminopropylpyrrole; the 1-g -dimethylaminopropyl-, 1-b -dimethylaminoethyl-, 1 - b - methyl - b - dimethylaminoethyl- and 1-b -diethylaminoethyl-, 3-propionyl indoles; the 9-g -dimethylaminopropyl-, 9-b -dimethylaminoethyl- and 9-b -dimethylaminopropyl-, 2-propionyl carbazoles and the 3-acetyl- and 3-phenylacetyl derivatives of 1-b -dimethylaminoethyl-indole; also the acid addition salts, such as acid maleates, the quaternary compounds, such as the methiodides, and the oximes of the above compounds are prepared.
GB24530/57A 1956-08-03 1957-08-02 Heterocyclic compounds and production thereof Expired GB832568A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR832568X 1956-08-03

Publications (1)

Publication Number Publication Date
GB832568A true GB832568A (en) 1960-04-13

Family

ID=9296098

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24530/57A Expired GB832568A (en) 1956-08-03 1957-08-02 Heterocyclic compounds and production thereof

Country Status (1)

Country Link
GB (1) GB832568A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2386541A1 (en) * 2010-05-14 2011-11-16 Affectis Pharmaceuticals AG Novel methods for the preparation of P2X7R antagonists
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 (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2386541A1 (en) * 2010-05-14 2011-11-16 Affectis Pharmaceuticals AG Novel methods for the preparation of P2X7R antagonists
WO2011141194A1 (en) * 2010-05-14 2011-11-17 Affectis Pharmaceuticals Ag Novel methods for the preparation of p2x7r antagonists
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
EP2802320A4 (en) * 2011-11-15 2015-08-12 Yissum Res Dev Co Tricyclic compounds, compositions comprising them and uses thereof
US9447040B2 (en) 2011-11-15 2016-09-20 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Tricyclic compounds, compositions comprising them and uses thereof
AU2012338362B2 (en) * 2011-11-15 2017-05-18 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Tricyclic compounds, compositions comprising them and uses thereof

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