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GB1013224A - Heterocyclic aminoethanols - Google Patents

Heterocyclic aminoethanols

Info

Publication number
GB1013224A
GB1013224A GB2392862A GB2392862A GB1013224A GB 1013224 A GB1013224 A GB 1013224A GB 2392862 A GB2392862 A GB 2392862A GB 2392862 A GB2392862 A GB 2392862A GB 1013224 A GB1013224 A GB 1013224A
Authority
GB
United Kingdom
Prior art keywords
acetyl
alkyl
bromoacetyl
compounds
heterocyclic 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
GB2392862A
Inventor
Walter Hepworth
Alan Mitchell
Madhukar Subraya Chodnekar
Ralph Howe
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2392862A priority Critical patent/GB1013224A/en
Priority to DK592564A priority patent/DK109775C/en
Priority to DK295663A priority patent/DK111032B/en
Priority to DK592764A priority patent/DK111895B/en
Priority to DK592664A priority patent/DK111003B/en
Publication of GB1013224A publication Critical patent/GB1013224A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1013224/C2/1> and salts thereof wherein R1 is hydrogen or an alkyl radical, R2 is hydrogen or an alkyl, or cycloalkyl radical optionally bearing hydroxy substituents or an aralkyl radical and A is a heterocyclic ring containing one or more nitrogen, oxygen or sulphur atoms as hetero-atoms optionally substituted by one or more alkyl, alkenyl, hydroxy, or oxo radicals or by the -CH = CH-CH = CH- radical (thus forming a further benzene nucleus) but excluding 2 - amino-, 2 - methylamino-, 2 - dimethylamino-, 2-ethylamino-, 2-diethylamino-, 2-n-propylamino-, 2 - di - n - propylamino-, 2-n-butylamino-, 2 - di - n - butylamino-, 2-n-pentylamino-, 2 - di - n - pentylamino-, 2-isopropylamino- and 2-isobutylamino-, 1-(1,3-benzodioxol - 5 - yl) ethanol, 1 - (1,4 - benzodioxan - 6 - yl) - 2 - methylaminoethanol, 2-amino - 1 - quinol - 6 - yl - ethanol, 2 - diethyl-amino- and 2 - di - n - butylamino - 1 - quinol-8-yl - ethanol, 2 - methylamino - 1 - (2 - methyl-benzimidazol - 5 - yl) - ethanol and 1 - (2 - benzimidazolon - 5 - yl) - 2 - methylaminoethanol. Preferably rings A and B together form a quinoline, 1-alkyl- or 1-alkenyl-4-quinolone, chroman, 3,4 - dihydro - 1,5 - benzodioxepine, 1,4 - benzodioxan, 1,3 - benzodioxole, benzofuran, dihydrobenzofuran, thianaphthen, 2,3-dimethylindole, benzothiazole, benzoxazole, 2-benzimidazolone, dibenzofuran or phenothiazine nucleus. The compounds are prepared by (a) reducing a haloacetyl derivative of a heterocyclic compound (AB) and reacting the product with an amine NHR1R2; (b) reacting a heterocyclic compound (AB) bearing a substituent group <FORM:1013224/C2/2> or -CHOH.CH2. Halogen with an amine NHR1R2; (c) reducing the group R1R2N. CH2.CO- in the corresponding ketone to an aminoethanol group; (d) reacting a heterocyclic compound (AB) bearing a substituent group -CO.CH2.NH2 or -CHOH.CH2.NH2 with a carbonyl compound R3.CO.R4 (wherein R3 = H1\t alkyl or hydroxyalkyl and R4 = alkyl, hydroxyalkyl or aralkyl) under reducing conditions to give the corresponding substituted aminoethanol derivatives and (e) reducing a heterocyclic compound (AB) bearing a substituent group -COR5, wherein R5 is a radical -CHO or -CH(OR6)OR7, where R6 and R7 are represent hydrogen or C1-6 alkyl, in the presence of an amine NHR1R2. The amino derivative used in process (d) is suitably generated in situ, e.g. by reducing corresponding compounds bearing a diazo, azido, O-benzyl, nitro, benzylamino, benzyloxycarbonylamino, hydroxyimino or cyano group. Glyoxals and glyoxal hydrates of the heterocyclic compounds (AB) are made by oxidizing the corresponding acetyl derivatives with selenium dioxide. 6 - Acetyl - 1 - methyl - quinolone is made by condensing sodium diethyl oxaloacetate with p-aminoacetophenone to give ethyl p-acetylphenyliminosuccinate, heating in diphenyl/diphenylether mixture to give 6-acetyl-2-ethoxycarboxyl - 4 - hydroxyquinoline; hydrolysing the free acid and heating to remove the carboxylic group giving 6-acetyl-4-hydroxyquinoline, and methylating to form the desired product. 5 - Acetyl - 2,3 - dihydrobenzofuran, 6 - acetylchroman, 5 - acetyl - 2 - benzothiazolone and 7 - acetyl - 3,4 - dihydro - 1,5 - benzodioxepine are made by the action of acetyl chloride and aluminum chloride on the appropriate heterocyclic compound. 6 - Bromoacetyl - 1,4 - benzodioxan, 5-bromoacetyl 1,3 - dimethyl - 2 - benzimidazolone, 5-bromoacetyl - 2 - benzothiazolone and 7 - bromoacetyl - 3,4 - dihydro - 1,5 - benzodioxepine are made by brominating the corresponding acetylheterocyclic compounds. 6 - Isopropylaminoacetyl - 1,4 - benzodioxan, 5 - (N - isopropyl - N - methylaminoacetyl)-1,3-benzodioxole and 3,4 - dihydro - 7 - isopropylaminoacetyl - 1,5 - benzodioxepine (hydrochlorides) are made by reaction of the appropriate amine with bromoacetyl derivative of the corresponding heterocyclic compound. 5 - Aminoacetyl - 1,3 - dimethyl - 2 - benzimidazolone, 5 - aminoacetyl - 2 - benzothiazolone 5-aminoacetyl - 2 - benzimidazolone and 6 - aminoacetyl 1,4 - benzodioxan (hydrohalides) are made by treating the corresponding bromoacetyl compounds with hexamine and decomposing the resulting hexaminium salt.
GB2392862A 1962-06-21 1962-06-21 Heterocyclic aminoethanols Expired GB1013224A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB2392862A GB1013224A (en) 1962-06-21 1962-06-21 Heterocyclic aminoethanols
DK592564A DK109775C (en) 1962-06-21 1963-06-21 Process for the preparation of heterocyclic aminoethanol derivatives.
DK295663A DK111032B (en) 1962-06-21 1963-06-21 Process for the preparation of heterocyclic 2-aminoethanol derivatives.
DK592764A DK111895B (en) 1962-06-21 1964-12-02 Process for the preparation of heterocyclic 2-aminoethanol derivatives.
DK592664A DK111003B (en) 1962-06-21 1964-12-02 Process for the preparation of heterocyclic aminoethanol derivatives.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2392862A GB1013224A (en) 1962-06-21 1962-06-21 Heterocyclic aminoethanols

Publications (1)

Publication Number Publication Date
GB1013224A true GB1013224A (en) 1965-12-15

Family

ID=10203572

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2392862A Expired GB1013224A (en) 1962-06-21 1962-06-21 Heterocyclic aminoethanols

Country Status (2)

Country Link
DK (4) DK111032B (en)
GB (1) GB1013224A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444173A (en) * 1965-03-10 1969-05-13 Pfizer & Co C Substituted 8-hydroxy-quinoline derivatives
US3668206A (en) * 1968-10-16 1972-06-06 Venkatachala Lakshmi Narayanan Heterocyclic amine derivatives of 5,8-dihydronaphthyloxy propanols
US4348398A (en) * 1980-12-23 1982-09-07 Merck Sharp & Dohme (I.A.) Corp. Quinolinyl ethanolamines
US4476132A (en) * 1981-03-24 1984-10-09 Ciba-Geigy Corporation Acylquinolinone derivatives, and antiallergic preparations and methods of inhibiting allergic reactions using them
US4638070A (en) * 1978-12-21 1987-01-20 Continental Pharma Heterocyclic amino-alcohol derivatives
DK151330B (en) * 1975-11-18 1987-11-23 Continental Pharma METHOD OF ANALOGUE FOR THE PREPARATION OF AMINOAL ALCOHOL DERIVATIVES OR PHARMACEUTICAL ACCEPTABLE SALTS THEREOF
US4728647A (en) * 1985-05-30 1988-03-01 Rhone-Poulenc Sante Amides derived from quinoline, and anxiolytic compositions containing them
FR2746395A1 (en) * 1996-03-22 1997-09-26 Adir New aryl ethanolamine and aryloxy propanolamine derivatives with affinity for beta 3 adrenergic receptors
JP2004510764A (en) * 2000-10-02 2004-04-08 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Metabotropic glutamate receptor antagonist
JP2005524679A (en) * 2002-03-29 2005-08-18 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444173A (en) * 1965-03-10 1969-05-13 Pfizer & Co C Substituted 8-hydroxy-quinoline derivatives
US3668206A (en) * 1968-10-16 1972-06-06 Venkatachala Lakshmi Narayanan Heterocyclic amine derivatives of 5,8-dihydronaphthyloxy propanols
DK151330B (en) * 1975-11-18 1987-11-23 Continental Pharma METHOD OF ANALOGUE FOR THE PREPARATION OF AMINOAL ALCOHOL DERIVATIVES OR PHARMACEUTICAL ACCEPTABLE SALTS THEREOF
US4638070A (en) * 1978-12-21 1987-01-20 Continental Pharma Heterocyclic amino-alcohol derivatives
US4348398A (en) * 1980-12-23 1982-09-07 Merck Sharp & Dohme (I.A.) Corp. Quinolinyl ethanolamines
US4476132A (en) * 1981-03-24 1984-10-09 Ciba-Geigy Corporation Acylquinolinone derivatives, and antiallergic preparations and methods of inhibiting allergic reactions using them
US4728647A (en) * 1985-05-30 1988-03-01 Rhone-Poulenc Sante Amides derived from quinoline, and anxiolytic compositions containing them
FR2746395A1 (en) * 1996-03-22 1997-09-26 Adir New aryl ethanolamine and aryloxy propanolamine derivatives with affinity for beta 3 adrenergic receptors
JP2004510764A (en) * 2000-10-02 2004-04-08 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Metabotropic glutamate receptor antagonist
JP2005524679A (en) * 2002-03-29 2005-08-18 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Radiolabeled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands

Also Published As

Publication number Publication date
DK111003B (en) 1968-04-29
DK111895B (en) 1968-10-21
DK109775C (en) 1968-07-01
DK111032B (en) 1968-05-13

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