GB725745A - Pyrrolinoquinolines and processes for making same - Google Patents

Pyrrolinoquinolines and processes for making same

Info

Publication number
GB725745A
GB725745A GB14698/53A GB1469853A GB725745A GB 725745 A GB725745 A GB 725745A GB 14698/53 A GB14698/53 A GB 14698/53A GB 1469853 A GB1469853 A GB 1469853A GB 725745 A GB725745 A GB 725745A
Authority
GB
United Kingdom
Prior art keywords
methyl
methoxy
dimethyl
diethylaminoethyl
hydroxy
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
GB14698/53A
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 GB725745A publication Critical patent/GB725745A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems

Landscapes

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

Abstract

The invention comprises pyrrolinoquinolines of general formula <FORM:0725745/IV (b)/1> wherein R is hydrogen, alkyl, dialkylaminoalkyl or aralkyl, R1 is hydrogen, alkyl, carboxy, or N-alkylcarbamyl, and R2 is one or two substituents which are hydrogen, hydroxy, alkoxy, N-alkylcarbamyl or halogen, while the two vicinal carbon atoms 8 and 9 may be part of a further heterocyclic ring. The compounds are prepared by reacting a 3-b -haloethyl-4-haloquinoline at an elevated temperature and in a suitable solvent medium such as an alcohol or phenol with ammonia or a primary amine (e.g. an alkylamine, aralkylamine, hydroxyalkylamine or aminoalkylamine). Using ammonia as a primary reactant compounds unsubstituted at the pyrrolino nitrogen atom are formed and these can be converted into N-metal compounds by treatment with metals such as sodium, potassium and lithium, or with Grignard compounds, and the products can then be further reacted with reactive esters (e.g. aliphatic or araliphatic halides or hydroxy- or amino-substituted aliphatic alcohols) to yield compounds substituted at the pyrrolino nitrogen atom. The examples describe the preparation of 4-methyl-, 1-methyl-, 4-methyl-6-methoxy-, 1-methyl-4-N-methylcarbamyl-, 1-methyl-4-carboxy-, 6-methoxy-, 1-benzyl-4-methyl-6-ethoxy-, 1,4-dimethyl-, 1,4-dimethyl-6-methoxy-, 1,4 - dimethyl - 6 - ethoxy -, 1,4 - dimethyl - 7 - hydroxy-, 1,4-dimethyl-7-methoxy-, 1,4-dimethyl - 8 - hydroxy -, 1,4 - dimethyl - 8 - methoxy -, 1,4 - dimethyl - 8 - ethoxy -, 1,4 - dimethyl - 8 - N - methylcarbamyl -, 1 - b - dimethylaminoethyl - 4 - methyl - 6 - methoxy -, 1 - b - diethylaminoethyl - 4 - methyl -, 1 - b - diethylaminoethyl - 4 - methyl - 6 - hydroxy -, 1 - b - diethylaminoethyl - 4 - methyl - 6 - methoxy -, 1 - b - diethylaminoethyl - 4 - methyl - 6 - methoxy - 9 - chloro -, 1 - b - diethylaminoethyl - 4 - methyl - 7,8 - dimethoxy -, 1 - b - diethylaminoethyl - 4 - methyl - 8 - chloro -, 1 - b - diethylaminoethyl - 4 - methyl - 8 - methoxy-, 1 - b - diethylaminoethyl - 4 - methyl - 7 - hydroxy-, 1-b -diethylaminoethyl-4-methyl-7-methoxy -, benzofurano - [9,8 - b] - 1,4 - dimethyl - 6 - methoxy -, benzopyrrolo - [9,8 - b] - 1 - b - diethylaminoethyl - 4 - methyl -, and benzopyrrolo - [8,9 - b] - 1,4 - dimethyl - 2,3 - dihydropyrroloquinoline. Salts of these compounds with maleic, hydrochloric, hydrobromic and naphthalene-1,5-disulphonic acid are also described. 2 - Carbethoxy - 3 - b - chloroethyl - 4 - chloroquinoline is prepared by treating with phosphorus oxychloride, the aniline-lactone-ester condensation product formed by saturating a suspension of the sodium salt of g -butyrolactone-a -ethyloxalate in a mixture of chloroform and aniline with gaseous hydrogen chloride. Benzopyrrolo - [5,6 - b] - 2 - methyl - 3 - b - chloroethyl - 4 - chloro -, benzopyrrolo - [6,5 - b] - 2 - methyl - 3 - b - chloroethyl - 4 - chloro -, and benzofurano - [5,6 - b] - 2 - methyl - 3 - b - chloroethyl - 4 - chloro - 8 - methoxy - quinoline are prepared by condensing a -aceto-g -butyrolactone with 2-aminocarbazole, 3-aminocarbazole and 2-amino-3-methoxy-diphenylene oxide respectively under conditions usual for formation of Schiff's bases and cyclizing the resulting products with phosphorus oxychloride. Specification 703,277 is referred to.
GB14698/53A 1952-05-26 1953-05-26 Pyrrolinoquinolines and processes for making same Expired GB725745A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE725745X 1952-05-26

Publications (1)

Publication Number Publication Date
GB725745A true GB725745A (en) 1955-03-09

Family

ID=6635053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14698/53A Expired GB725745A (en) 1952-05-26 1953-05-26 Pyrrolinoquinolines and processes for making same

Country Status (1)

Country Link
GB (1) GB725745A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5051508A (en) * 1987-07-24 1991-09-24 Smithkline Beckman Intercredit B.V. Dihydropyrrolo quinoline derivatives
GB2316072A (en) * 1996-08-05 1998-02-18 Pharmacia Spa Pyrrolo[3,2-c]quinoline derivatives
US8207187B2 (en) 2005-11-08 2012-06-26 Helperby Therapeutics Limited Use of pyrroloquinoline compounds to kill clinically latent microorganisms

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5051508A (en) * 1987-07-24 1991-09-24 Smithkline Beckman Intercredit B.V. Dihydropyrrolo quinoline derivatives
GB2316072A (en) * 1996-08-05 1998-02-18 Pharmacia Spa Pyrrolo[3,2-c]quinoline derivatives
GB2316072B (en) * 1996-08-05 2000-05-10 Pharmacia Spa Pyrrolo[3,2-c]quinoline derivatives
US8207187B2 (en) 2005-11-08 2012-06-26 Helperby Therapeutics Limited Use of pyrroloquinoline compounds to kill clinically latent microorganisms
US9694006B2 (en) 2005-11-08 2017-07-04 Helperby Therapeutics Limited Use of pyrroloquinoline compounds to kill clinically latent microorganisms
US10493071B2 (en) 2005-11-08 2019-12-03 Helperby Therapeutics Limited Use of pyrroloquinoline compounds to kill clinically latent microorganisms

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