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GB799366A - Process for the preparation of acridine compounds - Google Patents

Process for the preparation of acridine compounds

Info

Publication number
GB799366A
GB799366A GB797158A GB797158A GB799366A GB 799366 A GB799366 A GB 799366A GB 797158 A GB797158 A GB 797158A GB 797158 A GB797158 A GB 797158A GB 799366 A GB799366 A GB 799366A
Authority
GB
United Kingdom
Prior art keywords
chloro
acridine
oxide
methoxy
dichloro
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
GB797158A
Inventor
Ralph Edward Bowman
David John Tivey
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB799366A publication Critical patent/GB799366A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C07D219/12—Amino-alkylamino radicals attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
    • C22B60/02—Obtaining thorium, uranium, or other actinides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Substituted acridines of the general formula <FORM:0799366/IV (b)/1> or acid addition salts thereof, wherein R repre sents a divalent alkyl or hydroxyalkyl radical containing from 2 to 5 carbon atoms and R1 and R2 are the same or different and represent hydrogen or a normal or branched chain alkyl or hydroxyalkyl radical containing 2 to 8 carbon atoms or taken together with the nitrogen atom to which they are attached a saturated heterocyclic ring, and the methoxy group is in the 2- or 3-position, are prepared by condensing a 6,9-dichloro-acridine, 10-oxide of the general formula <FORM:0799366/IV (b)/2> with an aminoalkylamine of the general formula <FORM:0799366/IV (b)/3> or an acid addition salt thereof, R1 and R2 having the above significance, in the presence of an anhydrous organic solvent. The free substituted acridine compounds may be produced by neutralizing the hydrochloride salts initially produced by the condensation reaction. Substantially equivalent quantities of the reactants may be used in conjunction with the organic solvent. Suitable solvents mentioned are phenols, e.g. phenol itself, aliphatic alcohols such as ethanol, isopropanol, pentanol and octanol, aliphatic ketones such as methyl ethyl ketone and di-isobutyl ketone, aliphatic ethers such as dibutyl ether and monoalkyl ethers of ethylene glycol, cyclic ethers such as dioxane and hydrocarbons such as benzene, toluene and xylene. If desired, an excess of either of the reactants may be used, but it is preferable to employ the aminoalkylamine in excess since it can act as the solvent. The preferred acridine reactant is 6,9-dichloro-2-methoxy-acridine, 10-oxide. In the examples the following compounds are prepared: 6-chloro-9-(4-diethylamino - 1 - methylbutylamino)-, 6 - chloro - 9 - (3 - diethylaminopropylamino)-, 6 - chloro - 9 - (3 - diethylamino - 2 - hydroxypropylamino)-, 6 - chloro - 9 - (5 - piperidinopentylamino)-, 6-chloro - 9 - (3 - octylamino - propylamino)-, 6-chloro - 9 - (3 - hexamethyleneiminopropylamino)-, and 6 - chloro - 9 - (3 - isopropylaminopropylamino) - 2 - methoxy - acridine, 10 - oxide dihydrochlorides, and 2 - [2- (and 3) - (6-chloro-2 - methoxy - 9 - acridinylamino) - ethylamino] ethanol, 10-oxide, dihydrochlorides. Starting material. 6,9-Dichloro-2-methoxyacridine, 10-oxide is prepared by treating a solution of 6,9-dichloro-2-methoxy-acridine with perbenzoic acid.
GB797158A 1956-02-15 1956-02-15 Process for the preparation of acridine compounds Expired GB799366A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB474756A GB799361A (en) 1956-02-15 1956-02-15 Acridine compounds and the preparation thereof

Publications (1)

Publication Number Publication Date
GB799366A true GB799366A (en) 1958-08-06

Family

ID=9783019

Family Applications (2)

Application Number Title Priority Date Filing Date
GB474756A Expired GB799361A (en) 1956-02-15 1956-02-15 Acridine compounds and the preparation thereof
GB797158A Expired GB799366A (en) 1956-02-15 1956-02-15 Process for the preparation of acridine compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB474756A Expired GB799361A (en) 1956-02-15 1956-02-15 Acridine compounds and the preparation thereof

Country Status (2)

Country Link
DE (1) DE1109689B (en)
GB (2) GB799361A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1210430B (en) * 1961-02-09 1966-02-10 Parke Davis & Co Process for the production of new quinoline-N-oxides with antiparasitic, antibacterial, antiviral and anti-inflammatory properties

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH517096A (en) * 1968-08-31 1971-12-31 Starogardzkie Zakl Farma Process for the production of new, biologically active 1-nitro-9- (dialkyl-aminoalkylamino) -akridine-N10-oxides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2424061A (en) * 1944-06-29 1947-07-15 Lilly Co Eli 9-amino-alkyl-amino-substituted acridine derivatives
US2459777A (en) * 1944-07-17 1949-01-18 Lilly Co Eli Process of making quinacrine
US2424062A (en) * 1944-07-29 1947-07-15 Lilly Co Eli 2-methoxy-6-chloro-9-[4'-(diisopropylamino)-butylamino]-acridine
US2424063A (en) * 1944-08-07 1947-07-15 Lilly Co Eli 2-methoxy-6-chloro-9-[2'-hydroxy-3'-(ethyl-n-butylamino)-propyl-amino]-acridine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1210430B (en) * 1961-02-09 1966-02-10 Parke Davis & Co Process for the production of new quinoline-N-oxides with antiparasitic, antibacterial, antiviral and anti-inflammatory properties

Also Published As

Publication number Publication date
GB799361A (en) 1958-08-06
DE1109689B (en) 1961-06-29

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